5-Bromo-N-methyl­pyrimidin-2-amine

Yang, Q.; Xu, N.; Zhu, K.; Lv, X.; Han, P.

doi:10.1107/S1600536811051531

Volume 68
Part 1
Page o111
January 2012

Received 15 November 2011
Accepted 30 November 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
R = 0.056
wR = 0.100
Data-to-parameter ratio = 15.4
Details

5-Bromo-N-methylpyrimidin-2-amine

Qi Yang,^a Ning Xu,^b Kai Zhu,^a Xiaoping Lv ^a and Ping-fang Han ^a ^*

^aCollege of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and ^bCollege of Environment, Nanjing University of Technolgy, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: hpf@njut.edu.cn

In the title molecule, C₅H₆BrN₃, the pyrimidine ring is essentially planar, with an r.m.s. deviation of 0.007 Å. The Br and N atoms substituted to the pyrimidine ring are coplanar with the ring [displacements = 0.032 (1) and 0.009 (5) Å, respectively], while the methyl C atom lies 0.100 (15) Å from this plane with a dihedral angle between the pyrimidine ring and the methylamine group of 4.5 (3)°. In the crystal, C-HN, C-HBr and N-HN hydrogen bonds link the molecules into a two-dimensional network in the (011) plane.

Related literature

Derivatives of pyrimidine are important chemical materials, see: Yu et al. (2007). For a related structure, see: Aakeroey et al. (2005).

Experimental

Crystal data

C₅H₆BrN₃
M_r = 188.04
Triclinic, $[P \overline 1]$
a = 3.9900 (8) Å
b = 9.862 (2) Å
c = 10.006 (2) Å
= 61.57 (3)°
= 83.84 (3)°
= 87.45 (3)°
V = 344.24 (16) Å³
Z = 2
Mo K radiation
= 5.88 mm^-1
T = 293 K
0.10 × 0.05 × 0.05 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.591, T_max = 0.758
1454 measured reflections
1260 independent reflections
714 reflections with I > 2(I)
R_int = 0.089
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.100
S = 1.00
1260 reflections
82 parameters
H-atom parameters constrained
_max = 0.40 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AN2ⁱ	0.86	2.19	3.035 (7)	169
C1-H1BBrⁱⁱ	0.96	2.85	3.751 (8)	157
C5-H5AN3ⁱⁱⁱ	0.93	2.59	3.357 (7)	140
Symmetry codes: (i) -x, -y+2, -z; (ii) x-1, y+1, z; (iii) -x-1, -y+1, -z+1.

Data collection: CAD-4 Software (Enraf-Nonius, 1989); 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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2488 ).

Acknowledgements

The authors thank Dr Bo-nian Liu from Nanjing University of Technology for useful discussions and the Center of Testing and Analysis, Nanjing University, for support.

References

Aakeroey, C. B., Desper, J., Elisabeth, E., Helfrich, B. A., Levin, B. & Urbina, J. F. (2005). Z. Kristallogr. 220, 325-332.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yu, Z. H., Niu, C. W., Ban, S. R., Wen, X. & Xi, Z. (2007). Chin. Sci. Bull. 52, 1929-1941.

organic compounds