Crystal structure and Hirshfeld surface analysis of pulcherrin J

Abstract

The title compound, C29H36O4 [systematic name (4aR,5R,6aS,7R,11aS,11bR)-4a-hydroxy-4,4,7,11b-tetramethyl-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodecahydrophenanthro[3,2-b]furan-5-yl cinnamate], a natural diterpene known as pulcherrin J, was isolated from stem barks of medicinally important Caesalpinia pulcherrima (L.). The crystal structure of pulcherrin J shows it to be composed of a central core of three trans-fused cyclohexane rings and a near planar five-membered furan ring, along with an axially oriented cinnamate moiety and an hydroxy substituent attached at positions 4a and 5 of the steroid ring system, respectively. The absolute structure was established with the use of Cu Kα radiation. In the crystal, molecules are linked by O—H...O hydrogen bonds to generate [100] C(8) chains. Hirshfeld surface analysis indicates that the most significant contacts in packing are H...H (67.5%), followed by C...H (19.6%) and H...O (12.9%).

Keywords

• crystal structure
• Pulcherrin J
• Caesalpinia pulcherrima (L.)
• diterpene
• Hirshfeld surface analysis