V. N. Sonar, M. Venkatraj, S. Parkin
Jul 1, 2007
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Journal
Acta Crystallographica Section E-structure Reports Online
Abstract
Crystals of the title compound, C8H7NO6, were obtained by the reaction of methyl 2,6-dihydroxybenzoate with nitric acid and crystallization of the product from ethyl acetate. In the molecule, the nitro group is essentially coplanar with the attached benzene ring [O—N—C—C = 5.2 (3)°] indicating conjugation with the π-electron system. The methoxy group of the ester group is cis with respect to the ortho-nitrohydroxyl group. The crystal structure is stabilized by intra- and intermolecular hydrogen bonds. The ortho-nitrohydroxy group forms an intramolecular hydrogen bond with the nitro group and the para-nitrohydroxy group forms an intramolecular hydrogen bond with the ester carbonyl function. In addition, there is intermolecular hydrogen bonding between the ortho-nitrohydroxyl of one molecule and the O atom of para-nitrohydroxyl of another molecule.