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

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 ?-? inter-actions [centroid-centroid distance = 3.6707?(12)?Å].

SUBMITTER: Wysocki W 

PROVIDER: S-EPMC3009369 | biostudies-literature | 2010 Oct

REPOSITORIES: biostudies-literature