A hydrogen-bonded complex. The crystal structure of 1,5,12,16,23,26,29-heptaoxa[7][5.5]orthocyclophane–naphthalene-2,3-diol monohydrate

Abstract

Reaction between the macrobicyclic ether, 223 (systematically named in the title), and naphthalene-2,3-diol in the presence of water has been shown, by crystal structure analysis, to yield a 1 : 1 : 1 complex. In a monoclinic unit cell having a= 9.014(1), b= 33.302(7), c= 9.663(1)Å, β= 95.42(1)°, space group P2₁/a there are four molecules. Each consists of naphthalene-2,3-diol with the usual internal hydrogen bond and the second hydroxy hydrogen atom bonded to a water molecule (H ⋯ O 1.79 Å) which, in turn, forms hydrogen bonds to four oxygen atoms of the bicyclic molecule; one such bond is bifurcated (H ⋯ O 2.33 and 2.36 Å), while the other has unequal H ⋯ O distances 2.03 and 2.56 Å. Full matrix refinement with anisotropic vibration parameters for the oxygen atoms gave an R value of 0.069 for 3 006 observations from a CAD–4 diffractometer.