Crystal structure of 2-[(1R,2R,4aS,8aS)-2-hy-droxy-2,5,5,8a-tetra-methyl-deca-hydro-naphthalen-1-yl]-N-(o-tol-yl)acetamide

Acta Crystallogr E Crystallogr Commun. 2015 Sep 26;71(Pt 10):o788-9. doi: 10.1107/S2056989015017600. eCollection 2015 Oct 1.

Abstract

The title compound, C23H35NO2, is an amide derivative of the lactone (+)-sclareolide, and was synthesized from natural sclareol. In the mol-ecular structure, the two six-membered rings (A and B) of the labdane skeleton are trans-fused, and adopt chair conformations. There is an intra-molecular N-H⋯O hydrogen bond present forming an S(7) ring motif. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into helical chains propagating along the b-axis direction. The chains are linked via C-H⋯π inter-actions, forming a three-dimensional structure.

Keywords: C—H⋯π inter­actions; crystal structure; hydrogen bonding; sclareol; sclareolide.