Crystal structure of 4-{2-[4-(di-methyl-amino)-phen-yl]diazen-1-yl}-1-methyl-pyridinium iodide

Acta Crystallogr E Crystallogr Commun. 2015 Dec 19;71(Pt 12):o1069-70. doi: 10.1107/S2056989015023646. eCollection 2015 Dec 1.

Abstract

The mol-ecular geometry of the ionic title compound, C14H17N4 (+)·I(-) or DAZOP(+)·I(-), is essentially featureless. Regarding the crystal structure, in addition to the obvious cation-anion Coulombic inter-actions, the packing is mostly directed by non-covalent inter-actions involving both ring systems, as well as the iodide anion. It consists of cationic mol-ecules aligned along [101] and disposed in an anti-parallel fashion while linked into π-bonded dimeric entities by a stacking contact involving symmetry-related phenyl rings, with a centroid-centroid distance of 3.468 (3) Å and a slippage of 0.951 Å. The dimers are, in addition, sustained by a number of C-H⋯I and I⋯π (I⋯centroid = 3.876 Å) inter-actions involving the anion. Finally, inter-dimeric contacts are of the C-H⋯I and C-H⋯π types.

Keywords: C—H⋯ π inter­actions; I⋯π inter­action; NLO; [DAZOP+][I−]; crystal structure; dye; π–π inter­action.