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

The asymmetric unit of the title compound, C(19)H(18)I(4)N(2)O(2), comprises a potentially tetra-dentate Schiff base ligand. The disordered H atoms on the N and O atoms were refined with site occupancies of 0.54 (8)/0.46 (8) and 0.59 (7)/0.41 (7), respectively. The dihedral angle between the benzene rings is 73.3 (3)°. Intra-molecular O-H⋯N and N-H⋯O hydrogen bonds make S(6) ring motifs. Short I⋯I [3.8919 (7) Å] and I⋯Cg [Cg is a ring centroid; 3.911 (2) Å] contacts are present in the crystal structure. The crystal structure is further stabilized by inter-molecular π-π inter-actions [centroid-to-centroid distance = 3.827 (3) Å].

Related literature

For related structures, see for example: Kargar et al. (2011 ▶, 2012 ▶); Kia et al. (2010 ▶). For standard values of bond lengths, see: Allen et al. (1987 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

C19H18I4N2O2

M = 813.95

Orthorhombic,

a = 12.2057 (5) Å

b = 11.8169 (5) Å

c = 31.8157 (15) Å

V = 4588.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 5.45 mm−1

T = 291 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 = 0.441, T max = 0.670

39183 measured reflections

5472 independent reflections

2871 reflections with I > 2σ(I)

R int = 0.099

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.079

S = 1.00

5471 reflections

248 parameters

H-atom parameters constrained

Δρmax = 1.11 e Å−3

Δρmin = −0.94 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003704/vm2150sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003704/vm2150Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003704/vm2150Isup3.cml

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

C19H18I4N2O2	F(000) = 2992
Mr = 813.95	Dx = 2.356 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3211 reflections
a = 12.2057 (5) Å	θ = 2.5–27.5°
b = 11.8169 (5) Å	µ = 5.45 mm−1
c = 31.8157 (15) Å	T = 291 K
V = 4588.9 (3) Å3	Block, yellow
Z = 8	0.18 × 0.12 × 0.08 mm

Bruker SMART APEXII CCD area-detector diffractometer	5472 independent reflections
Radiation source: fine-focus sealed tube	2871 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.099
φ and ω scans	θmax = 27.9°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→16
Tmin = 0.441, Tmax = 0.670	k = −15→14
39183 measured reflections	l = −41→39

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0213P)2] where P = (Fo2 + 2Fc2)/3
5471 reflections	(Δ/σ)max = 0.001
248 parameters	Δρmax = 1.11 e Å−3
0 restraints	Δρmin = −0.94 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	Occ. (<1)
I1	0.67018 (4)	0.26848 (5)	0.383838 (17)	0.06718 (18)
I2	1.02767 (3)	0.17675 (4)	0.508635 (14)	0.04527 (13)
I3	0.82622 (4)	0.00536 (4)	0.001078 (17)	0.06243 (17)
I4	0.65930 (4)	−0.30987 (4)	0.131933 (17)	0.06028 (17)
O1	0.8328 (3)	0.1220 (4)	0.32918 (15)	0.0501 (12)
H1	0.8784	0.0964	0.3128	0.075*	0.46 (8)
O2	0.8775 (3)	−0.2231 (3)	0.17564 (15)	0.0475 (12)
H2	0.9371	−0.2077	0.1860	0.071*	0.59 (7)
N1	0.9942 (4)	−0.0017 (4)	0.31029 (17)	0.0421 (14)
H1A	0.9424	0.0253	0.3063	0.051*	0.54 (8)
N2	1.0582 (4)	−0.1182 (4)	0.18514 (18)	0.0421 (14)
H1B	1.0104	−0.1580	0.2007	0.051*	0.41 (7)
C1	0.8751 (5)	0.1317 (5)	0.3665 (2)	0.0337 (15)
C2	0.8201 (4)	0.1925 (5)	0.3985 (2)	0.0379 (16)
C3	0.8633 (5)	0.2052 (5)	0.4382 (2)	0.0365 (16)
H3	0.8259	0.2468	0.4584	0.044*
C4	0.9642 (5)	0.1548 (5)	0.44789 (19)	0.0333 (15)
C5	1.0178 (5)	0.0919 (5)	0.41839 (19)	0.0331 (15)
H5	1.0838	0.0574	0.4254	0.040*
C6	0.9755 (5)	0.0782 (5)	0.37794 (19)	0.0313 (14)
C7	1.0307 (5)	0.0096 (5)	0.3477 (2)	0.0370 (16)
H7	1.0947	−0.0278	0.3554	0.044*
C8	1.0466 (5)	−0.0734 (5)	0.2792 (2)	0.0436 (17)
H8A	0.9906	−0.1139	0.2637	0.052*
H8B	1.0916	−0.1290	0.2935	0.052*
C9	1.1191 (5)	−0.0066 (5)	0.2478 (2)	0.0381 (16)
C10	1.2243 (5)	0.0305 (6)	0.2697 (2)	0.067 (2)
H10A	1.2693	0.0719	0.2503	0.100*
H10B	1.2634	−0.0350	0.2794	0.100*
H10C	1.2065	0.0780	0.2932	0.100*
C11	1.0597 (5)	0.0973 (5)	0.2311 (2)	0.054 (2)
H11A	1.1027	0.1317	0.2093	0.081*
H11B	1.0490	0.1505	0.2535	0.081*
H11C	0.9898	0.0752	0.2198	0.081*
C12	1.1517 (4)	−0.0858 (5)	0.2119 (2)	0.0426 (17)
H12A	1.2066	−0.0488	0.1947	0.051*
H12B	1.1844	−0.1537	0.2236	0.051*
C13	1.0478 (5)	−0.0796 (5)	0.1485 (2)	0.0392 (17)
H13	1.1029	−0.0336	0.1377	0.047*
C14	0.9534 (5)	−0.1038 (5)	0.1222 (2)	0.0340 (15)
C15	0.9413 (5)	−0.0561 (5)	0.0826 (2)	0.0359 (16)
H15	0.9962	−0.0092	0.0723	0.043*
C16	0.8510 (5)	−0.0761 (5)	0.0583 (2)	0.0361 (16)
C17	0.7708 (5)	−0.1491 (5)	0.0727 (2)	0.0406 (17)
H17	0.7100	−0.1646	0.0560	0.049*
C18	0.7804 (5)	−0.1982 (5)	0.1111 (2)	0.0352 (16)
C19	0.8699 (5)	−0.1780 (5)	0.1381 (2)	0.0329 (15)

	U11	U22	U33	U12	U13	U23
I1	0.0476 (3)	0.1081 (5)	0.0458 (3)	0.0294 (3)	0.0003 (3)	−0.0007 (3)
I2	0.0508 (3)	0.0558 (3)	0.0292 (2)	0.0012 (2)	−0.0041 (2)	−0.0020 (2)
I3	0.0643 (3)	0.0714 (4)	0.0516 (4)	0.0043 (2)	−0.0106 (3)	0.0231 (3)
I4	0.0551 (3)	0.0626 (3)	0.0631 (4)	−0.0240 (2)	−0.0120 (3)	0.0108 (3)
O1	0.041 (3)	0.078 (3)	0.031 (3)	0.007 (2)	−0.005 (2)	−0.010 (3)
O2	0.049 (3)	0.056 (3)	0.037 (3)	−0.012 (2)	−0.002 (2)	0.005 (2)
N1	0.038 (3)	0.053 (4)	0.035 (4)	−0.002 (3)	0.009 (3)	−0.007 (3)
N2	0.044 (3)	0.055 (4)	0.027 (4)	0.000 (3)	−0.002 (3)	−0.008 (3)
C1	0.030 (4)	0.043 (4)	0.028 (4)	−0.009 (3)	0.005 (3)	0.003 (3)
C2	0.029 (4)	0.052 (4)	0.033 (4)	−0.001 (3)	0.002 (3)	0.002 (3)
C3	0.044 (4)	0.034 (4)	0.032 (4)	−0.004 (3)	0.006 (3)	−0.004 (3)
C4	0.042 (4)	0.037 (4)	0.022 (4)	−0.006 (3)	0.006 (3)	0.005 (3)
C5	0.030 (3)	0.043 (4)	0.027 (4)	−0.002 (3)	0.004 (3)	0.007 (3)
C6	0.039 (4)	0.032 (4)	0.023 (4)	−0.001 (3)	0.006 (3)	0.000 (3)
C7	0.047 (4)	0.034 (4)	0.030 (4)	−0.002 (3)	0.004 (3)	−0.005 (3)
C8	0.047 (4)	0.053 (4)	0.031 (4)	−0.001 (3)	0.002 (3)	−0.009 (4)
C9	0.038 (4)	0.050 (4)	0.027 (4)	−0.002 (3)	−0.002 (3)	−0.009 (3)
C10	0.046 (5)	0.103 (7)	0.051 (6)	−0.016 (4)	−0.008 (4)	−0.033 (5)
C11	0.069 (5)	0.054 (5)	0.038 (5)	0.002 (4)	0.008 (4)	0.001 (4)
C12	0.030 (4)	0.066 (5)	0.032 (4)	−0.003 (3)	−0.002 (3)	−0.011 (4)
C13	0.036 (4)	0.043 (4)	0.038 (5)	0.003 (3)	0.003 (3)	−0.016 (4)
C14	0.034 (4)	0.038 (4)	0.030 (4)	−0.002 (3)	−0.002 (3)	−0.003 (3)
C15	0.040 (4)	0.032 (4)	0.036 (4)	0.001 (3)	0.005 (3)	−0.001 (3)
C16	0.039 (4)	0.034 (4)	0.035 (4)	0.010 (3)	−0.002 (3)	0.000 (3)
C17	0.035 (4)	0.044 (4)	0.043 (5)	0.000 (3)	−0.009 (3)	−0.002 (4)
C18	0.037 (4)	0.031 (4)	0.038 (4)	−0.007 (3)	0.000 (3)	−0.005 (3)
C19	0.040 (4)	0.024 (4)	0.034 (4)	0.002 (3)	0.005 (3)	−0.004 (3)

I1—C2	2.091 (6)	C8—C9	1.550 (8)
I2—C4	2.098 (6)	C8—H8A	0.9700
I3—C16	2.081 (6)	C8—H8B	0.9700
I4—C18	2.090 (6)	C9—C11	1.522 (8)
O1—C1	1.301 (7)	C9—C10	1.526 (8)
O1—H1	0.8203	C9—C12	1.530 (8)
O2—C19	1.312 (7)	C10—H10A	0.9600
O2—H2	0.8201	C10—H10B	0.9600
N1—C7	1.278 (8)	C10—H10C	0.9600
N1—C8	1.452 (7)	C11—H11A	0.9600
N1—H1A	0.7184	C11—H11B	0.9600
N2—C13	1.259 (8)	C11—H11C	0.9600
N2—C12	1.474 (7)	C12—H12A	0.9700
N2—H1B	0.8984	C12—H12B	0.9700
C1—C2	1.416 (8)	C13—C14	1.452 (8)
C1—C6	1.426 (8)	C13—H13	0.9300
C2—C3	1.376 (8)	C14—C15	1.388 (8)
C3—C4	1.403 (8)	C14—C19	1.436 (8)
C3—H3	0.9300	C15—C16	1.367 (8)
C4—C5	1.364 (8)	C15—H15	0.9300
C5—C6	1.396 (8)	C16—C17	1.383 (8)
C5—H5	0.9300	C17—C18	1.359 (8)
C6—C7	1.427 (8)	C17—H17	0.9300
C7—H7	0.9300	C18—C19	1.408 (8)
C1—O1—H1	110.0	C12—C9—C8	108.6 (5)
C19—O2—H2	109.8	C9—C10—H10A	109.5
C7—N1—C8	122.8 (6)	C9—C10—H10B	109.5
C7—N1—H1A	115.1	H10A—C10—H10B	109.5
C8—N1—H1A	121.8	C9—C10—H10C	109.5
C13—N2—C12	121.2 (6)	H10A—C10—H10C	109.5
C13—N2—H1B	129.4	H10B—C10—H10C	109.5
C12—N2—H1B	108.7	C9—C11—H11A	109.5
O1—C1—C2	120.8 (6)	C9—C11—H11B	109.5
O1—C1—C6	122.4 (6)	H11A—C11—H11B	109.5
C2—C1—C6	116.7 (6)	C9—C11—H11C	109.5
C3—C2—C1	122.2 (6)	H11A—C11—H11C	109.5
C3—C2—I1	119.6 (5)	H11B—C11—H11C	109.5
C1—C2—I1	118.2 (5)	N2—C12—C9	112.8 (5)
C2—C3—C4	119.5 (6)	N2—C12—H12A	109.0
C2—C3—H3	120.2	C9—C12—H12A	109.0
C4—C3—H3	120.2	N2—C12—H12B	109.0
C5—C4—C3	120.0 (6)	C9—C12—H12B	109.0
C5—C4—I2	121.6 (5)	H12A—C12—H12B	107.8
C3—C4—I2	118.4 (4)	N2—C13—C14	122.8 (6)
C4—C5—C6	121.3 (6)	N2—C13—H13	118.6
C4—C5—H5	119.3	C14—C13—H13	118.6
C6—C5—H5	119.3	C15—C14—C19	119.4 (6)
C5—C6—C1	120.1 (5)	C15—C14—C13	121.8 (6)
C5—C6—C7	120.9 (6)	C19—C14—C13	118.8 (6)
C1—C6—C7	119.0 (6)	C16—C15—C14	122.0 (6)
N1—C7—C6	121.5 (6)	C16—C15—H15	119.0
N1—C7—H7	119.2	C14—C15—H15	119.0
C6—C7—H7	119.2	C15—C16—C17	119.4 (6)
N1—C8—C9	113.2 (5)	C15—C16—I3	122.2 (5)
N1—C8—H8A	108.9	C17—C16—I3	118.4 (5)
C9—C8—H8A	108.9	C18—C17—C16	120.2 (6)
N1—C8—H8B	108.9	C18—C17—H17	119.9
C9—C8—H8B	108.9	C16—C17—H17	119.9
H8A—C8—H8B	107.8	C17—C18—C19	122.9 (6)
C11—C9—C10	109.2 (5)	C17—C18—I4	119.6 (5)
C11—C9—C12	110.9 (5)	C19—C18—I4	117.6 (5)
C10—C9—C12	107.3 (5)	O2—C19—C18	122.7 (6)
C11—C9—C8	111.4 (5)	O2—C19—C14	121.2 (6)
C10—C9—C8	109.4 (6)	C18—C19—C14	116.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.72	1.90	2.526 (6)	145
O2—H2···N2	0.82	1.82	2.548 (6)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.72	1.90	2.526 (6)	145
O2—H2⋯N2	0.82	1.82	2.548 (6)	148