#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/53/2215396.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2215396
loop_
_publ_author_name
'Sadr, Moayad Hossaini '
'Khalilizadeh, Zahra '
'Tiekink, Edward R. T.'
_publ_section_title
;
 N-Phenylindazole-1-thiocarboxamide
;
_journal_coeditor_code           BV2071
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4126
_journal_page_last               o4126
_journal_paper_doi               10.1107/S1600536807045734
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H11 N3 S'
_chemical_formula_moiety         'C14 H11 N3 S'
_chemical_formula_sum            'C14 H11 N3 S'
_chemical_formula_weight         253.32
_chemical_name_systematic
;
N-Phenylindazole-1-thiocarboxamide
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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
_cell_angle_beta                 121.110(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.408(8)
_cell_length_b                   5.690(2)
_cell_length_c                   11.949(5)
_cell_measurement_reflns_used    5144
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      29.6
_cell_measurement_theta_min      3.4
_cell_volume                     1188.0(8)
_computing_cell_refinement
'CrystalClear (Rigaku Americas Corporation, 2005)'
_computing_data_collection
'CrystalClear (Rigaku Americas Corporation, 2005)'
_computing_data_reduction
'CrystalClear (Rigaku Americas Corporation, 2005)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      98(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku AFC12κ/SATURN724'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_sigmaI/netI    0.023
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6334
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.19
_refine_ls_abs_structure_details 'Flack (1983), 845 Friedel pairs'
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2202
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.030
_refine_ls_R_factor_gt           0.030
_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/[σ²(Fo²)+(0.0306P)²+1.0876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.068
_refine_ls_wR_factor_ref         0.069
_reflns_number_gt                2160
_reflns_number_total             2202
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv2071.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2215396
_cod_database_fobs_code          2215396
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.53512(3) 0.82070(8) 0.39615(4) 0.02211(12) Uani d . 1
N N1 0.45431(9) 1.0153(3) 0.15952(14) 0.0166(3) Uani d . 1
N N2 0.43439(9) 1.0280(3) 0.02939(14) 0.0192(3) Uani d . 1
N N3 0.55419(8) 0.7817(3) 0.19105(13) 0.0170(3) Uani d . 1
H H3 0.5407 0.8284 0.1118 0.020 Uiso calc R 1
C C1 0.38502(11) 1.1986(4) -0.02293(18) 0.0205(4) Uani d . 1
H H1 0.3618 1.2443 -0.1119 0.025 Uiso calc R 1
C C2 0.36965(9) 1.3095(4) 0.06872(15) 0.0183(4) Uani d . 1
C C3 0.32405(11) 1.4985(4) 0.0617(2) 0.0230(4) Uani d . 1
H H3A 0.2935 1.5815 -0.0178 0.028 Uiso calc R 1
C C4 0.32458(11) 1.5613(4) 0.1736(2) 0.0244(4) Uani d . 1
H H4 0.2943 1.6899 0.1717 0.029 Uiso calc R 1
C C5 0.36970(11) 1.4360(4) 0.29058(19) 0.0237(4) Uani d . 1
H H5 0.3689 1.4827 0.3662 0.028 Uiso calc R 1
C C6 0.41493(11) 1.2485(4) 0.29997(17) 0.0215(4) Uani d . 1
H H6 0.4448 1.1652 0.3796 0.026 Uiso calc R 1
C C7 0.41481(10) 1.1861(3) 0.18606(17) 0.0167(4) Uani d . 1
C C8 0.51513(10) 0.8685(3) 0.24509(16) 0.0174(4) Uani d . 1
C C9 0.61595(10) 0.6190(3) 0.25473(16) 0.0154(4) Uani d . 1
C C10 0.60810(11) 0.4125(4) 0.30926(17) 0.0189(4) Uani d . 1
H H10 0.5610 0.3779 0.3039 0.023 Uiso calc R 1
C C11 0.66871(11) 0.2582(3) 0.37105(17) 0.0205(4) Uani d . 1
H H11 0.6635 0.1188 0.4095 0.025 Uiso calc R 1
C C12 0.73743(10) 0.3055(4) 0.37739(16) 0.0208(4) Uani d . 1
H H12 0.7793 0.1996 0.4207 0.025 Uiso calc R 1
C C13 0.74437(11) 0.5080(3) 0.32012(18) 0.0201(4) Uani d . 1
H H13 0.7908 0.5393 0.3226 0.024 Uiso calc R 1
C C14 0.68392(10) 0.6660(3) 0.25904(17) 0.0185(4) Uani d . 1
H H14 0.6891 0.8054 0.2205 0.022 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 N1 C7 110.34(14)
N2 N1 C8 118.84(14)
C7 N1 C8 130.08(15)
C1 N2 N1 106.36(15)
C8 N3 C9 123.98(14)
C8 N3 H3 118.0
C9 N3 H3 118.0
N2 C1 C2 112.47(17)
N2 C1 H1 123.8
C2 C1 H1 123.8
C3 C2 C7 121.21(16)
C3 C2 C1 134.13(17)
C7 C2 C1 104.65(17)
C4 C3 C2 118.07(18)
C4 C3 H3A 121.0
C2 C3 H3A 121.0
C3 C4 C5 120.36(19)
C3 C4 H4 119.8
C5 C4 H4 119.8
C6 C5 C4 122.72(18)
C6 C5 H5 118.6
C4 C5 H5 118.6
C5 C6 C7 116.82(17)
C5 C6 H6 121.6
C7 C6 H6 121.6
N1 C7 C2 106.18(15)
N1 C7 C6 132.99(17)
C2 C7 C6 120.82(18)
N3 C8 N1 112.77(15)
N3 C8 S1 125.95(14)
N1 C8 S1 121.26(13)
C14 C9 C10 120.00(17)
C14 C9 N3 119.07(16)
C10 C9 N3 120.92(17)
C11 C10 C9 119.97(18)
C11 C10 H10 120.0
C9 C10 H10 120.0
C10 C11 C12 120.40(18)
C10 C11 H11 119.8
C12 C11 H11 119.8
C13 C12 C11 119.46(18)
C13 C12 H12 120.3
C11 C12 H12 120.3
C12 C13 C14 120.55(17)
C12 C13 H13 119.7
C14 C13 H13 119.7
C9 C14 C13 119.60(18)
C9 C14 H14 120.2
C13 C14 H14 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.6545(19)
N1 N2 1.391(2)
N1 C7 1.399(2)
N1 C8 1.405(2)
N2 C1 1.303(3)
N3 C8 1.352(2)
N3 C9 1.426(2)
N3 H3 0.8800
C1 C2 1.432(3)
C1 H1 0.9500
C2 C3 1.396(3)
C2 C7 1.405(3)
C3 C4 1.378(3)
C3 H3A 0.9500
C4 C5 1.407(3)
C4 H4 0.9500
C5 C6 1.377(3)
C5 H5 0.9500
C6 C7 1.405(3)
C6 H6 0.9500
C9 C14 1.387(3)
C9 C10 1.393(3)
C10 C11 1.379(3)
C10 H10 0.9500
C11 C12 1.391(3)
C11 H11 0.9500
C12 C13 1.384(3)
C12 H12 0.9500
C13 C14 1.390(3)
C13 H13 0.9500
C14 H14 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3 N2 2_655 0.88 2.30 3.097(3) 151 y
C5 H5 S1 2_666 0.95 3.14 3.881(2) 136 y
C6 H6 S1 2_656 0.95 3.17 4.040(3) 153 y
C1 H1 Cg(C9--C14) 2_665 0.95 ??? 2.47 ??? y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7 N1 N2 C1 0.2(2)
C8 N1 N2 C1 -170.97(16)
N1 N2 C1 C2 0.3(2)
N2 C1 C2 C3 178.1(2)
N2 C1 C2 C7 -0.7(2)
C7 C2 C3 C4 0.1(3)
C1 C2 C3 C4 -178.5(2)
C2 C3 C4 C5 -0.4(3)
C3 C4 C5 C6 0.2(3)
C4 C5 C6 C7 0.4(3)
N2 N1 C7 C2 -0.61(19)
C8 N1 C7 C2 169.24(17)
N2 N1 C7 C6 -179.06(19)
C8 N1 C7 C6 -9.2(3)
C3 C2 C7 N1 -178.21(17)
C1 C2 C7 N1 0.76(19)
C3 C2 C7 C6 0.5(3)
C1 C2 C7 C6 179.44(17)
C5 C6 C7 N1 177.58(19)
C5 C6 C7 C2 -0.7(3)
C9 N3 C8 N1 -176.69(16)
C9 N3 C8 S1 5.0(3)
N2 N1 C8 N3 9.0(2)
C7 N1 C8 N3 -160.10(18)
N2 N1 C8 S1 -172.60(13)
C7 N1 C8 S1 18.3(3)
C8 N3 C9 C14 -129.93(19)
C8 N3 C9 C10 51.7(2)
C14 C9 C10 C11 2.0(3)
N3 C9 C10 C11 -179.65(16)
C9 C10 C11 C12 -1.1(3)
C10 C11 C12 C13 -0.6(3)
C11 C12 C13 C14 1.4(3)
C10 C9 C14 C13 -1.2(3)
N3 C9 C14 C13 -179.58(16)
C12 C13 C14 C9 -0.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123410
