Herein, we report the single-crystal X-ray diffraction analysis of supramolecular host–guest systems based on triflate-functionalized pillar[5]arenes and 1,4-dibromobutane or n-hexane. The guest molecule was stabilized inside the pillar[5]arene cavity by C–H⋯π and C–H⋯O interactions. These inclusion complexes were further self-assembled into supramolecular networks by various non-bonding interactions such as C-H⋯O, C-H⋯F, Br⋯Br, F⋯F, etc. The intermolecular interactions present in these systems were investigated in detail. One of the supramolecular systems analyzed in this study exhibited intermolecular F⋯F interactions which were operative between the adjacent pillararene rims. It was observed that the type of guest molecule considerably influenced the mutual interactions of pillararene macrocycles and their networking pattern in the crystal. The inclusion complexes were further studied by Hirshfeld surface analysis which not only provided a visual representation of the intermolecular interactions experienced by the systems but gave a quantitative account of these various interactions.
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