supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

sj2502 scheme

Acta Cryst. (2008). E64, m837    [ doi:10.1107/S1600536808015080 ]

Bis[2-(butyliminomethyl)-4-chlorophenolato]iron(II)

D.-S. Xia, W. Chen, L.-L. Jiang and Q.-F. Zeng

Abstract top

In the title compound, [Fe(C11H13ClNO)2], the FeII atom is four-coordinated in a square-planar geometry by the O and N atoms of two 2-(butyliminomethyl)-4-chlorophenolate Schiff base ligands.

Comment top

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 iron(II) complex, (I), Fig. 1, derived from the Schiff base ligand 2-(butyliminomethyl)-4-chlorophenol.

The FeII atom in (I) is four-coordinated by two O and two N atoms from two Schiff base ligands, forming a square-planar geometry. The dihedral angle between the two benzene rings is 8.2 (3) °. The coordinate bond distances and angles (Table 1) are comparable to the values observed in other similar iron(II) complexes (Chen & Wang, 2006; Chen et al., 2007; Ran et al., 2006; Ye et al., 2007).

Related literature top

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

Experimental top

5-Chlorosalicylaldehyde (31.2 mg, 0.2 mmol), butylamine (14.6 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 in an atmosphere of argon. The resulting solution was left in air for a few days, yielding brown crystals.

Refinement top

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) and 1.5Ueq(methyl C).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme.
Bis[2-(butyliminomethyl)-4-chlorophenolato]iron(II) top
Crystal data top
[Fe(C11H13Cl1N1O1)2]Z = 2
Mr = 477.20F000 = 496
Triclinic, P1Dx = 1.414 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 10.059 (2) ÅCell parameters from 2122 reflections
b = 10.100 (2) Åθ = 2.3–24.5º
c = 11.569 (3) ŵ = 0.93 mm−1
α = 97.093 (3)ºT = 298 (2) K
β = 90.800 (2)ºBlock, brown
γ = 105.755 (3)º0.32 × 0.32 × 0.28 mm
V = 1121.2 (4) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer		4174 independent reflections
Radiation source: fine-focus sealed tube3009 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.023
T = 298(2) Kθmax = 25.5º
ω scansθmin = 1.8º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = 0→12
Tmin = 0.755, Tmax = 0.781k = −12→11
4427 measured reflectionsl = −14→14
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.065  w = 1/[σ2(Fo2) + (0.1206P)2 + 0.3449P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.201(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.91 e Å−3
4174 reflectionsΔρmin = −0.80 e Å−3
265 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.027 (4)
Secondary atom site location: difference Fourier map
Crystal data top
[Fe(C11H13Cl1N1O1)2]γ = 105.755 (3)º
Mr = 477.20V = 1121.2 (4) Å3
Triclinic, P1Z = 2
a = 10.059 (2) ÅMo Kα
b = 10.100 (2) ŵ = 0.93 mm−1
c = 11.569 (3) ÅT = 298 (2) K
α = 97.093 (3)º0.32 × 0.32 × 0.28 mm
β = 90.800 (2)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		4174 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3009 reflections with I > 2σ(I)
Tmin = 0.755, Tmax = 0.781Rint = 0.023
4427 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.065265 parameters
wR(F2) = 0.201H-atom parameters constrained
S = 1.06Δρmax = 0.91 e Å−3
4174 reflectionsΔρmin = −0.80 e Å−3
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
xyzUiso*/Ueq
Fe10.88207 (6)0.05266 (6)0.59267 (5)0.0378 (3)
Cl11.28816 (16)0.67927 (15)0.38259 (15)0.0708 (5)
Cl20.43021 (19)−0.54688 (18)0.80626 (17)0.0875 (6)
N11.0140 (4)0.2108 (5)0.6944 (3)0.0510 (10)
N20.7290 (4)−0.0862 (4)0.4948 (4)0.0505 (10)
O10.9611 (4)0.1217 (4)0.4557 (3)0.0585 (9)
O20.8151 (5)−0.0192 (4)0.7305 (3)0.0742 (12)
C11.0932 (5)0.3499 (5)0.5383 (4)0.0489 (12)
C21.0296 (5)0.2505 (5)0.4429 (4)0.0474 (11)
C31.0436 (6)0.2901 (6)0.3317 (5)0.0546 (13)
H30.99900.22700.26830.065*
C41.1218 (6)0.4204 (6)0.3124 (5)0.0554 (13)
H41.13090.44390.23710.067*
C51.1865 (5)0.5153 (5)0.4071 (5)0.0542 (13)
C61.1748 (5)0.4835 (5)0.5187 (5)0.0508 (12)
H61.21950.54840.58100.061*
C71.0854 (5)0.3227 (5)0.6570 (4)0.0500 (12)
H71.13690.39270.71280.060*
C81.0251 (6)0.2141 (6)0.8225 (4)0.0620 (14)
H8A1.11630.27030.85200.074*
H8B1.01370.12070.84100.074*
C90.9166 (7)0.2733 (6)0.8810 (5)0.0685 (16)
H9A0.93170.36820.86520.082*
H9B0.82630.22050.84690.082*
C100.9164 (8)0.2719 (8)1.0105 (5)0.089 (2)
H10A1.00810.31981.04460.107*
H10B0.89470.17661.02680.107*
C110.8128 (9)0.3404 (8)1.0668 (6)0.103 (3)
H11A0.82600.43031.04230.154*
H11B0.82590.35021.15010.154*
H11C0.72070.28421.04360.154*
C120.6426 (5)−0.2250 (5)0.6502 (5)0.0516 (12)
C130.7240 (6)−0.1362 (6)0.7427 (5)0.0597 (14)
C140.7078 (7)−0.1759 (7)0.8555 (6)0.0753 (18)
H140.7590−0.11690.91830.090*
C150.6177 (7)−0.3004 (6)0.8748 (5)0.0718 (17)
H150.6090−0.32530.94970.086*
C160.5405 (6)−0.3874 (6)0.7816 (6)0.0632 (15)
C170.5499 (5)−0.3530 (6)0.6707 (5)0.0571 (13)
H170.4963−0.41260.60930.069*
C180.6473 (5)−0.1940 (5)0.5322 (5)0.0528 (13)
H180.5860−0.25700.47730.063*
C190.7085 (6)−0.0779 (6)0.3698 (4)0.0551 (13)
H19A0.6551−0.16790.33130.066*
H19B0.7976−0.05470.33500.066*
C200.6344 (7)0.0292 (6)0.3507 (5)0.0688 (16)
H20A0.68640.11860.39130.083*
H20B0.54420.00440.38350.083*
C210.6166 (8)0.0414 (8)0.2213 (6)0.084 (2)
H21A0.58210.12120.21490.100*
H21B0.70700.05980.18850.100*
C220.5237 (12)−0.0799 (10)0.1499 (7)0.132 (4)
H22A0.5594−0.15880.15140.198*
H22B0.5178−0.06080.07110.198*
H22C0.4334−0.09930.18080.198*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0373 (4)0.0346 (4)0.0378 (4)0.0053 (3)0.0030 (3)0.0005 (2)
Cl10.0655 (9)0.0538 (8)0.0906 (11)0.0085 (7)0.0047 (8)0.0182 (7)
Cl20.0835 (12)0.0614 (10)0.1079 (13)−0.0007 (8)0.0180 (10)0.0201 (9)
N10.046 (2)0.058 (3)0.047 (2)0.013 (2)0.0061 (18)0.0053 (19)
N20.048 (2)0.045 (2)0.059 (3)0.015 (2)0.0049 (19)0.0032 (19)
O10.064 (2)0.050 (2)0.053 (2)0.0039 (18)0.0052 (17)0.0005 (16)
O20.085 (3)0.059 (2)0.057 (2)−0.012 (2)0.013 (2)−0.0011 (18)
C10.043 (3)0.052 (3)0.055 (3)0.019 (2)0.002 (2)0.003 (2)
C20.044 (3)0.046 (3)0.054 (3)0.016 (2)0.001 (2)0.006 (2)
C30.061 (3)0.049 (3)0.052 (3)0.014 (3)−0.002 (2)0.004 (2)
C40.060 (3)0.055 (3)0.056 (3)0.022 (3)0.001 (3)0.012 (2)
C50.046 (3)0.048 (3)0.074 (4)0.020 (2)0.010 (3)0.010 (3)
C60.047 (3)0.045 (3)0.061 (3)0.016 (2)0.001 (2)0.002 (2)
C70.041 (3)0.052 (3)0.055 (3)0.014 (2)0.002 (2)−0.003 (2)
C80.060 (3)0.070 (4)0.051 (3)0.012 (3)−0.002 (3)0.002 (3)
C90.078 (4)0.062 (4)0.062 (3)0.017 (3)0.003 (3)0.000 (3)
C100.110 (6)0.088 (5)0.059 (4)0.011 (4)0.009 (4)0.002 (3)
C110.114 (6)0.098 (6)0.089 (5)0.025 (5)0.036 (5)−0.012 (4)
C120.047 (3)0.050 (3)0.059 (3)0.018 (2)0.007 (2)0.002 (2)
C130.060 (3)0.047 (3)0.065 (3)0.004 (3)0.018 (3)0.002 (3)
C140.085 (5)0.063 (4)0.065 (4)0.001 (3)0.016 (3)0.002 (3)
C150.086 (4)0.062 (4)0.065 (4)0.014 (3)0.016 (3)0.013 (3)
C160.056 (3)0.051 (3)0.082 (4)0.014 (3)0.018 (3)0.011 (3)
C170.043 (3)0.048 (3)0.077 (4)0.011 (2)0.002 (3)0.001 (3)
C180.046 (3)0.047 (3)0.064 (3)0.016 (2)0.002 (2)−0.004 (2)
C190.057 (3)0.057 (3)0.051 (3)0.021 (3)−0.004 (2)−0.005 (2)
C200.075 (4)0.070 (4)0.070 (4)0.036 (3)0.004 (3)0.004 (3)
C210.087 (5)0.090 (5)0.091 (5)0.043 (4)0.016 (4)0.034 (4)
C220.186 (11)0.106 (7)0.102 (7)0.049 (7)−0.044 (7)−0.002 (5)
Geometric parameters (Å, °) top
Fe1—O21.890 (4)C10—C111.513 (10)
Fe1—O11.907 (4)C10—H10A0.9700
Fe1—N22.001 (4)C10—H10B0.9700
Fe1—N12.010 (4)C11—H11A0.9600
Cl1—C51.753 (5)C11—H11B0.9600
Cl2—C161.749 (6)C11—H11C0.9600
N1—C71.291 (7)C12—C131.399 (7)
N1—C81.480 (6)C12—C171.422 (7)
N2—C181.299 (7)C12—C181.438 (7)
N2—C191.474 (6)C13—C141.410 (8)
O1—C21.324 (6)C14—C151.381 (8)
O2—C131.309 (6)C14—H140.9300
C1—C21.412 (7)C15—C161.383 (9)
C1—C61.423 (7)C15—H150.9300
C1—C71.432 (7)C16—C171.368 (8)
C2—C31.392 (7)C17—H170.9300
C3—C41.384 (7)C18—H180.9300
C3—H30.9300C19—C201.506 (7)
C4—C51.388 (8)C19—H19A0.9700
C4—H40.9300C19—H19B0.9700
C5—C61.368 (7)C20—C211.529 (8)
C6—H60.9300C20—H20A0.9700
C7—H70.9300C20—H20B0.9700
C8—C91.510 (8)C21—C221.470 (10)
C8—H8A0.9700C21—H21A0.9700
C8—H8B0.9700C21—H21B0.9700
C9—C101.500 (8)C22—H22A0.9600
C9—H9A0.9700C22—H22B0.9600
C9—H9B0.9700C22—H22C0.9600
O2—Fe1—O1176.03 (18)H10A—C10—H10B107.9
O2—Fe1—N291.69 (17)C10—C11—H11A109.5
O1—Fe1—N290.18 (16)C10—C11—H11B109.5
O2—Fe1—N187.76 (17)H11A—C11—H11B109.5
O1—Fe1—N190.95 (16)C10—C11—H11C109.5
N2—Fe1—N1170.71 (16)H11A—C11—H11C109.5
C7—N1—C8114.2 (4)H11B—C11—H11C109.5
C7—N1—Fe1123.9 (4)C13—C12—C17120.1 (5)
C8—N1—Fe1121.6 (3)C13—C12—C18123.1 (5)
C18—N2—C19114.8 (5)C17—C12—C18116.8 (5)
C18—N2—Fe1124.0 (4)O2—C13—C12123.9 (5)
C19—N2—Fe1121.1 (3)O2—C13—C14118.1 (5)
C2—O1—Fe1128.2 (3)C12—C13—C14118.0 (5)
C13—O2—Fe1129.4 (4)C15—C14—C13121.6 (6)
C2—C1—C6120.0 (5)C15—C14—H14119.2
C2—C1—C7123.5 (5)C13—C14—H14119.2
C6—C1—C7116.5 (5)C14—C15—C16119.2 (6)
O1—C2—C3119.6 (4)C14—C15—H15120.4
O1—C2—C1122.4 (5)C16—C15—H15120.4
C3—C2—C1118.0 (5)C17—C16—C15121.7 (5)
C4—C3—C2122.1 (5)C17—C16—Cl2119.4 (5)
C4—C3—H3119.0C15—C16—Cl2118.9 (5)
C2—C3—H3119.0C16—C17—C12119.3 (5)
C3—C4—C5119.0 (5)C16—C17—H17120.4
C3—C4—H4120.5C12—C17—H17120.4
C5—C4—H4120.5N2—C18—C12126.2 (5)
C6—C5—C4121.7 (5)N2—C18—H18116.9
C6—C5—Cl1119.2 (4)C12—C18—H18116.9
C4—C5—Cl1119.0 (4)N2—C19—C20111.7 (4)
C5—C6—C1119.1 (5)N2—C19—H19A109.3
C5—C6—H6120.4C20—C19—H19A109.3
C1—C6—H6120.4N2—C19—H19B109.3
N1—C7—C1126.6 (5)C20—C19—H19B109.3
N1—C7—H7116.7H19A—C19—H19B107.9
C1—C7—H7116.7C19—C20—C21112.0 (5)
N1—C8—C9111.1 (5)C19—C20—H20A109.2
N1—C8—H8A109.4C21—C20—H20A109.2
C9—C8—H8A109.4C19—C20—H20B109.2
N1—C8—H8B109.4C21—C20—H20B109.2
C9—C8—H8B109.4H20A—C20—H20B107.9
H8A—C8—H8B108.0C22—C21—C20116.1 (6)
C10—C9—C8113.9 (6)C22—C21—H21A108.3
C10—C9—H9A108.8C20—C21—H21A108.3
C8—C9—H9A108.8C22—C21—H21B108.3
C10—C9—H9B108.8C20—C21—H21B108.3
C8—C9—H9B108.8H21A—C21—H21B107.4
H9A—C9—H9B107.7C21—C22—H22A109.5
C9—C10—C11112.3 (7)C21—C22—H22B109.5
C9—C10—H10A109.2H22A—C22—H22B109.5
C11—C10—H10A109.2C21—C22—H22C109.5
C9—C10—H10B109.2H22A—C22—H22C109.5
C11—C10—H10B109.2H22B—C22—H22C109.5
Table 1
Selected geometric parameters (Å, °) top
Fe1—O21.890 (4)Fe1—N22.001 (4)
Fe1—O11.907 (4)Fe1—N12.010 (4)
O2—Fe1—O1176.03 (18)O2—Fe1—N187.76 (17)
O2—Fe1—N291.69 (17)O1—Fe1—N190.95 (16)
O1—Fe1—N290.18 (16)N2—Fe1—N1170.71 (16)
Acknowledgements top

The authors appreciate the generous financial support of this work by the Chinese Funds for Zhicheng Project (2006BAC02A11) and Wuhan Yindao project(20066009138-07).

references
References top

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.

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.

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.