4-[(5-Chloro-2-hydroxybenzylidene)amino]-3-ethyl-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione
Yuan, Cai-Xia; Yao, Xu-Mei; Zhu, Miao-Li; Zhu, Hong-Mei; Acta Crystallographica Section E 70 (2014) o574–o575; doi:10.1107/S1600536814008320

data_2239369
_publ_section_title
;
 4-[(5-Chloro-2-hydroxybenzylidene)amino]-3-ethyl-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione
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_journal_coeditor_code           HB7205
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o574
_journal_page_last               o575
_journal_paper_doi               10.1107/S1600536814008320
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C11 H11 Cl N4 O S'
_chemical_formula_moiety         'C11 H11 Cl N4 O S'
_chemical_formula_sum            'C11 H11 Cl N4 O S'
_chemical_formula_weight         282.75
_chemical_name_systematic
4-[(5-Chloro-2-hydroxybenzylidene)amino]-3-ethyl-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 90.997(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.297(3)
_cell_length_b                   16.418(8)
_cell_length_c                   12.290(6)
_cell_measurement_reflns_used    1893
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.69
_cell_measurement_theta_min      2.48
_cell_volume                     1270.4(11)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '\w 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  0.0600
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14098
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.458
_exptl_absorpt_correction_T_max  0.9345
_exptl_absorpt_correction_T_min  0.9140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.274
_refine_ls_abs_structure_details 'Flack (1983), 2274 Friedel pairs'
_refine_ls_abs_structure_Flack   0.03(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         2451
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0368
_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/[\s^2^(Fo^2^)+(0.0375P)^2^+0.1830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0841
_reflns_number_gt                1924
_reflns_number_total             2451
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            hb7205sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1270.2(10)
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               2239369
_cod_database_fobs_code          2239369