Synthesis, Infrared and Molecular Structure of Adamantane-1-Ammonium Picrate Monohydrate: A Derivative of the Antiviral Symmetrel

• Published in: Crystallography reports 2020-11, Vol.65 (6), p.879-884
• Main Authors: Niquini, F. M., Moura, A. L. S., Machado, P. H., Oliveira, K. M., Correa, R. S.
• Format: Article
• Language: English
• Subjects: Crystallography and Scattering Methods; Physics; Physics and Astronomy; Structure of Organic Compounds
• ISSN: 1063-7745; 1562-689X
• DOI: 10.1134/S1063774520060231

The synthesis, infrared, and crystal structure investigations of adamantane-1-ammonium picrate monohydrate, (C 10 H 21 N)(C 6 H 2 N 3 O 7 ) ⋅ H 2 O, were performed. The title compound crystallizes in the space group P 2 1 / 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) Å 3 , 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 molecule acts bridging two picrate molecules connected by O1w–H1w⋅⋅⋅O1 and O1w–H2w⋅⋅⋅O4. These interactions form an infinite chain extended along the [101] direction. Finally, the main intermolecular contacts were analyzed based on Hirshfeld surfaces and their fingerprint plot.