Research Article: Methyl 2-(2-bromo­benzyl­idene)-5-(4-hy­droxy­phen­yl)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate

Date Published: April 01, 2012

Publisher: International Union of Crystallography

Author(s): H. Nagarajaiah, Nikhath Fathima, Noor Shahina Begum.


In the title compound, C22H17BrN2O4S, the central dihydropyrimidine ring, with a chiral C atom, is significantly puckered and adopts a half-chair conformation with the chiral C atom displaced from the mean plane of the remaining ring atoms by 0.305 (6) Å. The hydroxy-phenyl ring is positioned axially to the pyrimidine ring and almost bisects it, the dihedral angle between the mean-planes of the two rings being 89.78 (12)°. The meth­oxy­carbonyl group is disordered over two sites with an occupancy ratio of 0.568 (5):0.432 (5), resulting in a major and a minor conformer. In the crystal, O—H⋯N and C—H⋯S inter­actions result in sheets along the c axis. The supra­molecular assembly is stabilized by π–π stacking inter­actions between the 2-bromo­benzyl­idene and thia­zolopyrimidine rings [centroid–centroid distance = 3.632 (1) Å]. In addition, C—H⋯π inter­actions are also observed in the crystal structure.

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For therapeutic and medicinal properties of thia­zolopyrimidine derivatives, see: Kappe (2000 ▶); Ozair et al. (2010 ▶). For a related structure, see: Nagarajaiah & Begum (2011 ▶).