Tris[2-(propyl­imino­meth­yl)phenolato-κ2N,O]iron(III)

Hao, L.; Mu, C.; Kong, B.

doi:10.1107/S1600536808018540

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page m955

doi:10.1107/S1600536808018540

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RETRACTED ARTICLE

This article has been retracted. To view the retraction notice, click here.

Retracted: Tris[2-(propyliminomethyl)phenolato-κ²N,O]iron(III)

Lujiang Hao,^a ^* Chunhua Mu ^b and Binbin Kong ^a

^aCollege of Food and Biological Engineering, Shandong Institute of Light Industry, Jinan 250353, People's Republic of China, and ^bMaize Research Insitute, Shandong Academy of Agricultural Science, Jinan 250100, People's Republic of China
^*Correspondence e-mail: lujianghao001@yahoo.com.cn

(Received 14 June 2008; accepted 19 June 2008; online 25 June 2008)

The title compound, [Fe(C₁₀H₁₂NO)₃], is isostructural with its Co^III-containing analogue. The Fe^III cation is chelated by three Schiff base ligands via three N and three O atoms, and exhibits a slightly distorted octahedral geometry. The longest Fe—O and Fe—N bonds lie trans to each other and may be regarded as axial bonds, while the equatorial plane contains two mutually trans O and two trans N atoms.

Related literature

For related literature, see: Iskander et al. (2001 ); Caruso et al. (2005 ); Sangeetha & Pal (2000 ); Rajak et al. (2000 ); Sutradhar et al. (2006 ). For the isostructural Co complex, see: Li et al. (2008 ).

Experimental

Crystal data

[Fe(C₁₀H₁₂NO)₃]
M_r = 542.47
Tetragonal, I 4₁ /a
a = 19.369 (2) Å
c = 30.216 (3) Å
V = 11336 (2) Å³
Z = 16
Mo Kα radiation
μ = 0.57 mm⁻¹
T = 293 (2) K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.935, T_max = 0.956
41740 measured reflections
5198 independent reflections
3125 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.099
S = 1.00
5198 reflections
337 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018540/cf2206sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018540/cf2206Isup2.hkl

checkCIF report

Comment top

The design and construction of novel discrete Schiff-basd metal complexes has attracted long-lasting research interest, not only because of their appealing structural and topological features, but also due to their unusual optical, electronic, magnetic and catalytic properties, and their further potential medical value derived from their antiviral properties and inhibition of angiogenesis (Iskander et al. 2001; Caruso et al. 2005; Sangeetha & Pal, 2000; Rajak et al. 2000; Sutradhar et al. 2006). Here we report the synthesis and X-ray crystal structure analysis of the title compound, which is isostructural with its Co^III-containing analogue (Li et al., 2008).

As shown in Figure 1, the Fe^III cation is chelated by three Schiff base ligands via three N and three O atoms, and exhibits a slightly distorted octahedral geometry. The Fe—N and Fe—O bond lengths are in the ranges 1.917 (3)–1.969 (3) and 1.846 (2)–1.913 (2) Å, respectively. The Fe1—O2 and Fe1—N2 bonds are much longer than the other related ones. Thus the atoms O1, O3, N1, and N3 may be considered to lie in the equatorial plane, and O2 and N2 in the axial coordination sites.

Related literature top

For related literature, see: Iskander et al. (2001); Caruso et al. (2005); Sangeetha & Pal (2000); Rajak et al. (2000); Sutradhar et al. (2006). For the isostructural Co complex, see: Li et al. (2008).

Experimental top

A mixture of iron(III) acetylacetonate (0.5 mmol) and 2-(propyliminomethyl)phenol (0.5 mmol) in 20 ml methanol was refluxed for several hours. The filtrate obtained from this soution was allowed to evaporate at room temperature for three days. Brown crystals were obtained with a yield of 5%. Anal. Calc. for C₃₀H₃₆FeN₃O₃: C 65.36, H 6.64 N 7.74%; Found: C 65.21, H 6.59, N 7.67%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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

Fig. 1. The molecular structure of (I), drawn with 30% probability displacement ellipsoids for the non-hydrogen atoms.

Tris[2-(propyliminomethyl)phenolato-κ²N,O]iron(III) top

Crystal data top

[Fe(C₁₀H₁₂NO)₃]	D_x = 1.271 Mg m⁻³
M_r = 542.47	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 5198 reflections
Hall symbol: -I 4ad	θ = 1.3–25.5°
a = 19.369 (2) Å	µ = 0.57 mm⁻¹
c = 30.216 (3) Å	T = 293 K
V = 11336 (2) Å³	Block, green
Z = 16	0.12 × 0.10 × 0.08 mm
F(000) = 4592

Data collection top

Bruker APEXII CCD diffractometer	5198 independent reflections
Radiation source: fine-focus sealed tube	3125 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −23→22
T_min = 0.935, T_max = 0.956	k = −23→23
41740 measured reflections	l = −36→36

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0375P)²] where P = (F_o² + 2F_c²)/3
5198 reflections	(Δ/σ)_max < 0.001
337 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

[Fe(C₁₀H₁₂NO)₃]	Z = 16
M_r = 542.47	Mo Kα radiation
Tetragonal, I4₁/a	µ = 0.57 mm⁻¹
a = 19.369 (2) Å	T = 293 K
c = 30.216 (3) Å	0.12 × 0.10 × 0.08 mm
V = 11336 (2) Å³

Data collection top

Bruker APEXII CCD diffractometer	5198 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3125 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.956	R_int = 0.073
41740 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.00	Δρ_max = 0.33 e Å⁻³
5198 reflections	Δρ_min = −0.27 e Å⁻³
337 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

	x	y	z	U_iso*/U_eq
Fe1	0.22632 (2)	0.98149 (2)	0.992992 (13)	0.05735 (17)
C1	0.14742 (16)	0.94922 (15)	0.89961 (9)	0.0579 (8)
C2	0.10654 (19)	0.94259 (17)	0.86092 (10)	0.0703 (9)
H2	0.1202	0.9650	0.8352	0.084*
C3	0.04851 (19)	0.90467 (18)	0.86056 (12)	0.0783 (10)
H3	0.0213	0.9020	0.8353	0.094*
C4	0.03008 (16)	0.86948 (17)	0.89893 (12)	0.0755 (9)
H4	−0.0097	0.8426	0.8989	0.091*
C5	0.06917 (16)	0.87330 (15)	0.93694 (10)	0.0647 (8)
H5	0.0554	0.8488	0.9619	0.078*
C6	0.12904 (15)	0.91330 (14)	0.93872 (10)	0.0548 (7)
C7	0.09561 (16)	0.97163 (15)	1.05726 (9)	0.0577 (8)
C8	0.03352 (16)	0.95695 (16)	1.07764 (10)	0.0693 (9)
H8	−0.0047	0.9843	1.0713	0.083*
C9	0.02656 (19)	0.90334 (17)	1.10688 (11)	0.0745 (9)
H9	−0.0158	0.8943	1.1202	0.089*
C10	0.0822 (2)	0.86399 (18)	1.11603 (10)	0.0749 (9)
H10	0.0774	0.8266	1.1351	0.090*
C11	0.14583 (19)	0.87783 (16)	1.09771 (10)	0.0706 (9)
H11	0.1836	0.8506	1.1053	0.085*
C12	0.15458 (16)	0.93302 (15)	1.06737 (9)	0.0561 (8)
C13	0.34061 (18)	1.0494 (2)	1.03341 (11)	0.0738 (9)
C14	0.3673 (2)	1.1078 (2)	1.05590 (13)	0.1009 (12)
H14	0.3404	1.1474	1.0587	0.121*
C15	0.4327 (2)	1.1063 (3)	1.07356 (14)	0.1233 (17)
H15	0.4494	1.1449	1.0885	0.148*
C16	0.4732 (2)	1.0498 (3)	1.06961 (15)	0.1199 (16)
H16	0.5172	1.0495	1.0819	0.144*
C17	0.4490 (2)	0.9930 (3)	1.04737 (13)	0.1051 (13)
H17	0.4772	0.9544	1.0445	0.126*
C18	0.38262 (17)	0.9922 (2)	1.02892 (11)	0.0764 (10)
C19	0.36133 (19)	0.9318 (2)	1.00561 (11)	0.0781 (10)
H19	0.3945	0.8974	1.0026	0.094*
C20	0.20828 (17)	0.98920 (16)	0.89763 (11)	0.0678 (9)
H20	0.2235	1.0028	0.8698	0.081*
C21	0.09974 (16)	1.02899 (16)	1.02768 (10)	0.0660 (8)
H21	0.0631	1.0600	1.0285	0.079*
C22	0.14568 (17)	1.10734 (17)	0.97424 (12)	0.0844 (10)
H22A	0.1397	1.0951	0.9433	0.101*
H22B	0.1903	1.1297	0.9769	0.101*
C23	0.0919 (2)	1.15896 (17)	0.98566 (12)	0.0889 (11)
H23A	0.0971	1.1730	1.0163	0.107*
H23B	0.0465	1.1386	0.9821	0.107*
C24	0.0987 (2)	1.22091 (17)	0.95597 (13)	0.1048 (13)
H24A	0.1464	1.2340	0.9539	0.157*
H24B	0.0725	1.2586	0.9680	0.157*
H24C	0.0814	1.2098	0.9270	0.157*
C25	0.3097 (2)	1.0451 (3)	0.92058 (14)	0.1238 (15)
H25A	0.3341	1.0515	0.9483	0.149*
H25B	0.3373	1.0136	0.9029	0.149*
C26	0.3106 (3)	1.1023 (3)	0.9010 (2)	0.126 (3)
H26A	0.2831	1.1346	0.9182	0.240*
H26B	0.2878	1.0966	0.8727	0.240*
C27	0.3813 (2)	1.1356 (2)	0.89256 (15)	0.1331 (17)
H27A	0.3935	1.1643	0.9173	0.200*
H27B	0.3792	1.1632	0.8662	0.200*
H27C	0.4154	1.1001	0.8890	0.200*
C28	0.29461 (18)	0.85217 (19)	0.96588 (12)	0.0870 (11)
H28A	0.3396	0.8358	0.9565	0.104*
H28B	0.2665	0.8584	0.9396	0.104*
C29	0.2615 (2)	0.7984 (2)	0.99533 (14)	0.1041 (13)
H29A	0.2164	0.8152	1.0043	0.125*
H29B	0.2541	0.7569	0.9779	0.125*
C30	0.3005 (2)	0.7793 (2)	1.03570 (18)	0.1528 (19)
H30A	0.3439	0.7591	1.0274	0.229*
H30B	0.2743	0.7465	1.0526	0.229*
H30C	0.3087	0.8198	1.0532	0.229*
N1	0.30265 (14)	0.91895 (14)	0.98831 (8)	0.0679 (7)
N2	0.24462 (14)	1.00853 (13)	0.93127 (9)	0.0697 (7)
N3	0.14842 (12)	1.04268 (13)	0.99995 (8)	0.0635 (7)
O1	0.27883 (11)	1.05426 (11)	1.01689 (7)	0.0753 (6)
O2	0.21526 (10)	0.94675 (11)	1.05183 (6)	0.0651 (6)
O3	0.16501 (10)	0.91380 (10)	0.97551 (6)	0.0622 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0520 (3)	0.0673 (3)	0.0527 (3)	0.0034 (2)	0.0019 (2)	−0.0006 (2)
C1	0.068 (2)	0.0595 (19)	0.0458 (18)	0.0098 (17)	0.0056 (16)	−0.0015 (15)
C2	0.092 (3)	0.071 (2)	0.049 (2)	0.010 (2)	0.0032 (18)	−0.0026 (16)
C3	0.086 (3)	0.086 (3)	0.063 (2)	0.001 (2)	−0.011 (2)	−0.0124 (19)
C4	0.064 (2)	0.079 (2)	0.084 (3)	0.0000 (18)	−0.007 (2)	−0.021 (2)
C5	0.066 (2)	0.062 (2)	0.066 (2)	0.0029 (17)	0.0066 (17)	−0.0042 (16)
C6	0.060 (2)	0.0522 (18)	0.0517 (19)	0.0087 (15)	0.0042 (16)	−0.0050 (15)
C7	0.064 (2)	0.0522 (18)	0.0571 (19)	0.0062 (16)	0.0055 (16)	−0.0028 (15)
C8	0.070 (2)	0.064 (2)	0.074 (2)	0.0055 (17)	0.0133 (18)	−0.0013 (18)
C9	0.085 (3)	0.068 (2)	0.070 (2)	−0.005 (2)	0.0171 (19)	−0.0010 (19)
C10	0.104 (3)	0.064 (2)	0.057 (2)	−0.006 (2)	0.013 (2)	0.0015 (16)
C11	0.095 (3)	0.062 (2)	0.055 (2)	0.0135 (19)	−0.0056 (19)	−0.0051 (17)
C12	0.067 (2)	0.0582 (19)	0.0436 (17)	0.0072 (17)	0.0007 (16)	−0.0091 (15)
C13	0.057 (2)	0.095 (3)	0.069 (2)	−0.010 (2)	0.0062 (18)	−0.006 (2)
C14	0.072 (3)	0.126 (3)	0.105 (3)	−0.012 (2)	0.004 (2)	−0.034 (3)
C15	0.074 (3)	0.184 (5)	0.112 (3)	−0.033 (3)	−0.001 (3)	−0.050 (3)
C16	0.065 (3)	0.183 (5)	0.112 (4)	−0.007 (3)	−0.016 (3)	−0.023 (4)
C17	0.061 (3)	0.153 (4)	0.101 (3)	0.001 (3)	0.000 (2)	−0.001 (3)
C18	0.053 (2)	0.106 (3)	0.070 (2)	0.004 (2)	0.0030 (18)	−0.002 (2)
C19	0.066 (2)	0.095 (3)	0.074 (2)	0.019 (2)	0.013 (2)	0.002 (2)
C20	0.074 (2)	0.077 (2)	0.052 (2)	0.0004 (19)	0.0096 (17)	0.0060 (17)
C21	0.060 (2)	0.064 (2)	0.074 (2)	0.0074 (17)	0.0052 (17)	0.0079 (17)
C22	0.075 (2)	0.079 (2)	0.099 (3)	0.005 (2)	0.015 (2)	0.027 (2)
C23	0.104 (3)	0.074 (2)	0.089 (3)	0.007 (2)	−0.005 (2)	0.002 (2)
C24	0.130 (3)	0.065 (2)	0.120 (3)	0.001 (2)	−0.008 (3)	0.021 (2)
C25	0.127 (4)	0.144 (4)	0.100 (3)	−0.035 (3)	−0.002 (3)	0.037 (3)
C26	0.148 (8)	0.122 (7)	0.110 (7)	−0.007 (6)	−0.014 (6)	−0.005 (6)
C27	0.124 (4)	0.118 (3)	0.157 (4)	−0.063 (3)	0.028 (3)	0.000 (3)
C28	0.080 (3)	0.092 (3)	0.089 (3)	0.021 (2)	0.007 (2)	−0.024 (2)
C29	0.108 (3)	0.076 (3)	0.129 (4)	0.014 (2)	0.000 (3)	0.007 (3)
C30	0.139 (4)	0.138 (4)	0.182 (5)	0.003 (3)	−0.040 (4)	0.040 (4)
N1	0.0608 (17)	0.083 (2)	0.0596 (16)	0.0104 (15)	0.0072 (14)	−0.0056 (14)
N2	0.0630 (17)	0.0785 (19)	0.0675 (18)	−0.0054 (15)	0.0064 (15)	0.0089 (15)
N3	0.0560 (15)	0.0691 (17)	0.0653 (17)	0.0024 (13)	0.0007 (13)	0.0120 (14)
O1	0.0568 (14)	0.0766 (15)	0.0925 (17)	0.0006 (12)	−0.0033 (12)	−0.0077 (12)
O2	0.0572 (13)	0.0848 (15)	0.0532 (12)	0.0147 (11)	−0.0012 (10)	−0.0047 (11)
O3	0.0650 (13)	0.0710 (14)	0.0506 (12)	−0.0013 (10)	−0.0026 (10)	0.0063 (10)

Geometric parameters (Å, º) top

Fe1—O3	1.846 (2)	C17—C18	1.402 (5)
Fe1—O1	1.882 (2)	C17—H17	0.930
Fe1—O2	1.913 (2)	C18—C19	1.425 (5)
Fe1—N1	1.917 (3)	C19—N1	1.276 (4)
Fe1—N3	1.930 (2)	C19—H19	0.930
Fe1—N2	1.969 (3)	C20—N2	1.292 (4)
C1—C20	1.412 (4)	C20—H20	0.930
C1—C2	1.418 (4)	C21—N3	1.289 (3)
C1—C6	1.417 (4)	C21—H21	0.930
C2—C3	1.343 (4)	C22—N3	1.475 (4)
C2—H2	0.930	C22—C23	1.484 (4)
C3—C4	1.392 (4)	C22—H22A	0.970
C3—H3	0.930	C22—H22B	0.970
C4—C5	1.378 (4)	C23—C24	1.504 (4)
C4—H4	0.930	C23—H23A	0.970
C5—C6	1.396 (4)	C23—H23B	0.970
C5—H5	0.930	C24—H24A	0.960
C6—O3	1.312 (3)	C24—H24B	0.960
C7—C8	1.381 (4)	C24—H24C	0.960
C7—C12	1.399 (4)	C25—C26	1.257 (5)
C7—C21	1.428 (4)	C25—N2	1.481 (5)
C8—C9	1.370 (4)	C25—H25A	0.970
C8—H8	0.930	C25—H25B	0.970
C9—C10	1.348 (4)	C26—C27	1.535 (6)
C9—H9	0.930	C26—H26A	0.970
C10—C11	1.378 (4)	C26—H26B	0.970
C10—H10	0.930	C27—H27A	0.960
C11—C12	1.418 (4)	C27—H27B	0.960
C11—H11	0.930	C27—H27C	0.960
C12—O2	1.293 (3)	C28—N1	1.469 (4)
C13—O1	1.300 (4)	C28—C29	1.514 (5)
C13—C18	1.382 (5)	C28—H28A	0.970
C13—C14	1.418 (5)	C28—H28B	0.970
C14—C15	1.376 (5)	C29—C30	1.482 (5)
C14—H14	0.930	C29—H29A	0.970
C15—C16	1.352 (6)	C29—H29B	0.970
C15—H15	0.930	C30—H30A	0.960
C16—C17	1.372 (5)	C30—H30B	0.960
C16—H16	0.930	C30—H30C	0.960

O3—Fe1—O1	171.58 (9)	N2—C20—C1	125.5 (3)
O3—Fe1—O2	86.80 (8)	N2—C20—H20	117.2
O1—Fe1—O2	88.13 (9)	C1—C20—H20	117.2
O3—Fe1—N1	91.50 (11)	N3—C21—C7	127.4 (3)
O1—Fe1—N1	94.86 (11)	N3—C21—H21	116.3
O2—Fe1—N1	86.14 (9)	C7—C21—H21	116.3
O3—Fe1—N3	87.97 (10)	N3—C22—C23	118.4 (3)
O1—Fe1—N3	85.46 (10)	N3—C22—H22A	107.7
O2—Fe1—N3	91.56 (9)	C23—C22—H22A	107.7
N1—Fe1—N3	177.67 (10)	N3—C22—H22B	107.7
O3—Fe1—N2	91.93 (10)	C23—C22—H22B	107.7
O1—Fe1—N2	93.83 (11)	H22A—C22—H22B	107.1
O2—Fe1—N2	173.65 (9)	C22—C23—C24	109.7 (3)
N1—Fe1—N2	87.67 (10)	C22—C23—H23A	109.7
N3—Fe1—N2	94.62 (10)	C24—C23—H23A	109.7
C20—C1—C2	118.8 (3)	C22—C23—H23B	109.7
C20—C1—C6	121.0 (3)	C24—C23—H23B	109.7
C2—C1—C6	120.2 (3)	H23A—C23—H23B	108.2
C3—C2—C1	121.6 (3)	C23—C24—H24A	109.5
C3—C2—H2	119.2	C23—C24—H24B	109.5
C1—C2—H2	119.2	H24A—C24—H24B	109.5
C2—C3—C4	118.4 (3)	C23—C24—H24C	109.5
C2—C3—H3	120.8	H24A—C24—H24C	109.5
C4—C3—H3	120.8	H24B—C24—H24C	109.5
C5—C4—C3	121.8 (3)	C26—C25—N2	122.4 (5)
C5—C4—H4	119.1	C26—C25—H25A	106.7
C3—C4—H4	119.1	N2—C25—H25A	106.7
C4—C5—C6	121.2 (3)	C26—C25—H25B	106.7
C4—C5—H5	119.4	N2—C25—H25B	106.7
C6—C5—H5	119.4	H25A—C25—H25B	106.6
O3—C6—C5	118.6 (3)	C25—C26—C27	117.4 (5)
O3—C6—C1	124.7 (3)	C25—C26—H26A	108.0
C5—C6—C1	116.7 (3)	C27—C26—H26A	107.9
C8—C7—C12	120.2 (3)	C25—C26—H26B	107.9
C8—C7—C21	119.2 (3)	C27—C26—H26B	107.9
C12—C7—C21	120.5 (3)	H26A—C26—H26B	107.2
C9—C8—C7	122.0 (3)	C26—C27—H27A	109.5
C9—C8—H8	119.0	C26—C27—H27B	109.5
C7—C8—H8	119.0	H27A—C27—H27B	109.5
C10—C9—C8	118.8 (3)	C26—C27—H27C	109.5
C10—C9—H9	120.6	H27A—C27—H27C	109.5
C8—C9—H9	120.6	H27B—C27—H27C	109.5
C9—C10—C11	121.5 (3)	N1—C28—C29	112.3 (3)
C9—C10—H10	119.2	N1—C28—H28A	109.1
C11—C10—H10	119.2	C29—C28—H28A	109.1
C10—C11—C12	120.9 (3)	N1—C28—H28B	109.1
C10—C11—H11	119.6	C29—C28—H28B	109.1
C12—C11—H11	119.6	H28A—C28—H28B	107.9
O2—C12—C7	123.5 (3)	C30—C29—C28	116.0 (4)
O2—C12—C11	119.9 (3)	C30—C29—H29A	108.3
C7—C12—C11	116.5 (3)	C28—C29—H29A	108.3
O1—C13—C18	124.2 (3)	C30—C29—H29B	108.3
O1—C13—C14	117.5 (4)	C28—C29—H29B	108.3
C18—C13—C14	118.3 (3)	H29A—C29—H29B	107.4
C15—C14—C13	120.3 (4)	C29—C30—H30A	109.5
C15—C14—H14	119.9	C29—C30—H30B	109.5
C13—C14—H14	119.9	H30A—C30—H30B	109.5
C14—C15—C16	121.2 (4)	C29—C30—H30C	109.5
C14—C15—H15	119.4	H30A—C30—H30C	109.5
C16—C15—H15	119.4	H30B—C30—H30C	109.5
C15—C16—C17	119.6 (4)	C19—N1—C28	117.1 (3)
C15—C16—H16	120.2	C19—N1—Fe1	122.2 (2)
C17—C16—H16	120.2	C28—N1—Fe1	120.6 (2)
C16—C17—C18	121.2 (4)	C20—N2—C25	115.5 (3)
C16—C17—H17	119.4	C20—N2—Fe1	124.7 (2)
C18—C17—H17	119.4	C25—N2—Fe1	119.1 (2)
C17—C18—C13	119.5 (4)	C21—N3—C22	119.4 (3)
C17—C18—C19	118.1 (4)	C21—N3—Fe1	121.1 (2)
C13—C18—C19	122.4 (3)	C22—N3—Fe1	119.5 (2)
N1—C19—C18	128.3 (3)	C13—O1—Fe1	126.2 (2)
N1—C19—H19	115.8	C12—O2—Fe1	120.76 (18)
C18—C19—H19	115.8	C6—O3—Fe1	126.11 (18)

Experimental details

Crystal data
Chemical formula	[Fe(C₁₀H₁₂NO)₃]
M_r	542.47
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	293
a, c (Å)	19.369 (2), 30.216 (3)
V (Å³)	11336 (2)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.57
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.935, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	41740, 5198, 3125
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.099, 1.00
No. of reflections	5198
No. of parameters	337
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.27

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the National Ministry of Science and Technology of China (grant No. 2001CB6105–07).

References

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