##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_3
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_journal_date_recd_electronic     2021-04-30
_journal_date_accepted     2021-05-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2021
_journal_volume     77
_journal_issue      6
_journal_page_first     618
_journal_page_last     622
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989021004898
_journal_coeditor_code     MW2176
_publ_contact_author_name     'Stanislav I. Bezzubov'
_publ_contact_author_address
;
Kurnakov Institute of General and Inorganic Chemistry of Russian Academy of
 Sciences
;
_publ_contact_author_email     'bezzubov@igic.ras.ru'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '+79161671072'
_publ_section_title
;
Synthesis and crystal structures of N-H, N-phenyl and
N-benzyl-2-(4-hexyloxyphenyl)benzimidazoles
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Smirnov, Daniil E.' .
;
Department of Chemistry, Lomonosov Moscow State University, Lenin's Hills,
 1-3, Moscow, 119991, Russian Federation
N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian
Academy of Sciences, Leninsky pr. 31, Moscow 119991,
Russian Federation
;
    'Tatarin, Sergei V.' .
;
Department of Chemistry, Lomonosov Moscow State University, Lenin's Hills,
 1-3, Moscow, 119991, Russian Federation
N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian
Academy of Sciences, Leninsky pr. 31, Moscow 119991,
Russian Federation
;
    'Bezzubov, Stanislav I.' .
;
N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian
Academy of Sciences, Leninsky pr. 31, Moscow 119991,
Russian Federation
;
_publ_section_synopsis
;
N-H, N-phenyl and
N-benzyl-2-(4-hexyloxyphenyl)benzimidazoles were prepared and studied
by ¹H NMR and single-crystal X-ray analysis.  The unsubstituted
benzimidazole forms intermolecular N---H...N bonds while in the crystal
structures of the other two compounds, the molecules are assembled only
through π--π and C---H...π interactions.
;
_chemical_name_systematic
;
2-(4-Hexyloxyphenyl)-1H-benzimidazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C26 H28 N2 O'
_chemical_formula_sum     'C26 H28 N2 O'
_chemical_formula_iupac     'C26 H28 N2 O'
_chemical_formula_weight     384.50
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/n 1'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     14.3057(13)
_cell_length_b     9.6392(7)
_cell_length_c     16.3024(13)
_cell_angle_alpha     90
_cell_angle_beta     108.977(3)
_cell_angle_gamma     90
_cell_volume     2125.8(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5668
_cell_measurement_theta_min     2.304
_cell_measurement_theta_max     26.10
_cell_measurement_temperature     150.0
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.201
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     824
_exptl_absorpt_coefficient_mu     0.073
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_absorpt_correction_T_min     0.6942
_exptl_absorpt_correction_T_max     0.7454
_diffrn_ambient_temperature     150.0
_diffrn_source     'microfocus sealed X-ray tube'
_diffrn_source_power     0.07
_diffrn_source_voltage     50.0
_diffrn_source_current     1.4
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'focusing mirrors'
_diffrn_measurement_device_type     'Bruker D8 Venture'
_diffrn_measurement_device     '3-circle diffractometer'
_diffrn_measurement_method     ω-scan
_diffrn_detector     'Bruker PHOTON III CMOS'
_diffrn_detector_area_resol_mean     10.4
_diffrn_reflns_number     20533
_diffrn_reflns_av_R_equivalents     0.0514
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_theta_min     2.303
_diffrn_reflns_theta_max     25.148
_diffrn_reflns_theta_full     25.148
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     3813
_reflns_number_gt     2875
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0680
_refine_ls_R_factor_gt     0.0454
_refine_ls_wR_factor_gt     0.1061
_refine_ls_wR_factor_ref     0.1162
_refine_ls_goodness_of_fit_ref     1.032
_refine_ls_restrained_S_all     1.032
_refine_ls_number_reflns     3813
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0499P)²+0.8451P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.516
_refine_diff_density_min     -0.253
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_cell_refinement
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
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 0.35057(10) 0.68007(13) 0.63440(8) 0.0346(3) Uani d 1 . .
    N N2 0.71150(11) 0.25231(14) 0.65132(9) 0.0245(3) Uani d 1 . .
    N N1 0.57463(11) 0.13503(15) 0.57646(9) 0.0265(3) Uani d 1 . .
    C C7 0.61008(13) 0.25349(18) 0.61454(11) 0.0251(4) Uani d 1 . .
    C C9 0.83510(13) 0.43825(17) 0.65779(11) 0.0239(4) Uani d 1 . .
    C C6 0.74261(13) 0.12185(17) 0.63539(11) 0.0241(4) Uani d 1 . .
    C C15 0.54652(13) 0.37098(18) 0.61908(11) 0.0254(4) Uani d 1 . .
    C C1 0.65666(13) 0.05056(18) 0.58863(11) 0.0251(4) Uani d 1 . .
    C C17 0.50564(14) 0.61502(19) 0.61353(11) 0.0289(4) Uani d 1 . .
    H H17 0.522454 0.708718 0.606838 0.035 Uiso calc 1 . .
    C C18 0.41772(13) 0.58396(19) 0.62720(11) 0.0281(4) Uani d 1 . .
    C C8 0.77685(13) 0.35755(18) 0.70438(11) 0.0265(4) Uani d 1 . .
    H H8A 0.823789 0.311896 0.755747 0.032 Uiso calc 1 . .
    H H8B 0.736704 0.423506 0.725444 0.032 Uiso calc 1 . .
    C C5 0.83572(13) 0.06191(19) 0.65827(11) 0.0272(4) Uani d 1 . .
    H H5 0.893481 0.111446 0.690252 0.033 Uiso calc 1 . .
    C C19 0.39190(14) 0.44582(19) 0.63417(12) 0.0307(4) Uani d 1 . .
    H H19 0.330604 0.424005 0.642021 0.037 Uiso calc 1 . .
    C C2 0.66237(14) -0.08558(18) 0.56151(12) 0.0287(4) Uani d 1 . .
    H H2 0.604818 -0.134800 0.528710 0.034 Uiso calc 1 . .
    C C14 0.91141(13) 0.52387(18) 0.70620(12) 0.0287(4) Uani d 1 . .
    H H14 0.925754 0.530467 0.767205 0.034 Uiso calc 1 . .
    C C10 0.81481(14) 0.43126(18) 0.56852(11) 0.0278(4) Uani d 1 . .
    H H10 0.762893 0.373364 0.534517 0.033 Uiso calc 1 . .
    C C20 0.45566(14) 0.34143(19) 0.62962(11) 0.0298(4) Uani d 1 . .
    H H20 0.437451 0.247555 0.633726 0.036 Uiso calc 1 . .
    C C16 0.56943(14) 0.50850(18) 0.60961(11) 0.0275(4) Uani d 1 . .
    H H16 0.629935 0.530316 0.600256 0.033 Uiso calc 1 . .
    C C4 0.84007(14) -0.07356(19) 0.63211(12) 0.0303(4) Uani d 1 . .
    H H4 0.902394 -0.118716 0.646990 0.036 Uiso calc 1 . .
    C C3 0.75487(15) -0.14613(19) 0.58417(12) 0.0315(4) Uani d 1 . .
    H H3 0.760861 -0.238922 0.566880 0.038 Uiso calc 1 . .
    C C11 0.86981(14) 0.50819(19) 0.52880(12) 0.0322(5) Uani d 1 . .
    H H11 0.854981 0.503161 0.467686 0.039 Uiso calc 1 . .
    C C13 0.96659(14) 0.59952(19) 0.66617(13) 0.0327(5) Uani d 1 . .
    H H13 1.018967 0.656944 0.699922 0.039 Uiso calc 1 . .
    C C12 0.94587(14) 0.59196(19) 0.57721(13) 0.0337(5) Uani d 1 . .
    H H12 0.983728 0.644025 0.549780 0.040 Uiso calc 1 . .
    C C21 0.37783(15) 0.82380(19) 0.63491(13) 0.0363(5) Uani d 1 . .
    H H21A 0.380986 0.851037 0.577313 0.044 Uiso calc 1 . .
    H H21B 0.443518 0.839772 0.678704 0.044 Uiso calc 1 . .
    C C24 0.12096(16) 0.9823(2) 0.61640(14) 0.0414(5) Uani d 1 . .
    H H24A 0.054475 0.959653 0.575868 0.050 Uiso calc 1 . .
    H H24B 0.121849 0.957698 0.675606 0.050 Uiso calc 1 . .
    C C26 0.05543(16) 1.2226(2) 0.62688(14) 0.0416(5) Uani d 1 . .
    H H26A -0.007303 1.199254 0.582282 0.062 Uiso calc 1 . .
    H H26B 0.069379 1.321545 0.623109 0.062 Uiso calc 1 . .
    H H26C 0.050857 1.202249 0.684342 0.062 Uiso calc 1 . .
    C C25 0.13774(16) 1.1376(2) 0.61283(15) 0.0445(6) Uani d 1 . .
    H H25A 0.200929 1.162309 0.657797 0.053 Uiso calc 1 . .
    H H25B 0.143581 1.161314 0.555610 0.053 Uiso calc 1 . .
    C C23 0.19767(16) 0.8929(2) 0.59333(14) 0.0448(5) Uani d 1 . .
    H H23A 0.177602 0.794288 0.591145 0.054 Uiso calc 1 . .
    H H23B 0.198534 0.919180 0.534875 0.054 Uiso calc 1 . .
    C C22 0.29974(16) 0.9082(2) 0.65685(14) 0.0466(6) Uani d 1 . .
    H H22A 0.298728 0.880129 0.714969 0.056 Uiso calc 1 . .
    H H22B 0.318687 1.007348 0.660047 0.056 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C18 . 1.367(2) ?
    O1 C21 . 1.439(2) ?
    N2 C7 . 1.378(2) ?
    N2 C6 . 1.386(2) ?
    N2 C8 . 1.458(2) ?
    N1 C7 . 1.320(2) ?
    N1 C1 . 1.389(2) ?
    C7 C15 . 1.469(2) ?
    C9 C8 . 1.513(2) ?
    C9 C14 . 1.391(2) ?
    C9 C10 . 1.390(2) ?
    C6 C1 . 1.398(2) ?
    C6 C5 . 1.387(2) ?
    C15 C20 . 1.395(3) ?
    C15 C16 . 1.386(3) ?
    C1 C2 . 1.396(2) ?
    C17 H17 . 0.9500 ?
    C17 C18 . 1.380(3) ?
    C17 C16 . 1.389(2) ?
    C18 C19 . 1.396(3) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C5 H5 . 0.9500 ?
    C5 C4 . 1.381(3) ?
    C19 H19 . 0.9500 ?
    C19 C20 . 1.376(3) ?
    C2 H2 . 0.9500 ?
    C2 C3 . 1.382(3) ?
    C14 H14 . 0.9500 ?
    C14 C13 . 1.384(3) ?
    C10 H10 . 0.9500 ?
    C10 C11 . 1.385(3) ?
    C20 H20 . 0.9500 ?
    C16 H16 . 0.9500 ?
    C4 H4 . 0.9500 ?
    C4 C3 . 1.402(3) ?
    C3 H3 . 0.9500 ?
    C11 H11 . 0.9500 ?
    C11 C12 . 1.379(3) ?
    C13 H13 . 0.9500 ?
    C13 C12 . 1.385(3) ?
    C12 H12 . 0.9500 ?
    C21 H21A . 0.9900 ?
    C21 H21B . 0.9900 ?
    C21 C22 . 1.516(3) ?
    C24 H24A . 0.9900 ?
    C24 H24B . 0.9900 ?
    C24 C25 . 1.520(3) ?
    C24 C23 . 1.535(3) ?
    C26 H26A . 0.9800 ?
    C26 H26B . 0.9800 ?
    C26 H26C . 0.9800 ?
    C26 C25 . 1.512(3) ?
    C25 H25A . 0.9900 ?
    C25 H25B . 0.9900 ?
    C23 H23A . 0.9900 ?
    C23 H23B . 0.9900 ?
    C23 C22 . 1.498(3) ?
    C22 H22A . 0.9900 ?
    C22 H22B . 0.9900 ?
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
    C18 O1 C21 . . 117.15(15) ?
    C7 N2 C6 . . 106.42(14) ?
    C7 N2 C8 . . 129.33(14) ?
    C6 N2 C8 . . 124.01(15) ?
    C7 N1 C1 . . 105.21(15) ?
    N2 C7 C15 . . 124.45(16) ?
    N1 C7 N2 . . 112.75(15) ?
    N1 C7 C15 . . 122.76(16) ?
    C14 C9 C8 . . 118.62(15) ?
    C10 C9 C8 . . 122.63(16) ?
    C10 C9 C14 . . 118.74(16) ?
    N2 C6 C1 . . 105.60(15) ?
    N2 C6 C5 . . 131.77(17) ?
    C5 C6 C1 . . 122.63(16) ?
    C20 C15 C7 . . 117.75(16) ?
    C16 C15 C7 . . 123.98(16) ?
    C16 C15 C20 . . 118.20(16) ?
    N1 C1 C6 . . 110.01(15) ?
    N1 C1 C2 . . 129.78(17) ?
    C2 C1 C6 . . 120.21(16) ?
    C18 C17 H17 . . 120.2 ?
    C18 C17 C16 . . 119.61(17) ?
    C16 C17 H17 . . 120.2 ?
    O1 C18 C17 . . 124.75(17) ?
    O1 C18 C19 . . 115.30(16) ?
    C17 C18 C19 . . 119.95(17) ?
    N2 C8 C9 . . 114.30(14) ?
    N2 C8 H8A . . 108.7 ?
    N2 C8 H8B . . 108.7 ?
    C9 C8 H8A . . 108.7 ?
    C9 C8 H8B . . 108.7 ?
    H8A C8 H8B . . 107.6 ?
    C6 C5 H5 . . 121.7 ?
    C4 C5 C6 . . 116.52(17) ?
    C4 C5 H5 . . 121.7 ?
    C18 C19 H19 . . 120.2 ?
    C20 C19 C18 . . 119.69(17) ?
    C20 C19 H19 . . 120.2 ?
    C1 C2 H2 . . 121.2 ?
    C3 C2 C1 . . 117.51(18) ?
    C3 C2 H2 . . 121.2 ?
    C9 C14 H14 . . 119.7 ?
    C13 C14 C9 . . 120.51(17) ?
    C13 C14 H14 . . 119.7 ?
    C9 C10 H10 . . 119.8 ?
    C11 C10 C9 . . 120.42(18) ?
    C11 C10 H10 . . 119.8 ?
    C15 C20 H20 . . 119.4 ?
    C19 C20 C15 . . 121.19(17) ?
    C19 C20 H20 . . 119.4 ?
    C15 C16 C17 . . 121.28(17) ?
    C15 C16 H16 . . 119.4 ?
    C17 C16 H16 . . 119.4 ?
    C5 C4 H4 . . 119.2 ?
    C5 C4 C3 . . 121.69(17) ?
    C3 C4 H4 . . 119.2 ?
    C2 C3 C4 . . 121.43(17) ?
    C2 C3 H3 . . 119.3 ?
    C4 C3 H3 . . 119.3 ?
    C10 C11 H11 . . 119.7 ?
    C12 C11 C10 . . 120.56(18) ?
    C12 C11 H11 . . 119.7 ?
    C14 C13 H13 . . 119.8 ?
    C14 C13 C12 . . 120.37(18) ?
    C12 C13 H13 . . 119.8 ?
    C11 C12 C13 . . 119.39(17) ?
    C11 C12 H12 . . 120.3 ?
    C13 C12 H12 . . 120.3 ?
    O1 C21 H21A . . 110.2 ?
    O1 C21 H21B . . 110.2 ?
    O1 C21 C22 . . 107.40(16) ?
    H21A C21 H21B . . 108.5 ?
    C22 C21 H21A . . 110.2 ?
    C22 C21 H21B . . 110.2 ?
    H24A C24 H24B . . 107.6 ?
    C25 C24 H24A . . 108.7 ?
    C25 C24 H24B . . 108.7 ?
    C25 C24 C23 . . 114.15(18) ?
    C23 C24 H24A . . 108.7 ?
    C23 C24 H24B . . 108.7 ?
    H26A C26 H26B . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 109.5 ?
    C25 C26 H26A . . 109.5 ?
    C25 C26 H26B . . 109.5 ?
    C25 C26 H26C . . 109.5 ?
    C24 C25 H25A . . 109.0 ?
    C24 C25 H25B . . 109.0 ?
    C26 C25 C24 . . 112.80(18) ?
    C26 C25 H25A . . 109.0 ?
    C26 C25 H25B . . 109.0 ?
    H25A C25 H25B . . 107.8 ?
    C24 C23 H23A . . 109.0 ?
    C24 C23 H23B . . 109.0 ?
    H23A C23 H23B . . 107.8 ?
    C22 C23 C24 . . 112.89(17) ?
    C22 C23 H23A . . 109.0 ?
    C22 C23 H23B . . 109.0 ?
    C21 C22 H22A . . 108.7 ?
    C21 C22 H22B . . 108.7 ?
    C23 C22 C21 . . 114.30(18) ?
    C23 C22 H22A . . 108.7 ?
    C23 C22 H22B . . 108.7 ?
    H22A C22 H22B . . 107.6 ?
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 C18 C19 C20 . . . . -178.63(16) ?
    O1 C21 C22 C23 . . . . -60.9(2) ?
    N2 C7 C15 C20 . . . . -141.71(17) ?
    N2 C7 C15 C16 . . . . 41.3(3) ?
    N2 C6 C1 N1 . . . . -0.27(18) ?
    N2 C6 C1 C2 . . . . 179.56(15) ?
    N2 C6 C5 C4 . . . . 179.23(16) ?
    N1 C7 C15 C20 . . . . 36.1(2) ?
    N1 C7 C15 C16 . . . . -140.91(18) ?
    N1 C1 C2 C3 . . . . -178.94(16) ?
    C7 N2 C6 C1 . . . . 0.31(17) ?
    C7 N2 C6 C5 . . . . -178.80(17) ?
    C7 N2 C8 C9 . . . . -105.68(19) ?
    C7 N1 C1 C6 . . . . 0.12(18) ?
    C7 N1 C1 C2 . . . . -179.70(17) ?
    C7 C15 C20 C19 . . . . -179.81(16) ?
    C7 C15 C16 C17 . . . . 179.22(16) ?
    C9 C14 C13 C12 . . . . 0.6(3) ?
    C9 C10 C11 C12 . . . . 0.5(3) ?
    C6 N2 C7 N1 . . . . -0.26(18) ?
    C6 N2 C7 C15 . . . . 177.70(15) ?
    C6 N2 C8 C9 . . . . 80.8(2) ?
    C6 C1 C2 C3 . . . . 1.3(2) ?
    C6 C5 C4 C3 . . . . 0.6(2) ?
    C1 N1 C7 N2 . . . . 0.09(18) ?
    C1 N1 C7 C15 . . . . -177.91(15) ?
    C1 C6 C5 C4 . . . . 0.2(2) ?
    C1 C2 C3 C4 . . . . -0.4(3) ?
    C17 C18 C19 C20 . . . . 1.7(3) ?
    C18 O1 C21 C22 . . . . -171.66(15) ?
    C18 C17 C16 C15 . . . . 0.1(3) ?
    C18 C19 C20 C15 . . . . 0.7(3) ?
    C8 N2 C7 N1 . . . . -174.66(15) ?
    C8 N2 C7 C15 . . . . 3.3(3) ?
    C8 N2 C6 C1 . . . . 175.08(14) ?
    C8 N2 C6 C5 . . . . -4.0(3) ?
    C8 C9 C14 C13 . . . . 179.99(16) ?
    C8 C9 C10 C11 . . . . 179.44(16) ?
    C5 C6 C1 N1 . . . . 178.94(15) ?
    C5 C6 C1 C2 . . . . -1.2(2) ?
    C5 C4 C3 C2 . . . . -0.6(3) ?
    C14 C9 C8 N2 . . . . -169.16(15) ?
    C14 C9 C10 C11 . . . . 0.1(3) ?
    C14 C13 C12 C11 . . . . -0.1(3) ?
    C10 C9 C8 N2 . . . . 11.5(2) ?
    C10 C9 C14 C13 . . . . -0.6(3) ?
    C10 C11 C12 C13 . . . . -0.5(3) ?
    C20 C15 C16 C17 . . . . 2.3(3) ?
    C16 C15 C20 C19 . . . . -2.7(3) ?
    C16 C17 C18 O1 . . . . 178.27(16) ?
    C16 C17 C18 C19 . . . . -2.1(3) ?
    C21 O1 C18 C17 . . . . -5.4(2) ?
    C21 O1 C18 C19 . . . . 174.93(16) ?
    C24 C23 C22 C21 . . . . -178.67(18) ?
    C25 C24 C23 C22 . . . . 64.6(3) ?
    C23 C24 C25 C26 . . . . 174.14(18) ?
_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     0.977
_shelx_estimated_absorpt_T_max     0.998
data_2
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_chemical_name_systematic
;
2-(4-Hexyloxyphenyl)-1-phenyl-1H-benzimidazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C25 H26 N2 O'
_chemical_formula_sum     'C25 H26 N2 O'
_chemical_formula_iupac     'C25 H26 N2 O'
_chemical_formula_weight     370.48
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/n 1'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     9.0089(3)
_cell_length_b     16.6539(5)
_cell_length_c     13.8400(5)
_cell_angle_alpha     90
_cell_angle_beta     101.4190(10)
_cell_angle_gamma     90
_cell_volume     2035.36(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6945
_cell_measurement_theta_min     2.45
_cell_measurement_theta_max     29.99
_cell_measurement_temperature     100.0
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.23
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.209
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     792
_exptl_absorpt_coefficient_mu     0.074
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_absorpt_correction_T_min     0.6941
_exptl_absorpt_correction_T_max     0.7461
_diffrn_ambient_temperature     100.0
_diffrn_source     'microfocus sealed X-ray tube'
_diffrn_source_power     0.07
_diffrn_source_voltage     50.0
_diffrn_source_current     1.4
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'focusing mirrors'
_diffrn_measurement_device_type     'Bruker D8 Venture'
_diffrn_measurement_device     '3-circle diffractometer'
_diffrn_measurement_method     ω-scan
_diffrn_detector     'Bruker PHOTON III CMOS'
_diffrn_detector_area_resol_mean     10.4
_diffrn_reflns_number     22388
_diffrn_reflns_av_R_equivalents     0.0468
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_theta_min     1.936
_diffrn_reflns_theta_max     30.517
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -22
_diffrn_reflns_limit_k_max     23
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     6195
_reflns_number_gt     4489
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0733
_refine_ls_R_factor_gt     0.0471
_refine_ls_wR_factor_gt     0.1082
_refine_ls_wR_factor_ref     0.1192
_refine_ls_goodness_of_fit_ref     1.028
_refine_ls_restrained_S_all     1.028
_refine_ls_number_reflns     6195
_refine_ls_number_parameters     357
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0568P)²+0.2708P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.273
_refine_diff_density_min     -0.254
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_cell_refinement
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
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 0.41962(10) 0.79543(5) 0.47354(6) 0.02038(19) Uani d 1 . .
    N N2 0.36688(10) 0.42504(6) 0.31526(7) 0.0158(2) Uani d 1 . .
    N N1 0.59290(11) 0.46364(6) 0.28508(7) 0.0175(2) Uani d 1 . .
    C C1 0.56463(13) 0.38438(7) 0.25505(8) 0.0163(2) Uani d 1 . .
    C C7 0.47394(12) 0.48562(7) 0.32094(8) 0.0153(2) Uani d 1 . .
    C C18 0.36776(13) 0.65236(7) 0.48047(8) 0.0168(2) Uani d 1 . .
    C C14 0.45784(12) 0.56503(7) 0.36379(8) 0.0158(2) Uani d 1 . .
    C C17 0.43040(13) 0.71868(7) 0.44203(9) 0.0166(2) Uani d 1 . .
    C C15 0.52509(13) 0.63193(7) 0.32834(9) 0.0177(2) Uani d 1 . .
    C C8 0.22065(12) 0.42800(7) 0.34137(8) 0.0155(2) Uani d 1 . .
    C C6 0.42416(13) 0.35920(7) 0.27312(8) 0.0162(2) Uani d 1 . .
    C C19 0.38161(13) 0.57656(7) 0.44118(8) 0.0160(2) Uani d 1 . .
    C C16 0.51118(13) 0.70773(7) 0.36634(9) 0.0180(2) Uani d 1 . .
    C C9 0.19533(13) 0.38329(7) 0.42090(9) 0.0192(2) Uani d 1 . .
    C C5 0.36509(14) 0.28298(7) 0.24870(9) 0.0201(2) Uani d 1 . .
    C C11 -0.05825(14) 0.43579(7) 0.39489(9) 0.0215(3) Uani d 1 . .
    C C2 0.65337(14) 0.33068(7) 0.21309(9) 0.0201(2) Uani d 1 . .
    C C13 0.10770(13) 0.47566(7) 0.28723(9) 0.0200(2) Uani d 1 . .
    C C4 0.45431(14) 0.23105(8) 0.20649(9) 0.0218(3) Uani d 1 . .
    C C3 0.59663(14) 0.25456(8) 0.18966(9) 0.0216(3) Uani d 1 . .
    C C10 0.05474(14) 0.38751(8) 0.44755(9) 0.0224(3) Uani d 1 . .
    C C12 -0.03216(14) 0.47956(8) 0.31463(9) 0.0224(3) Uani d 1 . .
    C C20 0.32560(15) 0.80774(7) 0.54534(9) 0.0211(2) Uani d 1 . .
    C C23 0.23511(16) 1.03530(7) 0.50281(9) 0.0234(3) Uani d 1 . .
    C C21 0.32315(16) 0.89670(8) 0.56663(9) 0.0237(3) Uani d 1 . .
    C C22 0.24677(16) 0.94655(8) 0.47849(9) 0.0244(3) Uani d 1 . .
    C C24 0.15475(17) 1.08422(8) 0.41511(10) 0.0268(3) Uani d 1 . .
    C C25 0.1401(2) 1.17278(8) 0.43819(11) 0.0314(3) Uani d 1 . .
    H H15 0.5791(15) 0.6253(8) 0.2753(10) 0.020(3) Uiso d 1 . .
    H H20A 0.2200(16) 0.7877(8) 0.5168(10) 0.020(3) Uiso d 1 . .
    H H18 0.3139(15) 0.6582(8) 0.5347(10) 0.017(3) Uiso d 1 . .
    H H10 0.0330(17) 0.3558(9) 0.5043(12) 0.033(4) Uiso d 1 . .
    H H19 0.3366(14) 0.5308(8) 0.4683(10) 0.016(3) Uiso d 1 . .
    H H20B 0.3691(16) 0.7754(8) 0.6061(11) 0.025(4) Uiso d 1 . .
    H H21A 0.2665(18) 0.9038(9) 0.6220(12) 0.032(4) Uiso d 1 . .
    H H22A 0.3029(18) 0.9409(9) 0.4231(13) 0.039(4) Uiso d 1 . .
    H H23A 0.3409(17) 1.0592(8) 0.5256(11) 0.024(4) Uiso d 1 . .
    H H9 0.2784(16) 0.3505(8) 0.4602(11) 0.025(4) Uiso d 1 . .
    H H12 -0.1128(17) 0.5134(9) 0.2784(12) 0.030(4) Uiso d 1 . .
    H H4 0.4210(16) 0.1761(9) 0.1892(11) 0.028(4) Uiso d 1 . .
    H H13 0.1299(15) 0.5066(8) 0.2297(11) 0.025(4) Uiso d 1 . .
    H H22B 0.1433(19) 0.9249(9) 0.4523(12) 0.034(4) Uiso d 1 . .
    H H23B 0.1808(17) 1.0410(9) 0.5594(12) 0.031(4) Uiso d 1 . .
    H H2 0.7493(17) 0.3472(9) 0.1987(11) 0.029(4) Uiso d 1 . .
    H H21B 0.4285(17) 0.9151(8) 0.5899(11) 0.029(4) Uiso d 1 . .
    H H5 0.2680(16) 0.2683(8) 0.2613(10) 0.018(3) Uiso d 1 . .
    H H24A 0.0477(19) 1.0608(9) 0.3914(12) 0.040(5) Uiso d 1 . .
    H H24B 0.209(2) 1.0783(9) 0.3595(14) 0.044(5) Uiso d 1 . .
    H H3 0.6594(16) 0.2171(8) 0.1605(11) 0.023(4) Uiso d 1 . .
    H H11 -0.1567(16) 0.4405(8) 0.4156(10) 0.023(4) Uiso d 1 . .
    H H16 0.5570(16) 0.7553(9) 0.3410(11) 0.026(4) Uiso d 1 . .
    H H25A 0.0885(17) 1.2038(9) 0.3793(12) 0.032(4) Uiso d 1 . .
    H H25B 0.0814(19) 1.1804(10) 0.4929(13) 0.045(5) Uiso d 1 . .
    H H25C 0.243(2) 1.1968(11) 0.4611(14) 0.054(5) Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C17 . 1.3602(13) ?
    O1 C20 . 1.4423(14) ?
    N2 C7 . 1.3872(14) ?
    N2 C8 . 1.4342(14) ?
    N2 C6 . 1.3884(14) ?
    N1 C1 . 1.3921(15) ?
    N1 C7 . 1.3189(14) ?
    C1 C6 . 1.4019(16) ?
    C1 C2 . 1.4000(16) ?
    C7 C14 . 1.4683(15) ?
    C18 C17 . 1.3930(16) ?
    C18 C19 . 1.3899(16) ?
    C18 H18 . 0.976(13) ?
    C14 C15 . 1.4025(16) ?
    C14 C19 . 1.3954(16) ?
    C17 C16 . 1.4007(16) ?
    C15 C16 . 1.3826(16) ?
    C15 H15 . 0.964(14) ?
    C8 C9 . 1.3847(16) ?
    C8 C13 . 1.3874(16) ?
    C6 C5 . 1.3920(17) ?
    C19 H19 . 0.972(13) ?
    C16 H16 . 0.989(15) ?
    C9 C10 . 1.3893(17) ?
    C9 H9 . 0.996(14) ?
    C5 C4 . 1.3861(17) ?
    C5 H5 . 0.957(14) ?
    C11 C10 . 1.3857(17) ?
    C11 C12 . 1.3869(17) ?
    C11 H11 . 0.988(14) ?
    C2 C3 . 1.3812(18) ?
    C2 H2 . 0.964(15) ?
    C13 C12 . 1.3874(16) ?
    C13 H13 . 1.002(15) ?
    C4 C3 . 1.4034(18) ?
    C4 H4 . 0.978(14) ?
    C3 H3 . 0.981(14) ?
    C10 H10 . 0.997(15) ?
    C12 H12 . 0.976(15) ?
    C20 C21 . 1.5115(17) ?
    C20 H20A . 1.011(14) ?
    C20 H20B . 1.010(14) ?
    C23 C22 . 1.5241(17) ?
    C23 C24 . 1.5209(18) ?
    C23 H23A . 1.023(15) ?
    C23 H23B . 1.007(16) ?
    C21 C22 . 1.5226(18) ?
    C21 H21A . 1.008(16) ?
    C21 H21B . 0.989(15) ?
    C22 H22A . 1.002(17) ?
    C22 H22B . 0.999(17) ?
    C24 C25 . 1.5204(18) ?
    C24 H24A . 1.032(17) ?
    C24 H24B . 0.998(18) ?
    C25 H25A . 0.999(16) ?
    C25 H25B . 1.014(18) ?
    C25 H25C . 1.000(19) ?
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
    C17 O1 C20 . . 116.33(9) ?
    C7 N2 C8 . . 128.59(9) ?
    C7 N2 C6 . . 106.62(9) ?
    C6 N2 C8 . . 124.70(9) ?
    C7 N1 C1 . . 105.14(9) ?
    N1 C1 C6 . . 110.40(9) ?
    N1 C1 C2 . . 130.08(11) ?
    C2 C1 C6 . . 119.52(11) ?
    N2 C7 C14 . . 123.70(10) ?
    N1 C7 N2 . . 112.61(10) ?
    N1 C7 C14 . . 123.69(10) ?
    C17 C18 H18 . . 121.0(8) ?
    C19 C18 C17 . . 119.75(10) ?
    C19 C18 H18 . . 119.2(8) ?
    C15 C14 C7 . . 119.35(10) ?
    C19 C14 C7 . . 122.48(10) ?
    C19 C14 C15 . . 118.14(10) ?
    O1 C17 C18 . . 124.23(10) ?
    O1 C17 C16 . . 116.29(10) ?
    C18 C17 C16 . . 119.48(10) ?
    C14 C15 H15 . . 119.5(8) ?
    C16 C15 C14 . . 120.95(11) ?
    C16 C15 H15 . . 119.5(8) ?
    C9 C8 N2 . . 119.07(10) ?
    C9 C8 C13 . . 121.22(10) ?
    C13 C8 N2 . . 119.71(10) ?
    N2 C6 C1 . . 105.22(9) ?
    N2 C6 C5 . . 131.77(11) ?
    C5 C6 C1 . . 123.00(10) ?
    C18 C19 C14 . . 121.42(11) ?
    C18 C19 H19 . . 119.0(8) ?
    C14 C19 H19 . . 119.6(8) ?
    C17 C16 H16 . . 118.4(8) ?
    C15 C16 C17 . . 120.20(11) ?
    C15 C16 H16 . . 121.4(8) ?
    C8 C9 C10 . . 119.09(11) ?
    C8 C9 H9 . . 120.3(8) ?
    C10 C9 H9 . . 120.6(8) ?
    C6 C5 H5 . . 120.6(8) ?
    C4 C5 C6 . . 116.46(11) ?
    C4 C5 H5 . . 123.0(8) ?
    C10 C11 C12 . . 120.19(11) ?
    C10 C11 H11 . . 120.1(8) ?
    C12 C11 H11 . . 119.7(8) ?
    C1 C2 H2 . . 120.8(9) ?
    C3 C2 C1 . . 117.94(11) ?
    C3 C2 H2 . . 121.2(9) ?
    C8 C13 H13 . . 118.9(8) ?
    C12 C13 C8 . . 119.19(11) ?
    C12 C13 H13 . . 121.9(8) ?
    C5 C4 C3 . . 121.40(12) ?
    C5 C4 H4 . . 120.8(8) ?
    C3 C4 H4 . . 117.8(8) ?
    C2 C3 C4 . . 121.66(11) ?
    C2 C3 H3 . . 117.6(8) ?
    C4 C3 H3 . . 120.7(8) ?
    C9 C10 H10 . . 120.9(9) ?
    C11 C10 C9 . . 120.20(11) ?
    C11 C10 H10 . . 118.9(9) ?
    C11 C12 C13 . . 120.09(11) ?
    C11 C12 H12 . . 119.2(9) ?
    C13 C12 H12 . . 120.7(9) ?
    O1 C20 C21 . . 107.87(10) ?
    O1 C20 H20A . . 108.6(8) ?
    O1 C20 H20B . . 108.3(8) ?
    C21 C20 H20A . . 110.5(8) ?
    C21 C20 H20B . . 112.2(8) ?
    H20A C20 H20B . . 109.2(11) ?
    C22 C23 H23A . . 110.2(8) ?
    C22 C23 H23B . . 109.2(8) ?
    C24 C23 C22 . . 112.71(11) ?
    C24 C23 H23A . . 107.7(8) ?
    C24 C23 H23B . . 110.0(9) ?
    H23A C23 H23B . . 106.8(12) ?
    C20 C21 C22 . . 113.57(11) ?
    C20 C21 H21A . . 107.0(8) ?
    C20 C21 H21B . . 108.5(8) ?
    C22 C21 H21A . . 109.2(9) ?
    C22 C21 H21B . . 110.2(9) ?
    H21A C21 H21B . . 108.3(12) ?
    C23 C22 H22A . . 109.1(9) ?
    C23 C22 H22B . . 109.3(9) ?
    C21 C22 C23 . . 113.07(11) ?
    C21 C22 H22A . . 110.2(9) ?
    C21 C22 H22B . . 109.6(9) ?
    H22A C22 H22B . . 105.3(13) ?
    C23 C24 H24A . . 108.6(9) ?
    C23 C24 H24B . . 109.5(10) ?
    C25 C24 C23 . . 113.54(11) ?
    C25 C24 H24A . . 108.6(9) ?
    C25 C24 H24B . . 109.5(9) ?
    H24A C24 H24B . . 106.9(13) ?
    C24 C25 H25A . . 112.1(9) ?
    C24 C25 H25B . . 111.0(9) ?
    C24 C25 H25C . . 110.0(10) ?
    H25A C25 H25B . . 108.5(13) ?
    H25A C25 H25C . . 107.6(13) ?
    H25B C25 H25C . . 107.5(14) ?
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 C17 C16 C15 . . . . -178.63(10) ?
    O1 C20 C21 C22 . . . . 65.39(14) ?
    N2 C7 C14 C15 . . . . -150.27(11) ?
    N2 C7 C14 C19 . . . . 31.78(17) ?
    N2 C8 C9 C10 . . . . 178.61(11) ?
    N2 C8 C13 C12 . . . . -178.46(11) ?
    N2 C6 C5 C4 . . . . 179.78(12) ?
    N1 C1 C6 N2 . . . . -0.11(12) ?
    N1 C1 C6 C5 . . . . 178.73(11) ?
    N1 C1 C2 C3 . . . . -179.72(12) ?
    N1 C7 C14 C15 . . . . 30.87(16) ?
    N1 C7 C14 C19 . . . . -147.09(11) ?
    C1 N1 C7 N2 . . . . -0.66(13) ?
    C1 N1 C7 C14 . . . . 178.32(10) ?
    C1 C6 C5 C4 . . . . 1.28(18) ?
    C1 C2 C3 C4 . . . . 0.32(18) ?
    C7 N2 C8 C9 . . . . -112.83(13) ?
    C7 N2 C8 C13 . . . . 66.81(16) ?
    C7 N2 C6 C1 . . . . -0.28(12) ?
    C7 N2 C6 C5 . . . . -178.97(12) ?
    C7 N1 C1 C6 . . . . 0.47(13) ?
    C7 N1 C1 C2 . . . . -178.88(12) ?
    C7 C14 C15 C16 . . . . 179.44(11) ?
    C7 C14 C19 C18 . . . . -179.95(10) ?
    C18 C17 C16 C15 . . . . 1.73(17) ?
    C14 C15 C16 C17 . . . . 0.65(18) ?
    C17 O1 C20 C21 . . . . -177.40(10) ?
    C17 C18 C19 C14 . . . . 0.26(17) ?
    C15 C14 C19 C18 . . . . 2.07(17) ?
    C8 N2 C7 N1 . . . . -176.10(10) ?
    C8 N2 C7 C14 . . . . 4.92(18) ?
    C8 N2 C6 C1 . . . . 176.60(10) ?
    C8 N2 C6 C5 . . . . -2.10(19) ?
    C8 C9 C10 C11 . . . . 0.10(19) ?
    C8 C13 C12 C11 . . . . -0.39(19) ?
    C6 N2 C7 N1 . . . . 0.61(13) ?
    C6 N2 C7 C14 . . . . -178.37(10) ?
    C6 N2 C8 C9 . . . . 71.01(15) ?
    C6 N2 C8 C13 . . . . -109.35(13) ?
    C6 C1 C2 C3 . . . . 0.98(17) ?
    C6 C5 C4 C3 . . . . 0.08(18) ?
    C19 C18 C17 O1 . . . . 178.21(10) ?
    C19 C18 C17 C16 . . . . -2.17(17) ?
    C19 C14 C15 C16 . . . . -2.51(17) ?
    C9 C8 C13 C12 . . . . 1.17(18) ?
    C5 C4 C3 C2 . . . . -0.88(19) ?
    C2 C1 C6 N2 . . . . 179.31(10) ?
    C2 C1 C6 C5 . . . . -1.85(18) ?
    C13 C8 C9 C10 . . . . -1.03(18) ?
    C10 C11 C12 C13 . . . . -0.5(2) ?
    C12 C11 C10 C9 . . . . 0.7(2) ?
    C20 O1 C17 C18 . . . . -5.57(16) ?
    C20 O1 C17 C16 . . . . 174.80(10) ?
    C20 C21 C22 C23 . . . . 175.95(12) ?
    C22 C23 C24 C25 . . . . 179.25(13) ?
    C24 C23 C22 C21 . . . . -178.39(12) ?
_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     0.983
_shelx_estimated_absorpt_T_max     0.988
data_1
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_chemical_name_systematic
;
1-Benzyl-2-(4-hexyloxyphenyl)-1H-benzimidazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H22 N2 O'
_chemical_formula_sum     'C19 H22 N2 O'
_chemical_formula_iupac     'C19 H22 N2 O'
_chemical_formula_weight     294.38
_chemical_melting_point     ?
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P b c a'
_space_group_name_Hall     '-P 2ac 2ab'
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'
_cell_length_a     9.3802(13)
_cell_length_b     9.4076(13)
_cell_length_c     37.235(5)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     3285.8(8)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3935
_cell_measurement_theta_min     2.19
_cell_measurement_theta_max     22.22
_cell_measurement_temperature     150.0
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.16
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.01
_exptl_crystal_density_diffrn     1.190
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1264
_exptl_absorpt_coefficient_mu     0.074
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_absorpt_correction_T_min     0.6420
_exptl_absorpt_correction_T_max     0.7454
_diffrn_ambient_temperature     150.0
_diffrn_source     'microfocus sealed X-ray tube'
_diffrn_source_power     0.07
_diffrn_source_voltage     50.0
_diffrn_source_current     1.4
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'focusing mirrors'
_diffrn_measurement_device_type     'Bruker D8 Venture'
_diffrn_measurement_device     '3-circle diffractometer'
_diffrn_measurement_method     ω-scan
_diffrn_detector     'Bruker PHOTON III CMOS'
_diffrn_detector_area_resol_mean     10.4
_diffrn_reflns_number     26780
_diffrn_reflns_av_R_equivalents     0.0973
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_theta_min     2.188
_diffrn_reflns_theta_max     25.049
_diffrn_reflns_theta_full     25.049
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -44
_diffrn_reflns_limit_l_max     44
_diffrn_standards_number     0
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     2900
_reflns_number_gt     2171
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1250
_refine_ls_R_factor_gt     0.0988
_refine_ls_wR_factor_gt     0.2222
_refine_ls_wR_factor_ref     0.2332
_refine_ls_goodness_of_fit_ref     1.168
_refine_ls_restrained_S_all     1.168
_refine_ls_number_reflns     2900
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
             'w=1/[σ²(Fo²)+(0.0273P)²+15.0864P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.317
_refine_diff_density_min     -0.398
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_cell_refinement
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
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 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) ?
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
_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
