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Volume 69 
Part 5 
Page o636  
May 2013  

Received 1 March 2013
Accepted 19 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.003 Å
R = 0.030
wR = 0.074
Data-to-parameter ratio = 17.9
Details
Open access

Bis(4-nitrophenyl) selenide

aChemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637002, People's Republic of China
Correspondence e-mail: zuozongle1@163.com

In the title compound, C12H8N2O4Se, the Se atom is situated on a twofold rotational axis, so the asymmetric unit contains one half-molecule. In the molecule, the C-Se-C angle is 99.48 (13)°, the two benzene rings are inclined to each other at an angle of 63.8 (1)° and the nitro group is twisted by 15.9 (1)° from the attached benzene ring. In the crystal, molecules are held together through weak C-H...O interactions, forming a three-dimensional network.

Related literature

For applications of organoselenium compounds, see: Mugesh et al. (2001[Mugesh, G., du Mont, W. W. & Sies, H. (2001). Chem. Rev. 101, 2125-2179.]); Nogueira et al. (2004[Nogueira, C. W., Zeni, G. & Rocha, J. B. (2004). Chem. Rev. 104, 6255-6285.]); Wirth (1999[Wirth, T. (1999). Tetrahedron, 55, 1-28.]). For details of the synthesis, see: Taniguchi (2005[Taniguchi, N. (2005). Synlett, pp. 1687-1690.]). The crystal structures of the related compounds bis(p-tolyl) selenide and bis(4-acetylphenyl) selenide were reported by Blackmore & Abrahams (1955[Blackmore, W. R. & Abrahams, S. C. (1955). Acta Cryst. 8, 323-328.]) and Bouraoui et al. (2011[Bouraoui, H., Boudjada, A., Bouacida, S., Mechehoud, Y. & Meinnel, J. (2011). Acta Cryst. E67, o941.]), respectively.

[Scheme 1]

Experimental

Crystal data
  • C12H8N2O4Se

  • Mr = 323.16

  • Monoclinic, C 2/c

  • a = 7.207 (4) Å

  • b = 14.176 (7) Å

  • c = 11.686 (5) Å

  • [beta] = 101.870 (7)°

  • V = 1168.3 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.23 mm-1

  • T = 153 K

  • 0.47 × 0.34 × 0.34 mm

Data collection
  • Rigaku AFC10/Saturn724+ diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.314, Tmax = 0.402

  • 4848 measured reflections

  • 1557 independent reflections

  • 1298 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.074

  • S = 1.00

  • 1557 reflections

  • 87 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.70 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O2i 0.95 2.51 3.426 (3) 162
C6-H6...O2ii 0.95 2.50 3.427 (3) 164
Symmetry codes: (i) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) [x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CV5389 ).


References

Blackmore, W. R. & Abrahams, S. C. (1955). Acta Cryst. 8, 323-328.  [CrossRef] [ChemPort] [details]
Bouraoui, H., Boudjada, A., Bouacida, S., Mechehoud, Y. & Meinnel, J. (2011). Acta Cryst. E67, o941.  [CSD] [CrossRef] [details]
Mugesh, G., du Mont, W. W. & Sies, H. (2001). Chem. Rev. 101, 2125-2179.  [ISI] [CrossRef] [PubMed] [ChemPort]
Nogueira, C. W., Zeni, G. & Rocha, J. B. (2004). Chem. Rev. 104, 6255-6285.  [ISI] [CrossRef] [PubMed] [ChemPort]
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Taniguchi, N. (2005). Synlett, pp. 1687-1690.  [ISI] [CrossRef]
Wirth, T. (1999). Tetrahedron, 55, 1-28.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o636  [ doi:10.1107/S1600536813007526 ]

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