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2-[(E)-({4-[(4,6-Dimethylpyrimidin-2-yl)sulfamoyl]phenyl}iminio)methyl]-6-hydroxyphenolate
The title compound, C(19)H(18)N(4)O(4)S, exists as a zwitterion in the solid state, with nominal proton transfer from a phenol group to the imine N atom. The 2,3-dihydroxybenzaldehyde fragment is oriented at a dihedral angle of 35.51 (11)° to the adajacent aniline group and makes a dihedral angle...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3435708/ https://www.ncbi.nlm.nih.gov/pubmed/22969579 http://dx.doi.org/10.1107/S1600536812034757 |
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author | Tahir, M. Nawaz Khan, Abdul Haleem Iqbal, Mohammad S. Shad, Hazoor Ahmad Yaqub, Muhammad |
author_facet | Tahir, M. Nawaz Khan, Abdul Haleem Iqbal, Mohammad S. Shad, Hazoor Ahmad Yaqub, Muhammad |
author_sort | Tahir, M. Nawaz |
collection | PubMed |
description | The title compound, C(19)H(18)N(4)O(4)S, exists as a zwitterion in the solid state, with nominal proton transfer from a phenol group to the imine N atom. The 2,3-dihydroxybenzaldehyde fragment is oriented at a dihedral angle of 35.51 (11)° to the adajacent aniline group and makes a dihedral angle of 76.99 (6)° with the 4,6-dimethylpyrimidin-2-amine group. Intramolecular O—H⋯O and N—H⋯O hydrogen bonds close S(5) and S(6) rings, respectively; the same O atom accepts both bonds. In the crystal, polymeric chains along [001] are formed from molecules joined end-to-end by N—H⋯O and O—H⋯N hydrogen bonds; these feature R (2) (3)(6) loops. The polymeric chains are linked by C—H⋯O interactions and there are π–π interactions between the pyrimidine rings with a centroid–centroid distance of 3.446 (2) Å. |
format | Online Article Text |
id | pubmed-3435708 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-34357082012-09-11 2-[(E)-({4-[(4,6-Dimethylpyrimidin-2-yl)sulfamoyl]phenyl}iminio)methyl]-6-hydroxyphenolate Tahir, M. Nawaz Khan, Abdul Haleem Iqbal, Mohammad S. Shad, Hazoor Ahmad Yaqub, Muhammad Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(19)H(18)N(4)O(4)S, exists as a zwitterion in the solid state, with nominal proton transfer from a phenol group to the imine N atom. The 2,3-dihydroxybenzaldehyde fragment is oriented at a dihedral angle of 35.51 (11)° to the adajacent aniline group and makes a dihedral angle of 76.99 (6)° with the 4,6-dimethylpyrimidin-2-amine group. Intramolecular O—H⋯O and N—H⋯O hydrogen bonds close S(5) and S(6) rings, respectively; the same O atom accepts both bonds. In the crystal, polymeric chains along [001] are formed from molecules joined end-to-end by N—H⋯O and O—H⋯N hydrogen bonds; these feature R (2) (3)(6) loops. The polymeric chains are linked by C—H⋯O interactions and there are π–π interactions between the pyrimidine rings with a centroid–centroid distance of 3.446 (2) Å. International Union of Crystallography 2012-08-11 /pmc/articles/PMC3435708/ /pubmed/22969579 http://dx.doi.org/10.1107/S1600536812034757 Text en © Tahir et al. 2012 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 | Organic Papers Tahir, M. Nawaz Khan, Abdul Haleem Iqbal, Mohammad S. Shad, Hazoor Ahmad Yaqub, Muhammad 2-[(E)-({4-[(4,6-Dimethylpyrimidin-2-yl)sulfamoyl]phenyl}iminio)methyl]-6-hydroxyphenolate |
title | 2-[(E)-({4-[(4,6-Dimethylpyrimidin-2-yl)sulfamoyl]phenyl}iminio)methyl]-6-hydroxyphenolate |
title_full | 2-[(E)-({4-[(4,6-Dimethylpyrimidin-2-yl)sulfamoyl]phenyl}iminio)methyl]-6-hydroxyphenolate |
title_fullStr | 2-[(E)-({4-[(4,6-Dimethylpyrimidin-2-yl)sulfamoyl]phenyl}iminio)methyl]-6-hydroxyphenolate |
title_full_unstemmed | 2-[(E)-({4-[(4,6-Dimethylpyrimidin-2-yl)sulfamoyl]phenyl}iminio)methyl]-6-hydroxyphenolate |
title_short | 2-[(E)-({4-[(4,6-Dimethylpyrimidin-2-yl)sulfamoyl]phenyl}iminio)methyl]-6-hydroxyphenolate |
title_sort | 2-[(e)-({4-[(4,6-dimethylpyrimidin-2-yl)sulfamoyl]phenyl}iminio)methyl]-6-hydroxyphenolate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3435708/ https://www.ncbi.nlm.nih.gov/pubmed/22969579 http://dx.doi.org/10.1107/S1600536812034757 |
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