(E)-4-Chloro-2-[(2-hydroxy­phenyl)­iminometh­yl]phenol

Naser Eltaher Eltayeb; Siang Guan Teoh; Suchada Chantrapromma; Hoong-Kun Fun

doi:10.1107/S160053681001233X

. 2010 Apr 14;66(Pt 5):o1065–o1066. doi: 10.1107/S160053681001233X

(E)-4-Chloro-2-[(2-hydroxyphenyl)iminomethyl]phenol

Naser Eltaher Eltayeb ^a,^‡, Siang Guan Teoh ^a, Suchada Chantrapromma ^b,^§, Hoong-Kun Fun ^c,^*,^¶

PMCID: PMC2979173 PMID: 21579121

Abstract

The title compound, C₁₃H₁₀ClNO₂, exists in a trans configuration about the central C=N bond. The two benzene rings are almost coplanar, making a dihedral angle of 2.48 (10)°. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal structure, O—H⋯O hydrogen bonds link the molecules into chains along [101]. Short C⋯Cl contacts [3.584 (2)–3.646 (2) Å] are observed. A short intramolecular C—H⋯O contact occurs.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to Schiff bases and their applications, see: Dao et al. (2000 ▶); Eltayeb & Ahmed (2005a ▶,b ▶); Karthikeyan et al. (2006 ▶); Sriram et al. (2006 ▶); Wei & Atwood (1998 ▶). For related structures, see: Eltayeb et al. (2007a ▶,b ▶); Pu (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₃H₁₀ClNO₂
M _r = 247.67
Monoclinic,
a = 4.6681 (9) Å
b = 18.509 (3) Å
c = 6.2118 (11) Å
β = 90.980 (4)°
V = 536.63 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 100 K
0.55 × 0.14 × 0.07 mm

Data collection

Bruker APEX Duo CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.834, T _max = 0.976
4593 measured reflections
2680 independent reflections
2569 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.119
S = 1.20
2680 reflections
154 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.47 e Å⁻³
Absolute structure: Flack (1983 ▶), 1125 Friedel pairs
Flack parameter: −0.03 (7)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S160053681001233X/is2534sup1.cif

e-66-o1065-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001233X/is2534Isup2.hkl

e-66-o1065-Isup2.hkl^{(131.6KB, 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
O1—H1O1⋯O2ⁱ	0.82	1.74	2.553 (2)	169
O2—H1O2⋯N1	0.82	1.86	2.602 (2)	149
C7—H7⋯O1	0.93	2.16	2.789 (3)	124

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia for the RU research grants (PKIMIA/815002, and PKIMIA/811120). NEE would like to acknowledge Universiti Sains Malaysia for a post-doctoral fellowship and the International University of Africa (Sudan) for providing study leave. The authors also thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

We have been interested in synthesis of Schiff base ligands and their complexes (Eltayeb et al., 2007a,b) due to their applications such as analytical reagents for the determination of trace elements (Eltayeb & Ahmed, 2005a,b), pharmacological activities, anticancer (Dao et al., 2000), anti-HIV (Sriram et al., 2006), antibacterial and antifungal (Karthikeyan et al., 2006) activities. The title compound was used to synthesis the chelated borate catalyst (Wei & Atwood, 1998). Herein we report the crystal structure of the title Schiff base ligand (I).

The molecule of (I) (Fig. 1), C₁₃H₁₀ClNO₂, crystallizes in a trans configuration about the C═N bond [1.312 (3) Å] with a torsion angle C1–N1–C7–C8 = -179.2 (2)°. The molecule is almost planar with a dihedral angle between the two benzene rings being 2.48 (10)°. The chloro and two hydroxy groups lie on the same plane with their attached benzene rings with the r.m.s. of 0.0105 (2) Å for the seven non H atoms (C1, C2, C3, C4, C5, C6 and O1) and 0.0129 (2) Å for the eight non H atoms (C8, C9, C10, C11, C12, C13, O2 and Cl1). An intramolecular O—H···N hydrogen bond between the imine N atom and one hydroxy group generates an S(6) ring motif (Fig. 1 and Table 1) (Bernstein et al., 1995). The bond distances are of normal values (Allen et al., 1987) and are comparable with the related structure (Pu, 2008).

In the crystal packing (Fig. 2) , O—H···O hydrogen bonds (Table 1) which formed between the two hydroxy O atoms link the molecules into into chains along the [101] direction. The crystal is consolidated by O—H···O hydrogen bonds (Table 1) and C···Cl [3.584 (2)–3.646 (2) Å] short contacts.

Experimental

The title compound was synthesized by adding 5-chloro-2-hydroxybenzaldehyde (0.312 g, 2 mmol) to the solution of 2-aminophenol (0.218 g, 2 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for half an hour. The resultant yellow-orange solution was filtered and the filtrate was evaporated to give a yellow solid product. Yellow needle-shaped single crystals of the title compound suitable for x-ray structure determination were obtained from ethanol by slow evaporation at room temperature after a few days.