#------------------------------------------------------------------------------ #$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012298.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_2012298 _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 'C16 H15 N2 1+, I 1-, 0.5H2 O' _chemical_formula_sum 'C16 H16 I N2 O0.50' _chemical_formula_iupac 'C16 H15 N2 1+, I 1-, 0.5H2 O' _chemical_formula_weight 370.20 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.3795(19) _cell_length_b 13.8324(17) _cell_length_c 14.1690(17) _cell_angle_alpha 90.00 _cell_angle_beta 100.816(2) _cell_angle_gamma 90.00 _cell_volume 2960.7(6) _cell_formula_units_Z 8 _cell_measurement_temperature 110(2) _exptl_crystal_density_diffrn 1.661 _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 .56906(2) .20173(2) .57329(2) .04168(12) Uani d . 1 . . I N1 -.1758(12) .4242(15) .6083(17) .025(4) Uani d PU .50 A 1 N N2 .3688(9) .3180(13) .5375(15) .023(3) Uani d PDU .50 A 1 N H2N .4102 .2818 .5202 .027 Uiso calc PR .50 A 1 H C1 -.1191(12) .4889(13) .6588(14) .030(6) Uani d P .50 A 1 C H1 -.1427 .5351 .6968 .036 Uiso calc PR .50 A 1 H C2 -.0314(12) .4921(15) .6587(17) .026(3) Uani d P .50 A 1 C H2 .0057 .5365 .6987 .031 Uiso calc PR .50 A 1 H C3 .0035(9) .4294(8) .5992(9) .023(2) Uani d P .50 A 1 C C4 -.0567(10) .3644(9) .5464(10) .023(2) Uani d P .50 A 1 C H4 -.0357 .3177 .5069 .028 Uiso calc PR .50 A 1 H C5 -.1435(11) .3666(16) .5502(14) .032(4) Uani d P .50 A 1 C H5 -.1828 .3248 .5093 .038 Uiso calc PR .50 A 1 H C6 .0942(7) .4311(6) .5987(6) .0229(18) Uani d P .50 A 1 C H6 .1265 .4836 .6313 .027 Uiso calc PR .50 A 1 H C7 .1410(5) .3669(6) .5571(5) .0192(13) Uani d P .50 A 1 C H7 .1092 .3153 .5224 .023 Uiso calc PR .50 A 1 H C8 .2369(9) .3697(10) .5608(9) .019(2) Uani d PU .50 A 1 C C9 .2821(9) .2952(13) .5266(12) .028(3) Uani d PDU .50 A 1 C H9 .2562 .2367 .4994 .033 Uiso calc PR .50 A 1 H C10 .3812(11) .4058(15) .580(2) .022(4) Uani d PDU .50 A 1 C C11 .4581(14) .4607(12) .589(2) .036(8) Uani d PD .50 A 1 C H11 .5086 .4380 .5665 .043 Uiso calc PR .50 A 1 H C12 .4581(13) .5500(17) .634(2) .032(5) Uani d PDU .50 A 1 C H12 .5115 .5855 .6526 .039 Uiso calc PR .50 A 1 H C13 .3768(19) .587(3) .652(3) .065(11) Uani d PD .50 A 1 C H13 .3790 .6475 .6847 .078 Uiso calc PR .50 A 1 H C14 .294(2) .5438(14) .627(2) .036(6) Uani d PD .50 A 1 C H14 .2393 .5736 .6310 .043 Uiso calc PR .50 A 1 H C15 .3040(13) .4501(13) .5951(19) .032(7) Uani d PD .50 A 1 C C16 -.2697(12) .4208(11) .6182(12) .038(3) Uani d P .50 A 1 C H16A -.2735 .4029 .6842 .058 Uiso calc PR .50 A 1 H H16B -.3012 .3728 .5736 .058 Uiso calc PR .50 A 1 H H16C -.2967 .4846 .6034 .058 Uiso calc PR .50 A 1 H N1' -.1941(12) .4328(18) .6149(17) .031(4) Uani d PD .50 B 2 N N2' .3454(11) .3293(18) .537(2) .048(5) Uani d PD .50 B 2 N H2'N .3793 .2867 .5149 .057 Uiso calc PR .50 B 2 H C1' -.1761(12) .3592(15) .5520(13) .036(4) Uani d P .50 B 2 C H1' -.2230 .3187 .5215 .043 Uiso calc PR .50 B 2 H C2' -.0944(13) .3452(13) .5343(10) .040(4) Uani d P .50 B 2 C H2' -.0857 .2983 .4881 .048 Uiso calc PR .50 B 2 H C3' -.0224(8) .3972(12) .5817(10) .033(3) Uani d PD .50 B 2 C C4' -.0421(12) .4680(16) .6442(18) .034(4) Uani d PD .50 B 2 C H4' .0048 .5083 .6749 .040 Uiso calc PR .50 B 2 H C5' -.1258(11) .4837(16) .6649(19) .047(8) Uani d PD .50 B 2 C H5' -.1347 .5288 .7127 .056 Uiso calc PR .50 B 2 H C6' .0615(5) .3685(7) .5579(7) .049(2) Uani d PD .50 B 2 C H6' .0637 .3146 .5168 .058 Uiso calc PR .50 B 2 H C7' .1359(7) .4168(9) .5931(8) .042(3) Uani d PD .50 B 2 C H7' .1303 .4712 .6325 .051 Uiso calc PR .50 B 2 H C8' .2229(12) .3950(12) .5776(12) .036(4) Uani d P .50 B 2 C C9' .2591(11) .3159(12) .5405(11) .035(4) Uani d PD .50 B 2 C H9' .2272 .2585 .5200 .042 Uiso calc PR .50 B 2 H C10' .3735(15) .4218(16) .573(2) .032(5) Uani d P .50 B 2 C C11' .4570(14) .4679(16) .596(2) .037(7) Uani d PD .50 B 2 C H11' .5103 .4353 .5911 .045 Uiso calc PR .50 B 2 H C12' .4569(17) .5634(18) .627(3) .056(9) Uani d PD .50 B 2 C H12' .5076 .6032 .6290 .067 Uiso calc PR .50 B 2 H C13' .3811(14) .599(2) .655(2) .030(5) Uani d PD .50 B 2 C H13' .3818 .6623 .6814 .036 Uiso calc PR .50 B 2 H C14' .3077(17) .5469(17) .644(2) .029(5) Uani d P .50 B 2 C H14' .2597 .5728 .6695 .035 Uiso calc PR .50 B 2 H C15' .2944(18) .4538(17) .597(2) .034(7) Uani d P .50 B 2 C C16' -.2817(10) .4519(12) .6332(14) .043(4) Uani d P .50 B 2 C H16D -.2823 .5151 .6643 .065 Uiso calc PR .50 B 2 H H16E -.2979 .4016 .6754 .065 Uiso calc PR .50 B 2 H H16F -.3242 .4520 .5723 .065 Uiso calc PR .50 B 2 H I1B .209554(18) .03931(2) .59623(2) .03807(12) Uani d . 1 . . I N1B .4679(3) .3739(3) .8183(2) .0424(9) Uani d . 1 . . N N2B -.0902(3) .3226(4) .8488(3) .0543(11) Uani d . 1 . . N H2BN -.1347 .3448 .8735 .065 Uiso calc R 1 . . H C1B .4370(3) .2937(3) .7709(3) .0378(9) Uani d . 1 . . C H1B .4756 .2574 .7395 .045 Uiso calc R 1 . . H C2B .3529(3) .2620(3) .7658(3) .0383(9) Uani d . 1 . . C H2B .3351 .2032 .7332 .046 Uiso calc R 1 . . H C3B .2919(3) .3137(3) .8072(3) .0366(9) Uani d . 1 . . C C4B .3250(3) .3955(4) .8586(3) .0463(11) Uani d . 1 . . C H4B .2873 .4317 .8914 .056 Uiso calc R 1 . . H C5B .4117(4) .4254(4) .8633(3) .0547(14) Uani d . 1 . . C H5B .4323 .4823 .8982 .066 Uiso calc R 1 . . H C6B .2002(3) .2812(3) .7935(3) .0369(9) Uani d . 1 . . C H6B .1831 .2270 .7531 .044 Uiso calc R 1 . . H C7B .1392(3) .3239(4) .8349(3) .0397(10) Uani d . 1 . . C H7B .1595 .3750 .8782 .048 Uiso calc R 1 . . H C8B .0475(3) .3020(3) .8220(3) .0392(10) Uani d . 1 . . C C9B -.0060(4) .3508(4) .8736(3) .0480(12) Uani d . 1 . . C H9B .0143 .3984 .9209 .058 Uiso calc R 1 . . H C10B -.0960(3) .2524(3) .7774(3) .0401(10) Uani d . 1 . . C C11B -.1698(3) .2054(4) .7280(4) .0520(14) Uani d . 1 . . C H11B -.2269 .2174 .7417 .062 Uiso calc R 1 . . H C12B -.1577(3) .1404(4) .6580(4) .0535(14) Uani d . 1 . . C H12B -.2067 .1053 .6238 .064 Uiso calc R 1 . . H C13B -.0722(3) .1259(3) .6367(4) .0463(11) Uani d . 1 . . C H13B -.0653 .0818 .5873 .056 Uiso calc R 1 . . H C14B .0001(3) .1730(3) .6850(3) .0367(9) Uani d . 1 . . C H14B .0567 .1627 .6690 .044 Uiso calc R 1 . . H C15B -.0103(2) .2375(3) .7592(3) .0312(8) Uani d . 1 . . C C16B .5593(4) .4070(6) .8234(4) .079(2) Uani d . 1 . . C H16G .5811 .3846 .7665 .119 Uiso calc R 1 . . H H16H .5968 .3807 .8813 .119 Uiso calc R 1 . . H H16I .5611 .4778 .8259 .119 Uiso calc R 1 . . H O1 .2659(5) .8039(5) .5795(6) .126(2) Uani d . 1 . . O 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 .0541(2) .04020(19) .03137(18) .00772(12) .00956(13) -.00243(11) N1 .016(6) .025(4) .034(6) .011(5) .006(5) .010(4) N2 .025(5) .022(6) .019(4) .012(5) -.001(4) -.003(4) C1 .060(14) .017(6) .011(6) -.009(6) .006(6) -.008(4) C2 .026(6) .030(8) .020(7) -.007(5) -.002(5) -.008(5) C3 .031(6) .017(5) .020(5) -.008(4) .000(4) .004(4) C4 .018(8) .027(6) .023(6) .003(5) -.002(5) -.003(4) C5 .031(11) .031(7) .030(6) -.020(7) -.005(7) .005(4) C6 .032(5) .019(4) .017(4) .000(4) .001(4) -.001(3) C7 .027(4) .019(3) .009(3) .002(3) -.003(3) .000(3) C8 .019(5) .021(6) .017(5) .011(4) .006(3) -.005(4) C9 .028(6) .036(8) .021(5) .008(5) .007(4) -.010(4) C10 .025(5) .018(7) .021(6) .008(4) .001(4) .003(5) C11 .053(15) .017(7) .041(15) .009(7) .018(9) .012(7) C12 .032(6) .027(8) .040(8) -.009(5) .011(6) .008(6) C13 .10(2) .042(16) .049(15) .024(14) .009(16) -.006(11) C14 .039(9) .039(9) .025(13) .001(6) -.007(7) .010(6) C15 .036(13) .034(10) .024(9) -.013(9) .003(7) .001(7) C16 .041(8) .045(8) .033(6) .018(6) .015(5) .007(5) N1' .026(9) .045(7) .024(5) .010(6) .010(6) -.001(4) N2' .066(13) .034(6) .042(6) .035(9) .006(9) .000(4) C1' .055(12) .028(6) .021(5) -.021(8) -.003(8) .004(4) C2' .049(12) .045(9) .021(5) .018(8) -.003(7) .002(5) C3' .032(9) .039(10) .025(7) .004(6) .001(6) .011(6) C4' .025(6) .045(12) .027(9) -.016(6) -.004(6) -.006(6) C5' .029(9) .065(14) .052(12) .020(8) .022(8) .021(9) C6' .069(7) .038(5) .038(5) .012(5) .008(5) .005(4) C7' .054(8) .042(7) .030(5) .004(6) .008(6) .014(5) C8' .041(8) .036(7) .031(7) .023(6) .008(5) -.006(5) C9' .052(10) .032(9) .019(7) .007(7) .004(6) -.002(6) C10' .060(11) .018(7) .022(6) .019(6) .013(6) .013(5) C11' .029(11) .064(15) .021(9) .000(8) .010(7) -.002(8) C12' .081(14) .025(8) .056(13) .001(7) -.001(9) .013(8) C13' .048(11) .015(6) .028(9) -.006(6) .008(8) -.001(5) C14' .030(9) .047(9) .010(8) .015(6) .002(8) -.003(4) C15' .030(8) .052(12) .024(9) .032(8) .016(6) .024(7) C16' .016(5) .055(10) .059(10) .007(6) .006(5) .003(7) I1B .04182(18) .04034(19) .03536(18) -.00218(11) .01576(12) .00060(11) N1B .045(2) .058(2) .0235(17) -.0162(18) .0026(15) .0096(17) N2B .058(3) .077(3) .032(2) .024(2) .0199(18) .008(2) C1B .035(2) .051(3) .028(2) -.0006(18) .0069(16) .0063(17) C2B .041(2) .041(2) .033(2) -.0012(18) .0058(17) .0076(18) C3B .036(2) .044(2) .030(2) .0075(17) .0073(16) .0155(17) C4B .053(3) .050(3) .038(2) .014(2) .013(2) .010(2) C5B .082(4) .041(3) .035(2) -.013(3) -.003(2) .006(2) C6B .053(3) .031(2) .026(2) .0002(17) .0058(18) .0049(16) C7B .039(2) .047(2) .032(2) -.0002(19) .0047(18) .0076(19) C8B .043(2) .042(2) .029(2) .0072(18) -.0002(18) .0109(17) C9B .062(3) .057(3) .025(2) .017(2) .008(2) -.0013(19) C10B .037(2) .047(3) .038(2) .0037(19) .0128(18) .018(2) C11B .028(2) .069(3) .061(3) .004(2) .015(2) .033(3) C12B .051(3) .042(3) .061(3) -.016(2) -.007(2) .023(2) C13B .054(3) .034(2) .048(3) .0042(19) .001(2) .005(2) C14B .040(2) .033(2) .038(2) .0101(17) .0086(17) .0066(17) C15B .0262(18) .038(2) .0292(19) .0059(15) .0040(15) .0128(16) C16B .052(3) .136(6) .044(3) -.051(4) -.004(2) .027(3) O1 .129(5) .127(6) .134(6) -.022(4) .052(5) -.012(4) 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 . 1.356(15) no N1 C5 . 1.31(3) no N1 C16 . 1.48(2) no N2 C9 . 1.350(2) no N2 C10 . 1.35(3) no N2 H2N . .8800 no C1 C2 . 1.350(18) no C1 H1 . .9500 no C2 C3 . 1.39(2) no C2 H2 . .9500 no C3 C6 . 1.396(17) no C3 C4 . 1.402(13) no C4 C5 . 1.348(16) no C4 H4 . .9500 no C5 H5 . .9500 no C6 C7 . 1.347(10) no C6 H6 . .9500 no C7 C8 . 1.466(15) no C7 H7 . .9500 no C8 C9 . 1.382(13) no C8 C15 . 1.53(2) no C9 H9 . .9500 no C10 C11 . 1.390(2) no C10 C15 . 1.390(2) no C11 C12 . 1.390(2) no C11 H11 . .9500 no C12 C13 . 1.42(2) no C12 H12 . .9500 no C13 C14 . 1.390(2) no C13 H13 . .9500 no C14 C15 . 1.390(2) no C14 H14 . .9500 no C16 H16A . .9800 no C16 H16B . .9800 no C16 H16C . .9800 no N1' C1' . 1.41(3) no N1' C5' . 1.350(2) no N1' C16' . 1.44(2) no N2' C9' . 1.350(2) no N2' C10' . 1.42(3) no N2' H2'N . .8800 no C1' C2' . 1.34(2) no C1' H1' . .9500 no C2' C3' . 1.38(2) no C2' H2' . .9500 no C3' C4' . 1.39(2) no C3' C6' . 1.449(2) no C4' C5' . 1.390(2) no C4' H4' . .9500 no C5' H5' . .9500 no C6' C7' . 1.339(2) no C6' H6' . .9500 no C7' C8' . 1.43(2) no C7' H7' . .9500 no C8' C15' . 1.36(3) no C8' C9' . 1.376(15) no C9' H9' . .9500 no C10' C15' . 1.39(2) no C10' C11' . 1.417(18) no C11' C12' . 1.390(2) no C11' H11' . .9500 no C12' C13' . 1.390(2) no C12' H12' . .9500 no C13' C14' . 1.33(2) no C13' H13' . .9500 no C14' C15' . 1.45(2) no C14' H14' . .9500 no C16' H16D . .9800 no C16' H16E . .9800 no C16' H16F . .9800 no N1B C1B . 1.337(6) no N1B C5B . 1.367(7) no N1B C16B . 1.467(6) no N2B C9B . 1.334(7) no N2B C10B . 1.394(7) no N2B H2BN . .8800 no C1B C2B . 1.355(6) no C1B H1B . .9500 no C2B C3B . 1.394(6) no C2B H2B . .9500 no C3B C4B . 1.389(7) no C3B C6B . 1.457(6) no C4B C5B . 1.386(8) no C4B H4B . .9500 no C5B H5B . .9500 no C6B C7B . 1.335(7) no C6B H6B . .9500 no C7B C8B . 1.420(6) no C7B H7B . .9500 no C8B C9B . 1.375(7) no C8B C15B . 1.443(6) no C9B H9B . .9500 no C10B C11B . 1.379(7) no C10B C15B . 1.405(6) no C11B C12B . 1.377(8) no C11B H11B . .9500 no C12B C13B . 1.416(8) no C12B H12B . .9500 no C13B C14B . 1.358(7) no C13B H13B . .9500 no C14B C15B . 1.410(6) no C14B H14B . .9500 no C16B H16G . .9800 no C16B H16H . .9800 no C16B H16I . .9800 no