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

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

[img]
Preview
Text
Acta Cryst. (2017). E73, 1674.pdf - Published Version
Available under License Creative Commons Attribution Non-commercial No Derivatives.

Download (981kB) | Preview
Official URL: http://dx.doi.org/10.1107/S205698901701458X

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
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 Science and Technology > Research Centre for Crystalline Materials
Depositing User: Ms. Molly Chuah
Related URLs:
Date Deposited: 30 Oct 2017 03:17
Last Modified: 22 Apr 2019 06:17
URI: http://eprints.sunway.edu.my/id/eprint/629

Actions (login required)

View Item View Item