Encapsulation of ion pairs in small spaces that are isolated from the medium is expected to result in amplified interactions between the ions. Yet, sequestration of ion pairs in self-assembled capsules is complicated by competition of the acids and bases for binding directly to the assembly components. We describe here a hydrogen bonded capsule 1.2(8).1 that accommodates two gamma-picolines and two acids as ion pairs. The supramolecular structure of the discrete 14-component assembly is characterized by NMR spectroscopy. The structure reveals the acids in the tapered ends of the capsule and gamma-picoliniums near the glycoluril spacers in the capsules center. Similar acid base ion pairs are also obtained with 4-ethylpyridine, gamma-picoline with difluoroacetic acid, and gamma-picoline with trifluoromethanesulfonic acid. The H-1 NMR spectrum of the gamma-picoline/trifluoroacetic acid ion pair shows a signal at delta = 18.7 ppm, indicating the acidic proton is in contact with both the picoline nitrogen and the trifluoroacetate oxygen. Further details about the unusual structures of ion pairs in small spaces are reported.