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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...

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Autores principales: Karthikeyan, Ammasai, Jeeva Jasmine, Nithianantham, Thomas Muthiah, Packianathan, Perdih, Franc
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2016
Materias:
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.
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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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