Structural investigation of weak intermolecular interactions (Hydrogen and Halogen Bonds) in fluorine-substituted benzimidazoles

The structures of five fluorinated benzimidazoles and one intermediate (an open double amide) have been determined by X-ray crystallography. In the analysis of these heterocycles, particular attention has been paid to N-H⋯H hydrogen bonds and to fluorine-fluorine intermolecular contacts. Thus, one of the shortest F⋯F distances ever reported, 2.596(3) Å, has been observed in 4,5,6,7-tetrafluoro-1H-benzimidazole-2(3H)-one. The 13C, 15N, and 19F solid-state NMR data for all benzimidazoles are also given.Peer Reviewe