#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012299.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_2012299 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 1343 _journal_page_last 1348 _publ_section_title ; Indole- and carbazole-substituted pyridinium iodide salts: a rare case of conformational isomerism in crystals ; loop_ _publ_author_name 'Wang, Zheng' 'Nesterov, Vladimir N.' 'Borbulevych, Oleg Ya.' 'Clark, Ronald D.' 'Antipin, Mikhail Yu.' 'Timofeeva, Tatiana V.' _chemical_formula_moiety 'C22 H21 N2 1+, I 1-' _chemical_formula_sum 'C22 H21 I N2' _chemical_formula_iupac 'C22 H21 N2 1+, I 1-' _chemical_formula_weight 440.31 _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.554(2) _cell_length_b 16.046(6) _cell_length_c 16.295(5) _cell_angle_alpha 82.27(3) _cell_angle_beta 87.36(2) _cell_angle_gamma 87.42(3) _cell_volume 1953.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _exptl_crystal_density_diffrn 1.497 _diffrn_ambient_temperature 110(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_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 I1 .36199(3) .918785(14) .184615(12) .03059(8) Uani d . 1 . . I N1 .4388(3) .71476(17) .39461(15) .0272(6) Uani d . 1 . . N N2 -.1844(3) .81231(17) .98128(15) .0263(6) Uani d . 1 . . N C1 .4207(4) .7963(2) .40724(19) .0291(7) Uani d . 1 . . C H1 .4585 .8392 .3650 .035 Uiso calc R 1 . . H C2 .3483(4) .8174(2) .48051(19) .0293(7) Uani d . 1 . . C H2 .3377 .8749 .4889 .035 Uiso calc R 1 . . H C3 .2888(4) .7545(2) .54400(18) .0279(7) Uani d . 1 . . C C4 .3133(5) .6706(2) .5288(2) .0357(8) Uani d . 1 . . C H4 .2794 .6262 .5703 .043 Uiso calc R 1 . . H C5 .3864(5) .6524(2) .4540(2) .0348(8) Uani d . 1 . . C H5 .4002 .5955 .4439 .042 Uiso calc R 1 . . H C6 .2083(4) .7799(2) .62021(19) .0307(7) Uani d . 1 . . C H6 .2063 .8381 .6256 .037 Uiso calc R 1 . . H C7 .1366(4) .7282(2) .68358(19) .0307(7) Uani d . 1 . . C H7 .1413 .6698 .6789 .037 Uiso calc R 1 . . H C8 .0518(4) .7542(2) .75929(18) .0281(7) Uani d . 1 . . C C9 .0243(4) .8404(2) .76873(19) .0308(7) Uani d . 1 . . C H9 .0606 .8815 .7244 .037 Uiso calc R 1 . . H C10 -.0531(4) .8675(2) .83980(18) .0267(7) Uani d . 1 . . C H10 -.0713 .9256 .8448 .032 Uiso calc R 1 . . H C11 -.1035(4) .8039(2) .90449(18) .0246(6) Uani d . 1 . . C C12 -.0778(4) .7172(2) .89690(18) .0250(7) Uani d . 1 . . C C13 -.0023(4) .6928(2) .82357(18) .0266(7) Uani d . 1 . . C H13 .0123 .6348 .8174 .032 Uiso calc R 1 . . H C14 -.1467(4) .6707(2) .97358(18) .0262(7) Uani d . 1 . . C C15 -.1610(5) .5847(2) 1.0031(2) .0329(8) Uani d . 1 . . C H15 -.1214 .5431 .9694 .040 Uiso calc R 1 . . H C16 -.2341(5) .5613(2) 1.0826(2) .0360(8) Uani d . 1 . . C H16 -.2427 .5034 1.1035 .043 Uiso calc R 1 . . H C17 -.2951(5) .6230(2) 1.1319(2) .0344(8) Uani d . 1 . . C H17 -.3433 .6058 1.1861 .041 Uiso calc R 1 . . H C18 -.2867(4) .7090(2) 1.10334(19) .0303(7) Uani d . 1 . . C H18 -.3309 .7504 1.1364 .036 Uiso calc R 1 . . H C19 -.2106(4) .7316(2) 1.02402(18) .0241(6) Uani d . 1 . . C C20 .5187(5) .6932(2) .31522(19) .0342(8) Uani d . 1 . . C H20A .4655 .6425 .3015 .051 Uiso calc R 1 . . H H20B .6468 .6828 .3204 .051 Uiso calc R 1 . . H H20C .4967 .7400 .2712 .051 Uiso calc R 1 . . H C21 -.2402(4) .8916(2) 1.01209(19) .0285(7) Uani d . 1 . . C H21A -.3584 .8853 1.0406 .034 Uiso calc R 1 . . H H21B -.2513 .9366 .9645 .034 Uiso calc R 1 . . H C22 -.1095(5) .9174(2) 1.0720(2) .0418(9) Uani d . 1 . . C H22A -.1547 .9690 1.0931 .063 Uiso calc R 1 . . H H22B .0057 .9274 1.0430 .063 Uiso calc R 1 . . H H22C -.0955 .8723 1.1185 .063 Uiso calc R 1 . . H I1' .36709(10) .47233(4) .27656(3) .06087(17) Uani d P .83 A 1 I I1'' .3110(6) .4804(2) .2392(2) .0829(11) Uani d P .17 B 2 I N1' .6971(3) .28531(18) -.02850(15) .0291(6) Uani d . 1 . . N N2' .0910(4) .14567(17) .58059(16) .0291(6) Uani d . 1 . . N C1' .6416(5) .3492(2) .0140(2) .0338(8) Uani d . 1 . . C H1' .6533 .4056 -.0113 .041 Uiso calc R 1 . . H C2' .5696(5) .3340(2) .0920(2) .0362(8) Uani d . 1 . . C H2' .5325 .3800 .1207 .043 Uiso calc R 1 . . H C3' .5489(4) .2505(2) .1316(2) .0340(8) Uani d . 1 . . C C4' .6063(5) .1852(2) .0863(2) .0344(8) Uani d . 1 . . C H4' .5942 .1281 .1097 .041 Uiso calc R 1 . . H C5' .6810(5) .2049(2) .0070(2) .0355(8) Uani d . 1 . . C H5' .7220 .1606 -.0231 .043 Uiso calc R 1 . . H C6' .4684(5) .2398(2) .2164(2) .0377(8) Uani d . 1 . . C H6' .4406 .2897 .2404 .045 Uiso calc R 1 . . H C7' .4307(5) .1679(2) .2626(2) .0360(8) Uani d . 1 . . C H7' .4593 .1171 .2400 .043 Uiso calc R 1 . . H C8' .3473(5) .1613(2) .3468(2) .0356(8) Uani d . 1 . . C C9' .3119(5) .0810(2) .3889(2) .0372(8) Uani d . 1 . . C H9' .3459 .0331 .3624 .045 Uiso calc R 1 . . H C10' .2293(4) .0684(2) .4673(2) .0324(7) Uani d . 1 . . C H10' .2080 .0135 .4947 .039 Uiso calc R 1 . . H C11' .1786(4) .1405(2) .50445(19) .0302(7) Uani d . 1 . . C C12' .2143(4) .2226(2) .46416(19) .0300(7) Uani d . 1 . . C C13' .2981(4) .2325(2) .3843(2) .0334(8) Uani d . 1 . . C H13' .3207 .2871 .3565 .040 Uiso calc R 1 . . H C14' .1476(4) .2809(2) .5197(2) .0309(7) Uani d . 1 . . C C15' .1426(5) .3687(2) .5159(2) .0386(8) Uani d . 1 . . C H15' .1915 .4028 .4688 .046 Uiso calc R 1 . . H C16' .0656(5) .4047(3) .5813(3) .0472(10) Uani d . 1 . . C H16' .0615 .4642 .5795 .057 Uiso calc R 1 . . H C17' -.0084(5) .3538(3) .6521(2) .0458(10) Uani d . 1 . . C H17' -.0620 .3805 .6962 .055 Uiso calc R 1 . . H C18' -.0045(5) .2661(3) .6588(2) .0380(8) Uani d . 1 . . C H18' -.0523 .2324 .7064 .046 Uiso calc R 1 . . H C19' .0741(4) .2308(2) .5915(2) .0304(7) Uani d . 1 . . C C20' .7766(5) .3055(3) -.11310(19) .0393(9) Uani d . 1 . . C H20D .7685 .2571 -.1434 .059 Uiso calc R 1 . . H H20E .9015 .3184 -.1097 .059 Uiso calc R 1 . . H H20F .7126 .3544 -.1422 .059 Uiso calc R 1 . . H C21' .0529(4) .0743(2) .64429(19) .0319(7) Uani d . 1 . . C H21C .0256 .0249 .6173 .038 Uiso calc R 1 . . H H21D -.0524 .0887 .6788 .038 Uiso calc R 1 . . H C22' .2115(5) .0519(2) .6996(2) .0411(9) Uani d . 1 . . C H22D .1777 .0097 .7462 .062 Uiso calc R 1 . . H H22E .2481 .1026 .7207 .062 Uiso calc R 1 . . H H22F .3103 .0291 .6671 .062 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 I1 .03226(12) .03371(13) .02567(12) .00207(9) .00106(8) -.00530(8) N1 .0271(14) .0343(16) .0207(13) .0004(12) -.0003(11) -.0058(11) N2 .0288(14) .0300(15) .0205(13) -.0016(12) .0030(10) -.0056(11) C1 .0302(17) .0340(19) .0232(16) -.0036(14) .0002(13) -.0044(13) C2 .0299(17) .0325(19) .0263(16) -.0006(14) .0006(13) -.0072(13) C3 .0235(16) .040(2) .0216(15) -.0011(14) -.0009(12) -.0071(13) C4 .042(2) .038(2) .0258(17) -.0054(16) .0029(14) .0007(14) C5 .043(2) .0309(19) .0303(18) -.0014(16) .0019(15) -.0033(14) C6 .0289(17) .038(2) .0263(17) -.0030(15) .0001(13) -.0068(14) C7 .0290(17) .040(2) .0232(16) .0021(15) -.0010(13) -.0054(14) C8 .0255(16) .0353(19) .0230(16) -.0012(14) -.0015(13) -.0020(13) C9 .0295(17) .038(2) .0241(16) -.0043(15) .0002(13) -.0023(14) C10 .0260(16) .0282(17) .0255(16) -.0015(13) -.0009(13) -.0025(13) C11 .0212(15) .0306(18) .0218(15) -.0019(13) .0018(12) -.0037(12) C12 .0220(15) .0300(18) .0229(15) .0025(13) -.0012(12) -.0037(12) C13 .0257(16) .0291(17) .0248(16) .0024(13) .0016(12) -.0046(13) C14 .0224(16) .0316(18) .0243(16) .0002(13) .0020(12) -.0036(13) C15 .039(2) .0305(19) .0286(17) .0038(15) .0040(14) -.0043(14) C16 .044(2) .0294(19) .0317(18) -.0006(16) .0081(15) .0016(14) C17 .039(2) .039(2) .0237(16) -.0053(16) .0086(14) -.0028(14) C18 .0244(16) .041(2) .0255(16) .0002(14) .0074(13) -.0079(14) C19 .0220(15) .0264(17) .0240(15) .0011(13) .0001(12) -.0045(12) C20 .039(2) .040(2) .0242(17) -.0001(16) .0033(14) -.0082(14) C21 .0315(17) .0267(17) .0271(16) .0019(14) .0030(13) -.0056(13) C22 .046(2) .042(2) .040(2) -.0030(18) -.0045(17) -.0151(16) I1' .0908(4) .0245(2) .0643(4) -.0067(2) .0415(3) -.0082(2) I1'' .121(3) .0291(12) .096(3) -.0115(15) .055(2) -.0165(17) N1' .0270(14) .0377(17) .0232(13) -.0004(12) .0005(11) -.0069(11) N2' .0265(14) .0340(16) .0262(14) -.0029(12) .0034(11) -.0027(11) C1' .0356(19) .034(2) .0330(18) -.0037(15) .0017(14) -.0089(14) C2' .0351(19) .047(2) .0285(18) -.0022(16) .0022(14) -.0125(15) C3' .0250(17) .051(2) .0269(17) -.0035(16) -.0036(13) -.0081(15) C4' .0340(19) .0331(19) .0343(19) -.0053(15) -.0087(15) .0054(14) C5' .0348(19) .037(2) .0362(19) -.0001(16) -.0071(15) -.0095(15) C6' .0332(19) .041(2) .041(2) -.0011(16) -.0046(15) -.0101(16) C7' .0311(18) .041(2) .0377(19) -.0021(16) -.0068(15) -.0087(16) C8' .0283(18) .050(2) .0292(18) -.0049(16) -.0025(14) -.0081(16) C9' .0302(18) .049(2) .0342(19) -.0033(16) -.0008(15) -.0126(16) C10' .0296(18) .039(2) .0293(17) -.0028(15) .0008(14) -.0070(14) C11' .0222(16) .043(2) .0244(16) -.0022(14) -.0026(13) -.0012(14) C12' .0220(16) .040(2) .0275(17) -.0015(14) -.0052(13) .0003(14) C13' .0258(17) .042(2) .0296(17) -.0060(15) -.0046(14) .0075(15) C14' .0247(17) .0327(19) .0336(18) -.0005(14) -.0032(13) .0022(14) C15' .0310(19) .039(2) .045(2) -.0006(16) .0007(16) .0000(16) C16' .041(2) .033(2) .068(3) .0010(17) -.010(2) -.0048(19) C17' .036(2) .052(3) .051(2) .0031(19) .0004(17) -.0155(19) C18' .0300(18) .049(2) .0357(19) .0058(16) .0001(15) -.0104(16) C19' .0227(16) .037(2) .0315(17) .0001(14) -.0028(13) -.0035(14) C20' .037(2) .059(3) .0225(17) -.0070(18) .0017(14) -.0039(16) C21' .0288(17) .041(2) .0263(17) -.0083(15) .0028(13) -.0043(14) C22' .052(2) .042(2) .0291(18) -.0136(18) -.0078(16) .0037(15) 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 N1 C1 . 1.351(4) no N1 C5 . 1.355(4) no N1 C20 . 1.479(4) no N2 C11 . 1.387(4) no N2 C19 . 1.404(4) no N2 C21 . 1.467(4) no C1 C2 . 1.368(4) no C1 H1 . .9500 no C2 C3 . 1.417(5) no C2 H2 . .9500 no C3 C4 . 1.405(5) no C3 C6 . 1.457(4) no C4 C5 . 1.376(5) no C4 H4 . .9500 no C5 H5 . .9500 no C6 C7 . 1.344(5) no C6 H6 . .9500 no C7 C8 . 1.466(4) no C7 H7 . .9500 no C8 C13 . 1.398(4) no C8 C9 . 1.417(5) no C9 C10 . 1.386(4) no C9 H9 . .9500 no C10 C11 . 1.417(4) no C10 H10 . .9500 no C11 C12 . 1.417(4) no C12 C13 . 1.396(4) no C12 C14 . 1.454(4) no C13 H13 . .9500 no C14 C15 . 1.406(5) no C14 C19 . 1.415(4) no C15 C16 . 1.394(5) no C15 H15 . .9500 no C16 C17 . 1.407(5) no C16 H16 . .9500 no C17 C18 . 1.399(5) no C17 H17 . .9500 no C18 C19 . 1.399(4) no C18 H18 . .9500 no C20 H20A . .9800 no C20 H20B . .9800 no C20 H20C . .9800 no C21 C22 . 1.528(4) no C21 H21A . .9900 no C21 H21B . .9900 no C22 H22A . .9800 no C22 H22B . .9800 no C22 H22C . .9800 no N1' C1' . 1.353(4) no N1' C5' . 1.349(4) no N1' C20' . 1.479(4) no N2' C11' . 1.389(4) no N2' C19' . 1.400(4) no N2' C21' . 1.468(4) no C1' C2' . 1.355(5) no C1' H1' . .9500 no C2' C3' . 1.419(5) no C2' H2' . .9500 no C3' C4' . 1.403(5) no C3' C6' . 1.475(5) no C4' C5' . 1.389(5) no C4' H4' . .9500 no C5' H5' . .9500 no C6' C7' . 1.325(5) no C6' H6' . .9500 no C7' C8' . 1.476(5) no C7' H7' . .9500 no C8' C13' . 1.395(5) no C8' C9' . 1.406(5) no C9' C10' . 1.390(5) no C9' H9' . .9500 no C10' C11' . 1.407(5) no C10' H10' . .9500 no C11' C12' . 1.421(5) no C12' C13' . 1.413(5) no C12' C14' . 1.447(5) no C13' H13' . .9500 no C14' C15' . 1.400(5) no C14' C19' . 1.432(5) no C15' C16' . 1.374(5) no C15' H15' . .9500 no C16' C17' . 1.428(6) no C16' H16' . .9500 no C17' C18' . 1.395(5) no C17' H17' . .9500 no C18' C19' . 1.399(5) no C18' H18' . .9500 no C20' H20D . .9800 no C20' H20E . .9800 no C20' H20F . .9800 no C21' C22' . 1.533(5) no C21' H21C . .9900 no C21' H21D . .9900 no C22' H22D . .9800 no C22' H22E . .9800 no C22' H22F . .9800 no _cod_database_code 2012299