 
data_CuBrL6
 
_audit_creation_method            SHELXL-2013
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C16 H13 Br Cu N3 O' 
_chemical_formula_weight          406.74

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'
 'Cu'  'Cu'   0.3201   1.2651
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Br'  'Br'  -0.2901   2.4595
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            15
_space_group_name_H-M_alt         'C 2/c'
_space_group_name_Hall            '-C 2yc'
 
_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+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    14.5021(17)
_cell_length_b                    13.7543(16)
_cell_length_c                    15.5420(18)
_cell_angle_alpha                 90
_cell_angle_beta                  104.9890(10)
_cell_angle_gamma                 90
_cell_volume                      2994.6(6)
_cell_formula_units_Z             8
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     5051 
_cell_measurement_theta_min       2.26 
_cell_measurement_theta_max       27.56 
 
_exptl_crystal_description        platelet 
_exptl_crystal_colour             orange 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.804          
_exptl_crystal_F_000              1616
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.150
_exptl_crystal_size_mid           0.080
_exptl_crystal_size_min           0.030
_exptl_absorpt_coefficient_mu     4.131
_shelx_estimated_absorpt_T_min    0.576
_shelx_estimated_absorpt_T_max    0.886
_exptl_absorpt_correction_type    'multi-scan'  
_exptl_absorpt_correction_T_min   0.300 
_exptl_absorpt_correction_T_max   0.886
_exptl_absorpt_process_details    'SADABS v2008/1 (Bruker, 2008)'    
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       100(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             6994
_diffrn_reflns_av_unetI/netI      0.0567
_diffrn_reflns_av_R_equivalents   0.0814
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.075
_diffrn_reflns_theta_max          24.995
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.972
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.972
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.972
_reflns_number_total              2630
_reflns_number_gt                 2392
_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        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_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)+(0.0504P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2630
_refine_ls_number_parameters      203
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0325
_refine_ls_R_factor_gt            0.0302
_refine_ls_wR_factor_ref          0.0826
_refine_ls_wR_factor_gt           0.0816
_refine_ls_goodness_of_fit_ref    1.023
_refine_ls_restrained_S_all       1.023
_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
Br1 Br 0.07012(2) 0.41838(2) 0.11009(2) 0.01942(12) Uani 1 1 d . . . . .
Cu1 Cu 0.18251(2) 0.32654(2) 0.21010(2) 0.01946(13) Uani 1 1 d . . . . .
O1 O 0.42506(12) 0.15103(15) 0.36323(13) 0.0200(4) Uani 1 1 d . . . . .
N1 N 0.31774(15) 0.37582(16) 0.27343(16) 0.0192(5) Uani 1 1 d . . . . .
N2 N 0.18158(14) 0.24597(15) 0.32029(15) 0.0179(5) Uani 1 1 d . . . . .
C21 C 0.21602(19) 0.1801(2) 0.07498(19) 0.0205(6) Uani 1 1 d . . . . .
H1 H 0.1612 0.2088 0.0362 0.025 Uiso 1 1 calc R U . . .
N4 N 0.24160(15) 0.20888(15) 0.15990(15) 0.0175(5) Uani 1 1 d . . . . .
C2 C 0.26889(19) 0.13744(18) 0.43238(19) 0.0197(6) Uani 1 1 d . . . . .
H2 H 0.3257 0.1019 0.4573 0.024 Uiso 1 1 calc R U . . .
C3 C 0.47209(19) 0.3346(2) 0.36511(19) 0.0226(6) Uani 1 1 d . . . . .
H9 H 0.5161 0.2859 0.3932 0.027 Uiso 1 1 calc R U . . .
C4 C 0.36884(19) 0.09315(18) 0.1870(2) 0.0204(6) Uani 1 1 d . . . . .
H3 H 0.4210 0.0625 0.2277 0.025 Uiso 1 1 calc R U . . .
C5 C 0.31674(17) 0.16659(17) 0.21585(19) 0.0157(5) Uani 1 1 d . . . . .
C6 C 0.34577(17) 0.20259(19) 0.31300(18) 0.0158(5) Uani 1 1 d . . . . .
C7 C 0.11084(19) 0.1864(2) 0.43305(19) 0.0223(6) Uani 1 1 d . . . . .
H4 H 0.0578 0.1849 0.4583 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4335(2) 0.5009(2) 0.3272(2) 0.0272(7) Uani 1 1 d . . . . .
H10 H 0.4499 0.5679 0.3304 0.033 Uiso 1 1 calc R U . . .
C10 C 0.1925(2) 0.13313(19) 0.47061(19) 0.0232(6) Uani 1 1 d . . . . .
H5 H 0.1961 0.0942 0.5218 0.028 Uiso 1 1 calc R U . . .
C11 C 0.3446(2) 0.47028(19) 0.2788(2) 0.0232(6) Uani 1 1 d . . . . .
H11 H 0.3005 0.5175 0.2480 0.028 Uiso 1 1 calc R U . . .
C12 C 0.4982(2) 0.4321(2) 0.3709(2) 0.0290(7) Uani 1 1 d . . . . .
H12 H 0.5600 0.4512 0.4046 0.035 Uiso 1 1 calc R U . . .
C13 C 0.38004(18) 0.30978(19) 0.31720(18) 0.0162(5) Uani 1 1 d . . . . .
C14 C 0.26572(19) 0.11026(19) 0.04069(19) 0.0213(6) Uani 1 1 d . . . . .
H6 H 0.2472 0.0932 -0.0206 0.026 Uiso 1 1 calc R U . . .
C15 C 0.10815(19) 0.2417(2) 0.35837(19) 0.0232(6) Uani 1 1 d . . . . .
H7 H 0.0522 0.2783 0.3328 0.028 Uiso 1 1 calc R U . . .
C16 C 0.34301(19) 0.0662(2) 0.0984(2) 0.0231(6) Uani 1 1 d . . . . .
H8 H 0.3782 0.0176 0.0773 0.028 Uiso 1 1 calc R U . . .
C20 C 0.26093(17) 0.19452(18) 0.35708(18) 0.0158(5) Uani 1 1 d . . . . .
H13 H 0.411(3) 0.090(3) 0.359(3) 0.039(10) Uiso 1 1 d . . . . .
 
 
_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
Br1 Cu1 2.3147(4) . ?
Cu1 N2 2.043(2) . ?
Cu1 N1 2.068(2) . ?
Cu1 N4 2.076(2) . ?
O1 C6 1.404(3) . ?
O1 H13 0.86(3) . ?
N1 C13 1.337(4) . ?
N1 C11 1.353(4) . ?
N2 C20 1.346(3) . ?
N2 C15 1.347(3) . ?
C21 N4 1.335(4) . ?
C21 C14 1.388(4) . ?
C21 H1 0.9500 . ?
N4 C5 1.339(3) . ?
C2 C10 1.387(4) . ?
C2 C20 1.389(4) . ?
C2 H2 0.9500 . ?
C3 C12 1.391(4) . ?
C3 C13 1.392(4) . ?
C3 H9 0.9500 . ?
C4 C16 1.381(4) . ?
C4 C5 1.403(4) . ?
C4 H3 0.9500 . ?
C5 C6 1.541(4) . ?
C6 C13 1.552(3) . ?
C6 C20 1.559(3) . ?
C7 C15 1.380(4) . ?
C7 C10 1.387(4) . ?
C7 H4 0.9500 . ?
C8 C11 1.380(4) . ?
C8 C12 1.381(4) . ?
C8 H10 0.9500 . ?
C10 H5 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 C16 1.382(4) . ?
C14 H6 0.9500 . ?
C15 H7 0.9500 . ?
C16 H8 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
N2 Cu1 N1 89.42(9) . . ?
N2 Cu1 N4 89.14(8) . . ?
N1 Cu1 N4 90.09(9) . . ?
N2 Cu1 Br1 134.65(6) . . ?
N1 Cu1 Br1 123.86(6) . . ?
N4 Cu1 Br1 117.43(6) . . ?
C6 O1 H13 108(3) . . ?
C13 N1 C11 118.4(2) . . ?
C13 N1 Cu1 116.91(17) . . ?
C11 N1 Cu1 124.54(19) . . ?
C20 N2 C15 118.5(2) . . ?
C20 N2 Cu1 116.81(16) . . ?
C15 N2 Cu1 124.71(19) . . ?
N4 C21 C14 123.1(3) . . ?
N4 C21 H1 118.5 . . ?
C14 C21 H1 118.5 . . ?
C21 N4 C5 119.0(2) . . ?
C21 N4 Cu1 124.50(18) . . ?
C5 N4 Cu1 116.14(18) . . ?
C10 C2 C20 118.9(3) . . ?
C10 C2 H2 120.5 . . ?
C20 C2 H2 120.5 . . ?
C12 C3 C13 118.6(3) . . ?
C12 C3 H9 120.7 . . ?
C13 C3 H9 120.7 . . ?
C16 C4 C5 118.8(3) . . ?
C16 C4 H3 120.6 . . ?
C5 C4 H3 120.6 . . ?
N4 C5 C4 121.4(3) . . ?
N4 C5 C6 117.9(2) . . ?
C4 C5 C6 120.8(2) . . ?
O1 C6 C5 111.1(2) . . ?
O1 C6 C13 104.4(2) . . ?
C5 C6 C13 110.5(2) . . ?
O1 C6 C20 110.2(2) . . ?
C5 C6 C20 111.2(2) . . ?
C13 C6 C20 109.2(2) . . ?
C15 C7 C10 118.7(2) . . ?
C15 C7 H4 120.6 . . ?
C10 C7 H4 120.6 . . ?
C11 C8 C12 118.6(3) . . ?
C11 C8 H10 120.7 . . ?
C12 C8 H10 120.7 . . ?
C2 C10 C7 119.1(3) . . ?
C2 C10 H5 120.4 . . ?
C7 C10 H5 120.4 . . ?
N1 C11 C8 122.7(3) . . ?
N1 C11 H11 118.6 . . ?
C8 C11 H11 118.6 . . ?
C8 C12 C3 119.3(3) . . ?
C8 C12 H12 120.3 . . ?
C3 C12 H12 120.3 . . ?
N1 C13 C3 122.3(2) . . ?
N1 C13 C6 117.2(2) . . ?
C3 C13 C6 120.5(2) . . ?
C16 C14 C21 118.0(3) . . ?
C16 C14 H6 121.0 . . ?
C21 C14 H6 121.0 . . ?
N2 C15 C7 122.7(3) . . ?
N2 C15 H7 118.7 . . ?
C7 C15 H7 118.7 . . ?
C4 C16 C14 119.7(3) . . ?
C4 C16 H8 120.2 . . ?
C14 C16 H8 120.2 . . ?
N2 C20 C2 122.1(2) . . ?
N2 C20 C6 117.5(2) . . ?
C2 C20 C6 120.5(2) . . ?
 
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
C14 C21 N4 C5 -2.3(4) . . . . ?
C14 C21 N4 Cu1 170.52(19) . . . . ?
C21 N4 C5 C4 0.1(3) . . . . ?
Cu1 N4 C5 C4 -173.28(18) . . . . ?
C21 N4 C5 C6 178.9(2) . . . . ?
Cu1 N4 C5 C6 5.5(3) . . . . ?
C16 C4 C5 N4 1.7(4) . . . . ?
C16 C4 C5 C6 -177.0(2) . . . . ?
N4 C5 C6 O1 179.7(2) . . . . ?
C4 C5 C6 O1 -1.5(3) . . . . ?
N4 C5 C6 C13 -64.9(3) . . . . ?
C4 C5 C6 C13 113.9(3) . . . . ?
N4 C5 C6 C20 56.5(3) . . . . ?
C4 C5 C6 C20 -124.7(2) . . . . ?
C20 C2 C10 C7 -0.5(4) . . . . ?
C15 C7 C10 C2 0.3(4) . . . . ?
C13 N1 C11 C8 0.2(4) . . . . ?
Cu1 N1 C11 C8 175.1(2) . . . . ?
C12 C8 C11 N1 1.0(4) . . . . ?
C11 C8 C12 C3 -0.1(4) . . . . ?
C13 C3 C12 C8 -1.8(4) . . . . ?
C11 N1 C13 C3 -2.3(4) . . . . ?
Cu1 N1 C13 C3 -177.6(2) . . . . ?
C11 N1 C13 C6 177.5(2) . . . . ?
Cu1 N1 C13 C6 2.2(3) . . . . ?
C12 C3 C13 N1 3.1(4) . . . . ?
C12 C3 C13 C6 -176.7(3) . . . . ?
O1 C6 C13 N1 179.4(2) . . . . ?
C5 C6 C13 N1 59.9(3) . . . . ?
C20 C6 C13 N1 -62.7(3) . . . . ?
O1 C6 C13 C3 -0.7(3) . . . . ?
C5 C6 C13 C3 -120.2(3) . . . . ?
C20 C6 C13 C3 117.2(3) . . . . ?
N4 C21 C14 C16 2.5(4) . . . . ?
C20 N2 C15 C7 -0.4(4) . . . . ?
Cu1 N2 C15 C7 -179.8(2) . . . . ?
C10 C7 C15 N2 0.1(4) . . . . ?
C5 C4 C16 C14 -1.4(4) . . . . ?
C21 C14 C16 C4 -0.6(4) . . . . ?
C15 N2 C20 C2 0.2(4) . . . . ?
Cu1 N2 C20 C2 179.68(19) . . . . ?
C15 N2 C20 C6 -178.6(2) . . . . ?
Cu1 N2 C20 C6 0.8(3) . . . . ?
C10 C2 C20 N2 0.2(4) . . . . ?
C10 C2 C20 C6 179.0(2) . . . . ?
O1 C6 C20 N2 175.3(2) . . . . ?
C5 C6 C20 N2 -61.0(3) . . . . ?
C13 C6 C20 N2 61.1(3) . . . . ?
O1 C6 C20 C2 -3.5(3) . . . . ?
C5 C6 C20 C2 120.1(3) . . . . ?
C13 C6 C20 C2 -117.7(3) . . . . ?
 
_refine_diff_density_max    0.627
_refine_diff_density_min   -0.651
_refine_diff_density_rms    0.102

_shelxl_version_number 2013-4



