#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/78/7217828.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_7217828
loop_
_publ_author_name
'Kempf, Julie'
'Noujeim, Nadim'
'Schmitzer, Andreea R.'
_publ_section_title
;
 2,4,7-triphenylbenzimidazole : the monomeric unit of supramolecular
 helical rod-like transmembrane transporters
;
_journal_name_full               'RSC Advances'
_journal_paper_doi               10.1039/C4RA06887D
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_sum            'C26 H20 Cl4 N2'
_chemical_formula_weight         502.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2022(2)
_cell_length_b                   13.4802(4)
_cell_length_c                   23.7766(7)
_cell_measurement_reflns_used    9469
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.90
_cell_measurement_theta_min      3.72
_cell_volume                     2308.40(12)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL  (Bruker AXS, 2003)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.061
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            31032
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.209
_diffrn_reflns_theta_min         3.718
_diffrn_source                   'Incoatec I\muS Microsource '
_exptl_absorpt_coefficient_mu    4.792
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.4971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       needle
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_ls_abs_structure_details
'Flack, H.D. and Schwarzenbach, D. (1999), XXXX Friedel Pairs'
_refine_ls_abs_structure_Flack   0.027(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0788P)²+0.6880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1136
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                4239
_reflns_number_total             4456
_cod_data_source_file            c4ra06887d2.cif
_cod_data_source_block           JULIE2
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7217828
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.514
_shelx_estimated_absorpt_t_max   0.910
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C2 C 0.9778(5) 0.7827(2) 0.01539(15) 0.0186(7) Uani 1 1 d . .
C4 C 0.9860(5) 0.8901(3) 0.08653(15) 0.0196(7) Uani 1 1 d . .
C5 C 0.9570(5) 0.9421(3) 0.03628(15) 0.0190(7) Uani 1 1 d . .
C6 C 0.9360(5) 1.0459(3) 0.03435(16) 0.0205(7) Uani 1 1 d . .
C7 C 0.9332(5) 1.0914(3) 0.08629(16) 0.0235(7) Uani 1 1 d . .
H7 H 0.9153 1.1611 0.0878 0.028 Uiso 1 1 calc R U
C8 C 0.9554(5) 1.0397(3) 0.13677(16) 0.0231(7) Uani 1 1 d . .
H8 H 0.9526 1.0761 0.1710 0.028 Uiso 1 1 calc R U
C9 C 0.9816(5) 0.9370(3) 0.13942(16) 0.0210(7) Uani 1 1 d . .
C10 C 0.9797(5) 0.6906(3) -0.01775(16) 0.0195(7) Uani 1 1 d . .
C11 C 1.0237(5) 0.6944(3) -0.07527(16) 0.0216(7) Uani 1 1 d . .
H11 H 1.0547 0.7559 -0.0924 0.026 Uiso 1 1 calc R U
C12 C 1.0218(5) 0.6080(3) -0.10705(16) 0.0240(7) Uani 1 1 d . .
H12 H 1.0492 0.6104 -0.1461 0.029 Uiso 1 1 calc R U
C13 C 0.9793(5) 0.5175(3) -0.08142(17) 0.0253(8) Uani 1 1 d . .
H13 H 0.9794 0.4583 -0.1031 0.030 Uiso 1 1 calc R U
C14 C 0.9374(5) 0.5137(3) -0.02495(16) 0.0252(8) Uani 1 1 d . .
H14 H 0.9089 0.4519 -0.0079 0.030 Uiso 1 1 calc R U
C15 C 0.9366(5) 0.6001(3) 0.00740(15) 0.0213(7) Uani 1 1 d . .
H15 H 0.9068 0.5972 0.0463 0.026 Uiso 1 1 calc R U
C16 C 0.9308(5) 1.1050(2) -0.01860(15) 0.0209(7) Uani 1 1 d . .
C17 C 1.0453(5) 1.0818(3) -0.06364(15) 0.0231(7) Uani 1 1 d . .
H17 H 1.1191 1.0234 -0.0622 0.028 Uiso 1 1 calc R U
C18 C 1.0539(6) 1.1425(3) -0.11081(17) 0.0286(8) Uani 1 1 d . .
H18 H 1.1332 1.1258 -0.1413 0.034 Uiso 1 1 calc R U
C19 C 0.9450(6) 1.2283(3) -0.11301(17) 0.0304(8) Uani 1 1 d . .
H19 H 0.9507 1.2705 -0.1449 0.036 Uiso 1 1 calc R U
C20 C 0.8294(6) 1.2514(3) -0.06871(18) 0.0295(8) Uani 1 1 d . .
H20 H 0.7553 1.3097 -0.0704 0.035 Uiso 1 1 calc R U
C21 C 0.8200(6) 1.1901(3) -0.02140(17) 0.0259(8) Uani 1 1 d . .
H21 H 0.7387 1.2061 0.0087 0.031 Uiso 1 1 calc R U
C22 C 0.9931(5) 0.8869(3) 0.19467(15) 0.0205(7) Uani 1 1 d . .
C23 C 0.8905(6) 0.9244(3) 0.23979(16) 0.0251(7) Uani 1 1 d . .
H23 H 0.8116 0.9799 0.2339 0.030 Uiso 1 1 calc R U
C24 C 0.9008(6) 0.8830(3) 0.29257(16) 0.0287(8) Uani 1 1 d . .
H24 H 0.8321 0.9108 0.3228 0.034 Uiso 1 1 calc R U
C25 C 1.0124(6) 0.8002(3) 0.30143(17) 0.0293(9) Uani 1 1 d . .
H25 H 1.0187 0.7704 0.3376 0.035 Uiso 1 1 calc R U
C26 C 1.1140(6) 0.7614(3) 0.25722(17) 0.0278(8) Uani 1 1 d . .
H26 H 1.1900 0.7048 0.2632 0.033 Uiso 1 1 calc R U
C27 C 1.1060(6) 0.8048(3) 0.20398(15) 0.0224(7) Uani 1 1 d . .
H27 H 1.1778 0.7782 0.1740 0.027 Uiso 1 1 calc R U
N1 N 0.9527(4) 0.8730(2) -0.00676(13) 0.0183(6) Uani 1 1 d . .
H1 H 0.911(7) 0.878(3) -0.038(2) 0.022 Uiso 1 1 d . U
N3 N 1.0002(4) 0.7900(2) 0.07070(13) 0.0185(6) Uani 1 1 d . .
H3 H 1.031(7) 0.745(4) 0.0918(19) 0.022 Uiso 1 1 d . U
C28 C 0.6077(6) 0.5983(3) 0.20472(16) 0.0284(8) Uani 1 1 d . .
H28 H 0.4986 0.5836 0.1801 0.034 Uiso 1 1 calc R U
Cl2 Cl 0.81384(14) 0.58337(7) 0.16554(4) 0.0320(2) Uani 1 1 d . .
Cl3 Cl 0.60731(17) 0.51577(10) 0.26239(5) 0.0489(3) Uani 1 1 d . .
Cl4 Cl 0.59265(16) 0.72176(8) 0.22872(5) 0.0386(3) Uani 1 1 d . .
Cl1 Cl 0.73779(11) 0.89438(6) 0.88401(3) 0.0211(2) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
_geom_angle_publ_flag
N3 C2 N1 109.8(3) y
N3 C2 C10 126.3(3) y
N1 C2 C10 123.9(3) y
C5 C4 N3 105.2(3) y
C5 C4 C9 122.2(3) y
N3 C4 C9 132.3(3) y
N1 C5 C4 107.3(3) y
N1 C5 C6 129.9(3) y
C4 C5 C6 122.8(3) y
C7 C6 C5 114.5(3) y
C7 C6 C16 121.2(3) y
C5 C6 C16 124.2(3) y
C6 C7 C8 123.1(3) y
C6 C7 H7 118.5 ?
C8 C7 H7 118.5 ?
C7 C8 C9 123.2(3) y
C7 C8 H8 118.4 ?
C9 C8 H8 118.4 ?
C8 C9 C4 114.1(3) y
C8 C9 C22 120.0(3) y
C4 C9 C22 125.9(3) y
C15 C10 C11 120.0(3) y
C15 C10 C2 120.5(3) y
C11 C10 C2 119.6(3) y
C12 C11 C10 119.8(3) y
C12 C11 H11 120.1 ?
C10 C11 H11 120.1 ?
C11 C12 C13 119.8(3) y
C11 C12 H12 120.1 ?
C13 C12 H12 120.1 ?
C14 C13 C12 120.3(3) y
C14 C13 H13 119.8 ?
C12 C13 H13 119.8 ?
C13 C14 C15 120.5(3) y
C13 C14 H14 119.7 ?
C15 C14 H14 119.7 ?
C10 C15 C14 119.5(3) y
C10 C15 H15 120.2 ?
C14 C15 H15 120.2 ?
C17 C16 C21 119.2(3) y
C17 C16 C6 121.1(3) y
C21 C16 C6 119.5(3) y
C16 C17 C18 121.1(4) y
C16 C17 H17 119.5 ?
C18 C17 H17 119.5 ?
C17 C18 C19 119.5(4) y
C17 C18 H18 120.3 ?
C19 C18 H18 120.3 ?
C20 C19 C18 119.8(4) y
C20 C19 H19 120.1 ?
C18 C19 H19 120.1 ?
C19 C20 C21 120.7(4) y
C19 C20 H20 119.6 ?
C21 C20 H20 119.6 ?
C20 C21 C16 119.7(4) y
C20 C21 H21 120.1 ?
C16 C21 H21 120.1 ?
C27 C22 C23 118.3(3) y
C27 C22 C9 122.5(3) y
C23 C22 C9 119.1(3) y
C24 C23 C22 121.7(4) y
C24 C23 H23 119.2 ?
C22 C23 H23 119.2 ?
C23 C24 C25 119.6(4) y
C23 C24 H24 120.2 ?
C25 C24 H24 120.2 ?
C26 C25 C24 119.6(4) y
C26 C25 H25 120.2 ?
C24 C25 H25 120.2 ?
C25 C26 C27 120.6(4) y
C25 C26 H26 119.7 ?
C27 C26 H26 119.7 ?
C22 C27 C26 120.1(4) y
C22 C27 H27 119.9 ?
C26 C27 H27 119.9 ?
C2 N1 C5 108.5(3) y
C2 N1 H1 119(3) ?
C5 N1 H1 130(3) ?
C2 N3 C4 109.1(3) y
C2 N3 H3 126(3) ?
C4 N3 H3 125(3) ?
CL4 C28 CL2 109.3(2) y
CL4 C28 CL3 110.1(2) y
CL2 C28 CL3 109.8(2) y
CL4 C28 H28 109.2 ?
CL2 C28 H28 109.2 ?
CL3 C28 H28 109.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C2 N3 1.329(5) y
C2 N1 1.338(4) y
C2 C10 1.470(5) y
C4 C5 1.401(5) y
C4 N3 1.404(4) y
C4 C9 1.409(5) y
C5 N1 1.384(5) y
C5 C6 1.408(5) y
C6 C7 1.379(5) y
C6 C16 1.490(5) y
C7 C8 1.397(5) y
C7 H7 0.9500 ?
C8 C9 1.398(5) y
C8 H8 0.9500 ?
C9 C22 1.480(5) y
C10 C15 1.394(5) y
C10 C11 1.405(5) y
C11 C12 1.388(5) y
C11 H11 0.9500 ?
C12 C13 1.398(5) y
C12 H12 0.9500 ?
C13 C14 1.377(6) y
C13 H13 0.9500 ?
C14 C15 1.395(5) y
C14 H14 0.9500 ?
C15 H15 0.9500 ?
C16 C17 1.387(5) y
C16 C21 1.399(5) y
C17 C18 1.390(5) y
C17 H17 0.9500 ?
C18 C19 1.399(6) y
C18 H18 0.9500 ?
C19 C20 1.378(6) y
C19 H19 0.9500 ?
C20 C21 1.398(6) y
C20 H20 0.9500 ?
C21 H21 0.9500 ?
C22 C27 1.391(5) y
C22 C23 1.398(5) y
C23 C24 1.375(6) y
C23 H23 0.9500 ?
C24 C25 1.392(6) y
C24 H24 0.9500 ?
C25 C26 1.383(6) y
C25 H25 0.9500 ?
C26 C27 1.396(5) y
C26 H26 0.9500 ?
C27 H27 0.9500 ?
N1 H1 0.79(5) ?
N3 H3 0.82(5) ?
C28 Cl4 1.763(4) y
C28 Cl2 1.764(4) y
C28 Cl3 1.766(4) y
C28 H28 1.0000 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 CL1 0.79(5) 2.25(5) 3.037(3) 168(5) 1_554 y
N3 H3 CL1 0.82(5) 2.46(5) 3.204(3) 151(4) 3_566 y
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
N3 C4 C5 N1 0.7(4) y
C9 C4 C5 N1 -174.3(3) y
N3 C4 C5 C6 -179.8(3) y
C9 C4 C5 C6 5.1(6) y
N1 C5 C6 C7 175.0(4) y
C4 C5 C6 C7 -4.3(5) y
N1 C5 C6 C16 -9.4(6) y
C4 C5 C6 C16 171.3(3) y
C5 C6 C7 C8 2.0(5) y
C16 C6 C7 C8 -173.8(4) y
C6 C7 C8 C9 -0.3(6) y
C7 C8 C9 C4 0.7(6) y
C7 C8 C9 C22 -176.4(4) y
C5 C4 C9 C8 -3.0(5) y
N3 C4 C9 C8 -176.6(4) y
C5 C4 C9 C22 173.9(3) y
N3 C4 C9 C22 0.4(6) y
N3 C2 C10 C15 24.4(6) y
N1 C2 C10 C15 -155.7(3) y
N3 C2 C10 C11 -156.2(4) y
N1 C2 C10 C11 23.7(5) y
C15 C10 C11 C12 0.8(5) y
C2 C10 C11 C12 -178.6(3) y
C10 C11 C12 C13 -1.2(6) y
C11 C12 C13 C14 0.7(6) y
C12 C13 C14 C15 0.1(6) y
C11 C10 C15 C14 0.0(5) y
C2 C10 C15 C14 179.3(3) y
C13 C14 C15 C10 -0.4(6) y
C7 C6 C16 C17 136.6(4) y
C5 C6 C16 C17 -38.7(5) y
C7 C6 C16 C21 -38.1(5) y
C5 C6 C16 C21 146.6(4) y
C21 C16 C17 C18 1.1(5) y
C6 C16 C17 C18 -173.6(3) y
C16 C17 C18 C19 -0.1(6) y
C17 C18 C19 C20 -0.5(6) y
C18 C19 C20 C21 0.2(6) y
C19 C20 C21 C16 0.8(6) y
C17 C16 C21 C20 -1.5(6) y
C6 C16 C21 C20 173.3(3) y
C8 C9 C22 C27 -145.9(4) y
C4 C9 C22 C27 37.3(6) y
C8 C9 C22 C23 32.5(5) y
C4 C9 C22 C23 -144.3(4) y
C27 C22 C23 C24 0.8(6) y
C9 C22 C23 C24 -177.7(4) y
C22 C23 C24 C25 -1.6(6) y
C23 C24 C25 C26 1.0(6) y
C24 C25 C26 C27 0.2(6) y
C23 C22 C27 C26 0.5(5) y
C9 C22 C27 C26 178.9(4) y
C25 C26 C27 C22 -1.0(6) y
N3 C2 N1 C5 -0.7(4) y
C10 C2 N1 C5 179.4(3) y
C4 C5 N1 C2 -0.1(4) y
C6 C5 N1 C2 -179.5(4) y
N1 C2 N3 C4 1.1(4) y
C10 C2 N3 C4 -178.9(3) y
C5 C4 N3 C2 -1.1(4) y
C9 C4 N3 C2 173.2(4) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199123
