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Diversity of mutual orientations of Y–S and I–X and covalent bonds in molecular crystals complicate categorizing noncovalent chalcogen and halogen bonds. Here, the different types of S I interactions with short interatomic distances are analysed. The selection of S I interactions for the categorization of the chalcogen and halogen bonds has been made using angles that determine the mutual orientation of electron lone pairs and -holes interacted S and I atoms. In complicated cases of noncovalent interactions with ‘hole-to-hole’ of S and I orientations, distinguishing the chalcogen and halogen bonds is only possible if the atom is uniquely determined, which also provides the electrophilic site. The electronic criterion for chalcogen/halogen bonds categorizing that is based on analysis of dispositions of electron density and electrostatic potential minima along the interatomic lines has been suggested and its effectiveness has been demonstrated.

Electronic criterion for categorizing the chalcogen and halogen bonds: sulfuriodine interactions in crystals