Three ethyl 5-amino-1-aryl-1H-imidazole-4-carboxylates: hydrogen-bonded supramolecular structures in one, two and three dimensions

The molecules of ethyl 5-amino-1-(4-cyanophenyl)-1H-imidazole-4-carboxylate, C13H12N4O2, are linked into a chain of alternating R-2(2)(10) and R-4(4)(34) rings by a combination of N-H center dot center dot center dot N and C-H center dot center dot center dot N hydrogen bonds. In ethyl 5-amino-1-(4-chlorophenyl)-1H-imidazole-4-carboxylate, C12H12ClN3O2, where the ethyl group is disordered over two sets of sites, a combination of N-H center dot center dot center dot O, N-H center dot center dot center dot N, C-H center dot center dot center dot N and C-H center dot center dot center dot pi(arene) hydrogen bonds links the molecules into complex sheets. Two intermolecular hydrogen bonds, one each of N-H center dot center dot center dot N and C-H center dot center dot center dot O types, link the molecules of ethyl 5-amino-1-(2,6-difluorophenyl)-1H-imidazole-4-carboxylate, C12H11F2N3O2, into a continuous three-dimensional framework structure.