#------------------------------------------------------------------------------ #$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $ #$Revision: 14 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012548.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_2012548 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2002 _journal_volume 58 _journal_page_first o195 _journal_page_last o198 _publ_section_title ; Three ginkgolide hydrates from Ginkgo biloba L.: ginkgolide A monohydrate, ginkgolide C sesquihydrate and ginkgolide J dihydrate determined at 120 K ; loop_ _publ_author_name 'Jianping, Zhao ' 'Muhammad, Ilias ' 'Dunbar, D. Chuck ' 'Khan, Ikhlas A. ' 'Fischer, Nikolaus H. ' 'Fronczek, Frank R.' _chemical_name_common 'ginkgolide C sesquihydrate' _chemical_formula_moiety 'C20 H24 O11, 1.5H2 O' _chemical_formula_sum 'C20 H27 O12.50' _chemical_formula_iupac 'C20 H24 O11, 1.5H2 O' _chemical_formula_weight 467.42 _chemical_melting_point 558 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.4945(15) _cell_length_b 12.973(3) _cell_length_c 20.934(4) _cell_angle_alpha 90 _cell_angle_beta 91.00(2) _cell_angle_gamma 90 _cell_volume 2035.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120 _exptl_crystal_density_diffrn 1.526 _diffrn_ambient_temperature 120 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 O1A -.10445(15) .32753(11) .53160(6) .0182(2) Uani d . 1 . . O H1HA -.0863 .3537 .4956 .027 Uiso calc R 1 . . H O2A .18859(17) .13714(10) .69354(6) .0183(2) Uani d . 1 . . O H2HA .2881 .1164 .7075 .027 Uiso calc R 1 . . H O3A .47719(15) .21528(10) .57649(6) .0149(2) Uani d . 1 . . O O4A .15237(17) .04164(10) .53658(6) .0174(2) Uani d . 1 . . O O5A .11116(16) .38425(10) .43266(6) .0179(2) Uani d . 1 . . O H5HA .1080 .4312 .4051 .027 Uiso calc R 1 . . H O6A .33504(18) .52395(10) .50839(6) .0204(3) Uani d . 1 . . O O7A .48890(16) .38203(10) .53639(6) .0164(2) Uani d . 1 . . O O8A .37947(19) .00138(10) .60183(6) .0211(3) Uani d . 1 . . O O9A -.01476(17) .33786(10) .67684(6) .0193(2) Uani d . 1 . . O O10A .1254(2) .42475(12) .75432(7) .0286(3) Uani d . 1 . . O O11A .07426(19) .03387(11) .40540(6) .0219(3) Uani d . 1 . . O H11A .1357 -.0136 .4219 .033 Uiso calc R 1 . . H C1A .0605(2) .30858(13) .56292(8) .0136(3) Uani d . 1 . . C H1A .1285 .3746 .5674 .016 Uiso calc R 1 . . H C2A .0309(2) .26188(13) .62915(8) .0154(3) Uani d . 1 . . C H2A -.0606 .2058 .6270 .018 Uiso calc R 1 . . H C3A .2144(2) .21871(13) .64991(8) .0141(3) Uani d . 1 . . C C4A .2974(2) .18345(13) .58571(8) .0129(3) Uani d . 1 . . C C5A .1790(2) .22646(12) .53140(7) .0116(3) Uani d . 1 . . C C6A .0753(2) .13291(13) .50537(8) .0147(3) Uani d . 1 . . C H6A -.0559 .1390 .5124 .018 Uiso calc R 1 . . H C7A .1199(2) .12857(13) .43446(8) .0153(3) Uani d . 1 . . C H7A .0491 .1837 .4123 .018 Uiso calc R 1 . . H C8A .3188(2) .16099(13) .43317(7) .0134(3) Uani d . 1 . . C H8A .3870 .1058 .4563 .016 Uiso calc R 1 . . H C9A .3177(2) .25622(12) .47859(7) .0116(3) Uani d . 1 . . C C10A .2891(2) .36256(13) .44944(8) .0139(3) Uani d . 1 . . C H10A .3628 .3679 .4102 .017 Uiso calc R 1 . . H C11A .3674(2) .43433(14) .49988(8) .0151(3) Uani d . 1 . . C C12A .4887(2) .27250(13) .51990(7) .0131(3) Uani d . 1 . . C H12A .5978 .2536 .4957 .016 Uiso calc R 1 . . H C13A .2857(2) .06556(13) .57760(8) .0155(3) Uani d . 1 . . C C14A .2983(2) .31438(13) .68223(8) .0166(3) Uani d . 1 . . C H14A .3454 .3600 .6479 .020 Uiso calc R 1 . . H C15A .1343(3) .36608(14) .70958(9) .0204(3) Uani d . 1 . . C C16A .4481(3) .29640(16) .73098(9) .0252(4) Uani d . 1 . . C H16A .4875 .3627 .7487 .038 Uiso calc R 1 . . H H16B .5484 .2625 .7102 .038 Uiso calc R 1 . . H H16C .4047 .2524 .7655 .038 Uiso calc R 1 . . H C17A .4033(2) .17030(14) .36585(8) .0171(3) Uani d . 1 . . C C18A .2843(3) .23041(17) .31799(8) .0226(4) Uani d . 1 . . C H18A .3395 .2300 .2759 .034 Uiso calc R 1 . . H H18B .2712 .3017 .3327 .034 Uiso calc R 1 . . H H18C .1665 .1977 .3150 .034 Uiso calc R 1 . . H C19A .4275(3) .06132(16) .33818(9) .0270(4) Uani d . 1 . . C H19A .3101 .0305 .3296 .040 Uiso calc R 1 . . H H19B .4939 .0186 .3690 .040 Uiso calc R 1 . . H H19C .4938 .0656 .2983 .040 Uiso calc R 1 . . H C20A .5922(2) .21718(16) .37150(8) .0206(3) Uani d . 1 . . C H20A .6641 .1770 .4021 .031 Uiso calc R 1 . . H H20B .5839 .2886 .3864 .031 Uiso calc R 1 . . H H20C .6487 .2157 .3296 .031 Uiso calc R 1 . . H O1B .37642(16) .23496(10) .00320(6) .0178(2) Uani d . 1 . . O H1HB .3920 .2776 -.0264 .027 Uiso calc R 1 . . H O2B .61554(18) .04031(11) .16805(6) .0207(3) Uani d . 1 . . O H2HB .7072 .0121 .1837 .031 Uiso calc R 1 . . H O3B .94462(16) .10996(10) .06296(6) .0166(2) Uani d . 1 . . O O4B .62239(17) -.04148(9) .00060(6) .0170(2) Uani d . 1 . . O O5B .64412(17) .31774(10) -.08190(6) .0180(2) Uani d . 1 . . O H5HB .6562 .3666 -.1078 .027 Uiso calc R 1 . . H O6B .84724(19) .43445(11) .01391(7) .0235(3) Uani d . 1 . . O O7B .97973(16) .28380(10) .03741(6) .0182(2) Uani d . 1 . . O O8B .80101(19) -.09892(11) .07933(6) .0225(3) Uani d . 1 . . O O9B .45961(19) .25553(11) .15083(6) .0220(3) Uani d . 1 . . O O10B .6126(2) .33470(12) .22943(7) .0292(3) Uani d . 1 . . O O11B .57728(19) -.02014(11) -.13452(6) .0222(3) Uani d . 1 . . O H11B .6226 -.0747 -.1200 .033 Uiso calc R 1 . . H C1B .5365(2) .22233(13) .03826(8) .0133(3) Uani d . 1 . . C H1B .5987 .2901 .0433 .016 Uiso calc R 1 . . H C2B .4957(2) .17680(13) .10383(8) .0165(3) Uani d . 1 . . C H2B .3939 .1271 .1005 .020 Uiso calc R 1 . . H C3B .6665(2) .12164(13) .12719(8) .0159(3) Uani d . 1 . . C C4B .7584(2) .08721(13) .06466(8) .0139(3) Uani d . 1 . . C C5B .6639(2) .14185(12) .00859(7) .0118(3) Uani d . 1 . . C C6B .5623(2) .05577(12) -.02715(8) .0141(3) Uani d . 1 . . C H6B .4300 .0644 -.0248 .017 Uiso calc R 1 . . H C7B .6286(2) .06384(13) -.09516(8) .0146(3) Uani d . 1 . . C H7B .5730 .1270 -.1143 .018 Uiso calc R 1 . . H C8B .8299(2) .08659(13) -.08607(7) .0130(3) Uani d . 1 . . C H8B .8817 .0256 -.0632 .016 Uiso calc R 1 . . H C9B .82132(19) .17495(13) -.03565(7) .0119(3) Uani d . 1 . . C C10B .8125(2) .28688(13) -.05862(8) .0143(3) Uani d . 1 . . C H10B .9011 .2963 -.0933 .017 Uiso calc R 1 . . H C11B .8768(2) .34667(14) .00000(8) .0171(3) Uani d . 1 . . C C12B .9781(2) .17819(13) .01261(8) .0151(3) Uani d . 1 . . C H12B 1.0932 .1613 -.0084 .018 Uiso calc R 1 . . H C13B .7335(2) -.02818(14) .05136(8) .0162(3) Uani d . 1 . . C C14B .7643(2) .20958(14) .16239(8) .0187(3) Uani d . 1 . . C H14B .8269 .2514 .1295 .022 Uiso calc R 1 . . H C15B .6111(3) .27390(15) .18651(8) .0215(3) Uani d . 1 . . C C16B .9015(3) .18147(17) .21383(9) .0277(4) Uani d . 1 . . C H16D .9386 .2439 .2369 .042 Uiso calc R 1 . . H H16E 1.0055 .1499 .1940 .042 Uiso calc R 1 . . H H16F .8487 .1326 .2438 .042 Uiso calc R 1 . . H C17B .9404(2) .09985(14) -.14806(8) .0162(3) Uani d . 1 . . C C18B .8508(2) .17222(15) -.19726(8) .0196(3) Uani d . 1 . . C H18D .8451 .2421 -.1796 .029 Uiso calc R 1 . . H H18E .7298 .1476 -.2071 .029 Uiso calc R 1 . . H H18F .9206 .1730 -.2364 .029 Uiso calc R 1 . . H C19B .9631(3) -.00728(15) -.17895(9) .0232(4) Uani d . 1 . . C H19D .8470 -.0319 -.1950 .035 Uiso calc R 1 . . H H19E 1.0105 -.0558 -.1470 .035 Uiso calc R 1 . . H H19F 1.0461 -.0022 -.2145 .035 Uiso calc R 1 . . H C20B 1.1300(2) .13842(16) -.13184(9) .0205(3) Uani d . 1 . . C H20D 1.2022 .1371 -.1704 .031 Uiso calc R 1 . . H H20E 1.1846 .0936 -.0993 .031 Uiso calc R 1 . . H H20F 1.1240 .2091 -.1155 .031 Uiso calc R 1 . . H O1W .5019(2) .53009(13) .26802(8) .0334(3) Uani d . 1 . . O O2W .2407(13) -.0403(4) .1721(4) .0346(16) Uani d P .72(3) . . O O2W' .181(3) -.0269(7) .1514(11) .032(3) Uani d P .28(3) . . O O3W .2362(6) .5574(3) .36358(18) .0241(11) Uani d P .494(10) . . O O3W' .1490(7) .5294(3) .34387(18) .0307(14) Uani d P .506(10) . . 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 O1A .0114(5) .0213(6) .0219(6) .0031(4) -.0002(4) .0012(5) O2A .0233(6) .0159(6) .0158(5) .0005(5) .0049(5) .0039(5) O3A .0113(5) .0201(6) .0133(5) .0004(4) .0003(4) .0039(4) O4A .0214(6) .0121(5) .0186(5) -.0019(4) .0004(5) .0007(4) O5A .0142(5) .0172(6) .0219(6) .0033(4) -.0042(4) .0038(5) O6A .0229(6) .0132(6) .0252(6) -.0018(5) .0001(5) -.0016(5) O7A .0156(5) .0152(6) .0182(5) -.0021(4) -.0034(4) -.0006(4) O8A .0283(7) .0165(6) .0185(6) .0067(5) .0021(5) .0021(5) O9A .0240(6) .0169(6) .0171(6) .0029(5) .0070(5) -.0025(5) O10A .0425(8) .0221(7) .0213(6) .0017(6) .0048(6) -.0078(5) O11A .0278(7) .0159(6) .0220(6) -.0058(5) -.0020(5) -.0050(5) C1A .0111(6) .0134(7) .0164(7) .0004(5) .0008(5) -.0011(6) C2A .0161(7) .0127(7) .0175(7) .0004(6) .0056(6) -.0019(6) C3A .0178(7) .0117(6) .0130(7) -.0004(5) .0034(5) -.0001(5) C4A .0129(6) .0129(7) .0130(7) .0002(5) .0015(5) .0005(5) C5A .0105(6) .0121(6) .0122(6) .0000(5) .0008(5) .0003(5) C6A .0145(7) .0111(6) .0185(7) -.0012(5) .0007(5) .0006(6) C7A .0170(7) .0136(7) .0152(7) -.0022(6) -.0004(6) -.0028(6) C8A .0148(7) .0130(7) .0126(7) .0004(5) .0014(5) -.0003(5) C9A .0108(6) .0129(6) .0111(6) -.0006(5) .0000(5) -.0001(5) C10A .0131(7) .0133(7) .0154(7) .0004(5) -.0005(5) .0011(6) C11A .0146(7) .0152(7) .0155(7) -.0015(6) .0012(6) .0013(6) C12A .0115(6) .0147(7) .0132(6) -.0004(5) -.0002(5) .0008(6) C13A .0186(7) .0140(7) .0140(7) .0008(6) .0053(6) -.0005(6) C14A .0210(7) .0144(7) .0144(7) -.0025(6) .0011(6) -.0010(6) C15A .0298(9) .0144(7) .0170(7) -.0001(6) .0039(6) -.0003(6) C16A .0286(9) .0267(9) .0201(8) -.0026(7) -.0060(7) -.0021(7) C17A .0197(7) .0182(8) .0136(7) .0015(6) .0023(6) -.0008(6) C18A .0241(8) .0298(9) .0137(7) .0017(7) -.0020(6) .0009(7) C19A .0405(11) .0212(9) .0196(8) .0026(8) .0096(8) -.0040(7) C20A .0180(7) .0280(9) .0159(7) .0024(7) .0049(6) .0030(7) O1B .0120(5) .0169(6) .0243(6) .0014(4) -.0005(4) .0046(5) O2B .0267(6) .0183(6) .0173(5) .0028(5) .0045(5) .0066(5) O3B .0114(5) .0216(6) .0169(5) .0020(4) -.0013(4) .0017(5) O4B .0192(6) .0120(5) .0198(6) -.0018(4) -.0004(5) .0013(4) O5B .0166(5) .0156(6) .0218(6) .0004(5) -.0008(4) .0038(5) O6B .0246(6) .0163(6) .0298(7) -.0043(5) .0037(5) -.0054(5) O7B .0164(5) .0199(6) .0183(5) -.0045(5) -.0014(4) -.0033(5) O8B .0293(7) .0165(6) .0218(6) .0071(5) .0010(5) .0052(5) O9B .0280(7) .0205(6) .0176(6) .0070(5) .0067(5) -.0007(5) O10B .0503(9) .0204(7) .0170(6) .0047(6) .0058(6) -.0024(5) O11B .0271(7) .0181(6) .0214(6) -.0053(5) -.0026(5) -.0067(5) C1B .0105(6) .0133(7) .0161(7) .0006(5) .0022(5) .0018(6) C2B .0177(7) .0144(7) .0177(7) .0026(6) .0061(6) .0011(6) C3B .0199(7) .0141(7) .0137(7) .0016(6) .0028(6) .0028(6) C4B .0140(7) .0144(7) .0132(7) .0010(5) -.0001(5) .0009(5) C5B .0104(6) .0117(6) .0133(6) -.0007(5) .0006(5) .0018(5) C6B .0128(6) .0116(7) .0179(7) -.0011(5) -.0007(5) .0002(6) C7B .0149(7) .0141(7) .0147(7) -.0023(5) -.0018(5) -.0020(6) C8B .0132(7) .0126(7) .0132(6) .0002(5) .0003(5) .0001(5) C9B .0080(6) .0143(7) .0136(6) -.0012(5) .0019(5) .0003(5) C10B .0138(7) .0131(7) .0160(7) -.0012(5) .0022(5) -.0001(6) C11B .0141(7) .0182(7) .0192(7) -.0061(6) .0036(6) -.0014(6) C12B .0122(7) .0168(7) .0161(7) -.0007(6) .0001(5) -.0011(6) C13B .0168(7) .0158(7) .0162(7) .0025(6) .0042(6) .0002(6) C14B .0247(8) .0181(8) .0134(7) .0003(6) -.0006(6) -.0010(6) C15B .0321(9) .0173(8) .0152(7) .0027(7) .0045(7) .0029(6) C16B .0341(10) .0276(10) .0212(9) .0033(8) -.0090(8) -.0028(8) C17B .0159(7) .0183(7) .0145(7) .0012(6) .0028(5) .0003(6) C18B .0227(8) .0220(8) .0141(7) .0016(7) .0015(6) .0010(6) C19B .0284(9) .0202(8) .0212(8) .0040(7) .0059(7) -.0037(7) C20B .0157(7) .0259(9) .0199(8) .0001(6) .0039(6) .0006(7) O1W .0482(9) .0226(7) .0288(7) .0042(7) -.0135(7) -.0040(6) O2W .036(3) .0330(14) .035(2) .0011(15) -.001(2) -.0102(15) O2W' .035(6) .024(3) .037(6) .006(3) -.007(5) -.011(3) O3W .024(2) .0230(15) .0255(16) .0037(13) .0003(14) .0079(12) O3W' .036(3) .0327(18) .0235(17) .0104(18) .0065(17) .0123(14) 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 C1A . 1.411(2) ? O1A H1HA . .8400 ? O2A C3A . 1.413(2) ? O2A H2HA . .8400 ? O3A C12A . 1.402(2) ? O3A C4A . 1.426(2) ? O4A C13A . 1.342(2) ? O4A C6A . 1.466(2) ? O5A C10A . 1.402(2) ? O5A H5HA . .8400 ? O6A C11A . 1.202(2) ? O7A C11A . 1.360(2) ? O7A C12A . 1.462(2) ? O8A C13A . 1.197(2) ? O9A C15A . 1.351(2) ? O9A C2A . 1.448(2) ? O10A C15A . 1.210(2) ? O11A C7A . 1.410(2) ? O11A H11A . .8400 ? C1A C2A . 1.533(2) ? C1A C5A . 1.543(2) ? C1A H1A . 1.0000 ? C2A C3A . 1.540(2) ? C2A H2A . 1.0000 ? C3A C14A . 1.542(2) ? C3A C4A . 1.559(2) ? C4A C5A . 1.535(2) ? C4A C13A . 1.541(2) ? C5A C6A . 1.536(2) ? C5A C9A . 1.578(2) ? C6A C7A . 1.528(2) ? C6A H6A . 1.0000 ? C7A C8A . 1.550(2) ? C7A H7A . 1.0000 ? C8A C9A . 1.559(2) ? C8A C17A . 1.560(2) ? C8A H8A . 1.0000 ? C9A C10A . 1.522(2) ? C9A C12A . 1.548(2) ? C10A C11A . 1.518(2) ? C10A H10A . 1.0000 ? C12A H12A . 1.0000 ? C14A C15A . 1.521(3) ? C14A C16A . 1.522(2) ? C14A H14A . 1.0000 ? C16A H16A . .9800 ? C16A H16B . .9800 ? C16A H16C . .9800 ? C17A C19A . 1.540(3) ? C17A C18A . 1.542(2) ? C17A C20A . 1.544(2) ? C18A H18A . .9800 ? C18A H18B . .9800 ? C18A H18C . .9800 ? C19A H19A . .9800 ? C19A H19B . .9800 ? C19A H19C . .9800 ? C20A H20A . .9800 ? C20A H20B . .9800 ? C20A H20C . .9800 ? O1B C1B . 1.405(2) ? O1B H1HB . .8400 ? O2B C3B . 1.415(2) ? O2B H2HB . .8400 ? O3B C12B . 1.402(2) ? O3B C4B . 1.427(2) ? O4B C13B . 1.350(2) ? O4B C6B . 1.457(2) ? O5B C10B . 1.403(2) ? O5B H5HB . .8400 ? O6B C11B . 1.197(2) ? O7B C11B . 1.361(2) ? O7B C12B . 1.465(2) ? O8B C13B . 1.196(2) ? O9B C15B . 1.369(2) ? O9B C2B . 1.447(2) ? O10B C15B . 1.196(2) ? O11B C7B . 1.415(2) ? O11B H11B . .8400 ? C1B C2B . 1.530(2) ? C1B C5B . 1.552(2) ? C1B H1B . 1.0000 ? C2B C3B . 1.539(2) ? C2B H2B . 1.0000 ? C3B C14B . 1.537(2) ? C3B C4B . 1.555(2) ? C4B C13B . 1.533(2) ? C4B C5B . 1.534(2) ? C5B C6B . 1.538(2) ? C5B C9B . 1.572(2) ? C6B C7B . 1.520(2) ? C6B H6B . 1.0000 ? C7B C8B . 1.546(2) ? C7B H7B . 1.0000 ? C8B C9B . 1.560(2) ? C8B C17B . 1.561(2) ? C8B H8B . 1.0000 ? C9B C10B . 1.531(2) ? C9B C12B . 1.537(2) ? C10B C11B . 1.523(2) ? C10B H10B . 1.0000 ? C12B H12B . 1.0000 ? C14B C15B . 1.513(3) ? C14B C16B . 1.520(3) ? C14B H14B . 1.0000 ? C16B H16D . .9800 ? C16B H16E . .9800 ? C16B H16F . .9800 ? C17B C20B . 1.539(2) ? C17B C18B . 1.539(2) ? C17B C19B . 1.543(3) ? C18B H18D . .9800 ? C18B H18E . .9800 ? C18B H18F . .9800 ? C19B H19D . .9800 ? C19B H19E . .9800 ? C19B H19F . .9800 ? C20B H20D . .9800 ? C20B H20E . .9800 ? C20B H20F . .9800 ? O2W O2W' . .641(17) ? O3W O3W' . .849(4) ?