Crystal structure and Hirshfeld surface analysis of 2-oxo-13-epi-manoyl oxide isolated from Sideritis perfoliata

Acta Crystallogr E Crystallogr Commun. 2018 Apr 27;74(Pt 5):713-717. doi: 10.1107/S2056989018005807. eCollection 2018 May 1.

Abstract

The title compound, C20H32O2 (systematic name: 3-ethenyl-3,4a,7,7,10a-penta-methyl-dodeca-hydro-9H-benzo[f]chromen-9-one), was isolated from Sideritis perfoliata. In the crystal, mol-ecules pack in helical supra-molecular chains along the 21 screw axis running parallel to the a axis, bound by C-H⋯O hydrogen bonds. These chains are efficiently inter-locked in the other two unit-cell directions via van der Waals inter-actions. Hirshfeld surface analysis shows that van der Waals inter-actions constitute the major contribution to the inter-molecular inter-actions, with H⋯H contacts accounting for 86.0% of the surface.

Keywords: Hirshfeld surface analysis; crystal structure; cyclo­hexane rings; helical supra­molecular chains; tetra­hydro­pyran rings.

Grants and funding

This work was funded by The Scientific Research Project Fund of Cumhuriyet University grant F-567.