2-amino derivatives of 5-nitrophenylacetamide

Abstract

The structures of the potential non-linear optical (NLO) materials N-[2-(iso­propyl­amino)-5-nitro­phenyl]­acet­amide, (I) C11H15N3O3, and N-[2-(butyl­amino)-5-nitro­phenyl]­acet­amide, (II) C12H17N3O3, have been investigated by X-ray analysis. To compare them with the structure of N-[2-(di­methyl­amino)-5-nitro­phenyl]­acet­amide, (III) C10H13N3O3, a known NLO compound, we had to redetermine the structure of (III), since it was described only briefly in the literature. There are two mol­ecules in the asymmetric unit of compound (I), which have different orientations of the substituents with respect to the benzene ring. The packing of mol­ecules in (II) and (III) contains stacks but both (I) and (II) crystallize in a centrosymmetric space group, which renders them inappropriate for NLO applications.