#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/89/4508964.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4508964
loop_
_publ_author_name
'Stanton, Mary K.'
'Tufekcic, Sunita'
'Morgan, Carrie'
'Bak, Annette'
_publ_section_title
;
 Drug Substance and Former Structure Property Relationships in 15 Diverse
 Pharmaceutical Co-Crystals
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1344
_journal_paper_doi               10.1021/cg8005019
_journal_volume                  9
_journal_year                    2009
_chemical_formula_sum            'C23 H18 F3 N4 O4 S'
_chemical_formula_weight         503.47
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.098(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.559(2)
_cell_length_b                   9.528(2)
_cell_length_c                   22.396(5)
_cell_measurement_reflns_used    1017
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.53
_cell_measurement_theta_min      2.25
_cell_volume                     2235.9(8)
_computing_cell_refinement       'SMART (BRUKER, V5.625, 2001)'
_computing_data_collection       'ASTRO (BRUKER, V5.007, 1997)'
_computing_data_reduction        'SAINT (BRUKER, V6.22, 2001)'
_computing_molecular_graphics    'SHELXTL (BRUKER, 2000, V6.1)'
_computing_publication_material  'XCIF (Sheldrick and BRUKER, 1997, V5.1)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       'ω, 0.3 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19940
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_correction_T_min  0.9593
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1036
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.023
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0831P)²+0.0403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1446
_refine_ls_wR_factor_ref         0.1560
_reflns_number_gt                4022
_reflns_number_total             5338
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg8005019sup5.cif
_cod_data_source_block           amg3806t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2235.8(9)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4508964
loop_
_symmetry_equiv_pos_as_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'
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_symmetry_multiplicity
_atom_site_calc_flag
S1 S -0.01714(6) -0.33932(6) 0.24538(3) 0.03042(17) Uani 1 1 d
F1 F 0.3297(2) 0.7148(2) -0.10993(11) 0.0831(7) Uani 1 1 d
F2 F 0.3497(3) 0.5231(2) -0.15063(10) 0.1047(10) Uani 1 1 d
F3 F 0.47990(19) 0.5883(4) -0.07763(12) 0.1249(12) Uani 1 1 d
O1 O -0.13983(15) 0.02994(16) 0.09136(7) 0.0293(4) Uani 1 1 d
O2 O 0.20442(17) -0.48493(18) 0.26337(7) 0.0386(4) Uani 1 1 d
N1 N 0.03215(17) -0.16617(19) 0.16119(8) 0.0245(4) Uani 1 1 d
N2 N 0.20356(19) -0.3107(2) 0.19482(9) 0.0280(4) Uani 1 1 d
H1 H 0.243(2) -0.265(3) 0.1696(11) 0.027(6) Uiso 1 1 d
N3 N -0.0398(2) 0.1847(2) 0.16109(8) 0.0319(5) Uani 1 1 d
N4 N 0.0928(2) 0.3656(2) 0.12866(9) 0.0373(5) Uani 1 1 d
C1 C 0.0807(2) -0.2657(2) 0.19658(9) 0.0251(5) Uani 1 1 d
C2 C -0.1384(2) -0.2278(2) 0.21456(10) 0.0265(5) Uani 1 1 d
C3 C -0.0937(2) -0.1425(2) 0.17053(9) 0.0239(5) Uani 1 1 d
C4 C -0.1776(2) -0.0488(2) 0.13917(9) 0.0260(5) Uani 1 1 d
C5 C -0.3030(2) -0.0424(3) 0.15044(11) 0.0324(5) Uani 1 1 d
H2 H -0.359(2) 0.021(3) 0.1298(10) 0.028(6) Uiso 1 1 d
C6 C -0.3458(2) -0.1313(3) 0.19341(11) 0.0338(5) Uani 1 1 d
H3 H -0.439(3) -0.124(3) 0.1995(12) 0.040(7) Uiso 1 1 d
C7 C -0.2649(2) -0.2232(3) 0.22619(11) 0.0314(5) Uani 1 1 d
H4 H -0.293(2) -0.281(3) 0.2545(11) 0.029(6) Uiso 1 1 d
C8 C 0.2584(2) -0.4241(2) 0.22585(10) 0.0301(5) Uani 1 1 d
C9 C 0.3853(3) -0.4641(3) 0.20906(13) 0.0384(6) Uani 1 1 d
H5 H 0.416(3) -0.405(4) 0.1782(16) 0.077(11) Uiso 1 1 d
H6 H 0.443(3) -0.467(3) 0.2423(14) 0.047(8) Uiso 1 1 d
H7 H 0.380(3) -0.555(4) 0.1923(16) 0.073(11) Uiso 1 1 d
C10 C -0.0643(2) 0.1446(2) 0.10459(10) 0.0249(5) Uani 1 1 d
C11 C -0.0172(2) 0.2098(2) 0.05695(10) 0.0270(5) Uani 1 1 d
H8 H -0.043(3) 0.179(3) 0.0156(13) 0.043(8) Uiso 1 1 d
C12 C 0.0653(2) 0.3204(2) 0.07113(10) 0.0264(5) Uani 1 1 d
C13 C 0.0379(3) 0.2965(3) 0.16944(11) 0.0396(6) Uani 1 1 d
H9 H 0.056(2) 0.331(3) 0.2106(12) 0.035(7) Uiso 1 1 d
C14 C 0.1357(2) 0.3911(2) 0.02567(10) 0.0271(5) Uani 1 1 d
C15 C 0.1355(3) 0.3393(3) -0.03133(12) 0.0528(8) Uani 1 1 d
H10 H 0.087(3) 0.256(4) -0.0454(17) 0.083(11) Uiso 1 1 d
C16 C 0.2077(3) 0.4018(3) -0.07152(13) 0.0559(9) Uani 1 1 d
H11 H 0.209(3) 0.376(3) -0.1085(16) 0.069(10) Uiso 1 1 d
C17 C 0.2803(2) 0.5174(2) -0.05489(10) 0.0298(5) Uani 1 1 d
C18 C 0.2804(3) 0.5719(3) 0.00181(11) 0.0403(6) Uani 1 1 d
H12 H 0.336(3) 0.648(3) 0.0144(13) 0.053(9) Uiso 1 1 d
C19 C 0.2084(3) 0.5088(3) 0.04194(11) 0.0383(6) Uani 1 1 d
H13 H 0.205(3) 0.546(3) 0.0823(12) 0.041(7) Uiso 1 1 d
C20 C 0.3604(3) 0.5823(3) -0.09791(12) 0.0391(6) Uani 1 1 d
O1S O 0.17249(19) 0.9795(2) 0.08847(10) 0.0572(6) Uani 1 1 d
H1S H 0.126(3) 0.928(4) 0.1132(15) 0.065(10) Uiso 1 1 d
O2S O 0.33105(17) 0.82908(19) 0.10934(8) 0.0419(5) Uani 1 1 d
C1S C 0.2884(2) 0.9348(3) 0.08537(10) 0.0324(5) Uani 1 1 d
C2S C 0.3635(3) 1.0292(3) 0.04867(14) 0.0402(6) Uani 1 1 d
H2S H 0.408(3) 1.090(3) 0.0786(14) 0.054(9) Uiso 1 1 d
H3S H 0.305(3) 1.083(3) 0.0221(13) 0.050(8) Uiso 1 1 d
C3S C 0.4578(2) 0.9505(3) 0.01550(11) 0.0336(5) Uani 1 1 d
H4S H 0.508(2) 0.888(3) 0.0456(11) 0.035(7) Uiso 1 1 d
H5S H 0.411(3) 0.890(3) -0.0155(12) 0.040(7) 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 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'
F F 0.0171 0.0103 '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'
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
C2 S1 C1 88.25(11) . .
C10 O1 C4 118.42(16) . .
C1 N1 C3 109.82(18) . .
C1 N2 C8 124.9(2) . .
C1 N2 H1 113.1(16) . .
C8 N2 H1 121.8(16) . .
C10 N3 C13 114.1(2) . .
C13 N4 C12 116.1(2) . .
N1 C1 N2 120.89(19) . .
N1 C1 S1 117.17(17) . .
N2 C1 S1 121.94(17) . .
C7 C2 C3 121.8(2) . .
C7 C2 S1 128.39(18) . .
C3 C2 S1 109.73(16) . .
C4 C3 N1 126.30(19) . .
C4 C3 C2 118.6(2) . .
N1 C3 C2 115.01(19) . .
C5 C4 C3 120.2(2) . .
C5 C4 O1 119.0(2) . .
C3 C4 O1 120.38(19) . .
C4 C5 C6 119.9(2) . .
C4 C5 H2 120.2(15) . .
C6 C5 H2 119.8(15) . .
C7 C6 C5 121.4(2) . .
C7 C6 H3 121.6(15) . .
C5 C6 H3 117.0(15) . .
C6 C7 C2 118.0(2) . .
C6 C7 H4 121.6(15) . .
C2 C7 H4 120.4(15) . .
O2 C8 N2 121.3(2) . .
O2 C8 C9 124.5(2) . .
N2 C8 C9 114.3(2) . .
C8 C9 H5 115(2) . .
C8 C9 H6 109.8(19) . .
H5 C9 H6 110(3) . .
C8 C9 H7 109(2) . .
H5 C9 H7 105(3) . .
H6 C9 H7 108(3) . .
N3 C10 O1 118.80(19) . .
N3 C10 C11 124.5(2) . .
O1 C10 C11 116.74(19) . .
C10 C11 C12 116.4(2) . .
C10 C11 H8 120.9(16) . .
C12 C11 H8 122.7(16) . .
N4 C12 C11 121.1(2) . .
N4 C12 C14 116.0(2) . .
C11 C12 C14 122.8(2) . .
N4 C13 N3 127.8(2) . .
N4 C13 H9 115.9(15) . .
N3 C13 H9 116.3(15) . .
C15 C14 C19 118.4(2) . .
C15 C14 C12 122.0(2) . .
C19 C14 C12 119.5(2) . .
C14 C15 C16 121.0(3) . .
C14 C15 H10 122(2) . .
C16 C15 H10 117(2) . .
C17 C16 C15 120.3(3) . .
C17 C16 H11 115(2) . .
C15 C16 H11 125(2) . .
C16 C17 C18 119.5(2) . .
C16 C17 C20 120.1(2) . .
C18 C17 C20 120.4(2) . .
C17 C18 C19 120.0(2) . .
C17 C18 H12 119.4(18) . .
C19 C18 H12 120.4(18) . .
C14 C19 C18 120.8(2) . .
C14 C19 H13 117.3(16) . .
C18 C19 H13 121.9(16) . .
F3 C20 F2 108.1(3) . .
F3 C20 F1 103.5(3) . .
F2 C20 F1 103.8(2) . .
F3 C20 C17 113.5(2) . .
F2 C20 C17 114.5(2) . .
F1 C20 C17 112.5(2) . .
C1S O1S H1S 115(2) . .
O2S C1S O1S 123.5(2) . .
O2S C1S C2S 123.3(2) . .
O1S C1S C2S 113.2(2) . .
C1S C2S C3S 113.2(2) . .
C1S C2S H2S 102.9(18) . .
C3S C2S H2S 110.4(19) . .
C1S C2S H3S 108.7(18) . .
C3S C2S H3S 112.0(17) . .
H2S C2S H3S 109(3) . .
C2S C3S C3S 112.0(3) . 3_675
C2S C3S H4S 106.6(15) . .
C3S C3S H4S 112.8(15) 3_675 .
C2S C3S H5S 109.7(16) . .
C3S C3S H5S 108.2(16) 3_675 .
H4S C3S H5S 107(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C2 1.739(2) .
S1 C1 1.741(2) .
F1 C20 1.323(3) .
F2 C20 1.301(3) .
F3 C20 1.289(3) .
O1 C10 1.363(3) .
O1 C4 1.405(3) .
O2 C8 1.219(3) .
N1 C1 1.300(3) .
N1 C3 1.389(3) .
N2 C1 1.371(3) .
N2 C8 1.374(3) .
N2 H1 0.86(3) .
N3 C10 1.317(3) .
N3 C13 1.343(3) .
N4 C13 1.317(3) .
N4 C12 1.355(3) .
C2 C7 1.393(3) .
C2 C3 1.404(3) .
C3 C4 1.387(3) .
C4 C5 1.379(3) .
C5 C6 1.398(3) .
C5 H2 0.93(2) .
C6 C7 1.371(4) .
C6 H3 1.01(3) .
C7 H4 0.92(3) .
C8 C9 1.486(4) .
C9 H5 0.98(4) .
C9 H6 0.90(3) .
C9 H7 0.95(4) .
C10 C11 1.379(3) .
C11 C12 1.379(3) .
C11 H8 0.98(3) .
C12 C14 1.493(3) .
C13 H9 0.98(3) .
C14 C15 1.368(3) .
C14 C19 1.383(3) .
C15 C16 1.384(4) .
C15 H10 0.98(4) .
C16 C17 1.368(4) .
C16 H11 0.87(4) .
C17 C18 1.371(3) .
C17 C20 1.492(3) .
C18 C19 1.384(3) .
C18 H12 0.95(3) .
C19 H13 0.98(3) .
O1S C1S 1.305(3) .
O1S H1S 0.92(3) .
O2S C1S 1.203(3) .
C1S C2S 1.508(3) .
C2S C3S 1.513(4) .
C2S H2S 0.96(3) .
C2S H3S 0.95(3) .
C3S C3S 1.523(5) 3_675
C3S H4S 1.00(3) .
C3S H5S 0.99(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1 O2S 0.86(3) 1.95(3) 2.808(3) 176(2) 1_545
O1S H1S N1 0.92(3) 1.79(4) 2.715(3) 178(3) 1_565
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_4
C3 N1 C1 N2 178.52(19) .
C3 N1 C1 S1 -1.0(2) .
C8 N2 C1 N1 -173.0(2) .
C8 N2 C1 S1 6.6(3) .
C2 S1 C1 N1 1.23(18) .
C2 S1 C1 N2 -178.33(19) .
C1 S1 C2 C7 175.0(2) .
C1 S1 C2 C3 -0.99(16) .
C1 N1 C3 C4 -176.9(2) .
C1 N1 C3 C2 0.2(3) .
C7 C2 C3 C4 1.8(3) .
S1 C2 C3 C4 178.03(16) .
C7 C2 C3 N1 -175.6(2) .
S1 C2 C3 N1 0.7(2) .
N1 C3 C4 C5 175.7(2) .
C2 C3 C4 C5 -1.3(3) .
N1 C3 C4 O1 2.4(3) .
C2 C3 C4 O1 -174.65(18) .
C10 O1 C4 C5 108.4(2) .
C10 O1 C4 C3 -78.2(3) .
C3 C4 C5 C6 -0.4(3) .
O1 C4 C5 C6 173.0(2) .
C4 C5 C6 C7 1.8(4) .
C5 C6 C7 C2 -1.4(4) .
C3 C2 C7 C6 -0.4(3) .
S1 C2 C7 C6 -175.93(18) .
C1 N2 C8 O2 -8.6(4) .
C1 N2 C8 C9 171.0(2) .
C13 N3 C10 O1 178.5(2) .
C13 N3 C10 C11 -0.6(3) .
C4 O1 C10 N3 -6.4(3) .
C4 O1 C10 C11 172.84(19) .
N3 C10 C11 C12 3.0(3) .
O1 C10 C11 C12 -176.19(19) .
C13 N4 C12 C11 1.0(4) .
C13 N4 C12 C14 -175.2(2) .
C10 C11 C12 N4 -3.1(3) .
C10 C11 C12 C14 172.9(2) .
C12 N4 C13 N3 1.7(4) .
C10 N3 C13 N4 -1.9(4) .
N4 C12 C14 C15 167.6(3) .
C11 C12 C14 C15 -8.6(4) .
N4 C12 C14 C19 -9.3(3) .
C11 C12 C14 C19 174.5(2) .
C19 C14 C15 C16 0.9(5) .
C12 C14 C15 C16 -176.0(3) .
C14 C15 C16 C17 -0.3(6) .
C15 C16 C17 C18 -0.5(5) .
C15 C16 C17 C20 178.5(3) .
C16 C17 C18 C19 0.7(4) .
C20 C17 C18 C19 -178.3(3) .
C15 C14 C19 C18 -0.7(4) .
C12 C14 C19 C18 176.3(2) .
C17 C18 C19 C14 -0.1(4) .
C16 C17 C20 F3 -122.3(3) .
C18 C17 C20 F3 56.8(4) .
C16 C17 C20 F2 2.5(4) .
C18 C17 C20 F2 -178.5(3) .
C16 C17 C20 F1 120.6(3) .
C18 C17 C20 F1 -60.4(3) .
O2S C1S C2S C3S 32.7(4) .
O1S C1S C2S C3S -147.3(3) .
C1S C2S C3S C3S -173.7(3) 3_675
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1 PubChem 139146816
