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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 [sigma](C-C) = 0.004 Å
R = 0.050
wR = 0.135
Data-to-parameter ratio = 11.4
Details
Open access

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

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-H...N hydrogen bonds link the molecules into double layers parallel to the ab plane.

Related literature

For related structures, see: Özbey et al. (1999[Özbey, S., Kendi, E., Tozkoparan, B. & Ertan, M. (1999). Acta Cryst. C55, 1939-1941.]); Köysal et al. (2004[Köysal, Y., Isik, S., Dogdas, E., Tozkoparan, B. & Ertan, M. (2004). Acta Cryst. C60, o356-o357.]). For background to the biological properties of fused thiazolo[3,2-b][1,2,4]triazol derivatives, see: El-Sherif et al. (2006[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.]); Gilbertsen et al. (1999[Gilbertsen, R. B., Chan, K., Schrier, D. J., Guglietta, A., Bornemeier, D. A. & Dyer, R. D. (1999). J. Med. Chem. 42, 1151-1160.]); Karthikeyan (2009[Karthikeyan, M. S. (2009). Eur. J. Med. Chem. 44, 827-833.]); Lesyk et al. (2007[Lesyk, R., Vladzimirska, O., Holota, S., Zaprutko, L. & Gzella, A. (2007). Eur. J. Med.Chem. 42, 641-648.]); Martin et al. (1999[Martin, L., Rabasseda, X. & Castaner, J. (1999). Drugs Fut. 24, 853-857.]); Tozkoparan et al. (2000[Tozkoparan, B., Gokhan, N., Aktay, G., Yesilada, E. & Ertan, M. (2000). Eur. J. Med. Chem. 35, 743-750.], 2002[Tozkoparan, B., Aktayb, G. & Yesilada, E. (2002). Il Farmaco, 57, 145-152.], 2007[Tozkoparan, B., Küpeli, E., Yesilada, E. & Ertan, M. (2007). Bioorg. Med. Chem. 15, 1808-1814.]).

[Scheme 1]

Experimental

Crystal data
  • C13H11N3O3S

  • Mr = 289.31

  • Monoclinic, C 2

  • a = 11.5904 (13) Å

  • b = 7.0570 (8) Å

  • c = 16.4519 (18) Å

  • [beta] = 107.445 (2)°

  • V = 1283.8 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.]) Tmin = 0.314, Tmax = 1.000

  • 3567 measured reflections

  • 2096 independent reflections

  • 2022 reflections with I > 2[sigma](I)

  • Rint = 0.074

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.135

  • S = 1.07

  • 2096 reflections

  • 184 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 724 Friedel pairs

  • Flack parameter: 0.00 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9...N2i 0.93 2.46 3.375 (4) 167
C8-H8...N3ii 0.93 2.60 3.529 (4) 173
C1-H1...N3iii 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[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gilbertsen, R. B., Chan, K., Schrier, D. J., Guglietta, A., Bornemeier, D. A. & Dyer, R. D. (1999). J. Med. Chem. 42, 1151-1160.  [ISI] [PubMed]
Karthikeyan, M. S. (2009). Eur. J. Med. Chem. 44, 827-833.  [ISI] [CrossRef] [PubMed] [ChemPort]
Köysal, Y., Isik, S., Dogdas, E., Tozkoparan, B. & Ertan, M. (2004). Acta Cryst. C60, o356-o357.  [CSD] [CrossRef] [details]
Lesyk, R., Vladzimirska, O., Holota, S., Zaprutko, L. & Gzella, A. (2007). Eur. J. Med.Chem. 42, 641-648.  [CSD] [CrossRef] [ChemPort]
Martin, L., Rabasseda, X. & Castaner, J. (1999). Drugs Fut. 24, 853-857.  [ChemPort]
Özbey, S., Kendi, E., Tozkoparan, B. & Ertan, M. (1999). Acta Cryst. C55, 1939-1941.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tozkoparan, B., Aktayb, G. & Yesilada, E. (2002). Il Farmaco, 57, 145-152.  [CrossRef] [PubMed] [ChemPort]
Tozkoparan, B., Gokhan, N., Aktay, G., Yesilada, E. & Ertan, M. (2000). Eur. J. Med. Chem. 35, 743-750.  [ISI] [CrossRef] [PubMed] [ChemPort]
Tozkoparan, B., Küpeli, E., Yesilada, E. & Ertan, M. (2007). Bioorg. Med. Chem. 15, 1808-1814.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3139  [ doi:10.1107/S1600536812042559 ]

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