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Volume 68 
Part 1 
Page o34  
January 2012  

Received 15 November 2011
Accepted 29 November 2011
Online 7 December 2011

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.002 Å
R = 0.028
wR = 0.064
Data-to-parameter ratio = 21.7
Details
Open access

(5S)-5-Methyl-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one

aDepartment of Biological & Chemical Engineering, Taizhou Vocational & Technical College, Taizhou 318000, People's Republic of China
Correspondence e-mail: jiangjr@tzvtc.com

In the title molecule, C10H9NOS2, the 2-sulfanylidenethiazolidin-4-one mean plane and phenyl ring form a dihedral angle of 81.7 (1)°. In the crystal, C-H...[pi] interactions link molecules into helical chains in [010].

Related literature

For related structures, see: Gattow et al. (1983[Gattow, G., Kiel, G. & Rach, W. (1983). Z. Anorg. Allg. Chem. 506, 145-152.]); Rang et al. (1997[Rang, K., Liao, F. L., Sandstorm, J. & Wang, S. L. (1997). Chirality, 9, 568-577.]). For applications of 2-sulfanylidenethiazolidin-4-one derivatives, see: Zidar et al. (2010[Zidar, N., Tomasic, T., Sink, R., Rupnik, V., Kovac, A., Turk, S., Patin, D., Blanot, D., Martel, C. C., Dessen, A., Müller-Premru, M., Zega, A., Gobec, S., Masic, L. P. & Kikelj, D. (2010). J. Med. Chem. 53, 6584-6594.]); Powers et al. (2006[Powers, J. P., Piper, D. E., Li, Y., Mayorga, V., Anzola, J., Chen, J. M., Jaen, J. C., Lee, G., Liu, J., Peterson, M. G., Tonn, G. R., Ye, Q., Walker, N. P. & Wang, Z. (2006). J. Med. Chem. 49,1034-1046.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9NOS2

  • Mr = 223.30

  • Orthorhombic, P 21 21 21

  • a = 6.8527 (4) Å

  • b = 8.6643 (5) Å

  • c = 17.5572 (15) Å

  • V = 1042.44 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.48 mm-1

  • T = 153 K

  • 0.30 × 0.20 × 0.18 mm

Data collection
  • Rigaku AFC10/Saturn724+ diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008[Rigaku/MSC (2008). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.872, Tmax = 0.919

  • 9028 measured reflections

  • 2777 independent reflections

  • 2561 reflections with I > 2[sigma](I)

  • Rint = 0.029

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

  • wR(F2) = 0.064

  • S = 1.00

  • 2777 reflections

  • 128 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1155 Friedel pairs

  • Flack parameter: -0.01 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7-C12 ring.

D-H...A D-H H...A D...A D-H...A
C5-H5...Cgi 1.00 2.47 3.4321 (16) 162
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: CrystalClear (Rigaku/MSC, 2008[Rigaku/MSC (2008). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear ; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5203 ).


Acknowledgements

We are very grateful to the Foundation of Taizhou Vocational and Technical College (grant No. 2010ZD09) for financial support.

References

Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gattow, G., Kiel, G. & Rach, W. (1983). Z. Anorg. Allg. Chem. 506, 145-152.  [CrossRef] [ChemPort]
Powers, J. P., Piper, D. E., Li, Y., Mayorga, V., Anzola, J., Chen, J. M., Jaen, J. C., Lee, G., Liu, J., Peterson, M. G., Tonn, G. R., Ye, Q., Walker, N. P. & Wang, Z. (2006). J. Med. Chem. 49,1034-1046.  [ISI] [CrossRef] [PubMed] [ChemPort]
Rang, K., Liao, F. L., Sandstorm, J. & Wang, S. L. (1997). Chirality, 9, 568-577.  [CrossRef] [ChemPort] [ISI]
Rigaku/MSC (2008). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Zidar, N., Tomasic, T., Sink, R., Rupnik, V., Kovac, A., Turk, S., Patin, D., Blanot, D., Martel, C. C., Dessen, A., Müller-Premru, M., Zega, A., Gobec, S., Masic, L. P. & Kikelj, D. (2010). J. Med. Chem. 53, 6584-6594.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o34  [ doi:10.1107/S1600536811051312 ]

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