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Volume 69 
Part 6 
Page o848  
June 2013  

Received 14 March 2013
Accepted 18 April 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.052
wR = 0.157
Data-to-parameter ratio = 19.5
Details
Open access

Ethyl 3-bromo-4-cyano-5-[(2-ethoxy-2-oxoethyl)sulfanyl]thiophene-2-carboxylate

aTianjin Entry-Exit Inspection and Quarantine Bureau, Youyi road No. 33, Tianjin, People's Republic of China
Correspondence e-mail: xpli0705@163.com

The title compound, C12H12BrNO4S2, was obtained by the Sandmeyer reaction from ethyl 3-amino-4-cyano-5-[(2-ethoxy-2-oxoethyl)sulfanyl]thiophene-2-carboxylate. The dihedral angle between the thiophene ring and linked CO2 ester group is 2.0 (5)°.

Related literature

For background literature on the use of 3-amino-4-cyano-5-ethoxycarbonylmethylsulfanyl-thiophene-2-carboxylic acid ethyl ester as an important intermediate compound for the synthesis of thienopyrimidine derivatives, which are thought to be potential biologically active compounds or pharmaceuticals, see: Liu et al. (2008[Liu, M. G., Hu, Y. G. & Ding, M. W. (2008). Tetrahedron, 64, 9052-9059.]). For a related compound, see: Padmavathi et al. (2011[Padmavathi, V., Reddy, G. D., Reddy, S. N. & Mahesh, K. (2011). Eur. J. Med. Chem. 46, 1367-1373.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12BrNO4S2

  • Mr = 378.26

  • Monoclinic, P 21 /c

  • a = 8.5896 (17) Å

  • b = 10.837 (2) Å

  • c = 16.584 (3) Å

  • [beta] = 99.44 (3)°

  • V = 1522.8 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.98 mm-1

  • T = 293 K

  • 0.20 × 0.18 × 0.12 mm

Data collection
  • Rigaku Saturn diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.587, Tmax = 0.716

  • 15211 measured reflections

  • 3596 independent reflections

  • 2224 reflections with I > 2[sigma](I)

  • Rint = 0.067

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.157

  • S = 1.00

  • 3596 reflections

  • 184 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.71 e Å-3

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); 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: ZJ2102 ).


Acknowledgements

The authors appreciate the help of Dr Haibin Song in Nankai University for the crystal X-ray measurement.

References

Liu, M. G., Hu, Y. G. & Ding, M. W. (2008). Tetrahedron, 64, 9052-9059.  [ISI] [CSD] [CrossRef] [ChemPort]
Padmavathi, V., Reddy, G. D., Reddy, S. N. & Mahesh, K. (2011). Eur. J. Med. Chem. 46, 1367-1373.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o848  [ doi:10.1107/S1600536813010611 ]

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