Received 24 June 2013
In the title molecule, C24H19BrN2O5S, the pyrimidine ring is in a flattened half-chair conformation and the 4-acetoxyphenyl group is substituted axially to this ring. The thiazole ring is essentially planar [with a maximum deviation of 0.012 (2) Å for the N atom] and forms dihedral angles of 17.65 (13) and 88.95 (11)° with the bromo- and acetoxy-substituted benzene rings, respectively. The dihedral angle between the benzene rings is 81.84 (13) Å. In the crystal, pairs of weak C-HO hydrogen bonds lead to the formation of inversion dimers. A weak C-H interaction and - stacking interactions with centroid-centroid distances of 3.5903 (14) Å are observed.
For the biological activity of dihydropyrimidines, see: Alam et al. (2010); Kappe (2000); Atwal et al. (1991); Rovnyak et al. (1992). For related structures, see: Nagarajaiah et al. (2011, 2012). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5628 ).
NSB is thankful to the University Grants Commission (UGC), India, for financial assistance.
Alam, O., Khan, S. A., Siddiqui, N. & Ahsan, W. (2010). Med. Chem. Res. 19, 1245-1258.
Atwal, K. S., Swanson, B. N., Unger, S. E., Floyd, D. M., Moreland, S., Hedberg, A. & O'Reilly, B. C. (1991). J. Med. Chem. 34, 806-811.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. 34, 1555-1573.
Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Kappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043-1052.
Nagarajaiah, H. & Begum, N. S. (2011). Acta Cryst. E67, o3444.
Nagarajaiah, H., Fathima, N. & Begum, N. S. (2012). Acta Cryst. E68, o1257-o1258.
Rovnyak, G. C., Atwal, K. S., Hedberg, A., Kimball, S. D., Moreland, S., Gougoutas, J. Z., O'Reilly, B. C., Schwartz, J. & Malley, M. F. (1992). J. Med. Chem. 35, 3254-3263.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.