6-(2-Chlorobenzyl)-1-(4-chlorophenyl)-7-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

Abstract

The title compound, C19H15Cl2N3O2, was obtained by a one-step cyclocondensation of 2-amino-1-(4-chlorophenyl)imidazoline with diethyl (2-chlorobenzyl)malonate under basic conditions. In the crystalline state, the molecule exists as the 7-hydroxy-5-oxo tautomer. The dihedral angles between the fused imidazopyrimidine and aromatic chlorophenyl and chlorobenzyl rings are 14.2 (1) and 70.7 (1)°, respectively. The conformation of the molecule is influenced by the intramolecular C—H...O and C—H...N hydrogen bonds, giving a nearly planar five-ring fused system [maximum deviation from the mean plane = 0.296 (2) Å]. In the crystal structure, strong intermolecular O—H...O hydrogen bonds link the molecules into chains along the c axis. These chains are further stabilized by weak C—H...Cl and π–π interactions [centroid–centroid distance = 3.6707 (12) Å].