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

Jiang, J.-R.; Xu, F.; Ke, Z.-L.; Li, L.

doi:10.1107/S1600536811051312

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 (C-C) = 0.002 Å
R = 0.028
wR = 0.064
Data-to-parameter ratio = 21.7
Details

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

Jun-Rong Jiang,^a ^* Feng Xu,^a Zhong-Lu Ke ^a and Li Li ^a

^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); Rang et al. (1997). For applications of 2-sulfanylidenethiazolidin-4-one derivatives, see: Zidar et al. (2010); Powers et al. (2006).

Experimental

Crystal data

C₁₀H₉NOS₂
M_r = 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 radiation
= 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) T_min = 0.872, T_max = 0.919
9028 measured reflections
2777 independent reflections
2561 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.028
wR(F²) = 0.064
S = 1.00
2777 reflections
128 parameters
1 restraint
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.17 e Å^-3
Absolute structure: Flack (1983), 1155 Friedel pairs
Flack parameter: -0.01 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7-C12 ring.

D-HA	D-H	HA	DA	D-HA
C5-H5Cgⁱ	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); cell refinement: CrystalClear; data reduction: CrystalClear ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); 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.
Gattow, G., Kiel, G. & Rach, W. (1983). Z. Anorg. Allg. Chem. 506, 145-152.
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.
Rang, K., Liao, F. L., Sandstorm, J. & Wang, S. L. (1997). Chirality, 9, 568-577.
Rigaku/MSC (2008). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
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.

organic compounds