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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m63.
Published online 2007 December 6. doi:  10.1107/S1600536807063143
PMCID: PMC2914945

This article has been retractedRetraction in: Acta Crystallogr Sect E Struct Rep Online. 2012 July 01; 68(Pt 7): e14    See also: PMC Retraction Policy

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

Abstract

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 [triangle]); Chen et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-00m63-scheme1.jpg

Experimental

Crystal data

  • [Fe2(C16H12Br2N2O2)2O]
  • M r = 975.89
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-00m63-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.147
  • S = 1.00
  • 3182 reflections
  • 213 parameters
  • H-atom parameters constraned
  • Δρmax = 1.05 e Å−3
  • Δρmin = −0.70 e Å−3

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

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063143/hb2647Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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%.

Refinement

The H atoms were included in calculated positions (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Figures

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.

Crystal data

[Fe2(C16H12Br2N2O2)2O]F000 = 1904
Mr = 975.89Dx = 1.859 Mg m3
Orthorhombic, PccaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2a 2acCell parameters from 3182 reflections
a = 21.094 (2) Åθ = 3.0–25.4º
b = 13.8168 (18) ŵ = 5.46 mm1
c = 11.9619 (12) ÅT = 293 (2) K
V = 3486.3 (7) Å3Block, brown
Z = 40.43 × 0.28 × 0.22 mm

Data collection

Bruker APEX II CCD diffractometer3182 independent reflections
Radiation source: fine-focus sealed tube2257 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.049
T = 293(2) Kθmax = 25.4º
[var phi] and ω scansθmin = 3.0º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −25→25
Tmin = 0.202, Tmax = 0.380k = −16→16
11548 measured reflectionsl = 0→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.147  w = 1/[σ2(Fo2) + (0.077P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.018
3182 reflectionsΔρmax = 1.05 e Å3
213 parametersΔρmin = −0.70 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
Fe10.07194 (4)0.12987 (5)0.31467 (6)0.0342 (2)
Br10.10796 (4)0.66034 (5)0.24478 (7)0.0776 (3)
Br20.28253 (3)−0.28115 (5)0.48690 (6)0.0663 (3)
C10.0405 (3)0.3280 (4)0.4134 (4)0.0404 (13)
H10.02300.36700.46870.048*
C20.0734 (3)0.3750 (4)0.3197 (5)0.0392 (12)
C30.1029 (3)0.3259 (4)0.2294 (5)0.0405 (13)
C40.1303 (3)0.3799 (4)0.1413 (5)0.0514 (15)
H40.14770.34770.08030.062*
C50.1316 (3)0.4776 (4)0.1447 (6)0.0574 (17)
H50.15040.51260.08720.069*
C60.1039 (3)0.5260 (4)0.2367 (5)0.0519 (16)
C70.0744 (3)0.4748 (4)0.3235 (5)0.0476 (14)
H70.05570.50770.38290.057*
C80.0009 (3)0.1958 (4)0.5204 (5)0.0432 (14)
H8A−0.03820.16500.49700.052*
H8B−0.00910.24620.57410.052*
C90.0461 (3)0.1213 (4)0.5721 (4)0.0423 (13)
H9A0.07650.15340.62020.051*
H9B0.02240.07510.61660.051*
C100.1146 (3)−0.0002 (4)0.5091 (4)0.0385 (13)
H100.1140−0.01810.58400.046*
C110.1561 (3)−0.0556 (4)0.4331 (4)0.0370 (12)
C120.1643 (3)−0.0340 (3)0.3168 (4)0.0356 (11)
C130.2041 (3)−0.0949 (4)0.2516 (5)0.0410 (13)
H130.2075−0.08490.17490.049*
C140.2370 (3)−0.1675 (4)0.3005 (5)0.0474 (14)
H140.2640−0.20580.25760.057*
C150.2308 (3)−0.1858 (4)0.4169 (5)0.0463 (14)
C160.1901 (3)−0.1313 (4)0.4831 (5)0.0428 (14)
H160.1856−0.14480.55890.051*
N10.0797 (2)0.0703 (3)0.4793 (4)0.0363 (10)
N20.0348 (2)0.2370 (3)0.4227 (4)0.0360 (10)
O10.10571 (18)0.2321 (3)0.2223 (3)0.0435 (9)
O20.13721 (19)0.0409 (3)0.2686 (3)0.0414 (9)
O30.00000.0842 (4)0.25000.0388 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0433 (5)0.0267 (4)0.0327 (4)0.0006 (3)0.0003 (3)−0.0002 (3)
Br10.1084 (7)0.0293 (4)0.0950 (6)−0.0024 (3)0.0277 (5)0.0093 (4)
Br20.0660 (5)0.0586 (5)0.0744 (5)0.0225 (3)0.0087 (4)0.0251 (4)
C10.044 (3)0.036 (3)0.041 (3)0.001 (2)0.001 (3)−0.007 (2)
C20.042 (3)0.031 (3)0.045 (3)0.000 (2)−0.001 (3)0.002 (2)
C30.042 (3)0.037 (3)0.043 (3)−0.003 (2)0.003 (3)0.001 (3)
C40.062 (4)0.042 (3)0.050 (3)0.001 (3)0.007 (3)0.011 (3)
C50.067 (4)0.040 (3)0.066 (4)−0.007 (3)0.013 (3)0.009 (3)
C60.064 (4)0.029 (3)0.064 (4)−0.004 (3)0.005 (3)0.012 (3)
C70.051 (4)0.032 (3)0.060 (4)0.001 (3)0.004 (3)0.002 (3)
C80.050 (4)0.038 (3)0.042 (3)0.001 (3)0.011 (3)0.004 (3)
C90.052 (3)0.041 (3)0.034 (3)−0.001 (3)0.010 (3)0.001 (2)
C100.051 (4)0.030 (3)0.035 (3)−0.006 (2)−0.001 (3)0.001 (2)
C110.041 (3)0.030 (3)0.041 (3)−0.001 (2)−0.003 (2)0.003 (2)
C120.043 (3)0.027 (2)0.037 (3)−0.001 (2)0.001 (2)−0.001 (2)
C130.049 (3)0.034 (3)0.041 (3)0.003 (2)0.001 (3)0.001 (2)
C140.048 (3)0.038 (3)0.057 (4)0.005 (3)0.008 (3)0.002 (3)
C150.044 (3)0.043 (3)0.052 (3)0.003 (3)0.005 (3)0.016 (3)
C160.047 (3)0.038 (3)0.043 (3)−0.001 (3)0.002 (3)0.010 (3)
N10.045 (3)0.029 (2)0.035 (2)0.0013 (19)0.002 (2)−0.0019 (19)
N20.042 (3)0.025 (2)0.041 (2)−0.0042 (18)0.005 (2)0.0019 (19)
O10.055 (3)0.030 (2)0.045 (2)−0.0026 (17)0.0101 (19)0.0019 (17)
O20.056 (2)0.034 (2)0.0346 (18)0.0113 (17)−0.0020 (18)0.0024 (16)
O30.045 (3)0.028 (3)0.043 (3)0.000−0.009 (2)0.000

Geometric parameters (Å, °)

Fe1—O31.8162 (18)C8—C91.533 (8)
Fe1—O21.926 (4)C8—H8A0.9700
Fe1—O11.930 (4)C8—H8B0.9700
Fe1—N22.116 (4)C9—N11.493 (7)
Fe1—N12.141 (4)C9—H9A0.9700
Br1—C61.861 (6)C9—H9B0.9700
Br2—C151.905 (6)C10—N11.272 (7)
C1—N21.268 (6)C10—C111.474 (7)
C1—C21.470 (7)C10—H100.9300
C1—H10.9300C11—C161.404 (7)
C2—C71.380 (7)C11—C121.434 (7)
C2—C31.419 (8)C12—O21.314 (6)
C3—O11.299 (6)C12—C131.422 (7)
C3—C41.414 (8)C13—C141.354 (8)
C4—C51.351 (8)C13—H130.9300
C4—H40.9300C14—C151.421 (8)
C5—C61.414 (9)C14—H140.9300
C5—H50.9300C15—C161.388 (8)
C6—C71.402 (8)C16—H160.9300
C7—H70.9300O3—Fe1i1.8162 (18)
C8—N21.483 (7)
O3—Fe1—O2104.71 (16)N1—C9—C8108.2 (4)
O3—Fe1—O1108.58 (16)N1—C9—H9A110.1
O2—Fe1—O192.29 (16)C8—C9—H9A110.1
O3—Fe1—N2101.14 (16)N1—C9—H9B110.1
O2—Fe1—N2152.39 (17)C8—C9—H9B110.1
O1—Fe1—N288.51 (16)H9A—C9—H9B108.4
O3—Fe1—N1108.78 (15)N1—C10—C11124.6 (5)
O2—Fe1—N187.89 (16)N1—C10—H10117.7
O1—Fe1—N1141.27 (17)C11—C10—H10117.7
N2—Fe1—N174.66 (16)C16—C11—C12120.4 (5)
N2—C1—C2123.4 (5)C16—C11—C10115.4 (5)
N2—C1—H1118.3C12—C11—C10124.2 (5)
C2—C1—H1118.3O2—C12—C13118.8 (4)
C7—C2—C3119.8 (5)O2—C12—C11122.4 (5)
C7—C2—C1115.0 (5)C13—C12—C11118.7 (5)
C3—C2—C1125.1 (5)C14—C13—C12120.3 (5)
O1—C3—C2123.1 (5)C14—C13—H13119.8
O1—C3—C4117.3 (5)C12—C13—H13119.8
C2—C3—C4119.6 (5)C13—C14—C15120.5 (5)
C5—C4—C3120.9 (6)C13—C14—H14119.8
C5—C4—H4119.6C15—C14—H14119.8
C3—C4—H4119.6C16—C15—C14121.3 (5)
C4—C5—C6119.2 (6)C16—C15—Br2118.6 (4)
C4—C5—H5120.4C14—C15—Br2120.0 (4)
C6—C5—H5120.4C15—C16—C11118.5 (5)
C7—C6—C5121.4 (5)C15—C16—H16120.7
C7—C6—Br1119.0 (5)C11—C16—H16120.7
C5—C6—Br1119.5 (4)C10—N1—C9115.4 (4)
C2—C7—C6119.1 (6)C10—N1—Fe1126.6 (4)
C2—C7—H7120.5C9—N1—Fe1117.8 (3)
C6—C7—H7120.5C1—N2—C8119.7 (5)
N2—C8—C9106.0 (4)C1—N2—Fe1127.2 (4)
N2—C8—H8A110.5C8—N2—Fe1113.0 (3)
C9—C8—H8A110.5C3—O1—Fe1132.5 (3)
N2—C8—H8B110.5C12—O2—Fe1133.4 (3)
C9—C8—H8B110.5Fe1i—O3—Fe1139.4 (3)
H8A—C8—H8B108.7

Symmetry codes: (i) −x, y, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2647).

References

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

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