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Volume 69 
Part 12 
Page o1791  
December 2013  

Received 12 June 2013
Accepted 1 November 2013
Online 20 November 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.004 Å
R = 0.047
wR = 0.090
Data-to-parameter ratio = 38.2
Details
Open access

2-(Phenyl­selenon­yl)pyridine

aDepartment of Chemistry, D. A. V. College, Sector-10, Chandigarh, India,bDepartment of Chemistry & Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh 160 014, India,cA.E. Favorsky Irkutsk Institute of Chemistry, 1 Favorsky Street, Irkutsk, RUS-664033, Russian Federation, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: rbutcher99@yahoo.com

In the title compound, C11H9NO2Se, the pyridine and phenyl rings are almost perpendicular, with the dihedral angle between their mean planes being 79.16 (7)°. In the crystal, the mol­ecules pack so as to form ruffled sheets in the (110) plane connected by weak C-H...O inter­actions. In addition, there are weak [pi]-[pi] inter­actions between the mean planes of both the phenyl [centroid-centroid perpendicular distance of 3.591 (2) Å and slippage of 1.854 (2) Å] and pyridine rings [centroid-centroid perpendicular distance of 3.348 (2) Å and slippage of 1.854 (2) Å].

Related literature

For the pharmacological activity of selenone derivatives, see: Abdel-Hafez & Hussein (2008[Abdel-Hafez, S. H. & Hussein, M. A. (2008). Arch. Pharm. 341, 240-246.]); Zhao et al. (2012[Zhao, L., Li, J., Li, Y., Liu, J., Wirth, T. & Li, Z. (2012). Bioorg. Med. Chem. 20, 2558-2563.]); Hassan et al. (2011[Hassan, W., Narayanaperumal, S., Santos, M. M., Gul, K., Mohammadzai, I. U., Braga, A. L., Rodrigues, O. D. & Rocha, J. B. T. (2011). Pharm. Anal. Acta. doi:10.4172/2153-2435.S3-002.]); Bhabak et al. (2011[Bhabak, K. P., Vernekar, A. A., Jakka, S. R., Roy, G. & Mugesh, G. (2011). Org. Biomol. Chem. 9, 5193-5200.]). For the chemistry of selenium compounds bonded directly to pyridine, see: Bhasin et al. (2013[Bhasin K. K., Arora E., Grover A. S., Jyoti, Singh. H., Mehta S. K, Bhasin, A. K. K. & Jacob C. (2013). J. Organomet. Chem. 732, 137-141.]). For the synthesis of pharmaceuticals, see: Nogueira & Rocha (2011[Nogueira, C. W. & Rocha, J. B. (2011). Arch. Toxicol. 85, 1313-1359.]). For the synthesis of perfumes, fine chemicals and polymers, see: Zeng et al. (2013[Zeng, J., Zhu, J., Pan, X., Zhang, Z., Zhou, N., Cheng, Z., Zhang, W. & Zhu, X. (2013). Polym. Chem. Advance Article.]).

[Scheme 1]

Experimental

Crystal data
  • C11H9NO2Se

  • Mr = 266.15

  • Triclinic, [P \overline 1]

  • a = 6.1598 (5) Å

  • b = 7.7223 (6) Å

  • c = 11.4952 (7) Å

  • [alpha] = 80.683 (6)°

  • [beta] = 83.494 (6)°

  • [gamma] = 74.614 (7)°

  • V = 518.83 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 3.60 mm-1

  • T = 123 K

  • 0.50 × 0.26 × 0.16 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: analytical (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.383, Tmax = 0.613

  • 8688 measured reflections

  • 5196 independent reflections

  • 3965 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.090

  • S = 1.01

  • 5196 reflections

  • 136 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.64 e Å-3

  • [Delta][rho]min = -0.76 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2A-H2AA...O1i 0.95 2.50 3.331 (3) 146
C4A-H4AA...O1ii 0.95 2.53 3.341 (3) 143
C5A-H5AA...O2iii 0.95 2.35 3.188 (3) 146
Symmetry codes: (i) x-1, y, z; (ii) x-1, y+1, z; (iii) x, y+1, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. 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: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2170 ).


Acknowledgements

This work was supported by the Department of Science and Technology, DST, New Delhi (Research Grant SR/S1/IC-37/2009). RJB wishes to acknowledge the NSF-MRI program (grant CHE-0619278) for funds to purchase the diffractometer as well as the Howard University Nanoscience Facility for access to liquid nitro­gen.

References

Abdel-Hafez, S. H. & Hussein, M. A. (2008). Arch. Pharm. 341, 240-246.  [ChemPort]
Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Bhabak, K. P., Vernekar, A. A., Jakka, S. R., Roy, G. & Mugesh, G. (2011). Org. Biomol. Chem. 9, 5193-5200.  [CSD] [CrossRef] [ChemPort] [PubMed]
Bhasin K. K., Arora E., Grover A. S., Jyoti, Singh. H., Mehta S. K, Bhasin, A. K. K. & Jacob C. (2013). J. Organomet. Chem. 732, 137-141.
Hassan, W., Narayanaperumal, S., Santos, M. M., Gul, K., Mohammadzai, I. U., Braga, A. L., Rodrigues, O. D. & Rocha, J. B. T. (2011). Pharm. Anal. Acta. doi:10.4172/2153-2435.S3-002.
Nogueira, C. W. & Rocha, J. B. (2011). Arch. Toxicol. 85, 1313-1359.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Zeng, J., Zhu, J., Pan, X., Zhang, Z., Zhou, N., Cheng, Z., Zhang, W. & Zhu, X. (2013). Polym. Chem. Advance Article.
Zhao, L., Li, J., Li, Y., Liu, J., Wirth, T. & Li, Z. (2012). Bioorg. Med. Chem. 20, 2558-2563.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1791  [ doi:10.1107/S1600536813029978 ]

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