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

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Conformations
Crystal structure
crystal structure
rings
Hydrogen bonds
seats
Molecules
Chloroform
Chlorine compounds
Antennas
Atoms
chloroform
molecules
envelopes
hydrogen bonds
thiamorpholine
hydrogen
atoms
interactions
S(8)

Keywords

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

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Materials Science(all)
  • Chemistry(all)

Cite this

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

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, No. 2, 01.02.2015, p. o140-o141.

Research output: Contribution to journalArticle

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title = "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",
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.",
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author = "Ahmed Benharref and Mohamed Akssira and {El Ammari}, Lahcen and Mohamed Saadi and Moha Berraho and Harrison, {W.T. A.}",
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T1 - 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

AU - Benharref, Ahmed

AU - Akssira, Mohamed

AU - El Ammari, Lahcen

AU - Saadi, Mohamed

AU - Berraho, Moha

A2 - Harrison, W.T. A.

N1 - The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

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N2 - 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.

AB - 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.

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