metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Tetra­kis(μ2-ferrocene­carboxyl­ato-κ2O:O′)bis­­[(methanol-κO)copper(II)] methanol disolvate

aDepartamento de Química Inorgánica, Facultad de Ciencia y Tecnología, Universidad de País Vasco (UPV/EHU), PO Box 644, E-48080 Bilbao, Spain
*Correspondence e-mail: juanma.zorrilla@ehu.es

(Received 11 November 2011; accepted 22 November 2011; online 25 November 2011)

The complex mol­ecule of the title compound, [Cu2Fe4(C5H5)4(C6H4O2)4(CH3OH)2]·2CH3OH, lies about an inversion centre and contains two centrosymetrically related CuII atoms bridged by four O:O′-bidentante ferrocene­carboxyl­ate anions, leading to a dimeric tetra­bridged unit with a paddle-wheel geometry. The CuII atom has a distorted square-pyramidal coordination environment with four O atoms from four ferrocene­carboxyl­ate ligands in basal positions and an O atom from a methanol mol­ecule in an apical position. One of the two crystallographically independent ferrocenyl groups has a staggered conformation, while the other is eclipsed. The mol­ecules are connected into a chain along the b axis by O—H⋯O hydrogen bonds involving coordinated and uncoordinated methanol mol­ecules and the O atom from a ferrocene­carboxyl­ate unit.

Related literature

For related structures, see: Churchill et al. (1985[Churchill, M. R., Li, Y.-J., Nalewajek, D., Schaber, P. M. & Dorfman, J. (1985). Inorg. Chem. 24, 2684-2687.]); Cooke et al. (2002[Cooke, M. W., Cameron, T. S., Robertson, K. N., Swarts, J. C. & Aquino, M. A. S. (2002). Organometallics, 21, 5962-5971.]); Zhang et al. (2009[Zhang, E., Hou, H., Meng, X., Liu, Y., Liu, Y. & Fan, Y. (2009). Cryst. Growth Des. 9, 903-913.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu2Fe4(C5H5)4(C6H4O2)4(CH4O)2]·2CH4O

  • Mr = 1171.40

  • Triclinic, [P \overline 1]

  • a = 9.5112 (8) Å

  • b = 9.5884 (9) Å

  • c = 13.2478 (14) Å

  • α = 72.867 (7)°

  • β = 79.911 (8)°

  • γ = 85.399 (7)°

  • V = 1136.17 (19) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 2.23 mm−1

  • T = 100 K

  • 0.13 × 0.10 × 0.01 mm

Data collection
  • Stoe IPDS 2T diffractometer

  • Absorption correction: integration (X-RED; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.]) Tmin = 0.768, Tmax = 0.969

  • 8197 measured reflections

  • 3990 independent reflections

  • 2199 reflections with I > 2σ(I)

  • Rint = 0.071

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.080

  • S = 0.77

  • 3990 reflections

  • 306 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.38 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O5—H5O⋯O6i 0.82 (6) 1.95 (6) 2.759 (6) 170 (7)
O6—H6O⋯O2ii 0.84 (4) 2.18 (5) 2.925 (6) 147 (7)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1.

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.]); program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

The title compound, [Cu2{Fe(C5H5)(C5H4COO)}4(CH3OH)2].2CH3OH, was obtained in an attempted synthesis of a hybrid inorganic-metalorganic compound based on Keggin-type polyoxometalates and ferrocenecarboxylate-copper(II) complexes in methanol. Isolation of the compound was only observed in the presence of the [PW9O34]9- polyanion precursor.

The title compound (Fig. 1) contains two centrosymmetrically related copper(II) centers bridged by four ferrocenecarboxylate anions (L) in a O,O'-bidentantate fashion, leading to a dimeric tetrabridged [Cu22-L)4] unit. Each copper(II) ion has a square-pyramidal coordination environment with four oxygen atoms from four ferrocenecarboxylate ligands and an oxygen atom from a methanol molecule in apical position. The paddle-wheel structure of the complex brings the metal centers close to each other, being the intradimer Cu···Cui distance 2.5936 (14) Å [symmetry code: (i) -x, -y + 1, -z + 1], shorter than 2.605 (1) Å observed in the corresponding THF complex (Churchill et al., 1985). The two crystallographically independent ferrocenyl moieties have different conformations: that containing Fe1 is staggered, while that involving Fe2 is eclipsed. The crystal packing is built up by hydrogen bonding interactions involving coordinated and uncoordinated methanol molecules (Table 1). This hydrogen bonding network results in chains parallel to the b axis (Fig. 2). The connection among them is made by C—H···O and ππ type weak interactions.

Related literature top

For related structures, see: Churchill et al. (1985); Cooke et al. (2002); Zhang et al. (2009).

Experimental top

CuCl2.2H2O (34 mg, 0.2 mmol), ferrocenecarboxylic acid (46 mg, 0.2 mmol) and Na9[PW9O34].7H2O (244 mg, 0.1 mmol) were refluxed for 2 h in methanol (20 ml). Dark green prismatic single crystals were obtained by slow evaporation of the resulting yellow solution after two days.

Refinement top

H atoms bonded to O atoms were located in a Fourier difference map and refined with distance restraint of O—H = 0.84 (2) Å and with Uiso(H) = 1.5Ueq(O). H atoms attached to C atoms were positioned geometrically (C—H = 0.95 or 0.98 Å) and refined using a riding, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). A rotating-group model was applied for the methyl groups.

Structure description top

The title compound, [Cu2{Fe(C5H5)(C5H4COO)}4(CH3OH)2].2CH3OH, was obtained in an attempted synthesis of a hybrid inorganic-metalorganic compound based on Keggin-type polyoxometalates and ferrocenecarboxylate-copper(II) complexes in methanol. Isolation of the compound was only observed in the presence of the [PW9O34]9- polyanion precursor.

The title compound (Fig. 1) contains two centrosymmetrically related copper(II) centers bridged by four ferrocenecarboxylate anions (L) in a O,O'-bidentantate fashion, leading to a dimeric tetrabridged [Cu22-L)4] unit. Each copper(II) ion has a square-pyramidal coordination environment with four oxygen atoms from four ferrocenecarboxylate ligands and an oxygen atom from a methanol molecule in apical position. The paddle-wheel structure of the complex brings the metal centers close to each other, being the intradimer Cu···Cui distance 2.5936 (14) Å [symmetry code: (i) -x, -y + 1, -z + 1], shorter than 2.605 (1) Å observed in the corresponding THF complex (Churchill et al., 1985). The two crystallographically independent ferrocenyl moieties have different conformations: that containing Fe1 is staggered, while that involving Fe2 is eclipsed. The crystal packing is built up by hydrogen bonding interactions involving coordinated and uncoordinated methanol molecules (Table 1). This hydrogen bonding network results in chains parallel to the b axis (Fig. 2). The connection among them is made by C—H···O and ππ type weak interactions.

For related structures, see: Churchill et al. (1985); Cooke et al. (2002); Zhang et al. (2009).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) showing atom-labelling and 50% probability displacement ellipsoids [symmetry code: (i) -x, -y + 1, -z + 1].
[Figure 2] Fig. 2. Crystal packing of (I) viewed down the c axis, showing a chain of complexes connected via O—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.
Tetrakis(µ-ferrocenecarboxylato-κ2O:O')bis[(methanol- κO)copper(II)] methanol disolvate top
Crystal data top
[Cu2Fe4(C5H5)4(C6H4O2)4(CH4O)2]·2CH4OZ = 1
Mr = 1171.40F(000) = 598
Triclinic, P1Dx = 1.712 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5112 (8) ÅCell parameters from 4954 reflections
b = 9.5884 (9) Åθ = 2.2–25.5°
c = 13.2478 (14) ŵ = 2.23 mm1
α = 72.867 (7)°T = 100 K
β = 79.911 (8)°Plate, dark green
γ = 85.399 (7)°0.13 × 0.10 × 0.01 mm
V = 1136.17 (19) Å3
Data collection top
Stoe IPDS 2T
diffractometer
3990 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2199 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.071
Detector resolution: 6.67 pixels mm-1θmax = 25°, θmin = 2.2°
rotation method scansh = 1111
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 1110
Tmin = 0.768, Tmax = 0.969l = 1515
8197 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)] = 0.043Hydrogen site location: difference Fourier map
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 0.77 w = 1/[σ2(Fo2) + (0.0201P)2]
where P = (Fo2 + 2Fc2)/3
3990 reflections(Δ/σ)max < 0.001
306 parametersΔρmax = 0.38 e Å3
2 restraintsΔρmin = 0.38 e Å3
Crystal data top
[Cu2Fe4(C5H5)4(C6H4O2)4(CH4O)2]·2CH4Oγ = 85.399 (7)°
Mr = 1171.40V = 1136.17 (19) Å3
Triclinic, P1Z = 1
a = 9.5112 (8) ÅMo Kα radiation
b = 9.5884 (9) ŵ = 2.23 mm1
c = 13.2478 (14) ÅT = 100 K
α = 72.867 (7)°0.13 × 0.10 × 0.01 mm
β = 79.911 (8)°
Data collection top
Stoe IPDS 2T
diffractometer
3990 independent reflections
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
2199 reflections with I > 2σ(I)
Tmin = 0.768, Tmax = 0.969Rint = 0.071
8197 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0432 restraints
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 0.77Δρmax = 0.38 e Å3
3990 reflectionsΔρmin = 0.38 e Å3
306 parameters
Special details top

Experimental. IR (cm-1): 1620(w), 1566(s), 1474(s), 1389(s), 1358(m), 1188(w), 1103(w), 1026(w), 1003(w), 918(w), 818(m), 779(m), 532(m), 478(m).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cu10.06133 (7)0.61943 (7)0.49254 (6)0.02993 (19)
Fe10.45442 (9)0.32189 (9)0.27785 (7)0.0333 (2)
Fe20.18777 (9)0.77725 (9)0.12862 (7)0.0356 (2)
O10.2339 (4)0.5013 (4)0.4676 (3)0.0356 (9)
O20.1308 (4)0.2923 (4)0.4812 (3)0.0340 (9)
O30.0423 (4)0.6656 (4)0.3399 (3)0.0342 (9)
O40.0609 (4)0.4573 (4)0.3524 (3)0.0344 (9)
C10.2391 (6)0.3706 (6)0.4635 (4)0.0328 (13)
C20.3813 (6)0.3091 (6)0.4320 (4)0.0314 (13)
C30.4126 (6)0.1672 (6)0.4197 (4)0.0337 (13)
H30.34650.09140.43630.040*
C40.5609 (6)0.1587 (6)0.3779 (4)0.0363 (14)
H40.61140.07620.36190.044*
C50.6193 (6)0.2954 (6)0.3648 (4)0.0377 (14)
H50.71610.32050.33760.045*
C60.5097 (6)0.3889 (6)0.3988 (4)0.0344 (14)
H60.52010.48640.39930.041*
C70.2850 (7)0.3698 (7)0.1955 (5)0.0474 (16)
H70.18690.36410.22640.057*
C80.3719 (8)0.2578 (7)0.1675 (5)0.0543 (18)
H80.34250.16230.17550.065*
C90.5131 (7)0.3118 (7)0.1244 (5)0.0470 (16)
H90.59370.25800.10040.056*
C100.5100 (7)0.4575 (6)0.1243 (5)0.0423 (15)
H100.58760.52190.09870.051*
C110.3702 (7)0.4919 (7)0.1694 (5)0.0442 (16)
H110.33880.58370.18020.053*
C120.0144 (6)0.5822 (6)0.3026 (5)0.0311 (13)
C130.0278 (6)0.6391 (6)0.1868 (5)0.0373 (14)
C140.1018 (6)0.5751 (6)0.1275 (5)0.0399 (15)
H140.14990.48540.15460.048*
C150.0918 (6)0.6670 (6)0.0223 (5)0.0424 (15)
H150.13230.64980.03350.051*
C160.0124 (6)0.7879 (7)0.0132 (5)0.0431 (16)
H160.00930.86710.04950.052*
C170.0303 (6)0.7727 (6)0.1131 (5)0.0384 (15)
H170.08680.83850.12890.046*
C180.3181 (6)0.8241 (6)0.2552 (5)0.0405 (15)
H180.30500.79050.32810.049*
C190.3943 (6)0.7520 (6)0.2055 (5)0.0400 (15)
H190.44050.66190.23830.048*
C200.3906 (6)0.8365 (6)0.0978 (5)0.0414 (15)
H200.43410.81310.04580.050*
C210.3092 (6)0.9645 (6)0.0808 (5)0.0415 (15)
H210.28951.04080.01600.050*
C220.2635 (7)0.9545 (7)0.1811 (5)0.0475 (17)
H220.20741.02250.19470.057*
O50.1722 (4)0.8204 (4)0.4532 (3)0.0361 (10)
H5O0.162 (7)0.877 (6)0.490 (4)0.054*
C230.3032 (6)0.8342 (7)0.3782 (5)0.0436 (16)
H23A0.29840.77770.32820.065*
H23B0.38360.79720.41700.065*
H23C0.31690.93720.33830.065*
O60.8782 (4)0.0185 (4)0.4019 (3)0.0437 (10)
H6O0.898 (7)0.071 (3)0.412 (5)0.066*
C240.9929 (6)0.0836 (6)0.3229 (5)0.0448 (16)
H24A0.95950.17570.27670.067*
H24B1.02950.01740.27960.067*
H24C1.06930.10280.35750.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0298 (4)0.0248 (4)0.0363 (4)0.0026 (3)0.0068 (3)0.0105 (3)
Fe10.0353 (5)0.0302 (5)0.0349 (5)0.0035 (4)0.0067 (4)0.0106 (4)
Fe20.0375 (5)0.0326 (5)0.0377 (5)0.0038 (4)0.0083 (4)0.0112 (4)
O10.033 (2)0.032 (2)0.045 (3)0.0021 (17)0.0076 (18)0.0146 (19)
O20.035 (2)0.025 (2)0.041 (2)0.0006 (17)0.0024 (18)0.0102 (18)
O30.036 (2)0.031 (2)0.037 (2)0.0037 (18)0.0070 (18)0.0093 (19)
O40.042 (2)0.027 (2)0.034 (2)0.0026 (18)0.0090 (18)0.0065 (18)
C10.035 (3)0.031 (3)0.031 (3)0.001 (3)0.007 (3)0.006 (3)
C20.034 (3)0.024 (3)0.038 (3)0.002 (2)0.011 (3)0.011 (3)
C30.043 (3)0.021 (3)0.038 (3)0.002 (3)0.006 (3)0.010 (3)
C40.035 (3)0.037 (3)0.037 (3)0.005 (3)0.002 (3)0.013 (3)
C50.036 (3)0.045 (4)0.033 (3)0.001 (3)0.002 (3)0.014 (3)
C60.038 (3)0.030 (3)0.035 (3)0.002 (3)0.006 (3)0.011 (3)
C70.042 (4)0.060 (4)0.043 (4)0.007 (3)0.011 (3)0.015 (3)
C80.081 (5)0.042 (4)0.043 (4)0.013 (4)0.020 (4)0.009 (3)
C90.050 (4)0.055 (4)0.035 (4)0.008 (3)0.009 (3)0.012 (3)
C100.047 (4)0.034 (4)0.042 (4)0.005 (3)0.012 (3)0.002 (3)
C110.053 (4)0.040 (4)0.038 (4)0.014 (3)0.011 (3)0.010 (3)
C120.026 (3)0.032 (3)0.036 (3)0.003 (3)0.003 (3)0.013 (3)
C130.032 (3)0.034 (3)0.050 (4)0.005 (3)0.008 (3)0.019 (3)
C140.045 (4)0.032 (3)0.045 (4)0.004 (3)0.006 (3)0.017 (3)
C150.053 (4)0.037 (4)0.037 (4)0.013 (3)0.014 (3)0.011 (3)
C160.044 (4)0.041 (4)0.039 (4)0.009 (3)0.008 (3)0.005 (3)
C170.036 (3)0.036 (3)0.042 (4)0.001 (3)0.006 (3)0.009 (3)
C180.043 (4)0.040 (4)0.037 (4)0.002 (3)0.010 (3)0.009 (3)
C190.038 (3)0.033 (3)0.049 (4)0.007 (3)0.005 (3)0.015 (3)
C200.044 (4)0.045 (4)0.040 (4)0.004 (3)0.011 (3)0.018 (3)
C210.040 (3)0.034 (3)0.047 (4)0.006 (3)0.006 (3)0.010 (3)
C220.048 (4)0.045 (4)0.052 (4)0.004 (3)0.001 (3)0.024 (3)
O50.036 (2)0.034 (2)0.040 (3)0.0005 (19)0.0003 (19)0.0169 (19)
C230.043 (4)0.043 (4)0.043 (4)0.003 (3)0.002 (3)0.011 (3)
O60.042 (2)0.035 (2)0.055 (3)0.009 (2)0.007 (2)0.018 (2)
C240.044 (4)0.039 (3)0.050 (4)0.006 (3)0.006 (3)0.012 (3)
Geometric parameters (Å, º) top
Cu1—O11.954 (4)C6—H60.9500
Cu1—O4i1.966 (4)C7—C81.400 (9)
Cu1—O2i1.970 (4)C7—C111.400 (8)
Cu1—O31.977 (4)C7—H70.9500
Cu1—O52.154 (4)C8—C91.437 (9)
Cu1—Cu1i2.5936 (14)C8—H80.9500
Fe1—C22.009 (6)C9—C101.395 (9)
Fe1—C32.020 (6)C9—H90.9500
Fe1—C82.035 (7)C10—C111.415 (8)
Fe1—C92.040 (6)C10—H100.9500
Fe1—C112.044 (6)C11—H110.9500
Fe1—C72.049 (6)C12—C131.493 (8)
Fe1—C62.052 (6)C13—C141.428 (8)
Fe1—C42.056 (6)C13—C171.445 (8)
Fe1—C52.061 (6)C14—C151.404 (8)
Fe1—C102.069 (6)C14—H140.9500
Fe2—C132.038 (6)C15—C161.399 (8)
Fe2—C162.043 (6)C15—H150.9500
Fe2—C202.043 (6)C16—C171.415 (8)
Fe2—C182.044 (6)C16—H160.9500
Fe2—C192.045 (6)C17—H170.9500
Fe2—C142.045 (6)C18—C191.398 (8)
Fe2—C172.046 (6)C18—C221.414 (8)
Fe2—C152.052 (6)C18—H180.9500
Fe2—C212.053 (6)C19—C201.413 (8)
Fe2—C222.053 (6)C19—H190.9500
O1—C11.267 (6)C20—C211.444 (8)
O2—C11.271 (6)C20—H200.9500
O2—Cu1i1.970 (4)C21—C221.444 (9)
O3—C121.253 (6)C21—H210.9500
O4—C121.258 (6)C22—H220.9500
O4—Cu1i1.966 (4)O5—C231.440 (7)
C1—C21.474 (7)O5—H5O0.82 (2)
C2—C31.419 (7)C23—H23A0.9800
C2—C61.426 (7)C23—H23B0.9800
C3—C41.428 (7)C23—H23C0.9800
C3—H30.9500O6—C241.414 (7)
C4—C51.416 (8)O6—H6O0.84 (2)
C4—H40.9500C24—H24A0.9800
C5—C61.420 (7)C24—H24B0.9800
C5—H50.9500C24—H24C0.9800
O1—Cu1—O4i89.58 (16)C3—C4—Fe168.1 (3)
O1—Cu1—O2i169.83 (16)C5—C4—H4126.2
O4i—Cu1—O2i90.21 (16)C3—C4—H4126.2
O1—Cu1—O389.92 (16)Fe1—C4—H4127.2
O4i—Cu1—O3169.82 (16)C4—C5—C6108.9 (5)
O2i—Cu1—O388.50 (15)C4—C5—Fe169.7 (3)
O1—Cu1—O594.70 (15)C6—C5—Fe169.5 (3)
O4i—Cu1—O5102.23 (16)C4—C5—H5125.5
O2i—Cu1—O595.28 (15)C6—C5—H5125.5
O3—Cu1—O587.94 (16)Fe1—C5—H5126.9
O1—Cu1—Cu1i82.06 (11)C5—C6—C2107.2 (5)
O4i—Cu1—Cu1i86.42 (11)C5—C6—Fe170.1 (3)
O2i—Cu1—Cu1i87.77 (11)C2—C6—Fe167.8 (3)
O3—Cu1—Cu1i83.44 (11)C5—C6—H6126.4
O5—Cu1—Cu1i170.78 (12)C2—C6—H6126.4
C2—Fe1—C341.3 (2)Fe1—C6—H6127.2
C2—Fe1—C8132.1 (3)C8—C7—C11107.0 (6)
C3—Fe1—C8108.0 (2)C8—C7—Fe169.4 (4)
C2—Fe1—C9172.6 (3)C11—C7—Fe169.8 (4)
C3—Fe1—C9132.8 (2)C8—C7—H7126.5
C8—Fe1—C941.3 (3)C11—C7—H7126.5
C2—Fe1—C11115.1 (2)Fe1—C7—H7125.8
C3—Fe1—C11145.2 (2)C7—C8—C9108.5 (6)
C8—Fe1—C1167.0 (3)C7—C8—Fe170.5 (4)
C9—Fe1—C1167.4 (3)C9—C8—Fe169.6 (4)
C2—Fe1—C7108.4 (2)C7—C8—H8125.7
C3—Fe1—C7113.3 (2)C9—C8—H8125.7
C8—Fe1—C740.1 (3)Fe1—C8—H8125.8
C9—Fe1—C768.5 (3)C10—C9—C8107.5 (6)
C11—Fe1—C740.0 (2)C10—C9—Fe171.3 (4)
C2—Fe1—C641.1 (2)C8—C9—Fe169.1 (4)
C3—Fe1—C669.1 (2)C10—C9—H9126.3
C8—Fe1—C6172.3 (3)C8—C9—H9126.3
C9—Fe1—C6145.8 (2)Fe1—C9—H9124.9
C11—Fe1—C6111.1 (2)C9—C10—C11107.4 (6)
C7—Fe1—C6133.7 (2)C9—C10—Fe169.0 (3)
C2—Fe1—C468.9 (2)C11—C10—Fe168.9 (3)
C3—Fe1—C441.0 (2)C9—C10—H10126.3
C8—Fe1—C4114.5 (3)C11—C10—H10126.3
C9—Fe1—C4109.3 (2)Fe1—C10—H10127.3
C11—Fe1—C4173.7 (2)C7—C11—C10109.6 (6)
C7—Fe1—C4144.8 (2)C7—C11—Fe170.2 (4)
C6—Fe1—C468.4 (2)C10—C11—Fe170.9 (3)
C2—Fe1—C568.5 (2)C7—C11—H11125.2
C3—Fe1—C568.4 (2)C10—C11—H11125.2
C8—Fe1—C5146.1 (3)Fe1—C11—H11125.3
C9—Fe1—C5115.2 (2)O3—C12—O4126.8 (5)
C11—Fe1—C5135.4 (3)O3—C12—C13115.7 (5)
C7—Fe1—C5173.6 (3)O4—C12—C13117.5 (5)
C6—Fe1—C540.4 (2)C14—C13—C17106.4 (5)
C4—Fe1—C540.2 (2)C14—C13—C12127.4 (5)
C2—Fe1—C10146.4 (2)C17—C13—C12126.2 (5)
C3—Fe1—C10172.2 (2)C14—C13—Fe269.8 (3)
C8—Fe1—C1067.6 (3)C17—C13—Fe269.6 (3)
C9—Fe1—C1039.7 (2)C12—C13—Fe2124.4 (4)
C11—Fe1—C1040.2 (2)C15—C14—C13108.7 (5)
C7—Fe1—C1067.9 (3)C15—C14—Fe270.2 (3)
C6—Fe1—C10116.2 (2)C13—C14—Fe269.2 (3)
C4—Fe1—C10133.9 (2)C15—C14—H14125.7
C5—Fe1—C10111.3 (2)C13—C14—H14125.7
C13—Fe2—C1668.9 (2)Fe2—C14—H14126.5
C13—Fe2—C20156.2 (2)C16—C15—C14108.7 (6)
C16—Fe2—C20124.2 (2)C16—C15—Fe269.7 (3)
C13—Fe2—C18107.8 (2)C14—C15—Fe269.7 (3)
C16—Fe2—C18157.8 (3)C16—C15—H15125.7
C20—Fe2—C1867.7 (2)C14—C15—H15125.7
C13—Fe2—C19121.1 (2)Fe2—C15—H15126.5
C16—Fe2—C19160.7 (3)C15—C16—C17108.6 (5)
C20—Fe2—C1940.4 (2)C15—C16—Fe270.4 (3)
C18—Fe2—C1940.0 (2)C17—C16—Fe269.9 (3)
C13—Fe2—C1440.9 (2)C15—C16—H16125.7
C16—Fe2—C1467.7 (2)C17—C16—H16125.7
C20—Fe2—C14121.1 (2)Fe2—C16—H16125.6
C18—Fe2—C14125.1 (2)C16—C17—C13107.6 (6)
C19—Fe2—C14108.0 (2)C16—C17—Fe269.6 (4)
C13—Fe2—C1741.4 (2)C13—C17—Fe269.0 (3)
C16—Fe2—C1740.5 (2)C16—C17—H17126.2
C20—Fe2—C17160.8 (2)C13—C17—H17126.2
C18—Fe2—C17122.5 (2)Fe2—C17—H17126.8
C19—Fe2—C17157.4 (2)C19—C18—C22109.9 (6)
C14—Fe2—C1768.4 (2)C19—C18—Fe270.1 (3)
C13—Fe2—C1568.5 (2)C22—C18—Fe270.1 (3)
C16—Fe2—C1540.0 (2)C19—C18—H18125.1
C20—Fe2—C15107.8 (2)C22—C18—H18125.1
C18—Fe2—C15161.1 (2)Fe2—C18—H18126.3
C19—Fe2—C15124.8 (3)C18—C19—C20108.2 (5)
C14—Fe2—C1540.1 (2)C18—C19—Fe270.0 (3)
C17—Fe2—C1567.8 (2)C20—C19—Fe269.7 (3)
C13—Fe2—C21160.9 (2)C18—C19—H19125.9
C16—Fe2—C21107.3 (2)C20—C19—H19125.9
C20—Fe2—C2141.3 (2)Fe2—C19—H19126.0
C18—Fe2—C2168.2 (2)C19—C20—C21108.1 (5)
C19—Fe2—C2168.7 (2)C19—C20—Fe269.9 (3)
C14—Fe2—C21156.5 (2)C21—C20—Fe269.7 (3)
C17—Fe2—C21123.7 (2)C19—C20—H20126.0
C15—Fe2—C21121.4 (2)C21—C20—H20126.0
C13—Fe2—C22123.8 (3)Fe2—C20—H20126.0
C16—Fe2—C22121.9 (2)C22—C21—C20106.9 (5)
C20—Fe2—C2269.0 (3)C22—C21—Fe269.4 (3)
C18—Fe2—C2240.4 (2)C20—C21—Fe269.0 (3)
C19—Fe2—C2268.3 (2)C22—C21—H21126.6
C14—Fe2—C22161.1 (3)C20—C21—H21126.6
C17—Fe2—C22107.4 (3)Fe2—C21—H21126.6
C15—Fe2—C22157.2 (2)C18—C22—C21107.0 (6)
C21—Fe2—C2241.2 (2)C18—C22—Fe269.5 (4)
C1—O1—Cu1126.4 (4)C21—C22—Fe269.4 (3)
C1—O2—Cu1i118.9 (3)C18—C22—H22126.5
C12—O3—Cu1123.1 (3)C21—C22—H22126.5
C12—O4—Cu1i120.1 (4)Fe2—C22—H22126.2
O1—C1—O2124.7 (5)C23—O5—Cu1117.1 (3)
O1—C1—C2116.6 (5)C23—O5—H5O115 (5)
O2—C1—C2118.7 (5)Cu1—O5—H5O125 (4)
C3—C2—C6108.4 (5)O5—C23—H23A109.5
C3—C2—C1126.6 (5)O5—C23—H23B109.5
C6—C2—C1124.8 (5)H23A—C23—H23B109.5
C3—C2—Fe169.8 (3)O5—C23—H23C109.5
C6—C2—Fe171.1 (3)H23A—C23—H23C109.5
C1—C2—Fe1120.6 (4)H23B—C23—H23C109.5
C2—C3—C4107.9 (5)C24—O6—H6O102 (5)
C2—C3—Fe169.0 (3)O6—C24—H24A109.5
C4—C3—Fe170.9 (3)O6—C24—H24B109.5
C2—C3—H3126.1H24A—C24—H24B109.5
C4—C3—H3126.1O6—C24—H24C109.5
Fe1—C3—H3125.7H24A—C24—H24C109.5
C5—C4—C3107.6 (5)H24B—C24—H24C109.5
C5—C4—Fe170.1 (3)
O4i—Cu1—O1—C188.1 (4)C6—Fe1—C11—C10106.0 (4)
O2i—Cu1—O1—C10.8 (13)C4—Fe1—C11—C1022 (2)
O3—Cu1—O1—C181.8 (4)C5—Fe1—C11—C1066.5 (5)
O5—Cu1—O1—C1169.7 (4)Cu1—O3—C12—O43.5 (7)
Cu1i—Cu1—O1—C11.6 (4)Cu1—O3—C12—C13176.3 (3)
O1—Cu1—O3—C1282.8 (4)Cu1i—O4—C12—O34.6 (7)
O4i—Cu1—O3—C124.4 (11)Cu1i—O4—C12—C13175.2 (3)
O2i—Cu1—O3—C1287.1 (4)O3—C12—C13—C14172.3 (5)
O5—Cu1—O3—C12177.5 (4)O4—C12—C13—C147.6 (8)
Cu1i—Cu1—O3—C120.8 (4)O3—C12—C13—C176.3 (8)
Cu1—O1—C1—O24.2 (8)O4—C12—C13—C17173.8 (5)
Cu1—O1—C1—C2173.5 (4)O3—C12—C13—Fe282.4 (6)
Cu1i—O2—C1—O14.5 (7)O4—C12—C13—Fe297.5 (5)
Cu1i—O2—C1—C2173.2 (4)C16—Fe2—C13—C1479.9 (4)
O1—C1—C2—C3178.5 (5)C20—Fe2—C13—C1448.5 (7)
O2—C1—C2—C30.6 (9)C18—Fe2—C13—C14123.4 (3)
O1—C1—C2—C64.9 (9)C19—Fe2—C13—C1481.7 (4)
O2—C1—C2—C6173.0 (5)C17—Fe2—C13—C14117.2 (5)
O1—C1—C2—Fe192.1 (6)C15—Fe2—C13—C1436.8 (3)
O2—C1—C2—Fe185.8 (6)C21—Fe2—C13—C14161.8 (7)
C8—Fe1—C2—C366.4 (5)C22—Fe2—C13—C14165.1 (3)
C9—Fe1—C2—C340 (2)C16—Fe2—C13—C1737.4 (4)
C11—Fe1—C2—C3147.3 (3)C20—Fe2—C13—C17165.7 (5)
C7—Fe1—C2—C3104.6 (4)C18—Fe2—C13—C17119.3 (4)
C6—Fe1—C2—C3118.8 (5)C19—Fe2—C13—C17161.1 (3)
C4—Fe1—C2—C338.0 (3)C14—Fe2—C13—C17117.2 (5)
C5—Fe1—C2—C381.4 (4)C15—Fe2—C13—C1780.4 (4)
C10—Fe1—C2—C3177.8 (4)C21—Fe2—C13—C1744.6 (9)
C3—Fe1—C2—C6118.8 (5)C22—Fe2—C13—C1777.7 (4)
C8—Fe1—C2—C6174.7 (4)C16—Fe2—C13—C12158.0 (6)
C9—Fe1—C2—C6158.7 (18)C20—Fe2—C13—C1273.7 (8)
C11—Fe1—C2—C693.9 (4)C18—Fe2—C13—C121.3 (6)
C7—Fe1—C2—C6136.6 (3)C19—Fe2—C13—C1240.4 (6)
C4—Fe1—C2—C680.8 (3)C14—Fe2—C13—C12122.1 (6)
C5—Fe1—C2—C637.5 (3)C17—Fe2—C13—C12120.6 (6)
C10—Fe1—C2—C659.0 (5)C15—Fe2—C13—C12159.0 (6)
C3—Fe1—C2—C1121.3 (6)C21—Fe2—C13—C1276.0 (9)
C8—Fe1—C2—C154.9 (6)C22—Fe2—C13—C1242.9 (6)
C9—Fe1—C2—C181 (2)C17—C13—C14—C151.0 (6)
C11—Fe1—C2—C126.0 (5)C12—C13—C14—C15177.8 (5)
C7—Fe1—C2—C116.7 (5)Fe2—C13—C14—C1559.3 (4)
C6—Fe1—C2—C1119.9 (6)C17—C13—C14—Fe260.3 (4)
C4—Fe1—C2—C1159.3 (5)C12—C13—C14—Fe2118.5 (5)
C5—Fe1—C2—C1157.3 (5)C13—Fe2—C14—C15120.0 (5)
C10—Fe1—C2—C160.9 (6)C16—Fe2—C14—C1536.9 (4)
C6—C2—C3—C40.4 (6)C20—Fe2—C14—C1580.6 (4)
C1—C2—C3—C4174.1 (5)C18—Fe2—C14—C15163.8 (4)
Fe1—C2—C3—C460.5 (4)C19—Fe2—C14—C15123.0 (4)
C6—C2—C3—Fe160.9 (4)C17—Fe2—C14—C1580.7 (4)
C1—C2—C3—Fe1113.6 (6)C21—Fe2—C14—C1545.2 (7)
C8—Fe1—C3—C2134.4 (4)C22—Fe2—C14—C15161.5 (7)
C9—Fe1—C3—C2173.5 (4)C16—Fe2—C14—C1383.1 (4)
C11—Fe1—C3—C259.1 (5)C20—Fe2—C14—C13159.4 (3)
C7—Fe1—C3—C291.8 (4)C18—Fe2—C14—C1376.2 (4)
C6—Fe1—C3—C238.1 (3)C19—Fe2—C14—C13117.0 (4)
C4—Fe1—C3—C2118.8 (5)C17—Fe2—C14—C1339.3 (3)
C5—Fe1—C3—C281.6 (4)C15—Fe2—C14—C13120.0 (5)
C10—Fe1—C3—C2171.1 (18)C21—Fe2—C14—C13165.2 (5)
C2—Fe1—C3—C4118.8 (5)C22—Fe2—C14—C1341.5 (9)
C8—Fe1—C3—C4106.8 (4)C13—C14—C15—C160.2 (6)
C9—Fe1—C3—C467.7 (5)Fe2—C14—C15—C1658.9 (4)
C11—Fe1—C3—C4177.8 (4)C13—C14—C15—Fe258.7 (4)
C7—Fe1—C3—C4149.5 (3)C13—Fe2—C15—C1682.5 (4)
C6—Fe1—C3—C480.7 (3)C20—Fe2—C15—C16122.5 (4)
C5—Fe1—C3—C437.2 (3)C18—Fe2—C15—C16164.6 (7)
C10—Fe1—C3—C452 (2)C19—Fe2—C15—C16163.9 (3)
C2—C3—C4—C50.1 (7)C14—Fe2—C15—C16120.1 (5)
Fe1—C3—C4—C559.1 (4)C17—Fe2—C15—C1637.7 (3)
C2—C3—C4—Fe159.3 (4)C21—Fe2—C15—C1679.2 (4)
C2—Fe1—C4—C581.2 (3)C22—Fe2—C15—C1644.5 (8)
C3—Fe1—C4—C5119.5 (4)C13—Fe2—C15—C1437.6 (3)
C8—Fe1—C4—C5150.9 (3)C16—Fe2—C15—C14120.1 (5)
C9—Fe1—C4—C5106.5 (4)C20—Fe2—C15—C14117.5 (4)
C11—Fe1—C4—C549 (2)C18—Fe2—C15—C1444.5 (9)
C7—Fe1—C4—C5173.6 (4)C19—Fe2—C15—C1476.1 (4)
C6—Fe1—C4—C536.9 (3)C17—Fe2—C15—C1482.4 (4)
C10—Fe1—C4—C569.1 (4)C21—Fe2—C15—C14160.7 (3)
C2—Fe1—C4—C338.3 (3)C22—Fe2—C15—C14164.6 (6)
C8—Fe1—C4—C389.7 (4)C14—C15—C16—C170.7 (7)
C9—Fe1—C4—C3134.0 (3)Fe2—C15—C16—C1759.6 (4)
C11—Fe1—C4—C3169 (2)C14—C15—C16—Fe259.0 (4)
C7—Fe1—C4—C354.1 (5)C13—Fe2—C16—C1581.2 (4)
C6—Fe1—C4—C382.5 (3)C20—Fe2—C16—C1576.3 (4)
C5—Fe1—C4—C3119.5 (4)C18—Fe2—C16—C15166.8 (6)
C10—Fe1—C4—C3171.4 (4)C19—Fe2—C16—C1543.7 (9)
C3—C4—C5—C60.6 (7)C14—Fe2—C16—C1537.0 (4)
Fe1—C4—C5—C658.5 (4)C17—Fe2—C16—C15119.4 (5)
C3—C4—C5—Fe157.9 (4)C21—Fe2—C16—C15118.6 (4)
C2—Fe1—C5—C482.4 (3)C22—Fe2—C16—C15161.3 (4)
C3—Fe1—C5—C437.9 (3)C13—Fe2—C16—C1738.2 (3)
C8—Fe1—C5—C452.5 (6)C20—Fe2—C16—C17164.3 (3)
C9—Fe1—C5—C490.6 (4)C18—Fe2—C16—C1747.4 (8)
C11—Fe1—C5—C4173.2 (3)C19—Fe2—C16—C17163.2 (6)
C7—Fe1—C5—C4145 (2)C14—Fe2—C16—C1782.4 (4)
C6—Fe1—C5—C4120.5 (5)C15—Fe2—C16—C17119.4 (5)
C10—Fe1—C5—C4133.7 (3)C21—Fe2—C16—C17122.0 (4)
C2—Fe1—C5—C638.1 (3)C22—Fe2—C16—C1779.3 (4)
C3—Fe1—C5—C682.6 (3)C15—C16—C17—C131.3 (6)
C8—Fe1—C5—C6173.0 (4)Fe2—C16—C17—C1358.7 (4)
C9—Fe1—C5—C6148.9 (3)C15—C16—C17—Fe259.9 (4)
C11—Fe1—C5—C666.3 (4)C14—C13—C17—C161.4 (6)
C7—Fe1—C5—C624 (2)C12—C13—C17—C16177.5 (5)
C4—Fe1—C5—C6120.5 (5)Fe2—C13—C17—C1659.1 (4)
C10—Fe1—C5—C6105.8 (4)C14—C13—C17—Fe260.5 (4)
C4—C5—C6—C20.8 (7)C12—C13—C17—Fe2118.4 (5)
Fe1—C5—C6—C257.9 (4)C13—Fe2—C17—C16119.3 (5)
C4—C5—C6—Fe158.7 (4)C20—Fe2—C17—C1643.0 (9)
C3—C2—C6—C50.7 (6)C18—Fe2—C17—C16160.7 (3)
C1—C2—C6—C5173.9 (5)C19—Fe2—C17—C16165.6 (6)
Fe1—C2—C6—C559.3 (4)C14—Fe2—C17—C1680.5 (4)
C3—C2—C6—Fe160.0 (4)C15—Fe2—C17—C1637.2 (3)
C1—C2—C6—Fe1114.6 (6)C21—Fe2—C17—C1676.7 (4)
C2—Fe1—C6—C5119.1 (5)C22—Fe2—C17—C16119.1 (4)
C3—Fe1—C6—C580.9 (4)C16—Fe2—C17—C13119.3 (5)
C8—Fe1—C6—C5149.7 (18)C20—Fe2—C17—C13162.3 (7)
C9—Fe1—C6—C556.1 (6)C18—Fe2—C17—C1380.0 (4)
C11—Fe1—C6—C5136.5 (3)C19—Fe2—C17—C1346.3 (8)
C7—Fe1—C6—C5176.4 (4)C14—Fe2—C17—C1338.8 (3)
C4—Fe1—C6—C536.8 (3)C15—Fe2—C17—C1382.1 (4)
C10—Fe1—C6—C592.7 (4)C21—Fe2—C17—C13164.0 (3)
C3—Fe1—C6—C238.2 (3)C22—Fe2—C17—C13121.6 (4)
C8—Fe1—C6—C231 (2)C13—Fe2—C18—C19117.4 (4)
C9—Fe1—C6—C2175.2 (4)C16—Fe2—C18—C19164.8 (6)
C11—Fe1—C6—C2104.4 (3)C20—Fe2—C18—C1937.7 (3)
C7—Fe1—C6—C264.5 (4)C14—Fe2—C18—C1975.5 (4)
C4—Fe1—C6—C282.4 (3)C17—Fe2—C18—C19160.6 (3)
C5—Fe1—C6—C2119.1 (5)C15—Fe2—C18—C1942.0 (9)
C10—Fe1—C6—C2148.1 (3)C21—Fe2—C18—C1982.4 (4)
C2—Fe1—C7—C8134.6 (4)C22—Fe2—C18—C19121.1 (5)
C3—Fe1—C7—C890.6 (4)C13—Fe2—C18—C22121.5 (4)
C9—Fe1—C7—C838.1 (4)C16—Fe2—C18—C2243.8 (8)
C11—Fe1—C7—C8118.1 (5)C20—Fe2—C18—C2283.3 (4)
C6—Fe1—C7—C8173.3 (4)C19—Fe2—C18—C22121.1 (5)
C4—Fe1—C7—C855.3 (6)C14—Fe2—C18—C22163.5 (4)
C5—Fe1—C7—C8165 (2)C17—Fe2—C18—C2278.3 (4)
C10—Fe1—C7—C881.0 (4)C15—Fe2—C18—C22163.0 (7)
C2—Fe1—C7—C11107.3 (4)C21—Fe2—C18—C2238.6 (4)
C3—Fe1—C7—C11151.3 (3)C22—C18—C19—C200.5 (6)
C8—Fe1—C7—C11118.1 (5)Fe2—C18—C19—C2059.4 (4)
C9—Fe1—C7—C1179.9 (4)C22—C18—C19—Fe259.0 (4)
C6—Fe1—C7—C1168.6 (5)C13—Fe2—C19—C1880.6 (4)
C4—Fe1—C7—C11173.3 (4)C16—Fe2—C19—C18162.6 (7)
C5—Fe1—C7—C1147 (2)C20—Fe2—C19—C18119.3 (5)
C10—Fe1—C7—C1137.1 (4)C14—Fe2—C19—C18123.6 (4)
C11—C7—C8—C90.6 (7)C17—Fe2—C19—C1846.7 (7)
Fe1—C7—C8—C959.4 (5)C15—Fe2—C19—C18164.7 (3)
C11—C7—C8—Fe160.0 (4)C21—Fe2—C19—C1881.1 (4)
C2—Fe1—C8—C765.6 (5)C22—Fe2—C19—C1836.7 (4)
C3—Fe1—C8—C7105.1 (4)C13—Fe2—C19—C20160.1 (3)
C9—Fe1—C8—C7119.4 (5)C16—Fe2—C19—C2043.3 (8)
C11—Fe1—C8—C738.1 (4)C18—Fe2—C19—C20119.3 (5)
C6—Fe1—C8—C739 (2)C14—Fe2—C19—C20117.1 (4)
C4—Fe1—C8—C7148.7 (4)C17—Fe2—C19—C20166.0 (6)
C5—Fe1—C8—C7177.0 (4)C15—Fe2—C19—C2076.0 (4)
C10—Fe1—C8—C781.8 (4)C21—Fe2—C19—C2038.2 (3)
C2—Fe1—C8—C9175.0 (4)C22—Fe2—C19—C2082.6 (4)
C3—Fe1—C8—C9135.5 (4)C18—C19—C20—C210.2 (6)
C11—Fe1—C8—C981.4 (4)Fe2—C19—C20—C2159.5 (4)
C7—Fe1—C8—C9119.4 (5)C18—C19—C20—Fe259.6 (4)
C6—Fe1—C8—C9158.3 (17)C13—Fe2—C20—C1946.4 (7)
C4—Fe1—C8—C991.9 (4)C16—Fe2—C20—C19164.1 (3)
C5—Fe1—C8—C957.6 (6)C18—Fe2—C20—C1937.3 (3)
C10—Fe1—C8—C937.6 (4)C14—Fe2—C20—C1981.3 (4)
C7—C8—C9—C101.4 (7)C17—Fe2—C20—C19163.5 (7)
Fe1—C8—C9—C1061.3 (4)C15—Fe2—C20—C19123.1 (4)
C7—C8—C9—Fe160.0 (5)C21—Fe2—C20—C19119.2 (5)
C2—Fe1—C9—C10148.0 (18)C22—Fe2—C20—C1980.8 (4)
C3—Fe1—C9—C10176.7 (4)C13—Fe2—C20—C21165.6 (5)
C8—Fe1—C9—C10117.9 (6)C16—Fe2—C20—C2176.7 (4)
C11—Fe1—C9—C1037.5 (4)C18—Fe2—C20—C2181.9 (4)
C7—Fe1—C9—C1080.8 (4)C19—Fe2—C20—C21119.2 (5)
C6—Fe1—C9—C1057.1 (6)C14—Fe2—C20—C21159.5 (3)
C4—Fe1—C9—C10136.7 (4)C17—Fe2—C20—C2144.3 (9)
C5—Fe1—C9—C1093.5 (4)C15—Fe2—C20—C21117.7 (4)
C2—Fe1—C9—C830 (2)C22—Fe2—C20—C2138.3 (3)
C3—Fe1—C9—C865.4 (5)C19—C20—C21—C220.2 (6)
C11—Fe1—C9—C880.4 (4)Fe2—C20—C21—C2259.3 (4)
C7—Fe1—C9—C837.1 (4)C19—C20—C21—Fe259.6 (4)
C6—Fe1—C9—C8174.9 (4)C13—Fe2—C21—C2243.6 (9)
C4—Fe1—C9—C8105.4 (4)C16—Fe2—C21—C22119.0 (4)
C5—Fe1—C9—C8148.6 (4)C20—Fe2—C21—C22118.4 (5)
C10—Fe1—C9—C8117.9 (6)C18—Fe2—C21—C2237.9 (3)
C8—C9—C10—C111.6 (7)C19—Fe2—C21—C2281.0 (4)
Fe1—C9—C10—C1158.4 (4)C14—Fe2—C21—C22167.3 (5)
C8—C9—C10—Fe160.0 (4)C17—Fe2—C21—C2277.6 (4)
C2—Fe1—C10—C9172.9 (4)C15—Fe2—C21—C22160.4 (4)
C3—Fe1—C10—C918 (2)C13—Fe2—C21—C20162.1 (7)
C8—Fe1—C10—C939.1 (4)C16—Fe2—C21—C20122.5 (4)
C11—Fe1—C10—C9119.5 (6)C18—Fe2—C21—C2080.5 (4)
C7—Fe1—C10—C982.6 (4)C19—Fe2—C21—C2037.4 (3)
C6—Fe1—C10—C9148.3 (4)C14—Fe2—C21—C2048.8 (7)
C4—Fe1—C10—C963.9 (5)C17—Fe2—C21—C20164.0 (3)
C5—Fe1—C10—C9104.3 (4)C15—Fe2—C21—C2081.2 (4)
C2—Fe1—C10—C1153.4 (6)C22—Fe2—C21—C20118.4 (5)
C3—Fe1—C10—C11137.3 (18)C19—C18—C22—C210.6 (6)
C8—Fe1—C10—C1180.3 (4)Fe2—C18—C22—C2159.5 (4)
C9—Fe1—C10—C11119.5 (6)C19—C18—C22—Fe258.9 (4)
C7—Fe1—C10—C1136.9 (4)C20—C21—C22—C180.5 (6)
C6—Fe1—C10—C1192.3 (4)Fe2—C21—C22—C1859.6 (4)
C4—Fe1—C10—C11176.7 (4)C20—C21—C22—Fe259.1 (4)
C5—Fe1—C10—C11136.3 (4)C13—Fe2—C22—C1877.4 (4)
C8—C7—C11—C100.4 (7)C16—Fe2—C22—C18162.1 (4)
Fe1—C7—C11—C1060.1 (4)C20—Fe2—C22—C1879.9 (4)
C8—C7—C11—Fe159.7 (5)C19—Fe2—C22—C1836.3 (4)
C9—C10—C11—C71.2 (7)C14—Fe2—C22—C1846.0 (9)
Fe1—C10—C11—C759.7 (5)C17—Fe2—C22—C18120.1 (4)
C9—C10—C11—Fe158.5 (4)C15—Fe2—C22—C18165.9 (6)
C2—Fe1—C11—C789.2 (4)C21—Fe2—C22—C18118.3 (5)
C3—Fe1—C11—C750.5 (6)C13—Fe2—C22—C21164.3 (3)
C8—Fe1—C11—C738.1 (4)C16—Fe2—C22—C2179.6 (4)
C9—Fe1—C11—C783.1 (4)C20—Fe2—C22—C2138.4 (3)
C6—Fe1—C11—C7133.8 (4)C18—Fe2—C22—C21118.3 (5)
C4—Fe1—C11—C7142 (2)C19—Fe2—C22—C2182.0 (4)
C5—Fe1—C11—C7173.3 (4)C14—Fe2—C22—C21164.3 (7)
C10—Fe1—C11—C7120.2 (5)C17—Fe2—C22—C21121.6 (4)
C2—Fe1—C11—C10150.7 (4)C15—Fe2—C22—C2147.6 (8)
C3—Fe1—C11—C10170.7 (4)O1—Cu1—O5—C2328.6 (4)
C8—Fe1—C11—C1082.0 (4)O4i—Cu1—O5—C23119.2 (4)
C9—Fe1—C11—C1037.0 (4)O2i—Cu1—O5—C23149.5 (4)
C7—Fe1—C11—C10120.2 (5)O3—Cu1—O5—C2361.2 (4)
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5O···O6ii0.82 (6)1.95 (6)2.759 (6)170 (7)
O6—H6O···O2iii0.84 (4)2.18 (5)2.925 (6)147 (7)
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula[Cu2Fe4(C5H5)4(C6H4O2)4(CH4O)2]·2CH4O
Mr1171.40
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)9.5112 (8), 9.5884 (9), 13.2478 (14)
α, β, γ (°)72.867 (7), 79.911 (8), 85.399 (7)
V3)1136.17 (19)
Z1
Radiation typeMo Kα
µ (mm1)2.23
Crystal size (mm)0.13 × 0.10 × 0.01
Data collection
DiffractometerStoe IPDS 2T
Absorption correctionIntegration
(X-RED; Stoe & Cie, 2002)
Tmin, Tmax0.768, 0.969
No. of measured, independent and
observed [I > 2σ(I)] reflections
8197, 3990, 2199
Rint0.071
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.080, 0.77
No. of reflections3990
No. of parameters306
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.38, 0.38

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED (Stoe & Cie, 2002), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5O···O6i0.82 (6)1.95 (6)2.759 (6)170 (7)
O6—H6O···O2ii0.84 (4)2.18 (5)2.925 (6)147 (7)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+1.
 

Acknowledgements

This work was supported financially by Eusko Jaurlaritza/Gobierno Vasco (grant IT477–10). BA and AP thank EJ/GV for their predoctoral fellowships.

References

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First citationZhang, E., Hou, H., Meng, X., Liu, Y., Liu, Y. & Fan, Y. (2009). Cryst. Growth Des. 9, 903–913.  Web of Science CSD CrossRef CAS Google Scholar

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