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#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/19/2221954.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_2221954
loop_
_publ_author_name
'Lin, Jin Rui'
'He, Jia'
'Qian, Yang'
'Zhao, Hong'
_publ_section_title
;
 3-[(1H-Benzimidazol-2-yl)sulfanylmethyl]benzonitrile
;
_journal_coeditor_code           BX2210
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1358
_journal_paper_doi               10.1107/S1600536809018546
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H11 N3 S'
_chemical_formula_moiety         'C15 H11 N3 S'
_chemical_formula_sum            'C15 H11 N3 S'
_chemical_formula_weight         265.33
_chemical_name_systematic
;
3-[(1H-Benzimidazol-2-yl)sulfanylmethyl]benzonitrile
;
_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                 101.63(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.384(4)
_cell_length_b                   9.280(4)
_cell_length_c                   9.887(4)
_cell_measurement_reflns_used    2386
_cell_measurement_temperature    291.5
_cell_measurement_theta_max      27.4449
_cell_measurement_theta_min      2.5826
_cell_volume                     1382.5(9)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_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      291.5
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       ω
_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  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12254
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.9474
_exptl_absorpt_correction_T_min  0.9271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0701
_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/[σ²(Fo²)+(0.0802P)²+0.4001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1665
_refine_ls_wR_factor_ref         0.1835
_reflns_number_gt                1926
_reflns_number_total             2711
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2210.cif
_cod_data_source_block           I
_cod_original_cell_volume        1382.5(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221954
_cod_database_fobs_code          2221954
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3269(2) 0.2203(3) 0.2414(3) 0.0566(8) Uani d . 1 . .
C C2 0.3718(2) 0.4296(3) 0.3180(3) 0.0541(8) Uani d . 1 . .
C C3 0.3983(3) 0.5528(3) 0.3966(3) 0.0666(9) Uani d . 1 . .
H H3 0.3940 0.5575 0.4890 0.080 Uiso calc R 1 . .
C C4 0.4308(3) 0.6672(3) 0.3330(3) 0.0710(10) Uani d . 1 . .
H H4 0.4484 0.7505 0.3834 0.085 Uiso calc R 1 . .
C C5 0.4379(3) 0.6608(3) 0.1944(3) 0.0684(9) Uani d . 1 . .
H H5 0.4602 0.7398 0.1546 0.082 Uiso calc R 1 . .
C C6 0.4125(2) 0.5406(3) 0.1158(3) 0.0639(9) Uani d . 1 . .
H H6 0.4175 0.5362 0.0237 0.077 Uiso calc R 1 . .
C C7 0.3791(2) 0.4256(3) 0.1795(3) 0.0517(7) Uani d . 1 . .
C C8 0.2071(3) 0.0318(4) 0.3261(4) 0.0835(11) Uani d . 1 . .
H H8A 0.2330 0.0408 0.4236 0.100 Uiso calc R 1 . .
H H8B 0.1646 0.1092 0.3001 0.100 Uiso calc R 1 . .
C C9 0.1622(3) -0.1128(4) 0.2964(4) 0.0772(10) Uani d . 1 . .
C C10 0.1924(3) -0.2344(5) 0.3728(5) 0.0999(14) Uani d . 1 . .
H H10 0.2388 -0.2259 0.4489 0.120 Uiso calc R 1 . .
C C11 0.1549(4) -0.3684(5) 0.3378(6) 0.1166(17) Uani d . 1 . .
H H11 0.1762 -0.4493 0.3897 0.140 Uiso calc R 1 . .
C C12 0.0852(4) -0.3812(5) 0.2247(6) 0.1106(16) Uani d . 1 . .
H H12 0.0605 -0.4711 0.1993 0.133 Uiso calc R 1 . .
C C13 0.0527(3) -0.2595(4) 0.1495(5) 0.0899(12) Uani d . 1 . .
C C14 0.0911(3) -0.1256(4) 0.1844(4) 0.0814(11) Uani d . 1 . .
H H14 0.0694 -0.0446 0.1332 0.098 Uiso calc R 1 . .
C C15 -0.0208(4) -0.2675(6) 0.0345(6) 0.1185(18) Uani d . 1 . .
N N1 0.33875(19) 0.2979(3) 0.3553(2) 0.0602(7) Uani d . 1 . .
N N2 0.34898(18) 0.2904(2) 0.1329(2) 0.0572(7) Uani d . 1 . .
H H2A 0.3450 0.2572 0.0507 0.069 Uiso calc R 1 . .
N N3 -0.0786(4) -0.2759(6) -0.0567(6) 0.161(2) Uani d . 1 . .
S S1 0.29335(7) 0.03901(9) 0.22331(9) 0.0739(4) Uani d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 N2 . . 113.6(3) ?
N1 C1 S1 . . 126.6(2) ?
N2 C1 S1 . . 119.6(2) ?
C3 C2 C7 . . 119.7(3) ?
C3 C2 N1 . . 130.4(3) ?
C7 C2 N1 . . 109.9(2) ?
C4 C3 C2 . . 118.0(3) ?
C4 C3 H3 . . 121.0 ?
C2 C3 H3 . . 121.0 ?
C3 C4 C5 . . 121.4(3) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
C6 C5 C4 . . 121.4(3) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C7 . . 117.2(3) ?
C5 C6 H6 . . 121.4 ?
C7 C6 H6 . . 121.4 ?
N2 C7 C6 . . 132.4(3) ?
N2 C7 C2 . . 105.3(2) ?
C6 C7 C2 . . 122.3(3) ?
C9 C8 S1 . . 106.2(3) ?
C9 C8 H8A . . 110.5 ?
S1 C8 H8A . . 110.5 ?
C9 C8 H8B . . 110.5 ?
S1 C8 H8B . . 110.5 ?
H8A C8 H8B . . 108.7 ?
C10 C9 C14 . . 119.1(4) ?
C10 C9 C8 . . 121.8(4) ?
C14 C9 C8 . . 119.0(4) ?
C9 C10 C11 . . 121.2(5) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C10 C11 C12 . . 119.5(5) ?
C10 C11 H11 . . 120.2 ?
C12 C11 H11 . . 120.2 ?
C13 C12 C11 . . 119.8(4) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C12 C13 C14 . . 120.4(4) ?
C12 C13 C15 . . 121.6(4) ?
C14 C13 C15 . . 118.0(4) ?
C13 C14 C9 . . 119.9(4) ?
C13 C14 H14 . . 120.0 ?
C9 C14 H14 . . 120.0 ?
N3 C15 C13 . . 179.0(7) ?
C1 N1 C2 . . 104.3(2) ?
C1 N2 C7 . . 107.0(2) ?
C1 N2 H2A . . 126.5 ?
C7 N2 H2A . . 126.5 ?
C1 S1 C8 . . 102.13(15) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.319(3) ?
C1 N2 . 1.355(3) ?
C1 S1 . 1.758(3) ?
C2 C3 . 1.396(4) ?
C2 C7 . 1.397(4) ?
C2 N1 . 1.401(4) ?
C3 C4 . 1.379(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.398(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.370(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.390(4) ?
C6 H6 . 0.9300 ?
C7 N2 . 1.384(4) ?
C8 C9 . 1.510(5) ?
C8 S1 . 1.829(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.385(6) ?
C9 C14 . 1.396(6) ?
C10 C11 . 1.386(6) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.390(7) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.389(6) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.389(5) ?
C13 C15 . 1.435(8) ?
C14 H14 . 0.9300 ?
C15 N3 . 1.135(7) ?
N2 H2A . 0.8600 ?
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
N2 H2A N1 4_565 0.86 1.98 2.838(3) 173.8
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C2 C3 C4 . . . . 0.0(5) ?
N1 C2 C3 C4 . . . . 178.4(3) ?
C2 C3 C4 C5 . . . . -0.4(6) ?
C3 C4 C5 C6 . . . . 0.2(6) ?
C4 C5 C6 C7 . . . . 0.3(5) ?
C5 C6 C7 N2 . . . . -179.1(3) ?
C5 C6 C7 C2 . . . . -0.6(5) ?
C3 C2 C7 N2 . . . . 179.3(3) ?
N1 C2 C7 N2 . . . . 0.6(4) ?
C3 C2 C7 C6 . . . . 0.5(5) ?
N1 C2 C7 C6 . . . . -178.2(3) ?
S1 C8 C9 C10 . . . . 88.9(4) ?
S1 C8 C9 C14 . . . . -87.8(4) ?
C14 C9 C10 C11 . . . . 1.6(7) ?
C8 C9 C10 C11 . . . . -175.0(4) ?
C9 C10 C11 C12 . . . . -0.4(8) ?
C10 C11 C12 C13 . . . . -1.3(8) ?
C11 C12 C13 C14 . . . . 1.9(8) ?
C11 C12 C13 C15 . . . . -178.2(5) ?
C12 C13 C14 C9 . . . . -0.6(7) ?
C15 C13 C14 C9 . . . . 179.4(4) ?
C10 C9 C14 C13 . . . . -1.1(6) ?
C8 C9 C14 C13 . . . . 175.6(4) ?
C12 C13 C15 N3 . . . . -2E1(4) ?
C14 C13 C15 N3 . . . . 16E1(4) ?
N2 C1 N1 C2 . . . . -0.4(4) ?
S1 C1 N1 C2 . . . . 175.5(3) ?
C3 C2 N1 C1 . . . . -178.6(4) ?
C7 C2 N1 C1 . . . . -0.2(4) ?
N1 C1 N2 C7 . . . . 0.8(4) ?
S1 C1 N2 C7 . . . . -175.4(2) ?
C6 C7 N2 C1 . . . . 177.8(4) ?
C2 C7 N2 C1 . . . . -0.8(3) ?
N1 C1 S1 C8 . . . . 41.3(4) ?
N2 C1 S1 C8 . . . . -143.1(3) ?
C9 C8 S1 C1 . . . . 170.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6066945
