#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/43/2224333.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_2224333
loop_
_publ_author_name
'Zhao, Yu-Ling'
'Yu, Tian-Zhi'
'Meng, Jing'
_publ_section_title
;
 1-[6-(9H-Carbazol-9-yl)hexyl]-2-phenyl-1H-benzimidazole
;
_journal_coeditor_code           JH2111
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3076
_journal_paper_doi               10.1107/S1600536809046820
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C31 H29 N3'
_chemical_formula_moiety         'C31 H29 N3'
_chemical_formula_sum            'C31 H29 N3'
_chemical_formula_weight         443.57
_chemical_melting_point_gt       403
_chemical_melting_point_lt       405
_chemical_name_systematic
;
1-[6-(9H-Carbazol-9-yl)hexyl]-2-phenyl-1H-benzimidazole
;
_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                 96.3120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6623(6)
_cell_length_b                   31.582(2)
_cell_length_c                   8.9187(6)
_cell_measurement_reflns_used    3325
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.30
_cell_measurement_theta_min      2.37
_cell_volume                     2425.1(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13496
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0459
_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)+(0.0541P)²+0.1994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                3374
_reflns_number_total             4757
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2111.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224333
_cod_database_fobs_code          2224333
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
C C1 -0.02475(16) 0.43714(5) 0.59089(17) 0.0523(4) Uani d . 1 . .
C C2 -0.12646(18) 0.40495(6) 0.5389(2) 0.0653(4) Uani d . 1 . .
H H2 -0.1038 0.3866 0.4627 0.078 Uiso calc R 1 . .
C C3 -0.2618(2) 0.40148(7) 0.6050(2) 0.0791(5) Uani d . 1 . .
H H3 -0.3313 0.3800 0.5737 0.095 Uiso calc R 1 . .
C C4 -0.2981(2) 0.42893(7) 0.7167(2) 0.0820(6) Uani d . 1 . .
H H4 -0.3912 0.4256 0.7583 0.098 Uiso calc R 1 . .
C C5 -0.19874(19) 0.46114(6) 0.76719(19) 0.0693(5) Uani d . 1 . .
H H5 -0.2245 0.4798 0.8412 0.083 Uiso calc R 1 . .
C C6 -0.05852(17) 0.46530(5) 0.70515(16) 0.0539(4) Uani d . 1 . .
C C7 0.07318(18) 0.49316(5) 0.73388(16) 0.0543(4) Uani d . 1 . .
C C8 0.1095(2) 0.52700(6) 0.83139(19) 0.0702(5) Uani d . 1 . .
H H8 0.0393 0.5360 0.8964 0.084 Uiso calc R 1 . .
C C9 0.2502(3) 0.54688(7) 0.8303(2) 0.0851(6) Uani d . 1 . .
H H9 0.2746 0.5697 0.8945 0.102 Uiso calc R 1 . .
C C10 0.3566(2) 0.53354(6) 0.7351(2) 0.0851(6) Uani d . 1 . .
H H10 0.4517 0.5473 0.7376 0.102 Uiso calc R 1 . .
C C11 0.3241(2) 0.50022(6) 0.6364(2) 0.0682(5) Uani d . 1 . .
H H11 0.3956 0.4913 0.5726 0.082 Uiso calc R 1 . .
C C12 0.18125(17) 0.48054(5) 0.63596(16) 0.0524(4) Uani d . 1 . .
C C13 0.19565(18) 0.42690(5) 0.42926(17) 0.0581(4) Uani d . 1 . .
H H13A 0.2482 0.4483 0.3758 0.070 Uiso calc R 1 . .
H H13B 0.1172 0.4139 0.3578 0.070 Uiso calc R 1 . .
C C14 0.31251(17) 0.39346(5) 0.48825(18) 0.0567(4) Uani d . 1 . .
H H14A 0.3657 0.3830 0.4055 0.068 Uiso calc R 1 . .
H H14B 0.3895 0.4062 0.5617 0.068 Uiso calc R 1 . .
C C15 0.23723(17) 0.35671(5) 0.56068(18) 0.0548(4) Uani d . 1 . .
H H15A 0.1568 0.3451 0.4879 0.066 Uiso calc R 1 . .
H H15B 0.1870 0.3674 0.6450 0.066 Uiso calc R 1 . .
C C16 0.34575(17) 0.32109(5) 0.61709(19) 0.0592(4) Uani d . 1 . .
H H16A 0.4312 0.3327 0.6839 0.071 Uiso calc R 1 . .
H H16B 0.3888 0.3083 0.5319 0.071 Uiso calc R 1 . .
C C17 0.26530(18) 0.28701(5) 0.70071(17) 0.0571(4) Uani d . 1 . .
H H17A 0.3424 0.2672 0.7459 0.069 Uiso calc R 1 . .
H H17B 0.2156 0.3000 0.7814 0.069 Uiso calc R 1 . .
C C18 0.14417(17) 0.26304(5) 0.59738(16) 0.0545(4) Uani d . 1 . .
H H18A 0.0780 0.2833 0.5395 0.065 Uiso calc R 1 . .
H H18B 0.1966 0.2464 0.5268 0.065 Uiso calc R 1 . .
C C19 -0.07789(17) 0.24836(5) 0.74837(16) 0.0563(4) Uani d . 1 . .
C C20 -0.1313(2) 0.28859(6) 0.7791(2) 0.0696(5) Uani d . 1 . .
H H20 -0.0829 0.3129 0.7484 0.084 Uiso calc R 1 . .
C C21 -0.2595(2) 0.29058(8) 0.8573(2) 0.0839(6) Uani d . 1 . .
H H21 -0.2985 0.3170 0.8801 0.101 Uiso calc R 1 . .
C C22 -0.3322(2) 0.25458(9) 0.9029(2) 0.0886(6) Uani d . 1 . .
H H22 -0.4174 0.2573 0.9572 0.106 Uiso calc R 1 . .
C C23 -0.2812(2) 0.21486(8) 0.8698(2) 0.0789(5) Uani d . 1 . .
H H23 -0.3316 0.1908 0.8994 0.095 Uiso calc R 1 . .
C C24 -0.15163(18) 0.21176(6) 0.79052(18) 0.0615(4) Uani d . 1 . .
C C25 0.04203(18) 0.19127(5) 0.67728(17) 0.0557(4) Uani d . 1 . .
C C26 0.1556(2) 0.16414(5) 0.61244(17) 0.0583(4) Uani d . 1 . .
C C27 0.1020(2) 0.12817(6) 0.5325(2) 0.0752(5) Uani d . 1 . .
H H27 -0.0039 0.1225 0.5171 0.090 Uiso calc R 1 . .
C C28 0.2057(3) 0.10106(6) 0.4763(2) 0.0905(6) Uani d . 1 . .
H H28 0.1690 0.0772 0.4227 0.109 Uiso calc R 1 . .
C C29 0.3625(3) 0.10872(7) 0.4982(2) 0.0906(6) Uani d . 1 . .
H H29 0.4314 0.0900 0.4601 0.109 Uiso calc R 1 . .
C C30 0.4175(2) 0.14419(6) 0.5768(2) 0.0822(6) Uani d . 1 . .
H H30 0.5236 0.1496 0.5915 0.099 Uiso calc R 1 . .
C C31 0.3140(2) 0.17165(5) 0.63358(19) 0.0675(5) Uani d . 1 . .
H H31 0.3513 0.1955 0.6868 0.081 Uiso calc R 1 . .
N N1 0.12011(13) 0.44707(4) 0.54812(14) 0.0530(3) Uani d . 1 . .
N N2 0.04699(14) 0.23494(4) 0.67667(13) 0.0532(3) Uani d . 1 . .
N N3 -0.07470(16) 0.17632(4) 0.74442(15) 0.0653(4) Uani d . 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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 129.25(14) ?
N1 C1 C6 . . 108.82(13) ?
C2 C1 C6 . . 121.92(14) ?
C3 C2 C1 . . 117.02(17) ?
C3 C2 H2 . . 121.5 ?
C1 C2 H2 . . 121.5 ?
C2 C3 C4 . . 122.15(18) ?
C2 C3 H3 . . 118.9 ?
C4 C3 H3 . . 118.9 ?
C5 C4 C3 . . 121.04(16) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C4 C5 C6 . . 118.71(16) ?
C4 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
C5 C6 C1 . . 119.14(15) ?
C5 C6 C7 . . 133.92(15) ?
C1 C6 C7 . . 106.93(12) ?
C8 C7 C12 . . 119.05(15) ?
C8 C7 C6 . . 134.42(15) ?
C12 C7 C6 . . 106.53(13) ?
C9 C8 C7 . . 119.13(17) ?
C9 C8 H8 . . 120.4 ?
C7 C8 H8 . . 120.4 ?
C8 C9 C10 . . 121.08(18) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
C11 C10 C9 . . 121.31(18) ?
C11 C10 H10 . . 119.3 ?
C9 C10 H10 . . 119.3 ?
C10 C11 C12 . . 117.63(17) ?
C10 C11 H11 . . 121.2 ?
C12 C11 H11 . . 121.2 ?
C11 C12 N1 . . 129.06(14) ?
C11 C12 C7 . . 121.78(15) ?
N1 C12 C7 . . 109.16(13) ?
N1 C13 C14 . . 112.91(12) ?
N1 C13 H13A . . 109.0 ?
C14 C13 H13A . . 109.0 ?
N1 C13 H13B . . 109.0 ?
C14 C13 H13B . . 109.0 ?
H13A C13 H13B . . 107.8 ?
C15 C14 C13 . . 112.35(12) ?
C15 C14 H14A . . 109.1 ?
C13 C14 H14A . . 109.1 ?
C15 C14 H14B . . 109.1 ?
C13 C14 H14B . . 109.1 ?
H14A C14 H14B . . 107.9 ?
C14 C15 C16 . . 115.52(12) ?
C14 C15 H15A . . 108.4 ?
C16 C15 H15A . . 108.4 ?
C14 C15 H15B . . 108.4 ?
C16 C15 H15B . . 108.4 ?
H15A C15 H15B . . 107.5 ?
C15 C16 C17 . . 112.76(12) ?
C15 C16 H16A . . 109.0 ?
C17 C16 H16A . . 109.0 ?
C15 C16 H16B . . 109.0 ?
C17 C16 H16B . . 109.0 ?
H16A C16 H16B . . 107.8 ?
C18 C17 C16 . . 112.21(12) ?
C18 C17 H17A . . 109.2 ?
C16 C17 H17A . . 109.2 ?
C18 C17 H17B . . 109.2 ?
C16 C17 H17B . . 109.2 ?
H17A C17 H17B . . 107.9 ?
N2 C18 C17 . . 113.94(12) ?
N2 C18 H18A . . 108.8 ?
C17 C18 H18A . . 108.8 ?
N2 C18 H18B . . 108.8 ?
C17 C18 H18B . . 108.8 ?
H18A C18 H18B . . 107.7 ?
N2 C19 C20 . . 131.73(16) ?
N2 C19 C24 . . 106.03(14) ?
C20 C19 C24 . . 122.25(16) ?
C21 C20 C19 . . 116.48(19) ?
C21 C20 H20 . . 121.8 ?
C19 C20 H20 . . 121.8 ?
C20 C21 C22 . . 122.1(2) ?
C20 C21 H21 . . 119.0 ?
C22 C21 H21 . . 119.0 ?
C23 C22 C21 . . 121.35(19) ?
C23 C22 H22 . . 119.3 ?
C21 C22 H22 . . 119.3 ?
C22 C23 C24 . . 118.0(2) ?
C22 C23 H23 . . 121.0 ?
C24 C23 H23 . . 121.0 ?
N3 C24 C19 . . 109.88(14) ?
N3 C24 C23 . . 130.28(17) ?
C19 C24 C23 . . 119.83(18) ?
N3 C25 N2 . . 112.69(14) ?
N3 C25 C26 . . 123.34(15) ?
N2 C25 C26 . . 123.96(13) ?
C31 C26 C27 . . 118.61(17) ?
C31 C26 C25 . . 122.84(15) ?
C27 C26 C25 . . 118.47(16) ?
C28 C27 C26 . . 119.99(19) ?
C28 C27 H27 . . 120.0 ?
C26 C27 H27 . . 120.0 ?
C29 C28 C27 . . 121.0(2) ?
C29 C28 H28 . . 119.5 ?
C27 C28 H28 . . 119.5 ?
C28 C29 C30 . . 119.8(2) ?
C28 C29 H29 . . 120.1 ?
C30 C29 H29 . . 120.1 ?
C29 C30 C31 . . 119.6(2) ?
C29 C30 H30 . . 120.2 ?
C31 C30 H30 . . 120.2 ?
C30 C31 C26 . . 121.00(18) ?
C30 C31 H31 . . 119.5 ?
C26 C31 H31 . . 119.5 ?
C12 N1 C1 . . 108.55(12) ?
C12 N1 C13 . . 124.91(12) ?
C1 N1 C13 . . 126.53(13) ?
C25 N2 C19 . . 106.15(13) ?
C25 N2 C18 . . 129.05(13) ?
C19 N2 C18 . . 124.10(13) ?
C25 N3 C24 . . 105.24(14) ?
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
C1 N1 . 1.3870(18) ?
C1 C2 . 1.391(2) ?
C1 C6 . 1.407(2) ?
C2 C3 . 1.373(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.382(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.376(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.395(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.441(2) ?
C7 C8 . 1.392(2) ?
C7 C12 . 1.406(2) ?
C8 C9 . 1.372(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.386(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.380(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.384(2) ?
C11 H11 . 0.9300 ?
C12 N1 . 1.3858(19) ?
C13 N1 . 1.4527(18) ?
C13 C14 . 1.517(2) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.511(2) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.516(2) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.521(2) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C18 . 1.520(2) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 N2 . 1.4585(18) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 N2 . 1.3823(19) ?
C19 C20 . 1.390(2) ?
C19 C24 . 1.392(2) ?
C20 C21 . 1.377(3) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.383(3) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.373(3) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.395(2) ?
C23 H23 . 0.9300 ?
C24 N3 . 1.388(2) ?
C25 N3 . 1.3181(19) ?
C25 N2 . 1.3799(19) ?
C25 C26 . 1.470(2) ?
C26 C31 . 1.384(2) ?
C26 C27 . 1.393(2) ?
C27 C28 . 1.375(3) ?
C27 H27 . 0.9300 ?
C28 C29 . 1.372(3) ?
C28 H28 . 0.9300 ?
C29 C30 . 1.378(3) ?
C29 H29 . 0.9300 ?
C30 C31 . 1.383(2) ?
C30 H30 . 0.9300 ?
C31 H31 . 0.9300 ?
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
C28 H28 Cg1 0.930 2.783 3.665(2) 158.90
C18 H18A Cg2 0.969 2.867 3.596(3) 132.77
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743812
