Thionordazepam: strong intermolecular N—H···N hydrogen-bonded chains
Narasegowda, R. S.; Vijaya, T.; Yathirajan, H. S.; Nagaraja, P.; Narasimhamurthy, T.; Rathore, R. S.; Acta Crystallographica Section E 61 (2005) o2934–o2936; doi:10.1107/S1600536805025286

data_2206657
_publ_section_title
;
 Thionordazepam: strong intermolecular N---H&#x00B7;&#x00B7;&#x00B7;N
 hydrogen-bonded chains
;
_journal_coeditor_code           CI6627
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2934
_journal_page_last               o2936
_journal_paper_doi               10.1107/S1600536805025286
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C15 H11 Cl1 N2 S1'
_chemical_formula_moiety         'C15 H11 Cl1 N2 S1'
_chemical_formula_sum            'C15 H11 Cl N2 S'
_chemical_formula_weight         286.77
_chemical_melting_point          489
_chemical_name_common            Thionordazepam
_chemical_name_systematic
;
7-Chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-thione
;
_space_group_IT_number           30
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 -2bc'
_symmetry_space_group_name_H-M   'P n c 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.993(2)
_cell_length_b                   14.223(3)
_cell_length_c                   10.175(2)
_cell_measurement_reflns_used    1456
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35
_cell_measurement_theta_min      5
_cell_volume                     1446.2(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL  (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       \w
_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  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0786
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10960
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.37
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Thin-plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.148
_refine_ls_abs_structure_details 'Flack (1983), 1358 Friedel pairs'
_refine_ls_abs_structure_Flack   0.42(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3021
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1507
_refine_ls_R_factor_gt           0.0615
_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^)+(0.0619P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1416
_reflns_number_gt                1505
_reflns_number_total             3021
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ci6627.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C15 H11 Cl1 N2 S1'
_cod_database_code               2206657
_cod_database_fobs_code          2206657