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Crystal structure of 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidin-1-ium 3-hydroxypyridine-2-carboxylate
The asymmetric unit of the title salt, C(4)H(5)FN(3)O(+)·C(6)H(4)NO(3) (−), contains one 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidin-1-ium (5-fluorocytosinium, 5FC) cation and a 3-hydroxypicolinate (3HAP) anion. The 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidine molecule is protonated at one o...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4257234/ https://www.ncbi.nlm.nih.gov/pubmed/25484736 http://dx.doi.org/10.1107/S1600536814021898 |
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author | Karthikeyan, Ammasai Thomas Muthiah, Packianathan Perdih, Franc |
author_facet | Karthikeyan, Ammasai Thomas Muthiah, Packianathan Perdih, Franc |
author_sort | Karthikeyan, Ammasai |
collection | PubMed |
description | The asymmetric unit of the title salt, C(4)H(5)FN(3)O(+)·C(6)H(4)NO(3) (−), contains one 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidin-1-ium (5-fluorocytosinium, 5FC) cation and a 3-hydroxypicolinate (3HAP) anion. The 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidine molecule is protonated at one of the pyrimidine N atoms. The typical intramolecular N—H⋯F and O—H⋯O S(5) and S(6) hydrogen-bond ring motifs are observed in the cations and anions. The protonated N atom and 2-amine group of the 5FC cation interact with the 3HPA anion through a pair of nearly parallel N—H⋯O hydrogen bonds, forming a robust R (2) (2)(8) ring motif. The ions are further linked by N—H⋯N, O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds, generating R (2) (2)(7), R (3) (3)(12) and R (6) (5)(18) ring motifs, respectively, leading to supramolecular wave-like sheets parallel to (010). The crystal structure is further stabilized by C—H⋯π interactions, generating a three-dimensional architecture. |
format | Online Article Text |
id | pubmed-4257234 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-42572342014-12-05 Crystal structure of 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidin-1-ium 3-hydroxypyridine-2-carboxylate Karthikeyan, Ammasai Thomas Muthiah, Packianathan Perdih, Franc Acta Crystallogr Sect E Struct Rep Online Research Communications The asymmetric unit of the title salt, C(4)H(5)FN(3)O(+)·C(6)H(4)NO(3) (−), contains one 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidin-1-ium (5-fluorocytosinium, 5FC) cation and a 3-hydroxypicolinate (3HAP) anion. The 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidine molecule is protonated at one of the pyrimidine N atoms. The typical intramolecular N—H⋯F and O—H⋯O S(5) and S(6) hydrogen-bond ring motifs are observed in the cations and anions. The protonated N atom and 2-amine group of the 5FC cation interact with the 3HPA anion through a pair of nearly parallel N—H⋯O hydrogen bonds, forming a robust R (2) (2)(8) ring motif. The ions are further linked by N—H⋯N, O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds, generating R (2) (2)(7), R (3) (3)(12) and R (6) (5)(18) ring motifs, respectively, leading to supramolecular wave-like sheets parallel to (010). The crystal structure is further stabilized by C—H⋯π interactions, generating a three-dimensional architecture. International Union of Crystallography 2014-10-11 /pmc/articles/PMC4257234/ /pubmed/25484736 http://dx.doi.org/10.1107/S1600536814021898 Text en © Karthikeyan et al. 2014 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 Karthikeyan, Ammasai Thomas Muthiah, Packianathan Perdih, Franc Crystal structure of 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidin-1-ium 3-hydroxypyridine-2-carboxylate |
title | Crystal structure of 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidin-1-ium 3-hydroxypyridine-2-carboxylate |
title_full | Crystal structure of 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidin-1-ium 3-hydroxypyridine-2-carboxylate |
title_fullStr | Crystal structure of 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidin-1-ium 3-hydroxypyridine-2-carboxylate |
title_full_unstemmed | Crystal structure of 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidin-1-ium 3-hydroxypyridine-2-carboxylate |
title_short | Crystal structure of 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidin-1-ium 3-hydroxypyridine-2-carboxylate |
title_sort | crystal structure of 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidin-1-ium 3-hydroxypyridine-2-carboxylate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4257234/ https://www.ncbi.nlm.nih.gov/pubmed/25484736 http://dx.doi.org/10.1107/S1600536814021898 |
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