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

The asymmetric unit of the title compound, C(18)H(16)Cl(4)N(2)O(2), comprises half of a potentially tetra-dentate Schiff base ligand. It is located about a twofold rotation axis that bis-ects the central C-C bond of the butane-1,4-diamine group. There are two intra-molecular O-H⋯N hydrogen bonds making S(6) ring motifs. In the crystal, mol-ecules are linked by pairs of weak C-H⋯Cl inter-actions, forming inversion dimers, which are further connected by C-H⋯O hydrogen bonds into two-dimensional frameworks that lie parallel to (001).

Related literature

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

Experimental

Crystal data

C18H16Cl4N2O2

M = 434.13

Orthorhombic,

a = 15.871 (3) Å

b = 12.505 (3) Å

c = 9.4133 (18) Å

V = 1868.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.65 mm−1

T = 291 K

0.35 × 0.16 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.805, T max = 0.915

8772 measured reflections

2057 independent reflections

1264 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.095

S = 1.02

2057 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.27 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/S1600536812028693/su2460sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028693/su2460Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028693/su2460Isup3.cml

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

C18H16Cl4N2O2	F(000) = 888
Mr = 434.13	Dx = 1.543 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 851 reflections
a = 15.871 (3) Å	θ = 2.8–27.5°
b = 12.505 (3) Å	µ = 0.65 mm−1
c = 9.4133 (18) Å	T = 291 K
V = 1868.3 (6) Å3	Needle, yellow
Z = 4	0.35 × 0.16 × 0.14 mm

Bruker SMART APEXII CCD area-detector diffractometer	2057 independent reflections
Radiation source: fine-focus sealed tube	1264 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
φ and ω scans	θmax = 27.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −20→12
Tmin = 0.805, Tmax = 0.915	k = −16→15
8772 measured reflections	l = −10→12

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0259P)2 + 0.896P] where P = (Fo2 + 2Fc2)/3
2057 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.27 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	0.37204 (6)	0.74164 (6)	0.18745 (9)	0.0673 (3)
Cl2	0.44335 (5)	0.32968 (6)	0.08251 (9)	0.0613 (3)
O1	0.24660 (12)	0.65449 (13)	0.3845 (2)	0.0492 (5)
H1	0.2062	0.6189	0.4413	0.074*
N1	0.16734 (13)	0.50222 (17)	0.5089 (2)	0.0383 (5)
C1	0.29214 (16)	0.57913 (19)	0.3202 (3)	0.0356 (6)
C2	0.35462 (17)	0.60699 (19)	0.2224 (3)	0.0404 (7)
C3	0.40082 (17)	0.5318 (2)	0.1515 (3)	0.0428 (7)
H3	0.4418	0.5526	0.0866	0.051*
C4	0.38606 (17)	0.4244 (2)	0.1772 (3)	0.0413 (7)
C5	0.32680 (17)	0.3932 (2)	0.2738 (3)	0.0402 (7)
H5	0.3181	0.3209	0.2910	0.048*
C6	0.27940 (16)	0.46897 (19)	0.3465 (3)	0.0344 (6)
C7	0.21558 (16)	0.4352 (2)	0.4470 (3)	0.0379 (6)
H7	0.2096	0.3628	0.4670	0.046*
C8	0.10183 (16)	0.4624 (2)	0.6055 (3)	0.0435 (7)
H8A	0.0946	0.5125	0.6833	0.052*
H8B	0.1194	0.3944	0.6452	0.052*
C9	0.01787 (17)	0.4483 (2)	0.5280 (3)	0.0481 (8)
H9A	0.0258	0.3993	0.4492	0.058*
H9B	−0.0225	0.4163	0.5926	0.058*

	U11	U22	U33	U12	U13	U23
Cl1	0.0782 (6)	0.0361 (4)	0.0874 (6)	−0.0057 (4)	0.0253 (5)	0.0114 (4)
Cl2	0.0628 (5)	0.0484 (4)	0.0727 (6)	0.0047 (4)	0.0223 (4)	−0.0103 (4)
O1	0.0497 (12)	0.0349 (10)	0.0630 (12)	0.0051 (9)	0.0161 (11)	0.0044 (9)
N1	0.0308 (12)	0.0419 (12)	0.0421 (13)	−0.0032 (11)	0.0016 (11)	0.0050 (11)
C1	0.0305 (15)	0.0343 (13)	0.0420 (15)	0.0009 (12)	−0.0014 (13)	0.0019 (12)
C2	0.0410 (17)	0.0321 (13)	0.0481 (17)	−0.0052 (13)	0.0009 (14)	0.0058 (12)
C3	0.0362 (16)	0.0458 (16)	0.0465 (17)	−0.0041 (13)	0.0077 (14)	0.0027 (13)
C4	0.0394 (17)	0.0371 (14)	0.0475 (16)	−0.0003 (13)	0.0042 (14)	−0.0056 (13)
C5	0.0408 (16)	0.0324 (13)	0.0473 (17)	−0.0022 (12)	0.0036 (14)	0.0013 (12)
C6	0.0309 (15)	0.0353 (13)	0.0371 (15)	−0.0014 (12)	−0.0007 (12)	0.0026 (11)
C7	0.0354 (16)	0.0330 (13)	0.0453 (16)	−0.0042 (13)	−0.0035 (13)	0.0041 (12)
C8	0.0383 (16)	0.0475 (16)	0.0446 (16)	−0.0011 (14)	0.0032 (15)	0.0056 (13)
C9	0.0408 (18)	0.0456 (16)	0.0578 (19)	−0.0038 (14)	0.0128 (16)	0.0048 (14)

Cl1—C2	1.738 (2)	C4—C5	1.365 (3)
Cl2—C4	1.739 (3)	C5—C6	1.390 (3)
O1—C1	1.333 (3)	C5—H5	0.9300
O1—H1	0.9457	C6—C7	1.449 (3)
N1—C7	1.276 (3)	C7—H7	0.9300
N1—C8	1.468 (3)	C8—C9	1.530 (4)
C1—C2	1.397 (4)	C8—H8A	0.9700
C1—C6	1.414 (3)	C8—H8B	0.9700
C2—C3	1.366 (4)	C9—C9i	1.506 (5)
C3—C4	1.385 (3)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
C1—O1—H1	106.9	C5—C6—C7	120.1 (2)
C7—N1—C8	119.0 (2)	C1—C6—C7	119.9 (2)
O1—C1—C2	120.5 (2)	N1—C7—C6	121.8 (2)
O1—C1—C6	122.1 (2)	N1—C7—H7	119.1
C2—C1—C6	117.4 (2)	C6—C7—H7	119.1
C3—C2—C1	122.1 (2)	N1—C8—C9	111.1 (2)
C3—C2—Cl1	119.3 (2)	N1—C8—H8A	109.4
C1—C2—Cl1	118.6 (2)	C9—C8—H8A	109.4
C2—C3—C4	119.4 (3)	N1—C8—H8B	109.4
C2—C3—H3	120.3	C9—C8—H8B	109.4
C4—C3—H3	120.3	H8A—C8—H8B	108.0
C5—C4—C3	120.7 (2)	C9i—C9—C8	113.3 (3)
C5—C4—Cl2	120.5 (2)	C9i—C9—H9A	108.9
C3—C4—Cl2	118.9 (2)	C8—C9—H9A	108.9
C4—C5—C6	120.4 (2)	C9i—C9—H9B	108.9
C4—C5—H5	119.8	C8—C9—H9B	108.9
C6—C5—H5	119.8	H9A—C9—H9B	107.7
C5—C6—C1	120.0 (2)
O1—C1—C2—C3	−178.1 (2)	C4—C5—C6—C7	178.9 (2)
C6—C1—C2—C3	1.5 (4)	O1—C1—C6—C5	178.1 (2)
O1—C1—C2—Cl1	0.4 (4)	C2—C1—C6—C5	−1.5 (4)
C6—C1—C2—Cl1	−180.0 (2)	O1—C1—C6—C7	−0.5 (4)
C1—C2—C3—C4	−0.4 (4)	C2—C1—C6—C7	179.9 (2)
Cl1—C2—C3—C4	−178.8 (2)	C8—N1—C7—C6	177.7 (2)
C2—C3—C4—C5	−0.9 (4)	C5—C6—C7—N1	−175.5 (2)
C2—C3—C4—Cl2	178.2 (2)	C1—C6—C7—N1	3.1 (4)
C3—C4—C5—C6	1.0 (4)	C7—N1—C8—C9	−93.8 (3)
Cl2—C4—C5—C6	−178.2 (2)	N1—C8—C9—C9i	−63.4 (4)
C4—C5—C6—C1	0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.95	1.71	2.565 (3)	149
C5—H5···O1ii	0.93	2.48	3.370 (3)	160
C3—H3···Cl2iii	0.93	2.83	3.738 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.95	1.71	2.565 (3)	149
C5—H5⋯O1i	0.93	2.48	3.370 (3)	160
C3—H3⋯Cl2ii	0.93	2.83	3.738 (3)	165

Symmetry codes: (i) ; (ii) .