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4-(2,4-dihydroxyphenyl)-2,2,4-trimethylchroman: A diol counterpart of Dianin's compound

By T.W. Beresford, C.S. Frampton, J.H. Gall and D.D. MacNicol

Abstract

The title resorcinol forms true clathrates analogous to those formed by Dianin's compound itself; the ethyl acetate clathrate has space group R (3) over bar, with a = 27.222(3), c = 10.727(2) Angstrom, and Z = 18 (host). One of the diol host's OH groups participates ill a hydrogen-bonded [OH](6) unit, whilst the other forms an OH...O (ether) hydrogen bond to an adjacent hexameric unit stacked (infinitely) along the c axis. In contrast to Dia,lin's compound, sublimation in vacuo does not give the stable "empty" cage form, but leads to spontaneous resolution, the unsolvated crystal being orthorhombic, space group P2(1)2(1)2(1) with a = 9.9031(15), b = 10.599(3), c = 13.501(4) Angstrom, and Z = 4. Molecules are now linked head- to-tail by OH...O (ether) hydrogen bonds to form infinite chains translationally propagated along a. Two such adjacent, parallel chains, related by a 2(1) screw axis along a, form a pair consolidated by intermolecular hydrogen bands of OH...O(H) type, involving both hydroxyl groups of the diol

Topics: QD
Year: 1999
DOI identifier: 10.1007/bf02903446
OAI identifier: oai:eprints.gla.ac.uk:2001
Provided by: Enlighten
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