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#$Date: 2022-09-26 11:19:32 +0300 (Mon, 26 Sep 2022) $
#$Revision: 278166 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/58/8105861.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_8105861
loop_
_publ_author_name
'Yeo, Chien Ing'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione,
 C8H7N3S
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              819
_journal_page_last               820
_journal_paper_doi               10.1515/ncrs-2019-0128
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C8 H7 N3 S'
_chemical_formula_sum            'C8 H7 N3 S'
_chemical_formula_weight         177.23
_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
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 98.8710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.01550(10)
_cell_length_b                   14.10620(10)
_cell_length_c                   10.19900(10)
_cell_measurement_reflns_used    7111
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.8980
_cell_measurement_theta_min      5.3790
_cell_volume                     855.092(18)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL2018/3 [3]'
_computing_structure_refinement  'SHELXL2018/3 [3]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.5115
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9519
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         5.395
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.906
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.263
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1525
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0241
_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)+(0.0263P)²+0.4832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0609
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1477
_reflns_number_total             1525
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0128_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105861
_shelx_shelxl_version_number     2017/1
_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   0.536
_shelx_estimated_absorpt_t_max   0.711
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
S1 S 0.26316(5) 0.42759(2) -0.11406(3) 0.01791(11) Uani 1 1 d . . . . .
N1 N 0.17901(19) 0.43745(8) 0.13988(11) 0.0173(2) Uani 1 1 d D . . . .
H1N H 0.069(2) 0.4798(10) 0.1273(16) 0.026 Uiso 1 1 d D U . . .
N2 N 0.22991(19) 0.39594(8) 0.26285(11) 0.0219(3) Uani 1 1 d . . . . .
N3 N 0.42383(18) 0.33163(8) 0.11766(10) 0.0163(2) Uani 1 1 d . . . . .
C1 C 0.2907(2) 0.39986(9) 0.04831(13) 0.0153(3) Uani 1 1 d . . . . .
C2 C 0.3783(2) 0.33269(10) 0.24575(13) 0.0217(3) Uani 1 1 d . . . . .
H2 H 0.447849 0.291655 0.313813 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5751(2) 0.26640(9) 0.06913(12) 0.0165(3) Uani 1 1 d . . . . .
C4 C 0.5604(2) 0.17121(10) 0.10172(14) 0.0221(3) Uani 1 1 d . . . . .
H4 H 0.449929 0.150148 0.152328 0.027 Uiso 1 1 calc R U . . .
C5 C 0.7098(3) 0.10739(10) 0.05922(15) 0.0267(3) Uani 1 1 d . . . . .
H5 H 0.703335 0.042280 0.082143 0.032 Uiso 1 1 calc R U . . .
C6 C 0.8683(2) 0.13818(10) -0.01653(15) 0.0260(3) Uani 1 1 d . . . . .
H6 H 0.968920 0.094062 -0.046267 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8800(2) 0.23342(10) -0.04893(14) 0.0232(3) Uani 1 1 d . . . . .
H7 H 0.988158 0.254157 -0.101366 0.028 Uiso 1 1 calc R U . . .
C8 C 0.7345(2) 0.29868(9) -0.00521(13) 0.0187(3) Uani 1 1 d . . . . .
H8 H 0.744028 0.364092 -0.025813 0.022 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C1 N1 N2 113.69(11) . .
C1 N1 H1N 127.5(11) . .
N2 N1 H1N 118.4(11) . .
C2 N2 N1 103.42(10) . .
C2 N3 C1 107.17(11) . .
C2 N3 C3 124.36(11) . .
C1 N3 C3 128.40(11) . .
N1 C1 N3 103.48(11) . .
N1 C1 S1 127.51(10) . .
N3 C1 S1 128.96(10) . .
N2 C2 N3 112.24(12) . .
N2 C2 H2 123.9 . .
N3 C2 H2 123.9 . .
C8 C3 C4 121.49(12) . .
C8 C3 N3 120.42(12) . .
C4 C3 N3 118.06(12) . .
C5 C4 C3 118.98(13) . .
C5 C4 H4 120.5 . .
C3 C4 H4 120.5 . .
C6 C5 C4 120.32(13) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
C5 C6 C7 120.03(13) . .
C5 C6 H6 120.0 . .
C7 C6 H6 120.0 . .
C6 C7 C8 120.47(13) . .
C6 C7 H7 119.8 . .
C8 C7 H7 119.8 . .
C3 C8 C7 118.69(12) . .
C3 C8 H8 120.7 . .
C7 C8 H8 120.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.6847(13) .
N1 C1 1.3409(17) .
N1 N2 1.3752(16) .
N1 H1N 0.884(9) .
N2 C2 1.2927(18) .
N3 C2 1.3756(17) .
N3 C1 1.3760(16) .
N3 C3 1.4347(16) .
C2 H2 0.9500 .
C3 C8 1.3879(18) .
C3 C4 1.3893(19) .
C4 C5 1.388(2) .
C4 H4 0.9500 .
C5 C6 1.386(2) .
C5 H5 0.9500 .
C6 C7 1.388(2) .
C6 H6 0.9500 .
C7 C8 1.3901(19) .
C7 H7 0.9500 .
C8 H8 0.9500 .
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
C1 N1 N2 C2 0.92(15) . . . .
N2 N1 C1 N3 -1.20(14) . . . .
N2 N1 C1 S1 176.45(10) . . . .
C2 N3 C1 N1 0.99(14) . . . .
C3 N3 C1 N1 177.86(12) . . . .
C2 N3 C1 S1 -176.62(10) . . . .
C3 N3 C1 S1 0.3(2) . . . .
N1 N2 C2 N3 -0.22(15) . . . .
C1 N3 C2 N2 -0.50(16) . . . .
C3 N3 C2 N2 -177.52(12) . . . .
C2 N3 C3 C8 -132.95(14) . . . .
C1 N3 C3 C8 50.68(18) . . . .
C2 N3 C3 C4 45.40(18) . . . .
C1 N3 C3 C4 -130.97(14) . . . .
C8 C3 C4 C5 0.3(2) . . . .
N3 C3 C4 C5 -178.03(12) . . . .
C3 C4 C5 C6 -1.1(2) . . . .
C4 C5 C6 C7 0.8(2) . . . .
C5 C6 C7 C8 0.4(2) . . . .
C4 C3 C8 C7 0.9(2) . . . .
N3 C3 C8 C7 179.15(12) . . . .
C6 C7 C8 C3 -1.2(2) . . . .
