##############################################################################
# #
# 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. #
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##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 998763'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-(4-Bromobenzyl)-2-(4-bromophenyl)-1H-benzimidazole
;
_chemical_name_common 1-(4-bromobenzyl)-2-(4-bromophenyl)-1H-benzimidazole
_chemical_formula_moiety 'C20 H14 Br2 N2'
_chemical_formula_sum 'C20 H14 Br2 N2'
_chemical_formula_iupac 'C20 H14 Br2 N2'
_chemical_formula_weight 442.15
_chemical_melting_point ?
_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 9.7537(9)
_cell_length_b 10.5758(10)
_cell_length_c 17.8255(17)
_cell_angle_alpha 83.435(2)
_cell_angle_beta 81.702(2)
_cell_angle_gamma 75.621(2)
_cell_volume 1756.6(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?
_cell_measurement_temperature 293(2)
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.26
_exptl_crystal_size_min 0.20
_exptl_crystal_density_diffrn 1.672
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 872
_exptl_absorpt_coefficient_mu 4.618
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2004)'
_exptl_absorpt_correction_T_min 0.258
_exptl_absorpt_correction_T_max 0.398
_exptl_special_details ?
_diffrn_ambient_temperature 293(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'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 22195
_diffrn_reflns_av_R_equivalents 0.0337
_diffrn_reflns_av_sigmaI/netI 0.0458
_diffrn_reflns_theta_min 1.99
_diffrn_reflns_theta_max 27.61
_diffrn_reflns_theta_full 27.61
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_limit_l_max 23
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ 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 8094
_reflns_number_gt 5171
_reflns_threshold_expression >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0782
_refine_ls_R_factor_gt 0.0413
_refine_ls_wR_factor_gt 0.1117
_refine_ls_wR_factor_ref 0.1284
_refine_ls_goodness_of_fit_ref 1.031
_refine_ls_restrained_S_all 1.031
_refine_ls_number_reflns 8094
_refine_ls_number_parameters 433
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0682P)^2^+0.0252P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.782
_refine_diff_density_min -0.510
_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'
'Br' 'Br' -0.2901 2.4595
'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 'APEX2 (Bruker, 2004)'
_computing_cell_refinement 'SAINT (Bruker, 2004)'
_computing_data_reduction 'SAINT (Bruker, 2004)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
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
Br Br1 -0.15730(5) 0.89638(4) 0.54077(3) 0.08072(17) Uani d . 1 1 . .
Br Br2 -0.16242(6) 0.32973(6) 0.10730(4) 0.1089(2) Uani d . 1 1 . .
N N1 0.3305(3) 0.4230(3) 0.32967(15) 0.0433(6) Uani d . 1 1 . .
N N2 0.3833(3) 0.3609(3) 0.44875(15) 0.0500(7) Uani d . 1 1 . .
C C1 0.3026(3) 0.4476(3) 0.40547(18) 0.0428(7) Uani d . 1 1 . .
C C2 0.4706(3) 0.2743(3) 0.3994(2) 0.0501(8) Uani d . 1 1 . .
C C3 0.5784(4) 0.1635(4) 0.4142(2) 0.0675(11) Uani d . 1 1 . .
H H3 0.5986 0.1356 0.4636 0.081 Uiso calc R 1 1 . .
C C4 0.6537(4) 0.0968(4) 0.3541(3) 0.0782(13) Uani d . 1 1 . .
H H4 0.7261 0.0228 0.3629 0.094 Uiso calc R 1 1 . .
C C5 0.6235(4) 0.1382(4) 0.2798(3) 0.0742(12) Uani d . 1 1 . .
H H5 0.6784 0.0922 0.2400 0.089 Uiso calc R 1 1 . .
C C6 0.5146(4) 0.2452(4) 0.2633(2) 0.0621(10) Uani d . 1 1 . .
H H6 0.4926 0.2709 0.2140 0.075 Uiso calc R 1 1 . .
C C7 0.4402(3) 0.3118(3) 0.32494(19) 0.0471(8) Uani d . 1 1 . .
C C8 0.1638(3) 0.4571(3) 0.23018(17) 0.0411(7) Uani d . 1 1 . .
C C9 0.1261(3) 0.3402(3) 0.25350(19) 0.0478(8) Uani d . 1 1 . .
H H9 0.1660 0.2877 0.2940 0.057 Uiso calc R 1 1 . .
C C10 0.0299(4) 0.3001(4) 0.2176(2) 0.0602(10) Uani d . 1 1 . .
H H10 0.0055 0.2207 0.2331 0.072 Uiso calc R 1 1 . .
C C11 -0.0294(4) 0.3804(4) 0.1582(2) 0.0625(10) Uani d . 1 1 . .
C C12 0.0032(4) 0.4980(4) 0.1359(2) 0.0652(10) Uani d . 1 1 . .
H H12 -0.0391 0.5520 0.0965 0.078 Uiso calc R 1 1 . .
C C13 0.0992(4) 0.5355(4) 0.1723(2) 0.0547(9) Uani d . 1 1 . .
H H13 0.1211 0.6161 0.1574 0.066 Uiso calc R 1 1 . .
C C14 0.1930(3) 0.5584(3) 0.43392(17) 0.0431(7) Uani d . 1 1 . .
C C15 0.2257(3) 0.6373(3) 0.4824(2) 0.0525(8) Uani d . 1 1 . .
H H15 0.3189 0.6218 0.4937 0.063 Uiso calc R 1 1 . .
C C16 0.1234(4) 0.7384(4) 0.5144(2) 0.0584(9) Uani d . 1 1 . .
H H16 0.1461 0.7903 0.5473 0.070 Uiso calc R 1 1 . .
C C17 -0.0147(3) 0.7600(3) 0.49573(19) 0.0495(8) Uani d . 1 1 . .
C C18 -0.0515(3) 0.6844(3) 0.44837(19) 0.0523(9) Uani d . 1 1 . .
H H18 -0.1451 0.6999 0.4377 0.063 Uiso calc R 1 1 . .
C C19 0.0526(3) 0.5847(3) 0.41662(18) 0.0479(8) Uani d . 1 1 . .
H H19 0.0292 0.5341 0.3832 0.057 Uiso calc R 1 1 . .
C C20 0.2732(3) 0.5045(3) 0.26516(18) 0.0477(8) Uani d . 1 1 . .
H H20A 0.3518 0.5118 0.2261 0.057 Uiso calc R 1 1 . .
H H20B 0.2297 0.5917 0.2810 0.057 Uiso calc R 1 1 . .
Br Br3 0.63928(5) 1.35816(5) -0.04992(2) 0.07448(16) Uani d . 1 1 . .
Br Br4 0.74016(4) 0.49101(4) 0.33062(3) 0.07748(16) Uani d . 1 1 . .
N N3 0.2139(3) 0.9848(2) 0.18779(14) 0.0400(6) Uani d . 1 1 . .
N N4 0.1287(3) 1.0167(3) 0.07537(15) 0.0472(6) Uani d . 1 1 . .
C C21 0.2261(3) 1.0367(3) 0.11357(17) 0.0417(7) Uani d . 1 1 . .
C C22 0.0980(3) 0.9287(3) 0.19718(17) 0.0403(7) Uani d . 1 1 . .
C C23 0.0326(4) 0.8664(3) 0.2605(2) 0.0530(9) Uani d . 1 1 . .
H H23 0.0673 0.8531 0.3075 0.064 Uiso calc R 1 1 . .
C C24 -0.0858(4) 0.8261(4) 0.2497(2) 0.0593(9) Uani d . 1 1 . .
H H24 -0.1333 0.7851 0.2907 0.071 Uiso calc R 1 1 . .
C C25 -0.1374(4) 0.8444(4) 0.1792(2) 0.0605(10) Uani d . 1 1 . .
H H25 -0.2176 0.8148 0.1744 0.073 Uiso calc R 1 1 . .
C C26 -0.0721(3) 0.9056(4) 0.1164(2) 0.0542(9) Uani d . 1 1 . .
H H26 -0.1060 0.9171 0.0694 0.065 Uiso calc R 1 1 . .
C C27 0.0471(3) 0.9493(3) 0.12673(18) 0.0441(7) Uani d . 1 1 . .
C C28 0.3296(3) 1.1121(3) 0.07887(17) 0.0428(7) Uani d . 1 1 . .
C C29 0.4738(3) 1.0776(3) 0.08827(19) 0.0498(8) Uani d . 1 1 . .
H H29 0.5086 1.0045 0.1204 0.060 Uiso calc R 1 1 . .
C C30 0.5661(4) 1.1508(4) 0.0504(2) 0.0526(8) Uani d . 1 1 . .
H H30 0.6623 1.1272 0.0568 0.063 Uiso calc R 1 1 . .
C C31 0.5138(4) 1.2583(4) 0.00333(19) 0.0518(8) Uani d . 1 1 . .
C C32 0.3721(4) 1.2963(4) -0.0070(2) 0.0583(9) Uani d . 1 1 . .
H H32 0.3386 1.3704 -0.0387 0.070 Uiso calc R 1 1 . .
C C33 0.2796(4) 1.2225(3) 0.03065(19) 0.0523(8) Uani d . 1 1 . .
H H33 0.1836 1.2468 0.0237 0.063 Uiso calc R 1 1 . .
C C34 0.4011(3) 0.8685(3) 0.26853(17) 0.0405(7) Uani d . 1 1 . .
C C35 0.4468(4) 0.8454(4) 0.33915(19) 0.0593(10) Uani d . 1 1 . .
H H35 0.4098 0.9070 0.3745 0.071 Uiso calc R 1 1 . .
C C36 0.5462(4) 0.7330(4) 0.3592(2) 0.0663(11) Uani d . 1 1 . .
H H36 0.5747 0.7180 0.4077 0.080 Uiso calc R 1 1 . .
C C37 0.6015(3) 0.6445(3) 0.3062(2) 0.0499(8) Uani d . 1 1 . .
C C38 0.5589(3) 0.6633(3) 0.23460(19) 0.0490(8) Uani d . 1 1 . .
H H38 0.5971 0.6018 0.1992 0.059 Uiso calc R 1 1 . .
C C39 0.4581(3) 0.7755(3) 0.21666(18) 0.0468(8) Uani d . 1 1 . .
H H39 0.4277 0.7890 0.1686 0.056 Uiso calc R 1 1 . .
C C40 0.2950(3) 0.9941(3) 0.24839(18) 0.0459(8) Uani d . 1 1 . .
H H40A 0.2292 1.0191 0.2934 0.055 Uiso calc R 1 1 . .
H H40B 0.3456 1.0628 0.2331 0.055 Uiso calc R 1 1 . .
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
Br1 0.0788(3) 0.0672(3) 0.0755(3) 0.0185(2) 0.0038(2) -0.0161(2)
Br2 0.0928(4) 0.1135(4) 0.1374(5) -0.0157(3) -0.0652(3) -0.0351(4)
N1 0.0403(14) 0.0471(15) 0.0417(15) -0.0073(11) -0.0073(11) -0.0042(12)
N2 0.0452(15) 0.0564(17) 0.0450(15) -0.0001(13) -0.0116(12) -0.0090(13)
C1 0.0391(16) 0.0477(19) 0.0423(17) -0.0088(14) -0.0080(13) -0.0056(14)
C2 0.0403(17) 0.052(2) 0.056(2) -0.0013(15) -0.0109(15) -0.0112(16)
C3 0.055(2) 0.065(2) 0.076(3) 0.0094(19) -0.0206(19) -0.012(2)
C4 0.060(2) 0.062(3) 0.108(4) 0.009(2) -0.017(2) -0.031(2)
C5 0.061(2) 0.079(3) 0.077(3) 0.003(2) -0.001(2) -0.038(2)
C6 0.057(2) 0.070(3) 0.059(2) -0.0081(19) -0.0032(17) -0.0253(19)
C7 0.0357(16) 0.054(2) 0.053(2) -0.0091(14) -0.0043(14) -0.0145(16)
C8 0.0412(16) 0.0445(18) 0.0340(16) -0.0038(13) -0.0007(13) -0.0067(13)
C9 0.0463(18) 0.0428(19) 0.052(2) -0.0029(14) -0.0135(15) -0.0013(15)
C10 0.052(2) 0.047(2) 0.083(3) -0.0071(16) -0.0150(19) -0.0115(19)
C11 0.048(2) 0.070(3) 0.071(3) -0.0017(18) -0.0218(18) -0.022(2)
C12 0.067(2) 0.075(3) 0.051(2) -0.007(2) -0.0215(18) 0.0022(19)
C13 0.056(2) 0.053(2) 0.050(2) -0.0093(16) -0.0040(16) 0.0083(16)
C14 0.0463(17) 0.0454(18) 0.0344(16) -0.0051(14) -0.0062(13) -0.0010(13)
C15 0.0433(18) 0.057(2) 0.056(2) -0.0050(15) -0.0127(15) -0.0088(17)
C16 0.063(2) 0.052(2) 0.060(2) -0.0064(17) -0.0101(18) -0.0136(17)
C17 0.0503(19) 0.0428(18) 0.0465(19) 0.0003(15) 0.0011(15) 0.0001(15)
C18 0.0434(18) 0.058(2) 0.0468(19) 0.0004(15) -0.0058(15) 0.0036(16)
C19 0.0468(18) 0.053(2) 0.0421(18) -0.0064(15) -0.0083(14) -0.0032(15)
C20 0.0546(19) 0.0498(19) 0.0389(17) -0.0142(15) -0.0045(14) -0.0022(14)
Br3 0.0869(3) 0.1047(4) 0.0508(2) -0.0628(3) -0.0016(2) -0.0045(2)
Br4 0.0602(3) 0.0730(3) 0.0883(3) 0.0071(2) -0.0228(2) 0.0056(2)
N3 0.0405(13) 0.0419(14) 0.0366(14) -0.0078(11) -0.0078(10) 0.0007(11)
N4 0.0477(15) 0.0530(17) 0.0406(15) -0.0120(12) -0.0097(12) 0.0033(12)
C21 0.0403(16) 0.0435(18) 0.0386(17) -0.0061(13) -0.0054(13) 0.0004(13)
C22 0.0399(16) 0.0381(17) 0.0387(17) -0.0034(13) -0.0041(13) 0.0010(13)
C23 0.059(2) 0.0447(19) 0.0473(19) -0.0027(16) -0.0013(16) 0.0022(15)
C24 0.052(2) 0.057(2) 0.063(2) -0.0135(17) 0.0059(17) 0.0041(18)
C25 0.0438(19) 0.058(2) 0.079(3) -0.0147(17) -0.0080(18) 0.005(2)
C26 0.0481(19) 0.059(2) 0.057(2) -0.0134(16) -0.0150(16) 0.0036(17)
C27 0.0417(17) 0.0449(18) 0.0428(18) -0.0078(14) -0.0041(14) 0.0024(14)
C28 0.0454(17) 0.0474(18) 0.0381(17) -0.0148(14) -0.0061(13) -0.0033(14)
C29 0.0490(19) 0.051(2) 0.0502(19) -0.0103(16) -0.0106(15) -0.0028(16)
C30 0.0422(17) 0.068(2) 0.053(2) -0.0191(16) -0.0050(15) -0.0127(18)
C31 0.058(2) 0.065(2) 0.0413(18) -0.0330(18) 0.0018(15) -0.0090(16)
C32 0.068(2) 0.058(2) 0.051(2) -0.0204(19) -0.0123(18) 0.0050(17)
C33 0.0518(19) 0.057(2) 0.049(2) -0.0173(16) -0.0104(15) 0.0078(16)
C34 0.0406(16) 0.0464(18) 0.0355(16) -0.0124(13) -0.0041(12) -0.0032(13)
C35 0.058(2) 0.078(3) 0.0351(18) 0.0038(18) -0.0091(15) -0.0170(17)
C36 0.057(2) 0.094(3) 0.0408(19) 0.001(2) -0.0134(16) -0.0055(19)
C37 0.0405(17) 0.054(2) 0.052(2) -0.0066(15) -0.0065(15) 0.0020(16)
C38 0.0515(19) 0.0449(19) 0.0494(19) -0.0077(15) -0.0072(15) -0.0060(15)
C39 0.0542(19) 0.0493(19) 0.0395(17) -0.0134(15) -0.0133(14) -0.0022(14)
C40 0.0537(19) 0.0464(19) 0.0378(17) -0.0095(15) -0.0083(14) -0.0053(14)
_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
Br1 C17 . 1.899(3) ?
Br2 C11 . 1.895(4) ?
N1 C1 . 1.381(4) ?
N1 C7 . 1.381(4) ?
N1 C20 . 1.448(4) ?
N2 C1 . 1.308(4) ?
N2 C2 . 1.385(4) ?
C1 C14 . 1.460(4) ?
C2 C7 . 1.394(5) ?
C2 C3 . 1.395(4) ?
C3 C4 . 1.368(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.397(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.382(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.386(5) ?
C6 H6 . 0.9300 ?
C8 C13 . 1.372(4) ?
C8 C9 . 1.378(5) ?
C8 C20 . 1.519(5) ?
C9 C10 . 1.379(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.380(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.361(6) ?
C12 C13 . 1.368(5) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 C15 . 1.387(5) ?
C14 C19 . 1.400(4) ?
C15 C16 . 1.382(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.392(5) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.366(5) ?
C18 C19 . 1.380(5) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
Br3 C31 . 1.895(3) ?
Br4 C37 . 1.890(3) ?
N3 C21 . 1.374(4) ?
N3 C22 . 1.383(4) ?
N3 C40 . 1.453(4) ?
N4 C21 . 1.316(4) ?
N4 C27 . 1.379(4) ?
C21 C28 . 1.464(5) ?
C22 C27 . 1.391(4) ?
C22 C23 . 1.395(4) ?
C23 C24 . 1.372(5) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.396(5) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.382(5) ?
C25 H25 . 0.9300 ?
C26 C27 . 1.395(5) ?
C26 H26 . 0.9300 ?
C28 C29 . 1.392(4) ?
C28 C33 . 1.396(4) ?
C29 C30 . 1.384(5) ?
C29 H29 . 0.9300 ?
C30 C31 . 1.369(5) ?
C30 H30 . 0.9300 ?
C31 C32 . 1.373(5) ?
C32 C33 . 1.389(5) ?
C32 H32 . 0.9300 ?
C33 H33 . 0.9300 ?
C34 C35 . 1.371(4) ?
C34 C39 . 1.386(4) ?
C34 C40 . 1.509(4) ?
C35 C36 . 1.382(5) ?
C35 H35 . 0.9300 ?
C36 C37 . 1.366(5) ?
C36 H36 . 0.9300 ?
C37 C38 . 1.376(5) ?
C38 C39 . 1.379(4) ?
C38 H38 . 0.9300 ?
C39 H39 . 0.9300 ?
C40 H40A . 0.9700 ?
C40 H40B . 0.9700 ?
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
C1 N1 C7 . . 106.3(2) ?
C1 N1 C20 . . 128.2(3) ?
C7 N1 C20 . . 125.0(3) ?
C1 N2 C2 . . 104.9(3) ?
N2 C1 N1 . . 113.1(3) ?
N2 C1 C14 . . 123.8(3) ?
N1 C1 C14 . . 123.1(3) ?
N2 C2 C7 . . 110.5(3) ?
N2 C2 C3 . . 130.0(3) ?
C7 C2 C3 . . 119.5(3) ?
C4 C3 C2 . . 118.4(4) ?
C4 C3 H3 . . 120.8 ?
C2 C3 H3 . . 120.8 ?
C3 C4 C5 . . 121.0(4) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C6 C5 C4 . . 122.1(4) ?
C6 C5 H5 . . 118.9 ?
C4 C5 H5 . . 118.9 ?
C5 C6 C7 . . 115.9(4) ?
C5 C6 H6 . . 122.0 ?
C7 C6 H6 . . 122.0 ?
N1 C7 C6 . . 131.7(3) ?
N1 C7 C2 . . 105.2(3) ?
C6 C7 C2 . . 123.0(3) ?
C13 C8 C9 . . 118.5(3) ?
C13 C8 C20 . . 117.9(3) ?
C9 C8 C20 . . 123.7(3) ?
C8 C9 C10 . . 121.0(3) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
C9 C10 C11 . . 118.5(4) ?
C9 C10 H10 . . 120.7 ?
C11 C10 H10 . . 120.7 ?
C12 C11 C10 . . 121.3(3) ?
C12 C11 Br2 . . 118.6(3) ?
C10 C11 Br2 . . 120.1(3) ?
C11 C12 C13 . . 119.0(3) ?
C11 C12 H12 . . 120.5 ?
C13 C12 H12 . . 120.5 ?
C12 C13 C8 . . 121.6(4) ?
C12 C13 H13 . . 119.2 ?
C8 C13 H13 . . 119.2 ?
C15 C14 C19 . . 118.3(3) ?
C15 C14 C1 . . 119.6(3) ?
C19 C14 C1 . . 122.0(3) ?
C16 C15 C14 . . 121.7(3) ?
C16 C15 H15 . . 119.2 ?
C14 C15 H15 . . 119.2 ?
C15 C16 C17 . . 117.8(3) ?
C15 C16 H16 . . 121.1 ?
C17 C16 H16 . . 121.1 ?
C18 C17 C16 . . 122.4(3) ?
C18 C17 Br1 . . 119.3(3) ?
C16 C17 Br1 . . 118.3(3) ?
C17 C18 C19 . . 118.8(3) ?
C17 C18 H18 . . 120.6 ?
C19 C18 H18 . . 120.6 ?
C18 C19 C14 . . 121.0(3) ?
C18 C19 H19 . . 119.5 ?
C14 C19 H19 . . 119.5 ?
N1 C20 C8 . . 115.7(3) ?
N1 C20 H20A . . 108.4 ?
C8 C20 H20A . . 108.4 ?
N1 C20 H20B . . 108.4 ?
C8 C20 H20B . . 108.4 ?
H20A C20 H20B . . 107.4 ?
C21 N3 C22 . . 106.3(2) ?
C21 N3 C40 . . 128.8(3) ?
C22 N3 C40 . . 124.7(2) ?
C21 N4 C27 . . 105.3(3) ?
N4 C21 N3 . . 112.6(3) ?
N4 C21 C28 . . 121.6(3) ?
N3 C21 C28 . . 125.7(3) ?
N3 C22 C27 . . 105.6(3) ?
N3 C22 C23 . . 132.0(3) ?
C27 C22 C23 . . 122.4(3) ?
C24 C23 C22 . . 116.2(3) ?
C24 C23 H23 . . 121.9 ?
C22 C23 H23 . . 121.9 ?
C23 C24 C25 . . 122.2(3) ?
C23 C24 H24 . . 118.9 ?
C25 C24 H24 . . 118.9 ?
C26 C25 C24 . . 121.5(3) ?
C26 C25 H25 . . 119.2 ?
C24 C25 H25 . . 119.2 ?
C25 C26 C27 . . 117.1(3) ?
C25 C26 H26 . . 121.5 ?
C27 C26 H26 . . 121.5 ?
N4 C27 C22 . . 110.2(3) ?
N4 C27 C26 . . 129.3(3) ?
C22 C27 C26 . . 120.6(3) ?
C29 C28 C33 . . 118.7(3) ?
C29 C28 C21 . . 124.4(3) ?
C33 C28 C21 . . 116.9(3) ?
C30 C29 C28 . . 120.8(3) ?
C30 C29 H29 . . 119.6 ?
C28 C29 H29 . . 119.6 ?
C31 C30 C29 . . 119.1(3) ?
C31 C30 H30 . . 120.4 ?
C29 C30 H30 . . 120.4 ?
C30 C31 C32 . . 121.9(3) ?
C30 C31 Br3 . . 119.6(3) ?
C32 C31 Br3 . . 118.5(3) ?
C31 C32 C33 . . 119.0(3) ?
C31 C32 H32 . . 120.5 ?
C33 C32 H32 . . 120.5 ?
C32 C33 C28 . . 120.5(3) ?
C32 C33 H33 . . 119.7 ?
C28 C33 H33 . . 119.7 ?
C35 C34 C39 . . 118.0(3) ?
C35 C34 C40 . . 120.1(3) ?
C39 C34 C40 . . 121.9(3) ?
C34 C35 C36 . . 121.9(3) ?
C34 C35 H35 . . 119.1 ?
C36 C35 H35 . . 119.1 ?
C37 C36 C35 . . 118.4(3) ?
C37 C36 H36 . . 120.8 ?
C35 C36 H36 . . 120.8 ?
C36 C37 C38 . . 121.8(3) ?
C36 C37 Br4 . . 119.8(3) ?
C38 C37 Br4 . . 118.4(3) ?
C37 C38 C39 . . 118.4(3) ?
C37 C38 H38 . . 120.8 ?
C39 C38 H38 . . 120.8 ?
C38 C39 C34 . . 121.5(3) ?
C38 C39 H39 . . 119.2 ?
C34 C39 H39 . . 119.2 ?
N3 C40 C34 . . 113.7(3) ?
N3 C40 H40A . . 108.8 ?
C34 C40 H40A . . 108.8 ?
N3 C40 H40B . . 108.8 ?
C34 C40 H40B . . 108.8 ?
H40A C40 H40B . . 107.7 ?
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
C2 N2 C1 N1 . . . . 0.5(4) ?
C2 N2 C1 C14 . . . . 179.8(3) ?
C7 N1 C1 N2 . . . . -1.0(4) ?
C20 N1 C1 N2 . . . . -173.0(3) ?
C7 N1 C1 C14 . . . . 179.7(3) ?
C20 N1 C1 C14 . . . . 7.7(5) ?
C1 N2 C2 C7 . . . . 0.1(4) ?
C1 N2 C2 C3 . . . . 179.3(4) ?
N2 C2 C3 C4 . . . . -177.4(4) ?
C7 C2 C3 C4 . . . . 1.7(6) ?
C2 C3 C4 C5 . . . . -0.2(7) ?
C3 C4 C5 C6 . . . . -1.8(7) ?
C4 C5 C6 C7 . . . . 2.1(6) ?
C1 N1 C7 C6 . . . . -177.4(4) ?
C20 N1 C7 C6 . . . . -5.1(6) ?
C1 N1 C7 C2 . . . . 1.0(4) ?
C20 N1 C7 C2 . . . . 173.3(3) ?
C5 C6 C7 N1 . . . . 177.6(4) ?
C5 C6 C7 C2 . . . . -0.5(6) ?
N2 C2 C7 N1 . . . . -0.7(4) ?
C3 C2 C7 N1 . . . . -180.0(3) ?
N2 C2 C7 C6 . . . . 177.9(3) ?
C3 C2 C7 C6 . . . . -1.4(6) ?
C13 C8 C9 C10 . . . . 2.6(5) ?
C20 C8 C9 C10 . . . . -177.6(3) ?
C8 C9 C10 C11 . . . . -0.8(5) ?
C9 C10 C11 C12 . . . . -1.3(6) ?
C9 C10 C11 Br2 . . . . -179.9(3) ?
C10 C11 C12 C13 . . . . 1.4(6) ?
Br2 C11 C12 C13 . . . . -180.0(3) ?
C11 C12 C13 C8 . . . . 0.5(6) ?
C9 C8 C13 C12 . . . . -2.5(5) ?
C20 C8 C13 C12 . . . . 177.7(3) ?
N2 C1 C14 C15 . . . . 49.0(5) ?
N1 C1 C14 C15 . . . . -131.8(3) ?
N2 C1 C14 C19 . . . . -128.0(4) ?
N1 C1 C14 C19 . . . . 51.2(5) ?
C19 C14 C15 C16 . . . . 1.1(5) ?
C1 C14 C15 C16 . . . . -176.1(3) ?
C14 C15 C16 C17 . . . . -0.7(5) ?
C15 C16 C17 C18 . . . . 0.9(5) ?
C15 C16 C17 Br1 . . . . 178.8(3) ?
C16 C17 C18 C19 . . . . -1.4(5) ?
Br1 C17 C18 C19 . . . . -179.3(2) ?
C17 C18 C19 C14 . . . . 1.7(5) ?
C15 C14 C19 C18 . . . . -1.6(5) ?
C1 C14 C19 C18 . . . . 175.5(3) ?
C1 N1 C20 C8 . . . . -107.0(4) ?
C7 N1 C20 C8 . . . . 82.3(4) ?
C13 C8 C20 N1 . . . . 175.6(3) ?
C9 C8 C20 N1 . . . . -4.2(4) ?
C27 N4 C21 N3 . . . . 0.5(3) ?
C27 N4 C21 C28 . . . . -176.9(3) ?
C22 N3 C21 N4 . . . . -0.7(3) ?
C40 N3 C21 N4 . . . . -175.6(3) ?
C22 N3 C21 C28 . . . . 176.6(3) ?
C40 N3 C21 C28 . . . . 1.6(5) ?
C21 N3 C22 C27 . . . . 0.6(3) ?
C40 N3 C22 C27 . . . . 175.8(3) ?
C21 N3 C22 C23 . . . . -177.3(3) ?
C40 N3 C22 C23 . . . . -2.1(5) ?
N3 C22 C23 C24 . . . . 177.6(3) ?
C27 C22 C23 C24 . . . . 0.1(5) ?
C22 C23 C24 C25 . . . . 0.8(5) ?
C23 C24 C25 C26 . . . . -0.5(6) ?
C24 C25 C26 C27 . . . . -0.6(5) ?
C21 N4 C27 C22 . . . . -0.1(4) ?
C21 N4 C27 C26 . . . . 178.8(3) ?
N3 C22 C27 N4 . . . . -0.3(3) ?
C23 C22 C27 N4 . . . . 177.8(3) ?
N3 C22 C27 C26 . . . . -179.3(3) ?
C23 C22 C27 C26 . . . . -1.1(5) ?
C25 C26 C27 N4 . . . . -177.4(3) ?
C25 C26 C27 C22 . . . . 1.4(5) ?
N4 C21 C28 C29 . . . . -137.9(3) ?
N3 C21 C28 C29 . . . . 45.0(5) ?
N4 C21 C28 C33 . . . . 39.1(4) ?
N3 C21 C28 C33 . . . . -137.9(3) ?
C33 C28 C29 C30 . . . . -0.3(5) ?
C21 C28 C29 C30 . . . . 176.7(3) ?
C28 C29 C30 C31 . . . . 0.1(5) ?
C29 C30 C31 C32 . . . . 0.4(5) ?
C29 C30 C31 Br3 . . . . -179.2(3) ?
C30 C31 C32 C33 . . . . -0.8(6) ?
Br3 C31 C32 C33 . . . . 178.8(3) ?
C31 C32 C33 C28 . . . . 0.6(5) ?
C29 C28 C33 C32 . . . . -0.1(5) ?
C21 C28 C33 C32 . . . . -177.3(3) ?
C39 C34 C35 C36 . . . . -0.3(6) ?
C40 C34 C35 C36 . . . . -178.5(4) ?
C34 C35 C36 C37 . . . . 1.2(6) ?
C35 C36 C37 C38 . . . . -1.3(6) ?
C35 C36 C37 Br4 . . . . 178.9(3) ?
C36 C37 C38 C39 . . . . 0.4(5) ?
Br4 C37 C38 C39 . . . . -179.7(3) ?
C37 C38 C39 C34 . . . . 0.6(5) ?
C35 C34 C39 C38 . . . . -0.6(5) ?
C40 C34 C39 C38 . . . . 177.6(3) ?
C21 N3 C40 C34 . . . . -106.7(3) ?
C22 N3 C40 C34 . . . . 79.2(4) ?
C35 C34 C40 N3 . . . . -156.4(3) ?
C39 C34 C40 N3 . . . . 25.4(4) ?
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
C13 H13 Br3 2_675 0.93 2.85 3.433(4) 122
C26 H26 N4 2_575 0.93 2.62 3.513(4) 161
data_New_Global_Publ_Block
_journal_date_recd_electronic 2014-04-04
_journal_date_accepted 2014-04-22
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2014
_journal_volume 70
_journal_issue 5
_journal_page_first o610
_journal_page_last o611
_journal_paper_category QO
_journal_paper_doi 10.1107/S1600536814009076
_journal_coeditor_code BX2457
_publ_contact_author_name 'Dr Zhi-Rong Qu'
_publ_contact_author_address
;
Key Laboratory of Organosilicon Chemistry and Material Technology of
Ministry of Education, Hangzhou Normal University,
No.58, Haishu Road, Hangzhou, 311121, People's Republic of China
;
_publ_contact_author_email 'quzr@hznu.edu.cn'
_publ_contact_author_fax '8657128865135'
_publ_contact_author_phone '8657128868755'
_publ_section_title
;
1-(4-Bromobenzyl)-2-(4-bromophenyl)-1H-benzimidazole
;
_publ_section_title_footnote .
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Ma, Hua-Jun' .
;
Key Laboratory of Organosilicon Chemistry and Material Technology of the
Ministry of Education, Hangzhou Normal University
No. 58, Haishu Road, Hangzhou, 311121, People's Republic of China
;
'Qu, Zhi-Rong' .
;
Key Laboratory of Organosilicon Chemistry and Material Technology of the
Ministry of Education, Hangzhou Normal University
No. 58, Haishu Road, Hangzhou, 311121, People's Republic of China
;
_publ_section_synopsis .