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Halogen bonding is a supramolecular interaction that was first described 150 years ago and whose crystallographic description was awarded a Nobel prize in 1969. After having been overlooked for a long time, its applicability for molecular recognition processes has increasingly been recognized by the scientific community over the past decade. A comprehensive statistical analysis of the solid-state structures deposited in the Cambridge Structural Database is presented herein that clearly shows that halogen bonding to the π-system of a phenyl moiety is frequent and can be directional.
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Mooibroek et al. (2012) studied this question.
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