title: (E)-1-[2-(2-Cyano-phen-yl)diazen-2-ium-1-yl]naphthalen-2-olate.
abstract: There are two independent zwitterion mol-ecules (A and B) in the asymmetric unit of the title compound, C17H11N3O, which belongs to the family of azo dyes. The dihedral angle between the benzene ring and the naphthalene ring system is 6.99 (6)° in mol-ecule A and 4.38 (6)° in mol-ecule B. The azo group adopts an E conformation with respect to the -N=N- bond and each of the independent mol-ecules has an intra-molecular N-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯N hydrogen bonds, forming ribbons propagating along [-110]. The ribbons are linked via π-π inter-actions involving the benzene and naphthalene rings of inversion-related A and inversion-related B mol-ecules, forming a three-dimensional structure. The most significant centroid-centroid distances vary from 3.6599 (6) to 3.7538 (9) Å.
authors.affiliation: Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Département de Chimie, Université Mentouri de Constantine 1, 25000 Constantine, Algeria.
authors.forename: Hassiba
authors.initials: H
authors.lastname: Bougueria
authors.forename: Mohamed Amine
authors.initials: MA
authors.lastname: Benaouida
authors.forename: Sofiane
authors.initials: S
authors.lastname: Bouacida
authors.forename: Abd El Kader
authors.initials: Ael K
authors.lastname: Bouchoul
references.citation: J Org Chem. 2004 Apr 16;69(8):2902-5
references.pmid: 15074952
references.citation: Acta Crystallogr A. 2008 Jan;64(Pt 1):112-22
references.pmid: 18156677