N-[3-(2,6-Dimethylanilino)-1-methylbut-2-enylidene]-2,6-dimethylanilinium chlorideThis paper is dedicated to Professor Dr Dr mult. h.c. Herbert W. Roesky.

Abstract

The title salt, C21H27N2+·Cl− resulted from the condensation between 2,6-dimethylaniline and acetylacetone in acidified ethanol. The bulky cation is stabilized in a β-iminoenamine tautomeric form, and presents a W-shaped conformation. The benzene rings are arranged almost parallel, with a dihedral angle of 6.58 (4)° between the mean planes. Both N—H groups in the cation form strong hydrogen bonds with two symmetry-related chloride anions. The resulting supramolecular structure is a one dimensional polymer running along [001], alternating cations and anions. The π–π interaction observed in the molecule, characterized by a centroid–centroid separation of 4.298 (4) Å, is thus extended to the chains, with separations of 5.222 (4) Å between benzene rings of neighbouring cations in the crystal.