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Volume 69 
Part 10 
Pages o1553-o1554  
October 2013  

Received 29 July 2013
Accepted 11 September 2013
Online 18 September 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.118
Data-to-parameter ratio = 17.7
Details
Open access

Methyl 2-((2Z,5Z)-2-{(E)-2-[1-(4-hydroxyphenyl)ethylidene]hydrazin-1-ylidene}-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene)acetate

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England,bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt,cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA,dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

In the title compound, C20H17N3O4S, all non-H atoms, except those of the phenyl ring, are approximately coplanar [maximum deviation = 0.2214 (1) Å], and the dihedral angle between their best plane and the benzene ring is 53.13 (1)°. A short intramolecular O...S contact of 2.838 (1) Å is formed between the ester carbonyl O atom and the S atom of the thiazolidine ring. In the crystal, molecules associated via O-H...O, C-H...O and C-H...S hydrogen bonds form layers parallel to (010), with only C-H...O-type short contacts between the molecules in adjacent layers.

Related literature

For the biological activity of 4-thiazolidinones, see: Dayam et al. (2006[Dayam, R., Aiello, F., Deng, J., Wu, Y., Garofalo, A., Chen, X. & Neamati, N. (2006). J. Med. Chem. 49, 4526-4534.]); Srivastava et al. (2005[Srivastava, T., Gaikwad, A. K., Haq, W., Sinha, S. & Katti, S. B. (2005). ARKIVOC, ii, 120-130.]), Look et al. (1996[Look, G. C., Schullek, J. R., Homes, C. P., Chinn, J. P., Gordon, E. M. & Gallop, M. A. (1996). Bioorg. Med. Chem. Lett. 6, 707-712.]), Barreca et al. (2001[Barreca, M. L., Chimirri, A., Luca, L. D., Monforte, A., Monforte, P., Rao, A., Zappala, M., Balzarini, J., De Clercq, E., Pannecouque, C. & Witvrouw, M. (2001). Bioorg. Med. Chem. Lett. pp. 1793-1796.]); Diurno et al. (1992[Diurno, M. V., Mazzoni, O., Calignano, P. E., Giordano, F. & Bolognese, A. (1992). J. Med. Chem. 35, 2910-2912.]).

[Scheme 1]

Experimental

Crystal data
  • C20H17N3O4S

  • Mr = 395.42

  • Monoclinic, P 21 /n

  • a = 9.5049 (9) Å

  • b = 20.656 (2) Å

  • c = 10.1364 (10) Å

  • [beta] = 107.637 (1)°

  • V = 1896.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 150 K

  • 0.19 × 0.11 × 0.05 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.82, Tmax = 0.99

  • 16907 measured reflections

  • 4582 independent reflections

  • 3740 reflections with i > 2[sigma](i)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.118

  • S = 1.06

  • 4582 reflections

  • 259 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4O...O1i 0.84 (2) 1.96 (2) 2.7901 (16) 174.8 (19)
C8-H8...S1ii 0.95 2.82 3.7272 (17) 160
C10-H10...O4iii 0.95 2.52 3.452 (2) 167
C19-H19...O1i 0.95 2.47 3.200 (2) 133
Symmetry codes: (i) [x-{\script{3\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: GK2589 ).


Acknowledgements

Manchester Metropolitan University, Tulane University and Erciyes University are gratefully acknowledged for supporting this study.

References

Barreca, M. L., Chimirri, A., Luca, L. D., Monforte, A., Monforte, P., Rao, A., Zappala, M., Balzarini, J., De Clercq, E., Pannecouque, C. & Witvrouw, M. (2001). Bioorg. Med. Chem. Lett. pp. 1793-1796.  [CrossRef]
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dayam, R., Aiello, F., Deng, J., Wu, Y., Garofalo, A., Chen, X. & Neamati, N. (2006). J. Med. Chem. 49, 4526-4534.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Diurno, M. V., Mazzoni, O., Calignano, P. E., Giordano, F. & Bolognese, A. (1992). J. Med. Chem. 35, 2910-2912.  [CrossRef] [PubMed] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Look, G. C., Schullek, J. R., Homes, C. P., Chinn, J. P., Gordon, E. M. & Gallop, M. A. (1996). Bioorg. Med. Chem. Lett. 6, 707-712.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Srivastava, T., Gaikwad, A. K., Haq, W., Sinha, S. & Katti, S. B. (2005). ARKIVOC, ii, 120-130.  [CrossRef]


Acta Cryst (2013). E69, o1553-o1554   [ doi:10.1107/S1600536813025270 ]

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