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

Zhang, J.; He, Q.; Jiang, Q.; Mu, H.; Wan, R.

doi:10.1107/S1600536811052743

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 (C-C) = 0.005 Å
Disorder in main residue
R = 0.053
wR = 0.155
Data-to-parameter ratio = 11.9
Details

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

Jian-qiang Zhang,^a Qiu He,^a Qiang-hua Jiang,^a Hai-pin Mu ^a and Rong Wan ^a ^*

^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-HO and N-HN interactions involving the carbonyl and cyano groups as acceptors.

Related literature

For biological properties of N-pyrazole derivatives, see: Cheng et al. (2008); Liu et al. (2010); Hatton et al. (1993). For related structures, see: Yang et al. (2004); Zhang et al. (2005); Zhong et al. (2004).

Experimental

Crystal data

C₁₃H₆Cl₃F₃N₄O
M_r = 397.57
Triclinic, $[P \overline 1]$
a = 8.4190 (17) Å
b = 9.2650 (19) Å
c = 11.944 (2) Å
= 69.77 (3)°
= 76.74 (3)°
= 66.10 (3)°
V = 794.9 (3) Å³
Z = 2
Mo K radiation
= 0.62 mm^-1
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.837, T_max = 0.887
3133 measured reflections
2921 independent reflections
2313 reflections with I > 2(I)
R_int = 0.030
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.155
S = 1.01
2921 reflections
246 parameters
H-atom parameters constrained
_max = 0.60 e Å^-3
_min = -0.58 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H4AN3ⁱ	0.86	2.49	3.280 (5)	153
C4-H4BOⁱⁱ	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); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: 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.
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.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yang, Z., Zhong, P. & Guo, S. (2004). Acta Cryst. E60, o1277-o1278.
Zhang, X.-H., Chen, J.-Z., Zhong, P., Xiao, H.-P. & Hu, M.-L. (2005). Acta Cryst. E61, o3676-o3678.
Zhong, P., Yang, Z., Li, S. & Tang, R. (2004). Acta Cryst. E60, o2395-o2396.

organic compounds