2-((E)-{3-[(E)-2-Hy­droxy-3,5-diiodo­benzyl­idene­amino]-2,2-dimethyl­prop­yl}imino­meth­yl)-4,6-diiodo­phenol

Kargar, H.; Kia, R.; Shakarami, T.; Tahir, M.N.

doi:10.1107/S1600536812003704

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o564

doi:10.1107/S1600536812003704

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2-((E)-{3-[(E)-2-Hydroxy-3,5-diiodobenzylideneamino]-2,2-dimethylpropyl}iminomethyl)-4,6-diiodophenol

Hadi Kargar,^a Reza Kia,^b,^c ^* Tayebeh Shakarami ^a and Muhammad Nawaz Tahir ^d ^*

^aDepartment of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, I. R. of Iran, ^bX-ray Crystallography Laboratory, 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: zsrkk@yahoo.com, dmntahir_uos@yahoo.com

(Received 6 January 2012; accepted 27 January 2012; online 4 February 2012)

The asymmetric unit of the title compound, C₁₉H₁₈I₄N₂O₂, comprises a potentially tetradentate 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)°. Intramolecular 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 intermolecular π–π interactions [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_r = 813.95
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.079
S = 1.00
5471 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 1.11 e Å⁻³
Δρ_min = −0.94 e Å⁻³

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

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812003704/vm2150sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812003704/vm2150Isup3.cml

checkCIF report

Comment top

In continuation of our work on the crystal structure of Schiff base ligands (Kargar et al., 2011, 2012; Kia et al., 2010), we determined the X-ray structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises a potentially tetradentate Schiff base ligand. In the crystal structure the phenolic H atoms are disordered over a second position on the Schiff base N atoms. The bond lengths and angles are within the normal ranges (Allen et al., 1987) and are comparable to related structures (Kargar et al., 2011, 2012; Kia et al., 2010).

The intramolecular N—H···O and O—H···N hydrogen bonds (Table 1) make S(6) ring motifs (Bernstein et al., 1995). The dihedral angle between the benzene rings is 73.3 (3)°. Short I(1)···I(2)ⁱ [3.8919 (7) Å; (i) 1/2 + x, 1/2 - y, 1 - z ] and I4···Cg2ⁱⁱ [3.911 (2) Å; (ii) 3/2 - x, -1/2 + y, z; Cg2 is the centroid of the C14–C19 ring] contacts are present in the crystal structure (Fig. 2). The crystal structure is further stabilized by the intermolecular π–π interaction [Cg1···Cg2ⁱ = 3.827 (3)Å; (i) 2 - x, 1/2 + y, 1/2 - z; Cg1 and Cg2 are the centroids of the C1–C6 and C14–C19 benzene rings].

Related literature top

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 top

The title compound was synthesized by adding 3,5-diiodo-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 half an hour. The resultant solution was filtered. Yellow single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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. ORTEP plot of the title compound, showing 40% probability displacement ellipsoids and atomic numbering. The dashed lines show the intramolecular hydrogen bonds. The open bonds show the minor disordered components.
	Fig. 2. Packing diagram of the title compound viewed down the b-axis showing the short intermolecular I···I, I···Cg [C144–C19], and Cg [C1–C6]···Cg [C14–C19] contacts (dashed lines). All H atoms were omitted for clarity.

2-((E)-{3-[(E)-2-Hydroxy-3,5-diiodobenzylideneamino]- 2,2-dimethylpropyl}iminomethyl)-4,6-diiodophenol top

Crystal data top

C₁₉H₁₈I₄N₂O₂	F(000) = 2992
M_r = 813.95	D_x = 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

Data collection top

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

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0213P)²] where P = (F_o² + 2F_c²)/3
5471 reflections	(Δ/σ)_max = 0.001
248 parameters	Δρ_max = 1.11 e Å⁻³
0 restraints	Δρ_min = −0.94 e Å⁻³

Crystal data top

C₁₉H₁₈I₄N₂O₂	V = 4588.9 (3) Å³
M_r = 813.95	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.2057 (5) Å	µ = 5.45 mm⁻¹
b = 11.8169 (5) Å	T = 291 K
c = 31.8157 (15) Å	0.18 × 0.12 × 0.08 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5472 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2871 reflections with I > 2σ(I)
T_min = 0.441, T_max = 0.670	R_int = 0.099
39183 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.00	Δρ_max = 1.11 e Å⁻³
5471 reflections	Δρ_min = −0.94 e Å⁻³
248 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	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈I₄N₂O₂
M_r	813.95
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	291
a, b, c (Å)	12.2057 (5), 11.8169 (5), 31.8157 (15)
V (Å³)	4588.9 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.45
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	0.441, 0.670
No. of measured, independent and observed [I > 2σ(I)] reflections	39183, 5472, 2871
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.079, 1.00
No. of reflections	5471
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.11, −0.94

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
N1—H1A···O1	0.72	1.90	2.526 (6)	145
O2—H2···N2	0.82	1.82	2.548 (6)	148

Acknowledgements

HK and TS thank Payame Noor University for the financial support. MNT thanks the 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
Bondi, A. (1964). J. Phys. Chem. 68, 441–452. Web of Science CrossRef CAS Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kargar, H., Kia, R., Abbasian, S. & Tahir, M. N. (2012). Acta Cryst. E68, o142. Web of Science CSD CrossRef IUCr Journals 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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Volume 68| Part 3| March 2012| Page o564

doi:10.1107/S1600536812003704

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

2-((E)-{3-[(E)-2-Hy­dr­oxy-3,5-di­iodo­benzyl­­idene­amino]-2,2-di­methyl­prop­yl}imino­meth­yl)-4,6-di­iodo­phenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-((E)-{3-[(E)-2-Hydroxy-3,5-diiodobenzylideneamino]-2,2-dimethylpropyl}iminomethyl)-4,6-diiodophenol