4,6-Dimethyl­pyrimidin-2-amine

Fu, W.-W.; Liu, Y.; Huang, G.; Zhu, X.-M.

doi:10.1107/S1600536812049458

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 (C-C) = 0.004 Å
R = 0.062
wR = 0.175
Data-to-parameter ratio = 16.4
Details

4,6-Dimethylpyrimidin-2-amine

Wei-Wei Fu,^a ^* Yang Liu,^a Geng Huang ^a and Xiao-Ming Zhu ^a

^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-HN 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). For the properties and crystal structures of metal complexes of the title compound, see: Sun et al. (2010); Yang (2009). For the structure of a hydrate form of the title compound, see: Lin et al. (2008). For the synthesis, see: Fan et al. (2000); Yao & Qu (1997).

Experimental

Crystal data

C₆H₉N₃
M_r = 123.16
Monoclinic, C 2/c
a = 11.519 (7) Å
b = 11.021 (6) Å
c = 32.386 (18) Å
= 91.112 (10)°
V = 4111 (4) Å³
Z = 24
Mo K radiation
= 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) T_min = 0.980, T_max = 0.987
11005 measured reflections
4020 independent reflections
2252 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.062
wR(F²) = 0.175
S = 1.01
4020 reflections
245 parameters
H-atom parameters constrained
_max = 1.08 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AN2ⁱ	0.86	2.45	3.304 (4)	175
N1-H1BN8ⁱⁱ	0.86	2.52	3.376 (4)	173
N4-H4AN9ⁱⁱⁱ	0.86	2.21	3.050 (3)	167
N4-H4BN6^iv	0.86	2.45	3.243 (4)	154
N7-H7AN5^v	0.86	2.57	3.421 (4)	173
N7-H7BN3^vi	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); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2008); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010).

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.
Lin, C. H., Guo, H. M. & Jian, F. F. (2008). Z. Kristallogr. New Cryst. Struct., 223, 511-512.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sun, D., Zhang, N., Huang, R. B. & Zheng, L. S. (2010). Cryst. Growth Des. 10, 3699-3709.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Yang, H. (2009). Acta Cryst. E65, m1177.
Yao, Y. P. & Qu, H. X. (1997). Anhui Chem. Ind. 23, 23-24.

organic compounds