(E)-4-Chloro-2-[(2-hydroxy-phenyl)-iminometh-yl]phenol.

The title compound, C(13)H(10)ClNO(2), 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 intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. In the crystal structure, O-H⋯O hydrogen bonds link the mol-ecules 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 = 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

Δρmax = 0.47 e Å−3

Δρmin = −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 ▶).

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

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

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

C13H10ClNO2	F(000) = 256
Mr = 247.67	Dx = 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

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

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(Fo2) + (0.0756P)2 + 0.0404P] where P = (Fo2 + 2Fc2)/3
S = 1.20	(Δ/σ)max = 0.001
2680 reflections	Δρmax = 0.47 e Å−3
154 parameters	Δρmin = −0.47 e Å−3
1 restraint	Absolute structure: Flack (1983), 1125 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (7)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .