Received 16 November 2009
In the title compound, C14H11BrN2O3S, the 2,3-dihydrothiophene ring is almost planar [maximum deviation = 0.006 (1) Å]. The pyran ring is in an envelope conformation [puckering parameters Q = 0.115 (2) Å, = 77.5 (10), = 172.9 (10)°]. The pyran and phenyl rings are approximately perpendicular, making a dihedral angle of -76.4 (2)°. The crystal packing is stabilized by intermolecular N-HO hydrogen bonds, with the sulfone O atoms acting as acceptors.
For the use of thienopyranyl compounds, such as thieno[3,2-b]pyran derivatives, as antiviral agents, see: Friary et al. (1991) and as -2C adrenoreceptor agonists, see: Chao et al. (2009). For puckering parameters, see: Cremer & Pople (1975).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2262 ).
The authors acknowledge financial support by the Graduate Foundation of Xuzhou Normal University (No. 09YLB030).
Chao, J. H., Zheng, J. Y. & Aslanian, R. G. (2009). WO Patent No. 2009020578.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Friary, R. J., Schwerdt, J. H. & Ganguly, A. K. (1991). US Patent No. 5034531.
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.