Crystal structure of 2-[(1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl]-N-(o-tolyl)acetamide

Abstract

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

Keywords

• crystal structure
• sclareolide
• sclareol
• hydrogen bonding
• C—H...π interactions