#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/34/2233457.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_2233457
loop_
_publ_author_name
'Liu, Ming-Liang'
_publ_section_title
;
 Bis(2-trifluoromethyl-1H-benzimidazol-3-ium)
 naphthalene-1,5-disulfonate
;
_journal_coeditor_code           GO2042
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o342
_journal_paper_doi               10.1107/S1600536812000049
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '2C8 H6 F3 N2 +, C10 H6 O6 S2 2-'
_chemical_formula_moiety         '2(C8 H6 F3 N2 +), C10 H6 O6 S2 2-'
_chemical_formula_sum            'C26 H18 F6 N4 O6 S2'
_chemical_formula_weight         660.56
_chemical_name_systematic
;
2-Trifluoromethyl-1H-benzimidazol-3-ium naphthalene-1,5-disulfonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.32(3)
_cell_angle_beta                 96.86(3)
_cell_angle_gamma                119.59(3)
_cell_formula_units_Z            1
_cell_length_a                   9.3910(19)
_cell_length_b                   9.4943(19)
_cell_length_c                   9.976(2)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      3.36
_cell_volume                     685.2(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_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'
_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  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7215
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.9214
_exptl_absorpt_correction_T_min  0.9034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.420
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0517P)²+0.2409P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1315
_reflns_number_gt                2361
_reflns_number_total             3136
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            go2042.cif
_cod_data_source_block           I
_cod_database_code               2233457
_cod_database_fobs_code          2233457
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 1.05784(8) 0.72945(9) 0.37188(7) 0.03242(19) Uani d . 1 1 . .
O O1 0.9734(2) 0.8147(3) 0.3414(2) 0.0398(4) Uani d . 1 1 . .
O O2 1.2456(2) 0.8519(2) 0.4164(2) 0.0440(5) Uani d . 1 1 . .
O O3 1.0035(3) 0.6558(3) 0.4750(2) 0.0532(5) Uani d . 1 1 . .
C C11 0.9978(3) 0.5476(3) 0.1973(3) 0.0300(5) Uani d . 1 1 . .
C C12 0.9359(3) 0.3826(3) 0.1952(3) 0.0362(6) Uani d . 1 1 . .
H H12 0.9236 0.3679 0.2817 0.043 Uiso calc R 1 1 . .
C C13 0.8913(4) 0.2364(3) 0.0616(3) 0.0413(6) Uani d . 1 1 . .
H H13 0.8468 0.1234 0.0594 0.050 Uiso calc R 1 1 . .
C C14 0.9117(3) 0.2556(3) -0.0659(3) 0.0365(6) Uani d . 1 1 . .
H H14 0.8816 0.1559 -0.1531 0.044 Uiso calc R 1 1 . .
C C110 1.0219(3) 0.5750(3) 0.0670(3) 0.0286(5) Uani d . 1 1 . .
N N1 0.4697(3) 0.7605(3) 0.4315(2) 0.0360(5) Uani d . 1 1 . .
H H1 0.3796 0.7607 0.4033 0.043 Uiso calc R 1 1 . .
N N3 0.7062(3) 0.7706(3) 0.4334(2) 0.0339(5) Uani d . 1 1 . .
H H3 0.7924 0.7781 0.4066 0.041 Uiso calc R 1 1 . .
C C2 0.5853(3) 0.7790(3) 0.3630(3) 0.0352(6) Uani d . 1 1 A .
C C4 0.4442(4) 0.7162(4) 0.6660(4) 0.0518(7) Uani d . 1 1 . .
H H4 0.3417 0.7094 0.6641 0.062 Uiso calc R 1 1 . .
C C5 0.5303(5) 0.7028(5) 0.7769(4) 0.0608(9) Uani d . 1 1 . .
H H5 0.4851 0.6872 0.8528 0.073 Uiso calc R 1 1 . .
C C6 0.6826(5) 0.7115(5) 0.7797(4) 0.0581(8) Uani d . 1 1 . .
H H6 0.7369 0.7027 0.8579 0.070 Uiso calc R 1 1 . .
C C7 0.7555(4) 0.7326(4) 0.6704(3) 0.0468(7) Uani d . 1 1 . .
H H7 0.8567 0.7366 0.6718 0.056 Uiso calc R 1 1 . .
C C8 0.6707(3) 0.7477(3) 0.5582(3) 0.0335(5) Uani d . 1 1 . .
C C9 0.5194(3) 0.7408(3) 0.5562(3) 0.0353(6) Uani d . 1 1 . .
C C21 0.5768(4) 0.8018(5) 0.2213(4) 0.0523(7) Uani d . 1 1 . .
F F1 0.5176(12) 0.9023(10) 0.2234(8) 0.0857(19) Uani d PU 0.653(12) 1 A 1
F F2 0.4588(17) 0.6460(7) 0.1027(5) 0.119(3) Uani d PU 0.653(12) 1 A 1
F F3 0.7210(9) 0.8792(17) 0.2048(11) 0.113(3) Uani d PU 0.653(12) 1 A 1
F F1A 0.450(2) 0.797(4) 0.1674(19) 0.114(5) Uani d PU 0.347(12) 1 A 2
F F2A 0.590(3) 0.6822(19) 0.1208(11) 0.086(3) Uani d PU 0.347(12) 1 A 2
F F3A 0.720(2) 0.9515(16) 0.2418(15) 0.118(6) Uani d PU 0.347(12) 1 A 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O3 S1 O2 . . 113.71(13)
O3 S1 O1 . . 112.87(11)
O2 S1 O1 . . 110.44(11)
O3 S1 C11 . . 107.83(12)
O2 S1 C11 . . 104.13(11)
O1 S1 C11 . . 107.24(11)
C12 C11 C110 . . 121.5(2)
C12 C11 S1 . . 117.00(18)
C110 C11 S1 . . 121.37(17)
C11 C12 C13 . . 119.2(2)
C11 C12 H12 . . 120.4
C13 C12 H12 . . 120.4
C14 C13 C12 . . 121.4(2)
C14 C13 H13 . . 119.3
C12 C13 H13 . . 119.3
C13 C14 C110 . 2_765 120.9(2)
C13 C14 H14 . . 119.6
C110 C14 H14 2_765 . 119.6
C14 C110 C110 2_765 2_765 118.7(3)
C14 C110 C11 2_765 . 123.1(2)
C110 C110 C11 2_765 . 118.3(3)
C2 N1 C9 . . 107.7(2)
C2 N1 H1 . . 126.2
C9 N1 H1 . . 126.2
C2 N3 C8 . . 108.1(2)
C2 N3 H3 . . 126.0
C8 N3 H3 . . 126.0
N3 C2 N1 . . 111.2(2)
N3 C2 C21 . . 124.5(2)
N1 C2 C21 . . 124.3(2)
C5 C4 C9 . . 116.0(3)
C5 C4 H4 . . 122.0
C9 C4 H4 . . 122.0
C4 C5 C6 . . 122.2(3)
C4 C5 H5 . . 118.9
C6 C5 H5 . . 118.9
C7 C6 C5 . . 121.9(3)
C7 C6 H6 . . 119.0
C5 C6 H6 . . 119.0
C6 C7 C8 . . 116.5(3)
C6 C7 H7 . . 121.7
C8 C7 H7 . . 121.7
N3 C8 C7 . . 132.2(2)
N3 C8 C9 . . 106.2(2)
C7 C8 C9 . . 121.5(2)
N1 C9 C8 . . 106.8(2)
N1 C9 C4 . . 131.4(3)
C8 C9 C4 . . 121.7(3)
F1A C21 F2A . . 110.9(8)
F3 C21 F2 . . 112.5(5)
F1A C21 F3A . . 109.7(11)
F2A C21 F3A . . 99.4(8)
F3 C21 F1 . . 106.2(5)
F2 C21 F1 . . 103.2(5)
F3 C21 C2 . . 113.7(4)
F2 C21 C2 . . 110.7(3)
F1 C21 C2 . . 109.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 O3 . 1.435(2)
S1 O2 . 1.451(2)
S1 O1 . 1.4547(18)
S1 C11 . 1.774(3)
C11 C12 . 1.367(3)
C11 C110 . 1.430(3)
C12 C13 . 1.395(4)
C12 H12 . 0.9300
C13 C14 . 1.366(3)
C13 H13 . 0.9300
C14 C110 2_765 1.414(3)
C14 H14 . 0.9300
C110 C14 2_765 1.414(3)
C110 C110 2_765 1.419(5)
N1 C2 . 1.321(3)
N1 C9 . 1.380(3)
N1 H1 . 0.8600
N3 C2 . 1.312(3)
N3 C8 . 1.384(3)
N3 H3 . 0.8600
C2 C21 . 1.498(4)
C4 C5 . 1.369(5)
C4 C9 . 1.395(4)
C4 H4 . 0.9300
C5 C6 . 1.388(5)
C5 H5 . 0.9300
C6 C7 . 1.373(4)
C6 H6 . 0.9300
C7 C8 . 1.384(4)
C7 H7 . 0.9300
C8 C9 . 1.386(3)
C21 F1A . 1.223(11)
C21 F3 . 1.246(7)
C21 F2A . 1.311(8)
C21 F2 . 1.314(6)
C21 F3A . 1.314(12)
C21 F1 . 1.317(6)
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
N3 H3 O1 . 0.86 1.81 2.661(3) 172
N1 H1 O2 1_455 0.86 1.84 2.650(3) 155
C12 H12 O3 2_766 0.93 2.55 3.440(3) 159
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_4
_geom_torsion
O3 S1 C11 C12 . -8.3(2)
O2 S1 C11 C12 . 112.8(2)
O1 S1 C11 C12 . -130.1(2)
O3 S1 C11 C110 . 174.97(18)
O2 S1 C11 C110 . -63.9(2)
O1 S1 C11 C110 . 53.2(2)
C110 C11 C12 C13 . -1.5(4)
S1 C11 C12 C13 . -178.29(19)
C11 C12 C13 C14 . 1.4(4)
C12 C13 C14 C110 2_765 -0.4(4)
C12 C11 C110 C14 2_765 -179.0(2)
S1 C11 C110 C14 2_765 -2.3(3)
C12 C11 C110 C110 2_765 0.6(4)
S1 C11 C110 C110 2_765 177.3(2)
C8 N3 C2 N1 . -0.9(3)
C8 N3 C2 C21 . -179.5(2)
C9 N1 C2 N3 . 0.7(3)
C9 N1 C2 C21 . 179.3(2)
C9 C4 C5 C6 . -0.5(5)
C4 C5 C6 C7 . -0.6(5)
C5 C6 C7 C8 . 1.0(5)
C2 N3 C8 C7 . -179.3(3)
C2 N3 C8 C9 . 0.7(3)
C6 C7 C8 N3 . 179.7(3)
C6 C7 C8 C9 . -0.4(4)
C2 N1 C9 C8 . -0.2(3)
C2 N1 C9 C4 . -179.7(3)
N3 C8 C9 N1 . -0.3(3)
C7 C8 C9 N1 . 179.8(2)
N3 C8 C9 C4 . 179.2(2)
C7 C8 C9 C4 . -0.7(4)
C5 C4 C9 N1 . -179.5(3)
C5 C4 C9 C8 . 1.1(4)
N3 C2 C21 F1A . 176.3(14)
N1 C2 C21 F1A . -2.1(15)
N3 C2 C21 F3 . -25.8(8)
N1 C2 C21 F3 . 155.8(7)
N3 C2 C21 F2A . 50.4(10)
N1 C2 C21 F2A . -128.0(10)
N3 C2 C21 F2 . 101.9(8)
N1 C2 C21 F2 . -76.5(8)
N3 C2 C21 F3A . -58.3(10)
N1 C2 C21 F3A . 123.3(10)
N3 C2 C21 F1 . -144.7(5)
N1 C2 C21 F1 . 36.9(6)
