6-Ethyl-5-fluoro-2-methoxy­pyrimidin-4(3H)-one

Ye, Y.-Y.; Yang, K.

doi:10.1107/S1600536809035430

Volume 65
Part 10
Page o2582
October 2009

Received 23 August 2009
Accepted 2 September 2009
Online 30 September 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.047
wR = 0.106
Data-to-parameter ratio = 16.6
Details

6-Ethyl-5-fluoro-2-methoxypyrimidin-4(3H)-one

Yu-Yuan Ye ^a ^* and Kai Yang ^b

^aSchool of Life Science and Pharmaceutical and Chemical Engineering, Taizhou University, Linhai 317000, People's Republic of China, and ^bCollege of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
Correspondence e-mail: yeyuyuan@163.com

In the title compound, C₇H₉FN₂O₂, the methoxy and ethyl groups form dihedral angles of 1.4 (2) and 73.5 (3)°, respectively, with the mean plane of the pyrimidine ring. In the crystal structure, two molecules are linked by a pair of N-HO hydrogen bonds, forming a centrosymmetric dimer.

Related literature

For fluoro-containing pyrimidines as intermediates for the synthesis of some anticancer and antifungal drugs, see: Bergmann et al. (1959); Butters et al. (2001).

Experimental

Crystal data

C₇H₉FN₂O₂
M_r = 172.16
Triclinic, $[P \overline 1]$
a = 4.5711 (4) Å
b = 8.4985 (8) Å
c = 10.8546 (11) Å
= 88.043 (2)°
= 79.737 (3)°
= 79.616 (2)°
V = 408.13 (7) Å³
Z = 2
Mo K radiation
= 0.12 mm^-1
T = 296 K
0.40 × 0.28 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.948, T_max = 0.979
4010 measured reflections
1842 independent reflections
945 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.106
S = 1.00
1842 reflections
111 parameters
H-atom parameters constrained
_max = 0.39 e Å^-3
_min = -0.37 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2ⁱ	0.86	1.91	2.763 (2)	174
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2454 ).

Acknowledgements

The authors acknowledge support from the Educational Commission of Zhejiang Province (200803289).

References

Bergmann, E. D., Cohen, S. & Shahak, I. (1959). J. Chem. Soc. 11, 3278-3285.
Butters, M., Ebbs, J., Green, S. P., MacRae, J., Morland, M. C., Murtiashaw, C. W. & Pettman, A. J. (2001). Org. Process Res. Dev. 5, 28-36.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2004). PROCESS-AUTO and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds