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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...

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Autores principales: Tahir, M. Nawaz, Khan, Abdul Haleem, Iqbal, Mohammad S., Shad, Hazoor Ahmad, Yaqub, Muhammad
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
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.
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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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