2,4-Dibromo-6-[(E)-({3-[(E)-(3,5-dibromo-2-oxidobenzyl­idene)aza­nium­yl]-2,2-dimethyl­prop­yl}iminium­yl)meth­yl]phenolate

Kargar, H.; Kia, R.; Haghshenas, M.; Tahir, M.N.

doi:10.1107/S1600536811055899

Volume 68
Part 2
Page o323
February 2012

Received 25 December 2011
Accepted 27 December 2011
Online 11 January 2012

Key indicators
Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.007 Å
R = 0.047
wR = 0.138
Data-to-parameter ratio = 21.3
Details

2,4-Dibromo-6-[(E)-({3-[(E)-(3,5-dibromo-2-oxidobenzylidene)azaniumyl]-2,2-dimethylpropyl}iminiumyl)methyl]phenolate

Hadi Kargar,^a ^* Reza Kia,^b,^c Mahbubeh Haghshenas ^a and Muhammad Nawaz Tahir ^d ^*

^aDepartment of Chemistry, Payame Noor University, PO BOX 19395-3697 Tehran, I. R. of IRAN,^bX-ray Crystallography Lab., Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran,^cDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and ^dDepartment of Physics, University of Sargodha, Punjab, Pakistan
Correspondence e-mail: hkargar@pnu.ac.ir, dmntahir_uos@yahoo.com

In the title molecule, C₁₉H₁₈Br₄N₂O₂, the dihedral angle between the benzene rings is 73.9 (2)°. Two intramolecular N-HO hydrogen bonds make S(6) ring motifs. In the crystal, molecules are linked via C-HO interactions, forming chains propagating along the a-axis directon. A short CBr [3.401 (5) Å] contact is present in the crystal structure, which is further stabilized by a [pi] - [pi] interaction [centroid-centroid distance = 3.739 (3) Å].

Related literature

For standard bond lengths, see: Allen et al. (1987). For hydrogen bond motifs, see: Bernstein et al. (1995). For related structures, see: Kargar et al. (2011); Kia et al. (2010).

Experimental

Crystal data

C₁₉H₁₈Br₄N₂O
M_r = 625.99
Orthorhombic, P b c a
a = 11.6861 (3) Å
b = 11.4616 (3) Å
c = 31.3782 (9) Å
V = 4202.8 (2) Å³
Z = 8
Mo K radiation
= 7.68 mm^-1
T = 291 K
0.25 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.250, T_max = 0.459
38547 measured reflections
5242 independent reflections
2756 reflections with I > 2(I)
R_int = 0.090

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.138
S = 1.04
5242 reflections
246 parameters
H-atom parameters constrained
_max = 0.73 e Å^-3
_min = -0.64 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1	0.85	1.82	2.549 (5)	142
N2-H2O2	0.86	1.80	2.537 (5)	143
C8-H8AO2ⁱ	0.97	2.53	3.424 (7)	152
Symmetry code: (i) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

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: SU2354 ).

Acknowledgements

HK and MH thank PNU for financial support, and MNT thanks the 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.
Kargar, H., Kia, R., Pahlavani, E. & Tahir, M. N. (2011). Acta Cryst. E67, o614.
Kia, R., Kargar, H., Tahir, M. N. & Kianoosh, F. (2010). Acta Cryst. E66, o2296.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds