#------------------------------------------------------------------------------
#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/23/8102306.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_8102306
loop_
_publ_author_name
'Qi-Chun Ding'
'Yu-Lin Huang'
'Miao-Chang Liu'
'Li-Xue Zhang'
'Chang-Feng Zhou'
'Xiao-Qing Cai'
_publ_section_title
;
 Crystal structure of
 4-amino-3-(4-ethoxyphenyl)-1H-1,2,4-triazole-5(4H)-thione, C10H12N4OS
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              289
_journal_volume                  223
_journal_year                    2008
_chemical_formula_moiety         'C10 H12 N4 O S'
_chemical_formula_sum            'C10 H12 N4 O S'
_chemical_formula_weight         236.30
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.7903(10)
_cell_length_b                   29.269(3)
_cell_length_c                   6.7927(6)
_cell_measurement_reflns_used    3504
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.83
_cell_measurement_theta_min      2.71
_cell_volume                     2344.1(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL(Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11329
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.9328
_exptl_absorpt_correction_T_min  0.8982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0083(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0508
_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)+(0.0413P)²+1.6540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                1891
_reflns_number_total             2062
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            1267-2309.cff
_cod_data_source_block           lx
_cod_original_cell_volume        2344.1(3)
_cod_database_code               8102306
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.08350(6) 0.29801(2) 0.24714(10) 0.0509(3) Uani 1 1 d . . .
O1 O 0.10648(19) -0.00813(6) 0.2357(3) 0.0653(6) Uani 1 1 d . . .
N1 N -0.13126(18) 0.18931(8) 0.2530(4) 0.0500(6) Uani 1 1 d . . .
N2 N -0.02153(16) 0.20781(6) 0.2363(3) 0.0390(5) Uani 1 1 d . . .
N3 N 0.11476(17) 0.25319(8) 0.1878(3) 0.0469(5) Uani 1 1 d . . .
N4 N 0.16078(17) 0.20989(7) 0.1806(3) 0.0473(6) Uani 1 1 d . . .
C1 C 0.00343(19) 0.25333(8) 0.2234(3) 0.0399(6) Uani 1 1 d . . .
C2 C 0.07466(19) 0.18262(8) 0.2085(3) 0.0402(6) Uani 1 1 d . . .
C3 C 0.08241(19) 0.13280(8) 0.2120(4) 0.0418(6) Uani 1 1 d . . .
C4 C 0.0259(2) 0.10726(9) 0.3538(4) 0.0505(7) Uani 1 1 d . . .
H4 H -0.0190 0.1219 0.4470 0.061 Uiso 1 1 calc R . .
C5 C 0.0361(2) 0.06052(9) 0.3570(4) 0.0553(7) Uani 1 1 d . . .
H5 H -0.0019 0.0437 0.4524 0.066 Uiso 1 1 calc R . .
C6 C 0.1027(2) 0.03839(9) 0.2192(4) 0.0494(6) Uani 1 1 d . . .
C7 C 0.1604(2) 0.06340(9) 0.0800(4) 0.0573(7) Uani 1 1 d . . .
H7 H 0.2063 0.0488 -0.0117 0.069 Uiso 1 1 calc R . .
C8 C 0.1497(2) 0.11051(9) 0.0773(4) 0.0538(7) Uani 1 1 d . . .
H8 H 0.1886 0.1274 -0.0171 0.065 Uiso 1 1 calc R . .
C9 C 0.1672(3) -0.03360(10) 0.0909(5) 0.0661(8) Uani 1 1 d . . .
H9A H 0.2470 -0.0255 0.0935 0.079 Uiso 1 1 calc R . .
H9B H 0.1376 -0.0271 -0.0394 0.079 Uiso 1 1 calc R . .
C10 C 0.1522(3) -0.08326(10) 0.1395(6) 0.0825(11) Uani 1 1 d . . .
H10A H 0.1842 -0.0894 0.2667 0.124 Uiso 1 1 calc R . .
H10B H 0.1898 -0.1015 0.0421 0.124 Uiso 1 1 calc R . .
H10C H 0.0728 -0.0906 0.1409 0.124 Uiso 1 1 calc R . .
H1B H -0.156(3) 0.1978(12) 0.364(6) 0.099 Uiso 1 1 d . . .
H1A H -0.170(3) 0.2024(12) 0.161(6) 0.099 Uiso 1 1 d . . .
H3 H 0.162(3) 0.2774(13) 0.180(6) 0.099 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
C6 O1 C9 118.7(2) . . ?
N2 N1 H1B 106(3) . . ?
N2 N1 H1A 105(3) . . ?
H1B N1 H1A 110(4) . . ?
C2 N2 C1 109.78(19) . . ?
C2 N2 N1 124.5(2) . . ?
C1 N2 N1 125.3(2) . . ?
C1 N3 N4 113.3(2) . . ?
C1 N3 H3 128(2) . . ?
N4 N3 H3 118(2) . . ?
C2 N4 N3 104.5(2) . . ?
N3 C1 N2 102.7(2) . . ?
N3 C1 S1 128.6(2) . . ?
N2 C1 S1 128.69(18) . . ?
N4 C2 N2 109.6(2) . . ?
N4 C2 C3 124.3(2) . . ?
N2 C2 C3 126.0(2) . . ?
C8 C3 C4 118.8(2) . . ?
C8 C3 C2 119.9(2) . . ?
C4 C3 C2 121.2(2) . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
O1 C6 C7 124.8(2) . . ?
O1 C6 C5 115.4(2) . . ?
C7 C6 C5 119.8(3) . . ?
C6 C7 C8 119.6(3) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C3 C8 C7 121.1(2) . . ?
C3 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
O1 C9 C10 107.1(3) . . ?
O1 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
O1 C9 H9B 110.3 . . ?
C10 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
S1 C1 1.670(3) . ?
O1 C6 1.367(3) . ?
O1 C9 1.427(3) . ?
N1 N2 1.407(3) . ?
N1 H1B 0.85(4) . ?
N1 H1A 0.87(4) . ?
N2 C2 1.366(3) . ?
N2 C1 1.367(3) . ?
N3 C1 1.335(3) . ?
N3 N4 1.379(3) . ?
N3 H3 0.90(4) . ?
N4 C2 1.305(3) . ?
C2 C3 1.461(3) . ?
C3 C8 1.376(4) . ?
C3 C4 1.389(3) . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(4) . ?
C7 C8 1.385(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.501(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
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
N1 H1B S1 0.85(4) 2.74(4) 3.424(3) 139(3) 7_566
N1 H1A S1 0.87(4) 2.96(4) 3.384(2) 112(3) 2_455
N1 H1A S1 0.87(4) 2.99(4) 3.502(3) 120(3) 7_565
N3 H3 N4 0.90(4) 2.12(4) 2.859(3) 138(3) 2
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
C1 N3 N4 C2 1.3(3) . . . . ?
N4 N3 C1 N2 -0.8(3) . . . . ?
N4 N3 C1 S1 178.92(18) . . . . ?
C2 N2 C1 N3 0.0(3) . . . . ?
N1 N2 C1 N3 -173.2(2) . . . . ?
C2 N2 C1 S1 -179.71(18) . . . . ?
N1 N2 C1 S1 7.1(3) . . . . ?
N3 N4 C2 N2 -1.2(3) . . . . ?
N3 N4 C2 C3 179.7(2) . . . . ?
C1 N2 C2 N4 0.8(3) . . . . ?
N1 N2 C2 N4 174.1(2) . . . . ?
C1 N2 C2 C3 179.8(2) . . . . ?
N1 N2 C2 C3 -6.9(4) . . . . ?
N4 C2 C3 C8 -41.5(4) . . . . ?
N2 C2 C3 C8 139.6(3) . . . . ?
N4 C2 C3 C4 136.3(3) . . . . ?
N2 C2 C3 C4 -42.7(4) . . . . ?
C8 C3 C4 C5 -0.9(4) . . . . ?
C2 C3 C4 C5 -178.7(2) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C9 O1 C6 C7 -5.0(4) . . . . ?
C9 O1 C6 C5 175.9(3) . . . . ?
C4 C5 C6 O1 -179.8(3) . . . . ?
C4 C5 C6 C7 1.0(4) . . . . ?
O1 C6 C7 C8 179.8(3) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C4 C3 C8 C7 0.8(4) . . . . ?
C2 C3 C8 C7 178.6(3) . . . . ?
C6 C7 C8 C3 0.2(4) . . . . ?
C6 O1 C9 C10 -177.1(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4143341
2 PubChem 4961992
