#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/51/2015163.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_2015163
loop_
_publ_author_name
'Xue-Li Zhang'
'Sheng-Run Zheng'
'Yue-Peng Cai'
'Cheng-Yong Su'
_publ_section_title
;
 2,2'-(Iminodimethylene)bis(1H-benzimidazolium)(1+) chloride
;
_journal_coeditor_code           HJ1062
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o642
_journal_page_last               o644
_journal_paper_doi               10.1107/S0108270105021992
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C16 H16 N5 +, Cl -'
_chemical_formula_moiety         'C16 H16 N5, Cl'
_chemical_formula_sum            'C16 H16 Cl N5'
_chemical_formula_weight         313.79
_chemical_name_systematic
;
Bis(1H-benzimidazol-2-ylmethyl)aminium chloride
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                   7.607(2)
_cell_length_b                   13.615(3)
_cell_length_c                   14.544(3)
_cell_measurement_reflns_used    1785
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.56
_cell_measurement_theta_min      2.09
_cell_volume                     1506.3(6)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 1K CCD'
_diffrn_measurement_method       'φ and 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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6569
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.163
_refine_ls_abs_structure_details 'Flack (1983), 637 Friedel pairs?'
_refine_ls_abs_structure_Flack   0.36(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2020
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0266
_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)+(0.0419P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0672
_reflns_number_gt                1771
_reflns_number_total             2020
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hj1062.cif
_cod_data_source_block           I
_cod_database_code               2015163
_cod_database_fobs_code          2015163
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
loop_
_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
_atom_site_type_symbol
N1 -0.0512(2) 0.74555(12) 0.66884(14) 0.0374(4) Uani d . 1 . . N
H1 -0.0009 0.7723 0.7155 0.045 Uiso calc R 1 . . H
N2 -0.1621(2) 0.63180(12) 0.57910(13) 0.0361(4) Uani d . 1 . . N
H2 -0.1942 0.5752 0.5589 0.043 Uiso calc PR 0.50 . . H
N3 0.2418(2) 0.55635(13) 1.02709(13) 0.0371(4) Uani d . 1 . . N
H3 0.2397 0.4944 1.0385 0.044 Uiso calc PR 0.50 . . H
N4 0.2066(2) 0.69743(13) 0.95583(14) 0.0385(5) Uani d . 1 . . N
H4 0.1787 0.7387 0.9135 0.046 Uiso calc R 1 . . H
N5 0.0272(3) 0.61128(13) 0.80927(14) 0.0501(6) Uani d . 1 . . N
H5 -0.0758 0.6242 0.8371 0.060 Uiso calc R 1 . . H
C1 -0.0079(3) 0.57179(15) 0.71900(15) 0.0393(5) Uani d . 1 . . C
H1A -0.0932 0.5191 0.7239 0.047 Uiso calc R 1 . . H
H1B 0.0995 0.5446 0.6936 0.047 Uiso calc R 1 . . H
C2 -0.0771(3) 0.64963(15) 0.65605(16) 0.0349(5) Uani d . 1 . . C
C3 -0.1904(3) 0.72231(16) 0.53660(16) 0.0346(5) Uani d . 1 . . C
C4 -0.2672(3) 0.74615(19) 0.45354(17) 0.0444(6) Uani d . 1 . . C
H4A -0.3166 0.6984 0.4159 0.053 Uiso calc R 1 . . H
C5 -0.2673(3) 0.8434(2) 0.4290(2) 0.0549(7) Uani d . 1 . . C
H5A -0.3177 0.8618 0.3733 0.066 Uiso calc R 1 . . H
C6 -0.1941(4) 0.9153(2) 0.4851(2) 0.0562(8) Uani d . 1 . . C
H6 -0.1951 0.9803 0.4654 0.067 Uiso calc R 1 . . H
C7 -0.1206(3) 0.89294(16) 0.5687(2) 0.0469(6) Uani d . 1 . . C
H7 -0.0737 0.9412 0.6067 0.056 Uiso calc R 1 . . H
C8 -0.1198(3) 0.79431(14) 0.59359(17) 0.0351(5) Uani d . 1 . . C
C9 0.1284(3) 0.54739(17) 0.86727(18) 0.0437(6) Uani d . 1 . . C
H9A 0.2292 0.5230 0.8334 0.052 Uiso calc R 1 . . H
H9B 0.0571 0.4915 0.8851 0.052 Uiso calc R 1 . . H
C10 0.1896(3) 0.59992(15) 0.95112(17) 0.0364(5) Uani d . 1 . . C
C11 0.3012(3) 0.63025(15) 1.08526(17) 0.0361(5) Uani d . 1 . . C
C12 0.3706(3) 0.62602(17) 1.17369(18) 0.0448(6) Uani d . 1 . . C
H12 0.3865 0.5664 1.2038 0.054 Uiso calc R 1 . . H
C13 0.4146(3) 0.71369(19) 1.21459(19) 0.0505(7) Uani d . 1 . . C
H13 0.4630 0.7134 1.2733 0.061 Uiso calc R 1 . . H
C14 0.3881(3) 0.80322(19) 1.1696(2) 0.0549(7) Uani d . 1 . . C
H14 0.4187 0.8611 1.1995 0.066 Uiso calc R 1 . . H
C15 0.3187(3) 0.80842(17) 1.0828(2) 0.0479(6) Uani d . 1 . . C
H15 0.3004 0.8682 1.0534 0.058 Uiso calc R 1 . . H
C16 0.2773(3) 0.72020(16) 1.04122(17) 0.0387(5) Uani d . 1 . . C
Cl1 0.09411(8) 0.88137(4) 0.82646(5) 0.04764(17) Uani d . 1 . . Cl
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'
Cl Cl 0.1484 0.1585 '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
C2 N1 C8 107.71(19)
C2 N1 H1 126.1
C8 N1 H1 126.1
C2 N2 C3 106.84(18)
C2 N2 H2 126.6
C3 N2 H2 126.6
C10 N3 C11 106.43(18)
C10 N3 H3 126.8
C11 N3 H3 126.8
C10 N4 C16 107.78(19)
C10 N4 H4 126.1
C16 N4 H4 126.1
C9 N5 C1 114.08(18)
C9 N5 H5 108.7
C1 N5 H5 108.7
N5 C1 C2 110.96(17)
N5 C1 H1A 109.4
C2 C1 H1A 109.4
N5 C1 H1B 109.4
C2 C1 H1B 109.4
H1A C1 H1B 108.0
N2 C2 N1 111.83(19)
N2 C2 C1 124.26(19)
N1 C2 C1 123.8(2)
C4 C3 C8 121.3(2)
C4 C3 N2 131.3(2)
C8 C3 N2 107.4(2)
C5 C4 C3 117.1(2)
C5 C4 H4A 121.5
C3 C4 H4A 121.5
C4 C5 C6 121.8(3)
C4 C5 H5A 119.1
C6 C5 H5A 119.1
C7 C6 C5 121.8(2)
C7 C6 H6 119.1
C5 C6 H6 119.1
C6 C7 C8 116.5(2)
C6 C7 H7 121.7
C8 C7 H7 121.7
N1 C8 C7 132.2(2)
N1 C8 C3 106.20(17)
C7 C8 C3 121.6(2)
N5 C9 C10 110.98(18)
N5 C9 H9A 109.4
C10 C9 H9A 109.4
N5 C9 H9B 109.4
C10 C9 H9B 109.4
H9A C9 H9B 108.0
N3 C10 N4 112.1(2)
N3 C10 C9 124.46(19)
N4 C10 C9 123.4(2)
N3 C11 C12 131.0(2)
N3 C11 C16 108.3(2)
C12 C11 C16 120.7(2)
C13 C12 C11 117.2(2)
C13 C12 H12 121.4
C11 C12 H12 121.4
C12 C13 C14 121.3(3)
C12 C13 H13 119.4
C14 C13 H13 119.4
C15 C14 C13 122.1(3)
C15 C14 H14 118.9
C13 C14 H14 118.9
C14 C15 C16 116.5(2)
C14 C15 H15 121.7
C16 C15 H15 121.7
C15 C16 N4 132.4(2)
C15 C16 C11 122.2(2)
N4 C16 C11 105.38(19)
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
N1 C2 . 1.334(3) y
N1 C8 . 1.382(3) y
N1 H1 . 0.86 ?
N2 C2 . 1.315(3) y
N2 C3 . 1.395(3) y
N2 H2 . 0.86 ?
N3 C10 . 1.315(3) y
N3 C11 . 1.390(3) y
N3 H3 . 0.86 ?
N4 C10 . 1.336(3) y
N4 C16 . 1.388(3) y
N4 H4 . 0.86 ?
N5 C9 . 1.436(3) y
N5 C1 . 1.444(3) y
N5 H5 . 0.90 ?
C1 C2 . 1.496(3) ?
C1 H1A . 0.97 ?
C1 H1B . 0.97 ?
C3 C4 . 1.381(3) ?
C3 C8 . 1.392(3) ?
C4 C5 . 1.372(4) ?
C4 H4A . 0.93 ?
C5 C6 . 1.390(4) ?
C5 H5A . 0.93 ?
C6 C7 . 1.373(4) ?
C6 H6 . 0.93 ?
C7 C8 . 1.391(3) ?
C7 H7 . 0.93 ?
C9 C10 . 1.489(3) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C11 C12 . 1.391(3) ?
C11 C16 . 1.394(3) ?
C12 C13 . 1.375(3) ?
C12 H12 . 0.93 ?
C13 C14 . 1.398(4) ?
C13 H13 . 0.93 ?
C14 C15 . 1.370(4) ?
C14 H14 . 0.93 ?
C15 C16 . 1.381(3) ?
C15 H15 . 0.93 ?
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
_geom_hbond_publ_flag
N1 H1 Cl1 . 0.86 2.31 3.146(2) 164 y
N2 H2 N3 2_564 0.86 1.89 2.739(2) 172 y
N3 H3 N2 2_565 0.86 1.91 2.739(2) 161 y
N4 H4 Cl1 . 0.86 2.41 3.247(2) 166 y
N5 H5 Cl1 4_465 0.90 2.52 3.306(3) 147 y
