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Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxyl­ate: an unexpected salt arising from the deca­rboxylation of both precursors

Both the 3-amino-2H,4H-1,2,4-triazolium cation and the pyrazine-2-carboxyl­ate anion in the title salt, C(2)H(5)N(4) (+)·C(5)H(3)N(2)O(2) (−), were formed by an unexpected deca­rboxylation reaction, from 5-amino-1H-1,2,4-triazole-3-carb­oxy­lic acid and pyrazine-2,3-di­carb­oxy­lic acid, respectivel...

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Autores principales: Fernandes, José A., Liu, Bing, Tomé, João P. C., Cunha-Silva, Luís, Almeida Paz, Filipe A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4518908/
https://www.ncbi.nlm.nih.gov/pubmed/26279881
http://dx.doi.org/10.1107/S205698901501172X
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author Fernandes, José A.
Liu, Bing
Tomé, João P. C.
Cunha-Silva, Luís
Almeida Paz, Filipe A.
author_facet Fernandes, José A.
Liu, Bing
Tomé, João P. C.
Cunha-Silva, Luís
Almeida Paz, Filipe A.
author_sort Fernandes, José A.
collection PubMed
description Both the 3-amino-2H,4H-1,2,4-triazolium cation and the pyrazine-2-carboxyl­ate anion in the title salt, C(2)H(5)N(4) (+)·C(5)H(3)N(2)O(2) (−), were formed by an unexpected deca­rboxylation reaction, from 5-amino-1H-1,2,4-triazole-3-carb­oxy­lic acid and pyrazine-2,3-di­carb­oxy­lic acid, respectively. The dihedral angle between the pyrazine ring (r.m.s. deviation = 0.008 Å) and the carboxyl­ate group in the anion is 3.7 (3)°. The extended structure of the salt contains a supra­molecular zigzag tape in which cations and anions are engaged in strong and highly directional N—H⋯N,O hydrogen bonds, forming R (2) (2)(8) and R (2) (2)(9) graph-set motifs. The packing between the tapes is mediated by π–π stacking inter­actions between the triazole and pyrazine rings.
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spelling pubmed-45189082015-08-14 Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxyl­ate: an unexpected salt arising from the deca­rboxylation of both precursors Fernandes, José A. Liu, Bing Tomé, João P. C. Cunha-Silva, Luís Almeida Paz, Filipe A. Acta Crystallogr E Crystallogr Commun Research Communications Both the 3-amino-2H,4H-1,2,4-triazolium cation and the pyrazine-2-carboxyl­ate anion in the title salt, C(2)H(5)N(4) (+)·C(5)H(3)N(2)O(2) (−), were formed by an unexpected deca­rboxylation reaction, from 5-amino-1H-1,2,4-triazole-3-carb­oxy­lic acid and pyrazine-2,3-di­carb­oxy­lic acid, respectively. The dihedral angle between the pyrazine ring (r.m.s. deviation = 0.008 Å) and the carboxyl­ate group in the anion is 3.7 (3)°. The extended structure of the salt contains a supra­molecular zigzag tape in which cations and anions are engaged in strong and highly directional N—H⋯N,O hydrogen bonds, forming R (2) (2)(8) and R (2) (2)(9) graph-set motifs. The packing between the tapes is mediated by π–π stacking inter­actions between the triazole and pyrazine rings. International Union of Crystallography 2015-06-24 /pmc/articles/PMC4518908/ /pubmed/26279881 http://dx.doi.org/10.1107/S205698901501172X Text en © Fernandes et al. 2015 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 Research Communications
Fernandes, José A.
Liu, Bing
Tomé, João P. C.
Cunha-Silva, Luís
Almeida Paz, Filipe A.
Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxyl­ate: an unexpected salt arising from the deca­rboxylation of both precursors
title Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxyl­ate: an unexpected salt arising from the deca­rboxylation of both precursors
title_full Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxyl­ate: an unexpected salt arising from the deca­rboxylation of both precursors
title_fullStr Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxyl­ate: an unexpected salt arising from the deca­rboxylation of both precursors
title_full_unstemmed Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxyl­ate: an unexpected salt arising from the deca­rboxylation of both precursors
title_short Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxyl­ate: an unexpected salt arising from the deca­rboxylation of both precursors
title_sort crystal structure of 5-amino-4h-1,2,4-triazol-1-ium pyrazine-2-carboxyl­ate: an unexpected salt arising from the deca­rboxylation of both precursors
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4518908/
https://www.ncbi.nlm.nih.gov/pubmed/26279881
http://dx.doi.org/10.1107/S205698901501172X
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