Noncovalent derivatives of hydroquinone: Complexes with trigonal planar tris(N,N-dialkyl)trimesamides

The solid-state behavior of hydroquinone 1 with tris(N,N-diethyl)trimesamide 2 and tris(N,N-dimethyl)-trimesamide 3 has been determined using phase diagrams and X-ray diffraction techniques. A 3:2 complex, 4, forms between 1 and the diethyl derivative 2, while a 2:1 complex, 5, forms between 1 and the dimethyl derivative 3. X-ray structure determinations of the cocrystals reveal that the structures both contain a persistent R-4(4)(30) hydrogen bond ring system. The packing of the ring depends on the differing steric requirements of the methyl and ethyl substituents on trimesamides 2 and 3.