Crystal structure of obscurine: a natural product isolated from the stem bark of B. obscura

Abstract

The title compound, C24H31NO3 {systematic name: (E)-3-[(1R*,2S*,4aS*,8aR*)-2-(benzo[d][1,3]dioxol-5-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-N-isobutylacrylamide}, is a natural product isolated from the stem bark of B. obscura. It is composed of an octahydronaphthalene ring system substituted with an essentially planar benzodioxole ring system [r.m.s. deviation = 0.012 Å] and an extended isobutylacrylamide group. In the crystal, molecules are linked by N—H...O hydrogen bonds, forming chains propagating along [100]. The chains are linked by pairs of C—H...O hydrogen bonds, involving inversion-related benzodioxole ring systems, forming ribbons lying parallel to (010). There are also C—H...π interactions present within the ribbons.

Keywords

• crystal structure
• obscurine
• octahydronaphthalene
• benzodioxole
• isobutylacrylamide
• N—H...O hydrogen bonds