Supramolecular structures of three isomeric 2-chloro-N-(nitrophenyl) nicotinamides

Abstract

Molecules of 2-chloro-N-(2-nitrophenyl)nicotinamide, C12H 8ClN3O3, are linked by two C-H⋯O hydrogen bonds into a chain of edge-fused R22(14) and R44(24) rings. In 2-chloro-N-(3-nitrophenyl)nicotinamide monohydrate, C12H8ClN3O3· H2O, the molecules are linked by a combination of N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds into a chain of edge-fused rings containing two distinct types of R44(16) ring. In 2-chloro-N-(4-nitrophenyl)nicotinamide, C12H8ClN 3O3, which crystallizes with Z′ = 2 in space group P21/n, the molecules are linked by two N-H⋯N hydrogen bonds into simple C22(12) chains. © 2005 International Union of Crystallography.