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

The title compound, C(13)H(9)Cl(2)NO, was crystallized from a methanol solution of 5-chloro-salicylaldehyde and o-chloro-aniline. The mol-ecule displays a trans configuration with respect to the imine C=N double bond. The N atom is involved in an intra-molecular O-H⋯N hydrogen bond. The two aromatic rings are essentially coplanar, the dihedral angle between them being 7.1 (1)°. A C-H⋯π inter-action is present in the crystal.

Related literature

For the biological properties of Schiff bases containing O and N atoms, see: Antony et al. (1999 ▶); Lumme & Elo (1984 ▶); Yao et al. (1999 ▶). For its chemical behaviour, see: Ueno et al. (2006 ▶).

Experimental

Crystal data

C13H9Cl2NO

M = 266.11

Orthorhombic,

a = 7.2693 (13) Å

b = 13.0037 (19) Å

c = 25.2711 (16) Å

V = 2388.8 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.52 mm−1

T = 298 (2) K

0.50 × 0.48 × 0.47 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Siemens, 1996 ▶) T min = 0.780, T max = 0.791

11102 measured reflections

2103 independent reflections

1496 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.099

S = 1.08

2103 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003924/bq2118sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003924/bq2118Isup2.hkl

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

C13H9Cl2NO	F(000) = 1088
Mr = 266.11	Dx = 1.480 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3178 reflections
a = 7.2693 (13) Å	θ = 2.9–26.3°
b = 13.0037 (19) Å	µ = 0.52 mm−1
c = 25.2711 (16) Å	T = 298 K
V = 2388.8 (6) Å3	Block, yellow
Z = 8	0.50 × 0.48 × 0.47 mm

Siemens SMART CCD area-detector diffractometer	2103 independent reflections
Radiation source: fine-focus sealed tube	1496 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −8→8
Tmin = 0.780, Tmax = 0.791	k = −15→11
11102 measured reflections	l = −30→29

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0287P)2 + 1.7853P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2103 reflections	Δρmax = 0.20 e Å−3
155 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0069 (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	0.07629 (12)	1.13163 (6)	1.12839 (3)	0.0653 (3)
Cl2	0.41980 (14)	0.79479 (6)	0.83555 (3)	0.0760 (3)
N1	0.3625 (3)	0.96742 (15)	0.90783 (8)	0.0407 (5)
O1	0.2932 (4)	0.81908 (14)	0.97404 (8)	0.0734 (7)
H1	0.3252	0.8457	0.9461	0.110*
C1	0.3120 (3)	1.03135 (19)	0.94334 (9)	0.0396 (6)
H1A	0.3132	1.1013	0.9357	0.048*
C2	0.2530 (3)	0.99774 (18)	0.99498 (9)	0.0366 (6)
C3	0.2445 (4)	0.89294 (19)	1.00872 (10)	0.0482 (7)
C4	0.1860 (4)	0.8649 (2)	1.05868 (11)	0.0591 (8)
H4	0.1806	0.7956	1.0677	0.071*
C5	0.1357 (4)	0.9376 (2)	1.09521 (11)	0.0519 (7)
H5	0.0972	0.9178	1.1288	0.062*
C6	0.1427 (4)	1.04066 (19)	1.08177 (10)	0.0432 (6)
C7	0.1990 (4)	1.07049 (19)	1.03254 (10)	0.0422 (6)
H7	0.2014	1.1400	1.0239	0.051*
C8	0.4229 (3)	0.99867 (19)	0.85743 (9)	0.0393 (6)
C9	0.4587 (4)	0.9228 (2)	0.82003 (11)	0.0462 (7)
C10	0.5255 (4)	0.9469 (2)	0.77026 (11)	0.0588 (8)
H10	0.5487	0.8949	0.7459	0.071*
C11	0.5574 (4)	1.0476 (3)	0.75699 (12)	0.0627 (8)
H11	0.6026	1.0641	0.7236	0.075*
C12	0.5224 (5)	1.1235 (2)	0.79298 (12)	0.0635 (9)
H12	0.5439	1.1918	0.7839	0.076*
C13	0.4556 (4)	1.1001 (2)	0.84244 (11)	0.0544 (7)
H13	0.4319	1.1529	0.8663	0.065*

	U11	U22	U33	U12	U13	U23
Cl1	0.0859 (6)	0.0587 (5)	0.0515 (4)	0.0011 (4)	0.0102 (4)	−0.0135 (4)
Cl2	0.1089 (8)	0.0424 (4)	0.0766 (6)	−0.0022 (4)	0.0226 (5)	−0.0113 (4)
N1	0.0478 (13)	0.0375 (12)	0.0367 (11)	−0.0015 (10)	−0.0029 (10)	−0.0003 (10)
O1	0.128 (2)	0.0355 (10)	0.0562 (12)	0.0156 (12)	0.0259 (13)	0.0034 (9)
C1	0.0434 (15)	0.0330 (13)	0.0424 (14)	−0.0013 (11)	−0.0043 (12)	0.0023 (12)
C2	0.0385 (13)	0.0335 (12)	0.0377 (13)	−0.0001 (10)	−0.0036 (12)	0.0011 (11)
C3	0.0614 (18)	0.0379 (14)	0.0452 (15)	0.0094 (13)	0.0001 (14)	0.0028 (12)
C4	0.088 (2)	0.0384 (15)	0.0512 (16)	0.0129 (15)	0.0078 (16)	0.0119 (14)
C5	0.0633 (19)	0.0532 (17)	0.0391 (14)	0.0078 (14)	0.0032 (14)	0.0097 (13)
C6	0.0467 (16)	0.0428 (15)	0.0402 (14)	0.0026 (12)	−0.0029 (12)	−0.0038 (12)
C7	0.0481 (16)	0.0343 (13)	0.0443 (15)	−0.0037 (11)	−0.0030 (12)	−0.0001 (11)
C8	0.0390 (14)	0.0436 (14)	0.0353 (13)	−0.0006 (12)	−0.0059 (11)	0.0024 (11)
C9	0.0472 (17)	0.0435 (15)	0.0479 (15)	0.0012 (12)	−0.0004 (13)	−0.0024 (12)
C10	0.060 (2)	0.068 (2)	0.0478 (16)	0.0039 (16)	0.0083 (15)	−0.0077 (15)
C11	0.063 (2)	0.080 (2)	0.0456 (16)	−0.0032 (17)	0.0071 (15)	0.0107 (17)
C12	0.082 (2)	0.0572 (18)	0.0518 (17)	−0.0089 (17)	0.0014 (16)	0.0151 (15)
C13	0.073 (2)	0.0429 (15)	0.0475 (16)	−0.0042 (14)	−0.0005 (15)	0.0022 (13)

Cl1—C6	1.738 (3)	C5—H5	0.9300
Cl2—C9	1.733 (3)	C6—C7	1.366 (3)
N1—C1	1.277 (3)	C7—H7	0.9300
N1—C8	1.407 (3)	C8—C9	1.391 (4)
O1—C3	1.347 (3)	C8—C13	1.393 (4)
O1—H1	0.8200	C9—C10	1.384 (4)
C1—C2	1.441 (3)	C10—C11	1.371 (4)
C1—H1A	0.9300	C10—H10	0.9300
C2—C7	1.397 (3)	C11—C12	1.367 (4)
C2—C3	1.408 (3)	C11—H11	0.9300
C3—C4	1.381 (4)	C12—C13	1.375 (4)
C4—C5	1.371 (4)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.383 (4)
C1—N1—C8	122.5 (2)	C6—C7—H7	119.6
C3—O1—H1	109.5	C2—C7—H7	119.6
N1—C1—C2	121.6 (2)	C9—C8—C13	117.1 (2)
N1—C1—H1A	119.2	C9—C8—N1	117.9 (2)
C2—C1—H1A	119.2	C13—C8—N1	124.9 (2)
C7—C2—C3	118.4 (2)	C10—C9—C8	121.5 (3)
C7—C2—C1	119.6 (2)	C10—C9—Cl2	118.7 (2)
C3—C2—C1	122.0 (2)	C8—C9—Cl2	119.8 (2)
O1—C3—C4	119.2 (2)	C11—C10—C9	119.9 (3)
O1—C3—C2	121.2 (2)	C11—C10—H10	120.1
C4—C3—C2	119.6 (2)	C9—C10—H10	120.1
C5—C4—C3	121.0 (3)	C12—C11—C10	119.7 (3)
C5—C4—H4	119.5	C12—C11—H11	120.1
C3—C4—H4	119.5	C10—C11—H11	120.1
C4—C5—C6	119.5 (3)	C11—C12—C13	120.7 (3)
C4—C5—H5	120.2	C11—C12—H12	119.6
C6—C5—H5	120.2	C13—C12—H12	119.6
C7—C6—C5	120.6 (2)	C12—C13—C8	121.2 (3)
C7—C6—Cl1	120.5 (2)	C12—C13—H13	119.4
C5—C6—Cl1	118.9 (2)	C8—C13—H13	119.4
C6—C7—C2	120.7 (2)
C8—N1—C1—C2	−179.1 (2)	C1—C2—C7—C6	−179.9 (2)
N1—C1—C2—C7	180.0 (2)	C1—N1—C8—C9	−174.2 (2)
N1—C1—C2—C3	−1.2 (4)	C1—N1—C8—C13	8.1 (4)
C7—C2—C3—O1	179.4 (3)	C13—C8—C9—C10	0.6 (4)
C1—C2—C3—O1	0.6 (4)	N1—C8—C9—C10	−177.4 (3)
C7—C2—C3—C4	−0.8 (4)	C13—C8—C9—Cl2	−179.5 (2)
C1—C2—C3—C4	−179.6 (3)	N1—C8—C9—Cl2	2.5 (3)
O1—C3—C4—C5	179.8 (3)	C8—C9—C10—C11	−0.1 (4)
C2—C3—C4—C5	0.1 (5)	Cl2—C9—C10—C11	180.0 (2)
C3—C4—C5—C6	0.3 (5)	C9—C10—C11—C12	−0.2 (5)
C4—C5—C6—C7	0.1 (4)	C10—C11—C12—C13	0.1 (5)
C4—C5—C6—Cl1	179.4 (2)	C11—C12—C13—C8	0.4 (5)
C5—C6—C7—C2	−0.9 (4)	C9—C8—C13—C12	−0.7 (4)
Cl1—C6—C7—C2	179.8 (2)	N1—C8—C13—C12	177.1 (3)
C3—C2—C7—C6	1.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.603 (3)	147
C11—H11···Cg1i	0.93	2.97	3.549 (3)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.603 (3)	147
C11—H11⋯Cg1i	0.93	2.97	3.549 (3)	122

Symmetry code: (i) . Cg1 is the centroid of C8–C13 phenyl ring.