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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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Detalles Bibliográficos
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
Descripción
Sumario: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.