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Volume 69 
Part 7 
Page o1128  
July 2013  

Received 6 June 2013
Accepted 14 June 2013
Online 19 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.043
wR = 0.104
Data-to-parameter ratio = 11.8
Details
Open access

3-[(5-Chloro-2-hydroxybenzylidene)amino]-2-sulfanylidene-1,3-thiazolidin-4-one

aDepartment of Chemistry, Anadolu University, 26470 Eskisehir, Turkey
Correspondence e-mail: hakandal@anadolu.edu.tr

In the title compound, C10H7ClN2O2S2, the mean plane of the thioxothiazolidine ring [maximum deviation = 0.032 (2) Å] is inclined to the benzene ring by 12.25 (4)°. There is a strong intramolecular O-H...N hydrogen bond present. In the crystal, molecules are linked via pairs of C-H...Cl hydrogen bonds, forming inversion dimers.

Related literature

For general background to the chemistry, and pharmacological and biological activity of rhodanine and its derivatives, see: Raper (1985[Raper, E. S. (1985). Coord. Chem. Rev. 61, 115-184.]); Contello et al. (1994[Contello, B. C. C., Cawhorne, M. A., Haigh, D., Hindley, R. M., Smith, S. A. & Thurlby, P. L. (1994). Bioorg. Med. Chem. Lett. 4, 1181-1184.]); Villain-Guillot et al. (2007[Villain-Guillot, P., Gualtieri, M., Bastide, L., Roquet, F., Martinez, J., Amblard, M., Pugniere, M. & Leonetti, J. P. (2007). J. Med. Chem. 50, 4195-4204.]); Yan et al. (2007[Yan, S., Larson, G., Wu, J. Z., Applby, T., Ding, Y., Hamatake, R., Hong, Z. & Yao, N. (2007). Bioorg. Med. Chem. Lett. 17, 63-67.]); Kletzien et al. (1992[Kletzien, R. F., Clarke, S. D. & Ulrich, R. G. (1992). Mol. Pharmacol. 41, 393-398.]).

[Scheme 1]

Experimental

Crystal data
  • C10H7ClN2O2S2

  • Mr = 286.77

  • Monoclinic, P 21 /c

  • a = 9.8506 (3) Å

  • b = 10.0936 (3) Å

  • c = 12.1096 (4) Å

  • [beta] = 110.409 (2)°

  • V = 1128.45 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.70 mm-1

  • T = 100 K

  • 0.37 × 0.26 × 0.11 mm

Data collection
  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.783, Tmax = 0.927

  • 10564 measured reflections

  • 2816 independent reflections

  • 2427 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.028

  • wR(F2) = 0.081

  • S = 1.09

  • 2816 reflections

  • 162 parameters

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

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...N2 0.75 (2) 1.97 (2) 2.6291 (19) 147 (3)
C9-H9B...Cl1i 0.99 2.81 3.7860 (19) 169
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. 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: 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: SU2611 ).


Acknowledgements

The author is indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskisehir, Turkey, for the use of the X-ray diffractometer.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Contello, B. C. C., Cawhorne, M. A., Haigh, D., Hindley, R. M., Smith, S. A. & Thurlby, P. L. (1994). Bioorg. Med. Chem. Lett. 4, 1181-1184.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kletzien, R. F., Clarke, S. D. & Ulrich, R. G. (1992). Mol. Pharmacol. 41, 393-398.  [PubMed] [ChemPort]
Raper, E. S. (1985). Coord. Chem. Rev. 61, 115-184.  [CrossRef] [ChemPort] [Web of Science]
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]
Villain-Guillot, P., Gualtieri, M., Bastide, L., Roquet, F., Martinez, J., Amblard, M., Pugniere, M. & Leonetti, J. P. (2007). J. Med. Chem. 50, 4195-4204.  [Web of Science] [PubMed] [ChemPort]
Yan, S., Larson, G., Wu, J. Z., Applby, T., Ding, Y., Hamatake, R., Hong, Z. & Yao, N. (2007). Bioorg. Med. Chem. Lett. 17, 63-67.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1128  [ doi:10.1107/S1600536813016577 ]

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