4,6-Dichloro-2-{[(E)-(3-{[(E)-3,5-dichloro-2-hy-droxy-benzyl-idene]amino}-2,2-dimethyl-prop-yl)imino]-meth-yl}phenol.

In the title compound, C(19)H(18)Cl(4)N(2)O(2), a potential tetra-dentate Schiff base ligand, the dihedral angle between the two benzene rings is 48.01 (10)°. The configuration about the two C=N bonds is E and two intra-molecular O-H⋯N hydrogen bonds make S(6) ring motifs. In the crystal, mol-ecules are linked along the b axis via inter-molecular C-H⋯Cl inter-actions. The crystal structure is further stabilized by an inter-molecular π-π inter-action [centroid-centroid distance = 3.5744 (12) Å].

Related literature

For standard bond-lengths, see: Allen et al. (1987 ▶). For hydrogen bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Kargar et al. (2011 ▶); Kia et al. (2010 ▶).

Experimental

Crystal data

C19H18Cl4N2O2

M = 448.15

Monoclinic,

a = 16.5265 (5) Å

b = 10.3242 (3) Å

c = 12.6433 (4) Å

β = 104.796 (1)°

V = 2085.70 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.58 mm−1

T = 296 K

0.18 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.902, T max = 0.955

19903 measured reflections

5165 independent reflections

3427 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.119

S = 1.03

5165 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811053438/su2348sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053438/su2348Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053438/su2348Isup3.cml

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

C19H18Cl4N2O2	F(000) = 920
Mr = 448.15	Dx = 1.427 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2540 reflections
a = 16.5265 (5) Å	θ = 2.5–27.4°
b = 10.3242 (3) Å	µ = 0.58 mm−1
c = 12.6433 (4) Å	T = 296 K
β = 104.796 (1)°	Block, yellow
V = 2085.70 (11) Å3	0.18 × 0.12 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5165 independent reflections
Radiation source: fine-focus sealed tube	3427 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −22→22
Tmin = 0.902, Tmax = 0.955	k = −13→13
19903 measured reflections	l = −16→16

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0483P)2 + 0.5514P] where P = (Fo2 + 2Fc2)/3
5165 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	−0.21903 (4)	−0.02100 (8)	−0.20278 (6)	0.0929 (2)
Cl2	−0.10588 (6)	0.11487 (9)	0.21661 (6)	0.1149 (4)
Cl3	0.46259 (4)	0.99049 (7)	0.34212 (5)	0.0831 (2)
Cl4	0.41065 (4)	1.19135 (6)	−0.06309 (6)	0.0755 (2)
O1	0.03427 (11)	0.22770 (15)	0.14769 (12)	0.0690 (4)
H1	0.0791	0.2544	0.1216	0.104*
O2	0.39245 (10)	0.75500 (14)	0.22723 (12)	0.0621 (4)
H2A	0.3725	0.6889	0.1818	0.093*
N1	0.11973 (11)	0.27146 (15)	0.00940 (14)	0.0512 (4)
N2	0.33256 (10)	0.61812 (16)	0.05705 (15)	0.0540 (4)
C1	−0.01322 (12)	0.16963 (17)	−0.04155 (15)	0.0436 (4)
C2	−0.07424 (13)	0.1108 (2)	−0.12407 (17)	0.0529 (5)
H2	−0.0680	0.1085	−0.1951	0.063*
C3	−0.14354 (12)	0.0562 (2)	−0.10131 (19)	0.0561 (5)
C4	−0.15422 (13)	0.05939 (19)	0.0031 (2)	0.0583 (5)
H4	−0.2016	0.0231	0.0181	0.070*
C5	−0.09431 (14)	0.11660 (19)	0.08457 (18)	0.0561 (5)
C6	−0.02244 (13)	0.17359 (17)	0.06566 (16)	0.0488 (5)
C7	0.06112 (13)	0.22448 (17)	−0.06553 (16)	0.0484 (5)
H7	0.0657	0.2251	−0.1373	0.058*
C8	0.19538 (14)	0.32198 (19)	−0.01584 (19)	0.0563 (5)
H8A	0.1845	0.3363	−0.0940	0.068*
H8B	0.2399	0.2585	0.0049	0.068*
C9	0.22377 (12)	0.44956 (17)	0.04474 (16)	0.0478 (4)
C10	0.15394 (14)	0.5495 (2)	0.0148 (2)	0.0665 (6)
H10A	0.1729	0.6300	0.0508	0.100*
H10B	0.1062	0.5192	0.0377	0.100*
H10C	0.1387	0.5625	−0.0630	0.100*
C11	0.24805 (17)	0.4257 (3)	0.16823 (19)	0.0722 (6)
H11A	0.2659	0.5057	0.2057	0.108*
H11B	0.2929	0.3639	0.1862	0.108*
H11C	0.2006	0.3927	0.1903	0.108*
C12	0.30059 (13)	0.49455 (19)	0.00771 (19)	0.0565 (5)
H12A	0.3442	0.4296	0.0277	0.068*
H12B	0.2857	0.5031	−0.0713	0.068*
C13	0.33932 (12)	0.71454 (19)	−0.00290 (18)	0.0517 (5)
H13	0.3238	0.7055	−0.0786	0.062*
C14	0.37085 (11)	0.83825 (18)	0.04477 (17)	0.0476 (4)
C15	0.39724 (12)	0.85146 (19)	0.15984 (17)	0.0496 (5)
C16	0.42908 (12)	0.9726 (2)	0.20143 (18)	0.0541 (5)
C17	0.43340 (13)	1.0753 (2)	0.1340 (2)	0.0594 (6)
H17	0.4546	1.1546	0.1636	0.071*
C18	0.40590 (13)	1.0599 (2)	0.02195 (19)	0.0552 (5)
C19	0.37588 (12)	0.9427 (2)	−0.02257 (18)	0.0523 (5)
H19	0.3588	0.9332	−0.0982	0.063*

	U11	U22	U33	U12	U13	U23
Cl1	0.0543 (4)	0.1232 (6)	0.0882 (5)	−0.0138 (4)	−0.0059 (3)	−0.0123 (4)
Cl2	0.1553 (8)	0.1295 (7)	0.0893 (5)	−0.0722 (6)	0.0850 (6)	−0.0384 (5)
Cl3	0.0872 (5)	0.0918 (5)	0.0674 (4)	−0.0259 (4)	0.0148 (3)	−0.0268 (3)
Cl4	0.0754 (4)	0.0543 (3)	0.1042 (5)	0.0008 (3)	0.0363 (4)	0.0125 (3)
O1	0.0863 (11)	0.0739 (10)	0.0535 (9)	−0.0326 (9)	0.0301 (8)	−0.0173 (7)
O2	0.0711 (10)	0.0547 (8)	0.0578 (9)	−0.0074 (7)	0.0115 (8)	−0.0026 (7)
N1	0.0587 (10)	0.0428 (9)	0.0580 (10)	−0.0102 (7)	0.0258 (8)	−0.0038 (7)
N2	0.0503 (9)	0.0469 (9)	0.0671 (11)	−0.0085 (7)	0.0191 (8)	−0.0114 (8)
C1	0.0483 (10)	0.0370 (9)	0.0478 (10)	0.0032 (7)	0.0166 (8)	0.0044 (8)
C2	0.0533 (12)	0.0557 (12)	0.0478 (11)	0.0066 (9)	0.0094 (9)	0.0042 (9)
C3	0.0422 (10)	0.0541 (12)	0.0670 (14)	0.0042 (9)	0.0052 (9)	0.0007 (10)
C4	0.0523 (12)	0.0457 (11)	0.0840 (16)	−0.0002 (9)	0.0305 (11)	−0.0033 (11)
C5	0.0687 (13)	0.0475 (11)	0.0625 (13)	−0.0057 (10)	0.0358 (11)	−0.0058 (10)
C6	0.0617 (12)	0.0361 (9)	0.0540 (11)	−0.0032 (8)	0.0248 (10)	−0.0040 (8)
C7	0.0611 (12)	0.0419 (10)	0.0468 (11)	0.0022 (9)	0.0223 (9)	0.0032 (8)
C8	0.0621 (13)	0.0464 (11)	0.0688 (14)	−0.0103 (9)	0.0319 (11)	−0.0100 (10)
C9	0.0514 (11)	0.0403 (10)	0.0552 (11)	−0.0026 (8)	0.0202 (9)	−0.0067 (8)
C10	0.0596 (13)	0.0503 (12)	0.0909 (17)	0.0019 (10)	0.0214 (12)	−0.0018 (12)
C11	0.0799 (16)	0.0775 (16)	0.0589 (14)	−0.0062 (13)	0.0171 (12)	−0.0038 (12)
C12	0.0573 (12)	0.0485 (11)	0.0693 (14)	−0.0104 (9)	0.0262 (11)	−0.0170 (10)
C13	0.0462 (11)	0.0539 (12)	0.0560 (12)	−0.0055 (9)	0.0148 (9)	−0.0109 (10)
C14	0.0375 (9)	0.0459 (10)	0.0605 (12)	−0.0032 (8)	0.0147 (9)	−0.0068 (9)
C15	0.0398 (10)	0.0483 (11)	0.0615 (13)	−0.0013 (8)	0.0145 (9)	−0.0078 (9)
C16	0.0440 (10)	0.0583 (12)	0.0610 (13)	−0.0061 (9)	0.0150 (9)	−0.0164 (10)
C17	0.0486 (11)	0.0473 (11)	0.0863 (17)	−0.0085 (9)	0.0244 (11)	−0.0151 (11)
C18	0.0461 (11)	0.0479 (11)	0.0763 (15)	0.0008 (9)	0.0244 (10)	0.0006 (10)
C19	0.0432 (10)	0.0545 (11)	0.0613 (13)	−0.0014 (9)	0.0173 (9)	−0.0036 (10)

Cl1—C3	1.738 (2)	C8—H8A	0.9700
Cl2—C5	1.728 (2)	C8—H8B	0.9700
Cl3—C16	1.733 (2)	C9—C10	1.522 (3)
Cl4—C18	1.745 (2)	C9—C11	1.529 (3)
O1—C6	1.330 (2)	C9—C12	1.533 (3)
O1—H1	0.9260	C10—H10A	0.9600
O2—C15	1.326 (2)	C10—H10B	0.9600
O2—H2A	0.8989	C10—H10C	0.9600
N1—C7	1.266 (3)	C11—H11A	0.9600
N1—C8	1.463 (2)	C11—H11B	0.9600
N2—C13	1.273 (3)	C11—H11C	0.9600
N2—C12	1.459 (2)	C12—H12A	0.9700
C1—C2	1.392 (3)	C12—H12B	0.9700
C1—C6	1.403 (3)	C13—C14	1.451 (3)
C1—C7	1.453 (3)	C13—H13	0.9300
C2—C3	1.371 (3)	C14—C19	1.390 (3)
C2—H2	0.9300	C14—C15	1.415 (3)
C3—C4	1.377 (3)	C15—C16	1.406 (3)
C4—C5	1.367 (3)	C16—C17	1.374 (3)
C4—H4	0.9300	C17—C18	1.382 (3)
C5—C6	1.400 (3)	C17—H17	0.9300
C7—H7	0.9300	C18—C19	1.373 (3)
C8—C9	1.536 (3)	C19—H19	0.9300
C6—O1—H1	108.4	C9—C10—H10B	109.5
C15—O2—H2A	103.5	H10A—C10—H10B	109.5
C7—N1—C8	120.43 (17)	C9—C10—H10C	109.5
C13—N2—C12	120.43 (19)	H10A—C10—H10C	109.5
C2—C1—C6	120.03 (18)	H10B—C10—H10C	109.5
C2—C1—C7	120.20 (18)	C9—C11—H11A	109.5
C6—C1—C7	119.76 (18)	C9—C11—H11B	109.5
C3—C2—C1	120.40 (19)	H11A—C11—H11B	109.5
C3—C2—H2	119.8	C9—C11—H11C	109.5
C1—C2—H2	119.8	H11A—C11—H11C	109.5
C2—C3—C4	120.7 (2)	H11B—C11—H11C	109.5
C2—C3—Cl1	120.95 (18)	N2—C12—C9	111.85 (16)
C4—C3—Cl1	118.37 (17)	N2—C12—H12A	109.2
C5—C4—C3	119.14 (19)	C9—C12—H12A	109.2
C5—C4—H4	120.4	N2—C12—H12B	109.2
C3—C4—H4	120.4	C9—C12—H12B	109.2
C4—C5—C6	122.4 (2)	H12A—C12—H12B	107.9
C4—C5—Cl2	119.05 (16)	N2—C13—C14	121.18 (19)
C6—C5—Cl2	118.52 (17)	N2—C13—H13	119.4
O1—C6—C5	120.20 (18)	C14—C13—H13	119.4
O1—C6—C1	122.47 (17)	C19—C14—C15	120.27 (18)
C5—C6—C1	117.33 (19)	C19—C14—C13	120.01 (19)
N1—C7—C1	121.28 (18)	C15—C14—C13	119.72 (18)
N1—C7—H7	119.4	O2—C15—C16	120.39 (19)
C1—C7—H7	119.4	O2—C15—C14	122.35 (17)
N1—C8—C9	111.48 (16)	C16—C15—C14	117.26 (19)
N1—C8—H8A	109.3	C17—C16—C15	121.9 (2)
C9—C8—H8A	109.3	C17—C16—Cl3	120.06 (16)
N1—C8—H8B	109.3	C15—C16—Cl3	118.02 (17)
C9—C8—H8B	109.3	C16—C17—C18	119.44 (19)
H8A—C8—H8B	108.0	C16—C17—H17	120.3
C10—C9—C11	110.33 (18)	C18—C17—H17	120.3
C10—C9—C12	110.66 (17)	C19—C18—C17	120.8 (2)
C11—C9—C12	109.80 (18)	C19—C18—Cl4	120.06 (18)
C10—C9—C8	110.00 (18)	C17—C18—Cl4	119.17 (16)
C11—C9—C8	109.78 (17)	C18—C19—C14	120.3 (2)
C12—C9—C8	106.19 (15)	C18—C19—H19	119.8
C9—C10—H10A	109.5	C14—C19—H19	119.8
C6—C1—C2—C3	−0.1 (3)	C13—N2—C12—C9	−123.0 (2)
C7—C1—C2—C3	178.47 (18)	C10—C9—C12—N2	58.9 (2)
C1—C2—C3—C4	0.4 (3)	C11—C9—C12—N2	−63.2 (2)
C1—C2—C3—Cl1	−178.43 (15)	C8—C9—C12—N2	178.20 (18)
C2—C3—C4—C5	−0.7 (3)	C12—N2—C13—C14	179.89 (17)
Cl1—C3—C4—C5	178.21 (16)	N2—C13—C14—C19	−178.60 (18)
C3—C4—C5—C6	0.6 (3)	N2—C13—C14—C15	2.1 (3)
C3—C4—C5—Cl2	−177.50 (16)	C19—C14—C15—O2	179.00 (18)
C4—C5—C6—O1	−179.76 (19)	C13—C14—C15—O2	−1.7 (3)
Cl2—C5—C6—O1	−1.6 (3)	C19—C14—C15—C16	−0.8 (3)
C4—C5—C6—C1	−0.3 (3)	C13—C14—C15—C16	178.51 (17)
Cl2—C5—C6—C1	177.81 (15)	O2—C15—C16—C17	−178.70 (18)
C2—C1—C6—O1	179.48 (18)	C14—C15—C16—C17	1.1 (3)
C7—C1—C6—O1	0.9 (3)	O2—C15—C16—Cl3	0.7 (3)
C2—C1—C6—C5	0.1 (3)	C14—C15—C16—Cl3	−179.46 (14)
C7—C1—C6—C5	−178.52 (17)	C15—C16—C17—C18	−0.1 (3)
C8—N1—C7—C1	177.78 (17)	Cl3—C16—C17—C18	−179.55 (16)
C2—C1—C7—N1	−175.71 (18)	C16—C17—C18—C19	−1.2 (3)
C6—C1—C7—N1	2.9 (3)	C16—C17—C18—Cl4	179.39 (15)
C7—N1—C8—C9	137.80 (19)	C17—C18—C19—C14	1.5 (3)
N1—C8—C9—C10	−57.9 (2)	Cl4—C18—C19—C14	−179.09 (15)
N1—C8—C9—C11	63.7 (2)	C15—C14—C19—C18	−0.5 (3)
N1—C8—C9—C12	−177.66 (18)	C13—C14—C19—C18	−179.79 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.93	1.73	2.553 (2)	147
O2—H2A···N2	0.90	1.71	2.553 (2)	155
C12—H12B···Cl1i	0.97	2.80	3.749 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.93	1.73	2.553 (2)	147
O2—H2A⋯N2	0.90	1.71	2.553 (2)	155
C12—H12B⋯Cl1i	0.97	2.80	3.749 (2)	167

Symmetry code: (i) .