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Volume 66 
Part 10 
Page o2529  
October 2010  

Received 27 August 2010
Accepted 2 September 2010
Online 11 September 2010

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Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.094
Data-to-parameter ratio = 11.3
Details
Open access

7-[2-(3-Furyl)ethyl]-7,8-dimethyl-3,5,6,6a,7,8,9,10-octahydro-1H-naphtho[1,8a-c]furan-3-one

Akhtar Mohammad,a Muhammad Raza Shah,b* Itrat Anis,a Vickie McKeec and Josef W. A. Fresec

aDepartment of Chemistry, University of Karachi, Karachi 75270, Pakistan,bH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Science, University of Karachi, Karachi 75270, Pakistan, and cChemistry Department, Loughborough University, Loughborough, Leicestershire LE11 3TU, England
Correspondence e-mail: raza_shahm@yahoo.com

In the title molecule, C20H26O3, a clerodane diterpenoid isolated from Dodonaea viscosa, the trans-fused six-membered rings of the decaline system display chair conformations. The five-membered lactone ring adopts an envelope conformation and the five-membered furan ring is essentially planar with a maximum deviation of 0.0052 (12) Å.

Related literature

For the absolute stereochemistry of the title compound from NMR and literature data, see: Jefferies & Payne (1967[Jefferies, P. R. & Payne, T. G. (1967). Tetrahedron Lett. 1, 4777-4778.]). For background to natural product chemistry, see: Arfan et al. (2010[Arfan, M., Ali, M., Anis, I., Ahmad, H., Choudhary, M. I., Khan, A. & Shah, M. R. (2010). J. Enz. Inhib. Med. Chem. 25, 296-299.]); Khan et al. (2005[Khan, S. B., Azhar ul, H., Afza, N., Malik, A., Khan, M. T. H., Shah, M. R. & Choudhary, M. I. (2005). Chem. Pharm. Bull. 53, 86-89.]).

[Scheme 1]

Experimental

Crystal data

  • C20H26O3

  • Mr = 314.41

  • Orthorhombic, P 21 21 21

  • a = 9.1343 (8) Å

  • b = 11.8752 (10) Å

  • c = 15.5255 (13) Å

  • V = 1684.1 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 150 K

  • 0.46 × 0.21 × 0.08 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.963, Tmax = 0.994

  • 17210 measured reflections

  • 2378 independent reflections

  • 2124 reflections with I > 2[sigma](I)

  • Rint = 0.036
Refinement

  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.094

  • S = 1.05

  • 2378 reflections

  • 210 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Data collection: APEX2 (Bruker, 1998[Bruker (1998). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]) and OLEX2; molecular graphics: SHELXTL (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2325 ).

Acknowledgements

The authors thank the Higher Education Commission of Pakistan for financial support.

References

Arfan, M., Ali, M., Anis, I., Ahmad, H., Choudhary, M. I., Khan, A. & Shah, M. R. (2010). J. Enz. Inhib. Med. Chem. 25, 296-299.  [CrossRef] [ChemPort]
Bruker (1998). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Jefferies, P. R. & Payne, T. G. (1967). Tetrahedron Lett. 1, 4777-4778.
Khan, S. B., Azhar ul, H., Afza, N., Malik, A., Khan, M. T. H., Shah, M. R. & Choudhary, M. I. (2005). Chem. Pharm. Bull. 53, 86-89.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008a). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2010). E66, o2529  [ doi:10.1107/S1600536810035373 ]

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