Intermolecular recognition between hydrocarbon oxygen-donors and perfluorocarbon iodine-acceptors: the shortest O⋯I non-covalent bond

Heteroaromatic N-oxides are shown to work as effective electron donors towards perfluorocarbon iodides. This non-covalent interaction is strong enough to drive the self-assembly of perfluorocarbon and hydrocarbon modules into discrete aggregates or one dimensional infinite networks and to give rise to the shortest O⋯I intermolecular distance reported to now in the crystallographic literature. The effectiveness of the O⋯I–RF halogen bonding with respect to the better studied N⋯I–RF interaction is discussed.