Synthesis and Crystal Structure Analysis of Acridine Derivatives

Abstract

The title compounds were synthesised by the reaction of substituted benzaldehyde with dimedone in presence of liquid ammonia in a water–ethanol system. The yields of the synthesised products were 93 and 87%, respectively. Single crystals were obtained after chromatographic purification technique at the same temperature and under the same solvent conditions. The compounds 3a and 3b crystallize in orthorhombic and monoclinic crystal system in Iba2 and P21/c space groups. The aryl rings of both compounds 3a and 3b are oriented orthogonal to the plane of the pyridine ring with dihedral angles of 86.61° and 87.28°, respectively. The central pyridine ring of compounds 3a and 3b takes the shape of a boat and planar conformation, respectively. Crystal structures are stabilized by N–H⋅⋅⋅O, C–H⋅⋅⋅O and C–H⋅⋅⋅F intermolecular interactions. Compound 3a is stabilized by hydrogen bonds, whereas compound 3b is stabilized only by weak intermolecular interactions