#------------------------------------------------------------------------------
#$Date: 2016-02-19 23:18:51 +0100 (vie 19 de feb de 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/94/2019410.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2019410
loop_
_publ_author_name
'Li, Ai-Guo'
'Liu, Qi-Kui'
'Li, Yan-An'
'Liu, Zhi-Xian'
'Dong, Yu-Bin'
_publ_section_title
;
 Three one-dimensional coordination polymers based on
 1,1'-bis(pyridin-4-ylmethyl)-2,2'-bi-1H-benzimidazole and
 HgX₂ (X = Cl, Br and I)
;
_journal_coeditor_code           GZ3240
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              37
_journal_page_last               42
_journal_paper_doi               10.1107/S2053229613031598
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C26 H20 N6'
_chemical_formula_moiety         'C26 H20 N6'
_chemical_formula_sum            'C26 H20 N6'
_chemical_formula_weight         416.48
_chemical_name_systematic
;
1,1'-Bis(pyridin-4-ylmethyl)-2,2'-bi-1H-benzimidazole
;
_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           SHELXL97
_cell_angle_alpha                106.389(5)
_cell_angle_beta                 103.167(5)
_cell_angle_gamma                98.409(5)
_cell_formula_units_Z            2
_cell_length_a                   10.094(4)
_cell_length_b                   10.183(4)
_cell_length_c                   10.972(4)
_cell_measurement_reflns_used    1073
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.591
_cell_measurement_theta_min      2.413
_cell_volume                     1026.4(7)
_computing_cell_refinement       'SMART (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0689
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5451
_diffrn_reflns_theta_full        25.51
_diffrn_reflns_theta_max         25.51
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.284
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.0774
_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)+(0.0943P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1788
_refine_ls_wR_factor_ref         0.1997
_reflns_number_gt                2341
_reflns_number_total             3762
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gz3240sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1026.4(6)
_cod_database_code               2019410
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
C C1 0.4589(4) -0.0172(4) 0.1635(4) 0.0661(10) Uani d . 1 1
H H1 0.4161 -0.1078 0.1552 0.079 Uiso calc R 1 1
C C2 0.3778(4) 0.0619(3) 0.1108(3) 0.0568(9) Uani d . 1 1
H H2 0.2827 0.0254 0.0703 0.068 Uiso calc R 1 1
C C3 0.4378(3) 0.1945(3) 0.1182(3) 0.0427(7) Uani d . 1 1
C C4 0.5782(3) 0.2430(3) 0.1807(3) 0.0535(9) Uani d . 1 1
H H4 0.6240 0.3325 0.1887 0.064 Uiso calc R 1 1
C C5 0.6503(4) 0.1551(4) 0.2316(3) 0.0600(9) Uani d . 1 1
H H5 0.7455 0.1890 0.2733 0.072 Uiso calc R 1 1
C C6 0.3519(3) 0.2804(3) 0.0548(3) 0.0503(8) Uani d . 1 1
H H6A 0.3428 0.2499 -0.0394 0.060 Uiso calc R 1 1
H H6B 0.2590 0.2622 0.0656 0.060 Uiso calc R 1 1
C C7 0.4875(3) 0.5212(3) 0.0652(3) 0.0414(7) Uani d . 1 1
C C8 0.4107(3) 0.5116(3) 0.2359(3) 0.0446(8) Uani d . 1 1
C C9 0.4877(3) 0.6449(3) 0.2585(3) 0.0468(8) Uani d . 1 1
C C10 0.5095(4) 0.7521(4) 0.3783(3) 0.0604(9) Uani d . 1 1
H H10 0.5604 0.8422 0.3948 0.072 Uiso calc R 1 1
C C11 0.4526(4) 0.7180(4) 0.4694(4) 0.0660(10) Uani d . 1 1
H H11 0.4671 0.7864 0.5508 0.079 Uiso calc R 1 1
C C12 0.3733(4) 0.5841(4) 0.4454(4) 0.0637(10) Uani d . 1 1
H H12 0.3338 0.5668 0.5097 0.076 Uiso calc R 1 1
C C13 0.3525(3) 0.4777(4) 0.3292(3) 0.0551(9) Uani d . 1 1
H H13 0.3020 0.3876 0.3135 0.066 Uiso calc R 1 1
C C14 0.0140(3) 0.5264(3) 0.5713(3) 0.0413(7) Uani d . 1 1
C C15 0.0878(3) 0.5416(3) 0.7811(3) 0.0456(8) Uani d . 1 1
C C16 0.0232(3) 0.6517(3) 0.7687(3) 0.0473(8) Uani d . 1 1
C C17 0.0148(4) 0.7520(4) 0.8792(4) 0.0612(10) Uani d . 1 1
H H17 -0.0283 0.8252 0.8715 0.073 Uiso calc R 1 1
C C18 0.0719(4) 0.7413(4) 1.0015(4) 0.0678(11) Uani d . 1 1
H H18 0.0675 0.8079 1.0776 0.081 Uiso calc R 1 1
C C19 0.1369(4) 0.6304(4) 1.0125(4) 0.0678(11) Uani d . 1 1
H H19 0.1758 0.6259 1.0962 0.081 Uiso calc R 1 1
C C20 0.1445(3) 0.5300(4) 0.9045(3) 0.0580(9) Uani d . 1 1
H H20 0.1861 0.4560 0.9126 0.070 Uiso calc R 1 1
C C21 0.1332(3) 0.3328(3) 0.6268(3) 0.0511(8) Uani d . 1 1
H H21A 0.2264 0.3508 0.6857 0.061 Uiso calc R 1 1
H H21B 0.1399 0.3066 0.5367 0.061 Uiso calc R 1 1
C C22 0.0419(3) 0.2130(3) 0.6430(3) 0.0448(8) Uani d . 1 1
C C23 -0.1013(3) 0.1973(4) 0.6203(3) 0.0555(9) Uani d . 1 1
H H23 -0.1450 0.2643 0.5966 0.067 Uiso calc R 1 1
C C24 -0.1775(4) 0.0819(4) 0.6332(4) 0.0681(11) Uani d . 1 1
H H24 -0.2732 0.0739 0.6181 0.082 Uiso calc R 1 1
C C25 0.0122(5) -0.0037(4) 0.6856(4) 0.0721(11) Uani d . 1 1
H H25 0.0527 -0.0737 0.7067 0.087 Uiso calc R 1 1
C C26 0.0983(4) 0.1086(3) 0.6771(3) 0.0538(9) Uani d . 1 1
H H26 0.1939 0.1143 0.6942 0.065 Uiso calc R 1 1
N N1 0.5940(3) 0.0277(3) 0.2252(3) 0.0631(8) Uani d . 1 1
N N2 0.4121(3) 0.4319(2) 0.1107(2) 0.0440(6) Uani d . 1 1
N N3 0.5341(3) 0.6494(3) 0.1504(2) 0.0491(7) Uani d . 1 1
N N4 -0.0216(3) 0.6393(3) 0.6362(2) 0.0480(7) Uani d . 1 1
N N5 0.0810(3) 0.4621(2) 0.6554(2) 0.0454(7) Uani d . 1 1
N N6 -0.1243(4) -0.0196(3) 0.6660(3) 0.0762(10) Uani d . 1 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
N1 C1 C2 . 124.1(3)
N1 C1 H1 . 118.0
C2 C1 H1 . 118.0
C3 C2 C1 . 119.6(3)
C3 C2 H2 . 120.2
C1 C2 H2 . 120.2
C2 C3 C4 . 117.4(3)
C2 C3 C6 . 120.4(3)
C4 C3 C6 . 122.1(3)
C3 C4 C5 . 118.4(3)
C3 C4 H4 . 120.8
C5 C4 H4 . 120.8
N1 C5 C4 . 124.8(3)
N1 C5 H5 . 117.6
C4 C5 H5 . 117.6
N2 C6 C3 . 113.4(2)
N2 C6 H6A . 108.9
C3 C6 H6A . 108.9
N2 C6 H6B . 108.9
C3 C6 H6B . 108.9
H6A C6 H6B . 107.7
N3 C7 N2 . 113.0(3)
N3 C7 C7 2_665 123.4(3)
N2 C7 C7 2_665 123.6(3)
C9 C8 C13 . 122.5(3)
C9 C8 N2 . 105.6(3)
C13 C8 N2 . 132.0(3)
N3 C9 C8 . 110.5(3)
N3 C9 C10 . 129.0(3)
C8 C9 C10 . 120.5(3)
C11 C10 C9 . 116.7(3)
C11 C10 H10 . 121.6
C9 C10 H10 . 121.6
C10 C11 C12 . 122.5(3)
C10 C11 H11 . 118.7
C12 C11 H11 . 118.7
C13 C12 C11 . 121.4(3)
C13 C12 H12 . 119.3
C11 C12 H12 . 119.3
C12 C13 C8 . 116.4(3)
C12 C13 H13 . 121.8
C8 C13 H13 . 121.8
N4 C14 N5 . 112.1(3)
N4 C14 C14 2_566 124.4(3)
N5 C14 C14 2_566 123.4(3)
N5 C15 C20 . 132.3(3)
N5 C15 C16 . 106.5(3)
C20 C15 C16 . 121.3(3)
C17 C16 N4 . 130.2(3)
C17 C16 C15 . 120.5(3)
N4 C16 C15 . 109.3(3)
C18 C17 C16 . 118.2(4)
C18 C17 H17 . 120.9
C16 C17 H17 . 120.9
C17 C18 C19 . 120.6(3)
C17 C18 H18 . 119.7
C19 C18 H18 . 119.7
C20 C19 C18 . 121.8(4)
C20 C19 H19 . 119.1
C18 C19 H19 . 119.1
C19 C20 C15 . 117.5(4)
C19 C20 H20 . 121.2
C15 C20 H20 . 121.2
N5 C21 C22 . 112.8(2)
N5 C21 H21A . 109.0
C22 C21 H21A . 109.0
N5 C21 H21B . 109.0
C22 C21 H21B . 109.0
H21A C21 H21B . 107.8
C26 C22 C23 . 116.7(3)
C26 C22 C21 . 120.1(3)
C23 C22 C21 . 123.1(3)
C24 C23 C22 . 119.2(3)
C24 C23 H23 . 120.4
C22 C23 H23 . 120.4
N6 C24 C23 . 124.7(4)
N6 C24 H24 . 117.7
C23 C24 H24 . 117.7
N6 C25 C26 . 124.8(3)
N6 C25 H25 . 117.6
C26 C25 H25 . 117.6
C25 C26 C22 . 119.4(3)
C25 C26 H26 . 120.3
C22 C26 H26 . 120.3
C5 N1 C1 . 115.6(3)
C7 N2 C8 . 106.0(2)
C7 N2 C6 . 131.4(3)
C8 N2 C6 . 122.4(3)
C7 N3 C9 . 105.0(3)
C14 N4 C16 . 105.8(3)
C15 N5 C14 . 106.3(3)
C15 N5 C21 . 122.8(3)
C14 N5 C21 . 130.8(3)
C25 N6 C24 . 115.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.323(4)
C1 C2 . 1.376(5)
C1 H1 . 0.9300
C2 C3 . 1.369(4)
C2 H2 . 0.9300
C3 C4 . 1.372(4)
C3 C6 . 1.513(4)
C4 C5 . 1.389(5)
C4 H4 . 0.9300
C5 N1 . 1.314(4)
C5 H5 . 0.9300
C6 N2 . 1.466(4)
C6 H6A . 0.9700
C6 H6B . 0.9700
C7 N3 . 1.316(4)
C7 N2 . 1.372(4)
C7 C7 2_665 1.464(6)
C8 C9 . 1.386(4)
C8 C13 . 1.388(4)
C8 N2 . 1.389(4)
C9 N3 . 1.380(4)
C9 C10 . 1.399(4)
C10 C11 . 1.360(5)
C10 H10 . 0.9300
C11 C12 . 1.397(5)
C11 H11 . 0.9300
C12 C13 . 1.370(5)
C12 H12 . 0.9300
C13 H13 . 0.9300
C14 N4 . 1.317(4)
C14 N5 . 1.387(4)
C14 C14 2_566 1.448(6)
C15 N5 . 1.369(4)
C15 C20 . 1.390(4)
C15 C16 . 1.399(4)
C16 C17 . 1.377(4)
C16 N4 . 1.383(4)
C17 C18 . 1.376(5)
C17 H17 . 0.9300
C18 C19 . 1.406(5)
C18 H18 . 0.9300
C19 C20 . 1.355(5)
C19 H19 . 0.9300
C20 H20 . 0.9300
C21 N5 . 1.468(4)
C21 C22 . 1.495(4)
C21 H21A . 0.9700
C21 H21B . 0.9700
C22 C26 . 1.378(4)
C22 C23 . 1.387(4)
C23 C24 . 1.368(5)
C23 H23 . 0.9300
C24 N6 . 1.330(5)
C24 H24 . 0.9300
C25 N6 . 1.324(5)
C25 C26 . 1.370(5)
C25 H25 . 0.9300
C26 H26 . 0.9300
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
N1 C1 C2 C3 . 1.5(6)
C1 C2 C3 C4 . -0.8(5)
C1 C2 C3 C6 . 176.9(3)
C2 C3 C4 C5 . 0.2(5)
C6 C3 C4 C5 . -177.5(3)
C3 C4 C5 N1 . -0.3(5)
C2 C3 C6 N2 . 158.5(3)
C4 C3 C6 N2 . -23.9(4)
C13 C8 C9 N3 . 179.5(3)
N2 C8 C9 N3 . 0.9(3)
C13 C8 C9 C10 . -0.2(5)
N2 C8 C9 C10 . -178.8(3)
N3 C9 C10 C11 . -179.2(3)
C8 C9 C10 C11 . 0.4(5)
C9 C10 C11 C12 . -1.4(5)
C10 C11 C12 C13 . 2.2(5)
C11 C12 C13 C8 . -1.9(5)
C9 C8 C13 C12 . 0.9(5)
N2 C8 C13 C12 . 179.1(3)
N5 C15 C16 C17 . -179.1(3)
C20 C15 C16 C17 . 0.3(5)
N5 C15 C16 N4 . -0.4(3)
C20 C15 C16 N4 . 179.0(3)
N4 C16 C17 C18 . -178.2(3)
C15 C16 C17 C18 . 0.2(5)
C16 C17 C18 C19 . 0.0(5)
C17 C18 C19 C20 . -0.8(6)
C18 C19 C20 C15 . 1.2(5)
N5 C15 C20 C19 . 178.3(3)
C16 C15 C20 C19 . -1.0(5)
N5 C21 C22 C26 . -151.8(3)
N5 C21 C22 C23 . 30.8(4)
C26 C22 C23 C24 . 0.3(5)
C21 C22 C23 C24 . 177.8(3)
C22 C23 C24 N6 . -0.4(6)
N6 C25 C26 C22 . -1.5(6)
C23 C22 C26 C25 . 0.6(5)
C21 C22 C26 C25 . -177.1(3)
C4 C5 N1 C1 . 0.9(5)
C2 C1 N1 C5 . -1.5(6)
N3 C7 N2 C8 . 0.3(3)
C7 C7 N2 C8 2_665 -179.1(3)
N3 C7 N2 C6 . -174.3(3)
C7 C7 N2 C6 2_665 6.3(5)
C9 C8 N2 C7 . -0.7(3)
C13 C8 N2 C7 . -179.1(3)
C9 C8 N2 C6 . 174.5(2)
C13 C8 N2 C6 . -4.0(5)
C3 C6 N2 C7 . 101.2(3)
C3 C6 N2 C8 . -72.6(4)
N2 C7 N3 C9 . 0.3(3)
C7 C7 N3 C9 2_665 179.7(3)
C8 C9 N3 C7 . -0.8(3)
C10 C9 N3 C7 . 178.9(3)
N5 C14 N4 C16 . 0.1(3)
C14 C14 N4 C16 2_566 179.6(3)
C17 C16 N4 C14 . 178.8(3)
C15 C16 N4 C14 . 0.2(3)
C20 C15 N5 C14 . -178.9(3)
C16 C15 N5 C14 . 0.4(3)
C20 C15 N5 C21 . 3.2(5)
C16 C15 N5 C21 . -177.5(3)
N4 C14 N5 C15 . -0.4(3)
C14 C14 N5 C15 2_566 -179.9(3)
N4 C14 N5 C21 . 177.3(3)
C14 C14 N5 C21 2_566 -2.2(6)
C22 C21 N5 C15 . 72.9(4)
C22 C21 N5 C14 . -104.5(3)
C26 C25 N6 C24 . 1.4(6)
C23 C24 N6 C25 . -0.4(6)
