N-(4-Chlorophenyl)-5-(4,5-dihydro-1H-imidazol-2-yl)thieno[2,3-b]pyridin-4-amine

Abstract

In the title compound, C16H13ClN4S, the thienopyridine fused-ring system is nearly planar (r.m.s. deviation = 0.0333 Å) and forms a dihedral angle of 4.4 (3)° with the attached dihydroimidazole ring (r.m.s. deviation = 0.0429 Å) allowing for the formation of an intramolecular (exocyclic amine)N—H...N(imine) hydrogen bond. The benzene rings of the disordered (50:50) –N(H)—C6H4Cl residue form dihedral angles of 59.1 (3) and 50.59 (15)° with the fused ring system. In the crystal, (imidazole amine)N—H...N(pyridine) hydrogen bonds lead to a supramolecular helical chain along the b axis. The chains assemble into layers (ab plane) with inter-digitation of the chlorobenzene rings which results in weak C—H...Cl interactions in the c-axis direction.