#------------------------------------------------------------------------------
#$Date: 2021-05-15 07:50:58 +0300 (Sat, 15 May 2021) $
#$Revision: 265247 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243835.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_2243835
loop_
_publ_author_name
'Smirnov, Daniil E.'
'Tatarin, Sergei V.'
'Bezzubov, Stanislav I.'
_publ_section_title
;
 Synthesis and crystal structures of N-H, N-phenyl and
 N-benzyl-2-(4-hexyloxyphenyl)benzimidazoles
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              618
_journal_page_last               622
_journal_paper_doi               10.1107/S2056989021004898
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C19 H22 N2 O'
_chemical_formula_moiety         'C19 H22 N2 O'
_chemical_formula_sum            'C19 H22 N2 O'
_chemical_formula_weight         294.38
_chemical_name_systematic
;
1-Benzyl-2-(4-hexyloxyphenyl)-1H-benzimidazole
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.3802(13)
_cell_length_b                   9.4076(13)
_cell_length_c                   37.235(5)
_cell_measurement_reflns_used    3935
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      22.22
_cell_measurement_theta_min      2.19
_cell_volume                     3285.8(8)
_computing_cell_refinement
;
APEX3 (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'Bruker PHOTON III CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0973
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            26780
_diffrn_reflns_theta_full        25.049
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_min         2.188
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.398
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.0988
_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)+(0.0273P)²+15.0864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2222
_refine_ls_wR_factor_ref         0.2332
_reflns_number_gt                2171
_reflns_number_total             2900
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mw2176sup1.cif
_cod_data_source_block           1
_cod_database_code               2243835
_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   0.988
_shelx_estimated_absorpt_t_max   0.999
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.7545(4) 0.5030(4) 0.59420(9) 0.0414(9) Uani d 1 . .
N N2 0.2163(4) 0.2653(4) 0.68379(10) 0.0248(9) Uani d 1 . .
H H2 0.268160 0.187574 0.682290 0.030 Uiso calc 1 . .
N N1 0.1515(4) 0.4926(4) 0.67692(10) 0.0272(9) Uani d 1 . .
C C7 0.2513(5) 0.3952(5) 0.67041(11) 0.0244(10) Uani d 1 . .
C C6 0.0860(5) 0.2772(5) 0.69998(12) 0.0229(10) Uani d 1 . .
C C1 0.0453(5) 0.4199(5) 0.69573(12) 0.0244(10) Uani d 1 . .
C C8 0.3840(5) 0.4218(5) 0.65126(12) 0.0237(10) Uani d 1 . .
C C11 0.6376(5) 0.4715(5) 0.61439(13) 0.0311(11) Uani d 1 . .
C C2 -0.0840(5) 0.4681(5) 0.70942(12) 0.0298(11) Uani d 1 . .
H H2A -0.113329 0.564031 0.706417 0.036 Uiso calc 1 . .
C C4 -0.1271(5) 0.2283(5) 0.73179(12) 0.0299(11) Uani d 1 . .
H H4 -0.187766 0.164485 0.744326 0.036 Uiso calc 1 . .
C C9 0.5082(5) 0.3519(5) 0.66103(13) 0.0300(11) Uani d 1 . .
H H9 0.506235 0.285528 0.680252 0.036 Uiso calc 1 . .
C C5 -0.0007(5) 0.1807(5) 0.71803(12) 0.0292(11) Uani d 1 . .
H H5 0.027284 0.084213 0.720724 0.035 Uiso calc 1 . .
C C13 0.3884(5) 0.5194(5) 0.62292(12) 0.0300(11) Uani d 1 . .
H H13 0.304450 0.569382 0.616270 0.036 Uiso calc 1 . .
C C3 -0.1679(5) 0.3716(5) 0.72747(12) 0.0306(11) Uani d 1 . .
H H3 -0.256049 0.402423 0.737335 0.037 Uiso calc 1 . .
C C12 0.5135(5) 0.5432(5) 0.60466(13) 0.0318(11) Uani d 1 . .
H H12 0.515327 0.608955 0.585293 0.038 Uiso calc 1 . .
C C10 0.6359(5) 0.3777(5) 0.64308(13) 0.0334(12) Uani d 1 . .
H H10 0.720987 0.331308 0.650433 0.040 Uiso calc 1 . .
C C16 1.0202(6) 0.6351(6) 0.57073(14) 0.0403(13) Uani d 1 . .
H H16A 1.064798 0.675292 0.592588 0.048 Uiso calc 1 . .
H H16B 0.927145 0.682857 0.567265 0.048 Uiso calc 1 . .
C C15 0.9959(6) 0.4787(6) 0.57613(15) 0.0423(13) Uani d 1 . .
H H15A 1.087936 0.433602 0.582430 0.051 Uiso calc 1 . .
H H15B 0.963661 0.436941 0.553110 0.051 Uiso calc 1 . .
C C14 0.8880(5) 0.4424(7) 0.60488(15) 0.0448(14) Uani d 1 . .
H H14A 0.879059 0.337954 0.607315 0.054 Uiso calc 1 . .
H H14B 0.918389 0.482004 0.628292 0.054 Uiso calc 1 . .
C C17 1.1158(6) 0.6661(6) 0.53834(16) 0.0497(15) Uani d 1 . .
H H17A 1.213683 0.633557 0.543928 0.060 Uiso calc 1 . .
H H17B 1.081204 0.609693 0.517656 0.060 Uiso calc 1 . .
C C18 1.1219(7) 0.8192(7) 0.52750(17) 0.0563(17) Uani d 1 . .
H H18A 1.161793 0.875489 0.547597 0.068 Uiso calc 1 . .
H H18B 1.023846 0.853648 0.522954 0.068 Uiso calc 1 . .
C C19 1.2111(8) 0.8441(8) 0.49442(17) 0.072(2) Uani d 1 . .
H H19A 1.176104 0.784013 0.474815 0.108 Uiso calc 1 . .
H H19B 1.310699 0.820335 0.499581 0.108 Uiso calc 1 . .
H H19C 1.204377 0.944261 0.487356 0.108 Uiso calc 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'
O O 0.0106 0.0060 '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
C11 O1 C14 . . 117.7(4) ?
C7 N2 H2 . . 126.1 ?
C7 N2 C6 . . 107.7(4) ?
C6 N2 H2 . . 126.1 ?
C7 N1 C1 . . 104.8(4) ?
N2 C7 C8 . . 122.7(4) ?
N1 C7 N2 . . 112.4(4) ?
N1 C7 C8 . . 124.9(4) ?
N2 C6 C1 . . 105.7(4) ?
N2 C6 C5 . . 133.0(4) ?
C5 C6 C1 . . 121.3(4) ?
N1 C1 C6 . . 109.3(4) ?
C2 C1 N1 . . 130.2(4) ?
C2 C1 C6 . . 120.5(4) ?
C9 C8 C7 . . 120.5(4) ?
C9 C8 C13 . . 119.0(4) ?
C13 C8 C7 . . 120.5(4) ?
O1 C11 C12 . . 115.1(4) ?
O1 C11 C10 . . 125.0(4) ?
C10 C11 C12 . . 119.9(4) ?
C1 C2 H2A . . 121.2 ?
C3 C2 C1 . . 117.5(4) ?
C3 C2 H2A . . 121.2 ?
C5 C4 H4 . . 119.8 ?
C5 C4 C3 . . 120.4(4) ?
C3 C4 H4 . . 119.8 ?
C8 C9 H9 . . 119.5 ?
C8 C9 C10 . . 120.9(4) ?
C10 C9 H9 . . 119.5 ?
C6 C5 H5 . . 120.9 ?
C4 C5 C6 . . 118.3(4) ?
C4 C5 H5 . . 120.9 ?
C8 C13 H13 . . 119.8 ?
C12 C13 C8 . . 120.3(4) ?
C12 C13 H13 . . 119.8 ?
C2 C3 C4 . . 122.0(4) ?
C2 C3 H3 . . 119.0 ?
C4 C3 H3 . . 119.0 ?
C11 C12 H12 . . 119.8 ?
C13 C12 C11 . . 120.4(4) ?
C13 C12 H12 . . 119.8 ?
C11 C10 C9 . . 119.4(5) ?
C11 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
H16A C16 H16B . . 107.9 ?
C15 C16 H16A . . 109.1 ?
C15 C16 H16B . . 109.1 ?
C15 C16 C17 . . 112.4(5) ?
C17 C16 H16A . . 109.1 ?
C17 C16 H16B . . 109.1 ?
C16 C15 H15A . . 108.6 ?
C16 C15 H15B . . 108.6 ?
C16 C15 C14 . . 114.7(5) ?
H15A C15 H15B . . 107.6 ?
C14 C15 H15A . . 108.6 ?
C14 C15 H15B . . 108.6 ?
O1 C14 C15 . . 107.4(4) ?
O1 C14 H14A . . 110.2 ?
O1 C14 H14B . . 110.2 ?
C15 C14 H14A . . 110.2 ?
C15 C14 H14B . . 110.2 ?
H14A C14 H14B . . 108.5 ?
C16 C17 H17A . . 108.6 ?
C16 C17 H17B . . 108.6 ?
H17A C17 H17B . . 107.6 ?
C18 C17 C16 . . 114.7(5) ?
C18 C17 H17A . . 108.6 ?
C18 C17 H17B . . 108.6 ?
C17 C18 H18A . . 109.0 ?
C17 C18 H18B . . 109.0 ?
C17 C18 C19 . . 113.0(5) ?
H18A C18 H18B . . 107.8 ?
C19 C18 H18A . . 109.0 ?
C19 C18 H18B . . 109.0 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19B . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
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
O1 C11 . 1.362(6) ?
O1 C14 . 1.433(6) ?
N2 H2 . 0.8800 ?
N2 C7 . 1.360(6) ?
N2 C6 . 1.368(5) ?
N1 C7 . 1.333(6) ?
N1 C1 . 1.397(6) ?
C7 C8 . 1.456(6) ?
C6 C1 . 1.405(6) ?
C6 C5 . 1.392(6) ?
C1 C2 . 1.392(6) ?
C8 C9 . 1.387(6) ?
C8 C13 . 1.399(6) ?
C11 C12 . 1.394(7) ?
C11 C10 . 1.386(7) ?
C2 H2A . 0.9500 ?
C2 C3 . 1.377(6) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.367(7) ?
C4 C3 . 1.410(7) ?
C9 H9 . 0.9500 ?
C9 C10 . 1.392(7) ?
C5 H5 . 0.9500 ?
C13 H13 . 0.9500 ?
C13 C12 . 1.375(7) ?
C3 H3 . 0.9500 ?
C12 H12 . 0.9500 ?
C10 H10 . 0.9500 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C16 C15 . 1.503(8) ?
C16 C17 . 1.531(7) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C15 C14 . 1.512(7) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C17 C18 . 1.497(8) ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
C18 C19 . 1.507(8) ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
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
N2 H2 N1 8_655 0.88 1.99 2.861(5) 168.5 yes
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C11 C12 C13 . . . . 179.5(4) ?
O1 C11 C10 C9 . . . . -178.4(5) ?
N2 C7 C8 C9 . . . . -35.0(7) ?
N2 C7 C8 C13 . . . . 145.6(4) ?
N2 C6 C1 N1 . . . . 0.1(5) ?
N2 C6 C1 C2 . . . . -179.9(4) ?
N2 C6 C5 C4 . . . . 179.1(5) ?
N1 C7 C8 C9 . . . . 145.0(5) ?
N1 C7 C8 C13 . . . . -34.4(7) ?
N1 C1 C2 C3 . . . . -179.2(4) ?
C7 N2 C6 C1 . . . . -0.2(5) ?
C7 N2 C6 C5 . . . . -179.6(5) ?
C7 N1 C1 C6 . . . . -0.1(5) ?
C7 N1 C1 C2 . . . . 180.0(5) ?
C7 C8 C9 C10 . . . . -179.4(4) ?
C7 C8 C13 C12 . . . . -179.4(4) ?
C6 N2 C7 N1 . . . . 0.1(5) ?
C6 N2 C7 C8 . . . . -179.9(4) ?
C6 C1 C2 C3 . . . . 0.9(7) ?
C1 N1 C7 N2 . . . . 0.0(5) ?
C1 N1 C7 C8 . . . . -180.0(4) ?
C1 C6 C5 C4 . . . . -0.3(7) ?
C1 C2 C3 C4 . . . . -0.9(7) ?
C8 C9 C10 C11 . . . . -1.8(7) ?
C8 C13 C12 C11 . . . . -0.6(7) ?
C11 O1 C14 C15 . . . . 173.5(4) ?
C9 C8 C13 C12 . . . . 1.3(7) ?
C5 C6 C1 N1 . . . . 179.7(4) ?
C5 C6 C1 C2 . . . . -0.4(7) ?
C5 C4 C3 C2 . . . . 0.2(7) ?
C13 C8 C9 C10 . . . . 0.0(7) ?
C3 C4 C5 C6 . . . . 0.3(7) ?
C12 C11 C10 C9 . . . . 2.5(7) ?
C10 C11 C12 C13 . . . . -1.3(8) ?
C16 C15 C14 O1 . . . . 61.1(6) ?
C16 C17 C18 C19 . . . . -177.1(5) ?
C15 C16 C17 C18 . . . . 169.2(5) ?
C14 O1 C11 C12 . . . . 174.6(5) ?
C14 O1 C11 C10 . . . . -4.6(7) ?
C17 C16 C15 C14 . . . . -172.9(5) ?

_cod_database_fobs_code 2243835
