Acta Crystallographica Section C

Crystal Structure Communications

Volume 58, Part 3 (March 2002)

organic compounds

bk1627 scheme

Acta Cryst. (2002). C58, o195-o198    [ doi:10.1107/S0108270102000689 ]

Three ginkgolide hydrates from Ginkgo biloba L.: ginkgolide A monohydrate, ginkgolide C sesquihydrate and ginkgolide J dihydrate, all determined at 120 K

J.-P. Zhao, I. Muhammad, D. C. Dunbar, I. A. Khan, N. H. Fischer and F. R. Fronczek

Abstract: A low-temperature structure of ginkgolide A monohydrate, (1R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11aS)-3-(1,1-dimethylethyl)-hexa­hydro-4,7b-di­hydroxy-8-methyl-9H-1,7a-epoxymethano-1H,6aH-cyclo­penta­[c]­furo­[2,3-b]­furo­[3',2':3,4]­cyclopenta­[1,2-d]­furan-5,9,12(4H)-trione monohydrate, C20H24O9·H2O, obtained from Mo K[alpha] data, is a factor of three more precise than the previous room-temperature determination. A refinement of the ginkgolide A monohydrate structure with Cu K[alpha] data has allowed the assignment of the absolute configuration of the series of compounds. Ginkgolide C sesquihydrate, (1S,2R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11S,11aR)-3-(1,1-di­methyl­ethyl)-hexa­hydro-2,4,7b,11-tetrahydroxy-8-methyl-9H-1,7a-epoxy­methano-1H,6aH-cyclopenta­[c]­furo­[2,3-b]­furo­[3',2':3,4]­cyclo­penta­[1,2-d]­furan-5,9,12(4H)-trione sesquihydrate, C20H24O11·1.5H2O, has two independent diterpene mol­ecules, both of which exhibit intramolecular hydrogen bonding between OH groups. Ginkgolide J dihydrate, (1S,2R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11aS)-3-(1,1-di­methyl­ethyl)-hexa­hydro-2,4,7b-tri­hydroxy-8-methyl-9H-1,7a-epoxy­methano-1H,6aH-cyclo­penta­[c]­furo­[2,3-b]furo[3',2':3,4]­cyclo­penta­[1,2-d]­furan-5,9,12(4H)-trione dihydrate, C20H24O10·2H2O, has the same basic skeleton as the other ginkgolides, with its three OH groups having the same configurations as those in ginkgolide C. The conformations of the six five-membered rings are quite similar across ­ginkgolides A-C and J, except for the A and F rings of ginkgolide A.

Formula: C20H24O9·H2O, C20H24O11·1.5H2O and C20H24O10·2H2O

hkldisplay filedownload file

Structure factor file (CIF format) (203.1 kbytes)
[ doi:10.1107/S0108270102000689/bk1627Isup2.hkl ]
Contains datablock I

hkldisplay filedownload file

Structure factor file (CIF format) (289.9 kbytes)
[ doi:10.1107/S0108270102000689/bk1627IIIsup3.hkl ]
Contains datablock III

hkldisplay filedownload file

Structure factor file (CIF format) (132.3 kbytes)
[ doi:10.1107/S0108270102000689/bk1627IVsup4.hkl ]
Contains datablock IV


To open or display or play some files, you may need to set your browser up to use the appropriate software. See the full list of file types for an explanation of the different file types and their related mime types and, where available links to sites from where the appropriate software may be obtained.

The download button will force most browsers to prompt for a file name to store the data on your hard disk.

Where possible, images are represented by thumbnails.

 bibliographic record in  format

  Find reference:   Volume   Page   
  Search:     From   to      Advanced search

Copyright © International Union of Crystallography
IUCr Webmaster