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Volume 69 
Part 1 
Page o32  
January 2013  

Received 23 November 2012
Accepted 2 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.062
wR = 0.175
Data-to-parameter ratio = 16.4
Details
Open access

4,6-Dimethylpyrimidin-2-amine

aKey Laboratory of Functional Organometallic Materials of General Colleges and Universities in Hunan Province, Department of Chemistry and Materials Science, Hengyang Normal University, Hengyang 421008, People's Republic of China
Correspondence e-mail: w.w.fu@hotmail.com

The asymmetric unit of the title compound, C6H9N3, contains three crystallographically independent molecules of similar geometry. All of the molecules are almost planar, with r.m.s. deviations of 0.003, 0.016 and 0.005 Å. In the crystal, the molecules are linked by N-H...N hydrogen bonds into zigzag ribbons parallel to the c axis, generating rings of R22(8) graph-set motif.

Related literature

For background to sulfonylurea herbicides, see: Deng (2003[Deng, J. B. (2003). World Pesticides 25, 24-29.]). For the properties and crystal structures of metal complexes of the title compound, see: Sun et al. (2010[Sun, D., Zhang, N., Huang, R. B. & Zheng, L. S. (2010). Cryst. Growth Des. 10, 3699-3709.]); Yang (2009[Yang, H. (2009). Acta Cryst. E65, m1177.]). For the structure of a hydrate form of the title compound, see: Lin et al. (2008[Lin, C. H., Guo, H. M. & Jian, F. F. (2008). Z. Kristallogr. New Cryst. Struct., 223, 511-512.]). For the synthesis, see: Fan et al. (2000[Fan, Y. T., Lu, H. J., Hou, H. W., Zhou, Z. M., Zhao, Q. H., Zhang, L. P. & Cheng, F. H. (2000). J. Coord. Chem. 50, 65-72.]); Yao & Qu (1997[Yao, Y. P. & Qu, H. X. (1997). Anhui Chem. Ind. 23, 23-24.]).

[Scheme 1]

Experimental

Crystal data
  • C6H9N3

  • Mr = 123.16

  • Monoclinic, C 2/c

  • a = 11.519 (7) Å

  • b = 11.021 (6) Å

  • c = 32.386 (18) Å

  • [beta] = 91.112 (10)°

  • V = 4111 (4) Å3

  • Z = 24

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.26 × 0.18 × 0.17 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.980, Tmax = 0.987

  • 11005 measured reflections

  • 4020 independent reflections

  • 2252 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.175

  • S = 1.01

  • 4020 reflections

  • 245 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.08 e Å-3

  • [Delta][rho]min = -0.16 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 2.45 3.304 (4) 175
N1-H1B...N8ii 0.86 2.52 3.376 (4) 173
N4-H4A...N9iii 0.86 2.21 3.050 (3) 167
N4-H4B...N6iv 0.86 2.45 3.243 (4) 154
N7-H7A...N5v 0.86 2.57 3.421 (4) 173
N7-H7B...N3vi 0.86 2.36 3.219 (3) 176
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (iii) x-1, y-1, z; (iv) [-x, y, -z+{\script{3\over 2}}]; (v) x+1, y+1, z; (vi) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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.]) and DIAMOND (Brandenburg, 2008[Brandenburg, K. (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5030 ).


Acknowledgements

Financial support by the Doctoral Startup Foundation of Hengyang Normal University (09B02) and the Foundation of Hengyang Bureau of Science and Technology (2011 K J21) are gratefully acknowledged.

References

Brandenburg, K. (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Deng, J. B. (2003). World Pesticides 25, 24-29.
Fan, Y. T., Lu, H. J., Hou, H. W., Zhou, Z. M., Zhao, Q. H., Zhang, L. P. & Cheng, F. H. (2000). J. Coord. Chem. 50, 65-72.  [ISI] [CrossRef] [ChemPort]
Lin, C. H., Guo, H. M. & Jian, F. F. (2008). Z. Kristallogr. New Cryst. Struct., 223, 511-512.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sun, D., Zhang, N., Huang, R. B. & Zheng, L. S. (2010). Cryst. Growth Des. 10, 3699-3709.  [CSD] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Yang, H. (2009). Acta Cryst. E65, m1177.  [CSD] [CrossRef] [details]
Yao, Y. P. & Qu, H. X. (1997). Anhui Chem. Ind. 23, 23-24.


Acta Cryst (2013). E69, o32  [ doi:10.1107/S1600536812049458 ]

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