Journal of Structural Chemistry

, Volume 40, Issue 5, pp 705–713 | Cite as

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

  • T. W. Beresford
  • C. S. Frampton
  • J. H. Gall
  • D. D. MacNicol


The title resorcinol forms true clathrates analogous to those formed by Dianin’s compound itself; the ethyl acetate clathrate has space group R3, with a = 27.222(3), c = 10.727(2) å, and Z = 18 (host). One of the diol host’s OH groups participates in a hydrogen-bonded [OH]6 unit, whilst the other forms an 0H...0 (ether) hydrogen bond to an adjacent hexameric unit stacked (infinitely) along the c axis. In contrast to Dianin’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 P212121 with a = 9.9031(15), b = 10.599(3), c= 13.501(4) Å, and Z = 4. Molecules are now linked head- to- tail by OH...0 (ether) hydrogen bonds to form infinite chains translationally propagated along a. Two such adjacent, parallel chains, related by a 21 screw axis along a, form a pair consolidated by intemwlecular hydrogen bonds of OH...O(H) type, involving both hydroxyl groups of the diol.


Clathrate EtOAc Inclusion Compound Screw Axis Dimethyl Acetylenedicarboxylate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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Copyright information

© Kluwer Academic/Plenum Publishers 1999

Authors and Affiliations

  • T. W. Beresford
    • 1
  • C. S. Frampton
    • 1
  • J. H. Gall
    • 1
  • D. D. MacNicol
    • 1
  1. 1.Roche Discovery WelwynUniversity of GlasgowWelwyn Garden CityGreat Britain

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