6,6'-Dimethoxygossypolone

Acta Crystallogr C. 2010 Oct;66(Pt 10):o517-20. doi: 10.1107/S0108270110036541. Epub 2010 Sep 24.

Abstract

6,6'-Dimethoxygossypolone (systematic name: 7,7'-dihydroxy-5,5'-diisopropyl-6,6'-dimethoxy-3,3'-dimethyl-1,1',4,4'-tetraoxo-2,2'-binaphthalene-8,8'-dicarbaldehyde), C(32)H(30)O(10), is a dimeric molecule formed by oxidation of 6,6'-dimethoxygossypol. When crystallized from acetone, 6,6'-dimethoxygossypolone has monoclinic (P2(1)/c) symmetry, and there are two molecules within the asymmetric unit. Of the four independent quinoid rings, three display flattened boat conformations and one displays a flattened chair/half-chair conformation. The angles between the planes of the two bridged naphthoquinone structures are fairly acute, with values of about 68 and 69°. The structure has several intramolecular O-H...O and C-H...O hydrogen bonds and several weak intermolecular C-H...O hydrogen bonds, but no intermolecular O-H...O hydrogen bonds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • 7,7'-dihydroxy-5,5'-diisopropyl-6,6'-dimethoxy-3,3'-dimethyl-1,1',4,4'-tetraoxo-2,2'-binaphthalene-8,8'-dicarbaldehyde
  • Naphthalenes