Crystal structure of (1S,2R,4R,9S,11S,-12R)-9α-hydroxy-4,8-dimethyl-12-[(thio-morpholin-4-yl)methyl]-3,14-dioxatri-cyclo[9.3.0.02,4]tetradec-7-en-13-one

Ahmed Benharref*, Mohamed Akssira, Lahcen El Ammari, Mohamed Saadi, Moha Berraho, W.T. A. Harrison (Editor)

*Corresponding author for this work

Research output: Contribution to journalArticle

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Abstract

The title compound, C19H29NO4S, was synthesised from 9a-hydroxyparthenolide (9α-hydroxy-4, 8-dimethyl-12-methyl-ene-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 the plant Anvillea radiata. The molecule is built up from two fused five- and ten-membered rings, with an additional epoxy ring system and a thiomorpholine group as a substituent. The ten-membered ring adopts an approximate chair-chair conformation, while the thiomorpholine ring displays a chair conformation and the five-membered ring has an envelope conformation, with the C atom closest to the hydroxy group forming the flap. An intramolecular O - H⋯N hydrogen bond closes an S(8) ring. The crystal structure features weak C - H⋯O hydrogen-bonding interactions, which link the molecules into [010] chains.

Original languageEnglish
Pages (from-to)o140-o141
Number of pages2
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number2
Early online date31 Jan 2015
DOIs
Publication statusPublished - 1 Feb 2015

Keywords

  • Anvillea radiata
  • Crystal structure
  • Hydrogen bonding
  • Medicinal compound

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