Cargando…

4-[(5-Bromo-2-hydroxy­benzyl­idene)amino]-N-(4,6-dimethyl­pyrimidin-2-yl)benzene­sulfonamide–4-bromo-2-[(E)-({4-[(4,6-dimethyl­pyrimidin-2-yl)sulfamo­yl]phen­yl}iminio)meth­yl]phenolate [0.61 (7)/0.39 (7)]

The title compound, 0.61C(19)H(17)BrN(4)O(3)S·0.39C(19)H(17)BrN(4)O(3)S, is a Schiff base derived from 5-bromo­salicylaldehyde and 4-amino-N-(4,6-dimethyl-2-pyrimidin­yl)benzene­sulfonamide(sulfamethazine) and is isostructural with its chloro analogue. The geometry of the title mol­ecule points to t...

Descripción completa

Detalles Bibliográficos
Autores principales: Shad, Hazoor A., Tahir, M. Nawaz, Chohan, Zahid H.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968005/
https://www.ncbi.nlm.nih.gov/pubmed/21581736
http://dx.doi.org/10.1107/S1600536808041214
_version_ 1782189747481870336
author Shad, Hazoor A.
Tahir, M. Nawaz
Chohan, Zahid H.
author_facet Shad, Hazoor A.
Tahir, M. Nawaz
Chohan, Zahid H.
author_sort Shad, Hazoor A.
collection PubMed
description The title compound, 0.61C(19)H(17)BrN(4)O(3)S·0.39C(19)H(17)BrN(4)O(3)S, is a Schiff base derived from 5-bromo­salicylaldehyde and 4-amino-N-(4,6-dimethyl-2-pyrimidin­yl)benzene­sulfonamide(sulfamethazine) and is isostructural with its chloro analogue. The geometry of the title mol­ecule points to the enol (OH—C=C—C=N) form as the major tautomer, however two electron-density maxima corresponding to the H atoms of the OH and NH groups, found in the region of a strong intra­molecular N⋯H⋯O hydrogen bond, do not allow the elimination of the presence of the zwitterionic (O(−)—C=C—C=NH(+)) form in the crystal. Refinement of the occupancies of these H atoms gave a 0.61 (7):0.39 (7) ratio of the enolic and zwitterionic forms. The two benzene rings within the mol­ecule are nearly coplanar and the central benzene ring forms a dihedral angle of 84.1 (1)° with the pyrimidine fragment. An inter­molecular N—H⋯O hydrogen bond links mol­ecules into chains extended along the a axis and a C—H⋯O link is also present. The H atoms of one of the methyl groups are disordered over two sites with an occupancy ratio of 0.72 (7):0.28 (7).
format Text
id pubmed-2968005
institution National Center for Biotechnology Information
language English
publishDate 2008
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-29680052010-12-30 4-[(5-Bromo-2-hydroxy­benzyl­idene)amino]-N-(4,6-dimethyl­pyrimidin-2-yl)benzene­sulfonamide–4-bromo-2-[(E)-({4-[(4,6-dimethyl­pyrimidin-2-yl)sulfamo­yl]phen­yl}iminio)meth­yl]phenolate [0.61 (7)/0.39 (7)] Shad, Hazoor A. Tahir, M. Nawaz Chohan, Zahid H. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, 0.61C(19)H(17)BrN(4)O(3)S·0.39C(19)H(17)BrN(4)O(3)S, is a Schiff base derived from 5-bromo­salicylaldehyde and 4-amino-N-(4,6-dimethyl-2-pyrimidin­yl)benzene­sulfonamide(sulfamethazine) and is isostructural with its chloro analogue. The geometry of the title mol­ecule points to the enol (OH—C=C—C=N) form as the major tautomer, however two electron-density maxima corresponding to the H atoms of the OH and NH groups, found in the region of a strong intra­molecular N⋯H⋯O hydrogen bond, do not allow the elimination of the presence of the zwitterionic (O(−)—C=C—C=NH(+)) form in the crystal. Refinement of the occupancies of these H atoms gave a 0.61 (7):0.39 (7) ratio of the enolic and zwitterionic forms. The two benzene rings within the mol­ecule are nearly coplanar and the central benzene ring forms a dihedral angle of 84.1 (1)° with the pyrimidine fragment. An inter­molecular N—H⋯O hydrogen bond links mol­ecules into chains extended along the a axis and a C—H⋯O link is also present. The H atoms of one of the methyl groups are disordered over two sites with an occupancy ratio of 0.72 (7):0.28 (7). International Union of Crystallography 2008-12-13 /pmc/articles/PMC2968005/ /pubmed/21581736 http://dx.doi.org/10.1107/S1600536808041214 Text en © Shad et al. 2009 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
Shad, Hazoor A.
Tahir, M. Nawaz
Chohan, Zahid H.
4-[(5-Bromo-2-hydroxy­benzyl­idene)amino]-N-(4,6-dimethyl­pyrimidin-2-yl)benzene­sulfonamide–4-bromo-2-[(E)-({4-[(4,6-dimethyl­pyrimidin-2-yl)sulfamo­yl]phen­yl}iminio)meth­yl]phenolate [0.61 (7)/0.39 (7)]
title 4-[(5-Bromo-2-hydroxy­benzyl­idene)amino]-N-(4,6-dimethyl­pyrimidin-2-yl)benzene­sulfonamide–4-bromo-2-[(E)-({4-[(4,6-dimethyl­pyrimidin-2-yl)sulfamo­yl]phen­yl}iminio)meth­yl]phenolate [0.61 (7)/0.39 (7)]
title_full 4-[(5-Bromo-2-hydroxy­benzyl­idene)amino]-N-(4,6-dimethyl­pyrimidin-2-yl)benzene­sulfonamide–4-bromo-2-[(E)-({4-[(4,6-dimethyl­pyrimidin-2-yl)sulfamo­yl]phen­yl}iminio)meth­yl]phenolate [0.61 (7)/0.39 (7)]
title_fullStr 4-[(5-Bromo-2-hydroxy­benzyl­idene)amino]-N-(4,6-dimethyl­pyrimidin-2-yl)benzene­sulfonamide–4-bromo-2-[(E)-({4-[(4,6-dimethyl­pyrimidin-2-yl)sulfamo­yl]phen­yl}iminio)meth­yl]phenolate [0.61 (7)/0.39 (7)]
title_full_unstemmed 4-[(5-Bromo-2-hydroxy­benzyl­idene)amino]-N-(4,6-dimethyl­pyrimidin-2-yl)benzene­sulfonamide–4-bromo-2-[(E)-({4-[(4,6-dimethyl­pyrimidin-2-yl)sulfamo­yl]phen­yl}iminio)meth­yl]phenolate [0.61 (7)/0.39 (7)]
title_short 4-[(5-Bromo-2-hydroxy­benzyl­idene)amino]-N-(4,6-dimethyl­pyrimidin-2-yl)benzene­sulfonamide–4-bromo-2-[(E)-({4-[(4,6-dimethyl­pyrimidin-2-yl)sulfamo­yl]phen­yl}iminio)meth­yl]phenolate [0.61 (7)/0.39 (7)]
title_sort 4-[(5-bromo-2-hydroxy­benzyl­idene)amino]-n-(4,6-dimethyl­pyrimidin-2-yl)benzene­sulfonamide–4-bromo-2-[(e)-({4-[(4,6-dimethyl­pyrimidin-2-yl)sulfamo­yl]phen­yl}iminio)meth­yl]phenolate [0.61 (7)/0.39 (7)]
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968005/
https://www.ncbi.nlm.nih.gov/pubmed/21581736
http://dx.doi.org/10.1107/S1600536808041214
work_keys_str_mv AT shadhazoora 45bromo2hydroxybenzylideneaminon46dimethylpyrimidin2ylbenzenesulfonamide4bromo2e446dimethylpyrimidin2ylsulfamoylphenyliminiomethylphenolate06170397
AT tahirmnawaz 45bromo2hydroxybenzylideneaminon46dimethylpyrimidin2ylbenzenesulfonamide4bromo2e446dimethylpyrimidin2ylsulfamoylphenyliminiomethylphenolate06170397
AT chohanzahidh 45bromo2hydroxybenzylideneaminon46dimethylpyrimidin2ylbenzenesulfonamide4bromo2e446dimethylpyrimidin2ylsulfamoylphenyliminiomethylphenolate06170397