##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-[2-(4-Fluorobenzyloxy)-2-phenylethyl]-1H-benzimidazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H19 F N2 O'
_chemical_formula_sum     'C22 H19 F N2 O'
_chemical_formula_iupac     'C22 H19 F N2 O'
_chemical_formula_weight     346.39
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     12.6946(2)
_cell_length_b     18.1279(4)
_cell_length_c     15.3547(3)
_cell_angle_alpha     90.00
_cell_angle_beta     95.7470(10)
_cell_angle_gamma     90.00
_cell_volume     3515.76(12)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     8094
_cell_measurement_theta_min     2.910
_cell_measurement_theta_max     27.485
_cell_measurement_temperature     120(2)
_exptl_crystal_description     rod-shaped
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.309
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1456
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2007)'
_exptl_absorpt_correction_T_min     0.9530
_exptl_absorpt_correction_T_max     0.9877
_exptl_special_details
;
;
_diffrn_ambient_temperature     120(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--Nonius KappaCCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     '9.091'
_diffrn_reflns_number     41740
_diffrn_reflns_av_R_equivalents     0.0648
_diffrn_reflns_av_sigmaI/netI     0.0597
_diffrn_reflns_theta_min     3.00
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -23
_diffrn_reflns_limit_k_max     23
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_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 >
σ(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     8050
_reflns_number_gt     5679
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0866
_refine_ls_R_factor_gt     0.0546
_refine_ls_wR_factor_gt     0.1252
_refine_ls_wR_factor_ref     0.1422
_refine_ls_goodness_of_fit_ref     1.069
_refine_ls_restrained_S_all     1.069
_refine_ls_number_reflns     8050
_refine_ls_number_parameters     622
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0671P)²+0.7368P] where 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     0.433
_refine_diff_density_min     -0.430
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0237(14)
_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'
    'F' 'F' 0.0171 0.0103
                         '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     'COLLECT (Hooft, 1998)'
_computing_cell_refinement
                    'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction
                    'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
                                'WinGX (Farrugia, 1999) and PLATON (Spek, 2003)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    F F 1.32492(8) 0.12305(7) 1.08865(8) 0.0437(3) Uani d . 1 . .
    O O 0.89904(9) 0.13207(7) 0.84616(8) 0.0271(3) Uani d . 1 . .
    N N1 0.83956(11) 0.19499(8) 0.67743(9) 0.0249(3) Uani d . 1 . .
    N N2 0.98761(11) 0.20522(9) 0.61001(10) 0.0288(4) Uani d . 1 . .
    C C1 0.94433(14) 0.21182(11) 0.68318(12) 0.0289(4) Uani d . 1 . .
    H H1 0.9829(14) 0.2262(11) 0.7390(12) 0.027(5) Uiso d . 1 . .
    C C2 0.90500(13) 0.18153(9) 0.54985(11) 0.0236(4) Uani d . 1 . .
    C C3 0.90444(14) 0.16519(10) 0.46108(12) 0.0280(4) Uani d . 1 . .
    H H3 0.9686(16) 0.1703(12) 0.4301(13) 0.038(6) Uiso d . 1 . .
    C C4 0.81070(14) 0.14160(10) 0.41732(12) 0.0292(4) Uani d . 1 . .
    H H4 0.8070(16) 0.1292(12) 0.3561(15) 0.039(6) Uiso d . 1 . .
    C C5 0.71803(14) 0.13502(10) 0.45929(12) 0.0283(4) Uani d . 1 . .
    H H5 0.6542(15) 0.1181(11) 0.4275(13) 0.030(5) Uiso d . 1 . .
    C C6 0.71679(13) 0.15155(10) 0.54705(12) 0.0255(4) Uani d . 1 . .
    H H6 0.6538(16) 0.1488(12) 0.5780(13) 0.036(5) Uiso d . 1 . .
    C C7 0.81188(13) 0.17443(9) 0.59110(11) 0.0227(4) Uani d . 1 . .
    C C8 0.77179(14) 0.19141(11) 0.74888(12) 0.0274(4) Uani d . 1 . .
    H H81 0.7859(15) 0.2378(13) 0.7864(13) 0.037(6) Uiso d . 1 . .
    H H82 0.6946(16) 0.1908(11) 0.7251(13) 0.032(5) Uiso d . 1 . .
    C C9 0.79393(13) 0.12350(10) 0.80559(11) 0.0257(4) Uani d . 1 . .
    H H9 0.7892(14) 0.0767(12) 0.7672(13) 0.030(5) Uiso d . 1 . .
    C C10 0.71281(13) 0.11680(10) 0.87108(11) 0.0239(4) Uani d . 1 . .
    C C11 0.63294(14) 0.06463(11) 0.85919(12) 0.0275(4) Uani d . 1 . .
    H H11 0.6307(14) 0.0317(12) 0.8102(13) 0.030(5) Uiso d . 1 . .
    C C12 0.55543(14) 0.06074(11) 0.91698(12) 0.0294(4) Uani d . 1 . .
    H H12 0.5013(16) 0.0250(12) 0.9071(13) 0.036(5) Uiso d . 1 . .
    C C13 0.55847(14) 0.10849(11) 0.98734(12) 0.0302(4) Uani d . 1 . .
    H H13 0.5027(16) 0.1064(11) 1.0291(13) 0.034(5) Uiso d . 1 . .
    C C14 0.63851(14) 0.16059(11) 0.99970(12) 0.0300(4) Uani d . 1 . .
    H H14 0.6394(16) 0.1942(13) 1.0485(14) 0.042(6) Uiso d . 1 . .
    C C15 0.71528(14) 0.16487(10) 0.94216(12) 0.0277(4) Uani d . 1 . .
    H H15 0.7732(15) 0.2003(11) 0.9511(12) 0.028(5) Uiso d . 1 . .
    C C16 0.93679(14) 0.06654(11) 0.89152(13) 0.0294(4) Uani d . 1 . .
    H H161 0.9424(17) 0.0256(14) 0.8473(15) 0.048(6) Uiso d . 1 . .
    H H162 0.8831(15) 0.0495(11) 0.9330(13) 0.030(5) Uiso d . 1 . .
    C C17 1.04175(13) 0.08265(10) 0.94178(11) 0.0259(4) Uani d . 1 . .
    C C18 1.05046(14) 0.13885(11) 1.00380(12) 0.0301(4) Uani d . 1 . .
    H H18 0.9877(18) 0.1682(13) 1.0149(14) 0.048(6) Uiso d . 1 . .
    C C19 1.14550(15) 0.15275(11) 1.05316(13) 0.0323(4) Uani d . 1 . .
    H H19 1.1513(16) 0.1897(13) 1.0964(14) 0.038(6) Uiso d . 1 . .
    C C20 1.23161(14) 0.10960(11) 1.03963(12) 0.0297(4) Uani d . 1 . .
    C C21 1.22666(15) 0.05391(11) 0.97882(12) 0.0317(4) Uani d . 1 . .
    H H21 1.2875(16) 0.0263(12) 0.9714(13) 0.037(6) Uiso d . 1 . .
    C C22 1.13085(14) 0.04091(11) 0.92987(12) 0.0295(4) Uani d . 1 . .
    H H22 1.1258(15) -0.0001(12) 0.8881(14) 0.036(5) Uiso d . 1 . .
    F F' 0.72117(9) 0.07392(7) 0.18637(7) 0.0422(3) Uani d . 1 . .
    O O' 0.35374(9) 0.09943(7) 0.42429(9) 0.0319(3) Uani d . 1 . .
    N N1' 0.32870(11) 0.19095(8) 0.57339(9) 0.0250(3) Uani d . 1 . .
    N N2' 0.49161(11) 0.21227(8) 0.63993(10) 0.0274(3) Uani d . 1 . .
    C C1' 0.43292(13) 0.20470(10) 0.56517(12) 0.0265(4) Uani d . 1 . .
    H H1A 0.4581(15) 0.2084(11) 0.5054(13) 0.033(5) Uiso d . 1 . .
    C C2' 0.42077(13) 0.20278(9) 0.70299(12) 0.0242(4) Uani d . 1 . .
    C C3' 0.43907(14) 0.20280(10) 0.79409(12) 0.0277(4) Uani d . 1 . .
    H H3A 0.5121(16) 0.2104(11) 0.8237(13) 0.035(5) Uiso d . 1 . .
    C C4' 0.35328(14) 0.19125(11) 0.84097(12) 0.0290(4) Uani d . 1 . .
    H H4A 0.3623(15) 0.1912(11) 0.9025(14) 0.034(5) Uiso d . 1 . .
    C C5' 0.25116(14) 0.18014(10) 0.79938(12) 0.0284(4) Uani d . 1 . .
    H H5A 0.1897(14) 0.1719(10) 0.8350(12) 0.023(5) Uiso d . 1 . .
    C C6' 0.23161(13) 0.17905(10) 0.70912(12) 0.0252(4) Uani d . 1 . .
    H H6A 0.1612(15) 0.1685(11) 0.6825(12) 0.029(5) Uiso d . 1 . .
    C C7' 0.31895(13) 0.18983(9) 0.66247(11) 0.0234(4) Uani d . 1 . .
    C C8' 0.24572(14) 0.17291(10) 0.50377(12) 0.0267(4) Uani d . 1 . .
    H H8A 0.2466(15) 0.2088(12) 0.4553(13) 0.034(5) Uiso d . 1 . .
    H H8B 0.1797(16) 0.1747(12) 0.5281(13) 0.034(5) Uiso d . 1 . .
    C C9' 0.25876(14) 0.09658(10) 0.46651(12) 0.0282(4) Uani d . 1 . .
    H H9A 0.2690(15) 0.0595(12) 0.5175(13) 0.033(5) Uiso d . 1 . .
    C C10' 0.16396(13) 0.07542(10) 0.40381(12) 0.0278(4) Uani d . 1 . .
    C C11' 0.10205(14) 0.01572(11) 0.42324(13) 0.0311(4) Uani d . 1 . .
    H H11A 0.1273(17) -0.0142(13) 0.4771(15) 0.046(6) Uiso d . 1 . .
    C C12' 0.01201(15) -0.00234(12) 0.36915(13) 0.0356(5) Uani d . 1 . .
    H H12A -0.0308(18) -0.0463(14) 0.3827(15) 0.051(6) Uiso d . 1 . .
    C C13' -0.01693(15) 0.03929(12) 0.29548(13) 0.0367(5) Uani d . 1 . .
    H H13A -0.0804(18) 0.0252(13) 0.2610(14) 0.045(6) Uiso d . 1 . .
    C C14' 0.04507(16) 0.09780(12) 0.27391(13) 0.0380(5) Uani d . 1 . .
    H H14A 0.0274(17) 0.1268(13) 0.2198(15) 0.046(6) Uiso d . 1 . .
    C C15' 0.13594(16) 0.11604(12) 0.32758(13) 0.0334(4) Uani d . 1 . .
    H H15A 0.1795(16) 0.1575(13) 0.3127(14) 0.042(6) Uiso d . 1 . .
    C C16' 0.38651(15) 0.02982(11) 0.39365(14) 0.0313(4) Uani d . 1 . .
    H H16A 0.3236(17) 0.0054(12) 0.3565(14) 0.041(6) Uiso d . 1 . .
    H H16B 0.4113(16) -0.0028(13) 0.4487(14) 0.041(6) Uiso d . 1 . .
    C C17' 0.47598(13) 0.04194(10) 0.33826(11) 0.0263(4) Uani d . 1 . .
    C C18' 0.47972(15) 0.10525(11) 0.28687(12) 0.0295(4) Uani d . 1 . .
    H H18A 0.4234(15) 0.1408(12) 0.2871(13) 0.031(5) Uiso d . 1 . .
    C C19' 0.56238(15) 0.11670(11) 0.23553(12) 0.0316(4) Uani d . 1 . .
    H H19A 0.5682(16) 0.1634(13) 0.2001(14) 0.040(6) Uiso d . 1 . .
    C C20' 0.63892(14) 0.06312(11) 0.23568(12) 0.0295(4) Uani d . 1 . .
    C C21' 0.63728(15) -0.00091(11) 0.28360(13) 0.0330(4) Uani d . 1 . .
    H H21A 0.6947(18) -0.0365(14) 0.2804(14) 0.049(6) Uiso d . 1 . .
    C C22' 0.55530(14) -0.01061(11) 0.33574(12) 0.0300(4) Uani d . 1 . .
    H H22A 0.5502(16) -0.0561(13) 0.3701(14) 0.039(6) Uiso d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    F C20 . 1.360(2) ?
    O C9 . 1.423(2) ?
    O C16 . 1.435(2) ?
    N1 C1 . 1.359(2) ?
    N1 C7 . 1.388(2) ?
    N1 C8 . 1.462(2) ?
    N2 C1 . 1.305(2) ?
    N2 C2 . 1.394(2) ?
    C1 H1 . 0.980(19) ?
    C2 C3 . 1.394(3) ?
    C2 C7 . 1.402(2) ?
    C3 H3 . 0.99(2) ?
    C4 C3 . 1.375(3) ?
    C4 C5 . 1.402(3) ?
    C4 H4 . 0.96(2) ?
    C5 H5 . 0.95(2) ?
    C6 C5 . 1.382(3) ?
    C6 H6 . 0.97(2) ?
    C7 C6 . 1.387(2) ?
    C8 H81 . 1.03(2) ?
    C8 H82 . 1.011(19) ?
    C9 C8 . 1.518(3) ?
    C9 C10 . 1.514(2) ?
    C9 H9 . 1.03(2) ?
    C10 C15 . 1.395(3) ?
    C11 C10 . 1.385(3) ?
    C11 C12 . 1.391(3) ?
    C11 H11 . 0.96(2) ?
    C12 C13 . 1.382(3) ?
    C12 H12 . 0.95(2) ?
    C13 H13 . 1.00(2) ?
    C14 C13 . 1.386(3) ?
    C14 C15 . 1.382(3) ?
    C14 H14 . 0.97(2) ?
    C15 H15 . 0.97(2) ?
    C16 H161 . 1.01(2) ?
    C16 H162 . 1.03(2) ?
    C17 C16 . 1.500(2) ?
    C17 C18 . 1.391(3) ?
    C17 C22 . 1.388(2) ?
    C18 C19 . 1.382(3) ?
    C18 H18 . 0.99(2) ?
    C19 H19 . 0.94(2) ?
    C20 C19 . 1.377(3) ?
    C20 C21 . 1.372(3) ?
    C21 C22 . 1.384(3) ?
    C21 H21 . 0.94(2) ?
    C22 H22 . 0.98(2) ?
    F' C20' . 1.364(2) ?
    O' C9' . 1.426(2) ?
    O' C16' . 1.423(2) ?
    N1' C1' . 1.365(2) ?
    N1' C7' . 1.386(2) ?
    N1' C8' . 1.461(2) ?
    N2' C1' . 1.312(2) ?
    N2' C2' . 1.397(2) ?
    C1' H1A . 1.00(2) ?
    C2' C7' . 1.397(2) ?
    C3' C2' . 1.395(3) ?
    C3' C4' . 1.380(3) ?
    C3' H3A . 1.00(2) ?
    C4' C5' . 1.401(3) ?
    C4' H4A . 0.94(2) ?
    C5' C6' . 1.383(3) ?
    C5' H5A . 1.008(18) ?
    C6' H6A . 0.964(19) ?
    C7' C6' . 1.393(2) ?
    C8' C9' . 1.513(3) ?
    C8' H8A . 0.99(2) ?
    C8' H8B . 0.95(2) ?
    C9' C10' . 1.513(2) ?
    C9' H9A . 1.03(2) ?
    C10' C11' . 1.387(3) ?
    C10' C15' . 1.398(3) ?
    C11' C12' . 1.383(3) ?
    C11' H11A . 1.01(2) ?
    C12' H12A . 1.00(2) ?
    C13' C12' . 1.379(3) ?
    C13' C14' . 1.381(3) ?
    C13' H13A . 0.95(2) ?
    C14' H14A . 0.99(2) ?
    C15' C14' . 1.389(3) ?
    C15' H15A . 0.97(2) ?
    C16' H16A . 1.03(2) ?
    C16' H16B . 1.05(2) ?
    C17' C16' . 1.502(3) ?
    C17' C18' . 1.396(3) ?
    C17' C22' . 1.389(3) ?
    C18' C19' . 1.390(3) ?
    C18' H18A . 0.96(2) ?
    C19' H19A . 1.01(2) ?
    C20' C19' . 1.374(3) ?
    C20' C21' . 1.376(3) ?
    C21' C22' . 1.386(3) ?
    C21' H21A . 0.98(2) ?
    C22' H22A . 0.98(2) ?
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
    C9 O C16 . . 112.02(13) ?
    C1 N1 C7 . . 105.96(14) ?
    C1 N1 C8 . . 127.37(15) ?
    C7 N1 C8 . . 126.37(14) ?
    C1 N2 C2 . . 104.19(14) ?
    N1 C1 H1 . . 121.1(11) ?
    N2 C1 N1 . . 114.66(16) ?
    N2 C1 H1 . . 124.2(11) ?
    N2 C2 C7 . . 109.96(15) ?
    C3 C2 N2 . . 130.02(16) ?
    C3 C2 C7 . . 120.02(15) ?
    C2 C3 H3 . . 121.8(12) ?
    C4 C3 C2 . . 117.60(16) ?
    C4 C3 H3 . . 120.6(12) ?
    C3 C4 C5 . . 121.79(17) ?
    C3 C4 H4 . . 120.3(12) ?
    C5 C4 H4 . . 117.9(12) ?
    C4 C5 H5 . . 120.1(12) ?
    C6 C5 C4 . . 121.45(16) ?
    C6 C5 H5 . . 118.5(12) ?
    C5 C6 C7 . . 116.49(16) ?
    C5 C6 H6 . . 123.8(12) ?
    C7 C6 H6 . . 119.7(12) ?
    N1 C7 C2 . . 105.22(14) ?
    C6 C7 N1 . . 132.15(16) ?
    C6 C7 C2 . . 122.63(16) ?
    N1 C8 C9 . . 112.17(15) ?
    N1 C8 H81 . . 107.6(11) ?
    N1 C8 H82 . . 110.6(11) ?
    C9 C8 H81 . . 109.3(11) ?
    C9 C8 H82 . . 108.4(12) ?
    H81 C8 H82 . . 108.7(16) ?
    O C9 C8 . . 105.91(14) ?
    O C9 C10 . . 112.84(14) ?
    O C9 H9 . . 109.7(10) ?
    C8 C9 H9 . . 110.0(11) ?
    C10 C9 C8 . . 110.29(14) ?
    C10 C9 H9 . . 108.0(11) ?
    C11 C10 C9 . . 120.31(16) ?
    C11 C10 C15 . . 119.24(16) ?
    C15 C10 C9 . . 120.40(16) ?
    C10 C11 C12 . . 120.38(17) ?
    C10 C11 H11 . . 119.5(12) ?
    C12 C11 H11 . . 120.1(12) ?
    C11 C12 H12 . . 118.8(13) ?
    C13 C12 C11 . . 120.05(17) ?
    C13 C12 H12 . . 121.2(13) ?
    C12 C13 C14 . . 119.77(17) ?
    C12 C13 H13 . . 120.6(12) ?
    C14 C13 H13 . . 119.6(12) ?
    C13 C14 H14 . . 119.2(13) ?
    C15 C14 C13 . . 120.33(18) ?
    C15 C14 H14 . . 120.5(13) ?
    C10 C15 H15 . . 118.6(11) ?
    C14 C15 C10 . . 120.22(17) ?
    C14 C15 H15 . . 121.2(11) ?
    O C16 C17 . . 108.96(15) ?
    O C16 H161 . . 108.9(13) ?
    O C16 H162 . . 109.9(11) ?
    C17 C16 H162 . . 110.5(10) ?
    C17 C16 H161 . . 111.6(12) ?
    H162 C16 H161 . . 106.9(17) ?
    C18 C17 C16 . . 120.02(16) ?
    C22 C17 C18 . . 118.64(17) ?
    C22 C17 C16 . . 121.30(17) ?
    C17 C18 H18 . . 120.2(13) ?
    C19 C18 C17 . . 120.93(17) ?
    C19 C18 H18 . . 118.8(13) ?
    C18 C19 H19 . . 121.3(13) ?
    C20 C19 C18 . . 118.45(19) ?
    C20 C19 H19 . . 120.2(13) ?
    F C20 C19 . . 118.38(17) ?
    F C20 C21 . . 119.09(16) ?
    C21 C20 C19 . . 122.53(17) ?
    C20 C21 C22 . . 118.19(17) ?
    C20 C21 H21 . . 119.6(13) ?
    C22 C21 H21 . . 122.2(13) ?
    C17 C22 H22 . . 119.9(12) ?
    C21 C22 C17 . . 121.26(18) ?
    C21 C22 H22 . . 118.8(12) ?
    C16' O' C9' . . 113.99(14) ?
    C1' N1' C7' . . 106.09(14) ?
    C1' N1' C8' . . 127.44(15) ?
    C7' N1' C8' . . 126.15(14) ?
    C1' N2' C2' . . 104.19(14) ?
    N1' C1' H1A . . 119.8(11) ?
    N2' C1' N1' . . 114.16(16) ?
    N2' C1' H1A . . 126.0(11) ?
    N2' C2' C7' . . 110.07(15) ?
    C3' C2' N2' . . 129.88(16) ?
    C3' C2' C7' . . 120.03(16) ?
    C2' C3' H3A . . 120.6(11) ?
    C4' C3' C2' . . 117.52(16) ?
    C4' C3' H3A . . 121.8(11) ?
    C3' C4' C5' . . 121.77(17) ?
    C3' C4' H4A . . 120.1(12) ?
    C5' C4' H4A . . 118.2(12) ?
    C4' C5' H5A . . 120.3(10) ?
    C6' C5' C4' . . 121.58(17) ?
    C6' C5' H5A . . 118.1(10) ?
    C5' C6' C7' . . 116.17(16) ?
    C5' C6' H6A . . 119.6(11) ?
    C7' C6' H6A . . 124.2(11) ?
    N1' C7' C6' . . 131.61(15) ?
    N1' C7' C2' . . 105.49(14) ?
    C6' C7' C2' . . 122.90(16) ?
    N1' C8' C9' . . 112.54(15) ?
    N1' C8' H8A . . 110.0(11) ?
    N1' C8' H8B . . 107.7(12) ?
    C9' C8' H8A . . 107.9(12) ?
    C9' C8' H8B . . 108.2(13) ?
    H8A C8' H8B . . 110.5(17) ?
    O' C9' C8' . . 105.57(14) ?
    O' C9' C10' . . 112.01(15) ?
    O' C9' H9A . . 108.7(11) ?
    C8' C9' C10' . . 111.24(15) ?
    C8' C9' H9A . . 108.7(11) ?
    C10' C9' H9A . . 110.4(11) ?
    C11' C10' C15' . . 119.25(17) ?
    C11' C10' C9' . . 119.50(17) ?
    C15' C10' C9' . . 121.22(17) ?
    C10' C11' H11A . . 117.0(13) ?
    C12' C11' C10' . . 120.49(19) ?
    C12' C11' H11A . . 122.5(13) ?
    C11' C12' H12A . . 119.9(13) ?
    C13' C12' C11' . . 120.0(2) ?
    C13' C12' H12A . . 120.1(13) ?
    C12' C13' C14' . . 120.38(18) ?
    C12' C13' H13A . . 116.8(14) ?
    C14' C13' H13A . . 122.8(14) ?
    C13' C14' C15' . . 120.01(19) ?
    C13' C14' H14A . . 121.5(13) ?
    C15' C14' H14A . . 118.5(13) ?
    C10' C15' H15A . . 120.0(13) ?
    C14' C15' C10' . . 119.85(19) ?
    C14' C15' H15A . . 120.1(12) ?
    O' C16' C17' . . 108.67(15) ?
    O' C16' H16A . . 109.1(12) ?
    O' C16' H16B . . 107.8(12) ?
    C17' C16' H16A . . 109.7(12) ?
    C17' C16' H16B . . 110.8(11) ?
    H16A C16' H16B . . 110.7(17) ?
    C18' C17' C16' . . 120.72(16) ?
    C22' C17' C18' . . 118.82(17) ?
    C22' C17' C16' . . 120.45(17) ?
    C17' C18' H18A . . 118.8(12) ?
    C19' C18' C17' . . 120.91(17) ?
    C19' C18' H18A . . 120.3(12) ?
    C18' C19' H19A . . 121.9(12) ?
    C20' C19' C18' . . 117.87(18) ?
    C20' C19' H19A . . 120.2(12) ?
    F' C20' C19' . . 118.57(17) ?
    F' C20' C21' . . 118.13(16) ?
    C19' C20' C21' . . 123.30(18) ?
    C20' C21' C22' . . 117.92(18) ?
    C20' C21' H21A . . 118.6(14) ?
    C22' C21' H21A . . 123.5(14) ?
    C17' C22' H22A . . 118.2(12) ?
    C21' C22' C17' . . 121.14(18) ?
    C21' C22' H22A . . 120.6(12) ?
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
    C16 O C9 C8 . . . . -171.09(14) ?
    C16 O C9 C10 . . . . 68.15(19) ?
    C9 O C16 C17 . . . . -172.87(14) ?
    C7 N1 C1 N2 . . . . 0.7(2) ?
    C8 N1 C1 N2 . . . . 174.73(17) ?
    C1 N1 C7 C2 . . . . -0.70(18) ?
    C1 N1 C7 C6 . . . . 179.78(19) ?
    C8 N1 C7 C2 . . . . -174.84(16) ?
    C8 N1 C7 C6 . . . . 5.6(3) ?
    C1 N1 C8 C9 . . . . -73.6(2) ?
    C7 N1 C8 C9 . . . . 99.33(19) ?
    C2 N2 C1 N1 . . . . -0.3(2) ?
    C1 N2 C2 C3 . . . . -179.88(19) ?
    C1 N2 C2 C7 . . . . -0.15(19) ?
    N2 C2 C3 C4 . . . . 179.03(18) ?
    C7 C2 C3 C4 . . . . -0.7(3) ?
    N2 C2 C7 N1 . . . . 0.54(19) ?
    N2 C2 C7 C6 . . . . -179.88(16) ?
    C3 C2 C7 N1 . . . . -179.70(16) ?
    C3 C2 C7 C6 . . . . -0.1(3) ?
    C5 C4 C3 C2 . . . . 0.9(3) ?
    C3 C4 C5 C6 . . . . -0.4(3) ?
    C7 C6 C5 C4 . . . . -0.4(3) ?
    N1 C7 C6 C5 . . . . -179.90(18) ?
    C2 C7 C6 C5 . . . . 0.6(3) ?
    O C9 C8 N1 . . . . 65.00(18) ?
    C10 C9 C8 N1 . . . . -172.60(14) ?
    O C9 C10 C11 . . . . -136.59(17) ?
    O C9 C10 C15 . . . . 45.8(2) ?
    C8 C9 C10 C11 . . . . 105.18(19) ?
    C8 C9 C10 C15 . . . . -72.4(2) ?
    C9 C10 C15 C14 . . . . 177.27(16) ?
    C11 C10 C15 C14 . . . . -0.3(3) ?
    C12 C11 C10 C9 . . . . -176.91(16) ?
    C12 C11 C10 C15 . . . . 0.7(3) ?
    C10 C11 C12 C13 . . . . -0.8(3) ?
    C11 C12 C13 C14 . . . . 0.5(3) ?
    C15 C14 C13 C12 . . . . -0.1(3) ?
    C13 C14 C15 C10 . . . . 0.1(3) ?
    C18 C17 C16 O . . . . 57.8(2) ?
    C22 C17 C16 O . . . . -124.31(18) ?
    C16 C17 C18 C19 . . . . 177.53(17) ?
    C22 C17 C18 C19 . . . . -0.4(3) ?
    C16 C17 C22 C21 . . . . -177.36(17) ?
    C18 C17 C22 C21 . . . . 0.6(3) ?
    C17 C18 C19 C20 . . . . -0.1(3) ?
    F C20 C19 C18 . . . . -179.59(16) ?
    C21 C20 C19 C18 . . . . 0.4(3) ?
    F C20 C21 C22 . . . . 179.72(16) ?
    C19 C20 C21 C22 . . . . -0.3(3) ?
    C20 C21 C22 C17 . . . . -0.2(3) ?
    C16' O' C9' C8' . . . . 172.99(15) ?
    C16' O' C9' C10' . . . . -65.8(2) ?
    C9' O' C16' C17' . . . . 170.86(14) ?
    C7' N1' C1' N2' . . . . 0.3(2) ?
    C8' N1' C1' N2' . . . . -173.60(17) ?
    C1' N1' C7' C6' . . . . 179.34(18) ?
    C8' N1' C7' C6' . . . . -6.7(3) ?
    C1' N1' C7' C2' . . . . -0.44(18) ?
    C8' N1' C7' C2' . . . . 173.54(16) ?
    C1' N1' C8' C9' . . . . 70.5(2) ?
    C7' N1' C8' C9' . . . . -102.2(2) ?
    C2' N2' C1' N1' . . . . 0.0(2) ?
    C1' N2' C2' C3' . . . . 177.92(19) ?
    C1' N2' C2' C7' . . . . -0.30(19) ?
    C3' C2' C7' N1' . . . . -177.96(16) ?
    N2' C2' C7' N1' . . . . 0.47(19) ?
    C3' C2' C7' C6' . . . . 2.2(3) ?
    N2' C2' C7' C6' . . . . -179.33(16) ?
    C4' C3' C2' N2' . . . . -179.40(17) ?
    C4' C3' C2' C7' . . . . -1.3(3) ?
    C2' C3' C4' C5' . . . . -0.2(3) ?
    C3' C4' C5' C6' . . . . 1.0(3) ?
    C4' C5' C6' C7' . . . . -0.2(3) ?
    N1' C7' C6' C5' . . . . 178.82(18) ?
    C2' C7' C6' C5' . . . . -1.4(3) ?
    N1' C8' C9' O' . . . . -66.22(19) ?
    N1' C8' C9' C10' . . . . 172.07(15) ?
    O' C9' C10' C11' . . . . 125.14(18) ?
    C8' C9' C10' C11' . . . . -116.98(19) ?
    O' C9' C10' C15' . . . . -56.5(2) ?
    C8' C9' C10' C15' . . . . 61.4(2) ?
    C9' C10' C11' C12' . . . . 176.72(17) ?
    C15' C10' C11' C12' . . . . -1.7(3) ?
    C9' C10' C15' C14' . . . . -176.33(17) ?
    C11' C10' C15' C14' . . . . 2.1(3) ?
    C10' C11' C12' C13' . . . . -0.2(3) ?
    C14' C13' C12' C11' . . . . 1.8(3) ?
    C12' C13' C14' C15' . . . . -1.4(3) ?
    C10' C15' C14' C13' . . . . -0.5(3) ?
    C18' C17' C16' O' . . . . -33.7(2) ?
    C22' C17' C16' O' . . . . 147.83(17) ?
    C16' C17' C18' C19' . . . . 179.98(17) ?
    C22' C17' C18' C19' . . . . -1.5(3) ?
    C18' C17' C22' C21' . . . . 0.2(3) ?
    C16' C17' C22' C21' . . . . 178.70(17) ?
    C17' C18' C19' C20' . . . . 1.3(3) ?
    F' C20' C19' C18' . . . . -179.30(16) ?
    C21' C20' C19' C18' . . . . 0.3(3) ?
    F' C20' C21' C22' . . . . 178.03(16) ?
    C19' C20' C21' C22' . . . . -1.6(3) ?
    C20' C21' C22' C17' . . . . 1.3(3) ?
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
    C6 H6 N2' . 0.97(2) 2.62(2) 3.498(2) 150.5(17) yes
    C6' H6A N2 1_455 0.964(19) 2.459(19) 3.345(2) 152.7(16) yes
    C13 H13 F 1_455 1.00(2) 2.54(2) 3.493(2) 159.6(16) yes
    C19' H19A N2' 4_565 1.01(2) 2.59(2) 3.509(2) 151.1(16) yes
    C5 H5 Cg8 4_554 0.95(2) 2.662(19) 3.514(2) 149.0(15) yes
    C22' H22A Cg2 3_656 0.98(2) 2.62(9) 3.518(2) 141.9(16) yes
data_global
_journal_date_recd_electronic     2008-07-08
_journal_date_accepted     2008-07-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      8
_journal_page_first     o1496
_journal_page_last     o1497
_journal_paper_category     QO
_journal_coeditor_code     XU2436
_publ_contact_author
;
Dr. Tuncer Hökelek
Hacettepe University
Department of Physics
06800 Beytepe
Ankara
Turkey
;
_publ_contact_author_email     merzifon@hacettepe.edu.tr
_publ_contact_author_fax     '90(312)2352550'
_publ_contact_author_phone     '90(312)2977242'
_publ_section_title
;
1-[2-(4-Fluorobenzyloxy)-2-phenylethyl]-1H-benzimidazole
;
loop_
    _publ_author_name
    _publ_author_address
    'Özel Güven, Özden'
;
Zonguldak Karaelmas University,
Department of Chemistry,
67100 Zonguldak, Turkey
;
    'Erdoğan, Taner'
;
Zonguldak Karaelmas University,
Department of Chemistry,
67100 Zonguldak, Turkey
;
    'Coles, Simon J.'
;
Southampton University,
Department of Chemistry,
Southampton SO17 1BJ
England
;
    'Hökelek, Tuncer'
;
Hacettepe University,
Department of Physics,
06800 Beytepe
Ankara
Turkey
;
