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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 [sigma](C-C) = 0.007 Å
R = 0.047
wR = 0.138
Data-to-parameter ratio = 21.3
Details
Open access

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

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-H...O hydrogen bonds make S(6) ring motifs. In the crystal, molecules are linked via C-H...O interactions, forming chains propagating along the a-axis directon. A short C...Br [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[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
  • C19H18Br4N2O

  • Mr = 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[alpha] radiation

  • [mu] = 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.250, Tmax = 0.459

  • 38547 measured reflections

  • 5242 independent reflections

  • 2756 reflections with I > 2[sigma](I)

  • Rint = 0.090

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.138

  • S = 1.04

  • 5242 reflections

  • 246 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.73 e Å-3

  • [Delta][rho]min = -0.64 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1 0.85 1.82 2.549 (5) 142
N2-H2...O2 0.86 1.80 2.537 (5) 143
C8-H8A...O2i 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[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: 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.  [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, o323  [ doi:10.1107/S1600536811055899 ]

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