#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:25:12 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272632 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/40/7244061.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_7244061
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         '2(C9 H9 N3 O2 S2), C6 H8 N2'
_chemical_formula_sum            'C24 H26 N8 O4 S4'
_chemical_formula_weight         618.77
_chemical_name_common            'Sulfathiazole, adiponitrile solvate'
_chemical_name_systematic
'Sulfathiazole, 1,6-hexanenitrile (2:1) solvate'
_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   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                 101.32(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.154(2)
_cell_length_b                   17.399(3)
_cell_length_c                   10.077(2)
_cell_measurement_reflns_used    12559
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      3.76
_cell_volume                     1401.8(5)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0370
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12559
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.013
_diffrn_reflns_theta_max         25.013
_diffrn_reflns_theta_min         3.764
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_exptl_absorpt_coefficient_mu    0.386
_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    1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2466
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0331
_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)+(0.0435P)²+0.5492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2136
_reflns_number_total             2466
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01516h2.cif
_cod_data_source_block           36
_cod_depositor_comments
'Adding full bibliography for 7244056--7244077.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7244061
_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   0.927
_shelx_estimated_absorpt_t_max   0.927
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.93783(5) 0.67577(2) 0.42279(5) 0.02337(15) Uani 1 1 d . . . . .
S12 S 0.86506(7) 0.65317(3) 0.73124(5) 0.03304(16) Uani 1 1 d . . . . .
O11 O 1.05558(16) 0.67234(7) 0.33389(14) 0.0312(3) Uani 1 1 d . . . . .
O12 O 0.94648(16) 0.73959(7) 0.51571(13) 0.0309(3) Uani 1 1 d . . . . .
N11 N 0.2564(2) 0.66212(11) 0.08850(19) 0.0369(4) Uani 1 1 d D . . . .
H10 H 0.184(3) 0.6922(12) 0.103(2) 0.050(7) Uiso 1 1 d D . . . .
H11 H 0.240(3) 0.6475(13) 0.0082(19) 0.047(7) Uiso 1 1 d D . . . .
N12 N 0.96030(18) 0.59441(8) 0.50125(14) 0.0228(3) Uani 1 1 d . . . . .
N13 N 0.91845(19) 0.51497(9) 0.67519(15) 0.0236(3) Uani 1 1 d . . . . .
H17 H 0.949(3) 0.4772(13) 0.631(2) 0.040(6) Uiso 1 1 d . . . . .
C11 C 0.4131(2) 0.66725(10) 0.16573(19) 0.0270(4) Uani 1 1 d . . . . .
C12 C 0.5474(2) 0.62812(12) 0.12690(19) 0.0300(4) Uani 1 1 d . . . . .
H12 H 0.528412 0.598828 0.045769 0.036 Uiso 1 1 calc R U . . .
C13 C 0.7053(2) 0.63179(11) 0.20470(18) 0.0274(4) Uani 1 1 d . . . . .
H13 H 0.794489 0.605137 0.176866 0.033 Uiso 1 1 calc R U . . .
C14 C 0.7360(2) 0.67419(9) 0.32402(18) 0.0222(4) Uani 1 1 d . . . . .
C15 C 0.6047(2) 0.71252(10) 0.36518(19) 0.0267(4) Uani 1 1 d . . . . .
H15 H 0.624419 0.741061 0.447147 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4455(2) 0.70903(11) 0.2867(2) 0.0293(4) Uani 1 1 d . . . . .
H16 H 0.356595 0.735437 0.315412 0.035 Uiso 1 1 calc R U . . .
C17 C 0.9189(2) 0.58545(9) 0.62078(17) 0.0207(4) Uani 1 1 d . . . . .
C18 C 0.8779(2) 0.51200(12) 0.80191(19) 0.0310(4) Uani 1 1 d . . . . .
H18 H 0.874828 0.465918 0.851942 0.037 Uiso 1 1 calc R U . . .
C19 C 0.8436(3) 0.58117(12) 0.8457(2) 0.0370(5) Uani 1 1 d . . . . .
H19 H 0.811113 0.590109 0.929925 0.044 Uiso 1 1 calc R U . . .
N31 N 0.2907(2) 0.58776(12) 0.8130(2) 0.0472(5) Uani 1 1 d . . . . .
C31 C 0.3423(3) 0.58682(12) 0.7159(2) 0.0363(5) Uani 1 1 d . . . . .
C32 C 0.4087(3) 0.58316(12) 0.5911(2) 0.0358(5) Uani 1 1 d . . . . .
H32A H 0.504235 0.619022 0.598020 0.043 Uiso 1 1 calc R U . . .
H32B H 0.321081 0.599684 0.513922 0.043 Uiso 1 1 calc R U . . .
C33 C 0.4661(2) 0.50201(11) 0.56487(19) 0.0310(4) Uani 1 1 d . . . . .
H33A H 0.554259 0.485635 0.641817 0.037 Uiso 1 1 calc R U . . .
H33B H 0.370753 0.466101 0.558645 0.037 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
O11 S11 O12 118.82(8) . . ?
O11 S11 N12 104.09(8) . . ?
O12 S11 N12 111.72(8) . . ?
O11 S11 C14 108.29(8) . . ?
O12 S11 C14 107.56(8) . . ?
N12 S11 C14 105.59(8) . . ?
C19 S12 C17 90.44(9) . . ?
C11 N11 H10 119.0(15) . . ?
C11 N11 H11 121.6(15) . . ?
H10 N11 H11 112.6(16) . . ?
C17 N12 S11 121.65(12) . . ?
C17 N13 C18 115.59(15) . . ?
C17 N13 H17 117.4(15) . . ?
C18 N13 H17 126.9(15) . . ?
N11 C11 C16 121.82(17) . . ?
N11 C11 C12 120.21(18) . . ?
C16 C11 C12 117.95(18) . . ?
C13 C12 C11 120.85(18) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.57(17) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 119.53(17) . . ?
C13 C14 S11 119.36(14) . . ?
C15 C14 S11 121.07(14) . . ?
C16 C15 C14 119.96(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 121.12(17) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
N12 C17 N13 120.07(15) . . ?
N12 C17 S12 130.26(13) . . ?
N13 C17 S12 109.66(13) . . ?
C19 C18 N13 112.14(17) . . ?
C19 C18 H18 123.9 . . ?
N13 C18 H18 123.9 . . ?
C18 C19 S12 112.17(14) . . ?
C18 C19 H19 123.9 . . ?
S12 C19 H19 123.9 . . ?
N31 C31 C32 178.3(2) . . ?
C31 C32 C33 111.52(17) . . ?
C31 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
C31 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 108.0 . . ?
C33 C33 C32 111.6(2) 3_666 . ?
C33 C33 H33A 109.3 3_666 . ?
C32 C33 H33A 109.3 . . ?
C33 C33 H33B 109.3 3_666 . ?
C32 C33 H33B 109.3 . . ?
H33A C33 H33B 108.0 . . ?
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 O11 1.4373(14) . ?
S11 O12 1.4453(13) . ?
S11 N12 1.6142(15) . ?
S11 C14 1.748(2) . ?
S12 C19 1.735(2) . ?
S12 C17 1.7356(17) . ?
N11 C11 1.362(3) . ?
N11 H10 0.825(17) . ?
N11 H11 0.834(17) . ?
N12 C17 1.322(2) . ?
N13 C17 1.344(2) . ?
N13 C18 1.381(2) . ?
N13 H17 0.86(2) . ?
C11 C16 1.399(3) . ?
C11 C12 1.409(3) . ?
C12 C13 1.371(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(2) . ?
C15 C16 1.382(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.331(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C31 1.140(3) . ?
C31 C32 1.464(3) . ?
C32 C33 1.527(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C33 1.517(4) 3_666 ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
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 O12 0.825(17) 2.292(19) 3.020(2) 147.5(19) 4_475 yes
N11 H11 N31 0.834(17) 2.330(18) 3.124(3) 159.3(19) 1_554 yes
N13 H17 O11 0.86(2) 2.63(2) 3.268(2) 132.2(18) 3_766 yes
N13 H17 N12 0.86(2) 2.06(2) 2.907(2) 167(2) 3_766 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
O11 S11 N12 C17 156.34(14) . . . . ?
O12 S11 N12 C17 26.93(17) . . . . ?
C14 S11 N12 C17 -89.71(15) . . . . ?
N11 C11 C12 C13 -178.99(18) . . . . ?
C16 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C12 C13 C14 S11 178.50(14) . . . . ?
O11 S11 C14 C13 34.05(16) . . . . ?
O12 S11 C14 C13 163.63(13) . . . . ?
N12 S11 C14 C13 -76.95(15) . . . . ?
O11 S11 C14 C15 -148.14(14) . . . . ?
O12 S11 C14 C15 -18.56(16) . . . . ?
N12 S11 C14 C15 100.86(15) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
S11 C14 C15 C16 -178.60(13) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
N11 C11 C16 C15 178.81(17) . . . . ?
C12 C11 C16 C15 0.6(3) . . . . ?
S11 N12 C17 N13 171.28(13) . . . . ?
S11 N12 C17 S12 -10.4(2) . . . . ?
C18 N13 C17 N12 178.31(16) . . . . ?
C18 N13 C17 S12 -0.34(19) . . . . ?
C19 S12 C17 N12 -178.78(18) . . . . ?
C19 S12 C17 N13 -0.31(14) . . . . ?
C17 N13 C18 C19 1.1(2) . . . . ?
N13 C18 C19 S12 -1.3(2) . . . . ?
C17 S12 C19 C18 0.92(17) . . . . ?
C31 C32 C33 C33 179.6(2) . . . 3_666 ?
