#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/99/4509906.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_4509906
loop_
_publ_author_name
'Hu, Yun'
'Gniado, Katarzyna'
'Erxleben, Andrea'
'McArdle, Patrick'
_publ_section_title
;
 Mechanochemical Reaction of Sulfathiazole with Carboxylic Acids:
 Formation of a Cocrystal, a Salt, and Coamorphous Solids
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              803
_journal_paper_doi               10.1021/cg401673z
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C11 H11 N3 O6 S2'
_chemical_formula_weight         345.35
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 97.715(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0392(6)
_cell_length_b                   19.9339(10)
_cell_length_c                   8.6360(3)
_cell_measurement_reflns_used    1501
_cell_measurement_temperature    150.1(1)
_cell_measurement_theta_max      28.0730
_cell_measurement_theta_min      3.4080
_cell_volume                     1371.41(13)
_computing_cell_refinement
; 
'Wed Jun 26 21:22:31 2013' 
;
_computing_data_collection
; 
'Wed Jun 26 21:22:31 2013' 
;
_computing_data_reduction
; 
'Wed Jun 26 21:22:31 2013' 
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150.1(1)
_diffrn_detector_area_resol_mean 16.1048
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4727
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         3.137
_exptl_absorpt_coefficient_mu    0.423
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
'Wed Jun 26 21:22:31 2013' 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2510
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.211
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0399
_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)+(0.0596P)²+0.1566P] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1246
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2059
_reflns_number_total             2510
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            stz-oa.cif
_cod_data_source_block           stz-oa
_cod_database_code               4509906
#BEGIN Tags that were not found in dictionaries:
_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   0.913
_shelx_estimated_absorpt_t_max   0.967
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
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
S1 S 0.09993(8) 0.65673(4) 0.30783(8) 0.0196(2) Uani 1 1 d . .
S2 S 0.06511(10) 0.49450(4) 0.32142(9) 0.0261(2) Uani 1 1 d . .
O1 O 0.1878(3) 0.71961(10) 0.3072(3) 0.0292(5) Uani 1 1 d . .
O2 O 0.0913(2) 0.62492(10) 0.4570(2) 0.0248(5) Uani 1 1 d . .
N1 N -0.6058(3) 0.69814(12) 0.0084(3) 0.0201(5) Uani 1 1 d D .
H1N1 H -0.6724 0.6710 0.0540 0.026 Uiso 1 1 calc DR U
H2N1 H -0.6133 0.6882 -0.0927 0.026 Uiso 1 1 calc DR U
H3N1 H -0.6372 0.7405 0.0195 0.026 Uiso 1 1 calc DR U
N2 N 0.1797(3) 0.60970(12) 0.1863(3) 0.0184(5) Uani 1 1 d . .
N3 N 0.2167(3) 0.50377(11) 0.0844(3) 0.0187(5) Uani 1 1 d . .
H3 H 0.2669 0.5193 0.0101 0.024 Uiso 1 1 calc R U
O3 O 0.5003(3) 0.60871(10) -0.4940(2) 0.0269(5) Uani 1 1 d D .
H1O3 H 0.5069 0.5682 -0.5091 0.035 Uiso 1 1 calc DR U
O4 O 0.4282(3) 0.67556(10) -0.3114(2) 0.0259(5) Uani 1 1 d . .
O5 O 0.4337(3) 0.50177(10) -0.3345(2) 0.0287(5) Uani 1 1 d . .
O6 O 0.3675(3) 0.56642(10) -0.1362(2) 0.0289(5) Uani 1 1 d . .
C10 C 0.4469(4) 0.61916(14) -0.3585(3) 0.0208(6) Uani 1 1 d . .
C11 C 0.4123(4) 0.55577(15) -0.2670(3) 0.0218(6) Uani 1 1 d . .
C1 C -0.1093(3) 0.67163(13) 0.2224(3) 0.0165(6) Uani 1 1 d . .
C2 C -0.2361(3) 0.63083(13) 0.2640(3) 0.0172(6) Uani 1 1 d . .
H2A H -0.2121 0.5980 0.3402 0.022 Uiso 1 1 calc R U
C3 C -0.3991(3) 0.63964(13) 0.1906(3) 0.0165(6) Uani 1 1 d . .
H3A H -0.4848 0.6119 0.2153 0.021 Uiso 1 1 calc R U
C4 C -0.4327(3) 0.68953(13) 0.0814(3) 0.0161(6) Uani 1 1 d . .
C5 C -0.3079(4) 0.73063(14) 0.0393(3) 0.0229(7) Uani 1 1 d . .
H5 H -0.3335 0.7639 -0.0356 0.030 Uiso 1 1 calc R U
C6 C -0.1446(4) 0.72178(14) 0.1097(3) 0.0232(7) Uani 1 1 d . .
H6 H -0.0591 0.7489 0.0823 0.030 Uiso 1 1 calc R U
C7 C 0.1594(3) 0.54314(14) 0.1908(3) 0.0169(6) Uani 1 1 d . .
C8 C 0.1886(4) 0.43596(14) 0.1036(3) 0.0224(7) Uani 1 1 d . .
H8 H 0.2234 0.4031 0.0386 0.029 Uiso 1 1 calc R U
C9 C 0.1074(4) 0.42239(15) 0.2236(4) 0.0283(7) Uani 1 1 d . .
H9 H 0.0771 0.3795 0.2515 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
O1 S1 O2 117.89(13) . .
O1 S1 N2 105.47(13) . .
O2 S1 N2 113.44(12) . .
O1 S1 C1 106.97(13) . .
O2 S1 C1 106.78(12) . .
N2 S1 C1 105.46(12) . .
C9 S2 C7 90.87(14) . .
C4 N1 H1N1 109.5 . .
C4 N1 H2N1 109.5 . .
H1N1 N1 H2N1 109.5 . .
C4 N1 H3N1 109.5 . .
H1N1 N1 H3N1 109.5 . .
H2N1 N1 H3N1 109.5 . .
C7 N2 S1 119.96(19) . .
C7 N3 C8 114.4(2) . .
C7 N3 H3 122.8 . .
C8 N3 H3 122.8 . .
C10 O3 H1O3 109.5 . .
O6 O6 C11 0(10) 1 .
O4 C10 O3 121.0(3) . .
O4 C10 C11 123.5(3) . .
O3 C10 C11 115.5(2) . .
O5 C11 O6 130.1(3) . 1
O5 C11 O6 130.1(3) . .
O6 C11 O6 0.0(3) 1 .
O5 C11 C10 115.1(3) . .
O6 C11 C10 114.8(3) 1 .
O6 C11 C10 114.8(3) . .
C2 C1 C6 120.7(3) . .
C2 C1 S1 118.9(2) . .
C6 C1 S1 120.2(2) . .
C3 C2 C1 119.3(2) . .
C3 C2 H2A 120.4 . .
C1 C2 H2A 120.4 . .
C4 C3 C2 119.5(3) . .
C4 C3 H3A 120.2 . .
C2 C3 H3A 120.2 . .
C3 C4 C5 121.8(3) . .
C3 C4 N1 118.1(2) . .
C5 C4 N1 120.1(2) . .
C4 C5 C6 119.3(3) . .
C4 C5 H5 120.3 . .
C6 C5 H5 120.3 . .
C5 C6 C1 119.3(3) . .
C5 C6 H6 120.3 . .
C1 C6 H6 120.3 . .
N3 C7 N2 120.5(2) . .
N3 C7 S2 109.9(2) . .
N2 C7 S2 129.7(2) . .
C9 C8 N3 113.5(3) . .
C9 C8 H8 123.2 . .
N3 C8 H8 123.2 . .
C8 C9 S2 111.3(2) . .
C8 C9 H9 124.3 . .
S2 C9 H9 124.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.439(2) .
S1 O2 1.446(2) .
S1 N2 1.604(2) .
S1 C1 1.768(3) .
S2 C9 1.724(3) .
S2 C7 1.737(3) .
N1 C4 1.458(3) .
N1 H1N1 0.8900 .
N1 H2N1 0.8900 .
N1 H3N1 0.8900 .
N2 C7 1.338(4) .
N3 C7 1.337(3) .
N3 C8 1.384(3) .
N3 H3 0.8600 .
O3 C10 1.316(3) .
O3 H1O3 0.8200 .
O4 C10 1.212(3) .
O5 C11 1.247(3) .
O6 C11 1.249(3) .
C10 C11 1.535(4) .
C11 O6 1.249(3) 1
C1 C2 1.389(4) .
C1 C6 1.398(4) .
C2 C3 1.388(4) .
C2 H2A 0.9300 .
C3 C4 1.373(4) .
C3 H3A 0.9300 .
C4 C5 1.381(4) .
C5 C6 1.382(4) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C8 C9 1.325(4) .
C8 H8 0.9300 .
C9 H9 0.9300 .
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
N3 H3 O6 0.86 1.85 2.697(3) 170.5 1
N1 H2N1 O4 0.89 1.98 2.847(3) 165.4 1_455
N1 H3N1 O4 0.89 2.24 2.953(3) 137.3 2_465
N1 H1N1 N2 0.89 2.14 3.025(3) 174.1 1_455
O3 H1O3 O5 0.82 2.04 2.745(3) 143.4 3_664
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_4
O1 S1 N2 C7 161.6(2) . .
O2 S1 N2 C7 31.1(2) . .
C1 S1 N2 C7 -85.4(2) . .
O6 O6 C11 O5 0.0(2) 1 .
O6 O6 C11 C10 0.0(3) 1 .
O4 C10 C11 O5 178.1(3) . .
O3 C10 C11 O5 -2.3(4) . .
O4 C10 C11 O6 -2.1(4) . 1
O3 C10 C11 O6 177.6(3) . 1
O4 C10 C11 O6 -2.1(4) . .
O3 C10 C11 O6 177.6(3) . .
O1 S1 C1 C2 -153.3(2) . .
O2 S1 C1 C2 -26.2(2) . .
N2 S1 C1 C2 94.8(2) . .
O1 S1 C1 C6 29.6(3) . .
O2 S1 C1 C6 156.6(2) . .
N2 S1 C1 C6 -82.4(2) . .
C6 C1 C2 C3 0.9(4) . .
S1 C1 C2 C3 -176.2(2) . .
C1 C2 C3 C4 -1.7(4) . .
C2 C3 C4 C5 1.5(4) . .
C2 C3 C4 N1 -179.0(2) . .
C3 C4 C5 C6 -0.5(4) . .
N1 C4 C5 C6 180.0(3) . .
C4 C5 C6 C1 -0.3(4) . .
C2 C1 C6 C5 0.0(4) . .
S1 C1 C6 C5 177.1(2) . .
C8 N3 C7 N2 179.5(2) . .
C8 N3 C7 S2 -0.2(3) . .
S1 N2 C7 N3 176.04(19) . .
S1 N2 C7 S2 -4.3(3) . .
C9 S2 C7 N3 -0.3(2) . .
C9 S2 C7 N2 -180.0(3) . .
C7 N3 C8 C9 0.9(4) . .
N3 C8 C9 S2 -1.1(3) . .
C7 S2 C9 C8 0.8(3) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139147060
