Supramolecular architecture in a co-crystal of the N(7)—H tautomeric form of N6-benzoyladenine with adipic acid (1/0.5)

Acta Crystallographica Section E: Crystallographic Communications

Franc Perdih¹  Packianathan Thomas Muthiah²  Robert Swinton Darious² 

[1] Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, PO Box 537, SI-1000 Ljubljana, Slovenia;School of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamilnadu, India;

关键词: crystal structure;    N6-benzoyladenine;    adipic acid;    hydrogen bond;    supramolecular sheet;    π–π stacking;    co-crystal;   

DOI  :  10.1107/S2056989016007581

来源: DOAJ

【 摘 要 】

The asymmetric unit of the title co-crystal, C12H9N5O·0.5C6H10O4, consists of one molecule of N6-benzoyladenine (BA) and one half-molecule of adipic acid (AA), the other half being generated by inversion symmetry. The dihedral angle between the adenine and phenyl ring planes is 26.71 (7)°. The N6-benzoyladenine molecule crystallizes in the N(7)—H tautomeric form with three non-protonated N atoms. This tautomeric form is stabilized by intramolecular N—H...O hydrogen bonding between the carbonyl (C=O) group and the N(7)—H hydrogen atom on the Hoogsteen face of the purine ring, forming an S(7) ring motif. The two carboxyl groups of adipic acid interact with the Watson–Crick face of the BA molecules through O—H...N and N—H...O hydrogen bonds, generating an R22(8) ring motif. The latter units are linked by N—H...N hydrogen bonds, forming layers parallel to (10-5). A weak C—H...O hydrogen bond is also present, linking adipic acid molecules in neighbouring layers, enclosing R22(10) ring motifs and forming a three-dimensional structure. C=O...π and C—H...π interactions are also present in the structure.

【 授权许可】

Unknown