Halogen-bonded complexes are formed between 4-(N,N-dimethylamino)pyridine and iodobenzenes with different degrees of fluorination. The degree of fluorination correlates with the observed N···I distance, which is furthermore influenced by the assembly of the complexes into one-dimensional chains and two- or three-dimensional networks via π−π stacking and various intermolecular short contacts involving fluorine, hydrogen, nitrogen, iodine, and carbon atoms. A linear correlation is found between the N···I separation and the pKa of the analogous fluorophenol.
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Präsang et al. (2009) studied this question.