摘要：

Fourhalopyridinium salts, 3-chloro- and 3-bromopyridinium chloridesand bromides, have been successfully cocrystallized with two ditopicperfluorinated iodobenzenes, 1,4-diiodotetrafluorobenzene and 1,2-diiodotetrafluorobenzene.These halogen bond donor molecules were chosen because the differentpositionings of halogen bond donor atoms can lead to different supramoleculararchitectures. In this work, we present insight into the halogen bondacceptor potential of chloride and bromide ions, as well as the halogenbond donor potential of chlorine and bromine atoms substituted onthe pyridinium ring when combined with the expectedly very stronghydrogen bonds between halopyridinium ions and free halogenide anions.A series of eight cocrystals were obtained in which three pairs ofisostructural cocrystals were formed. Dominant interactions in theobtained cocrystals were charge-assisted hydrogen bonds between halopyridiniumcations and halogenide ions as well as halogen bonds between halogenatoms on the pyridinium ring and halogenide ions. 3-Chloro- and 3-bromopyridinium chloride and bromide havebeen cocrystallized with 1,4-diiodo- and 1,2-diiodotetrafluorobenzene,in order to evaluate both the hydrogen and halogen bond acceptor potentialof chloride and bromide ions in combination with the hydrogen andhalogen bond donor potential of the halopyridinium cations.

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