4,4′,6,6′-Tetra­bromo-2,2′-[(E,E)-ethane-1,2-diylbis(nitrilo­methanylyl­idene)]di­phenol

Kargar, H.; Kia, R.; Adabi Ardakani, A.; Tahir, M.N.

doi:10.1107/S1600536812029832

Volume 68
Part 8
Page o2348
August 2012

Received 28 June 2012
Accepted 30 June 2012
Online 7 July 2012

Key indicators
Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.010 Å
R = 0.069
wR = 0.202
Data-to-parameter ratio = 18.2
Details

4,4',6,6'-Tetrabromo-2,2'-[(E,E)-ethane-1,2-diylbis(nitrilomethanylylidene)]diphenol

Hadi Kargar,^a Reza Kia,^b ^*⁺ Amir Adabi Ardakani ^a and Muhammad Nawaz Tahir ^c ^*

^aDepartment of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, I. R. of IRAN,^bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and ^cDepartment of Physics, University of Sargodha, Punjab, Pakistan
Correspondence e-mail: zsrkk@yahoo.com, dmntahir_uos@yahoo.com

The asymmetric unit of the title compound, C₁₆H₁₂Br₄N₂O₂, comprises half of a potential tetradentate Schiff base ligand. The whole molecule is generated by an inversion center located in the middle of the C-C bond of the ethylene segment. There are intramolecular O-HN hydrogen bonds making S(6) ring motifs. In the crystal, no significant intermolecular interactions are observed.

Related literature

For standard values of bond lengths, see: Allen et al. (1987). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For the crystal structure of a similar compound, see: Kia et al. (2012).

Experimental

Crystal data

C₁₆H₁₂Br₄N₂O₂
M_r = 583.92
Monoclinic, P 2₁ /c
a = 12.723 (3) Å
b = 10.291 (2) Å
c = 6.9428 (18) Å
= 97.046 (15)°
V = 902.2 (4) Å³
Z = 2
Mo K radiation
= 8.93 mm^-1
T = 291 K
0.21 × 0.14 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.256, T_max = 0.535
6730 measured reflections
1981 independent reflections
1086 reflections with I > 2(I)
R_int = 0.075

Refinement

R[F² > 2(F²)] = 0.069
wR(F²) = 0.202
S = 0.98
1981 reflections
109 parameters
H-atom parameters constrained
_max = 1.40 e Å^-3
_min = -0.90 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.82	1.83	2.573 (7)	151

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2470 ).

Acknowledgements

HK and AAA thank PNU for financial support. MNT thanks GC University of Sargodha, Pakistan, for research facilities.

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Kia, R., Kargar, H., Adabi Ardakani, A. & Tahir, M. N. (2012). Acta Cryst. E68, o2242-o2243.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds