Hydrogen Bonded Supramolecular Assembly in N6-Benzyladeninium Nitrate and N6-Benzyladeninium 3-Hydroxy Picolinate: A Synthetic Cytokinin

N-6-benzyladeninium nitrate, (1), C12H12N5+NO3- crystallizes in P2(1)/c, with a = 15.0035(13), b = 5.3788(5), c = 16.8954(13) angstrom, beta = 107.331(6)degrees, Z = 4 and N-6-benzyladeninium 3-hydroxy picolinate, (2), C12H12N5+C6H4NO3-, crystallizes in P1, with a = 8.3017(4), b = 14.6170(7), c = 14.7909 (8) angstrom, alpha = 78.801 (4), beta = 81.979 (4), gamma = 88.849 (4)degrees, Z = 4. In both the salts, the cation exists as N(7)H tautomer with protonation at the N-3 atom. The dihedral angle of 76.64 (16)degrees for (1), 67.91(12)degrees for (cation A) and 68.27 (13)degrees for (cation B) in (2), between the adenine plane and phenyl ring plane, the distal orientation of the N6 substituent with respect to the imidazole ring and the free N1 position, make these benzyladeninium cations meet all the requirements necessary for cytokinin activity. The crystal structures are stabilized by N-H center dot center dot center dot N, N-H center dot center dot center dot O, C-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot pi stacking interaction between symmetry related benzyladenine molecule.