[Journal logo]

Volume 65 
Part 9 
Page o2163  
September 2009  

Received 10 August 2009
Accepted 11 August 2009
Online 15 August 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.007 Å
R = 0.041
wR = 0.105
Data-to-parameter ratio = 16.5
Details
Open access

4,4',6,6'-Tetrahydroseleno-2,2'-[(E,E)-cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenol

aEngineering Research Center for Clean Production of Textile Dyeing and Printing, Ministry of Education, Wuhan 430073, People's Republic of China
Correspondence e-mail: qfzeng@wuse.edu.cn

In the title molecule, C20H22N2O2Se4, the dihedral angle between the pendant aromatic rings is 67.1 (2)°. The conformation is stabilized by two intramolecular O-H...N hydrogen bonds.

Related literature

For background to the biological activity of Schiff base compounds, see: Shi et al. (2007[Shi, L., Ge, H.-M., Tan, S.-H., Li, H.-Q., Song, Y.-C., Zhu, H.-L. & Tan, R.-X. (2007). Eur. J. Med. Chem. 42, 558-564.]). For reference structural data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C20H22N2O2Se4

  • Mr = 638.24

  • Monoclinic, P 21 /c

  • a = 15.493 (2) Å

  • b = 9.2975 (15) Å

  • c = 16.353 (2) Å

  • [beta] = 109.865 (5)°

  • V = 2215.4 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 6.64 mm-1

  • T = 296 K

  • 0.32 × 0.28 × 0.24 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.225, Tmax = 0.299 (expected range = 0.153-0.203)

  • 11901 measured reflections

  • 4196 independent reflections

  • 2743 reflections with I > 2[sigma](I)

  • Rint = 0.048

  • 3 standard reflections every 200 reflections intensity decay: 1%

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

  • wR(F2) = 0.105

  • S = 1.06

  • 4196 reflections

  • 255 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.84 e Å-3

  • [Delta][rho]min = -0.54 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2A...N2 0.82 1.85 2.575 (5) 147
O1-H1...N1 0.82 1.90 2.619 (5) 145

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: HB5041 ).


Acknowledgements

The project was supported by the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry, Educational Commission of Hubei Province (D20091703) and the Natural Science Foundation of Hubei Province (2008CDB038).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shi, L., Ge, H.-M., Tan, S.-H., Li, H.-Q., Song, Y.-C., Zhu, H.-L. & Tan, R.-X. (2007). Eur. J. Med. Chem. 42, 558-564.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2009). E65, o2163  [ doi:10.1107/S1600536809031572 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.