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Volume 68 
Part 1 
Pages o156-o157  
January 2012  

Received 9 December 2011
Accepted 13 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.135
Data-to-parameter ratio = 22.7
Details
Open access

Methyl (Z)-2-[(2,4-dioxothiazolidin-3-yl)methyl]-3-(2-methylphenyl)prop-2-enoate

aDepartment of Physics, Sri Balaji Chokkalingam Engineering College, Arni, Thiruvannamalai 632 317, India,bDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, and cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: smurugavel27@gmail.com

The C=C bond in the title compound, C15H15NO4S, has a Z configuration. The thiazolidine ring is essentially planar [maximum deviation = 0.008 (1) Å for the N atom] and is oriented at a dihedral angle of 59.1 (1)° with respect to the benzene ring. In the crystal, pairs of C-H...O hydrogen bonds link centrosymmetrically related molecules into dimers, generating R22(18) ring motifs. The crystal packing is further stabilized by C-H...[pi] and C-O...[pi] [O...centroid = 3.412 (2) Å and C-O...centroid = 115.0 (1)°] interactions.

Related literature

For the biolgical activity of thiazolidine derivatives, see: Chen et al. (2000[Chen, H. S., Li, Z. M. & Han, Y. F. (2000). J. Agric. Food Chem. 48, 5312-5315.]); Jacop & Kutty (2004[Jacop, J. & Kutty, G. N. (2004). Indian Drugs, 41, 76-79.]); Kalia et al. (2007[Kalia, R., Rao, C. M. & Kutty, N. G. (2007). Arzneim. Forsch. (Drug Res.), 57, 616-622.]); Vicentini et al. (1998[Vicentini, C. B., Manfrini, M., Veronese, A. C. & Guarneri, M. (1998). J. Heterocycl. Chem. 35, 29-36.]); Vigorita et al. (1992[Vigorita, M. G., Basile, M., Zappala, C., Gabbrielli, G. & Pizzimenti, F. (1992). Farmaco, 47, 893-906.]). For resonance effects of acrylate, see: Merlino (1971[Merlino, S. (1971). Acta Cryst. B27, 2491-2492.]); Varghese et al. (1986[Varghese, B., Srinivasan, S., Padmanabhan, P. V. & Ramadas, S. R. (1986). Acta Cryst. C42, 1544-1546.]). For closely related structures, see: Fun et al. (2009[Fun, H.-K., Goh, J. H., Vinayaka, A. C. & Kalluraya, B. (2009). Acta Cryst. E65, o2094.]); Vennila et al. (2011[Vennila, J. P., Thiruvadigal, D. J., Kavitha, H. P., Chakkaravarthi, G. & Manivannan, V. (2011). Acta Cryst. E67, o1902.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C15H15NO4S

  • Mr = 305.34

  • Monoclinic, C 2/c

  • a = 21.3744 (10) Å

  • b = 6.9762 (3) Å

  • c = 20.3084 (10) Å

  • [beta] = 103.361 (2)°

  • V = 2946.3 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 293 K

  • 0.26 × 0.23 × 0.18 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.941, Tmax = 0.959

  • 18757 measured reflections

  • 4354 independent reflections

  • 2966 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.135

  • S = 1.04

  • 4354 reflections

  • 192 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7-C12 benzene ring.

D-H...A D-H H...A D...A D-H...A
C8-H8...O2i 0.93 2.55 3.379 (2) 148
C9-H9...Cg1ii 0.93 2.90 3.677 (2) 142
Symmetry codes: (i) [-x+1, y, -z+{\script{1\over 2}}]; (ii) [x+1, -y, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); 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: BT5747 ).


Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, H. S., Li, Z. M. & Han, Y. F. (2000). J. Agric. Food Chem. 48, 5312-5315.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Fun, H.-K., Goh, J. H., Vinayaka, A. C. & Kalluraya, B. (2009). Acta Cryst. E65, o2094.  [CSD] [CrossRef] [details]
Jacop, J. & Kutty, G. N. (2004). Indian Drugs, 41, 76-79.
Kalia, R., Rao, C. M. & Kutty, N. G. (2007). Arzneim. Forsch. (Drug Res.), 57, 616-622.  [ChemPort]
Merlino, S. (1971). Acta Cryst. B27, 2491-2492.  [CrossRef] [ChemPort] [details] [ISI]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Varghese, B., Srinivasan, S., Padmanabhan, P. V. & Ramadas, S. R. (1986). Acta Cryst. C42, 1544-1546.  [CrossRef] [details]
Vennila, J. P., Thiruvadigal, D. J., Kavitha, H. P., Chakkaravarthi, G. & Manivannan, V. (2011). Acta Cryst. E67, o1902.  [CSD] [CrossRef] [details]
Vicentini, C. B., Manfrini, M., Veronese, A. C. & Guarneri, M. (1998). J. Heterocycl. Chem. 35, 29-36.  [CrossRef] [ChemPort]
Vigorita, M. G., Basile, M., Zappala, C., Gabbrielli, G. & Pizzimenti, F. (1992). Farmaco, 47, 893-906.  [PubMed] [ChemPort]


Acta Cryst (2012). E68, o156-o157   [ doi:10.1107/S1600536811053682 ]

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