Received 3 July 2013
In the title compound, C20H18O7, the dioxolane ring adopts an envelope conformation with the dimethyl-substituted C atom as the flap, and its mean plane makes a dihedral angle of 73.25 (2)° with the pyran ring mean plane. The furan ring makes dihedral angles of 67.43 (12) and 6.20 (11)° with the mean plane of the dioxolane and pyran rings, respectively. The O atom attached to the pyran ring deviates by 0.0219 (2) Å from its mean plane. In the crystal, molecules are linked via C-HO hydrogen bonds, forming chains along  and enclosing R22(9) loops. They stack along the a axis with - interactions involving the 4H-chromene units [centroid-centroid distances of 3.6389 (13) and 3.6555 (13) Å]. The terminal CH2=CH- atoms of the allyl acetate group are disordered over two sets of sites with a refined occupancy ratio of 0.717 (6):0.283 (6).
For the biological importance of 4H-chromene derivatives, see: Cai (2007, 2008); Cai et al. (2006); Caine (1993); Gabor (1988); Brooks (1998); Valenti et al. (1993); Hyana & Saimoto (1987); Tang et al. (2007).
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2620 ).
The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. ZF, TS and DV acknowledge the UGC (SAP-CAS) for the departmental facilities. ZF also thanks the UGC for a meritorious fellowship and TS thanks the DST Inspire for a fellowship.
Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cai, S. X. (2007). Recent Patents Anticancer Drug Discov. 2, 79-101.
Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607.
Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627-2644.
Caine, B. (1993). Science, 260, 1814-1816.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91-126. Budapest: Akademiai Kiado.
Hyana, T. & Saimoto, H. (1987). Jpn Patent JP 621 812 768.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437-o1438.
Valenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349-360.