5-{[5-(4-Chlorophenyl)-3-methyl-1<i>H</i>-pyrazol-1-yl]methyl}-1,3,4-oxadiazole-2(3<i>H</i>)-thione
Mague, Joel T.; Mohamed, Shaaban K.; Akkurt, Mehmet; Marzouk, Adel A.; Hawaiz, Farouq E.; Abdel-Rahman, Hamdy M.; IUCrData 2 (2017) x170176–; doi:10.1107/S2414314617001766

data_1545500
_publ_section_title
;
 5-{[5-(4-Chlorophenyl)-3-methyl-1<i>H</i>-pyrazol-1-yl]methyl}-1,3,4-oxadiazole-2(3<i>H</i>)-thione
;
_journal_coeditor_code           SU4127
_journal_issue                   2
_journal_name_full               IUCrData
_journal_page_first              x170176
_journal_paper_doi               10.1107/S2414314617001766
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C13 H11 Cl N4 O S'
_chemical_formula_moiety         'C13 H11 Cl N4 O S'
_chemical_formula_sum            'C13 H11 Cl N4 O S'
_chemical_formula_weight         306.77
_chemical_name_systematic
5-{[5-(4-Chlorophenyl)-3-methyl-1<i>H</i>-pyrazol-1-yl]methyl}-1,3,4-oxadiazole-2(3<i>H</i>)-thione
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.189(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9309(2)
_cell_length_b                   17.1173(8)
_cell_length_c                   16.6517(7)
_cell_measurement_reflns_used    4259
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      69.8991
_cell_measurement_theta_min      3.7037
_cell_volume                     1405.16(11)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>SAINT</i>  (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012) and Mercury (Macrae <i>et
al.</i>,  2008)
;
_computing_publication_material
;
<i>SHELXTL</i> (Sheldrick, 2008)
;
_computing_structure_refinement
;
<i>SHELXL2014</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10669
_diffrn_reflns_theta_full        70.100
_diffrn_reflns_theta_max         70.119
_diffrn_reflns_theta_min         3.704
_exptl_absorpt_coefficient_mu    3.809
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.489
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2632
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0681
_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^)+(0.1060P)^2^+0.4524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.1950
_reflns_number_gt                1759
_reflns_number_total             2632
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            su4127sup1.cif
_cod_data_source_block           I
_cod_database_code               1545500
_cod_database_fobs_code          1545500
_shelx_estimated_absorpt_t_min   0.510
_shelx_estimated_absorpt_t_max   0.917
_shelx_hkl_checksum              85016
_shelx_res_checksum              64380