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Volume 69 
Part 8 
Page o1313  
August 2013  

Received 1 July 2013
Accepted 2 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.022
wR = 0.061
Data-to-parameter ratio = 12.9
Details
Open access

2-(4-Oxo-3-phenyl-1,3-thiazolidin-2-ylidene)propanedinitrile

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bChemistry Department, Faculty of Science, Sohag University, 82524-Sohag, Egypt,cSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, England, and dKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

In the title compound, C12H7N3OS, the five-membered 1,3-thiazolidine ring is nearly planar [maximum deviation = 0.032 (2) Å] and makes a dihedral angle of 84.14 (9)° with the phenyl ring. In the crystal, molecules are linked by C-H...N hydrogen bonds into infinite chains along [-101]. C-H...[pi] interactions contribute to the arrangement of the molecules into layers parallel to (101).

Related literature

For the diverse biological applications of thiazolidinone-containing compounds, see, for example: Bouzroura et al. (2010[Bouzroura, S., Bentarzi, Y., Kaoua, R., Kolli, B. N., Martini, S. P. & Dunach, E. (2010). Org. Commun. 3, 8-14.]); Abhinit et al. (2009[Abhinit, M., Ghodke, M. & Pratima, N. A. (2009). Int. J. Pharm. Pharm. Sci. 1, 47-64.]); Naeem et al. (2009[Naeem, M., Chaudhary, M. N., Baloch, F. H. & Amjad, R. (2009). J. Chem. Soc. Pak. 31, 633-637.]); Sharma et al. (2009[Sharma, M. C., Shahu, N. K., Kohli, D. V., Chaturvedi, S. C. & Sharma, S. (2009). Digest J. Nanomater. Biostruct. 4, 223-232.]); Mistry & Desai (2004[Mistry, K. M. & Desai, K. R. (2004). E-J. Chem. 1, 189-193.]); Ramalakshmi et al. (2009[Ramalakshmi, N., Aruloly, L., Arunkumar, S., Ilango, K. & Puratchikody, A. (2009). Malaysian J. Sci. 28, 197-203.]); Turgut et al. (2007[Turgut, Z., Yolacan, C., Aydogan, F. E., Bagdatli, E. & Ocal, N. (2007). Molecules, 12, 2151-2159.]). For the synthesis of similar compounds, see: Farhat et al. (2007[Farhat, M. F., El-Saghier, A. M. M., Makhlouf, M. A., Kreddan, K. M. & Elmezoughi, A. B. (2007). J. Sulfur Chem. 28, 563-572.]). For similar structures, see: Pomés Hernández et al. (1996[Pomés Hernández, R., Duque Rodríguez, J., Novoa de Armas, H. & Toscano, R. A. (1996). Acta Cryst. C52, 1731-1733.]).

[Scheme 1]

Experimental

Crystal data
  • C12H7N3OS

  • Mr = 241.28

  • Monoclinic, C c

  • a = 16.979 (9) Å

  • b = 9.407 (5) Å

  • c = 7.034 (4) Å

  • [beta] = 103.927 (11)°

  • V = 1090.5 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 100 K

  • 0.24 × 0.12 × 0.04 mm

Data collection
  • Rigaku AFC12 (Right) diffractometer

  • Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012[Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.944, Tmax = 1.000

  • 3632 measured reflections

  • 1986 independent reflections

  • 1955 reflections with I > 2[sigma](I)

  • Rint = 0.015

Refinement
  • R[F2 > 2[sigma](F2)] = 0.022

  • wR(F2) = 0.061

  • S = 1.08

  • 1986 reflections

  • 154 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

  • Absolute structure: Flack x parameter determined using 718 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004[Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.])

  • Flack parameter: 0.03 (3)

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C7-C12 phenyl ring.

D-H...A D-H H...A D...A D-H...A
C10-H10...N3i 0.95 2.58 3.479 (4) 157
C8-H8...Cg2ii 0.95 2.96 3.610 (3) 127
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -y+1, z+{\script{1\over 2}}].

Data collection: CrystalClear-SM Expert (Rigaku, 2012[Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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: HG5329 ).


Acknowledgements

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

References

Abhinit, M., Ghodke, M. & Pratima, N. A. (2009). Int. J. Pharm. Pharm. Sci. 1, 47-64.  [ChemPort]
Bouzroura, S., Bentarzi, Y., Kaoua, R., Kolli, B. N., Martini, S. P. & Dunach, E. (2010). Org. Commun. 3, 8-14.  [ChemPort]
Farhat, M. F., El-Saghier, A. M. M., Makhlouf, M. A., Kreddan, K. M. & Elmezoughi, A. B. (2007). J. Sulfur Chem. 28, 563-572.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Mistry, K. M. & Desai, K. R. (2004). E-J. Chem. 1, 189-193.  [CrossRef] [ChemPort]
Naeem, M., Chaudhary, M. N., Baloch, F. H. & Amjad, R. (2009). J. Chem. Soc. Pak. 31, 633-637.  [ChemPort]
Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.  [CrossRef] [IUCr Journals]
Pomés Hernández, R., Duque Rodríguez, J., Novoa de Armas, H. & Toscano, R. A. (1996). Acta Cryst. C52, 1731-1733.  [CSD] [CrossRef] [IUCr Journals]
Ramalakshmi, N., Aruloly, L., Arunkumar, S., Ilango, K. & Puratchikody, A. (2009). Malaysian J. Sci. 28, 197-203.  [ChemPort]
Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.
Sharma, M. C., Shahu, N. K., Kohli, D. V., Chaturvedi, S. C. & Sharma, S. (2009). Digest J. Nanomater. Biostruct. 4, 223-232.
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]
Turgut, Z., Yolacan, C., Aydogan, F. E., Bagdatli, E. & Ocal, N. (2007). Molecules, 12, 2151-2159.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1313  [ doi:10.1107/S1600536813018308 ]

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