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

Wang, Q.; Zha, R.-H.; Yuan, J.-W.; Zeng, Q.-F.

doi:10.1107/S1600536809031572

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 (C-C) = 0.007 Å
R = 0.041
wR = 0.105
Data-to-parameter ratio = 16.5
Details

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

Qiang Wang,^a Ru-Hua Zha,^a Ji-Wen Yuan ^a and Qing-Fu Zeng ^a ^*

^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-HN hydrogen bonds.

Related literature

For background to the biological activity of Schiff base compounds, see: Shi et al. (2007). For reference structural data, see: Allen et al. (1987).

Experimental

Crystal data

C₂₀H₂₂N₂O₂Se₄
M_r = 638.24
Monoclinic, P 2₁ /c
a = 15.493 (2) Å
b = 9.2975 (15) Å
c = 16.353 (2) Å
= 109.865 (5)°
V = 2215.4 (5) Å³
Z = 4
Mo K radiation
= 6.64 mm^-1
T = 296 K
0.32 × 0.28 × 0.24 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.225, T_max = 0.299 (expected range = 0.153-0.203)
11901 measured reflections
4196 independent reflections
2743 reflections with I > 2(I)
R_int = 0.048
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.105
S = 1.06
4196 reflections
255 parameters
H-atom parameters constrained
_max = 0.84 e Å^-3
_min = -0.54 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AN2	0.82	1.85	2.575 (5)	147
O1-H1N1	0.82	1.90	2.619 (5)	145

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.

organic compounds