Source of materialA mixture of rimantadine (0.18 g, 1.0 mmol) and 2-hydroxybenzaldehyde (0.13 g, 1.0 mmol) in absolute methanol (30 ml) was stirred and refluxed for 4 h. The solution was cooled to room temperature. Yellow single crystals suitable for X-ray diffraction were obtained by slow evaporation after about 5 d.
DiscussionFor many years, there has been considerable interest in the study of Schiff base compounds due to their biological activity [1,2]. Recently, we have already reported some organic complexes and metal-organic coordination complexes constructed by Schiff bases [3][4][5]. As an extension of our work in the structural characterization of Schiff base compounds, we synthesized the title compound and analyzed its crystal structure. The title crystal structure contains two independent C 19H25NO units. The compound crystallizes in the phenol-imine tautomeric form with O1C1 and O2C20 bond lengths of 1.350(5) Å and 1.354(5) Å, respectively. The C7=N1 bond length of 1.263(5) Å and the C26=N2 bond length of 1.262(5) Å correspond to the value for a double bond [6]. The dihedral angles between two neighboring benzene rings are 62.9°. Furthermore, there are strong OH···N intramolecular hydrogen bond involving hydroxy O1 atom and N1 atom as well as hydroxy O2 atom and N2 atom. Three C atoms, one N atom, one O atom and one H atom generate a six-membered ring through coordination and hydrogen bonds, which stabilize the three-dimensional network.