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

Vijayakumar, S.; Murugavel, S.; Kannan, D.; Bakthadoss, M.

doi:10.1107/S1600536811053682

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 (C-C) = 0.002 Å
R = 0.045
wR = 0.135
Data-to-parameter ratio = 22.7
Details

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

S. Vijayakumar,^a S. Murugavel,^b ^* D. Kannan ^c and M. Bakthadoss ^c ⁺

^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-HO 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] [Ocentroid = 3.412 (2) Å and C-Ocentroid = 115.0 (1)°] interactions.

Related literature

For the biolgical activity of thiazolidine derivatives, see: Chen et al. (2000); Jacop & Kutty (2004); Kalia et al. (2007); Vicentini et al. (1998); Vigorita et al. (1992). For resonance effects of acrylate, see: Merlino (1971); Varghese et al. (1986). For closely related structures, see: Fun et al. (2009); Vennila et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₅H₁₅NO₄S
M_r = 305.34
Monoclinic, C 2/c
a = 21.3744 (10) Å
b = 6.9762 (3) Å
c = 20.3084 (10) Å
= 103.361 (2)°
V = 2946.3 (2) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.941, T_max = 0.959
18757 measured reflections
4354 independent reflections
2966 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.135
S = 1.04
4354 reflections
192 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
C8-H8O2ⁱ	0.93	2.55	3.379 (2)	148
C9-H9Cg1ⁱⁱ	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); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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

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organic compounds