3-Methyl-6-trichloro­methyl-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole

Jia, W.; Wang, Z.; Jia, X.; Zhang, J.; Wang, W.

doi:10.1107/S1600536811012748

Volume 67
Part 5
Page o1093
May 2011

Received 30 March 2011
Accepted 6 April 2011
Online 13 April 2011

Key indicators
Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.003 Å
R = 0.029
wR = 0.113
Data-to-parameter ratio = 18.3
Details

3-Methyl-6-trichloromethyl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

Wei-min Jia,^a Zhi-jian Wang,^a ^* Xiao-yu Jia,^b Jing-jing Zhang ^b and Wei Wang ^a,^b

^aSchool of Perfume and Aroma Technology, Shanghai Istitute of Technology, Shanghai 200235, People's Republic of China, and ^bSchool of Chemical Engineering, University of Science and Technology LiaoNing, Anshan 114051, People's Republic of China
Correspondence e-mail: zhao_submit@yahoo.com.cn

In the crystal structure of the title compound, C₅H₃Cl₃N₄S, two molecules related by a centre of symmetry demonstrate extremely short intermolecular SN contacts of 2.783 (2) Å. The crystal packing also exhibits [pi] - [pi] interactions indicated by a short distance of 3.340 (1) Å between the centroids of the triazole rings of neighbouring molecules.

Related literature

For the antimicrobial and anti-inflammatory activity of 1,2,4-triazole and 1,3,4-thiodiazole derivatives, see: Karabasanagouda et al. (2007); Mathew et al. (2007); For related structures, see: Du et al. (2008); Khan et al. (2009); Haugwitz et al. (1977).

Experimental

Crystal data

C₅H₃Cl₃N₄S
M_r = 257.52
Monoclinic, P 2₁ /n
a = 5.8732 (12) Å
b = 9.4164 (19) Å
c = 16.750 (3) Å
= 91.82 (3)°
V = 925.9 (3) Å³
Z = 4
Mo K radiation
= 1.17 mm^-1
T = 153 K
0.30 × 0.20 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T_min = 0.721, T_max = 0.892
9841 measured reflections
2196 independent reflections
1934 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.113
S = 1.24
2196 reflections
120 parameters
H-atom parameters constrained
_max = 0.49 e Å^-3
_min = -0.44 e Å^-3

Data collection: CrystalClear (Rigaku/MSC, 2005); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5070 ).

Acknowledgements

We gratefully acknowledge financial support by the Key Laboratory Project of Liaoning Province (grant No. 2008S127) and the Doctor Starting Foundation of Liaoning Province (grant No. 20071103).

References

Du, H., Du, H., An, Y. & Li, S. (2008). Acta Cryst. E64, o1402.
Haugwitz, R. D., Toeplitz, B. & Gougoutas, J. Z. (1977). J. Chem. Soc. Chem. Commun. pp. 736-737.
Karabasanagouda, T., Adhikari, A. V. & Shetty, S. N. (2007). Eur. J. Med. Chem. 42, 521-529.
Khan, M.-H., Hameed, S., Tahir, M. N., Bokhari, T. H. & Khan, I. U. (2009). Acta Cryst. E65, o1437.
Mathew, V., Keshavayya, J., Vaidya, V. P. & Giles, D. (2007). Eur. J. Med. Chem. 42, 823-840.
Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds