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Volume 69 
Part 10 
Page o1497  
October 2013  

Received 6 August 2013
Accepted 22 August 2013
Online 4 September 2013

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.020 Å
R = 0.094
wR = 0.314
Data-to-parameter ratio = 12.0
Details
Open access

N-p-Tolyl-1,3-selenazolo[5,4-b]pyridin-2-amine

aDepartment of Chemistry, Jinan University, Guangzhou 510632, People's Republic of China, and bDepartment of Food Science and Technology, Jinan, University, Guangzhou 510632, People's Republic of China
Correspondence e-mail: zhouhua5460@jnu.edu.cn

In the title compound, C13H11N3Se, the dihedral angle between the mean plane of the fused selenoazolopyridine ring system and the p-toluidine ring is 14.260 (5)°. In the crystal, molecules are linked by N-H...N hydrogen bonds, forming zigzag chains extending along the b-axis direction.

Related literature

For the bioactivity of organoselenium, 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 on 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
  • C13H11N3Se

  • Mr = 288.21

  • Orthorhombic, P b c a

  • a = 13.138 (2) Å

  • b = 10.0323 (19) Å

  • c = 17.838 (3) Å

  • V = 2351.2 (7) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 4.15 mm-1

  • T = 153 K

  • 0.30 × 0.30 × 0.20 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 = 0.369, Tmax = 0.491

  • 5248 measured reflections

  • 1863 independent reflections

  • 1423 reflections with I > 2[sigma]I)

  • Rint = 0.064

Refinement
  • R[F2 > 2[sigma](F2)] = 0.094

  • wR(F2) = 0.314

  • S = 1.28

  • 1863 reflections

  • 155 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.47 e Å-3

  • [Delta][rho]min = -2.49 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N10-H10...N1i 0.88 2.11 2.983 (16) 175
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2275 ).


Acknowledgements

This work was supported by grants from the National Natural Science Fund (Nos. 31000816 and 21071062) and the high-performance computing platform of Jinan University.

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]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [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, o1497  [ doi:10.1107/S1600536813023659 ]

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