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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): m122.
Published online 2008 December 20. doi:  10.1107/S1600536808042992
PMCID: PMC2968022

Poly[(μ-4,4′-bipyridine)(μ-naph­tha­lene-1,4-dicarboxyl­ato)iron(II)]

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-0m122-scheme1.jpg

Experimental

Crystal data

  • [Fe(C12H6O4)(C10H8N2)]
  • M r = 426.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m122-efi2.jpg
  • a = 10.5169 (4) Å
  • b = 29.8928 (10) Å
  • c = 11.5578 (4) Å
  • β = 93.178 (3)°
  • V = 3627.9 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.87 mm−1
  • T = 293 (2) K
  • 0.09 × 0.09 × 0.08 mm

Data collection

  • STOE IPDS-2 diffractometer
  • Absorption correction: numerical (X-SHAPE and X-RED32; Stoe, 2008 [triangle]) T min = 0.923, T max = 0.933
  • 21152 measured reflections
  • 7116 independent reflections
  • 5305 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 0.141
  • S = 1.14
  • 7116 reflections
  • 523 parameters
  • H-atom parameters constrained
  • Δρmax = 0.39 e Å−3
  • Δρmin = −0.36 e Å−3

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

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042992/ng2529sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042992/ng2529Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

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.
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.
Fig. 3.
: Crystal structure of the title compound with view in the direction of the crystallographic a axis.

Crystal data

[Fe(C12H6O4)(C10H8N2)]F(000) = 1744
Mr = 426.20Dx = 1.561 Mg m3
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 mm1
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

STOE IPDS-2 diffractometer7116 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

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 = 1.14w = 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 Å3
0 restraintsΔρmin = −0.36 e Å3

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)

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)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2529).

References

  • Brandenburg, K. (2008). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • 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.

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