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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2017
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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 |
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. |
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