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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 [sigma](C-C) = 0.009 Å
R = 0.056
wR = 0.100
Data-to-parameter ratio = 15.4
Details
Open access

5-Bromo-N-methylpyrimidin-2-amine

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-H...N, C-H...Br and N-H...N 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[Yu, Z. H., Niu, C. W., Ban, S. R., Wen, X. & Xi, Z. (2007). Chin. Sci. Bull. 52, 1929-1941.]). For a related structure, see: Aakeroey et al. (2005[Aakeroey, C. B., Desper, J., Elisabeth, E., Helfrich, B. A., Levin, B. & Urbina, J. F. (2005). Z. Kristallogr. 220, 325-332.]).

[Scheme 1]

Experimental

Crystal data
  • C5H6BrN3

  • Mr = 188.04

  • Triclinic, [P \overline 1]

  • a = 3.9900 (8) Å

  • b = 9.862 (2) Å

  • c = 10.006 (2) Å

  • [alpha] = 61.57 (3)°

  • [beta] = 83.84 (3)°

  • [gamma] = 87.45 (3)°

  • V = 344.24 (16) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 5.88 mm-1

  • T = 293 K

  • 0.10 × 0.05 × 0.05 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 = 0.591, Tmax = 0.758

  • 1454 measured reflections

  • 1260 independent reflections

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

  • Rint = 0.089

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

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.100

  • S = 1.00

  • 1260 reflections

  • 82 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N2i 0.86 2.19 3.035 (7) 169
C1-H1B...Brii 0.96 2.85 3.751 (8) 157
C5-H5A...N3iii 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[Enraf-Nonius (1989). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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.  [ChemPort]
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.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yu, Z. H., Niu, C. W., Ban, S. R., Wen, X. & Xi, Z. (2007). Chin. Sci. Bull. 52, 1929-1941.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o111  [ doi:10.1107/S1600536811051531 ]

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