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

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ISSN: 2056-9890

Tris[4-chloro-2-(2-furylmethyl­imino­meth­yl)phenolato-κ2O1,N]iron(III)

aState Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, People's Republic of China
*Correspondence e-mail: changhongliu@163.com

(Received 11 May 2008; accepted 12 May 2008; online 17 May 2008)

The title complex, [Fe(C12H9ClNO2)3], is a mononuclear Schiff base iron(III) compound. The Fe atom is six-coordinated by three phenolic O and three imine N atoms from three Schiff base ligands in an octa­hedral geometry.

Related literature

For related structures see Chiari et al. (1983[Chiari, B., Piovesana, O., Tarantelli, T. & Zanazzi, P. F. (1983). Inorg. Chem. 22, 2781-2784.]); Hernandez-Molina et al. (1998[Hernandez-Molina, R., Mederos, A., Dominguez, S., Gili, P., Ruiz-Perez, C., Castineiras, A., Solans, X., Lloret, F. & Real, J. A. (1998). Inorg. Chem. 37, 5102-5108.]); Li et al. (2006[Li, Y.-G., Zhu, H.-L., Chen, X.-Z., Song, Y. & Huang, W.-Q. (2006). Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 36, 353-357.]); Liu et al. (2004[Liu, Z.-D., Tan, M.-Y. & Zhu, H.-L. (2004). Acta Cryst. E60, m910-m911.]); Yang et al. (2001[Yang, S.-P., Tong, Y.-X., Zhu, H.-L., Cao, H., Chen, X.-M. & Ji, L.-N. (2001). Polyhedron, 20, 223-229.]); You et al. (2005[You, Z.-L., Tang, L.-L. & Zhu, H.-L. (2005). Acta Cryst. E61, m36-m38.]); Zhang et al. (2005[Zhang, J.-H., Xi, Y., Wang, C., Li, J., Zhang, F.-X. & Ng, S. W. (2005). Acta Cryst. E61, m2338-m2339.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C12H9ClNO2)3]

  • Mr = 759.81

  • Triclinic, [P \overline 1]

  • a = 9.622 (2) Å

  • b = 11.542 (2) Å

  • c = 16.605 (3) Å

  • α = 103.00 (3)°

  • β = 102.81 (3)°

  • γ = 105.50 (3)°

  • V = 1651.7 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.75 mm−1

  • T = 293 (2) K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.806, Tmax = 0.864

  • 6546 measured reflections

  • 6150 independent reflections

  • 4172 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.114

  • S = 1.05

  • 6150 reflections

  • 442 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Schiff base iron(III) complexes have been widely investigated due to their versatile structures and properties (Li et al., 2006; Liu et al., 2004; Yang et al., 2001; Chiari et al., 1983). We report herein the crystal structure of the title complex (I), Fig 1.

The title complex is a mononuclear Schiff base iron(III) compound. The Fe atom is six-coordinated by three phenolic O and three imine N atoms from three Schiff base ligands, in an octahedral geometry. All the coordinate bond values (Table 1) are typical and comparable with those observed in other similar Schiff base iron(III) complexes (You et al., 2005; Hernandez-Molina et al., 1998; Zhang et al., 2005).

Related literature top

For related structures see Chiari et al. (1983); Hernandez-Molina et al. (1998); Li et al. (2006); Liu et al. (2004); Yang et al. (2001); You et al. (2005); Zhang et al. (2005).

Experimental top

5-Chlorosalicylaldehyde (0.3 mmol, 46.8 mg), furan-2-ylmethylamine (0.3 mmol, 29.1 mg) and FeCl3 (0.1 mmol, 16.2 mg) were dissolved in a methanol solution (30 ml). The mixture was stirred at room temperature for 30 min to give a deep brown solution. After keeping the solution in air for a few days, deep brown crystals were formed.

Refinement top

H atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93–0.97 Å, Uiso = 1.2Ueq(C) for aromatic, 0.97 Å, Uiso = 1.2Ueq (C) for CH2.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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).

Figures top
[Figure 1] Fig. 1. The structure of the complex with displacement parameters drawn at the 30% probability level. Hydrogen atoms have been omitted for clarity.
Tris[4-chloro-2-(2-furylmethyliminomethyl)phenolato-κ2O1,N]iron(III) top
Crystal data top
[Fe(C12H9ClNO2)3]Z = 2
Mr = 759.81F(000) = 778
Triclinic, P1Dx = 1.528 Mg m3
a = 9.622 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.542 (2) ÅCell parameters from 2732 reflections
c = 16.605 (3) Åθ = 2.3–25.1°
α = 103.00 (3)°µ = 0.75 mm1
β = 102.81 (3)°T = 293 K
γ = 105.50 (3)°Block, brown
V = 1651.7 (6) Å30.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
6150 independent reflections
Radiation source: fine-focus sealed tube4172 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scansθmax = 25.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 110
Tmin = 0.806, Tmax = 0.864k = 1313
6546 measured reflectionsl = 1920
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0309P)2 + 1.247P]
where P = (Fo2 + 2Fc2)/3
6150 reflections(Δ/σ)max < 0.001
442 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
[Fe(C12H9ClNO2)3]γ = 105.50 (3)°
Mr = 759.81V = 1651.7 (6) Å3
Triclinic, P1Z = 2
a = 9.622 (2) ÅMo Kα radiation
b = 11.542 (2) ŵ = 0.75 mm1
c = 16.605 (3) ÅT = 293 K
α = 103.00 (3)°0.30 × 0.20 × 0.20 mm
β = 102.81 (3)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
6150 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
4172 reflections with I > 2σ(I)
Tmin = 0.806, Tmax = 0.864Rint = 0.030
6546 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.05Δρmax = 0.30 e Å3
6150 reflectionsΔρmin = 0.29 e Å3
442 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
xyzUiso*/Ueq
C10.8963 (4)0.8886 (4)0.7319 (3)0.0377 (10)
C20.8341 (4)0.7860 (4)0.6545 (2)0.0332 (9)
C30.8877 (4)0.8012 (4)0.5837 (3)0.0408 (10)
H30.85270.73390.53310.049*
C40.9901 (5)0.9125 (4)0.5874 (3)0.0451 (11)
H41.02310.92010.53970.054*
C51.0444 (5)1.0139 (4)0.6628 (3)0.0461 (11)
C61.0023 (5)1.0026 (4)0.7347 (3)0.0450 (11)
H61.04321.06970.78550.054*
C70.8729 (5)0.8727 (4)0.8115 (3)0.0407 (10)
H70.93760.93400.86240.049*
C80.7906 (5)0.7713 (4)0.9083 (3)0.0477 (11)
H8A0.72020.69160.90540.057*
H8B0.76560.83830.94240.057*
C90.9470 (5)0.7789 (4)0.9530 (3)0.0497 (12)
C101.0404 (6)0.7212 (5)0.9308 (3)0.0724 (16)
H101.02120.65980.87890.087*
C111.1762 (6)0.7712 (5)1.0016 (4)0.0723 (16)
H111.26290.74901.00480.087*
C121.1551 (7)0.8537 (6)1.0606 (4)0.090 (2)
H121.22580.90071.11410.108*
C130.4529 (5)0.8389 (4)0.8092 (3)0.0394 (10)
C140.5093 (4)0.8639 (4)0.7410 (3)0.0345 (9)
C150.5156 (5)0.9808 (4)0.7261 (3)0.0452 (11)
H150.54750.99850.67990.054*
C160.4755 (5)1.0691 (4)0.7783 (3)0.0524 (12)
H160.48181.14590.76770.063*
C170.4261 (5)1.0431 (4)0.8460 (3)0.0512 (12)
C180.4107 (5)0.9310 (4)0.8610 (3)0.0494 (12)
H180.37240.91400.90540.059*
C190.4201 (5)0.7158 (4)0.8207 (3)0.0415 (10)
H190.35760.69700.85480.050*
C200.4115 (5)0.5014 (4)0.7962 (3)0.0482 (11)
H20A0.35050.44440.73920.058*
H20B0.49700.47400.81460.058*
C210.3201 (5)0.4868 (4)0.8563 (3)0.0472 (11)
C220.1753 (6)0.4256 (5)0.8454 (4)0.0735 (16)
H220.10040.38350.79260.088*
C230.1561 (8)0.4358 (6)0.9274 (4)0.086 (2)
H230.06670.40290.93970.103*
C240.2883 (8)0.5005 (7)0.9830 (4)0.087 (2)
H240.30850.51921.04270.104*
C250.5834 (4)0.3675 (3)0.6264 (3)0.0347 (9)
C260.6809 (4)0.4270 (4)0.7118 (3)0.0345 (9)
C270.7674 (4)0.3602 (4)0.7489 (3)0.0428 (10)
H270.82470.39360.80700.051*
C280.7684 (5)0.2470 (4)0.7012 (3)0.0454 (11)
H280.82710.20510.72670.054*
C290.6820 (5)0.1950 (4)0.6148 (3)0.0436 (11)
C300.5872 (4)0.2511 (4)0.5786 (3)0.0387 (10)
H300.52460.21250.52180.046*
C310.4788 (4)0.4211 (4)0.5857 (3)0.0341 (9)
H310.41300.37210.53110.041*
C320.3452 (4)0.5605 (4)0.5631 (2)0.0339 (9)
H32A0.38540.64650.56210.041*
H32B0.31280.50540.50400.041*
C330.2134 (4)0.5477 (4)0.5959 (3)0.0372 (10)
C340.1434 (5)0.6272 (5)0.6248 (3)0.0555 (13)
H340.17250.71330.63190.067*
C350.0168 (6)0.5541 (6)0.6421 (3)0.0671 (15)
H350.05250.58340.66400.080*
C360.0153 (6)0.4367 (6)0.6216 (3)0.0676 (15)
H360.05840.36890.62540.081*
Cl11.16738 (17)1.15609 (12)0.66343 (9)0.0758 (4)
Cl20.38023 (18)1.15945 (13)0.91252 (10)0.0792 (5)
Cl30.69996 (15)0.05941 (11)0.55247 (9)0.0668 (4)
Fe10.61221 (6)0.65594 (5)0.72051 (3)0.02604 (14)
N10.7708 (4)0.7817 (3)0.8190 (2)0.0370 (8)
N20.4705 (4)0.6291 (3)0.7876 (2)0.0351 (8)
N30.4665 (3)0.5287 (3)0.61637 (19)0.0295 (7)
O10.7387 (3)0.6767 (2)0.64791 (16)0.0370 (7)
O21.0136 (4)0.8618 (3)1.0329 (2)0.0808 (12)
O30.5480 (3)0.7841 (2)0.68880 (17)0.0358 (6)
O40.3940 (4)0.5377 (4)0.9423 (2)0.0744 (11)
O50.6944 (3)0.5392 (2)0.75910 (17)0.0394 (7)
O60.1379 (3)0.4282 (3)0.5938 (2)0.0537 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.036 (2)0.034 (2)0.038 (2)0.0084 (19)0.0110 (19)0.0072 (19)
C20.031 (2)0.032 (2)0.036 (2)0.0112 (18)0.0114 (18)0.0072 (18)
C30.038 (2)0.040 (2)0.040 (3)0.009 (2)0.017 (2)0.004 (2)
C40.044 (3)0.045 (3)0.048 (3)0.011 (2)0.019 (2)0.018 (2)
C50.043 (3)0.036 (2)0.053 (3)0.003 (2)0.011 (2)0.018 (2)
C60.047 (3)0.037 (2)0.039 (3)0.006 (2)0.008 (2)0.002 (2)
C70.044 (3)0.034 (2)0.032 (2)0.008 (2)0.006 (2)0.0016 (18)
C80.050 (3)0.055 (3)0.035 (2)0.017 (2)0.012 (2)0.009 (2)
C90.051 (3)0.053 (3)0.036 (3)0.014 (2)0.007 (2)0.006 (2)
C100.075 (4)0.087 (4)0.056 (3)0.037 (3)0.020 (3)0.008 (3)
C110.061 (4)0.085 (4)0.081 (4)0.040 (3)0.017 (3)0.028 (3)
C120.063 (4)0.100 (5)0.075 (4)0.037 (4)0.016 (3)0.009 (4)
C130.039 (2)0.039 (2)0.045 (3)0.0142 (19)0.020 (2)0.012 (2)
C140.030 (2)0.034 (2)0.037 (2)0.0075 (18)0.0092 (18)0.0103 (19)
C150.057 (3)0.037 (2)0.049 (3)0.018 (2)0.023 (2)0.017 (2)
C160.063 (3)0.037 (3)0.059 (3)0.022 (2)0.021 (3)0.009 (2)
C170.055 (3)0.045 (3)0.054 (3)0.025 (2)0.020 (2)0.004 (2)
C180.055 (3)0.055 (3)0.048 (3)0.029 (2)0.025 (2)0.012 (2)
C190.044 (3)0.049 (3)0.037 (2)0.016 (2)0.021 (2)0.014 (2)
C200.054 (3)0.044 (3)0.054 (3)0.014 (2)0.025 (2)0.022 (2)
C210.053 (3)0.052 (3)0.045 (3)0.021 (2)0.018 (2)0.023 (2)
C220.058 (4)0.085 (4)0.074 (4)0.006 (3)0.026 (3)0.031 (3)
C230.078 (4)0.119 (6)0.104 (5)0.043 (4)0.058 (4)0.074 (5)
C240.107 (5)0.141 (6)0.074 (4)0.079 (5)0.058 (4)0.075 (4)
C250.031 (2)0.029 (2)0.042 (2)0.0057 (17)0.0120 (19)0.0102 (18)
C260.027 (2)0.032 (2)0.046 (3)0.0076 (18)0.0144 (19)0.0141 (19)
C270.035 (2)0.045 (3)0.049 (3)0.012 (2)0.011 (2)0.020 (2)
C280.036 (2)0.043 (3)0.067 (3)0.021 (2)0.017 (2)0.026 (2)
C290.038 (2)0.031 (2)0.063 (3)0.0100 (19)0.023 (2)0.010 (2)
C300.035 (2)0.031 (2)0.047 (3)0.0074 (19)0.014 (2)0.010 (2)
C310.030 (2)0.032 (2)0.032 (2)0.0019 (17)0.0099 (18)0.0056 (18)
C320.033 (2)0.038 (2)0.032 (2)0.0120 (18)0.0106 (18)0.0110 (18)
C330.035 (2)0.041 (2)0.034 (2)0.0121 (19)0.0076 (19)0.0122 (19)
C340.049 (3)0.053 (3)0.070 (3)0.029 (2)0.017 (3)0.015 (3)
C350.053 (3)0.094 (4)0.073 (4)0.040 (3)0.033 (3)0.027 (3)
C360.045 (3)0.093 (4)0.077 (4)0.019 (3)0.034 (3)0.037 (3)
Cl10.0852 (10)0.0462 (7)0.0765 (10)0.0099 (7)0.0222 (8)0.0222 (7)
Cl20.0968 (11)0.0659 (9)0.0840 (10)0.0482 (8)0.0408 (9)0.0015 (7)
Cl30.0663 (8)0.0420 (7)0.0972 (11)0.0285 (6)0.0331 (8)0.0098 (7)
Fe10.0258 (3)0.0256 (3)0.0263 (3)0.0081 (2)0.0099 (2)0.0055 (2)
N10.041 (2)0.0364 (19)0.0294 (19)0.0086 (16)0.0126 (16)0.0050 (15)
N20.0360 (19)0.0362 (19)0.0355 (19)0.0126 (16)0.0135 (16)0.0119 (16)
N30.0255 (17)0.0315 (18)0.0330 (18)0.0096 (14)0.0117 (14)0.0094 (15)
O10.0350 (15)0.0317 (15)0.0401 (16)0.0045 (12)0.0196 (13)0.0024 (13)
O20.075 (3)0.084 (3)0.055 (2)0.039 (2)0.012 (2)0.0175 (19)
O30.0424 (16)0.0338 (15)0.0377 (16)0.0161 (13)0.0203 (13)0.0109 (13)
O40.066 (2)0.115 (3)0.053 (2)0.030 (2)0.0212 (19)0.043 (2)
O50.0408 (16)0.0350 (16)0.0375 (16)0.0144 (13)0.0053 (13)0.0059 (13)
O60.0452 (18)0.0497 (19)0.073 (2)0.0140 (15)0.0318 (17)0.0198 (17)
Geometric parameters (Å, º) top
C1—C21.416 (5)C20—H20A0.9700
C1—C61.417 (5)C20—H20B0.9700
C1—C71.433 (5)C21—C221.333 (6)
C2—O11.312 (4)C21—O41.356 (5)
C2—C31.412 (5)C22—C231.398 (7)
C3—C41.373 (5)C22—H220.9300
C3—H30.9300C23—C241.299 (8)
C4—C51.390 (6)C23—H230.9300
C4—H40.9300C24—O41.371 (6)
C5—C61.364 (6)C24—H240.9300
C5—Cl11.744 (4)C25—C261.411 (5)
C6—H60.9300C25—C301.412 (5)
C7—N11.283 (5)C25—C311.440 (5)
C7—H70.9300C26—O51.311 (4)
C8—N11.488 (5)C26—C271.412 (5)
C8—C91.493 (6)C27—C281.371 (6)
C8—H8A0.9700C27—H270.9300
C8—H8B0.9700C28—C291.387 (6)
C9—C101.320 (6)C28—H280.9300
C9—O21.345 (5)C29—C301.365 (6)
C10—C111.426 (7)C29—Cl31.746 (4)
C10—H100.9300C30—H300.9300
C11—C121.296 (7)C31—N31.280 (5)
C11—H110.9300C31—H310.9300
C12—O21.373 (6)C32—C331.473 (5)
C12—H120.9300C32—N31.482 (5)
C13—C141.413 (5)C32—H32A0.9700
C13—C181.417 (5)C32—H32B0.9700
C13—C191.437 (5)C33—C341.342 (6)
C14—O31.306 (4)C33—O61.366 (5)
C14—C151.413 (5)C34—C351.412 (7)
C15—C161.378 (6)C34—H340.9300
C15—H150.9300C35—C361.315 (7)
C16—C171.376 (6)C35—H350.9300
C16—H160.9300C36—O61.377 (5)
C17—C181.349 (6)C36—H360.9300
C17—Cl21.756 (4)Fe1—O31.882 (3)
C18—H180.9300Fe1—O51.894 (3)
C19—N21.291 (5)Fe1—O11.902 (3)
C19—H190.9300Fe1—N11.937 (3)
C20—C211.477 (6)Fe1—N31.948 (3)
C20—N21.482 (5)Fe1—N21.950 (3)
C2—C1—C6120.1 (4)C22—C23—H23126.9
C2—C1—C7120.7 (4)C23—C24—O4111.3 (5)
C6—C1—C7118.5 (4)C23—C24—H24124.3
O1—C2—C3119.2 (3)O4—C24—H24124.3
O1—C2—C1123.4 (3)C26—C25—C30119.5 (4)
C3—C2—C1117.2 (4)C26—C25—C31122.3 (3)
C4—C3—C2121.9 (4)C30—C25—C31118.2 (4)
C4—C3—H3119.0O5—C26—C25124.1 (4)
C2—C3—H3119.0O5—C26—C27118.1 (4)
C3—C4—C5119.8 (4)C25—C26—C27117.7 (4)
C3—C4—H4120.1C28—C27—C26121.3 (4)
C5—C4—H4120.1C28—C27—H27119.3
C6—C5—C4120.8 (4)C26—C27—H27119.3
C6—C5—Cl1120.7 (3)C27—C28—C29120.1 (4)
C4—C5—Cl1118.5 (3)C27—C28—H28120.0
C5—C6—C1120.1 (4)C29—C28—H28120.0
C5—C6—H6120.0C30—C29—C28120.4 (4)
C1—C6—H6120.0C30—C29—Cl3120.4 (4)
N1—C7—C1126.0 (4)C28—C29—Cl3119.2 (3)
N1—C7—H7117.0C29—C30—C25120.6 (4)
C1—C7—H7117.0C29—C30—H30119.7
N1—C8—C9113.5 (4)C25—C30—H30119.7
N1—C8—H8A108.9N3—C31—C25127.1 (4)
C9—C8—H8A108.9N3—C31—H31116.5
N1—C8—H8B108.9C25—C31—H31116.5
C9—C8—H8B108.9C33—C32—N3112.6 (3)
H8A—C8—H8B107.7C33—C32—H32A109.1
C10—C9—O2109.8 (4)N3—C32—H32A109.1
C10—C9—C8133.6 (4)C33—C32—H32B109.1
O2—C9—C8116.6 (4)N3—C32—H32B109.1
C9—C10—C11106.9 (5)H32A—C32—H32B107.8
C9—C10—H10126.5C34—C33—O6110.3 (4)
C11—C10—H10126.5C34—C33—C32134.5 (4)
C12—C11—C10106.5 (5)O6—C33—C32115.2 (3)
C12—C11—H11126.8C33—C34—C35106.4 (4)
C10—C11—H11126.8C33—C34—H34126.8
C11—C12—O2110.4 (5)C35—C34—H34126.8
C11—C12—H12124.8C36—C35—C34107.3 (4)
O2—C12—H12124.8C36—C35—H35126.4
C14—C13—C18120.0 (4)C34—C35—H35126.4
C14—C13—C19120.9 (4)C35—C36—O6110.7 (5)
C18—C13—C19118.7 (4)C35—C36—H36124.7
O3—C14—C13124.4 (4)O6—C36—H36124.7
O3—C14—C15118.5 (4)O3—Fe1—O5174.53 (12)
C13—C14—C15117.0 (4)O3—Fe1—O186.76 (11)
C16—C15—C14121.6 (4)O5—Fe1—O191.70 (12)
C16—C15—H15119.2O3—Fe1—N189.84 (13)
C14—C15—H15119.2O5—Fe1—N184.94 (13)
C17—C16—C15119.7 (4)O1—Fe1—N191.02 (13)
C17—C16—H16120.1O3—Fe1—N391.31 (12)
C15—C16—H16120.1O5—Fe1—N393.76 (12)
C18—C17—C16121.5 (4)O1—Fe1—N384.11 (12)
C18—C17—Cl2120.2 (4)N1—Fe1—N3174.93 (13)
C16—C17—Cl2118.3 (4)O3—Fe1—N292.00 (13)
C17—C18—C13120.1 (4)O5—Fe1—N289.87 (13)
C17—C18—H18120.0O1—Fe1—N2175.99 (13)
C13—C18—H18120.0N1—Fe1—N292.79 (14)
N2—C19—C13125.3 (4)N3—Fe1—N292.11 (13)
N2—C19—H19117.3C7—N1—C8115.3 (3)
C13—C19—H19117.3C7—N1—Fe1122.9 (3)
C21—C20—N2117.4 (4)C8—N1—Fe1121.5 (3)
C21—C20—H20A107.9C19—N2—C20118.9 (3)
N2—C20—H20A107.9C19—N2—Fe1122.7 (3)
C21—C20—H20B107.9C20—N2—Fe1118.3 (3)
N2—C20—H20B107.9C31—N3—C32116.8 (3)
H20A—C20—H20B107.2C31—N3—Fe1123.0 (3)
C22—C21—O4109.0 (4)C32—N3—Fe1119.8 (2)
C22—C21—C20133.7 (5)C2—O1—Fe1123.3 (2)
O4—C21—C20117.1 (4)C9—O2—C12106.5 (4)
C21—C22—C23107.9 (5)C14—O3—Fe1122.8 (2)
C21—C22—H22126.1C21—O4—C24105.5 (4)
C23—C22—H22126.1C26—O5—Fe1126.4 (3)
C24—C23—C22106.2 (5)C33—O6—C36105.4 (4)
C24—C23—H23126.9
C6—C1—C2—O1178.1 (4)O5—Fe1—N1—C7119.8 (3)
C7—C1—C2—O18.2 (6)O1—Fe1—N1—C728.2 (3)
C6—C1—C2—C33.0 (6)N3—Fe1—N1—C744.5 (17)
C7—C1—C2—C3166.9 (4)N2—Fe1—N1—C7150.6 (3)
O1—C2—C3—C4178.6 (4)O3—Fe1—N1—C8127.6 (3)
C1—C2—C3—C43.3 (6)O5—Fe1—N1—C854.0 (3)
C2—C3—C4—C50.4 (7)O1—Fe1—N1—C8145.6 (3)
C3—C4—C5—C62.9 (7)N3—Fe1—N1—C8129.3 (15)
C3—C4—C5—Cl1177.0 (3)N2—Fe1—N1—C835.6 (3)
C4—C5—C6—C13.2 (7)C13—C19—N2—C20172.4 (4)
Cl1—C5—C6—C1176.8 (3)C13—C19—N2—Fe13.8 (6)
C2—C1—C6—C50.1 (6)C21—C20—N2—C1911.3 (6)
C7—C1—C6—C5170.3 (4)C21—C20—N2—Fe1172.3 (3)
C2—C1—C7—N117.6 (7)O3—Fe1—N2—C1925.3 (3)
C6—C1—C7—N1172.3 (4)O5—Fe1—N2—C19149.5 (3)
N1—C8—C9—C1049.9 (8)O1—Fe1—N2—C1997.2 (18)
N1—C8—C9—O2129.2 (4)N1—Fe1—N2—C1964.6 (3)
O2—C9—C10—C110.1 (6)N3—Fe1—N2—C19116.7 (3)
C8—C9—C10—C11179.0 (5)O3—Fe1—N2—C20150.9 (3)
C9—C10—C11—C120.3 (7)O5—Fe1—N2—C2034.2 (3)
C10—C11—C12—O20.3 (8)O1—Fe1—N2—C2079.0 (19)
C18—C13—C14—O3178.5 (4)N1—Fe1—N2—C20119.2 (3)
C19—C13—C14—O36.1 (6)N3—Fe1—N2—C2059.5 (3)
C18—C13—C14—C152.2 (6)C25—C31—N3—C32177.7 (3)
C19—C13—C14—C15170.2 (4)C25—C31—N3—Fe19.8 (5)
O3—C14—C15—C16179.6 (4)C33—C32—N3—C31103.3 (4)
C13—C14—C15—C163.1 (6)C33—C32—N3—Fe183.9 (4)
C14—C15—C16—C170.9 (7)O3—Fe1—N3—C31160.0 (3)
C15—C16—C17—C182.3 (7)O5—Fe1—N3—C3118.0 (3)
C15—C16—C17—Cl2178.6 (4)O1—Fe1—N3—C3173.4 (3)
C16—C17—C18—C133.2 (7)N1—Fe1—N3—C3157.0 (17)
Cl2—C17—C18—C13177.7 (3)N2—Fe1—N3—C31108.0 (3)
C14—C13—C18—C170.8 (7)O3—Fe1—N3—C3212.4 (3)
C19—C13—C18—C17173.4 (4)O5—Fe1—N3—C32169.7 (3)
C14—C13—C19—N218.0 (7)O1—Fe1—N3—C3299.0 (3)
C18—C13—C19—N2169.5 (4)N1—Fe1—N3—C32115.3 (16)
N2—C20—C21—C22113.5 (6)N2—Fe1—N3—C3279.7 (3)
N2—C20—C21—O471.4 (5)C3—C2—O1—Fe1160.3 (3)
O4—C21—C22—C231.0 (6)C1—C2—O1—Fe124.7 (5)
C20—C21—C22—C23174.4 (5)O3—Fe1—O1—C252.8 (3)
C21—C22—C23—C240.6 (7)O5—Fe1—O1—C2122.0 (3)
C22—C23—C24—O42.0 (8)N1—Fe1—O1—C237.0 (3)
C30—C25—C26—O5174.6 (3)N3—Fe1—O1—C2144.4 (3)
C31—C25—C26—O55.6 (6)N2—Fe1—O1—C2124.9 (18)
C30—C25—C26—C276.6 (5)C10—C9—O2—C120.1 (6)
C31—C25—C26—C27173.3 (3)C8—C9—O2—C12179.4 (5)
O5—C26—C27—C28174.7 (4)C11—C12—O2—C90.3 (7)
C25—C26—C27—C286.4 (6)C13—C14—O3—Fe126.3 (5)
C26—C27—C28—C290.9 (6)C15—C14—O3—Fe1157.5 (3)
C27—C28—C29—C304.7 (6)O5—Fe1—O3—C1473.8 (13)
C27—C28—C29—Cl3173.5 (3)O1—Fe1—O3—C14147.6 (3)
C28—C29—C30—C254.4 (6)N1—Fe1—O3—C1456.5 (3)
Cl3—C29—C30—C25173.7 (3)N3—Fe1—O3—C14128.4 (3)
C26—C25—C30—C291.3 (6)N2—Fe1—O3—C1436.2 (3)
C31—C25—C30—C29178.5 (4)C22—C21—O4—C242.1 (6)
C26—C25—C31—N35.2 (6)C20—C21—O4—C24174.1 (4)
C30—C25—C31—N3174.9 (4)C23—C24—O4—C212.6 (7)
N3—C32—C33—C34119.8 (5)C25—C26—O5—Fe19.7 (5)
N3—C32—C33—O664.0 (4)C27—C26—O5—Fe1171.4 (3)
O6—C33—C34—C350.1 (5)O3—Fe1—O5—C26139.4 (12)
C32—C33—C34—C35176.5 (4)O1—Fe1—O5—C2665.9 (3)
C33—C34—C35—C361.2 (6)N1—Fe1—O5—C26156.7 (3)
C34—C35—C36—O61.9 (6)N3—Fe1—O5—C2618.3 (3)
C1—C7—N1—C8167.1 (4)N2—Fe1—O5—C26110.4 (3)
C1—C7—N1—Fe17.1 (6)C34—C33—O6—C361.0 (5)
C9—C8—N1—C747.8 (5)C32—C33—O6—C36176.2 (4)
C9—C8—N1—Fe1126.5 (3)C35—C36—O6—C331.8 (6)
O3—Fe1—N1—C758.6 (3)

Experimental details

Crystal data
Chemical formula[Fe(C12H9ClNO2)3]
Mr759.81
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.622 (2), 11.542 (2), 16.605 (3)
α, β, γ (°)103.00 (3), 102.81 (3), 105.50 (3)
V3)1651.7 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.75
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.806, 0.864
No. of measured, independent and
observed [I > 2σ(I)] reflections
6546, 6150, 4172
Rint0.030
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.114, 1.05
No. of reflections6150
No. of parameters442
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.29

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This project is supported by a research grant from Dalian Medical University.

References

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