##############################################################################
#                                                                            #
# 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_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
4-Methyl-N-(2-phenylethyl)-2-propyl-1H-benzimidazole-
6-carboxamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H23 N3 O'
_chemical_formula_sum     'C20 H23 N3 O'
_chemical_formula_iupac     'C20 H23 N3 O'
_chemical_formula_weight     321.41
_chemical_melting_point     ?
_chemical_melting_point_gt     ?
_chemical_melting_point_lt     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     10.2028(7)
_cell_length_b     11.9126(9)
_cell_length_c     17.0553(17)
_cell_angle_alpha     101.563(4)
_cell_angle_beta     99.110(4)
_cell_angle_gamma     113.808(2)
_cell_volume     1790.6(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     362
_cell_measurement_theta_min     1.95
_cell_measurement_theta_max     25.01
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.41
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.192
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     688
_exptl_absorpt_coefficient_mu     0.075
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2007)'
_exptl_absorpt_correction_T_min     0.6701
_exptl_absorpt_correction_T_max     0.7456
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     17517
_diffrn_reflns_av_R_equivalents     0.0290
_diffrn_reflns_av_sigmaI/netI     0.0317
_diffrn_reflns_theta_min     1.95
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.962
_diffrn_measured_fraction_theta_full     0.962
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     6081
_reflns_number_gt     4250
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0740
_refine_ls_R_factor_gt     0.0485
_refine_ls_wR_factor_gt     0.1295
_refine_ls_wR_factor_ref     0.1553
_refine_ls_goodness_of_fit_ref     1.075
_refine_ls_restrained_S_all     1.088
_refine_ls_number_reflns     6081
_refine_ls_number_parameters     450
_refine_ls_number_restraints     46
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w=1/[σ²(Fo²)+(0.0753P)²+0.4342P] P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.368
_refine_diff_density_min     -0.297
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0088(17)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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     'APEX2 (Bruker 2007)'
_computing_cell_refinement     'APEX2 and SAINT (Bruker 2007)'
_computing_data_reduction     'SAINT (Bruker 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    H H1 0.7674(19) 1.1106(15) 0.1249(14) 0.060(7) Uiso d D 1 1 . .
    H H4 -0.2645(15) 0.1827(16) -0.1485(14) 0.055(7) Uiso d D 1 1 . .
    H H5 0.2616(18) 0.460(2) 0.2126(15) 0.069(8) Uiso d D 1 1 . .
    H H6 0.7939(19) 0.598(2) 0.2321(15) 0.066(8) Uiso d D 1 1 . .
    C C1 0.3195(3) 1.2092(3) 0.08894(19) 0.0728(8) Uani d . 1 1 . .
    H H1A 0.2239 1.1948 0.0974 0.109 Uiso calc R 1 1 . .
    H H1B 0.3159 1.2026 0.0315 0.109 Uiso calc R 1 1 . .
    H H1C 0.3927 1.2932 0.1227 0.109 Uiso calc R 1 1 . .
    C C2 0.3606(3) 1.1097(3) 0.1127(2) 0.0710(8) Uani d . 1 1 . .
    H H2A 0.3619 1.1157 0.1704 0.085 Uiso calc R 1 1 . .
    H H2B 0.2848 1.0250 0.0793 0.085 Uiso calc R 1 1 . .
    C C3 0.5086(3) 1.1247(2) 0.10119(15) 0.0503(6) Uani d . 1 1 . .
    H H3A 0.5067 1.1194 0.0435 0.060 Uiso calc R 1 1 . .
    H H3B 0.5836 1.2098 0.1345 0.060 Uiso calc R 1 1 . .
    C C4 0.5540(2) 1.02936(19) 0.12349(13) 0.0427(5) Uani d . 1 1 . .
    C C5 0.7011(2) 0.93810(19) 0.14869(13) 0.0407(5) Uani d . 1 1 . .
    C C6 0.8141(2) 0.9008(2) 0.15921(14) 0.0473(5) Uani d . 1 1 . .
    C C7 0.7821(2) 0.7941(2) 0.18722(14) 0.0481(5) Uani d . 1 1 . .
    H H7A 0.8550 0.7666 0.1963 0.058 Uiso calc R 1 1 . .
    C C8 0.6452(2) 0.72490(19) 0.20267(13) 0.0416(5) Uani d . 1 1 . .
    C C9 0.5340(2) 0.76211(19) 0.18845(13) 0.0426(5) Uani d . 1 1 . .
    H H9A 0.4420 0.7163 0.1972 0.051 Uiso calc R 1 1 . .
    C C10 0.5623(2) 0.86912(19) 0.16083(13) 0.0403(5) Uani d . 1 1 . .
    C C11 0.9585(3) 0.9701(3) 0.1396(2) 0.0711(8) Uani d . 1 1 . .
    H H11A 1.0215 0.9301 0.1511 0.107 Uiso calc R 1 1 . .
    H H11B 1.0068 1.0580 0.1731 0.107 Uiso calc R 1 1 . .
    H H11C 0.9398 0.9664 0.0819 0.107 Uiso calc R 1 1 . .
    C C12 0.6116(2) 0.6129(2) 0.23587(13) 0.0437(5) Uani d . 1 1 . .
    C C13 0.6911(3) 0.4712(2) 0.29015(16) 0.0601(6) Uani d . 1 1 . .
    H H13A 0.6338 0.3898 0.2472 0.072 Uiso calc R 1 1 . .
    H H13B 0.6322 0.4768 0.3288 0.072 Uiso calc R 1 1 . .
    C C14 0.8298(3) 0.4735(3) 0.33495(18) 0.0699(7) Uani d . 1 1 . .
    H H14A 0.8900 0.5560 0.3765 0.084 Uiso calc R 1 1 . .
    H H14B 0.8866 0.4625 0.2961 0.084 Uiso calc R 1 1 . .
    C C15 0.7950(3) 0.3686(3) 0.37630(15) 0.0579(6) Uani d . 1 1 . .
    C C16 0.7603(3) 0.2458(3) 0.33270(16) 0.0689(7) Uani d . 1 1 . .
    H H16A 0.7644 0.2289 0.2777 0.083 Uiso calc R 1 1 . .
    C C17 0.7198(4) 0.1472(3) 0.3681(2) 0.0823(9) Uani d . 1 1 . .
    H H17A 0.6971 0.0649 0.3371 0.099 Uiso calc R 1 1 . .
    C C18 0.7128(4) 0.1698(4) 0.4486(2) 0.0923(10) Uani d . 1 1 . .
    H H18A 0.6830 0.1031 0.4725 0.111 Uiso calc R 1 1 . .
    C C19 0.7503(5) 0.2916(4) 0.4931(2) 0.1045(12) Uani d . 1 1 . .
    H H19A 0.7494 0.3084 0.5486 0.125 Uiso calc R 1 1 . .
    C C20 0.7896(4) 0.3905(3) 0.45784(18) 0.0886(10) Uani d . 1 1 . .
    H H20A 0.8127 0.4727 0.4892 0.106 Uiso calc R 1 1 . .
    C C21 -0.2363(7) 0.0418(5) -0.3386(3) 0.187(3) Uani d . 1 1 . .
    H H21A -0.3117 -0.0448 -0.3650 0.281 Uiso calc R 1 1 . .
    H H21B -0.1802 0.0466 -0.2861 0.281 Uiso calc R 1 1 . .
    H H21C -0.1711 0.0675 -0.3734 0.281 Uiso calc R 1 1 . .
    C C22 -0.3053(4) 0.1261(3) -0.32530(19) 0.0923(10) Uani d . 1 1 . .
    H H22A -0.3727 0.0981 -0.2912 0.111 Uiso calc R 1 1 . .
    H H22B -0.3637 0.1189 -0.3784 0.111 Uiso calc R 1 1 . .
    C C23 -0.1962(3) 0.2635(2) -0.28424(14) 0.0564(6) Uani d . 1 1 . .
    H H23A -0.1253 0.2884 -0.3168 0.068 Uiso calc R 1 1 . .
    H H23B -0.2494 0.3149 -0.2863 0.068 Uiso calc R 1 1 . .
    C C24 -0.1116(2) 0.2973(2) -0.19662(13) 0.0444(5) Uani d . 1 1 . .
    C C25 0.0603(2) 0.38852(19) -0.08105(12) 0.0388(5) Uani d . 1 1 . .
    C C26 -0.0660(2) 0.30365(19) -0.06467(12) 0.0381(5) Uani d . 1 1 . .
    C C27 -0.0696(2) 0.28931(19) 0.01351(13) 0.0412(5) Uani d . 1 1 . .
    H H27A -0.1556 0.2326 0.0231 0.049 Uiso calc R 1 1 . .
    C C28 0.0598(2) 0.36249(18) 0.07695(12) 0.0382(5) Uani d . 1 1 . .
    C C29 0.1881(2) 0.44721(19) 0.06003(13) 0.0421(5) Uani d . 1 1 . .
    H H29A 0.2743 0.4948 0.1034 0.050 Uiso calc R 1 1 . .
    C C30 0.1921(2) 0.46316(19) -0.01772(13) 0.0427(5) Uani d . 1 1 . .
    C C31 0.3295(3) 0.5560(2) -0.03364(15) 0.0644(7) Uani d . 1 1 . .
    H H31A 0.4081 0.5978 0.0169 0.097 Uiso calc R 1 1 . .
    H H31B 0.3093 0.6190 -0.0532 0.097 Uiso calc R 1 1 . .
    H H31C 0.3589 0.5105 -0.0748 0.097 Uiso calc R 1 1 . .
    C C32 0.0549(2) 0.34704(19) 0.16112(13) 0.0420(5) Uani d . 1 1 . .
    C C33 0.1868(3) 0.3983(2) 0.30617(14) 0.0545(6) Uani d . 1 1 . .
    H H33A 0.0883 0.3677 0.3150 0.065 Uiso calc R 1 1 . .
    H H33B 0.2496 0.4812 0.3469 0.065 Uiso calc R 1 1 . .
    C C34 0.2479(4) 0.3063(3) 0.31926(17) 0.0765(8) Uani d U 1 1 . .
    H H34A 0.3500 0.3417 0.3158 0.092 Uiso calc R 1 1 . .
    H H34B 0.1915 0.2267 0.2746 0.092 Uiso calc R 1 1 . .
    C C35 0.2442(3) 0.2766(3) 0.40085(16) 0.0652(7) Uani d U 1 1 . .
    C C36 0.1137(4) 0.2081(4) 0.4166(2) 0.0960(10) Uani d U 1 1 . .
    H H36A 0.0252 0.1813 0.3768 0.115 Uiso calc R 1 1 . .
    C C37 0.1083(6) 0.1767(4) 0.4904(3) 0.1156(13) Uani d U 1 1 . .
    H H37A 0.0175 0.1301 0.5001 0.139 Uiso calc R 1 1 . .
    C C38 0.2369(7) 0.2147(4) 0.5481(2) 0.1115(13) Uani d U 1 1 . .
    H H38A 0.2346 0.1926 0.5974 0.134 Uiso calc R 1 1 . .
    C C39 0.3665(6) 0.2835(4) 0.5348(2) 0.1176(14) Uani d U 1 1 . .
    H H39A 0.4544 0.3102 0.5751 0.141 Uiso calc R 1 1 . .
    C C40 0.3712(4) 0.3158(3) 0.4614(2) 0.0939(10) Uani d U 1 1 . .
    H H40A 0.4626 0.3650 0.4532 0.113 Uiso calc R 1 1 . .
    N N1 0.6923(2) 1.03909(17) 0.12434(11) 0.0445(4) Uani d D 1 1 . .
    N N2 0.47131(19) 0.92760(16) 0.14350(11) 0.0444(4) Uani d . 1 1 . .
    N N3 0.02963(19) 0.38310(16) -0.16468(10) 0.0438(4) Uani d . 1 1 . .
    N N4 -0.1741(2) 0.24659(17) -0.13948(11) 0.0439(4) Uani d D 1 1 . .
    N N5 0.1783(2) 0.41362(19) 0.22348(11) 0.0506(5) Uani d D 1 1 . .
    N N6 0.7166(2) 0.57415(18) 0.25232(12) 0.0502(5) Uani d D 1 1 . .
    O O1 0.49045(17) 0.55903(16) 0.25059(10) 0.0586(4) Uani d . 1 1 . .
    O O2 -0.06237(17) 0.27366(15) 0.17288(9) 0.0585(5) Uani d . 1 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
    C1 C2 . 1.511(4) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 C3 . 1.498(3) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.481(3) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 N2 . 1.315(3) ?
    C4 N1 . 1.366(3) ?
    C5 N1 . 1.380(3) ?
    C5 C6 . 1.393(3) ?
    C5 C10 . 1.395(3) ?
    C6 C7 . 1.382(3) ?
    C6 C11 . 1.500(3) ?
    C7 C8 . 1.406(3) ?
    C7 H7A . 0.9300 ?
    C8 C9 . 1.380(3) ?
    C8 C12 . 1.488(3) ?
    C9 C10 . 1.385(3) ?
    C9 H9A . 0.9300 ?
    C10 N2 . 1.397(3) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 O1 . 1.235(2) ?
    C12 N6 . 1.340(3) ?
    C13 N6 . 1.449(3) ?
    C13 C14 . 1.486(3) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 C15 . 1.503(3) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 C16 . 1.371(4) ?
    C15 C20 . 1.377(4) ?
    C16 C17 . 1.373(4) ?
    C16 H16A . 0.9300 ?
    C17 C18 . 1.364(4) ?
    C17 H17A . 0.9300 ?
    C18 C19 . 1.359(5) ?
    C18 H18A . 0.9300 ?
    C19 C20 . 1.375(4) ?
    C19 H19A . 0.9300 ?
    C20 H20A . 0.9300 ?
    C21 C22 . 1.444(6) ?
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
    C22 C23 . 1.494(4) ?
    C22 H22A . 0.9700 ?
    C22 H22B . 0.9700 ?
    C23 C24 . 1.487(3) ?
    C23 H23A . 0.9700 ?
    C23 H23B . 0.9700 ?
    C24 N3 . 1.326(3) ?
    C24 N4 . 1.357(3) ?
    C25 C26 . 1.392(3) ?
    C25 N3 . 1.394(3) ?
    C25 C30 . 1.399(3) ?
    C26 N4 . 1.381(3) ?
    C26 C27 . 1.382(3) ?
    C27 C28 . 1.383(3) ?
    C27 H27A . 0.9300 ?
    C28 C29 . 1.408(3) ?
    C28 C32 . 1.490(3) ?
    C29 C30 . 1.381(3) ?
    C29 H29A . 0.9300 ?
    C30 C31 . 1.500(3) ?
    C31 H31A . 0.9600 ?
    C31 H31B . 0.9600 ?
    C31 H31C . 0.9600 ?
    C32 O2 . 1.240(2) ?
    C32 N5 . 1.333(3) ?
    C33 N5 . 1.451(3) ?
    C33 C34 . 1.499(4) ?
    C33 H33A . 0.9700 ?
    C33 H33B . 0.9700 ?
    C34 C35 . 1.505(4) ?
    C34 H34A . 0.9700 ?
    C34 H34B . 0.9700 ?
    C35 C36 . 1.355(4) ?
    C35 C40 . 1.363(4) ?
    C36 C37 . 1.386(5) ?
    C36 H36A . 0.9300 ?
    C37 C38 . 1.352(6) ?
    C37 H37A . 0.9300 ?
    C38 C39 . 1.329(6) ?
    C38 H38A . 0.9300 ?
    C39 C40 . 1.385(5) ?
    C39 H39A . 0.9300 ?
    C40 H40A . 0.9300 ?
    N1 H1 . 0.883(10) ?
    N4 H4 . 0.892(10) ?
    N5 H5 . 0.879(10) ?
    N6 H6 . 0.875(10) ?
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
    C2 C1 H1A . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    C3 C2 C1 . . 113.1(2) ?
    C3 C2 H2A . . 109.0 ?
    C1 C2 H2A . . 109.0 ?
    C3 C2 H2B . . 109.0 ?
    C1 C2 H2B . . 109.0 ?
    H2A C2 H2B . . 107.8 ?
    C4 C3 C2 . . 115.24(19) ?
    C4 C3 H3A . . 108.5 ?
    C2 C3 H3A . . 108.5 ?
    C4 C3 H3B . . 108.5 ?
    C2 C3 H3B . . 108.5 ?
    H3A C3 H3B . . 107.5 ?
    N2 C4 N1 . . 112.09(19) ?
    N2 C4 C3 . . 126.25(19) ?
    N1 C4 C3 . . 121.65(19) ?
    N1 C5 C6 . . 132.18(19) ?
    N1 C5 C10 . . 105.01(18) ?
    C6 C5 C10 . . 122.79(19) ?
    C7 C6 C5 . . 115.18(19) ?
    C7 C6 C11 . . 122.6(2) ?
    C5 C6 C11 . . 122.2(2) ?
    C6 C7 C8 . . 123.4(2) ?
    C6 C7 H7A . . 118.3 ?
    C8 C7 H7A . . 118.3 ?
    C9 C8 C7 . . 119.63(19) ?
    C9 C8 C12 . . 116.51(19) ?
    C7 C8 C12 . . 123.85(19) ?
    C8 C9 C10 . . 118.61(19) ?
    C8 C9 H9A . . 120.7 ?
    C10 C9 H9A . . 120.7 ?
    C9 C10 C5 . . 120.31(19) ?
    C9 C10 N2 . . 129.93(19) ?
    C5 C10 N2 . . 109.74(18) ?
    C6 C11 H11A . . 109.5 ?
    C6 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C6 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    O1 C12 N6 . . 120.5(2) ?
    O1 C12 C8 . . 120.5(2) ?
    N6 C12 C8 . . 119.02(19) ?
    N6 C13 C14 . . 113.7(2) ?
    N6 C13 H13A . . 108.8 ?
    C14 C13 H13A . . 108.8 ?
    N6 C13 H13B . . 108.8 ?
    C14 C13 H13B . . 108.8 ?
    H13A C13 H13B . . 107.7 ?
    C13 C14 C15 . . 110.8(2) ?
    C13 C14 H14A . . 109.5 ?
    C15 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    C15 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 108.1 ?
    C16 C15 C20 . . 117.6(2) ?
    C16 C15 C14 . . 120.9(2) ?
    C20 C15 C14 . . 121.5(3) ?
    C15 C16 C17 . . 121.7(3) ?
    C15 C16 H16A . . 119.1 ?
    C17 C16 H16A . . 119.1 ?
    C18 C17 C16 . . 120.1(3) ?
    C18 C17 H17A . . 119.9 ?
    C16 C17 H17A . . 119.9 ?
    C19 C18 C17 . . 118.7(3) ?
    C19 C18 H18A . . 120.6 ?
    C17 C18 H18A . . 120.6 ?
    C18 C19 C20 . . 121.4(3) ?
    C18 C19 H19A . . 119.3 ?
    C20 C19 H19A . . 119.3 ?
    C19 C20 C15 . . 120.4(3) ?
    C19 C20 H20A . . 119.8 ?
    C15 C20 H20A . . 119.8 ?
    C22 C21 H21A . . 109.5 ?
    C22 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C22 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C21 C22 C23 . . 113.4(4) ?
    C21 C22 H22A . . 108.9 ?
    C23 C22 H22A . . 108.9 ?
    C21 C22 H22B . . 108.9 ?
    C23 C22 H22B . . 108.9 ?
    H22A C22 H22B . . 107.7 ?
    C24 C23 C22 . . 117.0(2) ?
    C24 C23 H23A . . 108.0 ?
    C22 C23 H23A . . 108.0 ?
    C24 C23 H23B . . 108.0 ?
    C22 C23 H23B . . 108.0 ?
    H23A C23 H23B . . 107.3 ?
    N3 C24 N4 . . 112.61(19) ?
    N3 C24 C23 . . 124.40(19) ?
    N4 C24 C23 . . 122.9(2) ?
    C26 C25 N3 . . 109.70(18) ?
    C26 C25 C30 . . 120.55(18) ?
    N3 C25 C30 . . 129.74(18) ?
    N4 C26 C27 . . 131.64(18) ?
    N4 C26 C25 . . 105.57(17) ?
    C27 C26 C25 . . 122.78(19) ?
    C26 C27 C28 . . 117.46(18) ?
    C26 C27 H27A . . 121.3 ?
    C28 C27 H27A . . 121.3 ?
    C27 C28 C29 . . 119.67(19) ?
    C27 C28 C32 . . 117.12(18) ?
    C29 C28 C32 . . 123.21(19) ?
    C30 C29 C28 . . 123.3(2) ?
    C30 C29 H29A . . 118.4 ?
    C28 C29 H29A . . 118.4 ?
    C29 C30 C25 . . 116.26(18) ?
    C29 C30 C31 . . 122.2(2) ?
    C25 C30 C31 . . 121.58(19) ?
    C30 C31 H31A . . 109.5 ?
    C30 C31 H31B . . 109.5 ?
    H31A C31 H31B . . 109.5 ?
    C30 C31 H31C . . 109.5 ?
    H31A C31 H31C . . 109.5 ?
    H31B C31 H31C . . 109.5 ?
    O2 C32 N5 . . 120.66(19) ?
    O2 C32 C28 . . 120.42(19) ?
    N5 C32 C28 . . 118.92(18) ?
    N5 C33 C34 . . 112.4(2) ?
    N5 C33 H33A . . 109.1 ?
    C34 C33 H33A . . 109.1 ?
    N5 C33 H33B . . 109.1 ?
    C34 C33 H33B . . 109.1 ?
    H33A C33 H33B . . 107.9 ?
    C33 C34 C35 . . 114.4(2) ?
    C33 C34 H34A . . 108.7 ?
    C35 C34 H34A . . 108.7 ?
    C33 C34 H34B . . 108.7 ?
    C35 C34 H34B . . 108.7 ?
    H34A C34 H34B . . 107.6 ?
    C36 C35 C40 . . 117.3(3) ?
    C36 C35 C34 . . 121.0(3) ?
    C40 C35 C34 . . 121.7(3) ?
    C35 C36 C37 . . 121.8(4) ?
    C35 C36 H36A . . 119.1 ?
    C37 C36 H36A . . 119.1 ?
    C38 C37 C36 . . 119.2(4) ?
    C38 C37 H37A . . 120.4 ?
    C36 C37 H37A . . 120.4 ?
    C39 C38 C37 . . 120.2(4) ?
    C39 C38 H38A . . 119.9 ?
    C37 C38 H38A . . 119.9 ?
    C38 C39 C40 . . 120.4(4) ?
    C38 C39 H39A . . 119.8 ?
    C40 C39 H39A . . 119.8 ?
    C35 C40 C39 . . 121.1(4) ?
    C35 C40 H40A . . 119.5 ?
    C39 C40 H40A . . 119.5 ?
    C4 N1 C5 . . 107.75(17) ?
    C4 N1 H1 . . 122.7(16) ?
    C5 N1 H1 . . 126.8(16) ?
    C4 N2 C10 . . 105.38(17) ?
    C24 N3 C25 . . 104.92(16) ?
    C24 N4 C26 . . 107.21(17) ?
    C24 N4 H4 . . 127.3(15) ?
    C26 N4 H4 . . 125.2(15) ?
    C32 N5 C33 . . 122.83(19) ?
    C32 N5 H5 . . 118.8(17) ?
    C33 N5 H5 . . 117.7(17) ?
    C12 N6 C13 . . 120.33(19) ?
    C12 N6 H6 . . 121.9(17) ?
    C13 N6 H6 . . 116.7(17) ?
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
    C1 C2 C3 C4 . . . . -179.9(2) ?
    C2 C3 C4 N2 . . . . 7.6(3) ?
    C2 C3 C4 N1 . . . . -173.1(2) ?
    N1 C5 C6 C7 . . . . 178.2(2) ?
    C10 C5 C6 C7 . . . . -3.5(3) ?
    N1 C5 C6 C11 . . . . -3.2(4) ?
    C10 C5 C6 C11 . . . . 175.1(2) ?
    C5 C6 C7 C8 . . . . 1.3(3) ?
    C11 C6 C7 C8 . . . . -177.3(2) ?
    C6 C7 C8 C9 . . . . 1.1(3) ?
    C6 C7 C8 C12 . . . . -177.6(2) ?
    C7 C8 C9 C10 . . . . -1.4(3) ?
    C12 C8 C9 C10 . . . . 177.36(18) ?
    C8 C9 C10 C5 . . . . -0.7(3) ?
    C8 C9 C10 N2 . . . . -178.6(2) ?
    N1 C5 C10 C9 . . . . -177.99(18) ?
    C6 C5 C10 C9 . . . . 3.3(3) ?
    N1 C5 C10 N2 . . . . 0.3(2) ?
    C6 C5 C10 N2 . . . . -178.35(19) ?
    C9 C8 C12 O1 . . . . -1.1(3) ?
    C7 C8 C12 O1 . . . . 177.6(2) ?
    C9 C8 C12 N6 . . . . -178.74(19) ?
    C7 C8 C12 N6 . . . . 0.0(3) ?
    N6 C13 C14 C15 . . . . 177.0(2) ?
    C13 C14 C15 C16 . . . . 82.9(3) ?
    C13 C14 C15 C20 . . . . -93.9(3) ?
    C20 C15 C16 C17 . . . . 0.8(4) ?
    C14 C15 C16 C17 . . . . -176.1(3) ?
    C15 C16 C17 C18 . . . . 0.1(5) ?
    C16 C17 C18 C19 . . . . -1.7(5) ?
    C17 C18 C19 C20 . . . . 2.3(6) ?
    C18 C19 C20 C15 . . . . -1.4(6) ?
    C16 C15 C20 C19 . . . . -0.1(5) ?
    C14 C15 C20 C19 . . . . 176.8(3) ?
    C21 C22 C23 C24 . . . . -67.5(4) ?
    C22 C23 C24 N3 . . . . 142.9(3) ?
    C22 C23 C24 N4 . . . . -40.1(3) ?
    N3 C25 C26 N4 . . . . -0.1(2) ?
    C30 C25 C26 N4 . . . . 179.95(18) ?
    N3 C25 C26 C27 . . . . -179.21(18) ?
    C30 C25 C26 C27 . . . . 0.8(3) ?
    N4 C26 C27 C28 . . . . -179.6(2) ?
    C25 C26 C27 C28 . . . . -0.7(3) ?
    C26 C27 C28 C29 . . . . -0.1(3) ?
    C26 C27 C28 C32 . . . . 179.64(17) ?
    C27 C28 C29 C30 . . . . 0.8(3) ?
    C32 C28 C29 C30 . . . . -178.92(19) ?
    C28 C29 C30 C25 . . . . -0.7(3) ?
    C28 C29 C30 C31 . . . . 178.8(2) ?
    C26 C25 C30 C29 . . . . -0.1(3) ?
    N3 C25 C30 C29 . . . . 179.91(19) ?
    C26 C25 C30 C31 . . . . -179.6(2) ?
    N3 C25 C30 C31 . . . . 0.4(3) ?
    C27 C28 C32 O2 . . . . -1.8(3) ?
    C29 C28 C32 O2 . . . . 177.9(2) ?
    C27 C28 C32 N5 . . . . 178.43(19) ?
    C29 C28 C32 N5 . . . . -1.9(3) ?
    N5 C33 C34 C35 . . . . -173.9(2) ?
    C33 C34 C35 C36 . . . . 68.7(4) ?
    C33 C34 C35 C40 . . . . -112.2(3) ?
    C40 C35 C36 C37 . . . . -1.1(5) ?
    C34 C35 C36 C37 . . . . 178.1(3) ?
    C35 C36 C37 C38 . . . . -0.4(6) ?
    C36 C37 C38 C39 . . . . 1.4(7) ?
    C37 C38 C39 C40 . . . . -0.7(7) ?
    C36 C35 C40 C39 . . . . 1.7(5) ?
    C34 C35 C40 C39 . . . . -177.5(3) ?
    C38 C39 C40 C35 . . . . -0.9(6) ?
    N2 C4 N1 C5 . . . . -1.6(2) ?
    C3 C4 N1 C5 . . . . 179.02(19) ?
    C6 C5 N1 C4 . . . . 179.2(2) ?
    C10 C5 N1 C4 . . . . 0.7(2) ?
    N1 C4 N2 C10 . . . . 1.8(2) ?
    C3 C4 N2 C10 . . . . -178.9(2) ?
    C9 C10 N2 C4 . . . . 176.8(2) ?
    C5 C10 N2 C4 . . . . -1.3(2) ?
    N4 C24 N3 C25 . . . . -0.2(2) ?
    C23 C24 N3 C25 . . . . 177.0(2) ?
    C26 C25 N3 C24 . . . . 0.2(2) ?
    C30 C25 N3 C24 . . . . -179.8(2) ?
    N3 C24 N4 C26 . . . . 0.2(2) ?
    C23 C24 N4 C26 . . . . -177.1(2) ?
    C27 C26 N4 C24 . . . . 179.0(2) ?
    C25 C26 N4 C24 . . . . -0.1(2) ?
    O2 C32 N5 C33 . . . . 4.5(3) ?
    C28 C32 N5 C33 . . . . -175.66(19) ?
    C34 C33 N5 C32 . . . . 95.4(3) ?
    O1 C12 N6 C13 . . . . -2.0(3) ?
    C8 C12 N6 C13 . . . . 175.6(2) ?
    C14 C13 N6 C12 . . . . -156.5(2) ?
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
    N1 H1 O2 1_665 0.884 1.91 2.744(2) 156.70 y
    N4 H4 N2 2_565 0.892 2.01 2.882(3) 164.50 y
    N5 H5 O1 1_555 0.879 2.06 2.849(4) 148.37 y
    N6 H6 N3 2_665 0.875 2.25 3.109(2) 168.50 y
data_global
_journal_date_recd_electronic     2012-06-14
_journal_date_accepted     2012-08-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue     10
_journal_page_first     o2824
_journal_page_last     o2824
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812036707
_journal_coeditor_code     ZJ2085
_publ_contact_author_name     'Dr. Jin-Liang Wang'
_publ_contact_author_address
;
R&D Center for Pharmaceuticals
School of Chemical Engineering & the Environment
Beijing Institute of Technology
Beijing 100081
People's Republic of China
;
_publ_contact_author_email     'jims-wang@hotmail.com'
_publ_contact_author_fax     '+86 010 6891-8982'
_publ_contact_author_phone     '+86 010 6891-8982'
_publ_section_title
;\
4-Methyl-N-(2-phenylethyl)-2-propyl-1H-benzimidazole-6-\
carboxamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Jin-Liang Wang'
;
R&D Center for Pharmaceuticals,
School of Chemical Engineering & the Environment,
Beijing Institute of Technology
Beijing 100083,
People's Republic of China
;
    'Wei-Fa Yu'
;
SINOPEC Research Institute of Petroleum Processing,
Beijing 100083,
People's Republic of China
;
