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.

Ammasai Karthikeyan, Nithianantham Jeeva Jasmine, Packianathan Thomas Muthiah, Franc Perdih
Author Information
  1. Ammasai Karthikeyan: School of Chemistry, Bharathidasan University, Tiruchirappalli 620024, Tamilnadu, India.
  2. Nithianantham Jeeva Jasmine: School of Chemistry, Bharathidasan University, Tiruchirappalli 620024, Tamilnadu, India.
  3. Packianathan Thomas Muthiah: School of Chemistry, Bharathidasan University, Tiruchirappalli 620024, Tamilnadu, India.
  4. Franc Perdih: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Vecna pot 113, PO Box 537, SI-1000 Ljubljana, Slovenia.

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.

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References

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