Date Published: July 01, 2011
Publisher: International Union of Crystallography
Author(s): Mohamed Moumou, Ahmed Benharref, Moha Berraho, Lahcen El Ammari, Mohamed Akssira, Ahmed Elhakmaoui.
The title compound, C19H29NO5, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The molecule is built up from two fused five- and ten-membered rings with the (morpholin-4-yl)methyl group as a substituent. The five-membered lactone ring has an envelope conformation, whereas the ten-membered and the morpholine rings display approximate chair–chair and chair conformations, respectively. The dihedral angle between the ten-membered ring and the lactone ring is 27.93 (6)°. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen-bond interactions. An intramolecular O—H⋯N hydrogen bond also occurs.
For background to the medicinal uses of the plant Anvillea radiata, see: Abdel Sattar et al. (1996 ▶); Bellakhdar (1997 ▶); El Hassany et al. (2004 ▶); Qureshi et al. (1990 ▶). For the reactivity of this sesquiterpene see: Der-Ren et al. (2006 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).