data_2008172
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  243
_journal_page_last  245
_publ_section_title
;
2,5-Dichloro-1-(p-chlorobenzyl)-1H-benzimidazole
;
loop_
_publ_author_name
  'Kend\.i, Eng\.in'
  '\"Ozbey, S\"uheyla'
  'G\"oker, Hakan'
_chemical_formula_moiety  'C14 H9 Cl3 N2'
_chemical_formula_sum  'C14 H9 Cl3 N2'
_chemical_formula_weight  311.598
_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  6.5118(4)
_cell_length_b  8.1702(6)
_cell_length_c  13.9142(8)
_cell_angle_alpha  72.501(5)
_cell_angle_beta  75.962(5)
_cell_angle_gamma  71.093(6)
_cell_volume  659.22(8)
_cell_formula_units_Z  2
_cell_measurement_temperature  295
_exptl_crystal_density_diffrn  1.5698
_refine_ls_R_factor_obs  0.030
_refine_ls_wR_factor_obs  0.031
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_type_symbol
  Cl1 1.24970(10)
  -0.21830(8) 0.27571(4) 0.0589(2) Ueq . . Cl
  Cl2 1.11100(10)
  0.53855(8) -0.21575(4) 0.0578(2) Ueq . . Cl
  Cl3 0.28660(10)
  0.39753(8) 0.54015(4) 0.0646(2) Ueq . . Cl
  N1 0.9503(3) 0.0175(2) 0.16360(10)
  0.0377(5) Ueq . . N
  N3 1.3003(3) 0.0329(2) 0.10680(10)
  0.0420(6) Ueq . . N
  C2 1.1654(3) -0.0442(3) 0.17600(10)
  0.0405(6) Ueq . . C
  C4 1.2185(3) 0.2788(2) -0.05020(10)
  0.0397(7) Ueq . . C
  C5 1.0489(3) 0.3867(2) -0.10160(10)
  0.0402(6) Ueq . . C
  C6 0.8308(3) 0.3802(3) -0.0677(2) 0.0440(7) Ueq . . C
  C7 0.7761(3) 0.2609(3) 0.02200(10)
  0.0415(7) Ueq . . C
  C8 0.9457(3) 0.1512(2) 0.07450(10)
  0.0344(5) Ueq . . C
  C9 1.1640(3) 0.1585(2) 0.04020(10)
  0.0360(6) Ueq . . C
  C10 0.7597(3) -0.0357(3) 0.23050(10)
  0.0430(7) Ueq . . C
  C11 0.6446(3) 0.0793(2) 0.30610(10)
  0.0384(6) Ueq . . C
  C12 0.4310(4) 0.1817(3) 0.3022(2) 0.0485(7) Ueq . . C
  C13 0.3202(4) 0.2826(3) 0.3735(2) 0.0525(7) Ueq . . C
  C14 0.4272(4) 0.2784(3) 0.4476(2) 0.0446(6) Ueq . . C
  C15 0.6408(4) 0.1808(3) 0.4523(2) 0.0488(7) Ueq . . C
  C16 0.7488(4) 0.0799(3) 0.3813(2) 0.0494(7) Ueq . . C
  H4 1.366 0.285 -0.076 0.052 Ueq . . H
  H6 0.720 0.458 -0.107 0.057 Ueq . . H
  H7 0.629 0.255 0.047 0.050 Ueq . . H
  H12 0.358 0.183 0.250 0.058 Ueq . . H
  H13 0.173 0.353 0.370 0.065 Ueq . . H
  H15 0.715 0.182 0.503 0.060 Ueq . . H
  H16 0.896 0.009 0.385 0.060 Ueq . . H
  H101 0.806 -0.156 0.268 0.053 Ueq . . H
  H102 0.657 -0.026 0.189 0.053 Ueq . . H
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
_atom_site_aniso_type_symbol
  Cl1 0.0630(3) 0.0541(3) 0.0484(3) -0.0025(3) -0.0159(2) -0.0053(2) Cl
  Cl2 0.0749(3) 0.0534(3) 0.0421(2) -0.0197(2) -0.0082(2) -0.0070(2) Cl
  Cl3 0.0724(4) 0.0636(3) 0.0582(3) -0.0153(3) 0.0110(3) -0.0343(2) Cl
  N1 0.0369(7) 0.0425(7) 0.0368(7) -0.0104(5) -0.0035(6) -0.0158(5) N
  N3 0.0359(7) 0.0512(8) 0.0399(7) -0.0073(6) -0.0077(6) -0.0153(6) N
  C2 0.0431(9) 0.0417(9) 0.0377(8) -0.0050(7) -0.0096(7) -0.0147(6) C
  C4 0.0392(9) 0.0475(8) 0.0376(8) -0.0141(7) -0.0013(7) -0.0186(6) C
  C5 0.0510(10) 0.0391(8) 0.0345(8) -0.0117(7) -0.0060(7) -0.0154(6) C
  C6 0.0447(9) 0.0453(9) 0.0442(9) -0.0026(7) -0.0145(7) -0.0173(7) C
  C7 0.0335(8) 0.0503(9) 0.0446(9) -0.0075(7) -0.0062(7) -0.0202(7) C
  C8 0.0363(8) 0.0377(7) 0.0343(7) -0.0091(6) -0.0032(6) -0.0182(5) C
  C9 0.0345(8) 0.0424(8) 0.0372(7) -0.0074(6) -0.0065(6) -0.0199(6) C
  C10 0.0473(9) 0.0466(8) 0.0408(9) -0.0200(7) 0.0006(7) -0.0172(7) C
  C11 0.0432(9) 0.0389(8) 0.0344(8) -0.0164(6) 0.0000(7) -0.0104(6) C
  C12 0.0490(10) 0.0550(10) 0.0456(9) -0.0113(8) -0.0118(8) -0.0174(7) C
  C13 0.0460(10) 0.0550(10) 0.0550(10) -0.0037(9) -0.0078(9) -0.0207(8) C
  C14 0.0530(10) 0.0400(8) 0.0390(9) -0.0132(8) 0.0036(8) -0.0148(7) C
  C15 0.0560(10) 0.0550(10) 0.0409(9) -0.0147(8) -0.0084(8) -0.0192(7) C
  C16 0.0440(10) 0.0520(10) 0.0476(9) -0.0083(8) 0.0062(8) -0.0205(7) C
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  Cl1 C2 . . 1.711(2) yes
  Cl2 C5 . . 1.748(2) yes
  Cl3 C14 . . 1.746(2) yes
  N1 C2 . . 1.361(3) yes
  N1 C8 . . 1.383(2) yes
  N1 C10 . . 1.464(2) yes
  N3 C2 . . 1.296(2) yes
  N3 C9 . . 1.391(2) yes
  C4 C5 . . 1.371(3) no
  C4 C9 . . 1.394(2) no
  C4 H4 . . 0.950 no
  C5 C6 . . 1.397(3) no
  C6 C7 . . 1.382(2) no
  C6 H6 . . 0.950 no
  C7 C8 . . 1.383(3) no
  C7 H7 . . 0.950 no
  C8 C9 . . 1.400(3) yes
  C10 C11 . . 1.518(3) yes
  C10 H101 . . 0.950 no
  C10 H102 . . 0.950 no
  C11 C12 . . 1.376(3) no
  C11 C16 . . 1.381(3) no
  C12 C13 . . 1.395(3) no
  C12 H12 . . 0.950 no
  C13 C14 . . 1.364(4) no
  C13 H13 . . 0.950 no
  C14 C15 . . 1.367(3) yes
  C15 C16 . . 1.388(3) no
  C15 H15 . . 0.950 no
  C16 H16 . . 0.950 no