2-Chloro-4-{(E)-[(4-chloro­phen­yl)imino]­meth­yl}phenol

Zarife Sibel Şahin; Şamil Işık

doi:10.1107/S1600536812005193

. 2012 Feb 10;68(Pt 3):o678. doi: 10.1107/S1600536812005193

2-Chloro-4-{(E)-[(4-chlorophenyl)imino]methyl}phenol

Zarife Sibel Şahin ^a,^*, Şamil Işık ^a

PMCID: PMC3295463 PMID: 22412574

Abstract

In the title Schiff base compound, C₁₃H₉Cl₂NO, the dihedral angle between the mean planes of the benzene rings is 10.20 (10)°. The crystal structure is stabilized by O—H⋯N hydrogen bonds and weak π–π stacking interactions [centroid–centroid distance = 3.757 (1) Å].

Related literature

For Schiff bases related to coordination chemistry, see: Calligaris et al. (1972 ▶); Cozzi (2004 ▶); Curini et al. (2002 ▶). For the antibacterial, anticancer, antiinflammatory and antitoxic properties, see: Williams (1972 ▶); Karia & Parsania (1999 ▶); Desai et al. (2001 ▶). For the industrial and biological properties of Schiff bases, see: Lozier et al. (1975 ▶); Aydogan et al. (2001 ▶). For structural studies of Schiff bases, see: Gül et al. (2007 ▶); Şahin et al. (2005 ▶); Şahin, Ağar et al. (2009 ▶); Şahin, Erşahin et al. (2009 ▶); Şahin, Işık et al. (2009 ▶). For the classification of hydrogen-bonding patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₃H₉Cl₂NO
M _r = 266.11
Orthorhombic,
a = 9.7438 (6) Å
b = 9.9953 (5) Å
c = 12.1342 (6) Å
V = 1181.78 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.53 mm⁻¹
T = 296 K
0.42 × 0.34 × 0.24 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.807, T _max = 0.901
11473 measured reflections
2325 independent reflections
1960 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.064
S = 0.96
2325 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ▶), 968 Friedel pairs
Flack parameter: 0.02 (6)

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005193/jj2120sup1.cif

e-68-0o678-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005193/jj2120Isup2.hkl

e-68-0o678-Isup2.hkl^{(111.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812005193/jj2120Isup3.cml

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
O1—H1⋯N1ⁱ	0.82	1.96	2.778 (2)	176

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences of Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant No. F279 of the University Research Grant of Ondokuz Mayıs University).

supplementary crystallographic information

Comment

Schiff bases are important in diverse fields of chemistry and biochemistry owing to their biological activites (Calligaris et al., 1972; Lozier et al., 1975). Most Schiff bases have antibacterial, anticancer, antinflammatory and antioxic properties (Williams, 1972). The present work is part of our structral study of Schiff bases (Gül et al., 2007; Şahin, Ağar et al., 2009; Şahin, Işık et al., 2009; Şahin, Erşahin et al., 2009) and we report here the structure of the title compound, C₁₃H₉Cl₂NO, (I).

The dihedral angle between the mean planes of the two aromatic rings is 10.20° and the C12—C13—N1—C3 torsion angle is 175.96 (17)° (Fig. 1). All bond lenghs are within normal values. The N1—C13 double bond length (1.268 (2)Å) is similar to the corresponding bond lengths in E-2-Methoxy-6-[(2-trifluoromethylphenylimino) methyl]phenol (1.270 (5) Å) (Şahin et al., 2005) and E-4-Methyl-2-[3-(trifluoromethyl)-phenyliminomethyl]phenol (1.270 (3) Å] (Gül et al., 2007).

In the crystal, the molecules are linked into sheets by O—H···N hydrogen bonds (Table 1) generating C(8) chains (Bernstein et al.,1995) along (011)(Fig. 2). Weak, symmetry independent π–π stacking interactions are observed which may influence crystal stability . The perpendicular distance from Cg1 to Cg1ⁱⁱ [symmetry code: (ii) = -x, 1 - y, z] is 3.62 (0)Å. The centroid-to-centroid distance is 3.757 (1)Å.

Experimental

The title compound, (I), was prepared by refluxing a solution mixture containing 3-chloro-4-hydroxybenzaldehyde (0.008 g 0.051 mmol) in 20 ml ethanol and 4-chloroaniline (0.007 g 0.051 mmol) in 20 ml ethanol for 1 h. Crystals of (I) suitable for X-ray analysis were obtained from ethyl alcohol by slow evaporation (yield %54; m.p 441–442 K).