data_2007295 _journal_name_full 'Acta Crystallographica' _journal_year 1998 _journal_volume C54 _journal_page_first 854 _journal_page_last 856 _publ_section_title ; 1-Benzyl-2-(2,6-dichloroanilinomethyl)-1H-benzimidazole ; loop_ _publ_author_name 'Kendi, Engin' '\"Ozbey, S\"uheyla' 'Tun\,cbilek, Meral' 'G\"oker, Hakan' audit_creation_date ? _chemical_formula_sum 'C21 H17 Cl2 N3' _chemical_formula_weight 382.291 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall ' -P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' '-x+1/2,y+1/2,-z+1/2' 'x+1/2,-y+1/2,z+1/2 ' _cell_length_a 11.2662(13) _cell_length_b 9.8162(10) _cell_length_c 17.2773(18) _cell_angle_alpha 90 _cell_angle_beta 102.470(10) _cell_angle_gamma 90 _cell_volume 1865.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295 _exptl_crystal_density_diffrn 1.3610 _refine_ls_R_factor_obs .0336 _refine_ls_wR_factor_obs .0390 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 1.00707(6) .05326(6) .13175(4) .0633(4) Ueq . . Cl Cl2 .73654(6) .39804(8) .26708(4) .0752(2) Ueq . . Cl N1 .8394(2) .5449(2) -.01560(10) .0447(5) Ueq . . N N2 .8199(2) .2703(2) .12860(10) .0500(6) Ueq . . N N3 .8399(2) .3169(2) -.02270(10) .0497(6) Ueq . . N C2 .8341(2) .4233(2) .02190(10) .0449(6) Ueq . . C C4 .8577(2) .3061(3) -.16580(10) .0577(6) Ueq . . C C5 .8641(2) .3862(3) -.23000(10) .0641(8) Ueq . . C C6 .8616(2) .5279(3) -.22620(10) .0594(9) Ueq . . C C7 .8535(2) .5947(3) -.15730(10) .0532(7) Ueq . . C C8 .8481(2) .5132(2) -.09250(10) .0440(6) Ueq . . C C9 .8494(2) .3712(2) -.09560(10) .0463(6) Ueq . . C C10 .8364(2) .6826(2) .01550(10) .0498(6) Ueq . . C C11 .7232(2) .7600(2) -.02210(10) .0413(6) Ueq . . C C12 .7276(2) .9003(2) -.02780(10) .0532(6) Ueq . . C C13 .6238(2) .9733(3) -.0602(2) .0702(9) Ueq . . C C14 .5161(2) .9073(3) -.0875(2) .0758(10) Ueq . . C C15 .5107(2) .7691(3) -.0826(2) .0686(8) Ueq . . C C16 .6143(2) .6953(3) -.04970(10) .0530(6) Ueq . . C C20 .8199(2) .4141(2) .10610(10) .0502(6) Ueq . . C C21 .8823(2) .2304(2) .20380(10) .0409(5) Ueq . . C C22 .9723(2) .1295(2) .21500(10) .0439(6) Ueq . . C C23 1.0357(2) .0898(2) .28890(10) .0552(6) Ueq . . C C24 1.0092(2) .1500(3) .35480(10) .0610(9) Ueq . . C C25 .9189(2) .2458(2) .34750(10) .0541(6) Ueq . . C C26 .8558(2) .2837(2) .27300(10) .0460(6) Ueq . . C H4 .859 .210 -.169 .075 Ueq . . H H5 .870 .344 -.278 .082 Ueq . . H H6 .866 .580 -.272 .076 Ueq . . H H7 .852 .691 -.154 .068 Ueq . . H H12 .802 .947 -.009 .070 Ueq . . H H13 .627 1.070 -.064 .091 Ueq . . H H14 .445 .958 -.110 .098 Ueq . . H H15 .436 .723 -.101 .089 Ueq . . H H16 .610 .599 -.047 .068 Ueq . . H H23 1.097 .022 .294 .071 Ueq . . H H24 1.054 .125 .406 .079 Ueq . . H H25 .900 .286 .393 .070 Ueq . . H H101 .905 .731 .006 .065 Ueq . . H H102 .841 .677 .071 .065 Ueq . . H H201 .885 .460 .140 .065 Ueq . . H H202 .745 .456 .111 .065 Ueq . . H HN .839 .220 .092 .062 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 .0732(3) .0520(3) .0676(3) .0134(3) .0216(3) -.0030(3) Cl Cl2 .0700(3) .0930(4) .0643(3) .0347(3) .0184(3) -.0014(3) Cl N1 .0476(9) .0406(9) .0421(9) .0056(8) .0014(7) -.0018(8) N N2 .0590(10) .0470(10) .0400(9) .0082(9) .0016(8) .0003(8) N N3 .0590(10) .0430(9) .0431(9) .0114(9) .0019(8) .0019(8) N C2 .0420(10) .0470(10) .0410(10) .0116(9) -.0012(9) .0030(10) C C4 .0670(10) .0530(10) .0500(10) .0120(10) .0060(10) -.0070(10) C C5 .0700(10) .078(2) .0450(10) .0070(10) .0140(10) -.0070(10) C C6 .0590(10) .070(2) .0490(10) -.0040(10) .0110(10) .0060(10) C C7 .0520(10) .0530(10) .0540(10) -.0060(10) .0102(9) .0030(10) C C8 .0381(9) .0480(10) .0430(10) .0029(9) .0026(8) -.0011(9) C C9 .0440(10) .0480(10) .0430(10) .0099(9) .0010(9) .0010(10) C C10 .0520(10) .0450(10) .0480(10) -.0010(10) -.0010(10) -.0070(10) C C11 .0440(10) .0450(10) .0340(9) .0039(9) .0064(8) -.0035(9) C C12 .0630(10) .0480(10) .0500(10) .0020(10) .0150(10) -.0040(10) C C13 .093(2) .0540(10) .0650(10) .0260(10) .0200(10) .0040(10) C C14 .0740(10) .090(2) .0610(10) .0380(10) .0090(10) -.0020(10) C C15 .0460(10) .094(2) .0620(10) .0060(10) .0030(10) -.0150(10) C C16 .0500(10) .0530(10) .0540(10) .0000(10) .0070(10) -.0070(10) C C20 .0560(10) .0490(10) .0420(10) .0130(10) .0028(9) .0020(10) C C21 .0378(9) .0400(10) .0430(10) -.0012(9) .0044(8) .0048(9) C C22 .0430(10) .0390(10) .0500(10) -.0017(9) .0107(8) .0042(9) C C23 .0490(10) .0460(10) .0660(10) .0080(10) .0020(10) .0140(10) C C24 .0700(10) .0590(10) .0470(10) .0030(10) -.0030(10) .0150(10) C C25 .0660(10) .0540(10) .0420(10) -.0030(10) .0110(10) .0060(10) C C26 .0430(10) .0470(10) .0480(10) .0040(10) .0098(8) .0050(10) 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 C22 . . 1.739(2) yes Cl2 C26 . . 1.737(2) yes N1 C2 . . 1.364(3) yes N1 C8 . . 1.389(3) no N1 C10 . . 1.458(3) yes N2 C20 . . 1.464(3) yes N2 C21 . . 1.393(2) no N2 HN . . .869(2) no N3 C2 . . 1.308(3) yes N3 C9 . . 1.394(3) no C2 C20 . . 1.500(3) no C4 C5 . . 1.374(4) no C4 C9 . . 1.391(3) no C4 H4 . . .950 no C5 C6 . . 1.393(4) no C5 H5 . . .950 no C6 C7 . . 1.380(3) no C6 H6 . . .950 no C7 C8 . . 1.388(3) no C7 H7 . . .950 no C8 C9 . . 1.395(3) no C10 C11 . . 1.506(3) no C25 C26 . . 1.381(3) no C10 H101 . . .950 no C10 H102 . . .950 no C11 C12 . . 1.382(3) no C11 C16 . . 1.373(3) no C12 C13 . . 1.383(3) no C12 H12 . . .950 no C13 C14 . . 1.367(4) no C13 H13 . . .950 no C14 C15 . . 1.361(4) no C14 H14 . . .950 no C15 C16 . . 1.387(3) no C15 H15 . . .950 no C16 H16 . . .950 no C20 H201 . . .950 no C20 H202 . . .950 no C21 C22 . . 1.400(3) no C21 C26 . . 1.395(3) no C22 C23 . . 1.379(3) no C23 C24 . . 1.372(4) no C23 H23 . . .950 no C24 C25 . . 1.372(3) no C24 H24 . . .950 no C25 H25 . . .950 no