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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Jun 18;67(Pt 7):m947. doi: 10.1107/S1600536811019398

4-Methyl-2,7-dioxo-3,6-dioxa-1(1,1′)-ferrocenacyclo­hepta­phane

Xin Leng a, Bingqin Yang a,*, Pengfei Zhang a, Xianwen Fang a
PMCID: PMC3151989  PMID: 21836929

Abstract

In the title compound, [Fe(C15H14O4)], the two cyclo­penta­dienyl (Cp) rings are nearly parallel, making a dihedral angle of 2.6 (1)°. The distance between the centroids of the Cp rings is 3.309 (8) Å. The relative orientation of the two Cp rings is characterized by a torsion angle of −43.99 (6)° defined by the two centroids and the two substituted C atoms.

Related literature

For the definition of ferrocenophanes, see: Otón et al. (2005 ▶). For the properties of ferrocenophanes, see: Cayuela et al. (2004 ▶); Kulbaba & Manners (2001 ▶); Lu et al. (2006 ▶); Mizuta et al. (2003 ▶); Nguyen et al. (1999 ▶); Otón et al. (2006a ▶,b ▶); Suzaki et al. (2006 ▶). For the synthesis and related structures, see: Gao et al. (2009 ▶); Leng et al. (2010 ▶). For studies of host structures for the investigation of mol­ecular recognition, see: Bond et al. (2009 ▶); Choi et al. (2006 ▶); Nakagaki et al. (2010 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).graphic file with name e-67-0m947-scheme1.jpg

Experimental

Crystal data

  • [Fe(C15H14O4)]

  • M r = 314.11

  • Monoclinic, Inline graphic

  • a = 7.1665 (14) Å

  • b = 20.131 (4) Å

  • c = 9.2464 (19) Å

  • β = 103.193 (2)°

  • V = 1298.7 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.17 mm−1

  • T = 296 K

  • 0.29 × 0.21 × 0.12 mm

Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.727, T max = 0.870

  • 3177 measured reflections

  • 1971 independent reflections

  • 1721 reflections with I > 2σ(I)

  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036

  • wR(F 2) = 0.087

  • S = 0.96

  • 1971 reflections

  • 182 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.41 e Å−3

  • Absolute structure: Flack (1983 ▶), 812 Friedel pairs

  • Flack parameter: 0.03 (3)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811019398/hy2432sup1.cif

e-67-0m947-sup1.cif (25.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019398/hy2432Isup2.hkl

e-67-0m947-Isup2.hkl (97KB, hkl)

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

Acknowledgments

Financial support from the National Natural Science Foundation of China (grant No. 20972125) is gratefully acknowledged.

supplementary crystallographic information

Comment

Ferrocenophanes, in which the two cyclopentadienyl (Cp) rings are joined by an atomic or molecular bridge (Otón et al., 2005), are found to be aromatic, highly stable and generally non-toxic, and have rversible redox characteristics (Mizuta et al., 2003). In particular, ferrocenophanes are useful precursors to poly-ferrocenyl materials (Kulbaba & Manners, 2001; Nguyen et al., 1999) and act as potentical receptor towards cation or anion recognition (Cayuela et al., 2004; Lu et al., 2006; Otón et al., 2006a,b; Suzaki et al., 2006). As a part of our ongoing investigation of ferrocenphanes, the title compound has been prepared and we report its crystal structure. Despite of the fact that structurally characterized ferrocenophanes are well presented in the Cambridge Structural Database (Allen, 2002; Version 5.27, release February 2009), there are only a few of structurally characterized compounds (Gao et al., 2009; Leng et al., 2010). Meanwhile, the study of the host structures is very helpful for the investigation of molecular recognition (Bond et al., 2009; Choi et al., 2006; Nakagaki et al., 2010). From this viewpoint, X-ray single-crystal study of the title compound presents a certain descriptive interest.

The structure of the title compound is shown in Fig. 1. The two cyclopentadienyl (Cp) rings are nearly parallel, making a dihedral angle of 2.6 (1)°. The distance between the centroids of the Cp rings is 3.309 (8) Å. The angle formed between the two centroids and Fe1 is 179.4 (6)°. The relative orientation of the two Cp rings is characterized by the C6—Cg1—Cg2—C9 torsion angle of -43.99 (6)° (Cg1 and Cg2 are the centroids of C1–C5 ring and C10–C14 ring, respectively). The Fe—C distances range from 2.027 (5) to 2.073 (5) Å. The exocyclic C5—C6 and C9—C10 bond lengths are 1.456 (7) and 1.461 (9) Å.

Experimental

The title compound was synthesized according to the published procedure (Gao et al., 2009). Melting point, IR and NMR spectra confirmed identity and purity of the prepared compound.

Yellow crystals of the title compoud suitable for X-ray diffraction analysis were obtained by slow concentration of a dichloromethane solution at room temperature.

Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.96–0.98 Å and Uiso(H) = 1.2(1.5 for methyl)Ueq(C).

Figures

Fig. 1.

Fig. 1.

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Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

[Fe(C15H14O4)] Z = 4
Mr = 314.11 F(000) = 648
Monoclinic, Cc Dx = 1.606 Mg m−3
Hall symbol: C -2yc Melting point: 405(6) K
a = 7.1665 (14) Å Mo Kα radiation, λ = 0.71073 Å
b = 20.131 (4) Å µ = 1.17 mm−1
c = 9.2464 (19) Å T = 296 K
β = 103.193 (2)° Block, yellow
V = 1298.7 (4) Å3 0.29 × 0.21 × 0.12 mm
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Data collection

Bruker APEXII CCD diffractometer 1971 independent reflections
Radiation source: fine-focus sealed tube 1721 reflections with I > 2σ(I)
graphite Rint = 0.024
φ and ω scans θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −8→8
Tmin = 0.727, Tmax = 0.870 k = −24→21
3177 measured reflections l = −8→11
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Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036 H-atom parameters constrained
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0495P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96 (Δ/σ)max < 0.001
1971 reflections Δρmax = 0.30 e Å−3
182 parameters Δρmin = −0.41 e Å−3
2 restraints Absolute structure: Flack (1983), 812 Friedel pairs
Primary atom site location: structure-invariant direct methods Flack parameter: 0.03 (3)
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Fe1 0.13087 (9) 0.36266 (2) 0.68667 (8) 0.04130 (18)
O1 0.5456 (6) 0.47208 (16) 0.8549 (4) 0.0654 (10)
O2 0.5650 (4) 0.37627 (13) 0.9814 (3) 0.0426 (7)
O3 0.2545 (5) 0.40433 (17) 1.0838 (4) 0.0562 (8)
O4 0.1738 (6) 0.2959 (2) 1.0643 (5) 0.0820 (12)
C1 0.3338 (7) 0.3998 (3) 0.5860 (6) 0.0522 (13)
H1 0.3431 0.4459 0.5541 0.063*
C2 0.2339 (10) 0.3478 (4) 0.4983 (7) 0.0609 (17)
H2 0.1593 0.3520 0.3957 0.073*
C3 0.2568 (7) 0.2893 (3) 0.5836 (6) 0.0523 (12)
H3 0.2011 0.2458 0.5510 0.063*
C4 0.3700 (7) 0.3047 (2) 0.7267 (5) 0.0480 (11)
H4 0.4074 0.2732 0.8091 0.058*
C5 0.4210 (9) 0.3728 (3) 0.7309 (7) 0.0404 (13)
C6 0.5160 (6) 0.4129 (2) 0.8576 (5) 0.0408 (10)
C7 0.5946 (7) 0.4116 (2) 1.1239 (5) 0.0465 (11)
H7 0.5878 0.4596 1.1062 0.056*
C8 0.4317 (8) 0.3902 (3) 1.1916 (7) 0.0585 (15)
H8A 0.4410 0.3431 1.2142 0.070*
H8B 0.4356 0.4144 1.2829 0.070*
C9 0.1550 (7) 0.3512 (3) 1.0141 (6) 0.0547 (13)
C10 0.0267 (9) 0.3693 (3) 0.8729 (7) 0.0475 (15)
C11 −0.0857 (7) 0.3239 (3) 0.7722 (6) 0.0592 (14)
H11 −0.1055 0.2768 0.7911 0.071*
C12 −0.1631 (11) 0.3581 (4) 0.6428 (9) 0.069 (2)
H12 −0.2445 0.3383 0.5536 0.083*
C13 −0.1028 (7) 0.4244 (3) 0.6556 (7) 0.0655 (15)
H13 −0.1372 0.4589 0.5793 0.079*
C14 0.0168 (8) 0.4324 (3) 0.7992 (6) 0.0582 (13)
H14 0.0788 0.4737 0.8414 0.070*
C15 0.7879 (9) 0.3938 (3) 1.2184 (7) 0.0636 (16)
H15A 0.7961 0.3465 1.2321 0.095*
H15B 0.8050 0.4152 1.3133 0.095*
H15C 0.8861 0.4083 1.1703 0.095*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Fe1 0.0369 (3) 0.0492 (3) 0.0394 (3) 0.0023 (3) 0.0120 (2) 0.0010 (4)
O1 0.093 (3) 0.053 (2) 0.048 (2) −0.0180 (17) 0.012 (2) 0.0077 (16)
O2 0.0533 (18) 0.0433 (16) 0.0294 (16) 0.0043 (13) 0.0056 (14) −0.0023 (13)
O3 0.0564 (19) 0.066 (2) 0.049 (2) −0.0042 (16) 0.0175 (17) −0.0113 (16)
O4 0.095 (3) 0.086 (3) 0.059 (3) −0.036 (2) 0.004 (2) 0.014 (2)
C1 0.046 (3) 0.071 (4) 0.043 (3) −0.004 (3) 0.016 (2) 0.012 (3)
C2 0.058 (4) 0.090 (4) 0.038 (4) −0.010 (3) 0.016 (3) −0.011 (3)
C3 0.050 (3) 0.060 (3) 0.046 (3) 0.008 (2) 0.010 (2) −0.008 (2)
C4 0.052 (3) 0.051 (3) 0.042 (3) 0.005 (2) 0.012 (2) −0.006 (2)
C5 0.037 (3) 0.052 (3) 0.034 (3) −0.002 (2) 0.011 (3) −0.002 (2)
C6 0.039 (2) 0.049 (3) 0.036 (3) 0.0002 (19) 0.012 (2) 0.004 (2)
C7 0.062 (3) 0.044 (2) 0.032 (2) −0.001 (2) 0.008 (2) −0.0051 (18)
C8 0.067 (4) 0.072 (3) 0.036 (3) −0.016 (3) 0.013 (3) −0.007 (2)
C9 0.052 (3) 0.071 (4) 0.050 (3) −0.015 (2) 0.028 (2) −0.002 (2)
C10 0.031 (3) 0.074 (4) 0.041 (4) 0.000 (2) 0.014 (3) −0.004 (2)
C11 0.045 (3) 0.079 (4) 0.057 (4) −0.014 (3) 0.019 (3) −0.016 (3)
C12 0.031 (3) 0.121 (7) 0.055 (5) 0.003 (3) 0.010 (3) −0.015 (4)
C13 0.051 (3) 0.084 (4) 0.062 (4) 0.019 (3) 0.013 (3) −0.002 (3)
C14 0.050 (3) 0.068 (3) 0.060 (4) 0.014 (2) 0.018 (3) −0.009 (3)
C15 0.065 (3) 0.071 (4) 0.046 (3) 0.004 (3) −0.005 (3) −0.013 (3)
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Geometric parameters (Å, °)

Fe1—C14 2.027 (5) C3—H3 0.9800
Fe1—C5 2.036 (6) C4—C5 1.418 (7)
Fe1—C4 2.037 (5) C4—H4 0.9800
Fe1—C10 2.032 (6) C5—C6 1.456 (7)
Fe1—C1 2.040 (5) C7—C15 1.503 (7)
Fe1—C12 2.054 (8) C7—C8 1.508 (7)
Fe1—C13 2.053 (5) C7—H7 0.9800
Fe1—C11 2.051 (5) C8—H8A 0.9700
Fe1—C2 2.063 (6) C8—H8B 0.9700
Fe1—C3 2.073 (5) C9—C10 1.461 (9)
O1—C6 1.212 (5) C10—C11 1.418 (7)
O2—C6 1.339 (5) C10—C14 1.437 (7)
O2—C7 1.469 (5) C11—C12 1.382 (10)
O3—C9 1.362 (6) C11—H11 0.9800
O3—C8 1.452 (7) C12—C13 1.401 (8)
O4—C9 1.202 (6) C12—H12 0.9800
C1—C2 1.415 (9) C13—C14 1.416 (8)
C1—C5 1.449 (8) C13—H13 0.9800
C1—H1 0.9800 C14—H14 0.9800
C2—C3 1.406 (9) C15—H15A 0.9600
C2—H2 0.9800 C15—H15B 0.9600
C3—C4 1.419 (6) C15—H15C 0.9600
C14—Fe1—C5 109.9 (2) C3—C4—Fe1 71.2 (3)
C14—Fe1—C4 136.5 (2) C5—C4—Fe1 69.6 (3)
C5—Fe1—C4 40.76 (18) C3—C4—H4 125.5
C14—Fe1—C10 41.5 (2) C5—C4—H4 125.5
C5—Fe1—C10 112.3 (2) Fe1—C4—H4 125.5
C4—Fe1—C10 109.9 (2) C4—C5—C6 128.9 (5)
C14—Fe1—C1 113.2 (3) C4—C5—C1 106.4 (5)
C5—Fe1—C1 41.7 (2) C6—C5—C1 124.1 (4)
C4—Fe1—C1 68.6 (2) C4—C5—Fe1 69.7 (3)
C10—Fe1—C1 143.3 (2) C6—C5—Fe1 119.1 (4)
C14—Fe1—C12 67.5 (3) C1—C5—Fe1 69.3 (3)
C5—Fe1—C12 176.8 (2) O1—C6—O2 123.1 (4)
C4—Fe1—C12 142.4 (3) O1—C6—C5 125.4 (4)
C10—Fe1—C12 67.1 (3) O2—C6—C5 111.5 (4)
C1—Fe1—C12 137.1 (3) O2—C7—C15 109.4 (4)
C14—Fe1—C13 40.6 (2) O2—C7—C8 105.5 (4)
C5—Fe1—C13 136.9 (2) C15—C7—C8 112.9 (5)
C4—Fe1—C13 176.9 (2) O2—C7—H7 109.7
C10—Fe1—C13 68.5 (2) C15—C7—H7 109.7
C1—Fe1—C13 111.0 (2) C8—C7—H7 109.7
C12—Fe1—C13 39.9 (2) O3—C8—C7 107.3 (5)
C14—Fe1—C11 68.7 (2) O3—C8—H8A 110.2
C5—Fe1—C11 142.1 (2) C7—C8—H8A 110.2
C4—Fe1—C11 113.0 (2) O3—C8—H8B 110.2
C10—Fe1—C11 40.6 (2) C7—C8—H8B 110.2
C1—Fe1—C11 175.7 (2) H8A—C8—H8B 108.5
C12—Fe1—C11 39.3 (3) O4—C9—O3 122.9 (5)
C13—Fe1—C11 67.6 (3) O4—C9—C10 124.6 (5)
C14—Fe1—C2 142.9 (3) O3—C9—C10 112.5 (5)
C5—Fe1—C2 68.8 (3) C11—C10—C14 107.4 (5)
C4—Fe1—C2 67.8 (3) C11—C10—C9 125.1 (5)
C10—Fe1—C2 175.4 (3) C14—C10—C9 126.6 (5)
C1—Fe1—C2 40.3 (2) C11—C10—Fe1 70.4 (3)
C12—Fe1—C2 112.0 (3) C14—C10—Fe1 69.1 (3)
C13—Fe1—C2 114.0 (3) C9—C10—Fe1 117.6 (4)
C11—Fe1—C2 135.9 (3) C12—C11—C10 107.6 (6)
C14—Fe1—C3 176.6 (2) C12—C11—Fe1 70.5 (4)
C5—Fe1—C3 68.4 (2) C10—C11—Fe1 69.0 (3)
C4—Fe1—C3 40.38 (18) C12—C11—H11 126.2
C10—Fe1—C3 136.0 (2) C10—C11—H11 126.2
C1—Fe1—C3 67.7 (2) Fe1—C11—H11 126.2
C12—Fe1—C3 114.3 (2) C11—C12—C13 110.3 (7)
C13—Fe1—C3 142.6 (2) C11—C12—Fe1 70.2 (4)
C11—Fe1—C3 110.7 (2) C13—C12—Fe1 70.0 (4)
C2—Fe1—C3 39.7 (2) C11—C12—H12 124.8
C6—O2—C7 117.2 (3) C13—C12—H12 124.8
C9—O3—C8 116.9 (4) Fe1—C12—H12 124.8
C2—C1—C5 107.9 (5) C12—C13—C14 107.2 (6)
C2—C1—Fe1 70.7 (3) C12—C13—Fe1 70.1 (4)
C5—C1—Fe1 69.0 (3) C14—C13—Fe1 68.7 (3)
C2—C1—H1 126.0 C12—C13—H13 126.4
C5—C1—H1 126.0 C14—C13—H13 126.4
Fe1—C1—H1 126.0 Fe1—C13—H13 126.4
C3—C2—C1 108.6 (6) C13—C14—C10 107.4 (5)
C3—C2—Fe1 70.5 (3) C13—C14—Fe1 70.7 (3)
C1—C2—Fe1 68.9 (3) C10—C14—Fe1 69.4 (3)
C3—C2—H2 125.7 C13—C14—H14 126.3
C1—C2—H2 125.7 C10—C14—H14 126.3
Fe1—C2—H2 125.7 Fe1—C14—H14 126.3
C2—C3—C4 108.0 (5) C7—C15—H15A 109.5
C2—C3—Fe1 69.8 (3) C7—C15—H15B 109.5
C4—C3—Fe1 68.4 (3) H15A—C15—H15B 109.5
C2—C3—H3 126.0 C7—C15—H15C 109.5
C4—C3—H3 126.0 H15A—C15—H15C 109.5
Fe1—C3—H3 126.0 H15B—C15—H15C 109.5
C3—C4—C5 109.0 (5)
C14—Fe1—C1—C2 −146.8 (4) O2—C7—C8—O3 −55.2 (5)
C5—Fe1—C1—C2 118.9 (5) C15—C7—C8—O3 −174.6 (4)
C4—Fe1—C1—C2 80.4 (4) C8—O3—C9—O4 21.6 (7)
C10—Fe1—C1—C2 175.4 (5) C8—O3—C9—C10 −157.7 (5)
C12—Fe1—C1—C2 −65.5 (6) O4—C9—C10—C11 −3.3 (9)
C13—Fe1—C1—C2 −102.9 (4) O3—C9—C10—C11 176.0 (5)
C3—Fe1—C1—C2 36.8 (4) O4—C9—C10—C14 −171.4 (6)
C14—Fe1—C1—C5 94.3 (3) O3—C9—C10—C14 7.9 (8)
C4—Fe1—C1—C5 −38.5 (3) O4—C9—C10—Fe1 −87.9 (6)
C10—Fe1—C1—C5 56.4 (5) O3—C9—C10—Fe1 91.5 (5)
C12—Fe1—C1—C5 175.6 (4) C14—Fe1—C10—C11 118.4 (5)
C13—Fe1—C1—C5 138.2 (3) C5—Fe1—C10—C11 −146.3 (3)
C2—Fe1—C1—C5 −118.9 (5) C4—Fe1—C10—C11 −102.5 (3)
C3—Fe1—C1—C5 −82.1 (3) C1—Fe1—C10—C11 176.9 (4)
C5—C1—C2—C3 −0.3 (7) C12—Fe1—C10—C11 37.1 (4)
Fe1—C1—C2—C3 −59.5 (4) C13—Fe1—C10—C11 80.3 (4)
C5—C1—C2—Fe1 59.2 (4) C3—Fe1—C10—C11 −64.8 (5)
C14—Fe1—C2—C3 176.6 (4) C5—Fe1—C10—C14 95.2 (4)
C5—Fe1—C2—C3 81.3 (4) C4—Fe1—C10—C14 139.0 (3)
C4—Fe1—C2—C3 37.3 (3) C1—Fe1—C10—C14 58.5 (5)
C1—Fe1—C2—C3 119.9 (5) C12—Fe1—C10—C14 −81.4 (4)
C12—Fe1—C2—C3 −102.0 (4) C13—Fe1—C10—C14 −38.1 (3)
C13—Fe1—C2—C3 −145.5 (3) C11—Fe1—C10—C14 −118.4 (5)
C11—Fe1—C2—C3 −63.4 (5) C3—Fe1—C10—C14 176.7 (3)
C14—Fe1—C2—C1 56.7 (6) C14—Fe1—C10—C9 −121.4 (6)
C5—Fe1—C2—C1 −38.6 (3) C5—Fe1—C10—C9 −26.2 (5)
C4—Fe1—C2—C1 −82.6 (4) C4—Fe1—C10—C9 17.6 (4)
C12—Fe1—C2—C1 138.1 (4) C1—Fe1—C10—C9 −62.9 (5)
C13—Fe1—C2—C1 94.6 (4) C12—Fe1—C10—C9 157.2 (5)
C11—Fe1—C2—C1 176.7 (4) C13—Fe1—C10—C9 −159.6 (5)
C3—Fe1—C2—C1 −119.9 (5) C11—Fe1—C10—C9 120.1 (5)
C1—C2—C3—C4 0.7 (7) C3—Fe1—C10—C9 55.3 (5)
Fe1—C2—C3—C4 −57.9 (4) C14—C10—C11—C12 −0.7 (6)
C1—C2—C3—Fe1 58.6 (4) C9—C10—C11—C12 −170.7 (6)
C5—Fe1—C3—C2 −82.4 (4) Fe1—C10—C11—C12 −60.1 (4)
C4—Fe1—C3—C2 −120.0 (5) C14—C10—C11—Fe1 59.4 (4)
C10—Fe1—C3—C2 177.4 (5) C9—C10—C11—Fe1 −110.5 (6)
C1—Fe1—C3—C2 −37.3 (4) C14—Fe1—C11—C12 80.1 (4)
C12—Fe1—C3—C2 95.8 (4) C5—Fe1—C11—C12 175.4 (4)
C13—Fe1—C3—C2 58.5 (6) C4—Fe1—C11—C12 −147.1 (4)
C11—Fe1—C3—C2 138.3 (4) C10—Fe1—C11—C12 118.7 (5)
C5—Fe1—C3—C4 37.6 (3) C13—Fe1—C11—C12 36.2 (4)
C10—Fe1—C3—C4 −62.6 (4) C2—Fe1—C11—C12 −65.8 (6)
C1—Fe1—C3—C4 82.7 (3) C3—Fe1—C11—C12 −103.5 (4)
C12—Fe1—C3—C4 −144.2 (4) C14—Fe1—C11—C10 −38.7 (3)
C13—Fe1—C3—C4 178.5 (4) C5—Fe1—C11—C10 56.7 (5)
C11—Fe1—C3—C4 −101.6 (3) C4—Fe1—C11—C10 94.2 (3)
C2—Fe1—C3—C4 120.0 (5) C12—Fe1—C11—C10 −118.7 (5)
C2—C3—C4—C5 −0.8 (6) C13—Fe1—C11—C10 −82.5 (4)
Fe1—C3—C4—C5 −59.5 (4) C2—Fe1—C11—C10 175.4 (5)
C2—C3—C4—Fe1 58.7 (4) C3—Fe1—C11—C10 137.8 (3)
C14—Fe1—C4—C3 178.1 (4) C10—C11—C12—C13 0.6 (7)
C5—Fe1—C4—C3 −119.6 (5) Fe1—C11—C12—C13 −58.6 (5)
C10—Fe1—C4—C3 139.0 (3) C10—C11—C12—Fe1 59.2 (4)
C1—Fe1—C4—C3 −80.3 (3) C14—Fe1—C12—C11 −83.4 (4)
C12—Fe1—C4—C3 60.9 (5) C4—Fe1—C12—C11 55.0 (6)
C11—Fe1—C4—C3 95.3 (3) C10—Fe1—C12—C11 −38.3 (4)
C2—Fe1—C4—C3 −36.7 (3) C1—Fe1—C12—C11 176.2 (4)
C14—Fe1—C4—C5 −62.3 (4) C13—Fe1—C12—C11 −121.6 (6)
C10—Fe1—C4—C5 −101.4 (3) C2—Fe1—C12—C11 136.8 (4)
C1—Fe1—C4—C5 39.3 (3) C3—Fe1—C12—C11 93.5 (4)
C12—Fe1—C4—C5 −179.4 (6) C14—Fe1—C12—C13 38.2 (4)
C11—Fe1—C4—C5 −145.1 (3) C4—Fe1—C12—C13 176.7 (4)
C2—Fe1—C4—C5 82.9 (4) C10—Fe1—C12—C13 83.3 (4)
C3—Fe1—C4—C5 119.6 (5) C1—Fe1—C12—C13 −62.2 (6)
C3—C4—C5—C6 172.0 (5) C11—Fe1—C12—C13 121.6 (6)
Fe1—C4—C5—C6 111.5 (6) C2—Fe1—C12—C13 −101.6 (5)
C3—C4—C5—C1 0.6 (6) C3—Fe1—C12—C13 −144.9 (4)
Fe1—C4—C5—C1 −59.9 (4) C11—C12—C13—C14 −0.2 (8)
C3—C4—C5—Fe1 60.5 (3) Fe1—C12—C13—C14 −58.9 (4)
C2—C1—C5—C4 −0.2 (6) C11—C12—C13—Fe1 58.7 (5)
Fe1—C1—C5—C4 60.1 (4) C14—Fe1—C13—C12 −118.6 (6)
C2—C1—C5—C6 −172.1 (6) C5—Fe1—C13—C12 −179.7 (6)
Fe1—C1—C5—C6 −111.8 (6) C10—Fe1—C13—C12 −79.7 (5)
C2—C1—C5—Fe1 −60.3 (4) C1—Fe1—C13—C12 139.9 (4)
C14—Fe1—C5—C4 139.6 (3) C11—Fe1—C13—C12 −35.7 (4)
C10—Fe1—C5—C4 95.1 (3) C2—Fe1—C13—C12 96.1 (5)
C1—Fe1—C5—C4 −117.5 (5) C3—Fe1—C13—C12 59.5 (6)
C13—Fe1—C5—C4 176.9 (4) C5—Fe1—C13—C14 −61.1 (5)
C11—Fe1—C5—C4 59.0 (5) C10—Fe1—C13—C14 38.9 (4)
C2—Fe1—C5—C4 −80.1 (4) C1—Fe1—C13—C14 −101.5 (4)
C3—Fe1—C5—C4 −37.3 (3) C12—Fe1—C13—C14 118.6 (6)
C14—Fe1—C5—C6 15.5 (5) C11—Fe1—C13—C14 82.9 (4)
C4—Fe1—C5—C6 −124.1 (6) C2—Fe1—C13—C14 −145.3 (4)
C10—Fe1—C5—C6 −29.0 (5) C3—Fe1—C13—C14 178.1 (4)
C1—Fe1—C5—C6 118.4 (5) C12—C13—C14—C10 −0.2 (7)
C13—Fe1—C5—C6 52.8 (6) Fe1—C13—C14—C10 −60.0 (4)
C11—Fe1—C5—C6 −65.0 (5) C12—C13—C14—Fe1 59.8 (4)
C2—Fe1—C5—C6 155.8 (5) C11—C10—C14—C13 0.6 (6)
C3—Fe1—C5—C6 −161.4 (5) C9—C10—C14—C13 170.3 (5)
C14—Fe1—C5—C1 −102.9 (4) Fe1—C10—C14—C13 60.8 (4)
C4—Fe1—C5—C1 117.5 (5) C11—C10—C14—Fe1 −60.2 (4)
C10—Fe1—C5—C1 −147.4 (3) C9—C10—C14—Fe1 109.5 (6)
C13—Fe1—C5—C1 −65.6 (4) C5—Fe1—C14—C13 140.5 (4)
C11—Fe1—C5—C1 176.6 (4) C4—Fe1—C14—C13 178.4 (4)
C2—Fe1—C5—C1 37.4 (4) C10—Fe1—C14—C13 −118.0 (5)
C3—Fe1—C5—C1 80.2 (3) C1—Fe1—C14—C13 95.7 (4)
C7—O2—C6—O1 20.9 (6) C12—Fe1—C14—C13 −37.6 (4)
C7—O2—C6—C5 −157.9 (4) C11—Fe1—C14—C13 −80.1 (4)
C4—C5—C6—O1 −175.5 (5) C2—Fe1—C14—C13 59.6 (6)
C1—C5—C6—O1 −5.5 (9) C5—Fe1—C14—C10 −101.5 (4)
Fe1—C5—C6—O1 −89.0 (6) C4—Fe1—C14—C10 −63.6 (5)
C4—C5—C6—O2 3.2 (8) C1—Fe1—C14—C10 −146.3 (3)
C1—C5—C6—O2 173.3 (5) C12—Fe1—C14—C10 80.4 (4)
Fe1—C5—C6—O2 89.7 (4) C13—Fe1—C14—C10 118.0 (5)
C6—O2—C7—C15 −126.9 (5) C11—Fe1—C14—C10 37.9 (3)
C6—O2—C7—C8 111.4 (5) C2—Fe1—C14—C10 177.6 (5)
C9—O3—C8—C7 108.1 (5)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2432).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811019398/hy2432sup1.cif

e-67-0m947-sup1.cif (25.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019398/hy2432Isup2.hkl

e-67-0m947-Isup2.hkl (97KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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