Hydrogen-bonding and carbonyl-carbonyl interactions in violuric acid methanol solvate

Abstract

Violuric acid [systematic name: pyrimidine-2,4,5,6(1H,3H)-tetrone 5-oxime] crystallizes from a methanol solution stored at approximately 278 K as a monosolvate, C4N3N3O4·CH 3OH, in the form of very small and fragile needles. Synchrotron radiation was needed to collect an adequate data set. Analysis of the crystal structure reveals that the isonitroso group of violuric acid is disordered over two positions with refined occupancies of approximately 3:1 for the major and minor disorder components. This fact has some important consequences for the hydrogen-bonding motifs found in the crystal packing, which are different for each component, although the overall packing pattern does not change. The crystal packing consists of closely stacked hydrogen-bonded sheets. Between the sheets are found carbonyl-carbonyl dipolar interactions, which are the principal intermolecular forces holding the sheets together. © 2005 International Union of Crystallography.