Hydrogen bonding and halogen bonding co-existing in the reaction of heptafluorobenzyl iodide with N,N,N′,N′-tetramethylethylene diamine

Two novel assembling systems 3 and 4, with the structures of C6F5CF2−⋯H+N(Me)2CH2CH2(Me2)N+H⋯−CF2C6F5 and C6F5CF2I⋯N(Me)2CH2CH2(Me)2N⋯ICF2C6F5, respectively, have been generated from the solution of heptafluorobenzyl iodide 1 and N,N,N′,N′-tetramethylethylenediamine 2 in dichloromethane. Their structures have been characterized by X-ray diffraction analysis, NMR and IR spectroscopy. Intermolecular N⋯I halogen bond and F⋯H hydrogen bond are revealed to be the driving forces for their formation.