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
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Acta Cryst. (2017). E73, 1674.pdf - Published Version Available under License Creative Commons Attribution Non-commercial No Derivatives. Download (981kB) | Preview |
Abstract
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.
| Item Type: | Article |
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| Additional Information: | First author is with Research & Development Centre, Bharathiar University; 2nd author is with Govt. Science College, Bangalore and SSMRV College, Bangalore; 3rd author is with SSMRV College, Bangalore; 4th author is with Department of Physics, Bhavan’s Sheth R. A. College of Science, Ahmedabad; 5th author is with Research Centre for Crystalline Materials, School of Science and Technology, Sunway University |
| Uncontrolled Keywords: | crystal structure; zwitterion; Schiff base; hydrogen bonding; Hirshfeld surface analysis |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Others > Non Sunway Academics Sunway University > School of Engineering and Technology [formerly School of Science and Technology until 2020] > Research Centre for Crystalline Materials moved to SMLS wef 2021 |
| Depositing User: | Ms. Molly Chuah |
| Related URLs: | |
| Date Deposited: | 30 Oct 2017 03:17 |
| Last Modified: | 07 Oct 2020 09:43 |
| URI: | http://eprints.sunway.edu.my/id/eprint/629 |
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