Crystal structure of (Z)-ethyl 3-[2-(5-methyl-7-nitro-1H-indole-2-carbonyl)-hydrazinylidene]butanoate

Abstract

The reaction of 5-methyl-7-nitro-1H-indole-2-carbohydrazide with ethyl acetoacetate yielded the title molecule, C16H18-N4O5, in which the indole ring is almost planar, with the greatest deviation from the mean plane being 0.006 (2) A . The nine atoms of the indole ring are almost perpendicular to the mean plane through the ethyl acetate group, as indicated by the dihedral angle of 87.02 (4)° between them. In the crystal, centrosymmetric supramolecular dimers are formed via N- H⋯O hydrogen bonds and eight-membered amide {⋯HNCO}2 synthons. These are consolidated into a threedimensional architecture by C-H⋯O contacts, and by π-π interactions between six-membered rings [inter-centroid distance = 3.499 (2) A ].