4,6-Dichloro-2-{[(E)-(3-{[(E)-3,5-dichloro-2-hy­droxy­benzyl­idene]amino}-2,2-dimethyl­prop­yl)imino]­meth­yl}phenol

Kargar, H.; Kia, R.; Abbasian, S.; Tahir, M.N.

doi:10.1107/S1600536811053438

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o142

doi:10.1107/S1600536811053438

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4,6-Dichloro-2-{[(E)-(3-{[(E)-3,5-dichloro-2-hydroxybenzylidene]amino}-2,2-dimethylpropyl)imino]methyl}phenol

Hadi Kargar,^a ^* Reza Kia,^b,^c Saeideh Abbasian ^a and Muhammad Nawaz Tahir ^d ^*

^aDepartment of Chemistry, Payame Noor University, PO BOX 19395-3697 Tehran, I.R. of Iran, ^bX-ray Crystallography Lab., Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran, ^cDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and ^dDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: hkargar@pnu.ac.ir, dmntahir_uos@yahoo.com

(Received 9 December 2011; accepted 12 December 2011; online 17 December 2011)

In the title compound, C₁₉H₁₈Cl₄N₂O₂, a potential tetradentate 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 intramolecular O—H⋯N hydrogen bonds make S(6) ring motifs. In the crystal, molecules are linked along the b axis via intermolecular C—H⋯Cl interactions. The crystal structure is further stabilized by an intermolecular π–π interaction [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_r = 448.15
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 1.03
5165 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.93	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) $[-x, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811053438/su2348sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811053438/su2348Isup3.cml

checkCIF report

Comment top

In continuation of our work on Schiff base ligands (Kargar et al., 2011; Kia et al., 2010), we present herein the crystal structure of the title compound.

The title molecule, Fig. 1, is a potential tetradentate Schiff base ligand. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those found for similar structures, for example 4,4-Dimethoxy-2,2-[2,2-dimethylpropane-1,3-diylbis(nitrilomethanylylidene)] diphenol (Kargar et al., 2011) and 5,5-Bis(diethylamino)-2,2-[2,2-dimethylpropane-1,3-diylbis(nitrilomethylidyne)] diphenol (Kia et al., 2010). There are two intramolecular O—H···N hydrogen bonds (Table 1) making S(6) ring motifs (Bernstein et al., 1995), and the configuration about both C═ N bonds is E. The two benzene rings, (C1-C6) and (C14-C19), are inclined to one another by 48.01 (10)°.

In the crystal, neighbouring molecules are linked along the b-axis direction through intermolecular C—H···Cl interactions (Table 1 and Fig. 2). The crystal structure is further stabilized by an intermolecular π-π interaction involving inversion related molecules [Cg1···Cg1ⁱ = 3.5744 (12)Å; (i) -x, -y, -z; Cg1 is the centroid of ring (C1-C6)].

Related literature top

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 top

The title compound was synthesized by adding 3,5-dichloro-salicylaldehyde (2 mmol) to a solution of 2,2-dimethyl-1,3-propanediamine (1 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for 30 min. The resultant solution was filtered. Yellow single crystals of the title compound, suitable for X-ray analysis, were obtained by recrystallization from ethanol on slow evaporation of the solvent at room temperature over several days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering. The dashed lines indicate the intramolecular N-H···O hydrogen bonds (see Table 1 for details).
	Fig. 2. A partial view of the crystal packing of the title compound, viewed down the c-axis, showing the intermolecular C—H···Cl interactions (dashed lines; only the H atoms involved in these interactions are shown].

4,6-Dichloro-2-{[(E)-(3-{[(E)-3,5-dichloro-2- hydroxybenzylidene]amino}-2,2-dimethylpropyl)imino]methyl}phenol top

Crystal data top

C₁₉H₁₈Cl₄N₂O₂	F(000) = 920
M_r = 448.15	D_x = 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

Data collection top

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

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0483P)² + 0.5514P] where P = (F_o² + 2F_c²)/3
5165 reflections	(Δ/σ)_max = 0.001
246 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₉H₁₈Cl₄N₂O₂	V = 2085.70 (11) Å³
M_r = 448.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.5265 (5) Å	µ = 0.58 mm⁻¹
b = 10.3242 (3) Å	T = 296 K
c = 12.6433 (4) Å	0.18 × 0.12 × 0.08 mm
β = 104.796 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5165 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3427 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.955	R_int = 0.027
19903 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	Δρ_max = 0.40 e Å⁻³
5165 reflections	Δρ_min = −0.38 e Å⁻³
246 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y+1/2, −z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈Cl₄N₂O₂
M_r	448.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.5265 (5), 10.3242 (3), 12.6433 (4)
β (°)	104.796 (1)
V (Å³)	2085.70 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.18 × 0.12 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.902, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	19903, 5165, 3427
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 1.03
No. of reflections	5165
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.38

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x, y+1/2, −z−1/2.

Acknowledgements

HK and SA thank PNU for financial support. MNT thanks GC University of Sargodha, Pakistan, for research facilities.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kargar, H., Kia, R., Pahlavani, E. & Tahir, M. N. (2011). Acta Cryst. E67, o614. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kia, R., Kargar, H., Tahir, M. N. & Kianoosh, F. (2010). Acta Cryst. E66, o2296. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

4,6-Di­chloro-2-{[(E)-(3-{[(E)-3,5-di­chloro-2-hy­dr­oxy­benzyl­­idene]amino}-2,2-di­methyl­prop­yl)imino]­meth­yl}phenol

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4,6-Dichloro-2-{[(E)-(3-{[(E)-3,5-dichloro-2-hydroxybenzylidene]amino}-2,2-dimethylpropyl)imino]methyl}phenol