#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012547.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_2012547
_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 A monohydrate'
_chemical_formula_moiety  'C20 H24 O9, H2 O'
_chemical_formula_sum  'C20 H26 O10'
_chemical_formula_iupac  'C20 H24 O9, H2 O'
_chemical_formula_weight  426.41
_chemical_melting_point  583
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  8.931(2)
_cell_length_b  12.338(2)
_cell_length_c  17.779(3)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  1959.2(6)
_cell_formula_units_Z  4
_cell_measurement_temperature  120
_exptl_crystal_density_diffrn  1.446
_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
  O2  .58578(10)  .27144(8)  .31825(5)  .02002(18) Uani d . 1 . . O
  H2O  .6126  .2190  .3452  .030 Uiso calc R 1 . . H
  O3  .24970(10)  .41947(7)  .27989(5)  .01649(16) Uani d . 1 . . O
  O4  .41751(11)  .23326(9)  .16733(5)  .02142(19) Uani d . 1 . . O
  O5  -.04901(11)  .11715(7)  .30436(5)  .01907(17) Uani d . 1 . . O
  H5O  -.1284  .1001  .3268  .029 Uiso calc R 1 . . H
  O6  -.07587(11)  .27195(9)  .42798(5)  .02288(19) Uani d . 1 . . O
  O7  .03324(10)  .39217(7)  .35017(5)  .01712(16) Uani d . 1 . . O
  O8  .50061(11)  .40372(9)  .17777(6)  .0236(2) Uani d . 1 . . O
  O9  .27240(10)  .30683(7)  .44388(5)  .01737(17) Uani d . 1 . . O
  O10  .28594(13)  .47482(8)  .48987(6)  .0244(2) Uani d . 1 . . O
  C1  .26641(14)  .16387(10)  .34871(7)  .0164(2) Uani d . 1 . . C
  H1A  .1682  .1515  .3731  .020 Uiso calc R 1 . . H
  H1B  .3152  .0928  .3404  .020 Uiso calc R 1 . . H
  C2  .36437(13)  .23569(10)  .39779(6)  .0156(2) Uani d . 1 . . C
  H2  .4345  .1917  .4293  .019 Uiso calc R 1 . . H
  C3  .44985(13)  .31425(10)  .34594(7)  .0160(2) Uani d . 1 . . C
  C4  .34378(13)  .32591(9)  .27695(6)  .01434(19) Uani d . 1 . . C
  C5  .24565(13)  .22449(9)  .27271(6)  .01373(18) Uani d . 1 . . C
  C6  .30576(14)  .16278(10)  .20308(7)  .0175(2) Uani d . 1 . . C
  H6  .3491  .0908  .2171  .021 Uiso calc R 1 . . H
  C7  .17387(15)  .15090(11)  .15005(7)  .0191(2) Uani d . 1 . . C
  H7A  .1120  .0872  .1636  .023 Uiso calc R 1 . . H
  H7B  .2080  .1432  .0973  .023 Uiso calc R 1 . . H
  C8  .08596(14)  .25680(10)  .16095(6)  .0156(2) Uani d . 1 . . C
  H8  .1523  .3154  .1409  .019 Uiso calc R 1 . . H
  C9  .08828(12)  .27060(9)  .24849(6)  .01333(18) Uani d . 1 . . C
  C10  -.04446(13)  .22997(10)  .29420(6)  .01510(19) Uani d . 1 . . C
  H10  -.1383  .2525  .2678  .018 Uiso calc R 1 . . H
  C11  -.03200(13)  .29514(10)  .36653(7)  .0163(2) Uani d . 1 . . C
  C12  .09822(13)  .38938(9)  .27503(6)  .01452(19) Uani d . 1 . . C
  H12  .0425  .4385  .2401  .017 Uiso calc R 1 . . H
  C13  .43176(13)  .32779(11)  .20352(7)  .0180(2) Uani d . 1 . . C
  C14  .46471(14)  .41759(10)  .39373(7)  .0179(2) Uani d . 1 . . C
  H14  .4540  .4838  .3617  .021 Uiso calc R 1 . . H
  C15  .33331(14)  .40665(10)  .44711(7)  .0182(2) Uani d . 1 . . C
  C16  .61053(16)  .42162(13)  .43927(9)  .0270(3) Uani d . 1 . . C
  H16A  .6073  .4831  .4741  .041 Uiso calc R 1 . . H
  H16B  .6956  .4301  .4050  .041 Uiso calc R 1 . . H
  H16C  .6218  .3542  .4678  .041 Uiso calc R 1 . . H
  C17  -.06227(15)  .26571(11)  .11536(7)  .0189(2) Uani d . 1 . . C
  C18  -.17177(17)  .17144(12)  .12845(8)  .0257(3) Uani d . 1 . . C
  H18A  -.2021  .1702  .1814  .039 Uiso calc R 1 . . H
  H18B  -.1226  .1029  .1157  .039 Uiso calc R 1 . . H
  H18C  -.2603  .1812  .0966  .039 Uiso calc R 1 . . H
  C19  -.01925(18)  .26524(14)  .03146(7)  .0282(3) Uani d . 1 . . C
  H19A  .0253  .1951  .0184  .042 Uiso calc R 1 . . H
  H19B  .0533  .3231  .0217  .042 Uiso calc R 1 . . H
  H19C  -.1090  .2771  .0008  .042 Uiso calc R 1 . . H
  C20  -.14044(16)  .37442(11)  .13101(8)  .0227(2) Uani d . 1 . . C
  H20A  -.2285  .3813  .0984  .034 Uiso calc R 1 . . H
  H20B  -.0709  .4340  .1208  .034 Uiso calc R 1 . . H
  H20C  -.1718  .3772  .1838  .034 Uiso calc R 1 . . H
  O1W  .32204(11)  .57887(8)  .12744(6)  .02132(18) Uani d . 1 . . O
  H1W  .372(3)  .5233(17)  .1416(12)  .032 Uiso d . 1 . . H
  H2W  .301(2)  .5633(17)  .0835(12)  .032 Uiso d . 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
  O2  .0155(4)  .0230(4)  .0216(4)  .0046(4)  .0025(3)  .0049(4)
  O3  .0133(4)  .0133(3)  .0229(4)  .0006(3)  .0003(3)  .0021(3)
  O4  .0182(4)  .0271(5)  .0190(4)  .0010(4)  .0060(3)  -.0002(4)
  O5  .0197(4)  .0137(3)  .0238(4)  -.0018(3)  .0045(3)  .0006(3)
  O6  .0242(4)  .0269(5)  .0176(4)  -.0017(4)  .0067(3)  .0003(4)
  O7  .0192(4)  .0154(4)  .0168(3)  -.0002(3)  .0039(3)  -.0022(3)
  O8  .0178(4)  .0277(5)  .0252(4)  .0012(4)  .0049(3)  .0101(4)
  O9  .0179(4)  .0184(4)  .0158(3)  .0007(3)  .0015(3)  .0011(3)
  O10  .0306(5)  .0213(4)  .0212(4)  .0029(4)  .0015(4)  -.0025(4)
  C1  .0179(5)  .0143(5)  .0169(4)  .0005(4)  .0000(4)  .0028(4)
  C2  .0160(5)  .0162(5)  .0147(4)  .0013(4)  .0010(4)  .0023(4)
  C3  .0138(4)  .0172(5)  .0171(5)  .0014(4)  .0002(4)  .0023(4)
  C4  .0140(4)  .0144(4)  .0146(4)  .0007(4)  .0016(4)  .0023(4)
  C5  .0139(4)  .0133(4)  .0140(4)  .0010(4)  .0021(4)  .0008(4)
  C6  .0177(5)  .0176(5)  .0173(5)  .0038(4)  .0034(4)  -.0005(4)
  C7  .0215(5)  .0192(5)  .0165(5)  .0027(5)  .0012(4)  -.0030(4)
  C8  .0168(5)  .0169(5)  .0131(4)  .0008(4)  .0004(4)  -.0002(4)
  C9  .0134(4)  .0130(4)  .0136(4)  .0011(4)  .0014(4)  .0005(4)
  C10  .0154(5)  .0143(4)  .0156(4)  -.0003(4)  .0019(4)  -.0006(4)
  C11  .0142(5)  .0166(5)  .0181(5)  .0008(4)  .0023(4)  -.0002(4)
  C12  .0143(4)  .0139(4)  .0154(4)  .0007(4)  .0011(4)  .0006(4)
  C13  .0133(4)  .0230(5)  .0179(5)  .0033(4)  .0020(4)  .0049(4)
  C14  .0178(5)  .0172(5)  .0188(5)  -.0017(4)  -.0001(4)  .0004(4)
  C15  .0187(5)  .0195(5)  .0165(5)  .0014(4)  -.0024(4)  .0013(4)
  C16  .0213(6)  .0284(7)  .0314(7)  -.0029(5)  -.0064(5)  -.0035(6)
  C17  .0205(5)  .0198(5)  .0164(5)  .0001(5)  -.0026(4)  .0007(4)
  C18  .0268(6)  .0251(6)  .0253(6)  -.0063(5)  -.0068(5)  -.0002(5)
  C19  .0327(7)  .0359(7)  .0159(5)  .0036(7)  -.0035(5)  .0004(5)
  C20  .0209(6)  .0221(6)  .0252(6)  .0034(5)  -.0056(5)  .0007(5)
  O1W  .0223(4)  .0192(4)  .0224(4)  .0011(4)  -.0016(4)  -.0011(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
  O2 C3 . 1.413(2) ?
  O2 H2O .  .8400 ?
  O3 C12 . 1.406(2) ?
  O3 C4 . 1.429(2) ?
  O4 C13 . 1.338(2) ?
  O4 C6 . 1.469(2) ?
  O5 C10 . 1.404(2) ?
  O5 H5O .  .8400 ?
  O6 C11 . 1.196(2) ?
  O7 C11 . 1.363(2) ?
  O7 C12 . 1.457(2) ?
  O8 C13 . 1.210(2) ?
  O9 C15 . 1.348(2) ?
  O9 C2 . 1.455(2) ?
  O10 C15 . 1.210(2) ?
  C1 C2 . 1.521(2) ?
  C1 C5 . 1.555(2) ?
  C1 H1A .  .9900 ?
  C1 H1B .  .9900 ?
  C2 C3 . 1.540(2) ?
  C2 H2 . 1.0000 ?
  C3 C14 . 1.538(2) ?
  C3 C4 . 1.556(2) ?
  C4 C13 . 1.524(2) ?
  C4 C5 . 1.530(2) ?
  C5 C6 . 1.549(2) ?
  C5 C9 . 1.576(2) ?
  C6 C7 . 1.516(2) ?
  C6 H6 . 1.0000 ?
  C7 C8 . 1.537(2) ?
  C7 H7A .  .9900 ?
  C7 H7B .  .9900 ?
  C8 C17 . 1.556(2) ?
  C8 C9 . 1.566(2) ?
  C8 H8 . 1.0000 ?
  C9 C10 . 1.522(2) ?
  C9 C12 . 1.542(2) ?
  C10 C11 . 1.521(2) ?
  C10 H10 . 1.0000 ?
  C12 H12 . 1.0000 ?
  C14 C15 . 1.515(2) ?
  C14 C16 . 1.534(2) ?
  C14 H14 . 1.0000 ?
  C16 H16A .  .9800 ?
  C16 H16B .  .9800 ?
  C16 H16C .  .9800 ?
  C17 C18 . 1.537(2) ?
  C17 C20 . 1.538(2) ?
  C17 C19 . 1.540(2) ?
  C18 H18A .  .9800 ?
  C18 H18B .  .9800 ?
  C18 H18C .  .9800 ?
  C19 H19A .  .9800 ?
  C19 H19B .  .9800 ?
  C19 H19C .  .9800 ?
  C20 H20A .  .9800 ?
  C20 H20B .  .9800 ?
  C20 H20C .  .9800 ?
  O1W H1W .  .86(2) ?
  O1W H2W .  .83(2) ?