#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:25:12 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272632 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/40/7244065.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_7244065
loop_
_publ_author_name
'Hughes, David S.'
'Bingham, Ann L.'
'Hursthouse, Michael B.'
'Threlfall, Terry L.'
'Bond, Andrew D.'
_publ_section_title
;
 The extensive solid-form landscape of sulfathiazole: geometrical
 similarity and interaction energies
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              609
_journal_page_last               619
_journal_paper_doi               10.1039/D1CE01516H
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C4 H7 N'
_chemical_formula_sum            'C13 H16 N4 O2 S2'
_chemical_formula_weight         324.42
_chemical_name_common            'Sulfathiazole, butyronitrile solvate'
_chemical_name_systematic        'Sulfathiazole, butyronitrile (1:1) solvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2021-11-08 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.534(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2478(2)
_cell_length_b                   21.0191(6)
_cell_length_c                   9.0739(3)
_cell_measurement_reflns_used    5540
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      40.25
_cell_measurement_theta_min      2.91
_cell_volume                     1562.85(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9149
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.316
_diffrn_reflns_theta_min         3.545
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3897
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0662P)²+0.9188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1486
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2723
_reflns_number_total             3897
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01516h2.cif
_cod_data_source_block           31
_cod_depositor_comments
'Adding full bibliography for 7244056--7244077.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7244065
_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.
;
_shelx_estimated_absorpt_t_min   0.902
_shelx_estimated_absorpt_t_max   0.993
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'
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
S11 S 0.57094(7) 0.14231(3) 0.39754(7) 0.02568(18) Uani 1 1 d . . . . .
S12 S 0.68867(9) 0.13076(3) 0.75613(8) 0.0362(2) Uani 1 1 d . . . . .
O11 O 0.5543(2) 0.12305(8) 0.24377(18) 0.0317(4) Uani 1 1 d . . . . .
O12 O 0.7107(2) 0.18008(8) 0.4517(2) 0.0350(4) Uani 1 1 d . . . . .
N11 N -0.0301(3) 0.27729(11) 0.5102(3) 0.0351(5) Uani 1 1 d D . . . .
H10 H -0.032(4) 0.3039(15) 0.586(3) 0.066(11) Uiso 1 1 d D . . . .
H11 H -0.119(3) 0.2534(14) 0.499(3) 0.056(10) Uiso 1 1 d D . . . .
N12 N 0.5674(2) 0.07631(9) 0.4863(2) 0.0245(4) Uani 1 1 d . . . . .
N13 N 0.5934(3) 0.01827(10) 0.7027(2) 0.0288(5) Uani 1 1 d . . . . .
H17 H 0.553(4) -0.0141(15) 0.652(3) 0.045(9) Uiso 1 1 d . . . . .
C11 C 0.1097(3) 0.24601(11) 0.4865(3) 0.0258(5) Uani 1 1 d . . . . .
C12 C 0.1043(3) 0.19401(11) 0.3892(3) 0.0278(5) Uani 1 1 d . . . . .
H12 H 0.001965 0.179742 0.342079 0.033 Uiso 1 1 calc R U . . .
C13 C 0.2442(3) 0.16348(11) 0.3609(3) 0.0262(5) Uani 1 1 d . . . . .
H13 H 0.238435 0.128368 0.294585 0.031 Uiso 1 1 calc R U . . .
C14 C 0.3958(3) 0.18396(11) 0.4297(3) 0.0237(5) Uani 1 1 d . . . . .
C15 C 0.4040(3) 0.23552(11) 0.5266(3) 0.0255(5) Uani 1 1 d . . . . .
H15 H 0.506527 0.249673 0.573385 0.031 Uiso 1 1 calc R U . . .
C16 C 0.2625(3) 0.26590(11) 0.5543(3) 0.0256(5) Uani 1 1 d . . . . .
H16 H 0.268669 0.301010 0.620639 0.031 Uiso 1 1 calc R U . . .
C17 C 0.6103(3) 0.07304(11) 0.6311(3) 0.0248(5) Uani 1 1 d . . . . .
C18 C 0.6373(3) 0.01982(13) 0.8541(3) 0.0349(6) Uani 1 1 d . . . . .
H18 H 0.630952 -0.015798 0.917654 0.042 Uiso 1 1 calc R U . . .
C19 C 0.6896(4) 0.07693(14) 0.9005(3) 0.0413(7) Uani 1 1 d . . . . .
H19 H 0.723512 0.087077 1.001356 0.050 Uiso 1 1 calc R U . . .
N31 N 0.0937(4) 0.11722(14) 1.0194(3) 0.0607(8) Uani 1 1 d . . . . .
C31 C 0.1335(4) 0.11537(15) 0.9041(4) 0.0475(8) Uani 1 1 d . . . . .
C32 C 0.1818(6) 0.1096(2) 0.7544(5) 0.0790(13) Uani 1 1 d . . . . .
H32A H 0.115635 0.139834 0.689160 0.095 Uiso 1 1 calc R U . . .
H32B H 0.297249 0.122934 0.757621 0.095 Uiso 1 1 calc R U . . .
C33 C 0.1662(8) 0.0493(3) 0.6893(6) 0.114(2) Uani 1 1 d . . . . .
H33A H 0.145239 0.057746 0.581447 0.137 Uiso 1 1 calc R U . . .
H33B H 0.277317 0.030886 0.705365 0.137 Uiso 1 1 calc R U . . .
C34 C 0.0644(7) -0.0002(2) 0.7135(5) 0.0997(18) Uani 1 1 d . . . . .
H34A H 0.116613 -0.040535 0.691962 0.150 Uiso 1 1 calc R U . . .
H34B H -0.038306 0.004287 0.648501 0.150 Uiso 1 1 calc R U . . .
H34C H 0.042066 0.000145 0.817267 0.150 Uiso 1 1 calc R U . . .
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'
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
_geom_angle_publ_flag
O12 S11 O11 117.95(11) . . ?
O12 S11 N12 111.40(11) . . ?
O11 S11 N12 103.73(10) . . ?
O12 S11 C14 108.24(11) . . ?
O11 S11 C14 108.24(11) . . ?
N12 S11 C14 106.70(11) . . ?
C19 S12 C17 90.40(13) . . ?
C11 N11 H10 121(2) . . ?
C11 N11 H11 114(2) . . ?
H10 N11 H11 111.3(16) . . ?
C17 N12 S11 121.67(16) . . ?
C17 N13 C18 115.6(2) . . ?
C17 N13 H17 118(2) . . ?
C18 N13 H17 126(2) . . ?
N11 C11 C16 121.4(2) . . ?
N11 C11 C12 120.5(2) . . ?
C16 C11 C12 118.1(2) . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 S11 121.01(18) . . ?
C13 C14 S11 119.10(18) . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 121.3(2) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
N12 C17 N13 119.8(2) . . ?
N12 C17 S12 130.59(18) . . ?
N13 C17 S12 109.65(18) . . ?
C19 C18 N13 112.1(2) . . ?
C19 C18 H18 124.0 . . ?
N13 C18 H18 124.0 . . ?
C18 C19 S12 112.2(2) . . ?
C18 C19 H19 123.9 . . ?
S12 C19 H19 123.9 . . ?
N31 C31 C32 177.0(4) . . ?
C33 C32 C31 116.5(3) . . ?
C33 C32 H32A 108.2 . . ?
C31 C32 H32A 108.2 . . ?
C33 C32 H32B 108.2 . . ?
C31 C32 H32B 108.2 . . ?
H32A C32 H32B 107.3 . . ?
C34 C33 C32 130.5(4) . . ?
C34 C33 H33A 104.7 . . ?
C32 C33 H33A 104.7 . . ?
C34 C33 H33B 104.7 . . ?
C32 C33 H33B 104.7 . . ?
H33A C33 H33B 105.7 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
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
S11 O12 1.4393(18) . ?
S11 O11 1.4444(18) . ?
S11 N12 1.606(2) . ?
S11 C14 1.742(2) . ?
S12 C19 1.731(3) . ?
S12 C17 1.735(2) . ?
N11 C11 1.365(3) . ?
N11 H10 0.88(2) . ?
N11 H11 0.88(2) . ?
N12 C17 1.323(3) . ?
N13 C17 1.337(3) . ?
N13 C18 1.381(3) . ?
N13 H17 0.87(3) . ?
C11 C16 1.402(3) . ?
C11 C12 1.403(3) . ?
C12 C13 1.370(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(3) . ?
C15 C16 1.378(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.328(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C31 1.132(4) . ?
C31 C32 1.463(5) . ?
C32 C33 1.397(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.371(6) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
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
_geom_hbond_publ_flag
N11 H10 O11 0.88(2) 2.17(2) 3.005(3) 158(3) 4_566 yes
N11 H11 O12 0.88(2) 2.10(2) 2.961(3) 165(3) 1_455 yes
N13 H17 O11 0.87(3) 2.67(3) 3.267(3) 127(2) 3_656 yes
N13 H17 N12 0.87(3) 2.00(3) 2.852(3) 169(3) 3_656 yes
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
O12 S11 N12 C17 39.1(2) . . . . ?
O11 S11 N12 C17 166.95(18) . . . . ?
C14 S11 N12 C17 -78.9(2) . . . . ?
N11 C11 C12 C13 177.9(2) . . . . ?
C16 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C12 C13 C14 S11 177.44(18) . . . . ?
O12 S11 C14 C15 -15.2(2) . . . . ?
O11 S11 C14 C15 -144.12(19) . . . . ?
N12 S11 C14 C15 104.8(2) . . . . ?
O12 S11 C14 C13 167.26(18) . . . . ?
O11 S11 C14 C13 38.3(2) . . . . ?
N12 S11 C14 C13 -72.8(2) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
S11 C14 C15 C16 -177.38(18) . . . . ?
C14 C15 C16 C11 -0.1(4) . . . . ?
N11 C11 C16 C15 -177.9(2) . . . . ?
C12 C11 C16 C15 0.1(4) . . . . ?
S11 N12 C17 N13 174.71(17) . . . . ?
S11 N12 C17 S12 -4.5(3) . . . . ?
C18 N13 C17 N12 -178.4(2) . . . . ?
C18 N13 C17 S12 1.0(3) . . . . ?
C19 S12 C17 N12 178.1(2) . . . . ?
C19 S12 C17 N13 -1.25(19) . . . . ?
C17 N13 C18 C19 -0.1(3) . . . . ?
N13 C18 C19 S12 -0.9(3) . . . . ?
C17 S12 C19 C18 1.2(2) . . . . ?
C31 C32 C33 C34 26.0(10) . . . . ?
