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

Hadi Kargar; Reza Kia; Mahbubeh Haghshenas; Muhammad Nawaz Tahir

doi:10.1107/S1600536811055899

. 2012 Jan 11;68(Pt 2):o323. doi: 10.1107/S1600536811055899

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, Muhammad Nawaz Tahir ^d,^*

PMCID: PMC3275012 PMID: 22346957

Abstract

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 π–π 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,
a = 11.6861 (3) Å
b = 11.4616 (3) Å
c = 31.3782 (9) Å
V = 4202.8 (2) Å³
Z = 8
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.090

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.138
S = 1.04
5242 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.64 e Å⁻³

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 Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055899/su2354sup1.cif

e-68-0o323-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055899/su2354Isup2.hkl

e-68-0o323-Isup2.hkl^{(256.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

In continuation of our work on the crystal structure analysis of Schiff base ligands (Kargar et al., 2011; Kia et al., 2010), we synthesized the title compound and report herein on its crystal structure.

The title compound (Fig. 1) is a potential tetradentate Zwitterionic Schiff base ligand. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to thoses observed for related structures (Kargar et al., 2011; Kia et al., 2010).

In the molecule there are two intramolecular N—H···O hydrogen bonds (Table 1) making S(6) ring motifs (Bernstein et al., 1995). The dihedral angle between the benzene rings is 73.9 (2)°. An interesting feature of the crystal structure is the short C6···Br1ⁱⁱ contact [3.401 (5) Å; (ii) -x+1/2, y-1/2, z] , which is shorter than the sum of the van der Waals radii [3.55 Å] of these atoms.

In the crystal, molecules are linked together along the a axis into chains through an intermolecular C—H···O interaction (Fig. 2 and Table 1). The crystal structure is further stabilized by an intermolecular π-π interaction [Cg1···Cg2ⁱⁱⁱ = 3.739 (3)Å; (iii) x, -y-1/2, z+1/2; Cg1 and Cg2 are the centroid of benzene rings (C1–C6) and (C14–19), respectively].

Experimental

The title compound was synthesized by adding 3,5-dibromo-salicylaldehyde (2 mmol) to a solution of 2,2-dimethyl-1,3-propanediamine (1 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for 30 min. The resultant solution was filtered. Yellow single crystals of the title compound, suitable for X-ray structure determination, were recrystallized from ethanol by slow evaporation of the solvent at room temperature over several days.