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Volume 68 
Part 1 
Page o39  
January 2012  

Received 9 October 2011
Accepted 1 December 2011
Online 7 December 2011

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.048
wR = 0.157
Data-to-parameter ratio = 10.6
Details
Open access

5,6-Dimethyl-1,2,4-triazin-3-amine

Man-Hua Wu,a Qi-Ming Qiu,a Sen Gao,a Qiong-Hua Jina* and Cun-Lin Zhangb

aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China, and bKey Laboratory of Terahertz Optoelectronic, Ministry of Education, Department of Physics, Capital Normal University, Beijing 100048, People's Republic of China
Correspondence e-mail: jinqh204@163.com

In the crystal structure of the title compound, C5H8N4, adjacent molecules are connected through N-H...N hydrogen bonds, resulting in a zigzag chain along [100]. The amino groups and heterocyclic N atoms are involved in further N-H...N hydrogen bonds, forming R22(8) motifs.

Related literature

For the biological and medical applications of triazine, see: Anderson et al.(2003[Anderson, R. F., Shinde, S. S., Hay, M. P., Gamage, S. A. & Denny, W. A. (2003). J. Am. Chem. Soc. 125, 748-756.]); Gavai et al. (2009[Gavai, A. V., Fink, B. E., Fairfax, D. J., Martin, G. S. & Rossiter, L. M. (2009). J. Med. Chem. 52, 6527-6530.]); Hunt et al. (2004[Hunt, J. T., Mitt, T., Borzilleri, R., Brown, J. G. & Fargnoli, J. (2004). J. Med. Chem. 47, 4054-4059.]). For the structures of complexes containing triazine, see: Drew et al. (2001[Drew, M. G. B., Guillaneux, D., Hudson, M. J., Iveson, P. B., Russell, M. L. & Madic, C. (2001). Inorg. Chem. Commun. 4, 12-15.]); Li et al. (2009[Li, L. X., Turnbull, M. M., Ackers, J., Chen, J. P., Lin, H. Y., Pan, B. F., Wang, H. & Foxman, B. M. (2009). Inorg. Chim. Acta, 362, 3845-3852.]); Machura et al. (2008[Machura, B., Switlicka, A., Kruszynski, R., Mrozinski, J., Klak, J. & Kusz, J. (2008). Polyhedron, 27, 2959-2967.]). For the structures of complexes containing the title compound, see: Jiang et al. (2011[Jiang, Y.-H., Cui, L.-N., Huang, X., Jin, Q.-H. & Zhang, C.-L. (2011). Acta Cryst. E67, m1526-m1527.]); Self et al. (1991[Self, M. F., Pennington, W. T. & Robinson, G. H. (1991). J. Coord. Chem. 24, 69-76.]); Wu et al. (2011[Wu, M. H., Wang, R., Li, Z. F., Xiao, Y. L., Jin, Q. H. & Zhang, C. L. (2011). Z. Kristallogr. New Cryst. Struct. 226, 555-556.]). For the structures of compounds containing R22(8)-type hydrogen bonds, see: Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]); Glidewell et al. (2003[Glidewell, C., Low, J. N., Melguizo, M. & Quesada, A. (2003). Acta Cryst. C59, o9-o13.]).

[Scheme 1]

Experimental

Crystal data

  • C5H8N4

  • Mr = 124.14

  • Orthorhombic, P n m a

  • a = 7.4877 (8) Å

  • b = 6.7530 (7) Å

  • c = 12.6615 (13) Å

  • V = 640.22 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.50 × 0.39 × 0.38 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Wisconsin, USA.]) Tmin = 0.960, Tmax = 0.969

  • 2997 measured reflections

  • 614 independent reflections

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

  • Rint = 0.034
Refinement

  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.157

  • S = 1.11

  • 614 reflections

  • 58 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 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
N4-H4A...N3i 0.86 2.19 3.045 (4) 179
N4-H4B...N2ii 0.86 2.09 2.947 (4) 176
Symmetry codes: (i) [x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]; (ii) [x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2007[Bruker (2007). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Wisconsin, USA.]); data reduction: SAINT-Plus; 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.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RN2097 ).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 21171119), the CAIQ Basic Research Program (No. 2010 J K022), the National Keystone Basic Research Program (973 Program) under grant Nos. 2007CB310408 and 2006CB302901, the Funding Project for Academic Human Resources Development in Institutions of Higher Learning under the Jurisdiction of Beijing Municipality and the State Key Laboratory of Functional Materials for Informatics, Shanghai Institute of Microsystem and Information Technology, Chinese Academy of Sciences.

References

Anderson, R. F., Shinde, S. S., Hay, M. P., Gamage, S. A. & Denny, W. A. (2003). J. Am. Chem. Soc. 125, 748-756.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2007). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Wisconsin, USA.
Drew, M. G. B., Guillaneux, D., Hudson, M. J., Iveson, P. B., Russell, M. L. & Madic, C. (2001). Inorg. Chem. Commun. 4, 12-15.  [ISI] [CSD] [CrossRef] [ChemPort]
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [ISI]
Gavai, A. V., Fink, B. E., Fairfax, D. J., Martin, G. S. & Rossiter, L. M. (2009). J. Med. Chem. 52, 6527-6530.  [ISI] [CrossRef] [PubMed] [ChemPort]
Glidewell, C., Low, J. N., Melguizo, M. & Quesada, A. (2003). Acta Cryst. C59, o9-o13.  [CSD] [CrossRef] [details]
Hunt, J. T., Mitt, T., Borzilleri, R., Brown, J. G. & Fargnoli, J. (2004). J. Med. Chem. 47, 4054-4059.  [ISI] [CrossRef] [PubMed] [ChemPort]
Jiang, Y.-H., Cui, L.-N., Huang, X., Jin, Q.-H. & Zhang, C.-L. (2011). Acta Cryst. E67, m1526-m1527.  [CSD] [CrossRef] [details]
Li, L. X., Turnbull, M. M., Ackers, J., Chen, J. P., Lin, H. Y., Pan, B. F., Wang, H. & Foxman, B. M. (2009). Inorg. Chim. Acta, 362, 3845-3852.  [ISI] [CSD] [CrossRef] [ChemPort]
Machura, B., Switlicka, A., Kruszynski, R., Mrozinski, J., Klak, J. & Kusz, J. (2008). Polyhedron, 27, 2959-2967.  [ISI] [CSD] [CrossRef] [ChemPort]
Self, M. F., Pennington, W. T. & Robinson, G. H. (1991). J. Coord. Chem. 24, 69-76.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wu, M. H., Wang, R., Li, Z. F., Xiao, Y. L., Jin, Q. H. & Zhang, C. L. (2011). Z. Kristallogr. New Cryst. Struct. 226, 555-556.

Acta Cryst (2012). E68, o39  [ doi:10.1107/S1600536811051920 ]

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