Methyl 2,6‐dihydroxy‐3‐nitrobenzoate

Publisher: John Wiley & Sons Inc

E-ISSN: 1600-5368|63|7|o3227-o3227

ISSN: 1600-5368

Source: Acta Crystallographica Section E, Vol.63, Iss.7, 2007-07, pp. : o3227-o3227

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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.