2-Chloro-6-methyl­pyrimidin-4-amine

Dong, S.-L.; Cheng, X.

doi:10.1107/S1600536812047794

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 (C-C) = 0.003 Å
R = 0.057
wR = 0.143
Data-to-parameter ratio = 13.9
Details

2-Chloro-6-methylpyrimidin-4-amine

Su-Lan Dong ^a ^* and Xiaochun Cheng ^a

^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-HN hydrogen bonds, forming inversion dimers. These dimers are linked via N-HN 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). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₅H₆ClN₃
M_r = 143.58
Monoclinic, P 2₁ /c
a = 7.1256 (8) Å
b = 7.8537 (8) Å
c = 13.0769 (15) Å
= 115.678 (1)°
V = 659.54 (13) Å³
Z = 4
Mo K radiation
= 0.48 mm^-1
T = 296 K
0.14 × 0.12 × 0.12 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.935, T_max = 0.944
5910 measured reflections
1157 independent reflections
1103 reflections with I > 2(I)
R_int = 0.077
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.143
S = 1.17
1157 reflections
83 parameters
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.76 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3AN2ⁱ	0.86	2.24	3.090 (3)	170
N3-H3BN1ⁱⁱ	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); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds