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You, Tang and Zhu [Fe2(C17H16N2O2)2O] doi:10.1107/S1600536804031368 Acta Cryst.(2005). E61, m36±m38 Acta Crystallographica Section EStructure Reports Online
ISSN 1600-5368
A dinuclear oxygen-bridged Schiff base iron(III)
complex derived from
N
,
N
000-bis(2-hydroxy-benzylidene)-1,2-diaminopropane
Zhong-Lu You,a,bLu-Lu Tanga
and Hai-Liang Zhua*
aDepartment of Chemistry, Fuyang Normal
College, Fuyang Anhui 236041, People's Republic of China, andbDepartment of
Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China
Correspondence e-mail: [email protected]
Key indicators Single-crystal X-ray study
T= 298 K
Mean(C±C) = 0.08 AÊ
Rfactor = 0.056
wRfactor = 0.161
Data-to-parameter ratio = 13.3
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography Printed in Great Britain ± all rights reserved
The title compound, -oxo-bis({2,2-[propane-1,2-diylbis-(nitrilomethylidyne)]diphenolato}iron(III)), [Fe2(C17H16N2
-O2)2O], is an unusual dinuclear iron(III) complex. Each FeIII
ion has a distorted square-pyramidal coordination geometry. In the basal plane, the Fe atom is coordinated by two N atoms and two O atoms of the Schiff base ligand. The apical position is occupied by a bridging O2ÿion, which links to the other FeIII
ion in the complex. In the crystal structure, pairs of dinuclear iron(III) units form dimers by way of a pair of intermolecular CÐH O interactions. The dimers stack along theaaxis and there are no other short intermolecular contacts.
Comment
Investigation into the magnetic properties of molecule-based materials containing a polynuclear assembly has become a fascinating subject in the ®eld of condensed matter physics and materials chemistry (Dalai et al., 2002; Bhaduri et al., 2003). Much attention has been focused on coordination complexes with novel magnetic properties, which may have potentially useful applications in materials science (Rayet al., 2003). The prime strategy for designing these molecular materials is to use a suitable bridging ligand that determines the nature of the magnetic interactions (Koner et al., 2003). Schiff base iron(III) complexes with O atoms as the bridging ligands have been of great interest in the past few years (Ashmawyet al., 1991; Corazzaet al., 1987). Recently, we have reported some Schiff base complexes (Youet al., 2004; You & Zhu, 2004; Youet al., 2004). As an extension of this work, a novel dinuclear iron(III) complex, (I) (Fig. 1), is reported here. Its most interesting feature is a bridging oxide ligand.
Each iron(III) ion in (I) has a square-pyramidal coordina-tion geometry, involving two N atoms and two O atoms from a Schiff base ligand, and one apical O5 atom. The O5 atom acts as a bridging function, and coordinates to both Fe1 and Fe2 atoms.The Fe Fe separation is 3.418 (4) AÊ. The signi®cant distortion of each of the square pyramids is revealed by the
bond angles between the apical and basal donor atoms (Table 1), which show deviations, of 17.2 (2) for the Fe1 grouping,
and 16.4 (2)for the Fe2 grouping, from the ideal 90angle in
a regular square pyramid. The smallest bond angles for the basal donor atoms [76.29 (19) for N1ÐFe1ÐN2 and
75.81 (19) for N3ÐFe2ÐN4] correlate with the strained
ligand bite angle for the ®ve-membered chelate rings. The other basal angles are closer to 90[86.17 (18)±90.24 (15)for
Fe1 and 86.23 (18)±93.19 (17) for Fe2].
The FeÐO5 bond lengths (Table 1) are substantially shorter than the average bond lengths between the Fe atoms and the basal donor atoms [2.005 (4) AÊ for the Fe1 moiety, and 2.012 (4) AÊ for the Fe2 moiety]. The Fe1ÐO5ÐFe2 bond angle of 147.5 (2)is comparable to the corresponding value of
146.69 (3)observed in a similar Schiff base iron(III) complex
(Ashmawyet al., 1991).
Atoms C8 and C9 deviate by 0.759 (7) and 0.220 (7) AÊ, respectively, from the N1/Fe1/N2 plane. Atoms C25 and C26 deviate by 0.831 (7) and 0.320 (7) AÊ, respectively, from the N3/ Fe2/N4 plane. The deviations of atoms Fe1 and Fe2 from the N1/N2/O2/O1 and N3/N4/O4/O3 square planes are 0.600 (2) and 0.573 (2) AÊ, respectively. The dihedral angle between the two benzene rings associated with the Fe1 moiety is 32.5 (6),
with a corresponding value of 38.2 (6)for Fe2.
The average value of the C1 N1, C10 N2, C18 N3 and C27 N4 bond lengths in (I) is 1.269 (6) AÊ, which conforms to the value for a C N double bond, while the average value of the C8ÐN1, C9ÐN2, C25ÐN3 and C26ÐN4 bond lengths is 1.471 (7) AÊ, which conforms to the value for a CÐN single bond.
In the crystal structure of (I), the dinuclear molecules form dimers by way of a pair of intermolecular CÐH O inter-actions (Table 2). The dimers stack along theaaxis and there are no other short intermolecular contacts (Fig. 2).
Experimental
1,2-Diaminopropane (0.1 mmol, 7.4 mg) and salicylaldehyde (0.2 mmol, 24.4 mg) were dissolved in methanol (5 ml). The mixture was stirred for 10 min at room temperature to give a clear yellow solution. To the solution was added a methanol solution (5 ml) of Fe(NO3)39H2O (0.1 mmol, 34.2 mg), with stirring. The mixture was
stirred for another 10 min, and allowed to stand in air for 12 d. Some brown block-shaped crystals of (I) were formed at the bottom of the vessel on slow evaporation of the solvent. The crystals were isolated, washed three times with methanol and dried in a vacuum desiccator using anhydrous CaCl2(yield 71.3%). Analysis found: C 59.1, H 4.7,
N 8.2%; calculated for C34H32Fe2N4O5: C 59.3, H 4.7, N 8.1%. Crystal data
[Fe2(C17H16N2O2)2O]
Mr= 688.34
Triclinic,P1 a= 11.462 (4) AÊ b= 12.478 (4) AÊ c= 13.230 (5) AÊ
= 95.491 (6) = 115.070 (5) = 110.291 (5)
V= 1540.6 (9) AÊ3
Z= 2
Dx= 1.484 Mg mÿ3
MoKradiation Cell parameters from 1812
re¯ections
= 2.2±24.3 = 0.99 mmÿ1
T= 298 (2) K Block, brown 0.290.230.16 mm
Data collection
Bruker SMART CCD area-detector diffractometer
!scan
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin= 0.762,Tmax= 0.858
8247 measured re¯ections
5385 independent re¯ections 2776 re¯ections withI> 2(I) Rint= 0.029
max= 25.0
h=ÿ13!13 k=ÿ10!14 l=ÿ15!15
metal-organic papers
Acta Cryst.(2005). E61, m36±m38 You, Tang and Zhu [Fe2(C17H16N2O2)2O]
m37
Figure 2The crystal packing of (I), showing the C34ÐH34A O5 interactions as dashed lines. All other H atoms have been omitted for clarity.
Figure 1
Refinement
Re®nement onF2
R[F2> 2(F2)] = 0.056
wR(F2) = 0.161
S= 0.91 5385 re¯ections 406 parameters
H-atom parameters constrained w= 1/[2(F
o2) + (0.0834P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.0001
max= 0.61 e AÊÿ3
min=ÿ0.39 e AÊÿ3
Table 1
Selected geometric parameters (AÊ,).
Fe1ÐO5 1.770 (4) Fe1ÐO1 1.910 (4) Fe1ÐO2 1.914 (4) Fe1ÐN1 2.090 (4) Fe1ÐN2 2.105 (5)
Fe2ÐO5 1.790 (3) Fe2ÐO3 1.897 (4) Fe2ÐO4 1.928 (4) Fe2ÐN3 2.099 (4) Fe2ÐN4 2.123 (4)
O5ÐFe1ÐO1 114.84 (16) O5ÐFe1ÐO2 107.35 (17) O1ÐFe1ÐO2 90.24 (15) O5ÐFe1ÐN1 100.94 (16) O1ÐFe1ÐN1 87.01 (16) O2ÐFe1ÐN1 149.90 (18) O5ÐFe1ÐN2 105.87 (16) O1ÐFe1ÐN2 138.24 (17) O2ÐFe1ÐN2 86.17 (18) N1ÐFe1ÐN2 76.29 (19)
O5ÐFe2ÐO3 113.35 (17) O5ÐFe2ÐO4 106.04 (16) O3ÐFe2ÐO4 93.19 (17) O5ÐFe2ÐN3 101.02 (16) O3ÐFe2ÐN3 86.25 (17) O4ÐFe2ÐN3 150.66 (17) O5ÐFe2ÐN4 105.23 (17) O3ÐFe2ÐN4 139.89 (17) O4ÐFe2ÐN4 86.23 (18) N3ÐFe2ÐN4 75.81 (19)
Table 2
Hydrogen-bond geometry (AÊ,).
DÐH H A D A DÐH A
C34ÐH34A O5i 0.96 2.56 3.454 (7) 155 Symmetry code: (i)ÿx;ÿy1;ÿz1.
All H atoms were placed in geometrically idealized positions and allowed to ride on their parent atoms, with CÐH distances of 0.93± 0.98 AÊ andUiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Data collection:SMART(Bruker, 1998); cell re®nement:SAINT
(Bruker, 1998); data reduction:SAINT; program(s) used to solve structure:SHELXS97 (Sheldrick, 1997a); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997a); molecular graphics:
SHELXTL(Sheldrick, 1997b); software used to prepare material for publication:SHELXTL.
The authors thank the Education Of®ce of Anhui Province, Peoples Republic of China, for research grant No. 2004kj300zd.
References
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Bhaduri, S., Tasiopoulos, A. J., Bolcar, M. A., Abbound, K. A., Streib, W. E. & Christou, G. (2003).Inorg. Chem.42, 1483±1492.
Bruker (1998).SMART(Version 5.628) andSAINT(Version 6.02). Bruker AXS Inc., Madison, Wisconsin, USA.
Corazza, F., Floriani, C. & Zehnder, M. (1987).J. Chem. Soc. Dalton Trans.
709, 709±714.
Dalai, S., Mukherjee, P. S., Drew, M. G. B., Lu, T.-H. & Chaudhuri, N. R. (2002).Inorg. Chim. Acta,335, 85±90.
Koner, S., Saha, S., Okamoto, K.-I. & Tuchagues, J.-P. (2003).Inorg. Chem.42, 4668±4672.
Ray, M. S., Mukhopadhyay, G., Drew, M. G. B., Lu, T.-H., Chaudhuri, S. & Ghosh, A. (2003).Inorg. Chem. Commun.6, 961±965.
Sheldrick, G. M. (1996).SADABS.University of GoÈttingen, Germany. Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of
GoÈttingen, Germany.
Sheldrick, G. M. (1997b).SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.
You, Z.-L., Xiong, Z.-D. & Zhu, H.-L. (2004).Acta Cryst.E60, m1114±m1116. You, Z.-L. & Zhu, H.-L. (2004).Acta Cryst.C60, m445±m446.
You, Z.-L., Zhu, H.-L. & Liu, W.-S. (2004).Acta Cryst.E60, m587±m589.
metal-organic papers
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Acta Cryst. (2005). E61, m36–m38
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Acta Cryst. (2005). E61, m36–m38 [https://doi.org/10.1107/S1600536804031368]
A dinuclear oxygen-bridged Schiff base iron(III) complex derived from
N
,
N
′
-bis-(2-hydroxybenzylidene)-1,2-diaminopropane
Zhong-Lu You, Lu-Lu Tang and Hai-Liang Zhu
µ-oxo-bis({2,2-[propane-1,2-diylbis(nitrilomethylidyne)]diphenolato}iron(III))
Crystal data
[Fe2(C17H16N2O2)2O] Mr = 688.34
Triclinic, P1 Hall symbol: -P 1 a = 11.462 (4) Å b = 12.478 (4) Å c = 13.230 (5) Å α = 95.491 (6)° β = 115.070 (5)° γ = 110.291 (5)° V = 1540.6 (9) Å3
Z = 2 F(000) = 712 Dx = 1.484 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 1812 reflections θ = 2.2–24.3°
µ = 0.99 mm−1 T = 298 K Block, brown
0.29 × 0.23 × 0.16 mm
Data collection
Bruker SMART CCD area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin = 0.762, Tmax = 0.858
8247 measured reflections 5385 independent reflections 2776 reflections with I > 2σ(I) Rint = 0.029
θmax = 25.0°, θmin = 1.8° h = −13→13
k = −10→14 l = −15→15
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.056 wR(F2) = 0.161 S = 0.91 5385 reflections 406 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.0834P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.61 e Å−3
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Acta Cryst. (2005). E61, m36–m38
Special details
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)
x y z Uiso*/Ueq
Fe1 0.22639 (8) 0.84200 (6) 0.46757 (6) 0.0600 (3) Fe2 −0.05254 (8) 0.60038 (6) 0.24314 (6) 0.0623 (3) N1 0.1763 (5) 0.9865 (4) 0.4410 (4) 0.0643 (12) N2 0.3078 (5) 0.9057 (4) 0.3585 (4) 0.0699 (12) N3 −0.0835 (5) 0.4531 (4) 0.3099 (4) 0.0702 (12) N4 0.0861 (5) 0.5326 (4) 0.2254 (4) 0.0672 (12) O1 0.2670 (4) 0.8924 (3) 0.6244 (3) 0.0755 (11) O2 0.3648 (4) 0.7786 (3) 0.5174 (3) 0.0793 (11) O3 −0.2503 (4) 0.5558 (3) 0.1839 (3) 0.0819 (11) O4 −0.0480 (4) 0.6694 (3) 0.1199 (3) 0.0812 (11) O5 0.0579 (4) 0.7209 (3) 0.3746 (3) 0.0705 (10) C1 0.1645 (6) 1.0521 (5) 0.5099 (5) 0.0696 (15)
H1 0.1293 1.1060 0.4815 0.084*
C2 0.1989 (6) 1.0537 (4) 0.6276 (5) 0.0663 (15) C3 0.2558 (6) 0.9773 (5) 0.6816 (5) 0.0665 (14) C4 0.3062 (7) 0.9944 (6) 0.8010 (6) 0.0860 (18)
H4 0.3436 0.9449 0.8376 0.103*
C5 0.3005 (8) 1.0849 (6) 0.8645 (6) 0.098 (2)
H5 0.3366 1.0975 0.9444 0.118*
C6 0.2417 (8) 1.1567 (6) 0.8108 (7) 0.096 (2)
H6 0.2355 1.2159 0.8538 0.115*
C7 0.1935 (6) 1.1412 (5) 0.6966 (6) 0.0812 (17)
H7 0.1550 1.1910 0.6619 0.097*
C8 0.1472 (7) 0.9961 (5) 0.3226 (5) 0.0823 (18)
H8 0.0646 0.9218 0.2684 0.099*
C9 0.2684 (7) 0.9946 (6) 0.3096 (5) 0.0902 (19)
H9A 0.2418 0.9762 0.2278 0.108*
H9B 0.3489 1.0724 0.3493 0.108*
C10 0.3836 (6) 0.8679 (5) 0.3286 (5) 0.0758 (16)
H10 0.4050 0.8971 0.2735 0.091*
C11 0.4370 (6) 0.7856 (5) 0.3727 (5) 0.0706 (15) C12 0.4256 (6) 0.7445 (5) 0.4650 (5) 0.0655 (14) C13 0.4858 (7) 0.6667 (5) 0.5030 (6) 0.0876 (18)
H13 0.4812 0.6397 0.5649 0.105*
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Acta Cryst. (2005). E61, m36–m38
H14 0.5912 0.5770 0.4796 0.115*
C15 0.5600 (7) 0.6663 (7) 0.3600 (7) 0.104 (2)
H15 0.6034 0.6390 0.3247 0.125*
C16 0.5045 (6) 0.7434 (6) 0.3209 (5) 0.0848 (18)
H16 0.5108 0.7691 0.2589 0.102*
C17 0.1094 (8) 1.0941 (6) 0.2866 (6) 0.109 (2)
H17A 0.0295 1.0900 0.2959 0.163*
H17B 0.0849 1.0860 0.2064 0.163*
H17C 0.1894 1.1695 0.3341 0.163*
C18 −0.1993 (7) 0.3778 (5) 0.2981 (5) 0.0710 (15)
H18 −0.1952 0.3169 0.3329 0.085*
C19 −0.3363 (6) 0.3783 (5) 0.2356 (4) 0.0607 (13) C20 −0.3557 (6) 0.4677 (5) 0.1817 (4) 0.0624 (14) C21 −0.4946 (7) 0.4581 (6) 0.1235 (5) 0.0745 (16)
H21 −0.5098 0.5172 0.0894 0.089*
C22 −0.6082 (7) 0.3657 (7) 0.1149 (5) 0.093 (2)
H22 −0.6994 0.3610 0.0729 0.111*
C23 −0.5888 (7) 0.2796 (6) 0.1676 (6) 0.094 (2)
H23 −0.6662 0.2172 0.1632 0.113*
C24 −0.4543 (7) 0.2862 (6) 0.2269 (5) 0.0859 (18)
H24 −0.4416 0.2273 0.2624 0.103*
C25 0.0546 (7) 0.4450 (6) 0.3728 (6) 0.096 (2)
H25 0.1197 0.5194 0.4360 0.115*
C26 0.1118 (7) 0.4468 (6) 0.2902 (6) 0.0908 (19)
H26A 0.2134 0.4689 0.3331 0.109*
H26B 0.0656 0.3679 0.2364 0.109*
C27 0.1463 (6) 0.5588 (5) 0.1641 (5) 0.0778 (17)
H27 0.2038 0.5213 0.1642 0.093*
C28 0.1352 (6) 0.6393 (6) 0.0951 (5) 0.0791 (17) C29 0.0430 (7) 0.6946 (5) 0.0810 (5) 0.0788 (17) C30 0.0478 (8) 0.7786 (6) 0.0174 (6) 0.102 (2)
H30 −0.0130 0.8154 0.0052 0.122*
C31 0.1388 (10) 0.8077 (8) −0.0271 (7) 0.124 (3)
H31 0.1408 0.8648 −0.0675 0.148*
C32 0.2276 (9) 0.7523 (9) −0.0121 (7) 0.133 (3)
H32 0.2896 0.7727 −0.0424 0.160*
C33 0.2263 (7) 0.6687 (7) 0.0457 (6) 0.105 (2)
H33 0.2851 0.6305 0.0531 0.126*
C34 0.0565 (8) 0.3482 (7) 0.4268 (7) 0.133 (3)
H34A 0.0196 0.3511 0.4795 0.199*
H34B 0.1526 0.3569 0.4688 0.199*
H34C −0.0016 0.2730 0.3675 0.199*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
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sup-4
Acta Cryst. (2005). E61, m36–m38
N1 0.067 (3) 0.056 (3) 0.058 (3) 0.026 (2) 0.022 (2) 0.011 (2) N2 0.072 (3) 0.060 (3) 0.060 (3) 0.020 (3) 0.025 (3) 0.016 (2) N3 0.062 (3) 0.064 (3) 0.078 (3) 0.030 (3) 0.026 (3) 0.026 (2) N4 0.059 (3) 0.057 (3) 0.071 (3) 0.025 (2) 0.021 (3) 0.009 (2) O1 0.108 (3) 0.066 (2) 0.062 (2) 0.051 (2) 0.038 (2) 0.0192 (19) O2 0.094 (3) 0.099 (3) 0.068 (3) 0.062 (3) 0.040 (2) 0.034 (2) O3 0.065 (3) 0.072 (3) 0.099 (3) 0.032 (2) 0.027 (2) 0.039 (2) O4 0.087 (3) 0.094 (3) 0.069 (3) 0.048 (3) 0.036 (3) 0.033 (2) O5 0.079 (3) 0.052 (2) 0.070 (2) 0.0237 (19) 0.032 (2) 0.0118 (18) C1 0.058 (4) 0.059 (4) 0.079 (4) 0.025 (3) 0.021 (3) 0.024 (3) C2 0.061 (4) 0.048 (3) 0.089 (4) 0.023 (3) 0.037 (3) 0.010 (3) C3 0.066 (4) 0.060 (4) 0.063 (4) 0.022 (3) 0.030 (3) 0.004 (3) C4 0.094 (5) 0.090 (5) 0.080 (5) 0.047 (4) 0.043 (4) 0.015 (4) C5 0.105 (6) 0.101 (5) 0.076 (5) 0.032 (5) 0.048 (4) 0.005 (4) C6 0.100 (6) 0.083 (5) 0.112 (6) 0.043 (4) 0.061 (5) 0.011 (4) C7 0.075 (4) 0.072 (4) 0.100 (5) 0.032 (3) 0.047 (4) 0.018 (4) C8 0.079 (5) 0.082 (4) 0.086 (5) 0.039 (4) 0.032 (4) 0.046 (4) C9 0.099 (6) 0.088 (5) 0.078 (4) 0.037 (4) 0.039 (4) 0.037 (4) C10 0.063 (4) 0.079 (4) 0.058 (4) 0.013 (3) 0.024 (3) 0.005 (3) C11 0.047 (3) 0.077 (4) 0.065 (4) 0.017 (3) 0.020 (3) 0.000 (3) C12 0.051 (4) 0.067 (4) 0.053 (3) 0.017 (3) 0.015 (3) 0.000 (3) C13 0.079 (5) 0.083 (4) 0.103 (5) 0.042 (4) 0.041 (4) 0.020 (4) C14 0.079 (5) 0.083 (5) 0.122 (6) 0.038 (4) 0.046 (5) 0.019 (4) C15 0.073 (5) 0.098 (6) 0.117 (7) 0.035 (4) 0.036 (5) −0.010 (5) C16 0.050 (4) 0.100 (5) 0.074 (4) 0.010 (4) 0.028 (3) −0.001 (4) C17 0.125 (6) 0.100 (5) 0.115 (6) 0.066 (5) 0.054 (5) 0.047 (5) C18 0.072 (4) 0.060 (4) 0.075 (4) 0.029 (3) 0.030 (4) 0.022 (3) C19 0.061 (4) 0.060 (3) 0.053 (3) 0.023 (3) 0.024 (3) 0.011 (3) C20 0.060 (4) 0.069 (4) 0.051 (3) 0.030 (3) 0.021 (3) 0.009 (3) C21 0.079 (5) 0.094 (5) 0.058 (4) 0.046 (4) 0.033 (4) 0.019 (3) C22 0.065 (5) 0.139 (7) 0.066 (4) 0.039 (5) 0.032 (4) 0.020 (4) C23 0.062 (5) 0.118 (6) 0.083 (5) 0.017 (4) 0.037 (4) 0.031 (4) C24 0.075 (5) 0.094 (5) 0.075 (4) 0.025 (4) 0.035 (4) 0.026 (3) C25 0.078 (5) 0.108 (5) 0.115 (6) 0.059 (4) 0.036 (4) 0.067 (5) C26 0.081 (5) 0.088 (5) 0.114 (5) 0.050 (4) 0.045 (4) 0.036 (4) C27 0.058 (4) 0.074 (4) 0.071 (4) 0.018 (3) 0.019 (4) −0.003 (3) C28 0.058 (4) 0.093 (5) 0.054 (4) 0.017 (4) 0.017 (3) 0.003 (3) C29 0.077 (5) 0.082 (4) 0.049 (4) 0.020 (4) 0.019 (3) 0.012 (3) C30 0.094 (6) 0.120 (6) 0.075 (5) 0.030 (4) 0.037 (4) 0.039 (4) C31 0.111 (7) 0.146 (8) 0.087 (6) 0.033 (6) 0.040 (6) 0.054 (5) C32 0.097 (7) 0.180 (10) 0.075 (6) 0.020 (6) 0.033 (5) 0.038 (6) C33 0.073 (5) 0.145 (7) 0.065 (5) 0.026 (4) 0.027 (4) 0.010 (4) C34 0.109 (6) 0.146 (7) 0.172 (8) 0.075 (6) 0.069 (6) 0.088 (6)
Geometric parameters (Å, º)
Fe1—O5 1.770 (4) C12—C13 1.391 (7)
supporting information
sup-5
Acta Cryst. (2005). E61, m36–m38
Fe1—O2 1.914 (4) C13—H13 0.9300
Fe1—N1 2.090 (4) C14—C15 1.371 (9)
Fe1—N2 2.105 (5) C14—H14 0.9300
Fe2—O5 1.790 (3) C15—C16 1.356 (9)
Fe2—O3 1.897 (4) C15—H15 0.9300
Fe2—O4 1.928 (4) C16—H16 0.9300
Fe2—N3 2.099 (4) C17—H17A 0.9600
Fe2—N4 2.123 (4) C17—H17B 0.9600
N1—C1 1.248 (6) C17—H17C 0.9600
N1—C8 1.484 (7) C18—C19 1.434 (7)
N2—C10 1.294 (7) C18—H18 0.9300
N2—C9 1.446 (7) C19—C24 1.389 (7)
N3—C18 1.265 (6) C19—C20 1.411 (7)
N3—C25 1.489 (7) C20—C21 1.398 (7)
N4—C27 1.269 (7) C21—C22 1.358 (8)
N4—C26 1.466 (7) C21—H21 0.9300
O1—C3 1.318 (6) C22—C23 1.367 (8)
O2—C12 1.305 (6) C22—H22 0.9300
O3—C20 1.309 (6) C23—C24 1.369 (8)
O4—C29 1.307 (7) C23—H23 0.9300
C1—C2 1.432 (7) C24—H24 0.9300
C1—H1 0.9300 C25—C34 1.463 (8)
C2—C7 1.389 (7) C25—C26 1.492 (8)
C2—C3 1.418 (7) C25—H25 0.9800
C3—C4 1.397 (7) C26—H26A 0.9700
C4—C5 1.378 (8) C26—H26B 0.9700
C4—H4 0.9300 C27—C28 1.423 (8)
C5—C6 1.377 (8) C27—H27 0.9300
C5—H5 0.9300 C28—C29 1.411 (8)
C6—C7 1.337 (8) C28—C33 1.418 (8)
C6—H6 0.9300 C29—C30 1.406 (8)
C7—H7 0.9300 C30—C31 1.366 (10)
C8—C9 1.477 (8) C30—H30 0.9300
C8—C17 1.488 (7) C31—C32 1.377 (11)
C8—H8 0.9800 C31—H31 0.9300
C9—H9A 0.9700 C32—C33 1.351 (10)
C9—H9B 0.9700 C32—H32 0.9300
C10—C11 1.420 (8) C33—H33 0.9300
C10—H10 0.9300 C34—H34A 0.9600
C11—C12 1.408 (7) C34—H34B 0.9600
C11—C16 1.417 (8) C34—H34C 0.9600
O5—Fe1—O1 114.84 (16) C14—C13—C12 121.9 (7)
O5—Fe1—O2 107.35 (17) C14—C13—H13 119.1
O1—Fe1—O2 90.24 (15) C12—C13—H13 119.1
O5—Fe1—N1 100.94 (16) C13—C14—C15 120.7 (7)
O1—Fe1—N1 87.01 (16) C13—C14—H14 119.7
supporting information
sup-6
Acta Cryst. (2005). E61, m36–m38
O5—Fe1—N2 105.87 (16) C16—C15—C14 119.6 (7)
O1—Fe1—N2 138.24 (17) C16—C15—H15 120.2
O2—Fe1—N2 86.17 (18) C14—C15—H15 120.2
N1—Fe1—N2 76.29 (19) C15—C16—C11 121.2 (7)
O5—Fe2—O3 113.35 (17) C15—C16—H16 119.4
O5—Fe2—O4 106.04 (16) C11—C16—H16 119.4
O3—Fe2—O4 93.19 (17) C8—C17—H17A 109.5
O5—Fe2—N3 101.02 (16) C8—C17—H17B 109.5
O3—Fe2—N3 86.25 (17) H17A—C17—H17B 109.5
O4—Fe2—N3 150.66 (17) C8—C17—H17C 109.5
O5—Fe2—N4 105.23 (17) H17A—C17—H17C 109.5
O3—Fe2—N4 139.89 (17) H17B—C17—H17C 109.5
O4—Fe2—N4 86.23 (18) N3—C18—C19 125.6 (5)
N3—Fe2—N4 75.81 (19) N3—C18—H18 117.2
C1—N1—C8 123.9 (5) C19—C18—H18 117.2
C1—N1—Fe1 126.5 (4) C24—C19—C20 119.0 (5)
C8—N1—Fe1 109.5 (3) C24—C19—C18 118.4 (5)
C10—N2—C9 118.5 (5) C20—C19—C18 122.6 (5)
C10—N2—Fe1 125.3 (4) O3—C20—C21 120.4 (5)
C9—N2—Fe1 116.2 (4) O3—C20—C19 122.6 (5)
C18—N3—C25 122.8 (5) C21—C20—C19 117.0 (5)
C18—N3—Fe2 127.7 (4) C22—C21—C20 122.5 (6)
C25—N3—Fe2 109.5 (4) C22—C21—H21 118.7
C27—N4—C26 118.2 (5) C20—C21—H21 118.7
C27—N4—Fe2 126.2 (4) C21—C22—C23 120.2 (6)
C26—N4—Fe2 115.6 (4) C21—C22—H22 119.9
C3—O1—Fe1 133.8 (3) C23—C22—H22 119.9
C12—O2—Fe1 131.5 (3) C22—C23—C24 119.3 (6)
C20—O3—Fe2 135.2 (3) C22—C23—H23 120.4
C29—O4—Fe2 131.5 (4) C24—C23—H23 120.4
Fe1—O5—Fe2 147.5 (2) C23—C24—C19 121.9 (6)
N1—C1—C2 127.4 (5) C23—C24—H24 119.1
N1—C1—H1 116.3 C19—C24—H24 119.1
C2—C1—H1 116.3 C34—C25—N3 118.3 (6)
C7—C2—C3 117.9 (6) C34—C25—C26 112.5 (6)
C7—C2—C1 120.0 (5) N3—C25—C26 106.4 (5)
C3—C2—C1 121.7 (5) C34—C25—H25 106.3
O1—C3—C4 118.2 (5) N3—C25—H25 106.3
O1—C3—C2 122.7 (5) C26—C25—H25 106.3
C4—C3—C2 119.1 (5) N4—C26—C25 109.8 (5)
C5—C4—C3 119.8 (6) N4—C26—H26A 109.7
C5—C4—H4 120.1 C25—C26—H26A 109.7
C3—C4—H4 120.1 N4—C26—H26B 109.7
C6—C5—C4 120.6 (7) C25—C26—H26B 109.7
C6—C5—H5 119.7 H26A—C26—H26B 108.2
C4—C5—H5 119.7 N4—C27—C28 126.9 (6)
C7—C6—C5 119.9 (6) N4—C27—H27 116.6
supporting information
sup-7
Acta Cryst. (2005). E61, m36–m38
C5—C6—H6 120.0 C29—C28—C33 120.1 (7)
C6—C7—C2 122.6 (6) C29—C28—C27 121.8 (6)
C6—C7—H7 118.7 C33—C28—C27 118.0 (7)
C2—C7—H7 118.7 O4—C29—C30 119.1 (6)
C9—C8—N1 107.0 (5) O4—C29—C28 124.0 (6)
C9—C8—C17 113.2 (5) C30—C29—C28 116.8 (7)
N1—C8—C17 117.9 (5) C31—C30—C29 122.2 (8)
C9—C8—H8 105.9 C31—C30—H30 118.9
N1—C8—H8 105.9 C29—C30—H30 118.9
C17—C8—H8 105.9 C30—C31—C32 119.8 (8)
N2—C9—C8 109.4 (5) C30—C31—H31 120.1
N2—C9—H9A 109.8 C32—C31—H31 120.1
C8—C9—H9A 109.8 C33—C32—C31 121.3 (9)
N2—C9—H9B 109.8 C33—C32—H32 119.4
C8—C9—H9B 109.8 C31—C32—H32 119.4
H9A—C9—H9B 108.2 C32—C33—C28 119.8 (8)
N2—C10—C11 125.6 (5) C32—C33—H33 120.1
N2—C10—H10 117.2 C28—C33—H33 120.1
C11—C10—H10 117.2 C25—C34—H34A 109.5
C12—C11—C16 119.0 (6) C25—C34—H34B 109.5
C12—C11—C10 122.9 (5) H34A—C34—H34B 109.5
C16—C11—C10 118.2 (6) C25—C34—H34C 109.5
O2—C12—C13 119.5 (6) H34A—C34—H34C 109.5
O2—C12—C11 122.9 (5) H34B—C34—H34C 109.5
C13—C12—C11 117.6 (6)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
C34—H34A···O5i 0.96 2.56 3.454 (7) 155 (2)
