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Comparison of the structures of 1,5-dichloro- and 1,5-dibromonaphthalene-2,6-diol and their co-crystalline compounds with dioxane

Abstract

The 1,5-dichloro-(1) and 1,5-dibromo-(2) naphthalene-2,6-diols form isostructural lattices incorporating ...O−H...O−H...O−H... hydrogen bonding surrounding 21 screw axes. Each phenolic hydroxy group participates in one donor and one acceptor hydrogen bond. When crystallised from dioxane, both compounds form new 1:1 co-crystalline materials whose lattices are closely related but not isostructural. All inter-phenolic hydrogen bonding is now absent with each hydroxy group acting instead as a donor to a dioxane oxygen atom. In consequence, the hydrogen bonded layer structures of pure1 or2 are now replaced by hydrogen bonded chain arrangements. All four crystal structures are analysed and compared in crystal engineering terms through discussion of the various types of other weak intermolecular attractions involved in their lattice constructions.

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Correspondence to Roger Bishop.

Additional information

Supplementary Data relating to this article are deposited with the British Library as supplementary publication No. SUP 82202 (19 pages).

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Ahn, P.D., Bishop, R., Craig, D.C. et al. Comparison of the structures of 1,5-dichloro- and 1,5-dibromonaphthalene-2,6-diol and their co-crystalline compounds with dioxane. J Incl Phenom Macrocycl Chem 23, 313–327 (1995). https://doi.org/10.1007/BF00707935

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Key words

  • Phenols
  • dioxane
  • hydrogen bonding
  • screw axes
  • aromatic ring interactions
  • weak attractive forces