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Volume 68 
Part 1 
Page o104  
January 2012  

Received 27 October 2011
Accepted 7 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.053
wR = 0.155
Data-to-parameter ratio = 11.9
Details
Open access

2-Chloro-N-{3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazol-5-yl}acetamide

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: rwan@njut.edu.cn

The title compound, C13H6Cl3F3N4O, was synthesized by the reaction of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile and 2-chloroacetyl chloride. The five-membered pyrazole ring makes a dihedral angle of 71.5 (3)° with the benzene ring. The -CF3 group is disordered by rotation, and the F atoms are split over two sets of sites with occupancies of 0.59 (2) and 0.41 (2). The crystal structure features weak C-H...O and N-H...N interactions involving the carbonyl and cyano groups as acceptors.

Related literature

For biological properties of N-pyrazole derivatives, see: Cheng et al. (2008[Cheng, J. L., Wei, F. L., Zhu, L., Zhao, J. H. & Zhu, G. N. (2008). Chin. J. Org. Chem. 28, 622-627.]); Liu et al. (2010[Liu, Y. Y., Shi, H., Li, Y. F. & Zhu, H. J. (2010). J. Heterocycl. Chem. 47, 897-902.]); Hatton et al. (1993[Hatton, L. R., Buntain, I. G., Hawkins, D. W., Parnell, E. W. & Pearson, C. J. (1993). US Patent 5232940.]). For related structures, see: Yang et al. (2004[Yang, Z., Zhong, P. & Guo, S. (2004). Acta Cryst. E60, o1277-o1278.]); Zhang et al. (2005[Zhang, X.-H., Chen, J.-Z., Zhong, P., Xiao, H.-P. & Hu, M.-L. (2005). Acta Cryst. E61, o3676-o3678.]); Zhong et al. (2004[Zhong, P., Yang, Z., Li, S. & Tang, R. (2004). Acta Cryst. E60, o2395-o2396.]).

[Scheme 1]

Experimental

Crystal data
  • C13H6Cl3F3N4O

  • Mr = 397.57

  • Triclinic, [P \overline 1]

  • a = 8.4190 (17) Å

  • b = 9.2650 (19) Å

  • c = 11.944 (2) Å

  • [alpha] = 69.77 (3)°

  • [beta] = 76.74 (3)°

  • [gamma] = 66.10 (3)°

  • V = 794.9 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.62 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.837, Tmax = 0.887

  • 3133 measured reflections

  • 2921 independent reflections

  • 2313 reflections with I > 2[sigma](I)

  • Rint = 0.030

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.155

  • S = 1.01

  • 2921 reflections

  • 246 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.60 e Å-3

  • [Delta][rho]min = -0.58 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4A...N3i 0.86 2.49 3.280 (5) 153
C4-H4B...Oii 0.93 2.53 3.349 (5) 148
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z.

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2393 ).


Acknowledgements

The authors thank Professor Hua-qin Wang of the Analysis Centre, Nanjing University, for providing help during the X-ray crystallographic analysis.

References

Cheng, J. L., Wei, F. L., Zhu, L., Zhao, J. H. & Zhu, G. N. (2008). Chin. J. Org. Chem. 28, 622-627.  [ChemPort]
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Hatton, L. R., Buntain, I. G., Hawkins, D. W., Parnell, E. W. & Pearson, C. J. (1993). US Patent 5232940.
Liu, Y. Y., Shi, H., Li, Y. F. & Zhu, H. J. (2010). J. Heterocycl. Chem. 47, 897-902.  [CrossRef] [ChemPort]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yang, Z., Zhong, P. & Guo, S. (2004). Acta Cryst. E60, o1277-o1278.  [CSD] [CrossRef] [details]
Zhang, X.-H., Chen, J.-Z., Zhong, P., Xiao, H.-P. & Hu, M.-L. (2005). Acta Cryst. E61, o3676-o3678.  [CSD] [CrossRef] [details]
Zhong, P., Yang, Z., Li, S. & Tang, R. (2004). Acta Cryst. E60, o2395-o2396.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o104  [ doi:10.1107/S1600536811052743 ]

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