X-ray structure of beta-cyclodextrin-2,7-dihydroxy-naphthalene.4.6 H(2)O: an unusually distorted macrocycle

Carbohydr Res. 2001 Jul 12;333(3):251-6. doi: 10.1016/s0008-6215(01)00131-8.

Abstract

The inclusion complex beta-cyclodextrin.2,7-dihydroxynaphthalene.4.6 H(2)O crystallized in the monoclinic space group P2(1), with a=14.082(3), b=19.079(4), c=12.417(3) A, beta=109.28(3) degrees, V=3149.0(11) A(3), and Z=2. An X-ray study performed at room temperature shows that the crystal packing is of the herringbone type with one 2,7-dihydroxynaphthalene included completely in the beta-CD cavity, its long axis being oriented along the beta-CD molecular axis, and 4.6 water molecules are placed in the interstitial space. The beta-CD macrocycle is elliptically distorted, and the guest molecule is held in the hydrophobic beta-CD cavity by C-H...O and C-H...pi interactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Cyclodextrins / chemistry*
  • Hydrogen Bonding
  • Ligands
  • Molecular Conformation
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Oligosaccharides / chemistry
  • Water
  • beta-Cyclodextrins*

Substances

  • Cyclodextrins
  • Ligands
  • Naphthalenes
  • Oligosaccharides
  • beta-Cyclodextrins
  • cyclodextrin-2,7-dihydroxy-naphthalene
  • Water