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Comparison of isomeric meta- and para-diiodotetrafluorobenzene as halogen bond donors in crystal engineering

Abstract

We provide a systematic investigation of the structures and composition of halogen-bonded cocrystals involving the bent (meta) halogen bond donor 1,3-diiodotetrafluorobenzene (1,3-tfib), in comparison to analogous systems based on its linear (para) 1,4-isomer. In particular, whereas 1,4-tfib has now been established as an archetypal, ubiqitous example of a halogen bond donor, its meta-isomer has remained almost completely unexplored. This study investigates the structures of 14 new cocrystals of 1,3-tfib and 9 new, analogous cocrystals of 1,4-tfib, with 9 monotopic and 7 ditopic nitrogen-based aliphatic and aromatic halogen bond acceptors. Combined with previosuly reported structures of cocrystals of 1,4-tfib the results of our study indicate that, whereas halogen bond lengths and thermal stability of the investigated cocrystals are similar, the change in molecular shape between the two halogen bond donors brings about important consequences in supramolecular architectures and preferred stoichiometric compositions of otherwise analogous cocrystals. These preliminary results suggest that the principal factor responsible for such differences might be different abilities of cocrystals based on 1,3-tfib and 1,4-tfib to form close-packed structures.

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Publication details

The article was received on 20 Mar 2018, accepted on 27 Apr 2018 and first published on 27 Apr 2018


Article type: Paper
DOI: 10.1039/C8NJ01368C
Citation: New J. Chem., 2018, Accepted Manuscript
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    Comparison of isomeric meta- and para-diiodotetrafluorobenzene as halogen bond donors in crystal engineering

    N. Bedekovic, V. Stilinovic, T. Friščić and D. Cinčić, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ01368C

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