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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)...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2016
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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 |
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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 |
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