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Volume 68 
Part 1 
Page o155  
January 2012  

Received 17 October 2011
Accepted 12 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 113 K
Mean [sigma](C-C) = 0.006 Å
R = 0.088
wR = 0.273
Data-to-parameter ratio = 13.0
Details
Open access

5-(3-Chlorophenylsulfanyl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde O-[(2-chloro-1,3-thiazol-5-yl)methyl]oxime

aCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, People's Republic of China, and bState Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China
Correspondence e-mail: daihong_2001@yahoo.com.cn

In the title compound, C16H11Cl2F3N4OS2, the benzene ring and the thiazole ring make dihedral angles of 83.2 (3) and 78.3 (3)°, respectively, with the pyrazole ring. The crystal packing shows S...N contacts of 3.309 (2) Å.

Related literature

For the bioactivity of pyrazole oxime derivatives, see: Takao et al. (1994[Takao, H., Wakisaka, S. & Murai, K. (1994). Jpn Patent No. 06329633.]); Watanabe et al. (2001[Watanabe, M., Kuwata, T., Okada, T., Ohita, S., Asahara, T., Noritake, T. & Fukuda, Y. (2001). Jpn Patent No. 2001233861.]). For the biological activity of thiazole derivatives, see: Fahmy & Bekhit (2002[Fahmy, H. Y. T. & Bekhit, A. A. (2002). Pharmazie, 57, 800-803.]); Sidoova et al. (1999[Sidoova, E., Kralova, K. & Loos, D. (1999). Molecules, 4, 73-80.]); Zhang et al. (2000[Zhang, A. G., Kayser, H., Maienfisch, P. & Casida, J. E. (2000). J. Neurochem. 75, 1294-1303.]).

[Scheme 1]

Experimental

Crystal data
  • C16H11Cl2F3N4OS2

  • Mr = 467.31

  • Monoclinic, P 21 /n

  • a = 12.328 (3) Å

  • b = 12.787 (3) Å

  • c = 13.139 (3) Å

  • [beta] = 110.16 (3)°

  • V = 1944.3 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.59 mm-1

  • T = 113 K

  • 0.20 × 0.16 × 0.10 mm

Data collection
  • Rigaku Saturn diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Toyko, Japan.]) Tmin = 0.891, Tmax = 0.943

  • 9881 measured reflections

  • 3309 independent reflections

  • 2725 reflections with I > 2[sigma](I)

  • Rint = 0.116

Refinement
  • R[F2 > 2[sigma](F2)] = 0.088

  • wR(F2) = 0.273

  • S = 1.10

  • 3309 reflections

  • 254 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.81 e Å-3

  • [Delta][rho]min = -0.94 e Å-3

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Toyko, Japan.]); 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: 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: AA2035 ).


Acknowledgements

This work was supported by the National Natural Science Foundation of China (NNSFC) (grant No. 20772068), the Science and Technology Projects Fund of Nantong City (grant Nos. K2010016, AS2010005), the Science Foundation of Nantong University (grant Nos. 09Z010, 09 C001) and the Scientific Research Foundation for Talent Introduction of Nantong University.

References

Fahmy, H. Y. T. & Bekhit, A. A. (2002). Pharmazie, 57, 800-803.  [PubMed] [ChemPort]
Rigaku (2008). CrystalClear. Rigaku Corporation, Toyko, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sidoova, E., Kralova, K. & Loos, D. (1999). Molecules, 4, 73-80.  [CrossRef] [ChemPort]
Takao, H., Wakisaka, S. & Murai, K. (1994). Jpn Patent No. 06329633.
Watanabe, M., Kuwata, T., Okada, T., Ohita, S., Asahara, T., Noritake, T. & Fukuda, Y. (2001). Jpn Patent No. 2001233861.
Zhang, A. G., Kayser, H., Maienfisch, P. & Casida, J. E. (2000). J. Neurochem. 75, 1294-1303.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o155  [ doi:10.1107/S160053681105358X ]

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