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

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ISSN: 2056-9890

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

aKey Laboratory of Synthetic and Natural Chemistry of the Ministry of Education, College of Chemistry and Materials Science, Northwest University of Xi'an, Taibai Bei Avenue 229, Xi'an 710069, Shaanxi, People's Republic of China
*Correspondence e-mail: yangbq@nwu.edu.cn

(Received 15 May 2011; accepted 23 May 2011; online 18 June 2011)

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[Otón, F., Tarraga, A., Espinosa, A., Velasco, M. D., Bautista, D. & Molina, P. (2005). J. Org. Chem. 70, 6603-6608.]). For the properties of ferrocenophanes, see: Cayuela et al. (2004[Cayuela, E., Jalon, F. A., Manzano, B. R., Espino, G., Weissensteiner, W. & Mereiter, K. (2004). J. Am. Chem. Soc. 126, 7049-7062.]); Kulbaba & Manners (2001[Kulbaba, K. & Manners, I. (2001). Macromol. Rapid Commun. 22, 711-724.]); Lu et al. (2006[Lu, J., Baker, M. V. & Brown, D. H. (2006). Inorg. Chim. Acta, 359, 1299-1302.]); Mizuta et al. (2003[Mizuta, T., Imamura, Y. & Miyoshi, K. (2003). J. Am. Chem. Soc. 125, 2068-2069.]); Nguyen et al. (1999[Nguyen, P., Gómez-Elipe, P. & Manners, I. (1999). Chem. Rev. 99, 1515-1548.]); Otón et al. (2006a[Otón, F., Tarraga, A., Espinosa, A., Velasco, M. D. & Molina, P. (2006a). J. Org. Chem. 71, 4590-4598.],b[Otón, F., Tarraga, A. & Molina, P. (2006b). Org. Lett. 8, 2107-2110.]); Suzaki et al. (2006[Suzaki, Y., Horie, M., Sakano, T. & Osakada, K. (2006). J. Organomet. Chem. 691, 3403-3407.]). For the synthesis and related structures, see: Gao et al. (2009[Gao, B., Yang, B.-Q., Li, T. & Zhang, B.-L. (2009). Synth. Commun. 39, 2973-2981.]); Leng et al. (2010[Leng, X., Yang, B., Cui, L. & Liu, B. (2010). Acta Cryst. E66, m1528.]). For studies of host structures for the investigation of mol­ecular recognition, see: Bond et al. (2009[Bond, A. D., Fleming, A., Gaire, J., Kelleher, F., McGinley, J. & Mckee, V. (2009). Tetrahedron, 65, 7942-7947.]); Choi et al. (2006[Choi, H. J., Park, Y. S., Kim, M. G., Park, Y. J., Yoon, N. S. & Bell, T. W. (2006). Tetrahedron, 62, 8696-8701.]); Nakagaki et al. (2010[Nakagaki, T., Shin-ichiro, K., Harano, A. & Shinmyozu, T. (2010). Tetrahedron, 66, 976-985.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C15H14O4)]

  • Mr = 314.11

  • Monoclinic, C c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.727, Tmax = 0.870

  • 3177 measured reflections

  • 1971 independent reflections

  • 1721 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 812 Friedel pairs

  • Flack parameter: 0.03 (3)

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS 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: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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.

Related literature top

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 the investigation 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).

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
propane-1,2-diyl ferrocene-1,1'-dicarboxylate top
Crystal data top
[Fe(C15H14O4)]Z = 4
Mr = 314.11F(000) = 648
Monoclinic, CcDx = 1.606 Mg m3
Hall symbol: C -2ycMelting point: 405(6) K
a = 7.1665 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 20.131 (4) ŵ = 1.17 mm1
c = 9.2464 (19) ÅT = 296 K
β = 103.193 (2)°Block, yellow
V = 1298.7 (4) Å30.29 × 0.21 × 0.12 mm
Data collection top
Bruker APEXII CCD
diffractometer
1971 independent reflections
Radiation source: fine-focus sealed tube1721 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ϕ and ω scansθmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.727, Tmax = 0.870k = 2421
3177 measured reflectionsl = 811
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-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 reflectionsΔρmax = 0.30 e Å3
182 parametersΔρmin = 0.41 e Å3
2 restraintsAbsolute structure: Flack (1983), 812 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (3)
Crystal data top
[Fe(C15H14O4)]V = 1298.7 (4) Å3
Mr = 314.11Z = 4
Monoclinic, CcMo Kα radiation
a = 7.1665 (14) ŵ = 1.17 mm1
b = 20.131 (4) ÅT = 296 K
c = 9.2464 (19) Å0.29 × 0.21 × 0.12 mm
β = 103.193 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
1971 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1721 reflections with I > 2σ(I)
Tmin = 0.727, Tmax = 0.870Rint = 0.024
3177 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.087Δρmax = 0.30 e Å3
S = 0.96Δρmin = 0.41 e Å3
1971 reflectionsAbsolute structure: Flack (1983), 812 Friedel pairs
182 parametersAbsolute structure parameter: 0.03 (3)
2 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.13087 (9)0.36266 (2)0.68667 (8)0.04130 (18)
O10.5456 (6)0.47208 (16)0.8549 (4)0.0654 (10)
O20.5650 (4)0.37627 (13)0.9814 (3)0.0426 (7)
O30.2545 (5)0.40433 (17)1.0838 (4)0.0562 (8)
O40.1738 (6)0.2959 (2)1.0643 (5)0.0820 (12)
C10.3338 (7)0.3998 (3)0.5860 (6)0.0522 (13)
H10.34310.44590.55410.063*
C20.2339 (10)0.3478 (4)0.4983 (7)0.0609 (17)
H20.15930.35200.39570.073*
C30.2568 (7)0.2893 (3)0.5836 (6)0.0523 (12)
H30.20110.24580.55100.063*
C40.3700 (7)0.3047 (2)0.7267 (5)0.0480 (11)
H40.40740.27320.80910.058*
C50.4210 (9)0.3728 (3)0.7309 (7)0.0404 (13)
C60.5160 (6)0.4129 (2)0.8576 (5)0.0408 (10)
C70.5946 (7)0.4116 (2)1.1239 (5)0.0465 (11)
H70.58780.45961.10620.056*
C80.4317 (8)0.3902 (3)1.1916 (7)0.0585 (15)
H8A0.44100.34311.21420.070*
H8B0.43560.41441.28290.070*
C90.1550 (7)0.3512 (3)1.0141 (6)0.0547 (13)
C100.0267 (9)0.3693 (3)0.8729 (7)0.0475 (15)
C110.0857 (7)0.3239 (3)0.7722 (6)0.0592 (14)
H110.10550.27680.79110.071*
C120.1631 (11)0.3581 (4)0.6428 (9)0.069 (2)
H120.24450.33830.55360.083*
C130.1028 (7)0.4244 (3)0.6556 (7)0.0655 (15)
H130.13720.45890.57930.079*
C140.0168 (8)0.4324 (3)0.7992 (6)0.0582 (13)
H140.07880.47370.84140.070*
C150.7879 (9)0.3938 (3)1.2184 (7)0.0636 (16)
H15A0.79610.34651.23210.095*
H15B0.80500.41521.31330.095*
H15C0.88610.40831.17030.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0369 (3)0.0492 (3)0.0394 (3)0.0023 (3)0.0120 (2)0.0010 (4)
O10.093 (3)0.053 (2)0.048 (2)0.0180 (17)0.012 (2)0.0077 (16)
O20.0533 (18)0.0433 (16)0.0294 (16)0.0043 (13)0.0056 (14)0.0023 (13)
O30.0564 (19)0.066 (2)0.049 (2)0.0042 (16)0.0175 (17)0.0113 (16)
O40.095 (3)0.086 (3)0.059 (3)0.036 (2)0.004 (2)0.014 (2)
C10.046 (3)0.071 (4)0.043 (3)0.004 (3)0.016 (2)0.012 (3)
C20.058 (4)0.090 (4)0.038 (4)0.010 (3)0.016 (3)0.011 (3)
C30.050 (3)0.060 (3)0.046 (3)0.008 (2)0.010 (2)0.008 (2)
C40.052 (3)0.051 (3)0.042 (3)0.005 (2)0.012 (2)0.006 (2)
C50.037 (3)0.052 (3)0.034 (3)0.002 (2)0.011 (3)0.002 (2)
C60.039 (2)0.049 (3)0.036 (3)0.0002 (19)0.012 (2)0.004 (2)
C70.062 (3)0.044 (2)0.032 (2)0.001 (2)0.008 (2)0.0051 (18)
C80.067 (4)0.072 (3)0.036 (3)0.016 (3)0.013 (3)0.007 (2)
C90.052 (3)0.071 (4)0.050 (3)0.015 (2)0.028 (2)0.002 (2)
C100.031 (3)0.074 (4)0.041 (4)0.000 (2)0.014 (3)0.004 (2)
C110.045 (3)0.079 (4)0.057 (4)0.014 (3)0.019 (3)0.016 (3)
C120.031 (3)0.121 (7)0.055 (5)0.003 (3)0.010 (3)0.015 (4)
C130.051 (3)0.084 (4)0.062 (4)0.019 (3)0.013 (3)0.002 (3)
C140.050 (3)0.068 (3)0.060 (4)0.014 (2)0.018 (3)0.009 (3)
C150.065 (3)0.071 (4)0.046 (3)0.004 (3)0.005 (3)0.013 (3)
Geometric parameters (Å, º) top
Fe1—C142.027 (5)C3—H30.9800
Fe1—C52.036 (6)C4—C51.418 (7)
Fe1—C42.037 (5)C4—H40.9800
Fe1—C102.032 (6)C5—C61.456 (7)
Fe1—C12.040 (5)C7—C151.503 (7)
Fe1—C122.054 (8)C7—C81.508 (7)
Fe1—C132.053 (5)C7—H70.9800
Fe1—C112.051 (5)C8—H8A0.9700
Fe1—C22.063 (6)C8—H8B0.9700
Fe1—C32.073 (5)C9—C101.461 (9)
O1—C61.212 (5)C10—C111.418 (7)
O2—C61.339 (5)C10—C141.437 (7)
O2—C71.469 (5)C11—C121.382 (10)
O3—C91.362 (6)C11—H110.9800
O3—C81.452 (7)C12—C131.401 (8)
O4—C91.202 (6)C12—H120.9800
C1—C21.415 (9)C13—C141.416 (8)
C1—C51.449 (8)C13—H130.9800
C1—H10.9800C14—H140.9800
C2—C31.406 (9)C15—H15A0.9600
C2—H20.9800C15—H15B0.9600
C3—C41.419 (6)C15—H15C0.9600
C14—Fe1—C5109.9 (2)C3—C4—Fe171.2 (3)
C14—Fe1—C4136.5 (2)C5—C4—Fe169.6 (3)
C5—Fe1—C440.76 (18)C3—C4—H4125.5
C14—Fe1—C1041.5 (2)C5—C4—H4125.5
C5—Fe1—C10112.3 (2)Fe1—C4—H4125.5
C4—Fe1—C10109.9 (2)C4—C5—C6128.9 (5)
C14—Fe1—C1113.2 (3)C4—C5—C1106.4 (5)
C5—Fe1—C141.7 (2)C6—C5—C1124.1 (4)
C4—Fe1—C168.6 (2)C4—C5—Fe169.7 (3)
C10—Fe1—C1143.3 (2)C6—C5—Fe1119.1 (4)
C14—Fe1—C1267.5 (3)C1—C5—Fe169.3 (3)
C5—Fe1—C12176.8 (2)O1—C6—O2123.1 (4)
C4—Fe1—C12142.4 (3)O1—C6—C5125.4 (4)
C10—Fe1—C1267.1 (3)O2—C6—C5111.5 (4)
C1—Fe1—C12137.1 (3)O2—C7—C15109.4 (4)
C14—Fe1—C1340.6 (2)O2—C7—C8105.5 (4)
C5—Fe1—C13136.9 (2)C15—C7—C8112.9 (5)
C4—Fe1—C13176.9 (2)O2—C7—H7109.7
C10—Fe1—C1368.5 (2)C15—C7—H7109.7
C1—Fe1—C13111.0 (2)C8—C7—H7109.7
C12—Fe1—C1339.9 (2)O3—C8—C7107.3 (5)
C14—Fe1—C1168.7 (2)O3—C8—H8A110.2
C5—Fe1—C11142.1 (2)C7—C8—H8A110.2
C4—Fe1—C11113.0 (2)O3—C8—H8B110.2
C10—Fe1—C1140.6 (2)C7—C8—H8B110.2
C1—Fe1—C11175.7 (2)H8A—C8—H8B108.5
C12—Fe1—C1139.3 (3)O4—C9—O3122.9 (5)
C13—Fe1—C1167.6 (3)O4—C9—C10124.6 (5)
C14—Fe1—C2142.9 (3)O3—C9—C10112.5 (5)
C5—Fe1—C268.8 (3)C11—C10—C14107.4 (5)
C4—Fe1—C267.8 (3)C11—C10—C9125.1 (5)
C10—Fe1—C2175.4 (3)C14—C10—C9126.6 (5)
C1—Fe1—C240.3 (2)C11—C10—Fe170.4 (3)
C12—Fe1—C2112.0 (3)C14—C10—Fe169.1 (3)
C13—Fe1—C2114.0 (3)C9—C10—Fe1117.6 (4)
C11—Fe1—C2135.9 (3)C12—C11—C10107.6 (6)
C14—Fe1—C3176.6 (2)C12—C11—Fe170.5 (4)
C5—Fe1—C368.4 (2)C10—C11—Fe169.0 (3)
C4—Fe1—C340.38 (18)C12—C11—H11126.2
C10—Fe1—C3136.0 (2)C10—C11—H11126.2
C1—Fe1—C367.7 (2)Fe1—C11—H11126.2
C12—Fe1—C3114.3 (2)C11—C12—C13110.3 (7)
C13—Fe1—C3142.6 (2)C11—C12—Fe170.2 (4)
C11—Fe1—C3110.7 (2)C13—C12—Fe170.0 (4)
C2—Fe1—C339.7 (2)C11—C12—H12124.8
C6—O2—C7117.2 (3)C13—C12—H12124.8
C9—O3—C8116.9 (4)Fe1—C12—H12124.8
C2—C1—C5107.9 (5)C12—C13—C14107.2 (6)
C2—C1—Fe170.7 (3)C12—C13—Fe170.1 (4)
C5—C1—Fe169.0 (3)C14—C13—Fe168.7 (3)
C2—C1—H1126.0C12—C13—H13126.4
C5—C1—H1126.0C14—C13—H13126.4
Fe1—C1—H1126.0Fe1—C13—H13126.4
C3—C2—C1108.6 (6)C13—C14—C10107.4 (5)
C3—C2—Fe170.5 (3)C13—C14—Fe170.7 (3)
C1—C2—Fe168.9 (3)C10—C14—Fe169.4 (3)
C3—C2—H2125.7C13—C14—H14126.3
C1—C2—H2125.7C10—C14—H14126.3
Fe1—C2—H2125.7Fe1—C14—H14126.3
C2—C3—C4108.0 (5)C7—C15—H15A109.5
C2—C3—Fe169.8 (3)C7—C15—H15B109.5
C4—C3—Fe168.4 (3)H15A—C15—H15B109.5
C2—C3—H3126.0C7—C15—H15C109.5
C4—C3—H3126.0H15A—C15—H15C109.5
Fe1—C3—H3126.0H15B—C15—H15C109.5
C3—C4—C5109.0 (5)
C14—Fe1—C1—C2146.8 (4)O2—C7—C8—O355.2 (5)
C5—Fe1—C1—C2118.9 (5)C15—C7—C8—O3174.6 (4)
C4—Fe1—C1—C280.4 (4)C8—O3—C9—O421.6 (7)
C10—Fe1—C1—C2175.4 (5)C8—O3—C9—C10157.7 (5)
C12—Fe1—C1—C265.5 (6)O4—C9—C10—C113.3 (9)
C13—Fe1—C1—C2102.9 (4)O3—C9—C10—C11176.0 (5)
C3—Fe1—C1—C236.8 (4)O4—C9—C10—C14171.4 (6)
C14—Fe1—C1—C594.3 (3)O3—C9—C10—C147.9 (8)
C4—Fe1—C1—C538.5 (3)O4—C9—C10—Fe187.9 (6)
C10—Fe1—C1—C556.4 (5)O3—C9—C10—Fe191.5 (5)
C12—Fe1—C1—C5175.6 (4)C14—Fe1—C10—C11118.4 (5)
C13—Fe1—C1—C5138.2 (3)C5—Fe1—C10—C11146.3 (3)
C2—Fe1—C1—C5118.9 (5)C4—Fe1—C10—C11102.5 (3)
C3—Fe1—C1—C582.1 (3)C1—Fe1—C10—C11176.9 (4)
C5—C1—C2—C30.3 (7)C12—Fe1—C10—C1137.1 (4)
Fe1—C1—C2—C359.5 (4)C13—Fe1—C10—C1180.3 (4)
C5—C1—C2—Fe159.2 (4)C3—Fe1—C10—C1164.8 (5)
C14—Fe1—C2—C3176.6 (4)C5—Fe1—C10—C1495.2 (4)
C5—Fe1—C2—C381.3 (4)C4—Fe1—C10—C14139.0 (3)
C4—Fe1—C2—C337.3 (3)C1—Fe1—C10—C1458.5 (5)
C1—Fe1—C2—C3119.9 (5)C12—Fe1—C10—C1481.4 (4)
C12—Fe1—C2—C3102.0 (4)C13—Fe1—C10—C1438.1 (3)
C13—Fe1—C2—C3145.5 (3)C11—Fe1—C10—C14118.4 (5)
C11—Fe1—C2—C363.4 (5)C3—Fe1—C10—C14176.7 (3)
C14—Fe1—C2—C156.7 (6)C14—Fe1—C10—C9121.4 (6)
C5—Fe1—C2—C138.6 (3)C5—Fe1—C10—C926.2 (5)
C4—Fe1—C2—C182.6 (4)C4—Fe1—C10—C917.6 (4)
C12—Fe1—C2—C1138.1 (4)C1—Fe1—C10—C962.9 (5)
C13—Fe1—C2—C194.6 (4)C12—Fe1—C10—C9157.2 (5)
C11—Fe1—C2—C1176.7 (4)C13—Fe1—C10—C9159.6 (5)
C3—Fe1—C2—C1119.9 (5)C11—Fe1—C10—C9120.1 (5)
C1—C2—C3—C40.7 (7)C3—Fe1—C10—C955.3 (5)
Fe1—C2—C3—C457.9 (4)C14—C10—C11—C120.7 (6)
C1—C2—C3—Fe158.6 (4)C9—C10—C11—C12170.7 (6)
C5—Fe1—C3—C282.4 (4)Fe1—C10—C11—C1260.1 (4)
C4—Fe1—C3—C2120.0 (5)C14—C10—C11—Fe159.4 (4)
C10—Fe1—C3—C2177.4 (5)C9—C10—C11—Fe1110.5 (6)
C1—Fe1—C3—C237.3 (4)C14—Fe1—C11—C1280.1 (4)
C12—Fe1—C3—C295.8 (4)C5—Fe1—C11—C12175.4 (4)
C13—Fe1—C3—C258.5 (6)C4—Fe1—C11—C12147.1 (4)
C11—Fe1—C3—C2138.3 (4)C10—Fe1—C11—C12118.7 (5)
C5—Fe1—C3—C437.6 (3)C13—Fe1—C11—C1236.2 (4)
C10—Fe1—C3—C462.6 (4)C2—Fe1—C11—C1265.8 (6)
C1—Fe1—C3—C482.7 (3)C3—Fe1—C11—C12103.5 (4)
C12—Fe1—C3—C4144.2 (4)C14—Fe1—C11—C1038.7 (3)
C13—Fe1—C3—C4178.5 (4)C5—Fe1—C11—C1056.7 (5)
C11—Fe1—C3—C4101.6 (3)C4—Fe1—C11—C1094.2 (3)
C2—Fe1—C3—C4120.0 (5)C12—Fe1—C11—C10118.7 (5)
C2—C3—C4—C50.8 (6)C13—Fe1—C11—C1082.5 (4)
Fe1—C3—C4—C559.5 (4)C2—Fe1—C11—C10175.4 (5)
C2—C3—C4—Fe158.7 (4)C3—Fe1—C11—C10137.8 (3)
C14—Fe1—C4—C3178.1 (4)C10—C11—C12—C130.6 (7)
C5—Fe1—C4—C3119.6 (5)Fe1—C11—C12—C1358.6 (5)
C10—Fe1—C4—C3139.0 (3)C10—C11—C12—Fe159.2 (4)
C1—Fe1—C4—C380.3 (3)C14—Fe1—C12—C1183.4 (4)
C12—Fe1—C4—C360.9 (5)C4—Fe1—C12—C1155.0 (6)
C11—Fe1—C4—C395.3 (3)C10—Fe1—C12—C1138.3 (4)
C2—Fe1—C4—C336.7 (3)C1—Fe1—C12—C11176.2 (4)
C14—Fe1—C4—C562.3 (4)C13—Fe1—C12—C11121.6 (6)
C10—Fe1—C4—C5101.4 (3)C2—Fe1—C12—C11136.8 (4)
C1—Fe1—C4—C539.3 (3)C3—Fe1—C12—C1193.5 (4)
C12—Fe1—C4—C5179.4 (6)C14—Fe1—C12—C1338.2 (4)
C11—Fe1—C4—C5145.1 (3)C4—Fe1—C12—C13176.7 (4)
C2—Fe1—C4—C582.9 (4)C10—Fe1—C12—C1383.3 (4)
C3—Fe1—C4—C5119.6 (5)C1—Fe1—C12—C1362.2 (6)
C3—C4—C5—C6172.0 (5)C11—Fe1—C12—C13121.6 (6)
Fe1—C4—C5—C6111.5 (6)C2—Fe1—C12—C13101.6 (5)
C3—C4—C5—C10.6 (6)C3—Fe1—C12—C13144.9 (4)
Fe1—C4—C5—C159.9 (4)C11—C12—C13—C140.2 (8)
C3—C4—C5—Fe160.5 (3)Fe1—C12—C13—C1458.9 (4)
C2—C1—C5—C40.2 (6)C11—C12—C13—Fe158.7 (5)
Fe1—C1—C5—C460.1 (4)C14—Fe1—C13—C12118.6 (6)
C2—C1—C5—C6172.1 (6)C5—Fe1—C13—C12179.7 (6)
Fe1—C1—C5—C6111.8 (6)C10—Fe1—C13—C1279.7 (5)
C2—C1—C5—Fe160.3 (4)C1—Fe1—C13—C12139.9 (4)
C14—Fe1—C5—C4139.6 (3)C11—Fe1—C13—C1235.7 (4)
C10—Fe1—C5—C495.1 (3)C2—Fe1—C13—C1296.1 (5)
C1—Fe1—C5—C4117.5 (5)C3—Fe1—C13—C1259.5 (6)
C13—Fe1—C5—C4176.9 (4)C5—Fe1—C13—C1461.1 (5)
C11—Fe1—C5—C459.0 (5)C10—Fe1—C13—C1438.9 (4)
C2—Fe1—C5—C480.1 (4)C1—Fe1—C13—C14101.5 (4)
C3—Fe1—C5—C437.3 (3)C12—Fe1—C13—C14118.6 (6)
C14—Fe1—C5—C615.5 (5)C11—Fe1—C13—C1482.9 (4)
C4—Fe1—C5—C6124.1 (6)C2—Fe1—C13—C14145.3 (4)
C10—Fe1—C5—C629.0 (5)C3—Fe1—C13—C14178.1 (4)
C1—Fe1—C5—C6118.4 (5)C12—C13—C14—C100.2 (7)
C13—Fe1—C5—C652.8 (6)Fe1—C13—C14—C1060.0 (4)
C11—Fe1—C5—C665.0 (5)C12—C13—C14—Fe159.8 (4)
C2—Fe1—C5—C6155.8 (5)C11—C10—C14—C130.6 (6)
C3—Fe1—C5—C6161.4 (5)C9—C10—C14—C13170.3 (5)
C14—Fe1—C5—C1102.9 (4)Fe1—C10—C14—C1360.8 (4)
C4—Fe1—C5—C1117.5 (5)C11—C10—C14—Fe160.2 (4)
C10—Fe1—C5—C1147.4 (3)C9—C10—C14—Fe1109.5 (6)
C13—Fe1—C5—C165.6 (4)C5—Fe1—C14—C13140.5 (4)
C11—Fe1—C5—C1176.6 (4)C4—Fe1—C14—C13178.4 (4)
C2—Fe1—C5—C137.4 (4)C10—Fe1—C14—C13118.0 (5)
C3—Fe1—C5—C180.2 (3)C1—Fe1—C14—C1395.7 (4)
C7—O2—C6—O120.9 (6)C12—Fe1—C14—C1337.6 (4)
C7—O2—C6—C5157.9 (4)C11—Fe1—C14—C1380.1 (4)
C4—C5—C6—O1175.5 (5)C2—Fe1—C14—C1359.6 (6)
C1—C5—C6—O15.5 (9)C5—Fe1—C14—C10101.5 (4)
Fe1—C5—C6—O189.0 (6)C4—Fe1—C14—C1063.6 (5)
C4—C5—C6—O23.2 (8)C1—Fe1—C14—C10146.3 (3)
C1—C5—C6—O2173.3 (5)C12—Fe1—C14—C1080.4 (4)
Fe1—C5—C6—O289.7 (4)C13—Fe1—C14—C10118.0 (5)
C6—O2—C7—C15126.9 (5)C11—Fe1—C14—C1037.9 (3)
C6—O2—C7—C8111.4 (5)C2—Fe1—C14—C10177.6 (5)
C9—O3—C8—C7108.1 (5)

Experimental details

Crystal data
Chemical formula[Fe(C15H14O4)]
Mr314.11
Crystal system, space groupMonoclinic, Cc
Temperature (K)296
a, b, c (Å)7.1665 (14), 20.131 (4), 9.2464 (19)
β (°) 103.193 (2)
V3)1298.7 (4)
Z4
Radiation typeMo Kα
µ (mm1)1.17
Crystal size (mm)0.29 × 0.21 × 0.12
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.727, 0.870
No. of measured, independent and
observed [I > 2σ(I)] reflections
3177, 1971, 1721
Rint0.024
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.087, 0.96
No. of reflections1971
No. of parameters182
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.41
Absolute structureFlack (1983), 812 Friedel pairs
Absolute structure parameter0.03 (3)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999).

 

Acknowledgements

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

References

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