rac-1-(Furan-2-ylmethyl)-N-nitro-5-(oxolan-2-ylmethyl)-1,3,5-triazinan-2-imine

Abstract

In the title compound C13H19N5O4, which belongs to the insecticidally active neonicotinoid group of compounds, the triazane ring exhibits a half-chair conformation. The large discrepancy between the two nitro O—N—N bond angles [116.1 (2) and 123.98 (19)°] may be attributed to intramolecular N—H...O hydrogen bonding involving one of the nitro O atoms as the acceptor. The delocalization of the electrons extends as far as the nitro group, forming coplanar π-electron networks. In the crystal, inversion dimers lined by pairs of N—H...O hydrogen bonds occur.