data_mo_20181101-thf-2-a_0m
_audit_creation_date               2018-11-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C23 H19 F2 N O4 S'
_chemical_formula_sum              'C23 H19 F2 N O4 S'
_chemical_formula_weight           443.45
_chemical_melting_point            ?
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'
 'F' 'F' 0.0171 0.0103 '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'
 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
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                     11.187(6)
_cell_length_b                     9.038(5)
_cell_length_c                     20.928(11)
_cell_angle_alpha                  90
_cell_angle_beta                   97.133(17)
_cell_angle_gamma                  90
_cell_volume                       2099.6(19)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      375
_cell_measurement_temperature      210
_cell_measurement_theta_max        19.71
_cell_measurement_theta_min        2.46
_shelx_estimated_absorpt_T_max     0.996
_shelx_estimated_absorpt_T_min     0.963
_exptl_absorpt_coefficient_mu      0.202
_exptl_absorpt_correction_T_max    0.7453
_exptl_absorpt_correction_T_min    0.6496
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0922 before and 0.0687 after correction. The Ratio of minimum to maximum transmission is 0.8716. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.403
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               920
_exptl_crystal_size_max            0.19
_exptl_crystal_size_mid            0.07
_exptl_crystal_size_min            0.02
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0833
_diffrn_reflns_av_unetI/netI       0.0824
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.992
_diffrn_reflns_limit_h_max         12
_diffrn_reflns_limit_h_min         -13
_diffrn_reflns_limit_k_max         10
_diffrn_reflns_limit_k_min         -11
_diffrn_reflns_limit_l_max         25
_diffrn_reflns_limit_l_min         -25
_diffrn_reflns_number              15163
_diffrn_reflns_point_group_measured_fraction_full  0.997
_diffrn_reflns_point_group_measured_fraction_max  0.992
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           26.017
_diffrn_reflns_theta_min           1.961
_diffrn_ambient_temperature        210
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.992
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2555
_reflns_number_total               4096
_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.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.244
_refine_diff_density_min           -0.425
_refine_diff_density_rms           0.069
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     0.980
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       281
_refine_ls_number_reflns           4096
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0967
_refine_ls_R_factor_gt             0.0525
_refine_ls_restrained_S_all        0.980
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0597P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1142
_refine_ls_wR_factor_ref           0.1388
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C19(H19), C12(H12), C3(H3), C23(H23), C6(H6), C16(H16), C20(H20),
 C21(H21), C7(H7), C13(H13), C14(H14), C22(H22), C15(H15)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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
 S1 S 0.09439(6) 0.26147(8) 0.60702(3) 0.0318(2) Uani 1 1 d . . . . .
 F2 F 0.31315(13) 0.17905(18) 0.64359(7) 0.0364(4) Uani 1 1 d . . . . .
 F1 F 0.29361(15) 0.40028(18) 0.60281(7) 0.0415(5) Uani 1 1 d . . . . .
 O1 O 0.47829(18) 0.1387(2) 0.77980(9) 0.0435(5) Uani 1 1 d . . . . .
 O2 O 0.05370(18) 0.1440(2) 0.64452(9) 0.0435(5) Uani 1 1 d . . . . .
 O3 O 0.03152(18) 0.3998(2) 0.60196(10) 0.0474(6) Uani 1 1 d . . . . .
 N1 N 0.2495(2) 0.2653(2) 0.76091(10) 0.0289(5) Uani 1 1 d . . . . .
 O4 O -0.0456(2) 0.3302(3) 0.95486(11) 0.0672(7) Uani 1 1 d . . . . .
 C8 C 0.3594(2) 0.3501(3) 0.75859(12) 0.0302(6) Uani 1 1 d . . . . .
 H8 H 0.3722 0.4303 0.7909 0.036 Uiso 1 1 calc R . . . .
 C5 C 0.1761(3) 0.2916(3) 0.81136(13) 0.0315(7) Uani 1 1 d . . . . .
 C9 C 0.2525(2) 0.3718(3) 0.70887(12) 0.0296(6) Uani 1 1 d . . . . .
 H9 H 0.2059 0.4641 0.7121 0.035 Uiso 1 1 calc R . . . .
 C17 C 0.2481(2) 0.3051(3) 0.64336(12) 0.0286(6) Uani 1 1 d . . . . .
 C10 C 0.4693(2) 0.2575(3) 0.75275(12) 0.0302(6) Uani 1 1 d . . . . .
 C18 C 0.1150(2) 0.1986(3) 0.53004(12) 0.0302(6) Uani 1 1 d . . . . .
 C4 C 0.2196(3) 0.2469(3) 0.87272(13) 0.0354(7) Uani 1 1 d . . . . .
 H4 H 0.2980 0.2085 0.8810 0.042 Uiso 1 1 calc R . . . .
 C11 C 0.5677(2) 0.3151(3) 0.71797(13) 0.0341(7) Uani 1 1 d . . . . .
 C19 C 0.1499(3) 0.0544(3) 0.52162(13) 0.0394(7) Uani 1 1 d . . . . .
 H19 H 0.1625 -0.0109 0.5568 0.047 Uiso 1 1 calc R . . . .
 C12 C 0.5595(3) 0.4487(3) 0.68524(15) 0.0416(8) Uani 1 1 d . . . . .
 H12 H 0.4907 0.5083 0.6858 0.050 Uiso 1 1 calc R . . . .
 C3 C 0.1488(3) 0.2580(3) 0.92240(14) 0.0427(8) Uani 1 1 d . . . . .
 H3 H 0.1788 0.2268 0.9642 0.051 Uiso 1 1 calc R . . . .
 C23 C 0.0969(3) 0.2957(3) 0.47849(13) 0.0432(8) Uani 1 1 d . . . . .
 H23 H 0.0742 0.3943 0.4848 0.052 Uiso 1 1 calc R . . . .
 C2 C 0.0340(3) 0.3153(4) 0.90993(15) 0.0462(8) Uani 1 1 d . . . . .
 C6 C 0.0599(3) 0.3465(3) 0.79927(14) 0.0404(8) Uani 1 1 d . . . . .
 H6 H 0.0286 0.3750 0.7573 0.048 Uiso 1 1 calc R . . . .
 C16 C 0.6702(3) 0.2292(4) 0.71691(16) 0.0439(8) Uani 1 1 d . . . . .
 H16 H 0.6769 0.1383 0.7389 0.053 Uiso 1 1 calc R . . . .
 C20 C 0.1660(3) 0.0079(4) 0.46076(15) 0.0500(9) Uani 1 1 d . . . . .
 H20 H 0.1902 -0.0900 0.4543 0.060 Uiso 1 1 calc R . . . .
 C21 C 0.1471(3) 0.1025(4) 0.40938(15) 0.0524(9) Uani 1 1 d . . . . .
 H21 H 0.1579 0.0689 0.3680 0.063 Uiso 1 1 calc R . . . .
 C7 C -0.0095(3) 0.3592(4) 0.84869(16) 0.0483(8) Uani 1 1 d . . . . .
 H7 H -0.0877 0.3985 0.8405 0.058 Uiso 1 1 calc R . . . .
 C13 C 0.6517(3) 0.4948(4) 0.65179(17) 0.0544(9) Uani 1 1 d . . . . .
 H13 H 0.6454 0.5849 0.6292 0.065 Uiso 1 1 calc R . . . .
 C14 C 0.7534(3) 0.4079(4) 0.65166(18) 0.0546(9) Uani 1 1 d . . . . .
 H14 H 0.8166 0.4397 0.6293 0.066 Uiso 1 1 calc R . . . .
 C22 C 0.1126(3) 0.2459(4) 0.41792(14) 0.0537(9) Uani 1 1 d . . . . .
 H22 H 0.0998 0.3102 0.3824 0.064 Uiso 1 1 calc R . . . .
 C15 C 0.7623(3) 0.2763(4) 0.68385(18) 0.0553(10) Uani 1 1 d . . . . .
 H15 H 0.8316 0.2176 0.6835 0.066 Uiso 1 1 calc R . . . .
 C1 C -0.0041(4) 0.2888(5) 1.01920(18) 0.0885(15) Uani 1 1 d . . . . .
 H1A H 0.0145 0.1839 1.0208 0.133 Uiso 1 1 calc GR . . . .
 H1B H -0.0661 0.3095 1.0465 0.133 Uiso 1 1 calc GR . . . .
 H1C H 0.0679 0.3448 1.0343 0.133 Uiso 1 1 calc GR . . . .


_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
 S1 O2 1.428(2) . ?
 S1 O3 1.432(2) . ?
 S1 C17 1.835(3) . ?
 S1 C18 1.750(3) . ?
 F2 C17 1.351(3) . ?
 F1 C17 1.352(3) . ?
 O1 C10 1.212(3) . ?
 N1 C8 1.455(3) . ?
 N1 C5 1.436(3) . ?
 N1 C9 1.457(3) . ?
 O4 C2 1.380(3) . ?
 O4 C1 1.419(5) . ?
 C8 H8 0.9900 . ?
 C8 C9 1.498(4) . ?
 C8 C10 1.504(4) . ?
 C5 C4 1.376(4) . ?
 C5 C6 1.385(4) . ?
 C9 H9 0.9900 . ?
 C9 C17 1.493(4) . ?
 C10 C11 1.487(4) . ?
 C18 C19 1.379(4) . ?
 C18 C23 1.386(4) . ?
 C4 H4 0.9400 . ?
 C4 C3 1.386(4) . ?
 C11 C12 1.386(4) . ?
 C11 C16 1.388(4) . ?
 C19 H19 0.9400 . ?
 C19 C20 1.374(4) . ?
 C12 H12 0.9400 . ?
 C12 C13 1.381(4) . ?
 C3 H3 0.9400 . ?
 C3 C2 1.379(5) . ?
 C23 H23 0.9400 . ?
 C23 C22 1.377(4) . ?
 C2 C7 1.372(5) . ?
 C6 H6 0.9400 . ?
 C6 C7 1.373(4) . ?
 C16 H16 0.9400 . ?
 C16 C15 1.378(4) . ?
 C20 H20 0.9400 . ?
 C20 C21 1.370(5) . ?
 C21 H21 0.9400 . ?
 C21 C22 1.370(5) . ?
 C7 H7 0.9400 . ?
 C13 H13 0.9400 . ?
 C13 C14 1.382(4) . ?
 C14 H14 0.9400 . ?
 C14 C15 1.364(5) . ?
 C22 H22 0.9400 . ?
 C15 H15 0.9400 . ?
 C1 H1A 0.9700 . ?
 C1 H1B 0.9700 . ?
 C1 H1C 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
 O2 S1 O3 120.17(13) . . ?
 O2 S1 C17 106.16(12) . . ?
 O2 S1 C18 110.61(13) . . ?
 O3 S1 C17 105.64(13) . . ?
 O3 S1 C18 109.56(13) . . ?
 C18 S1 C17 103.17(13) . . ?
 C8 N1 C9 61.91(17) . . ?
 C5 N1 C8 120.0(2) . . ?
 C5 N1 C9 120.5(2) . . ?
 C2 O4 C1 117.2(3) . . ?
 N1 C8 H8 114.4 . . ?
 N1 C8 C9 59.13(17) . . ?
 N1 C8 C10 114.3(2) . . ?
 C9 C8 H8 114.4 . . ?
 C9 C8 C10 127.3(2) . . ?
 C10 C8 H8 114.4 . . ?
 C4 C5 N1 118.0(3) . . ?
 C4 C5 C6 119.4(3) . . ?
 C6 C5 N1 122.3(3) . . ?
 N1 C9 C8 58.96(17) . . ?
 N1 C9 H9 116.4 . . ?
 N1 C9 C17 114.7(2) . . ?
 C8 C9 H9 116.4 . . ?
 C17 C9 C8 121.2(2) . . ?
 C17 C9 H9 116.4 . . ?
 F2 C17 S1 107.27(18) . . ?
 F2 C17 F1 107.1(2) . . ?
 F2 C17 C9 112.4(2) . . ?
 F1 C17 S1 106.45(18) . . ?
 F1 C17 C9 110.3(2) . . ?
 C9 C17 S1 112.94(19) . . ?
 O1 C10 C8 118.4(3) . . ?
 O1 C10 C11 121.0(3) . . ?
 C11 C10 C8 120.5(2) . . ?
 C19 C18 S1 119.8(2) . . ?
 C19 C18 C23 121.0(3) . . ?
 C23 C18 S1 119.2(2) . . ?
 C5 C4 H4 119.7 . . ?
 C5 C4 C3 120.7(3) . . ?
 C3 C4 H4 119.7 . . ?
 C12 C11 C10 122.6(3) . . ?
 C12 C11 C16 118.9(3) . . ?
 C16 C11 C10 118.4(3) . . ?
 C18 C19 H19 120.7 . . ?
 C20 C19 C18 118.6(3) . . ?
 C20 C19 H19 120.7 . . ?
 C11 C12 H12 119.8 . . ?
 C13 C12 C11 120.3(3) . . ?
 C13 C12 H12 119.8 . . ?
 C4 C3 H3 120.3 . . ?
 C2 C3 C4 119.3(3) . . ?
 C2 C3 H3 120.3 . . ?
 C18 C23 H23 120.4 . . ?
 C22 C23 C18 119.1(3) . . ?
 C22 C23 H23 120.4 . . ?
 C3 C2 O4 124.9(3) . . ?
 C7 C2 O4 115.1(3) . . ?
 C7 C2 C3 120.0(3) . . ?
 C5 C6 H6 120.1 . . ?
 C7 C6 C5 119.9(3) . . ?
 C7 C6 H6 120.1 . . ?
 C11 C16 H16 119.8 . . ?
 C15 C16 C11 120.4(3) . . ?
 C15 C16 H16 119.8 . . ?
 C19 C20 H20 119.6 . . ?
 C21 C20 C19 120.8(3) . . ?
 C21 C20 H20 119.6 . . ?
 C20 C21 H21 119.8 . . ?
 C20 C21 C22 120.4(3) . . ?
 C22 C21 H21 119.8 . . ?
 C2 C7 C6 120.7(3) . . ?
 C2 C7 H7 119.6 . . ?
 C6 C7 H7 119.6 . . ?
 C12 C13 H13 120.1 . . ?
 C12 C13 C14 119.8(3) . . ?
 C14 C13 H13 120.1 . . ?
 C13 C14 H14 119.9 . . ?
 C15 C14 C13 120.3(3) . . ?
 C15 C14 H14 119.9 . . ?
 C23 C22 H22 120.0 . . ?
 C21 C22 C23 120.0(3) . . ?
 C21 C22 H22 120.0 . . ?
 C16 C15 H15 119.9 . . ?
 C14 C15 C16 120.2(3) . . ?
 C14 C15 H15 119.9 . . ?
 O4 C1 H1A 109.5 . . ?
 O4 C1 H1B 109.5 . . ?
 O4 C1 H1C 109.5 . . ?
 H1A C1 H1B 109.5 . . ?
 H1A C1 H1C 109.5 . . ?
 H1B C1 H1C 109.5 . . ?

_olex2_submission_special_instructions  'No special instructions were received'
