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 dete rmined 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 wit h 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 i s directed towards a methylene C atom, approximately bisecting the H-C -H angles, and intramolecular C-H ... O hydrogen bonds involving the a romatic H and carboxyl O atoms are observed. In all three cases, the c rystal structures are stabilized by intermolecular N-H ... O [and O-H ... O in (III)], as well as weak C-H ... O, hydrogen bonds.