Acta Crystallographica Section E

Structure Reports Online

Volume 70, Part 5 (May 2014)


organic compounds



sj5394 scheme

Acta Cryst. (2014). E70, o530-o531    [ doi:10.1107/S1600536814007430 ]

9[alpha]-Hy­droxy-12-{[4-(4-hy­droxy­phen­yl)piperazin-1-yl]meth­yl}-4,8-dimethyl-3,14-dioxatri­cyclo­[9.3.0.02,4]tetra­dec-7-en-13-one

M. Loubidi, A. Benharref, L. El Ammari, M. Saadi and M. Berraho

Abstract: The title compound, C25H34N2O5, was synthesized from 9[alpha]-hy­droxy­parthenolide (9[alpha]-hy­droxy-4,8-dimethyl-12-methylen-3, 14-dioxa-tri­cyclo­[9.3.0.02,4]tetra­dec-7-en-13-one), which in turn was isolated from the chloro­form extract of the aerial parts of Anvillea radiata. The mol­ecule comprises a ten-membered ring fused to a five-membered ring with an additional ep­oxy ring system fused to the ten-membered ring. The five-membered ring also carries a 4-hy­droxy­phenyl-piperazin-1-ylmethyl substituent. The ten-membered ring adopts an approximate chair-chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hy­droxy group forming the flap. Two C atoms in the phenyl ring and the O atom of the hydroxyl group are disordered over two sites, with an occupancy ratio of 0.53 (5):0.47 (5). An intra­molecular O-H...N hydrogen-bond stabilizes the mol­ecular conformation. In the crystal, C-H...O hydrogen bonds link the mol­ecules into zigzag chains running along the a-axis direction.

CCDC reference: 995311


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