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Supramolecular hydrogen-bonding patterns in the N(9)—H protonated and N(7)—H tautomeric form of an N(6)-benzoyladenine salt: N (6)-benzoyladeninium nitrate
In the title molecular salt, C(12)H(10)N(5)O(+)·NO(3) (−), the adenine unit has an N (9)-protonated N(7)—H tautomeric form with non-protonated N(1) and N(3) atoms. The dihedral angle between the adenine ring system and the phenyl ring is 51.10 (10)°. The typical intramolecular N(7)—H⋯O hydrogen bon...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2016
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4770981/ https://www.ncbi.nlm.nih.gov/pubmed/26958373 http://dx.doi.org/10.1107/S2056989015024871 |
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author | Karthikeyan, Ammasai Jeeva Jasmine, Nithianantham Thomas Muthiah, Packianathan Perdih, Franc |
author_facet | Karthikeyan, Ammasai Jeeva Jasmine, Nithianantham Thomas Muthiah, Packianathan Perdih, Franc |
author_sort | Karthikeyan, Ammasai |
collection | PubMed |
description | In the title molecular salt, C(12)H(10)N(5)O(+)·NO(3) (−), the adenine unit has an N (9)-protonated N(7)—H tautomeric form with non-protonated N(1) and N(3) atoms. The dihedral angle between the adenine ring system and the phenyl ring is 51.10 (10)°. The typical intramolecular N(7)—H⋯O hydrogen bond with an S(7) graph-set motif is also present. The benzoyladeninium cations also form base pairs through N—H⋯O and C—H⋯N hydrogen bonds involving the Watson–Crick face of the adenine ring and the C and O atoms of the benzoyl ring of an adjacent cation, forming a supramolecular ribbon with R (2) (2)(9) rings. Benzoyladeninum cations are also bridged by one of the oxygen atoms of the nitrate anion, which acts as a double acceptor, forming a pair of N—H⋯O hydrogen bonds to generate a second ribbon motif. These ribbons together with π–π stacking interactions between the phenyl ring and the five- and six-membered adenine rings of adjacent molecules generate a three-dimensional supramolecular architecture. |
format | Online Article Text |
id | pubmed-4770981 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-47709812016-03-08 Supramolecular hydrogen-bonding patterns in the N(9)—H protonated and N(7)—H tautomeric form of an N(6)-benzoyladenine salt: N (6)-benzoyladeninium nitrate Karthikeyan, Ammasai Jeeva Jasmine, Nithianantham Thomas Muthiah, Packianathan Perdih, Franc Acta Crystallogr E Crystallogr Commun Research Communications In the title molecular salt, C(12)H(10)N(5)O(+)·NO(3) (−), the adenine unit has an N (9)-protonated N(7)—H tautomeric form with non-protonated N(1) and N(3) atoms. The dihedral angle between the adenine ring system and the phenyl ring is 51.10 (10)°. The typical intramolecular N(7)—H⋯O hydrogen bond with an S(7) graph-set motif is also present. The benzoyladeninium cations also form base pairs through N—H⋯O and C—H⋯N hydrogen bonds involving the Watson–Crick face of the adenine ring and the C and O atoms of the benzoyl ring of an adjacent cation, forming a supramolecular ribbon with R (2) (2)(9) rings. Benzoyladeninum cations are also bridged by one of the oxygen atoms of the nitrate anion, which acts as a double acceptor, forming a pair of N—H⋯O hydrogen bonds to generate a second ribbon motif. These ribbons together with π–π stacking interactions between the phenyl ring and the five- and six-membered adenine rings of adjacent molecules generate a three-dimensional supramolecular architecture. International Union of Crystallography 2016-01-09 /pmc/articles/PMC4770981/ /pubmed/26958373 http://dx.doi.org/10.1107/S2056989015024871 Text en © Karthikeyan et al. 2016 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 Jeeva Jasmine, Nithianantham Thomas Muthiah, Packianathan Perdih, Franc Supramolecular hydrogen-bonding patterns in the N(9)—H protonated and N(7)—H tautomeric form of an N(6)-benzoyladenine salt: N (6)-benzoyladeninium nitrate |
title | Supramolecular hydrogen-bonding patterns in the N(9)—H protonated and N(7)—H tautomeric form of an N(6)-benzoyladenine salt: N
(6)-benzoyladeninium nitrate |
title_full | Supramolecular hydrogen-bonding patterns in the N(9)—H protonated and N(7)—H tautomeric form of an N(6)-benzoyladenine salt: N
(6)-benzoyladeninium nitrate |
title_fullStr | Supramolecular hydrogen-bonding patterns in the N(9)—H protonated and N(7)—H tautomeric form of an N(6)-benzoyladenine salt: N
(6)-benzoyladeninium nitrate |
title_full_unstemmed | Supramolecular hydrogen-bonding patterns in the N(9)—H protonated and N(7)—H tautomeric form of an N(6)-benzoyladenine salt: N
(6)-benzoyladeninium nitrate |
title_short | Supramolecular hydrogen-bonding patterns in the N(9)—H protonated and N(7)—H tautomeric form of an N(6)-benzoyladenine salt: N
(6)-benzoyladeninium nitrate |
title_sort | supramolecular hydrogen-bonding patterns in the n(9)—h protonated and n(7)—h tautomeric form of an n(6)-benzoyladenine salt: n
(6)-benzoyladeninium nitrate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4770981/ https://www.ncbi.nlm.nih.gov/pubmed/26958373 http://dx.doi.org/10.1107/S2056989015024871 |
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