Nitro Derivatives of 3-Acetamidobenzyl Acetate

The structures of 3-acetamido-2-nitrobenzyl acetate, C₁₁H₁₂N₂O₅, (I), 3-acetamido-6-nitrobenzyl acetate, C₁₁H₁₂N₂O₅, (II) and 3-acetamido-6-nitrobenzyl acetate monohydrate, C₁₁H₁₂N₂O₅.H₂O, (III), have been determined at low temperature – 150 K for (I) and (III), and 100 K for (II). The molecules differ mainly in the conformation of the acetamide and acetate groups with respect to the aromatic ring plane: in (II) they are almost coplanar, in (I) they are markedly distorted from planarity while in (III) they are intermediate. The nitro group is twisted with respect to the aromatic ring in (I), but is almost coplanar with it in (II) and (III). In all three structures one of the nitro O atoms is directed towards a methylene C atom, approximately bisecting the H—C—H angles, and intramolecular C—H...O hydrogen bonds involving the aromatic H and carboxyl O atoms are observed. In all three cases the crystal structures are stabilized by intermolecular N—H...O [and O—H...O in (III)] as well as weak C—H...O hydrogen bonds.

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