CRYSTAL ENGINEERING USING POLYPHENOLS - HOST-GUEST BEHAVIOR OF PLANARRIBBONS IN ESORCINARENE-4,4'-TRIMETHYLENE-DIPYRIDINE-METHANOL (1 2/0.5), AND CAPTURE OF 2,2'-BIPYRIDYL MOLECULES BY PAIRED CALIXARENE BOWLSIN ALIX[4]RESORCINARENE-2,2'-BIPYRIDYL-METHANOL-WATER (1/1/1/1.16)/

Co-crystallisation of the rccc isomer of C-methylcalix[4]resorcinarene 1 with 4,4'-trimethylenedipyridine from methanol yields a solvated 1: 2 adduct 2 in which the resorcinarene acts as a quadruple donor and th e dipyridines both act as double accepters, in O-H ... N hydrogen bond s. The supramolecular structure consists of linear and nearly planar r ibbons with the bowls of the resorcinarene units in one ribbon acting as hosts towards the -(CH2)(3)-spacer units of a neighbouring ribbon, acting as guests. Co-crystallisation of the same resorcinarene 1 with 2,2'-bipyridyl yields a doubly solvated 1 : 1 adduct resorcinarene-2,2 '-bipyridyl-methanol-water (1/1/1/1.16) 3. The resorcinarene, methanol and water molecules combine by means of multiple O-H ... O hydrogen b onds to form paired, essentially-planar two-dimensional nets in which centrosymmetric pairs of resorcinarene bowls act as self-assembled,car cerands to form large cavities in which pairs of 2,2'-bipyridyl molecu les are held by a combination of O-H ... N and C-H ... O hydrogen bond s.