Tris[μ-2,2′-(azinodimethylidyne)diphenolato-κ4O,N:N′,O′]diiron(III) tetra­hydro­furan tetra­solvate

Wang, J.; Liu, B.; Yang, B.

doi:10.1107/S1600536808027438

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1210

doi:10.1107/S1600536808027438

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Tris[μ-2,2′-(azinodimethylidyne)diphenolato-κ⁴O,N:N′,O′]diiron(III) tetrahydrofuran tetrasolvate

Jinglin Wang,^a Bin Liu ^a and Binsheng Yang ^a ^*

^aInstitute of Molecular Science, Chemical Biology and Molecular Engineering Laboratory of the Education Ministry, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China
^*Correspondence e-mail: yangbs@sxu.edu.cn

(Received 22 July 2008; accepted 26 August 2008; online 30 August 2008)

In the title binuclear iron(III) complex, [Fe₂(C₁₄H₁₀N₂O₂)₃]·4C₄H₈O or [Fe₂(salda)₃]·4THF [H₂salda = 2,2′-(azinidimethylene)diphenolate and THF is tetrahydrofuran], the ligand possesses a rotationally flexible single N—N bond. Three dinucleating O,N:N′,O′-donor ligands provide three diazine (=N—N=) bridges between the metal ions, yielding a binuclear triple helicate structure with crystallographic C₂ symmetry, the rotation axis bisecting one N—N bond.

Related literature

For related literature, see: Seo et al. (2000 ); Gao et al. (2004 ); Oleksi et al. (2006 ).

Experimental

Crystal data

[Fe₂(C₁₄H₁₀N₂O₂)₃]·4C₄H₈O
M_r = 1114.84
Orthorhombic, P b c n
a = 15.189 (5) Å
b = 19.163 (6) Å
c = 18.917 (6) Å
V = 5506 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 293 (2) K
0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.798, T_max = 0.891
21523 measured reflections
4856 independent reflections
3520 reflections with I > 2σ(I)
R_int = 0.080

Refinement

R[F² > 2σ(F²)] = 0.083
wR(F²) = 0.222
S = 1.08
4856 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 0.96 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536808027438/cf2210sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027438/cf2210Isup2.hkl

checkCIF report

Comment top

During recent decades, the study of helical coordination complexes or helicates has become an area of intense research activity, due to their intriguing potential applications in enantioselective synthesis and asymmetric catalysis, designing nonlinear optical materials, magnetic materials and porous materials, probing DNA structures, and understanding helical self-organization processes operative in nature (Seo et al., 2000; Gao et al., 2004; Oleksi et al., 2006). In this paper, we report the synthesis and crystal structure of the title complex [Fe₂(salda)₃].4THF. Due to the presence of 6 aromatic rings around two Fe(III) ions, the complex displays a large hydrophobic surface and a small diameter (~1.5 nm). These characteristics can be driving forces for the non-covalent recognition of DNA, biological labels and nanoparticle probes by the helicate. The molecular structure of [Fe₂(salda)₃].4THF is shown in Fig. 1. In the complex, each of the three ligands coordinates the two metal ions via the two phenolate O and the two imine N atoms. Thus, the metal ions are in facial O₃N₃ coordination environments and are connected by three diaza (═N—N═) bridges to yield a binuclear triple helicate. The Fe···Fe distance spanned by the triple N—N bridges is 3.9615 (16) Å. The three Fe—N—N—Fe torsion angles are -48.1 (5)° and two symmetry-equivalent at -67.6 (3)°; The complex has C₂ symmetry with a 2-fold rotation axis through the midpoints of Fe1···Fe1A and N2—N2A (symmetry code as in Fig. 2). A packing diagram is shown in Fig. 3.

Related literature top

For related literature, see: Seo et al. (2000); Gao et al. (2004); Oleksi et al. (2006).

Experimental top

The ligand H₂salda was prepared by reacting hydrazine with 2 equiv of salicylaldehyde followed by recrystallization from methanol. To a solution of 360 mg (1.5 mmol) of H₂salda dissolved in 30 ml of methanol was added a solution of 3% (g/100 ml) sodium methoxide in 0.4 ml methanol. FeCl_3.H₂O (270 mg, 1 mmol) in methanol (15 ml) was added dropwise to the resulting brownish-black solution. The reaction mixture was stirred and refluxed on a water bath for 2 h. The resulting precipitate was filtered off, and washed successively with methanol and THF prior to drying in vacuo. The dried powder was dissolved in THF and crystals suitable for X-ray analysis were obtained after two weeks at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: A, -x, y, 1/2-z.]
	Fig. 2. The coordination environment of the Fe(III) atoms. All non-hydrogen atoms are represented by 30% displacement probability ellipsoids. [Symmetry code: A, -x, y, 1/2-z.]
	Fig. 3. The packing of the title compound.

Tris[µ-2,2'-(azinodimethylidyne)diphenolato-κ⁴O,N:N',O']diiron(III) tetrahydrofuran tetrasolvate top

Crystal data top

[Fe₂(C₁₄H₁₀N₂O₂)₃]·4C₄H₈O	D_x = 1.345 Mg m⁻³
M_r = 1114.84	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 30326 reflections
a = 15.189 (5) Å	θ = 1.7–25.0°
b = 19.163 (6) Å	µ = 0.59 mm⁻¹
c = 18.917 (6) Å	T = 293 K
V = 5506 (3) Å³	Block, black
Z = 4	0.40 × 0.40 × 0.20 mm
F(000) = 2336

Data collection top

Bruker SMART CCD diffractometer	4856 independent reflections
Radiation source: fine-focus sealed tube	3520 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→11
T_min = 0.798, T_max = 0.891	k = −21→22
21523 measured reflections	l = −21→22

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)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.222	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.1154P)² + 5.1454P] where P = (F_o² + 2F_c²)/3
4856 reflections	(Δ/σ)_max < 0.001
343 parameters	Δρ_max = 0.96 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Fe₂(C₁₄H₁₀N₂O₂)₃]·4C₄H₈O	V = 5506 (3) Å³
M_r = 1114.84	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 15.189 (5) Å	µ = 0.59 mm⁻¹
b = 19.163 (6) Å	T = 293 K
c = 18.917 (6) Å	0.40 × 0.40 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	4856 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3520 reflections with I > 2σ(I)
T_min = 0.798, T_max = 0.891	R_int = 0.080
21523 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.083	0 restraints
wR(F²) = 0.222	H-atom parameters constrained
S = 1.09	Δρ_max = 0.96 e Å⁻³
4856 reflections	Δρ_min = −0.42 e Å⁻³
343 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
C22	0.140 (2)	0.6626 (11)	0.2989 (14)	0.317 (18)
H22A	0.1376	0.6984	0.2628	0.380*
H22B	0.0997	0.6757	0.3364	0.380*
Fe1	0.10583 (4)	0.30805 (3)	0.18882 (3)	0.0431 (3)
O2	0.0996 (2)	0.34432 (18)	0.09508 (17)	0.0530 (9)
O3	0.2127 (2)	0.35565 (19)	0.21251 (18)	0.0560 (9)
O1	0.1549 (2)	0.21832 (18)	0.16629 (19)	0.0539 (9)
N2	0.0242 (2)	0.39989 (19)	0.21748 (19)	0.0423 (9)
N1	−0.0194 (2)	0.2536 (2)	0.17748 (18)	0.0410 (9)
N3	0.0962 (2)	0.2897 (2)	0.3007 (2)	0.0416 (9)
C7	−0.0316 (3)	0.1927 (2)	0.1519 (3)	0.0478 (11)
H7	−0.0896	0.1779	0.1467	0.057*
C6	0.0360 (3)	0.1452 (2)	0.1305 (3)	0.0473 (11)
C5	0.0111 (4)	0.0804 (3)	0.1022 (3)	0.0631 (15)
H5	−0.0485	0.0704	0.0975	0.076*
C4	0.0709 (4)	0.0318 (3)	0.0814 (3)	0.0728 (17)
H4	0.0528	−0.0110	0.0631	0.087*
C3	0.1602 (4)	0.0479 (3)	0.0882 (3)	0.0688 (16)
H3	0.2021	0.0153	0.0742	0.083*
C2	0.1870 (4)	0.1102 (3)	0.1147 (3)	0.0604 (14)
H2	0.2469	0.1197	0.1176	0.072*
C1	0.1264 (3)	0.1605 (2)	0.1380 (2)	0.0461 (11)
C14	0.0218 (3)	0.4552 (3)	0.1792 (2)	0.0462 (11)
H14	−0.0117	0.4923	0.1961	0.055*
C13	0.0658 (3)	0.4651 (3)	0.1129 (2)	0.0464 (11)
C12	0.0676 (4)	0.5322 (3)	0.0848 (3)	0.0568 (13)
H12	0.0416	0.5684	0.1100	0.068*
C11	0.1067 (4)	0.5466 (3)	0.0209 (3)	0.0662 (16)
H11	0.1088	0.5920	0.0036	0.079*
C10	0.1426 (4)	0.4923 (3)	−0.0169 (3)	0.0673 (16)
H10	0.1685	0.5013	−0.0605	0.081*
C9	0.1413 (4)	0.4253 (3)	0.0082 (3)	0.0619 (14)
H9	0.1664	0.3899	−0.0186	0.074*
C8	0.1028 (3)	0.4088 (3)	0.0735 (2)	0.0481 (12)
C21	0.1480 (3)	0.3112 (2)	0.3498 (2)	0.0453 (11)
H21	0.1329	0.3008	0.3963	0.054*
C20	0.2278 (3)	0.3502 (2)	0.3381 (3)	0.0484 (12)
C19	0.2779 (4)	0.3683 (3)	0.3974 (3)	0.0654 (15)
H19	0.2580	0.3560	0.4422	0.078*
C18	0.3563 (4)	0.4040 (4)	0.3904 (4)	0.083 (2)
H18	0.3898	0.4153	0.4300	0.100*
C17	0.3842 (4)	0.4227 (4)	0.3237 (4)	0.080 (2)
H17	0.4367	0.4472	0.3188	0.096*
C16	0.3368 (4)	0.4064 (3)	0.2649 (3)	0.0660 (16)
H16	0.3577	0.4196	0.2206	0.079*
C15	0.2565 (3)	0.3698 (2)	0.2702 (3)	0.0490 (12)
C23	0.2248 (11)	0.6588 (9)	0.3259 (10)	0.250 (13)
H23A	0.2241	0.6661	0.3766	0.300*
H23B	0.2616	0.6944	0.3046	0.300*
C24	0.2577 (6)	0.5921 (6)	0.3100 (5)	0.125 (3)
H24A	0.2754	0.5683	0.3529	0.149*
H24B	0.3084	0.5957	0.2790	0.149*
C25	0.1866 (5)	0.5537 (5)	0.2749 (5)	0.103 (2)
H25A	0.2058	0.5390	0.2284	0.123*
H25B	0.1721	0.5124	0.3021	0.123*
C26	0.0389 (9)	0.2553 (8)	0.5461 (8)	0.195 (6)
H26A	0.0013	0.2226	0.5212	0.234*
H26B	0.0078	0.2988	0.5537	0.234*
O5	0.1208 (6)	0.2653 (5)	0.5114 (4)	0.182 (4)
C27	0.074 (2)	0.2259 (13)	0.6122 (9)	0.319 (16)
H27A	0.1107	0.2581	0.6382	0.382*
H27B	0.0281	0.2068	0.6427	0.382*
O4	0.1119 (6)	0.5964 (7)	0.2687 (6)	0.210 (4)
C29	0.1815 (9)	0.2172 (7)	0.5369 (8)	0.176 (5)
H29A	0.2243	0.2388	0.5681	0.212*
H29B	0.2118	0.1931	0.4989	0.212*
C28	0.123 (2)	0.1724 (9)	0.5741 (11)	0.336 (19)
H28A	0.1541	0.1412	0.6058	0.403*
H28B	0.0860	0.1456	0.5424	0.403*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C22	0.46 (4)	0.135 (14)	0.35 (3)	0.10 (2)	0.18 (3)	0.072 (18)
Fe1	0.0335 (4)	0.0488 (4)	0.0470 (4)	−0.0021 (3)	0.0011 (3)	−0.0014 (3)
O2	0.057 (2)	0.057 (2)	0.0457 (18)	0.0009 (17)	0.0023 (16)	−0.0001 (16)
O3	0.042 (2)	0.070 (2)	0.055 (2)	−0.0128 (17)	0.0025 (17)	0.0021 (17)
O1	0.0350 (18)	0.054 (2)	0.073 (2)	0.0036 (16)	−0.0004 (17)	−0.0111 (18)
N2	0.037 (2)	0.046 (2)	0.044 (2)	−0.0020 (17)	0.0004 (17)	0.0001 (17)
N1	0.031 (2)	0.046 (2)	0.046 (2)	0.0018 (17)	0.0020 (16)	−0.0027 (17)
N3	0.031 (2)	0.045 (2)	0.048 (2)	−0.0015 (16)	0.0011 (17)	0.0037 (17)
C7	0.037 (3)	0.052 (3)	0.055 (3)	−0.007 (2)	0.003 (2)	−0.004 (2)
C6	0.044 (3)	0.044 (3)	0.054 (3)	−0.003 (2)	0.009 (2)	−0.003 (2)
C5	0.055 (3)	0.051 (3)	0.083 (4)	−0.006 (3)	0.012 (3)	−0.007 (3)
C4	0.074 (4)	0.054 (3)	0.091 (4)	−0.003 (3)	0.015 (3)	−0.018 (3)
C3	0.065 (4)	0.058 (3)	0.083 (4)	0.013 (3)	0.021 (3)	−0.008 (3)
C2	0.048 (3)	0.057 (3)	0.076 (4)	0.006 (3)	0.010 (3)	−0.005 (3)
C1	0.048 (3)	0.044 (3)	0.047 (3)	0.005 (2)	0.004 (2)	0.004 (2)
C14	0.041 (3)	0.046 (3)	0.052 (3)	0.003 (2)	−0.005 (2)	−0.001 (2)
C13	0.037 (3)	0.055 (3)	0.047 (3)	−0.003 (2)	−0.003 (2)	0.006 (2)
C12	0.052 (3)	0.057 (3)	0.061 (3)	−0.002 (3)	−0.003 (3)	0.010 (3)
C11	0.061 (4)	0.072 (4)	0.066 (4)	−0.010 (3)	−0.007 (3)	0.024 (3)
C10	0.061 (4)	0.092 (5)	0.049 (3)	−0.014 (3)	0.000 (3)	0.016 (3)
C9	0.052 (3)	0.083 (4)	0.050 (3)	−0.004 (3)	0.002 (3)	0.002 (3)
C8	0.036 (3)	0.064 (3)	0.044 (3)	−0.005 (2)	−0.009 (2)	0.006 (2)
C21	0.040 (3)	0.054 (3)	0.042 (2)	0.007 (2)	0.001 (2)	−0.002 (2)
C20	0.038 (3)	0.049 (3)	0.058 (3)	−0.001 (2)	−0.005 (2)	−0.009 (2)
C19	0.049 (3)	0.078 (4)	0.069 (4)	−0.001 (3)	0.000 (3)	−0.016 (3)
C18	0.054 (4)	0.115 (5)	0.080 (4)	−0.020 (4)	−0.015 (3)	−0.032 (4)
C17	0.048 (3)	0.103 (5)	0.090 (5)	−0.028 (3)	−0.002 (3)	−0.023 (4)
C16	0.044 (3)	0.077 (4)	0.077 (4)	−0.020 (3)	0.009 (3)	−0.011 (3)
C15	0.038 (3)	0.050 (3)	0.059 (3)	−0.002 (2)	0.000 (2)	−0.011 (2)
C23	0.224 (17)	0.188 (15)	0.34 (2)	−0.160 (15)	0.196 (18)	−0.177 (16)
C24	0.085 (6)	0.165 (9)	0.124 (7)	−0.052 (6)	0.006 (5)	0.001 (6)
C25	0.073 (5)	0.115 (6)	0.120 (6)	−0.013 (5)	0.002 (5)	0.006 (5)
C26	0.164 (12)	0.233 (15)	0.187 (13)	0.079 (11)	0.089 (10)	0.075 (11)
O5	0.163 (7)	0.243 (9)	0.139 (6)	0.081 (7)	0.057 (5)	0.088 (6)
C27	0.52 (4)	0.32 (3)	0.115 (11)	−0.11 (3)	0.108 (18)	−0.027 (15)
O4	0.122 (7)	0.246 (12)	0.264 (12)	0.049 (8)	−0.028 (7)	−0.002 (10)
C29	0.148 (11)	0.176 (11)	0.204 (12)	0.071 (10)	−0.064 (10)	−0.009 (10)
C28	0.62 (5)	0.151 (14)	0.24 (2)	−0.18 (2)	−0.12 (3)	0.118 (15)

Geometric parameters (Å, º) top

C22—C23	1.39 (3)	C10—C9	1.368 (8)
C22—O4	1.46 (3)	C10—H10	0.930
C22—H22A	0.970	C9—C8	1.402 (7)
C22—H22B	0.970	C9—H9	0.930
Fe1—O2	1.907 (3)	C21—C20	1.441 (7)
Fe1—O3	1.916 (3)	C21—H21	0.930
Fe1—O1	1.922 (3)	C20—C19	1.399 (7)
Fe1—N3	2.150 (4)	C20—C15	1.406 (7)
Fe1—N1	2.180 (4)	C19—C18	1.381 (8)
Fe1—N2	2.220 (4)	C19—H19	0.930
O2—C8	1.303 (6)	C18—C17	1.378 (9)
O3—C15	1.306 (6)	C18—H18	0.930
O1—C1	1.304 (6)	C17—C16	1.362 (8)
N2—C14	1.285 (6)	C17—H17	0.930
N2—N2ⁱ	1.433 (7)	C16—C15	1.411 (7)
N1—C7	1.276 (6)	C16—H16	0.930
N1—N3ⁱ	1.419 (5)	C23—C24	1.406 (18)
N3—C21	1.286 (6)	C23—H23A	0.970
N3—N1ⁱ	1.419 (5)	C23—H23B	0.970
C7—C6	1.430 (7)	C24—C25	1.465 (11)
C7—H7	0.930	C24—H24A	0.970
C6—C5	1.403 (7)	C24—H24B	0.970
C6—C1	1.411 (7)	C25—O4	1.403 (12)
C5—C4	1.360 (8)	C25—H25A	0.970
C5—H5	0.930	C25—H25B	0.970
C4—C3	1.398 (9)	C26—O5	1.420 (13)
C4—H4	0.930	C26—C27	1.47 (2)
C3—C2	1.357 (8)	C26—H26A	0.970
C3—H3	0.930	C26—H26B	0.970
C2—C1	1.405 (7)	O5—C29	1.389 (12)
C2—H2	0.930	C27—C28	1.46 (3)
C14—C13	1.433 (7)	C27—H27A	0.970
C14—H14	0.930	C27—H27B	0.970
C13—C12	1.393 (7)	C29—C28	1.42 (2)
C13—C8	1.426 (7)	C29—H29A	0.970
C12—C11	1.375 (8)	C29—H29B	0.970
C12—H12	0.930	C28—H28A	0.970
C11—C10	1.375 (9)	C28—H28B	0.970
C11—H11	0.930

C23—C22—O4	111.8 (16)	C10—C9—H9	119.2
C23—C22—H22A	109.3	C8—C9—H9	119.2
O4—C22—H22A	109.3	O2—C8—C9	120.3 (5)
C23—C22—H22B	109.3	O2—C8—C13	122.6 (4)
O4—C22—H22B	109.3	C9—C8—C13	117.0 (5)
H22A—C22—H22B	107.9	N3—C21—C20	124.7 (4)
O2—Fe1—O3	94.95 (15)	N3—C21—H21	117.7
O2—Fe1—O1	98.00 (15)	C20—C21—H21	117.7
O3—Fe1—O1	98.58 (15)	C19—C20—C15	119.9 (5)
O2—Fe1—N3	166.26 (15)	C19—C20—C21	117.5 (5)
O3—Fe1—N3	84.55 (14)	C15—C20—C21	122.6 (4)
O1—Fe1—N3	95.65 (15)	C18—C19—C20	121.0 (6)
O2—Fe1—N1	92.27 (14)	C18—C19—H19	119.5
O3—Fe1—N1	172.09 (14)	C20—C19—H19	119.5
O1—Fe1—N1	83.57 (14)	C17—C18—C19	118.8 (6)
N3—Fe1—N1	87.67 (13)	C17—C18—H18	120.6
O2—Fe1—N2	84.86 (14)	C19—C18—H18	120.6
O3—Fe1—N2	92.21 (15)	C16—C17—C18	121.8 (6)
O1—Fe1—N2	168.52 (14)	C16—C17—H17	119.1
N3—Fe1—N2	81.44 (14)	C18—C17—H17	119.1
N1—Fe1—N2	85.21 (14)	C17—C16—C15	120.8 (6)
C8—O2—Fe1	129.4 (3)	C17—C16—H16	119.6
C15—O3—Fe1	136.5 (3)	C15—C16—H16	119.6
C1—O1—Fe1	136.2 (3)	O3—C15—C20	123.4 (4)
C14—N2—N2ⁱ	118.0 (3)	O3—C15—C16	118.9 (5)
C14—N2—Fe1	122.2 (3)	C20—C15—C16	117.8 (5)
N2ⁱ—N2—Fe1	119.75 (17)	C22—C23—C24	107.4 (14)
C7—N1—N3ⁱ	115.9 (4)	C22—C23—H23A	110.2
C7—N1—Fe1	127.0 (3)	C24—C23—H23A	110.2
N3ⁱ—N1—Fe1	117.1 (3)	C22—C23—H23B	110.2
C21—N3—N1ⁱ	116.7 (4)	C24—C23—H23B	110.2
C21—N3—Fe1	128.2 (3)	H23A—C23—H23B	108.5
N1ⁱ—N3—Fe1	115.0 (3)	C23—C24—C25	106.9 (10)
N1—C7—C6	125.8 (5)	C23—C24—H24A	110.3
N1—C7—H7	117.1	C25—C24—H24A	110.3
C6—C7—H7	117.1	C23—C24—H24B	110.3
C5—C6—C1	119.0 (5)	C25—C24—H24B	110.3
C5—C6—C7	118.5 (5)	H24A—C24—H24B	108.6
C1—C6—C7	122.5 (4)	O4—C25—C24	110.0 (9)
C4—C5—C6	122.5 (5)	O4—C25—H25A	109.7
C4—C5—H5	118.7	C24—C25—H25A	109.7
C6—C5—H5	118.7	O4—C25—H25B	109.7
C5—C4—C3	118.0 (5)	C24—C25—H25B	109.7
C5—C4—H4	121.0	H25A—C25—H25B	108.2
C3—C4—H4	121.0	O5—C26—C27	97.6 (14)
C2—C3—C4	121.3 (5)	O5—C26—H26A	112.2
C2—C3—H3	119.3	C27—C26—H26A	112.2
C4—C3—H3	119.3	O5—C26—H26B	112.2
C3—C2—C1	121.6 (5)	C27—C26—H26B	112.2
C3—C2—H2	119.2	H26A—C26—H26B	109.8
C1—C2—H2	119.2	C29—O5—C26	109.3 (10)
O1—C1—C2	119.6 (5)	C28—C27—C26	91.9 (13)
O1—C1—C6	122.8 (4)	C28—C27—H27A	113.3
C2—C1—C6	117.6 (5)	C26—C27—H27A	113.3
N2—C14—C13	126.0 (5)	C28—C27—H27B	113.3
N2—C14—H14	117.0	C26—C27—H27B	113.3
C13—C14—H14	117.0	H27A—C27—H27B	110.6
C12—C13—C8	119.3 (5)	C25—O4—C22	103.8 (14)
C12—C13—C14	117.8 (5)	O5—C29—C28	99.1 (14)
C8—C13—C14	122.8 (4)	O5—C29—H29A	112.0
C11—C12—C13	122.1 (5)	C28—C29—H29A	112.0
C11—C12—H12	119.0	O5—C29—H29B	112.0
C13—C12—H12	119.0	C28—C29—H29B	112.0
C12—C11—C10	118.4 (5)	H29A—C29—H29B	109.6
C12—C11—H11	120.8	C29—C28—C27	98.2 (14)
C10—C11—H11	120.8	C29—C28—H28A	112.1
C9—C10—C11	121.6 (5)	C27—C28—H28A	112.1
C9—C10—H10	119.2	C29—C28—H28B	112.1
C11—C10—H10	119.2	C27—C28—H28B	112.1
C10—C9—C8	121.5 (6)	H28A—C28—H28B	109.8

O3—Fe1—O2—C8	−52.8 (4)	C4—C3—C2—C1	1.4 (9)
O1—Fe1—O2—C8	−152.2 (4)	Fe1—O1—C1—C2	165.2 (4)
N3—Fe1—O2—C8	34.5 (9)	Fe1—O1—C1—C6	−15.9 (7)
N1—Fe1—O2—C8	123.9 (4)	C3—C2—C1—O1	176.7 (5)
N2—Fe1—O2—C8	39.0 (4)	C3—C2—C1—C6	−2.2 (8)
O2—Fe1—O3—C15	165.6 (5)	C5—C6—C1—O1	−177.2 (5)
O1—Fe1—O3—C15	−95.5 (5)	C7—C6—C1—O1	1.5 (7)
N3—Fe1—O3—C15	−0.6 (5)	C5—C6—C1—C2	1.6 (7)
N1—Fe1—O3—C15	9.8 (14)	C7—C6—C1—C2	−179.7 (5)
N2—Fe1—O3—C15	80.6 (5)	N2ⁱ—N2—C14—C13	179.9 (5)
O2—Fe1—O1—C1	−73.9 (5)	Fe1—N2—C14—C13	3.2 (7)
O3—Fe1—O1—C1	−170.2 (4)	N2—C14—C13—C12	−169.5 (5)
N3—Fe1—O1—C1	104.5 (5)	N2—C14—C13—C8	14.1 (8)
N1—Fe1—O1—C1	17.5 (4)	C8—C13—C12—C11	−2.2 (8)
N2—Fe1—O1—C1	29.8 (10)	C14—C13—C12—C11	−178.7 (5)
O2—Fe1—N2—C14	−22.5 (4)	C13—C12—C11—C10	1.9 (8)
O3—Fe1—N2—C14	72.3 (4)	C12—C11—C10—C9	−1.0 (9)
O1—Fe1—N2—C14	−127.5 (7)	C11—C10—C9—C8	0.3 (9)
N3—Fe1—N2—C14	156.4 (4)	Fe1—O2—C8—C9	147.1 (4)
N1—Fe1—N2—C14	−115.2 (4)	Fe1—O2—C8—C13	−34.9 (6)
O2—Fe1—N2—N2ⁱ	160.9 (4)	C10—C9—C8—O2	177.6 (5)
O3—Fe1—N2—N2ⁱ	−104.4 (4)	C10—C9—C8—C13	−0.5 (7)
O1—Fe1—N2—N2ⁱ	55.8 (9)	C12—C13—C8—O2	−176.6 (4)
N3—Fe1—N2—N2ⁱ	−20.2 (4)	C14—C13—C8—O2	−0.3 (7)
N1—Fe1—N2—N2ⁱ	68.2 (4)	C12—C13—C8—C9	1.4 (7)
O2—Fe1—N1—C7	86.4 (4)	C14—C13—C8—C9	177.8 (5)
O3—Fe1—N1—C7	−117.7 (11)	N1ⁱ—N3—C21—C20	−178.5 (4)
O1—Fe1—N1—C7	−11.4 (4)	Fe1—N3—C21—C20	−3.4 (7)
N3—Fe1—N1—C7	−107.4 (4)	N3—C21—C20—C19	−178.6 (5)
N2—Fe1—N1—C7	171.0 (4)	N3—C21—C20—C15	1.1 (7)
O2—Fe1—N1—N3ⁱ	−92.2 (3)	C15—C20—C19—C18	−1.3 (8)
O3—Fe1—N1—N3ⁱ	63.7 (12)	C21—C20—C19—C18	178.3 (5)
O1—Fe1—N1—N3ⁱ	170.0 (3)	C20—C19—C18—C17	1.0 (10)
N3—Fe1—N1—N3ⁱ	74.1 (3)	C19—C18—C17—C16	−0.5 (11)
N2—Fe1—N1—N3ⁱ	−7.5 (3)	C18—C17—C16—C15	0.4 (11)
O2—Fe1—N3—C21	−85.7 (7)	Fe1—O3—C15—C20	−1.1 (8)
O3—Fe1—N3—C21	2.8 (4)	Fe1—O3—C15—C16	178.7 (4)
O1—Fe1—N3—C21	100.9 (4)	C19—C20—C15—O3	−179.0 (5)
N1—Fe1—N3—C21	−175.8 (4)	C21—C20—C15—O3	1.3 (7)
N2—Fe1—N3—C21	−90.2 (4)	C19—C20—C15—C16	1.2 (7)
O2—Fe1—N3—N1ⁱ	89.4 (7)	C21—C20—C15—C16	−178.5 (5)
O3—Fe1—N3—N1ⁱ	177.9 (3)	C17—C16—C15—O3	179.5 (6)
O1—Fe1—N3—N1ⁱ	−84.0 (3)	C17—C16—C15—C20	−0.7 (8)
N1—Fe1—N3—N1ⁱ	−0.7 (3)	O4—C22—C23—C24	4 (2)
N2—Fe1—N3—N1ⁱ	84.9 (3)	C22—C23—C24—C25	−2.9 (19)
N3ⁱ—N1—C7—C6	−176.0 (4)	C23—C24—C25—O4	0.7 (13)
Fe1—N1—C7—C6	5.4 (7)	C27—C26—O5—C29	27.3 (18)
N1—C7—C6—C5	−179.0 (5)	O5—C26—C27—C28	−54 (2)
N1—C7—C6—C1	2.3 (8)	C24—C25—O4—C22	1.6 (15)
C1—C6—C5—C4	−0.3 (8)	C23—C22—O4—C25	−4 (2)
C7—C6—C5—C4	−179.1 (5)	C26—O5—C29—C28	12.4 (18)
C6—C5—C4—C3	−0.5 (9)	O5—C29—C28—C27	−48 (2)
C5—C4—C3—C2	0.0 (9)	C26—C27—C28—C29	64 (2)

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Fe₂(C₁₄H₁₀N₂O₂)₃]·4C₄H₈O
M_r	1114.84
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	293
a, b, c (Å)	15.189 (5), 19.163 (6), 18.917 (6)
V (Å³)	5506 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.40 × 0.40 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.798, 0.891
No. of measured, independent and observed [I > 2σ(I)] reflections	21523, 4856, 3520
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.222, 1.09
No. of reflections	4856
No. of parameters	343
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.96, −0.42

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 20771068) and the Provincial Natural Science Foundation of Shanxi (grant No. 2007011024) for support of this work.

References

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