#------------------------------------------------------------------------------ #$Date: 2009-11-16 03:43:51 +0200 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2012396.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2012396 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 1410 _journal_page_last 1414 _publ_section_title ; Intermolecular interactions in two (ferrocenylmethyl)benzimidazoles incorporating the 4-MeOC~6~H~4~- and 3,4-(MeO)~2~C~6~H~3~- groups: analysis of MeO-C-C distortions from ideal 120\% geometry ; _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _[local]_cod_cif_authors_sg_H-M 'P 21/n' loop_ _publ_author_name 'Gallagher, John F.' 'Hanlon, Keith' 'Howarth, Joshua' _chemical_formula_moiety 'C25 H22 Fe N2 O' _chemical_formula_sum 'C25 H22 Fe N2 O' _chemical_formula_structural 'C25 H22 Fe N2 O' _chemical_formula_iupac '[Fe (C5 H5) (C20 H17 N2 O)]' _chemical_formula_weight 422.30 _chemical_melting_point 417 _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.4326(10) _cell_length_b 9.5414(7) _cell_length_c 17.1682(8) _cell_angle_alpha 90 _cell_angle_beta 97.400(5) _cell_angle_gamma 90 _cell_volume 2019.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 294.0(10) _exptl_crystal_density_diffrn 1.389 _diffrn_ambient_temperature 294.0(10) 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 Fe1 .20014(2) .22243(3) .039503(15) .04622(11) Uani d . 1 . . Fe O1 .75282(13) .3498(2) .15949(11) .0743(5) Uani d . 1 . . O N1 .36909(13) .23245(17) .36578(9) .0441(4) Uani d . 1 . . N N2 .26635(11) .34679(16) .26896(8) .0403(3) Uani d . 1 . . N C1 .36807(14) .29632(18) .29742(10) .0400(4) Uani d . 1 . . C C2 .22763(16) .4107(2) .19349(11) .0468(4) Uani d . 1 . . C C3 .19879(15) .31226(19) .32413(11) .0423(4) Uani d . 1 . . C C4 .26415(16) .2417(2) .38366(11) .0430(4) Uani d . 1 . . C C5 .21942(19) .1921(2) .44920(12) .0548(5) Uani d . 1 . . C C6 .1110(2) .2165(3) .45187(14) .0628(6) Uani d . 1 . . C C7 .0468(2) .2868(2) .39238(15) .0629(6) Uani d . 1 . . C C8 .08922(17) .3360(2) .32640(13) .0545(5) Uani d . 1 . . C C11 .15878(14) .3132(2) .13943(10) .0412(4) Uani d . 1 . . C C12 .08558(15) .3548(2) .07288(11) .0496(5) Uani d . 1 . . C C13 .03625(18) .2326(3) .03748(13) .0622(6) Uani d . 1 . . C C14 .07835(19) .1157(3) .08187(13) .0615(6) Uani d . 1 . . C C15 .15371(16) .1654(2) .14463(11) .0492(4) Uani d . 1 . . C C21 .3405(2) .3105(3) .01361(17) .0742(7) Uani d . 1 . . C C22 .2627(2) .3083(3) -.05327(15) .0713(7) Uani d . 1 . . C C23 .2331(2) .1685(3) -.06988(14) .0730(7) Uani d . 1 . . C C24 .2926(2) .0837(3) -.01265(16) .0786(8) Uani d . 1 . . C C25 .3594(2) .1723(4) .03887(16) .0772(8) Uani d . 1 . . C C31 .46557(14) .3102(2) .25770(11) .0423(4) Uani d . 1 . . C C32 .53745(16) .1987(2) .26164(13) .0508(5) Uani d . 1 . . C C33 .63338(17) .2065(2) .22893(14) .0568(5) Uani d . 1 . . C C34 .65926(16) .3282(3) .19243(12) .0544(5) Uani d . 1 . . C C35 .58890(17) .4412(2) .18803(13) .0564(5) Uani d . 1 . . C C36 .49319(16) .4329(2) .22102(12) .0503(5) Uani d . 1 . . C C37 .8327(2) .2429(4) .1688(2) .0964(10) Uani d . 1 . . C H2A .2895 .4402 .1684 .056 Uiso calc R 1 . . H H2B .1857 .4936 .2023 .056 Uiso calc R 1 . . H H5 .2615 .1445 .4894 .066 Uiso calc R 1 . . H H6 .0797 .1849 .4950 .075 Uiso calc R 1 . . H H7 -.0261 .3014 .3966 .075 Uiso calc R 1 . . H H8 .0464 .3823 .2860 .065 Uiso calc R 1 . . H H12 .0724 .4464 .0556 .060 Uiso calc R 1 . . H H13 -.0148 .2298 -.0071 .075 Uiso calc R 1 . . H H14 .0598 .0224 .0717 .074 Uiso calc R 1 . . H H15 .1932 .1103 .1828 .059 Uiso calc R 1 . . H H21 .3738 .3900 .0370 .089 Uiso calc R 1 . . H H22 .2353 .3862 -.0817 .086 Uiso calc R 1 . . H H23 .1832 .1375 -.1113 .088 Uiso calc R 1 . . H H24 .2886 -.0134 -.0093 .094 Uiso calc R 1 . . H H25 .4074 .1437 .0820 .093 Uiso calc R 1 . . H H32 .5209 .1167 .2869 .061 Uiso calc R 1 . . H H33 .6801 .1300 .2316 .068 Uiso calc R 1 . . H H35 .6060 .5230 .1628 .068 Uiso calc R 1 . . H H36 .4470 .5098 .2187 .060 Uiso calc R 1 . . H H37A .8511 .2221 .2236 .145 Uiso calc R 1 . . H H37B .8964 .2741 .1476 .145 Uiso calc R 1 . . H H37C .8049 .1601 .1415 .145 Uiso calc R 1 . . 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 Fe1 .05016(17) .04883(18) .04048(16) .00396(12) .00895(11) .00459(12) O1 .0522(9) .0929(13) .0835(11) .0052(9) .0310(8) .0129(10) N1 .0443(8) .0477(9) .0399(8) -.0052(7) .0038(6) .0017(7) N2 .0403(7) .0441(8) .0367(7) -.0023(6) .0060(6) .0021(6) C1 .0411(9) .0398(10) .0392(8) -.0062(7) .0057(7) -.0038(7) C2 .0498(10) .0448(10) .0454(9) -.0027(8) .0041(8) .0090(8) C3 .0447(9) .0421(9) .0415(9) -.0061(8) .0106(7) -.0032(7) C4 .0480(10) .0425(10) .0388(9) -.0081(8) .0072(7) -.0045(7) C5 .0675(13) .0562(12) .0428(10) -.0099(10) .0156(9) .0029(9) C6 .0723(15) .0655(14) .0569(12) -.0128(12) .0319(11) -.0011(11) C7 .0538(12) .0671(15) .0731(15) -.0070(11) .0285(11) -.0070(12) C8 .0481(11) .0563(12) .0605(12) -.0021(9) .0126(9) .0005(10) C11 .0374(8) .0478(10) .0389(9) -.0005(7) .0073(7) .0067(7) C12 .0420(9) .0609(12) .0453(10) .0091(9) .0035(8) .0066(9) C13 .0489(11) .0889(17) .0466(11) -.0052(11) -.0030(9) -.0031(11) C14 .0655(13) .0652(14) .0537(11) -.0189(11) .0076(10) -.0026(11) C15 .0561(11) .0496(11) .0414(9) -.0071(9) .0047(8) .0085(8) C21 .0687(15) .0766(17) .0857(18) -.0062(13) .0421(14) -.0105(14) C22 .0874(17) .0695(16) .0647(14) .0179(13) .0393(13) .0180(12) C23 .0937(18) .0792(17) .0495(12) .0075(15) .0218(12) -.0063(12) C24 .104(2) .0579(15) .0806(16) .0242(14) .0379(16) .0052(13) C25 .0613(14) .105(2) .0682(15) .0244(15) .0208(12) .0079(15) C31 .0384(9) .0456(10) .0432(9) -.0058(7) .0061(7) -.0033(8) C32 .0492(11) .0456(11) .0583(12) -.0026(8) .0096(9) .0046(9) C33 .0484(11) .0577(13) .0655(13) .0077(9) .0124(10) -.0020(10) C34 .0440(10) .0707(14) .0508(11) -.0026(10) .0153(8) -.0041(10) C35 .0516(11) .0558(12) .0651(12) -.0053(10) .0200(9) .0100(10) C36 .0458(10) .0438(10) .0634(11) -.0016(8) .0156(9) .0025(9) C37 .0579(15) .118(3) .121(3) .0206(16) .0404(17) .012(2) 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 Fe1 C11 . 2.0456(18) no Fe1 C12 . 2.040(2) no Fe1 C13 . 2.036(2) no Fe1 C14 . 2.036(2) no Fe1 C15 . 2.0384(19) no Fe1 C21 . 2.038(2) no Fe1 C22 . 2.033(2) no Fe1 C23 . 2.039(2) no Fe1 C24 . 2.035(2) no Fe1 C25 . 2.038(2) no O1 C34 . 1.373(2) yes O1 C37 . 1.418(3) yes N1 C1 . 1.321(2) yes N1 C4 . 1.381(2) yes N2 C1 . 1.382(2) yes N2 C2 . 1.457(2) yes N2 C3 . 1.384(2) yes C1 C31 . 1.471(2) yes C2 C11 . 1.502(3) yes C3 C4 . 1.394(3) no C3 C8 . 1.386(3) no C4 C5 . 1.400(3) no C5 C6 . 1.375(3) no C6 C7 . 1.385(4) no C7 C8 . 1.391(3) no C11 C12 . 1.423(3) no C11 C15 . 1.414(3) no C12 C13 . 1.418(3) no C13 C14 . 1.413(3) no C14 C15 . 1.416(3) no C21 C22 . 1.403(4) no C21 C25 . 1.399(4) no C22 C23 . 1.403(4) no C23 C24 . 1.407(4) no C24 C25 . 1.413(4) no C31 C32 . 1.385(3) no C31 C36 . 1.393(3) no C32 C33 . 1.384(3) no C33 C34 . 1.378(3) no C34 C35 . 1.384(3) no C35 C36 . 1.384(3) no C2 H2A . .9700 no C2 H2B . .9700 no C5 H5 . .9300 no C6 H6 . .9300 no C7 H7 . .9300 no C8 H8 . .9300 no C12 H12 . .9300 no C13 H13 . .9300 no C14 H14 . .9300 no C15 H15 . .9300 no C21 H21 . .9300 no C22 H22 . .9300 no C23 H23 . .9300 no C24 H24 . .9300 no C25 H25 . .9300 no C32 H32 . .9300 no C33 H33 . .9300 no C35 H35 . .9300 no C36 H36 . .9300 no C37 H37A . .9600 no C37 H37B . .9600 no C37 H37C . .9600 no