Solid state 1:1 adduct via O–H⋯N hydrogen bond of the aminal 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane (TATD) and hydroquinone

Single crystal X-ray diffraction analysis of a 1:1 adduct of hydroquinone and 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane (TATD) provides structural information on molecular geometry of TATD. The adduct [C14H22N4O2] crystallizes in monoclinic symmetry, space group C2/c, with lattice constants: a = 11.188(1) Å, b = 7.447(1) Å, c = 16.909(3) Å, β = 90.84(1) deg, V = 1408.7(4) Å3, Z = 4, F(000) = 600, R1 = 4.2%, wR2 = 10.2%. This is the first crystal structure of a TATD–phenol complex, whose structure is stabilized by a N⋯H–O hydrogen bond. These intermolecular interactions are very important because they suggest that hydrogen bonds clearly play a role in the Mannich-type reactions in basic medium not only between TATD but also between other cyclic aminals with phenols.