( E )-1-[2-(3,4-Dimethylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate

( E )-1-[2-(3,4-Dimethylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate

The title zwitterion, C 18 H 16 N 2 O, features an intramolecular N—H...O hydrogen bond. The dimethylbenzene ring is rotationally disordered about the N—C bond over two adjacent orientations in a 0.75:0.25 ratio. The dihedral angle between the major orientation of the benzene ring and the naphthalen...

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Veröffentlicht in:IUCrData 2017-02, Vol.2 (2), p.x170259, Article x170259
Hauptverfasser: Chetioui, Souheyla, Boutebdja, Mehdi, Boudraa, Mhamed, Touzani, Rachid, Merazig, Hocine
Format: Artikel
Sprache:eng
Schlagworte:
azo dyes
crystal structure
hydrogen bonding
zwitterion
π–π stacking
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Beschreibung
Zusammenfassung:The title zwitterion, C 18 H 16 N 2 O, features an intramolecular N—H...O hydrogen bond. The dimethylbenzene ring is rotationally disordered about the N—C bond over two adjacent orientations in a 0.75:0.25 ratio. The dihedral angle between the major orientation of the benzene ring and the naphthalene ring system is 6.06 (2)°. In the crystal, aromatic π–π stacking occurs [shortest centroid–centroid distance = 3.574 (3) Å] and C—H...O interactions are also observed.
ISSN:2414-3146
2414-3146
DOI:10.1107/S2414314617002590