3-{[5-(4-Chlorophenyl)-3-methyl-1<i>H</i>-pyrazol-1-yl]methyl}-4-<i>m</i>-tolyl-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione
Farrukh, Muhammad A.; Ahmed, Maqsood; Mohamed, Shaaban K.; Marzouk, Adel A.; El-Moghazy, Samir M.; Acta Crystallographica Section E 69 (2013) o936–o937; doi:10.1107/S1600536813013494

data_2237848
_publ_section_title
;
 3-{[5-(4-Chlorophenyl)-3-methyl-1<i>H</i>-pyrazol-1-yl]methyl}-4-<i>m</i>-tolyl-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione
;
_journal_coeditor_code           GW2132
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o936
_journal_page_last               o937
_journal_paper_doi               10.1107/S1600536813013494
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C20 H18 Cl N5 S'
_chemical_formula_moiety         'C20 H18 Cl N5 S'
_chemical_formula_sum            'C20 H18 Cl N5 S'
_chemical_formula_weight         395.90
_chemical_name_systematic
3-{[5-(4-Chlorophenyl)-3-methyl-1<i>H</i>-pyrazol-1-yl]methyl}-4-<i>m</i>-tolyl-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione
_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                 99.509(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.328(5)
_cell_length_b                   16.407(5)
_cell_length_c                   14.759(5)
_cell_measurement_reflns_used    143
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      1.87
_cell_volume                     1988.9(15)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
and Mercury (Macrae <i>et al.</i>, 2008)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare <i>et al.</i>, 1993)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD detector'
_diffrn_measurement_method       '\w and \f scans'
_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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38237
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.87
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_T_max  0.8548
_exptl_absorpt_correction_T_min  0.8327
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '{SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.52
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+0.8662P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                3207
_reflns_number_total             3914
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gw2132.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2237848
_cod_database_fobs_code          2237848