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Volume 69 
Part 10 
Page o1537  
October 2013  

Received 10 July 2013
Accepted 26 August 2013
Online 12 September 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.007 Å
R = 0.052
wR = 0.132
Data-to-parameter ratio = 12.4
Details
Open access

N-(2-Bromophenyl)-1,3-selenazolo[5,4-b]pyridin-2-amine

aCollege of Science, Honghe University, Mengzi 661100, People's Republic of China, and bDepartment of Chemistry, Jinan University, Guangzhou 510632, People's Republic of China
Correspondence e-mail: liuwei4728@126.com;zhoubo432@163.com

The molecular structure of the title molecule, C12H8BrN3Se, is built up from fused selenazolo and pyridine rings, linked to a 2-bromoaniline group. In the crystal, pairs of molecules are linked by N-H...N hydrogen bonds into dimers, forming eight-membered ring motifs.

Related literature

For the bioactivity of organoselenium compounds, see: Garud et al. (2007[Garud, D. R., Koketsu, M. & Ishihara, H. (2007). Molecules, 12, 504-535.]); Ling et al. (2010[Ling, C., Zheng, Z., Jiang, X., Zhong, W. & Li, S. (2010). Bioorg. Med. Chem. Lett. 20, 5123-5125.]); Plamen et al. (2010[Plamen, K. A., Anthony, L. & Heinz, H. (2010). Helv. Chim. Acta, 93, 395-404.]). For crystallographic studies of selenazolo derivatives, see: Plamen et al. (2004[Plamen, K. A., Anthony, L. & Heinz, H. (2004). Helv. Chim. Acta, 87, 1883-1887.]).

[Scheme 1]

Experimental

Crystal data
  • C12H8BrN3Se

  • Mr = 353.08

  • Monoclinic, P 21 /n

  • a = 12.5312 (5) Å

  • b = 7.4562 (3) Å

  • c = 13.8913 (5) Å

  • [beta] = 112.331 (4)°

  • V = 1200.60 (8) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 7.96 mm-1

  • T = 295 K

  • 0.30 × 0.30 × 0.10 mm

Data collection
  • Agilent Xcalibur (Sapphire3, Gemini ultra) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.] Tmin = 0.199, Tmax = 0.299

  • 4420 measured reflections

  • 1921 independent reflections

  • 1779 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.132

  • S = 1.11

  • 1921 reflections

  • 155 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.66 e Å-3

  • [Delta][rho]min = -1.88 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3...N2i 1.06 1.88 2.933 (4) 174
Symmetry code: (i) -x+1, -y, -z.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: 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: FJ2639 ).


Acknowledgements

This work was supported by grants from the National Natural Science Fund (Nos. 31000816 and 21071062).

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Garud, D. R., Koketsu, M. & Ishihara, H. (2007). Molecules, 12, 504-535.  [CrossRef] [PubMed] [ChemPort]
Ling, C., Zheng, Z., Jiang, X., Zhong, W. & Li, S. (2010). Bioorg. Med. Chem. Lett. 20, 5123-5125.  [CrossRef] [ChemPort] [PubMed]
Plamen, K. A., Anthony, L. & Heinz, H. (2004). Helv. Chim. Acta, 87, 1883-1887.
Plamen, K. A., Anthony, L. & Heinz, H. (2010). Helv. Chim. Acta, 93, 395-404.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1537  [ doi:10.1107/S1600536813023969 ]

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