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Acta Cryst. (2008). E64, m380    [ doi:10.1107/S1600536808001566 ]

Tris[2-(benzyliminomethyl)phenolato-[kappa]2N,O]iron(III)

H.-B. Gong, L. Wang and W.-T. Zhao

Abstract top

In the title compound, [Fe(C14H12NO)3], the FeIII atom has a slightly distorted octahedral geometry and is coordinated by three Schiff base ligands, viz. 2-(benzyliminomethyl)phenolate. The crystal structure is stabilized by intramolecular C-H...O and C-H...N hydrogen bonds.

Comment top

Due to its interesting physical and biological properties, many iron complexes with amines or imines have been structurally studied (Liu et al., 2004; You & Zhu, 2004; You et al.,2004, 2005; Zhu, Xia et al., 2003; Zhu, Zeng et al., 2003). We report here the title structure of (I). Compound (I) is an electronically neutral mononuclear iron (III) compound (Fig. 1). In the complex the central iron(III) atom is six coordinated by three nitrogen atoms and three oxygen atoms from three Schiff base ligands. In the crystal structure, (I) is stabilized by intramolecular C—H···O and C—H···N hydrogen bonds.

Related literature top

For related literature, see: Liu et al. (2004); You & Zhu (2004); You et al. (2004, 2005); Zhu, Xia et al. (2003); Zhu, Zeng et al. (2003).

Experimental top

Benzylamine and salicylaldehyde were available commercially and were used without further purification. Benzylamine (0.3 mmol, 32.0 mg) and salicylaldehyde (0.3 mmol, 36.7 mg) were dissolved in acetonitrile solution (20 ml). The mixture was stirred for 1 h to obtain a clear red solution of HL (0.3 mmol), where HL is 2-(benzyliminomethyl)phenol.To the solution of HL was added a solution of

Fe(ClO4)2×6×H2O (0.1 mmol, 38.9 mg) in acetonitrile (10 ml), with stirring. After keeping the resulting solution in air for 2 days, yielding large purple crystals. The crystals were isolated, washed three times with acetonitrile and methanol (yield 79%).

Refinement top

C-bound H atoms were included in the riding model approximation with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 molecular structure of (I), showing 30% probability displacement ellipsoids. H atoms unrelated to the hydrogen bonds have been omitted for clarity, showing hydrogen bond interactions as dashed lines.
Tris[2-(benzyliminomethyl)phenolato-κ2N,O]iron(III) top
Crystal data top
[Fe(C14H12NO)3]Z = 2
Mr = 686.59F000 = 718
Triclinic, P1Dx = 1.350 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 9.3470 (8) ÅCell parameters from 2702 reflections
b = 10.9248 (13) Åθ = 2.7–27.9º
c = 16.7702 (19) ŵ = 0.49 mm−1
α = 95.42 (3)ºT = 293 (2) K
β = 96.47 (3)ºPrism, purple
γ = 93.88 (3)º0.40 × 0.30 × 0.20 mm
V = 1688.6 (3) Å3
Data collection top
Bruker APEX area-detector
diffractometer		6624 independent reflections
Radiation source: fine-focus sealed tube4330 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.035
T = 293(2) Kθmax = 26.0º
φ and ω scansθmin = 1.2º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = 0→11
Tmin = 0.828, Tmax = 0.908k = −13→13
7053 measured reflectionsl = −20→20
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.152  w = 1/[σ2(Fo2) + (0.0661P)2 + 0.6392P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
6624 reflectionsΔρmax = 0.59 e Å−3
442 parametersΔρmin = −0.52 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Fe(C14H12NO)3]γ = 93.88 (3)º
Mr = 686.59V = 1688.6 (3) Å3
Triclinic, P1Z = 2
a = 9.3470 (8) ÅMo Kα
b = 10.9248 (13) ŵ = 0.49 mm−1
c = 16.7702 (19) ÅT = 293 (2) K
α = 95.42 (3)º0.40 × 0.30 × 0.20 mm
β = 96.47 (3)º
Data collection top
Bruker APEX area-detector
diffractometer		6624 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4330 reflections with I > 2σ(I)
Tmin = 0.828, Tmax = 0.908Rint = 0.035
7053 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.057442 parameters
wR(F2) = 0.152H-atom parameters constrained
S = 1.04Δρmax = 0.59 e Å−3
6624 reflectionsΔρmin = −0.52 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
Fe0.82215 (5)0.23502 (4)0.78274 (3)0.03716 (16)
O11.0232 (3)0.2737 (2)0.78948 (16)0.0554 (7)
O20.7939 (3)0.4060 (2)0.79542 (15)0.0497 (6)
O30.6202 (3)0.2022 (2)0.76423 (15)0.0458 (6)
N10.8205 (3)0.2453 (2)0.89852 (18)0.0440 (7)
N20.8234 (3)0.2396 (3)0.66785 (18)0.0461 (7)
N30.8477 (3)0.0590 (3)0.77627 (18)0.0449 (7)
C11.0614 (4)0.3518 (3)0.9288 (3)0.0515 (10)
C21.1043 (4)0.3354 (3)0.8506 (3)0.0511 (10)
C31.2425 (5)0.3852 (4)0.8396 (3)0.0690 (13)
H31.27420.37340.78910.083*
C41.3309 (5)0.4502 (4)0.9013 (4)0.0800 (15)
H41.42160.48210.89210.096*
C51.2884 (5)0.4696 (4)0.9774 (4)0.0767 (15)
H51.34900.51581.01880.092*
C61.1556 (5)0.4201 (4)0.9913 (3)0.0646 (12)
H61.12740.43181.04270.077*
C70.9239 (4)0.3019 (3)0.9480 (2)0.0492 (9)
H70.90870.31181.00200.059*
C80.6871 (4)0.2082 (3)0.9334 (2)0.0498 (9)
H8A0.60510.23820.90250.060*
H8B0.69340.24740.98820.060*
C90.6603 (4)0.0696 (3)0.9346 (2)0.0491 (9)
C100.5434 (5)0.0044 (4)0.8898 (3)0.0606 (11)
H100.48070.04480.85600.073*
C110.5173 (6)−0.1225 (4)0.8942 (3)0.0735 (13)
H110.4382−0.16630.86330.088*
C120.6085 (6)−0.1811 (4)0.9442 (3)0.0737 (14)
H120.5919−0.26540.94700.088*
C130.7231 (6)−0.1176 (4)0.9900 (3)0.0779 (15)
H130.7840−0.15811.02460.093*
C140.7501 (5)0.0081 (4)0.9854 (3)0.0657 (12)
H140.82920.05121.01690.079*
C150.6688 (4)0.4070 (3)0.6628 (2)0.0469 (9)
C160.7035 (4)0.4535 (3)0.7443 (2)0.0462 (9)
C170.6398 (4)0.5617 (3)0.7711 (3)0.0554 (10)
H170.66310.59640.82420.066*
C180.5452 (5)0.6154 (4)0.7204 (3)0.0678 (12)
H180.50580.68690.73940.081*
C190.5059 (5)0.5666 (4)0.6413 (3)0.0706 (13)
H190.43770.60230.60800.085*
C200.5700 (5)0.4642 (4)0.6128 (3)0.0627 (11)
H200.54700.43250.55910.075*
C210.7481 (4)0.3114 (3)0.6284 (2)0.0519 (10)
H210.74410.30110.57250.062*
C220.9185 (5)0.1603 (4)0.6228 (3)0.0639 (12)
H22A0.85930.09060.59330.077*
H22B0.98750.12820.66160.077*
C231.0000 (4)0.2252 (4)0.5645 (3)0.0560 (10)
C241.0837 (6)0.3340 (5)0.5903 (4)0.1012 (19)
H241.08970.36790.64370.121*
C251.1584 (8)0.3918 (7)0.5359 (6)0.142 (3)
H251.21310.46590.55270.171*
C261.1532 (8)0.3413 (8)0.4574 (5)0.126 (3)
H261.20520.38010.42150.151*
C271.0715 (7)0.2346 (7)0.4328 (3)0.1002 (19)
H271.06700.19980.37970.120*
C280.9951 (5)0.1775 (4)0.4861 (3)0.0682 (12)
H280.93870.10450.46830.082*
C290.6256 (4)0.0056 (3)0.6874 (2)0.0460 (9)
C300.5625 (4)0.1171 (3)0.7069 (2)0.0452 (9)
C310.4290 (4)0.1352 (4)0.6627 (3)0.0578 (11)
H310.38370.20670.67450.069*
C320.3658 (5)0.0481 (4)0.6025 (3)0.0719 (13)
H320.27860.06240.57370.086*
C330.4289 (5)−0.0614 (4)0.5834 (3)0.0701 (13)
H330.3855−0.11920.54200.084*
C340.5557 (5)−0.0814 (4)0.6269 (3)0.0607 (11)
H340.5969−0.15530.61590.073*
C350.7575 (4)−0.0208 (3)0.7334 (2)0.0494 (9)
H350.7788−0.10290.73170.059*
C360.9731 (5)0.0181 (4)0.8270 (3)0.0612 (11)
H36A0.94600.01170.88060.073*
H36B1.05150.08230.83170.073*
C371.0300 (4)−0.1014 (3)0.7987 (2)0.0467 (9)
C380.9776 (5)−0.2134 (4)0.8207 (3)0.0614 (11)
H380.9019−0.21590.85220.074*
C391.0363 (6)−0.3212 (4)0.7965 (3)0.0774 (14)
H391.0000−0.39590.81150.093*
C401.1473 (6)−0.3183 (5)0.7507 (3)0.0885 (17)
H401.1868−0.39100.73430.106*
C411.2012 (6)−0.2080 (5)0.7286 (3)0.0886 (17)
H411.2770−0.20620.69710.106*
C421.1431 (5)−0.1001 (4)0.7529 (3)0.0686 (13)
H421.1806−0.02570.73820.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe0.0438 (3)0.0289 (3)0.0396 (3)0.0075 (2)0.0040 (2)0.00545 (19)
O10.0523 (16)0.0539 (16)0.0604 (18)0.0033 (13)0.0096 (14)0.0044 (14)
O20.0623 (17)0.0343 (13)0.0516 (16)0.0088 (12)−0.0008 (13)0.0056 (11)
O30.0483 (15)0.0395 (14)0.0496 (15)0.0072 (11)0.0036 (12)0.0044 (12)
N10.0534 (19)0.0324 (15)0.0471 (18)0.0086 (14)0.0039 (15)0.0072 (13)
N20.059 (2)0.0386 (16)0.0424 (17)0.0098 (15)0.0091 (15)0.0054 (14)
N30.0519 (19)0.0393 (17)0.0439 (18)0.0114 (15)0.0047 (15)0.0027 (14)
C10.054 (2)0.0336 (19)0.065 (3)0.0123 (18)−0.006 (2)0.0040 (18)
C20.050 (2)0.0339 (19)0.068 (3)0.0071 (17)−0.004 (2)0.0069 (19)
C30.051 (3)0.061 (3)0.095 (4)0.006 (2)0.002 (3)0.012 (3)
C40.058 (3)0.060 (3)0.117 (5)−0.004 (2)−0.010 (3)0.017 (3)
C50.068 (3)0.047 (3)0.105 (4)0.008 (2)−0.029 (3)−0.002 (3)
C60.069 (3)0.041 (2)0.079 (3)0.021 (2)−0.014 (2)−0.001 (2)
C70.066 (3)0.0358 (19)0.046 (2)0.0175 (19)0.000 (2)0.0028 (16)
C80.066 (3)0.039 (2)0.047 (2)0.0129 (18)0.0143 (19)0.0051 (17)
C90.063 (3)0.041 (2)0.047 (2)0.0123 (19)0.016 (2)0.0061 (17)
C100.072 (3)0.055 (3)0.058 (3)0.004 (2)0.017 (2)0.015 (2)
C110.093 (4)0.058 (3)0.069 (3)−0.011 (3)0.023 (3)−0.001 (2)
C120.105 (4)0.041 (2)0.083 (3)0.010 (3)0.039 (3)0.009 (2)
C130.103 (4)0.053 (3)0.088 (4)0.033 (3)0.022 (3)0.027 (3)
C140.076 (3)0.055 (3)0.068 (3)0.016 (2)0.005 (2)0.017 (2)
C150.055 (2)0.0370 (19)0.050 (2)0.0077 (17)0.0059 (18)0.0103 (17)
C160.048 (2)0.037 (2)0.055 (2)0.0049 (17)0.0079 (19)0.0098 (17)
C170.059 (3)0.045 (2)0.062 (3)0.0129 (19)0.006 (2)0.0025 (19)
C180.071 (3)0.052 (3)0.082 (3)0.025 (2)0.006 (3)0.006 (2)
C190.067 (3)0.062 (3)0.086 (4)0.027 (2)−0.002 (3)0.019 (3)
C200.070 (3)0.059 (3)0.060 (3)0.008 (2)0.001 (2)0.015 (2)
C210.069 (3)0.045 (2)0.044 (2)0.008 (2)0.007 (2)0.0100 (17)
C220.085 (3)0.054 (3)0.057 (3)0.018 (2)0.022 (2)0.003 (2)
C230.051 (2)0.058 (3)0.060 (3)0.005 (2)0.010 (2)0.007 (2)
C240.100 (4)0.097 (4)0.097 (4)−0.036 (4)0.018 (3)−0.018 (3)
C250.127 (6)0.127 (6)0.166 (8)−0.064 (5)0.045 (6)−0.003 (6)
C260.106 (5)0.149 (7)0.136 (7)−0.017 (5)0.061 (5)0.042 (5)
C270.097 (4)0.136 (6)0.074 (4)0.012 (4)0.034 (3)0.014 (4)
C280.071 (3)0.072 (3)0.061 (3)0.002 (2)0.018 (2)−0.003 (2)
C290.055 (2)0.0351 (19)0.047 (2)0.0031 (17)0.0041 (18)0.0047 (16)
C300.047 (2)0.044 (2)0.046 (2)0.0031 (17)0.0070 (18)0.0132 (17)
C310.049 (2)0.060 (3)0.065 (3)0.007 (2)0.002 (2)0.010 (2)
C320.056 (3)0.073 (3)0.082 (3)−0.004 (2)−0.009 (2)0.012 (3)
C330.068 (3)0.060 (3)0.074 (3)−0.009 (2)−0.011 (2)−0.003 (2)
C340.069 (3)0.045 (2)0.066 (3)−0.002 (2)0.004 (2)0.001 (2)
C350.065 (3)0.0331 (19)0.051 (2)0.0102 (18)0.009 (2)0.0040 (17)
C360.073 (3)0.048 (2)0.062 (3)0.023 (2)−0.008 (2)0.005 (2)
C370.050 (2)0.041 (2)0.051 (2)0.0124 (17)0.0021 (18)0.0083 (17)
C380.066 (3)0.052 (2)0.071 (3)0.011 (2)0.018 (2)0.017 (2)
C390.089 (4)0.040 (2)0.106 (4)0.012 (2)0.004 (3)0.023 (2)
C400.103 (4)0.071 (3)0.097 (4)0.048 (3)0.014 (3)0.006 (3)
C410.082 (4)0.097 (4)0.101 (4)0.043 (3)0.038 (3)0.025 (3)
C420.056 (3)0.065 (3)0.093 (3)0.016 (2)0.019 (2)0.032 (3)
Geometric parameters (Å, °) top
Fe—O31.883 (3)C18—C191.382 (6)
Fe—O11.887 (3)C18—H180.9300
Fe—O21.899 (2)C19—C201.375 (6)
Fe—N21.934 (3)C19—H190.9300
Fe—N11.936 (3)C20—H200.9300
Fe—N31.948 (3)C21—H210.9300
O1—C21.306 (4)C22—C231.506 (6)
O2—C161.304 (4)C22—H22A0.9700
O3—C301.314 (4)C22—H22B0.9700
N1—C71.283 (5)C23—C281.363 (6)
N1—C81.485 (5)C23—C241.383 (6)
N2—C211.271 (4)C24—C251.383 (9)
N2—C221.497 (5)C24—H240.9300
N3—C351.279 (5)C25—C261.372 (9)
N3—C361.488 (5)C25—H250.9300
C1—C61.409 (6)C26—C271.353 (8)
C1—C21.413 (6)C26—H260.9300
C1—C71.444 (6)C27—C281.373 (7)
C2—C31.406 (6)C27—H270.9300
C3—C41.358 (6)C28—H280.9300
C3—H30.9300C29—C341.394 (5)
C4—C51.380 (7)C29—C301.416 (5)
C4—H40.9300C29—C351.440 (5)
C5—C61.373 (7)C30—C311.413 (5)
C5—H50.9300C31—C321.371 (6)
C6—H60.9300C31—H310.9300
C7—H70.9300C32—C331.396 (6)
C8—C91.520 (5)C32—H320.9300
C8—H8A0.9700C33—C341.362 (6)
C8—H8B0.9700C33—H330.9300
C9—C101.369 (6)C34—H340.9300
C9—C141.380 (5)C35—H350.9300
C10—C111.402 (6)C36—C371.499 (5)
C10—H100.9300C36—H36A0.9700
C11—C121.362 (7)C36—H36B0.9700
C11—H110.9300C37—C421.375 (6)
C12—C131.354 (7)C37—C381.385 (5)
C12—H120.9300C38—C391.380 (6)
C13—C141.390 (6)C38—H380.9300
C13—H130.9300C39—C401.359 (7)
C14—H140.9300C39—H390.9300
C15—C201.396 (5)C40—C411.374 (7)
C15—C161.406 (5)C40—H400.9300
C15—C211.436 (5)C41—C421.378 (6)
C16—C171.418 (5)C41—H410.9300
C17—C181.358 (6)C42—H420.9300
C17—H170.9300
O3—Fe—O1173.53 (12)C17—C18—C19121.7 (4)
O3—Fe—O288.52 (11)C17—C18—H18119.1
O1—Fe—O289.71 (12)C19—C18—H18119.1
O3—Fe—N288.56 (12)C20—C19—C18118.6 (4)
O1—Fe—N285.23 (13)C20—C19—H19120.7
O2—Fe—N290.60 (12)C18—C19—H19120.7
O3—Fe—N191.87 (12)C19—C20—C15121.5 (4)
O1—Fe—N194.17 (13)C19—C20—H20119.3
O2—Fe—N184.64 (11)C15—C20—H20119.3
N2—Fe—N1175.21 (12)N2—C21—C15125.5 (4)
O3—Fe—N390.66 (12)N2—C21—H21117.2
O1—Fe—N391.47 (13)C15—C21—H21117.2
O2—Fe—N3176.53 (12)N2—C22—C23114.6 (3)
N2—Fe—N392.76 (12)N2—C22—H22A108.6
N1—Fe—N392.01 (12)C23—C22—H22A108.6
C2—O1—Fe125.9 (3)N2—C22—H22B108.6
C16—O2—Fe120.7 (2)C23—C22—H22B108.6
C30—O3—Fe119.9 (2)H22A—C22—H22B107.6
C7—N1—C8116.2 (3)C28—C23—C24118.8 (5)
C7—N1—Fe122.3 (3)C28—C23—C22121.0 (4)
C8—N1—Fe120.6 (2)C24—C23—C22120.1 (4)
C21—N2—C22117.7 (3)C23—C24—C25119.2 (6)
C21—N2—Fe122.0 (3)C23—C24—H24120.4
C22—N2—Fe120.3 (2)C25—C24—H24120.4
C35—N3—C36120.0 (3)C26—C25—C24121.0 (6)
C35—N3—Fe122.2 (3)C26—C25—H25119.5
C36—N3—Fe117.7 (2)C24—C25—H25119.5
C6—C1—C2119.2 (4)C27—C26—C25119.3 (6)
C6—C1—C7117.9 (4)C27—C26—H26120.3
C2—C1—C7122.9 (4)C25—C26—H26120.3
O1—C2—C3119.2 (4)C26—C27—C28120.2 (6)
O1—C2—C1123.0 (4)C26—C27—H27119.9
C3—C2—C1117.8 (4)C28—C27—H27119.9
C4—C3—C2121.4 (5)C23—C28—C27121.5 (5)
C4—C3—H3119.3C23—C28—H28119.3
C2—C3—H3119.3C27—C28—H28119.3
C3—C4—C5121.2 (5)C34—C29—C30119.9 (4)
C3—C4—H4119.4C34—C29—C35120.1 (3)
C5—C4—H4119.4C30—C29—C35119.9 (3)
C6—C5—C4119.3 (5)O3—C30—C31119.1 (3)
C6—C5—H5120.3O3—C30—C29123.5 (3)
C4—C5—H5120.3C31—C30—C29117.4 (4)
C5—C6—C1121.0 (5)C32—C31—C30120.6 (4)
C5—C6—H6119.5C32—C31—H31119.7
C1—C6—H6119.5C30—C31—H31119.7
N1—C7—C1126.9 (4)C31—C32—C33121.7 (4)
N1—C7—H7116.5C31—C32—H32119.1
C1—C7—H7116.5C33—C32—H32119.1
N1—C8—C9113.7 (3)C34—C33—C32118.3 (4)
N1—C8—H8A108.8C34—C33—H33120.8
C9—C8—H8A108.8C32—C33—H33120.8
N1—C8—H8B108.8C33—C34—C29122.0 (4)
C9—C8—H8B108.8C33—C34—H34119.0
H8A—C8—H8B107.7C29—C34—H34119.0
C10—C9—C14118.6 (4)N3—C35—C29125.5 (3)
C10—C9—C8121.5 (4)N3—C35—H35117.3
C14—C9—C8119.8 (4)C29—C35—H35117.3
C9—C10—C11120.6 (4)N3—C36—C37117.2 (3)
C9—C10—H10119.7N3—C36—H36A108.0
C11—C10—H10119.7C37—C36—H36A108.0
C12—C11—C10119.6 (5)N3—C36—H36B108.0
C12—C11—H11120.2C37—C36—H36B108.0
C10—C11—H11120.2H36A—C36—H36B107.2
C13—C12—C11120.5 (4)C42—C37—C38118.4 (4)
C13—C12—H12119.8C42—C37—C36119.3 (4)
C11—C12—H12119.8C38—C37—C36122.2 (4)
C12—C13—C14120.2 (5)C39—C38—C37120.8 (4)
C12—C13—H13119.9C39—C38—H38119.6
C14—C13—H13119.9C37—C38—H38119.6
C9—C14—C13120.5 (5)C40—C39—C38120.0 (4)
C9—C14—H14119.7C40—C39—H39120.0
C13—C14—H14119.7C38—C39—H39120.0
C20—C15—C16119.8 (4)C39—C40—C41120.1 (5)
C20—C15—C21119.6 (4)C39—C40—H40119.9
C16—C15—C21120.1 (3)C41—C40—H40119.9
O2—C16—C15124.1 (3)C40—C41—C42120.1 (5)
O2—C16—C17118.4 (3)C40—C41—H41120.0
C15—C16—C17117.4 (3)C42—C41—H41120.0
C18—C17—C16120.9 (4)C37—C42—C41120.7 (4)
C18—C17—H17119.6C37—C42—H42119.7
C16—C17—H17119.6C41—C42—H42119.7
O3—Fe—O1—C2134.2 (9)C14—C9—C10—C11−1.3 (6)
O2—Fe—O1—C260.1 (3)C8—C9—C10—C11−177.3 (4)
N2—Fe—O1—C2150.7 (3)C9—C10—C11—C120.6 (7)
N1—Fe—O1—C2−24.5 (3)C10—C11—C12—C130.6 (7)
N3—Fe—O1—C2−116.7 (3)C11—C12—C13—C14−1.0 (7)
O3—Fe—O2—C16−46.1 (3)C10—C9—C14—C130.9 (6)
O1—Fe—O2—C16127.7 (3)C8—C9—C14—C13177.0 (4)
N2—Fe—O2—C1642.4 (3)C12—C13—C14—C90.2 (7)
N1—Fe—O2—C16−138.1 (3)Fe—O2—C16—C15−28.7 (5)
N3—Fe—O2—C16−122 (2)Fe—O2—C16—C17153.8 (3)
O1—Fe—O3—C3063.8 (10)C20—C15—C16—O2179.7 (4)
O2—Fe—O3—C30138.0 (3)C21—C15—C16—O2−8.4 (6)
N2—Fe—O3—C3047.4 (3)C20—C15—C16—C17−2.7 (6)
N1—Fe—O3—C30−137.4 (2)C21—C15—C16—C17169.1 (3)
N3—Fe—O3—C30−45.4 (3)O2—C16—C17—C18179.8 (4)
O3—Fe—N1—C7−158.8 (3)C15—C16—C17—C182.2 (6)
O1—Fe—N1—C718.9 (3)C16—C17—C18—C190.7 (7)
O2—Fe—N1—C7−70.4 (3)C17—C18—C19—C20−3.0 (7)
N2—Fe—N1—C7−63.8 (17)C18—C19—C20—C152.3 (7)
N3—Fe—N1—C7110.5 (3)C16—C15—C20—C190.5 (6)
O3—Fe—N1—C89.6 (2)C21—C15—C20—C19−171.3 (4)
O1—Fe—N1—C8−172.7 (2)C22—N2—C21—C15−169.7 (4)
O2—Fe—N1—C898.0 (2)Fe—N2—C21—C158.2 (6)
N2—Fe—N1—C8104.6 (16)C20—C15—C21—N2−168.4 (4)
N3—Fe—N1—C8−81.1 (2)C16—C15—C21—N219.7 (6)
O3—Fe—N2—C2155.8 (3)C21—N2—C22—C2343.0 (5)
O1—Fe—N2—C21−122.3 (3)Fe—N2—C22—C23−135.0 (3)
O2—Fe—N2—C21−32.7 (3)N2—C22—C23—C28−128.0 (4)
N1—Fe—N2—C21−39.3 (18)N2—C22—C23—C2453.2 (6)
N3—Fe—N2—C21146.4 (3)C28—C23—C24—C250.7 (9)
O3—Fe—N2—C22−126.2 (3)C22—C23—C24—C25179.6 (6)
O1—Fe—N2—C2255.6 (3)C23—C24—C25—C26−1.5 (12)
O2—Fe—N2—C22145.3 (3)C24—C25—C26—C271.2 (13)
N1—Fe—N2—C22138.7 (16)C25—C26—C27—C28−0.2 (12)
N3—Fe—N2—C22−35.6 (3)C24—C23—C28—C270.2 (8)
O3—Fe—N3—C3529.1 (3)C22—C23—C28—C27−178.6 (5)
O1—Fe—N3—C35−144.7 (3)C26—C27—C28—C23−0.5 (9)
O2—Fe—N3—C35105 (2)Fe—O3—C30—C31−144.6 (3)
N2—Fe—N3—C35−59.4 (3)Fe—O3—C30—C2936.7 (4)
N1—Fe—N3—C35121.0 (3)C34—C29—C30—O3178.5 (4)
O3—Fe—N3—C36−147.6 (3)C35—C29—C30—O32.1 (6)
O1—Fe—N3—C3638.6 (3)C34—C29—C30—C31−0.2 (5)
O2—Fe—N3—C36−71 (2)C35—C29—C30—C31−176.6 (4)
N2—Fe—N3—C36123.9 (3)O3—C30—C31—C32−179.9 (4)
N1—Fe—N3—C36−55.7 (3)C29—C30—C31—C32−1.1 (6)
Fe—O1—C2—C3−163.3 (3)C30—C31—C32—C330.9 (7)
Fe—O1—C2—C118.6 (5)C31—C32—C33—C340.8 (7)
C6—C1—C2—O1−179.8 (3)C32—C33—C34—C29−2.2 (7)
C7—C1—C2—O1−0.1 (6)C30—C29—C34—C332.0 (6)
C6—C1—C2—C32.1 (5)C35—C29—C34—C33178.4 (4)
C7—C1—C2—C3−178.2 (3)C36—N3—C35—C29174.3 (4)
O1—C2—C3—C4179.9 (4)Fe—N3—C35—C29−2.4 (5)
C1—C2—C3—C4−1.9 (6)C34—C29—C35—N3162.9 (4)
C2—C3—C4—C50.1 (7)C30—C29—C35—N3−20.7 (6)
C3—C4—C5—C61.4 (7)C35—N3—C36—C3728.5 (6)
C4—C5—C6—C1−1.2 (6)Fe—N3—C36—C37−154.7 (3)
C2—C1—C6—C5−0.6 (6)N3—C36—C37—C4294.3 (5)
C7—C1—C6—C5179.6 (3)N3—C36—C37—C38−89.2 (5)
C8—N1—C7—C1−177.2 (3)C42—C37—C38—C39−0.7 (6)
Fe—N1—C7—C1−8.3 (5)C36—C37—C38—C39−177.3 (4)
C6—C1—C7—N1174.7 (3)C37—C38—C39—C400.2 (7)
C2—C1—C7—N1−5.1 (6)C38—C39—C40—C410.1 (8)
C7—N1—C8—C9−110.8 (4)C39—C40—C41—C420.1 (9)
Fe—N1—C8—C980.2 (4)C38—C37—C42—C410.9 (7)
N1—C8—C9—C10−115.1 (4)C36—C37—C42—C41177.6 (4)
N1—C8—C9—C1469.0 (5)C40—C41—C42—C37−0.7 (8)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O30.972.342.830 (2)111
C22—H22B···O10.972.522.978 (2)109
C22—H22B···N30.972.593.018 (2)107
C36—H36B···O10.972.292.938 (2)123
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O30.972.342.830 (2)111
C22—H22B···O10.972.522.978 (2)109
C22—H22B···N30.972.593.018 (2)107
C36—H36B···O10.972.292.938 (2)123
Acknowledgements top

This work was supported by the National Natural Science Foundation of China (No. 30572073), the Natural Science Foundation of Jiangsu Province of China (No. DK2005428), the Medical Science and Technology Development Foundation, Jiangsu Province Department of Health (No. K200402), and the Social Development Foundation of Xuzhou (No. X2003025).

references
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