Two (+)-α,4-dimethyl-2-oxocyclohexaneacetic acids: Hydrogen bonding in a terpenoid γ-keto acid and in a diastereomeric lactol

Mark Davison, Elizabeth M. Kikolski, David Mostafavi, Roger A. Lalancette, Hugh W. Thompson

Research output: Contribution to journalArticlepeer-review

2 Scopus citations


The (+)-(αS,1S,4R)-diastereomer of the title structure, C 10H16O3, aggregates in the solid as non-symmetric dimers with disorder in both carboxyl groups [O⋯O = 2.710 (5) and 2.638 (5) Å]. The two molecules constituting the asymmetric unit pair around a pseudo-twofold rotational axis and differ only slightly in their distances and angles, but one methyl group displays rotational disorder absent in the other molecule. Five intermolecular C-H⋯O close contacts exist, involving both ketone groups. The (+)-(αR,1R,4R)-diastereomer exists in the crystal in its closed-ring lactol form, (3R,3aR,6R,7aR)-2,3,3a,4,5,6,7,7a- octahydro-7a-hydroxy-3,6-dimethylbenzo[b]furan-2-one, C10H 16O3, and aggregates as hydrogen-bonded catemers that extend from the hydroxyl group of one molecule to the carbonyl group of a neighbor screw-related along b [O⋯O = 2.830 (3) Å and O-H⋯O = 169°]. One close intermolecular C-H⋯O contact exists involving the carbonyl group.

Original languageEnglish (US)
Pages (from-to)o249-o252
JournalActa Crystallographica Section C: Crystal Structure Communications
Issue number4
StatePublished - Apr 2005

All Science Journal Classification (ASJC) codes

  • Biochemistry, Genetics and Molecular Biology(all)


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