2-Chloro-4-{(E)-[(4-chloro-phen-yl)imino]-meth-yl}phenol.

In the title Schiff base compound, C(13)H(9)Cl(2)NO, the dihedral angle between the mean planes of the benzene rings is 10.20 (10)°. The crystal structure is stabilized by O-H⋯N hydrogen bonds and weak π-π stacking inter-actions [centroid-centroid distance = 3.757 (1) Å].

Related literature

For Schiff bases related to coordination chemistry, see: Calligaris et al. (1972 ▶); Cozzi (2004 ▶); Curini et al. (2002 ▶). For the anti­bacterial, anti­cancer, anti­inflammatory and antitoxic properties, see: Williams (1972 ▶); Karia & Parsania (1999 ▶); Desai et al. (2001 ▶). For the industrial and biological properties of Schiff bases, see: Lozier et al. (1975 ▶); Aydogan et al. (2001 ▶). For structural studies of Schiff bases, see: Gül et al. (2007 ▶); Şahin et al. (2005 ▶); Şahin, Ağar et al. (2009 ▶); Şahin, Erşahin et al. (2009 ▶); Şahin, Işık et al. (2009 ▶). For the classification of hydrogen-bonding patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H9Cl2NO

M = 266.11

Orthorhombic,

a = 9.7438 (6) Å

b = 9.9953 (5) Å

c = 12.1342 (6) Å

V = 1181.78 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.53 mm−1

T = 296 K

0.42 × 0.34 × 0.24 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.807, T max = 0.901

11473 measured reflections

2325 independent reflections

1960 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.064

S = 0.96

2325 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 968 Friedel pairs

Flack parameter: 0.02 (6)

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005193/jj2120sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005193/jj2120Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005193/jj2120Isup3.cml

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

C13H9Cl2NO	F(000) = 544
Mr = 266.11	Dx = 1.496 Mg m−3
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 20026 reflections
a = 9.7438 (6) Å	θ = 1.7–27.3°
b = 9.9953 (5) Å	µ = 0.53 mm−1
c = 12.1342 (6) Å	T = 296 K
V = 1181.78 (11) Å3	Prism, yellow
Z = 4	0.42 × 0.34 × 0.24 mm

Stoe IPDS II diffractometer	2325 independent reflections
Radiation source: fine-focus sealed tube	1960 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 1.7°
ω scans	h = −11→12
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
Tmin = 0.807, Tmax = 0.901	l = −14→14
11473 measured reflections

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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.064	w = 1/[σ2(Fo2) + (0.0363P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max = 0.003
2325 reflections	Δρmax = 0.12 e Å−3
154 parameters	Δρmin = −0.17 e Å−3
0 restraints	Absolute structure: Flack (1983), 968 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (6)

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
Cl1	−0.02767 (6)	0.22741 (7)	0.73432 (4)	0.06816 (19)
Cl2	0.78712 (7)	1.02829 (7)	0.54617 (5)	0.0792 (2)
O1	0.01370 (14)	0.20491 (15)	0.96945 (11)	0.0596 (4)
H1	0.0307	0.1983	1.0354	0.089*
N1	0.42961 (15)	0.66841 (17)	0.80818 (13)	0.0474 (4)
C12	0.25372 (18)	0.4980 (2)	0.82414 (15)	0.0491 (5)
C9	0.09145 (18)	0.3021 (2)	0.92525 (15)	0.0475 (5)
C11	0.16101 (18)	0.4218 (2)	0.76339 (16)	0.0532 (5)
H11	0.1528	0.4365	0.6880	0.064*
C6	0.6818 (2)	0.9216 (2)	0.62138 (17)	0.0562 (5)
C8	0.1838 (2)	0.3779 (2)	0.98593 (16)	0.0568 (5)
H8	0.1924	0.3631	1.0613	0.068*
C13	0.33844 (19)	0.5943 (2)	0.76529 (17)	0.0541 (5)
H13	0.3245	0.6022	0.6897	0.065*
C1	0.68403 (19)	0.9260 (2)	0.73602 (17)	0.0562 (5)
H1A	0.7417	0.9850	0.7730	0.067*
C10	0.08170 (19)	0.3259 (2)	0.81251 (15)	0.0487 (5)
C2	0.5999 (2)	0.8419 (2)	0.79293 (17)	0.0596 (6)
H2	0.6014	0.8442	0.8695	0.072*
C4	0.5127 (2)	0.7514 (2)	0.62570 (17)	0.0675 (6)
H4	0.4552	0.6925	0.5885	0.081*
C5	0.5955 (2)	0.8342 (2)	0.56650 (18)	0.0685 (6)
H5	0.5940	0.8320	0.4899	0.082*
C7	0.2623 (2)	0.4739 (2)	0.93676 (16)	0.0527 (5)
H7	0.3227	0.5241	0.9794	0.063*
C3	0.51177 (17)	0.75259 (19)	0.74034 (15)	0.0469 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0696 (3)	0.0808 (4)	0.0541 (3)	−0.0187 (3)	−0.0139 (2)	−0.0002 (3)
Cl2	0.0909 (4)	0.0874 (4)	0.0592 (3)	−0.0312 (3)	0.0115 (3)	0.0010 (3)
O1	0.0660 (8)	0.0659 (9)	0.0468 (7)	−0.0123 (7)	0.0010 (6)	0.0061 (7)
N1	0.0488 (9)	0.0486 (10)	0.0448 (9)	0.0033 (8)	0.0035 (7)	0.0006 (8)
C12	0.0462 (10)	0.0534 (12)	0.0477 (11)	0.0029 (9)	0.0022 (8)	0.0021 (9)
C9	0.0450 (9)	0.0526 (12)	0.0447 (10)	−0.0002 (9)	0.0026 (8)	0.0009 (9)
C11	0.0550 (10)	0.0667 (13)	0.0379 (10)	−0.0020 (10)	−0.0040 (9)	0.0050 (10)
C6	0.0606 (12)	0.0551 (13)	0.0528 (12)	−0.0015 (11)	0.0068 (9)	−0.0004 (10)
C8	0.0636 (12)	0.0680 (14)	0.0387 (11)	−0.0075 (11)	−0.0017 (9)	0.0044 (9)
C13	0.0536 (11)	0.0650 (13)	0.0438 (11)	0.0004 (10)	−0.0004 (9)	0.0027 (10)
C1	0.0545 (11)	0.0591 (13)	0.0549 (12)	−0.0096 (10)	−0.0027 (10)	−0.0073 (10)
C10	0.0464 (10)	0.0563 (13)	0.0433 (10)	0.0008 (9)	−0.0038 (8)	−0.0006 (9)
C2	0.0635 (12)	0.0741 (16)	0.0413 (11)	−0.0017 (12)	−0.0010 (9)	−0.0027 (10)
C4	0.0827 (14)	0.0689 (16)	0.0510 (12)	−0.0199 (13)	−0.0014 (11)	−0.0100 (12)
C5	0.0920 (15)	0.0728 (16)	0.0406 (11)	−0.0281 (13)	0.0017 (11)	−0.0082 (11)
C7	0.0552 (10)	0.0596 (13)	0.0432 (10)	−0.0070 (10)	−0.0054 (9)	−0.0026 (10)
C3	0.0482 (9)	0.0446 (11)	0.0480 (10)	0.0051 (8)	0.0021 (8)	−0.0001 (9)

Cl1—C10	1.733 (2)	C6—C1	1.392 (3)
Cl2—C6	1.738 (2)	C8—C7	1.364 (3)
O1—C9	1.344 (2)	C8—H8	0.9300
O1—H1	0.8200	C13—H13	0.9300
N1—C13	1.268 (2)	C1—C2	1.362 (3)
N1—C3	1.424 (2)	C1—H1A	0.9300
C12—C7	1.390 (3)	C2—C3	1.394 (3)
C12—C11	1.392 (3)	C2—H2	0.9300
C12—C13	1.456 (3)	C4—C5	1.360 (3)
C9—C8	1.388 (3)	C4—C3	1.391 (3)
C9—C10	1.392 (3)	C4—H4	0.9300
C11—C10	1.368 (3)	C5—H5	0.9300
C11—H11	0.9300	C7—H7	0.9300
C6—C5	1.384 (3)
C9—O1—H1	109.5	C2—C1—H1A	120.7
C13—N1—C3	120.11 (16)	C6—C1—H1A	120.7
C7—C12—C11	117.68 (18)	C11—C10—C9	120.60 (18)
C7—C12—C13	124.26 (18)	C11—C10—Cl1	120.45 (15)
C11—C12—C13	118.02 (17)	C9—C10—Cl1	118.90 (16)
O1—C9—C8	123.27 (17)	C1—C2—C3	122.28 (19)
O1—C9—C10	118.49 (17)	C1—C2—H2	118.9
C8—C9—C10	118.21 (18)	C3—C2—H2	118.9
C10—C11—C12	121.26 (18)	C5—C4—C3	121.8 (2)
C10—C11—H11	119.4	C5—C4—H4	119.1
C12—C11—H11	119.4	C3—C4—H4	119.1
C5—C6—C1	120.6 (2)	C4—C5—C6	119.4 (2)
C5—C6—Cl2	119.58 (16)	C4—C5—H5	120.3
C1—C6—Cl2	119.77 (16)	C6—C5—H5	120.3
C7—C8—C9	121.02 (19)	C8—C7—C12	121.22 (19)
C7—C8—H8	119.5	C8—C7—H7	119.4
C9—C8—H8	119.5	C12—C7—H7	119.4
N1—C13—C12	125.60 (19)	C4—C3—C2	117.33 (18)
N1—C13—H13	117.2	C4—C3—N1	125.25 (18)
C12—C13—H13	117.2	C2—C3—N1	117.42 (16)
C2—C1—C6	118.58 (19)
C7—C12—C11—C10	−0.5 (3)	C8—C9—C10—Cl1	177.26 (15)
C13—C12—C11—C10	177.53 (18)	C6—C1—C2—C3	−0.3 (3)
O1—C9—C8—C7	178.76 (19)	C3—C4—C5—C6	0.4 (4)
C10—C9—C8—C7	0.5 (3)	C1—C6—C5—C4	−0.3 (4)
C3—N1—C13—C12	175.96 (17)	Cl2—C6—C5—C4	−179.65 (19)
C7—C12—C13—N1	−0.3 (3)	C9—C8—C7—C12	−0.8 (3)
C11—C12—C13—N1	−178.15 (18)	C11—C12—C7—C8	0.7 (3)
C5—C6—C1—C2	0.3 (3)	C13—C12—C7—C8	−177.13 (19)
Cl2—C6—C1—C2	179.62 (16)	C5—C4—C3—C2	−0.3 (3)
C12—C11—C10—C9	0.2 (3)	C5—C4—C3—N1	−179.3 (2)
C12—C11—C10—Cl1	−177.24 (16)	C1—C2—C3—C4	0.3 (3)
O1—C9—C10—C11	−178.58 (17)	C1—C2—C3—N1	179.32 (18)
C8—C9—C10—C11	−0.2 (3)	C13—N1—C3—C4	−7.7 (3)
O1—C9—C10—Cl1	−1.1 (3)	C13—N1—C3—C2	173.35 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	1.96	2.778 (2)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	1.96	2.778 (2)	176

Symmetry code: (i) .