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4-[(2,4-Dihydroxy­benzyl­idene)ammonio]benzene­sulfonate trihydrate

The title Schiff base compound, C(13)H(11)NO(5)S·3H(2)O, formed from sulfanilic acid and 2,4-dihydroxy­benzaldehyde, crystallized out as a zwitterion with the N atom protonated. The asymmetric unit consists of one 4-[(2,4-dihydroxy­benzyl­idene)ammonio]benzene­sulfonate and three water mol­ecules. T...

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Autores principales: Yeap, Chin Sing, Hemamalini, Madhukar, Fun, Hoong-Kun
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983714/
https://www.ncbi.nlm.nih.gov/pubmed/21580347
http://dx.doi.org/10.1107/S1600536810004526
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author Yeap, Chin Sing
Hemamalini, Madhukar
Fun, Hoong-Kun
author_facet Yeap, Chin Sing
Hemamalini, Madhukar
Fun, Hoong-Kun
author_sort Yeap, Chin Sing
collection PubMed
description The title Schiff base compound, C(13)H(11)NO(5)S·3H(2)O, formed from sulfanilic acid and 2,4-dihydroxy­benzaldehyde, crystallized out as a zwitterion with the N atom protonated. The asymmetric unit consists of one 4-[(2,4-dihydroxy­benzyl­idene)ammonio]benzene­sulfonate and three water mol­ecules. The zwitterion exists in an E configuration with respect to the central C=N double bond. The two benzene rings of the mol­ecule are oriented at a dihedral angle of 27.33 (8)°. An intra­molecular N–H⋯O hydrogen bond stabilizes the mol­ecular structure. In the crystal, the zwitterions are linked into chains along [101] by inter­molecular O—H⋯O and N—H⋯O hydrogen bonds. The three water mol­ecules link these chains into a three-dimensional framework by additional inter­molecular O—H⋯O hydrogen bonds. A π⋯π inter­action [3.5485 (9) Å] further stabilizes the crystal structure.
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spelling pubmed-29837142010-12-30 4-[(2,4-Dihydroxy­benzyl­idene)ammonio]benzene­sulfonate trihydrate Yeap, Chin Sing Hemamalini, Madhukar Fun, Hoong-Kun Acta Crystallogr Sect E Struct Rep Online Organic Papers The title Schiff base compound, C(13)H(11)NO(5)S·3H(2)O, formed from sulfanilic acid and 2,4-dihydroxy­benzaldehyde, crystallized out as a zwitterion with the N atom protonated. The asymmetric unit consists of one 4-[(2,4-dihydroxy­benzyl­idene)ammonio]benzene­sulfonate and three water mol­ecules. The zwitterion exists in an E configuration with respect to the central C=N double bond. The two benzene rings of the mol­ecule are oriented at a dihedral angle of 27.33 (8)°. An intra­molecular N–H⋯O hydrogen bond stabilizes the mol­ecular structure. In the crystal, the zwitterions are linked into chains along [101] by inter­molecular O—H⋯O and N—H⋯O hydrogen bonds. The three water mol­ecules link these chains into a three-dimensional framework by additional inter­molecular O—H⋯O hydrogen bonds. A π⋯π inter­action [3.5485 (9) Å] further stabilizes the crystal structure. International Union of Crystallography 2010-02-10 /pmc/articles/PMC2983714/ /pubmed/21580347 http://dx.doi.org/10.1107/S1600536810004526 Text en © Yeap et al. 2010 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
Yeap, Chin Sing
Hemamalini, Madhukar
Fun, Hoong-Kun
4-[(2,4-Dihydroxy­benzyl­idene)ammonio]benzene­sulfonate trihydrate
title 4-[(2,4-Dihydroxy­benzyl­idene)ammonio]benzene­sulfonate trihydrate
title_full 4-[(2,4-Dihydroxy­benzyl­idene)ammonio]benzene­sulfonate trihydrate
title_fullStr 4-[(2,4-Dihydroxy­benzyl­idene)ammonio]benzene­sulfonate trihydrate
title_full_unstemmed 4-[(2,4-Dihydroxy­benzyl­idene)ammonio]benzene­sulfonate trihydrate
title_short 4-[(2,4-Dihydroxy­benzyl­idene)ammonio]benzene­sulfonate trihydrate
title_sort 4-[(2,4-dihydroxy­benzyl­idene)ammonio]benzene­sulfonate trihydrate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983714/
https://www.ncbi.nlm.nih.gov/pubmed/21580347
http://dx.doi.org/10.1107/S1600536810004526
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