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

Molecules of 2-chloro-N-(2-nitrophenyl) nicotinamide, C12H8ClN3O3, are linked by two C-H center dot center dot center dot O hydrogen bonds into a chain of edge-fused R(2)(2)2(14) and R-4(4)(24) rings. In 2-chloro-N-(3-nitrophenyl) nicotinamide monohydrate, C(12)H(8)ClN(3)O(3)center dot H2O, the molecules are linked by a combination of N-H center dot center dot center dot O, O-H center dot center dot center dot O and O-H center dot center dot center dot N hydrogen bonds into a chain of edge-fused rings containing two distinct types of R-4(4)(16) ring. In 2-chloro-N-(4-nitrophenyl)nicotinamide, C12H8ClN3O3, which crystallizes with Z' = 2 in space group P2(1)/n, the molecules are linked by two N-H center dot center dot center dot N hydrogen bonds into simple C-2(2)(12) chains.