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

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ISSN: 2056-9890

1-[(2,3,4,5,6-Penta­fluoro­phen­yl)ethyn­yl]ferrocene

aKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
*Correspondence e-mail: zhangchan20050333@163.com

(Received 29 June 2010; accepted 6 July 2010; online 10 July 2010)

The mol­ecular structure of the title compound, [Fe(C5H5)(C13H4F5)], consists of a ferrocenyl group and a 2,3,4,5,6-penta­fluoro­benzene group linked through an ethyne spacer. The crystal packing is dominated by inter­molecular C—H⋯F hydrogen bonds, C—F⋯π inter­actions between the penta­fluoro­benzene groups [F⋯centroid distances = 3.882 (2) and 3.884 (2) Å] and ππ inter­actions between the penta­fluoro­benzene and cyclo­penta­dienyl rings [centroid–centroid distance = 3.741 (1) Å].

Related literature

For general background to ferrocene derivatives, see: Debroy & Roy (2007[Debroy, P. & Roy, S. (2007). Coord. Chem. Rev. 251, 203-221.]). For a related structure, see: Valdebenito et al. (2010[Valdebenito, C., Garland, M. T., Fuentealba, M. & Escobar, C. A. (2010). Acta Cryst. E66, m838.]). For the synthesis, see: Torres et al. (2002[Torres, J. C., Pilli, R. A., Vargas, M. D., Violante, F. A., Garden, S. J. & Pinto, A. C. (2002). Tetrahedron, 58, 4487-4492.]); Zora et al. (2006[Zora, M., Açıkgöz, C., Tumay, T. A., Odabaşoğlu, M. & Büyükgüngör, O. (2006). Acta Cryst. C62, m327-m330.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C13H4F5)]

  • Mr = 376.10

  • Triclinic, [P \overline 1]

  • a = 6.0767 (9) Å

  • b = 10.7164 (15) Å

  • c = 12.6014 (18) Å

  • α = 65.725 (2)°

  • β = 89.364 (3)°

  • γ = 78.726 (2)°

  • V = 731.41 (18) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.08 mm−1

  • T = 292 K

  • 0.30 × 0.04 × 0.02 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • 4793 measured reflections

  • 2533 independent reflections

  • 2169 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.105

  • S = 1.05

  • 2533 reflections

  • 217 parameters

  • H-atom parameters constrained

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10⋯F5i 0.93 2.50 3.176 (3) 130
Symmetry code: (i) -x+1, -y+2, -z+2.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART 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: 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 derivatives with linear, unsaturated side-arms show altered unique properties, such as electrical conductivity, thermal stability, magnetic, electronic, redox and non-linear optical behaviors, compared to their saturated derivatives (Debroy & Roy, 2007).

The molecular structure of the title compound is composed of a ferrocenyl group and a pentafluorobenzene group joined by an organic ethyne spacer. Two cyclopentadienyl rings of the ferrocenyl group are parallel (Valdebenito et al., 2010). The main features of the structure are an intermolecular C—H···F hydrogen bond between the ferrocenyl and pentafluorobenzene (Table 1), C—F···π interactions between the pentafluorobenzene groups [F···centroid distances = 3.882 (2) and 3.884 (2) Å] and a ππ interaction between the pentafluorobenzene and cyclopentadienyl rings [centroid–centroid distance = 3.741 (1) Å].

Related literature top

For general background to ferrocene derivatives, see: Debroy & Roy (2007). For a related structure, see: Valdebenito et al. (2010). For the synthesis, see: Torres et al. (2002); Zora et al. (2006).

Experimental top

The title compound was synthesized according to a modified literature procedure (Torres et al., 2002; Zora et al., 2006). 1,2,3,4,5-Pentafluoro-6-iodobenzene (735 mg, 2.5 mmol) and ethynylferrocene (525 mg, 2.5 mmol) were added to a mixture of Cu(CH3CO2)2 (40 mg, 0.2 mmol), Pd(PPh3)2Cl2 (140 mg, 0.2 mmol) and iPr2NH (30 ml) under argon. The resulting mixture was refluxed at 365 K for 18 h. The solution was then extracted with dichloromethane, washed with water and dried over Na2SO4. Final purification was achieved by flash column chromatography on silica gel using dichloromethane/petroleum (1:4) as eluant. The product was obtained in 30% yield. Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a solution of the compound in dichloromethane/hexane (1:10 v/v) at room temperature.

Refinement top

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and with Uiso(H) = 1.2Ueq(C).

Structure description top

Ferrocene derivatives with linear, unsaturated side-arms show altered unique properties, such as electrical conductivity, thermal stability, magnetic, electronic, redox and non-linear optical behaviors, compared to their saturated derivatives (Debroy & Roy, 2007).

The molecular structure of the title compound is composed of a ferrocenyl group and a pentafluorobenzene group joined by an organic ethyne spacer. Two cyclopentadienyl rings of the ferrocenyl group are parallel (Valdebenito et al., 2010). The main features of the structure are an intermolecular C—H···F hydrogen bond between the ferrocenyl and pentafluorobenzene (Table 1), C—F···π interactions between the pentafluorobenzene groups [F···centroid distances = 3.882 (2) and 3.884 (2) Å] and a ππ interaction between the pentafluorobenzene and cyclopentadienyl rings [centroid–centroid distance = 3.741 (1) Å].

For general background to ferrocene derivatives, see: Debroy & Roy (2007). For a related structure, see: Valdebenito et al. (2010). For the synthesis, see: Torres et al. (2002); Zora et al. (2006).

Computing details top

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
1-[(2,3,4,5,6-Pentafluorophenyl)ethynyl]ferrocene top
Crystal data top
[Fe(C5H5)(C13H4F5)]Z = 2
Mr = 376.10F(000) = 376
Triclinic, P1Dx = 1.708 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.0767 (9) ÅCell parameters from 1760 reflections
b = 10.7164 (15) Åθ = 3.3–25.1°
c = 12.6014 (18) ŵ = 1.08 mm1
α = 65.725 (2)°T = 292 K
β = 89.364 (3)°Plate, yellow
γ = 78.726 (2)°0.30 × 0.04 × 0.02 mm
V = 731.41 (18) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer
2169 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
φ and ω scansh = 77
4793 measured reflectionsk = 1212
2533 independent reflectionsl = 1314
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0602P)2 + 0.0784P]
where P = (Fo2 + 2Fc2)/3
2533 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
[Fe(C5H5)(C13H4F5)]γ = 78.726 (2)°
Mr = 376.10V = 731.41 (18) Å3
Triclinic, P1Z = 2
a = 6.0767 (9) ÅMo Kα radiation
b = 10.7164 (15) ŵ = 1.08 mm1
c = 12.6014 (18) ÅT = 292 K
α = 65.725 (2)°0.30 × 0.04 × 0.02 mm
β = 89.364 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer
2169 reflections with I > 2σ(I)
4793 measured reflectionsRint = 0.021
2533 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 1.05Δρmax = 0.41 e Å3
2533 reflectionsΔρmin = 0.25 e Å3
217 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.72848 (6)0.78028 (4)0.74835 (3)0.03952 (17)
C10.7513 (5)0.5868 (3)0.8801 (3)0.0544 (8)
H10.79670.56070.95780.065*
C20.8930 (6)0.5793 (3)0.7932 (3)0.0603 (9)
H21.04830.54720.80310.072*
C30.7575 (6)0.6290 (3)0.6885 (3)0.0629 (9)
H30.80790.63600.61670.075*
C40.5318 (5)0.6666 (3)0.7110 (3)0.0550 (8)
H40.40740.70220.65700.066*
C50.5292 (5)0.6405 (3)0.8295 (3)0.0534 (8)
H50.40240.65610.86790.064*
C60.8628 (5)0.8977 (3)0.8131 (3)0.0466 (7)
C70.9602 (5)0.9037 (3)0.7080 (3)0.0537 (8)
H71.11200.87560.70010.064*
C80.7850 (6)0.9598 (3)0.6182 (3)0.0612 (9)
H80.80170.97530.54060.073*
C90.5823 (6)0.9883 (3)0.6656 (3)0.0620 (9)
H90.44171.02640.62450.074*
C100.6256 (5)0.9498 (3)0.7858 (3)0.0535 (8)
H100.51950.95690.83790.064*
C110.9780 (5)0.8492 (3)0.9247 (3)0.0506 (7)
C121.0717 (5)0.8129 (3)1.0184 (3)0.0524 (7)
C131.1670 (5)0.7703 (3)1.1340 (2)0.0434 (6)
C141.3917 (5)0.7049 (3)1.1689 (2)0.0441 (7)
C151.4796 (5)0.6621 (3)1.2811 (3)0.0496 (7)
C161.3452 (6)0.6841 (3)1.3614 (2)0.0539 (8)
C171.1218 (6)0.7482 (3)1.3302 (3)0.0551 (8)
C181.0362 (5)0.7906 (3)1.2187 (3)0.0518 (8)
F11.5272 (3)0.68281 (19)1.09132 (16)0.0650 (5)
F21.6961 (3)0.59629 (19)1.31194 (17)0.0709 (5)
F31.4306 (4)0.6459 (2)1.46997 (16)0.0892 (7)
F40.9884 (4)0.7688 (2)1.40989 (18)0.0896 (7)
F50.8196 (3)0.85479 (19)1.19000 (19)0.0741 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0398 (3)0.0418 (3)0.0403 (3)0.01159 (17)0.00257 (18)0.01908 (19)
C10.067 (2)0.0416 (15)0.0485 (18)0.0124 (14)0.0050 (16)0.0118 (14)
C20.0542 (19)0.0474 (17)0.085 (3)0.0053 (14)0.0022 (18)0.0358 (17)
C30.085 (2)0.0606 (19)0.065 (2)0.0260 (17)0.0217 (19)0.0425 (18)
C40.0571 (19)0.0602 (18)0.060 (2)0.0209 (15)0.0019 (16)0.0336 (16)
C50.0535 (19)0.0519 (17)0.059 (2)0.0222 (14)0.0127 (16)0.0228 (15)
C60.0520 (18)0.0408 (14)0.0502 (17)0.0126 (12)0.0047 (14)0.0207 (13)
C70.0466 (17)0.0569 (17)0.057 (2)0.0210 (14)0.0025 (15)0.0188 (15)
C80.069 (2)0.0617 (19)0.0443 (18)0.0308 (17)0.0013 (16)0.0060 (15)
C90.056 (2)0.0463 (17)0.071 (2)0.0078 (14)0.0208 (17)0.0127 (16)
C100.0512 (18)0.0439 (15)0.067 (2)0.0031 (13)0.0014 (15)0.0278 (15)
C110.0554 (19)0.0433 (15)0.0563 (19)0.0155 (13)0.0044 (15)0.0215 (14)
C120.0585 (19)0.0470 (16)0.055 (2)0.0173 (14)0.0031 (16)0.0210 (15)
C130.0499 (17)0.0384 (14)0.0460 (16)0.0157 (12)0.0008 (13)0.0188 (13)
C140.0471 (17)0.0444 (14)0.0464 (17)0.0138 (12)0.0086 (14)0.0228 (13)
C150.0514 (18)0.0406 (15)0.0554 (19)0.0124 (13)0.0034 (15)0.0173 (14)
C160.085 (2)0.0417 (15)0.0356 (16)0.0192 (15)0.0014 (16)0.0136 (13)
C170.080 (2)0.0444 (16)0.0496 (19)0.0222 (15)0.0240 (17)0.0240 (14)
C180.0484 (18)0.0395 (15)0.068 (2)0.0123 (13)0.0092 (16)0.0218 (15)
F10.0653 (12)0.0744 (11)0.0630 (11)0.0143 (9)0.0201 (9)0.0366 (10)
F20.0557 (12)0.0658 (11)0.0808 (13)0.0075 (9)0.0152 (10)0.0222 (10)
F30.147 (2)0.0710 (12)0.0463 (11)0.0216 (13)0.0146 (12)0.0211 (10)
F40.1264 (19)0.0795 (13)0.0750 (13)0.0281 (12)0.0557 (13)0.0424 (11)
F50.0497 (11)0.0640 (11)0.1014 (15)0.0069 (9)0.0147 (10)0.0299 (11)
Geometric parameters (Å, º) top
Fe1—C32.029 (3)C6—C101.430 (4)
Fe1—C22.032 (3)C7—C81.411 (4)
Fe1—C12.034 (3)C7—H70.9300
Fe1—C72.037 (3)C8—C91.398 (4)
Fe1—C82.040 (3)C8—H80.9300
Fe1—C102.042 (3)C9—C101.409 (4)
Fe1—C52.044 (3)C9—H90.9300
Fe1—C62.044 (3)C10—H100.9300
Fe1—C92.045 (3)C11—C121.191 (4)
Fe1—C42.047 (3)C12—C131.427 (4)
C1—C21.404 (4)C13—C181.386 (4)
C1—C51.405 (4)C13—C141.391 (4)
C1—H10.9300C14—F11.336 (3)
C2—C31.406 (5)C14—C151.372 (4)
C2—H20.9300C15—F21.342 (3)
C3—C41.412 (4)C15—C161.360 (4)
C3—H30.9300C16—F31.335 (3)
C4—C51.402 (4)C16—C171.376 (5)
C4—H40.9300C17—F41.345 (3)
C5—H50.9300C17—C181.360 (4)
C6—C111.421 (4)C18—F51.337 (3)
C6—C71.426 (4)
C3—Fe1—C240.51 (13)C5—C4—C3107.6 (3)
C3—Fe1—C167.85 (13)C5—C4—Fe169.83 (16)
C2—Fe1—C140.41 (12)C3—C4—Fe169.08 (17)
C3—Fe1—C7118.88 (13)C5—C4—H4126.2
C2—Fe1—C7108.34 (13)C3—C4—H4126.2
C1—Fe1—C7128.23 (13)Fe1—C4—H4126.4
C3—Fe1—C8109.38 (14)C4—C5—C1108.2 (3)
C2—Fe1—C8129.09 (14)C4—C5—Fe170.07 (16)
C1—Fe1—C8166.63 (13)C1—C5—Fe169.47 (16)
C7—Fe1—C840.51 (12)C4—C5—H5125.9
C3—Fe1—C10166.11 (14)C1—C5—H5125.9
C2—Fe1—C10151.56 (14)Fe1—C5—H5126.1
C1—Fe1—C10117.85 (13)C11—C6—C7126.8 (3)
C7—Fe1—C1068.73 (12)C11—C6—C10125.8 (3)
C8—Fe1—C1068.07 (14)C7—C6—C10107.4 (3)
C3—Fe1—C567.75 (13)C11—C6—Fe1126.48 (19)
C2—Fe1—C567.92 (13)C7—C6—Fe169.29 (15)
C1—Fe1—C540.30 (12)C10—C6—Fe169.44 (16)
C7—Fe1—C5165.96 (12)C8—C7—C6107.7 (3)
C8—Fe1—C5152.15 (13)C8—C7—Fe169.85 (17)
C10—Fe1—C5107.70 (13)C6—C7—Fe169.79 (16)
C3—Fe1—C6152.12 (14)C8—C7—H7126.1
C2—Fe1—C6117.98 (13)C6—C7—H7126.1
C1—Fe1—C6107.64 (12)Fe1—C7—H7125.8
C7—Fe1—C640.92 (11)C9—C8—C7108.5 (3)
C8—Fe1—C668.29 (13)C9—C8—Fe170.17 (17)
C10—Fe1—C640.98 (11)C7—C8—Fe169.64 (17)
C5—Fe1—C6127.66 (12)C9—C8—H8125.8
C3—Fe1—C9129.10 (14)C7—C8—H8125.8
C2—Fe1—C9166.84 (14)Fe1—C8—H8126.0
C1—Fe1—C9151.75 (14)C8—C9—C10108.9 (3)
C7—Fe1—C967.90 (13)C8—C9—Fe169.80 (18)
C8—Fe1—C940.03 (13)C10—C9—Fe169.72 (16)
C10—Fe1—C940.35 (12)C8—C9—H9125.5
C5—Fe1—C9118.81 (13)C10—C9—H9125.5
C6—Fe1—C968.10 (12)Fe1—C9—H9126.5
C3—Fe1—C440.53 (13)C9—C10—C6107.4 (3)
C2—Fe1—C468.12 (13)C9—C10—Fe169.93 (17)
C1—Fe1—C467.74 (13)C6—C10—Fe169.58 (15)
C7—Fe1—C4152.61 (13)C9—C10—H10126.3
C8—Fe1—C4119.34 (13)C6—C10—H10126.3
C10—Fe1—C4127.70 (12)Fe1—C10—H10125.8
C5—Fe1—C440.10 (12)C12—C11—C6177.7 (3)
C6—Fe1—C4165.50 (12)C11—C12—C13175.5 (3)
C9—Fe1—C4109.02 (13)C18—C13—C14116.4 (3)
C2—C1—C5108.3 (3)C18—C13—C12120.9 (3)
C2—C1—Fe169.73 (17)C14—C13—C12122.7 (3)
C5—C1—Fe170.23 (16)F1—C14—C15118.6 (3)
C2—C1—H1125.8F1—C14—C13119.4 (3)
C5—C1—H1125.8C15—C14—C13122.0 (3)
Fe1—C1—H1125.8F2—C15—C16120.2 (3)
C1—C2—C3107.6 (3)F2—C15—C14120.1 (3)
C1—C2—Fe169.86 (16)C16—C15—C14119.6 (3)
C3—C2—Fe169.65 (17)F3—C16—C15120.0 (3)
C1—C2—H2126.2F3—C16—C17119.9 (3)
C3—C2—H2126.2C15—C16—C17120.0 (3)
Fe1—C2—H2125.9F4—C17—C18120.1 (3)
C2—C3—C4108.3 (3)F4—C17—C16120.0 (3)
C2—C3—Fe169.84 (17)C18—C17—C16119.9 (3)
C4—C3—Fe170.39 (17)F5—C18—C17118.8 (3)
C2—C3—H3125.8F5—C18—C13119.2 (3)
C4—C3—H3125.8C17—C18—C13122.0 (3)
Fe1—C3—H3125.5
C3—Fe1—C1—C237.99 (19)C1—Fe1—C6—C10112.43 (19)
C7—Fe1—C1—C272.1 (2)C7—Fe1—C6—C10118.9 (3)
C8—Fe1—C1—C242.6 (6)C8—Fe1—C6—C1081.1 (2)
C10—Fe1—C1—C2155.99 (19)C5—Fe1—C6—C1072.4 (2)
C5—Fe1—C1—C2119.2 (3)C9—Fe1—C6—C1037.84 (18)
C6—Fe1—C1—C2112.7 (2)C4—Fe1—C6—C1043.4 (5)
C9—Fe1—C1—C2170.9 (2)C11—C6—C7—C8179.5 (3)
C4—Fe1—C1—C281.9 (2)C10—C6—C7—C80.6 (3)
C3—Fe1—C1—C581.3 (2)Fe1—C6—C7—C859.8 (2)
C2—Fe1—C1—C5119.2 (3)C11—C6—C7—Fe1120.7 (3)
C7—Fe1—C1—C5168.67 (17)C10—C6—C7—Fe159.20 (19)
C8—Fe1—C1—C5161.9 (5)C3—Fe1—C7—C886.4 (2)
C10—Fe1—C1—C584.8 (2)C2—Fe1—C7—C8129.4 (2)
C6—Fe1—C1—C5128.05 (18)C1—Fe1—C7—C8169.92 (19)
C9—Fe1—C1—C551.7 (3)C10—Fe1—C7—C880.7 (2)
C4—Fe1—C1—C537.32 (18)C5—Fe1—C7—C8158.5 (4)
C5—C1—C2—C30.2 (3)C6—Fe1—C7—C8118.8 (3)
Fe1—C1—C2—C359.7 (2)C9—Fe1—C7—C837.2 (2)
C5—C1—C2—Fe159.9 (2)C4—Fe1—C7—C851.7 (4)
C3—Fe1—C2—C1118.6 (3)C3—Fe1—C7—C6154.81 (18)
C7—Fe1—C2—C1128.06 (19)C2—Fe1—C7—C6111.85 (19)
C8—Fe1—C2—C1168.36 (18)C1—Fe1—C7—C671.3 (2)
C10—Fe1—C2—C149.0 (3)C8—Fe1—C7—C6118.8 (3)
C5—Fe1—C2—C137.52 (18)C10—Fe1—C7—C638.03 (17)
C6—Fe1—C2—C184.6 (2)C5—Fe1—C7—C639.7 (6)
C9—Fe1—C2—C1160.8 (5)C9—Fe1—C7—C681.60 (19)
C4—Fe1—C2—C180.9 (2)C4—Fe1—C7—C6170.5 (2)
C1—Fe1—C2—C3118.6 (3)C6—C7—C8—C90.1 (3)
C7—Fe1—C2—C3113.3 (2)Fe1—C7—C8—C959.6 (2)
C8—Fe1—C2—C373.0 (2)C6—C7—C8—Fe159.75 (19)
C10—Fe1—C2—C3167.7 (2)C3—Fe1—C8—C9128.4 (2)
C5—Fe1—C2—C381.1 (2)C2—Fe1—C8—C9169.54 (19)
C6—Fe1—C2—C3156.79 (19)C1—Fe1—C8—C9156.0 (5)
C9—Fe1—C2—C342.2 (6)C7—Fe1—C8—C9119.5 (3)
C4—Fe1—C2—C337.74 (18)C10—Fe1—C8—C937.05 (19)
C1—C2—C3—C40.3 (3)C5—Fe1—C8—C949.5 (4)
Fe1—C2—C3—C460.1 (2)C6—Fe1—C8—C981.4 (2)
C1—C2—C3—Fe159.8 (2)C4—Fe1—C8—C985.0 (2)
C1—Fe1—C3—C237.89 (19)C3—Fe1—C8—C7112.1 (2)
C7—Fe1—C3—C284.7 (2)C2—Fe1—C8—C770.9 (2)
C8—Fe1—C3—C2128.1 (2)C1—Fe1—C8—C736.5 (6)
C10—Fe1—C3—C2155.0 (5)C10—Fe1—C8—C782.5 (2)
C5—Fe1—C3—C281.6 (2)C5—Fe1—C8—C7169.0 (2)
C6—Fe1—C3—C248.1 (3)C6—Fe1—C8—C738.17 (19)
C9—Fe1—C3—C2168.64 (19)C9—Fe1—C8—C7119.5 (3)
C4—Fe1—C3—C2119.1 (3)C4—Fe1—C8—C7155.52 (19)
C2—Fe1—C3—C4119.1 (3)C7—C8—C9—C100.4 (4)
C1—Fe1—C3—C481.2 (2)Fe1—C8—C9—C1058.9 (2)
C7—Fe1—C3—C4156.23 (18)C7—C8—C9—Fe159.3 (2)
C8—Fe1—C3—C4112.8 (2)C3—Fe1—C9—C872.4 (2)
C10—Fe1—C3—C435.9 (6)C2—Fe1—C9—C838.2 (6)
C5—Fe1—C3—C437.50 (18)C1—Fe1—C9—C8168.5 (2)
C6—Fe1—C3—C4167.2 (2)C7—Fe1—C9—C837.59 (19)
C9—Fe1—C3—C472.3 (2)C10—Fe1—C9—C8120.3 (3)
C2—C3—C4—C50.3 (3)C5—Fe1—C9—C8156.08 (19)
Fe1—C3—C4—C559.5 (2)C6—Fe1—C9—C881.9 (2)
C2—C3—C4—Fe159.8 (2)C4—Fe1—C9—C8113.3 (2)
C3—Fe1—C4—C5119.0 (3)C3—Fe1—C9—C10167.30 (18)
C2—Fe1—C4—C581.3 (2)C2—Fe1—C9—C10158.5 (5)
C1—Fe1—C4—C537.50 (18)C1—Fe1—C9—C1048.2 (3)
C7—Fe1—C4—C5169.1 (2)C7—Fe1—C9—C1082.72 (19)
C8—Fe1—C4—C5155.12 (19)C8—Fe1—C9—C10120.3 (3)
C10—Fe1—C4—C571.3 (2)C5—Fe1—C9—C1083.6 (2)
C6—Fe1—C4—C536.5 (5)C6—Fe1—C9—C1038.43 (18)
C9—Fe1—C4—C5112.5 (2)C4—Fe1—C9—C10126.40 (19)
C2—Fe1—C4—C337.72 (19)C8—C9—C10—C60.8 (3)
C1—Fe1—C4—C381.5 (2)Fe1—C9—C10—C659.73 (19)
C7—Fe1—C4—C350.1 (4)C8—C9—C10—Fe158.9 (2)
C8—Fe1—C4—C385.9 (2)C11—C6—C10—C9179.2 (3)
C10—Fe1—C4—C3169.76 (19)C7—C6—C10—C90.8 (3)
C5—Fe1—C4—C3119.0 (3)Fe1—C6—C10—C960.0 (2)
C6—Fe1—C4—C3155.5 (4)C11—C6—C10—Fe1120.8 (3)
C9—Fe1—C4—C3128.6 (2)C7—C6—C10—Fe159.11 (19)
C3—C4—C5—C10.2 (3)C3—Fe1—C10—C945.3 (6)
Fe1—C4—C5—C159.2 (2)C2—Fe1—C10—C9169.9 (2)
C3—C4—C5—Fe159.0 (2)C1—Fe1—C10—C9156.46 (19)
C2—C1—C5—C40.0 (3)C7—Fe1—C10—C980.5 (2)
Fe1—C1—C5—C459.6 (2)C8—Fe1—C10—C936.76 (19)
C2—C1—C5—Fe159.6 (2)C5—Fe1—C10—C9113.9 (2)
C3—Fe1—C5—C437.89 (19)C6—Fe1—C10—C9118.5 (3)
C2—Fe1—C5—C481.8 (2)C4—Fe1—C10—C974.1 (2)
C1—Fe1—C5—C4119.4 (3)C3—Fe1—C10—C6163.8 (5)
C7—Fe1—C5—C4158.9 (5)C2—Fe1—C10—C651.5 (3)
C8—Fe1—C5—C451.7 (3)C1—Fe1—C10—C685.1 (2)
C10—Fe1—C5—C4128.14 (19)C7—Fe1—C10—C637.97 (17)
C6—Fe1—C5—C4169.15 (17)C8—Fe1—C10—C681.69 (19)
C9—Fe1—C5—C485.7 (2)C5—Fe1—C10—C6127.62 (18)
C3—Fe1—C5—C181.5 (2)C9—Fe1—C10—C6118.5 (3)
C2—Fe1—C5—C137.61 (19)C4—Fe1—C10—C6167.43 (17)
C7—Fe1—C5—C139.5 (6)C18—C13—C14—F1179.7 (2)
C8—Fe1—C5—C1171.1 (3)C12—C13—C14—F11.4 (4)
C10—Fe1—C5—C1112.45 (19)C18—C13—C14—C150.2 (4)
C6—Fe1—C5—C171.4 (2)C12—C13—C14—C15178.7 (3)
C9—Fe1—C5—C1154.93 (19)F1—C14—C15—F21.7 (4)
C4—Fe1—C5—C1119.4 (3)C13—C14—C15—F2178.4 (2)
C3—Fe1—C6—C1168.3 (4)F1—C14—C15—C16179.7 (2)
C2—Fe1—C6—C1135.1 (3)C13—C14—C15—C160.2 (4)
C1—Fe1—C6—C117.5 (3)F2—C15—C16—F33.0 (4)
C7—Fe1—C6—C11121.1 (3)C14—C15—C16—F3178.4 (2)
C8—Fe1—C6—C11158.9 (3)F2—C15—C16—C17178.2 (2)
C10—Fe1—C6—C11120.0 (3)C14—C15—C16—C170.4 (4)
C5—Fe1—C6—C1147.6 (3)F3—C16—C17—F41.9 (4)
C9—Fe1—C6—C11157.8 (3)C15—C16—C17—F4179.4 (3)
C4—Fe1—C6—C1176.5 (5)F3—C16—C17—C18178.2 (2)
C3—Fe1—C6—C752.8 (3)C15—C16—C17—C180.6 (4)
C2—Fe1—C6—C786.0 (2)F4—C17—C18—F51.2 (4)
C1—Fe1—C6—C7128.66 (18)C16—C17—C18—F5178.9 (2)
C8—Fe1—C6—C737.81 (19)F4—C17—C18—C13179.3 (2)
C10—Fe1—C6—C7118.9 (3)C16—C17—C18—C130.6 (4)
C5—Fe1—C6—C7168.71 (17)C14—C13—C18—F5179.1 (2)
C9—Fe1—C6—C781.1 (2)C12—C13—C18—F52.0 (4)
C4—Fe1—C6—C7162.3 (4)C14—C13—C18—C170.4 (4)
C3—Fe1—C6—C10171.8 (2)C12—C13—C18—C17178.5 (3)
C2—Fe1—C6—C10155.05 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···F5i0.932.503.176 (3)130
Symmetry code: (i) x+1, y+2, z+2.

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C13H4F5)]
Mr376.10
Crystal system, space groupTriclinic, P1
Temperature (K)292
a, b, c (Å)6.0767 (9), 10.7164 (15), 12.6014 (18)
α, β, γ (°)65.725 (2), 89.364 (3), 78.726 (2)
V3)731.41 (18)
Z2
Radiation typeMo Kα
µ (mm1)1.08
Crystal size (mm)0.30 × 0.04 × 0.02
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4793, 2533, 2169
Rint0.021
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.105, 1.05
No. of reflections2533
No. of parameters217
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.25

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···F5i0.932.503.176 (3)130
Symmetry code: (i) x+1, y+2, z+2.
 

Acknowledgements

The authors are grateful to Mr Xianggao Meng for the data collection.

References

First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDebroy, P. & Roy, S. (2007). Coord. Chem. Rev. 251, 203–221.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTorres, J. C., Pilli, R. A., Vargas, M. D., Violante, F. A., Garden, S. J. & Pinto, A. C. (2002). Tetrahedron, 58, 4487–4492.  Web of Science CrossRef CAS Google Scholar
First citationValdebenito, C., Garland, M. T., Fuentealba, M. & Escobar, C. A. (2010). Acta Cryst. E66, m838.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationZora, M., Açıkgöz, C., Tumay, T. A., Odabaşoğlu, M. & Büyükgüngör, O. (2006). Acta Cryst. C62, m327–m330.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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