4-Bromo-2-[(E)-(4-chloro­phen­yl)imino­meth­yl]phenol

Amir Adabi Ardakani; Reza Kia; Hadi Kargar; Muhammad Nawaz Tahir

doi:10.1107/S1600536811004417

. 2011 Feb 12;67(Pt 3):o597. doi: 10.1107/S1600536811004417

4-Bromo-2-[(E)-(4-chlorophenyl)iminomethyl]phenol

Amir Adabi Ardakani ^a, Reza Kia ^b,^*, Hadi Kargar ^c, Muhammad Nawaz Tahir ^d,^*

PMCID: PMC3052075 PMID: 21522356

Abstract

In the title compound, C₁₃H₉BrClNO, the dihedral angle between the substituted benzene rings is 43.90 (11)°. Strong intramolecular O—H⋯N hydrogen bonds generate S(6) ring motifs. The crystal structure features short intemolecular Br⋯Br [3.554 (2) Å] and Cl⋯Cl [3.412 (2) Å] contacts. The crystal packing is further stabilized by intermolecular C—H⋯O and C—H⋯π interactions.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

C₁₃H₉BrClNO
M _r = 310.57
Monoclinic,
a = 27.652 (11) Å
b = 7.011 (3) Å
c = 6.219 (3) Å
β = 96.38 (2)°
V = 1198.2 (8) Å³
Z = 4
Mo Kα radiation
μ = 3.63 mm⁻¹
T = 296 K
0.35 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.363, T _max = 0.502
5719 measured reflections
2170 independent reflections
1718 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.078
S = 1.02
2170 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004417/jh2265sup1.cif

e-67-0o597-sup1.cif^{(16.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004417/jh2265Isup2.hkl

e-67-0o597-Isup2.hkl^{(106.7KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.594 (3)	147
C9—H9⋯O1ⁱ	0.93	2.60	3.459 (4)	154
C10—H10⋯Cg1ⁱⁱ	0.93	2.77	3.474 (3)	134
C13—H13⋯Cg1ⁱⁱⁱ	0.03	2.80	3.501 (3)	133

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

AAA thanks the Islamic Azad University, Ardakan Branch, for the research facilities (this paper was extracted from a research project). HK thanks the PNU for financial support. RK thanks the Science and Research Branch, Islamic Azad University, Tehran. MNT thanks Sargodha University for the research facilities.

supplementary crystallographic information

Comment

Schiff base ligands are one of the most prevalent systems in coordination chemistry. As part of a general study of Schiff bases, we have determined the crystal structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises a potentially bidentate Schiff base ligand. The bond lengths (Allen et al., 1987) and angles are within the normal ranges. The dihedral angle between the substituted benzene rings is 43.90 (11)Å. Strong intramolecular O—H···N hydrogen bonds generate S(6) ring motifs (Bernstein et al., 1995). The remarkable features of the crystal structure is the intemolecular Br···Br [3.554 (2)Å] and Cl···Cl [3.412 (2)Å] contacts which are shorter than the sum of the van der Waals radii of these atoms (Bondi 1964). The crystal packing is further stabilized by the intermolecular C—H···O hydrogen bond (Table 1) and C—H···π interaction [C10—H10···Cg1ⁱⁱ = 3.474 (3)Å, (ii) X, 3/2 - Y, -1/2 + Z; C13—H13···Cg1ⁱⁱⁱ = 3.501 (3)Å, (iii) X, 1/2 - Y, 1/2 + Z, Cg1 is the centroid of the C1–C6 benzene ring].

Experimental

The title compound was synthesized by adding 5-bromo-salicylaldehyde (2 mmol) to a solution of p-chloroaniline (2 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for half an hour. The resulting light-yellow solution was filtered. Light-yellow single crystals suitable for X-ray diffraction were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.