μ-Oxido-bis­({4,4′-dibromo-2,2′-ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato}iron(III))

Meng, Q.; Wang, L.; Liu, Y.; Pang, Y.

doi:10.1107/S1600536807063143

metal-organic compounds

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Volume 64| Part 1| January 2008| Page m63

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RETRACTED ARTICLE

This article has been retracted. To view the retraction notice, click here.

Retracted: μ-Oxido-bis({4,4′-dibromo-2,2′-ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}iron(III))

Qingguo Meng,^a ^* Lintong Wang,^a Yanzhen Liu ^a and Yan Pang ^a

^aCollege of Chemistry and Chemical Engineering, Weifang University, Weifang, 261061, People's Republic of China
^*Correspondence e-mail: qgmeng_weifang@yahoo.cn

(Received 8 November 2007; accepted 25 November 2007; online 6 December 2007)

In the title compound, [Fe₂(C₁₆H₁₂Br₂N₂O₂)₂O], the complete molecule is generated by twofold symmetry, with the bridging O atom, which links the iron centres, lying on the roatation rotation axis. The Fe(III) ion is chelated by the N,N,O,O-tetradentate Schiff base dianion, resulting in an FeN₂O₃ square-based pyramid, with the two N atoms in the basal plane.

Related literature

For related literature, see: Karacan & Somer (2004 ); Chen et al. (2006 ).

Experimental

Crystal data

[Fe₂(C₁₆H₁₂Br₂N₂O₂)₂O]
M_r = 975.89
Orthorhombic, P c c a
a = 21.094 (2) Å
b = 13.8168 (18) Å
c = 11.9619 (12) Å
V = 3486.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 5.46 mm⁻¹
T = 293 (2) K
0.43 × 0.28 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.202, T_max = 0.380 (expected range = 0.160–0.301)
11548 measured reflections
3182 independent reflections
2257 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.147
S = 1.00
3182 reflections
213 parameters
H-atom parameters constraned
Δρ_max = 1.05 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Fe1—O3	1.8162 (18)
Fe1—O2	1.926 (4)
Fe1—O1	1.930 (4)
Fe1—N2	2.116 (4)
Fe1—N1	2.141 (4)

Fe1ⁱ—O3—Fe1	139.4 (3)
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807063143/hb2647sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063143/hb2647Isup2.hkl

checkCIF report

Comment top

Recently, Schiff base ligands, especially flexible symmetrical or unsymmetrical Schiff base ligands and their hydrogenated derivatives have been widely employed to assembly alkoxo- or phenoxo-bridged manganese clusters and polymers with novel topological structures and interesting magnetic, catalysis and photochemical properties. (Karacan & Somer, 2004; Chen et al., 2006). In this paper, we report the structure of the title compound, (I).

As shown in Fig. 1, the Fe(III) ion in (I) is chelated by the dianionic Schiff base ligand in a tetradentate N,N,O,O coordination in an approximately square planar arrangement. An oxo ligand (site symmetry 2) caps the FeN₂O₂ grouping to result in a square based pyramid. The oxo ligand also bridges to a second, crystallographically generated Fe atom. The Fe—O capping distance is much shorter than the other bonds (Table 1). The Fe···Feⁱ (i = -x, y, 1/2 - z) distance is 3.4066 (12) %A.

Related literature top

For related literature, see: Karacan & Somer (2004); Chen et al. (2006).

Experimental top

A mixture of iron(III) chloride (1 mmol) and N,N'-bis(2-hydroxy-5-bromobenzyl)ethylenediamine (1 mmol) in 20 ml me thanol was refluxed for two hours. The above cooled solution was filterated and the filtrate was evaporated naturally at room temperature. Two days later, brown blocks of (I) were obtained with a yield of 32%. Anal. Calc. for C₃₂H₂₄Br₄Fe₂N₄O₅: C 39.34, H 2.46, N 5.74%; Found: C 39.32, H 2.48, N 5.69%.

Structure description top

For related literature, see: Karacan & Somer (2004); Chen et al. (2006).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

Fig. 1. The molecular structure of (I), drawn with 50% probability displacement ellipsoids for the non-hydrogen atoms. Symmetry code: (i) -x, y, 1/2 - z.

µ-Oxido-bis({4,4'-dibromo-2,2'-ethane-1,2- diylbis(nitrilomethylidyne)]diphenolato}iron(III)) top

Crystal data top

[Fe₂(C₁₆H₁₂Br₂N₂O₂)₂O]	F(000) = 1904
M_r = 975.89	D_x = 1.859 Mg m⁻³
Orthorhombic, Pcca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2ac	Cell parameters from 3182 reflections
a = 21.094 (2) Å	θ = 3.0–25.4°
b = 13.8168 (18) Å	µ = 5.46 mm⁻¹
c = 11.9619 (12) Å	T = 293 K
V = 3486.3 (7) Å³	Block, brown
Z = 4	0.43 × 0.28 × 0.22 mm

Data collection top

Bruker APEX II CCD diffractometer	3182 independent reflections
Radiation source: fine-focus sealed tube	2257 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
φ and ω scans	θ_max = 25.4°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −25→25
T_min = 0.202, T_max = 0.380	k = −16→16
11548 measured reflections	l = 0→14

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.077P)²] where P = (F_o² + 2F_c²)/3
3182 reflections	(Δ/σ)_max = 0.018
213 parameters	Δρ_max = 1.05 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

[Fe₂(C₁₆H₁₂Br₂N₂O₂)₂O]	V = 3486.3 (7) Å³
M_r = 975.89	Z = 4
Orthorhombic, Pcca	Mo Kα radiation
a = 21.094 (2) Å	µ = 5.46 mm⁻¹
b = 13.8168 (18) Å	T = 293 K
c = 11.9619 (12) Å	0.43 × 0.28 × 0.22 mm

Data collection top

Bruker APEX II CCD diffractometer	3182 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2257 reflections with I > 2σ(I)
T_min = 0.202, T_max = 0.380	R_int = 0.049
11548 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.00	Δρ_max = 1.05 e Å⁻³
3182 reflections	Δρ_min = −0.70 e Å⁻³
213 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Fe1	0.07194 (4)	0.12987 (5)	0.31467 (6)	0.0342 (2)
Br1	0.10796 (4)	0.66034 (5)	0.24478 (7)	0.0776 (3)
Br2	0.28253 (3)	−0.28115 (5)	0.48690 (6)	0.0663 (3)
C1	0.0405 (3)	0.3280 (4)	0.4134 (4)	0.0404 (13)
H1	0.0230	0.3670	0.4687	0.048*
C2	0.0734 (3)	0.3750 (4)	0.3197 (5)	0.0392 (12)
C3	0.1029 (3)	0.3259 (4)	0.2294 (5)	0.0405 (13)
C4	0.1303 (3)	0.3799 (4)	0.1413 (5)	0.0514 (15)
H4	0.1477	0.3477	0.0803	0.062*
C5	0.1316 (3)	0.4776 (4)	0.1447 (6)	0.0574 (17)
H5	0.1504	0.5126	0.0872	0.069*
C6	0.1039 (3)	0.5260 (4)	0.2367 (5)	0.0519 (16)
C7	0.0744 (3)	0.4748 (4)	0.3235 (5)	0.0476 (14)
H7	0.0557	0.5077	0.3829	0.057*
C8	0.0009 (3)	0.1958 (4)	0.5204 (5)	0.0432 (14)
H8A	−0.0382	0.1650	0.4970	0.052*
H8B	−0.0091	0.2462	0.5741	0.052*
C9	0.0461 (3)	0.1213 (4)	0.5721 (4)	0.0423 (13)
H9A	0.0765	0.1534	0.6202	0.051*
H9B	0.0224	0.0751	0.6166	0.051*
C10	0.1146 (3)	−0.0002 (4)	0.5091 (4)	0.0385 (13)
H10	0.1140	−0.0181	0.5840	0.046*
C11	0.1561 (3)	−0.0556 (4)	0.4331 (4)	0.0370 (12)
C12	0.1643 (3)	−0.0340 (3)	0.3168 (4)	0.0356 (11)
C13	0.2041 (3)	−0.0949 (4)	0.2516 (5)	0.0410 (13)
H13	0.2075	−0.0849	0.1749	0.049*
C14	0.2370 (3)	−0.1675 (4)	0.3005 (5)	0.0474 (14)
H14	0.2640	−0.2058	0.2576	0.057*
C15	0.2308 (3)	−0.1858 (4)	0.4169 (5)	0.0463 (14)
C16	0.1901 (3)	−0.1313 (4)	0.4831 (5)	0.0428 (14)
H16	0.1856	−0.1448	0.5589	0.051*
N1	0.0797 (2)	0.0703 (3)	0.4793 (4)	0.0363 (10)
N2	0.0348 (2)	0.2370 (3)	0.4227 (4)	0.0360 (10)
O1	0.10571 (18)	0.2321 (3)	0.2223 (3)	0.0435 (9)
O2	0.13721 (19)	0.0409 (3)	0.2686 (3)	0.0414 (9)
O3	0.0000	0.0842 (4)	0.2500	0.0388 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0433 (5)	0.0267 (4)	0.0327 (4)	0.0006 (3)	0.0003 (3)	−0.0002 (3)
Br1	0.1084 (7)	0.0293 (4)	0.0950 (6)	−0.0024 (3)	0.0277 (5)	0.0093 (4)
Br2	0.0660 (5)	0.0586 (5)	0.0744 (5)	0.0225 (3)	0.0087 (4)	0.0251 (4)
C1	0.044 (3)	0.036 (3)	0.041 (3)	0.001 (2)	0.001 (3)	−0.007 (2)
C2	0.042 (3)	0.031 (3)	0.045 (3)	0.000 (2)	−0.001 (3)	0.002 (2)
C3	0.042 (3)	0.037 (3)	0.043 (3)	−0.003 (2)	0.003 (3)	0.001 (3)
C4	0.062 (4)	0.042 (3)	0.050 (3)	0.001 (3)	0.007 (3)	0.011 (3)
C5	0.067 (4)	0.040 (3)	0.066 (4)	−0.007 (3)	0.013 (3)	0.009 (3)
C6	0.064 (4)	0.029 (3)	0.064 (4)	−0.004 (3)	0.005 (3)	0.012 (3)
C7	0.051 (4)	0.032 (3)	0.060 (4)	0.001 (3)	0.004 (3)	0.002 (3)
C8	0.050 (4)	0.038 (3)	0.042 (3)	0.001 (3)	0.011 (3)	0.004 (3)
C9	0.052 (3)	0.041 (3)	0.034 (3)	−0.001 (3)	0.010 (3)	0.001 (2)
C10	0.051 (4)	0.030 (3)	0.035 (3)	−0.006 (2)	−0.001 (3)	0.001 (2)
C11	0.041 (3)	0.030 (3)	0.041 (3)	−0.001 (2)	−0.003 (2)	0.003 (2)
C12	0.043 (3)	0.027 (2)	0.037 (3)	−0.001 (2)	0.001 (2)	−0.001 (2)
C13	0.049 (3)	0.034 (3)	0.041 (3)	0.003 (2)	0.001 (3)	0.001 (2)
C14	0.048 (3)	0.038 (3)	0.057 (4)	0.005 (3)	0.008 (3)	0.002 (3)
C15	0.044 (3)	0.043 (3)	0.052 (3)	0.003 (3)	0.005 (3)	0.016 (3)
C16	0.047 (3)	0.038 (3)	0.043 (3)	−0.001 (3)	0.002 (3)	0.010 (3)
N1	0.045 (3)	0.029 (2)	0.035 (2)	0.0013 (19)	0.002 (2)	−0.0019 (19)
N2	0.042 (3)	0.025 (2)	0.041 (2)	−0.0042 (18)	0.005 (2)	0.0019 (19)
O1	0.055 (3)	0.030 (2)	0.045 (2)	−0.0026 (17)	0.0101 (19)	0.0019 (17)
O2	0.056 (2)	0.034 (2)	0.0346 (18)	0.0113 (17)	−0.0020 (18)	0.0024 (16)
O3	0.045 (3)	0.028 (3)	0.043 (3)	0.000	−0.009 (2)	0.000

Geometric parameters (Å, º) top

Fe1—O3	1.8162 (18)	C8—C9	1.533 (8)
Fe1—O2	1.926 (4)	C8—H8A	0.9700
Fe1—O1	1.930 (4)	C8—H8B	0.9700
Fe1—N2	2.116 (4)	C9—N1	1.493 (7)
Fe1—N1	2.141 (4)	C9—H9A	0.9700
Br1—C6	1.861 (6)	C9—H9B	0.9700
Br2—C15	1.905 (6)	C10—N1	1.272 (7)
C1—N2	1.268 (6)	C10—C11	1.474 (7)
C1—C2	1.470 (7)	C10—H10	0.9300
C1—H1	0.9300	C11—C16	1.404 (7)
C2—C7	1.380 (7)	C11—C12	1.434 (7)
C2—C3	1.419 (8)	C12—O2	1.314 (6)
C3—O1	1.299 (6)	C12—C13	1.422 (7)
C3—C4	1.414 (8)	C13—C14	1.354 (8)
C4—C5	1.351 (8)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.421 (8)
C5—C6	1.414 (9)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.388 (8)
C6—C7	1.402 (8)	C16—H16	0.9300
C7—H7	0.9300	O3—Fe1ⁱ	1.8162 (18)
C8—N2	1.483 (7)

O3—Fe1—O2	104.71 (16)	N1—C9—C8	108.2 (4)
O3—Fe1—O1	108.58 (16)	N1—C9—H9A	110.1
O2—Fe1—O1	92.29 (16)	C8—C9—H9A	110.1
O3—Fe1—N2	101.14 (16)	N1—C9—H9B	110.1
O2—Fe1—N2	152.39 (17)	C8—C9—H9B	110.1
O1—Fe1—N2	88.51 (16)	H9A—C9—H9B	108.4
O3—Fe1—N1	108.78 (15)	N1—C10—C11	124.6 (5)
O2—Fe1—N1	87.89 (16)	N1—C10—H10	117.7
O1—Fe1—N1	141.27 (17)	C11—C10—H10	117.7
N2—Fe1—N1	74.66 (16)	C16—C11—C12	120.4 (5)
N2—C1—C2	123.4 (5)	C16—C11—C10	115.4 (5)
N2—C1—H1	118.3	C12—C11—C10	124.2 (5)
C2—C1—H1	118.3	O2—C12—C13	118.8 (4)
C7—C2—C3	119.8 (5)	O2—C12—C11	122.4 (5)
C7—C2—C1	115.0 (5)	C13—C12—C11	118.7 (5)
C3—C2—C1	125.1 (5)	C14—C13—C12	120.3 (5)
O1—C3—C2	123.1 (5)	C14—C13—H13	119.8
O1—C3—C4	117.3 (5)	C12—C13—H13	119.8
C2—C3—C4	119.6 (5)	C13—C14—C15	120.5 (5)
C5—C4—C3	120.9 (6)	C13—C14—H14	119.8
C5—C4—H4	119.6	C15—C14—H14	119.8
C3—C4—H4	119.6	C16—C15—C14	121.3 (5)
C4—C5—C6	119.2 (6)	C16—C15—Br2	118.6 (4)
C4—C5—H5	120.4	C14—C15—Br2	120.0 (4)
C6—C5—H5	120.4	C15—C16—C11	118.5 (5)
C7—C6—C5	121.4 (5)	C15—C16—H16	120.7
C7—C6—Br1	119.0 (5)	C11—C16—H16	120.7
C5—C6—Br1	119.5 (4)	C10—N1—C9	115.4 (4)
C2—C7—C6	119.1 (6)	C10—N1—Fe1	126.6 (4)
C2—C7—H7	120.5	C9—N1—Fe1	117.8 (3)
C6—C7—H7	120.5	C1—N2—C8	119.7 (5)
N2—C8—C9	106.0 (4)	C1—N2—Fe1	127.2 (4)
N2—C8—H8A	110.5	C8—N2—Fe1	113.0 (3)
C9—C8—H8A	110.5	C3—O1—Fe1	132.5 (3)
N2—C8—H8B	110.5	C12—O2—Fe1	133.4 (3)
C9—C8—H8B	110.5	Fe1ⁱ—O3—Fe1	139.4 (3)
H8A—C8—H8B	108.7

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Fe₂(C₁₆H₁₂Br₂N₂O₂)₂O]
M_r	975.89
Crystal system, space group	Orthorhombic, Pcca
Temperature (K)	293
a, b, c (Å)	21.094 (2), 13.8168 (18), 11.9619 (12)
V (Å³)	3486.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.46
Crystal size (mm)	0.43 × 0.28 × 0.22

Data collection
Diffractometer	Bruker APEX II CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.202, 0.380
No. of measured, independent and observed [I > 2σ(I)] reflections	11548, 3182, 2257
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.147, 1.00
No. of reflections	3182
No. of parameters	213
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.05, −0.70

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).

Selected geometric parameters (Å, º) top

Fe1—O3	1.8162 (18)	Fe1—N2	2.116 (4)
Fe1—O2	1.926 (4)	Fe1—N1	2.141 (4)
Fe1—O1	1.930 (4)

Fe1ⁱ—O3—Fe1	139.4 (3)

Symmetry code: (i) −x, y, −z+1/2.

Acknowledgements

The authors thank Liaocheng University for financial support and Professor Jianmin Dou for his help.

References

Bruker (2001). SAINT-Plus and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, P., Fan, B. B., Song, M. G., Jin, C., Ma, J. H. & Li, R. F. (2006). Catal. Commun. 7, 969–973. Web of Science CrossRef CAS Google Scholar
Karacan, M. S. & Somer, G. J. (2004). Photochem. Photobiol. A Chem. 163, 307–310. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar

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

Retracted: μ-Oxido-bis­­({4,4′-di­bromo-2,2′-ethane-1,2-diylbis(nitrilo­methyl­­idyne)]diphenolato}iron(III))

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Retracted: μ-Oxido-bis({4,4′-dibromo-2,2′-ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}iron(III))