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Acta Cryst. (2007). E63, m1845-m1846    [ doi:10.1107/S1600536807027973 ]

Tetraaquabis(4,4'-bipyridine)iron(II) pyridine-2,6-dicarboxylate tetrahydrate

Y.-X. Gao, L.-B. Wang and Y.-L. Niu

Abstract top

The title compound, [Fe(C10H8N2)2(H2O)4](C7H3NO4)·4H2O, prepared by hydrothermal synthesis, contains isolated tetraaquabis(4,4'-bipyridine)iron(II) cations, comprising two 4,4'-bipyridine molecules bound to FeII in a trans manner. The cations lie in layers, with pyridine-2,6-dicarboxylate dianions and water molecules forming an extensive hydrogen-bond network between them. The cations exhibit noncrystallographic inversion symmetry. The crystal was a partial inversion twin.

Comment top

Metal-organic frameworks have applications in catalysis, optical materials, membranes, and sorption (Evans, Ngo & Lin, 2001; Vioux et al., 2004; Sanchez et al., 2003; Evans & Lin, 2001; Jannasch, 2003; Javaid et al., 2001; Honma et al., 2001; Sudik et al., 2005; Rowsell et al., 2004; Kitaura et al., 2004; Suzuki et al., 2002).

Design of metal-organic frameworks often utilizes a metal cation, metal cluster, or metal oxide substructure as a node, from which rigid or flexible multitopic organic ligands radiate to act as tethers to adjacent nodes for the bottom-up construction of complex extended architectures. While a variety of organic molecules have been investigated as potential tethers, materials incorporating multitopic carboxylates and pyridine ligands have been employed most extensively.

In the title compound, FeII is hexa-coordinated in an octahedral manner by four water molecules in the equatorial plane and two N atoms in the axial positions from two 4,4'-bipyridine molecules (Fig. 1). The Fe—N and Fe—O bond lengths are in the range 2.265 (4)–2.266 (4) and 2.161 (3)–2.202 (4) Å, respectively. The cations lie in layers in the bc planes. Pyridine-2,6-dicarboxylate anions and water molecules lie between these layers, forming an extensive hydrogen-bond network.

Related literature top

For literature concerning metal–organic frameworks, see: Evans, Ngo & Lin (2001); Vioux et al. (2004); Sanchez et al. (2003); Evans & Lin (2001); Jannasch (2003); Javaid et al. (2001); Honma et al. (2001); Sudik et al. (2005); Rowsell et al. (2004); Kitaura et al. (2004); Suzuki et al. (2002).

Experimental top

A mixture of FeCl2 (0.5 mmol), pyridine-2,6-dicarboxylic acid (0.5 mmol), NaOH (1 mmol), 4,4'-bipyridine (0.5 mmol), H2O (8 ml) and ethanol (8 ml) were place in a 25 ml Teflon-lined stainless steel autoclave and heated at 433 K for two days. On cooling to room temperature, blue crystals were obtained with a yield of 12%. Elemental analysis calculated: C 47.83, H 5.17, N 10.33, Fe 8.27%; found: C 47.87, H 5.21, N 10.27, Fe 8.16%.

Refinement top

H atoms bound to C atoms were placed geometrically and refined as riding atoms with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). H atoms of the water molecules were located from difference Fourier maps and were refined with distance restraints of O—H = 0.82 (1) Å and H···H = 1.35 (2) Å, and with Uiso(H) = 1.5Ueq(O). The [Fe(C10H8N2)2(H2O)4]2+ cations exhibit non-crystallographic inversion symmetry. The refined Flack parameter (Flack, 1983) from 530 Freidel pairs is 0.36 (3).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXL97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids for non-H atoms.
Tetraaquabis(4,4'-bipyridine)iron(II) pyridine-2,6-dicarboxylate tetrahydrate top
Crystal data top
[Fe(C10H8N2)2(H2O)4](C7H3NO4)·4H2OF(000) = 1416
Mr = 677.45Dx = 1.452 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 3290 reflections
a = 18.201 (1) Åθ = 2.0–55.0°
b = 6.900 (1) ŵ = 0.56 mm−1
c = 25.010 (1) ÅT = 293 K
β = 99.40 (3)°Block, blue
V = 3098.9 (5) Å30.10 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		2946 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 25.1°, θmin = 1.7°
ω scansh = −19→21
5104 measured reflectionsk = −8→4
3180 independent reflectionsl = −29→12
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0702P)2 + 1.0906P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3180 reflectionsΔρmax = 0.35 e Å−3
455 parametersΔρmin = −0.38 e Å−3
26 restraintsAbsolute structure: Flack (1983), with 530 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.36 (3)
Crystal data top
[Fe(C10H8N2)2(H2O)4](C7H3NO4)·4H2OV = 3098.9 (5) Å3
Mr = 677.45Z = 4
Monoclinic, CcMo Kα radiation
a = 18.201 (1) ŵ = 0.56 mm−1
b = 6.900 (1) ÅT = 293 K
c = 25.010 (1) Å0.10 × 0.10 × 0.10 mm
β = 99.40 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2946 reflections with I > 2σ(I)
5104 measured reflectionsRint = 0.018
3180 independent reflectionsθmax = 25.1°
Refinement top
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.105Δρmax = 0.35 e Å−3
S = 1.05Δρmin = −0.38 e Å−3
3180 reflectionsAbsolute structure: Flack (1983), with 530 Friedel pairs
455 parametersFlack parameter: 0.36 (3)
26 restraints
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
Fe10.82218 (7)0.73736 (9)0.62280 (5)0.03412 (16)
C10.5731 (3)0.1741 (7)0.8192 (2)0.0385 (11)
C20.5712 (5)0.2657 (6)0.8733 (4)0.0335 (7)
C30.5690 (3)0.4671 (6)0.8799 (2)0.0395 (10)
H3A0.56800.54730.84980.047*
C40.5683 (3)0.5490 (6)0.9306 (2)0.0405 (10)
H4A0.56630.68290.93430.049*
C50.5706 (2)0.4311 (6)0.97538 (19)0.0391 (10)
H5A0.57030.48661.00920.047*
C60.5735 (3)0.2278 (6)0.9706 (3)0.0342 (13)
C70.5791 (2)0.0996 (6)1.02025 (18)0.0347 (9)
C80.8773 (3)0.8254 (9)0.7460 (2)0.0476 (13)
H8A0.92280.81220.73400.057*
C90.8770 (3)0.8418 (8)0.8006 (2)0.0448 (12)
H9A0.92200.84160.82440.054*
C100.8112 (3)0.8587 (6)0.82083 (18)0.0279 (9)
C110.7468 (3)0.8708 (8)0.7815 (2)0.0481 (13)
H11A0.70070.89110.79200.058*
C120.7517 (3)0.8526 (9)0.7275 (2)0.0503 (14)
H12A0.70790.85820.70250.060*
C130.8081 (2)0.8626 (6)0.87930 (18)0.0287 (10)
C140.8730 (3)0.8650 (7)0.91726 (18)0.0379 (11)
H14A0.91940.86540.90620.045*
C150.8673 (3)0.8668 (7)0.9720 (2)0.0397 (11)
H15A0.91110.86850.99710.048*
C160.7424 (3)0.8637 (7)0.9536 (2)0.0450 (12)
H16A0.69700.86250.96610.054*
C170.7409 (3)0.8628 (7)0.8989 (2)0.0402 (11)
H17A0.69580.86230.87520.048*
C180.8956 (3)0.6415 (7)0.51671 (19)0.0387 (11)
H18A0.94010.64010.54100.046*
C190.8987 (3)0.6324 (8)0.46210 (18)0.0414 (12)
H19A0.94430.62450.45010.050*
C200.8331 (3)0.6353 (6)0.42539 (18)0.0285 (10)
C210.7673 (3)0.6404 (7)0.4459 (2)0.0418 (12)
H21A0.72180.63820.42270.050*
C220.7698 (3)0.6488 (8)0.5007 (2)0.0457 (12)
H22A0.72470.65210.51370.055*
C230.8328 (3)0.6379 (6)0.36586 (18)0.0294 (10)
C240.7669 (3)0.6306 (8)0.3286 (2)0.0478 (13)
H24A0.72140.62190.34080.057*
C250.7689 (3)0.6362 (8)0.2741 (2)0.0482 (13)
H25A0.72390.63110.25020.058*
C260.8947 (4)0.6555 (9)0.2887 (2)0.0576 (15)
H26A0.93940.66410.27530.069*
C270.8981 (3)0.6507 (8)0.3441 (2)0.0467 (13)
H27A0.94390.65600.36680.056*
N10.5734 (3)0.1479 (6)0.91981 (19)0.0466 (10)
N20.8150 (2)0.8275 (5)0.70892 (16)0.0345 (9)
N30.8037 (3)0.8662 (5)0.99043 (16)0.0383 (10)
N40.8316 (2)0.6524 (5)0.53671 (15)0.0322 (9)
N50.8321 (3)0.6486 (5)0.25322 (17)0.0424 (10)
O10.7848 (2)1.0205 (5)0.59307 (15)0.0469 (9)
H110.757 (3)1.098 (6)0.605 (2)0.070*
H120.799 (3)1.074 (7)0.5671 (17)0.070*
O20.9377 (2)0.8418 (5)0.63036 (16)0.0457 (8)
H210.947 (3)0.957 (2)0.631 (3)0.069*
H220.974 (2)0.785 (6)0.646 (3)0.069*
O30.8599 (2)0.4528 (5)0.65227 (14)0.0477 (9)
H310.894 (2)0.384 (8)0.646 (2)0.072*
H320.856 (3)0.445 (8)0.6841 (8)0.072*
O40.70693 (19)0.6295 (5)0.61352 (15)0.0407 (8)
H410.693 (3)0.516 (2)0.611 (3)0.061*
H420.672 (2)0.697 (6)0.600 (3)0.061*
O50.4859 (3)0.7286 (6)0.6359 (2)0.0577 (14)
H510.511 (3)0.738 (9)0.612 (2)0.087*
H520.514 (3)0.724 (11)0.6650 (14)0.087*
O60.5641 (3)0.6916 (7)0.73867 (17)0.0714 (11)
H610.569 (4)0.761 (9)0.7655 (19)0.107*
H620.597 (3)0.610 (9)0.744 (3)0.107*
O70.5641 (3)0.1491 (5)0.68152 (16)0.0554 (10)
H710.571 (4)0.180 (8)0.7137 (8)0.083*
H720.543 (4)0.044 (5)0.679 (2)0.083*
O80.6593 (3)0.2454 (5)0.6074 (2)0.0487 (13)
H810.636 (3)0.220 (9)0.6318 (17)0.073*
H820.635 (3)0.209 (9)0.5790 (13)0.073*
O90.5726 (3)0.2898 (6)0.77972 (17)0.0533 (11)
O100.5739 (2)−0.0063 (5)0.81586 (14)0.0472 (8)
O110.5811 (2)0.1826 (5)1.06512 (14)0.0470 (9)
O120.5839 (2)−0.0786 (4)1.01353 (13)0.0453 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0355 (3)0.0432 (3)0.0237 (2)0.0010 (3)0.00518 (18)0.0011 (3)
C10.028 (2)0.049 (3)0.038 (3)0.005 (2)0.0020 (19)−0.001 (2)
C20.0201 (14)0.0445 (18)0.0342 (17)0.002 (2)−0.0004 (12)0.004 (2)
C30.034 (2)0.0435 (19)0.039 (3)0.002 (2)−0.0002 (19)0.003 (2)
C40.040 (2)0.032 (2)0.048 (3)0.0044 (19)0.002 (2)−0.003 (2)
C50.036 (2)0.044 (2)0.037 (2)−0.001 (2)0.0022 (19)−0.012 (2)
C60.026 (2)0.041 (2)0.036 (3)−0.0011 (19)0.006 (2)−0.007 (2)
C70.028 (2)0.045 (2)0.032 (2)−0.0034 (19)0.0064 (17)−0.0061 (19)
C80.030 (3)0.087 (4)0.027 (3)−0.003 (3)0.010 (2)−0.007 (3)
C90.024 (2)0.081 (4)0.027 (3)−0.002 (2)−0.002 (2)−0.005 (2)
C100.030 (2)0.0301 (19)0.023 (2)0.0014 (17)0.0050 (19)−0.0006 (17)
C110.029 (3)0.081 (3)0.036 (3)0.007 (2)0.012 (2)−0.009 (3)
C120.039 (3)0.081 (4)0.029 (3)0.014 (3)0.001 (2)−0.005 (2)
C130.033 (3)0.0258 (18)0.026 (2)0.0020 (17)0.003 (2)−0.0030 (16)
C140.035 (3)0.059 (3)0.020 (2)−0.001 (2)0.006 (2)−0.003 (2)
C150.037 (3)0.051 (2)0.028 (3)−0.004 (2)−0.006 (2)−0.003 (2)
C160.044 (3)0.059 (3)0.035 (3)0.002 (2)0.016 (2)0.000 (2)
C170.035 (3)0.057 (3)0.030 (3)0.003 (2)0.009 (2)−0.004 (2)
C180.030 (3)0.060 (3)0.025 (2)0.008 (2)0.000 (2)−0.005 (2)
C190.033 (3)0.070 (3)0.021 (2)0.004 (2)0.003 (2)−0.003 (2)
C200.035 (3)0.0285 (18)0.022 (2)0.0008 (18)0.0047 (18)−0.0012 (16)
C210.030 (3)0.070 (3)0.025 (2)−0.007 (2)0.003 (2)−0.006 (2)
C220.033 (3)0.074 (4)0.031 (3)−0.008 (3)0.008 (2)−0.007 (2)
C230.034 (3)0.0307 (19)0.025 (2)0.0023 (18)0.0105 (19)−0.0012 (17)
C240.034 (3)0.075 (3)0.035 (3)0.002 (2)0.008 (2)0.000 (2)
C250.047 (3)0.071 (3)0.028 (3)0.003 (3)0.007 (2)0.001 (2)
C260.054 (4)0.090 (4)0.034 (3)−0.008 (3)0.022 (3)−0.008 (3)
C270.034 (3)0.074 (3)0.033 (3)−0.005 (2)0.006 (2)−0.005 (2)
N10.036 (2)0.056 (2)0.048 (3)0.003 (2)0.0065 (19)−0.002 (2)
N20.035 (2)0.042 (2)0.027 (2)0.0029 (17)0.0048 (17)−0.0016 (16)
N30.050 (3)0.044 (2)0.023 (2)0.0024 (18)0.0102 (18)−0.0008 (16)
N40.033 (2)0.041 (2)0.022 (2)−0.0026 (16)0.0033 (17)−0.0015 (16)
N50.054 (3)0.046 (2)0.028 (2)−0.005 (2)0.0100 (19)−0.0045 (18)
O10.061 (2)0.0487 (18)0.0351 (19)0.0179 (17)0.0201 (17)0.0103 (15)
O20.037 (2)0.0534 (18)0.047 (2)−0.0058 (16)0.0062 (17)−0.0034 (17)
O30.069 (3)0.0472 (18)0.0299 (17)0.0214 (17)0.0172 (17)0.0102 (15)
O40.036 (2)0.0444 (16)0.0406 (19)−0.0041 (14)0.0036 (16)0.0007 (15)
O50.054 (3)0.067 (3)0.058 (3)0.008 (2)0.026 (3)0.014 (2)
O60.083 (3)0.084 (3)0.046 (2)−0.006 (3)0.010 (2)−0.011 (2)
O70.070 (3)0.053 (2)0.045 (2)−0.009 (2)0.013 (2)−0.0043 (18)
O80.050 (3)0.054 (3)0.042 (3)−0.0061 (16)0.010 (2)−0.0065 (16)
O90.067 (3)0.065 (2)0.028 (2)0.006 (2)0.007 (2)0.0021 (19)
O100.055 (2)0.0498 (19)0.0355 (17)0.0017 (16)0.0048 (15)−0.0096 (15)
O110.052 (2)0.059 (2)0.0322 (19)−0.0061 (18)0.0110 (16)−0.0121 (16)
O120.057 (2)0.0426 (17)0.0350 (17)0.0006 (16)0.0052 (15)−0.0001 (14)
Geometric parameters (Å, º) top
Fe1—O12.161 (3)C16—H16A0.930
Fe1—O32.169 (3)C17—H17A0.930
Fe1—O22.202 (4)C18—N41.342 (6)
Fe1—O42.202 (4)C18—C191.377 (7)
Fe1—N42.265 (4)C18—H18A0.930
Fe1—N22.266 (4)C19—C201.381 (6)
C1—O101.248 (6)C19—H19A0.930
C1—O91.268 (7)C20—C211.379 (7)
C1—C21.499 (10)C20—C231.488 (6)
C2—C31.401 (6)C21—C221.366 (7)
C2—N11.414 (9)C21—H21A0.930
C3—C41.390 (7)C22—N41.321 (6)
C3—H3A0.930C22—H22A0.930
C4—C51.380 (7)C23—C271.389 (7)
C4—H4A0.930C23—C241.394 (7)
C5—C61.410 (6)C24—C251.371 (7)
C5—H5A0.930C24—H24A0.930
C6—N11.385 (7)C25—N51.341 (7)
C6—C71.514 (7)C25—H25A0.930
C7—O121.246 (5)C26—N51.327 (8)
C7—O111.255 (5)C26—C271.378 (8)
C8—N21.342 (6)C26—H26A0.930
C8—C91.371 (7)C27—H27A0.930
C8—H8A0.930O1—H110.82 (1)
C9—C101.379 (7)O1—H120.82 (1)
C9—H9A0.930O2—H210.82 (1)
C10—C111.405 (7)O2—H220.82 (1)
C10—C131.473 (6)O3—H310.81 (1)
C11—C121.373 (7)O3—H320.81 (1)
C11—H11A0.930O4—H410.82 (1)
C12—N21.323 (7)O4—H420.82 (1)
C12—H12A0.930O5—H510.82 (1)
C13—C171.389 (7)O5—H520.82 (1)
C13—C141.391 (6)O6—H610.82 (1)
C14—C151.390 (7)O6—H620.82 (1)
C14—H14A0.930O7—H710.82 (1)
C15—N31.314 (7)O7—H720.82 (1)
C15—H15A0.930O8—H810.82 (1)
C16—N31.326 (7)O8—H820.81 (1)
C16—C171.366 (7)
O1—Fe1—O3179.73 (19)N3—C16—H16A117.5
O1—Fe1—O288.66 (15)C17—C16—H16A117.5
O3—Fe1—O291.28 (16)C16—C17—C13118.6 (5)
O1—Fe1—O491.61 (15)C16—C17—H17A120.7
O3—Fe1—O488.44 (15)C13—C17—H17A120.7
O2—Fe1—O4178.69 (18)N4—C18—C19123.4 (4)
O1—Fe1—N488.59 (14)N4—C18—H18A118.3
O3—Fe1—N491.14 (13)C19—C18—H18A118.3
O2—Fe1—N486.94 (15)C18—C19—C20119.2 (5)
O4—Fe1—N491.79 (15)C18—C19—H19A120.4
O1—Fe1—N290.87 (14)C20—C19—H19A120.4
O3—Fe1—N289.40 (14)C21—C20—C19117.5 (4)
O2—Fe1—N291.78 (16)C21—C20—C23120.7 (4)
O4—Fe1—N289.50 (15)C19—C20—C23121.8 (4)
N4—Fe1—N2178.62 (18)C22—C21—C20119.1 (5)
O10—C1—O9125.1 (5)C22—C21—H21A120.5
O10—C1—C2118.9 (5)C20—C21—H21A120.5
O9—C1—C2116.0 (4)N4—C22—C21124.7 (5)
C3—C2—N1118.1 (7)N4—C22—H22A117.7
C3—C2—C1122.0 (6)C21—C22—H22A117.7
N1—C2—C1119.9 (4)C27—C23—C24116.0 (5)
C4—C3—C2121.0 (6)C27—C23—C20121.9 (4)
C4—C3—H3A119.5C24—C23—C20122.1 (4)
C2—C3—H3A119.5C25—C24—C23120.3 (5)
C5—C4—C3119.9 (4)C25—C24—H24A119.8
C5—C4—H4A120.1C23—C24—H24A119.8
C3—C4—H4A120.1N5—C25—C24123.5 (5)
C4—C5—C6121.0 (5)N5—C25—H25A118.3
C4—C5—H5A119.5C24—C25—H25A118.3
C6—C5—H5A119.5N5—C26—C27124.4 (6)
N1—C6—C5118.6 (5)N5—C26—H26A117.8
N1—C6—C7120.7 (4)C27—C26—H26A117.8
C5—C6—C7120.7 (5)C26—C27—C23119.7 (5)
O12—C7—O11125.3 (4)C26—C27—H27A120.2
O12—C7—C6117.5 (4)C23—C27—H27A120.2
O11—C7—C6117.1 (4)C6—N1—C2121.5 (4)
N2—C8—C9123.2 (5)C12—N2—C8116.4 (4)
N2—C8—H8A118.4C12—N2—Fe1124.0 (3)
C9—C8—H8A118.4C8—N2—Fe1118.7 (3)
C8—C9—C10121.1 (5)C15—N3—C16116.6 (4)
C8—C9—H9A119.4C22—N4—C18116.1 (4)
C10—C9—H9A119.4C22—N4—Fe1117.6 (3)
C9—C10—C11115.1 (4)C18—N4—Fe1125.0 (3)
C9—C10—C13122.9 (4)C26—N5—C25116.2 (5)
C11—C10—C13122.0 (4)Fe1—O1—H11130 (4)
C12—C11—C10120.1 (5)Fe1—O1—H12124 (4)
C12—C11—H11A119.9H11—O1—H12106.3 (18)
C10—C11—H11A119.9Fe1—O2—H21121 (4)
N2—C12—C11123.9 (5)Fe1—O2—H22125 (4)
N2—C12—H12A118.1H21—O2—H22107.8 (19)
C11—C12—H12A118.1Fe1—O3—H31132 (4)
C17—C13—C14117.3 (4)Fe1—O3—H32109 (4)
C17—C13—C10122.0 (4)H31—O3—H32109.4 (19)
C14—C13—C10120.7 (4)Fe1—O4—H41127 (4)
C15—C14—C13118.7 (5)Fe1—O4—H42121 (4)
C15—C14—H14A120.6H41—O4—H42107.8 (19)
C13—C14—H14A120.6H51—O5—H52108.4 (19)
N3—C15—C14123.9 (5)H61—O6—H62107.2 (19)
N3—C15—H15A118.1H71—O7—H72106.9 (19)
C14—C15—H15A118.1H81—O8—H82108.6 (19)
N3—C16—C17125.0 (5)
O10—C1—C2—C3−179.0 (7)C19—C20—C23—C24176.6 (4)
O9—C1—C2—C30.1 (10)C27—C23—C24—C250.0 (8)
O10—C1—C2—N12.5 (10)C20—C23—C24—C25179.0 (4)
O9—C1—C2—N1−178.5 (6)C23—C24—C25—N50.0 (9)
N1—C2—C3—C4−0.6 (11)N5—C26—C27—C230.0 (9)
C1—C2—C3—C4−179.2 (6)C24—C23—C27—C260.0 (7)
C2—C3—C4—C50.7 (9)C20—C23—C27—C26−179.0 (5)
C3—C4—C5—C6−0.2 (8)C5—C6—N1—C20.5 (9)
C4—C5—C6—N1−0.4 (8)C7—C6—N1—C2−177.4 (6)
C4—C5—C6—C7177.5 (4)C3—C2—N1—C6−0.1 (11)
N1—C6—C7—O120.2 (7)C1—C2—N1—C6178.6 (5)
C5—C6—C7—O12−177.7 (5)C11—C12—N2—C8−1.8 (8)
N1—C6—C7—O11177.9 (5)C11—C12—N2—Fe1167.1 (4)
C5—C6—C7—O110.0 (7)C9—C8—N2—C122.0 (8)
N2—C8—C9—C101.0 (9)C9—C8—N2—Fe1−167.5 (5)
C8—C9—C10—C11−4.1 (8)O1—Fe1—N2—C1272.5 (4)
C8—C9—C10—C13175.5 (5)O3—Fe1—N2—C12−107.6 (4)
C9—C10—C11—C124.3 (8)O2—Fe1—N2—C12161.2 (4)
C13—C10—C11—C12−175.3 (5)O4—Fe1—N2—C12−19.1 (4)
C10—C11—C12—N2−1.5 (9)O1—Fe1—N2—C8−118.9 (4)
C9—C10—C13—C17−174.3 (4)O3—Fe1—N2—C861.1 (4)
C11—C10—C13—C175.2 (7)O2—Fe1—N2—C8−30.2 (4)
C9—C10—C13—C145.3 (7)O4—Fe1—N2—C8149.5 (4)
C11—C10—C13—C14−175.1 (4)C14—C15—N3—C160.0 (7)
C17—C13—C14—C150.2 (7)C17—C16—N3—C15−0.3 (8)
C10—C13—C14—C15−179.4 (4)C21—C22—N4—C18−1.9 (8)
C13—C14—C15—N30.0 (7)C21—C22—N4—Fe1165.8 (4)
N3—C16—C17—C130.6 (8)C19—C18—N4—C221.8 (7)
C14—C13—C17—C16−0.6 (7)C19—C18—N4—Fe1−164.9 (4)
C10—C13—C17—C16179.1 (4)O1—Fe1—N4—C22−63.8 (4)
N4—C18—C19—C200.3 (8)O3—Fe1—N4—C22116.3 (4)
C18—C19—C20—C21−2.2 (7)O2—Fe1—N4—C22−152.5 (4)
C18—C19—C20—C23176.3 (4)O4—Fe1—N4—C2227.8 (4)
C19—C20—C21—C222.1 (7)O1—Fe1—N4—C18102.7 (4)
C23—C20—C21—C22−176.4 (4)O3—Fe1—N4—C18−77.2 (4)
C20—C21—C22—N40.0 (8)O2—Fe1—N4—C1814.0 (4)
C21—C20—C23—C27174.0 (4)O4—Fe1—N4—C18−165.7 (4)
C19—C20—C23—C27−4.4 (7)C27—C26—N5—C250.0 (9)
C21—C20—C23—C24−5.0 (7)C24—C25—N5—C260.0 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H11···O8i0.82 (1)2.06 (3)2.831 (7)156 (6)
O1—H12···N3ii0.82 (1)1.98 (3)2.759 (5)158 (6)
O2—H21···O5iii0.82 (1)2.00 (2)2.806 (6)172 (5)
O2—H22···O7iii0.82 (1)1.96 (1)2.781 (6)178 (8)
O3—H31···O5iv0.81 (1)2.04 (1)2.851 (7)175 (7)
O3—H32···N5v0.81 (1)1.96 (2)2.745 (5)162 (6)
O4—H41···O80.82 (1)1.97 (1)2.785 (5)177 (7)
O4—H42···O11vi0.82 (1)1.93 (2)2.736 (5)170 (5)
O5—H52···O60.82 (1)1.93 (3)2.739 (8)170 (7)
O5—H51···O11vi0.82 (1)1.94 (2)2.742 (7)166 (7)
O6—H62···O90.82 (1)2.46 (8)2.952 (6)120 (7)
O6—H61···O10i0.82 (1)2.03 (2)2.827 (5)164 (7)
O7—H72···O5vii0.82 (1)2.57 (2)3.349 (7)159 (5)
O7—H71···O90.82 (1)1.81 (2)2.622 (6)168 (7)
O8—H81···O70.82 (1)2.01 (3)2.817 (7)170 (6)
O8—H82···O12viii0.81 (1)1.97 (2)2.768 (6)170 (7)
Symmetry codes: (i) x, y+1, z; (ii) x, −y+2, z−1/2; (iii) x+1/2, y+1/2, z; (iv) x+1/2, y−1/2, z; (v) x, −y+1, z+1/2; (vi) x, −y+1, z−1/2; (vii) x, y−1, z; (viii) x, −y, z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H11···O8i0.82 (1)2.06 (3)2.831 (7)156 (6)
O1—H12···N3ii0.82 (1)1.98 (3)2.759 (5)158 (6)
O2—H21···O5iii0.82 (1)2.00 (2)2.806 (6)172 (5)
O2—H22···O7iii0.82 (1)1.96 (1)2.781 (6)178 (8)
O3—H31···O5iv0.81 (1)2.04 (1)2.851 (7)175 (7)
O3—H32···N5v0.81 (1)1.96 (2)2.745 (5)162 (6)
O4—H41···O80.82 (1)1.97 (1)2.785 (5)177 (7)
O4—H42···O11vi0.82 (1)1.93 (2)2.736 (5)170 (5)
O5—H52···O60.82 (1)1.93 (3)2.739 (8)170 (7)
O5—H51···O11vi0.82 (1)1.94 (2)2.742 (7)166 (7)
O6—H62···O90.82 (1)2.46 (8)2.952 (6)120 (7)
O6—H61···O10i0.82 (1)2.03 (2)2.827 (5)164 (7)
O7—H72···O5vii0.82 (1)2.57 (2)3.349 (7)159 (5)
O7—H71···O90.82 (1)1.81 (2)2.622 (6)168 (7)
O8—H81···O70.82 (1)2.01 (3)2.817 (7)170 (6)
O8—H82···O12viii0.81 (1)1.97 (2)2.768 (6)170 (7)
Symmetry codes: (i) x, y+1, z; (ii) x, −y+2, z−1/2; (iii) x+1/2, y+1/2, z; (iv) x+1/2, y−1/2, z; (v) x, −y+1, z+1/2; (vi) x, −y+1, z−1/2; (vii) x, y−1, z; (viii) x, −y, z−1/2.
Acknowledgements top

The authors thank the Natural Scince Foundation of China (grant No. 20501017) and Tonghua Teachers' College.

references
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