#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/49/2214942.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_2214942
loop_
_publ_author_name
'Yang, Shu-Ping'
'Wang, Da-Qi'
'Han, Li-Jun'
'Xia, Hai-Tao'
_publ_section_title
;
 1-(4-Chlorobenzyl)-2-(4-chlorophenyl)-1H-benzimidazole
;
_journal_coeditor_code           AT2364
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3758
_journal_page_last               o3758
_journal_paper_doi               10.1107/S1600536807038871
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C20 H14 Cl2 N2'
_chemical_formula_moiety         'C20 H14 Cl2 N2'
_chemical_formula_sum            'C20 H14 Cl2 N2'
_chemical_formula_weight         353.23
_chemical_melting_point          450
_chemical_name_systematic
;
1-(4-Chlorobenzyl)-2-(4-chlorophenyl)-1H-benzimidazole
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 90.936(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.6427(17)
_cell_length_b                   5.4420(7)
_cell_length_c                   13.2339(19)
_cell_measurement_reflns_used    1152
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.34
_cell_measurement_theta_min      2.311
_cell_volume                     838.4(2)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0575
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4248
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.390
_exptl_absorpt_correction_T_max  0.9438
_exptl_absorpt_correction_T_min  0.8350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.185
_refine_ls_abs_structure_details 'Flack (1983), 1102 Freidel pairs'
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2749
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0423
_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)+(0.0295P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0858
_reflns_number_gt                1744
_reflns_number_total             2749
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2364.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2214942
_cod_database_fobs_code          2214942
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
Cl Cl1 0.33404(9) 0.0815(2) 0.63346(7) 0.0884(4) Uani d . 1
Cl Cl2 0.75909(8) 1.0489(3) 0.12846(9) 0.1146(5) Uani d . 1
N N1 0.2015(2) 0.8712(5) 0.24471(19) 0.0480(7) Uani d . 1
N N2 0.0955(2) 1.0188(6) 0.3711(2) 0.0587(8) Uani d . 1
C C1 0.1724(3) 0.8546(7) 0.3452(2) 0.0481(9) Uani d . 1
C C2 0.0722(3) 1.1501(6) 0.2833(3) 0.0549(10) Uani d . 1
C C3 0.1370(2) 1.0590(7) 0.2042(2) 0.0499(8) Uani d . 1
C C4 0.1289(3) 1.1528(7) 0.1067(3) 0.0618(10) Uani d . 1
H H4 0.1722 1.0892 0.0543 0.074 Uiso calc R 1
C C5 0.0540(3) 1.3436(8) 0.0918(3) 0.0710(12) Uani d . 1
H H5 0.0457 1.4107 0.0274 0.085 Uiso calc R 1
C C6 -0.0100(3) 1.4397(8) 0.1699(4) 0.0788(13) Uani d . 1
H H6 -0.0592 1.5710 0.1568 0.095 Uiso calc R 1
C C7 -0.0027(3) 1.3453(8) 0.2671(3) 0.0698(11) Uani d . 1
H H7 -0.0460 1.4099 0.3192 0.084 Uiso calc R 1
C C8 0.2738(3) 0.7104(6) 0.1855(2) 0.0545(9) Uani d . 1
H H8A 0.2384 0.6883 0.1193 0.065 Uiso calc R 1
H H8B 0.2772 0.5507 0.2180 0.065 Uiso calc R 1
C C9 0.3948(3) 0.8033(6) 0.1723(2) 0.0439(8) Uani d . 1
C C10 0.4364(3) 1.0114(7) 0.2183(2) 0.0596(10) Uani d . 1
H H10 0.3889 1.1036 0.2595 0.071 Uiso calc R 1
C C11 0.5489(3) 1.0852(8) 0.2038(3) 0.0680(10) Uani d . 1
H H11 0.5764 1.2271 0.2350 0.082 Uiso calc R 1
C C12 0.6190(3) 0.9516(8) 0.1443(3) 0.0657(11) Uani d . 1
C C13 0.5794(3) 0.7433(8) 0.0987(3) 0.0681(11) Uani d . 1
H H13 0.6278 0.6500 0.0587 0.082 Uiso calc R 1
C C14 0.4680(3) 0.6721(6) 0.1120(2) 0.0579(10) Uani d . 1
H H14 0.4410 0.5315 0.0795 0.069 Uiso calc R 1
C C15 0.2178(3) 0.6688(6) 0.4160(2) 0.0506(9) Uani d . 1
C C16 0.3296(3) 0.5778(8) 0.4130(2) 0.0588(9) Uani d . 1
H H16 0.3803 0.6379 0.3653 0.071 Uiso calc R 1
C C17 0.3657(3) 0.3989(7) 0.4805(3) 0.0642(11) Uani d . 1
H H17 0.4397 0.3357 0.4772 0.077 Uiso calc R 1
C C18 0.2917(3) 0.3150(7) 0.5521(2) 0.0579(10) Uani d . 1
C C19 0.1828(3) 0.4092(7) 0.5594(3) 0.0609(10) Uani d . 1
H H19 0.1339 0.3547 0.6096 0.073 Uiso calc R 1
C C20 0.1469(3) 0.5865(8) 0.4911(2) 0.0587(9) Uani d . 1
H H20 0.0734 0.6515 0.4959 0.070 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'
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
C3 N1 C1 106.5(3)
C3 N1 C8 123.8(3)
C1 N1 C8 129.3(3)
C1 N2 C2 104.9(3)
N2 C1 N1 112.7(3)
N2 C1 C15 122.8(3)
N1 C1 C15 124.5(3)
N2 C2 C7 129.6(4)
N2 C2 C3 110.2(3)
C7 C2 C3 120.2(3)
N1 C3 C4 131.7(3)
N1 C3 C2 105.7(3)
C4 C3 C2 122.6(4)
C5 C4 C3 116.5(4)
C5 C4 H4 121.8
C3 C4 H4 121.8
C4 C5 C6 121.9(4)
C4 C5 H5 119.1
C6 C5 H5 119.1
C7 C6 C5 121.7(4)
C7 C6 H6 119.1
C5 C6 H6 119.1
C6 C7 C2 117.2(4)
C6 C7 H7 121.4
C2 C7 H7 121.4
N1 C8 C9 114.2(3)
N1 C8 H8A 108.7
C9 C8 H8A 108.7
N1 C8 H8B 108.7
C9 C8 H8B 108.7
H8A C8 H8B 107.6
C10 C9 C14 117.9(3)
C10 C9 C8 123.4(3)
C14 C9 C8 118.7(3)
C9 C10 C11 120.4(3)
C9 C10 H10 119.8
C11 C10 H10 119.8
C12 C11 C10 120.3(4)
C12 C11 H11 119.8
C10 C11 H11 119.8
C11 C12 C13 120.1(4)
C11 C12 Cl2 119.0(4)
C13 C12 Cl2 120.9(3)
C12 C13 C14 119.6(4)
C12 C13 H13 120.2
C14 C13 H13 120.2
C13 C14 C9 121.7(3)
C13 C14 H14 119.2
C9 C14 H14 119.2
C20 C15 C16 118.4(3)
C20 C15 C1 118.0(3)
C16 C15 C1 123.5(3)
C17 C16 C15 120.4(3)
C17 C16 H16 119.8
C15 C16 H16 119.8
C18 C17 C16 119.6(3)
C18 C17 H17 120.2
C16 C17 H17 120.2
C17 C18 C19 121.1(3)
C17 C18 Cl1 119.9(3)
C19 C18 Cl1 118.9(3)
C18 C19 C20 118.9(3)
C18 C19 H19 120.5
C20 C19 H19 120.5
C15 C20 C19 121.4(3)
C15 C20 H20 119.3
C19 C20 H20 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C18 1.732(4) ?
Cl2 C12 1.731(4) ?
N1 C3 1.373(4) no
N1 C1 1.381(3) no
N1 C8 1.453(4) no
N2 C1 1.314(4) no
N2 C2 1.387(4) ?
C1 C15 1.471(4) ?
C2 C7 1.388(5) ?
C2 C3 1.392(4) ?
C3 C4 1.389(4) ?
C4 C5 1.369(5) ?
C4 H4 0.9300 ?
C5 C6 1.387(5) ?
C5 H5 0.9300 ?
C6 C7 1.386(5) ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C8 C9 1.509(4) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 C10 1.371(4) ?
C9 C14 1.377(4) ?
C10 C11 1.387(4) ?
C10 H10 0.9300 ?
C11 C12 1.354(5) ?
C11 H11 0.9300 ?
C12 C13 1.361(5) ?
C13 C14 1.368(4) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C15 C20 1.376(4) ?
C15 C16 1.394(4) ?
C16 C17 1.382(5) ?
C16 H16 0.9300 ?
C17 C18 1.369(4) ?
C17 H17 0.9300 ?
C18 C19 1.373(4) ?
C19 C20 1.382(5) ?
C19 H19 0.9300 ?
C20 H20 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
C11 H11 Cl1 2_666 0.93 2.79 3.701(4) 166.8
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
_geom_torsion_publ_flag
C2 N2 C1 N1 0.3(4) ?
C2 N2 C1 C15 -177.5(3) ?
C3 N1 C1 N2 -0.6(3) ?
C8 N1 C1 N2 -173.5(3) no
C3 N1 C1 C15 177.1(3) ?
C8 N1 C1 C15 4.3(5) no
C1 N2 C2 C7 180.0(3) ?
C1 N2 C2 C3 0.2(4) ?
C1 N1 C3 C4 -178.3(3) ?
C8 N1 C3 C4 -5.0(5) ?
C1 N1 C3 C2 0.7(3) ?
C8 N1 C3 C2 174.0(3) ?
N2 C2 C3 N1 -0.6(3) ?
C7 C2 C3 N1 179.6(3) ?
N2 C2 C3 C4 178.5(3) ?
C7 C2 C3 C4 -1.3(5) ?
N1 C3 C4 C5 179.5(3) ?
C2 C3 C4 C5 0.6(5) ?
C3 C4 C5 C6 0.4(5) ?
C4 C5 C6 C7 -0.9(6) ?
C5 C6 C7 C2 0.3(5) ?
N2 C2 C7 C6 -179.0(3) ?
C3 C2 C7 C6 0.8(5) ?
C3 N1 C8 C9 88.7(3) ?
C1 N1 C8 C9 -99.6(4) no
N1 C8 C9 C10 4.8(4) ?
N1 C8 C9 C14 -175.9(3) ?
C14 C9 C10 C11 0.1(5) ?
C8 C9 C10 C11 179.3(3) ?
C9 C10 C11 C12 -0.4(5) ?
C10 C11 C12 C13 -0.2(5) ?
C10 C11 C12 Cl2 -179.7(3) ?
C11 C12 C13 C14 1.0(6) ?
Cl2 C12 C13 C14 -179.5(3) ?
C12 C13 C14 C9 -1.3(5) ?
C10 C9 C14 C13 0.8(5) ?
C8 C9 C14 C13 -178.5(3) ?
N2 C1 C15 C20 30.5(5) ?
N1 C1 C15 C20 -147.0(3) ?
N2 C1 C15 C16 -147.4(3) ?
N1 C1 C15 C16 35.1(5) ?
C20 C15 C16 C17 3.7(5) ?
C1 C15 C16 C17 -178.4(3) ?
C15 C16 C17 C18 -1.5(5) ?
C16 C17 C18 C19 -1.3(5) ?
C16 C17 C18 Cl1 177.3(3) ?
C17 C18 C19 C20 1.9(5) ?
Cl1 C18 C19 C20 -176.7(3) ?
C16 C15 C20 C19 -3.1(5) ?
C1 C15 C20 C19 178.9(3) ?
C18 C19 C20 C15 0.3(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4365631
2 PubChem 5194054
