Crystal structure of (4b S,8a R)-1-isopropyl-4b,8,8-trimethyl-7-oxo-4b,7,8,8a,9,10-hexa-hydro-phenanthren-2-yl acetate

Acta Crystallogr E Crystallogr Commun. 2018 Apr 27;74(Pt 5):728-730. doi: 10.1107/S2056989018005510. eCollection 2018 May 1.

Abstract

The title compound, C22H28O3, was prepared by a direct acetyl-ation reaction of naturally occurring totarolenone. The mol-ecule contains three fused rings, which exhibit different conformations. The central ring has a half-chair conformation, while the non-aromatic oxo-substituted ring has a screw-boat conformation. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds and C-H⋯π inter-actions, forming sheets parallel to the bc plane. The carbonyl O atoms and the C atom at the 6-position of the cyclo-hexene ring are each disordered over two sets of sites with major occupancy components of 0.63 (7) and 0.793 (14), respectively.

Keywords: C—H⋯O hydrogen bond; C—H⋯π inter­actions; crystal structure; natural product; phenanthrene.

Grants and funding

This work was funded by Cadi Ayyad University grant .