(E)-4-Chloro-2-{[4-(3,5-dichloro-pyridin-2-yl-oxy)phenyl-imino]-meth-yl}phenol.

In the title mol-ecule, C(18)H(11)Cl(3)N(2)O(2), the central benzene ring is oriented at 8.44 (12) and 70.57 (11)° with respect to the terminal chloro-phenol and dichloro-pyridine rings, respectively. The mol-ecular structure is stabilized by an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) ring motif. In the crystal, π-π stacking between parallel pyridine rings is observed [centroid-centroid distance = 3.6561 (14) Å].

Related literature

For general background to the pharmacological activity of Schiff base compounds, see: Shapiro (1998 ▶); Venugopal & Jayashree (2008 ▶); Pandey et al. (2003 ▶); Bhat et al. (2005 ▶); Wadher et al. (2009 ▶). For a related structure, see: Fun et al. (2011 ▶).

Experimental

Crystal data

C18H11Cl3N2O2

M = 393.64

Monoclinic,

a = 13.8981 (7) Å

b = 11.7006 (8) Å

c = 10.5034 (5) Å

β = 95.318 (5)°

V = 1700.67 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.55 mm−1

T = 293 K

0.38 × 0.36 × 0.29 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.817, T max = 0.856

7882 measured reflections

3107 independent reflections

2186 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.100

S = 1.03

3107 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811041584/xu5335sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041584/xu5335Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041584/xu5335Isup3.cml

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

C18H11Cl3N2O2	F(000) = 800
Mr = 393.64	Dx = 1.537 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1892 reflections
a = 13.8981 (7) Å	θ = 2.9–29.5°
b = 11.7006 (8) Å	µ = 0.55 mm−1
c = 10.5034 (5) Å	T = 293 K
β = 95.318 (5)°	Block, yellow
V = 1700.67 (16) Å3	0.38 × 0.36 × 0.29 mm
Z = 4

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	3107 independent reflections
Radiation source: fine-focus sealed tube	2186 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 10.3592 pixels mm-1	θmax = 25.4°, θmin = 2.9°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −14→8
Tmin = 0.817, Tmax = 0.856	l = −12→12
7882 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0376P)2 + 0.5849P] where P = (Fo2 + 2Fc2)/3
3107 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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	−0.24721 (6)	0.26343 (9)	1.31374 (10)	0.1009 (3)
Cl2	0.53771 (6)	0.21299 (7)	0.55024 (6)	0.0716 (2)
Cl3	0.41754 (6)	0.53738 (7)	0.20843 (6)	0.0723 (2)
O1	0.08837 (14)	0.54210 (18)	1.22171 (19)	0.0727 (6)
H1	0.1140	0.5196	1.1591	0.109*
O2	0.37377 (13)	0.29274 (16)	0.67705 (16)	0.0629 (5)
N1	0.11798 (14)	0.40766 (18)	1.03385 (17)	0.0464 (5)
N2	0.32327 (15)	0.4354 (2)	0.53329 (19)	0.0570 (6)
C1	0.01103 (17)	0.4760 (2)	1.2388 (2)	0.0503 (6)
C2	−0.0441 (2)	0.5020 (3)	1.3378 (2)	0.0618 (7)
H2	−0.0275	0.5646	1.3899	0.074*
C3	−0.1226 (2)	0.4374 (3)	1.3606 (3)	0.0635 (8)
H3	−0.1592	0.4560	1.4274	0.076*
C4	−0.14696 (18)	0.3448 (3)	1.2841 (3)	0.0605 (7)
C5	−0.09479 (18)	0.3184 (2)	1.1840 (2)	0.0556 (6)
H5	−0.1130	0.2563	1.1320	0.067*
C6	−0.01468 (16)	0.3832 (2)	1.1588 (2)	0.0452 (6)
C7	0.04132 (17)	0.3533 (2)	1.0541 (2)	0.0479 (6)
H7	0.0209	0.2932	1.0004	0.057*
C8	0.17777 (16)	0.3761 (2)	0.9376 (2)	0.0439 (6)
C9	0.16860 (18)	0.2763 (2)	0.8667 (2)	0.0587 (7)
H9	0.1192	0.2251	0.8796	0.070*
C10	0.23239 (19)	0.2524 (3)	0.7770 (2)	0.0580 (7)
H10	0.2258	0.1856	0.7290	0.070*
C11	0.30536 (18)	0.3275 (2)	0.7592 (2)	0.0506 (6)
C12	0.31653 (19)	0.4262 (2)	0.8286 (3)	0.0605 (7)
H12	0.3665	0.4766	0.8159	0.073*
C13	0.25235 (18)	0.4498 (2)	0.9179 (2)	0.0545 (6)
H13	0.2596	0.5167	0.9657	0.065*
C14	0.38386 (18)	0.3526 (2)	0.5682 (2)	0.0483 (6)
C15	0.45916 (17)	0.3205 (2)	0.4973 (2)	0.0463 (6)
C16	0.47057 (17)	0.3767 (2)	0.3851 (2)	0.0475 (6)
H16	0.5199	0.3571	0.3351	0.057*
C17	0.40660 (18)	0.4631 (2)	0.3490 (2)	0.0495 (6)
C18	0.33466 (19)	0.4902 (2)	0.4238 (2)	0.0580 (7)
H18	0.2921	0.5488	0.3978	0.070*

	U11	U22	U33	U12	U13	U23
Cl1	0.0704 (5)	0.0995 (7)	0.1413 (8)	−0.0127 (5)	0.0547 (5)	0.0032 (6)
Cl2	0.0835 (5)	0.0768 (5)	0.0579 (4)	0.0333 (4)	0.0250 (3)	0.0073 (4)
Cl3	0.0867 (5)	0.0815 (6)	0.0517 (4)	0.0132 (4)	0.0228 (3)	0.0158 (3)
O1	0.0733 (13)	0.0749 (15)	0.0738 (13)	−0.0208 (11)	0.0273 (10)	−0.0201 (11)
O2	0.0720 (12)	0.0679 (13)	0.0535 (10)	0.0212 (10)	0.0307 (9)	0.0124 (9)
N1	0.0459 (11)	0.0541 (13)	0.0406 (10)	0.0016 (10)	0.0124 (9)	0.0025 (9)
N2	0.0572 (13)	0.0677 (15)	0.0487 (12)	0.0133 (11)	0.0180 (10)	0.0065 (11)
C1	0.0479 (14)	0.0581 (17)	0.0461 (13)	−0.0003 (12)	0.0102 (11)	0.0045 (12)
C2	0.0675 (18)	0.0693 (19)	0.0505 (15)	0.0029 (15)	0.0158 (13)	−0.0090 (14)
C3	0.0595 (17)	0.080 (2)	0.0543 (15)	0.0136 (15)	0.0251 (13)	0.0055 (15)
C4	0.0474 (14)	0.0638 (19)	0.0734 (18)	0.0041 (13)	0.0226 (13)	0.0107 (15)
C5	0.0516 (14)	0.0543 (16)	0.0623 (16)	0.0013 (13)	0.0120 (13)	−0.0016 (13)
C6	0.0448 (13)	0.0490 (15)	0.0426 (12)	0.0053 (11)	0.0082 (10)	0.0051 (11)
C7	0.0503 (14)	0.0495 (15)	0.0445 (13)	0.0045 (12)	0.0079 (11)	−0.0029 (11)
C8	0.0442 (13)	0.0513 (15)	0.0372 (12)	0.0039 (11)	0.0083 (10)	0.0028 (11)
C9	0.0523 (15)	0.0645 (19)	0.0617 (16)	−0.0102 (13)	0.0188 (13)	−0.0100 (14)
C10	0.0607 (16)	0.0637 (18)	0.0505 (15)	0.0014 (14)	0.0097 (12)	−0.0125 (13)
C11	0.0549 (15)	0.0577 (17)	0.0415 (13)	0.0128 (13)	0.0164 (11)	0.0074 (12)
C12	0.0572 (15)	0.0607 (19)	0.0674 (17)	−0.0055 (13)	0.0259 (13)	−0.0009 (14)
C13	0.0580 (15)	0.0552 (17)	0.0523 (14)	−0.0028 (13)	0.0157 (12)	−0.0065 (12)
C14	0.0541 (14)	0.0533 (16)	0.0393 (13)	0.0034 (12)	0.0139 (11)	−0.0016 (11)
C15	0.0499 (13)	0.0476 (15)	0.0426 (12)	0.0033 (11)	0.0104 (11)	−0.0053 (11)
C16	0.0478 (13)	0.0570 (16)	0.0398 (12)	−0.0020 (12)	0.0149 (11)	−0.0093 (11)
C17	0.0555 (15)	0.0561 (16)	0.0377 (12)	−0.0022 (12)	0.0080 (11)	−0.0001 (11)
C18	0.0603 (16)	0.0653 (18)	0.0499 (15)	0.0129 (14)	0.0129 (13)	0.0074 (13)

Cl1—C4	1.739 (3)	C5—H5	0.9300
Cl2—C15	1.724 (2)	C6—C7	1.448 (3)
Cl3—C17	1.732 (2)	C7—H7	0.9300
O1—C1	1.349 (3)	C8—C13	1.379 (3)
O1—H1	0.8200	C8—C9	1.384 (3)
O2—C14	1.359 (3)	C9—C10	1.381 (3)
O2—C11	1.402 (3)	C9—H9	0.9300
N1—C7	1.275 (3)	C10—C11	1.368 (4)
N1—C8	1.416 (3)	C10—H10	0.9300
N2—C14	1.314 (3)	C11—C12	1.367 (4)
N2—C18	1.339 (3)	C12—C13	1.381 (3)
C1—C2	1.381 (3)	C12—H12	0.9300
C1—C6	1.400 (3)	C13—H13	0.9300
C2—C3	1.366 (4)	C14—C15	1.391 (3)
C2—H2	0.9300	C15—C16	1.371 (3)
C3—C4	1.372 (4)	C16—C17	1.376 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.366 (3)	C17—C18	1.365 (3)
C5—C6	1.393 (3)	C18—H18	0.9300
C1—O1—H1	109.5	C10—C9—H9	119.8
C14—O2—C11	119.80 (19)	C8—C9—H9	119.8
C7—N1—C8	122.9 (2)	C11—C10—C9	119.6 (3)
C14—N2—C18	118.0 (2)	C11—C10—H10	120.2
O1—C1—C2	118.6 (2)	C9—C10—H10	120.2
O1—C1—C6	121.8 (2)	C12—C11—C10	121.2 (2)
C2—C1—C6	119.6 (2)	C12—C11—O2	121.6 (2)
C3—C2—C1	121.1 (3)	C10—C11—O2	116.9 (2)
C3—C2—H2	119.4	C11—C12—C13	118.9 (2)
C1—C2—H2	119.4	C11—C12—H12	120.6
C2—C3—C4	119.5 (3)	C13—C12—H12	120.6
C2—C3—H3	120.3	C8—C13—C12	121.2 (2)
C4—C3—H3	120.3	C8—C13—H13	119.4
C5—C4—C3	120.6 (3)	C12—C13—H13	119.4
C5—C4—Cl1	120.3 (2)	N2—C14—O2	120.1 (2)
C3—C4—Cl1	119.0 (2)	N2—C14—C15	123.0 (2)
C4—C5—C6	120.9 (3)	O2—C14—C15	116.9 (2)
C4—C5—H5	119.5	C16—C15—C14	118.9 (2)
C6—C5—H5	119.5	C16—C15—Cl2	120.45 (18)
C5—C6—C1	118.2 (2)	C14—C15—Cl2	120.63 (18)
C5—C6—C7	120.6 (2)	C15—C16—C17	117.8 (2)
C1—C6—C7	121.2 (2)	C15—C16—H16	121.1
N1—C7—C6	121.5 (2)	C17—C16—H16	121.1
N1—C7—H7	119.2	C18—C17—C16	120.0 (2)
C6—C7—H7	119.2	C18—C17—Cl3	120.1 (2)
C13—C8—C9	118.7 (2)	C16—C17—Cl3	119.89 (19)
C13—C8—N1	116.3 (2)	N2—C18—C17	122.3 (2)
C9—C8—N1	125.0 (2)	N2—C18—H18	118.8
C10—C9—C8	120.3 (2)	C17—C18—H18	118.8

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.586 (3)	147.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.86	2.586 (3)	147