title: Supra-molecular hydrogen-bonding patterns in the N(9)-H protonated and N(7)-H tautomeric form of an N(6) -benzoyl-adenine salt: N (6)-benzoyl-adeninium nitrate.
abstract: In the title molecular salt, C12H10N5O(+)·NO3 (-), 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 intra-molecular N(7)-H⋯O hydrogen bond with an S(7) graph-set motif is also present. The benzoyl-adeninium 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 supra-molecular ribbon with R 2 (2)(9) rings. Benzoyl-adeninum 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 inter-actions between the phenyl ring and the five- and six-membered adenine rings of adjacent mol-ecules generate a three-dimensional supra-molecular architecture.
authors.affiliation: School of Chemistry, Bharathidasan University, Tiruchirappalli 620024, Tamilnadu, India.
authors.forename: Ammasai
authors.initials: A
authors.lastname: Karthikeyan
authors.affiliation: School of Chemistry, Bharathidasan University, Tiruchirappalli 620024, Tamilnadu, India.
authors.forename: Nithianantham
authors.initials: N
authors.lastname: Jeeva Jasmine
authors.affiliation: School of Chemistry, Bharathidasan University, Tiruchirappalli 620024, Tamilnadu, India.
authors.forename: Packianathan
authors.initials: P
authors.lastname: Thomas Muthiah
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Vecna pot 113, PO Box 537, SI-1000 Ljubljana, Slovenia.
authors.forename: Franc
authors.initials: F
authors.lastname: Perdih
keywords: N6-benzoyl adenine; crystal structure; hydrogen bonding; nitrate anion; supra­molecular architecture