The absolute structure of ptilosarcenone 2.5-hydrate, a diterpenoid briarane from the orange sea pen Ptilosarcus gurneyi (Gray)

In the title compound, C24H29ClO8·2.5H2O, which contains two organic molecules (A and B) and five heavily disordered water molecules in the asymmetric unit, the γ-lactone ring and the cyclohexenone ring are both trans-fused to the central cyclodecene ring. The cyclehexenone...

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Main Authors: Elaine Tran, Nathan S. Shapiro, Douglas E. Conklin, Daniel J. Nurco
Format: Article
Language:English
Published: International Union of Crystallography 2011-01-01
Series:Acta Crystallographica Section E
Online Access:http://scripts.iucr.org/cgi-bin/paper?S1600536810050142
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spelling doaj-f7687d7c489b403eac9e12436e401d972020-11-25T01:13:22ZengInternational Union of CrystallographyActa Crystallographica Section E1600-53682011-01-01671o181o18210.1107/S1600536810050142The absolute structure of ptilosarcenone 2.5-hydrate, a diterpenoid briarane from the orange sea pen Ptilosarcus gurneyi (Gray)Elaine TranNathan S. ShapiroDouglas E. ConklinDaniel J. NurcoIn the title compound, C24H29ClO8·2.5H2O, which contains two organic molecules (A and B) and five heavily disordered water molecules in the asymmetric unit, the γ-lactone ring and the cyclohexenone ring are both trans-fused to the central cyclodecene ring. The cyclehexenone ring features an α,β-unsaturated ketone with torsion angles between the conjugated carbonyl and alkene bonds of 0.6 (3) and 7.4 (4)° for molecules A and B, respectively. The ptilosarcenone torsion angles between conjugated alkene bonds are 56.2 (5) and 55.4 (6)° for A and B, respectively. In the crystal, the components are linked by O—H...O hydrogen bonds. The absolute configuration of ptilosarcenone was determined unambiguously and exhibits similar absolute stereochemistry to that found in the crystal structures of other octocoralline briaranes. http://scripts.iucr.org/cgi-bin/paper?S1600536810050142
collection DOAJ
language English
format Article
sources DOAJ
author Elaine Tran
Nathan S. Shapiro
Douglas E. Conklin
Daniel J. Nurco
spellingShingle Elaine Tran
Nathan S. Shapiro
Douglas E. Conklin
Daniel J. Nurco
The absolute structure of ptilosarcenone 2.5-hydrate, a diterpenoid briarane from the orange sea pen Ptilosarcus gurneyi (Gray)
Acta Crystallographica Section E
author_facet Elaine Tran
Nathan S. Shapiro
Douglas E. Conklin
Daniel J. Nurco
author_sort Elaine Tran
title The absolute structure of ptilosarcenone 2.5-hydrate, a diterpenoid briarane from the orange sea pen Ptilosarcus gurneyi (Gray)
title_short The absolute structure of ptilosarcenone 2.5-hydrate, a diterpenoid briarane from the orange sea pen Ptilosarcus gurneyi (Gray)
title_full The absolute structure of ptilosarcenone 2.5-hydrate, a diterpenoid briarane from the orange sea pen Ptilosarcus gurneyi (Gray)
title_fullStr The absolute structure of ptilosarcenone 2.5-hydrate, a diterpenoid briarane from the orange sea pen Ptilosarcus gurneyi (Gray)
title_full_unstemmed The absolute structure of ptilosarcenone 2.5-hydrate, a diterpenoid briarane from the orange sea pen Ptilosarcus gurneyi (Gray)
title_sort absolute structure of ptilosarcenone 2.5-hydrate, a diterpenoid briarane from the orange sea pen ptilosarcus gurneyi (gray)
publisher International Union of Crystallography
series Acta Crystallographica Section E
issn 1600-5368
publishDate 2011-01-01
description In the title compound, C24H29ClO8·2.5H2O, which contains two organic molecules (A and B) and five heavily disordered water molecules in the asymmetric unit, the γ-lactone ring and the cyclohexenone ring are both trans-fused to the central cyclodecene ring. The cyclehexenone ring features an α,β-unsaturated ketone with torsion angles between the conjugated carbonyl and alkene bonds of 0.6 (3) and 7.4 (4)° for molecules A and B, respectively. The ptilosarcenone torsion angles between conjugated alkene bonds are 56.2 (5) and 55.4 (6)° for A and B, respectively. In the crystal, the components are linked by O—H...O hydrogen bonds. The absolute configuration of ptilosarcenone was determined unambiguously and exhibits similar absolute stereochemistry to that found in the crystal structures of other octocoralline briaranes.
url http://scripts.iucr.org/cgi-bin/paper?S1600536810050142
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