[Journal logo]

Volume 66 
Part 8 
Page o1927  
August 2010  

Received 29 June 2010
Accepted 29 June 2010
Online 7 July 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.098
Data-to-parameter ratio = 10.0
Details
Open access

14-Deoxyxyloccensin K from Chisocheton ceramicus (Meliaceae)

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and bDepartment of Pharmacy, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The title limonoid 14-deoxyxyloccensin K, C27H34O7, isolated from Chisocheton ceramicus (Meliaceae), features an oxygen linkage between carbon-3 and carbon-8 along with a tetrahydrofuryl sub-unit. The six-membered rings adopt chair configurations and the tetrahydrofuryl sub-unit has an envelope shape.

Related literature

For the synthesis of 14-deoxyxyloccensin K from xyloccensin K, see: Kim et al. (2004[Kim, J.-G., Cho, D. H. & Jang, D. O. (2004). Tetrahedron Lett. 45, 3031-3033.]). For the crystal structure of xyloccensin K, see: Kokpol et al. (1996[Kokpol, U., Chavasiri, W., Tip-Pyang, S., Veerachato, G., Zhao, F., Simpson, J. & Weavers, R. T. (1996). Phytochemistry, 41, 903-905.]). For a description of other xyloccensin limonoids, see: Wu et al. (2003[Wu, J., Zhang, S., Xiao, Q., Li, Q.-X., Huang, J.-S., Xiao, Z.-H. & Long, L.-J. (2003). Z. Naturforsch. Teil B, 58, 1216-1219.]).

[Scheme 1]

Experimental

Crystal data
  • C27H34O7

  • Mr = 470.54

  • Orthorhombic, P 21 21 21

  • a = 8.7174 (6) Å

  • b = 11.7401 (8) Å

  • c = 23.1106 (16) Å

  • V = 2365.2 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.25 × 0.15 × 0.05 mm

Data collection
  • Bruker SMART APEX diffractometer

  • 22814 measured reflections

  • 3083 independent reflections

  • 2674 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.098

  • S = 1.03

  • 3083 reflections

  • 307 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5284 ).


Acknowledgements

We thank the University of Malaya (PPP PS378/009B) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kim, J.-G., Cho, D. H. & Jang, D. O. (2004). Tetrahedron Lett. 45, 3031-3033.  [ISI] [CrossRef] [ChemPort]
Kokpol, U., Chavasiri, W., Tip-Pyang, S., Veerachato, G., Zhao, F., Simpson, J. & Weavers, R. T. (1996). Phytochemistry, 41, 903-905.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Wu, J., Zhang, S., Xiao, Q., Li, Q.-X., Huang, J.-S., Xiao, Z.-H. & Long, L.-J. (2003). Z. Naturforsch. Teil B, 58, 1216-1219.  [ChemPort]


Acta Cryst (2010). E66, o1927  [ doi:10.1107/S160053681002564X ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.