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Volume 68 
Part 1 
Page o65  
January 2012  

Received 23 November 2011
Accepted 3 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.048
wR = 0.123
Data-to-parameter ratio = 6.1
Details
Open access

5-Amino-1-(4-nitrophenyl)-1H-pyrazole-3-carbonitrile

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, C10H7N5O2, was synthesized by the reaction of 4-nitroaniline and 2,3-dicyanopropionic acid ethyl ester. In the crystal, N-H...O and C-H...O hydrogen bonds link the molecules, forming a three-dimensional network.

Related literature

N-pyrazole derivatives are of great interest because of their chemical and pharmaceutical properties, 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.]). They also exhibit diverse biological activity such as insecticidal (Zhao et al., 2010[Zhao, Q. Q., Li, Y. Q., Xiong, L. X. & Wang, Q. M. (2010). J. Agric. Food Chem. 58, 4992-4998.]) and antifungal activities (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.]).

[Scheme 1]

Experimental

Crystal data
  • C10H7N5O2

  • Mr = 229.21

  • Monoclinic, C c

  • a = 3.7685 (2) Å

  • b = 27.3441 (17) Å

  • c = 10.1294 (8) Å

  • [beta] = 96.20 (3)°

  • V = 1037.70 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.10 mm

Data collection
  • Enaf-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 = 0.968, Tmax = 0.989

  • 2148 measured reflections

  • 951 independent reflections

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

  • Rint = 0.071

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

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.123

  • S = 1.00

  • 951 reflections

  • 155 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4B...O2i 0.86 2.53 3.335 (5) 156
C4-H4A...O1ii 0.93 2.52 3.216 (5) 132
Symmetry codes: (i) [x, -y, z-{\script{1\over 2}}]; (ii) [x-1, -y, z-{\script{1\over 2}}].

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: HG5146 ).


Acknowledgements

The authors gratefully acknowledge Professor Hua-Qin Wang of the Analysis Center, Nanjing University, for the use of the diffractometer for this research project.

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.
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.
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]
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, o65  [ doi:10.1107/S1600536811052147 ]

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