Research Article: Ethyl 2-{3-[(6-chloro­pyridin-3-yl)meth­yl]-2-(nitro­imino)­imidazolidin-1-yl}acetate

Date Published: April 01, 2012

Publisher: International Union of Crystallography

Author(s): Kamini Kapoor, Madhukar B. Deshmukh, Chetan S. Shripanavar, Vivek K. Gupta, Rajni Kant.


In the title compound, C13H16ClN5O4, the imidazole ring is in a slight envelope conformation. The dihedral angle between the pyridine ring and the four essentially planar atoms [maximum deviation 0.015 (2) Å] of the imidazole ring is 80.8 (1)°. In, the crystal, weak C—H⋯O and C—H⋯N hydrogen bonds are present. In addition, there are weak π–π stacking inter­actions between symmetry-related pyridine rings with a centroid–centroid distance of 3.807 (1) Å.

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For background to the insecticidal applications of imidacloprid [systematic name: (E)-1-(6-chloro-3-pyridyl­meth­yl)-N-nitro­imidazolidin-2-yl­idene­amine], see: Deshmukh et al. (2011 ▶, 2012 ▶); Zhao et al. (2010 ▶). For related structures, see: Kapoor et al. (2011 ▶, 2012 ▶); Kant et al. (2012 ▶).