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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): m844.
Published online 2008 May 30. doi:  10.1107/S1600536808015559
PMCID: PMC2961607

Bis[(E)-4-chloro-2-(2-furylmethyl­imino­meth­yl)phenolato]iron(II)

Abstract

The Fe atom of the title compound, [Fe(C12H9ClNO2)2], lies on a crystallographic twofold rotation axis. The FeII atom is four-coordinated in a tetra­hedral geometry by the O and N atoms of the two Schiff base ligands. The O atom of the furan substituent in the ligand unit is not involved in coordination to the Fe atom.

Related literature

For related structures, see: Chen & Wang (2006 [triangle]); Chen et al. (2007 [triangle]); Ran et al. (2006 [triangle]); Ye et al. (2007 [triangle]); Zhu et al. (2003 [triangle]).

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Object name is e-64-0m844-scheme1.jpg

Experimental

Crystal data

  • [Fe(C12H9ClNO2)2]
  • M r = 525.15
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m844-efi1.jpg
  • a = 22.550 (4) Å
  • b = 4.6270 (6) Å
  • c = 13.822 (3) Å
  • β = 127.73 (3)°
  • V = 1140.6 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.93 mm−1
  • T = 298 (2) K
  • 0.21 × 0.21 × 0.20 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.829, T max = 0.836
  • 1314 measured reflections
  • 1262 independent reflections
  • 973 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.203
  • S = 1.06
  • 1262 reflections
  • 151 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.60 e Å−3
  • Δρmin = −0.40 e Å−3
  • Absolute structure: Flack (1983 [triangle]), with no Friedel pairs
  • Flack parameter: −0.02 (9)

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [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/S1600536808015559/sj2505sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015559/sj2505Isup2.hkl

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

Acknowledgments

The authors appreciate the generous financial support of this work by the Chinese Funds for Zhicheng Project (No. 2006BAC02A11) and Wuhan Yindao project (No. 20066009138-07).

supplementary crystallographic information

Comment

As part of our ongoing interest in the structure of iron complexes (Zhu et al., 2003), we report herein the crystal structure of the title compound, a new mononuclear iron(II) complex, (I), Fig. 1, derived from the Schiff base ligand 4-chloro-2-[(furan-2-ylmethylimino)methyl]phenol.

Compound (I) possesses crystallographic two-fold symmetry. The FeII atom in (I) is four-coordinate in a tetrahedral geometry, binding to the O and N atoms of two Schiff base ligands. The O atom of the furan substituent in the ligand lies well away from the coordination sphere of the Fe atom. The coordinate bond values (Table 1) are comparable to values observed in other iron(II) complexes (Chen & Wang, 2006; Chen et al., 2007; Ran et al., 2006; Ye et al., 2007).

Experimental

5-Chlorosalicylaldehyde (62.4 mg, 0.2 mmol), furan-2-ylmethylamine (19.4 mg, 0.2 mmol), and FeCl2 (12.6 mg, 0.1 mmol) were dissolved in methanol (30 ml). The mixture was stirred for 30 min at room temperature. The resulting solution was kept still in air for a few days, yielding brown crystals.

Refinement

H atoms were placed in idealized positions and constrained to ride on their parent atoms with C–H distances in the range 0.93–0.97 Å, and with Uiso(H) set at 1.2Ueq(C).

Figures

Fig. 1.
The structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme. Numbered atoms are related to un-numbered atoms by the symmetry code 1-x, y, 1-z.

Crystal data

[Fe(C12H9ClNO2)2]F000 = 536
Mr = 525.15Dx = 1.529 Mg m3
Monoclinic, C2Mo Kα radiation λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 823 reflections
a = 22.550 (4) Åθ = 2.4–26.2º
b = 4.6270 (6) ŵ = 0.93 mm1
c = 13.822 (3) ÅT = 298 (2) K
β = 127.73 (3)ºBlock, brown
V = 1140.6 (4) Å30.21 × 0.21 × 0.20 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer1262 independent reflections
Radiation source: fine-focus sealed tube973 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.035
T = 298(2) Kθmax = 26.0º
ω scansθmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −21→27
Tmin = 0.829, Tmax = 0.836k = −5→0
1314 measured reflectionsl = −17→0

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.060  w = 1/[σ2(Fo2) + (0.1149P)2 + 2.2051P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.203(Δ/σ)max = 0.001
S = 1.06Δρmax = 0.60 e Å3
1262 reflectionsΔρmin = −0.40 e Å3
151 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.011 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 0 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.02 (9)

Special details

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)

xyzUiso*/Ueq
Fe10.50000.5044 (3)0.50000.0419 (6)
Cl10.87863 (17)0.7649 (11)1.0179 (3)0.0929 (13)
N10.5246 (5)0.728 (2)0.6435 (8)0.055 (2)
O10.5933 (4)0.313 (2)0.5865 (7)0.067 (2)
O20.4619 (6)0.600 (3)0.7844 (9)0.102 (4)
C10.6584 (5)0.630 (3)0.7611 (9)0.053 (2)
C20.6554 (5)0.419 (2)0.6848 (9)0.053 (3)
C30.7253 (6)0.309 (3)0.7192 (11)0.069 (3)
H30.72500.16860.67090.083*
C40.7929 (6)0.406 (3)0.8218 (11)0.068 (3)
H40.83770.33170.84290.081*
C50.7933 (6)0.620 (3)0.8943 (10)0.065 (3)
C60.7284 (6)0.737 (3)0.8663 (10)0.070 (3)
H60.73000.88240.91450.084*
C70.5937 (6)0.759 (3)0.7390 (10)0.066 (3)
H70.60210.87860.80030.079*
C80.4677 (6)0.890 (3)0.6455 (11)0.067 (3)
H8A0.49261.03360.71000.080*
H8B0.43290.98820.56810.080*
C90.4259 (6)0.683 (3)0.6671 (10)0.061 (3)
C100.4146 (12)0.427 (6)0.786 (2)0.137 (10)
H100.42420.34980.85600.164*
C110.3509 (10)0.381 (4)0.6710 (18)0.105 (6)
H110.31090.26060.64660.126*
C120.3594 (7)0.555 (4)0.5982 (13)0.087 (5)
H120.32380.57810.51410.104*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0384 (9)0.0462 (11)0.0399 (9)0.0000.0233 (7)0.000
Cl10.0661 (17)0.122 (3)0.0664 (18)−0.012 (2)0.0279 (15)0.017 (2)
N10.062 (5)0.047 (5)0.065 (5)0.000 (5)0.044 (4)−0.005 (4)
O10.065 (4)0.068 (6)0.066 (4)−0.001 (4)0.040 (4)−0.017 (4)
O20.093 (6)0.136 (12)0.089 (6)0.016 (7)0.062 (5)0.022 (7)
C10.052 (5)0.054 (6)0.053 (5)0.001 (5)0.032 (5)0.006 (5)
C20.053 (5)0.050 (8)0.053 (5)0.005 (5)0.031 (5)0.009 (5)
C30.061 (6)0.062 (8)0.088 (8)−0.007 (6)0.048 (6)−0.008 (7)
C40.056 (6)0.070 (9)0.081 (7)0.012 (6)0.043 (6)0.019 (7)
C50.048 (6)0.081 (9)0.055 (6)0.001 (6)0.026 (5)0.013 (6)
C60.071 (7)0.077 (9)0.059 (6)−0.001 (7)0.038 (6)0.010 (7)
C70.074 (7)0.067 (8)0.054 (6)−0.004 (7)0.038 (6)0.002 (6)
C80.070 (7)0.059 (7)0.079 (7)0.019 (6)0.049 (6)0.009 (6)
C90.061 (6)0.067 (8)0.070 (7)0.011 (6)0.048 (6)0.005 (6)
C100.161 (17)0.15 (3)0.199 (19)0.037 (18)0.158 (17)0.06 (2)
C110.112 (12)0.085 (11)0.167 (17)0.000 (11)0.110 (13)−0.004 (13)
C120.080 (8)0.088 (14)0.102 (9)−0.001 (9)0.061 (8)−0.007 (9)

Geometric parameters (Å, °)

Fe1—O11.888 (8)C3—H30.9300
Fe1—O1i1.888 (8)C4—C51.402 (17)
Fe1—N11.992 (8)C4—H40.9300
Fe1—N1i1.992 (8)C5—C61.377 (16)
Cl1—C51.746 (12)C6—H60.9300
N1—C71.294 (13)C7—H70.9300
N1—C81.499 (12)C8—C91.493 (16)
O1—C21.310 (12)C8—H8A0.9700
O2—C101.34 (2)C8—H8B0.9700
O2—C91.352 (14)C9—C121.328 (18)
C1—C21.411 (14)C10—C111.35 (2)
C1—C71.424 (15)C10—H100.9300
C1—C61.429 (15)C11—C121.39 (2)
C2—C31.431 (15)C11—H110.9300
C3—C41.374 (16)C12—H120.9300
O1—Fe1—O1i124.0 (6)C4—C5—Cl1119.4 (9)
O1—Fe1—N195.2 (3)C5—C6—C1118.1 (13)
O1i—Fe1—N1113.5 (3)C5—C6—H6121.0
O1—Fe1—N1i113.5 (3)C1—C6—H6121.0
O1i—Fe1—N1i95.2 (3)N1—C7—C1127.6 (11)
N1—Fe1—N1i117.3 (5)N1—C7—H7116.2
C7—N1—C8115.9 (9)C1—C7—H7116.2
C7—N1—Fe1120.0 (8)C9—C8—N1109.7 (10)
C8—N1—Fe1123.9 (7)C9—C8—H8A109.7
C2—O1—Fe1123.4 (7)N1—C8—H8A109.7
C10—O2—C9106.7 (14)C9—C8—H8B109.7
C2—C1—C7123.7 (10)N1—C8—H8B109.7
C2—C1—C6121.3 (10)H8A—C8—H8B108.2
C7—C1—C6115.0 (11)C12—C9—O2108.5 (12)
O1—C2—C1124.5 (9)C12—C9—C8135.8 (12)
O1—C2—C3118.3 (10)O2—C9—C8115.7 (11)
C1—C2—C3117.3 (9)O2—C10—C11111.3 (16)
C4—C3—C2121.8 (12)O2—C10—H10124.4
C4—C3—H3119.1C11—C10—H10124.4
C2—C3—H3119.1C10—C11—C12103.7 (16)
C3—C4—C5119.1 (10)C10—C11—H11128.2
C3—C4—H4120.5C12—C11—H11128.2
C5—C4—H4120.5C9—C12—C11109.7 (14)
C6—C5—C4122.4 (11)C9—C12—H12125.2
C6—C5—Cl1117.9 (11)C11—C12—H12125.2

Symmetry codes: (i) −x+1, y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2505).

References

  • Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chen, K. & Wang, J.-H. (2006). Acta Cryst. E62, m2305–m2306.
  • Chen, K., Zhang, Y.-L., Feng, M.-Q. & Liu, C.-H. (2007). Acta Cryst. E63, m2033.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Ran, J.-W., Gong, D.-J. & Li, Y.-H. (2006). Acta Cryst. E62, m2668–m2669.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Ye, Y.-H., Han, Y., Chen, T.-T. & Liu, C.-H. (2007). Acta Cryst. E63, m1963.
  • Zhu, H.-L., Xia, D.-S., Zeng, Q.-F., Wang, Z.-G. & Wang, D.-Q. (2003). Acta Cryst. E59, m1020–m1021.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography