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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 [sigma](C-C) = 0.004 Å
R = 0.037
wR = 0.099
Data-to-parameter ratio = 15.1
Details
Open access

2-Chloro-N-[1-(4-chlorophenyl)-3-cyano-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, 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-H...O hydrogen bonds link the molecules into chains along [001]. C-H...N 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[Zhao, Q. Q., Li, Y. Q., Xiong, L. X. & Wang, Q. M. (2010). J. Agric. Food Chem. 58, 4992-4998.]); Liu et al. (2010[Liu, Y. Y., Shi, H., Li, Y. F. & Zhu, H. J. (2010). J. Heterocycl. Chem. 47, 897-902.]). For bond-length data, see: Allen et al. (1987[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.]). 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[Zhang, J., He, Q., Jiang, Q., Mu, H. & Wan, R. (2012). Acta Cryst. E68, o104.]).

[Scheme 1]

Experimental

Crystal data
  • C12H8Cl2N4O

  • Mr = 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[alpha] radiation

  • [mu] = 0.50 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 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 = 0.865, Tmax = 0.952

  • 2646 measured reflections

  • 2606 independent reflections

  • 2255 reflections with I > 2[sigma](I)

  • Rint = 0.024

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

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.099

  • S = 1.01

  • 2606 reflections

  • 173 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1271 Friedel pairs

  • Flack parameter: 0.09 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...Oi 0.86 2.16 2.858 (3) 137
C12-H12C...N2ii 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[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; 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: 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.  [CrossRef] [details]
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.  [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]
Zhang, J., He, Q., Jiang, Q., Mu, H. & Wan, R. (2012). Acta Cryst. E68, o104.  [CrossRef] [details]
Zhao, Q. Q., Li, Y. Q., Xiong, L. X. & Wang, Q. M. (2010). J. Agric. Food Chem. 58, 4992-4998.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o3249  [ doi:10.1107/S1600536812043966 ]

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