#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/27/2222721.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_2222721
loop_
_publ_author_name
'Cui, Li-Jing'
'Xu, Hai-Jun'
'Pang, Yi-Jie'
_publ_section_title
;
 2-(3-Pyridinio)benzimidazolium pentachloridobismuthate(III)
 monohydrate
;
_journal_coeditor_code           HK2717
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m852
_journal_paper_doi               10.1107/S1600536809024568
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '(C12 H11 N3) [Bi Cl5], H2 O'
_chemical_formula_moiety         'C12 H11 N3 2+, Bi Cl5 2-, H2 O'
_chemical_formula_sum            'C12 H13 Bi Cl5 N3 O'
_chemical_formula_weight         601.48
_chemical_name_systematic
;
2-(3-Pyridinio)benzimidazolium pentachloridobismuthate(III) monohydrate
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.78(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3297(19)
_cell_length_b                   13.391(3)
_cell_length_c                   14.476(3)
_cell_measurement_reflns_used    1647
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      3.03
_cell_volume                     1770.5(7)
_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  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_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  0.1154
_diffrn_reflns_av_sigmaI/netI    0.0955
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17812
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.04
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    10.715
_exptl_absorpt_correction_T_max  0.180
_exptl_absorpt_correction_T_min  0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.281
_refine_diff_density_min         -2.365
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0524
_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)+(0.0236P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1157
_reflns_number_gt                2822
_reflns_number_total             4049
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2717.cif
_cod_data_source_block           I
_cod_original_cell_volume        1770.6(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222721
_cod_database_fobs_code          2222721
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
Bi Bi1 0.50077(4) 0.91031(3) 0.12159(2) 0.03242(14) Uani d . 1 . .
Cl Cl1 0.4928(3) 0.7336(2) 0.1799(2) 0.0538(8) Uani d . 1 . .
Cl Cl2 0.7784(3) 0.8830(2) 0.1188(2) 0.0516(8) Uani d . 1 . .
Cl Cl3 0.4576(3) 0.8682(2) -0.07062(17) 0.0432(6) Uani d . 1 . .
Cl Cl4 0.1991(3) 0.8994(2) 0.09655(18) 0.0461(7) Uani d . 1 . .
Cl Cl5 0.5648(3) 0.9799(2) 0.29758(18) 0.0474(7) Uani d . 1 . .
O O1W 0.6526(7) 0.8372(5) 0.4766(5) 0.060(2) Uani d . 1 . .
H H1WA 0.6470 0.7747 0.4854 0.072 Uiso d R 1 . .
H H1WB 0.6594 0.8234 0.4204 0.072 Uiso d R 1 . .
N N1 0.1677(8) 0.8703(6) 0.6102(6) 0.041(2) Uani d . 1 . .
H H1A 0.2466 0.8720 0.6529 0.049 Uiso calc R 1 . .
N N2 -0.0597(8) 0.8600(6) 0.5442(5) 0.0296(18) Uani d . 1 . .
H H2A -0.1532 0.8541 0.5371 0.036 Uiso calc R 1 . .
N N3 0.0630(10) 0.8739(7) 0.8836(6) 0.046(2) Uani d . 1 . .
H H3B 0.1305 0.8813 0.9333 0.055 Uiso calc R 1 . .
C C1 0.0159(10) 0.8685(8) 0.4712(7) 0.034(2) Uani d . 1 . .
C C2 0.1627(10) 0.8756(8) 0.5147(7) 0.039(3) Uani d . 1 . .
C C3 0.2710(12) 0.8833(10) 0.4600(8) 0.066(4) Uani d . 1 . .
H H3A 0.3700 0.8858 0.4880 0.079 Uiso calc R 1 . .
C C4 0.2242(12) 0.8869(9) 0.3637(9) 0.061(4) Uani d . 1 . .
H H4A 0.2924 0.8938 0.3253 0.073 Uiso calc R 1 . .
C C5 0.0769(12) 0.8804(8) 0.3231(7) 0.049(3) Uani d . 1 . .
H H5A 0.0494 0.8827 0.2577 0.058 Uiso calc R 1 . .
C C6 -0.0300(11) 0.8709(8) 0.3738(7) 0.041(3) Uani d . 1 . .
H H6A -0.1284 0.8662 0.3448 0.049 Uiso calc R 1 . .
C C7 0.0345(9) 0.8625(7) 0.6271(7) 0.030(2) Uani d . 1 . .
C C8 -0.0055(10) 0.8596(7) 0.7183(7) 0.030(2) Uani d . 1 . .
C C9 0.1021(11) 0.8701(8) 0.8005(7) 0.042(3) Uani d . 1 . .
H H9A 0.2003 0.8745 0.7970 0.051 Uiso calc R 1 . .
C C10 -0.0742(12) 0.8670(8) 0.8940(7) 0.041(3) Uani d . 1 . .
H H10A -0.0956 0.8702 0.9539 0.050 Uiso calc R 1 . .
C C11 -0.1834(11) 0.8552(8) 0.8174(7) 0.041(3) Uani d . 1 . .
H H11A -0.2800 0.8491 0.8243 0.049 Uiso calc R 1 . .
C C12 -0.1504(10) 0.8524(7) 0.7299(7) 0.032(2) Uani d . 1 . .
H H12A -0.2255 0.8457 0.6771 0.039 Uiso calc R 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 '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
Cl1 Bi1 Cl2 . . 88.33(9) ?
Cl1 Bi1 Cl3 . . 97.85(9) ?
Cl1 Bi1 Cl4 . . 83.99(8) ?
Cl1 Bi1 Cl5 . . 91.41(10) ?
Cl2 Bi1 Cl3 . . 84.18(9) ?
Cl2 Bi1 Cl4 . . 166.23(9) ?
Cl2 Bi1 Cl5 . . 91.96(9) ?
Cl4 Bi1 Cl3 . . 85.56(8) ?
Cl5 Bi1 Cl3 . . 169.84(8) ?
Cl5 Bi1 Cl4 . . 99.63(8) ?
H1WA O1W H1WB . . 87.0 ?
C2 N1 H1A . . 124.7 ?
C7 N1 C2 . . 110.5(8) ?
C7 N1 H1A . . 124.7 ?
C1 N2 H2A . . 125.1 ?
C7 N2 C1 . . 109.7(8) ?
C7 N2 H2A . . 125.1 ?
C9 N3 H3B . . 118.2 ?
C10 N3 C9 . . 123.5(10) ?
C10 N3 H3B . . 118.2 ?
C6 C1 C2 . . 122.0(9) ?
C6 C1 N2 . . 132.4(9) ?
C2 C1 N2 . . 105.5(8) ?
N1 C2 C1 . . 106.2(9) ?
N1 C2 C3 . . 133.4(10) ?
C1 C2 C3 . . 120.3(10) ?
C4 C3 C2 . . 117.2(10) ?
C4 C3 H3A . . 121.4 ?
C2 C3 H3A . . 121.4 ?
C3 C4 C5 . . 120.7(10) ?
C3 C4 H4A . . 119.6 ?
C5 C4 H4A . . 119.6 ?
C6 C5 C4 . . 123.5(10) ?
C6 C5 H5A . . 118.2 ?
C4 C5 H5A . . 118.2 ?
C5 C6 C1 . . 116.2(10) ?
C5 C6 H6A . . 121.9 ?
C1 C6 H6A . . 121.9 ?
N1 C7 N2 . . 107.9(8) ?
N1 C7 C8 . . 126.9(9) ?
N2 C7 C8 . . 125.1(8) ?
C9 C8 C12 . . 116.6(9) ?
C9 C8 C7 . . 120.1(9) ?
C12 C8 C7 . . 123.3(8) ?
N3 C9 C8 . . 119.5(10) ?
N3 C9 H9A . . 120.2 ?
C8 C9 H9A . . 120.2 ?
N3 C10 C11 . . 120.0(10) ?
N3 C10 H10A . . 120.0 ?
C11 C10 H10A . . 120.0 ?
C10 C11 C12 . . 119.3(10) ?
C10 C11 H11A . . 120.4 ?
C12 C11 H11A . . 120.4 ?
C11 C12 C8 . . 121.1(9) ?
C11 C12 H12A . . 119.4 ?
C8 C12 H12A . . 119.4 ?
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
Bi1 Cl1 . 2.519(3) ?
Bi1 Cl2 . 2.624(3) ?
Bi1 Cl3 . 2.787(3) ?
Bi1 Cl4 . 2.767(3) ?
Bi1 Cl5 . 2.664(3) ?
O1W H1WA . 0.8500 ?
O1W H1WB . 0.8500 ?
N1 H1A . 0.8600 ?
N2 H2A . 0.8600 ?
N3 H3B . 0.8600 ?
C1 C6 . 1.389(13) ?
C1 C2 . 1.389(12) ?
C1 N2 . 1.390(11) ?
C2 N1 . 1.376(12) ?
C2 C3 . 1.409(14) ?
C3 C4 . 1.375(15) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.383(14) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.359(13) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 N1 . 1.319(11) ?
C7 N2 . 1.335(10) ?
C7 C8 . 1.443(12) ?
C8 C9 . 1.399(12) ?
C8 C12 . 1.400(12) ?
C9 N3 . 1.327(12) ?
C9 H9A . 0.9300 ?
C10 N3 . 1.322(13) ?
C10 C11 . 1.354(13) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.363(13) ?
C11 H11A . 0.9300 ?
C12 H12A . 0.9300 ?
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 H1A Cl5 3_676 0.86 2.65 3.267(8) 129.6
N1 H1A Cl1 4_576 0.86 2.66 3.302(8) 132.8
N2 H2A O1W 1_455 0.86 1.86 2.680(9) 159.2
N3 H3B Cl4 1_556 0.86 2.33 3.104(9) 149.7
O1W H1WA Cl3 4_576 0.85 2.62 3.292(7) 137.0
O1W H1WB Cl5 . 0.85 2.77 3.190(7) 111.9
