First hydrogen-bonded adduct of sterically hindered 2-tert-butyl-4-methylphenol (TBMP) with 1,3,6,8-tetraazatricyclo[4.4.1.1^3,8]dodecane (TATD) via coupling of classical hydrogen bonds and C—H...π non-covalent interactions

The title compound, C8H16N4·2C11H16O, was synthesized from the corresponding sterically crowded phenol by treatment with the aminal cage polyamine. Single-crystal X-ray diffraction structural analysis revealed the three-molecule aggregate to crystallize in the monoclinic space group P2/c with one half of a 1,3,6,8-tetraaztricyclo[4.4.1.13,8]dodecane (TATD) molecule and one 2-tert-butyl-4-methylphenol molecule per asymmetric unit. The crystal structure features intermolecular O—H...N and C—H...O hydrogen bonds, as well as intermolecular C—H...π interactions.