Influence of halogen size on the supramolecular and energy landscape of the THF solvates of the halogen derivatives of dianthranilide

The synthesis, crystallisation and detailed description of the crystal structure of the THF solvates of four halogen (F, Cl, Br and I) derivatives of dianthranilide (5H,11H-dibenzo[b,f][1,5]diazocine-6,12-dione) have been reported. The influence of the halogen size on the conformation of the halogen derivative, the overall supramolecular architecture including the existing scheme of intermolecular interactions and the selected energy issues have been discussed in detail. The solvates which are described in this paper exhibit an interesting arrangement of molecules in their crystals resembling a "honeycomb". The variety of interactions between the respective molecules, including hydrogen bonds, halogen-mediated noncovalent interactions and pi-pi contacts, makes them an attractive target for crystallographic studies. The results of our analysis may lead to a better understanding of the role of a halogen functional group in the rational design of specific multicomponent crystalline networks based on compounds consisting of two substituted phenyl rings separated by a fused heterocyclic moiety.