#------------------------------------------------------------------------------ #$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: svn://www.crystallography.net/cod/cif/2/2011153.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_2011153 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first 884 _journal_page_last 887 _publ_section_title ; Red, orange, and yellow crystals of 4,5-bis(4-methoxyphenyl)-2-(3-nitrophenyl)-1H-imidazole ; _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _[local]_cod_cif_authors_sg_H-M 'P 21/a' loop_ _publ_author_name 'Inouye, Yoshinobu' 'Sakaino, Yoshiko' _chemical_formula_moiety 'C23 H19 N3 O4' _chemical_formula_sum 'C23 H19 N3 O4' _chemical_formula_weight 401.41 _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 21.004(5) _cell_length_b 13.061(3) _cell_length_c 14.441(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.266(11) _cell_angle_gamma 90.00 _cell_volume 3920.5(17) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_meas 1.34(2) _diffrn_ambient_temperature 293(2) 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_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1A .2439(2) .2953(3) .4164(3) .0667(13) Uani d . 1 . O O2A .1865(2) .4026(4) .3281(4) .0691(14) Uani d . 1 . O N3A .2329(2) .3820(4) .3852(4) .0498(13) Uani d . 1 . N C4A .2787(3) .4634(4) .4193(4) .0407(14) Uani d . 1 . C C5A .3331(3) .4396(4) .4793(4) .0399(13) Uani d . 1 . C H5A .339(3) .378(4) .501(4) .039(16) Uiso d . 1 . H C6A .3768(3) .5178(4) .5096(4) .0380(13) Uani d . 1 . C C7A .3622(3) .6165(4) .4780(4) .050(2) Uani d . 1 . C H7A .390(2) .672(4) .494(4) .034(14) Uiso d . 1 . H C8A .3066(3) .6384(5) .4173(5) .054(2) Uani d . 1 . C H8A .300(3) .705(5) .394(4) .054(17) Uiso d . 1 . H C9A .2645(3) .5622(5) .3864(4) .047(2) Uani d . 1 . C H9A .228(3) .570(5) .341(5) .07(2) Uiso d . 1 . H C10A .4358(3) .4938(4) .5736(4) .0386(13) Uani d . 1 . C N11A .4809(2) .5643(4) .6061(3) .0423(12) Uani d . 1 . N H11A .481(3) .627(4) .586(4) .044(17) Uiso d . 1 . H C12A .5279(3) .5180(4) .6688(4) .0378(13) Uani d . 1 . C C13A .5078(3) .4172(4) .6719(4) .0361(12) Uani d . 1 . C N14A .4509(2) .4030(3) .6110(3) .0420(11) Uani d . 1 . N C15A .5839(3) .5742(4) .7141(4) .0402(13) Uani d . 1 . C C16A .5891(3) .6784(5) .7016(6) .060(2) Uani d . 1 . C H16A .561(3) .712(5) .665(4) .054(19) Uiso d . 1 . H C17A .6408(3) .7348(5) .7417(6) .063(2) Uani d . 1 . C H17A .643(4) .809(7) .731(6) .12(3) Uiso d . 1 . H C18A .6894(3) .6887(5) .8011(5) .052(2) Uani d . 1 . C C19A .6867(3) .5846(5) .8149(5) .063(2) Uani d . 1 . C H19A .718(3) .547(5) .854(5) .06(2) Uiso d . 1 . H C20A .6349(3) .5284(5) .7716(5) .057(2) Uani d . 1 . C H20A .633(3) .461(5) .778(4) .053(18) Uiso d . 1 . H O21A .7385(2) .7504(3) .8403(4) .0753(15) Uani d . 1 . O C22A .7878(4) .7075(6) .9060(6) .088(3) Uani d . 1 . C H22A .8176 .7601 .9299 .133 Uiso calc R 1 . H H22B .8100 .6555 .8762 .133 Uiso calc R 1 . H H22C .7692 .6777 .9567 .133 Uiso calc R 1 . H C23A .5360(3) .3315(4) .7305(4) .0394(13) Uani d . 1 . C C24A .5419(3) .3356(5) .8280(4) .055(2) Uani d . 1 . C H24A .521(4) .395(6) .848(5) .09(3) Uiso d . 1 . H C25A .5675(3) .2557(5) .8829(5) .058(2) Uani d . 1 . C H25A .574(3) .260(4) .948(4) .047(16) Uiso d . 1 . H C26A .5888(3) .1688(4) .8414(4) .0472(15) Uani d . 1 . C C27A .5832(3) .1624(4) .7463(4) .0450(15) Uani d . 1 . C H27A .598(3) .102(5) .716(4) .051(17) Uiso d . 1 . H C28A .5571(3) .2433(4) .6917(5) .0444(14) Uani d . 1 . C H28A .554(2) .231(4) .626(4) .041(15) Uiso d . 1 . H O29A .6143(2) .0936(3) .9027(3) .0650(13) Uani d . 1 . O C30A .6351(4) .0017(5) .8646(5) .079(2) Uani d . 1 . C H30A .6503 -.0448 .9144 .118 Uiso calc R 1 . H H30B .6693 .0164 .8292 .118 Uiso calc R 1 . H H30C .5998 -.0290 .8244 .118 Uiso calc R 1 . H O1B .4617(2) -.2000(3) .5717(4) .078(2) Uani d . 1 . O O2B .5198(9) -.090(2) .6596(11) .067(6) Uani d PD .54 1 O O2C .5008(12) -.101(3) .6840(11) .074(8) Uani d PD .46 2 O N3B .4712(3) -.1135(4) .6036(4) .060(2) Uani d D 1 . N C4B .4317(3) -.0290(4) .5606(4) .0415(14) Uani d . 1 . C C5B .3832(3) -.0513(4) .4901(4) .0411(14) Uani d . 1 . C H5B .379(2) -.120(4) .475(3) .033(14) Uiso d . 1 . H C6B .3446(3) .0273(4) .4490(4) .0365(13) Uani d . 1 . C C7B .3581(3) .1261(4) .4803(4) .046(2) Uani d . 1 . C H7B .332(3) .181(4) .453(4) .039(15) Uiso d . 1 . H C8B .4078(3) .1476(5) .5514(5) .054(2) Uani d . 1 . C H8B .419(3) .216(5) .570(5) .08(2) Uiso d . 1 . H C9B .4447(3) .0684(5) .5926(5) .050(2) Uani d . 1 . C H9B .474(3) .078(5) .634(4) .051(19) Uiso d . 1 . H C10B .2906(3) .0012(4) .3784(4) .0397(13) Uani d . 1 . C N11B .2444(2) .0667(4) .3387(4) .0444(12) Uani d . 1 . N H11B .248(3) .130(5) .354(5) .07(2) Uiso d . 1 . H C12B .2014(3) .0120(4) .2770(4) .0453(15) Uani d D 1 . C C13B .2243(3) -.0864(4) .2812(4) .0426(14) Uani d . 1 . C N14B .2803(2) -.0929(3) .3442(3) .0457(12) Uani d . 1 . N C15B .1488(8) .0549(13) .2124(9) .050(5) Uani d PD .54 1 C C16B .1148(6) .1365(11) .2444(9) .054(4) Uani d PD .54 1 C H16B .1281 .1633 .3037 .065 Uiso calc PR .54 1 H C17B .0624(6) .1777(11) .1897(8) .056(3) Uani d PD .54 1 C H17B .0418 .2356 .2085 .068 Uiso calc PR .54 1 H C18B .0411(4) .1297(11) .1054(7) .043(3) Uani d PD .54 1 C C19B .0754(6) .0520(9) .0692(8) .055(3) Uani d PD .54 1 C H19B .0624 .0268 .0092 .066 Uiso calc PR .54 1 H C20B .1288(6) .0132(9) .1236(8) .052(3) Uani d PD .54 1 C H20B .1517 -.0404 .1017 .063 Uiso calc PR .54 1 H O21B -.0128(4) .1642(7) .0426(6) .068(2) Uani d PD .54 1 O C22B -.0498(9) .2458(13) .0708(14) .092(6) Uani d PD .54 1 C H22D -.0906 .2482 .0312 .138 Uiso calc PR .54 1 H H22E -.0273 .3092 .0659 .138 Uiso calc PR .54 1 H H22F -.0565 .2355 .1345 .138 Uiso calc PR .54 1 H C15C .1447(9) .0688(13) .2325(13) .033(4) Uiso d PD .46 2 C C16C .1273(7) .1677(11) .2586(12) .041(5) Uiso d PD .46 2 C H16C .1519 .1977 .3102 .049 Uiso calc PR .46 2 H C17C .0767(7) .2227(12) .2132(11) .054(5) Uiso d PD .46 2 C H17C .0684 .2887 .2325 .065 Uiso calc PR .46 2 H C18C .0378(7) .1780(11) .1378(10) .045(4) Uiso d PD .46 2 C C19C .0548(10) .0845(13) .1025(15) .063(7) Uiso d PD .46 2 C H19C .0327 .0584 .0471 .075 Uiso calc PR .46 2 H C20C .1054(6) .0319(11) .1520(9) .046(4) Uiso d PD .46 2 C H20C .1143 -.0330 .1307 .056 Uiso calc PR .46 2 H O21C -.0119(6) .2440(9) .0956(8) .072(4) Uiso d PD .46 2 O C22C -.0633(9) .1929(16) .0402(15) .081(7) Uiso d PD .46 2 C H22G -.0886 .2417 .0010 .122 Uiso calc PR .46 2 H H22H -.0898 .1600 .0802 .122 Uiso calc PR .46 2 H H22I -.0464 .1425 .0020 .122 Uiso calc PR .46 2 H C23B .1989(3) -.1808(4) .2324(4) .0418(14) Uani d . 1 . C C24B .1371(3) -.2149(5) .2380(5) .052(2) Uani d . 1 . C H24B .115(3) -.178(5) .275(5) .07(2) Uiso d . 1 . H C25B .1138(3) -.3057(5) .1960(5) .051(2) Uani d . 1 . C H25B .070(3) -.330(4) .200(4) .042(15) Uiso d . 1 . H C26B .1524(3) -.3622(5) .1465(4) .052(2) Uani d . 1 . C C27B .2136(3) -.3286(5) .1389(5) .063(2) Uani d . 1 . C H27B .243(3) -.365(5) .107(5) .08(2) Uiso d . 1 . H C28B .2371(4) -.2394(6) .1828(5) .062(2) Uani d . 1 . C H28B .277(4) -.217(6) .177(6) .12(3) Uiso d . 1 . H O29B .1346(2) -.4534(3) .1012(3) .0700(14) Uani d . 1 . O C30B .0743(4) -.4946(6) .1109(6) .093(3) Uani d . 1 . C H30D .0694 -.5601 .0805 .140 Uiso calc R 1 . H H30E .0410 -.4493 .0828 .140 Uiso calc R 1 . H H30F .0710 -.5027 .1762 .140 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 O1A .066(3) .044(3) .083(3) -.008(2) -.013(3) -.001(2) O2A .049(3) .067(3) .083(3) -.004(2) -.018(3) -.001(3) N3A .042(3) .050(3) .054(3) -.003(2) -.001(3) -.002(3) C4A .049(4) .030(3) .042(3) .001(3) .006(3) -.001(3) C5A .044(3) .033(3) .043(3) .002(3) .007(3) .003(3) C6A .042(3) .035(3) .037(3) .004(2) .002(3) .004(3) C7A .061(4) .032(3) .052(4) -.007(3) -.007(3) -.001(3) C8A .069(4) .038(3) .052(4) .008(3) -.007(3) .009(3) C9A .048(4) .045(4) .044(4) .007(3) -.005(3) -.005(3) C10A .050(4) .034(3) .031(3) -.001(3) .003(3) -.004(2) N11A .047(3) .027(2) .051(3) .001(2) .003(2) .004(2) C12A .036(3) .031(3) .046(3) .007(2) .007(3) .002(3) C13A .036(3) .037(3) .035(3) .001(2) .003(2) -.002(2) N14A .049(3) .036(2) .040(3) .001(2) .002(2) .004(2) C15A .038(3) .036(3) .046(3) .002(3) .004(3) .004(3) C16A .039(4) .048(4) .085(5) -.005(3) -.015(4) .014(4) C17A .046(4) .046(4) .094(6) -.010(3) -.003(4) .011(4) C18A .039(3) .049(4) .066(4) -.004(3) .001(3) -.005(3) C19A .051(4) .051(4) .080(5) .007(3) -.012(4) .009(4) C20A .052(4) .040(4) .072(5) -.001(3) -.016(4) .009(3) O21A .058(3) .058(3) .102(4) -.016(2) -.014(3) .002(3) C22A .065(5) .097(6) .091(6) -.002(5) -.030(5) .000(5) C23A .038(3) .039(3) .038(3) -.006(3) -.004(3) -.001(3) C24A .067(4) .058(4) .042(4) .020(4) .012(3) .000(3) C25A .071(5) .064(4) .036(4) .023(4) .000(3) .007(3) C26A .047(3) .045(3) .048(4) .004(3) -.001(3) .013(3) C27A .056(4) .032(3) .044(4) .003(3) -.003(3) .006(3) C28A .052(4) .043(3) .037(3) -.005(3) .004(3) -.001(3) O29A .086(3) .061(3) .045(3) .017(3) -.001(2) .017(2) C30A .104(6) .052(4) .075(5) .022(4) -.005(5) .024(4) O1B .092(4) .033(2) .094(4) .009(2) -.034(3) -.001(2) O2B .062(10) .048(8) .078(10) .004(7) -.034(9) .003(8) O2C .080(15) .068(11) .060(9) -.011(11) -.039(11) -.002(10) N3B .067(4) .038(3) .068(4) .003(3) -.015(3) .001(3) C4B .039(3) .035(3) .047(3) .001(2) -.003(3) .002(3) C5B .051(4) .026(3) .045(3) -.006(3) .001(3) -.006(3) C6B .034(3) .035(3) .038(3) .006(2) -.001(2) -.001(2) C7B .051(4) .029(3) .054(4) .003(3) -.008(3) -.002(3) C8B .064(4) .029(3) .064(4) -.004(3) -.009(3) -.005(3) C9B .051(4) .039(3) .054(4) -.012(3) -.014(3) -.006(3) C10B .036(3) .033(3) .048(3) -.004(3) .001(3) -.002(3) N11B .046(3) .032(3) .051(3) -.001(2) -.007(2) .003(2) C12B .042(3) .044(3) .044(3) -.014(3) -.011(3) .004(3) C13B .044(3) .038(3) .044(3) -.006(3) -.002(3) -.005(3) N14B .043(3) .040(3) .052(3) -.003(2) -.002(2) -.005(2) C15B .060(9) .056(9) .030(9) -.022(7) -.007(8) .001(6) C16B .052(8) .064(9) .041(7) -.014(8) -.016(6) .002(7) C17B .043(7) .063(9) .060(9) -.007(7) -.004(7) .003(8) C18B .014(5) .076(11) .038(7) .001(6) -.004(5) -.006(8) C19B .063(8) .056(8) .042(7) -.003(7) -.007(7) -.006(6) C20B .050(8) .053(7) .052(8) .003(6) .001(7) .002(6) O21B .049(5) .089(7) .065(6) .014(5) .000(4) .017(5) C22B .054(10) .129(18) .096(14) -.001(12) .021(10) .046(14) C23B .047(3) .039(3) .037(3) -.004(3) -.005(3) -.003(3) C24B .056(4) .048(4) .052(4) -.013(3) .010(3) -.010(3) C25B .051(4) .043(3) .057(4) -.012(3) .005(3) -.007(3) C26B .066(4) .045(4) .041(3) -.012(3) -.007(3) -.007(3) C27B .057(4) .055(4) .077(5) -.001(4) .011(4) -.017(4) C28B .054(4) .059(4) .073(5) -.008(4) .010(4) -.017(4) O29B .078(3) .056(3) .074(3) -.016(3) .005(3) -.025(2) C30B .094(6) .075(5) .107(7) -.036(5) .004(5) -.032(5) 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 O1A N3A . 1.229(6) ? O2A N3A . 1.213(6) ? N3A C4A . 1.469(7) ? C4A C5A . 1.366(8) ? C4A C9A . 1.392(8) ? C5A C6A . 1.400(8) ? C5A H5A . .87(5) ? C6A C7A . 1.388(8) ? C6A C10A . 1.471(7) ? C7A C8A . 1.384(8) ? C7A H7A . .94(5) ? C8A C9A . 1.363(9) ? C8A H8A . .94(6) ? C9A H9A . .95(7) ? C10A N14A . 1.322(7) ? C10A N11A . 1.355(7) ? N11A C12A . 1.380(7) ? N11A H11A . .87(6) ? C12A C13A . 1.385(7) ? C12A C15A . 1.460(7) ? C13A N14A . 1.390(7) ? C13A C23A . 1.475(7) ? C15A C16A . 1.380(8) ? C15A C20A . 1.392(8) ? C16A C17A . 1.371(9) ? C16A H16A . .86(6) ? C17A C18A . 1.375(9) ? C17A H17A . .99(9) ? C18A O21A . 1.366(7) ? C18A C19A . 1.376(9) ? C19A C20A . 1.385(9) ? C19A H19A . .94(6) ? C20A H20A . .89(6) ? O21A C22A . 1.415(8) ? C22A H22A . .96 ? C22A H22B . .96 ? C22A H22C . .96 ? C23A C28A . 1.381(8) ? C23A C24A . 1.397(8) ? C24A C25A . 1.373(9) ? C24A H24A . .95(7) ? C25A C26A . 1.388(9) ? C25A H25A . .94(6) ? C26A C27A . 1.364(8) ? C26A O29A . 1.377(7) ? C27A C28A . 1.383(8) ? C27A H27A . .98(6) ? C28A H28A . .96(5) ? O29A C30A . 1.416(8) ? C30A H30A . .96 ? C30A H30B . .96 ? C30A H30C . .96 ? O1B N3B . 1.226(6) ? O2B N3B . 1.246(9) ? O2C N3B . 1.247(10) ? N3B C4B . 1.465(7) ? C4B C5B . 1.364(8) ? C4B C9B . 1.368(8) ? C5B C6B . 1.387(7) ? C5B H5B . .93(5) ? C6B C7B . 1.382(7) ? C6B C10B . 1.453(7) ? C7B C8B . 1.385(8) ? C7B H7B . .96(5) ? C8B C9B . 1.374(9) ? C8B H8B . .96(7) ? C9B H9B . .81(6) ? C10B N14B . 1.330(7) ? C10B N11B . 1.357(7) ? N11B C12B . 1.374(7) ? N11B H11B . .85(6) ? C12B C13B . 1.370(8) ? C12B C15B . 1.452(10) ? C12B C15C . 1.470(10) ? C13B N14B . 1.382(7) ? C13B C23B . 1.479(7) ? C15B C20B . 1.400(9) ? C15B C16B . 1.399(9) ? C16B C17B . 1.370(10) ? C16B H16B . .93 ? C17B C18B . 1.386(11) ? C17B H17B . .93 ? C18B C19B . 1.390(11) ? C18B O21B . 1.418(11) ? C19B C20B . 1.371(10) ? C19B H19B . .93 ? C20B H20B . .93 ? O21B C22B . 1.413(13) ? C22B H22D . .96 ? C22B H22E . .96 ? C22B H22F . .96 ? C15C C16C . 1.409(9) ? C15C C20C . 1.411(9) ? C16C C17C . 1.370(10) ? C16C H16C . .93 ? C17C C18C . 1.392(11) ? C17C H17C . .93 ? C18C C19C . 1.390(11) ? C18C O21C . 1.422(12) ? C19C C20C . 1.377(11) ? C19C H19C . .93 ? C20C H20C . .93 ? O21C C22C . 1.414(13) ? C22C H22G . .96 ? C22C H22H . .96 ? C22C H22I . .96 ? C23B C28B . 1.381(8) ? C23B C24B . 1.386(8) ? C24B C25B . 1.388(8) ? C24B H24B . .91(6) ? C25B C26B . 1.372(9) ? C25B H25B . .99(5) ? C26B O29B . 1.384(7) ? C26B C27B . 1.378(9) ? C27B C28B . 1.383(9) ? C27B H27B . .95(7) ? C28B H28B . .91(8) ? O29B C30B . 1.404(8) ? C30B H30D . .96 ? C30B H30E . .96 ? C30B H30F . .96 ? _cod_database_code 2011153