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Volume 69 
Part 5 
Page o674  
May 2013  

Received 12 March 2013
Accepted 29 March 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.058
wR = 0.124
Data-to-parameter ratio = 12.3
Details
Open access

4-(1H-Pyrrolo[2,3-b]pyridin-2-yl)pyridine

aCardinal Tien College of Healthcare & Management, Taipei, Taiwan 231, Republic of China,bInstitute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan, Republic of China, and cDepartment of Chemistry, National Taiwan University, Taipei, Taiwan, Republic of China
Correspondence e-mail: pshuang@ctcn.edu.tw

The asymmetric unit of the title compound, C12H9N3, contains two independent molecules in which the dihedral angle between the pyridine and azaindole rings are 8.23 (6) and 9.89 (2)°. In the crystal, both types of molecule are connected by pairs of N-H-N hydrogen bonds into inversion dimers.

Related literature

For the production of luminescent organic compounds, see: Liu et al. (2000[Liu, S. F., Wu, Q., Schmider, H. L., Aziz, H., Hu, N. X., Popovic, Z. & Wang, S. (2000). J. Am. Chem. Soc. 122, 3671-3678.]); Parcerisa et al. (2008[Parcerisa, J., Romero, M. & Pujol, M. D. (2008). Tetrahedron, 64, 500-507.]). For related structures, see: Huang et al. (2012[Huang, P.-H., Wen, Y.-S. & Shen, J.-Y. (2012). Acta Cryst. E68, o1943.]).

[Scheme 1]

Experimental

Crystal data
  • C12H9N3

  • Mr = 195.22

  • Triclinic, [P \overline 1]

  • a = 6.5529 (5) Å

  • b = 10.0457 (8) Å

  • c = 14.5282 (11) Å

  • [alpha] = 83.372 (2)°

  • [beta] = 86.697 (2)°

  • [gamma] = 87.427 (2)°

  • V = 947.69 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 295 K

  • 0.30 × 0.20 × 0.05 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.975, Tmax = 0.996

  • 10193 measured reflections

  • 3329 independent reflections

  • 2573 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.124

  • S = 1.14

  • 3329 reflections

  • 271 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N2i 0.86 2.22 3.061 (3) 167
N4-H4A...N5ii 0.86 2.22 3.066 (3) 169
Symmetry codes: (i) -x, -y+2, -z+2; (ii) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. 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: NC2308 ).


Acknowledgements

This work is partially supported by the instrumentation center, National Taiwan University, and Cardinal Tien College of Healthcare & Management.

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Huang, P.-H., Wen, Y.-S. & Shen, J.-Y. (2012). Acta Cryst. E68, o1943.  [CSD] [CrossRef] [details]
Liu, S. F., Wu, Q., Schmider, H. L., Aziz, H., Hu, N. X., Popovic, Z. & Wang, S. (2000). J. Am. Chem. Soc. 122, 3671-3678.  [ISI] [CrossRef] [ChemPort]
Parcerisa, J., Romero, M. & Pujol, M. D. (2008). Tetrahedron, 64, 500-507.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o674  [ doi:10.1107/S1600536813008672 ]

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