C–H⋯O hydrogen bonds in molecular complexes of 1,3,5-trinitrobenzene with some N-heterocycles

Abstract

The crystal structures of the molecular complexes of sym-trinitrobenzene (TNB) with acridine, 1,10-phenanthroline and phenazine are discussed. In all three cases, the structures are held together by C–H⋯O and π⋯π interactions, and TNB forms hydrogen bonded dimers and tapes that are not found in its native crystal structure. Acridine and 1,10-phenanthroline yield 1 ∶ 1 complexes that have very similar structures. The related molecule phenazine, however, gives a different 2 ∶ 3 complex in which guest exchange, as seen in other recently reported examples, is not observed. A case is made for the reporting of such ‘low yield’ supramolecular reactions because they still provide valuable information about the packing characteristics of organic molecules.