Received 29 June 2010
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.
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).
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 ).
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.
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.