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Volume 69 
Part 3 
Page o349  
March 2013  

Received 30 November 2012
Accepted 31 January 2013
Online 6 February 2013

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.031
wR = 0.074
Data-to-parameter ratio = 11.7
Details
Open access

N-(Pyrazin-2-yl)-1,8-naphthyridin-2-amine

Yan-Shan Duan,a Wen-Zhen Wang,a* Yuh-Sheng Wen,b Yu-Qin Zhua and Shie-Ming Pengc

aSchool of Chemistry and Chemical Engineering, Xi'an Shiyou University, Xi'an 710065, People's Republic of China,bInstitute of Chemistry, Academia Sinica, Taipei, Taiwan, and cDepartment of Chemistry, National Taiwan University, Taipei 106, Taiwan
Correspondence e-mail: wzwang@xsyu.edu.cn, smpeng@ntu.edu.tw

There are two independent molecules in the asymmetric unit of the title compound, C12H9N5, in which the C-N(amine)-C angles differ slightly [129.63 (11) and 132.02 (11)°]. In each independent molecule, an intramolecular C-H...N hydrogen bond stabilizes the molecular structure, forming an S(6) ring motif. The independent molecules are linked via an N-H...N hydrogen bond. Further N-H...N and C-H...N hydrogen bonds connect the molecules into chains along c axis. Pairs of C-H...[pi] interactions between the chains lead to sheets parallel to the b axis. These are linked by [pi]-[pi] interactions between the naphthyridine and pyrazine rings [centroid-centroid separations of 3.553 (8) Å] into a three-dimensional supramolecular network.

Related literature

For related structures, see: Alvarez-Rua et al. (2004[Alvarez-Rua, C., García-Granda, S., Goswami, S., Mukherjee, R., Dey, S., Claramunt, R. M., María, M. D. S., Rozas, I., Jagerovic, N., Alkortae, I. & Elguero, J. (2004). New J. Chem. 28, 700-707.]); Basato et al. (2006[Basato, M., Biffis, A., Martinati, G., Tubaro, C., Graiff, C., Tiripicchio, A., Aronica, L. A. & Caporusso, A. M. (2006). J. Organomet. Chem. 691, 3464-3471.]); Ghosh et al. (2010[Ghosh, K., Sen, T. & Fröhlich, R. (2010). J. Incl. Phenom. Macrocycl. Chem. 68, 193-199.]); Jin et al. (2010[Jin, S.-W., Zhang, W.-B., Liu, L., Gao, H.-F., Wang, D.-Q., Chen, R.-P. & Xu, X.-L. (2010). J. Mol. Struct. 975, 128-136.], 2011[Jin, S.-W., Liu, L., Wang, D.-Q. & Guo, J.-Z. (2011). J. Mol. Struct. 1005, 59-69.]). For graph-set analysis, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C12H9N5

  • Mr = 223.24

  • Triclinic, [P \overline 1]

  • a = 7.8608 (3) Å

  • b = 11.8200 (5) Å

  • c = 11.9356 (4) Å

  • [alpha] = 105.096 (2)°

  • [beta] = 98.086 (2)°

  • [gamma] = 101.854 (2)°

  • V = 1025.53 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.28 × 0.2 × 0.18 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.927, Tmax = 0.991

  • 16351 measured reflections

  • 3606 independent reflections

  • 2557 reflections with I > 2[sigma](I)

  • Rint = 0.037
Refinement

  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.074

  • S = 0.93

  • 3606 reflections

  • 308 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N22/C23-C25/C29/C30 ring.
D-H...A D-H H...A D...A D-H...A
C27-H27...N33 0.93 2.33 2.9318 (17) 122
C17-H17...N1 0.93 2.24 2.8518 (17) 123
N31-H31...N2 0.86 2.14 2.9396 (15) 154
N11-H11...N22i 0.86 2.23 3.0766 (15) 171
C26-H26...N16ii 0.93 2.51 3.3608 (17) 152
C15-H15...Cg1iii 0.93 2.74 3.472 (2) 136
Symmetry codes: (i) -x, -y+1, -z; (ii) -x, -y+1, -z+1; (iii) x, y+1, z.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2390 ).

Acknowledgements

Financial support for this study came from the National Science Council of the Republic of China, the Natural Science Foundation of Shaanxi Province (No. 2012JM2011) and the Education Department of Shaanxi Province special scientific research plan (No. 11JK0606).

References

Alvarez-Rua, C., García-Granda, S., Goswami, S., Mukherjee, R., Dey, S., Claramunt, R. M., María, M. D. S., Rozas, I., Jagerovic, N., Alkortae, I. & Elguero, J. (2004). New J. Chem. 28, 700-707.  [ChemPort]
Basato, M., Biffis, A., Martinati, G., Tubaro, C., Graiff, C., Tiripicchio, A., Aronica, L. A. & Caporusso, A. M. (2006). J. Organomet. Chem. 691, 3464-3471.  [CSD] [CrossRef] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ghosh, K., Sen, T. & Fröhlich, R. (2010). J. Incl. Phenom. Macrocycl. Chem. 68, 193-199.  [CSD] [CrossRef] [ChemPort]
Jin, S.-W., Liu, L., Wang, D.-Q. & Guo, J.-Z. (2011). J. Mol. Struct. 1005, 59-69.  [ISI] [CSD] [CrossRef] [ChemPort]
Jin, S.-W., Zhang, W.-B., Liu, L., Gao, H.-F., Wang, D.-Q., Chen, R.-P. & Xu, X.-L. (2010). J. Mol. Struct. 975, 128-136.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2013). E69, o349  [ doi:10.1107/S160053681300319X ]

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