5-Amino-7-(3-chloro­phen­yl)-3,7-di­hydro-2H-thieno[3,2-b]pyran-6-carbo­nitrile 1,1-dioxide

Shen, S.-D.; Feng, X.-D.; Yang, W.-H.; Wang, C.-H.; Yao, C.-S.

doi:10.1107/S1600536809055202

Volume 66
Part 2
Page o282
February 2010

Received 15 December 2009
Accepted 23 December 2009
Online 9 January 2010

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.004 Å
R = 0.053
wR = 0.134
Data-to-parameter ratio = 12.5
Details

5-Amino-7-(3-chlorophenyl)-3,7-dihydro-2H-thieno[3,2-b]pyran-6-carbonitrile 1,1-dioxide

Shi-De Shen,^a ^* Xiao-Dong Feng,^b,^c Wei-Hua Yang,^c Cui-Hua Wang ^b,^c and Chang-Sheng Yao ^b,^c

^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: chshengyaonk@mail.nankai.edu.cn

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.

Related literature

For the use of thienopyranyl compounds, such as thieno[3,2-b]pyran derivatives, as antiviral agents, see: Friary et al. (1991) and as [alpha] -2C adrenoreceptor agonists, see: Chao et al. (2009). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₄H₁₁ClN₂O₃S
M_r = 322.76
Monoclinic, P 2₁ /c
a = 9.5802 (19) Å
b = 17.364 (4) Å
c = 8.2521 (17) Å
= 97.83 (3)°
V = 1360.0 (5) Å³
Z = 4
Mo K radiation
= 0.45 mm^-1
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T_min = 0.916, T_max = 0.949
9115 measured reflections
2393 independent reflections
1705 reflections with I > 2(I)
R_int = 0.096

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.134
S = 1.08
2393 reflections
191 parameters
H-atom parameters constrained
_max = 0.67 e Å^-3
_min = -0.49 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2CN1ⁱ	0.88	2.20	3.060 (4)	165
N2-H2DO1ⁱⁱ	0.88	2.04	2.912 (4)	174
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x, y, z-1.

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 ).

Acknowledgements

The authors acknowledge financial support by the Graduate Foundation of Xuzhou Normal University (No. 09YLB030).

References

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.

organic compounds