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Volume 69 
Part 10 
Page o1538  
October 2013  

Received 20 August 2013
Accepted 5 September 2013
Online 12 September 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.006 Å
R = 0.041
wR = 0.095
Data-to-parameter ratio = 13.8
Details
Open access

N-(2-Methylphenyl)-1,2-benzoselenazol-3(2H)-one

aThe School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, People's Republic of China,bDepartment of Chemistry, Taiyuan Normal University, Taiyuan 030031, People's Republic of China, and cInstitute of Applied Chemistry, Shanxi University, Taiyuan 030006, People's Republic of China
Correspondence e-mail: hfhan001@163.com;_gzq@sxu.edu.cn

In the title Ebselen [systematic name: (2-phenyl-1,2-benzoisoselenazol-3-(2H)-one)] analogue, C14H11NOSe, the benzisoselenazolyl moiety (r.m.s. deviation = 0.0209 Å) is nearly perpendicular to the N-arenyl ring, making a dihedral angle of 78.15 (11)°. In the crystal, molecules are linked by C-H...O and Se...O interactions into chains along the c-axis direction. The Se...O distance [2.733 (3) Å] is longer than that in Ebselen (2.571 (3) Å].

Related literature

For general background to the properties of Ebselen, see: Bhabak & Mugesh (2010[Bhabak, K. P. & Mugesh, G. (2010). Acc. Chem. Res, 43, 1408-1419.]); Mugesh et al. (2001a[Mugesh, G., Mont, W. W. & Sies, H. (2001a). Chem. Rev. 101, 2125-2180.],b[Mugesh, G., Panda, A. & Singh, H. B. (2001b). J. Am. Chem. Soc. 123, 839-850.]); Mugesh & Singh (2000[Mugesh, G. & Singh, H. B. (2000). Chem. Soc. Rev. 29, 347-357.]); Engman (1989[Engman, L. (1989). J. Org. Chem. 54, 2964-2966.]); Parnham & Graf (1991[Parnham, M. J. & Graf, E. (1991). Prog. Drug Res. 36, 9-47.]). For related structures, see: Balkrishna et al. (2010[Balkrishna, S. J., Bhakuni, B. S., Chopra, D. & Kumar, S. (2010). Org. Lett. 12, 5394-5397.]); Bhabak & Mugesh (2007[Bhabak, K. P. & Mugesh, G. (2007). Chem. Eur. J. 13, 4594-4601.]); Chang et al. (2003[Chang, T. C., Huang, M. L., Hsu, W. L., Hwang, J. M. & Hsu, L. Y. (2003). Chem. Pharm. Bull. 51, 1413-1416.]); Dupont et al. (1990[Dupont, L., Dideberg, O. & Jacquemin, P. (1990). Acta Cryst. C46, 484-486.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11NOSe

  • Mr = 288.20

  • Monoclinic, P 21 /n

  • a = 7.7319 (14) Å

  • b = 13.491 (2) Å

  • c = 11.913 (2) Å

  • [beta] = 102.625 (3)°

  • V = 1212.6 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.08 mm-1

  • T = 273 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.459, Tmax = 0.578

  • 4948 measured reflections

  • 2133 independent reflections

  • 1840 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.095

  • S = 1.10

  • 2133 reflections

  • 155 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...Oi 0.93 2.45 3.132 (4) 130
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. 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: 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: BG2515 ).


Acknowledgements

We thank the NSFC (20772074; 31070295), SXNSFC (2008011021; 2008012013-2; 2011021011-1) and the Research Project Supported by the Shanxi Scholarship Council of China for financial support.

References

Balkrishna, S. J., Bhakuni, B. S., Chopra, D. & Kumar, S. (2010). Org. Lett. 12, 5394-5397.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Bhabak, K. P. & Mugesh, G. (2007). Chem. Eur. J. 13, 4594-4601.  [CSD] [CrossRef] [PubMed] [ChemPort]
Bhabak, K. P. & Mugesh, G. (2010). Acc. Chem. Res, 43, 1408-1419.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chang, T. C., Huang, M. L., Hsu, W. L., Hwang, J. M. & Hsu, L. Y. (2003). Chem. Pharm. Bull. 51, 1413-1416.  [CrossRef] [PubMed] [ChemPort]
Dupont, L., Dideberg, O. & Jacquemin, P. (1990). Acta Cryst. C46, 484-486.  [CSD] [CrossRef] [IUCr Journals]
Engman, L. (1989). J. Org. Chem. 54, 2964-2966.  [CrossRef] [ChemPort]
Mugesh, G., Mont, W. W. & Sies, H. (2001a). Chem. Rev. 101, 2125-2180.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Mugesh, G., Panda, A. & Singh, H. B. (2001b). J. Am. Chem. Soc. 123, 839-850.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Mugesh, G. & Singh, H. B. (2000). Chem. Soc. Rev. 29, 347-357.  [Web of Science] [CrossRef] [ChemPort]
Parnham, M. J. & Graf, E. (1991). Prog. Drug Res. 36, 9-47.  [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1538  [ doi:10.1107/S1600536813024744 ]

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