2-Chloro-N-[1-(4-chloro­phen­yl)-3-cyano-1H-pyrazol-5-yl]acetamide

Mu, H.; Yang, Y.; Jiang, Q.; Fu, X.; Wan, R.

doi:10.1107/S1600536812043966

Volume 68
Part 11
Page o3249
November 2012

Received 6 July 2012
Accepted 23 October 2012
Online 31 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.037
wR = 0.099
Data-to-parameter ratio = 15.1
Details

2-Chloro-N-[1-(4-chlorophenyl)-3-cyano-1H-pyrazol-5-yl]acetamide

Hai-ping Mu,^a Yang Yang,^a Qiang-hua Jiang,^a Xiao-dong Fu ^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, C₁₂H₈Cl₂N₄O, was synthesized by the reaction of 5-amino-1-(4-chlorophenyl)-1H-pyrazole-3-carbonitrile and 2-chloroacetyl chloride. The dihedral angle between the pyrazole and benzene rings is 30.7 (3)°. In the crystal structure, strong N-HO hydrogen bonds link the molecules into chains along [001]. C-HN hydrogen bonds are also present.

Related literature

The title compound is important in the synthesis of derivatives of the insecticide Fipronil {systematic name: (RS)-5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrile}. For the biological activity of N-pyrazole derivatives, see: Zhao et al. (2010); Liu et al. (2010). For bond-length data, see: Allen et al. (1987). For the structure of 2-chloro-N-(3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazol-5-yl)acetamide, see: Zhang et al. (2012).

Experimental

Crystal data

C₁₂H₈Cl₂N₄O
M_r = 295.12
Orthorhombic, P n a 2₁
a = 18.493 (4) Å
b = 13.815 (3) Å
c = 5.060 (1) Å
V = 1292.7 (4) Å³
Z = 4
Mo K radiation
= 0.50 mm^-1
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.865, T_max = 0.952
2646 measured reflections
2606 independent reflections
2255 reflections with I > 2(I)
R_int = 0.024
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.099
S = 1.01
2606 reflections
173 parameters
1 restraint
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.24 e Å^-3
Absolute structure: Flack (1983), 1271 Friedel pairs
Flack parameter: 0.09 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3AOⁱ	0.86	2.16	2.858 (3)	137
C12-H12CN2ⁱⁱ	0.97	2.52	3.445 (3)	160
Symmetry codes: (i) x, y, z+1; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1989); cell refinement: CAD-4 EXPRESS; 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: SHELXS97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RN2106 ).

Acknowledgements

The authors thank the Science and Technology Project of Jiangsu Province (No. BE2011352) for financial support and acknowledge the help of members of the laboratory.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
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.
Zhang, J., He, Q., Jiang, Q., Mu, H. & Wan, R. (2012). Acta Cryst. E68, o104.
Zhao, Q. Q., Li, Y. Q., Xiong, L. X. & Wang, Q. M. (2010). J. Agric. Food Chem. 58, 4992-4998.

organic compounds