#------------------------------------------------------------------------------
#$Date: 2021-12-07 04:54:30 +0200 (Tue, 07 Dec 2021) $
#$Revision: 271160 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/37/7243764.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7243764
loop_
_publ_author_name
'Okayasu, Misaki'
'Kikkawa, Shoko'
'Hikawa, Hidemasa'
'Azumaya, Isao'
_publ_section_title
;
 Relationship between crystal shape and unit cell shape: crystal shape
 modification via co-crystallization toward SXRD-suitable crystals
;
_journal_issue                   44
_journal_name_full               CrystEngComm
_journal_page_first              7760
_journal_page_last               7770
_journal_paper_doi               10.1039/D1CE00897H
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C23 H20 F N3 O2 S'
_chemical_formula_sum            'C23 H20 F N3 O2 S'
_chemical_formula_weight         421.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 98.168(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   10.2247(6)
_cell_length_b                   13.3486(6)
_cell_length_c                   15.0139(13)
_cell_measurement_reflns_used    5124
_cell_measurement_temperature    93
_cell_measurement_theta_max      28.52
_cell_measurement_theta_min      2.74
_cell_volume                     2028.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31848
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.525
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             880.00
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4638
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0632
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0608P)²+1.0180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1620
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2687
_reflns_number_total             4638
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d1ce00897h2.cif
_cod_data_source_block           akt004_1d_s03a15N
_cod_depositor_comments
'Adding full bibliography for 7243759--7243776.cif.'
_cod_database_code               7243764
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
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 0.67983(7) 0.50602(5) 0.68231(6) 0.0545(3) Uani 1 1 d . . . . .
F1 F 0.97777(18) 0.29737(15) 0.94097(15) 0.0729(6) Uani 1 1 d . . . . .
O1 O 0.6394(2) 0.56747(13) 0.60511(17) 0.0646(7) Uani 1 1 d . . . . .
O2 O 0.7219(2) 0.55168(13) 0.76796(17) 0.0615(6) Uani 1 1 d . . . . .
N1 N 0.8013(2) 0.43856(18) 0.6559(2) 0.0507(7) Uani 1 1 d . . . . .
N2 N 0.7867(2) 0.42077(18) 0.4650(2) 0.0588(7) Uani 1 1 d . . . . .
N3 N 0.6961(3) 0.4450(2) -0.0129(2) 0.0710(8) Uani 1 1 d . . . . .
C1 C 0.8715(2) 0.36478(19) 0.7097(2) 0.0452(8) Uani 1 1 d . . . . .
C2 C 0.8847(3) 0.3661(2) 0.8029(2) 0.0510(8) Uani 1 1 d . . . . .
H2 H 0.840936 0.414866 0.834002 0.061 Uiso 1 1 calc R U . . .
C3 C 0.9640(3) 0.2935(2) 0.8487(2) 0.0531(8) Uani 1 1 d . . . . .
C4 C 1.0296(3) 0.2216(2) 0.8088(3) 0.0551(9) Uani 1 1 d . . . . .
H4 H 1.084330 0.174214 0.843524 0.066 Uiso 1 1 calc R U . . .
C5 C 1.0141(3) 0.2200(2) 0.7167(3) 0.0520(8) Uani 1 1 d . . . . .
H5 H 1.058118 0.169985 0.687140 0.062 Uiso 1 1 calc R U . . .
C6 C 0.9352(3) 0.28985(19) 0.6655(2) 0.0478(8) Uani 1 1 d . . . . .
H6 H 0.924334 0.287118 0.601636 0.057 Uiso 1 1 calc R U . . .
C7 C 0.5515(3) 0.42076(18) 0.6958(2) 0.0448(8) Uani 1 1 d . . . . .
C8 C 0.4801(3) 0.37846(18) 0.6196(2) 0.0483(8) Uani 1 1 d . . . . .
H8 H 0.497156 0.397025 0.561227 0.058 Uiso 1 1 calc R U . . .
C9 C 0.3819(3) 0.30735(18) 0.6306(2) 0.0476(8) Uani 1 1 d . . . . .
C10 C 0.3606(3) 0.28282(19) 0.7173(2) 0.0494(8) Uani 1 1 d . . . . .
H10 H 0.295261 0.234425 0.725504 0.059 Uiso 1 1 calc R U . . .
C11 C 0.4315(3) 0.3267(2) 0.7910(2) 0.0495(8) Uani 1 1 d . . . . .
H11 H 0.414089 0.309283 0.849545 0.059 Uiso 1 1 calc R U . . .
C12 C 0.5289(3) 0.39660(18) 0.7808(2) 0.0480(8) Uani 1 1 d . . . . .
H12 H 0.578777 0.427041 0.831897 0.058 Uiso 1 1 calc R U . . .
C13 C 0.3019(3) 0.2589(2) 0.5513(2) 0.0598(9) Uani 1 1 d . . . . .
H13A H 0.329683 0.284705 0.495841 0.072 Uiso 1 1 calc R U . . .
H13B H 0.315313 0.186241 0.554483 0.072 Uiso 1 1 calc R U . . .
H13C H 0.208157 0.273996 0.551608 0.072 Uiso 1 1 calc R U . . .
C14 C 0.8402(3) 0.4940(2) 0.4206(3) 0.0547(9) Uani 1 1 d . . . . .
H14 H 0.892367 0.543025 0.455099 0.066 Uiso 1 1 calc R U . . .
C15 C 0.8242(2) 0.50248(19) 0.3293(2) 0.0475(8) Uani 1 1 d . . . . .
H15 H 0.864867 0.556033 0.301816 0.057 Uiso 1 1 calc R U . . .
C16 C 0.7484(2) 0.43245(18) 0.2766(2) 0.0440(8) Uani 1 1 d . . . . .
C17 C 0.6916(3) 0.3567(2) 0.3211(3) 0.0551(9) Uani 1 1 d . . . . .
H17 H 0.638121 0.307335 0.288091 0.066 Uiso 1 1 calc R U . . .
C18 C 0.7130(3) 0.3536(2) 0.4133(3) 0.0620(9) Uani 1 1 d . . . . .
H18 H 0.673417 0.300788 0.442467 0.074 Uiso 1 1 calc R U . . .
C19 C 0.6073(4) 0.4032(3) 0.0324(3) 0.0811(13) Uani 1 1 d . . . . .
H19 H 0.530540 0.374857 -0.001390 0.097 Uiso 1 1 calc R U . . .
C20 C 0.6190(3) 0.3981(2) 0.1245(3) 0.0642(10) Uani 1 1 d . . . . .
H20 H 0.551126 0.367622 0.152174 0.077 Uiso 1 1 calc R U . . .
C21 C 0.7298(3) 0.43755(18) 0.1774(2) 0.0481(8) Uani 1 1 d . . . . .
C22 C 0.8213(3) 0.4826(2) 0.1296(3) 0.0548(9) Uani 1 1 d . . . . .
H22 H 0.898632 0.512420 0.161218 0.066 Uiso 1 1 calc R U . . .
C23 C 0.8010(3) 0.4843(2) 0.0376(3) 0.0639(10) Uani 1 1 d . . . . .
H23 H 0.866145 0.515524 0.007797 0.077 Uiso 1 1 calc R U . . .
H1 H 0.790(3) 0.435(2) 0.601(2) 0.045(11) Uiso 1 1 d . . . . .
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
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 S1 O2 119.87(13) . . ?
O1 S1 N1 105.17(16) . . ?
O2 S1 N1 108.19(16) . . ?
O1 S1 C7 109.11(14) . . ?
O2 S1 C7 107.69(15) . . ?
N1 S1 C7 106.00(12) . . ?
C1 N1 S1 126.3(3) . . ?
C1 N1 H1 122(2) . . ?
S1 N1 H1 106(2) . . ?
C14 N2 C18 115.7(3) . . ?
C23 N3 C19 115.3(3) . . ?
C2 C1 N1 122.7(3) . . ?
C2 C1 C6 119.9(3) . . ?
N1 C1 C6 117.3(3) . . ?
C3 C2 C1 117.4(3) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C4 C3 F1 119.0(3) . . ?
C4 C3 C2 124.5(3) . . ?
F1 C3 C2 116.4(3) . . ?
C3 C4 C5 117.6(3) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C12 C7 C8 122.4(3) . . ?
C12 C7 S1 119.0(2) . . ?
C8 C7 S1 118.7(2) . . ?
C7 C8 C9 118.6(3) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C10 C9 C8 118.5(3) . . ?
C10 C9 C13 120.3(3) . . ?
C8 C9 C13 121.2(3) . . ?
C11 C10 C9 121.5(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 118.7(3) . . ?
C7 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 124.1(3) . . ?
N2 C14 H14 117.9 . . ?
C15 C14 H14 117.9 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 117.1(3) . . ?
C17 C16 C21 121.2(3) . . ?
C15 C16 C21 121.7(3) . . ?
C18 C17 C16 119.5(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
N2 C18 C17 123.9(3) . . ?
N2 C18 H18 118.0 . . ?
C17 C18 H18 118.0 . . ?
N3 C19 C20 124.5(3) . . ?
N3 C19 H19 117.7 . . ?
C20 C19 H19 117.7 . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C22 114.8(3) . . ?
C20 C21 C16 122.5(3) . . ?
C22 C21 C16 122.7(3) . . ?
C23 C22 C21 120.7(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
N3 C23 C22 124.3(3) . . ?
N3 C23 H23 117.8 . . ?
C22 C23 H23 117.8 . . ?
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 O1 1.432(2) . ?
S1 O2 1.433(2) . ?
S1 N1 1.628(3) . ?
S1 C7 1.770(3) . ?
F1 C3 1.373(4) . ?
N1 C1 1.405(4) . ?
N1 H1 0.82(3) . ?
N2 C14 1.342(4) . ?
N2 C18 1.344(4) . ?
N3 C23 1.330(4) . ?
N3 C19 1.332(4) . ?
C1 C2 1.386(4) . ?
C1 C6 1.410(4) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.358(4) . ?
C4 C5 1.369(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.368(4) . ?
C7 C8 1.386(4) . ?
C8 C9 1.409(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(4) . ?
C9 C13 1.492(4) . ?
C10 C11 1.365(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.362(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(4) . ?
C16 C21 1.475(4) . ?
C17 C18 1.371(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.372(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.392(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(4) . ?
C22 C23 1.367(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N2 . . . 2.859(5) 0.82(3) 2.04(3) 173(3) no
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 S1 N1 C1 -178.4(2) . . . . ?
O2 S1 N1 C1 52.4(3) . . . . ?
C7 S1 N1 C1 -62.9(3) . . . . ?
S1 N1 C1 C2 -26.8(4) . . . . ?
S1 N1 C1 C6 156.1(2) . . . . ?
N1 C1 C2 C3 -175.4(2) . . . . ?
C6 C1 C2 C3 1.6(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C1 C2 C3 F1 178.8(2) . . . . ?
F1 C3 C4 C5 -179.9(2) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C2 C1 C6 C5 -2.1(4) . . . . ?
N1 C1 C6 C5 175.1(2) . . . . ?
O1 S1 C7 C12 -143.5(2) . . . . ?
O2 S1 C7 C12 -11.9(2) . . . . ?
N1 S1 C7 C12 103.7(2) . . . . ?
O1 S1 C7 C8 38.5(2) . . . . ?
O2 S1 C7 C8 170.10(19) . . . . ?
N1 S1 C7 C8 -74.3(2) . . . . ?
C12 C7 C8 C9 -0.7(4) . . . . ?
S1 C7 C8 C9 177.29(18) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C7 C8 C9 C13 -179.9(2) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C13 C9 C10 C11 -179.4(2) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C8 C7 C12 C11 0.4(4) . . . . ?
S1 C7 C12 C11 -177.50(18) . . . . ?
C10 C11 C12 C7 0.4(4) . . . . ?
C18 N2 C14 C15 -0.4(4) . . . . ?
N2 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C14 C15 C16 C21 -179.1(2) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C21 C16 C17 C18 178.9(2) . . . . ?
C14 N2 C18 C17 0.2(4) . . . . ?
C16 C17 C18 N2 0.3(4) . . . . ?
C23 N3 C19 C20 -0.6(5) . . . . ?
N3 C19 C20 C21 -0.6(6) . . . . ?
C19 C20 C21 C22 1.5(4) . . . . ?
C19 C20 C21 C16 -178.9(3) . . . . ?
C17 C16 C21 C20 27.2(4) . . . . ?
C15 C16 C21 C20 -153.4(3) . . . . ?
C17 C16 C21 C22 -153.1(3) . . . . ?
C15 C16 C21 C22 26.3(4) . . . . ?
C20 C21 C22 C23 -1.3(4) . . . . ?
C16 C21 C22 C23 179.0(3) . . . . ?
C19 N3 C23 C22 0.7(5) . . . . ?
C21 C22 C23 N3 0.2(5) . . . . ?
