data_publication_text
_publ_requested_journal          'Beilstein J.Org.Chem.'
_publ_contact_author_name        'Rybalova T.V.'
_publ_contact_author_email       rybalova@nioch.nsc.ru
loop_
_publ_author_name
_publ_author_address
'Gulman M.M.' ''
'Polienko Yu.F.' ''
'Trakhinina S.Yu.' ''
'Gatilov Yu.V.' ''
'Rybalova T.V.' ''
'Dobrynin S.A.' ''
'Kirilyuk I.A.' ''

data_comp2d_gke5
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         
;
 2,2,5-triethyl-3,4-bis(hydroxymethyl)-5-((trimethylsilyl)ethynyl)pyrrolidin-1-
 oxyl
;
_chemical_name_common             ?
_chemical_melting_point           342
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C17 H32 N O3 Si' 
_chemical_formula_weight          326.52

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Si'  'Si'   0.0817   0.0704
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    12.4707(5)
_cell_length_b                    17.5991(8)
_cell_length_c                    19.5933(9)
_cell_angle_alpha                 82.553(2)
_cell_angle_beta                  79.474(2)
_cell_angle_gamma                 71.963(2)
_cell_volume                      4007.8(3)
_cell_formula_units_Z             8
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used       9849
_cell_measurement_theta_min         2.27
_cell_measurement_theta_max        25.10
 
_exptl_crystal_description        'block' 
_exptl_crystal_colour             'yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.082          
_exptl_crystal_F_000              1432
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.800
_exptl_crystal_size_mid           0.400
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.128
_shelx_estimated_absorpt_T_min    0.904
_shelx_estimated_absorpt_T_max    0.975
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.7068 
_exptl_absorpt_correction_T_max    0.7453
_exptl_absorpt_process_details    'SADABS-2016/2'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed tube'
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'   
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             56190
_diffrn_reflns_av_unetI/netI      0.0342
_diffrn_reflns_av_R_equivalents   0.0348
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -21
_diffrn_reflns_limit_k_max        21
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          1.553
_diffrn_reflns_theta_max          26.127
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.995
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.995
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.995
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              15904
_reflns_number_gt                 10265
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1235P)²+1.2150P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          15904
_refine_ls_number_parameters      840
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0995
_refine_ls_R_factor_gt            0.0635
_refine_ls_wR_factor_ref          0.2149
_refine_ls_wR_factor_gt           0.1795
_refine_ls_goodness_of_fit_ref    1.003
_refine_ls_restrained_S_all       1.003
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Si1 Si 1.04759(7) 0.35535(5) -0.04866(4) 0.0583(2) Uani 1 1 d . . . . .
O1 O 1.23048(14) 0.17081(11) 0.16258(9) 0.0622(5) Uani 1 1 d . . . . .
C6 C 0.8284(2) 0.2116(2) 0.26405(15) 0.0699(8) Uani 0.639(5) 1 d . . P A 1
H6A H 0.837245 0.217643 0.307388 0.084 Uiso 0.639(5) 1 calc R U P A 1
H6B H 0.765269 0.250025 0.253847 0.084 Uiso 0.639(5) 1 calc R U P A 1
O2 O 0.8102(3) 0.1384(2) 0.26433(18) 0.0848(13) Uani 0.639(5) 1 d . . P A 1
H2O H 0.794563 0.134130 0.226411 0.127 Uiso 0.639(5) 1 calc R U P A 1
C6' C 0.8284(2) 0.2116(2) 0.26405(15) 0.0699(8) Uani 0.361(5) 1 d . . P A 2
H6C H 0.832825 0.159241 0.267061 0.084 Uiso 0.361(5) 1 calc R U P A 2
H6D H 0.831067 0.224190 0.306644 0.084 Uiso 0.361(5) 1 calc R U P A 2
O3 O 0.7226(4) 0.2578(4) 0.2429(3) 0.080(2) Uani 0.361(5) 1 d . . P A 2
H3O H 0.712362 0.238726 0.209461 0.120 Uiso 0.361(5) 1 calc R U P A 2
O4 O 0.8861(3) 0.44002(16) 0.2317(2) 0.1378(12) Uani 1 1 d . . . . .
H4O H 0.826443 0.476668 0.237415 0.207 Uiso 1 1 calc R U . . .
N1 N 1.12703(15) 0.20448(11) 0.18797(10) 0.0454(5) Uani 1 1 d . . . . .
C1 C 0.8984(3) 0.4174(3) -0.0533(2) 0.1151(15) Uani 1 1 d . . . . .
H26 H 0.891159 0.472254 -0.047614 0.173 Uiso 1 1 calc R U . . .
H27 H 0.847884 0.398332 -0.017011 0.173 Uiso 1 1 calc R U . . .
H1 H 0.878951 0.413869 -0.097761 0.173 Uiso 1 1 calc R U . . .
C2 C 1.0682(2) 0.31437(15) 0.10450(14) 0.0548(6) Uani 1 1 d . . . . .
C3 C 1.0763(2) 0.29288(14) 0.17889(13) 0.0498(6) Uani 1 1 d . . . . .
C4 C 0.9570(2) 0.30263(14) 0.22226(12) 0.0503(6) Uani 1 1 d . . . . .
H7 H 0.965001 0.301768 0.271216 0.060 Uiso 1 1 calc R U . . .
C5 C 0.93104(19) 0.22562(14) 0.21342(12) 0.0474(5) Uani 1 1 d . . . . .
H10 H 0.914223 0.228931 0.165995 0.057 Uiso 1 1 calc R U . A 1
C8 C 1.0799(4) 0.2601(2) -0.08860(19) 0.0922(11) Uani 1 1 d . . . . .
H3 H 1.066019 0.270983 -0.136008 0.138 Uiso 1 1 calc R U . . .
H32 H 1.032063 0.229273 -0.063118 0.138 Uiso 1 1 calc R U . . .
H31 H 1.158506 0.230458 -0.087502 0.138 Uiso 1 1 calc R U . . .
C9 C 1.0621(2) 0.33115(16) 0.04378(15) 0.0602(7) Uani 1 1 d . . . . .
C10 C 1.04505(19) 0.15942(14) 0.21850(12) 0.0469(5) Uani 1 1 d . . . . .
C11 C 0.8674(3) 0.37926(17) 0.20513(17) 0.0753(9) Uani 1 1 d . . . . .
H11A H 0.870894 0.389444 0.155034 0.090 Uiso 1 1 calc R U . . .
H11B H 0.792192 0.374719 0.224763 0.090 Uiso 1 1 calc R U . . .
C13 C 1.0643(3) 0.08707(16) 0.17716(15) 0.0651(7) Uani 1 1 d . . . . .
H12 H 1.139153 0.050575 0.182392 0.078 Uiso 1 1 calc R U . . .
H11 H 1.008635 0.059440 0.198192 0.078 Uiso 1 1 calc R U . . .
C14 C 1.0570(3) 0.10362(19) 0.10068(15) 0.0728(8) Uani 1 1 d . . . . .
H13 H 0.981482 0.136219 0.094364 0.109 Uiso 1 1 calc R U . . .
H14 H 1.073748 0.053884 0.080011 0.109 Uiso 1 1 calc R U . . .
H15 H 1.111206 0.131312 0.078824 0.109 Uiso 1 1 calc R U . . .
C15 C 1.0589(2) 0.13253(17) 0.29575(13) 0.0615(7) Uani 1 1 d . . . . .
H16 H 1.040907 0.180123 0.320729 0.074 Uiso 1 1 calc R U . . .
H17 H 1.003098 0.104556 0.315429 0.074 Uiso 1 1 calc R U . . .
C16 C 1.1759(3) 0.0787(2) 0.30901(16) 0.0771(9) Uani 1 1 d . . . . .
H19 H 1.191972 0.028911 0.288604 0.116 Uiso 1 1 calc R U . . .
H18 H 1.176872 0.068586 0.358264 0.116 Uiso 1 1 calc R U . . .
H20 H 1.232721 0.104724 0.288534 0.116 Uiso 1 1 calc R U . . .
C17 C 1.1532(3) 0.33510(19) 0.20225(18) 0.0753(8) Uani 1 1 d . . . . .
H21 H 1.225328 0.323122 0.171142 0.090 Uiso 1 1 calc R U . . .
H25 H 1.117637 0.392513 0.196808 0.090 Uiso 1 1 calc R U . . .
C18 C 1.1774(3) 0.3132(2) 0.2756(2) 0.0972(12) Uani 1 1 d . . . . .
H24 H 1.108510 0.332981 0.307424 0.146 Uiso 1 1 calc R U . . .
H22 H 1.233810 0.336769 0.283072 0.146 Uiso 1 1 calc R U . . .
H23 H 1.205239 0.256004 0.283415 0.146 Uiso 1 1 calc R U . . .
C19 C 1.1493(4) 0.4100(2) -0.0898(2) 0.1012(12) Uani 1 1 d . . . . .
H29 H 1.121154 0.464389 -0.077159 0.152 Uiso 1 1 calc R U . . .
H30 H 1.158455 0.409513 -0.139430 0.152 Uiso 1 1 calc R U . . .
H28 H 1.221666 0.384722 -0.074166 0.152 Uiso 1 1 calc R U . . .
Si2 Si 0.03576(7) 0.55196(5) 0.36230(5) 0.0665(2) Uani 1 1 d . . . . .
O5 O -0.26025(17) 0.83038(12) 0.36863(12) 0.0774(6) Uani 1 1 d . . . . .
O6 O 0.13702(16) 0.90932(17) 0.44022(12) 0.0903(8) Uani 1 1 d . . . . .
H6O H 0.180736 0.880546 0.410961 0.135 Uiso 1 1 calc R U . . .
O7 O 0.0872(2) 0.8086(2) 0.55118(12) 0.1073(9) Uani 1 1 d . . . . .
H7O H 0.126059 0.832612 0.523962 0.161 Uiso 1 1 calc R U . . .
N2 N -0.18831(17) 0.84379(13) 0.40050(12) 0.0562(5) Uani 1 1 d . . . . .
C20 C 0.1747(4) 0.5041(3) 0.3944(2) 0.1200(15) Uani 1 1 d . . . . .
H62 H 0.213460 0.543710 0.393390 0.180 Uiso 1 1 calc R U . . .
H63 H 0.220772 0.462667 0.365036 0.180 Uiso 1 1 calc R U . . .
H33 H 0.161419 0.481325 0.441236 0.180 Uiso 1 1 calc R U . . .
C21 C -0.0777(3) 0.70973(18) 0.42723(15) 0.0655(7) Uani 1 1 d . . . . .
C22 C -0.1406(2) 0.78698(17) 0.45734(14) 0.0600(7) Uani 1 1 d . . . . .
C23 C -0.0309(3) 0.64743(18) 0.40165(17) 0.0709(8) Uani 1 1 d . . . . .
C24 C -0.1340(2) 0.90895(16) 0.37720(14) 0.0567(6) Uani 1 1 d . . . . .
C25 C -0.2142(3) 0.98795(18) 0.4071(2) 0.0774(9) Uani 1 1 d . . . . .
H51 H -0.222456 0.980578 0.457523 0.093 Uiso 1 1 calc R U . . .
H50 H -0.177626 1.029860 0.392417 0.093 Uiso 1 1 calc R U . . .
C26 C -0.3326(3) 1.0167(2) 0.3862(3) 0.1086(14) Uani 1 1 d . . . . .
H48 H -0.326105 1.021477 0.336346 0.163 Uiso 1 1 calc R U . . .
H49 H -0.372940 1.067967 0.403760 0.163 Uiso 1 1 calc R U . . .
H34 H -0.373598 0.978833 0.405260 0.163 Uiso 1 1 calc R U . . .
C27 C 0.0576(4) 0.5733(2) 0.26736(19) 0.0965(11) Uani 1 1 d . . . . .
H35 H -0.014871 0.591550 0.251077 0.145 Uiso 1 1 calc R U . . .
H65 H 0.103550 0.525403 0.245806 0.145 Uiso 1 1 calc R U . . .
H64 H 0.095682 0.614085 0.255559 0.145 Uiso 1 1 calc R U . . .
C28 C -0.0620(4) 0.4896(2) 0.3894(2) 0.1117(14) Uani 1 1 d . . . . .
H37 H -0.063330 0.473109 0.438141 0.168 Uiso 1 1 calc R U . . .
H38 H -0.036124 0.443184 0.363178 0.168 Uiso 1 1 calc R U . . .
H36 H -0.137455 0.520219 0.381015 0.168 Uiso 1 1 calc R U . . .
C29 C -0.0615(2) 0.82800(18) 0.47921(13) 0.0605(7) Uani 1 1 d . . . . .
H44 H -0.107517 0.866717 0.512695 0.073 Uiso 1 1 calc R U . . .
C30 C 0.0355(3) 0.7709(2) 0.51374(17) 0.0872(10) Uani 1 1 d . . . . .
H42 H 0.006455 0.731984 0.545103 0.105 Uiso 1 1 calc R U . . .
H43 H 0.092888 0.741956 0.478194 0.105 Uiso 1 1 calc R U . . .
C32 C -0.0256(2) 0.87543(16) 0.41206(13) 0.0540(6) Uani 1 1 d . . . . .
H47 H 0.030217 0.836818 0.381726 0.065 Uiso 1 1 calc R U . . .
C33 C 0.0278(2) 0.9402(2) 0.41915(18) 0.0740(8) Uani 1 1 d . . . . .
H45 H 0.034495 0.971279 0.374767 0.089 Uiso 1 1 calc R U . . .
H46 H -0.022357 0.976079 0.452937 0.089 Uiso 1 1 calc R U . . .
C34 C -0.1118(3) 0.9195(2) 0.29791(17) 0.0843(9) Uani 1 1 d . . . . .
H52 H -0.184134 0.931822 0.280969 0.101 Uiso 1 1 calc R U . . .
H56 H -0.083475 0.965645 0.284622 0.101 Uiso 1 1 calc R U . . .
C35 C -0.0287(4) 0.8491(3) 0.26093(18) 0.1043(13) Uani 1 1 d . . . . .
H55 H 0.047047 0.842915 0.269441 0.157 Uiso 1 1 calc R U . . .
H54 H -0.031137 0.858586 0.211793 0.157 Uiso 1 1 calc R U . . .
H53 H -0.049448 0.801154 0.278141 0.157 Uiso 1 1 calc R U . . .
C36 C -0.2388(3) 0.7733(3) 0.5154(2) 0.0974(12) Uani 1 1 d . . . . .
H61 H -0.282364 0.747004 0.495581 0.117 Uiso 1 1 calc R U . . .
H57 H -0.204098 0.736462 0.552014 0.117 Uiso 1 1 calc R U . . .
C37 C -0.3184(4) 0.8436(3) 0.5475(3) 0.1313(18) Uani 1 1 d . . . . .
H60 H -0.276763 0.872327 0.565320 0.197 Uiso 1 1 calc R U . . .
H58 H -0.369744 0.827034 0.584859 0.197 Uiso 1 1 calc R U . . .
H59 H -0.361076 0.877840 0.513278 0.197 Uiso 1 1 calc R U . . .
Si3 Si 0.40465(7) 0.66027(5) 0.54408(4) 0.0648(2) Uani 1 1 d . . . . .
O8 O 0.26643(13) 0.85004(11) 0.31547(9) 0.0568(4) Uani 1 1 d . . . . .
O9 O 0.70194(18) 0.58089(11) 0.26813(12) 0.0741(6) Uani 1 1 d D . . . .
H9Q H 0.735(3) 0.6171(19) 0.275(2) 0.111 Uiso 1 1 d D U . . .
O10 O 0.77521(15) 0.71004(12) 0.27395(11) 0.0680(5) Uani 1 1 d D . . . .
H10Q H 0.782(3) 0.726(2) 0.3092(14) 0.102 Uiso 1 1 d D U . . .
N3 N 0.36919(15) 0.80623(11) 0.30020(9) 0.0414(4) Uani 1 1 d . . . . .
C7 C 0.56696(18) 0.76451(13) 0.28966(12) 0.0407(5) Uani 1 1 d . . . . .
H7A H 0.575235 0.761799 0.338775 0.049 Uiso 1 1 calc R U . . .
C38 C 0.5491(4) 0.5878(3) 0.5458(2) 0.1344(19) Uani 1 1 d . . . . .
H72 H 0.545393 0.534516 0.543754 0.202 Uiso 1 1 calc R U . . .
H73 H 0.575773 0.590895 0.588053 0.202 Uiso 1 1 calc R U . . .
H66 H 0.600690 0.600702 0.506539 0.202 Uiso 1 1 calc R U . . .
C39 C 0.3908(2) 0.69922(14) 0.39036(13) 0.0502(6) Uani 1 1 d . . . . .
C40 C 0.40003(19) 0.71759(13) 0.31396(12) 0.0437(5) Uani 1 1 d . . . . .
C41 C 0.3885(2) 0.68432(16) 0.45152(14) 0.0590(7) Uani 1 1 d . . . . .
C42 C 0.46687(18) 0.83904(13) 0.27572(11) 0.0410(5) Uani 1 1 d . . . . .
C43 C 0.4564(2) 0.90982(14) 0.31740(13) 0.0532(6) Uani 1 1 d . . . . .
H82 H 0.524189 0.927215 0.302449 0.064 Uiso 1 1 calc R U . . .
H79 H 0.391826 0.953846 0.305269 0.064 Uiso 1 1 calc R U . . .
C44 C 0.4416(2) 0.89467(17) 0.39603(14) 0.0615(7) Uani 1 1 d . . . . .
H80 H 0.381214 0.870437 0.411375 0.092 Uiso 1 1 calc R U . . .
H81 H 0.422808 0.944583 0.416744 0.092 Uiso 1 1 calc R U . . .
H67 H 0.511289 0.859394 0.409750 0.092 Uiso 1 1 calc R U . . .
C45 C 0.2933(3) 0.6153(2) 0.58938(19) 0.0943(11) Uani 1 1 d . . . . .
H68 H 0.219540 0.653390 0.587195 0.142 Uiso 1 1 calc R U . . .
H93 H 0.303716 0.600763 0.637187 0.142 Uiso 1 1 calc R U . . .
H94 H 0.298482 0.568366 0.567385 0.142 Uiso 1 1 calc R U . . .
C46 C 0.3945(4) 0.7551(2) 0.57933(18) 0.0958(11) Uani 1 1 d . . . . .
H69 H 0.451566 0.777653 0.552793 0.144 Uiso 1 1 calc R U . . .
H70 H 0.406377 0.744720 0.627113 0.144 Uiso 1 1 calc R U . . .
H71 H 0.320215 0.792084 0.576396 0.144 Uiso 1 1 calc R U . . .
C47 C 0.3193(2) 0.68393(16) 0.28473(14) 0.0589(7) Uani 1 1 d . . . . .
H77 H 0.344936 0.625915 0.291612 0.071 Uiso 1 1 calc R U . . .
H78 H 0.243713 0.702039 0.311441 0.071 Uiso 1 1 calc R U . . .
C48 C 0.3104(3) 0.7072(2) 0.20846(16) 0.0739(8) Uani 1 1 d . . . . .
H75 H 0.284565 0.764562 0.200862 0.111 Uiso 1 1 calc R U . . .
H74 H 0.257142 0.684734 0.195002 0.111 Uiso 1 1 calc R U . . .
H76 H 0.383937 0.687152 0.181097 0.111 Uiso 1 1 calc R U . . .
C49 C 0.52666(19) 0.69295(13) 0.28012(12) 0.0422(5) Uani 1 1 d . . . . .
H83 H 0.529342 0.690469 0.230136 0.051 Uiso 1 1 calc R U . . .
C50 C 0.5952(2) 0.61103(14) 0.30916(14) 0.0580(6) Uani 1 1 d . . . . .
H84 H 0.606919 0.615399 0.355926 0.070 Uiso 1 1 calc R U . . .
H85 H 0.551520 0.573387 0.312146 0.070 Uiso 1 1 calc R U . . .
C51 C 0.6808(2) 0.76662(16) 0.24633(14) 0.0537(6) Uani 1 1 d . . . . .
H86 H 0.681914 0.755180 0.199053 0.064 Uiso 1 1 calc R U . . .
H87 H 0.688486 0.820036 0.244721 0.064 Uiso 1 1 calc R U . . .
C52 C 0.4709(2) 0.86509(14) 0.19715(12) 0.0503(6) Uani 1 1 d . . . . .
H88 H 0.534579 0.886984 0.182196 0.060 Uiso 1 1 calc R U . . .
H92 H 0.486621 0.817574 0.172426 0.060 Uiso 1 1 calc R U . . .
C53 C 0.3651(3) 0.92596(16) 0.17491(14) 0.0637(7) Uani 1 1 d . . . . .
H90 H 0.300200 0.906612 0.191286 0.096 Uiso 1 1 calc R U . . .
H91 H 0.374723 0.934092 0.125031 0.096 Uiso 1 1 calc R U . . .
H89 H 0.353317 0.975800 0.194318 0.096 Uiso 1 1 calc R U . . .
Si4 Si 0.50621(7) 0.44745(5) 0.14808(5) 0.0651(2) Uani 1 1 d . . . . .
O11 O 0.75627(17) 0.13807(13) 0.13419(11) 0.0767(6) Uani 1 1 d . . . . .
O12 O 0.32921(16) 0.17197(17) 0.01925(11) 0.0853(7) Uani 1 1 d . . . . .
H12O H 0.285529 0.193341 0.052617 0.128 Uiso 1 1 calc R U . . .
O13 O 0.4327(2) 0.26569(14) -0.07395(10) 0.0822(6) Uani 1 1 d . . . . .
H13O H 0.400781 0.231739 -0.057105 0.123 Uiso 1 1 calc R U . . .
N4 N 0.67944(16) 0.14932(11) 0.09624(10) 0.0480(5) Uani 1 1 d . . . . .
C54 C 0.4823(5) 0.4235(3) 0.2432(2) 0.1265(17) Uani 1 1 d . . . . .
H95 H 0.431807 0.390619 0.254176 0.190 Uiso 1 1 calc R U . . .
H97 H 0.448918 0.472219 0.266111 0.190 Uiso 1 1 calc R U . . .
H123 H 0.553887 0.395116 0.258697 0.190 Uiso 1 1 calc R U . . .
C55 C 0.6142(2) 0.29209(15) 0.07896(14) 0.0555(6) Uani 1 1 d . . . . .
C56 C 0.6587(2) 0.21739(13) 0.04302(12) 0.0473(5) Uani 1 1 d . . . . .
C57 C 0.5760(3) 0.35271(16) 0.10737(15) 0.0633(7) Uani 1 1 d . . . . .
C58 C 0.5969(2) 0.10240(14) 0.10691(13) 0.0501(6) Uani 1 1 d . . . . .
C59 C 0.6547(3) 0.02153(15) 0.07361(17) 0.0718(8) Uani 1 1 d . . . . .
H106 H 0.599362 -0.008258 0.080368 0.086 Uiso 1 1 calc R U . . .
H109 H 0.673743 0.032864 0.023857 0.086 Uiso 1 1 calc R U . . .
C60 C 0.7616(4) -0.0319(2) 0.1009(2) 0.1133(14) Uani 1 1 d . . . . .
H107 H 0.816669 -0.002872 0.095866 0.170 Uiso 1 1 calc R U . . .
H108 H 0.792866 -0.078419 0.074800 0.170 Uiso 1 1 calc R U . . .
H96 H 0.742881 -0.048124 0.149130 0.170 Uiso 1 1 calc R U . . .
C61 C 0.3725(4) 0.4950(3) 0.1127(3) 0.154(2) Uani 1 1 d . . . . .
H99 H 0.389356 0.510142 0.064043 0.231 Uiso 1 1 calc R U . . .
H100 H 0.329856 0.541760 0.136832 0.231 Uiso 1 1 calc R U . . .
H98 H 0.328402 0.457860 0.118889 0.231 Uiso 1 1 calc R U . . .
C62 C 0.7710(2) 0.21793(19) -0.00622(16) 0.0685(8) Uani 1 1 d . . . . .
H101 H 0.753833 0.262004 -0.041640 0.082 Uiso 1 1 calc R U . . .
H105 H 0.822461 0.228383 0.020521 0.082 Uiso 1 1 calc R U . . .
C63 C 0.8321(3) 0.1421(2) -0.04191(19) 0.0863(10) Uani 1 1 d . . . . .
H102 H 0.850687 0.097916 -0.007526 0.130 Uiso 1 1 calc R U . . .
H103 H 0.900915 0.147694 -0.070453 0.130 Uiso 1 1 calc R U . . .
H104 H 0.783654 0.132305 -0.070502 0.130 Uiso 1 1 calc R U . . .
C64 C 0.5561(3) 0.0879(2) 0.18521(15) 0.0755(8) Uani 1 1 d . . . . .
H114 H 0.501251 0.057963 0.190342 0.091 Uiso 1 1 calc R U . . .
H110 H 0.620987 0.054318 0.206484 0.091 Uiso 1 1 calc R U . . .
C65 C 0.5026(3) 0.1610(2) 0.22538(15) 0.0893(11) Uani 1 1 d . . . . .
H111 H 0.553253 0.193733 0.218016 0.134 Uiso 1 1 calc R U . . .
H112 H 0.488515 0.144922 0.274092 0.134 Uiso 1 1 calc R U . . .
H113 H 0.431811 0.191126 0.209688 0.134 Uiso 1 1 calc R U . . .
C66 C 0.50361(19) 0.15783(14) 0.06701(11) 0.0456(5) Uani 1 1 d . . . . .
H117 H 0.454055 0.197589 0.098636 0.055 Uiso 1 1 calc R U . . .
C67 C 0.4282(2) 0.11713(19) 0.04252(15) 0.0663(7) Uani 1 1 d . . . . .
H115 H 0.472174 0.084632 0.004814 0.080 Uiso 1 1 calc R U . . .
H116 H 0.405049 0.081581 0.080480 0.080 Uiso 1 1 calc R U . . .
C68 C 0.4933(3) 0.27952(17) -0.02475(14) 0.0655(7) Uani 1 1 d . . . . .
H119 H 0.439259 0.309784 0.011410 0.079 Uiso 1 1 calc R U . . .
H118 H 0.541923 0.311849 -0.047636 0.079 Uiso 1 1 calc R U . . .
C69 C 0.5998(3) 0.51228(19) 0.1256(2) 0.0930(11) Uani 1 1 d . . . . .
H120 H 0.671016 0.486083 0.142290 0.140 Uiso 1 1 calc R U . . .
H122 H 0.563931 0.561962 0.146833 0.140 Uiso 1 1 calc R U . . .
H121 H 0.613412 0.522714 0.075964 0.140 Uiso 1 1 calc R U . . .
C70 C 0.5664(2) 0.20265(14) 0.00871(12) 0.0452(5) Uani 1 1 d . . . . .
H70A H 0.604546 0.166116 -0.027924 0.054 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Si1 C9 1.835(3) . ?
Si1 C19 1.835(4) . ?
Si1 C8 1.841(3) . ?
Si1 C1 1.855(4) . ?
O1 N1 1.277(2) . ?
C6 O2 1.373(5) . ?
C6 C5 1.534(4) . ?
C6 H6A 0.9000 . ?
C6 H6B 0.9000 . ?
O2 H2O 0.8200 . ?
C6' O3 1.421(6) . ?
C6' C5 1.534(4) . ?
C6' H6C 0.9000 . ?
C6' H6D 0.9000 . ?
O3 H3O 0.8200 . ?
O4 C11 1.346(4) . ?
O4 H4O 0.8200 . ?
N1 C10 1.479(3) . ?
N1 C3 1.487(3) . ?
C1 H26 0.9600 . ?
C1 H27 0.9600 . ?
C1 H1 0.9600 . ?
C2 C9 1.198(4) . ?
C2 C3 1.471(4) . ?
C3 C17 1.539(4) . ?
C3 C4 1.543(3) . ?
C4 C11 1.506(3) . ?
C4 C5 1.525(3) . ?
C4 H7 0.9800 . ?
C5 C10 1.544(3) . ?
C5 H10 0.9800 . ?
C8 H3 0.9600 . ?
C8 H32 0.9600 . ?
C8 H31 0.9600 . ?
C10 C13 1.530(3) . ?
C10 C15 1.551(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 C14 1.503(4) . ?
C13 H12 0.9700 . ?
C13 H11 0.9700 . ?
C14 H13 0.9600 . ?
C14 H14 0.9600 . ?
C14 H15 0.9600 . ?
C15 C16 1.520(4) . ?
C15 H16 0.9700 . ?
C15 H17 0.9700 . ?
C16 H19 0.9600 . ?
C16 H18 0.9600 . ?
C16 H20 0.9600 . ?
C17 C18 1.500(5) . ?
C17 H21 0.9700 . ?
C17 H25 0.9700 . ?
C18 H24 0.9600 . ?
C18 H22 0.9600 . ?
C18 H23 0.9600 . ?
C19 H29 0.9600 . ?
C19 H30 0.9600 . ?
C19 H28 0.9600 . ?
Si2 C23 1.829(3) . ?
Si2 C27 1.837(4) . ?
Si2 C28 1.848(4) . ?
Si2 C20 1.861(4) . ?
O5 N2 1.275(3) . ?
O6 C33 1.417(4) . ?
O6 H6O 0.8200 . ?
O7 C30 1.399(4) . ?
O7 H7O 0.8200 . ?
N2 C22 1.476(4) . ?
N2 C24 1.488(3) . ?
C20 H62 0.9600 . ?
C20 H63 0.9600 . ?
C20 H33 0.9600 . ?
C21 C23 1.197(4) . ?
C21 C22 1.480(4) . ?
C22 C29 1.535(4) . ?
C22 C36 1.566(4) . ?
C24 C34 1.525(4) . ?
C24 C32 1.543(4) . ?
C24 C25 1.553(4) . ?
C25 C26 1.519(5) . ?
C25 H51 0.9700 . ?
C25 H50 0.9700 . ?
C26 H48 0.9600 . ?
C26 H49 0.9600 . ?
C26 H34 0.9600 . ?
C27 H35 0.9600 . ?
C27 H65 0.9600 . ?
C27 H64 0.9600 . ?
C28 H37 0.9600 . ?
C28 H38 0.9600 . ?
C28 H36 0.9600 . ?
C29 C30 1.517(4) . ?
C29 C32 1.536(4) . ?
C29 H44 0.9800 . ?
C30 H42 0.9700 . ?
C30 H43 0.9700 . ?
C32 C33 1.519(4) . ?
C32 H47 0.9800 . ?
C33 H45 0.9700 . ?
C33 H46 0.9700 . ?
C34 C35 1.516(5) . ?
C34 H52 0.9700 . ?
C34 H56 0.9700 . ?
C35 H55 0.9600 . ?
C35 H54 0.9600 . ?
C35 H53 0.9600 . ?
C36 C37 1.457(6) . ?
C36 H61 0.9700 . ?
C36 H57 0.9700 . ?
C37 H60 0.9600 . ?
C37 H58 0.9600 . ?
C37 H59 0.9600 . ?
Si3 C45 1.841(3) . ?
Si3 C41 1.841(3) . ?
Si3 C46 1.847(4) . ?
Si3 C38 1.860(4) . ?
O8 N3 1.278(2) . ?
O9 C50 1.408(3) . ?
O9 H9Q 0.901(18) . ?
O10 C51 1.427(3) . ?
O10 H10Q 0.809(18) . ?
N3 C42 1.482(3) . ?
N3 C40 1.487(3) . ?
C7 C51 1.524(3) . ?
C7 C49 1.537(3) . ?
C7 C42 1.540(3) . ?
C7 H7A 0.9800 . ?
C38 H72 0.9600 . ?
C38 H73 0.9600 . ?
C38 H66 0.9600 . ?
C39 C41 1.190(3) . ?
C39 C40 1.481(3) . ?
C40 C47 1.536(3) . ?
C40 C49 1.546(3) . ?
C42 C43 1.536(3) . ?
C42 C52 1.545(3) . ?
C43 C44 1.516(4) . ?
C43 H82 0.9700 . ?
C43 H79 0.9700 . ?
C44 H80 0.9600 . ?
C44 H81 0.9600 . ?
C44 H67 0.9600 . ?
C45 H68 0.9600 . ?
C45 H93 0.9600 . ?
C45 H94 0.9600 . ?
C46 H69 0.9600 . ?
C46 H70 0.9600 . ?
C46 H71 0.9600 . ?
C47 C48 1.512(4) . ?
C47 H77 0.9700 . ?
C47 H78 0.9700 . ?
C48 H75 0.9600 . ?
C48 H74 0.9600 . ?
C48 H76 0.9600 . ?
C49 C50 1.528(3) . ?
C49 H83 0.9800 . ?
C50 H84 0.9700 . ?
C50 H85 0.9700 . ?
C51 H86 0.9700 . ?
C51 H87 0.9700 . ?
C52 C53 1.514(4) . ?
C52 H88 0.9700 . ?
C52 H92 0.9700 . ?
C53 H90 0.9600 . ?
C53 H91 0.9600 . ?
C53 H89 0.9600 . ?
Si4 C69 1.834(4) . ?
Si4 C61 1.835(4) . ?
Si4 C57 1.835(3) . ?
Si4 C54 1.847(4) . ?
O11 N4 1.271(3) . ?
O12 C67 1.421(4) . ?
O12 H12O 0.8200 . ?
O13 C68 1.414(3) . ?
O13 H13O 0.8200 . ?
N4 C56 1.474(3) . ?
N4 C58 1.479(3) . ?
C54 H95 0.9600 . ?
C54 H97 0.9600 . ?
C54 H123 0.9600 . ?
C55 C57 1.191(3) . ?
C55 C56 1.476(3) . ?
C56 C70 1.536(3) . ?
C56 C62 1.551(4) . ?
C58 C66 1.533(3) . ?
C58 C64 1.540(4) . ?
C58 C59 1.550(3) . ?
C59 C60 1.516(5) . ?
C59 H106 0.9700 . ?
C59 H109 0.9700 . ?
C60 H107 0.9600 . ?
C60 H108 0.9600 . ?
C60 H96 0.9600 . ?
C61 H99 0.9600 . ?
C61 H100 0.9600 . ?
C61 H98 0.9600 . ?
C62 C63 1.506(4) . ?
C62 H101 0.9700 . ?
C62 H105 0.9700 . ?
C63 H102 0.9600 . ?
C63 H103 0.9600 . ?
C63 H104 0.9600 . ?
C64 C65 1.503(5) . ?
C64 H114 0.9700 . ?
C64 H110 0.9700 . ?
C65 H111 0.9600 . ?
C65 H112 0.9600 . ?
C65 H113 0.9600 . ?
C66 C67 1.516(3) . ?
C66 C70 1.537(3) . ?
C66 H117 0.9800 . ?
C67 H115 0.9700 . ?
C67 H116 0.9700 . ?
C68 C70 1.522(4) . ?
C68 H119 0.9700 . ?
C68 H118 0.9700 . ?
C69 H120 0.9600 . ?
C69 H122 0.9600 . ?
C69 H121 0.9600 . ?
C70 H70A 0.9800 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C9 Si1 C19 108.85(16) . . ?
C9 Si1 C8 107.58(15) . . ?
C19 Si1 C8 110.31(18) . . ?
C9 Si1 C1 107.41(16) . . ?
C19 Si1 C1 111.3(2) . . ?
C8 Si1 C1 111.3(2) . . ?
O2 C6 C5 116.3(3) . . ?
O2 C6 H6A 108.2 . . ?
C5 C6 H6A 108.2 . . ?
O2 C6 H6B 108.2 . . ?
C5 C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
C6 O2 H2O 109.5 . . ?
O3 C6' C5 112.4(3) . . ?
O3 C6' H6C 109.1 . . ?
C5 C6' H6C 109.1 . . ?
O3 C6' H6D 109.1 . . ?
C5 C6' H6D 109.1 . . ?
H6C C6' H6D 107.9 . . ?
C6' O3 H3O 109.5 . . ?
C11 O4 H4O 109.5 . . ?
O1 N1 C10 123.28(18) . . ?
O1 N1 C3 121.2(2) . . ?
C10 N1 C3 114.94(17) . . ?
Si1 C1 H26 109.5 . . ?
Si1 C1 H27 109.5 . . ?
H26 C1 H27 109.5 . . ?
Si1 C1 H1 109.5 . . ?
H26 C1 H1 109.5 . . ?
H27 C1 H1 109.5 . . ?
C9 C2 C3 179.4(3) . . ?
C2 C3 N1 107.49(19) . . ?
C2 C3 C17 110.0(2) . . ?
N1 C3 C17 109.8(2) . . ?
C2 C3 C4 111.0(2) . . ?
N1 C3 C4 100.65(19) . . ?
C17 C3 C4 117.2(2) . . ?
C11 C4 C5 115.5(2) . . ?
C11 C4 C3 115.1(2) . . ?
C5 C4 C3 103.59(18) . . ?
C11 C4 H7 107.4 . . ?
C5 C4 H7 107.4 . . ?
C3 C4 H7 107.4 . . ?
C4 C5 C6 114.1(2) . . ?
C4 C5 C6' 114.1(2) . . ?
C4 C5 C10 104.23(19) . . ?
C6 C5 C10 114.9(2) . . ?
C6' C5 C10 114.9(2) . . ?
C4 C5 H10 107.7 . . ?
C6 C5 H10 107.7 . . ?
C10 C5 H10 107.7 . . ?
Si1 C8 H3 109.5 . . ?
Si1 C8 H32 109.5 . . ?
H3 C8 H32 109.5 . . ?
Si1 C8 H31 109.5 . . ?
H3 C8 H31 109.5 . . ?
H32 C8 H31 109.5 . . ?
C2 C9 Si1 177.6(3) . . ?
N1 C10 C13 110.32(19) . . ?
N1 C10 C5 100.45(18) . . ?
C13 C10 C5 115.0(2) . . ?
N1 C10 C15 109.2(2) . . ?
C13 C10 C15 110.9(2) . . ?
C5 C10 C15 110.51(18) . . ?
O4 C11 C4 108.9(3) . . ?
O4 C11 H11A 109.9 . . ?
C4 C11 H11A 109.9 . . ?
O4 C11 H11B 109.9 . . ?
C4 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C14 C13 C10 117.0(2) . . ?
C14 C13 H12 108.1 . . ?
C10 C13 H12 108.1 . . ?
C14 C13 H11 108.1 . . ?
C10 C13 H11 108.1 . . ?
H12 C13 H11 107.3 . . ?
C13 C14 H13 109.5 . . ?
C13 C14 H14 109.5 . . ?
H13 C14 H14 109.5 . . ?
C13 C14 H15 109.5 . . ?
H13 C14 H15 109.5 . . ?
H14 C14 H15 109.5 . . ?
C16 C15 C10 116.2(2) . . ?
C16 C15 H16 108.2 . . ?
C10 C15 H16 108.2 . . ?
C16 C15 H17 108.2 . . ?
C10 C15 H17 108.2 . . ?
H16 C15 H17 107.4 . . ?
C15 C16 H19 109.5 . . ?
C15 C16 H18 109.5 . . ?
H19 C16 H18 109.5 . . ?
C15 C16 H20 109.5 . . ?
H19 C16 H20 109.5 . . ?
H18 C16 H20 109.5 . . ?
C18 C17 C3 115.9(3) . . ?
C18 C17 H21 108.3 . . ?
C3 C17 H21 108.3 . . ?
C18 C17 H25 108.3 . . ?
C3 C17 H25 108.3 . . ?
H21 C17 H25 107.4 . . ?
C17 C18 H24 109.5 . . ?
C17 C18 H22 109.5 . . ?
H24 C18 H22 109.5 . . ?
C17 C18 H23 109.5 . . ?
H24 C18 H23 109.5 . . ?
H22 C18 H23 109.5 . . ?
Si1 C19 H29 109.5 . . ?
Si1 C19 H30 109.5 . . ?
H29 C19 H30 109.5 . . ?
Si1 C19 H28 109.5 . . ?
H29 C19 H28 109.5 . . ?
H30 C19 H28 109.5 . . ?
C23 Si2 C27 107.89(16) . . ?
C23 Si2 C28 107.54(18) . . ?
C27 Si2 C28 111.4(2) . . ?
C23 Si2 C20 107.98(18) . . ?
C27 Si2 C20 110.7(2) . . ?
C28 Si2 C20 111.2(2) . . ?
C33 O6 H6O 109.5 . . ?
C30 O7 H7O 109.5 . . ?
O5 N2 C22 120.8(2) . . ?
O5 N2 C24 123.3(2) . . ?
C22 N2 C24 115.3(2) . . ?
Si2 C20 H62 109.5 . . ?
Si2 C20 H63 109.5 . . ?
H62 C20 H63 109.5 . . ?
Si2 C20 H33 109.5 . . ?
H62 C20 H33 109.5 . . ?
H63 C20 H33 109.5 . . ?
C23 C21 C22 177.2(3) . . ?
N2 C22 C21 107.4(2) . . ?
N2 C22 C29 101.9(2) . . ?
C21 C22 C29 112.7(2) . . ?
N2 C22 C36 110.4(3) . . ?
C21 C22 C36 108.5(3) . . ?
C29 C22 C36 115.6(2) . . ?
C21 C23 Si2 178.0(3) . . ?
N2 C24 C34 110.4(2) . . ?
N2 C24 C32 99.8(2) . . ?
C34 C24 C32 114.7(2) . . ?
N2 C24 C25 108.8(2) . . ?
C34 C24 C25 110.3(3) . . ?
C32 C24 C25 112.3(2) . . ?
C26 C25 C24 115.9(3) . . ?
C26 C25 H51 108.3 . . ?
C24 C25 H51 108.3 . . ?
C26 C25 H50 108.3 . . ?
C24 C25 H50 108.3 . . ?
H51 C25 H50 107.4 . . ?
C25 C26 H48 109.5 . . ?
C25 C26 H49 109.5 . . ?
H48 C26 H49 109.5 . . ?
C25 C26 H34 109.5 . . ?
H48 C26 H34 109.5 . . ?
H49 C26 H34 109.5 . . ?
Si2 C27 H35 109.5 . . ?
Si2 C27 H65 109.5 . . ?
H35 C27 H65 109.5 . . ?
Si2 C27 H64 109.5 . . ?
H35 C27 H64 109.5 . . ?
H65 C27 H64 109.5 . . ?
Si2 C28 H37 109.5 . . ?
Si2 C28 H38 109.5 . . ?
H37 C28 H38 109.5 . . ?
Si2 C28 H36 109.5 . . ?
H37 C28 H36 109.5 . . ?
H38 C28 H36 109.5 . . ?
C30 C29 C22 114.0(3) . . ?
C30 C29 C32 115.6(2) . . ?
C22 C29 C32 103.7(2) . . ?
C30 C29 H44 107.8 . . ?
C22 C29 H44 107.8 . . ?
C32 C29 H44 107.8 . . ?
O7 C30 C29 114.0(3) . . ?
O7 C30 H42 108.8 . . ?
C29 C30 H42 108.8 . . ?
O7 C30 H43 108.8 . . ?
C29 C30 H43 108.8 . . ?
H42 C30 H43 107.7 . . ?
C33 C32 C29 117.3(2) . . ?
C33 C32 C24 112.2(2) . . ?
C29 C32 C24 105.0(2) . . ?
C33 C32 H47 107.3 . . ?
C29 C32 H47 107.3 . . ?
C24 C32 H47 107.3 . . ?
O6 C33 C32 113.2(3) . . ?
O6 C33 H45 108.9 . . ?
C32 C33 H45 108.9 . . ?
O6 C33 H46 108.9 . . ?
C32 C33 H46 108.9 . . ?
H45 C33 H46 107.7 . . ?
C35 C34 C24 116.7(3) . . ?
C35 C34 H52 108.1 . . ?
C24 C34 H52 108.1 . . ?
C35 C34 H56 108.1 . . ?
C24 C34 H56 108.1 . . ?
H52 C34 H56 107.3 . . ?
C34 C35 H55 109.5 . . ?
C34 C35 H54 109.5 . . ?
H55 C35 H54 109.5 . . ?
C34 C35 H53 109.5 . . ?
H55 C35 H53 109.5 . . ?
H54 C35 H53 109.5 . . ?
C37 C36 C22 117.5(4) . . ?
C37 C36 H61 107.9 . . ?
C22 C36 H61 107.9 . . ?
C37 C36 H57 107.9 . . ?
C22 C36 H57 107.9 . . ?
H61 C36 H57 107.2 . . ?
C36 C37 H60 109.5 . . ?
C36 C37 H58 109.5 . . ?
H60 C37 H58 109.5 . . ?
C36 C37 H59 109.5 . . ?
H60 C37 H59 109.5 . . ?
H58 C37 H59 109.5 . . ?
C45 Si3 C41 109.56(16) . . ?
C45 Si3 C46 112.32(17) . . ?
C41 Si3 C46 106.73(15) . . ?
C45 Si3 C38 110.9(2) . . ?
C41 Si3 C38 106.02(16) . . ?
C46 Si3 C38 111.0(2) . . ?
C50 O9 H9Q 99(2) . . ?
C51 O10 H10Q 108(3) . . ?
O8 N3 C42 123.43(18) . . ?
O8 N3 C40 121.03(18) . . ?
C42 N3 C40 115.18(16) . . ?
C51 C7 C49 115.12(18) . . ?
C51 C7 C42 113.94(19) . . ?
C49 C7 C42 104.95(17) . . ?
C51 C7 H7A 107.5 . . ?
C49 C7 H7A 107.5 . . ?
C42 C7 H7A 107.5 . . ?
Si3 C38 H72 109.5 . . ?
Si3 C38 H73 109.5 . . ?
H72 C38 H73 109.5 . . ?
Si3 C38 H66 109.5 . . ?
H72 C38 H66 109.5 . . ?
H73 C38 H66 109.5 . . ?
C41 C39 C40 177.0(3) . . ?
C39 C40 N3 107.61(18) . . ?
C39 C40 C47 110.10(19) . . ?
N3 C40 C47 110.59(19) . . ?
C39 C40 C49 110.11(19) . . ?
N3 C40 C49 101.06(17) . . ?
C47 C40 C49 116.72(19) . . ?
C39 C41 Si3 172.6(2) . . ?
N3 C42 C43 110.34(18) . . ?
N3 C42 C7 100.44(17) . . ?
C43 C42 C7 113.80(18) . . ?
N3 C42 C52 109.26(18) . . ?
C43 C42 C52 110.94(19) . . ?
C7 C42 C52 111.54(17) . . ?
C44 C43 C42 116.7(2) . . ?
C44 C43 H82 108.1 . . ?
C42 C43 H82 108.1 . . ?
C44 C43 H79 108.1 . . ?
C42 C43 H79 108.1 . . ?
H82 C43 H79 107.3 . . ?
C43 C44 H80 109.5 . . ?
C43 C44 H81 109.5 . . ?
H80 C44 H81 109.5 . . ?
C43 C44 H67 109.5 . . ?
H80 C44 H67 109.5 . . ?
H81 C44 H67 109.5 . . ?
Si3 C45 H68 109.5 . . ?
Si3 C45 H93 109.5 . . ?
H68 C45 H93 109.5 . . ?
Si3 C45 H94 109.5 . . ?
H68 C45 H94 109.5 . . ?
H93 C45 H94 109.5 . . ?
Si3 C46 H69 109.5 . . ?
Si3 C46 H70 109.5 . . ?
H69 C46 H70 109.5 . . ?
Si3 C46 H71 109.5 . . ?
H69 C46 H71 109.5 . . ?
H70 C46 H71 109.5 . . ?
C48 C47 C40 115.2(2) . . ?
C48 C47 H77 108.5 . . ?
C40 C47 H77 108.5 . . ?
C48 C47 H78 108.5 . . ?
C40 C47 H78 108.5 . . ?
H77 C47 H78 107.5 . . ?
C47 C48 H75 109.5 . . ?
C47 C48 H74 109.5 . . ?
H75 C48 H74 109.5 . . ?
C47 C48 H76 109.5 . . ?
H75 C48 H76 109.5 . . ?
H74 C48 H76 109.5 . . ?
C50 C49 C7 116.1(2) . . ?
C50 C49 C40 113.2(2) . . ?
C7 C49 C40 103.29(16) . . ?
C50 C49 H83 108.0 . . ?
C7 C49 H83 108.0 . . ?
C40 C49 H83 108.0 . . ?
O9 C50 C49 112.8(2) . . ?
O9 C50 H84 109.0 . . ?
C49 C50 H84 109.0 . . ?
O9 C50 H85 109.0 . . ?
C49 C50 H85 109.0 . . ?
H84 C50 H85 107.8 . . ?
O10 C51 C7 112.2(2) . . ?
O10 C51 H86 109.2 . . ?
C7 C51 H86 109.2 . . ?
O10 C51 H87 109.2 . . ?
C7 C51 H87 109.2 . . ?
H86 C51 H87 107.9 . . ?
C53 C52 C42 116.8(2) . . ?
C53 C52 H88 108.1 . . ?
C42 C52 H88 108.1 . . ?
C53 C52 H92 108.1 . . ?
C42 C52 H92 108.1 . . ?
H88 C52 H92 107.3 . . ?
C52 C53 H90 109.5 . . ?
C52 C53 H91 109.5 . . ?
H90 C53 H91 109.5 . . ?
C52 C53 H89 109.5 . . ?
H90 C53 H89 109.5 . . ?
H91 C53 H89 109.5 . . ?
C69 Si4 C61 109.8(2) . . ?
C69 Si4 C57 108.95(16) . . ?
C61 Si4 C57 107.50(18) . . ?
C69 Si4 C54 110.5(2) . . ?
C61 Si4 C54 112.5(3) . . ?
C57 Si4 C54 107.54(17) . . ?
C67 O12 H12O 109.5 . . ?
C68 O13 H13O 109.5 . . ?
O11 N4 C56 121.0(2) . . ?
O11 N4 C58 123.5(2) . . ?
C56 N4 C58 115.16(18) . . ?
Si4 C54 H95 109.5 . . ?
Si4 C54 H97 109.5 . . ?
H95 C54 H97 109.5 . . ?
Si4 C54 H123 109.5 . . ?
H95 C54 H123 109.5 . . ?
H97 C54 H123 109.5 . . ?
C57 C55 C56 178.5(3) . . ?
N4 C56 C55 108.15(19) . . ?
N4 C56 C70 101.81(17) . . ?
C55 C56 C70 111.1(2) . . ?
N4 C56 C62 110.5(2) . . ?
C55 C56 C62 109.4(2) . . ?
C70 C56 C62 115.4(2) . . ?
C55 C57 Si4 175.2(3) . . ?
N4 C58 C66 100.88(18) . . ?
N4 C58 C64 110.2(2) . . ?
C66 C58 C64 113.8(2) . . ?
N4 C58 C59 109.0(2) . . ?
C66 C58 C59 112.0(2) . . ?
C64 C58 C59 110.5(2) . . ?
C60 C59 C58 116.4(3) . . ?
C60 C59 H106 108.2 . . ?
C58 C59 H106 108.2 . . ?
C60 C59 H109 108.2 . . ?
C58 C59 H109 108.2 . . ?
H106 C59 H109 107.3 . . ?
C59 C60 H107 109.5 . . ?
C59 C60 H108 109.5 . . ?
H107 C60 H108 109.5 . . ?
C59 C60 H96 109.5 . . ?
H107 C60 H96 109.5 . . ?
H108 C60 H96 109.5 . . ?
Si4 C61 H99 109.5 . . ?
Si4 C61 H100 109.5 . . ?
H99 C61 H100 109.5 . . ?
Si4 C61 H98 109.5 . . ?
H99 C61 H98 109.5 . . ?
H100 C61 H98 109.5 . . ?
C63 C62 C56 115.5(2) . . ?
C63 C62 H101 108.4 . . ?
C56 C62 H101 108.4 . . ?
C63 C62 H105 108.4 . . ?
C56 C62 H105 108.4 . . ?
H101 C62 H105 107.5 . . ?
C62 C63 H102 109.5 . . ?
C62 C63 H103 109.5 . . ?
H102 C63 H103 109.5 . . ?
C62 C63 H104 109.5 . . ?
H102 C63 H104 109.5 . . ?
H103 C63 H104 109.5 . . ?
C65 C64 C58 116.7(3) . . ?
C65 C64 H114 108.1 . . ?
C58 C64 H114 108.1 . . ?
C65 C64 H110 108.1 . . ?
C58 C64 H110 108.1 . . ?
H114 C64 H110 107.3 . . ?
C64 C65 H111 109.5 . . ?
C64 C65 H112 109.5 . . ?
H111 C65 H112 109.5 . . ?
C64 C65 H113 109.5 . . ?
H111 C65 H113 109.5 . . ?
H112 C65 H113 109.5 . . ?
C67 C66 C58 115.3(2) . . ?
C67 C66 C70 114.7(2) . . ?
C58 C66 C70 105.02(19) . . ?
C67 C66 H117 107.1 . . ?
C58 C66 H117 107.1 . . ?
C70 C66 H117 107.1 . . ?
O12 C67 C66 113.3(2) . . ?
O12 C67 H115 108.9 . . ?
C66 C67 H115 108.9 . . ?
O12 C67 H116 108.9 . . ?
C66 C67 H116 108.9 . . ?
H115 C67 H116 107.7 . . ?
O13 C68 C70 113.2(2) . . ?
O13 C68 H119 108.9 . . ?
C70 C68 H119 108.9 . . ?
O13 C68 H118 108.9 . . ?
C70 C68 H118 108.9 . . ?
H119 C68 H118 107.8 . . ?
Si4 C69 H120 109.5 . . ?
Si4 C69 H122 109.5 . . ?
H120 C69 H122 109.5 . . ?
Si4 C69 H121 109.5 . . ?
H120 C69 H121 109.5 . . ?
H122 C69 H121 109.5 . . ?
C68 C70 C56 112.2(2) . . ?
C68 C70 C66 116.3(2) . . ?
C56 C70 C66 103.93(18) . . ?
C68 C70 H70A 108.0 . . ?
C56 C70 H70A 108.0 . . ?
C66 C70 H70A 108.0 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O1 N1 C3 C2 67.6(3) . . . . ?
C10 N1 C3 C2 -103.7(2) . . . . ?
O1 N1 C3 C17 -52.1(3) . . . . ?
C10 N1 C3 C17 136.6(2) . . . . ?
O1 N1 C3 C4 -176.27(19) . . . . ?
C10 N1 C3 C4 12.4(2) . . . . ?
C2 C3 C4 C11 -45.7(3) . . . . ?
N1 C3 C4 C11 -159.2(2) . . . . ?
C17 C3 C4 C11 81.8(3) . . . . ?
C2 C3 C4 C5 81.4(2) . . . . ?
N1 C3 C4 C5 -32.1(2) . . . . ?
C17 C3 C4 C5 -151.0(2) . . . . ?
C11 C4 C5 C6 -65.8(3) . . . . ?
C3 C4 C5 C6 167.4(2) . . . . ?
C11 C4 C5 C6' -65.8(3) . . . . ?
C3 C4 C5 C6' 167.4(2) . . . . ?
C11 C4 C5 C10 168.1(2) . . . . ?
C3 C4 C5 C10 41.2(2) . . . . ?
O2 C6 C5 C4 -172.0(3) . . . . ?
O2 C6 C5 C10 -51.7(4) . . . . ?
O3 C6' C5 C4 79.1(4) . . . . ?
O3 C6' C5 C10 -160.6(3) . . . . ?
O1 N1 C10 C13 -37.3(3) . . . . ?
C3 N1 C10 C13 133.8(2) . . . . ?
O1 N1 C10 C5 -159.0(2) . . . . ?
C3 N1 C10 C5 12.0(2) . . . . ?
O1 N1 C10 C15 84.8(2) . . . . ?
C3 N1 C10 C15 -104.2(2) . . . . ?
C4 C5 C10 N1 -32.1(2) . . . . ?
C6 C5 C10 N1 -157.7(2) . . . . ?
C6' C5 C10 N1 -157.7(2) . . . . ?
C4 C5 C10 C13 -150.5(2) . . . . ?
C6 C5 C10 C13 84.0(3) . . . . ?
C6' C5 C10 C13 84.0(3) . . . . ?
C4 C5 C10 C15 83.1(2) . . . . ?
C6 C5 C10 C15 -42.4(3) . . . . ?
C6' C5 C10 C15 -42.4(3) . . . . ?
C5 C4 C11 O4 164.3(3) . . . . ?
C3 C4 C11 O4 -74.9(3) . . . . ?
N1 C10 C13 C14 -57.1(3) . . . . ?
C5 C10 C13 C14 55.5(3) . . . . ?
C15 C10 C13 C14 -178.3(2) . . . . ?
N1 C10 C15 C16 -59.8(3) . . . . ?
C13 C10 C15 C16 62.0(3) . . . . ?
C5 C10 C15 C16 -169.4(2) . . . . ?
C2 C3 C17 C18 -175.0(3) . . . . ?
N1 C3 C17 C18 -56.9(3) . . . . ?
C4 C3 C17 C18 57.0(4) . . . . ?
O5 N2 C22 C21 61.9(3) . . . . ?
C24 N2 C22 C21 -109.3(2) . . . . ?
O5 N2 C22 C29 -179.5(2) . . . . ?
C24 N2 C22 C29 9.2(3) . . . . ?
O5 N2 C22 C36 -56.2(3) . . . . ?
C24 N2 C22 C36 132.5(2) . . . . ?
O5 N2 C24 C34 -35.9(3) . . . . ?
C22 N2 C24 C34 135.1(2) . . . . ?
O5 N2 C24 C32 -157.0(2) . . . . ?
C22 N2 C24 C32 14.1(3) . . . . ?
O5 N2 C24 C25 85.3(3) . . . . ?
C22 N2 C24 C25 -103.7(3) . . . . ?
N2 C24 C25 C26 -59.1(4) . . . . ?
C34 C24 C25 C26 62.1(4) . . . . ?
C32 C24 C25 C26 -168.7(3) . . . . ?
N2 C22 C29 C30 -155.2(2) . . . . ?
C21 C22 C29 C30 -40.5(3) . . . . ?
C36 C22 C29 C30 85.0(3) . . . . ?
N2 C22 C29 C32 -28.8(2) . . . . ?
C21 C22 C29 C32 85.9(3) . . . . ?
C36 C22 C29 C32 -148.5(3) . . . . ?
C22 C29 C30 O7 -162.5(3) . . . . ?
C32 C29 C30 O7 77.5(3) . . . . ?
C30 C29 C32 C33 -70.3(3) . . . . ?
C22 C29 C32 C33 164.3(2) . . . . ?
C30 C29 C32 C24 164.4(2) . . . . ?
C22 C29 C32 C24 39.0(2) . . . . ?
N2 C24 C32 C33 -160.2(2) . . . . ?
C34 C24 C32 C33 81.9(3) . . . . ?
C25 C24 C32 C33 -45.0(3) . . . . ?
N2 C24 C32 C29 -31.7(2) . . . . ?
C34 C24 C32 C29 -149.7(2) . . . . ?
C25 C24 C32 C29 83.4(3) . . . . ?
C29 C32 C33 O6 68.2(3) . . . . ?
C24 C32 C33 O6 -170.2(2) . . . . ?
N2 C24 C34 C35 -63.5(4) . . . . ?
C32 C24 C34 C35 48.3(4) . . . . ?
C25 C24 C34 C35 176.2(3) . . . . ?
N2 C22 C36 C37 -56.9(4) . . . . ?
C21 C22 C36 C37 -174.3(4) . . . . ?
C29 C22 C36 C37 58.0(5) . . . . ?
O8 N3 C40 C39 -70.3(2) . . . . ?
C42 N3 C40 C39 103.1(2) . . . . ?
O8 N3 C40 C47 50.0(3) . . . . ?
C42 N3 C40 C47 -136.6(2) . . . . ?
O8 N3 C40 C49 174.31(18) . . . . ?
C42 N3 C40 C49 -12.3(2) . . . . ?
O8 N3 C42 C43 41.3(3) . . . . ?
C40 N3 C42 C43 -131.91(19) . . . . ?
O8 N3 C42 C7 161.67(19) . . . . ?
C40 N3 C42 C7 -11.5(2) . . . . ?
O8 N3 C42 C52 -80.9(2) . . . . ?
C40 N3 C42 C52 105.9(2) . . . . ?
C51 C7 C42 N3 157.86(18) . . . . ?
C49 C7 C42 N3 31.0(2) . . . . ?
C51 C7 C42 C43 -84.3(2) . . . . ?
C49 C7 C42 C43 148.92(19) . . . . ?
C51 C7 C42 C52 42.2(3) . . . . ?
C49 C7 C42 C52 -84.6(2) . . . . ?
N3 C42 C43 C44 53.8(3) . . . . ?
C7 C42 C43 C44 -58.2(3) . . . . ?
C52 C42 C43 C44 175.0(2) . . . . ?
C39 C40 C47 C48 173.1(2) . . . . ?
N3 C40 C47 C48 54.3(3) . . . . ?
C49 C40 C47 C48 -60.5(3) . . . . ?
C51 C7 C49 C50 69.5(3) . . . . ?
C42 C7 C49 C50 -164.42(19) . . . . ?
C51 C7 C49 C40 -166.02(19) . . . . ?
C42 C7 C49 C40 -39.9(2) . . . . ?
C39 C40 C49 C50 43.8(3) . . . . ?
N3 C40 C49 C50 157.34(19) . . . . ?
C47 C40 C49 C50 -82.7(3) . . . . ?
C39 C40 C49 C7 -82.6(2) . . . . ?
N3 C40 C49 C7 31.0(2) . . . . ?
C47 C40 C49 C7 151.0(2) . . . . ?
C7 C49 C50 O9 -74.3(3) . . . . ?
C40 C49 C50 O9 166.4(2) . . . . ?
C49 C7 C51 O10 -75.7(3) . . . . ?
C42 C7 C51 O10 162.98(19) . . . . ?
N3 C42 C52 C53 57.2(3) . . . . ?
C43 C42 C52 C53 -64.7(3) . . . . ?
C7 C42 C52 C53 167.4(2) . . . . ?
O11 N4 C56 C55 -66.3(3) . . . . ?
C58 N4 C56 C55 107.0(2) . . . . ?
O11 N4 C56 C70 176.5(2) . . . . ?
C58 N4 C56 C70 -10.2(2) . . . . ?
O11 N4 C56 C62 53.4(3) . . . . ?
C58 N4 C56 C62 -133.2(2) . . . . ?
O11 N4 C58 C66 160.8(2) . . . . ?
C56 N4 C58 C66 -12.3(2) . . . . ?
O11 N4 C58 C64 40.3(3) . . . . ?
C56 N4 C58 C64 -132.9(2) . . . . ?
O11 N4 C58 C59 -81.2(3) . . . . ?
C56 N4 C58 C59 105.7(2) . . . . ?
N4 C58 C59 C60 58.8(4) . . . . ?
C66 C58 C59 C60 169.6(3) . . . . ?
C64 C58 C59 C60 -62.5(4) . . . . ?
N4 C56 C62 C63 55.9(3) . . . . ?
C55 C56 C62 C63 174.9(3) . . . . ?
C70 C56 C62 C63 -58.9(4) . . . . ?
N4 C58 C64 C65 56.9(4) . . . . ?
C66 C58 C64 C65 -55.6(4) . . . . ?
C59 C58 C64 C65 177.5(3) . . . . ?
N4 C58 C66 C67 157.0(2) . . . . ?
C64 C58 C66 C67 -85.0(3) . . . . ?
C59 C58 C66 C67 41.2(3) . . . . ?
N4 C58 C66 C70 29.8(2) . . . . ?
C64 C58 C66 C70 147.8(2) . . . . ?
C59 C58 C66 C70 -86.0(2) . . . . ?
C58 C66 C67 O12 167.4(2) . . . . ?
C70 C66 C67 O12 -70.4(3) . . . . ?
O13 C68 C70 C56 161.7(2) . . . . ?
O13 C68 C70 C66 -78.8(3) . . . . ?
N4 C56 C70 C68 154.9(2) . . . . ?
C55 C56 C70 C68 39.9(3) . . . . ?
C62 C56 C70 C68 -85.4(3) . . . . ?
N4 C56 C70 C66 28.4(2) . . . . ?
C55 C56 C70 C66 -86.6(2) . . . . ?
C62 C56 C70 C66 148.1(2) . . . . ?
C67 C66 C70 C68 71.2(3) . . . . ?
C58 C66 C70 C68 -161.3(2) . . . . ?
C67 C66 C70 C56 -164.9(2) . . . . ?
C58 C66 C70 C56 -37.3(2) . . . . ?
 
_refine_diff_density_max    1.574
_refine_diff_density_min   -0.495
_refine_diff_density_rms    0.062



 
data_comp4a_S_1135_3
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic 
;
6-(azidomethyl)-3b,5,5-triethyl-3b,4,5,6,6a,7-hexahydropyrrolo
[2',3':3,4]pyrrolo[1,2-c][1,2,3]triazol-4-oxyl 
;
_chemical_name_common             ?
_chemical_melting_point           399
_chemical_formula_moiety          'C14 H22 N7 O'
_chemical_formula_sum
 'C14 H22 N7 O' 
_chemical_formula_weight          304.38

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            4
_space_group_name_H-M_alt         'P 21'
_space_group_name_Hall            'P 2yb'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    7.4655(5)
_cell_length_b                    11.8859(6)
_cell_length_c                    9.1833(5)
_cell_angle_alpha                 90
_cell_angle_beta                  95.219(2)
_cell_angle_gamma                 90
_cell_volume                      811.49(8)
_cell_formula_units_Z             2
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     7670
_cell_measurement_theta_min       2.23
_cell_measurement_theta_max       28.49
 
_exptl_crystal_description        'block'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.246          
_exptl_crystal_F_000              326
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.720
_exptl_crystal_size_mid           0.410
_exptl_crystal_size_min           0.310
_exptl_absorpt_coefficient_mu     0.085
_shelx_estimated_absorpt_T_min    0.941
_shelx_estimated_absorpt_T_max    0.974
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8770
_exptl_absorpt_correction_T_max   0.9281
_exptl_absorpt_process_details    SADABS-2016/2
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed tube'
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             14376
_diffrn_reflns_av_unetI/netI      0.0353
_diffrn_reflns_av_R_equivalents   0.0452
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          2.740
_diffrn_reflns_theta_max          28.536
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              4103
_reflns_number_gt                 3584
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.908
_reflns_Friedel_fraction_max      0.997
_reflns_Friedel_fraction_full     0.999
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0733P)²+0.1292P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 1514 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.0(6)
_chemical_absolute_configuration  syn
_refine_ls_number_reflns          4103
_refine_ls_number_parameters      202
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0580
_refine_ls_R_factor_gt            0.0486
_refine_ls_wR_factor_ref          0.1395
_refine_ls_wR_factor_gt           0.1295
_refine_ls_goodness_of_fit_ref    1.054
_refine_ls_restrained_S_all       1.054
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.9889(3) 0.4906(3) 0.3454(3) 0.0670(7) Uani 1 1 d . . . . .
N1 N 0.5204(5) 0.3556(2) 0.6805(3) 0.0631(8) Uani 1 1 d . . . . .
N2 N 0.6825(5) 0.3170(2) 0.7198(3) 0.0693(8) Uani 1 1 d . . . . .
C3B C 0.7311(3) 0.5516(2) 0.4596(3) 0.0368(5) Uani 1 1 d . . . . .
C3A C 0.7151(4) 0.4563(2) 0.5650(3) 0.0415(5) Uani 1 1 d . . . . .
C3 C 0.8052(5) 0.3767(3) 0.6519(3) 0.0571(7) Uani 1 1 d . . . . .
H3 H 0.929061 0.365645 0.662351 0.069 Uiso 1 1 calc R U . . .
N4 N 0.8230(3) 0.5159(2) 0.3325(2) 0.0413(5) Uani 1 1 d . . . . .
N5 N 0.3420(5) 0.4493(3) 0.0260(4) 0.0842(11) Uani 1 1 d . . . . .
C5 C 0.7073(3) 0.5141(2) 0.1917(2) 0.0401(5) Uani 1 1 d . . . . .
C6A C 0.5328(3) 0.5649(2) 0.3947(2) 0.0355(5) Uani 1 1 d . . . . .
H6A H 0.502899 0.644162 0.375839 0.043 Uiso 1 1 calc R U . . .
C6 C 0.5229(3) 0.4970(2) 0.2512(2) 0.0349(4) Uani 1 1 d . . . . .
H6 H 0.511934 0.417219 0.276034 0.042 Uiso 1 1 calc R U . . .
N6 N 0.2598(4) 0.4832(3) -0.0844(3) 0.0621(7) Uani 1 1 d . . . . .
N7 N 0.1822(6) 0.5024(5) -0.1918(4) 0.1025(14) Uani 1 1 d . . . . .
C7 C 0.4148(4) 0.5143(3) 0.5067(3) 0.0479(6) Uani 1 1 d . . . . .
H7A H 0.371404 0.571704 0.569934 0.057 Uiso 1 1 calc R U . . .
H7B H 0.313278 0.473324 0.459340 0.057 Uiso 1 1 calc R U . . .
N8 N 0.5424(3) 0.43943(19) 0.5865(2) 0.0446(5) Uani 1 1 d . . . . .
C9 C 0.8227(4) 0.6566(3) 0.5289(3) 0.0547(7) Uani 1 1 d . . . . .
H9A H 0.947481 0.638865 0.558861 0.066 Uiso 1 1 calc R U . . .
H9B H 0.821254 0.715363 0.455561 0.066 Uiso 1 1 calc R U . . .
C10 C 0.7362(7) 0.7010(3) 0.6593(4) 0.0795(11) Uani 1 1 d . . . . .
H10A H 0.613105 0.720084 0.630505 0.119 Uiso 1 1 calc R U . . .
H10B H 0.799582 0.766774 0.696245 0.119 Uiso 1 1 calc R U . . .
H10C H 0.740762 0.644380 0.734073 0.119 Uiso 1 1 calc R U . . .
C11 C 0.7690(5) 0.4192(3) 0.0975(4) 0.0636(9) Uani 1 1 d . . . . .
H11A H 0.702073 0.423929 0.002079 0.076 Uiso 1 1 calc R U . . .
H11B H 0.894879 0.431088 0.083709 0.076 Uiso 1 1 calc R U . . .
C12 C 0.7481(6) 0.3018(4) 0.1561(6) 0.0919(14) Uani 1 1 d . . . . .
H12A H 0.796763 0.298862 0.256438 0.138 Uiso 1 1 calc R U . . .
H12B H 0.811304 0.249574 0.099610 0.138 Uiso 1 1 calc R U . . .
H12C H 0.622830 0.282225 0.149501 0.138 Uiso 1 1 calc R U . . .
C13 C 0.7165(4) 0.6312(3) 0.1153(3) 0.0523(7) Uani 1 1 d . . . . .
H13A H 0.639564 0.628905 0.024355 0.063 Uiso 1 1 calc R U . . .
H13B H 0.667527 0.687333 0.177324 0.063 Uiso 1 1 calc R U . . .
C14 C 0.9009(5) 0.6687(4) 0.0823(4) 0.0703(10) Uani 1 1 d . . . . .
H14A H 0.977567 0.674353 0.171726 0.105 Uiso 1 1 calc R U . . .
H14B H 0.892659 0.740733 0.034929 0.105 Uiso 1 1 calc R U . . .
H14C H 0.950251 0.614818 0.018991 0.105 Uiso 1 1 calc R U . . .
C15 C 0.3575(4) 0.5295(3) 0.1513(3) 0.0490(6) Uani 1 1 d . . . . .
H15A H 0.250838 0.525408 0.204034 0.059 Uiso 1 1 calc R U . . .
H15B H 0.369388 0.605823 0.116179 0.059 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 N4 1.270(3) . ?
N1 N2 1.313(5) . ?
N1 N8 1.338(3) . ?
N2 C3 1.355(5) . ?
C3B N4 1.469(3) . ?
C3B C3A 1.502(3) . ?
C3B C9 1.533(4) . ?
C3B C6A 1.553(3) . ?
C3A N8 1.337(4) . ?
C3A C3 1.374(4) . ?
C3 H3 0.9300 . ?
N4 C5 1.488(3) . ?
N5 N6 1.206(4) . ?
N5 C15 1.490(4) . ?
C5 C11 1.518(4) . ?
C5 C6 1.540(3) . ?
C5 C13 1.563(4) . ?
C6A C7 1.536(3) . ?
C6A C6 1.542(3) . ?
C6A H6A 0.9800 . ?
C6 C15 1.520(3) . ?
C6 H6 0.9800 . ?
N6 N7 1.121(4) . ?
C7 N8 1.453(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.506(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.509(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.504(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
N2 N1 N8 105.9(3) . . ?
N1 N2 C3 109.6(3) . . ?
N4 C3B C3A 111.4(2) . . ?
N4 C3B C9 110.0(2) . . ?
C3A C3B C9 113.9(2) . . ?
N4 C3B C6A 102.84(18) . . ?
C3A C3B C6A 101.24(19) . . ?
C9 C3B C6A 116.7(2) . . ?
N8 C3A C3 103.8(3) . . ?
N8 C3A C3B 110.0(2) . . ?
C3 C3A C3B 146.2(3) . . ?
N2 C3 C3A 108.2(3) . . ?
N2 C3 H3 125.9 . . ?
C3A C3 H3 125.9 . . ?
O1 N4 C3B 121.1(2) . . ?
O1 N4 C5 124.2(2) . . ?
C3B N4 C5 114.75(18) . . ?
N6 N5 C15 115.7(3) . . ?
N4 C5 C11 108.9(2) . . ?
N4 C5 C6 99.25(17) . . ?
C11 C5 C6 115.6(2) . . ?
N4 C5 C13 109.3(2) . . ?
C11 C5 C13 112.2(2) . . ?
C6 C5 C13 110.7(2) . . ?
C7 C6A C6 112.4(2) . . ?
C7 C6A C3B 106.76(19) . . ?
C6 C6A C3B 104.16(18) . . ?
C7 C6A H6A 111.1 . . ?
C6 C6A H6A 111.1 . . ?
C3B C6A H6A 111.1 . . ?
C15 C6 C5 117.1(2) . . ?
C15 C6 C6A 110.87(19) . . ?
C5 C6 C6A 105.01(19) . . ?
C15 C6 H6 107.8 . . ?
C5 C6 H6 107.8 . . ?
C6A C6 H6 107.8 . . ?
N7 N6 N5 172.2(5) . . ?
N8 C7 C6A 100.80(19) . . ?
N8 C7 H7A 111.6 . . ?
C6A C7 H7A 111.6 . . ?
N8 C7 H7B 111.6 . . ?
C6A C7 H7B 111.6 . . ?
H7A C7 H7B 109.4 . . ?
C3A N8 N1 112.6(3) . . ?
C3A N8 C7 115.5(2) . . ?
N1 N8 C7 131.9(3) . . ?
C10 C9 C3B 114.1(3) . . ?
C10 C9 H9A 108.7 . . ?
C3B C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C3B C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C5 115.9(3) . . ?
C12 C11 H11A 108.3 . . ?
C5 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C5 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C5 115.6(3) . . ?
C14 C13 H13A 108.4 . . ?
C5 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C5 C13 H13B 108.4 . . ?
H13A C13 H13B 107.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N5 C15 C6 107.8(2) . . ?
N5 C15 H15A 110.2 . . ?
C6 C15 H15A 110.2 . . ?
N5 C15 H15B 110.2 . . ?
C6 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
N8 N1 N2 C3 0.4(3) . . . . ?
N4 C3B C3A N8 -122.9(2) . . . . ?
C9 C3B C3A N8 112.0(3) . . . . ?
C6A C3B C3A N8 -14.2(3) . . . . ?
N4 C3B C3A C3 57.5(5) . . . . ?
C9 C3B C3A C3 -67.7(5) . . . . ?
C6A C3B C3A C3 166.2(4) . . . . ?
N1 N2 C3 C3A -0.4(4) . . . . ?
N8 C3A C3 N2 0.1(3) . . . . ?
C3B C3A C3 N2 179.8(4) . . . . ?
C3A C3B N4 O1 -68.4(3) . . . . ?
C9 C3B N4 O1 58.8(3) . . . . ?
C6A C3B N4 O1 -176.1(2) . . . . ?
C3A C3B N4 C5 112.4(2) . . . . ?
C9 C3B N4 C5 -120.4(2) . . . . ?
C6A C3B N4 C5 4.7(3) . . . . ?
O1 N4 C5 C11 34.0(4) . . . . ?
C3B N4 C5 C11 -146.9(2) . . . . ?
O1 N4 C5 C6 155.2(3) . . . . ?
C3B N4 C5 C6 -25.7(3) . . . . ?
O1 N4 C5 C13 -88.9(3) . . . . ?
C3B N4 C5 C13 90.2(2) . . . . ?
N4 C3B C6A C7 137.9(2) . . . . ?
C3A C3B C6A C7 22.6(2) . . . . ?
C9 C3B C6A C7 -101.6(3) . . . . ?
N4 C3B C6A C6 18.7(2) . . . . ?
C3A C3B C6A C6 -96.5(2) . . . . ?
C9 C3B C6A C6 139.3(2) . . . . ?
N4 C5 C6 C15 159.5(2) . . . . ?
C11 C5 C6 C15 -84.3(3) . . . . ?
C13 C5 C6 C15 44.7(3) . . . . ?
N4 C5 C6 C6A 36.0(2) . . . . ?
C11 C5 C6 C6A 152.2(2) . . . . ?
C13 C5 C6 C6A -78.8(2) . . . . ?
C7 C6A C6 C15 82.3(3) . . . . ?
C3B C6A C6 C15 -162.5(2) . . . . ?
C7 C6A C6 C5 -150.3(2) . . . . ?
C3B C6A C6 C5 -35.1(2) . . . . ?
C6 C6A C7 N8 91.1(2) . . . . ?
C3B C6A C7 N8 -22.5(3) . . . . ?
C3 C3A N8 N1 0.1(3) . . . . ?
C3B C3A N8 N1 -179.6(2) . . . . ?
C3 C3A N8 C7 179.6(2) . . . . ?
C3B C3A N8 C7 -0.2(3) . . . . ?
N2 N1 N8 C3A -0.4(3) . . . . ?
N2 N1 N8 C7 -179.7(3) . . . . ?
C6A C7 N8 C3A 14.6(3) . . . . ?
C6A C7 N8 N1 -166.1(3) . . . . ?
N4 C3B C9 C10 179.1(3) . . . . ?
C3A C3B C9 C10 -55.1(4) . . . . ?
C6A C3B C9 C10 62.4(4) . . . . ?
N4 C5 C11 C12 64.5(4) . . . . ?
C6 C5 C11 C12 -46.2(4) . . . . ?
C13 C5 C11 C12 -174.4(3) . . . . ?
N4 C5 C13 C14 58.7(3) . . . . ?
C11 C5 C13 C14 -62.2(4) . . . . ?
C6 C5 C13 C14 167.1(3) . . . . ?
N6 N5 C15 C6 -156.0(3) . . . . ?
C5 C6 C15 N5 67.8(3) . . . . ?
C6A C6 C15 N5 -171.7(3) . . . . ?
 
_refine_diff_density_max    0.294
_refine_diff_density_min   -0.196
_refine_diff_density_rms    0.046



 
 
data_comp4b_MMM_51
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic 
;
6-(azidomethyl)-3b,5,5-triethyl-3-phenyl-
3b,4,5,6,6a,7-hexahydropyrrolo[2',3':3,4]
pyrrolo[1,2-c][1,2,3]triazol-4-oxyl 
;
_chemical_name_common             ?
_chemical_melting_point            381
_chemical_formula_moiety          'C20 H26 N7 O'
_chemical_formula_sum
 'C20 H26 N7 O' 
_chemical_formula_weight          380.48

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    8.403(3)
_cell_length_b                    8.881(3)
_cell_length_c                    27.001(10)
_cell_angle_alpha                 90
_cell_angle_beta                  93.113(10)
_cell_angle_gamma                 90
_cell_volume                      2012.0(13)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     9927
_cell_measurement_theta_min       2.41
_cell_measurement_theta_max       25.27
 
_exptl_crystal_description        'plate'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.256          
_exptl_crystal_F_000              812
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.410
_exptl_crystal_size_mid           0.240
_exptl_crystal_size_min           0.070
_exptl_absorpt_coefficient_mu     0.083
_shelx_estimated_absorpt_T_min    0.967
_shelx_estimated_absorpt_T_max    0.994
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.9086
_exptl_absorpt_correction_T_max   0.9587
_exptl_absorpt_process_details    'SADABS-2016/2'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed-tube'
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             43855
_diffrn_reflns_av_unetI/netI      0.0346
_diffrn_reflns_av_R_equivalents   0.0690
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -35
_diffrn_reflns_limit_l_max        35
_diffrn_reflns_theta_min          2.746
_diffrn_reflns_theta_max          28.013
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              4848
_reflns_number_gt                 3551
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0596P)²+0.6479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4848
_refine_ls_number_parameters      253
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0728
_refine_ls_R_factor_gt            0.0488
_refine_ls_wR_factor_ref          0.1392
_refine_ls_wR_factor_gt           0.1224
_refine_ls_goodness_of_fit_ref    1.019
_refine_ls_restrained_S_all       1.019
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O001 O 0.56926(17) 0.71841(15) 0.69039(4) 0.0621(4) Uani 1 1 d . . . . .
N003 N 0.66139(15) 0.47356(13) 0.55353(5) 0.0380(3) Uani 1 1 d . . . . .
N004 N 0.47782(17) 0.31233(15) 0.55909(5) 0.0454(3) Uani 1 1 d . . . . .
N005 N 0.58360(17) 0.36388(15) 0.52877(5) 0.0457(3) Uani 1 1 d . . . . .
N00M N 0.9506(2) 1.2384(2) 0.53157(10) 0.0939(8) Uani 1 1 d . . . . .
N02C N 0.62284(15) 0.73463(14) 0.64766(4) 0.0373(3) Uani 1 1 d . . . . .
N06C N 0.90577(17) 1.12079(17) 0.53659(6) 0.0531(4) Uani 1 1 d . . . . .
N07C N 0.87551(17) 0.98993(17) 0.54374(6) 0.0552(4) Uani 1 1 d . . . . .
C008 C 0.48969(18) 0.38967(16) 0.60324(6) 0.0375(3) Uani 1 1 d . . . . .
C009 C 0.61076(17) 0.49390(16) 0.59953(5) 0.0338(3) Uani 1 1 d . . . . .
C00C C 0.77997(17) 0.69601(16) 0.57903(5) 0.0330(3) Uani 1 1 d . . . . .
H00C H 0.885922 0.738490 0.586980 0.040 Uiso 1 1 calc R U . . .
C00D C 0.37913(19) 0.35468(17) 0.64219(6) 0.0425(4) Uani 1 1 d . . . . .
C00E C 0.60304(18) 0.87566(16) 0.61835(5) 0.0370(3) Uani 1 1 d . . . . .
C00F C 0.78533(19) 0.57610(17) 0.53828(6) 0.0406(4) Uani 1 1 d . . . . .
H00D H 0.759600 0.618219 0.505678 0.049 Uiso 1 1 calc R U . . .
H00E H 0.888484 0.527022 0.538463 0.049 Uiso 1 1 calc R U . . .
C00G C 0.70886(19) 0.94123(17) 0.53162(6) 0.0417(4) Uani 1 1 d . . . . .
H00F H 0.700407 0.902046 0.498044 0.050 Uiso 1 1 calc R U . . .
H00G H 0.638467 1.027487 0.533112 0.050 Uiso 1 1 calc R U . . .
C00H C 0.8390(2) 0.5447(2) 0.66120(7) 0.0493(4) Uani 1 1 d . . . . .
H00H H 0.784099 0.492699 0.686847 0.059 Uiso 1 1 calc R U . . .
H00I H 0.898458 0.469958 0.643629 0.059 Uiso 1 1 calc R U . . .
C00I C 0.2423(2) 0.2717(2) 0.63012(8) 0.0573(5) Uani 1 1 d . . . . .
H00J H 0.220341 0.241388 0.597491 0.069 Uiso 1 1 calc R U . . .
C00J C 0.7139(2) 0.99879(19) 0.64130(6) 0.0518(4) Uani 1 1 d . . . . .
H00A H 0.823183 0.964888 0.639416 0.062 Uiso 1 1 calc R U . . .
H00B H 0.701619 1.088538 0.620981 0.062 Uiso 1 1 calc R U . . .
C00K C 0.4071(2) 0.4012(2) 0.69099(7) 0.0563(5) Uani 1 1 d . . . . .
H00L H 0.497495 0.457640 0.699815 0.068 Uiso 1 1 calc R U . . .
C00L C 0.4292(2) 0.9269(2) 0.61671(7) 0.0550(5) Uani 1 1 d . . . . .
H00M H 0.404878 0.959785 0.649708 0.066 Uiso 1 1 calc R U . . .
H00N H 0.418442 1.013720 0.595000 0.066 Uiso 1 1 calc R U . . .
C00N C 0.3010(3) 0.3639(3) 0.72664(8) 0.0720(6) Uani 1 1 d . . . . .
H00O H 0.319943 0.396514 0.759160 0.086 Uiso 1 1 calc R U . . .
C00O C 0.9560(2) 0.6547(3) 0.68579(8) 0.0679(6) Uani 1 1 d . . . . .
H00P H 1.029365 0.601198 0.707890 0.102 Uiso 1 1 calc R U . . .
H00Q H 1.013722 0.704898 0.660893 0.102 Uiso 1 1 calc R U . . .
H00R H 0.899134 0.727685 0.704198 0.102 Uiso 1 1 calc R U . . .
C00P C 0.3057(2) 0.8113(3) 0.59940(10) 0.0777(7) Uani 1 1 d . . . . .
H00S H 0.201284 0.855143 0.599803 0.117 Uiso 1 1 calc R U . . .
H00T H 0.325501 0.779907 0.566285 0.117 Uiso 1 1 calc R U . . .
H00U H 0.311895 0.725808 0.621160 0.117 Uiso 1 1 calc R U . . .
C00Q C 0.1387(3) 0.2337(3) 0.66603(11) 0.0773(7) Uani 1 1 d . . . . .
H00V H 0.048298 0.177033 0.657484 0.093 Uiso 1 1 calc R U . . .
C00R C 0.1679(3) 0.2789(3) 0.71412(11) 0.0800(7) Uani 1 1 d . . . . .
H00W H 0.098085 0.252277 0.738226 0.096 Uiso 1 1 calc R U . . .
C00S C 0.6884(3) 1.0425(3) 0.69484(8) 0.0807(7) Uani 1 1 d . . . . .
H00X H 0.763368 1.119358 0.705184 0.121 Uiso 1 1 calc R U . . .
H00Y H 0.581940 1.079833 0.697295 0.121 Uiso 1 1 calc R U . . .
H00Z H 0.703892 0.955788 0.715789 0.121 Uiso 1 1 calc R U . . .
C00A C 0.71406(17) 0.61509(16) 0.62468(5) 0.0334(3) Uani 1 1 d . . . . .
C00B C 0.65637(17) 0.82075(16) 0.56731(5) 0.0326(3) Uani 1 1 d . . . . .
H01A H 0.563541 0.771181 0.550930 0.039 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O001 N02C 1.2692(16) . ?
N003 N005 1.3326(18) . ?
N003 C009 1.3468(19) . ?
N003 C00F 1.4595(19) . ?
N004 N005 1.3225(19) . ?
N004 C008 1.375(2) . ?
N00M N06C 1.121(2) . ?
N02C C00A 1.4668(18) . ?
N02C C00E 1.4861(19) . ?
N06C N07C 1.207(2) . ?
N07C C00G 1.485(2) . ?
C008 C009 1.383(2) . ?
C008 C00D 1.474(2) . ?
C009 C00A 1.520(2) . ?
C00C C00F 1.534(2) . ?
C00C C00B 1.540(2) . ?
C00C C00A 1.5546(19) . ?
C00C H00C 0.9800 . ?
C00D C00K 1.389(3) . ?
C00D C00I 1.390(2) . ?
C00E C00L 1.528(2) . ?
C00E C00B 1.551(2) . ?
C00E C00J 1.544(2) . ?
C00F H00D 0.9700 . ?
C00F H00E 0.9700 . ?
C00G C00B 1.521(2) . ?
C00G H00F 0.9700 . ?
C00G H00G 0.9700 . ?
C00H C00O 1.513(3) . ?
C00H C00A 1.534(2) . ?
C00H H00H 0.9700 . ?
C00H H00I 0.9700 . ?
C00I C00Q 1.380(3) . ?
C00I H00J 0.9300 . ?
C00J C00S 1.523(3) . ?
C00J H00A 0.9700 . ?
C00J H00B 0.9700 . ?
C00K C00N 1.387(3) . ?
C00K H00L 0.9300 . ?
C00L C00P 1.515(3) . ?
C00L H00M 0.9700 . ?
C00L H00N 0.9700 . ?
C00N C00R 1.377(3) . ?
C00N H00O 0.9300 . ?
C00O H00P 0.9600 . ?
C00O H00Q 0.9600 . ?
C00O H00R 0.9600 . ?
C00P H00S 0.9600 . ?
C00P H00T 0.9600 . ?
C00P H00U 0.9600 . ?
C00Q C00R 1.368(4) . ?
C00Q H00V 0.9300 . ?
C00R H00W 0.9300 . ?
C00S H00X 0.9600 . ?
C00S H00Y 0.9600 . ?
C00S H00Z 0.9600 . ?
C00B H01A 0.9800 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
N005 N003 C009 112.95(12) . . ?
N005 N003 C00F 130.73(13) . . ?
C009 N003 C00F 116.27(12) . . ?
N005 N004 C008 110.14(13) . . ?
N003 N005 N004 105.67(12) . . ?
O001 N02C C00A 121.45(12) . . ?
O001 N02C C00E 123.01(12) . . ?
C00A N02C C00E 115.51(11) . . ?
N00M N06C N07C 172.4(2) . . ?
N06C N07C C00G 116.70(15) . . ?
N004 C008 C009 106.90(13) . . ?
N004 C008 C00D 119.65(14) . . ?
C009 C008 C00D 133.42(14) . . ?
N003 C009 C008 104.32(13) . . ?
N003 C009 C00A 107.80(12) . . ?
C008 C009 C00A 147.82(13) . . ?
C00F C00C C00B 113.46(12) . . ?
C00F C00C C00A 105.87(12) . . ?
C00B C00C C00A 103.31(11) . . ?
C00F C00C H00C 111.3 . . ?
C00B C00C H00C 111.3 . . ?
C00A C00C H00C 111.3 . . ?
C00K C00D C00I 118.41(16) . . ?
C00K C00D C008 122.24(16) . . ?
C00I C00D C008 119.34(16) . . ?
N02C C00E C00L 110.21(13) . . ?
N02C C00E C00B 100.30(11) . . ?
C00L C00E C00B 112.93(13) . . ?
N02C C00E C00J 109.60(13) . . ?
C00L C00E C00J 110.85(14) . . ?
C00B C00E C00J 112.46(12) . . ?
N003 C00F C00C 100.46(11) . . ?
N003 C00F H00D 111.7 . . ?
C00C C00F H00D 111.7 . . ?
N003 C00F H00E 111.7 . . ?
C00C C00F H00E 111.7 . . ?
H00D C00F H00E 109.4 . . ?
N07C C00G C00B 111.57(13) . . ?
N07C C00G H00F 109.3 . . ?
C00B C00G H00F 109.3 . . ?
N07C C00G H00G 109.3 . . ?
C00B C00G H00G 109.3 . . ?
H00F C00G H00G 108.0 . . ?
C00O C00H C00A 115.14(15) . . ?
C00O C00H H00H 108.5 . . ?
C00A C00H H00H 108.5 . . ?
C00O C00H H00I 108.5 . . ?
C00A C00H H00I 108.5 . . ?
H00H C00H H00I 107.5 . . ?
C00Q C00I C00D 120.7(2) . . ?
C00Q C00I H00J 119.7 . . ?
C00D C00I H00J 119.7 . . ?
C00S C00J C00E 116.63(16) . . ?
C00S C00J H00A 108.1 . . ?
C00E C00J H00A 108.1 . . ?
C00S C00J H00B 108.1 . . ?
C00E C00J H00B 108.1 . . ?
H00A C00J H00B 107.3 . . ?
C00D C00K C00N 120.3(2) . . ?
C00D C00K H00L 119.8 . . ?
C00N C00K H00L 119.8 . . ?
C00P C00L C00E 116.44(16) . . ?
C00P C00L H00M 108.2 . . ?
C00E C00L H00M 108.2 . . ?
C00P C00L H00N 108.2 . . ?
C00E C00L H00N 108.2 . . ?
H00M C00L H00N 107.3 . . ?
C00R C00N C00K 120.3(2) . . ?
C00R C00N H00O 119.8 . . ?
C00K C00N H00O 119.8 . . ?
C00H C00O H00P 109.5 . . ?
C00H C00O H00Q 109.5 . . ?
H00P C00O H00Q 109.5 . . ?
C00H C00O H00R 109.5 . . ?
H00P C00O H00R 109.5 . . ?
H00Q C00O H00R 109.5 . . ?
C00L C00P H00S 109.5 . . ?
C00L C00P H00T 109.5 . . ?
H00S C00P H00T 109.5 . . ?
C00L C00P H00U 109.5 . . ?
H00S C00P H00U 109.5 . . ?
H00T C00P H00U 109.5 . . ?
C00R C00Q C00I 120.5(2) . . ?
C00R C00Q H00V 119.7 . . ?
C00I C00Q H00V 119.7 . . ?
C00Q C00R C00N 119.7(2) . . ?
C00Q C00R H00W 120.2 . . ?
C00N C00R H00W 120.2 . . ?
C00J C00S H00X 109.5 . . ?
C00J C00S H00Y 109.5 . . ?
H00X C00S H00Y 109.5 . . ?
C00J C00S H00Z 109.5 . . ?
H00X C00S H00Z 109.5 . . ?
H00Y C00S H00Z 109.5 . . ?
N02C C00A C009 113.75(12) . . ?
N02C C00A C00H 112.22(13) . . ?
C009 C00A C00H 110.68(13) . . ?
N02C C00A C00C 102.57(11) . . ?
C009 C00A C00C 101.11(11) . . ?
C00H C00A C00C 115.91(12) . . ?
C00G C00B C00C 114.88(12) . . ?
C00G C00B C00E 116.71(12) . . ?
C00C C00B C00E 105.54(11) . . ?
C00G C00B H01A 106.3 . . ?
C00C C00B H01A 106.3 . . ?
C00E C00B H01A 106.3 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C009 N003 N005 N004 0.82(17) . . . . ?
C00F N003 N005 N004 -176.57(15) . . . . ?
C008 N004 N005 N003 -0.25(17) . . . . ?
N005 N004 C008 C009 -0.37(17) . . . . ?
N005 N004 C008 C00D 177.89(13) . . . . ?
N005 N003 C009 C008 -1.03(17) . . . . ?
C00F N003 C009 C008 176.76(13) . . . . ?
N005 N003 C009 C00A 176.96(12) . . . . ?
C00F N003 C009 C00A -5.25(17) . . . . ?
N004 C008 C009 N003 0.81(16) . . . . ?
C00D C008 C009 N003 -177.10(16) . . . . ?
N004 C008 C009 C00A -175.6(2) . . . . ?
C00D C008 C009 C00A 6.5(4) . . . . ?
N004 C008 C00D C00K 164.42(15) . . . . ?
C009 C008 C00D C00K -17.9(3) . . . . ?
N004 C008 C00D C00I -15.2(2) . . . . ?
C009 C008 C00D C00I 162.48(17) . . . . ?
O001 N02C C00E C00L -49.24(19) . . . . ?
C00A N02C C00E C00L 132.76(14) . . . . ?
O001 N02C C00E C00B -168.52(14) . . . . ?
C00A N02C C00E C00B 13.49(15) . . . . ?
O001 N02C C00E C00J 73.00(18) . . . . ?
C00A N02C C00E C00J -104.99(14) . . . . ?
N005 N003 C00F C00C 164.02(15) . . . . ?
C009 N003 C00F C00C -13.29(17) . . . . ?
C00B C00C C00F N003 -86.88(14) . . . . ?
C00A C00C C00F N003 25.71(15) . . . . ?
N06C N07C C00G C00B -145.39(16) . . . . ?
C00K C00D C00I C00Q -1.4(3) . . . . ?
C008 C00D C00I C00Q 178.28(17) . . . . ?
N02C C00E C00J C00S -59.8(2) . . . . ?
C00L C00E C00J C00S 62.1(2) . . . . ?
C00B C00E C00J C00S -170.45(16) . . . . ?
C00I C00D C00K C00N 0.6(3) . . . . ?
C008 C00D C00K C00N -179.07(17) . . . . ?
N02C C00E C00L C00P -53.0(2) . . . . ?
C00B C00E C00L C00P 58.2(2) . . . . ?
C00J C00E C00L C00P -174.55(17) . . . . ?
C00D C00K C00N C00R 0.8(3) . . . . ?
C00D C00I C00Q C00R 0.8(3) . . . . ?
C00I C00Q C00R C00N 0.5(3) . . . . ?
C00K C00N C00R C00Q -1.3(3) . . . . ?
O001 N02C C00A C009 82.15(17) . . . . ?
C00E N02C C00A C009 -99.82(14) . . . . ?
O001 N02C C00A C00H -44.48(19) . . . . ?
C00E N02C C00A C00H 133.55(14) . . . . ?
O001 N02C C00A C00C -169.56(13) . . . . ?
C00E N02C C00A C00C 8.47(15) . . . . ?
N003 C009 C00A N02C 130.21(13) . . . . ?
C008 C009 C00A N02C -53.4(3) . . . . ?
N003 C009 C00A C00H -102.36(14) . . . . ?
C008 C009 C00A C00H 74.0(3) . . . . ?
N003 C009 C00A C00C 21.02(14) . . . . ?
C008 C009 C00A C00C -162.6(2) . . . . ?
C00O C00H C00A N02C -55.76(19) . . . . ?
C00O C00H C00A C009 175.98(15) . . . . ?
C00O C00H C00A C00C 61.6(2) . . . . ?
C00F C00C C00A N02C -146.51(12) . . . . ?
C00B C00C C00A N02C -27.01(13) . . . . ?
C00F C00C C00A C009 -28.85(14) . . . . ?
C00B C00C C00A C009 90.65(12) . . . . ?
C00F C00C C00A C00H 90.86(15) . . . . ?
C00B C00C C00A C00H -149.64(13) . . . . ?
N07C C00G C00B C00C -43.90(17) . . . . ?
N07C C00G C00B C00E 80.43(16) . . . . ?
C00F C00C C00B C00G -79.31(16) . . . . ?
C00A C00C C00B C00G 166.55(12) . . . . ?
C00F C00C C00B C00E 150.65(12) . . . . ?
C00A C00C C00B C00E 36.52(14) . . . . ?
N02C C00E C00B C00G -159.25(12) . . . . ?
C00L C00E C00B C00G 83.49(17) . . . . ?
C00J C00E C00B C00G -42.88(18) . . . . ?
N02C C00E C00B C00C -30.29(14) . . . . ?
C00L C00E C00B C00C -147.56(13) . . . . ?
C00J C00E C00B C00C 86.07(15) . . . . ?
 
_refine_diff_density_max    0.251
_refine_diff_density_min   -0.178
_refine_diff_density_rms    0.037



 
data_comp4c_mmm_82
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic 
;
3,6-bis(azidomethyl)-3b,5,5-triethyl-3b,4,5,6,6a,7-
hexahydropyrrolo[2',3':3,4]pyrrolo[1,2-c][1,2,3]
triazol-4-oxyl
;
_chemical_name_common             ?
_chemical_melting_point           358.6
_chemical_formula_moiety          'C15 H23 N10 O'
_chemical_formula_sum
 'C15 H23 N10 O' 
_chemical_formula_weight          359.43

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    12.2895(7)
_cell_length_b                    9.5375(4)
_cell_length_c                    15.8665(7)
_cell_angle_alpha                 90
_cell_angle_beta                  98.802(2)
_cell_angle_gamma                 90
_cell_volume                      1837.83(15)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     9927
_cell_measurement_theta_min       2.50
_cell_measurement_theta_max       27/08
 
_exptl_crystal_description        'block'
_exptl_crystal_colour             'yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.299          
_exptl_crystal_F_000              764
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.680
_exptl_crystal_size_mid           0.580
_exptl_crystal_size_min           0.250
_exptl_absorpt_coefficient_mu     0.090
_shelx_estimated_absorpt_T_min    0.941
_shelx_estimated_absorpt_T_max    0.978
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.8971
_exptl_absorpt_correction_T_max   0.9367
_exptl_absorpt_process_details    'SADABS-2016/2'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed tube'
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             30287
_diffrn_reflns_av_unetI/netI      0.0333
_diffrn_reflns_av_R_equivalents   0.0600
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          2.897
_diffrn_reflns_theta_max          27.521
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              4221
_reflns_number_gt                 3182
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0896P)²+0.5493P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4221
_refine_ls_number_parameters      238
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0710
_refine_ls_R_factor_gt            0.0513
_refine_ls_wR_factor_ref          0.1649
_refine_ls_wR_factor_gt           0.1422
_refine_ls_goodness_of_fit_ref    1.017
_refine_ls_restrained_S_all       1.017
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.92465(10) 0.56724(16) 0.62156(9) 0.0582(4) Uani 1 1 d . . . . .
N14 N 0.4165(2) 0.5760(3) 0.84059(16) 0.0949(8) Uani 1 1 d . . . . .
N11 N 0.6856(3) 0.1301(3) 0.4534(2) 0.1153(10) Uani 1 1 d . . . . .
N8 N 0.61045(11) 0.63409(15) 0.47182(8) 0.0401(3) Uani 1 1 d . . . . .
N13 N 0.49537(16) 0.60646(17) 0.81720(10) 0.0574(4) Uani 1 1 d . . . . .
N12 N 0.58521(17) 0.6336(3) 0.80132(12) 0.0805(7) Uani 1 1 d . . . . .
C16 C 0.59159(15) 0.7291(2) 0.72876(11) 0.0495(4) Uani 1 1 d . . . . .
H16A H 0.622035 0.818488 0.749812 0.059 Uiso 1 1 calc R U . . .
H16B H 0.518299 0.745417 0.697855 0.059 Uiso 1 1 calc R U . . .
C6 C 0.66395(12) 0.66473(16) 0.66927(9) 0.0346(3) Uani 1 1 d . . . . .
H6 H 0.628783 0.577486 0.646657 0.041 Uiso 1 1 calc R U . . .
C6A C 0.67275(13) 0.76193(17) 0.59291(9) 0.0362(3) Uani 1 1 d . . . . .
H6A H 0.684602 0.859584 0.611262 0.043 Uiso 1 1 calc R U . . .
C3B C 0.77331(12) 0.70358(16) 0.55591(9) 0.0341(3) Uani 1 1 d . . . . .
C3A C 0.71813(12) 0.60393(17) 0.48888(9) 0.0357(3) Uani 1 1 d . . . . .
C3 C 0.73202(14) 0.49707(19) 0.43359(10) 0.0433(4) Uani 1 1 d . . . . .
C9 C 0.83107(17) 0.4155(2) 0.42135(15) 0.0640(6) Uani 1 1 d . . . . .
H9A H 0.830646 0.401660 0.360731 0.077 Uiso 1 1 calc R U . . .
H9B H 0.896068 0.469830 0.443006 0.077 Uiso 1 1 calc R U . . .
N9 N 0.8391(2) 0.2773(3) 0.4638(2) 0.1004(8) Uani 1 1 d . . . . .
N10 N 0.7558(2) 0.2057(2) 0.45526(16) 0.0813(6) Uani 1 1 d . . . . .
C5 C 0.78387(12) 0.62973(17) 0.70797(9) 0.0360(3) Uani 1 1 d . . . . .
C12 C 0.80026(15) 0.4861(2) 0.75052(12) 0.0510(4) Uani 1 1 d . . . . .
H12A H 0.878732 0.468606 0.764230 0.061 Uiso 1 1 calc R U . . .
H12B H 0.771037 0.489703 0.803908 0.061 Uiso 1 1 calc R U . . .
C13 C 0.7483(2) 0.3637(2) 0.69958(19) 0.0774(7) Uani 1 1 d . . . . .
H13A H 0.669597 0.370017 0.694816 0.116 Uiso 1 1 calc R U . . .
H13B H 0.772990 0.277832 0.727767 0.116 Uiso 1 1 calc R U . . .
H13C H 0.769039 0.365224 0.643672 0.116 Uiso 1 1 calc R U . . .
N4 N 0.83584(10) 0.63004(14) 0.62883(8) 0.0362(3) Uani 1 1 d . . . . .
C10 C 0.84412(16) 0.8095(2) 0.51635(11) 0.0477(4) Uani 1 1 d . . . . .
H10A H 0.901136 0.758837 0.492990 0.057 Uiso 1 1 calc R U . . .
H10B H 0.798349 0.855908 0.469323 0.057 Uiso 1 1 calc R U . . .
C11 C 0.8985(2) 0.9207(2) 0.57738(14) 0.0673(6) Uani 1 1 d . . . . .
H11A H 0.843035 0.970621 0.601764 0.101 Uiso 1 1 calc R U . . .
H11B H 0.938283 0.984977 0.546928 0.101 Uiso 1 1 calc R U . . .
H11C H 0.948418 0.876578 0.621996 0.101 Uiso 1 1 calc R U . . .
C7 C 0.57350(14) 0.7485(2) 0.52177(10) 0.0459(4) Uani 1 1 d . . . . .
H7A H 0.506942 0.723985 0.544288 0.055 Uiso 1 1 calc R U . . .
H7B H 0.561212 0.834039 0.488587 0.055 Uiso 1 1 calc R U . . .
N2 N 0.63145(13) 0.46928(18) 0.38675(10) 0.0537(4) Uani 1 1 d . . . . .
N1 N 0.55653(13) 0.55387(19) 0.40994(9) 0.0517(4) Uani 1 1 d . . . . .
C14 C 0.83619(15) 0.7462(2) 0.76861(10) 0.0480(4) Uani 1 1 d . . . . .
H14A H 0.822256 0.835586 0.739841 0.058 Uiso 1 1 calc R U . . .
H14B H 0.798879 0.747607 0.818236 0.058 Uiso 1 1 calc R U . . .
C15 C 0.95856(18) 0.7341(3) 0.79904(14) 0.0676(6) Uani 1 1 d . . . . .
H15A H 0.972698 0.654216 0.835887 0.101 Uiso 1 1 calc R U . . .
H15B H 0.984295 0.817441 0.829730 0.101 Uiso 1 1 calc R U . . .
H15C H 0.996400 0.723025 0.750820 0.101 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 N4 1.2657(17) . ?
N14 N13 1.127(3) . ?
N11 N10 1.120(3) . ?
N8 N1 1.338(2) . ?
N8 C3A 1.341(2) . ?
N8 C7 1.461(2) . ?
N13 N12 1.198(3) . ?
N12 C16 1.479(2) . ?
C16 C6 1.521(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C6 C6A 1.543(2) . ?
C6 C5 1.544(2) . ?
C6 H6 0.9800 . ?
C6A C7 1.535(2) . ?
C6A C3B 1.550(2) . ?
C6A H6A 0.9800 . ?
C3B N4 1.4659(19) . ?
C3B C3A 1.508(2) . ?
C3B C10 1.529(2) . ?
C3A C3 1.372(2) . ?
C3 N2 1.367(2) . ?
C3 C9 1.482(3) . ?
C9 N9 1.476(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N9 N10 1.222(3) . ?
C5 N4 1.4933(19) . ?
C5 C12 1.527(2) . ?
C5 C14 1.544(2) . ?
C12 C13 1.505(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C10 C11 1.520(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N2 N1 1.318(2) . ?
C14 C15 1.512(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
N1 N8 C3A 112.85(14) . . ?
N1 N8 C7 131.68(14) . . ?
C3A N8 C7 115.46(14) . . ?
N14 N13 N12 172.4(2) . . ?
N13 N12 C16 117.19(18) . . ?
N12 C16 C6 109.89(15) . . ?
N12 C16 H16A 109.7 . . ?
C6 C16 H16A 109.7 . . ?
N12 C16 H16B 109.7 . . ?
C6 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C16 C6 C6A 111.28(13) . . ?
C16 C6 C5 116.97(13) . . ?
C6A C6 C5 105.36(12) . . ?
C16 C6 H6 107.6 . . ?
C6A C6 H6 107.6 . . ?
C5 C6 H6 107.6 . . ?
C7 C6A C6 112.59(14) . . ?
C7 C6A C3B 106.34(12) . . ?
C6 C6A C3B 103.74(12) . . ?
C7 C6A H6A 111.3 . . ?
C6 C6A H6A 111.3 . . ?
C3B C6A H6A 111.3 . . ?
N4 C3B C3A 112.33(13) . . ?
N4 C3B C10 112.17(13) . . ?
C3A C3B C10 110.45(12) . . ?
N4 C3B C6A 103.00(11) . . ?
C3A C3B C6A 101.24(12) . . ?
C10 C3B C6A 117.07(14) . . ?
N8 C3A C3 104.23(14) . . ?
N8 C3A C3B 109.30(13) . . ?
C3 C3A C3B 146.36(15) . . ?
N2 C3 C3A 107.51(15) . . ?
N2 C3 C9 121.28(16) . . ?
C3A C3 C9 131.19(16) . . ?
N9 C9 C3 114.06(19) . . ?
N9 C9 H9A 108.7 . . ?
C3 C9 H9A 108.7 . . ?
N9 C9 H9B 108.7 . . ?
C3 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N10 N9 C9 116.9(2) . . ?
N11 N10 N9 172.5(3) . . ?
N4 C5 C12 109.21(13) . . ?
N4 C5 C14 109.37(13) . . ?
C12 C5 C14 110.84(13) . . ?
N4 C5 C6 99.80(11) . . ?
C12 C5 C6 115.03(13) . . ?
C14 C5 C6 111.93(14) . . ?
C13 C12 C5 116.22(15) . . ?
C13 C12 H12A 108.2 . . ?
C5 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
C5 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 N4 C3B 120.65(12) . . ?
O1 N4 C5 124.15(12) . . ?
C3B N4 C5 115.13(11) . . ?
C11 C10 C3B 114.92(14) . . ?
C11 C10 H10A 108.5 . . ?
C3B C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C3B C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N8 C7 C6A 100.55(12) . . ?
N8 C7 H7A 111.7 . . ?
C6A C7 H7A 111.7 . . ?
N8 C7 H7B 111.7 . . ?
C6A C7 H7B 111.7 . . ?
H7A C7 H7B 109.4 . . ?
N1 N2 C3 109.97(14) . . ?
N2 N1 N8 105.44(13) . . ?
C15 C14 C5 116.32(17) . . ?
C15 C14 H14A 108.2 . . ?
C5 C14 H14A 108.2 . . ?
C15 C14 H14B 108.2 . . ?
C5 C14 H14B 108.2 . . ?
H14A C14 H14B 107.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
N13 N12 C16 C6 -129.6(2) . . . . ?
N12 C16 C6 C6A -179.80(16) . . . . ?
N12 C16 C6 C5 -58.7(2) . . . . ?
C16 C6 C6A C7 -81.73(17) . . . . ?
C5 C6 C6A C7 150.56(13) . . . . ?
C16 C6 C6A C3B 163.72(14) . . . . ?
C5 C6 C6A C3B 36.02(15) . . . . ?
C7 C6A C3B N4 -142.19(13) . . . . ?
C6 C6A C3B N4 -23.26(15) . . . . ?
C7 C6A C3B C3A -25.86(15) . . . . ?
C6 C6A C3B C3A 93.06(13) . . . . ?
C7 C6A C3B C10 94.24(16) . . . . ?
C6 C6A C3B C10 -146.83(14) . . . . ?
N1 N8 C3A C3 -0.06(18) . . . . ?
C7 N8 C3A C3 -178.85(14) . . . . ?
N1 N8 C3A C3B 177.19(12) . . . . ?
C7 N8 C3A C3B -1.60(18) . . . . ?
N4 C3B C3A N8 126.43(13) . . . . ?
C10 C3B C3A N8 -107.51(15) . . . . ?
C6A C3B C3A N8 17.19(15) . . . . ?
N4 C3B C3A C3 -58.4(3) . . . . ?
C10 C3B C3A C3 67.7(3) . . . . ?
C6A C3B C3A C3 -167.6(2) . . . . ?
N8 C3A C3 N2 -0.17(18) . . . . ?
C3B C3A C3 N2 -175.5(2) . . . . ?
N8 C3A C3 C9 -178.75(19) . . . . ?
C3B C3A C3 C9 5.9(4) . . . . ?
N2 C3 C9 N9 -79.3(3) . . . . ?
C3A C3 C9 N9 99.1(3) . . . . ?
C3 C9 N9 N10 45.8(3) . . . . ?
C16 C6 C5 N4 -157.16(14) . . . . ?
C6A C6 C5 N4 -32.97(15) . . . . ?
C16 C6 C5 C12 86.14(19) . . . . ?
C6A C6 C5 C12 -149.66(14) . . . . ?
C16 C6 C5 C14 -41.54(19) . . . . ?
C6A C6 C5 C14 82.65(15) . . . . ?
N4 C5 C12 C13 -62.3(2) . . . . ?
C14 C5 C12 C13 177.18(18) . . . . ?
C6 C5 C12 C13 48.9(2) . . . . ?
C3A C3B N4 O1 71.29(18) . . . . ?
C10 C3B N4 O1 -53.83(19) . . . . ?
C6A C3B N4 O1 179.41(14) . . . . ?
C3A C3B N4 C5 -105.69(14) . . . . ?
C10 C3B N4 C5 129.19(14) . . . . ?
C6A C3B N4 C5 2.43(16) . . . . ?
C12 C5 N4 O1 -36.7(2) . . . . ?
C14 C5 N4 O1 84.73(18) . . . . ?
C6 C5 N4 O1 -157.72(15) . . . . ?
C12 C5 N4 C3B 140.14(14) . . . . ?
C14 C5 N4 C3B -98.41(15) . . . . ?
C6 C5 N4 C3B 19.14(16) . . . . ?
N4 C3B C10 C11 -57.3(2) . . . . ?
C3A C3B C10 C11 176.59(17) . . . . ?
C6A C3B C10 C11 61.5(2) . . . . ?
N1 N8 C7 C6A 166.60(16) . . . . ?
C3A N8 C7 C6A -14.89(18) . . . . ?
C6 C6A C7 N8 -88.22(15) . . . . ?
C3B C6A C7 N8 24.73(16) . . . . ?
C3A C3 N2 N1 0.3(2) . . . . ?
C9 C3 N2 N1 179.10(18) . . . . ?
C3 N2 N1 N8 -0.4(2) . . . . ?
C3A N8 N1 N2 0.27(19) . . . . ?
C7 N8 N1 N2 178.81(17) . . . . ?
N4 C5 C14 C15 -60.93(19) . . . . ?
C12 C5 C14 C15 59.5(2) . . . . ?
C6 C5 C14 C15 -170.57(15) . . . . ?
 
_refine_diff_density_max    0.352
_refine_diff_density_min   -0.280
_refine_diff_density_rms    0.041



 
data_comp6_MMM_20
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic 
;
2,2,6a-triethyl-3-(hydroxymethyl)-1-6-(2-oxoethylidene)
hexahydro-1H-furo[3,4-b]pyrrol-1-oxyl
;
_chemical_name_common             ?
_chemical_melting_point           373
_chemical_formula_moiety          'C15 H24 N O4'
_chemical_formula_sum
 'C15 H24 N O4' 
_chemical_formula_weight          282.35

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    8.0418(7)
_cell_length_b                    12.0546(13)
_cell_length_c                    15.9887(15)
_cell_angle_alpha                 90
_cell_angle_beta                  102.711(4)
_cell_angle_gamma                 90
_cell_volume                      1512.0(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     1679
_cell_measurement_theta_min       2.61
_cell_measurement_theta_max       20.23
 
_exptl_crystal_description        'block'
_exptl_crystal_colour             'yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.240          
_exptl_crystal_F_000              612
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.290
_exptl_crystal_size_mid           0.130
_exptl_crystal_size_min           0.040
_exptl_absorpt_coefficient_mu     0.089
_shelx_estimated_absorpt_T_min    0.975
_shelx_estimated_absorpt_T_max    0.996
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.8830
_exptl_absorpt_correction_T_max   0.9579
_exptl_absorpt_process_details    'SADAVS-2016/2'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed tube'
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             9999
_diffrn_reflns_av_unetI/netI      0.0791
_diffrn_reflns_av_R_equivalents   0.0789
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          3.132
_diffrn_reflns_theta_max          25.097
_diffrn_reflns_theta_full         25.097
_diffrn_measured_fraction_theta_max   0.989
_diffrn_measured_fraction_theta_full  0.989
_diffrn_reflns_Laue_measured_fraction_max    0.989
_diffrn_reflns_Laue_measured_fraction_full   0.989
_diffrn_reflns_point_group_measured_fraction_max   0.989
_diffrn_reflns_point_group_measured_fraction_full  0.989
_reflns_number_total              2661
_reflns_number_gt                 1428
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1029P)²+1.1871P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2661
_refine_ls_number_parameters      188
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1520
_refine_ls_R_factor_gt            0.0768
_refine_ls_wR_factor_ref          0.2304
_refine_ls_wR_factor_gt           0.1881
_refine_ls_goodness_of_fit_ref    1.000
_refine_ls_restrained_S_all       1.000
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.6343(4) 0.4403(3) 0.6833(2) 0.0830(10) Uani 1 1 d . . . . .
N1 N 0.5931(4) 0.3373(3) 0.6861(2) 0.0540(9) Uani 1 1 d . . . . .
O2 O 0.3020(4) 0.0697(3) 0.52275(19) 0.0785(10) Uani 1 1 d . . . . .
H2 H 0.185(11) 0.070(6) 0.549(5) 0.19(3) Uiso 1 1 d . . . . .
C2 C 0.5075(4) 0.2732(3) 0.6080(2) 0.0476(9) Uani 1 1 d . . . . .
O3 O 0.4706(4) 0.5705(3) 0.8940(2) 0.0874(11) Uani 1 1 d . . . . .
C3A C 0.5906(4) 0.1553(3) 0.7337(2) 0.0465(9) Uani 1 1 d . . . . .
H3A H 0.690911 0.115494 0.723929 0.056 Uiso 1 1 calc R U . . .
C3 C 0.4557(4) 0.1693(3) 0.6501(2) 0.0435(9) Uani 1 1 d . . . . .
H3 H 0.347212 0.185533 0.665949 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5239(6) 0.1036(4) 0.8061(3) 0.0698(13) Uani 1 1 d . . . . .
H4A H 0.440855 0.046346 0.784378 0.084 Uiso 1 1 calc R U . . .
H4B H 0.616328 0.070893 0.848188 0.084 Uiso 1 1 calc R U . . .
O5 O 0.4473(4) 0.1913(3) 0.8430(2) 0.0812(10) Uani 1 1 d . . . . .
C6A C 0.6364(5) 0.2726(3) 0.7665(2) 0.0533(10) Uani 1 1 d . . . . .
C6 C 0.5130(5) 0.2859(4) 0.8268(2) 0.0585(11) Uani 1 1 d . . . . .
C7 C 0.3576(5) 0.3405(4) 0.5566(3) 0.0651(12) Uani 1 1 d . . . . .
H7A H 0.403352 0.405005 0.533175 0.078 Uiso 1 1 calc R U . . .
H7B H 0.300246 0.295534 0.508483 0.078 Uiso 1 1 calc R U . . .
C8 C 0.2261(6) 0.3797(5) 0.6039(3) 0.0912(17) Uani 1 1 d . . . . .
H8A H 0.173031 0.316781 0.624048 0.137 Uiso 1 1 calc R U . . .
H8B H 0.141191 0.422879 0.566018 0.137 Uiso 1 1 calc R U . . .
H8C H 0.280138 0.424514 0.651855 0.137 Uiso 1 1 calc R U . . .
C9 C 0.6377(5) 0.2459(4) 0.5528(3) 0.0628(12) Uani 1 1 d . . . . .
H9A H 0.729858 0.203630 0.587875 0.075 Uiso 1 1 calc R U . . .
H9B H 0.582036 0.198065 0.506187 0.075 Uiso 1 1 calc R U . . .
C10 C 0.7139(7) 0.3417(5) 0.5150(4) 0.0931(17) Uani 1 1 d . . . . .
H10A H 0.625379 0.382111 0.477172 0.140 Uiso 1 1 calc R U . . .
H10B H 0.794377 0.314659 0.483545 0.140 Uiso 1 1 calc R U . . .
H10C H 0.771005 0.389748 0.560186 0.140 Uiso 1 1 calc R U . . .
C11 C 0.4314(5) 0.0623(3) 0.5978(3) 0.0585(11) Uani 1 1 d . . . . .
H11A H 0.537882 0.043624 0.582130 0.070 Uiso 1 1 calc R U . . .
H11B H 0.404048 0.002701 0.633200 0.070 Uiso 1 1 calc R U . . .
C12 C 0.4592(6) 0.3771(5) 0.8623(3) 0.0754(14) Uani 1 1 d . . . . .
H12 H 0.374979 0.367501 0.893314 0.090 Uiso 1 1 calc R U . . .
C13 C 0.5193(6) 0.4835(5) 0.8563(4) 0.0900(17) Uani 1 1 d . . . . .
H13 H 0.599831 0.494190 0.823250 0.108 Uiso 1 1 calc R U . . .
C14 C 0.8214(5) 0.2893(4) 0.8170(3) 0.0740(14) Uani 1 1 d . . . . .
H14A H 0.833302 0.364909 0.838090 0.089 Uiso 1 1 calc R U . . .
H14B H 0.841243 0.240515 0.866437 0.089 Uiso 1 1 calc R U . . .
C15 C 0.9537(6) 0.2686(5) 0.7692(4) 0.1005(19) Uani 1 1 d . . . . .
H15A H 0.952038 0.191744 0.753307 0.151 Uiso 1 1 calc R U . . .
H15B H 1.063160 0.286741 0.804481 0.151 Uiso 1 1 calc R U . . .
H15C H 0.932995 0.313725 0.718514 0.151 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 N1 1.288(4) . ?
N1 C6A 1.478(5) . ?
N1 C2 1.501(5) . ?
O2 C11 1.408(5) . ?
O2 H2 1.11(9) . ?
C2 C3 1.523(5) . ?
C2 C7 1.533(5) . ?
C2 C9 1.546(5) . ?
O3 C13 1.312(7) . ?
C3A C4 1.512(5) . ?
C3A C6A 1.525(5) . ?
C3A C3 1.535(5) . ?
C3A H3A 0.9800 . ?
C3 C11 1.527(5) . ?
C3 H3 0.9800 . ?
C4 O5 1.416(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
O5 C6 1.307(5) . ?
C6A C6 1.536(6) . ?
C6A C14 1.541(5) . ?
C6 C12 1.352(6) . ?
C7 C8 1.506(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.496(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.382(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.461(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O1 N1 C6A 121.7(3) . . ?
O1 N1 C2 122.8(3) . . ?
C6A N1 C2 115.4(3) . . ?
C11 O2 H2 102(4) . . ?
N1 C2 C3 100.1(3) . . ?
N1 C2 C7 109.7(3) . . ?
C3 C2 C7 114.4(3) . . ?
N1 C2 C9 109.9(3) . . ?
C3 C2 C9 111.3(3) . . ?
C7 C2 C9 111.0(3) . . ?
C4 C3A C6A 102.6(3) . . ?
C4 C3A C3 114.2(3) . . ?
C6A C3A C3 105.5(3) . . ?
C4 C3A H3A 111.3 . . ?
C6A C3A H3A 111.3 . . ?
C3 C3A H3A 111.3 . . ?
C2 C3 C11 117.8(3) . . ?
C2 C3 C3A 105.5(3) . . ?
C11 C3 C3A 111.4(3) . . ?
C2 C3 H3 107.2 . . ?
C11 C3 H3 107.2 . . ?
C3A C3 H3 107.2 . . ?
O5 C4 C3A 105.7(3) . . ?
O5 C4 H4A 110.6 . . ?
C3A C4 H4A 110.6 . . ?
O5 C4 H4B 110.6 . . ?
C3A C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
C6 O5 C4 109.7(3) . . ?
N1 C6A C3A 101.4(3) . . ?
N1 C6A C6 115.4(3) . . ?
C3A C6A C6 99.9(3) . . ?
N1 C6A C14 113.7(3) . . ?
C3A C6A C14 115.6(3) . . ?
C6 C6A C14 109.9(3) . . ?
O5 C6 C12 116.5(4) . . ?
O5 C6 C6A 112.2(3) . . ?
C12 C6 C6A 131.3(5) . . ?
C8 C7 C2 116.9(3) . . ?
C8 C7 H7A 108.1 . . ?
C2 C7 H7A 108.1 . . ?
C8 C7 H7B 108.1 . . ?
C2 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C2 117.1(4) . . ?
C10 C9 H9A 108.0 . . ?
C2 C9 H9A 108.0 . . ?
C10 C9 H9B 108.0 . . ?
C2 C9 H9B 108.0 . . ?
H9A C9 H9B 107.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 C3 113.3(3) . . ?
O2 C11 H11A 108.9 . . ?
C3 C11 H11A 108.9 . . ?
O2 C11 H11B 108.9 . . ?
C3 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C6 C12 C13 125.2(5) . . ?
C6 C12 H12 117.4 . . ?
C13 C12 H12 117.4 . . ?
O3 C13 C12 124.4(5) . . ?
O3 C13 H13 117.8 . . ?
C12 C13 H13 117.8 . . ?
C15 C14 C6A 115.8(4) . . ?
C15 C14 H14A 108.3 . . ?
C6A C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
C6A C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O1 N1 C2 C3 -168.3(3) . . . . ?
C6A N1 C2 C3 15.1(4) . . . . ?
O1 N1 C2 C7 -47.8(4) . . . . ?
C6A N1 C2 C7 135.6(3) . . . . ?
O1 N1 C2 C9 74.6(4) . . . . ?
C6A N1 C2 C9 -102.1(4) . . . . ?
N1 C2 C3 C11 -155.0(3) . . . . ?
C7 C2 C3 C11 87.8(4) . . . . ?
C9 C2 C3 C11 -38.9(4) . . . . ?
N1 C2 C3 C3A -30.0(3) . . . . ?
C7 C2 C3 C3A -147.1(3) . . . . ?
C9 C2 C3 C3A 86.1(3) . . . . ?
C4 C3A C3 C2 148.0(3) . . . . ?
C6A C3A C3 C2 36.1(4) . . . . ?
C4 C3A C3 C11 -83.1(4) . . . . ?
C6A C3A C3 C11 165.0(3) . . . . ?
C6A C3A C4 O5 31.5(4) . . . . ?
C3 C3A C4 O5 -82.1(4) . . . . ?
C3A C4 O5 C6 -23.8(5) . . . . ?
O1 N1 C6A C3A -170.4(3) . . . . ?
C2 N1 C6A C3A 6.2(4) . . . . ?
O1 N1 C6A C6 82.7(4) . . . . ?
C2 N1 C6A C6 -100.6(4) . . . . ?
O1 N1 C6A C14 -45.6(5) . . . . ?
C2 N1 C6A C14 131.0(3) . . . . ?
C4 C3A C6A N1 -145.0(3) . . . . ?
C3 C3A C6A N1 -25.1(3) . . . . ?
C4 C3A C6A C6 -26.4(4) . . . . ?
C3 C3A C6A C6 93.5(3) . . . . ?
C4 C3A C6A C14 91.5(4) . . . . ?
C3 C3A C6A C14 -148.6(3) . . . . ?
C4 O5 C6 C12 -176.3(4) . . . . ?
C4 O5 C6 C6A 5.7(4) . . . . ?
N1 C6A C6 O5 121.9(4) . . . . ?
C3A C6A C6 O5 14.2(4) . . . . ?
C14 C6A C6 O5 -107.9(4) . . . . ?
N1 C6A C6 C12 -55.7(6) . . . . ?
C3A C6A C6 C12 -163.5(4) . . . . ?
C14 C6A C6 C12 74.5(6) . . . . ?
N1 C2 C7 C8 -54.4(5) . . . . ?
C3 C2 C7 C8 57.0(5) . . . . ?
C9 C2 C7 C8 -176.1(4) . . . . ?
N1 C2 C9 C10 -63.8(5) . . . . ?
C3 C2 C9 C10 -173.7(4) . . . . ?
C7 C2 C9 C10 57.8(5) . . . . ?
C2 C3 C11 O2 -61.3(4) . . . . ?
C3A C3 C11 O2 176.7(3) . . . . ?
O5 C6 C12 C13 176.7(4) . . . . ?
C6A C6 C12 C13 -5.8(8) . . . . ?
C6 C12 C13 O3 -177.2(4) . . . . ?
N1 C6A C14 C15 -54.4(6) . . . . ?
C3A C6A C14 C15 62.3(6) . . . . ?
C6 C6A C14 C15 174.5(5) . . . . ?
 
_refine_diff_density_max    0.459
_refine_diff_density_min   -0.184
_refine_diff_density_rms    0.049



 
data_comp7a_mmm49
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic 
;
2,2,5-triethyl-3,4-bis(hydroxymethyl)-5-(3-phenyl-1H-pyrazol-
5-yl)pyrrolidin-1-oxyl
;
_chemical_name_common             ?
_chemical_melting_point           457
_chemical_formula_moiety          'C21 H30 N3 O3'
_chemical_formula_sum
 'C21 H30 N3 O3' 
_chemical_formula_weight          372.48

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    14.501(3)
_cell_length_b                    10.311(2)
_cell_length_c                    14.717(3)
_cell_angle_alpha                 90
_cell_angle_beta                  115.511(6)
_cell_angle_gamma                 90
_cell_volume                      1985.9(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     200(2)
_cell_measurement_reflns_used     2997
_cell_measurement_theta_min       2.50
_cell_measurement_theta_max       23.99
 
_exptl_crystal_description        'needle'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.246          
_exptl_crystal_F_000              804
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.400
_exptl_crystal_size_mid           0.100
_exptl_crystal_size_min           0.060
_exptl_absorpt_coefficient_mu     0.084
_shelx_estimated_absorpt_T_min    0.967
_shelx_estimated_absorpt_T_max    0.995
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.9013
_exptl_absorpt_correction_T_max   0.9705
_exptl_absorpt_process_details    'SADABS-2016/2'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       200(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed tube'
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             23165
_diffrn_reflns_av_unetI/netI      0.0654
_diffrn_reflns_av_R_equivalents   0.0914
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.277
_diffrn_reflns_theta_max          25.077
_diffrn_reflns_theta_full         25.077
_diffrn_measured_fraction_theta_max   0.990
_diffrn_measured_fraction_theta_full  0.990
_diffrn_reflns_Laue_measured_fraction_max    0.990
_diffrn_reflns_Laue_measured_fraction_full   0.990
_diffrn_reflns_point_group_measured_fraction_max   0.990
_diffrn_reflns_point_group_measured_fraction_full  0.990
_reflns_number_total              3507
_reflns_number_gt                 2299
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0535P)²+0.0950P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3507
_refine_ls_number_parameters      259
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0902
_refine_ls_R_factor_gt            0.0450
_refine_ls_wR_factor_ref          0.1110
_refine_ls_wR_factor_gt           0.0947
_refine_ls_goodness_of_fit_ref    1.002
_refine_ls_restrained_S_all       1.002
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.71979(10) 0.65688(14) 0.44788(9) 0.0329(4) Uani 1 1 d . . . . .
O2 O 1.01263(11) 0.81200(14) 0.86284(10) 0.0323(4) Uani 1 1 d . . . . .
H2O H 1.0805(19) 0.825(2) 0.9006(18) 0.062(8) Uiso 1 1 d . . . . .
O3 O 0.92117(11) 0.60331(15) 0.89910(10) 0.0332(4) Uani 1 1 d . . . . .
H3O H 0.963(2) 0.673(3) 0.9051(19) 0.074(9) Uiso 1 1 d . . . . .
N1 N 0.56967(12) 0.83552(18) 0.61320(12) 0.0248(4) Uani 1 1 d . . . . .
H1N H 0.5517(16) 0.921(2) 0.6006(16) 0.046(7) Uiso 1 1 d . . . . .
N2 N 0.65443(12) 0.79991(16) 0.60295(12) 0.0265(4) Uani 1 1 d . . . . .
C1 C 0.93683(18) 0.6600(3) 0.45555(17) 0.0483(7) Uani 1 1 d . . . . .
H13 H 0.876920 0.603625 0.424176 0.072 Uiso 1 1 calc R U . . .
H1 H 0.996152 0.617883 0.452783 0.072 Uiso 1 1 calc R U . . .
H14 H 0.923555 0.742723 0.419312 0.072 Uiso 1 1 calc R U . . .
C2 C 0.95835(15) 0.6845(2) 0.56474(15) 0.0337(5) Uani 1 1 d . . . . .
H12 H 1.019460 0.740732 0.595277 0.040 Uiso 1 1 calc R U . . .
H11 H 0.975532 0.600617 0.600951 0.040 Uiso 1 1 calc R U . . .
C3 C 0.87141(14) 0.74778(19) 0.58258(14) 0.0262(5) Uani 1 1 d . . . . .
N4C N 0.78043(11) 0.66014(16) 0.54201(11) 0.0246(4) Uani 1 1 d . . . . .
C5 C 0.75147(13) 0.59913(19) 0.61730(13) 0.0228(5) Uani 1 1 d . . . . .
C6 C 0.66046(13) 0.67216(19) 0.61729(13) 0.0218(4) Uani 1 1 d . . . . .
C7 C 0.57942(14) 0.6262(2) 0.63582(14) 0.0268(5) Uani 1 1 d . . . . .
H24 H 0.566632 0.539007 0.647764 0.032 Uiso 1 1 calc R U . . .
C8 C 0.52178(14) 0.73425(19) 0.63314(14) 0.0236(5) Uani 1 1 d . . . . .
C9 C 0.43056(14) 0.7500(2) 0.65115(14) 0.0269(5) Uani 1 1 d . . . . .
C10 C 0.38699(16) 0.8717(2) 0.64764(16) 0.0388(6) Uani 1 1 d . . . . .
H3 H 0.414780 0.945886 0.630143 0.047 Uiso 1 1 calc R U . . .
C11 C 0.30397(17) 0.8853(3) 0.66933(17) 0.0483(7) Uani 1 1 d . . . . .
H27 H 0.275484 0.968764 0.667530 0.058 Uiso 1 1 calc R U . . .
C12 C 0.26222(18) 0.7784(3) 0.69359(17) 0.0499(7) Uani 1 1 d . . . . .
H2 H 0.205714 0.788312 0.709544 0.060 Uiso 1 1 calc R U . . .
C13 C 0.84964(13) 0.62283(18) 0.71485(13) 0.0228(5) Uani 1 1 d . . . . .
H4 H 0.898918 0.551709 0.721149 0.027 Uiso 1 1 calc R U . . .
C14 C 0.89405(14) 0.75054(19) 0.69605(14) 0.0241(5) Uani 1 1 d . . . . .
H5 H 0.853983 0.823618 0.705988 0.029 Uiso 1 1 calc R U . . .
C15 C 0.83803(16) 0.8794(2) 0.53028(15) 0.0338(5) Uani 1 1 d . . . . .
H9 H 0.823771 0.869118 0.458566 0.041 Uiso 1 1 calc R U . . .
H10 H 0.773263 0.904859 0.532647 0.041 Uiso 1 1 calc R U . . .
C16 C 0.91470(18) 0.9892(2) 0.57471(18) 0.0522(7) Uani 1 1 d . . . . .
H7 H 0.924378 1.006641 0.643706 0.078 Uiso 1 1 calc R U . . .
H6 H 0.888906 1.067485 0.533723 0.078 Uiso 1 1 calc R U . . .
H8 H 0.980148 0.964226 0.575276 0.078 Uiso 1 1 calc R U . . .
C17 C 1.00631(15) 0.7727(2) 0.76696(14) 0.0289(5) Uani 1 1 d . . . . .
H15 H 1.045617 0.691747 0.774203 0.035 Uiso 1 1 calc R U . . .
H16 H 1.035333 0.840791 0.739519 0.035 Uiso 1 1 calc R U . . .
C18 C 0.82966(14) 0.61950(19) 0.80848(13) 0.0265(5) Uani 1 1 d . . . . .
H17 H 0.795960 0.701339 0.812592 0.032 Uiso 1 1 calc R U . . .
H18 H 0.782318 0.547260 0.802221 0.032 Uiso 1 1 calc R U . . .
C19 C 0.72415(14) 0.45609(19) 0.59249(15) 0.0282(5) Uani 1 1 d . . . . .
H19 H 0.708160 0.418471 0.645941 0.034 Uiso 1 1 calc R U . . .
H23 H 0.661183 0.451252 0.528639 0.034 Uiso 1 1 calc R U . . .
C20 C 0.80527(16) 0.3722(2) 0.58211(16) 0.0377(6) Uani 1 1 d . . . . .
H20 H 0.826570 0.412176 0.533775 0.057 Uiso 1 1 calc R U . . .
H21 H 0.777148 0.285817 0.558143 0.057 Uiso 1 1 calc R U . . .
H22 H 0.864395 0.364577 0.647706 0.057 Uiso 1 1 calc R U . . .
C21 C 0.38633(16) 0.6433(2) 0.67366(15) 0.0358(5) Uani 1 1 d . . . . .
H26 H 0.413808 0.559378 0.674701 0.043 Uiso 1 1 calc R U . . .
C22 C 0.30245(17) 0.6573(3) 0.69471(17) 0.0482(7) Uani 1 1 d . . . . .
H25 H 0.272718 0.583206 0.709909 0.058 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 N4C 1.2823(18) . ?
O2 C17 1.433(2) . ?
O2 H2O 0.91(3) . ?
O3 C18 1.429(2) . ?
O3 H3O 0.92(3) . ?
N1 N2 1.352(2) . ?
N1 C8 1.354(3) . ?
N1 H1N 0.92(2) . ?
N2 C6 1.331(3) . ?
C1 C2 1.520(3) . ?
C1 H13 0.9800 . ?
C1 H1 0.9800 . ?
C1 H14 0.9800 . ?
C2 C3 1.539(3) . ?
C2 H12 0.9900 . ?
C2 H11 0.9900 . ?
C3 N4C 1.495(2) . ?
C3 C15 1.532(3) . ?
C3 C14 1.557(3) . ?
N4C C5 1.483(2) . ?
C5 C6 1.519(3) . ?
C5 C19 1.530(3) . ?
C5 C13 1.545(2) . ?
C6 C7 1.398(3) . ?
C7 C8 1.383(3) . ?
C7 H24 0.9500 . ?
C8 C9 1.466(3) . ?
C9 C21 1.384(3) . ?
C9 C10 1.396(3) . ?
C10 C11 1.379(3) . ?
C10 H3 0.9500 . ?
C11 C12 1.376(4) . ?
C11 H27 0.9500 . ?
C12 C22 1.376(3) . ?
C12 H2 0.9500 . ?
C13 C18 1.526(3) . ?
C13 C14 1.542(3) . ?
C13 H4 1.0000 . ?
C14 C17 1.526(3) . ?
C14 H5 1.0000 . ?
C15 C16 1.523(3) . ?
C15 H9 0.9900 . ?
C15 H10 0.9900 . ?
C16 H7 0.9800 . ?
C16 H6 0.9800 . ?
C16 H8 0.9800 . ?
C17 H15 0.9900 . ?
C17 H16 0.9900 . ?
C18 H17 0.9900 . ?
C18 H18 0.9900 . ?
C19 C20 1.520(3) . ?
C19 H19 0.9900 . ?
C19 H23 0.9900 . ?
C20 H20 0.9800 . ?
C20 H21 0.9800 . ?
C20 H22 0.9800 . ?
C21 C22 1.386(3) . ?
C21 H26 0.9500 . ?
C22 H25 0.9500 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C17 O2 H2O 103.7(16) . . ?
C18 O3 H3O 107.7(16) . . ?
N2 N1 C8 112.98(17) . . ?
N2 N1 H1N 115.6(14) . . ?
C8 N1 H1N 131.2(14) . . ?
C6 N2 N1 104.59(16) . . ?
C2 C1 H13 109.5 . . ?
C2 C1 H1 109.5 . . ?
H13 C1 H1 109.5 . . ?
C2 C1 H14 109.5 . . ?
H13 C1 H14 109.5 . . ?
H1 C1 H14 109.5 . . ?
C1 C2 C3 116.13(17) . . ?
C1 C2 H12 108.3 . . ?
C3 C2 H12 108.3 . . ?
C1 C2 H11 108.3 . . ?
C3 C2 H11 108.3 . . ?
H12 C2 H11 107.4 . . ?
N4C C3 C15 107.54(15) . . ?
N4C C3 C2 108.81(16) . . ?
C15 C3 C2 113.23(17) . . ?
N4C C3 C14 100.46(15) . . ?
C15 C3 C14 113.43(16) . . ?
C2 C3 C14 112.38(16) . . ?
O1 N4C C5 120.85(14) . . ?
O1 N4C C3 121.59(15) . . ?
C5 N4C C3 116.30(14) . . ?
N4C C5 C6 108.37(15) . . ?
N4C C5 C19 110.98(15) . . ?
C6 C5 C19 110.01(15) . . ?
N4C C5 C13 100.55(14) . . ?
C6 C5 C13 111.98(15) . . ?
C19 C5 C13 114.49(15) . . ?
N2 C6 C7 111.26(16) . . ?
N2 C6 C5 119.23(17) . . ?
C7 C6 C5 129.42(18) . . ?
C8 C7 C6 105.68(18) . . ?
C8 C7 H24 127.2 . . ?
C6 C7 H24 127.2 . . ?
N1 C8 C7 105.49(17) . . ?
N1 C8 C9 122.72(18) . . ?
C7 C8 C9 131.74(19) . . ?
C21 C9 C10 118.3(2) . . ?
C21 C9 C8 120.17(19) . . ?
C10 C9 C8 121.49(19) . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H3 119.7 . . ?
C9 C10 H3 119.7 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H27 119.9 . . ?
C10 C11 H27 119.9 . . ?
C11 C12 C22 119.9(2) . . ?
C11 C12 H2 120.1 . . ?
C22 C12 H2 120.1 . . ?
C18 C13 C14 115.96(16) . . ?
C18 C13 C5 112.23(15) . . ?
C14 C13 C5 104.90(14) . . ?
C18 C13 H4 107.8 . . ?
C14 C13 H4 107.8 . . ?
C5 C13 H4 107.8 . . ?
C17 C14 C13 114.20(16) . . ?
C17 C14 C3 113.98(16) . . ?
C13 C14 C3 105.39(15) . . ?
C17 C14 H5 107.6 . . ?
C13 C14 H5 107.6 . . ?
C3 C14 H5 107.6 . . ?
C16 C15 C3 115.38(17) . . ?
C16 C15 H9 108.4 . . ?
C3 C15 H9 108.4 . . ?
C16 C15 H10 108.4 . . ?
C3 C15 H10 108.4 . . ?
H9 C15 H10 107.5 . . ?
C15 C16 H7 109.5 . . ?
C15 C16 H6 109.5 . . ?
H7 C16 H6 109.5 . . ?
C15 C16 H8 109.5 . . ?
H7 C16 H8 109.5 . . ?
H6 C16 H8 109.5 . . ?
O2 C17 C14 108.24(16) . . ?
O2 C17 H15 110.1 . . ?
C14 C17 H15 110.1 . . ?
O2 C17 H16 110.1 . . ?
C14 C17 H16 110.1 . . ?
H15 C17 H16 108.4 . . ?
O3 C18 C13 112.61(15) . . ?
O3 C18 H17 109.1 . . ?
C13 C18 H17 109.1 . . ?
O3 C18 H18 109.1 . . ?
C13 C18 H18 109.1 . . ?
H17 C18 H18 107.8 . . ?
C20 C19 C5 116.13(17) . . ?
C20 C19 H19 108.3 . . ?
C5 C19 H19 108.3 . . ?
C20 C19 H23 108.3 . . ?
C5 C19 H23 108.3 . . ?
H19 C19 H23 107.4 . . ?
C19 C20 H20 109.5 . . ?
C19 C20 H21 109.5 . . ?
H20 C20 H21 109.5 . . ?
C19 C20 H22 109.5 . . ?
H20 C20 H22 109.5 . . ?
H21 C20 H22 109.5 . . ?
C9 C21 C22 120.8(2) . . ?
C9 C21 H26 119.6 . . ?
C22 C21 H26 119.6 . . ?
C12 C22 C21 120.0(2) . . ?
C12 C22 H25 120.0 . . ?
C21 C22 H25 120.0 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C8 N1 N2 C6 -0.3(2) . . . . ?
C1 C2 C3 N4C 61.3(2) . . . . ?
C1 C2 C3 C15 -58.3(3) . . . . ?
C1 C2 C3 C14 171.60(19) . . . . ?
C15 C3 N4C O1 42.5(2) . . . . ?
C2 C3 N4C O1 -80.5(2) . . . . ?
C14 C3 N4C O1 161.36(15) . . . . ?
C15 C3 N4C C5 -124.77(17) . . . . ?
C2 C3 N4C C5 112.23(18) . . . . ?
C14 C3 N4C C5 -5.9(2) . . . . ?
O1 N4C C5 C6 -65.3(2) . . . . ?
C3 N4C C5 C6 102.06(17) . . . . ?
O1 N4C C5 C19 55.6(2) . . . . ?
C3 N4C C5 C19 -137.05(16) . . . . ?
O1 N4C C5 C13 177.10(15) . . . . ?
C3 N4C C5 C13 -15.5(2) . . . . ?
N1 N2 C6 C7 0.5(2) . . . . ?
N1 N2 C6 C5 -176.43(15) . . . . ?
N4C C5 C6 N2 -35.8(2) . . . . ?
C19 C5 C6 N2 -157.31(16) . . . . ?
C13 C5 C6 N2 74.2(2) . . . . ?
N4C C5 C6 C7 147.91(18) . . . . ?
C19 C5 C6 C7 26.4(3) . . . . ?
C13 C5 C6 C7 -102.1(2) . . . . ?
N2 C6 C7 C8 -0.5(2) . . . . ?
C5 C6 C7 C8 175.98(17) . . . . ?
N2 N1 C8 C7 -0.1(2) . . . . ?
N2 N1 C8 C9 177.55(16) . . . . ?
C6 C7 C8 N1 0.3(2) . . . . ?
C6 C7 C8 C9 -176.97(19) . . . . ?
N1 C8 C9 C21 -178.39(18) . . . . ?
C7 C8 C9 C21 -1.5(3) . . . . ?
N1 C8 C9 C10 0.7(3) . . . . ?
C7 C8 C9 C10 177.6(2) . . . . ?
C21 C9 C10 C11 2.1(3) . . . . ?
C8 C9 C10 C11 -177.01(19) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C22 -1.0(4) . . . . ?
N4C C5 C13 C18 157.36(15) . . . . ?
C6 C5 C13 C18 42.5(2) . . . . ?
C19 C5 C13 C18 -83.6(2) . . . . ?
N4C C5 C13 C14 30.62(18) . . . . ?
C6 C5 C13 C14 -84.26(18) . . . . ?
C19 C5 C13 C14 149.63(16) . . . . ?
C18 C13 C14 C17 73.5(2) . . . . ?
C5 C13 C14 C17 -162.05(16) . . . . ?
C18 C13 C14 C3 -160.59(15) . . . . ?
C5 C13 C14 C3 -36.19(19) . . . . ?
N4C C3 C14 C17 151.26(16) . . . . ?
C15 C3 C14 C17 -94.3(2) . . . . ?
C2 C3 C14 C17 35.8(2) . . . . ?
N4C C3 C14 C13 25.26(18) . . . . ?
C15 C3 C14 C13 139.72(16) . . . . ?
C2 C3 C14 C13 -90.24(19) . . . . ?
N4C C3 C15 C16 169.54(18) . . . . ?
C2 C3 C15 C16 -70.2(2) . . . . ?
C14 C3 C15 C16 59.4(2) . . . . ?
C13 C14 C17 O2 -76.1(2) . . . . ?
C3 C14 C17 O2 162.73(16) . . . . ?
C14 C13 C18 O3 -76.6(2) . . . . ?
C5 C13 C18 O3 162.89(16) . . . . ?
N4C C5 C19 C20 55.7(2) . . . . ?
C6 C5 C19 C20 175.66(16) . . . . ?
C13 C5 C19 C20 -57.2(2) . . . . ?
C10 C9 C21 C22 -1.6(3) . . . . ?
C8 C9 C21 C22 177.48(19) . . . . ?
C11 C12 C22 C21 1.5(4) . . . . ?
C9 C21 C22 C12 -0.1(3) . . . . ?
 
_refine_diff_density_max    0.175
_refine_diff_density_min   -0.245
_refine_diff_density_rms    0.047



