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.