Cargando…

Zwitterionic 1-{(1E)-[(4-hy­droxy­phen­yl)iminio]meth­yl}naphthalen-2-olate: crystal structure and Hirshfeld surface analysis

The title zwitterion, C(17)H(13)NO(2) (systematic name: 1-{(1E)-[(4-hy­droxy­phen­yl)iminium­yl]meth­yl}naphthalen-2-olate), features an intra­molecular charge-assisted N(+)—H⋯O(−) hydrogen bond. A twist in the mol­ecule is evident around the N—C(hy­droxy­benzene) bond [C—N—C—C torsion angle = 39.42...

Descripción completa

Detalles Bibliográficos
Autores principales: Devika, Bhai R., Girija, C. R., Shalini, Suresh, Jotani, Mukesh M., Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5683488/
https://www.ncbi.nlm.nih.gov/pubmed/29152348
http://dx.doi.org/10.1107/S205698901701458X
Descripción
Sumario:The title zwitterion, C(17)H(13)NO(2) (systematic name: 1-{(1E)-[(4-hy­droxy­phen­yl)iminium­yl]meth­yl}naphthalen-2-olate), features an intra­molecular charge-assisted N(+)—H⋯O(−) hydrogen bond. A twist in the mol­ecule is evident around the N—C(hy­droxy­benzene) bond [C—N—C—C torsion angle = 39.42 (8)°] and is reflected in the dihedral angle of 39.42 (8)° formed between the aromatic regions of the mol­ecule. In the crystal, zigzag supra­molecular chains along the a axis are formed by charge-assisted hy­droxy-O—H⋯O(phenoxide) hydrogen bonding. These are connected into a layer in the ab plane by charge-assisted hy­droxy­benzene-C—H⋯O(phenoxide) inter­actions and π–π contacts [inter-centroid distance between naphthyl-C(6) rings = 3.4905 (12) Å]. Layers stack along the c axis with no specific inter­actions between them. The Hirshfeld surface analysis points to the significance C⋯H contacts between layers.