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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 [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.088
Data-to-parameter ratio = 17.4
Details
Open access

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

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-H...O 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[Friary, R. J., Schwerdt, J. H. & Ganguly, A. K. (1991). US Patent No. 5034531.]) and as [alpha]-2C adrenoreceptor agonists, see: Chao et al. (2009[Chao, J. H., Zheng, J. Y. & Aslanian, R. G. (2009). WO Patent No. 2009020578.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11BrN2O3S

  • Mr = 367.22

  • Monoclinic, P 21 /c

  • a = 8.3743 (18) Å

  • b = 14.003 (3) Å

  • c = 12.673 (3) Å

  • [beta] = 103.059 (3)°

  • V = 1447.7 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.534, Tmax = 0.715

  • 14473 measured reflections

  • 3440 independent reflections

  • 2636 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.95 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H1...O2i 0.88 (3) 2.26 (3) 2.989 (3) 140 (2)
N2-H2...O3ii 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[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [ChemPort] [ISI]
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.  [CrossRef] [details]


Acta Cryst (2010). E66, o264  [ doi:10.1107/S1600536809055214 ]

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