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The propensity of the carbonyl functional group for halogen bonding in 1, 4-diiodotetrafluorobenzene cocrystals

The halogen bond is a useful complementary interaction to the hydrogen bond in crystal engineering, because it can be used to establish strong interactions with functional groups that are strong Lewis bases. One of such potential acceptors is the oxygen atom in the carbonyl group. A search of the Cambridge Structural Database for carbonyl groups participating in halogen bonding has revealed 4371 hits, with only 77 of them corresponding to cocrystals of perfluorinated donors. Since data corresponding to simple, smaller building blocks is scarce, we have focused our studies on aromatic amines or aromatic aldehydes as acceptor species. In our work, we synthesized six cocrystals with 1, 4-diiodotetrafluorobenzene via both mechanochemical synthesis and traditional solution synthesis. Halogen bonding to the carbonyl group is present in five out of these six cases. In one case, the oxygen atom preferentially participates in a N–H···O hydrogen bond, while the halogen bond is formed with the phenyl π-system.

aldehydes, cocrystals, halogen bonding

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