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Ionic cocrystals derived from 3-halogenpyridinum halogenides and perfluorinated iodobenzenes

The halogen bond presents a highly directional class of intermolecular interaction frequently employed in crystal engineering [1]. The usage of neutral halogen bond acceptors in supramolecular systems is very well established, while anionic acceptor species are considerably less represented. Halogenide ions have been proven to be good halogen and hydrogen bond acceptors, because of the large charge concentration on one atom [2]. In this work, halogenpyridinium salts, 3-chloro- and 3- bromopyridinium chloride and bromide have been successfully cocrystallized with two geometrically different perfluorinated halogen bond donors: 1, 4-diiodotetrafluorobenzene (14tfib) and 1, 2-diiodotetrafluorobenzene (12tfib). Using halogenide ions as templates for the formation of halogen and hydrogen bonded multi-component systems, series of 8 cocrystals was obtained in which 3 pairs of isostructural cocrystals were formed. [1] G. Cavallo, P. Metrangolo, R. Milani, T. Pilati, A. Priimagi, G. Resnati, G. Terraneo, Chem. Rev., 116 (2016) 2478. [2] P. Metrangolo, T. Pilati, S. Biella, G. Terraneo, G. Resnati, CrystEngComm., 11 (2009) 1087.

ionic cocrystal ; halogen bond

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