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Volume 69 
Part 5 
Page o772  
May 2013  

Received 12 April 2013
Accepted 15 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.044
wR = 0.097
Data-to-parameter ratio = 12.0
Details
Open access

[(2S,3aR,6aR)-5-Oxohexahydrofuro[3,2-b]furan-2-yl]methyl acetate

aDepartamento Quimica Organica, Facultade de Quimica, Universidade de Vigo, E-36310 Vigo, Spain, and bDepartamento Quimica Organica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Correspondence e-mail: mariacmatos@gmail.com

The title compound, C9H12O5, is a bicyclic lactone, presenting a 2,6-dioxabicyclo[3.3.0]octan-3-one skeleton, which was obtained through an intramolecular lactonization. The bicyclic lactone presents a cis ring-junction and a 1,5-trans-substituted tetrahydrofuran. Both five-membered rings are in twisted envelope conformations with one of the fused C atoms as the flap. The dihedral angle between the mean planes of the bicyclic lactone residue, defined by the dihydrofuran-2(3H)-one and the tetrahydrofuran rings, is 69.5 (2)°. The atoms of the ester chain are coplanar [maximum deviation = 0.013 (2) Å]. The absolute structure was not determined.

Related literature

For the stereoselective synthesis, applications and structures of related 2,6-dioxabicyclo[3.3.0]octan-3-ones, see: Agrawal et al. (2006[Agrawal, D., Sriramurthy, V. & Yadav, V. K. (2006). Tetrahedron Lett. 47, 7615-7618.]); Banda & Chakravarthy (2006[Banda, G. & Chakravarthy, I. E. (2006). Tetrahedron Asymmetry, 17, 1684-1687.]); Paddon-Jones et al. (2001[Paddon-Jones, G. C., McErlean, C. S. P., Hayes, P., Moore, C. J., Konig, W. A. & Kitching, W. (2001). J. Org. Chem. 66, 7487-7495.]). For the biological activity of target compounds, see: Hayes et al. (2003[Hayes, P. Y., Fletcher, M. T., Crow, S., McGrath, M. J., Tu, Y. Q., Zhang, H., Hungerford, N. L., McErlean, C. S. P., Stok, J. E., Moore, C. J., DeVoss, J. J. & Kitching, W. (2003). Quirality, 15, S116-S127.]). For the synthesis of chiral tetrahydrofurans using L-malic acid, see: Álvarez et al. (2010[Álvarez, C., Pérez, M., Zúñiga, A., Gómez, G. & Fall, Y. (2010). Synthesis, 22, 3883-3890.]). For pseudorotation parameters, see: Rao et al. (1981[Rao, S. T., Westhof, E. & Sundaralingam, M. (1981). Acta Cryst. A37, 421-425.]).

[Scheme 1]

Experimental

Crystal data
  • C9H12O5

  • Mr = 200.19

  • Monoclinic, P 21

  • a = 10.015 (5) Å

  • b = 4.647 (3) Å

  • c = 10.904 (5) Å

  • [beta] = 109.755 (7)°

  • V = 477.6 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 293 K

  • 0.49 × 0.11 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.602, Tmax = 0.745

  • 2551 measured reflections

  • 1530 independent reflections

  • 1313 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.097

  • S = 1.07

  • 1530 reflections

  • 128 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2086 ).


Acknowledgements

This work was supported financially by the Xunta de Galicia (No. EXPTE. CN 2012/184). The work of the MS and X-ray divisions of the research support service of the University of Vigo (CACTI) is also gratefully acknowledged. MG thanks the University of Vigo for a PhD fellowship.

References

Agrawal, D., Sriramurthy, V. & Yadav, V. K. (2006). Tetrahedron Lett. 47, 7615-7618.  [ISI] [CrossRef] [ChemPort]
Álvarez, C., Pérez, M., Zúñiga, A., Gómez, G. & Fall, Y. (2010). Synthesis, 22, 3883-3890.
Banda, G. & Chakravarthy, I. E. (2006). Tetrahedron Asymmetry, 17, 1684-1687.  [ISI] [CrossRef] [ChemPort]
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Hayes, P. Y., Fletcher, M. T., Crow, S., McGrath, M. J., Tu, Y. Q., Zhang, H., Hungerford, N. L., McErlean, C. S. P., Stok, J. E., Moore, C. J., DeVoss, J. J. & Kitching, W. (2003). Quirality, 15, S116-S127.  [ChemPort]
Paddon-Jones, G. C., McErlean, C. S. P., Hayes, P., Moore, C. J., Konig, W. A. & Kitching, W. (2001). J. Org. Chem. 66, 7487-7495.  [PubMed] [ChemPort]
Rao, S. T., Westhof, E. & Sundaralingam, M. (1981). Acta Cryst. A37, 421-425.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o772  [ doi:10.1107/S1600536813010313 ]

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