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Volume 68 
Part 12 
Page o3455  
December 2012  

Received 13 November 2012
Accepted 21 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.057
wR = 0.143
Data-to-parameter ratio = 13.9
Details
Open access

2-Chloro-6-methylpyrimidin-4-amine

aCollege of Life Science and Chemical Engineering, Huaiyin Institute of Technology, Huaiyin 223003, Jiangsu, People's Republic of China
Correspondence e-mail: dsl710221@163.com

In the crystal structure of the title compound, C5H6ClN3, molecules are linked by pairs of N-H...N hydrogen bonds, forming inversion dimers. These dimers are linked via N-H...N hydrogen bonds, forming a two-dimensional network lying parallel to (100). Inversion-related molecules are also linked via a slipped [pi]-[pi] interaction, with a centroid-centroid distance of 3.5259 (11) Å, a normal separation of 3.4365 (7) Å and a slippage of 0.789 Å.

Related literature

The title compound is an important organic intermediate which has been used to synthesise a drug that has shown promising activity against, for example, inflammatory bowel disease. For the synthetic procedure, see: Graceffa et al. (2010[Graceffa, R., Kaller, M. & La, D. (2010). US Patent No. 20100120774.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C5H6ClN3

  • Mr = 143.58

  • Monoclinic, P 21 /c

  • a = 7.1256 (8) Å

  • b = 7.8537 (8) Å

  • c = 13.0769 (15) Å

  • [beta] = 115.678 (1)°

  • V = 659.54 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.48 mm-1

  • T = 296 K

  • 0.14 × 0.12 × 0.12 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.935, Tmax = 0.944

  • 5910 measured reflections

  • 1157 independent reflections

  • 1103 reflections with I > 2[sigma](I)

  • Rint = 0.077

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.143

  • S = 1.17

  • 1157 reflections

  • 83 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.76 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...N2i 0.86 2.24 3.090 (3) 170
N3-H3B...N1ii 0.86 2.26 3.045 (2) 152
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CAD-4 Software (Enraf-Nonius, 1985[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2530 ).


Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

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.
Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Graceffa, R., Kaller, M. & La, D. (2010). US Patent No. 20100120774.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3455  [ doi:10.1107/S1600536812047794 ]

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