Cargando…

Zwitterionic 4-bromo-6-meth­oxy-2-{[tris­(hy­droxy­meth­yl)methyl]­iminiumyl­meth­yl}phenolate: crystal structure and Hirshfeld surface analysis

In the solid state, the title compound, C(12)H(16)BrNO(5) [systematic name: 4-bromo-2-((1E)-{[1,3-dihy­droxy-2-(hy­droxy­meth­yl)propan-2-yl]iminium­yl}meth­yl)-6-meth­oxy­benzen-1-olate], C(12)H(16)BrNO(5), is found in the keto–amine tautomeric form, with an intra­molecular iminium-N—H⋯O(phenolate)...

Descripción completa

Detalles Bibliográficos
Autores principales: Lee, See Mun, Lo, Kong Mun, Tan, Sang Loon, Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4971878/
https://www.ncbi.nlm.nih.gov/pubmed/27536419
http://dx.doi.org/10.1107/S2056989016012159
_version_ 1782446180504961024
author Lee, See Mun
Lo, Kong Mun
Tan, Sang Loon
Tiekink, Edward R. T.
author_facet Lee, See Mun
Lo, Kong Mun
Tan, Sang Loon
Tiekink, Edward R. T.
author_sort Lee, See Mun
collection PubMed
description In the solid state, the title compound, C(12)H(16)BrNO(5) [systematic name: 4-bromo-2-((1E)-{[1,3-dihy­droxy-2-(hy­droxy­meth­yl)propan-2-yl]iminium­yl}meth­yl)-6-meth­oxy­benzen-1-olate], C(12)H(16)BrNO(5), is found in the keto–amine tautomeric form, with an intra­molecular iminium-N—H⋯O(phenolate) hydrogen bond and an E conformation about the C=N bond. Both gauche (two) and anti relationships are found for the methyl­hydroxy groups. In the crystal, a supra­molecular layer in the bc plane is formed via hy­droxy-O—H⋯O(hy­droxy) and charge-assisted hy­droxy-O—H⋯O(phenolate) hydrogen-bonding inter­actions; various C—H⋯O inter­actions provide additional cohesion to the layers, which stack along the a axis with no directional inter­actions between them. A Hirshfeld surface analysis confirms the lack of specific inter­actions in the inter-layer region.
format Online
Article
Text
id pubmed-4971878
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-49718782016-08-17 Zwitterionic 4-bromo-6-meth­oxy-2-{[tris­(hy­droxy­meth­yl)methyl]­iminiumyl­meth­yl}phenolate: crystal structure and Hirshfeld surface analysis Lee, See Mun Lo, Kong Mun Tan, Sang Loon Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications In the solid state, the title compound, C(12)H(16)BrNO(5) [systematic name: 4-bromo-2-((1E)-{[1,3-dihy­droxy-2-(hy­droxy­meth­yl)propan-2-yl]iminium­yl}meth­yl)-6-meth­oxy­benzen-1-olate], C(12)H(16)BrNO(5), is found in the keto–amine tautomeric form, with an intra­molecular iminium-N—H⋯O(phenolate) hydrogen bond and an E conformation about the C=N bond. Both gauche (two) and anti relationships are found for the methyl­hydroxy groups. In the crystal, a supra­molecular layer in the bc plane is formed via hy­droxy-O—H⋯O(hy­droxy) and charge-assisted hy­droxy-O—H⋯O(phenolate) hydrogen-bonding inter­actions; various C—H⋯O inter­actions provide additional cohesion to the layers, which stack along the a axis with no directional inter­actions between them. A Hirshfeld surface analysis confirms the lack of specific inter­actions in the inter-layer region. International Union of Crystallography 2016-07-29 /pmc/articles/PMC4971878/ /pubmed/27536419 http://dx.doi.org/10.1107/S2056989016012159 Text en © Lee et al. 2016 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Research Communications
Lee, See Mun
Lo, Kong Mun
Tan, Sang Loon
Tiekink, Edward R. T.
Zwitterionic 4-bromo-6-meth­oxy-2-{[tris­(hy­droxy­meth­yl)methyl]­iminiumyl­meth­yl}phenolate: crystal structure and Hirshfeld surface analysis
title Zwitterionic 4-bromo-6-meth­oxy-2-{[tris­(hy­droxy­meth­yl)methyl]­iminiumyl­meth­yl}phenolate: crystal structure and Hirshfeld surface analysis
title_full Zwitterionic 4-bromo-6-meth­oxy-2-{[tris­(hy­droxy­meth­yl)methyl]­iminiumyl­meth­yl}phenolate: crystal structure and Hirshfeld surface analysis
title_fullStr Zwitterionic 4-bromo-6-meth­oxy-2-{[tris­(hy­droxy­meth­yl)methyl]­iminiumyl­meth­yl}phenolate: crystal structure and Hirshfeld surface analysis
title_full_unstemmed Zwitterionic 4-bromo-6-meth­oxy-2-{[tris­(hy­droxy­meth­yl)methyl]­iminiumyl­meth­yl}phenolate: crystal structure and Hirshfeld surface analysis
title_short Zwitterionic 4-bromo-6-meth­oxy-2-{[tris­(hy­droxy­meth­yl)methyl]­iminiumyl­meth­yl}phenolate: crystal structure and Hirshfeld surface analysis
title_sort zwitterionic 4-bromo-6-meth­oxy-2-{[tris­(hy­droxy­meth­yl)methyl]­iminiumyl­meth­yl}phenolate: crystal structure and hirshfeld surface analysis
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4971878/
https://www.ncbi.nlm.nih.gov/pubmed/27536419
http://dx.doi.org/10.1107/S2056989016012159
work_keys_str_mv AT leeseemun zwitterionic4bromo6methoxy2trishydroxymethylmethyliminiumylmethylphenolatecrystalstructureandhirshfeldsurfaceanalysis
AT lokongmun zwitterionic4bromo6methoxy2trishydroxymethylmethyliminiumylmethylphenolatecrystalstructureandhirshfeldsurfaceanalysis
AT tansangloon zwitterionic4bromo6methoxy2trishydroxymethylmethyliminiumylmethylphenolatecrystalstructureandhirshfeldsurfaceanalysis
AT tiekinkedwardrt zwitterionic4bromo6methoxy2trishydroxymethylmethyliminiumylmethylphenolatecrystalstructureandhirshfeldsurfaceanalysis