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

Eltayeb, N.E.; Teoh, S.G.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S160053681001233X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages o1065-o1066

https://doi.org/10.1107/S160053681001233X

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

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

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 31 March 2010; accepted 1 April 2010; online 14 April 2010)

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, P 2₁
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[F² > 2σ(F²)] = 0.034
wR(F²) = 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)

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
Symmetry code: (i) x+1, y, z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681001233X/is2534sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001233X/is2534Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Structure description top

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).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme. The hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound viewed down the a axis, showing chains running along the [101] direction. Hydrogen bonds are shown as dashed lines.

(E)-4-Chloro-2-[(2-hydroxyphenylimino)methyl]phenol top

Crystal data top

C₁₃H₁₀ClNO₂	F(000) = 256
M_r = 247.67	D_x = 1.533 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2680 reflections
a = 4.6681 (9) Å	θ = 4.4–30.0°
b = 18.509 (3) Å	µ = 0.34 mm⁻¹
c = 6.2118 (11) Å	T = 100 K
β = 90.980 (4)°	Needle, yellow
V = 536.63 (17) Å³	0.55 × 0.14 × 0.07 mm
Z = 2

Data collection top

Bruker APEX Duo CCD area detector diffractometer	2680 independent reflections
Radiation source: sealed tube	2569 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
φ and ω scans	θ_max = 30.0°, θ_min = 4.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
T_min = 0.834, T_max = 0.976	k = −24→26
4593 measured reflections	l = −8→8

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0756P)² + 0.0404P] where P = (F_o² + 2F_c²)/3
S = 1.20	(Δ/σ)_max = 0.001
2680 reflections	Δρ_max = 0.47 e Å⁻³
154 parameters	Δρ_min = −0.47 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1125 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (7)

Crystal data top

C₁₃H₁₀ClNO₂	V = 536.63 (17) Å³
M_r = 247.67	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 4.6681 (9) Å	µ = 0.34 mm⁻¹
b = 18.509 (3) Å	T = 100 K
c = 6.2118 (11) Å	0.55 × 0.14 × 0.07 mm
β = 90.980 (4)°

Data collection top

Bruker APEX Duo CCD area detector diffractometer	2680 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2569 reflections with I > 2σ(I)
T_min = 0.834, T_max = 0.976	R_int = 0.023
4593 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.119	Δρ_max = 0.47 e Å⁻³
S = 1.20	Δρ_min = −0.47 e Å⁻³
2680 reflections	Absolute structure: Flack (1983), 1125 Friedel pairs
154 parameters	Absolute structure parameter: −0.03 (7)
1 restraint

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.02845 (11)	1.08595 (3)	0.36240 (8)	0.01689 (14)
O1	1.1428 (4)	0.82828 (9)	0.5209 (2)	0.0167 (3)
H1O1	1.2817	0.8379	0.5983	0.025*
O2	0.5318 (4)	0.86922 (9)	−0.2123 (2)	0.0151 (3)
H1O2	0.6550	0.8463	−0.1462	0.018*
N1	0.8674 (4)	0.83076 (10)	0.1062 (3)	0.0116 (3)
C1	1.0806 (4)	0.78021 (11)	0.1679 (3)	0.0113 (4)
C2	1.2187 (4)	0.77923 (11)	0.3724 (3)	0.0119 (4)
C3	1.4270 (5)	0.72625 (12)	0.4139 (3)	0.0144 (4)
H3	1.5136	0.7236	0.5496	0.017*
C4	1.5066 (5)	0.67719 (12)	0.2539 (4)	0.0157 (4)
H4	1.6481	0.6430	0.2828	0.019*
C5	1.3732 (5)	0.67964 (12)	0.0506 (4)	0.0147 (4)
H5	1.4255	0.6471	−0.0559	0.018*
C6	1.1629 (5)	0.73071 (12)	0.0089 (3)	0.0140 (4)
H6	1.0747	0.7323	−0.1264	0.017*
C7	0.7386 (5)	0.87972 (12)	0.2228 (3)	0.0122 (4)
H7	0.7886	0.8845	0.3677	0.015*
C8	0.5237 (5)	0.92579 (11)	0.1321 (3)	0.0114 (4)
C9	0.4240 (5)	0.91833 (11)	−0.0859 (3)	0.0115 (4)
C10	0.2019 (5)	0.96567 (12)	−0.1572 (3)	0.0132 (4)
H10	0.1328	0.9622	−0.2981	0.016*
C11	0.0865 (5)	1.01690 (12)	−0.0213 (3)	0.0136 (4)
H11	−0.0572	1.0476	−0.0720	0.016*
C12	0.1857 (5)	1.02276 (11)	0.1934 (3)	0.0127 (4)
C13	0.4000 (5)	0.97834 (12)	0.2706 (3)	0.0124 (4)
H13	0.4641	0.9825	0.4126	0.015*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0209 (3)	0.0156 (2)	0.0141 (2)	0.00493 (18)	−0.00206 (15)	−0.0037 (2)
O1	0.0172 (8)	0.0217 (8)	0.0111 (7)	0.0046 (6)	−0.0046 (5)	−0.0049 (6)
O2	0.0166 (8)	0.0178 (8)	0.0108 (7)	0.0039 (5)	−0.0021 (5)	−0.0036 (6)
N1	0.0124 (8)	0.0118 (8)	0.0106 (8)	−0.0001 (6)	−0.0010 (5)	−0.0005 (6)
C1	0.0108 (9)	0.0113 (9)	0.0116 (9)	0.0006 (7)	−0.0013 (6)	0.0001 (7)
C2	0.0120 (9)	0.0139 (9)	0.0098 (9)	−0.0003 (6)	−0.0006 (6)	0.0006 (7)
C3	0.0148 (10)	0.0187 (11)	0.0097 (9)	0.0017 (7)	−0.0025 (6)	0.0017 (8)
C4	0.0143 (10)	0.0143 (10)	0.0183 (11)	0.0024 (7)	−0.0012 (7)	0.0015 (8)
C5	0.0157 (10)	0.0145 (10)	0.0140 (10)	−0.0002 (7)	0.0012 (7)	−0.0013 (8)
C6	0.0152 (10)	0.0154 (10)	0.0113 (10)	−0.0010 (7)	−0.0011 (7)	−0.0025 (7)
C7	0.0117 (9)	0.0138 (9)	0.0111 (9)	0.0001 (6)	0.0000 (6)	0.0000 (7)
C8	0.0120 (9)	0.0128 (9)	0.0092 (9)	0.0002 (6)	−0.0012 (6)	−0.0003 (7)
C9	0.0126 (10)	0.0130 (9)	0.0090 (9)	0.0001 (7)	−0.0002 (6)	0.0004 (7)
C10	0.0155 (10)	0.0157 (9)	0.0083 (9)	0.0009 (7)	−0.0011 (7)	0.0016 (7)
C11	0.0142 (10)	0.0134 (9)	0.0132 (10)	0.0006 (7)	−0.0008 (6)	0.0016 (8)
C12	0.0143 (10)	0.0121 (9)	0.0117 (9)	−0.0007 (7)	0.0017 (6)	−0.0012 (8)
C13	0.0138 (10)	0.0155 (10)	0.0077 (9)	−0.0011 (7)	−0.0001 (6)	−0.0005 (7)

Geometric parameters (Å, º) top

Cl1—C12	1.742 (2)	C5—C6	1.384 (3)
O1—C2	1.346 (3)	C5—H5	0.9300
O1—H1O1	0.8200	C6—H6	0.9300
O2—C9	1.308 (3)	C7—C8	1.425 (3)
O2—H1O2	0.8200	C7—H7	0.9300
N1—C7	1.312 (3)	C8—C13	1.427 (3)
N1—C1	1.414 (3)	C8—C9	1.431 (3)
C1—C6	1.405 (3)	C9—C10	1.422 (3)
C1—C2	1.415 (3)	C10—C11	1.385 (3)
C2—C3	1.402 (3)	C10—H10	0.9300
C3—C4	1.401 (3)	C11—C12	1.408 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.399 (3)	C12—C13	1.375 (3)
C4—H4	0.9300	C13—H13	0.9300

C2—O1—H1O1	109.5	N1—C7—C8	121.39 (19)
C9—O2—H1O2	109.5	N1—C7—H7	119.3
C7—N1—C1	129.38 (18)	C8—C7—H7	119.3
C6—C1—N1	116.14 (18)	C7—C8—C13	117.29 (18)
C6—C1—C2	119.79 (18)	C7—C8—C9	122.13 (19)
N1—C1—C2	124.01 (19)	C13—C8—C9	120.52 (18)
O1—C2—C3	122.39 (18)	O2—C9—C10	121.83 (18)
O1—C2—C1	119.04 (18)	O2—C9—C8	120.86 (18)
C3—C2—C1	118.56 (19)	C10—C9—C8	117.30 (18)
C4—C3—C2	120.96 (19)	C11—C10—C9	121.41 (18)
C4—C3—H3	119.5	C11—C10—H10	119.3
C2—C3—H3	119.5	C9—C10—H10	119.3
C5—C4—C3	120.0 (2)	C10—C11—C12	120.33 (19)
C5—C4—H4	120.0	C10—C11—H11	119.8
C3—C4—H4	120.0	C12—C11—H11	119.8
C6—C5—C4	119.6 (2)	C13—C12—C11	120.7 (2)
C6—C5—H5	120.2	C13—C12—Cl1	120.17 (16)
C4—C5—H5	120.2	C11—C12—Cl1	119.16 (17)
C5—C6—C1	121.0 (2)	C12—C13—C8	119.77 (19)
C5—C6—H6	119.5	C12—C13—H13	120.1
C1—C6—H6	119.5	C8—C13—H13	120.1

C7—N1—C1—C6	175.5 (2)	N1—C7—C8—C9	4.0 (3)
C7—N1—C1—C2	−7.2 (4)	C7—C8—C9—O2	−1.3 (3)
C6—C1—C2—O1	178.20 (19)	C13—C8—C9—O2	−178.44 (19)
N1—C1—C2—O1	1.0 (3)	C7—C8—C9—C10	177.9 (2)
C6—C1—C2—C3	−2.8 (3)	C13—C8—C9—C10	0.8 (3)
N1—C1—C2—C3	180.0 (2)	O2—C9—C10—C11	179.1 (2)
O1—C2—C3—C4	−178.3 (2)	C8—C9—C10—C11	−0.1 (3)
C1—C2—C3—C4	2.8 (3)	C9—C10—C11—C12	−0.6 (3)
C2—C3—C4—C5	−1.4 (3)	C10—C11—C12—C13	0.6 (3)
C3—C4—C5—C6	0.0 (3)	C10—C11—C12—Cl1	−178.08 (17)
C4—C5—C6—C1	−0.1 (3)	C11—C12—C13—C8	0.1 (3)
N1—C1—C6—C5	178.9 (2)	Cl1—C12—C13—C8	178.79 (15)
C2—C1—C6—C5	1.5 (3)	C7—C8—C13—C12	−178.1 (2)
C1—N1—C7—C8	−179.2 (2)	C9—C8—C13—C12	−0.8 (3)
N1—C7—C8—C13	−178.77 (19)

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀ClNO₂
M_r	247.67
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	4.6681 (9), 18.509 (3), 6.2118 (11)
β (°)	90.980 (4)
V (Å³)	536.63 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.55 × 0.14 × 0.07

Data collection
Diffractometer	Bruker APEX Duo CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.834, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	4593, 2680, 2569
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.119, 1.20
No. of reflections	2680
No. of parameters	154
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.47
Absolute structure	Flack (1983), 1125 Friedel pairs
Absolute structure parameter	−0.03 (7)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x+1, y, z+1.

Footnotes

‡On study leave from Department of Chemistry, International University of Africa, Khartoum, Sudan, e-mail: nasertaha90@hotmail.com.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

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.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
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