The hydrogen bonding interactions of 6:1 cyclamers composed of 1,3-diones in their enol forms and both fluoro- and perfluorobenzene have been examined by the AM1 molecular orbital method. These structures are analogous to those found experimentally in cocrystals of benzene with these diones. The fluorobenzne host-guest complexes are predicted to be stable, but the perfluorobenzene complexes are not. However, it is unlikely that the stabilization of fluorobenzene in the cocrystal would be greater than the interaction between molecules of fluorobenzene in solution.