4-Chloro-2-[(4-chloro-benzyl-idene)amino]-phenol.

In the title Schiff base compound, C(13)H(9)Cl(2)NO, the mol-ecule 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, mol-ecules 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 ▶); Fn class="Chemical">aridbod 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 ▶).

Experimental

Crystal data

C13H9Cl2NO

M = 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

Δρmax = 0.21 e Å−3

Δρmin = −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-n class="Chemical">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 ▶).

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

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

Supplementary material file. DOI: 10.1107/S1600536812019770/zs2205Isup3.cml

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

C13H9Cl2NO	Dx = 1.427 Mg m−3
Mr = 266.11	Melting point = 396–398 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 16508 reflections
a = 4.6615 (2) Å	θ = 1.6–27.2°
b = 10.5375 (5) Å	µ = 0.51 mm−1
c = 25.2153 (15) Å	T = 296 K
V = 1238.59 (11) Å3	Prism, brown
Z = 4	0.53 × 0.41 × 0.31 mm
F(000) = 544

Stoe IPDS 2 CCD diffractometer	2562 independent reflections
Radiation source: fine-focus sealed tube	1910 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
rotation method scans	θmax = 26.5°, θmin = 1.6°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −5→5
Tmin = 0.815, Tmax = 0.882	k = −13→13
2562 measured reflections	l = −31→31

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0496P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max < 0.001
2562 reflections	Δρmax = 0.21 e Å−3
159 parameters	Δρmin = −0.24 e Å−3
0 restraints	Absolute structure: Flack (1983), 1024 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (7)

Experimental. IR: 3071, 2911, 1626 (C=N),1586, 1568, 1478, 1423, 1369, 1271, 1238, 1194, 1154, 1082, 1009, 909, 856, 812, 696, 607 cm-1. 1H NMR (CDCl3): δ 8.66 (s, 1H, N=CH), 7.91 (d, J = 8.4 Hz, 2H, Ar), 7.54 (d, J = 8.4 Hz, 2H, Ar), 7.34 (s, 1H, Ar), 7.24 (d, J = 8.6 Hz, 1H, Ar), 7.02 (d, J = 8.6 Hz, 1H, Ar). 13CNMR (CDCl3): δ 156.75 (N=C), 150.94, 138.21, 135.86, 133.87, 130.06, 129.28, 128.77, 125.07, 116.19. Elemental Anal. Calcd for C13H9Cl2NO: C, 58,67; H, 3,41; N, 5,26. Found: C, 57.74; H, 3.42; N, 5.26%.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
C1	−0.1216 (4)	0.47092 (19)	0.57988 (7)	0.0537 (5)
C2	−0.2380 (5)	0.4456 (2)	0.53004 (8)	0.0616 (6)
C3	−0.4413 (6)	0.5255 (3)	0.50863 (9)	0.0769 (6)
H3	−0.5168	0.5082	0.4753	0.092*
C4	−0.5333 (6)	0.6303 (2)	0.53591 (9)	0.0760 (7)
H4	−0.6710	0.6839	0.5213	0.091*
C5	−0.4197 (6)	0.6552 (2)	0.58495 (9)	0.0713 (6)
C6	−0.2162 (5)	0.5778 (2)	0.60712 (8)	0.0628 (6)
H6	−0.1414	0.5968	0.6404	0.075*
C7	0.1973 (5)	0.3864 (2)	0.64196 (7)	0.0561 (5)
H7	0.1415	0.4505	0.6651	0.067*
C8	0.4106 (4)	0.29397 (18)	0.65979 (7)	0.0523 (4)
C9	0.5145 (5)	0.2984 (2)	0.71173 (8)	0.0653 (6)
H9	0.4480	0.3612	0.7346	0.078*
C10	0.7136 (5)	0.2117 (2)	0.72989 (8)	0.0663 (6)
H10	0.7827	0.2163	0.7644	0.080*
C11	0.8069 (5)	0.1196 (2)	0.69631 (8)	0.0606 (5)
C12	0.7106 (5)	0.1122 (2)	0.64475 (8)	0.0634 (6)
H12	0.7792	0.0493	0.6222	0.076*
C13	0.5123 (5)	0.19875 (19)	0.62699 (7)	0.0605 (5)
H13	0.4452	0.1933	0.5923	0.073*
N1	0.0866 (4)	0.38240 (15)	0.59657 (6)	0.0554 (4)
O1	−0.1527 (4)	0.34241 (18)	0.50249 (6)	0.0813 (5)
Cl1	−0.5403 (2)	0.78790 (6)	0.61993 (3)	0.1114 (3)
Cl2	1.05363 (14)	0.00872 (6)	0.71919 (3)	0.0847 (2)
H1	−0.021 (6)	0.303 (2)	0.5193 (9)	0.088 (9)*

	U11	U22	U33	U12	U13	U23
C1	0.0469 (11)	0.0618 (12)	0.0525 (10)	−0.0110 (10)	0.0007 (9)	0.0069 (9)
C2	0.0571 (13)	0.0738 (14)	0.0538 (11)	−0.0057 (11)	0.0013 (10)	0.0010 (10)
C3	0.0699 (14)	0.1008 (17)	0.0599 (12)	−0.0012 (16)	−0.0072 (12)	0.0118 (12)
C4	0.0673 (15)	0.0796 (15)	0.0810 (15)	0.0034 (14)	0.0001 (14)	0.0274 (12)
C5	0.0709 (14)	0.0595 (12)	0.0834 (14)	−0.0046 (13)	0.0028 (13)	0.0115 (11)
C6	0.0658 (14)	0.0580 (12)	0.0646 (12)	−0.0084 (11)	−0.0036 (12)	−0.0010 (10)
C7	0.0544 (12)	0.0618 (12)	0.0522 (10)	−0.0065 (11)	0.0008 (10)	−0.0054 (9)
C8	0.0465 (11)	0.0578 (10)	0.0526 (9)	−0.0073 (10)	−0.0004 (9)	−0.0009 (9)
C9	0.0635 (14)	0.0747 (13)	0.0578 (11)	0.0046 (12)	−0.0047 (11)	−0.0110 (10)
C10	0.0597 (13)	0.0806 (15)	0.0586 (11)	0.0007 (13)	−0.0060 (11)	−0.0009 (11)
C11	0.0520 (12)	0.0595 (12)	0.0704 (13)	−0.0066 (10)	0.0059 (11)	0.0149 (10)
C12	0.0680 (14)	0.0581 (12)	0.0642 (12)	−0.0003 (11)	0.0127 (11)	−0.0008 (10)
C13	0.0696 (14)	0.0629 (11)	0.0490 (10)	−0.0084 (12)	0.0022 (10)	0.0001 (9)
N1	0.0556 (10)	0.0584 (9)	0.0521 (9)	−0.0072 (9)	−0.0013 (8)	0.0006 (7)
O1	0.0827 (12)	0.1033 (13)	0.0580 (8)	0.0137 (10)	−0.0125 (9)	−0.0136 (9)
Cl1	0.1263 (7)	0.0703 (4)	0.1377 (6)	0.0207 (5)	−0.0080 (6)	−0.0116 (4)
Cl2	0.0697 (3)	0.0794 (4)	0.1051 (4)	0.0080 (4)	0.0068 (3)	0.0285 (3)

C1—C6	1.391 (3)	C7—H7	0.9300
C1—C2	1.395 (3)	C8—C13	1.384 (3)
C1—N1	1.411 (3)	C8—C9	1.397 (3)
C2—O1	1.350 (3)	C9—C10	1.381 (3)
C2—C3	1.378 (3)	C9—H9	0.9300
C3—C4	1.370 (3)	C10—C11	1.359 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.371 (3)	C11—C12	1.378 (3)
C4—H4	0.9300	C11—Cl2	1.738 (2)
C5—C6	1.370 (3)	C12—C13	1.374 (3)
C5—Cl1	1.746 (2)	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300
C7—N1	1.256 (2)	O1—H1	0.86 (3)
C7—C8	1.462 (3)
C6—C1—C2	118.48 (19)	C13—C8—C9	117.77 (19)
C6—C1—N1	127.32 (18)	C13—C8—C7	122.12 (17)
C2—C1—N1	114.19 (18)	C9—C8—C7	120.10 (18)
O1—C2—C3	119.6 (2)	C10—C9—C8	121.4 (2)
O1—C2—C1	120.2 (2)	C10—C9—H9	119.3
C3—C2—C1	120.2 (2)	C8—C9—H9	119.3
C4—C3—C2	120.8 (2)	C11—C10—C9	118.75 (19)
C4—C3—H3	119.6	C11—C10—H10	120.6
C2—C3—H3	119.6	C9—C10—H10	120.6
C3—C4—C5	119.1 (2)	C10—C11—C12	121.6 (2)
C3—C4—H4	120.5	C10—C11—Cl2	119.01 (16)
C5—C4—H4	120.5	C12—C11—Cl2	119.37 (18)
C6—C5—C4	121.5 (2)	C13—C12—C11	119.3 (2)
C6—C5—Cl1	119.56 (19)	C13—C12—H12	120.4
C4—C5—Cl1	119.0 (2)	C11—C12—H12	120.4
C5—C6—C1	120.0 (2)	C12—C13—C8	121.13 (18)
C5—C6—H6	120.0	C12—C13—H13	119.4
C1—C6—H6	120.0	C8—C13—H13	119.4
N1—C7—C8	122.50 (19)	C7—N1—C1	122.18 (17)
N1—C7—H7	118.8	C2—O1—H1	110.6 (17)
C8—C7—H7	118.8
C6—C1—C2—O1	−179.7 (2)	N1—C7—C8—C9	−176.3 (2)
N1—C1—C2—O1	1.0 (3)	C13—C8—C9—C10	0.5 (3)
C6—C1—C2—C3	0.2 (3)	C7—C8—C9—C10	179.33 (19)
N1—C1—C2—C3	−179.2 (2)	C8—C9—C10—C11	−0.7 (3)
O1—C2—C3—C4	179.5 (2)	C9—C10—C11—C12	0.9 (3)
C1—C2—C3—C4	−0.4 (4)	C9—C10—C11—Cl2	−179.06 (16)
C2—C3—C4—C5	0.2 (4)	C10—C11—C12—C13	−1.0 (3)
C3—C4—C5—C6	0.2 (4)	Cl2—C11—C12—C13	179.01 (16)
C3—C4—C5—Cl1	−179.31 (19)	C11—C12—C13—C8	0.8 (3)
C4—C5—C6—C1	−0.3 (4)	C9—C8—C13—C12	−0.6 (3)
Cl1—C5—C6—C1	179.12 (17)	C7—C8—C13—C12	−179.35 (19)
C2—C1—C6—C5	0.2 (3)	C8—C7—N1—C1	179.19 (18)
N1—C1—C6—C5	179.4 (2)	C6—C1—N1—C7	5.9 (3)
N1—C7—C8—C13	2.5 (3)	C2—C1—N1—C7	−174.84 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.86 (3)	2.18 (2)	2.655 (2)	115 (2)
O1—H1···O1i	0.86 (3)	2.36 (3)	3.040 (2)	136 (2)

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)

Symmetry code: (i) .