#------------------------------------------------------------------------------
#$Date: 2025-08-21 04:34:05 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/05/4510523.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_4510523
loop_
_publ_author_name
'Phukan, Nithi'
'Baruah, Jubaraj B.'
_publ_section_title
;
 Polymorphs of 1-(5-Methylthiazol-2-yl)-3-phenylthiourea and Various
 Anion-Assisted Assemblies of Two Positional Isomers
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2640
_journal_paper_doi               10.1021/cg5003379
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C11 H12 N4 O3 S2'
_chemical_formula_weight         312.39
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.005(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.2755(8)
_cell_length_b                   18.3129(14)
_cell_length_c                   14.0015(10)
_cell_measurement_temperature    296(2)
_cell_volume                     2817.0(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_av_sigmaI/netI    0.0988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28852
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.390
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         4899
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1479
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+1.9000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0873
_reflns_number_gt                2500
_reflns_number_total             4899
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            3b.cif
_cod_data_source_block           3b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4510508--4510523.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               4510523
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
_atom_site_refinement_flags
S1 S 0.73680(10) 0.19890(5) 0.83531(8) 0.0590(3) Uani 1 1 d .
S3 S 0.16480(11) 0.39259(7) 0.63528(8) 0.0692(4) Uani 1 1 d .
S4 S 0.16578(12) 0.26406(6) 0.76703(9) 0.0771(4) Uani 1 1 d .
S2 S 0.64511(12) 0.28166(6) 0.98872(9) 0.0800(4) Uani 1 1 d .
C6 C 0.6645(3) 0.4544(2) 1.0544(3) 0.0425(10) Uani 1 1 d .
C11 C 0.6490(4) 0.5292(3) 1.0490(3) 0.0524(12) Uani 1 1 d .
C10 C 0.6000(4) 0.5660(3) 1.1171(4) 0.0623(13) Uani 1 1 d D
C7 C 0.6348(4) 0.4171(3) 1.1314(3) 0.0645(14) Uani 1 1 d .
C5 C 0.6987(3) 0.3536(2) 0.9428(3) 0.0474(11) Uani 1 1 d .
C8 C 0.5845(5) 0.4553(4) 1.1982(4) 0.0760(16) Uani 1 1 d .
C9 C 0.5665(5) 0.5286(4) 1.1914(4) 0.0714(15) Uani 1 1 d .
C4 C 0.7546(3) 0.2875(2) 0.8058(3) 0.0438(10) Uani 1 1 d .
C2 C 0.8156(3) 0.2280(3) 0.6814(3) 0.0490(11) Uani 1 1 d .
C3 C 0.7893(4) 0.1725(3) 0.7338(3) 0.0594(14) Uani 1 1 d .
C1 C 0.8622(3) 0.2288(2) 0.5899(3) 0.0637(12) Uani 1 1 d .
H1A H 0.8747 0.1796 0.5708 0.095 Uiso 1 1 calc R
H1B H 0.9379 0.2549 0.6014 0.095 Uiso 1 1 calc R
H1C H 0.8039 0.2524 0.5386 0.095 Uiso 1 1 calc R
C17 C 0.0508(4) 0.2395(3) 0.9650(3) 0.0551(12) Uani 1 1 d .
C21 C -0.0230(5) 0.1846(4) 1.0951(4) 0.0796(16) Uani 1 1 d .
C18 C 0.0719(5) 0.1716(3) 0.9318(4) 0.0776(16) Uani 1 1 d .
C22 C 0.0040(4) 0.2467(3) 1.0476(4) 0.0673(14) Uani 1 1 d .
C19 C 0.0447(6) 0.1103(3) 0.9808(5) 0.0958(19) Uani 1 1 d .
C20 C -0.0046(6) 0.1171(4) 1.0611(5) 0.0891(19) Uani 1 1 d .
C16 C 0.1085(3) 0.3203(2) 0.8362(3) 0.0469(11) Uani 1 1 d .
C15 C 0.1163(3) 0.4280(3) 0.7326(3) 0.0453(11) Uani 1 1 d .
C13 C 0.1168(4) 0.5293(3) 0.6355(3) 0.0579(12) Uani 1 1 d .
C14 C 0.1544(4) 0.4782(3) 0.5821(4) 0.0698(16) Uani 1 1 d .
C12 C 0.0935(4) 0.6082(2) 0.6163(3) 0.0851(15) Uani 1 1 d .
H12A H 0.1081 0.6204 0.5533 0.128 Uiso 1 1 calc R
H12B H 0.1469 0.6362 0.6660 0.128 Uiso 1 1 calc R
H12C H 0.0105 0.6191 0.6173 0.128 Uiso 1 1 calc R
N7 N 0.5647(3) 0.0400(2) 0.5997(2) 0.0506(10) Uani 1 1 d .
N8 N 0.7240(4) 0.9797(2) 0.8293(3) 0.0550(10) Uani 1 1 d .
N4 N 0.0968(3) 0.4991(2) 0.7220(3) 0.0475(10) Uani 1 1 d .
N6 N 0.0714(3) 0.3058(2) 0.9191(3) 0.0554(10) Uani 1 1 d D
N5 N 0.0941(3) 0.3937(2) 0.8125(3) 0.0483(9) Uani 1 1 d D
N3 N 0.7116(3) 0.4218(2) 0.9786(2) 0.0477(9) Uani 1 1 d D
N2 N 0.7377(3) 0.34897(19) 0.8553(3) 0.0502(9) Uani 1 1 d D
N1 N 0.7954(3) 0.2940(2) 0.7245(3) 0.0471(9) Uani 1 1 d D
O6 O 0.7913(3) 0.97200(14) 0.7705(2) 0.0649(9) Uani 1 1 d .
O5 O 0.6653(2) 0.92644(15) 0.85235(19) 0.0617(8) Uani 1 1 d .
O4 O 0.7124(3) 1.04011(16) 0.8642(2) 0.0975(12) Uani 1 1 d .
O3 O 0.6328(3) 0.07165(15) 0.5543(2) 0.0657(9) Uani 1 1 d .
O2 O 0.4877(3) 0.07516(15) 0.6329(2) 0.0716(9) Uani 1 1 d .
O1 O 0.5728(2) -0.02772(16) 0.61137(18) 0.0597(8) Uani 1 1 d .
H3 H 0.796(3) 0.1238(17) 0.722(2) 0.043(12) Uiso 1 1 d .
H2 H 0.743(3) 0.3884(11) 0.8231(19) 0.037(12) Uiso 1 1 d D
H3A H 0.751(3) 0.4518(15) 0.951(2) 0.047(14) Uiso 1 1 d D
H1 H 0.808(3) 0.3363(13) 0.698(2) 0.060(15) Uiso 1 1 d D
H11 H 0.668(2) 0.5544(15) 0.994(2) 0.027(10) Uiso 1 1 d .
H9 H 0.534(3) 0.556(2) 1.240(3) 0.080(16) Uiso 1 1 d .
H8 H 0.559(3) 0.4234(19) 1.247(3) 0.072(14) Uiso 1 1 d .
H7 H 0.649(3) 0.3644(19) 1.137(2) 0.065(14) Uiso 1 1 d .
H18 H 0.113(3) 0.1670(18) 0.874(2) 0.062(13) Uiso 1 1 d .
H20 H -0.023(4) 0.072(2) 1.089(3) 0.11(2) Uiso 1 1 d .
H19 H 0.053(4) 0.063(3) 0.949(4) 0.14(2) Uiso 1 1 d .
H22 H -0.009(3) 0.294(2) 1.069(3) 0.067(15) Uiso 1 1 d .
H6 H 0.061(3) 0.3446(13) 0.951(2) 0.045(13) Uiso 1 1 d D
H5 H 0.050(3) 0.4212(16) 0.842(2) 0.051(14) Uiso 1 1 d D
H4 H 0.066(3) 0.5274(19) 0.761(3) 0.059(15) Uiso 1 1 d .
H10 H 0.588(3) 0.6176(11) 1.110(2) 0.056(14) Uiso 1 1 d D
H14 H 0.176(4) 0.485(2) 0.524(3) 0.090(17) Uiso 1 1 d .
H21 H -0.058(3) 0.1965(19) 1.153(3) 0.073(15) 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'
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'
H H 0.0000 0.0000 '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
C4 S1 C3 89.2(2)
C15 S3 C14 89.8(3)
C7 C6 C11 119.0(4)
C7 C6 N3 125.0(4)
C11 C6 N3 116.0(4)
C10 C11 C6 120.8(5)
C9 C10 C11 120.3(5)
C6 C7 C8 119.0(5)
N3 C5 N2 110.9(3)
N3 C5 S2 128.3(3)
N2 C5 S2 120.8(3)
C9 C8 C7 121.9(5)
C8 C9 C10 119.0(5)
N1 C4 N2 118.6(3)
N1 C4 S1 112.2(3)
N2 C4 S1 129.1(3)
C3 C2 N1 110.3(4)
C3 C2 C1 130.5(4)
N1 C2 C1 119.2(4)
C2 C3 S1 113.7(3)
C18 C17 C22 120.1(5)
C18 C17 N6 124.5(5)
C22 C17 N6 115.5(4)
C20 C21 C22 120.8(6)
C17 C18 C19 119.5(6)
C17 C22 C21 119.3(5)
C20 C19 C18 120.7(6)
C21 C20 C19 119.6(6)
N6 C16 N5 110.8(4)
N6 C16 S4 128.7(4)
N5 C16 S4 120.5(3)
N4 C15 N5 119.5(4)
N4 C15 S3 111.0(4)
N5 C15 S3 129.5(4)
C14 C13 N4 110.0(5)
C14 C13 C12 130.7(5)
N4 C13 C12 119.2(4)
C13 C14 S3 113.4(4)
O3 N7 O2 120.7(4)
O3 N7 O1 119.5(4)
O2 N7 O1 119.8(4)
O4 N8 O6 119.9(4)
O4 N8 O5 119.0(4)
O6 N8 O5 121.0(4)
C15 N4 C13 115.7(4)
C16 N6 C17 132.4(4)
C15 N5 C16 127.9(4)
C5 N3 C6 130.0(4)
C4 N2 C5 127.4(4)
C4 N1 C2 114.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.698(4)
S1 C3 1.727(4)
S3 C15 1.707(4)
S3 C14 1.728(5)
S4 C16 1.642(4)
S2 C5 1.640(4)
C6 C7 1.379(5)
C6 C11 1.382(5)
C6 N3 1.421(4)
C11 C10 1.379(5)
C10 C9 1.368(6)
C7 C8 1.387(6)
C5 N3 1.342(4)
C5 N2 1.395(4)
C8 C9 1.359(6)
C4 N1 1.326(4)
C4 N2 1.357(4)
C2 C3 1.327(5)
C2 N1 1.392(5)
C2 C1 1.490(5)
C17 C18 1.367(5)
C17 C22 1.382(6)
C17 N6 1.418(5)
C21 C20 1.358(7)
C21 C22 1.385(6)
C18 C19 1.385(6)
C19 C20 1.366(7)
C16 N6 1.345(5)
C16 N5 1.386(4)
C15 N4 1.322(5)
C15 N5 1.354(5)
C13 C14 1.326(6)
C13 N4 1.396(5)
C13 C12 1.481(5)
N7 O3 1.244(4)
N7 O2 1.251(4)
N7 O1 1.252(4)
N8 O4 1.229(4)
N8 O6 1.248(4)
N8 O5 1.260(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139147242
