4-Chloro-2-[(4-chloro­benzyl­idene)amino]­phenol

Kürşat Efil; Fatih Şen; Yunus Bekdemir; Orhan Büyükgüngör

doi:10.1107/S1600536812019770

. 2012 May 12;68(Pt 6):o1696. doi: 10.1107/S1600536812019770

4-Chloro-2-[(4-chlorobenzylidene)amino]phenol

Kürşat Efil ^a,^*, Fatih Şen ^b, Yunus Bekdemir ^a, Orhan Büyükgüngör ^c

PMCID: PMC3379291 PMID: 22719489

Abstract

In the title Schiff base compound, C₁₃H₉Cl₂NO, the molecule displays an E conformation about the imine C=N double bond, with a dihedral angle of 8.09 (11)° between the two benzene rings. In the crystal, molecules are linked by a single O—H⋯O hydrogen bond, giving one-dimensional chains which extend along (100).

Related literature

For related Schiff base compounds and applications, see: Asiri & Khan (2010 ▶); Bekircan et al. (2006 ▶); Faridbod et al. (2008 ▶); Fun et al. (2009 ▶); Ghanwate et al. (2008 ▶); Jarrahpour et al. (2007 ▶); Layer (1963 ▶); Shi et al. (2007 ▶); Zhao et al. (2010 ▶). For related structures, see: Xu et al. (2009 ▶); Zhou et al. (2009 ▶). graphic file with name e-68-o1696-scheme1.jpg

Experimental

Crystal data

C₁₃H₉Cl₂NO
M _r = 266.11
Orthorhombic,
a = 4.6615 (2) Å
b = 10.5375 (5) Å
c = 25.2153 (15) Å
V = 1238.59 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 296 K
0.53 × 0.41 × 0.31 mm

Data collection

Stoe IPDS 2 Image-Plate diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.815, T _max = 0.882
2562 measured reflections
2562 independent reflections
1910 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.082
S = 0.93
2562 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ▶), 1024 Friedel pairs
Flack parameter: 0.01 (7)

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 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019770/zs2205sup1.cif

e-68-o1696-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019770/zs2205Isup2.hkl

e-68-o1696-Isup2.hkl^{(123.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812019770/zs2205Isup3.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⋯O1ⁱ	0.86 (3)	2.36 (3)	3.040 (2)	136 (2)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

The compounds containing the C═N group, are known as Schiff bases (also imines or azomethines), are generally synthesized by condensation of primary amines with active carbonyl compounds (Asiri & Khan, 2010; Faridbod et al., 2008). The reaction is acid-catalyzed and is usually performed by refluxing the carbonyl compound and amine (Layer, 1963). These compounds show biological activity as antitumor (Zhao, et al., 2010), anticancer (Bekircan, et al., 2006), antifungal (Shi, et al., 2007), antimicrobial (Ghanwate, et al., 2008) or antiviral agents (Jarrahpour, et al., 2007), furthermore they are used as intermediates and ligands in the formation of a complex with some metal ions (Fun et al., 2009). As part of our ongoing study of the structural relationships between the compounds containing Schiff bases, a crystal structure determination of the title compound, C₁₃H₉Cl₂NO, has been undertaken and the results are presented here.

The structure of the title compound (Fig. 1) is similar to those of analogous derivatives (Xu et al., 2009; Zhou et al., 2009) and displays a trans configuration with respect to the imine C═N with a C8—C7—N1—C1 torsion angle of 179.19 (18)°. The molecule is close to planar, as indicated by the dihedral angle between the two benzene rings [8.09 (11)°]. The crystal packing is stabilized by a single intermolecular O—H···O hydrogen-bonding interaction (Table 1, Fig. 2), giving a one-dimensional chain structure which extends down (100) (Fig. 3). An intramolecular O—H···N interaction is also present.

Experimental

4-Chlorobenzaldehyde (0.141 g; 1 mmol), 2-hydroxy-5-chloroaniline (0.144 g; 1 mmol) and two drops of β-ethoxyethanol as a wetting solvent were mixed in a beaker and then exposed to microwaves in an oven (360 W). It was observed that the reaction was completed within 2 minutes (thin layer chromatography). The resulting solid product was washed with cold ethanol and recrystallized from ethanol, giving the title compound. Yield: 92%, m.p. 396–398 °K.