2-(2-Oxazolin-2-yl)benzene-1,4-diol: X-ray and density functional theory studies

Acta Crystallogr C. 2007 Mar;63(Pt 3):o187-9. doi: 10.1107/S0108270107004131. Epub 2007 Feb 17.

Abstract

In the crystal structure of the title compound, C(9)H(9)NO(3), there are strong intramolecular O-H...N and intermolecular O-H...O hydrogen bonds which, together with weak intermolecular C-H...O hydrogen bonds, lead to the formation of infinite chains of molecules. The calculated intermolecular hydrogen-bond energies are -11.3 and -2.7 kJ mol(-1), respectively, showing the dominant role of the O-H...O hydrogen bonding. A natural bond orbital analysis revealed the electron contribution of the lone pairs of the oxazoline N and O atoms, and of the two hydroxy O atoms, to the order of the relevant bonds.