##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 2.1.    #
#                                                                            #
# 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_global
_audit_creation_method     SHELXL97
_journal_date_recd_electronic     2005-09-12
_journal_date_accepted     2005-09-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue     10
_journal_page_first     o3476
_journal_page_last     o3477
_journal_paper_category     EO
_journal_coeditor_code     CV6580
_publ_contact_author_name     'Jian-Wu Wang'
_publ_contact_author_address
;
School of Chemistry and Chemical Engineering
Shandong University
Jinan 250100
People's Republic of China
;
_publ_contact_author_email     yugp2005@yahoo.com.cn
_publ_contact_author_fax     '+86-531-88564464'
_publ_contact_author_phone     '+86-531-88564464'
_publ_section_title
;
Bis(benzimidazol-2-yl)methane
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Gui-Yun Duan' .
;
School of Chemistry and Chemical Engineering
Shandong University
Jinan 250100
People's Republic of China
;
    'Ya-Wei Sun' .
;
School of Chemistry and Chemical Engineering
Shandong University
Jinan 250100
People's Republic of China
;
    'Jun-Zhi Liu' .
;
School of Chemistry and Chemical Engineering
Shandong University
Jinan 250100
People's Republic of China
;
    'Jian-Wu Wang' .
;
School of Chemistry and Chemical Engineering
Shandong University
Jinan 250100
People's Republic of China
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
 Bis(benzimidazol-2-yl)methane
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H12 N4'
_chemical_formula_sum     'C15 H12 N4'
_chemical_formula_iupac     'C15 H12 N4'
_chemical_formula_weight     248.29
_chemical_melting_point     ?
_symmetry_cell_setting     Tetragonal
_symmetry_space_group_name_H-M     I41/a
_symmetry_space_group_name_Hall     '-I 4ad'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-y+3/4, x+1/4, z+1/4'
    'y+3/4, -x+3/4, z+3/4'
    'x+1/2, y+1/2, z+1/2'
    '-x+1, -y+1/2, z+1'
    '-y+5/4, x+3/4, z+3/4'
    'y+5/4, -x+5/4, z+5/4'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'y-3/4, -x-1/4, -z-1/4'
    '-y-3/4, x-3/4, -z-3/4'
    '-x+1/2, -y+1/2, -z+1/2'
    'x, y+1/2, -z'
    'y-1/4, -x+1/4, -z+1/4'
    '-y-1/4, x-1/4, -z-1/4'
_cell_length_a     18.296(4)
_cell_length_b     18.296(4)
_cell_length_c     15.728(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     5264.6(18)
_cell_formula_units_Z     16
_cell_measurement_reflns_used     4441
_cell_measurement_theta_min     2.225
_cell_measurement_theta_max     25.832
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.253
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     2080
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9500
_exptl_absorpt_correction_T_max     0.9791
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     298(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 SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10662
_diffrn_reflns_av_R_equivalents     0.0353
_diffrn_reflns_av_sigmaI/netI     0.0244
_diffrn_reflns_theta_min     2.81
_diffrn_reflns_theta_max     25.05
_diffrn_reflns_theta_full     25.05
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     21
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_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     2307
_reflns_number_gt     1798
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0555
_refine_ls_R_factor_gt     0.0416
_refine_ls_wR_factor_gt     0.1159
_refine_ls_wR_factor_ref     0.1303
_refine_ls_goodness_of_fit_ref     1.000
_refine_ls_restrained_S_all     1.000
_refine_ls_number_reflns     2307
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w = 1/[σ²(Fo²)+(0.075P)²+1.5659P] 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     0.201
_refine_diff_density_min     -0.157
_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'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1999)'
_computing_publication_material     'SHELXTL'
loop_
    _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
    _atom_site_type_symbol
    N1 0.57166(10) 0.30536(8) 0.09757(10) 0.0708(5) Uani d . 1 . . N
    N2 0.58129(8) 0.42431(7) 0.11565(8) 0.0560(4) Uani d . 1 . . N
    H2A 0.5790 0.4704 0.1049 0.067 Uiso calc R 1 . . H
    N3 0.41074(8) 0.42962(7) -0.06625(8) 0.0578(4) Uani d . 1 . . N
    N4 0.41095(8) 0.32348(7) 0.00088(8) 0.0563(4) Uani d . 1 . . N
    H4A 0.4271 0.2856 0.0273 0.068 Uiso calc R 1 . . H
    C1 0.60520(9) 0.39271(9) 0.18957(11) 0.0563(4) Uani d . 1 . . C
    C2 0.63143(12) 0.42248(11) 0.26529(12) 0.0767(6) Uani d . 1 . . C
    H2 0.6354 0.4727 0.2728 0.092 Uiso calc R 1 . . H
    C3 0.65094(15) 0.37490(13) 0.32774(14) 0.0954(8) Uani d . 1 . . C
    H3 0.6693 0.3931 0.3786 0.114 Uiso calc R 1 . . H
    C4 0.64421(17) 0.30066(14) 0.31753(17) 0.1144(10) Uani d . 1 . . C
    H4 0.6575 0.2699 0.3620 0.137 Uiso calc R 1 . . H
    C5 0.61850(17) 0.27091(12) 0.24371(17) 0.1101(10) Uani d . 1 . . C
    H5 0.6142 0.2206 0.2372 0.132 Uiso calc R 1 . . H
    C6 0.59899(11) 0.31847(10) 0.17871(12) 0.0669(5) Uani d . 1 . . C
    C7 0.56216(9) 0.37014(8) 0.06352(10) 0.0514(4) Uani d . 1 . . C
    C8 0.53220(10) 0.38310(11) -0.02331(10) 0.0635(5) Uani d . 1 . . C
    H8A 0.5526 0.3470 -0.0617 0.076 Uiso calc R 1 . . H
    H8B 0.5481 0.4309 -0.0427 0.076 Uiso calc R 1 . . H
    C9 0.45082(9) 0.37953(8) -0.02848(9) 0.0511(4) Uani d . 1 . . C
    C10 0.33919(10) 0.40476(9) -0.06135(10) 0.0557(4) Uani d . 1 . . C
    C11 0.27477(12) 0.43470(11) -0.09232(13) 0.0752(6) Uani d . 1 . . C
    H11 0.2745 0.4795 -0.1203 0.090 Uiso calc R 1 . . H
    C12 0.21142(12) 0.39574(13) -0.08007(14) 0.0813(6) Uani d . 1 . . C
    H12 0.1675 0.4146 -0.1000 0.098 Uiso calc R 1 . . H
    C13 0.21165(12) 0.32914(13) -0.03878(14) 0.0782(6) Uani d . 1 . . C
    H13 0.1679 0.3040 -0.0321 0.094 Uiso calc R 1 . . H
    C14 0.27489(11) 0.29906(11) -0.00732(12) 0.0699(5) Uani d . 1 . . C
    H14 0.2748 0.2544 0.0208 0.084 Uiso calc R 1 . . H
    C15 0.33900(9) 0.33830(9) -0.01940(9) 0.0538(4) Uani d . 1 . . C
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    N1 0.1020(12) 0.0503(8) 0.0599(9) 0.0033(8) -0.0166(8) -0.0050(7)
    N2 0.0746(9) 0.0432(7) 0.0503(8) -0.0022(6) -0.0062(6) 0.0046(6)
    N3 0.0764(10) 0.0527(8) 0.0442(7) -0.0072(7) -0.0072(6) 0.0067(6)
    N4 0.0748(9) 0.0468(7) 0.0472(8) 0.0037(6) 0.0050(6) 0.0072(6)
    C1 0.0640(10) 0.0522(9) 0.0527(10) -0.0008(7) -0.0092(8) 0.0029(7)
    C2 0.0981(15) 0.0647(11) 0.0672(12) -0.0069(10) -0.0244(11) -0.0038(9)
    C3 0.126(2) 0.0895(16) 0.0703(14) -0.0084(14) -0.0436(13) 0.0050(11)
    C4 0.172(3) 0.0834(16) 0.0881(17) -0.0068(16) -0.0636(18) 0.0252(13)
    C5 0.173(3) 0.0557(12) 0.1017(19) -0.0041(13) -0.0560(18) 0.0158(12)
    C6 0.0873(13) 0.0515(10) 0.0618(11) 0.0012(8) -0.0199(9) 0.0017(8)
    C7 0.0573(9) 0.0510(9) 0.0460(9) 0.0001(7) 0.0037(7) -0.0005(7)
    C8 0.0739(11) 0.0769(12) 0.0398(9) -0.0046(9) 0.0032(8) 0.0018(8)
    C9 0.0706(10) 0.0504(9) 0.0324(7) -0.0023(7) 0.0006(7) -0.0002(6)
    C10 0.0725(11) 0.0548(9) 0.0397(8) -0.0040(8) -0.0025(7) -0.0037(7)
    C11 0.0876(14) 0.0743(12) 0.0639(12) 0.0041(10) -0.0142(10) 0.0057(9)
    C12 0.0713(13) 0.1036(17) 0.0690(13) 0.0044(11) -0.0093(10) -0.0094(12)
    C13 0.0715(13) 0.0945(15) 0.0686(13) -0.0101(11) 0.0116(10) -0.0168(11)
    C14 0.0827(13) 0.0652(11) 0.0618(11) -0.0112(9) 0.0167(10) -0.0051(9)
    C15 0.0702(11) 0.0519(9) 0.0393(8) -0.0007(8) 0.0067(7) -0.0075(7)
_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
    N1 C7 . 1.312(2) yes
    N1 C6 . 1.391(2) yes
    N2 C7 . 1.333(2) yes
    N2 C1 . 1.370(2) yes
    N2 H2A . 0.8600 ?
    N3 C9 . 1.315(2) yes
    N3 C10 . 1.388(2) yes
    N4 C9 . 1.340(2) yes
    N4 C15 . 1.381(2) yes
    N4 H4A . 0.8600 ?
    C1 C6 . 1.374(2) ?
    C1 C2 . 1.395(2) ?
    C2 C3 . 1.360(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.373(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.366(4) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.389(3) ?
    C5 H5 . 0.9300 ?
    C7 C8 . 1.491(2) yes
    C8 C9 . 1.493(2) yes
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C10 C15 . 1.384(2) ?
    C10 C11 . 1.388(3) ?
    C11 C12 . 1.374(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.381(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.373(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.388(2) ?
    C14 H14 . 0.9300 ?
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
    C7 N1 C6 . . 105.43(14) yes
    C7 N2 C1 . . 106.98(13) yes
    C7 N2 H2A . . 126.5 ?
    C1 N2 H2A . . 126.5 ?
    C9 N3 C10 . . 105.81(13) yes
    C9 N4 C15 . . 106.79(13) yes
    C9 N4 H4A . . 126.6 ?
    C15 N4 H4A . . 126.6 ?
    N2 C1 C6 . . 106.58(14) ?
    N2 C1 C2 . . 132.04(16) ?
    C6 C1 C2 . . 121.38(16) ?
    C3 C2 C1 . . 117.20(19) ?
    C3 C2 H2 . . 121.4 ?
    C1 C2 H2 . . 121.4 ?
    C2 C3 C4 . . 121.7(2) ?
    C2 C3 H3 . . 119.2 ?
    C4 C3 H3 . . 119.2 ?
    C5 C4 C3 . . 121.6(2) ?
    C5 C4 H4 . . 119.2 ?
    C3 C4 H4 . . 119.2 ?
    C4 C5 C6 . . 117.7(2) ?
    C4 C5 H5 . . 121.2 ?
    C6 C5 H5 . . 121.2 ?
    C1 C6 C5 . . 120.44(18) ?
    C1 C6 N1 . . 108.32(14) ?
    C5 C6 N1 . . 131.25(18) ?
    N1 C7 N2 . . 112.69(14) ?
    N1 C7 C8 . . 124.49(15) ?
    N2 C7 C8 . . 122.81(15) ?
    C7 C8 C9 . . 114.19(14) yes
    C7 C8 H8A . . 108.7 ?
    C9 C8 H8A . . 108.7 ?
    C7 C8 H8B . . 108.7 ?
    C9 C8 H8B . . 108.7 ?
    H8A C8 H8B . . 107.6 ?
    N3 C9 N4 . . 112.65(15) ?
    N3 C9 C8 . . 123.38(14) ?
    N4 C9 C8 . . 123.89(15) ?
    C15 C10 C11 . . 120.81(17) ?
    C15 C10 N3 . . 108.47(14) ?
    C11 C10 N3 . . 130.70(16) ?
    C12 C11 C10 . . 117.53(19) ?
    C12 C11 H11 . . 121.2 ?
    C10 C11 H11 . . 121.2 ?
    C11 C12 C13 . . 121.4(2) ?
    C11 C12 H12 . . 119.3 ?
    C13 C12 H12 . . 119.3 ?
    C14 C13 C12 . . 121.72(19) ?
    C14 C13 H13 . . 119.1 ?
    C12 C13 H13 . . 119.1 ?
    C13 C14 C15 . . 117.08(19) ?
    C13 C14 H14 . . 121.5 ?
    C15 C14 H14 . . 121.5 ?
    N4 C15 C10 . . 106.27(14) ?
    N4 C15 C14 . . 132.23(17) ?
    C10 C15 C14 . . 121.46(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
    C7 N2 C1 C6 . . . . -0.26(19) ?
    C7 N2 C1 C2 . . . . -179.9(2) ?
    N2 C1 C2 C3 . . . . 179.9(2) ?
    C6 C1 C2 C3 . . . . 0.3(3) ?
    C1 C2 C3 C4 . . . . -1.0(4) ?
    C2 C3 C4 C5 . . . . 0.9(5) ?
    C3 C4 C5 C6 . . . . -0.2(5) ?
    N2 C1 C6 C5 . . . . -179.3(2) ?
    C2 C1 C6 C5 . . . . 0.4(3) ?
    N2 C1 C6 N1 . . . . 0.4(2) ?
    C2 C1 C6 N1 . . . . -179.91(18) ?
    C4 C5 C6 C1 . . . . -0.4(4) ?
    C4 C5 C6 N1 . . . . 179.9(3) ?
    C7 N1 C6 C1 . . . . -0.4(2) ?
    C7 N1 C6 C5 . . . . 179.3(3) ?
    C6 N1 C7 N2 . . . . 0.2(2) ?
    C6 N1 C7 C8 . . . . -178.84(16) ?
    C1 N2 C7 N1 . . . . 0.0(2) ?
    C1 N2 C7 C8 . . . . 179.10(15) ?
    N1 C7 C8 C9 . . . . 81.0(2) ?
    N2 C7 C8 C9 . . . . -97.94(19) ?
    C10 N3 C9 N4 . . . . 0.06(17) ?
    C10 N3 C9 C8 . . . . 176.91(14) ?
    C15 N4 C9 N3 . . . . -0.03(17) ?
    C15 N4 C9 C8 . . . . -176.87(14) ?
    C7 C8 C9 N3 . . . . 131.44(16) ?
    C7 C8 C9 N4 . . . . -52.1(2) ?
    C9 N3 C10 C15 . . . . -0.06(17) ?
    C9 N3 C10 C11 . . . . -178.29(18) ?
    C15 C10 C11 C12 . . . . -0.3(3) ?
    N3 C10 C11 C12 . . . . 177.74(17) ?
    C10 C11 C12 C13 . . . . -0.2(3) ?
    C11 C12 C13 C14 . . . . 0.7(3) ?
    C12 C13 C14 C15 . . . . -0.5(3) ?
    C9 N4 C15 C10 . . . . -0.01(16) ?
    C9 N4 C15 C14 . . . . 177.71(17) ?
    C11 C10 C15 N4 . . . . 178.48(15) ?
    N3 C10 C15 N4 . . . . 0.04(17) ?
    C11 C10 C15 C14 . . . . 0.5(2) ?
    N3 C10 C15 C14 . . . . -177.98(14) ?
    C13 C14 C15 N4 . . . . -177.49(17) ?
    C13 C14 C15 C10 . . . . -0.1(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
    N2 H2A N3 9_665 0.86 1.94 2.7869(18) 169
    N4 H4A N1 6_554 0.86 2.00 2.823(2) 160
