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

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ISSN: 2056-9890

Bis(ferrocene­carboxyl­ato-κO)bis­­(2-pyridyl­methanol-κ2N,O)cobalt(II)

aDepartment of Chemistry and Environmental Engineering, Anyang Institute of Technology, Henan 455000, People's Republic of China, and bCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: lidacheng@lcu.edu.cn

(Received 25 May 2010; accepted 1 June 2010; online 5 June 2010)

The title complex mol­ecule, [Fe2Co(C5H5)2(C6H4O2)2(C6H7NO)2], has a crystallographic imposed centre of symmetry. The CoII atom displays a distorted octa­hedral coordination geometry, provided by the O atoms of two monodentate ferrocene­carboxyl­ate anions and by the N and O atoms of two 2-pyridyl­methanol mol­ecule. The mol­ecular conformation is stabilized by intra­molecular C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Salazar-Mendoza et al. (2007[Salazar-Mendoza, D., Baudron, S. A., Hosseini, M. W., Kyritsakas, N. & De Cian, A. (2007). Dalton Trans. pp. 565-569.]); Meng et al. (2004[Meng, X. R., Hou, H. W., Li, G., Ye, B.-X., Ge, T.-Z., Fan, Y.-T., Zhu, Y. & Sakiyama, H. (2004). J. Organomet. Chem. 689, 1218-1229.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe2Co(C5H5)2(C6H4O2)2(C6H7NO)2]

  • Mr = 735.25

  • Monoclinic, P 21 /n

  • a = 12.5790 (12) Å

  • b = 7.7905 (9) Å

  • c = 15.2975 (15) Å

  • β = 90.141 (1)°

  • V = 1499.1 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.55 mm−1

  • T = 298 K

  • 0.40 × 0.37 × 0.28 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.576, Tmax = 0.670

  • 7475 measured reflections

  • 2642 independent reflections

  • 1651 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.125

  • S = 1.01

  • 2642 reflections

  • 205 parameters

  • H-atom parameters constrained

  • Δρmax = 0.50 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O6—H6⋯O4 0.82 1.70 2.516 (5) 176

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Ferrocene is an interesting redox centre for the construction of molecular architectures presenting magnetic, optical or electrochemical properties. As a contribution to this field, we report here the synthesis and structure of the title compound.

The title compound possesses crystallographic imposed centre of symmetry (Fig. 1). The cobalt(II) atom is six-coordinated in a distorted octahedral geometry by two O atoms of two monodentate ferrocenecarboxylare anions, two N and two O atoms of two pyridinemethanol molecules. Bond lengths and angles involving the metal centre are typical and comparable with those observed in related cobalt(II) complexes (Salazar-Mendoza et al., 2007; Meng et al., 2004). The conformation of the complex molecule is stabilized by intramolecular C—H···O hydrogen bonds (Table 1).

Related literature top

For related structures, see: Salazar-Mendoza et al. (2007); Meng et al. (2004).

Experimental top

A methanol solution of 2-pyridinemethanol (0.4 mmol, 3 ml) was added into a 10 ml methanol solution of cobalt(II) dichloride (0.2 mmol, 47.6 mg) at 293 K, then 10 ml of a methanol solution of ferrocenecarboxyl sodium (0.4 mmol, 100.8 mg) was added dropwise and the mixture stirred for 6 h. The resulting orange solution was allowed to stand at room temperature for about one week, whereupon red block crystals suitable for X-ray diffraction analysis were obtained.

Refinement top

All H atoms were placed in geometrically idealized positions and treated as riding on their parent atoms, with C—H = 0.93-0.98 Å, O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids. Atoms labelled wit suffix A are generated by the symmetry operation -x, -y, -z. Hydrogen atoms are omitted for clarity.
Bis(ferrocenecarboxylato-κO)bis(2-pyridylmethanol- κ2N,O)cobalt(II) top
Crystal data top
[Fe2Co(C5H5)2(C6H4O2)2(C6H7NO)2]F(000) = 754
Mr = 735.25Dx = 1.629 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1624 reflections
a = 12.5790 (12) Åθ = 2.9–26.5°
b = 7.7905 (9) ŵ = 1.55 mm1
c = 15.2975 (15) ÅT = 298 K
β = 90.141 (1)°Block, red
V = 1499.1 (3) Å30.40 × 0.37 × 0.28 mm
Z = 2
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2642 independent reflections
Radiation source: fine-focus sealed tube1651 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
phi and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.576, Tmax = 0.670k = 99
7475 measured reflectionsl = 1318
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0581P)2 + 0.7962P]
where P = (Fo2 + 2Fc2)/3
2642 reflections(Δ/σ)max < 0.001
205 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
[Fe2Co(C5H5)2(C6H4O2)2(C6H7NO)2]V = 1499.1 (3) Å3
Mr = 735.25Z = 2
Monoclinic, P21/nMo Kα radiation
a = 12.5790 (12) ŵ = 1.55 mm1
b = 7.7905 (9) ÅT = 298 K
c = 15.2975 (15) Å0.40 × 0.37 × 0.28 mm
β = 90.141 (1)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2642 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1651 reflections with I > 2σ(I)
Tmin = 0.576, Tmax = 0.670Rint = 0.045
7475 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 1.01Δρmax = 0.50 e Å3
2642 reflectionsΔρmin = 0.30 e Å3
205 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.00000.00000.00000.0433 (3)
Fe10.10119 (5)0.12834 (9)0.35046 (4)0.0398 (2)
N30.1164 (3)0.1549 (5)0.0649 (2)0.0447 (10)
O40.0149 (3)0.1926 (5)0.1934 (2)0.0590 (10)
C50.1235 (3)0.1298 (6)0.3445 (3)0.0413 (11)
H50.07290.21870.36250.050*
O60.1077 (3)0.1896 (4)0.0475 (2)0.0546 (9)
H60.07500.18870.09390.082*
O70.0864 (2)0.0167 (4)0.1132 (2)0.0506 (9)
C80.0616 (4)0.0908 (6)0.1841 (3)0.0442 (12)
C90.1318 (4)0.0544 (6)0.2604 (3)0.0400 (11)
C100.0427 (4)0.2295 (7)0.3206 (3)0.0529 (13)
H100.09130.18870.27490.063*
C110.2153 (3)0.0659 (7)0.2616 (3)0.0479 (13)
H110.23820.13710.21230.057*
C120.0401 (4)0.1730 (7)0.4084 (3)0.0567 (15)
H120.08670.08590.43420.068*
C130.2033 (4)0.0544 (7)0.3968 (3)0.0506 (13)
H130.21650.08000.45860.061*
C140.2592 (4)0.0674 (7)0.3461 (3)0.0549 (14)
H140.31810.13980.36630.066*
C150.0390 (5)0.2629 (8)0.4519 (3)0.0628 (15)
H150.05840.24940.51360.075*
C160.0875 (5)0.3736 (7)0.3926 (4)0.0669 (16)
H160.14660.45160.40560.080*
C170.0368 (4)0.3548 (7)0.3105 (4)0.0600 (15)
H170.05390.41720.25670.072*
C190.2825 (4)0.1471 (8)0.1388 (3)0.0591 (15)
H190.34200.08510.15610.071*
C180.2036 (4)0.0693 (7)0.0893 (3)0.0470 (12)
C220.1832 (5)0.4044 (8)0.1359 (3)0.0652 (16)
H220.17460.51950.15050.078*
C200.1064 (4)0.3190 (7)0.0874 (3)0.0562 (14)
H200.04600.37860.07010.067*
C230.2716 (5)0.3163 (8)0.1619 (4)0.0665 (16)
H230.32380.37040.19490.080*
C210.2095 (4)0.1131 (7)0.0597 (4)0.0672 (16)
H21A0.24860.11800.00500.081*
H21B0.24870.17920.10260.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0505 (6)0.0436 (6)0.0359 (5)0.0067 (5)0.0074 (4)0.0007 (4)
Fe10.0420 (4)0.0437 (4)0.0338 (4)0.0004 (3)0.0057 (3)0.0016 (3)
N30.050 (2)0.045 (3)0.039 (2)0.000 (2)0.0047 (18)0.0012 (19)
O40.060 (2)0.064 (2)0.053 (2)0.019 (2)0.0047 (17)0.0092 (18)
C50.042 (3)0.038 (3)0.043 (3)0.009 (2)0.008 (2)0.007 (2)
O60.057 (2)0.050 (2)0.056 (2)0.0128 (17)0.0021 (17)0.0002 (17)
O70.054 (2)0.062 (2)0.0353 (19)0.0065 (18)0.0044 (15)0.0044 (17)
C80.048 (3)0.041 (3)0.044 (3)0.008 (3)0.007 (2)0.006 (2)
C90.037 (3)0.044 (3)0.039 (3)0.004 (2)0.010 (2)0.001 (2)
C100.046 (3)0.056 (3)0.056 (3)0.012 (3)0.001 (2)0.004 (3)
C110.039 (3)0.064 (3)0.040 (3)0.003 (2)0.013 (2)0.003 (2)
C120.052 (3)0.063 (4)0.055 (4)0.017 (3)0.024 (3)0.006 (3)
C130.051 (3)0.066 (4)0.036 (3)0.014 (3)0.001 (2)0.008 (2)
C140.038 (3)0.078 (4)0.049 (3)0.002 (3)0.000 (2)0.003 (3)
C150.081 (4)0.067 (4)0.040 (3)0.023 (3)0.000 (3)0.015 (3)
C160.087 (4)0.044 (3)0.069 (4)0.003 (3)0.003 (3)0.009 (3)
C170.071 (4)0.050 (3)0.060 (4)0.013 (3)0.005 (3)0.011 (3)
C190.046 (3)0.073 (4)0.059 (4)0.008 (3)0.002 (3)0.013 (3)
C180.046 (3)0.048 (3)0.047 (3)0.001 (3)0.001 (2)0.007 (2)
C220.089 (5)0.053 (4)0.053 (4)0.018 (3)0.004 (3)0.001 (3)
C200.071 (4)0.051 (3)0.046 (3)0.002 (3)0.010 (3)0.005 (3)
C230.070 (4)0.075 (5)0.054 (4)0.029 (3)0.008 (3)0.010 (3)
C210.049 (3)0.068 (4)0.085 (4)0.013 (3)0.001 (3)0.004 (3)
Geometric parameters (Å, º) top
Co1—O7i2.046 (3)C10—C171.406 (7)
Co1—O72.046 (3)C10—C121.413 (7)
Co1—O6i2.133 (3)C10—H100.9800
Co1—O62.133 (3)C11—C141.405 (6)
Co1—N3i2.142 (4)C11—H110.9800
Co1—N32.142 (4)C12—C151.386 (7)
Fe1—C122.018 (5)C12—H120.9800
Fe1—C92.019 (5)C13—C141.415 (7)
Fe1—C162.024 (5)C13—H130.9800
Fe1—C102.026 (5)C14—H140.9800
Fe1—C152.031 (5)C15—C161.393 (7)
Fe1—C52.033 (5)C15—H150.9800
Fe1—C172.034 (5)C16—C171.414 (7)
Fe1—C112.038 (4)C16—H160.9800
Fe1—C132.043 (5)C17—H170.9800
Fe1—C142.045 (5)C19—C231.371 (8)
N3—C201.330 (6)C19—C181.388 (7)
N3—C181.338 (6)C19—H190.9300
O4—C81.255 (5)C18—C21i1.493 (7)
C5—C131.411 (6)C22—C231.367 (8)
C5—C91.418 (6)C22—C201.389 (7)
C5—H50.9800C22—H220.9300
O6—C211.424 (6)C20—H200.9300
O6—H60.8200C23—H230.9300
O7—C81.269 (5)C21—C18i1.493 (7)
C8—C91.488 (6)C21—H21A0.9700
C9—C111.408 (6)C21—H21B0.9700
O7i—Co1—O7180.0 (2)C11—C9—C5108.7 (4)
O7i—Co1—O6i90.26 (12)C11—C9—C8125.3 (4)
O7—Co1—O6i89.74 (12)C5—C9—C8126.0 (4)
O7i—Co1—O689.74 (12)C11—C9—Fe170.4 (3)
O7—Co1—O690.26 (12)C5—C9—Fe170.0 (3)
O6i—Co1—O6180.0 (2)C8—C9—Fe1123.7 (3)
O7i—Co1—N3i89.65 (14)C17—C10—C12107.8 (5)
O7—Co1—N3i90.35 (14)C17—C10—Fe170.1 (3)
O6i—Co1—N3i101.73 (14)C12—C10—Fe169.3 (3)
O6—Co1—N3i78.27 (14)C17—C10—H10126.1
O7i—Co1—N390.35 (14)C12—C10—H10126.1
O7—Co1—N389.65 (14)Fe1—C10—H10126.1
O6i—Co1—N378.27 (14)C14—C11—C9108.0 (4)
O6—Co1—N3101.73 (14)C14—C11—Fe170.2 (3)
N3i—Co1—N3180.0 (3)C9—C11—Fe169.0 (3)
C12—Fe1—C9126.2 (2)C14—C11—H11126.0
C12—Fe1—C1667.8 (2)C9—C11—H11126.0
C9—Fe1—C16154.1 (2)Fe1—C11—H11126.0
C12—Fe1—C1040.91 (19)C15—C12—C10108.3 (5)
C9—Fe1—C10107.01 (19)C15—C12—Fe170.5 (3)
C16—Fe1—C1068.1 (2)C10—C12—Fe169.8 (3)
C12—Fe1—C1540.1 (2)C15—C12—H12125.9
C9—Fe1—C15163.7 (2)C10—C12—H12125.9
C16—Fe1—C1540.2 (2)Fe1—C12—H12125.9
C10—Fe1—C1568.0 (2)C5—C13—C14108.8 (4)
C12—Fe1—C5108.2 (2)C5—C13—Fe169.4 (3)
C9—Fe1—C540.98 (17)C14—C13—Fe169.8 (3)
C16—Fe1—C5163.8 (2)C5—C13—H13125.6
C10—Fe1—C5119.9 (2)C14—C13—H13125.6
C15—Fe1—C5126.8 (2)Fe1—C13—H13125.6
C12—Fe1—C1768.4 (2)C11—C14—C13107.7 (4)
C9—Fe1—C17118.9 (2)C11—C14—Fe169.6 (3)
C16—Fe1—C1740.8 (2)C13—C14—Fe169.7 (3)
C10—Fe1—C1740.5 (2)C11—C14—H14126.2
C15—Fe1—C1768.2 (2)C13—C14—H14126.2
C5—Fe1—C17154.1 (2)Fe1—C14—H14126.2
C12—Fe1—C11163.0 (2)C12—C15—C16108.4 (5)
C9—Fe1—C1140.62 (18)C12—C15—Fe169.5 (3)
C16—Fe1—C11119.9 (2)C16—C15—Fe169.6 (3)
C10—Fe1—C11125.0 (2)C12—C15—H15125.8
C15—Fe1—C11154.9 (2)C16—C15—H15125.8
C5—Fe1—C1168.70 (19)Fe1—C15—H15125.8
C17—Fe1—C11106.7 (2)C15—C16—C17108.4 (5)
C12—Fe1—C13121.4 (2)C15—C16—Fe170.2 (3)
C9—Fe1—C1367.95 (19)C17—C16—Fe170.0 (3)
C16—Fe1—C13127.0 (2)C15—C16—H16125.8
C10—Fe1—C13155.5 (2)C17—C16—H16125.8
C15—Fe1—C13109.7 (2)Fe1—C16—H16125.8
C5—Fe1—C1340.49 (18)C10—C17—C16107.1 (5)
C17—Fe1—C13163.3 (2)C10—C17—Fe169.4 (3)
C11—Fe1—C1367.80 (19)C16—C17—Fe169.2 (3)
C12—Fe1—C14155.7 (2)C10—C17—H17126.5
C9—Fe1—C1468.1 (2)C16—C17—H17126.5
C16—Fe1—C14108.2 (2)Fe1—C17—H17126.5
C10—Fe1—C14162.0 (2)C23—C19—C18119.3 (5)
C15—Fe1—C14121.4 (2)C23—C19—H19120.4
C5—Fe1—C1468.6 (2)C18—C19—H19120.4
C17—Fe1—C14125.3 (2)N3—C18—C19121.5 (5)
C11—Fe1—C1440.24 (18)N3—C18—C21i115.4 (5)
C13—Fe1—C1440.5 (2)C19—C18—C21i123.1 (5)
C20—N3—C18118.9 (4)C23—C22—C20118.8 (6)
C20—N3—Co1126.7 (3)C23—C22—H22120.6
C18—N3—Co1114.2 (3)C20—C22—H22120.6
C13—C5—C9106.7 (4)N3—C20—C22122.3 (5)
C13—C5—Fe170.2 (3)N3—C20—H20118.9
C9—C5—Fe169.0 (3)C22—C20—H20118.9
C13—C5—H5126.6C22—C23—C19119.2 (5)
C9—C5—H5126.6C22—C23—H23120.4
Fe1—C5—H5126.6C19—C23—H23120.4
C21—O6—Co1109.1 (3)O6—C21—C18i113.2 (4)
C21—O6—H6109.5O6—C21—H21A108.9
Co1—O6—H688.3C18i—C21—H21A108.9
C8—O7—Co1128.4 (3)O6—C21—H21B108.9
O4—C8—O7125.0 (4)C18i—C21—H21B108.9
O4—C8—C9119.0 (4)H21A—C21—H21B107.8
O7—C8—C9116.0 (4)
O7i—Co1—N3—C2074.7 (4)C15—Fe1—C12—C10119.0 (5)
O7—Co1—N3—C20105.3 (4)C5—Fe1—C12—C10115.0 (3)
O6i—Co1—N3—C20164.9 (4)C17—Fe1—C12—C1037.7 (3)
O6—Co1—N3—C2015.1 (4)C11—Fe1—C12—C1038.5 (9)
O7i—Co1—N3—C18100.3 (3)C13—Fe1—C12—C10157.4 (3)
O7—Co1—N3—C1879.7 (3)C14—Fe1—C12—C10167.0 (5)
O6i—Co1—N3—C1810.1 (3)C9—C5—C13—C140.7 (5)
O6—Co1—N3—C18169.9 (3)Fe1—C5—C13—C1458.8 (4)
C12—Fe1—C5—C13117.4 (3)C9—C5—C13—Fe159.5 (3)
C9—Fe1—C5—C13117.8 (4)C12—Fe1—C13—C581.2 (3)
C16—Fe1—C5—C1344.6 (9)C9—Fe1—C13—C538.7 (3)
C10—Fe1—C5—C13160.6 (3)C16—Fe1—C13—C5165.8 (3)
C15—Fe1—C5—C1376.9 (4)C10—Fe1—C13—C543.9 (6)
C17—Fe1—C5—C13164.7 (4)C15—Fe1—C13—C5124.0 (3)
C11—Fe1—C5—C1380.3 (3)C17—Fe1—C13—C5156.4 (6)
C14—Fe1—C5—C1337.0 (3)C11—Fe1—C13—C582.7 (3)
C12—Fe1—C5—C9124.8 (3)C14—Fe1—C13—C5120.4 (4)
C16—Fe1—C5—C9162.5 (7)C12—Fe1—C13—C14158.4 (3)
C10—Fe1—C5—C981.6 (3)C9—Fe1—C13—C1481.7 (3)
C15—Fe1—C5—C9165.3 (3)C16—Fe1—C13—C1473.8 (4)
C17—Fe1—C5—C946.9 (6)C10—Fe1—C13—C14164.3 (4)
C11—Fe1—C5—C937.5 (3)C15—Fe1—C13—C14115.6 (3)
C13—Fe1—C5—C9117.8 (4)C5—Fe1—C13—C14120.4 (4)
C14—Fe1—C5—C980.8 (3)C17—Fe1—C13—C1436.0 (8)
O7i—Co1—O6—C2165.6 (3)C11—Fe1—C13—C1437.7 (3)
O7—Co1—O6—C21114.4 (3)C9—C11—C14—C130.8 (5)
N3—Co1—O6—C21155.9 (3)Fe1—C11—C14—C1359.5 (3)
O6i—Co1—O7—C8168.1 (4)C9—C11—C14—Fe158.8 (3)
O6—Co1—O7—C811.9 (4)C5—C13—C14—C110.9 (6)
N3i—Co1—O7—C866.4 (4)Fe1—C13—C14—C1159.5 (3)
N3—Co1—O7—C8113.6 (4)C5—C13—C14—Fe158.5 (3)
Co1—O7—C8—O412.2 (7)C12—Fe1—C14—C11168.8 (5)
Co1—O7—C8—C9169.2 (3)C9—Fe1—C14—C1137.7 (3)
C13—C5—C9—C110.3 (5)C16—Fe1—C14—C11115.0 (3)
Fe1—C5—C9—C1160.0 (3)C10—Fe1—C14—C1139.8 (8)
C13—C5—C9—C8178.1 (4)C15—Fe1—C14—C11157.2 (3)
Fe1—C5—C9—C8117.8 (5)C5—Fe1—C14—C1181.9 (3)
C13—C5—C9—Fe160.3 (3)C17—Fe1—C14—C1173.0 (4)
O4—C8—C9—C11175.0 (4)C13—Fe1—C14—C11118.9 (4)
O7—C8—C9—C116.4 (7)C12—Fe1—C14—C1349.9 (7)
O4—C8—C9—C52.5 (7)C9—Fe1—C14—C1381.2 (3)
O7—C8—C9—C5176.1 (4)C16—Fe1—C14—C13126.1 (3)
O4—C8—C9—Fe186.2 (5)C10—Fe1—C14—C13158.7 (6)
O7—C8—C9—Fe195.2 (5)C15—Fe1—C14—C1383.9 (4)
C12—Fe1—C9—C11165.3 (3)C5—Fe1—C14—C1337.0 (3)
C16—Fe1—C9—C1149.5 (6)C17—Fe1—C14—C13168.1 (3)
C10—Fe1—C9—C11124.3 (3)C11—Fe1—C14—C13118.9 (4)
C15—Fe1—C9—C11166.1 (7)C10—C12—C15—C160.9 (6)
C5—Fe1—C9—C11119.4 (4)Fe1—C12—C15—C1659.0 (4)
C17—Fe1—C9—C1182.0 (3)C10—C12—C15—Fe159.8 (3)
C13—Fe1—C9—C1181.1 (3)C9—Fe1—C15—C1237.0 (9)
C14—Fe1—C9—C1137.3 (3)C16—Fe1—C15—C12119.9 (5)
C12—Fe1—C9—C575.3 (3)C10—Fe1—C15—C1238.1 (3)
C16—Fe1—C9—C5168.9 (5)C5—Fe1—C15—C1273.5 (4)
C10—Fe1—C9—C5116.2 (3)C17—Fe1—C15—C1282.0 (3)
C15—Fe1—C9—C546.6 (8)C11—Fe1—C15—C12164.7 (4)
C17—Fe1—C9—C5158.6 (3)C13—Fe1—C15—C12115.7 (3)
C11—Fe1—C9—C5119.4 (4)C14—Fe1—C15—C12159.0 (3)
C13—Fe1—C9—C538.3 (3)C12—Fe1—C15—C16119.9 (5)
C14—Fe1—C9—C582.1 (3)C9—Fe1—C15—C16156.8 (7)
C12—Fe1—C9—C845.3 (5)C10—Fe1—C15—C1681.7 (4)
C16—Fe1—C9—C870.5 (7)C5—Fe1—C15—C16166.6 (3)
C10—Fe1—C9—C84.3 (4)C17—Fe1—C15—C1637.9 (3)
C15—Fe1—C9—C873.9 (9)C11—Fe1—C15—C1644.9 (6)
C5—Fe1—C9—C8120.6 (5)C13—Fe1—C15—C16124.4 (4)
C17—Fe1—C9—C838.0 (5)C14—Fe1—C15—C1681.1 (4)
C11—Fe1—C9—C8120.0 (5)C12—C15—C16—C170.9 (6)
C13—Fe1—C9—C8158.9 (4)Fe1—C15—C16—C1759.7 (4)
C14—Fe1—C9—C8157.3 (5)C12—C15—C16—Fe158.9 (4)
C12—Fe1—C10—C17119.0 (5)C12—Fe1—C16—C1537.1 (3)
C9—Fe1—C10—C17114.8 (3)C9—Fe1—C16—C15165.4 (4)
C16—Fe1—C10—C1738.2 (3)C10—Fe1—C16—C1581.4 (4)
C15—Fe1—C10—C1781.7 (4)C5—Fe1—C16—C1541.5 (9)
C5—Fe1—C10—C17157.5 (3)C17—Fe1—C16—C15119.3 (5)
C11—Fe1—C10—C1773.8 (4)C11—Fe1—C16—C15159.8 (3)
C13—Fe1—C10—C17171.2 (4)C13—Fe1—C16—C1576.3 (4)
C14—Fe1—C10—C1743.5 (8)C14—Fe1—C16—C15117.4 (4)
C9—Fe1—C10—C12126.2 (3)C12—Fe1—C16—C1782.2 (4)
C16—Fe1—C10—C1280.9 (4)C9—Fe1—C16—C1746.1 (6)
C15—Fe1—C10—C1237.4 (3)C10—Fe1—C16—C1737.9 (3)
C5—Fe1—C10—C1283.4 (4)C15—Fe1—C16—C17119.3 (5)
C17—Fe1—C10—C12119.0 (5)C5—Fe1—C16—C17160.8 (7)
C11—Fe1—C10—C12167.2 (3)C11—Fe1—C16—C1780.9 (4)
C13—Fe1—C10—C1252.1 (6)C13—Fe1—C16—C17164.4 (3)
C14—Fe1—C10—C12162.5 (7)C14—Fe1—C16—C17123.3 (3)
C5—C9—C11—C140.3 (5)C12—C10—C17—C160.0 (6)
C8—C9—C11—C14177.6 (4)Fe1—C10—C17—C1659.2 (4)
Fe1—C9—C11—C1459.5 (3)C12—C10—C17—Fe159.2 (3)
C5—C9—C11—Fe159.8 (3)C15—C16—C17—C100.5 (6)
C8—C9—C11—Fe1118.1 (4)Fe1—C16—C17—C1059.3 (4)
C12—Fe1—C11—C14164.1 (7)C15—C16—C17—Fe159.8 (4)
C9—Fe1—C11—C14119.4 (4)C12—Fe1—C17—C1038.0 (3)
C16—Fe1—C11—C1483.1 (4)C9—Fe1—C17—C1082.5 (3)
C10—Fe1—C11—C14166.1 (3)C16—Fe1—C17—C10118.6 (5)
C15—Fe1—C11—C1451.4 (6)C15—Fe1—C17—C1081.3 (3)
C5—Fe1—C11—C1481.6 (3)C5—Fe1—C17—C1049.3 (6)
C17—Fe1—C11—C14125.4 (3)C11—Fe1—C17—C10124.8 (3)
C13—Fe1—C11—C1437.9 (3)C13—Fe1—C17—C10167.2 (6)
C12—Fe1—C11—C944.7 (8)C14—Fe1—C17—C10164.9 (3)
C16—Fe1—C11—C9157.5 (3)C12—Fe1—C17—C1680.6 (4)
C10—Fe1—C11—C974.5 (4)C9—Fe1—C17—C16158.9 (3)
C15—Fe1—C11—C9170.8 (5)C10—Fe1—C17—C16118.6 (5)
C5—Fe1—C11—C937.8 (3)C15—Fe1—C17—C1637.3 (3)
C17—Fe1—C11—C9115.2 (3)C5—Fe1—C17—C16167.9 (4)
C13—Fe1—C11—C981.5 (3)C11—Fe1—C17—C16116.6 (4)
C14—Fe1—C11—C9119.4 (4)C13—Fe1—C17—C1648.6 (9)
C17—C10—C12—C150.5 (6)C14—Fe1—C17—C1676.5 (4)
Fe1—C10—C12—C1560.2 (4)C20—N3—C18—C191.2 (7)
C17—C10—C12—Fe159.7 (3)Co1—N3—C18—C19174.3 (4)
C9—Fe1—C12—C15167.9 (3)C20—N3—C18—C21i178.7 (4)
C16—Fe1—C12—C1537.2 (3)Co1—N3—C18—C21i5.8 (5)
C10—Fe1—C12—C15119.0 (5)C23—C19—C18—N31.1 (8)
C5—Fe1—C12—C15126.0 (3)C23—C19—C18—C21i178.8 (5)
C17—Fe1—C12—C1581.3 (4)C18—N3—C20—C220.4 (7)
C11—Fe1—C12—C15157.5 (7)Co1—N3—C20—C22174.5 (4)
C13—Fe1—C12—C1583.6 (4)C23—C22—C20—N30.5 (8)
C14—Fe1—C12—C1548.0 (7)C20—C22—C23—C190.6 (8)
C9—Fe1—C12—C1073.1 (4)C18—C19—C23—C220.2 (8)
C16—Fe1—C12—C1081.8 (3)Co1—O6—C21—C18i34.6 (5)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O40.821.702.516 (5)176

Experimental details

Crystal data
Chemical formula[Fe2Co(C5H5)2(C6H4O2)2(C6H7NO)2]
Mr735.25
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)12.5790 (12), 7.7905 (9), 15.2975 (15)
β (°) 90.141 (1)
V3)1499.1 (3)
Z2
Radiation typeMo Kα
µ (mm1)1.55
Crystal size (mm)0.40 × 0.37 × 0.28
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.576, 0.670
No. of measured, independent and
observed [I > 2σ(I)] reflections
7475, 2642, 1651
Rint0.045
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.125, 1.01
No. of reflections2642
No. of parameters205
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.50, 0.30

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O40.821.702.516 (5)176
 

Acknowledgements

This work was supported by the Natural Science Foundation of China (grant No. 20971063)

References

First citationMeng, X. R., Hou, H. W., Li, G., Ye, B.-X., Ge, T.-Z., Fan, Y.-T., Zhu, Y. & Sakiyama, H. (2004). J. Organomet. Chem. 689, 1218–1229.  Web of Science CSD CrossRef CAS Google Scholar
First citationSalazar-Mendoza, D., Baudron, S. A., Hosseini, M. W., Kyritsakas, N. & De Cian, A. (2007). Dalton Trans. pp. 565–569.  Web of Science CSD CrossRef Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar

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