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...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2017
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| Online Access: | http://eprints.sunway.edu.my/629/ http://eprints.sunway.edu.my/629/1/Acta%20Cryst.%20%282017%29.%20E73%2C%201674.pdf |
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| author | Devika, Bhai R. Girija, C. R. Shalini, Suresh Jotani, Mukesh M. Tiekink, Edward R. T. * |
| author_facet | Devika, Bhai R. Girija, C. R. Shalini, Suresh Jotani, Mukesh M. Tiekink, Edward R. T. * |
| author_sort | Devika, Bhai R. |
| building | SU Institutional Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T21:14:14Z |
| format | Article |
| id | sunway-629 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:14:14Z |
| publishDate | 2017 |
| publisher | International Union of Crystallography |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-6292020-10-07T09:43:59Z http://eprints.sunway.edu.my/629/ Zwitterionic 1-{(1E)-[(4-hydroxyphenyl)iminio]methyl}naphthalen-2-olate: crystal structure and Hirshfeld surface analysis Devika, Bhai R. Girija, C. R. Shalini, Suresh Jotani, Mukesh M. Tiekink, Edward R. T. * QD Chemistry 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. International Union of Crystallography 2017 Article PeerReviewed text en cc_by_nc_nd http://eprints.sunway.edu.my/629/1/Acta%20Cryst.%20%282017%29.%20E73%2C%201674.pdf Devika, Bhai R. and Girija, C. R. and Shalini, Suresh and Jotani, Mukesh M. and Tiekink, Edward R. T. * (2017) Zwitterionic 1-{(1E)-[(4-hydroxyphenyl)iminio]methyl}naphthalen-2-olate: crystal structure and Hirshfeld surface analysis. Acta Crystallographica Section E Crystallographic Communications, 73 (11). pp. 1674-1678. ISSN 2056-9890 http://dx.doi.org/10.1107/S205698901701458X doi:10.1107/S205698901701458X |
| spellingShingle | QD Chemistry Devika, Bhai R. Girija, C. R. Shalini, Suresh Jotani, Mukesh M. Tiekink, Edward R. T. * Zwitterionic 1-{(1E)-[(4-hydroxyphenyl)iminio]methyl}naphthalen-2-olate: crystal structure and Hirshfeld surface analysis |
| title | Zwitterionic 1-{(1E)-[(4-hydroxyphenyl)iminio]methyl}naphthalen-2-olate: crystal structure and Hirshfeld surface analysis |
| title_full | Zwitterionic 1-{(1E)-[(4-hydroxyphenyl)iminio]methyl}naphthalen-2-olate: crystal structure and Hirshfeld surface analysis |
| title_fullStr | Zwitterionic 1-{(1E)-[(4-hydroxyphenyl)iminio]methyl}naphthalen-2-olate: crystal structure and Hirshfeld surface analysis |
| title_full_unstemmed | Zwitterionic 1-{(1E)-[(4-hydroxyphenyl)iminio]methyl}naphthalen-2-olate: crystal structure and Hirshfeld surface analysis |
| title_short | Zwitterionic 1-{(1E)-[(4-hydroxyphenyl)iminio]methyl}naphthalen-2-olate: crystal structure and Hirshfeld surface analysis |
| title_sort | zwitterionic 1-{(1e)-[(4-hydroxyphenyl)iminio]methyl}naphthalen-2-olate: crystal structure and hirshfeld surface analysis |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/629/ http://eprints.sunway.edu.my/629/ http://eprints.sunway.edu.my/629/ http://eprints.sunway.edu.my/629/1/Acta%20Cryst.%20%282017%29.%20E73%2C%201674.pdf |