Synthesis, infrared and molecular structure of adamantane-1-ammonium picrate monohydrate : a derivative of the antiviral symmetrel.

Abstract

The synthesis, infrared, and crystal structure investigations of adamantane-1-ammonium picrate monohydrate, (C10H21N)(C6H2N3O7) ⋅ H2O, were performed. The title compound crystallizes in the space group P21/n with the monoclinic unit cell parameters: a = 12.7211(9) Å, b = 6.8233(4) Å, c = 21.4130(14) Å and β = 105.950(7)°, V = 1787.1(2) Å3 , Z = 4. The asymmetric unit of the studied compound consists of one Adamantane-1-ammonium cation, one water and one picrate anion with two disordered nitro groups. The molecules are connected by strong H-bonds. As can be seen, the ionic pair is linked through two bifurcate N–H⋅⋅⋅O hydrogen bonds, identified as N1–H1A⋅⋅⋅O1 and N1–H1A⋅⋅⋅O2, to form a dimer. Also, water mol ecule acts bridging two picrate molecules connected by O1w–H1w⋅⋅⋅O1 and O1w–H2w⋅⋅⋅O4. These interac tions form an infinite chain extended along the [101] direction. Finally, the main intermolecular contacts were analyzed based on Hirshfeld surfaces and their fingerprint plot.