4,6-Dichloro-2-{[(E)-(3-{[(E)-3,5-dichloro-2-hy­droxy­benzyl­idene]amino}-2,2-dimethyl­prop­yl)imino]­meth­yl}phenol

Kargar, H.; Kia, R.; Abbasian, S.; Tahir, M.N.

doi:10.1107/S1600536811053438

Volume 68
Part 1
Page o142
January 2012

Received 9 December 2011
Accepted 12 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.042
wR = 0.119
Data-to-parameter ratio = 21.0
Details

4,6-Dichloro-2-{[(E)-(3-{[(E)-3,5-dichloro-2-hydroxybenzylidene]amino}-2,2-dimethylpropyl)imino]methyl}phenol

Hadi Kargar,^a ^* Reza Kia,^b,^c Saeideh Abbasian ^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 compound, C₁₉H₁₈Cl₄N₂O₂, a potential tetradentate Schiff base ligand, the dihedral angle between the two benzene rings is 48.01 (10)°. The configuration about the two C=N bonds is E and two intramolecular O-HN hydrogen bonds make S(6) ring motifs. In the crystal, molecules are linked along the b axis via intermolecular C-HCl interactions. The crystal structure is further stabilized by an intermolecular [pi] - [pi] interaction [centroid-centroid distance = 3.5744 (12) 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

C₁₉H₁₈Cl₄N₂O₂
M_r = 448.15
Monoclinic, P 2₁ /c
a = 16.5265 (5) Å
b = 10.3242 (3) Å
c = 12.6433 (4) Å
= 104.796 (1)°
V = 2085.70 (11) Å³
Z = 4
Mo K radiation
= 0.58 mm^-1
T = 296 K
0.18 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.902, T_max = 0.955
19903 measured reflections
5165 independent reflections
3427 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.119
S = 1.03
5165 reflections
246 parameters
H-atom parameters constrained
_max = 0.40 e Å^-3
_min = -0.38 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.93	1.73	2.553 (2)	147
O2-H2AN2	0.90	1.71	2.553 (2)	155
C12-H12BCl1ⁱ	0.97	2.80	3.749 (2)	167
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

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: SU2348 ).

Acknowledgements

HK and SA 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.
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