#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/76/2227688.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227688
loop_
_publ_author_name
'A. Shaker, Shayma'
'Khaledi, Hamid'
'Mohd Ali, Hapipah'
_publ_section_title
;
 2-Methylbenzimidazolium thiocyanate
;
_journal_coeditor_code           IS2616
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2913
_journal_paper_doi               10.1107/S1600536810042145
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H9 N2 +, S C N -'
_chemical_formula_moiety         'C8 H9 N2 +, C N S -'
_chemical_formula_sum            'C9 H9 N3 S'
_chemical_formula_weight         191.25
_chemical_name_systematic
;
2-Methylbenzimidazolium thiocyanate
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.879(2)
_cell_length_b                   7.2157(15)
_cell_length_c                   12.890(3)
_cell_measurement_reflns_used    4285
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.25
_cell_measurement_theta_min      2.60
_cell_volume                     918.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10495
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.9557
_exptl_absorpt_correction_T_min  0.8878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.284
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         1133
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0337
_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)+(0.0395P)²+0.9286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0900
_reflns_number_gt                1000
_reflns_number_total             1133
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is2616.cif
_cod_data_source_block           I
_cod_original_cell_volume        918.9(3)
_cod_database_code               2227688
_cod_database_fobs_code          2227688
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
'x-1/2, y, -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
S S1 -0.11964(6) 0.2500 0.31732(5) 0.02094(18) Uani d S 1 . .
N N1 0.15210(19) 0.2500 0.37930(15) 0.0193(4) Uani d S 1 . .
C C1 0.0383(2) 0.2500 0.35335(17) 0.0162(4) Uani d S 1 . .
H H2 0.2584(17) 0.485(2) 0.3813(13) 0.019 Uiso d D 1 . .
N N2 0.28838(12) 0.60009(17) 0.38143(10) 0.0155(3) Uani d D 1 . .
C C2 0.0609(2) 0.7500 0.38575(17) 0.0191(5) Uani d S 1 . .
H H2A 0.0277 0.8779 0.3825 0.029 Uiso calc PR 0.50 . .
H H2B 0.0299 0.6922 0.4503 0.029 Uiso calc PR 0.50 . .
H H2BA 0.0258 0.6800 0.3264 0.029 Uiso calc PR 0.50 . .
C C3 0.2103(2) 0.7500 0.38283(15) 0.0156(4) Uani d S 1 . .
C C4 0.42343(15) 0.6534(2) 0.37939(11) 0.0148(3) Uani d . 1 . .
C C5 0.54317(15) 0.5525(2) 0.37848(11) 0.0179(3) Uani d . 1 . .
H H5 0.5432 0.4209 0.3774 0.022 Uiso calc R 1 . .
C C6 0.66199(15) 0.6529(2) 0.37921(11) 0.0189(3) Uani d . 1 . .
H H6 0.7460 0.5887 0.3797 0.023 Uiso calc R 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0159(3) 0.0182(3) 0.0287(3) 0.000 -0.0020(2) 0.000
N1 0.0179(9) 0.0140(9) 0.0260(10) 0.000 0.0024(7) 0.000
C1 0.0200(10) 0.0105(9) 0.0182(10) 0.000 0.0034(8) 0.000
N2 0.0169(6) 0.0104(6) 0.0191(6) -0.0018(5) 0.0000(5) 0.0004(5)
C2 0.0170(10) 0.0192(11) 0.0211(11) 0.000 0.0015(8) 0.000
C3 0.0193(10) 0.0151(10) 0.0126(9) 0.000 -0.0012(8) 0.000
C4 0.0168(7) 0.0141(7) 0.0135(6) -0.0007(6) -0.0004(5) 0.0004(5)
C5 0.0215(7) 0.0126(7) 0.0197(7) 0.0023(6) -0.0015(6) -0.0003(6)
C6 0.0175(7) 0.0200(8) 0.0193(7) 0.0026(6) -0.0007(6) 0.0001(6)
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 S1 . . 180.0(2) ?
C3 N2 C4 . . 109.44(13) ?
C3 N2 H2 . . 124.8(12) ?
C4 N2 H2 . . 125.7(12) ?
C3 C2 H2A . . 109.5 ?
C3 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C3 C2 H2BA . . 109.5 ?
H2A C2 H2BA . . 109.5 ?
H2B C2 H2BA . . 109.5 ?
N2 C3 N2 . 7_575 108.97(18) ?
N2 C3 C2 . . 125.52(9) ?
N2 C4 C5 . . 132.32(14) ?
N2 C4 C4 . 7_575 106.08(8) ?
C5 C4 C4 . 7_575 121.60(9) ?
C6 C5 C4 . . 116.72(15) ?
C6 C5 H5 . . 121.6 ?
C4 C5 H5 . . 121.6 ?
C5 C6 C6 . 7_575 121.67(9) ?
C5 C6 H6 . . 119.2 ?
C6 C6 H6 7_575 . 119.2 ?
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
S1 C1 . 1.628(2) ?
N1 C1 . 1.173(3) ?
N2 C3 . 1.3289(18) ?
N2 C4 . 1.3888(19) ?
N2 H2 . 0.881(15) ?
C2 C3 . 1.477(3) ?
C2 H2A . 0.9800 ?
C2 H2B . 0.9800 ?
C2 H2BA . 0.9800 ?
C4 C5 . 1.389(2) ?
C4 C4 7_575 1.394(3) ?
C5 C6 . 1.379(2) ?
C5 H5 . 0.9500 ?
C6 C6 7_575 1.401(3) ?
C6 H6 . 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
N2 H2 N1 . 0.881(15) 1.995(15) 2.8627(16) 167.9(16)
