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The title compound, [Cu2Fe3(C5H5)3(C2H3O2)(C6H4O2)3(C3H7NO)2], contains a dinuclear copper(II) paddlewheel unit, where the metal ions are bridged by the O atoms of three ferrocenecarboxyl­ate groups and one acetate group. The crystal packing is mainly determined by van der Waals inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059041/rz2167sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059041/rz2167Isup2.hkl
Contains datablock I

CCDC reference: 1176502

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.012 Å
  • R factor = 0.060
  • wR factor = 0.184
  • Data-to-parameter ratio = 18.7

checkCIF/PLATON results

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Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.75 Ratio PLAT230_ALERT_2_B Hirshfeld Test Diff for N1 - C37 .. 12.79 su PLAT230_ALERT_2_B Hirshfeld Test Diff for N1 - C38 .. 7.32 su PLAT230_ALERT_2_B Hirshfeld Test Diff for N2 - C40 .. 9.72 su PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Fe3 - C32 .. 10.11 su PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Fe3 - C33 .. 10.72 su PLAT432_ALERT_2_B Short Inter X...Y Contact C3 .. C3 .. 3.02 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.65 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C41 .. 6.32 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe3 - C29 .. 9.16 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe3 - C30 .. 7.01 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C19 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C29 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C30 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C31 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C32 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C33 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 12
0 ALERT level A = In general: serious problem 7 ALERT level B = Potentially serious problem 18 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 21 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

It is well known that dicopper(II) carboxylates form a class of compounds in which a pair of copper atoms are symmetrically bridged by four carboxylates to give a paddlewheel or lantern structure (Chung & Wei, 1999; Chen et al., 2006). There are few examples of this kind of complexes consisting of two different carboxylate acids, especially bulky acids (Maspoch et al., 2002; Erre et al., 1985). Ferrocenecarboxylic acid was used to synthesize the title compound, resulting in a complex molecule containing three ferrocenecarboxylate groups and one acetate group which, as far as we know, is the first example of a dinuclear copper(II) carboxylate of this type.

In the structure of the title compound, the copper(II) metal atoms display a square-pyramidal coordination with the oxygen atoms of three ferrocenecarboxylate groups and one acetate group occupying the basal positions (Fig. 1). The four carboxylates bridge between the copper ions, forming a paddlewheel cage with a Cu—Cu separation of 2.6182 (11) Å. This value is a little larger than that observed for the tetrakis(ferrocenecarboxylato-O,O')bis(tetrahydrofuran)dicopper(ii) complex (Churchill et al., 1985). The Cu1 and Cu2 atoms are displaced 0.2143 (10) and 0.2059 (10) Å respectively from the basal plane. The Cu—O distances (Table 1) are in the range 1.946 (3)–1.9884 (4) Å, as observed in other dicopper complexes (Maspoch at al., 2002; Porter & Doedens, 1984; Viossat et al., 2005). The oxygen atom of a DMF molecule occupies the apical position, with Cu1—O10 and Cu2—O9 bond lengths of 2.166 (4) and 2.161 (4) Å, respectively. The ferrocenecarboxylate groups containing Fe1 and Fe2 are cis-oriented with respect to the C1···C12 vector. The crystal packing is mainly determined by van der Waals interactions (Fig. 2).

Related literature top

For related literature, see: Chung & Wei (1999); Churchill et al. (1985); Erre et al. (1985); Maspoch et al. (2002); Porter & Doedens (1984); Viossat et al. (2005); Chen et al. (2006).

Experimental top

A solution of ferrocenecarboxylic acid (0.046 g 0.02 mmol) in methanol (10 ml) and NaHCO3 (0.017 g 0.02 mmol) was stirred for half an hour. Then Cu(OAc)2.H2O (0.025 g, 0.013 mmol) was added. The mixture was stirred for 3 h at room temperature. All the volatiles were removed under vacuum and the residue was recrystallized from CCl2H2—DMF mixture (1:1 v/v) to give green crystal of the title compound suitable for X-ray analysis.

Refinement top

All of H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93–0.96 Å and Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: RAPID-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1993); software used to prepare material for publication: SHELXL97-2 (Sheldrick,1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme and 30% probability displacemene ellipsoids. H atoms are omitted for clarity.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed along the a axis. H atoms are omitted for clarity.
µ-Acetato-tri-µ-ferrocenecarboxylato-bis[(N,N-dimethylformamide)copper(II)] top
Crystal data top
[Cu2Fe3(C5H5)3(C2H3O2)(C6H4O2)3(C3H7NO)2]Z = 2
Mr = 1019.41F(000) = 1040
Triclinic, P1Dx = 1.666 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.948 (2) ÅCell parameters from 14862 reflections
b = 13.548 (3) Åθ = 3.1–27.5°
c = 15.828 (3) ŵ = 2.14 mm1
α = 108.96 (3)°T = 295 K
β = 94.57 (3)°Block, green
γ = 110.33 (3)°0.22 × 0.18 × 0.18 mm
V = 2032.3 (10) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
6613 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
Oscillation scansh = 1413
19821 measured reflectionsk = 1717
9106 independent reflectionsl = 2020
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0962P)2 + 3.4415P]
where P = (Fo2 + 2Fc2)/3
9106 reflections(Δ/σ)max < 0.001
486 parametersΔρmax = 0.76 e Å3
0 restraintsΔρmin = 1.39 e Å3
Crystal data top
[Cu2Fe3(C5H5)3(C2H3O2)(C6H4O2)3(C3H7NO)2]γ = 110.33 (3)°
Mr = 1019.41V = 2032.3 (10) Å3
Triclinic, P1Z = 2
a = 10.948 (2) ÅMo Kα radiation
b = 13.548 (3) ŵ = 2.14 mm1
c = 15.828 (3) ÅT = 295 K
α = 108.96 (3)°0.22 × 0.18 × 0.18 mm
β = 94.57 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
6613 reflections with I > 2σ(I)
19821 measured reflectionsRint = 0.045
9106 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.184H-atom parameters constrained
S = 1.05Δρmax = 0.76 e Å3
9106 reflectionsΔρmin = 1.39 e Å3
486 parameters
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
Cu10.61220 (6)0.29677 (5)0.14850 (4)0.02853 (16)
Cu20.87075 (6)0.35953 (5)0.16691 (4)0.02790 (16)
Fe20.73811 (9)0.15331 (7)0.19309 (5)0.0366 (2)
Fe10.76655 (8)0.22841 (7)0.46343 (5)0.0373 (2)
Fe30.74862 (10)0.73109 (8)0.36609 (7)0.0506 (2)
O30.8335 (4)0.3589 (3)0.0433 (2)0.0351 (8)
O70.8240 (4)0.1930 (3)0.1141 (3)0.0381 (8)
O60.6555 (4)0.4598 (3)0.1752 (3)0.0359 (8)
O40.6113 (4)0.2705 (3)0.0184 (2)0.0380 (8)
O50.8760 (4)0.5149 (3)0.2192 (3)0.0388 (9)
O20.6557 (4)0.3314 (4)0.2820 (2)0.0420 (9)
O10.8682 (4)0.3497 (4)0.2867 (2)0.0402 (9)
O80.6111 (4)0.1451 (3)0.1259 (3)0.0398 (9)
O100.3985 (4)0.2433 (4)0.1349 (3)0.0463 (10)
O91.0815 (4)0.4089 (4)0.1694 (3)0.0443 (9)
N11.2437 (6)0.4268 (6)0.0902 (5)0.0675 (18)
N20.2132 (7)0.2176 (6)0.1945 (6)0.0697 (19)
C10.7695 (6)0.3445 (4)0.3222 (3)0.0343 (11)
C20.7867 (6)0.3563 (5)0.4188 (4)0.0395 (12)
C30.9086 (7)0.3769 (5)0.4743 (4)0.0460 (14)
H30.98860.38470.45550.055*
C40.8882 (8)0.3834 (5)0.5624 (4)0.0548 (17)
H40.95230.39770.61190.066*
C50.7540 (9)0.3645 (6)0.5617 (4)0.0573 (18)
H50.71320.36260.61090.069*
C60.6905 (8)0.3487 (6)0.4738 (4)0.0521 (16)
H60.60150.33570.45550.063*
C70.6141 (8)0.0739 (7)0.4289 (6)0.068 (2)
H70.52520.06070.43040.082*
C80.7128 (10)0.0913 (6)0.5000 (5)0.069 (2)
H80.70040.09210.55770.083*
C90.8316 (9)0.1072 (6)0.4718 (6)0.069 (2)
H90.91230.11960.50600.083*
C100.8074 (9)0.1012 (6)0.3804 (6)0.068 (2)
H100.87040.11000.34430.082*
C110.6745 (8)0.0800 (6)0.3539 (5)0.0597 (18)
H110.63230.07120.29700.072*
C120.7189 (5)0.3073 (4)0.0066 (3)0.0301 (10)
C130.7077 (5)0.2853 (4)0.1057 (3)0.0314 (10)
C140.8150 (6)0.3260 (5)0.1483 (4)0.0387 (12)
H140.90260.37490.11830.046*
C150.7639 (7)0.2787 (5)0.2438 (4)0.0483 (15)
H150.81200.29000.28810.058*
C160.6262 (7)0.2108 (5)0.2599 (4)0.0459 (14)
H160.56850.17010.31700.055*
C170.5908 (6)0.2146 (5)0.1762 (4)0.0403 (12)
H170.50610.17760.16810.048*
C180.6875 (9)0.0107 (6)0.1635 (7)0.068 (2)
H180.61540.01700.13830.082*
C190.6858 (10)0.0179 (7)0.2583 (7)0.077 (3)
H190.61320.06720.30650.092*
C200.8156 (10)0.0431 (7)0.2648 (5)0.070 (2)
H200.84400.04130.31890.084*
C210.8948 (7)0.1067 (6)0.1768 (5)0.0547 (16)
H210.98490.15400.16210.066*
C220.8153 (8)0.0872 (6)0.1148 (5)0.0521 (16)
H220.84310.11980.05140.062*
C230.7722 (5)0.5336 (4)0.2103 (3)0.0316 (10)
C240.7895 (6)0.6546 (5)0.2447 (4)0.0390 (12)
C250.9056 (7)0.7480 (6)0.3031 (5)0.0557 (17)
H250.98560.74440.32310.067*
C260.8796 (7)0.8480 (6)0.3260 (6)0.064 (2)
H260.93890.92110.36360.076*
C270.7461 (8)0.8160 (6)0.2810 (5)0.0613 (18)
H270.70260.86460.28350.074*
C280.6914 (7)0.6974 (6)0.2318 (5)0.0517 (15)
H280.60500.65430.19670.062*
C290.7967 (13)0.7074 (11)0.4817 (7)0.1035 (17)
H290.87650.70390.50220.124*
C300.7749 (13)0.8055 (11)0.5033 (7)0.1035 (17)
H300.83480.87890.53980.124*
C310.6402 (13)0.7706 (11)0.4575 (7)0.1035 (17)
H310.59550.81810.45890.124*
C320.5877 (13)0.6540 (11)0.4106 (7)0.1035 (17)
H320.50190.60940.37490.124*
C330.6860 (13)0.6156 (12)0.4263 (7)0.1035 (17)
H330.67790.54060.40320.124*
C350.6934 (8)0.0006 (5)0.0838 (5)0.0558 (17)
H35A0.74190.00800.13310.084*
H35B0.72730.02320.02980.084*
H35C0.60050.04830.07200.084*
C361.1219 (7)0.3952 (6)0.0992 (6)0.0590 (18)
H361.05690.35710.04520.071*
C371.3472 (11)0.4908 (11)0.1742 (10)0.112 (2)
H37A1.31680.46570.22180.168*
H37B1.36590.57030.19230.168*
H37C1.42680.47840.16380.168*
C381.2905 (11)0.4134 (11)0.0096 (9)0.112 (2)
H38A1.21700.36620.04200.168*
H38B1.35320.37840.00930.168*
H38C1.33360.48650.00600.168*
C340.7101 (6)0.1220 (5)0.1097 (4)0.0373 (12)
C400.1239 (11)0.1510 (11)0.1034 (10)0.112 (2)
H40A0.17000.16900.05790.168*
H40B0.04660.16910.10170.168*
H40C0.09670.07140.09130.168*
C410.1499 (11)0.2274 (10)0.2676 (9)0.112 (2)
H41A0.21510.27530.32370.168*
H41B0.10430.15350.26910.168*
H41C0.08670.26010.26060.168*
C390.3427 (8)0.2540 (7)0.1983 (6)0.062 (2)
H390.39770.29240.25650.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0279 (3)0.0294 (3)0.0301 (3)0.0118 (2)0.0105 (2)0.0119 (2)
Cu20.0276 (3)0.0293 (3)0.0285 (3)0.0122 (3)0.0081 (2)0.0116 (2)
Fe20.0524 (5)0.0332 (4)0.0312 (4)0.0214 (4)0.0126 (3)0.0154 (3)
Fe10.0448 (5)0.0330 (4)0.0328 (4)0.0120 (4)0.0073 (3)0.0149 (3)
Fe30.0512 (5)0.0473 (5)0.0511 (5)0.0241 (4)0.0134 (4)0.0103 (4)
O30.035 (2)0.040 (2)0.0288 (17)0.0120 (17)0.0066 (16)0.0147 (16)
O70.041 (2)0.0286 (18)0.047 (2)0.0154 (17)0.0158 (18)0.0137 (16)
O60.036 (2)0.0304 (18)0.0402 (19)0.0146 (17)0.0078 (17)0.0113 (16)
O40.040 (2)0.043 (2)0.0296 (17)0.0147 (18)0.0102 (16)0.0132 (16)
O50.043 (2)0.0306 (19)0.043 (2)0.0169 (17)0.0132 (18)0.0111 (16)
O20.049 (2)0.050 (2)0.0316 (18)0.021 (2)0.0152 (18)0.0183 (17)
O10.045 (2)0.048 (2)0.0312 (18)0.0200 (19)0.0103 (17)0.0179 (17)
O80.039 (2)0.0298 (19)0.053 (2)0.0129 (17)0.0192 (19)0.0176 (17)
O100.032 (2)0.046 (2)0.066 (3)0.0177 (18)0.020 (2)0.023 (2)
O90.033 (2)0.051 (2)0.052 (2)0.0152 (19)0.0143 (19)0.023 (2)
N10.044 (3)0.069 (4)0.108 (5)0.027 (3)0.039 (4)0.047 (4)
N20.058 (4)0.091 (5)0.111 (6)0.050 (4)0.050 (4)0.073 (5)
C10.045 (3)0.031 (3)0.030 (2)0.016 (2)0.007 (2)0.014 (2)
C20.053 (3)0.039 (3)0.029 (2)0.018 (3)0.009 (2)0.016 (2)
C30.053 (4)0.029 (3)0.046 (3)0.003 (3)0.000 (3)0.019 (2)
C40.075 (5)0.036 (3)0.039 (3)0.012 (3)0.006 (3)0.011 (3)
C50.099 (6)0.057 (4)0.032 (3)0.043 (4)0.020 (3)0.022 (3)
C60.073 (5)0.066 (4)0.041 (3)0.045 (4)0.024 (3)0.028 (3)
C70.054 (4)0.054 (4)0.080 (5)0.003 (4)0.010 (4)0.024 (4)
C80.102 (7)0.045 (4)0.059 (4)0.018 (4)0.015 (4)0.029 (3)
C90.086 (6)0.043 (4)0.078 (5)0.032 (4)0.001 (5)0.019 (4)
C100.077 (5)0.044 (4)0.078 (5)0.022 (4)0.038 (4)0.013 (4)
C110.071 (5)0.043 (4)0.042 (3)0.009 (3)0.001 (3)0.006 (3)
C120.040 (3)0.024 (2)0.031 (2)0.017 (2)0.010 (2)0.0118 (19)
C130.041 (3)0.033 (3)0.028 (2)0.018 (2)0.009 (2)0.016 (2)
C140.051 (3)0.033 (3)0.041 (3)0.017 (3)0.017 (3)0.022 (2)
C150.080 (5)0.048 (3)0.040 (3)0.036 (4)0.029 (3)0.030 (3)
C160.063 (4)0.045 (3)0.032 (3)0.022 (3)0.004 (3)0.017 (2)
C170.044 (3)0.040 (3)0.041 (3)0.018 (3)0.008 (3)0.019 (2)
C180.079 (5)0.048 (4)0.110 (7)0.035 (4)0.041 (5)0.055 (4)
C190.090 (6)0.042 (4)0.088 (6)0.036 (4)0.012 (5)0.009 (4)
C200.123 (8)0.074 (5)0.049 (4)0.071 (6)0.038 (5)0.026 (4)
C210.056 (4)0.053 (4)0.068 (4)0.032 (3)0.017 (3)0.028 (3)
C220.078 (5)0.056 (4)0.051 (3)0.045 (4)0.024 (3)0.034 (3)
C230.040 (3)0.031 (3)0.028 (2)0.017 (2)0.013 (2)0.012 (2)
C240.046 (3)0.027 (3)0.044 (3)0.016 (2)0.015 (3)0.010 (2)
C250.046 (4)0.044 (4)0.075 (5)0.020 (3)0.020 (3)0.016 (3)
C260.055 (4)0.036 (3)0.092 (5)0.013 (3)0.021 (4)0.017 (4)
C270.072 (5)0.045 (4)0.077 (5)0.031 (4)0.019 (4)0.025 (4)
C280.056 (4)0.048 (4)0.053 (4)0.026 (3)0.009 (3)0.017 (3)
C290.129 (4)0.127 (4)0.081 (3)0.069 (4)0.058 (3)0.044 (3)
C300.129 (4)0.127 (4)0.081 (3)0.069 (4)0.058 (3)0.044 (3)
C310.129 (4)0.127 (4)0.081 (3)0.069 (4)0.058 (3)0.044 (3)
C320.129 (4)0.127 (4)0.081 (3)0.069 (4)0.058 (3)0.044 (3)
C330.129 (4)0.127 (4)0.081 (3)0.069 (4)0.058 (3)0.044 (3)
C350.072 (5)0.034 (3)0.072 (4)0.026 (3)0.029 (4)0.024 (3)
C360.046 (4)0.061 (4)0.081 (5)0.025 (3)0.024 (4)0.034 (4)
C370.088 (4)0.122 (5)0.184 (6)0.067 (4)0.074 (4)0.091 (5)
C380.088 (4)0.122 (5)0.184 (6)0.067 (4)0.074 (4)0.091 (5)
C340.052 (3)0.028 (3)0.032 (2)0.014 (2)0.014 (2)0.014 (2)
C400.088 (4)0.122 (5)0.184 (6)0.067 (4)0.074 (4)0.091 (5)
C410.088 (4)0.122 (5)0.184 (6)0.067 (4)0.074 (4)0.091 (5)
C390.067 (4)0.077 (5)0.085 (5)0.047 (4)0.048 (4)0.057 (4)
Geometric parameters (Å, º) top
Cu1—O81.964 (4)C7—C111.416 (11)
Cu1—O41.970 (4)C7—H70.9300
Cu1—O61.978 (4)C8—C91.377 (12)
Cu1—O21.987 (4)C8—H80.9300
Cu1—O102.164 (4)C9—C101.420 (12)
Cu1—Cu22.6183 (11)C9—H90.9300
Cu2—O11.945 (4)C10—C111.381 (11)
Cu2—O31.963 (4)C10—H100.9300
Cu2—O51.973 (4)C11—H110.9300
Cu2—O71.988 (4)C12—C131.485 (7)
Cu2—O92.161 (4)C13—C171.424 (8)
Fe2—C132.025 (5)C13—C141.434 (7)
Fe2—C222.034 (6)C14—C151.413 (8)
Fe2—C142.036 (6)C14—H140.9300
Fe2—C182.036 (7)C15—C161.416 (10)
Fe2—C202.042 (7)C15—H150.9300
Fe2—C212.048 (7)C16—C171.399 (8)
Fe2—C152.049 (6)C16—H160.9300
Fe2—C192.049 (7)C17—H170.9300
Fe2—C162.053 (6)C18—C221.388 (11)
Fe2—C172.054 (6)C18—C191.420 (12)
Fe1—C32.013 (6)C18—H180.9300
Fe1—C102.014 (7)C19—C201.405 (13)
Fe1—C22.025 (6)C19—H190.9300
Fe1—C112.028 (7)C20—C211.394 (11)
Fe1—C82.031 (7)C20—H200.9300
Fe1—C72.037 (8)C21—C221.391 (9)
Fe1—C92.039 (7)C21—H210.9300
Fe1—C62.042 (7)C22—H220.9300
Fe1—C52.046 (6)C23—C241.486 (7)
Fe1—C42.055 (6)C24—C281.416 (9)
Fe3—C312.000 (9)C24—C251.416 (9)
Fe3—C292.018 (12)C25—C261.419 (9)
Fe3—C282.019 (7)C25—H250.9300
Fe3—C322.022 (11)C26—C271.423 (11)
Fe3—C302.023 (10)C26—H260.9300
Fe3—C242.033 (5)C27—C281.411 (9)
Fe3—C252.037 (6)C27—H270.9300
Fe3—C332.038 (12)C28—H280.9300
Fe3—C272.040 (8)C29—C331.364 (16)
Fe3—C262.046 (8)C29—C301.371 (16)
O3—C121.249 (6)C29—H290.9300
O7—C341.264 (7)C30—C311.431 (16)
O6—C231.257 (6)C30—H300.9300
O4—C121.261 (6)C31—C321.384 (16)
O5—C231.255 (6)C31—H310.9300
O2—C11.279 (7)C32—C331.386 (15)
O1—C11.249 (6)C32—H320.9300
O8—C341.250 (7)C33—H330.9300
O10—C391.211 (7)C35—C341.515 (8)
O9—C361.210 (8)C35—H35A0.9600
N1—C361.287 (8)C35—H35B0.9600
N1—C381.393 (12)C35—H35C0.9600
N1—C371.460 (15)C36—H360.9300
N2—C391.319 (9)C37—H37A0.9600
N2—C411.389 (12)C37—H37B0.9600
N2—C401.472 (15)C37—H37C0.9600
C1—C21.474 (7)C38—H38A0.9600
C2—C61.416 (8)C38—H38B0.9600
C2—C31.423 (9)C38—H38C0.9600
C3—C41.408 (9)C40—H40A0.9600
C3—H30.9300C40—H40B0.9600
C4—C51.399 (11)C40—H40C0.9600
C4—H40.9300C41—H41A0.9600
C5—C61.420 (9)C41—H41B0.9600
C5—H50.9300C41—H41C0.9600
C6—H60.9300C39—H390.9300
C7—C81.396 (12)
O8—Cu1—O489.37 (17)C4—C5—H5125.6
O8—Cu1—O6167.62 (15)C6—C5—H5125.6
O4—Cu1—O689.89 (16)Fe1—C5—H5126.1
O8—Cu1—O288.57 (18)C2—C6—C5107.8 (6)
O4—Cu1—O2167.40 (16)C2—C6—Fe169.0 (3)
O6—Cu1—O289.46 (17)C5—C6—Fe169.8 (4)
O8—Cu1—O1095.06 (16)C2—C6—H6126.1
O4—Cu1—O1096.20 (17)C5—C6—H6126.1
O6—Cu1—O1097.31 (16)Fe1—C6—H6126.6
O2—Cu1—O1096.36 (17)C8—C7—C11107.2 (7)
O8—Cu1—Cu284.26 (12)C8—C7—Fe169.7 (4)
O4—Cu1—Cu284.55 (12)C11—C7—Fe169.3 (4)
O6—Cu1—Cu283.36 (11)C8—C7—H7126.4
O2—Cu1—Cu282.87 (12)C11—C7—H7126.4
O10—Cu1—Cu2178.98 (12)Fe1—C7—H7126.2
O1—Cu2—O3168.23 (16)C9—C8—C7109.5 (7)
O1—Cu2—O589.34 (17)C9—C8—Fe170.5 (4)
O3—Cu2—O589.81 (17)C7—C8—Fe170.2 (4)
O1—Cu2—O788.32 (17)C9—C8—H8125.2
O3—Cu2—O790.03 (17)C7—C8—H8125.2
O5—Cu2—O7167.72 (16)Fe1—C8—H8125.6
O1—Cu2—O999.92 (17)C8—C9—C10107.0 (8)
O3—Cu2—O991.85 (16)C8—C9—Fe169.9 (4)
O5—Cu2—O996.55 (17)C10—C9—Fe168.5 (4)
O7—Cu2—O995.72 (16)C8—C9—H9126.5
O1—Cu2—Cu185.06 (12)C10—C9—H9126.5
O3—Cu2—Cu183.17 (11)Fe1—C9—H9126.6
O5—Cu2—Cu184.36 (12)C11—C10—C9108.6 (7)
O7—Cu2—Cu183.44 (12)C11—C10—Fe170.6 (4)
O9—Cu2—Cu1174.93 (11)C9—C10—Fe170.4 (4)
C13—Fe2—C22106.6 (2)C11—C10—H10125.7
C13—Fe2—C1441.3 (2)C9—C10—H10125.7
C22—Fe2—C14115.7 (3)Fe1—C10—H10124.9
C13—Fe2—C18116.4 (3)C10—C11—C7107.8 (7)
C22—Fe2—C1839.9 (3)C10—C11—Fe169.5 (4)
C14—Fe2—C18148.9 (3)C7—C11—Fe170.0 (4)
C13—Fe2—C20166.1 (3)C10—C11—H11126.1
C22—Fe2—C2067.1 (3)C7—C11—H11126.1
C14—Fe2—C20128.8 (3)Fe1—C11—H11126.0
C18—Fe2—C2067.4 (3)O3—C12—O4126.5 (5)
C13—Fe2—C21127.6 (3)O3—C12—C13117.1 (4)
C22—Fe2—C2139.8 (3)O4—C12—C13116.4 (5)
C14—Fe2—C21107.1 (3)C17—C13—C14107.6 (5)
C18—Fe2—C2167.1 (3)C17—C13—C12126.3 (5)
C20—Fe2—C2139.9 (3)C14—C13—C12126.0 (5)
C13—Fe2—C1568.7 (2)C17—C13—Fe270.6 (3)
C22—Fe2—C15149.3 (3)C14—C13—Fe269.7 (3)
C14—Fe2—C1540.5 (2)C12—C13—Fe2122.2 (3)
C18—Fe2—C15169.9 (3)C15—C14—C13107.8 (5)
C20—Fe2—C15109.9 (3)C15—C14—Fe270.2 (3)
C21—Fe2—C15117.7 (3)C13—C14—Fe268.9 (3)
C13—Fe2—C19150.7 (3)C15—C14—H14126.1
C22—Fe2—C1967.7 (3)C13—C14—H14126.1
C14—Fe2—C19167.7 (3)Fe2—C14—H14126.3
C18—Fe2—C1940.7 (4)C14—C15—C16107.6 (5)
C20—Fe2—C1940.2 (4)C14—C15—Fe269.3 (3)
C21—Fe2—C1967.5 (3)C16—C15—Fe270.0 (3)
C15—Fe2—C19131.0 (3)C14—C15—H15126.2
C13—Fe2—C1668.0 (2)C16—C15—H15126.2
C22—Fe2—C16167.9 (3)Fe2—C15—H15126.1
C14—Fe2—C1667.9 (3)C17—C16—C15109.3 (5)
C18—Fe2—C16131.6 (3)C17—C16—Fe270.1 (3)
C20—Fe2—C16120.6 (3)C15—C16—Fe269.6 (4)
C21—Fe2—C16151.9 (3)C17—C16—H16125.3
C15—Fe2—C1640.4 (3)C15—C16—H16125.3
C19—Fe2—C16111.4 (3)Fe2—C16—H16126.5
C13—Fe2—C1740.9 (2)C16—C17—C13107.7 (5)
C22—Fe2—C17129.2 (2)C16—C17—Fe270.1 (3)
C14—Fe2—C1768.7 (2)C13—C17—Fe268.5 (3)
C18—Fe2—C17109.5 (3)C16—C17—H17126.2
C20—Fe2—C17152.5 (3)C13—C17—H17126.2
C21—Fe2—C17166.4 (3)Fe2—C17—H17126.8
C15—Fe2—C1768.1 (2)C22—C18—C19108.3 (7)
C19—Fe2—C17119.2 (3)C22—C18—Fe270.0 (4)
C16—Fe2—C1739.8 (2)C19—C18—Fe270.2 (4)
C3—Fe1—C10108.2 (3)C22—C18—H18125.9
C3—Fe1—C241.3 (2)C19—C18—H18125.9
C10—Fe1—C2114.7 (3)Fe2—C18—H18125.6
C3—Fe1—C11130.4 (3)C20—C19—C18106.4 (8)
C10—Fe1—C1140.0 (3)C20—C19—Fe269.6 (4)
C2—Fe1—C11107.5 (3)C18—C19—Fe269.2 (4)
C3—Fe1—C8148.2 (3)C20—C19—H19126.8
C10—Fe1—C867.6 (3)C18—C19—H19126.8
C2—Fe1—C8170.3 (3)Fe2—C19—H19126.0
C11—Fe1—C867.7 (3)C21—C20—C19108.8 (7)
C3—Fe1—C7169.9 (3)C21—C20—Fe270.3 (4)
C10—Fe1—C767.8 (3)C19—C20—Fe270.2 (4)
C2—Fe1—C7130.9 (3)C21—C20—H20125.6
C11—Fe1—C740.8 (3)C19—C20—H20125.6
C8—Fe1—C740.1 (3)Fe2—C20—H20125.5
C3—Fe1—C9116.1 (3)C22—C21—C20108.0 (7)
C10—Fe1—C941.0 (3)C22—C21—Fe269.5 (4)
C2—Fe1—C9147.8 (3)C20—C21—Fe269.8 (4)
C11—Fe1—C968.0 (3)C22—C21—H21126.0
C8—Fe1—C939.6 (4)C20—C21—H21126.0
C7—Fe1—C967.5 (4)Fe2—C21—H21126.2
C3—Fe1—C668.5 (3)C18—C22—C21108.5 (7)
C10—Fe1—C6147.1 (3)C18—C22—Fe270.2 (4)
C2—Fe1—C640.8 (2)C21—C22—Fe270.6 (4)
C11—Fe1—C6115.9 (3)C18—C22—H22125.7
C8—Fe1—C6132.6 (3)C21—C22—H22125.7
C7—Fe1—C6109.5 (3)Fe2—C22—H22125.1
C9—Fe1—C6170.7 (3)O5—C23—O6126.1 (5)
C3—Fe1—C567.9 (3)O5—C23—C24116.6 (5)
C10—Fe1—C5170.6 (4)O6—C23—C24117.2 (5)
C2—Fe1—C568.5 (2)C28—C24—C25107.3 (5)
C11—Fe1—C5149.0 (3)C28—C24—C23126.9 (5)
C8—Fe1—C5110.9 (3)C25—C24—C23125.6 (5)
C7—Fe1—C5117.5 (3)C28—C24—Fe369.0 (3)
C9—Fe1—C5132.0 (3)C25—C24—Fe369.8 (3)
C6—Fe1—C540.7 (3)C23—C24—Fe3122.7 (4)
C3—Fe1—C440.5 (3)C24—C25—C26108.6 (6)
C10—Fe1—C4131.7 (3)C24—C25—Fe369.5 (3)
C2—Fe1—C468.7 (2)C26—C25—Fe370.0 (4)
C11—Fe1—C4169.5 (3)C24—C25—H25125.7
C8—Fe1—C4117.5 (3)C26—C25—H25125.7
C7—Fe1—C4148.9 (3)Fe3—C25—H25126.4
C9—Fe1—C4109.7 (3)C25—C26—C27107.5 (6)
C6—Fe1—C468.0 (3)C25—C26—Fe369.3 (4)
C5—Fe1—C439.9 (3)C27—C26—Fe369.4 (4)
C31—Fe3—C2967.2 (5)C25—C26—H26126.3
C31—Fe3—C28122.9 (4)C27—C26—H26126.3
C29—Fe3—C28159.9 (4)Fe3—C26—H26126.6
C31—Fe3—C3240.2 (4)C28—C27—C26107.8 (6)
C29—Fe3—C3266.7 (5)C28—C27—Fe368.9 (4)
C28—Fe3—C32108.6 (4)C26—C27—Fe369.9 (4)
C31—Fe3—C3041.7 (4)C28—C27—H27126.1
C29—Fe3—C3039.7 (4)C26—C27—H27126.1
C28—Fe3—C30159.1 (4)Fe3—C27—H27126.7
C32—Fe3—C3068.7 (5)C27—C28—C24108.8 (6)
C31—Fe3—C24158.7 (4)C27—C28—Fe370.4 (4)
C29—Fe3—C24123.7 (4)C24—C28—Fe370.1 (4)
C28—Fe3—C2440.9 (2)C27—C28—H28125.6
C32—Fe3—C24123.1 (4)C24—C28—H28125.6
C30—Fe3—C24158.1 (4)Fe3—C28—H28125.5
C31—Fe3—C25159.4 (4)C33—C29—C30111.1 (13)
C29—Fe3—C25108.3 (4)C33—C29—Fe371.1 (7)
C28—Fe3—C2568.4 (3)C30—C29—Fe370.3 (7)
C32—Fe3—C25158.6 (4)C33—C29—H29124.4
C30—Fe3—C25121.8 (4)C30—C29—H29124.4
C24—Fe3—C2540.7 (3)Fe3—C29—H29125.7
C31—Fe3—C3367.2 (5)C29—C30—C31105.0 (12)
C29—Fe3—C3339.3 (5)C29—C30—Fe370.0 (6)
C28—Fe3—C33124.6 (4)C31—C30—Fe368.3 (6)
C32—Fe3—C3339.9 (4)C29—C30—H30127.5
C30—Fe3—C3367.5 (5)C31—C30—H30127.5
C24—Fe3—C33108.5 (4)Fe3—C30—H30125.8
C25—Fe3—C33123.0 (4)C32—C31—C30108.3 (12)
C31—Fe3—C27107.9 (4)C32—C31—Fe370.7 (6)
C29—Fe3—C27158.3 (4)C30—C31—Fe370.0 (6)
C28—Fe3—C2740.7 (3)C32—C31—H31125.8
C32—Fe3—C27124.1 (4)C30—C31—H31125.8
C30—Fe3—C27122.4 (4)Fe3—C31—H31125.0
C24—Fe3—C2768.7 (3)C31—C32—C33107.7 (13)
C25—Fe3—C2768.4 (3)C31—C32—Fe369.0 (7)
C33—Fe3—C27160.4 (4)C33—C32—Fe370.7 (7)
C31—Fe3—C26123.3 (4)C31—C32—H32126.2
C29—Fe3—C26122.8 (5)C33—C32—H32126.2
C28—Fe3—C2668.6 (3)Fe3—C32—H32125.7
C32—Fe3—C26159.9 (4)C29—C33—C32107.8 (12)
C30—Fe3—C26106.4 (4)C29—C33—Fe369.6 (7)
C24—Fe3—C2668.7 (3)C32—C33—Fe369.4 (7)
C25—Fe3—C2640.7 (3)C29—C33—H33126.1
C33—Fe3—C26158.0 (4)C32—C33—H33126.1
C27—Fe3—C2640.8 (3)Fe3—C33—H33126.5
C12—O3—Cu2121.8 (3)C34—C35—H35A109.5
C34—O7—Cu2121.7 (3)C34—C35—H35B109.5
C23—O6—Cu1121.6 (3)H35A—C35—H35B109.5
C12—O4—Cu1120.3 (3)C34—C35—H35C109.5
C23—O5—Cu2121.2 (4)H35A—C35—H35C109.5
C1—O2—Cu1121.8 (3)H35B—C35—H35C109.5
C1—O1—Cu2122.0 (4)O9—C36—N1128.0 (8)
C34—O8—Cu1122.4 (3)O9—C36—H36116.0
C39—O10—Cu1124.8 (5)N1—C36—H36116.0
C36—O9—Cu2121.0 (5)N1—C37—H37A109.5
C36—N1—C38128.2 (9)N1—C37—H37B109.5
C36—N1—C37116.8 (8)H37A—C37—H37B109.5
C38—N1—C37114.9 (8)N1—C37—H37C109.5
C39—N2—C41127.3 (9)H37A—C37—H37C109.5
C39—N2—C40117.3 (7)H37B—C37—H37C109.5
C41—N2—C40115.2 (8)N1—C38—H38A109.5
O1—C1—O2125.2 (5)N1—C38—H38B109.5
O1—C1—C2117.1 (5)H38A—C38—H38B109.5
O2—C1—C2117.6 (5)N1—C38—H38C109.5
C6—C2—C3107.0 (5)H38A—C38—H38C109.5
C6—C2—C1128.6 (6)H38B—C38—H38C109.5
C3—C2—C1124.4 (5)O8—C34—O7125.3 (5)
C6—C2—Fe170.2 (3)O8—C34—C35117.8 (5)
C3—C2—Fe168.9 (3)O7—C34—C35116.9 (5)
C1—C2—Fe1125.3 (4)N2—C40—H40A109.5
C4—C3—C2108.8 (6)N2—C40—H40B109.5
C4—C3—Fe171.4 (4)H40A—C40—H40B109.5
C2—C3—Fe169.8 (3)N2—C40—H40C109.5
C4—C3—H3125.6H40A—C40—H40C109.5
C2—C3—H3125.6H40B—C40—H40C109.5
Fe1—C3—H3124.8N2—C41—H41A109.5
C5—C4—C3107.6 (6)N2—C41—H41B109.5
C5—C4—Fe169.7 (4)H41A—C41—H41B109.5
C3—C4—Fe168.2 (3)N2—C41—H41C109.5
C5—C4—H4126.2H41A—C41—H41C109.5
C3—C4—H4126.2H41B—C41—H41C109.5
Fe1—C4—H4127.5O10—C39—N2127.7 (9)
C4—C5—C6108.8 (6)O10—C39—H39116.2
C4—C5—Fe170.4 (4)N2—C39—H39116.2
C6—C5—Fe169.5 (4)

Experimental details

Crystal data
Chemical formula[Cu2Fe3(C5H5)3(C2H3O2)(C6H4O2)3(C3H7NO)2]
Mr1019.41
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)10.948 (2), 13.548 (3), 15.828 (3)
α, β, γ (°)108.96 (3), 94.57 (3), 110.33 (3)
V3)2032.3 (10)
Z2
Radiation typeMo Kα
µ (mm1)2.14
Crystal size (mm)0.22 × 0.18 × 0.18
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
19821, 9106, 6613
Rint0.045
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.184, 1.05
No. of reflections9106
No. of parameters486
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.76, 1.39

Computer programs: RAPID-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1993), SHELXL97-2 (Sheldrick,1997).

Selected bond lengths (Å) top
Cu1—O81.964 (4)O3—C121.249 (6)
Cu1—O41.970 (4)O7—C341.264 (7)
Cu1—O61.978 (4)O6—C231.257 (6)
Cu1—O21.987 (4)O4—C121.261 (6)
Cu1—O102.164 (4)O5—C231.255 (6)
Cu1—Cu22.6183 (11)O2—C11.279 (7)
Cu2—O11.945 (4)O1—C11.249 (6)
Cu2—O31.963 (4)O8—C341.250 (7)
Cu2—O51.973 (4)O10—C391.211 (7)
Cu2—O71.988 (4)O9—C361.210 (8)
Cu2—O92.161 (4)
 

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