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Volume 69 
Part 9 
Page o1387  
September 2013  

Received 23 June 2013
Accepted 1 August 2013
Online 7 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.030
wR = 0.074
Data-to-parameter ratio = 11.8
Details
Open access

(2E,4E)-Ethyl 5-(2,4-dichlorophenylsulfonyl)penta-2,4-dienoate

aDepartment of Chemistry, Pachaiyappa's College, Chennai 600 030, India,bDepartment of Physics, Presidency College, Chennai 600 005, India, and cDepartment of Chemistry, B.S. Abdur Rahman University, Chennai 600 048, India
Correspondence e-mail: aravindhanpresidency@gmail.com

In the title compound, C13H12Cl2O4S, both C=C double bonds adopt an E conformation. The S atom has a distorted tetrahedral geometry with bond angles ranging from 103.03 (12) to 118.12 (13)°. The ethoxycarbonyl group is disordered over two sets of sites, with site-occupancy factors of 0.739 (11) and 0.261 (11). In the crystal, C-H...O interactions link the molecules into chains molecules running parallel to the a axis.

Related literature

For the biological activity of phenylsulfonyl-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.]). For related structures, see: Li (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.]).

[Scheme 1]

Experimental

Crystal data
  • C13H12Cl2O4S

  • Mr = 335.19

  • Monoclinic, P 21

  • a = 5.773 (5) Å

  • b = 9.939 (5) Å

  • c = 13.268 (5) Å

  • [beta] = 95.876 (5)°

  • V = 757.3 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.57 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.824, Tmax = 0.847

  • 6848 measured reflections

  • 2471 independent reflections

  • 2314 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.074

  • S = 1.06

  • 2471 reflections

  • 209 parameters

  • 74 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1054 Friedel pairs

  • Absolute structure parameter: 0.04 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...O1i 0.93 2.36 3.217 (4) 153
C9-H9...O1i 0.93 2.50 3.312 (4) 146
Symmetry code: (i) x+1, 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: PV2638 ).


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

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]
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]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
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.  [CSD] [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] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1387  [ doi:10.1107/S1600536813021429 ]

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