Zwitterionic 1-{(1E)-[(4-hydroxyphenyl)iminio]methyl}naphthalen-2-olate: crystal structure and Hirshfeld surface analysis
The title zwitterion, C17H13NO2 (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)°] a...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
International Union of Crystallography
2017
|
| Subjects: | |
| Online Access: | http://eprints.sunway.edu.my/629/ http://eprints.sunway.edu.my/629/1/Acta%20Cryst.%20%282017%29.%20E73%2C%201674.pdf |
| Summary: | The title zwitterion, C17H13NO2 (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-C6 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. |
|---|