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Volume 69 
Part 4 
Page o488  
April 2013  

Received 11 January 2013
Accepted 27 February 2013
Online 6 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.039
wR = 0.116
Data-to-parameter ratio = 20.2
Details
Open access

Ethyl (2E,4E)-5-(3-bromophenylsulfonyl)penta-2,4-dienoate

aDepartment of Physics, Presidency College, Chennai 600 005, India, and bDepartment of Chemistry, Pachaiyappa's College, Chennai 600 030, India
Correspondence e-mail: aravindhanpresidency@gmail.com

In the title compound, C13H13BrO4S, both C=C double bonds adopt an E conformation. The S atom has a distorted tetrahedral geometry with bond angles ranging from 102.17 (13) to 119.77 (14)°. The ethyl acrylate substituent adopts an extented conformation with all torsion angles close to 180°. In the crystal, molecules are linked into centrosymmetric R22(14) dimers via pairs of C-H...O hydrogen bonds.

Related literature

For the biological activity of phenyl sulfonyl-containing compounds, see: De-Benedetti et al. (1985[De-Benedetti, P. G., Folli, U., Iarossi, D. & Frassineti, C. (1985). J. Chem. Soc. Perkin Trans. 2, pp. 1527-1532.]); Chumakov et al. (2006[Chumakov, Y. M., Tsapkov, V. I., Bocelli, G., Antonsyak, B. Y., Palomares-Sánches, S. A., Ortiz, R. S. & Gulya, A. P. (2006). J. Struct. Chem. 47, 923-929.]); Kremer et al. (2006[Kremer, E., Facchin, G., Estévez, E., Alborés, P., Baran, E. J., Ellena, J. & Torre, M. H. (2006). J. Inorg. Biochem. 100, 1167-1175.]). For related structures, see: Li et al. (2011[Li, X.-L. (2011). Acta Cryst. E67, o2622.]); Sankar et al. (2012[Sankar, U., Sabari, V., Suresh, G., Uma, R. & Aravindhan, S. (2012). Acta Cryst. E68, o1093.]); Chakkaravarthi et al. (2008[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.]); Rodriguez et al. (1995[Rodriguez, J. G., del Valle, C., Esteban-Calderon, C. & Martinez-Repoll, M. (1995). J. Chem. Crystallogr. 25, 249-257.]). For graph-set analysis of hydrogen bonds, see: Sankar et al. (2012[Sankar, U., Sabari, V., Suresh, G., Uma, R. & Aravindhan, S. (2012). Acta Cryst. E68, o1093.]).

[Scheme 1]

Experimental

Crystal data
  • C13H13BrO4S

  • Mr = 345.20

  • Monoclinic, C 2/c

  • a = 27.883 (5) Å

  • b = 6.001 (5) Å

  • c = 17.256 (5) Å

  • [beta] = 94.020 (5)°

  • V = 2880 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 3.01 mm-1

  • T = 293 K

  • 0.32 × 0.20 × 0.10 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.972, Tmax = 0.992

  • 14906 measured reflections

  • 3479 independent reflections

  • 2360 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.116

  • S = 1.01

  • 3479 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.73 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...O3i 0.93 2.37 3.235 (4) 154
Symmetry code: (i) -x+2, -y, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6881 ).


Acknowledgements

SA and VS thank the UGC, India, for financial support. The authors thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the X-ray intensity data collection.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.  [CSD] [CrossRef] [details]
Chumakov, Y. M., Tsapkov, V. I., Bocelli, G., Antonsyak, B. Y., Palomares-Sánches, S. A., Ortiz, R. S. & Gulya, A. P. (2006). J. Struct. Chem. 47, 923-929.  [ISI] [CrossRef] [ChemPort]
De-Benedetti, P. G., Folli, U., Iarossi, D. & Frassineti, C. (1985). J. Chem. Soc. Perkin Trans. 2, pp. 1527-1532.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kremer, E., Facchin, G., Estévez, E., Alborés, P., Baran, E. J., Ellena, J. & Torre, M. H. (2006). J. Inorg. Biochem. 100, 1167-1175.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Li, X.-L. (2011). Acta Cryst. E67, o2622.  [CSD] [CrossRef] [details]
Rodriguez, J. G., del Valle, C., Esteban-Calderon, C. & Martinez-Repoll, M. (1995). J. Chem. Crystallogr. 25, 249-257.  [CrossRef] [ISI]
Sankar, U., Sabari, V., Suresh, G., Uma, R. & Aravindhan, S. (2012). Acta Cryst. E68, o1093.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o488  [ doi:10.1107/S1600536813005771 ]

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