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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 [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.119
Data-to-parameter ratio = 21.0
Details
Open access

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

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-H...N hydrogen bonds make S(6) ring motifs. In the crystal, molecules are linked along the b axis via intermolecular C-H...Cl 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[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.]). For hydrogen bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For related structures, see: Kargar et al. (2011[Kargar, H., Kia, R., Pahlavani, E. & Tahir, M. N. (2011). Acta Cryst. E67, o614.]); Kia et al. (2010[Kia, R., Kargar, H., Tahir, M. N. & Kianoosh, F. (2010). Acta Cryst. E66, o2296.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18Cl4N2O2

  • Mr = 448.15

  • Monoclinic, P 21 /c

  • a = 16.5265 (5) Å

  • b = 10.3242 (3) Å

  • c = 12.6433 (4) Å

  • [beta] = 104.796 (1)°

  • V = 2085.70 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.902, Tmax = 0.955

  • 19903 measured reflections

  • 5165 independent reflections

  • 3427 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.119

  • S = 1.03

  • 5165 reflections

  • 246 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.93 1.73 2.553 (2) 147
O2-H2A...N2 0.90 1.71 2.553 (2) 155
C12-H12B...Cl1i 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [CrossRef] [ChemPort] [ISI]
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.  [CSD] [CrossRef] [details]
Kia, R., Kargar, H., Tahir, M. N. & Kianoosh, F. (2010). Acta Cryst. E66, o2296.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o142  [ doi:10.1107/S1600536811053438 ]

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