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Volume 69 
Part 3 
Page o381  
March 2013  

Received 9 February 2013
Accepted 11 February 2013
Online 16 February 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.006 Å
R = 0.035
wR = 0.092
Data-to-parameter ratio = 13.0
Details
Open access

5-Bromo-1H-pyrrolo[2,3-b]pyridine

aDepartment of Inorganic Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, CZ-771 46 Olomouc, Czech Republic
Correspondence e-mail: zdenek.travnicek@upol.cz

In the title compound, C7H5BrN2, fused six-membered pyridine and five-membered pyrrole rings form the essentially planar azaindole skeleton (r.m.s. deviation = 0.017 Å). In the crystal, pairs of N-H...N hydrogen bonds connect the molecules into inversion dimers.

Related literature

For the structure of 7-azaindole (C7H6N2), see: Dufour et al. (1990[Dufour, P., Dartiguenave, Y., Dartiguenave, M., Dufour, N., Lebuis, A. M., Belanger-Gariepy, F. & Beauchamp, A. L. (1990). Can. J. Chem. 68, 193-202.]) and for the structure of 3-iodo-7-azaindole (C7H5IN2), see: Chou et al. (2000[Chou, P. T., Liao, J. H., Wei, C. Y., Yang, C. Y., Yu, W. S. & Chou, Y. H. (2000). J. Am. Chem. Soc. 122, 986-987.]). For the utilization of the title compound as the N-donor carrier ligand of highly cytotoxic platinum(II) dichlorido complexes, see: Starha et al. (2012[Starha, P., Trávnícek, Z., Popa, A., Popa, I., Muchová, T. & Brabec, V. (2012). J. Inorg. Biochem. 115, 57-63.]).

[Scheme 1]

Experimental

Crystal data
  • C7H5BrN2

  • Mr = 197.04

  • Monoclinic, P 21 /c

  • a = 8.9082 (4) Å

  • b = 13.3632 (6) Å

  • c = 5.8330 (3) Å

  • [beta] = 103.403 (5)°

  • V = 675.47 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 6.00 mm-1

  • T = 100 K

  • 0.24 × 0.24 × 0.12 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire2 CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.327, Tmax = 0.533

  • 3977 measured reflections

  • 1185 independent reflections

  • 1047 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.092

  • S = 1.13

  • 1185 reflections

  • 91 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.69 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N7i 0.88 2.12 2.960 (5) 159
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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: DIAMOND (Brandenburg et al., 2011[Brandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: 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: TK5196 ).


Acknowledgements

This work was supported by Palacký University (grant No. PrF_2012_009). The authors wish to thank Dr Igor Popa for carrying out the NMR spectroscopy measurements and Mr Tomás Silha for performing the CHN elemental analysis.

References

Brandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Chou, P. T., Liao, J. H., Wei, C. Y., Yang, C. Y., Yu, W. S. & Chou, Y. H. (2000). J. Am. Chem. Soc. 122, 986-987.  [ISI] [CrossRef] [ChemPort]
Dufour, P., Dartiguenave, Y., Dartiguenave, M., Dufour, N., Lebuis, A. M., Belanger-Gariepy, F. & Beauchamp, A. L. (1990). Can. J. Chem. 68, 193-202.  [CrossRef] [ChemPort] [ISI]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Starha, P., Trávnícek, Z., Popa, A., Popa, I., Muchová, T. & Brabec, V. (2012). J. Inorg. Biochem. 115, 57-63.  [ISI] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o381  [ doi:10.1107/S1600536813004157 ]

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