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Volume 68 
Part 4 
Page o1142  
April 2012  

Received 7 March 2012
Accepted 16 March 2012
Online 24 March 2012

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.052
wR = 0.142
Data-to-parameter ratio = 16.8
Details
Open access

1-(2,4-Dichlorophenyl)-5-(2-nitroanilino)-1H-pyrazole-4-carbonitrile

Ju Liu,a Zhi-Qiang Cai,b* Yang Wang,a Chun-Yan Lic and Li-Feng Xua

aCollege of Pharmacy, Liaoning University, Shenyang 110036, People's Republic of China,bTianjin Key Laboratory of Molecular Design and Drug Discovery, State Key Laboratory of Drug Delivery Technology and Pharmacokinetics, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, People's Republic of China, and cShenlong Pharmaceutical Limited Company, Shenyang 110141, People's Republic of China
Correspondence e-mail: caizq@tjipr.com

In the title compound, C16H9Cl2N5O2, the folded molecular conformation is characterized by a dihedral angle between the two benzene rings of 74.03 (5)°. An intramolecular N-H...O hydrogen bond is observed between the H atom of the amide group and a nitro-group O atom. Intermolecular C-H...O and N-H...N hydrogen bonds feature in the crystal packing.

Related literature

For general background to N-1-diaryl-1H-pyrazol-5-amine derivatives as synthetic intermediates in the preparation of medicinal compounds and the synthesis of the title compound, see: Markwalder et al. (2004[Markwalder, J. A., Arnone, M. R., Benfield, P. A., Boisclair, M., Burton, C. R., Chang, C. H., Cox, S. S., Czerniak, P. M., Dean, C. L., Doleniak, D., Grafstrom, R., Harrison, B. A., Kaltenbach, R. F., Nugiel, D. A., Rossi, K. A., Sherk, S. R., Sisk, L. M., Stouten, P., Trainor, G. L., Worland, P. & Seitz, S. P. (2004). J. Med. Chem. 47, 5894-5911.]); Mehdi et al. (2010[Mehdi, B., Ghodsieh, B., Maryam, V., Ali, S., Mehdi, P., Mansour, M., Parvaneh, P. & Maryam, A. (2010). Tetrahedron, 60, 2897-2902.]). For the pharmacological activity of the 5-aminopyrazole nucleus, see: Nils et al. (2010[Nils, G., Lars, B., Heinrich, M., Dirk, S., Nicole, T., Klemens, L., Raimund, K. & Peter, K. (2010). Bioorg. Med. Chem. Lett. 20, 5891-5894.]); Aymn et al. (2005[Aymn, E. R., Ahmed, H. S., Mohamed, I. H. & Hassan, M. A. (2005). Acta Chim. Slov. 52, 429-434.]).

[Scheme 1]

Experimental

Crystal data

  • C16H9Cl2N5O2

  • Mr = 374.18

  • Orthorhombic, P b c n

  • a = 13.878 (3) Å

  • b = 13.475 (3) Å

  • c = 17.421 (4) Å

  • V = 3257.7 (11) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.42 mm-1

  • T = 293 K

  • 0.20 × 0.18 × 0.12 mm
Data collection

  • Rigaku Saturn724 CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)[Rigaku/MSC (2005). Crystal Structure. Rigaku/MSC, The Woodlands, Texas, USA.] Tmin = 0.921, Tmax = 0.951

  • 31011 measured reflections

  • 3888 independent reflections

  • 2738 reflections with I > 2[sigma](I)

  • Rint = 0.050
Refinement

  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.142

  • S = 1.04

  • 3888 reflections

  • 231 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9...O2i 0.93 2.51 3.050 (3) 117
C5-H5...O1ii 0.93 2.58 3.374 (3) 143
N4-H4...N3iii 0.82 (3) 2.62 (3) 3.201 (3) 129 (2)
N4-H4...O1 0.82 (3) 2.02 (3) 2.608 (2) 128 (2)
Symmetry codes: (i) [x, -y+1, z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (iii) -x+1, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2005)[Rigaku/MSC (2005). Crystal Structure. Rigaku/MSC, The Woodlands, Texas, USA.]; 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: KP2396 ).

Acknowledgements

The authors thank the State Key Laboratory of Elemento-organic Chemistry, Nankai University, for the X-ray data collection.

References

Aymn, E. R., Ahmed, H. S., Mohamed, I. H. & Hassan, M. A. (2005). Acta Chim. Slov. 52, 429-434.
Markwalder, J. A., Arnone, M. R., Benfield, P. A., Boisclair, M., Burton, C. R., Chang, C. H., Cox, S. S., Czerniak, P. M., Dean, C. L., Doleniak, D., Grafstrom, R., Harrison, B. A., Kaltenbach, R. F., Nugiel, D. A., Rossi, K. A., Sherk, S. R., Sisk, L. M., Stouten, P., Trainor, G. L., Worland, P. & Seitz, S. P. (2004). J. Med. Chem. 47, 5894-5911.  [ISI] [CrossRef] [PubMed] [ChemPort]
Mehdi, B., Ghodsieh, B., Maryam, V., Ali, S., Mehdi, P., Mansour, M., Parvaneh, P. & Maryam, A. (2010). Tetrahedron, 60, 2897-2902.
Nils, G., Lars, B., Heinrich, M., Dirk, S., Nicole, T., Klemens, L., Raimund, K. & Peter, K. (2010). Bioorg. Med. Chem. Lett. 20, 5891-5894.  [PubMed]
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2005). Crystal Structure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2012). E68, o1142  [ doi:10.1107/S1600536812011506 ]

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