(E)-4-Chloro-2-{[4-(3,5-dichloro­pyridin-2-yl­oxy)phenyl­imino]­meth­yl}phenol

Ji, H.-B.; Zhang, P.-Z.; Wu, J.

doi:10.1107/S1600536811041584

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2984

doi:10.1107/S1600536811041584

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(E)-4-Chloro-2-{[4-(3,5-dichloropyridin-2-yloxy)phenylimino]methyl}phenol

Hong-Bo Ji,^a Pei-Zhi Zhang ^b and Jun Wu ^a ^*

^aDepartment of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China, and ^bSchool of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310012, People's Republic of China
^*Correspondence e-mail: wujunwu@zju.edu.cn

(Received 24 September 2011; accepted 10 October 2011; online 22 October 2011)

In the title molecule, C₁₈H₁₁Cl₃N₂O₂, the central benzene ring is oriented at 8.44 (12) and 70.57 (11)° with respect to the terminal chlorophenol and dichloropyridine rings, respectively. The molecular structure is stabilized by an intramolecular 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_r = 393.64
Monoclinic, P 2₁ /c
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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.100
S = 1.03
3107 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811041584/xu5335sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811041584/xu5335Isup3.cml

checkCIF report

Comment top

In 2011, much attention has been focused on the biological properties of Schiff bases compounds, Schiff base ligands may contain a variety of substituents with different electron-donating or electron-withdrawing groups and therefore may have interesting chemical properties. They have attracted particular interest due to their biological activities (Shapiro, 1998). They have been found to posses the pharmacological activities such as antimalarial, anticancer, antibacterial (Venugopal & Jayashree, 2008), antifungal (Pandey et al., 2003), antitubercular (Bhat et al., 2005), anti-inflammatoryand antimicrobial (Wadher et al., 2009) properties.

The crystal structures of a number of Schiff bases compounds have also been determined. Herein, we report on the synthesis and crystal structure of a new Schiff bases compound, prepared by the reaction of 5-chloro-2-hydroxybenzaldehyde with 4-(3,5-dichloropyridin-2-yloxy) benzenamine.

In the title molecule (Fig. 1), the C8-benzene ring forms dihedral angles of 8.5 (2)° and 70.6 (1)° with the chlorophenol and dichloropyridine rings, respectively. The title molecule exists in trans configuration with respect to the C7=N1 bond [C7=N1 = 1.275 (3) Å]. In the crystal packing, π-π stacking interactions between the centroid of C1—C6 (Cg1) and C8—C13 (Cg2) benzene rings, with Cg1···Cg2ⁱ distance of 3.792 (2) Å [symmetry code: (i) -x, 1 - y, 2 - z] are observed. N2/C14—C18 (Cg3)···Cg3ⁱⁱ distance of 3.656 (1)Å [symmetry code: (ii), 1 - x,1 - y,1 - z]. The molecular structure is stabilized by an intramolecular O–H···N hydrogen bond, which generates an S(6) ring motif (Table 1). No significant intermolecular hydrogen bonds are observed.

Related literature top

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 top

The title compound was prepared by the condensation reaction of 5-chloro-2-hydroxybenzaldehyde (5 mmol, 0.78 g) and 4-(3,5-dichloropyridin-2-yloxy)benzenamine (5 mmol, 1.27 g) in anhydrous methanol (30 ml) at ambient temperature. The solution was magnetically stirred at ambient temperature for 10 min until it turned to yellow. Yellow single crystals suitable for X-ray structural determination were obtained by slow evaporation of the solution for 7 d.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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 (Dolomanov et al., 2009).

Figures top

Fig. 1. The molecular structure of title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.

(E)-4-Chloro-2-{[4-(3,5-dichloropyridin-2-yloxy)phenylimino]methyl}phenol top

Crystal data top

C₁₈H₁₁Cl₃N₂O₂	F(000) = 800
M_r = 393.64	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0376P)² + 0.5849P] where P = (F_o² + 2F_c²)/3
3107 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₈H₁₁Cl₃N₂O₂	V = 1700.67 (16) Å³
M_r = 393.64	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.8981 (7) Å	µ = 0.55 mm⁻¹
b = 11.7006 (8) Å	T = 293 K
c = 10.5034 (5) Å	0.38 × 0.36 × 0.29 mm
β = 95.318 (5)°

Data collection top

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	3107 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2186 reflections with I > 2σ(I)
T_min = 0.817, T_max = 0.856	R_int = 0.025
7882 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.03	Δρ_max = 0.27 e Å⁻³
3107 reflections	Δρ_min = −0.26 e Å⁻³
227 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₁Cl₃N₂O₂
M_r	393.64
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.8981 (7), 11.7006 (8), 10.5034 (5)
β (°)	95.318 (5)
V (Å³)	1700.67 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.55
Crystal size (mm)	0.38 × 0.36 × 0.29

Data collection
Diffractometer	Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.817, 0.856
No. of measured, independent and observed [I > 2σ(I)] reflections	7882, 3107, 2186
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.100, 1.03
No. of reflections	3107
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.26

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.586 (3)	146.8

Acknowledgements

The project was supported by the National Natural Science Foundation of China (grant No. 31071720) and the Natural Science Foundation of Zhejiang Province, China (grant No. D3080282).

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2984

doi:10.1107/S1600536811041584

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-4-Chloro-2-{[4-(3,5-di­chloro­pyridin-2-yl­­oxy)phenyl­imino]­meth­yl}phenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-4-Chloro-2-{[4-(3,5-dichloropyridin-2-yloxy)phenylimino]methyl}phenol