5-Benzoyl-4-(4-fluoro­phen­yl)-3,4-dihydro­pyrimidin-2(1H)-one

Kant, R.; Gupta, V.K.; Kapoor, K.; Patil, D.R.; Deshmukh, M.B.

doi:10.1107/S1600536812052105

Volume 69
Part 2
Page o196
February 2013

Received 27 December 2012
Accepted 31 December 2012
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.048
wR = 0.131
Data-to-parameter ratio = 14.0
Details

5-Benzoyl-4-(4-fluorophenyl)-3,4-dihydropyrimidin-2(1H)-one

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a D. R. Patil ^b and Madhukar B. Deshmukh ^b

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^bDepartment of Chemistry, Shivaji University, Kolhapur 416 004(MS), India
Correspondence e-mail: rkvk.paper11@gmail.com

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).

Related literature

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).

Experimental

Crystal data

C₁₇H₁₃FN₂O₂
M_r = 296.29
Monoclinic, P 2₁ /n
a = 12.7911 (5) Å
b = 8.1862 (3) Å
c = 13.7325 (5) Å
= 98.850 (4)°
V = 1420.82 (9) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.777, T_max = 1.000
27552 measured reflections
2786 independent reflections
1836 reflections with I > 2(I)
R_int = 0.075

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.131
S = 1.04
2786 reflections
199 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2ⁱ	0.86	1.96	2.777 (2)	159
N3-H3O1ⁱⁱ	0.86	2.12	2.937 (2)	159
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Acknowledgements

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.

References

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.

organic compounds