#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/91/2229184.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_2229184
loop_
_publ_author_name
'Ziaulla, Mohamed'
'Manjunatha, M. N.'
'Sankolli, Ravish'
'Nagasundara, K. R.'
'Begum, Noor Shahina'
_publ_section_title
;
 2-(4-Methylsulfanylphenyl)-1H-benzimidazol-3-ium bromide
;
_journal_coeditor_code           PB2053
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o341
_journal_page_last               o342
_journal_paper_doi               10.1107/S1600536811000146
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H13  N2 S +, Br -'
_chemical_formula_moiety         'C14 H13  N2 S +, Br -'
_chemical_formula_sum            'C14 H13 Br N2 S'
_chemical_formula_weight         321.23
_chemical_name_systematic
;
2-(4-Methylsulfanylphenyl)-1H-benzimidazol-3-ium bromide
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 100.113(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3289(2)
_cell_length_b                   24.0195(12)
_cell_length_c                   10.9544(5)
_cell_measurement_reflns_used    3009
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      1.70
_cell_volume                     1380.35(11)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23823
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    3.112
_exptl_absorpt_correction_T_max  0.6358
_exptl_absorpt_correction_T_min  0.5749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Kappa APEX'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0289
_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)+(0.0338P)²+0.3109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0690
_reflns_number_gt                2273
_reflns_number_total             3009
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            pb2053.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C14 H13 Br N2 S '
_cod_database_code               2229184
_cod_database_fobs_code          2229184
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.27225(4) 0.295277(10) 0.33608(2) 0.04982(10) Uani d . 1 . .
S S1 0.57379(16) -0.00128(3) 0.21720(8) 0.0710(2) Uani d . 1 . .
N N1 0.6485(4) 0.28057(8) 0.13508(19) 0.0421(5) Uani d . 1 . .
N N2 0.9186(4) 0.25577(8) 0.01982(17) 0.0408(4) Uani d . 1 . .
C C1 0.9109(4) 0.31328(10) 0.0161(2) 0.0415(5) Uani d . 1 . .
C C2 1.0437(5) 0.35189(11) -0.0424(2) 0.0555(6) Uani d . 1 . .
C C3 0.9910(6) 0.40696(12) -0.0233(3) 0.0644(7) Uani d . 1 . .
C C4 0.8149(6) 0.42307(12) 0.0504(3) 0.0659(8) Uani d . 1 . .
C C5 0.6847(5) 0.38481(11) 0.1084(3) 0.0555(6) Uani d . 1 . .
C C6 0.7381(4) 0.32913(10) 0.0906(2) 0.0430(5) Uani d . 1 . .
C C7 0.7610(4) 0.23676(9) 0.09243(19) 0.0387(5) Uani d . 1 . .
C C8 0.7198(4) 0.17861(9) 0.1213(2) 0.0391(5) Uani d . 1 . .
C C9 0.5449(5) 0.16389(11) 0.1960(2) 0.0516(6) Uani d . 1 . .
C C10 0.5058(5) 0.10930(11) 0.2220(2) 0.0558(6) Uani d . 1 . .
C C11 0.6392(5) 0.06710(10) 0.1762(2) 0.0453(5) Uani d . 1 . .
C C12 0.8139(6) 0.08164(11) 0.1013(3) 0.0586(7) Uani d . 1 . .
C C13 0.8530(5) 0.13648(11) 0.0746(3) 0.0548(7) Uani d . 1 . .
C C14 0.7734(8) -0.04379(14) 0.1398(4) 0.0721(9) Uani d . 1 . .
H H1N 0.562(5) 0.2802(10) 0.181(2) 0.042(7) Uiso d . 1 . .
H H9 0.464(5) 0.1907(12) 0.233(2) 0.062(8) Uiso d . 1 . .
H H2N 0.991(5) 0.2357(11) -0.017(2) 0.049(8) Uiso d . 1 . .
H H12 0.909(5) 0.0539(11) 0.070(2) 0.065(8) Uiso d . 1 . .
H H14C 0.736(6) -0.0776(16) 0.159(3) 0.086(11) Uiso d . 1 . .
H H14B 0.947(7) -0.0359(13) 0.169(3) 0.090(11) Uiso d . 1 . .
H H5 0.567(5) 0.3946(12) 0.163(2) 0.075(9) Uiso d . 1 . .
H H4 0.781(6) 0.4619(13) 0.063(3) 0.085(10) Uiso d . 1 . .
H H2 1.159(5) 0.3398(11) -0.092(2) 0.058(7) Uiso d . 1 . .
H H13 0.975(5) 0.1462(12) 0.022(3) 0.079(9) Uiso d . 1 . .
H H10 0.389(5) 0.0996(11) 0.276(2) 0.064(7) Uiso d . 1 . .
H H3 1.080(5) 0.4350(12) -0.060(2) 0.070(8) Uiso d . 1 . .
H H14A 0.736(6) -0.0374(14) 0.054(3) 0.097(12) Uiso d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
Br Br -0.2901 2.4595 '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'
C C 0.0033 0.0016 '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
C11 S1 C14 . . 104.57(15) ?
C7 N1 C6 . . 109.73(19) ?
C7 N1 H1N . . 127.0(19) ?
C6 N1 H1N . . 123.0(19) ?
C7 N2 C1 . . 109.94(18) ?
C7 N2 H2N . . 121.6(19) ?
C1 N2 H2N . . 128.3(19) ?
N2 C1 C6 . . 106.04(19) ?
N2 C1 C2 . . 131.7(2) ?
C6 C1 C2 . . 122.2(2) ?
C3 C2 C1 . . 115.9(3) ?
C3 C2 H2 . . 124.1(16) ?
C1 C2 H2 . . 120.0(16) ?
C2 C3 C4 . . 122.1(3) ?
C2 C3 H3 . . 119.2(17) ?
C4 C3 H3 . . 118.7(17) ?
C5 C4 C3 . . 121.9(3) ?
C5 C4 H4 . . 117.2(19) ?
C3 C4 H4 . . 121.0(19) ?
C4 C5 C6 . . 116.5(3) ?
C4 C5 H5 . . 123.9(18) ?
C6 C5 H5 . . 119.5(18) ?
N1 C6 C1 . . 106.4(2) ?
N1 C6 C5 . . 132.2(2) ?
C1 C6 C5 . . 121.4(2) ?
N2 C7 N1 . . 107.9(2) ?
N2 C7 C8 . . 126.29(19) ?
N1 C7 C8 . . 125.82(18) ?
C13 C8 C9 . . 118.2(2) ?
C13 C8 C7 . . 120.93(19) ?
C9 C8 C7 . . 120.9(2) ?
C10 C9 C8 . . 120.6(2) ?
C10 C9 H9 . . 118.9(17) ?
C8 C9 H9 . . 120.3(17) ?
C9 C10 C11 . . 121.5(2) ?
C9 C10 H10 . . 120.0(16) ?
C11 C10 H10 . . 118.4(16) ?
C10 C11 C12 . . 118.1(2) ?
C10 C11 S1 . . 117.15(18) ?
C12 C11 S1 . . 124.79(19) ?
C13 C12 C11 . . 120.6(2) ?
C13 C12 H12 . . 119.2(17) ?
C11 C12 H12 . . 120.2(17) ?
C12 C13 C8 . . 121.1(2) ?
C12 C13 H13 . . 120.1(17) ?
C8 C13 H13 . . 118.9(18) ?
S1 C14 H14C . . 104(2) ?
S1 C14 H14B . . 111(2) ?
H14C C14 H14B . . 111(3) ?
S1 C14 H14A . . 110(2) ?
H14C C14 H14A . . 112(3) ?
H14B C14 H14A . . 109(3) ?
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 C11 . 1.754(2) ?
S1 C14 . 1.791(4) ?
N1 C7 . 1.335(3) ?
N1 C6 . 1.381(3) ?
N1 H1N . 0.74(3) ?
N2 C7 . 1.334(3) ?
N2 C1 . 1.382(3) ?
N2 H2N . 0.77(3) ?
C1 C6 . 1.386(3) ?
C1 C2 . 1.390(3) ?
C2 C3 . 1.376(4) ?
C2 H2 . 0.93(3) ?
C3 C4 . 1.395(4) ?
C3 H3 . 0.95(3) ?
C4 C5 . 1.373(4) ?
C4 H4 . 0.96(3) ?
C5 C6 . 1.388(3) ?
C5 H5 . 0.97(3) ?
C7 C8 . 1.457(3) ?
C8 C13 . 1.384(3) ?
C8 C9 . 1.390(3) ?
C9 C10 . 1.365(4) ?
C9 H9 . 0.91(3) ?
C10 C11 . 1.382(3) ?
C10 H10 . 0.96(3) ?
C11 C12 . 1.389(3) ?
C12 C13 . 1.373(4) ?
C12 H12 . 0.94(3) ?
C13 H13 . 0.97(3) ?
C14 H14C . 0.87(4) ?
C14 H14B . 0.94(3) ?
C14 H14A . 0.94(3) ?
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
N1 H1N Br1 1_555 0.74(2) 2.51(2) 3.247(2) 171(2)
N2 H2N Br1 4_654 0.77(3) 2.50(2) 3.231(2) 159
C5 H5 S1 2_655 0.97(3) 2.98(3) 3.736(3) 135
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 N2 C1 C6 . . . . -0.2(3) ?
C7 N2 C1 C2 . . . . 177.8(3) ?
N2 C1 C2 C3 . . . . -178.5(2) ?
C6 C1 C2 C3 . . . . -0.8(4) ?
C1 C2 C3 C4 . . . . 0.0(4) ?
C2 C3 C4 C5 . . . . 0.3(5) ?
C3 C4 C5 C6 . . . . 0.3(4) ?
C7 N1 C6 C1 . . . . 0.8(3) ?
C7 N1 C6 C5 . . . . -179.2(3) ?
N2 C1 C6 N1 . . . . -0.4(2) ?
C2 C1 C6 N1 . . . . -178.6(2) ?
N2 C1 C6 C5 . . . . 179.6(2) ?
C2 C1 C6 C5 . . . . 1.4(4) ?
C4 C5 C6 N1 . . . . 178.9(3) ?
C4 C5 C6 C1 . . . . -1.1(4) ?
C1 N2 C7 N1 . . . . 0.7(3) ?
C1 N2 C7 C8 . . . . -178.83(19) ?
C6 N1 C7 N2 . . . . -0.9(3) ?
C6 N1 C7 C8 . . . . 178.60(19) ?
N2 C7 C8 C13 . . . . 1.4(3) ?
N1 C7 C8 C13 . . . . -178.0(2) ?
N2 C7 C8 C9 . . . . -178.3(2) ?
N1 C7 C8 C9 . . . . 2.2(3) ?
C13 C8 C9 C10 . . . . -0.2(4) ?
C7 C8 C9 C10 . . . . 179.5(2) ?
C8 C9 C10 C11 . . . . 0.6(4) ?
C9 C10 C11 C12 . . . . -0.7(4) ?
C9 C10 C11 S1 . . . . 179.5(2) ?
C14 S1 C11 C10 . . . . 178.8(2) ?
C14 S1 C11 C12 . . . . -1.0(3) ?
C10 C11 C12 C13 . . . . 0.4(4) ?
S1 C11 C12 C13 . . . . -179.8(2) ?
C11 C12 C13 C8 . . . . -0.1(5) ?
C9 C8 C13 C12 . . . . -0.1(4) ?
C7 C8 C13 C12 . . . . -179.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656482
