6-(2-Chloro-benz-yl)-1-(4-chloro-phen-yl)-7-hy-droxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

Acta Crystallogr Sect E Struct Rep Online. 2010 Oct 9;66(Pt 11):o2742-3. doi: 10.1107/S160053681003919X.

Abstract

The title compound, C(19)H(15)Cl(2)N(3)O(2), was obtained by a one-step cyclo-condensation of 2-amino-1-(4-chloro-phen-yl)imidazoline with diethyl (2-chloro-benz-yl)malonate under basic conditions. In the crystalline state, the mol-ecule exists as the 7-hy-droxy-5-oxo tautomer. The dihedral angles between the fused imidazopyrimidine and aromatic chloro-phenyl and chloro-benzyl rings are 14.2 (1) and 70.7 (1)°, respectively. The conformation of the mol-ecule is influenced by the intra-molecular 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 inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains along the c axis. These chains are further stabilized by weak C-H⋯Cl and π-π inter-actions [centroid-centroid distance = 3.6707 (12) Å].