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Volume 67 
Part 6 
Page o1472  
June 2011  

Received 27 April 2011
Accepted 15 May 2011
Online 20 May 2011

[hb5863sup1]
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Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.046
wR = 0.113
Data-to-parameter ratio = 11.1
Details
Open access

Fraxinellone

Hong-Mei Gu,a Hao Xu,a Zhao-Zhao Zhong,a Hai-Liang Zhua and Qing-Shan Lia*

aJiangsu Chiatai Tianqing Pharmaceutical Co. Ltd, Nanjing 210042, People's Repulic of China, and, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, People's Republic of China
Correspondence e-mail: benbenshell@yahoo.com.cn

In the title compound, C14H16O3 [systematic name: (3R*,3aR*)-3-(3-furanyl)-3a,7-dimethyl-3a,4,5,6-tetrahydro-2-benzofuran-1(3H)-one], the pendant methyl and furan groups attached to the stereogenic centres lie to the same side of the fused ring system. The dihedral angle between the five-membered rings is 74.8 (2)°; the fused five-membered ring adopts a twisted conformation. In the crystal, molecules are linked by weak C-H...O interactions, which generate [100] chains.

Related literature

For background to fraxinellone and its biological activity, see: Kim et al. (2009[Kim, J. H., Park, Y. M., Shin, J. S., Park, S. J., Choi, J. H., Jung, H. J., Park, H. J. & Lee, K. T. (2009). Biol. Pharm. Bull. pp. 1062-1068.]); Sun et al. (2009[Sun, Y., Qin, Y., Gong, F. Y., Wu, X. F., Hua, Z. C., Chen, T. & Xu, Q. (2009). Biochem. Pharmacol. pp. 1717-1724.]); Liu et al. (2009[Liu, Z. L., Ho, S. H. & Goh, S. H. (2009). Insect Sci., pp. 147-155.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C14H16O3

  • Mr = 232.27

  • Orthorhombic, P 21 21 21

  • a = 5.940 (3) Å

  • b = 12.661 (6) Å

  • c = 15.921 (7) Å

  • V = 1197.3 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.20 × 0.20 × 0.18 mm
Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.982, Tmax = 0.984

  • 10397 measured reflections

  • 1733 independent reflections

  • 1331 reflections with I > 2[sigma](I)

  • Rint = 0.049
Refinement

  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.113

  • S = 1.07

  • 1733 reflections

  • 156 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8...O1i 0.98 2.58 3.510 (3) 158
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5863 ).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Kim, J. H., Park, Y. M., Shin, J. S., Park, S. J., Choi, J. H., Jung, H. J., Park, H. J. & Lee, K. T. (2009). Biol. Pharm. Bull. pp. 1062-1068.
Liu, Z. L., Ho, S. H. & Goh, S. H. (2009). Insect Sci., pp. 147-155.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sun, Y., Qin, Y., Gong, F. Y., Wu, X. F., Hua, Z. C., Chen, T. & Xu, Q. (2009). Biochem. Pharmacol. pp. 1717-1724.

Acta Cryst (2011). E67, o1472  [ doi:10.1107/S1600536811018393 ]

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