1-(3-Chloro­pyridin-2-yl)hydrazine

Wang, P.; Wan, R.; Yu, P.; He, Q.; Zhang, J.

doi:10.1107/S1600536810036950

Volume 66
Part 10
Page o2599
October 2010

Received 29 June 2010
Accepted 15 September 2010
Online 18 September 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.032
wR = 0.082
Data-to-parameter ratio = 12.4
Details

1-(3-Chloropyridin-2-yl)hydrazine

Peng Wang,^a Rong Wan,^a ^* Peng Yu,^a Qiu He ^a and Jian-qiang Zhang ^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, C₅H₆ClN₃, was synthesized by the reaction of 2,3-dichloropyridine and hydrazine hydrate. An intramolecular N-HCl hydrogen bond results in the formation of a planar (mean deviation 0.038 Å) five-membered ring. In the crystal, intermolecular N-HN hydrogen bonds link the molecules into a three-dimensional network.

Related literature

The title compound is an intermediate in the synthesis of Rynaxypyr, a new insecticidal anthranilic diamide. For the synthesis and biological properties of Rynaxypyr, see: Lahm et al. (2007). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₅H₆ClN₃
M_r = 143.58
Monoclinic, P 2₁ /c
a = 11.637 (2) Å
b = 3.9060 (8) Å
c = 13.946 (3) Å
= 103.46 (3)°
V = 616.5 (2) Å³
Z = 4
Mo K radiation
= 0.52 mm^-1
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.860, T_max = 0.950
2173 measured reflections
1124 independent reflections
936 reflections with I > 2(I)
R_int = 0.036
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.082
S = 1.04
1124 reflections
91 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.17 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2ACl	0.88 (2)	2.58 (2)	2.970 (2)	108 (2)
N2-H2AN3ⁱ	0.88 (2)	2.28 (2)	3.058 (3)	148 (2)
N3-H3AN1ⁱⁱ	0.94 (2)	2.41 (2)	3.243 (3)	148 (2)
N3-H3BN2ⁱⁱⁱ	0.90 (2)	2.68 (2)	3.492 (3)	151 (2)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{5\over 2}}]$ ; (iii) x, y+1, z.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; 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: IM2217 ).

Acknowledgements

The authors gratefully acknowledge Professor Hua-Qin Wang of the Analysis Center, Nanjing University, for allowing the Enraf-Nonius CAD-4 diffractometer to be used 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.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Lahm, G. P., Stevenson, T. M., Selby, T. P., Cordova, F. D., Flexner, L., Bellin, C. A., Dubas, C. M., Smith, B. K., Hughes, K. A., Hollingshaus, J. G., Clark, C. E. & Benner, E. A. (2007). Bioorg. Med. Chem. Lett. 17, 6274-6279.
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