(-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid

Juan Zinczuk, Edmundo A. Ruveda, Roger A. Lalancette, Hugh W. Thompson

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

The title diketo acid, (1R,3aS,6aS,7R,9S)-(-)-α,3a,7-trimethyl-5,8- dioxo-1,4-ethanoperhydropentalene-1-acetic acid (C15H 20O4), is shown to aggregate in the crystal structure as acid-to-ketone hydrogen-bonding catemers, whose chains follow 21 screw axes from each carboxyl to a ketone in a neighbouring molecule [O⋯O = 2.7472(13) and O⋯H - O = 172.7(17)°]. Two parallel counterdirectional screw-related single-strand hydrogen-bonding chains pass through the cell in the a direction. Six intermolecular C - H⋯O=C close contacts are found. Comparisons are drawn with a diastereomer having the opposite configuration at the methylated chiral centre adjacent to the carboxyl group.

Original languageEnglish (US)
Pages (from-to)o2120-o2122
JournalActa Crystallographica Section E: Structure Reports Online
Volume62
Issue number6
DOIs
StatePublished - Jun 2006

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • General Materials Science
  • Condensed Matter Physics

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