5-(4-Chlorophenyl)-3-hydroxy-4-methylthiazole-2(3<i>H</i>)-thione: an instance of bifurcated hydrogen bonding
Hartung, Jens; Gross, Andreas; Bergsträsser, Uwe; Acta Crystallographica Section E 63 (2007) o2743–o2745; doi:10.1107/S1600536807018016

data_2213563
_publ_section_title
;
 5-(4-Chlorophenyl)-3-hydroxy-4-methylthiazole-2(3<i>H</i>)-thione: an
 instance of bifurcated hydrogen bonding
;
_journal_coeditor_code           SJ2277
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2743
_journal_page_last               o2745
_journal_paper_doi               10.1107/S1600536807018016
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H8 Cl N O S2'
_chemical_formula_moiety         'C10 H8 Cl N O S2'
_chemical_formula_sum            'C10 H8 Cl N O S2'
_chemical_formula_weight         257.74
_chemical_name_systematic
;
5-(4-Chlorophenyl)-3-hydroxy-4-methylthiazole-2(3H)-thione:
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.34(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.843(2)
_cell_length_b                   14.707(3)
_cell_length_c                   15.312(3)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      24.05
_cell_measurement_theta_min      1.90
_cell_volume                     2214.7(8)
_computing_cell_refinement       'CELL in IPDS Software'
_computing_data_collection       'EXPOSE in IPDS Software (Stoe & Cie, 1998)'
_computing_data_reduction        'INTEGRATE in IPDS Software'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1994)'
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       \f
_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  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25254
_diffrn_reflns_theta_full        24.11
_diffrn_reflns_theta_max         24.11
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        0
_diffrn_standards_number         50
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.245
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0492P)^2^+0.4154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0824
_reflns_number_gt                3008
_reflns_number_total             3499
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sj2277.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2213563
_cod_database_fobs_code          2213563