Self-Assembly of Sticky TABs: Inclusion Complexes and Hydrates from 1,3,5-Tris(4-hydroxybenzoyl)benzene

Six structures of crystalline materials obtained via the self-assembly of a 1,3,5-triaroylbenzene (TAB) derivative
peripherally functionalized with phenol residues (“sticky” groups) have been determined. Two general structural types were
observed:  highly symmetrical assemblies mediated by direct ArOH···OC hydrogen bonding (space group R3c) and extensively
hydrated structures in which water molecules occupy bridging positions between phenol and carbonyl groups (space group P21/n).
The former architecture accommodates included solvate molecules (EtOAc or H2O) within an interpenetrated α-Po type TAB network.
In the case of the hydrate, water molecules do not appear to be involved in any intermolecular interactions despite excellent hydrogen-bonding ability. Structures of the latter type feature well-defined voids for guest enclathration (guest = acetone, EtOH, MeOH). The
observed supramolecular interactions are discussed in the context of potential applications in crystal engineering.