2-Chloro-5-nitro­pyridin-4-amine

He, J.-L.

doi:10.1107/S1600536812017643

Volume 68
Part 5
Page o1540
May 2012

Received 11 April 2012
Accepted 20 April 2012
Online 28 April 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.028
wR = 0.082
Data-to-parameter ratio = 9.9
Details

2-Chloro-5-nitropyridin-4-amine

Jian-Ling He ^a ^*

^aCollege of Chemical and Biological Engineering, Yancheng Institute of Technology, Yinbing Road No.9 Yancheng, Yancheng 224051, People's Republic of China
Correspondence e-mail: jlheyc@163.com

The title molecule, C₅H₄ClN₃O₂, possesses mirror symmetry, with all of the atoms lying in the mirror plane. There is an intramolecular N-HO hydrogen bond involving the adjacent -NO₂ and -NH₂ groups. A short C-HO interaction is also observed. In the crystal, adjacent molecules are linked via N-HCl and N-HN hydrogen bonds, forming chains propagating along [100].

Related literature

For details concerning the importance of the title compound as an intermediate in organic synthesis, and for the synthetic procedure, see: Hu et al. (2011). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₅H₄ClN₃O₂
M_r = 173.5
Orthorhombic, P n m a
a = 14.596 (2) Å
b = 6.2782 (10) Å
c = 7.3018 (12) Å
V = 669.11 (18) Å³
Z = 4
Mo K radiation
= 0.52 mm^-1
T = 296 K
0.18 × 0.17 × 0.15 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: multi-scan (North et al., 1968) T_min = 0.913, T_max = 0.927
3496 measured reflections
663 independent reflections
625 reflections with I > 2(I)
R_int = 0.034
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.028
wR(F²) = 0.082
S = 1.16
663 reflections
67 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2BO2	0.85	2.06	2.673 (3)	128
C5-H5O1	0.93	2.34	2.682 (2)	101
N2-H2ACl1ⁱ	0.80	2.77	3.3023 (18)	126
N2-H2BN1ⁱ	0.85	2.61	3.213 (2)	128
Symmetry code: (i) x, y, z-1.

Data collection: CAD-4 Software (Enraf-Nonius, 1985); 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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2408 ).

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

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 (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Hu, Y., Jin, Y. Z., Xiong, Y. P. & Li, Z. C. (2011). Sci. Technol. Eng. 11, 1841-1843.
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.

organic compounds