Conservation of the Hydrogen-Bonded Pyridone Homosynthon in Halogen-Bonded Cocrystals

Seven cocrystals of pyridone and perfluorinated halocarbons have been prepared. In all cases pairs of pyridone molecules are connected into dimers by two N-HmiddotmiddotmiddotO hydrogen bonds, forming the characteristic pyridone homosynthon of R22(8) topology. These dimers further act as acceptors of halogen bonds through the two pyridone oxygen atoms, forming two (in six cases) or three (in one case) halogen bonds with the donor molecules. The stoichiometry of the cocrystals obtained and the overall topology of the supramolecular architecture depend primarily on the topicity of the halogen bond donor, with the monotopic donor yielding a cocrystal of 1:1 stoichiometry comprising discrete supramolecular complexes, the ditopic donors cocrystals of 1:2 stoichiometry comprising chains, and the tritopic donor a cocrystal of 1:2 stoichiometry comprising hydrogen- and halogen-bonded layers. The results indicate that the pyridone homosynthon is a robust and reliable supramolecular synthon that is conserved in halogen-bonded cocrystals of pyridone.