Ammasai Karthikeyan, Nithianantham Jeeva Jasmine, Packianathan Thomas Muthiah, Franc Perdih
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.
Chem Cent J. 2014 Oct 29;8(1):58
[PMID:
25392712]
Acta Crystallogr D Biol Crystallogr. 2009 Feb;65(Pt 2):148-55
[PMID:
19171970]
Acta Crystallogr C. 2003 Jan;59(Pt 1):o27-9
[PMID:
12506229]
Acta Crystallogr C. 2005 Oct;61(Pt 10):o586-8
[PMID:
16210764]
Inorg Chem. 2004 Sep 6;43(18):5761-70
[PMID:
15332829]
J Pharm Sci. 2014 Apr;103(4):1126-32
[PMID:
24515970]
Acta Crystallogr C. 2011 May;67(Pt 5):o192-4
[PMID:
21540547]
Acta Crystallogr C Struct Chem. 2015 Nov;71(Pt 11):985-90
[PMID:
26524172]