Synthesis of 2-pyridone-fused 2,2′-bipyridine derivatives. An unexpectedly complex solid state structure of 3,6-dimethyl-9H-4,5,9-triazaphenanthren-10-one

2-Pyridone-fused 2,2′-bipyridine derivatives 1a and 1b were synthesised. X-Ray diffraction analysis of 1b revealed a highly complex solid state structure with a disordered molecule imbedded in a channel structure formed by a centrosymmetric lattice of hexagonally packed, hydrogen bonded columns. The columns are assembled from three symmetry independent molecules. Dimerisation of the self-complementary cis-amide hydrogen bond motif is overridden by the fulfilment of the proton coordination ability of the phenanthroline nitrogens in accordance with Etter's rules of hydrogen bond priorities.