Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Devika, Bhai R., Girija, C. R., Shalini, Suresh, Jotani, Mukesh M., Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
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
_version_ 1783278291493322752
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.
collection PubMed
description 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.
format Online
Article
Text
id pubmed-5683488
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-56834882017-11-17 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. Acta Crystallogr E Crystallogr Commun Research Communications 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. International Union of Crystallography 2017-10-20 /pmc/articles/PMC5683488/ /pubmed/29152348 http://dx.doi.org/10.1107/S205698901701458X Text en © Devika et al. 2017 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/
spellingShingle Research Communications
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 Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5683488/
https://www.ncbi.nlm.nih.gov/pubmed/29152348
http://dx.doi.org/10.1107/S205698901701458X
work_keys_str_mv AT devikabhair zwitterionic11e4hydroxyphenyliminiomethylnaphthalen2olatecrystalstructureandhirshfeldsurfaceanalysis
AT girijacr zwitterionic11e4hydroxyphenyliminiomethylnaphthalen2olatecrystalstructureandhirshfeldsurfaceanalysis
AT shalinisuresh zwitterionic11e4hydroxyphenyliminiomethylnaphthalen2olatecrystalstructureandhirshfeldsurfaceanalysis
AT jotanimukeshm zwitterionic11e4hydroxyphenyliminiomethylnaphthalen2olatecrystalstructureandhirshfeldsurfaceanalysis
AT tiekinkedwardrt zwitterionic11e4hydroxyphenyliminiomethylnaphthalen2olatecrystalstructureandhirshfeldsurfaceanalysis