rac-Methyl 4-azido-3-hydroxy-3-(2-nitrophenyl)butanoate

Abstract

In the title compound, C11H12N4O5, the mean plane through the nitro substituent on the benzene ring is inclined to the benzene mean plane by 85.8 (2)°, which avoids steric interactions with the ortho substituents. The hydroxy group is involved in bifurcated hydrogen bonds. The first is an intramolecular O—H...O hydrogen bond, involving the ester carbonyl O atom, which gives rise to the formation of a boat-like hydrogen-bonded chelate ring. The second is an intermolecular O—H...N hydrogen bond involving the first N atom of the azide group of a symmetry-related molecule. In the crystal structure this leads to the formation of a polmer chain extending in the c-axis direction.