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4-Amino-N-(4,6-dimethyl­pyrimidin-2-yl)­benzene­sulfonamide–4-nitro­benzoic acid (1/1)

In the asymmetric unit of the title co-crystal, C(7)H(5)NO(4)·C(12)H(14)N(4)O(2)S, there are two independent but conformationally similar heterodimers, which are formed through inter­molecular N—H⋯O(carb­oxy) and carbox­yl–pyrimidine O—H⋯N hydrogen-bond pairs, giving a cyclic motif [graph set R (2)...

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Autores principales: Smith, Graham, Wermuth, Urs D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379250/
https://www.ncbi.nlm.nih.gov/pubmed/22719448
http://dx.doi.org/10.1107/S1600536812019563
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author Smith, Graham
Wermuth, Urs D.
author_facet Smith, Graham
Wermuth, Urs D.
author_sort Smith, Graham
collection PubMed
description In the asymmetric unit of the title co-crystal, C(7)H(5)NO(4)·C(12)H(14)N(4)O(2)S, there are two independent but conformationally similar heterodimers, which are formed through inter­molecular N—H⋯O(carb­oxy) and carbox­yl–pyrimidine O—H⋯N hydrogen-bond pairs, giving a cyclic motif [graph set R (2) (2)(8)]. The dihedral angles between the rings in the sulfonamide molecules are 78.77 (8) and 82.33 (9)° while the dihedral angles between the ring and the CO(2)H group in the acids are 2.19 (9) and 7.02 (10)°. A two-dimensional structure parallel to the ab plane is generated from the heterodimer units through hydrogen-bonding associations between NH(2) and sulfone groups. Between neighbouring two-dimensional arrays there are two types of aromatic π–π stacking inter­actions involving either one of the pyrimidine rings and a 4-nitro­benzoic acid mol­ecule [minimum ring centroid separation = 3.5886 (9) Å] or two acid mol­ecules [minimum ring centroid separation = 3.7236 (10) Å].
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spelling pubmed-33792502012-06-20 4-Amino-N-(4,6-dimethyl­pyrimidin-2-yl)­benzene­sulfonamide–4-nitro­benzoic acid (1/1) Smith, Graham Wermuth, Urs D. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the asymmetric unit of the title co-crystal, C(7)H(5)NO(4)·C(12)H(14)N(4)O(2)S, there are two independent but conformationally similar heterodimers, which are formed through inter­molecular N—H⋯O(carb­oxy) and carbox­yl–pyrimidine O—H⋯N hydrogen-bond pairs, giving a cyclic motif [graph set R (2) (2)(8)]. The dihedral angles between the rings in the sulfonamide molecules are 78.77 (8) and 82.33 (9)° while the dihedral angles between the ring and the CO(2)H group in the acids are 2.19 (9) and 7.02 (10)°. A two-dimensional structure parallel to the ab plane is generated from the heterodimer units through hydrogen-bonding associations between NH(2) and sulfone groups. Between neighbouring two-dimensional arrays there are two types of aromatic π–π stacking inter­actions involving either one of the pyrimidine rings and a 4-nitro­benzoic acid mol­ecule [minimum ring centroid separation = 3.5886 (9) Å] or two acid mol­ecules [minimum ring centroid separation = 3.7236 (10) Å]. International Union of Crystallography 2012-05-05 /pmc/articles/PMC3379250/ /pubmed/22719448 http://dx.doi.org/10.1107/S1600536812019563 Text en © Smith and Wermuth 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
Smith, Graham
Wermuth, Urs D.
4-Amino-N-(4,6-dimethyl­pyrimidin-2-yl)­benzene­sulfonamide–4-nitro­benzoic acid (1/1)
title 4-Amino-N-(4,6-dimethyl­pyrimidin-2-yl)­benzene­sulfonamide–4-nitro­benzoic acid (1/1)
title_full 4-Amino-N-(4,6-dimethyl­pyrimidin-2-yl)­benzene­sulfonamide–4-nitro­benzoic acid (1/1)
title_fullStr 4-Amino-N-(4,6-dimethyl­pyrimidin-2-yl)­benzene­sulfonamide–4-nitro­benzoic acid (1/1)
title_full_unstemmed 4-Amino-N-(4,6-dimethyl­pyrimidin-2-yl)­benzene­sulfonamide–4-nitro­benzoic acid (1/1)
title_short 4-Amino-N-(4,6-dimethyl­pyrimidin-2-yl)­benzene­sulfonamide–4-nitro­benzoic acid (1/1)
title_sort 4-amino-n-(4,6-dimethyl­pyrimidin-2-yl)­benzene­sulfonamide–4-nitro­benzoic acid (1/1)
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379250/
https://www.ncbi.nlm.nih.gov/pubmed/22719448
http://dx.doi.org/10.1107/S1600536812019563
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