Crystal structure of 5-(4-fluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C9H8FN3S
Aouad, Mohamed Reda; Messali, Mouslim; Alharbi, Khalid; Rezki, Nadjet; Zarrouk, Abdelkader; Warad, Ismail; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 345–346; doi:10.1515/ncrs-2018-0406

data_8105640
_publ_section_title
;
 Crystal structure of
 5-(4-fluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione,
 C9H8FN3S
;
_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              345
_journal_page_last               346
_journal_paper_doi               10.1515/ncrs-2018-0406
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C9 H8 F N3 S'
_chemical_formula_sum            'C9 H8 F N3 S'
_chemical_formula_weight         209.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 106.016(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8636(6)
_cell_length_b                   7.6641(3)
_cell_length_c                   16.4472(7)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.67
_cell_measurement_theta_min      6.55
_cell_volume                     1922.04(13)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker X8 PROSPECTOR APEX2 CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19511
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        66.672
_diffrn_reflns_theta_max         66.672
_diffrn_reflns_theta_min         3.427
_exptl_absorpt_coefficient_mu    2.831
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0348
_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/[\s^2^(Fo^2^)+(0.0621P)^2^+0.4155P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3170
_reflns_number_total             3320
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2018-0406_suppl.cif
_cod_data_source_block           1
_cod_depositor_comments
;

2025-04-22
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C18 H16 F2 N6 S2'
_cod_original_formula_weight         418.49
_cod_original_formula_moiety         '2(C9 H8 F N3 S)'
_cod_original_formula_units_Z            4
_cod_database_code               8105640
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2B(H2B), C4B(H4B), C5B(H5B), C7B(H7B), C8B(H8B), N2A(H2A), C4A(H4A),
 C5A(H5A), C7A(H7A), C8A(H8A)
2.b Idealised Me refined as rotating group:
 C9B(H9BA,H9BB,H9BC), C9A(H9AA,H9AB,H9AC)
;