Received 12 April 2013
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.
For the stereoselective synthesis, applications and structures of related 2,6-dioxabicyclo[3.3.0]octan-3-ones, see: Agrawal et al. (2006); Banda & Chakravarthy (2006); Paddon-Jones et al. (2001). For the biological activity of target compounds, see: Hayes et al. (2003). For the synthesis of chiral tetrahydrofurans using L-malic acid, see: Álvarez et al. (2010). For pseudorotation parameters, see: Rao et al. (1981).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2086 ).
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.
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