Received 15 December 2009
aXuzhou Institute of Architectural Technology, Xuzhou 221116, People's Republic of China,bSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China, and cKey Laboratory of Biotechnology for Medicinal Plants, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
Correspondence e-mail: firstname.lastname@example.org
The title compound, C14H11ClN2O3S, with fused thiophene and pyran rings, was synthesized via the condensation of dihydrothiophen-3(2H)-one 1,1-dioxide and 2-(3-chlorobenzylidene)malononitrile catalysed by triethylamine in ethanol. The thiophene ring adopts an envelope conformation and the pyran ring is planar (r.m.s. deviation = 0.0067 Å). The dihedral angle between the pyran and phenyl rings is 80.8 (1)°. The crystal packing is stabilized by intermolecular N-HN and N-HO hydrogen bonds in which the cyano N and sulphone O atoms, respectively, 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: HG2619 ).
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.