Single crystal X-ray structures of halogen-bonded assemblies formed between host -hexylammonium resorcinarene bromide () or -cyclohexylammonium resorcinarene chloride (), and 1,4-diiodooctafluorobutane and accompanying small solvent guests (methanol, acetonitrile and water) are presented. The guests' inclusion affects the geometry of the cavity of the receptors and , while the divalent halogen bond donor 1,4-diiodooctafluorobutane determines the overall nature of the halogen bond assembly. The crystal lattice of contains two structurally different dimeric assemblies A and B, formally resulting in the mixture of a capsular dimer and a dimeric pseudo-capsule. H and F NMR analyses supports the existence of these halogen-bonded complexes and enhanced guest inclusion in solution.