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Volume 69 
Part 5 
Page o626  
May 2013  

Received 12 March 2013
Accepted 25 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.034
wR = 0.096
Data-to-parameter ratio = 13.6
Details
Open access

2-Chloro-5-fluoro-6-methyl-N-o-tolylpyrimidin-4-amine

aCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, People's Republic of China
Correspondence e-mail: zhouwei@zjut.edu.cn

In the title compound, C12H11ClFN3, the benzene ring forms a dihedral angle of 72.43 (5)° with the pyrimidine ring. In the crystal, N-H...N hydrogen bonds link the molecules into a chain running along the c axis.

Related literature

For background to and applications of fluoro-pyrimidines, see: Riccaboni et al. (2010[Riccaboni, M., Bianchi, I. & Petrillo, P. (2010). Drug Discov. Today, 15, 517-530.]). For the antitumor activity of 4-aniline-substituted 5-fluoropyrimidines, see: Lawrence et al. (2012[Lawrence, H. R., Martin, M. P., Luo, Y. & Pireddu, R. (2012). J. Med. Chem. 55, 7392-7416.]).

[Scheme 1]

Experimental

Crystal data
  • C12H11ClFN3

  • Mr = 251.69

  • Monoclinic, P 21 /c

  • a = 12.0593 (7) Å

  • b = 8.3684 (4) Å

  • c = 12.8611 (6) Å

  • [beta] = 113.021 (6)°

  • V = 1194.54 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 293 K

  • 0.5 × 0.3 × 0.2 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • 4692 measured reflections

  • 2125 independent reflections

  • 1750 reflections with I > 2[sigma](I)

  • Rint = 0.014

  • 3 standard reflections every 60 min intensity decay: none

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.096

  • S = 1.04

  • 2125 reflections

  • 156 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N2i 0.86 2.34 3.0768 (19) 145
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CAD-4 Software (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD4. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD4. Enraf-Nonius, Delft, The Netherlands.]); data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5256 ).


Acknowledgements

We are acknowledge the support of Education Department Fund (Y201018689) of Zhejiang Province.

References

Enraf-Nonius (1994). CAD4. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Lawrence, H. R., Martin, M. P., Luo, Y. & Pireddu, R. (2012). J. Med. Chem. 55, 7392-7416.  [ISI] [CrossRef] [ChemPort] [PubMed]
Riccaboni, M., Bianchi, I. & Petrillo, P. (2010). Drug Discov. Today, 15, 517-530.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o626  [ doi:10.1107/S160053681300812X ]

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