#------------------------------------------------------------------------------
#$Date: 2022-09-08 01:46:06 +0300 (Thu, 08 Sep 2022) $
#$Revision: 277721 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/54/7245454.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_7245454
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: hydrogen-bond
 topology and node shape
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00964A
_journal_year                    2022
_chemical_formula_moiety         'C9 H8 N3 O2 S2 -, C H6 N3 +, H2 O'
_chemical_formula_sum            'C10 H16 N6 O3 S2'
_chemical_formula_weight         332.41
_chemical_name_common            'Sulfathiazole guanidinium hydrate'
_chemical_name_systematic        'Sulfathiazole guanidinium hydrate (1:1:1)'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2022-07-11 deposited with the CCDC.	2022-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                101.353(2)
_cell_angle_beta                 92.999(3)
_cell_angle_gamma                97.446(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6295(2)
_cell_length_b                   8.7769(5)
_cell_length_c                   11.3046(6)
_cell_measurement_reflns_used    9430
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.27
_cell_measurement_theta_min      3.15
_cell_volume                     733.56(6)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0468
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9430
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        23.274
_diffrn_reflns_theta_max         23.274
_diffrn_reflns_theta_min         3.146
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0270
_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)+(0.0308P)²+0.4060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0706
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2007
_reflns_number_total             2107
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00964a7.cif
_cod_data_source_block           96
_cod_database_code               7245454
_shelx_shelxl_version_number     2019/1
_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   0.878
_shelx_estimated_absorpt_t_max   0.927
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
S11 S 0.69622(5) 0.60268(5) 0.73942(4) 0.01612(15) Uani 1 1 d . . . . .
S12 S 0.39916(6) 0.82030(5) 0.83581(4) 0.02322(16) Uani 1 1 d . . . . .
O11 O 0.81589(16) 0.52410(13) 0.65902(10) 0.0210(3) Uani 1 1 d . . . . .
O12 O 0.52556(15) 0.50883(13) 0.74159(11) 0.0217(3) Uani 1 1 d . . . . .
N11 N 1.0450(2) 0.74728(19) 1.23925(14) 0.0212(4) Uani 1 1 d . . . . .
H10 H 1.036(3) 0.668(3) 1.274(2) 0.031(6) Uiso 1 1 d . . . . .
H11 H 1.147(3) 0.810(3) 1.2502(19) 0.031(6) Uiso 1 1 d . . . . .
N12 N 0.68667(18) 0.76371(16) 0.69886(12) 0.0171(3) Uani 1 1 d . . . . .
N13 N 0.61478(19) 1.01810(16) 0.75340(13) 0.0205(3) Uani 1 1 d . . . . .
C11 C 0.9660(2) 0.70958(19) 1.12157(15) 0.0170(4) Uani 1 1 d . . . . .
C12 C 1.0241(2) 0.7961(2) 1.03563(16) 0.0188(4) Uani 1 1 d . . . . .
H12 H 1.121778 0.877838 1.057008 0.023 Uiso 1 1 calc R U . . .
C13 C 0.9411(2) 0.76379(19) 0.92049(16) 0.0183(4) Uani 1 1 d . . . . .
H13 H 0.981716 0.823046 0.862938 0.022 Uiso 1 1 calc R U . . .
C14 C 0.7978(2) 0.64455(19) 0.88836(15) 0.0167(4) Uani 1 1 d . . . . .
C15 C 0.7389(2) 0.5575(2) 0.97253(16) 0.0193(4) Uani 1 1 d . . . . .
H15 H 0.641355 0.475750 0.950625 0.023 Uiso 1 1 calc R U . . .
C16 C 0.8221(2) 0.5900(2) 1.08803(16) 0.0199(4) Uani 1 1 d . . . . .
H16 H 0.781045 0.530328 1.145239 0.024 Uiso 1 1 calc R U . . .
C17 C 0.5835(2) 0.8688(2) 0.75731(15) 0.0167(4) Uani 1 1 d . . . . .
C18 C 0.4906(2) 1.0986(2) 0.81351(16) 0.0237(4) Uani 1 1 d . . . . .
H18 H 0.492241 1.208158 0.818645 0.028 Uiso 1 1 calc R U . . .
C19 C 0.3677(2) 1.0145(2) 0.86417(16) 0.0246(4) Uani 1 1 d . . . . .
H19 H 0.276639 1.055881 0.909117 0.029 Uiso 1 1 calc R U . . .
N21 N 0.7230(2) 0.0820(2) 0.46600(15) 0.0218(4) Uani 1 1 d . . . . .
H21 H 0.699(3) -0.013(3) 0.4516(19) 0.029(6) Uiso 1 1 d . . . . .
H22 H 0.649(3) 0.136(3) 0.4959(19) 0.026(6) Uiso 1 1 d . . . . .
N22 N 0.9029(2) 0.30667(18) 0.45130(16) 0.0259(4) Uani 1 1 d . . . . .
H23 H 0.835(3) 0.358(3) 0.494(2) 0.035(6) Uiso 1 1 d . . . . .
H24 H 0.988(3) 0.351(2) 0.4162(19) 0.029(6) Uiso 1 1 d . . . . .
N23 N 0.9762(2) 0.0678(2) 0.36416(14) 0.0214(4) Uani 1 1 d . . . . .
H25 H 1.078(3) 0.114(3) 0.3467(19) 0.030(6) Uiso 1 1 d . . . . .
H26 H 0.953(3) -0.032(3) 0.3413(19) 0.028(6) Uiso 1 1 d . . . . .
C21 C 0.8657(2) 0.1507(2) 0.42661(15) 0.0177(4) Uani 1 1 d . . . . .
O1W O 0.42345(18) 0.24338(16) 0.55034(14) 0.0259(3) Uani 1 1 d . . . . .
H1W H 0.387(3) 0.266(3) 0.487(3) 0.048(8) Uiso 1 1 d . . . . .
H2W H 0.438(3) 0.328(3) 0.604(2) 0.041(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'
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 114.16(7) . . ?
O12 S11 N12 114.83(7) . . ?
O11 S11 N12 104.79(7) . . ?
O12 S11 C14 106.80(8) . . ?
O11 S11 C14 108.04(7) . . ?
N12 S11 C14 107.93(8) . . ?
C19 S12 C17 89.20(9) . . ?
C11 N11 H10 112.5(14) . . ?
C11 N11 H11 115.6(14) . . ?
H10 N11 H11 118(2) . . ?
C17 N12 S11 120.10(12) . . ?
C17 N13 C18 110.31(15) . . ?
N11 C11 C16 120.87(16) . . ?
N11 C11 C12 120.44(16) . . ?
C16 C11 C12 118.63(16) . . ?
C13 C12 C11 120.66(16) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.11(16) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.88(16) . . ?
C15 C14 S11 120.80(13) . . ?
C13 C14 S11 119.30(13) . . ?
C16 C15 C14 120.02(16) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 120.70(16) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
N13 C17 N12 120.67(15) . . ?
N13 C17 S12 113.82(13) . . ?
N12 C17 S12 125.46(13) . . ?
C19 C18 N13 116.68(16) . . ?
C19 C18 H18 121.7 . . ?
N13 C18 H18 121.7 . . ?
C18 C19 S12 109.99(14) . . ?
C18 C19 H19 125.0 . . ?
S12 C19 H19 125.0 . . ?
C21 N21 H21 120.6(15) . . ?
C21 N21 H22 119.3(14) . . ?
H21 N21 H22 119(2) . . ?
C21 N22 H23 117.7(15) . . ?
C21 N22 H24 118.9(14) . . ?
H23 N22 H24 123(2) . . ?
C21 N23 H25 120.5(14) . . ?
C21 N23 H26 121.4(14) . . ?
H25 N23 H26 118(2) . . ?
N21 C21 N23 121.42(17) . . ?
N21 C21 N22 119.85(17) . . ?
N23 C21 N22 118.71(17) . . ?
H1W O1W H2W 106(2) . . ?
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 1.4519(12) . ?
S11 O11 1.4624(12) . ?
S11 N12 1.5784(14) . ?
S11 C14 1.7654(17) . ?
S12 C19 1.7217(18) . ?
S12 C17 1.7523(17) . ?
N11 C11 1.391(2) . ?
N11 H10 0.86(2) . ?
N11 H11 0.88(2) . ?
N12 C17 1.382(2) . ?
N13 C17 1.311(2) . ?
N13 C18 1.382(2) . ?
C11 C16 1.397(2) . ?
C11 C12 1.402(3) . ?
C12 C13 1.378(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C15 C16 1.382(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.340(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N21 C21 1.317(2) . ?
N21 H21 0.81(2) . ?
N21 H22 0.83(2) . ?
N22 C21 1.332(2) . ?
N22 H23 0.84(2) . ?
N22 H24 0.87(2) . ?
N23 C21 1.326(2) . ?
N23 H25 0.88(2) . ?
N23 H26 0.85(2) . ?
O1W H1W 0.82(3) . ?
O1W H2W 0.85(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
_geom_hbond_publ_flag
N11 H10 O11 0.86(2) 2.37(2) 3.1189(19) 146.4(18) 2_767 yes
N11 H11 N13 0.88(2) 2.22(2) 3.084(2) 169.1(19) 2_777 yes
N21 H21 O1W 0.81(2) 2.11(2) 2.895(2) 162(2) 2_656 yes
N21 H22 O1W 0.83(2) 2.13(2) 2.945(2) 169(2) . yes
N22 H23 O11 0.84(2) 2.15(2) 2.885(2) 145(2) . yes
N22 H24 O11 0.87(2) 2.06(2) 2.924(2) 174.6(19) 2_766 yes
N23 H25 N12 0.88(2) 2.11(2) 2.988(2) 176.3(19) 2_766 yes
N23 H26 N11 0.85(2) 2.27(2) 3.013(2) 145.7(18) 1_544 yes
O1W H1W N12 0.82(3) 2.10(3) 2.884(2) 158(2) 2_666 yes
O1W H2W S11 0.85(3) 3.00(3) 3.7449(15) 146.2(19) . yes
O1W H2W O12 0.85(3) 2.01(3) 2.8424(19) 166(2) . 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 54.07(14) . . . . ?
O11 S11 N12 C17 -179.87(12) . . . . ?
C14 S11 N12 C17 -64.90(14) . . . . ?
N11 C11 C12 C13 -177.07(15) . . . . ?
C16 C11 C12 C13 0.0(2) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
C12 C13 C14 S11 -178.76(13) . . . . ?
O12 S11 C14 C15 17.50(16) . . . . ?
O11 S11 C14 C15 -105.73(14) . . . . ?
N12 S11 C14 C15 141.46(14) . . . . ?
O12 S11 C14 C13 -164.00(13) . . . . ?
O11 S11 C14 C13 72.77(14) . . . . ?
N12 S11 C14 C13 -40.04(15) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
S11 C14 C15 C16 178.77(12) . . . . ?
C14 C15 C16 C11 -0.2(2) . . . . ?
N11 C11 C16 C15 177.09(15) . . . . ?
C12 C11 C16 C15 0.0(2) . . . . ?
C18 N13 C17 N12 177.38(14) . . . . ?
C18 N13 C17 S12 -0.14(18) . . . . ?
S11 N12 C17 N13 158.25(13) . . . . ?
S11 N12 C17 S12 -24.54(19) . . . . ?
C19 S12 C17 N13 -0.44(13) . . . . ?
C19 S12 C17 N12 -177.81(15) . . . . ?
C17 N13 C18 C19 0.9(2) . . . . ?
N13 C18 C19 S12 -1.2(2) . . . . ?
C17 S12 C19 C18 0.89(14) . . . . ?
