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The compounds 2-(1-benzo-furan-2-yl)-2-oxoethyl 2-nitro-benzoate, C 17 H 11 NO 6 (I), and 2-(1-benzo-furan-2-yl)-2-oxoethyl 2-amino-benzoate, C 17 H 13 NO 4 (II), were synthesized under mild conditions. Their mol-ecular structures were characterized by both spectroscopic and single-crystal X-ray diffraction analysis. The mol-ecular conformations of both title compounds are generally similar. However, different ortho -substituted moieties at the phenyl ring of the two compounds cause deviations in the torsion angles between the carbonyl group and the attached phenyl ring. In compound (I), the ortho -nitro-phenyl ring is twisted away from the adjacent carbonyl group whereas in compound (II), the ortho -amino-phenyl ring is almost co-planar with the carbonyl group. In the crystal of compound (I), two C-H⋯O hydrogen bonds link the mol-ecules into chains propagating along the c- axis direction and the chains are inter-digitated, forming sheets parallel to [20-1]. Conversely, pairs of N-H⋯O hydrogen bonds in compound (II) link inversion-related mol-ecules into dimers, which are further extended by C-H⋯O hydrogen bonds into dimer chains. These chains are inter-connected by π-π inter-actions involving the furan rings, forming sheets parallel to the ac plane.

Two closely related 2-(benzofuran-2-yl)-2-oxoethyl benzoates: structural differences and C—H...O hydrogen-bonded supramolecular assemblies