N-[3-(2,6-Dimethylanilino)-1-methylbut-2-enylidene]-2,6-dimethylanilinium chloride

Acta Crystallogr Sect E Struct Rep Online. 2009 Jun 24;65(Pt 7):o1671-2. doi: 10.1107/S1600536809020571.

Abstract

The title salt, C(21)H(27)N(2) (+)·Cl(-) resulted from the condensation between 2,6-dimethyl-aniline and acetyl-acetone in acidified ethanol. The bulky cation is stabilized in a β-imino-enamine 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 supra-molecular structure is a one dimensional polymer running along [001], alternating cations and anions. The π-π inter-action observed in the mol-ecule, 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.