#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/27/2232717.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_2232717
loop_
_publ_author_name
'Liu, Ming-Liang'
_publ_section_title
;
 2-Trifluoromethyl-1H-benzimidazol-3-ium hydrogen sulfate
;
_journal_coeditor_code           HB6491
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3473
_journal_paper_doi               10.1107/S1600536811048811
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C8 H6 F3 N2 +, H S O4 -'
_chemical_formula_moiety         'C8 H6 F3 N2 +, H O4 S -'
_chemical_formula_sum            'C8 H7 F3 N2 O4 S'
_chemical_formula_weight         284.22
_chemical_name_systematic
;
2-Trifluoromethyl-1H-benzimidazol-3-ium hydrogen sulfate
;
_space_group_IT_number           170
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_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                120.00
_cell_formula_units_Z            6
_cell_length_a                   9.4119(13)
_cell_length_b                   9.4119(13)
_cell_length_c                   21.960(4)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      3.07
_cell_volume                     1684.7(4)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Mercury2 CCD'
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14287
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_T_max  0.9353
_exptl_absorpt_correction_T_min  0.9353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.253
_refine_ls_abs_structure_details 'Flack (1983), 957 Friedel pairs'
_refine_ls_abs_structure_Flack   0.03(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1977
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.228
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0522
_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)+(0.0593P)²+1.9666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                1941
_reflns_number_total             1977
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6491.cif
_cod_data_source_block           I
_cod_original_cell_volume        1684.7(5)
_cod_original_sg_symbol_Hall     'P 65 '
_cod_original_sg_symbol_H-M      'P 65 '
_cod_database_code               2232717
_cod_database_fobs_code          2232717
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'
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_symmetry_multiplicity
S S1 0.09970(14) 0.72553(17) 0.16867(6) 0.0442(3) Uani d . 1 1
N N1 0.4873(5) 0.7391(5) 0.1735(2) 0.0418(9) Uani d . 1 1
H H1A 0.3843 0.7058 0.1770 0.050 Uiso calc R 1 1
N N2 0.7169(4) 0.7349(5) 0.16388(17) 0.0348(8) Uani d . 1 1
H H2A 0.7835 0.6981 0.1596 0.042 Uiso calc R 1 1
C C3 0.6124(6) 0.9017(6) 0.1722(2) 0.0418(11) Uani d . 1 1
C C8 0.7613(5) 0.9011(6) 0.1675(2) 0.0371(10) Uani d . 1 1
C C4 0.6126(7) 1.0512(7) 0.1762(3) 0.0508(13) Uani d . 1 1
H H4 0.5152 1.0535 0.1792 0.061 Uiso calc R 1 1
O O3 -0.0637(4) 0.6347(5) 0.14218(18) 0.0558(11) Uani d . 1 1
F F3 0.5450(5) 0.4034(5) 0.1391(3) 0.0928(15) Uani d . 1 1
C C6 0.9082(7) 1.1891(7) 0.1712(3) 0.0527(13) Uani d . 1 1
H H6 1.0066 1.2883 0.1710 0.063 Uiso calc R 1 1
O O1 0.0866(5) 0.8248(5) 0.2230(2) 0.0627(11) Uani d D 1 1
C C5 0.7592(8) 1.1907(7) 0.1755(3) 0.0589(15) Uani d . 1 1
H H5 0.7623 1.2909 0.1780 0.071 Uiso calc R 1 1
F F1 0.3262(5) 0.4077(6) 0.1346(3) 0.116(2) Uani d . 1 1
F F2 0.4211(10) 0.3991(6) 0.2195(2) 0.157(3) Uani d U 1 1
O O4 0.1589(5) 0.6207(5) 0.19150(19) 0.0571(11) Uani d . 1 1
C C7 0.9120(6) 1.0455(7) 0.1670(3) 0.0456(11) Uani d . 1 1
H H7 1.0103 1.0448 0.1641 0.055 Uiso calc R 1 1
C C1 0.4609(6) 0.4596(7) 0.1670(3) 0.0520(13) Uani d U 1 1
O O2 0.2184(6) 0.8507(9) 0.1300(3) 0.110(2) Uani d . 1 1
C C2 0.5531(5) 0.6434(6) 0.1683(2) 0.0373(9) Uani d . 1 1
H H1 0.041(10) 0.754(9) 0.251(3) 0.10(3) Uiso d D 1 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 0.0252(5) 0.0626(9) 0.0458(6) 0.0227(5) 0.0080(5) 0.0144(6)
N1 0.0295(19) 0.051(2) 0.051(2) 0.0252(19) -0.0012(18) -0.0049(19)
N2 0.0243(17) 0.044(2) 0.040(2) 0.0205(16) 0.0009(16) -0.0062(18)
C3 0.037(2) 0.050(3) 0.043(3) 0.025(2) 0.001(2) -0.002(2)
C8 0.037(2) 0.043(3) 0.037(2) 0.024(2) -0.006(2) -0.005(2)
C4 0.057(3) 0.058(3) 0.059(3) 0.044(3) -0.002(3) 0.003(3)
O3 0.0362(19) 0.087(3) 0.059(2) 0.042(2) -0.0057(16) -0.015(2)
F3 0.070(2) 0.058(2) 0.158(4) 0.038(2) 0.018(3) -0.012(3)
C6 0.044(3) 0.045(3) 0.062(3) 0.017(2) 0.006(3) 0.009(3)
O1 0.056(3) 0.048(2) 0.079(3) 0.022(2) -0.009(2) -0.012(2)
C5 0.073(4) 0.052(3) 0.070(4) 0.045(3) -0.005(3) 0.005(3)
F1 0.047(2) 0.070(3) 0.213(6) 0.0161(19) -0.039(3) -0.044(3)
F2 0.246(6) 0.055(3) 0.072(3) 0.002(3) 0.038(4) 0.009(2)
O4 0.0403(19) 0.074(3) 0.072(3) 0.039(2) 0.0007(17) 0.007(2)
C7 0.030(2) 0.055(3) 0.050(3) 0.020(2) -0.002(2) 0.003(2)
C1 0.036(3) 0.043(3) 0.067(3) 0.012(2) 0.014(3) -0.001(3)
O2 0.057(3) 0.155(5) 0.108(4) 0.045(3) 0.032(3) 0.093(4)
C2 0.030(2) 0.040(2) 0.042(2) 0.0176(19) 0.0001(19) -0.010(2)
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
O2 S1 O4 111.1(3)
O2 S1 O3 114.0(3)
O4 S1 O3 113.1(3)
O2 S1 O1 103.0(4)
O4 S1 O1 108.5(3)
O3 S1 O1 106.3(2)
C2 N1 C3 108.6(4)
C2 N1 H1A 125.7
C3 N1 H1A 125.7
C2 N2 C8 108.5(3)
C2 N2 H2A 125.8
C8 N2 H2A 125.8
N1 C3 C8 107.2(4)
N1 C3 C4 132.5(4)
C8 C3 C4 120.3(5)
C7 C8 N2 132.7(4)
C7 C8 C3 121.9(4)
N2 C8 C3 105.4(4)
C5 C4 C3 117.5(5)
C5 C4 H4 121.2
C3 C4 H4 121.2
C7 C6 C5 122.0(5)
C7 C6 H6 119.0
C5 C6 H6 119.0
S1 O1 H1 104(7)
C4 C5 C6 121.9(5)
C4 C5 H5 119.1
C6 C5 H5 119.1
C6 C7 C8 116.5(4)
C6 C7 H7 121.8
C8 C7 H7 121.8
F2 C1 F3 110.5(7)
F2 C1 F1 108.3(6)
F3 C1 F1 105.2(5)
F2 C1 C2 112.0(5)
F3 C1 C2 111.0(4)
F1 C1 C2 109.5(5)
N1 C2 N2 110.3(4)
N1 C2 C1 125.9(4)
N2 C2 C1 123.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.429(5)
S1 O4 1.444(4)
S1 O3 1.456(4)
S1 O1 1.558(5)
N1 C2 1.329(6)
N1 C3 1.388(6)
N1 H1A 0.8600
N2 C2 1.341(6)
N2 C8 1.405(6)
N2 H2A 0.8600
C3 C8 1.407(6)
C3 C4 1.409(7)
C8 C7 1.390(7)
C4 C5 1.348(9)
C4 H4 0.9300
F3 C1 1.304(6)
C6 C7 1.373(8)
C6 C5 1.414(8)
C6 H6 0.9300
O1 H1 0.86(2)
C5 H5 0.9300
F1 C1 1.317(8)
F2 C1 1.258(8)
C7 H7 0.9300
C1 C2 1.499(7)
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 O3 1_655 0.86 1.85 2.707(5) 173
N1 H1A O4 . 0.86 1.88 2.740(7) 174
O1 H1 O2 5_455 0.86(2) 1.86(6) 2.608(7) 145(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657225
