Benzyl 2,6-dihydroxy-3-nitrobenzoate

Crystals of the title compound, C14H11NO6, were obtained by the reaction of benzyl 2,6-dihydroxy-benzoate with nitric acid and crystallization of the product from ethyl acetate. In the mol-ecule, the nitro group is essentially coplanar with the attached benzene ring [O - N - C - C = 176.75 (11)°], indicating conjugation with the π-electron system. The benzyloxy group of the ester group is cis with respect to the 2-hydroxy group. The crystal structure is stabilized by intra- and inter-molecular hydrogen bonds. The 2-hydroxy group forms an intra-molecular hydrogen bond with the nitro group, and the 6-hydroxy group forms an intra-molecular hydrogen bond with the ester carbonyl function. In addition, there is inter-molecular hydrogen bonding between the 2-hydroxy group of one mol-ecule and the O atom of the 6-hydroxy group of another mol-ecule.