Received 27 December 2012
In the title molecule, C17H13FN2O2, the 3,4-dihydropyrimidine ring adopts a flattened sofa conformation with the flap atom (which bears the fluorophenyl substituent) deviating from the plane defined by the remaining five ring atoms by 0.281 (2) Å. This plane forms dihedral angles of 85.98 (6) and 60.63 (6)° with the 4-fluorophenyl and benzoyl-phenyl rings, respectively. The dihedral angle between the 4-fluorophenyl group and the benzene ring is 71.78 (6)°. In the crystal, N-HO hydrogen bonds link molecules into inversion dimers that are further connected by another N-HO interaction into a two-dimensional supramolecular structure parallel to (101).
For general background to and pharmaceutical applications of pyrimidinones, see: Ghorab et al. (2000); Shivarama Holla et al. (2004); Stefani et al. (2006). For related structures, see: Fun et al. (2009); Chitra et al. (2009). For asymmetry parameters, see: Duax & Norton (1975).
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010); 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); software used to prepare material for publication: PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2549 ).
RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.
Chitra, S., Pandiarajan, K., Anuradha, N. & Thiruvalluvar, A. (2009). Acta Cryst. E65, o23.
Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Fun, H.-K., Yeap, C. S., Babu, M. & Kalluraya, B. (2009). Acta Cryst. E65, o1188-o1189.
Ghorab, M. M., Abdel-Gawad, S. M. & El-Gaby, M. S. A. (2000). Il Farmaco, 55, 249-255.
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shivarama Holla, B., Sooryanarayana Rao, B., Sarojini, B. K. & Akberali, P. M. (2004). Eur. J. Med. Chem. 39, 777-783.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stefani, H. A., Oliveira, C. B., Almeida, R. B., Pereira, C. M. P., Braga, R. C., Cella, R., Borges, V. C., Savegnago, L. & Nogueira, C. W. (2006). Eur. J. Med. Chem. 41, 513-518.