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Volume 65 
Part 6 
Pages o1188-o1189  
June 2009  

Received 24 April 2009
Accepted 28 April 2009
Online 7 May 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.068
wR = 0.173
Data-to-parameter ratio = 11.6
Details
Open access

Ethyl 4-(2,4-difluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C14H14F2N2O3, the dihydropyrimidinone ring adopts a flattened boat conformation. The difluorophenyl group is disordered over two orientations with occupancies of 0.544 (3) and 0.456 (3). The methoxycarbonyl group is disordered over two positions with occupancies of 0.580 (8) and 0.420 (8). In the crystal, molecules are linked into centrosymmetric dimers by paired N-H...O hydrogen bonds and the dimers are linked into a ribbon-like structure along [100] by further N-H...O hydrogen bonds.

Related literature

For general background and pharmaceutical applications of pyrimidinones, see: Kalluraya & Rai (2003[Kalluraya, B. & Rai, G. (2003). Synth. Commun. 33, 3589-3595.]); Atwal (1990[Atwal, K. S. (1990). J. Med. Chem. 33, 1510-1515.]); Sadanandam et al. (1992[Sadanandam, Y. S., Shetty, M. M. & Diwan, P. V. (1992). Eur. J. Med. Chem. 27, 87-92.]); Steele et al. (1998[Steele, T. G., Coburn, C. A., Patane, M. A. & Bock, M. G. (1998). Tetrahedron Lett. 39, 9315-9318.]); Manjula et al. (2004[Manjula, A., Rao, B. V. & Neelakantan, P. (2004). Synth. Commun. 34, 2665-2671.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C14H14F2N2O3

  • Mr = 296.27

  • Triclinic, [P \overline 1]

  • a = 7.5176 (1) Å

  • b = 8.0483 (1) Å

  • c = 11.9323 (2) Å

  • [alpha] = 90.147 (1)°

  • [beta] = 100.839 (1)°

  • [gamma] = 108.421 (1)°

  • V = 671.25 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 100 K

  • 0.43 × 0.32 × 0.13 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.949, Tmax = 0.985

  • 17515 measured reflections

  • 3075 independent reflections

  • 2703 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.173

  • S = 1.08

  • 3075 reflections

  • 266 parameters

  • 45 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.66 e Å-3

  • [Delta][rho]min = -0.84 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O2i 0.89 (3) 2.14 (3) 3.007 (2) 165 (2)
N2-H1N2...O1ii 0.86 (3) 1.99 (3) 2.840 (2) 177 (3)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2792 ).


Acknowledgements

HKF thanks Universiti Sains Malaysia for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). CSY thanks the Malaysian Government and Universiti Sains Malaysia for the award of a post of research officer under the Science Fund (grant No. 305/PFIZIK/613312).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Atwal, K. S. (1990). J. Med. Chem. 33, 1510-1515.  [CrossRef] [ChemPort] [PubMed] [ISI]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Kalluraya, B. & Rai, G. (2003). Synth. Commun. 33, 3589-3595.  [ISI] [CrossRef] [ChemPort]
Manjula, A., Rao, B. V. & Neelakantan, P. (2004). Synth. Commun. 34, 2665-2671.  [ISI] [CrossRef] [ChemPort]
Sadanandam, Y. S., Shetty, M. M. & Diwan, P. V. (1992). Eur. J. Med. Chem. 27, 87-92.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Steele, T. G., Coburn, C. A., Patane, M. A. & Bock, M. G. (1998). Tetrahedron Lett. 39, 9315-9318.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2009). E65, o1188-o1189   [ doi:10.1107/S1600536809015918 ]

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