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

Jiang, Q.-H.; He, Q.; Zhang, J.-Q.; Yang, Y.; Wan, R.

doi:10.1107/S1600536811052147

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 (C-C) = 0.005 Å
R = 0.048
wR = 0.123
Data-to-parameter ratio = 6.1
Details

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

Qiang-Hua Jiang,^a Qiu He,^a Jian-Qiang Zhang,^a Yang Yang ^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, C₁₀H₇N₅O₂, was synthesized by the reaction of 4-nitroaniline and 2,3-dicyanopropionic acid ethyl ester. In the crystal, N-HO and C-HO 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). They also exhibit diverse biological activity such as insecticidal (Zhao et al., 2010) and antifungal activities (Liu et al., 2010). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₀H₇N₅O₂
M_r = 229.21
Monoclinic, C c
a = 3.7685 (2) Å
b = 27.3441 (17) Å
c = 10.1294 (8) Å
= 96.20 (3)°
V = 1037.70 (12) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 293 K
0.30 × 0.30 × 0.10 mm

Data collection

Enaf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.968, T_max = 0.989
2148 measured reflections
951 independent reflections
856 reflections with I > 2(I)
R_int = 0.071
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.123
S = 1.00
951 reflections
155 parameters
2 restraints
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H4BO2ⁱ	0.86	2.53	3.335 (5)	156
C4-H4AO1ⁱⁱ	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); 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: 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.
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.
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.
Zhao, Q. Q., Li, Y. Q., Xiong, L. X. & Wang, Q. M. (2010). J. Agric. Food Chem. 58, 4992-4998.

organic compounds