5-Amino-7-(4-bromo­phen­yl)-3,7-di­hydro-2H-thieno[3,2-b]pyran-6-carbo­nitrile 1,1-dioxide

Yu, C.-X.; Feng, X.-D.; Jiang, B.; Wang, C.-H.; Yao, C.-S.

doi:10.1107/S1600536809055214

Volume 66
Part 2
Page o264
February 2010

Received 16 November 2009
Accepted 23 December 2009
Online 9 January 2010

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.003 Å
R = 0.036
wR = 0.088
Data-to-parameter ratio = 17.4
Details

5-Amino-7-(4-bromophenyl)-3,7-dihydro-2H-thieno[3,2-b]pyran-6-carbonitrile 1,1-dioxide

Chen-Xia Yu,^a Xiao-Dong Feng,^a Bei Jiang,^a Cui-Hua Wang ^a and Chang-Sheng Yao ^a ^*

^aSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China, and, Key Laboratory of Biotechnology for Medicinal Plants, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
Correspondence e-mail: chshengyaonk@mail.nankai.edu.cn

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, [theta] = 77.5 (10), [varphi] = 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.

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

C₁₄H₁₁BrN₂O₃S
M_r = 367.22
Monoclinic, P 2₁ /c
a = 8.3743 (18) Å
b = 14.003 (3) Å
c = 12.673 (3) Å
= 103.059 (3)°
V = 1447.7 (5) Å³
Z = 4
Mo K radiation
= 2.99 mm^-1
T = 113 K
0.24 × 0.22 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T_min = 0.534, T_max = 0.715
14473 measured reflections
3440 independent reflections
2636 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.088
S = 0.99
3440 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.43 e Å^-3
_min = -0.95 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H1O2ⁱ	0.88 (3)	2.26 (3)	2.989 (3)	140 (2)
N2-H2O3ⁱⁱ	0.91 (3)	2.02 (3)	2.919 (3)	169 (2)
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) x+1, y, z.

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 ).

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