supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportcited insimilar papers Open access

Acta Cryst. (2009). E65, m122    [ doi:10.1107/S1600536808042992 ]

Poly[([mu]-4,4'-bipyridine)([mu]-naphthalene-1,4-dicarboxylato)iron(II)]

J. Boeckmann, I. Jess and C. Näther

Abstract top

The asymmetric unit of the title compound, [Fe(C12H6O4)(C10H8N2)], consists of two independent Fe(II) atoms, two naphthalene-1,4-dicarboxylate anions and two 4,4'-bipyridine ligands. The Fe(II) atoms are each coordinated by four O atoms of the naphthalene-1,4-dicarboxylate anions and two N atoms of the 4,4'-bipyridine ligands within a distorted octahedron. Two Fe(II) atoms are bridged via the carboxylate groups of two symmetry-related anions into dimers, which are further connected into chains. These chains are linked by additional anions into layers that are finally connected by the 4,4'-bipyridine ligands into a three-dimensional coordination network.

Comment top

The structure determination of the title compound was performed as a part of a project on the synthesis of new metal organic frameworks. In this project we have reacted iron(II)sulfate with naphthalene-1,4-dicarboxylic acid in sodium hydroxide and water, which leads to the formation of bis(µ2-4,4'-bipyridine)-bis(µ2-naphthalene-1,4-dicarboxylate)diiron(II).

In the crystal structure of the title compound each of the two crystallographically iron atoms are surrounded by two N atoms of two symmetry related 4,4'-bipyridine ligands and four O atoms of three naphthalene-1,4-dicarboxylate anions, of which two are related by symmetry. The coordination polyhedron can be described as a distorted octahedra (Fig 1 and tab 1). Two symmetry related anions bridges two different Fe atoms into dimers, which are further connected into chains by these anions (Fig. 2). Such dimers are also found in the structure of [Eu2(naphthalene-1,4-dicarboxylate)3(4,4'-bipyridine)0.5(H2O)3]- (4,4'-bipyridine) reported by Zheng et al. (2005). The second crystallographically independent napthalene-1,4-dicarboxylate anion is coordinated with both O atoms of its carboxyl group to the metal centers. These anions entangle the Fe-naphthalene-1,4-dicarboxylate chains into layers which are parallel to the a/b plane. These layers are further linked by the 4,4'-bipyridine ligands into a three-dimensional coordination network (Fig 3).

Related literature top

For a related structure, see: Zheng et al. (2005).

Experimental top

27.9 mg FeSO4 . 7 H2O (0.10 mmol), 33.0 mg naphthalene-1,4-dicarboxylic acid (0.15 mmol), 10.4 mg NaOH (0.26 mmol), 20.0 mg 4,4'-Bipyridine (0.10 mmol) and 5 ml of water were transfered into a glass tube and heated to 150° C for 4 d. On cooling yellow platelets of the title compound were obtained.

Refinement top

All H atoms were located in difference map but were positioned with idealized geometry and were refined isotropic with Ueq(H) = 1.2 Ueq(C) of the parent atom using a riding model with C—H = 0.93 Å.

Computing details top

Data collection: X-AREA (Stoe, 2008); cell refinement: X-AREA (Stoe, 2008); data reduction: X-AREA (Stoe, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008) and XP in SHELXTL ((Sheldrick, 2008); software used to prepare material for publication: XCIF in SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. : Crystal structure of the title compund with labelling and displacement ellipsoids drawn at the 50% probability level. Symmetry codes: i = x + 1, y, z; ii = x, y, z + 1; iii = 1.5 - x, -1/2 + y, 1.5 - z; iv = x, y, -1 + z.
[Figure 2] Fig. 2. : Crystal structure of the title compound with view of the Fe naphthalene-1,4-dicarboxylate coordination. The co-ligands, 4,4'-bipyridine, are omitted for clarity.
[Figure 3] Fig. 3. : Crystal structure of the title compound with view in the direction of the crystallographic a axis.
Poly[(µ-4,4'-bipyridine)(µ-naphthalene-1,4-dicarboxylato)iron(II)] top
Crystal data top
[Fe(C12H6O4)(C10H8N2)]F(000) = 1744
Mr = 426.20Dx = 1.561 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 18988 reflections
a = 10.5169 (4) Åθ = 1.4–27.2°
b = 29.8928 (10) ŵ = 0.87 mm−1
c = 11.5578 (4) ÅT = 293 K
β = 93.178 (3)°Platelets, yellow
V = 3627.9 (2) Å30.09 × 0.09 × 0.08 mm
Z = 8
Data collection top
STOE IPDS-2
diffractometer		7116 independent reflections
Radiation source: fine-focus sealed tube5305 reflections with I > 2σ(I)
graphiteRint = 0.050
Detector resolution: 0.150 pixels mm-1θmax = 26.0°, θmin = 1.4°
ω scansh = −12→12
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe, 2008)		k = −36→36
Tmin = 0.923, Tmax = 0.933l = −14→12
21152 measured reflections
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0499P)2 + 3.8737P]
where P = (Fo2 + 2Fc2)/3
7116 reflections(Δ/σ)max = 0.001
523 parametersΔρmax = 0.39 e Å−3
0 restraintsΔρmin = −0.36 e Å−3
Crystal data top
[Fe(C12H6O4)(C10H8N2)]V = 3627.9 (2) Å3
Mr = 426.20Z = 8
Monoclinic, P21/nMo Kα radiation
a = 10.5169 (4) ŵ = 0.87 mm−1
b = 29.8928 (10) ÅT = 293 K
c = 11.5578 (4) Å0.09 × 0.09 × 0.08 mm
β = 93.178 (3)°
Data collection top
STOE IPDS-2
diffractometer		7116 independent reflections
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe, 2008)		5305 reflections with I > 2σ(I)
Tmin = 0.923, Tmax = 0.933Rint = 0.050
21152 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.141Δρmax = 0.39 e Å−3
S = 1.14Δρmin = −0.36 e Å−3
7116 reflectionsAbsolute structure: ?
523 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Fe10.78027 (6)0.713313 (19)0.77830 (5)0.03191 (15)
Fe20.77587 (6)0.580113 (19)0.67647 (5)0.03453 (16)
C10.4126 (4)0.64573 (15)0.7149 (4)0.0431 (10)
C20.3452 (5)0.68369 (16)0.7351 (5)0.0508 (12)
H20.38880.71060.74530.061*
C30.2125 (5)0.68347 (16)0.7410 (5)0.0527 (12)
H30.17090.71040.75300.063*
C40.1427 (4)0.64543 (15)0.7297 (4)0.0408 (10)
C50.1460 (5)0.56099 (17)0.7074 (5)0.0546 (12)
H50.05840.55980.71430.065*
C60.2098 (6)0.52337 (18)0.6930 (6)0.0707 (17)
H60.16580.49640.68940.085*
C70.3436 (6)0.52322 (18)0.6828 (6)0.0742 (18)
H70.38710.49660.67250.089*
C80.4058 (5)0.56222 (17)0.6883 (5)0.0571 (13)
H80.49360.56200.68170.069*
C90.3448 (4)0.60389 (15)0.7037 (4)0.0452 (11)
C100.2088 (5)0.60334 (15)0.7128 (4)0.0447 (10)
C110.5559 (4)0.64965 (14)0.7160 (3)0.0352 (9)
O10.6054 (3)0.68234 (10)0.7693 (3)0.0449 (7)
O20.6173 (3)0.61999 (11)0.6670 (3)0.0469 (8)
C12−0.0004 (4)0.64874 (14)0.7344 (3)0.0371 (9)
O3−0.0671 (3)0.61916 (11)0.6834 (3)0.0493 (8)
O4−0.0452 (3)0.68212 (11)0.7840 (3)0.0458 (7)
C210.7445 (4)0.94353 (14)0.8160 (4)0.0389 (9)
C220.7291 (5)0.91732 (15)0.9107 (4)0.0506 (12)
H220.71170.93060.98090.061*
C230.7392 (5)0.87040 (16)0.9035 (4)0.0498 (12)
H230.72630.85310.96870.060*
C240.7674 (4)0.84988 (14)0.8032 (4)0.0376 (9)
C250.8134 (6)0.85673 (17)0.5951 (4)0.0609 (14)
H250.82180.82590.58920.073*
C260.8274 (7)0.8826 (2)0.5001 (5)0.0779 (19)
H260.84560.86920.43030.093*
C270.8147 (7)0.9291 (2)0.5054 (5)0.0775 (19)
H270.82420.94640.43950.093*
C280.7886 (6)0.94909 (17)0.6072 (4)0.0570 (13)
H280.78020.98000.61010.068*
C290.7740 (4)0.92362 (15)0.7085 (4)0.0426 (10)
C300.7863 (4)0.87590 (14)0.7025 (4)0.0402 (10)
C310.7294 (5)0.99401 (15)0.8233 (4)0.0434 (10)
O110.8268 (4)1.01802 (11)0.8276 (3)0.0608 (9)
O120.6222 (4)1.01085 (12)0.8235 (4)0.0677 (11)
C320.7764 (4)0.79956 (14)0.7960 (4)0.0379 (9)
O130.8823 (3)0.78071 (10)0.7884 (3)0.0496 (8)
O140.6754 (3)0.77705 (10)0.7947 (3)0.0450 (7)
C410.7818 (4)0.70824 (15)0.3412 (4)0.0403 (10)
C420.8945 (4)0.71142 (17)0.4109 (4)0.0454 (11)
H420.97280.71090.37730.054*
C430.8896 (4)0.71524 (17)0.5294 (4)0.0452 (11)
H430.96650.71680.57310.054*
N10.7819 (4)0.71690 (12)0.5860 (3)0.0407 (8)
C440.6740 (4)0.71451 (16)0.5187 (4)0.0447 (10)
H440.59720.71590.55480.054*
C450.6691 (5)0.71017 (17)0.3990 (4)0.0476 (11)
H450.59100.70860.35740.057*
C460.7822 (4)0.70478 (15)0.2126 (4)0.0393 (10)
C470.8938 (4)0.70362 (16)0.1559 (4)0.0458 (11)
H470.97170.70260.19810.055*
C480.8901 (4)0.70399 (16)0.0356 (4)0.0430 (10)
H480.96690.7032−0.00050.052*
N20.7827 (3)0.70538 (11)−0.0306 (3)0.0370 (8)
C490.6737 (4)0.70524 (16)0.0248 (4)0.0443 (11)
H490.59700.7054−0.01930.053*
C500.6701 (4)0.70486 (16)0.1438 (4)0.0442 (10)
H500.59210.70470.17800.053*
C510.7816 (5)0.58619 (16)1.1148 (4)0.0496 (12)
C520.8930 (6)0.5839 (2)1.0576 (5)0.0728 (17)
H520.97120.58461.09940.087*
C530.8884 (6)0.5806 (2)0.9386 (5)0.0684 (16)
H530.96540.57920.90290.082*
N110.7819 (4)0.57940 (13)0.8710 (3)0.0492 (9)
C540.6749 (6)0.5807 (2)0.9274 (4)0.0596 (14)
H540.59800.57940.88380.071*
C550.6709 (6)0.5839 (2)1.0456 (4)0.0642 (15)
H550.59260.58451.07930.077*
C560.7805 (5)0.58971 (16)1.2434 (4)0.0466 (11)
C570.8913 (5)0.58902 (19)1.3130 (4)0.0573 (13)
H570.96980.58941.27970.069*
C580.8858 (5)0.58781 (19)1.4322 (4)0.0562 (13)
H580.96200.58731.47710.067*
N120.7758 (4)0.58739 (13)1.4864 (3)0.0441 (9)
C590.6696 (5)0.59193 (17)1.4197 (4)0.0512 (12)
H590.59270.59451.45510.061*
C600.6680 (5)0.59301 (18)1.3002 (4)0.0536 (12)
H600.59100.59601.25740.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0347 (3)0.0338 (3)0.0273 (3)−0.0002 (2)0.0020 (2)−0.0013 (2)
Fe20.0383 (3)0.0346 (3)0.0307 (3)−0.0001 (3)0.0018 (2)−0.0012 (2)
C10.039 (2)0.046 (2)0.044 (2)0.0056 (19)0.0007 (19)−0.006 (2)
C20.049 (3)0.040 (2)0.063 (3)−0.004 (2)0.002 (2)−0.002 (2)
C30.049 (3)0.043 (3)0.067 (3)0.000 (2)0.008 (2)−0.004 (2)
C40.036 (2)0.045 (2)0.042 (2)−0.0040 (19)0.0024 (19)−0.0012 (19)
C50.045 (3)0.055 (3)0.064 (3)−0.009 (2)0.003 (2)0.000 (2)
C60.068 (4)0.042 (3)0.101 (5)−0.006 (3)0.002 (3)−0.001 (3)
C70.067 (4)0.038 (3)0.116 (5)0.004 (3)−0.001 (4)−0.008 (3)
C80.039 (3)0.053 (3)0.079 (4)0.001 (2)0.000 (2)−0.012 (3)
C90.043 (3)0.044 (2)0.049 (3)0.001 (2)0.002 (2)−0.001 (2)
C100.046 (3)0.042 (2)0.046 (3)−0.002 (2)0.003 (2)−0.001 (2)
C110.037 (2)0.037 (2)0.032 (2)−0.0013 (18)0.0017 (17)0.0018 (17)
O10.0465 (18)0.0490 (18)0.0393 (17)−0.0134 (14)0.0032 (14)−0.0098 (14)
O20.0446 (18)0.0493 (18)0.0471 (18)0.0060 (15)0.0068 (15)−0.0029 (15)
C120.041 (2)0.040 (2)0.030 (2)0.0008 (19)0.0008 (17)0.0007 (17)
O30.0446 (18)0.0543 (19)0.0489 (19)−0.0092 (15)0.0013 (15)−0.0082 (15)
O40.0478 (18)0.0520 (18)0.0376 (16)0.0123 (15)0.0022 (14)−0.0081 (14)
C210.042 (2)0.035 (2)0.040 (2)−0.0005 (18)0.0016 (19)−0.0020 (18)
C220.072 (3)0.039 (2)0.043 (3)0.006 (2)0.016 (2)−0.002 (2)
C230.068 (3)0.041 (2)0.041 (3)0.002 (2)0.013 (2)0.007 (2)
C240.040 (2)0.034 (2)0.039 (2)−0.0016 (18)0.0039 (18)0.0017 (17)
C250.098 (4)0.044 (3)0.041 (3)0.000 (3)0.010 (3)−0.005 (2)
C260.131 (6)0.064 (4)0.039 (3)0.006 (4)0.016 (3)−0.004 (3)
C270.129 (6)0.064 (4)0.041 (3)0.010 (4)0.017 (3)0.010 (3)
C280.083 (4)0.044 (3)0.045 (3)0.003 (3)0.008 (3)0.006 (2)
C290.050 (3)0.039 (2)0.038 (2)−0.001 (2)−0.001 (2)0.0025 (18)
C300.048 (3)0.037 (2)0.035 (2)−0.0007 (19)−0.0009 (19)−0.0019 (18)
C310.055 (3)0.039 (2)0.035 (2)0.002 (2)0.003 (2)0.0033 (19)
O110.067 (2)0.0405 (18)0.075 (3)−0.0081 (17)0.005 (2)−0.0023 (17)
O120.055 (2)0.049 (2)0.098 (3)0.0128 (17)0.000 (2)−0.003 (2)
C320.042 (2)0.038 (2)0.033 (2)−0.0023 (19)−0.0006 (18)0.0007 (17)
O130.0375 (17)0.0417 (18)0.070 (2)0.0018 (14)0.0034 (15)−0.0044 (15)
O140.0412 (17)0.0352 (16)0.059 (2)−0.0033 (13)0.0029 (15)−0.0015 (14)
C410.043 (2)0.045 (2)0.034 (2)−0.003 (2)0.0057 (18)−0.0001 (18)
C420.037 (2)0.066 (3)0.034 (2)−0.004 (2)0.0033 (18)0.003 (2)
C430.040 (2)0.065 (3)0.031 (2)−0.007 (2)−0.0013 (18)0.002 (2)
N10.050 (2)0.0400 (19)0.0321 (19)−0.0006 (17)0.0028 (16)0.0004 (15)
C440.044 (2)0.062 (3)0.028 (2)0.005 (2)0.0056 (19)0.002 (2)
C450.044 (3)0.068 (3)0.031 (2)0.003 (2)0.0010 (19)0.004 (2)
C460.041 (2)0.046 (2)0.031 (2)−0.0022 (19)0.0037 (18)0.0001 (18)
C470.040 (2)0.063 (3)0.034 (2)0.001 (2)−0.0013 (19)−0.004 (2)
C480.036 (2)0.060 (3)0.033 (2)−0.002 (2)0.0019 (18)−0.003 (2)
N20.043 (2)0.0399 (19)0.0282 (17)−0.0001 (15)0.0033 (15)0.0012 (14)
C490.037 (2)0.062 (3)0.034 (2)0.002 (2)−0.0006 (18)−0.004 (2)
C500.040 (2)0.060 (3)0.033 (2)0.003 (2)0.0018 (18)−0.002 (2)
C510.068 (3)0.050 (3)0.031 (2)0.006 (2)0.004 (2)−0.001 (2)
C520.061 (3)0.121 (5)0.037 (3)0.017 (3)0.000 (2)−0.005 (3)
C530.061 (3)0.106 (5)0.038 (3)0.013 (3)0.005 (2)0.004 (3)
N110.066 (3)0.047 (2)0.035 (2)0.002 (2)0.0051 (19)−0.0004 (17)
C540.065 (3)0.081 (4)0.032 (2)−0.010 (3)−0.004 (2)−0.001 (2)
C550.062 (3)0.097 (4)0.034 (3)−0.005 (3)0.005 (2)−0.001 (3)
C560.058 (3)0.051 (3)0.030 (2)0.004 (2)−0.001 (2)0.0001 (19)
C570.059 (3)0.075 (4)0.038 (3)0.001 (3)0.005 (2)−0.001 (2)
C580.054 (3)0.081 (4)0.033 (2)0.000 (3)0.002 (2)−0.006 (2)
N120.051 (2)0.050 (2)0.0309 (19)0.0037 (18)0.0040 (17)−0.0018 (16)
C590.059 (3)0.062 (3)0.033 (2)0.005 (2)0.003 (2)−0.006 (2)
C600.055 (3)0.071 (3)0.034 (2)0.008 (3)−0.003 (2)−0.003 (2)
Geometric parameters (Å, °) top
Fe1—O4i2.056 (3)C28—C291.412 (6)
Fe1—O12.057 (3)C28—H280.9300
Fe1—O142.215 (3)C29—C301.435 (6)
Fe1—N2ii2.220 (3)C31—O121.235 (6)
Fe1—N12.227 (4)C31—O111.249 (6)
Fe1—O132.283 (3)O11—Fe2vi2.147 (4)
Fe2—O3i2.020 (3)O12—Fe2vi2.332 (4)
Fe2—O22.048 (3)C32—O131.256 (5)
Fe2—O11iii2.147 (4)C32—O141.257 (5)
Fe2—N12iv2.207 (4)C41—C451.393 (6)
Fe2—N112.246 (4)C41—C421.399 (6)
Fe2—O12iii2.332 (4)C41—C461.490 (6)
C1—C21.365 (6)C42—C431.377 (6)
C1—C91.442 (6)C42—H420.9300
C1—C111.512 (6)C43—N11.340 (6)
C2—C31.400 (7)C43—H430.9300
C2—H20.9300N1—C441.341 (6)
C3—C41.356 (6)C44—C451.388 (6)
C3—H30.9300C44—H440.9300
C4—C101.456 (6)C45—H450.9300
C4—C121.512 (6)C46—C471.377 (6)
C5—C61.325 (8)C46—C501.385 (6)
C5—C101.428 (7)C47—C481.388 (6)
C5—H50.9300C47—H470.9300
C6—C71.419 (8)C48—N21.330 (5)
C6—H60.9300C48—H480.9300
C7—C81.336 (7)N2—C491.344 (5)
C7—H70.9300N2—Fe1iv2.220 (3)
C8—C91.417 (7)C49—C501.378 (6)
C8—H80.9300C49—H490.9300
C9—C101.440 (7)C50—H500.9300
C11—O21.250 (5)C51—C551.377 (7)
C11—O11.253 (5)C51—C521.379 (7)
C12—O31.255 (5)C51—C561.490 (6)
C12—O41.256 (5)C52—C531.377 (7)
O3—Fe2v2.020 (3)C52—H520.9300
O4—Fe1v2.056 (3)C53—N111.330 (7)
C21—C221.363 (6)C53—H530.9300
C21—C291.427 (6)N11—C541.331 (7)
C21—C311.520 (6)C54—C551.373 (7)
C22—C231.410 (6)C54—H540.9300
C22—H220.9300C55—H550.9300
C23—C241.358 (6)C56—C571.379 (7)
C23—H230.9300C56—C601.387 (7)
C24—C301.423 (6)C57—C581.382 (7)
C24—C321.510 (6)C57—H570.9300
C25—C261.358 (7)C58—N121.346 (6)
C25—C301.410 (6)C58—H580.9300
C25—H250.9300N12—C591.329 (6)
C26—C271.398 (8)N12—Fe2ii2.207 (4)
C26—H260.9300C59—C601.381 (6)
C27—C281.361 (8)C59—H590.9300
C27—H270.9300C60—H600.9300
O4i—Fe1—O1126.27 (13)C27—C28—C29121.1 (5)
O4i—Fe1—O14146.62 (12)C27—C28—H28119.4
O1—Fe1—O1486.76 (12)C29—C28—H28119.4
O4i—Fe1—N2ii87.63 (13)C28—C29—C21122.4 (4)
O1—Fe1—N2ii87.88 (13)C28—C29—C30118.8 (4)
O14—Fe1—N2ii89.13 (12)C21—C29—C30118.8 (4)
O4i—Fe1—N189.88 (13)C25—C30—C24122.8 (4)
O1—Fe1—N191.57 (13)C25—C30—C29118.0 (4)
O14—Fe1—N194.34 (13)C24—C30—C29119.1 (4)
N2ii—Fe1—N1176.46 (13)O12—C31—O11120.8 (4)
O4i—Fe1—O1389.00 (12)O12—C31—C21120.2 (4)
O1—Fe1—O13144.73 (12)O11—C31—C21118.9 (4)
O14—Fe1—O1358.08 (11)C31—O11—Fe2vi94.9 (3)
N2ii—Fe1—O1393.68 (13)C31—O12—Fe2vi86.7 (3)
N1—Fe1—O1388.78 (13)O13—C32—O14120.7 (4)
O3i—Fe2—O2109.11 (13)O13—C32—C24120.6 (4)
O3i—Fe2—O11iii155.44 (14)O14—C32—C24118.6 (4)
O2—Fe2—O11iii95.45 (13)C32—O13—Fe189.1 (2)
O3i—Fe2—N12iv86.43 (14)C32—O14—Fe192.1 (3)
O2—Fe2—N12iv86.23 (13)C45—C41—C42115.9 (4)
O11iii—Fe2—N12iv95.24 (15)C45—C41—C46122.0 (4)
O3i—Fe2—N1189.30 (15)C42—C41—C46122.0 (4)
O2—Fe2—N1192.12 (14)C43—C42—C41120.1 (4)
O11iii—Fe2—N1189.99 (15)C43—C42—H42120.0
N12iv—Fe2—N11174.64 (15)C41—C42—H42120.0
O3i—Fe2—O12iii97.94 (13)N1—C43—C42124.5 (4)
O2—Fe2—O12iii152.87 (13)N1—C43—H43117.7
O11iii—Fe2—O12iii57.51 (13)C42—C43—H43117.7
N12iv—Fe2—O12iii93.59 (15)C43—N1—C44115.2 (4)
N11—Fe2—O12iii90.21 (15)C43—N1—Fe1122.6 (3)
C2—C1—C9118.5 (4)C44—N1—Fe1121.5 (3)
C2—C1—C11117.5 (4)N1—C44—C45124.4 (4)
C9—C1—C11123.8 (4)N1—C44—H44117.8
C1—C2—C3122.2 (4)C45—C44—H44117.8
C1—C2—H2118.9C44—C45—C41119.8 (4)
C3—C2—H2118.9C44—C45—H45120.1
C4—C3—C2122.3 (5)C41—C45—H45120.1
C4—C3—H3118.8C47—C46—C50116.6 (4)
C2—C3—H3118.8C47—C46—C41121.8 (4)
C3—C4—C10118.5 (4)C50—C46—C41121.6 (4)
C3—C4—C12118.5 (4)C46—C47—C48119.9 (4)
C10—C4—C12123.0 (4)C46—C47—H47120.0
C6—C5—C10121.5 (5)C48—C47—H47120.0
C6—C5—H5119.3N2—C48—C47123.6 (4)
C10—C5—H5119.3N2—C48—H48118.2
C5—C6—C7121.6 (5)C47—C48—H48118.2
C5—C6—H6119.2C48—N2—C49116.4 (4)
C7—C6—H6119.2C48—N2—Fe1iv122.6 (3)
C8—C7—C6118.6 (5)C49—N2—Fe1iv120.8 (3)
C8—C7—H7120.7N2—C49—C50123.2 (4)
C6—C7—H7120.7N2—C49—H49118.4
C7—C8—C9123.3 (5)C50—C49—H49118.4
C7—C8—H8118.4C49—C50—C46120.3 (4)
C9—C8—H8118.4C49—C50—H50119.9
C8—C9—C10117.3 (4)C46—C50—H50119.9
C8—C9—C1123.2 (4)C55—C51—C52115.6 (4)
C10—C9—C1119.4 (4)C55—C51—C56122.0 (5)
C5—C10—C9117.8 (4)C52—C51—C56122.4 (5)
C5—C10—C4123.3 (4)C53—C52—C51119.9 (5)
C9—C10—C4118.9 (4)C53—C52—H52120.0
O2—C11—O1124.4 (4)C51—C52—H52120.0
O2—C11—C1118.7 (4)N11—C53—C52124.8 (5)
O1—C11—C1116.8 (4)N11—C53—H53117.6
C11—O1—Fe1136.2 (3)C52—C53—H53117.6
C11—O2—Fe2145.8 (3)C53—N11—C54114.8 (4)
O3—C12—O4124.1 (4)C53—N11—Fe2124.3 (3)
O3—C12—C4118.0 (4)C54—N11—Fe2120.7 (3)
O4—C12—C4117.9 (4)N11—C54—C55124.2 (5)
C12—O3—Fe2v149.3 (3)N11—C54—H54117.9
C12—O4—Fe1v134.6 (3)C55—C54—H54117.9
C22—C21—C29120.0 (4)C54—C55—C51120.7 (5)
C22—C21—C31120.6 (4)C54—C55—H55119.7
C29—C21—C31119.4 (4)C51—C55—H55119.7
C21—C22—C23120.8 (4)C57—C56—C60116.1 (4)
C21—C22—H22119.6C57—C56—C51121.8 (5)
C23—C22—H22119.6C60—C56—C51122.1 (4)
C24—C23—C22121.4 (4)C56—C57—C58120.1 (5)
C24—C23—H23119.3C56—C57—H57119.9
C22—C23—H23119.3C58—C57—H57119.9
C23—C24—C30119.9 (4)N12—C58—C57123.3 (5)
C23—C24—C32120.9 (4)N12—C58—H58118.4
C30—C24—C32119.2 (4)C57—C58—H58118.4
C26—C25—C30121.1 (5)C59—N12—C58116.4 (4)
C26—C25—H25119.5C59—N12—Fe2ii122.8 (3)
C30—C25—H25119.5C58—N12—Fe2ii120.8 (3)
C25—C26—C27121.1 (5)N12—C59—C60123.1 (5)
C25—C26—H26119.5N12—C59—H59118.4
C27—C26—H26119.5C60—C59—H59118.4
C28—C27—C26119.9 (5)C59—C60—C56120.5 (5)
C28—C27—H27120.0C59—C60—H60119.7
C26—C27—H27120.0C56—C60—H60119.7
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) −x+3/2, y−1/2, −z+3/2; (iv) x, y, z−1; (v) x−1, y, z; (vi) −x+3/2, y+1/2, −z+3/2.
Table 1
Selected geometric parameters (Å, °) top
Fe1—O4i2.056 (3)Fe2—O22.048 (3)
Fe1—O12.057 (3)Fe2—O11iii2.147 (4)
Fe1—O142.215 (3)Fe2—N12iv2.207 (4)
Fe1—N2ii2.220 (3)Fe2—N112.246 (4)
Fe1—N12.227 (4)Fe2—O12iii2.332 (4)
Fe1—O132.283 (3)N12—Fe2ii2.207 (4)
Fe2—O3i2.020 (3)
O4i—Fe1—O1126.27 (13)O3i—Fe2—O2109.11 (13)
O4i—Fe1—O14146.62 (12)O3i—Fe2—O11iii155.44 (14)
O1—Fe1—O1486.76 (12)O2—Fe2—O11iii95.45 (13)
O4i—Fe1—N2ii87.63 (13)O3i—Fe2—N12iv86.43 (14)
O1—Fe1—N2ii87.88 (13)O2—Fe2—N12iv86.23 (13)
O14—Fe1—N2ii89.13 (12)O11iii—Fe2—N12iv95.24 (15)
O4i—Fe1—N189.88 (13)O3i—Fe2—N1189.30 (15)
O1—Fe1—N191.57 (13)O2—Fe2—N1192.12 (14)
O14—Fe1—N194.34 (13)O11iii—Fe2—N1189.99 (15)
N2ii—Fe1—N1176.46 (13)N12iv—Fe2—N11174.64 (15)
O4i—Fe1—O1389.00 (12)O3i—Fe2—O12iii97.94 (13)
O1—Fe1—O13144.73 (12)O2—Fe2—O12iii152.87 (13)
O14—Fe1—O1358.08 (11)O11iii—Fe2—O12iii57.51 (13)
N2ii—Fe1—O1393.68 (13)N12iv—Fe2—O12iii93.59 (15)
N1—Fe1—O1388.78 (13)N11—Fe2—O12iii90.21 (15)
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) −x+3/2, y−1/2, −z+3/2; (iv) x, y, z−1.
Acknowledgements top

This work is supported by the state of Schleswig-Holstein. We thank Professor Dr Wolfgang Bensch for the facility to use his equipment.

references
References top

Brandenburg, K. (2008). DIAMOND. Bonn, Germany

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Stoe (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.

Zheng, X.-J., Jin, L.-P., Gao, S. & Lu, S.-Z. (2005). New J. Chem. pp. 798–804.