Halogen bonding is an effective tool in crystal engineering at the disposal of the supramolecular chemist. Indeed, halogen bonding has been successfully exploited in the design and synthesis of inclusion hosts, in topochemical reactions, in heteroditopic receptors, in the construction of conducting and NLO active materials, and as a means of resolving racemic halocarbons. The 1,3,5-triaroylbenzene (TAB) molecular framework combines synthetic accessibility and conformational flexibility to afford an attractive platform for the systematic study of solid-state supramolecular interactions such as halogen bonding. Toward this end, various halotriaroylbenzenes have been prepared and structurally characterized to gain insight into the relative importance of X•••O=C and X•••X interactions in solid-state assembly.