5-[(Z)-2,3-Dimeth­oxy­benzyl­idene]-1,2,4-triazolo[3,2-b][1,3]thia­zol-6(5H)-one

Guo, L.; Lin, G.-T.; Wang, J.; Ni, L.; Ge, R.-S.

doi:10.1107/S1600536812042559

Volume 68
Part 11
Page o3139
November 2012

Received 2 September 2012
Accepted 11 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.050
wR = 0.135
Data-to-parameter ratio = 11.4
Details

5-[(Z)-2,3-Dimethoxybenzylidene]-1,2,4-triazolo[3,2-b][1,3]thiazol-6(5H)-one

Lu Guo,^a Gao-Tong Lin,^a Jia Wang,^a Li Ni ^a and Ren-Shan Ge ^a ^*

^aWenzhou Medical College, School of Pharmacy, Wenzhou 325035, People's Republic of China
Correspondence e-mail: profgrs@163.com

The title compound, C₁₃H₁₁N₃O₃S, was synthesized from 1H-1,2,4-triazole-5-thiol in a one pot reaction. The fused thiazolo[3,2-b][1,2,4]triazole system is essentially coplanar with the benzene ring: they enclose an interplanar angle of 1.37 (13)°. The olefinic double bond is in a Z conformation. In the crystal, C-HN hydrogen bonds link the molecules into double layers parallel to the ab plane.

Related literature

For related structures, see: Özbey et al. (1999); Köysal et al. (2004). For background to the biological properties of fused thiazolo[3,2-b][1,2,4]triazol derivatives, see: El-Sherif et al. (2006); Gilbertsen et al. (1999); Karthikeyan (2009); Lesyk et al. (2007); Martin et al. (1999); Tozkoparan et al. (2000, 2002, 2007).

Experimental

Crystal data

C₁₃H₁₁N₃O₃S
M_r = 289.31
Monoclinic, C 2
a = 11.5904 (13) Å
b = 7.0570 (8) Å
c = 16.4519 (18) Å
= 107.445 (2)°
V = 1283.8 (2) Å³
Z = 4
Mo K radiation
= 0.26 mm^-1
T = 293 K
0.32 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002) T_min = 0.314, T_max = 1.000
3567 measured reflections
2096 independent reflections
2022 reflections with I > 2(I)
R_int = 0.074

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.135
S = 1.07
2096 reflections
184 parameters
1 restraint
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.40 e Å^-3
Absolute structure: Flack (1983), 724 Friedel pairs
Flack parameter: 0.00 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C9-H9N2ⁱ	0.93	2.46	3.375 (4)	167
C8-H8N3ⁱⁱ	0.93	2.60	3.529 (4)	173
C1-H1N3ⁱⁱⁱ	0.93	2.65	3.556 (4)	164
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{3\over 2}}, z]$ ; (ii) -x, y-1, -z; (iii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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: FY2070 ).

Acknowledgements

This work was supported by the Zhejiang Provincial Natural Science Foundation of China (grant Nos. LY12H16003 and Y4110197) and the Project of Wenzhou Sci & Tech Bureau (Y20100273). The X-ray crystallographic facility at the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences is gratefully acknowledged for the data collection.

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.
El-Sherif, H. A. H., Mahmoud, A. M., Sarhan, A. A. O., Hozien, Z. A. & Habib, O. M. A. (2006). J. Sulfur Chem. 27 ,65-85.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gilbertsen, R. B., Chan, K., Schrier, D. J., Guglietta, A., Bornemeier, D. A. & Dyer, R. D. (1999). J. Med. Chem. 42, 1151-1160.
Karthikeyan, M. S. (2009). Eur. J. Med. Chem. 44, 827-833.
Köysal, Y., Isik, S., Dogdas, E., Tozkoparan, B. & Ertan, M. (2004). Acta Cryst. C60, o356-o357.
Lesyk, R., Vladzimirska, O., Holota, S., Zaprutko, L. & Gzella, A. (2007). Eur. J. Med.Chem. 42, 641-648.
Martin, L., Rabasseda, X. & Castaner, J. (1999). Drugs Fut. 24, 853-857.
Özbey, S., Kendi, E., Tozkoparan, B. & Ertan, M. (1999). Acta Cryst. C55, 1939-1941.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tozkoparan, B., Aktayb, G. & Yesilada, E. (2002). Il Farmaco, 57, 145-152.
Tozkoparan, B., Gokhan, N., Aktay, G., Yesilada, E. & Ertan, M. (2000). Eur. J. Med. Chem. 35, 743-750.
Tozkoparan, B., Küpeli, E., Yesilada, E. & Ertan, M. (2007). Bioorg. Med. Chem. 15, 1808-1814.

organic compounds