Received 8 December 2011
The title compound, C9H12ClN4+·Cl-, is a natural metabolic product of imidacloprid [systematic name: (E)-1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine] and was obtained by the reduction of the latter using Fe in HCl. The dihedral angle between the pyridine and imidazole rings is 62.09 (12)°. The crystal structure is stabilized by N-HCl and C-HCl interactions involving the chloride anion. The pyridine N and the chloride atoms are not involved in intermolecular interactions.
For background to the insecticidal applications of imidacloprid, see: Kanne et al. (2005); Schulz-Jander et al. (2002); Dai et al. (2010); Tanner (2010). For ring conformations, see: Duax & Norton (1975). For related structures, see: Kapoor et al. (2011).
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009) and PARST (Nardelli, 1995).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2070 ).
RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. He also thanks the UGC for research funding under research project F. No. 37-415/2009 (J&K) (SR).
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