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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): m461.
Published online 2009 March 28. doi:  10.1107/S1600536809011039
PMCID: PMC2969081

N-(2-Ferrocenylethyl­idene)-4-(trifluoro­meth­yl)aniline

Abstract

The title compound, [Fe(C5H5)(C13H9F3N)], was prepared by a condensation reaction from ferrocenylcarbaldehyde and 4-(trifluoro­meth­yl)aniline. The cyclo­penta­dienyl (Cp) rings are coplanar [dihedral angle = 1.4 (3)°] and the imine function is situated in the same plane. The aromatic substituent is bent out of the plane of the Cp ring to which the imine group is attached by 44.5 (4)°. The F atoms of the trifluoro­methyl substituent are disordered [occupancies 0.52 (2)/0.48 (2)].

Related literature

For the structures of ferrocenylpropenal and imines derived from it, see: Imhof (1997 [triangle], 1998 [triangle], 2004 [triangle], 2005 [triangle]).

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Object name is e-65-0m461-scheme1.jpg

Experimental

Crystal data

  • [Fe(C5H5)(C13H9F3N)]
  • M r = 357.15
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m461-efi1.jpg
  • a = 5.8446 (7) Å
  • b = 10.383 (1) Å
  • c = 12.972 (2) Å
  • α = 100.467 (8)°
  • β = 91.670 (5)°
  • γ = 99.152 (8)°
  • V = 762.9 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.02 mm−1
  • T = 183 K
  • 0.12 × 0.08 × 0.02 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: none
  • 2064 measured reflections
  • 2064 independent reflections
  • 1937 reflections with I > 2σ(I)
  • θmax = 23.3°

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.099
  • S = 0.79
  • 2064 reflections
  • 236 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: COLLECT (Nonius, 1998 [triangle]); cell refinement: DENZO (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP (Siemens, 1990 [triangle]); software used to prepare material for publication: XP.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011039/hg2490sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011039/hg2490Isup2.hkl

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

Acknowledgments

The author thanks the Deutsche Forschungsgemeinschaft (SFB 436) for financial support.

supplementary crystallographic information

Comment

In the course of a study on imines derived from aldehydes and amines exhibiting ferrocenyl substituents we recognized that ferrocenyl-prop-2-enal as well as some of the corresponding imines crystallize in non-centrosymmetric space groups (Imhof, 1997, 1998, 2004, 2005). The title compound crystallizes in the centrosymmetric space group P1. All bond lengths and bond angles are of expected values. The Cp rings are coplanar (dihedral angle 1.4 (3)°) and the imine function is situated in the same plane. The aromatic substituent is bent out of the plane of the Cp the imine moiety is attached to by 44.5 (4)°. The shortest intermolecular distances are observed between fluorine atoms and hydrogen atoms of a Cp ring. Nevertheless, since the CF3 substituent is highly disordered these contacts should not be discussed as C–H···F hydrogen bonds.

Experimental

500 mg ferrocenylcarbaldehyde (2.34 mmol) were dissolved in 20 ml of anhydrous ethanol together with an equimolar amount of 4-trifluoromethyl-aniline (376 mg) and 10 mg of p-toluenesulfonic acid. The solution was stirred at room temperature for 1 h. After evaporation of 15 ml of the solvent the remaining solution was put into the refrigerator at 277 K resulting in the precipitation of the title compound as crystalline material (yield: 600 mg, 72%). MS (EI) [m/z, %]: 357 (M+, 100), 338 (M+ - F, 11), 292 (M+ - Cp, 3), 236 (M+ - CpFe, 3), 216 (C12H8NF2+, 71), 186 (C10H10Fe+, 11), 167 (C12H9N+, 49, 121 (CpFe+, 19), 56 (Fe+, 13); 1H-NMR (CDCl3, 298 K) [p.p.m.]: 4.12 (s, 5H, Cp), 4.18–4.45 (m, 4H, Cp), 7.14–7.19 (m, 2H, CHar), 7.58–7.61 (m, 2H, CHar), 8.08 (m, 1H, CH=N).

Refinement

Hydrogen atoms were positioned geometrically at distances of 0.95 Å for aromatic C—H functions and the imine C—H group and were refined riding on their parent atoms with isotropic thermal parameters of 1.2 times the corresponding values of their parent atoms.

Figures

Fig. 1.
Molecular structure of the title compound with displacement ellipsoids at the 40% probability level.

Crystal data

[Fe(C5H5)(C13H9F3N)]Z = 2
Mr = 357.15F(000) = 364
Triclinic, P1Dx = 1.555 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.8446 (7) ÅCell parameters from 2064 reflections
b = 10.383 (1) Åθ = 3.2–23.3°
c = 12.972 (2) ŵ = 1.02 mm1
α = 100.467 (8)°T = 183 K
β = 91.670 (5)°Plate, red
γ = 99.152 (8)°0.12 × 0.08 × 0.02 mm
V = 762.9 (2) Å3

Data collection

Nonius KappaCCD diffractometer1937 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeθmax = 23.3°, θmin = 3.5°
graphiteh = 0→6
ω and [var phi] scansk = −11→11
2064 measured reflectionsl = −14→14
2064 independent reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 0.79w = 1/[σ2(Fo2) + (0.0772P)2 + 0.4666P] where P = (Fo2 + 2Fc2)/3
2064 reflections(Δ/σ)max = 0.003
236 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = −0.41 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
Fe10.48698 (5)0.24098 (3)0.23674 (3)0.03550 (19)
C10.3215 (5)0.3525 (3)0.0515 (2)0.0442 (6)
H10.44210.36030.00430.053*
N10.1114 (4)0.3180 (2)0.01264 (18)0.0461 (6)
C20.0736 (5)0.2917 (3)−0.0978 (2)0.0420 (6)
C30.2148 (5)0.2243 (3)−0.1663 (2)0.0467 (7)
H30.34360.1928−0.13910.056*
C40.1667 (5)0.2035 (3)−0.2739 (2)0.0483 (7)
H40.26360.1586−0.32020.058*
C5−0.0220 (5)0.2480 (3)−0.3142 (2)0.0463 (7)
C6−0.1655 (5)0.3124 (3)−0.2467 (2)0.0467 (7)
H6−0.29610.3420−0.27400.056*
C7−0.1173 (4)0.3332 (3)−0.1395 (2)0.0463 (7)
H7−0.21670.3767−0.09350.056*
C8−0.0774 (7)0.2247 (4)−0.4301 (3)0.0617 (9)
F1−0.056 (3)0.3334 (12)−0.4661 (11)0.101 (5)0.52 (2)
F20.1063 (14)0.1998 (13)−0.4864 (8)0.108 (4)0.52 (2)
F3−0.312 (3)0.184 (3)−0.4518 (9)0.170 (8)0.52 (2)
F1X−0.140 (4)0.3235 (14)−0.4636 (12)0.124 (6)0.48 (2)
F2X0.020 (5)0.144 (2)−0.4837 (9)0.195 (9)0.48 (2)
F3X−0.225 (3)0.1227 (9)−0.4659 (7)0.097 (4)0.48 (2)
C90.3850 (4)0.3802 (3)0.1628 (2)0.0417 (6)
C100.2396 (5)0.3601 (3)0.2476 (2)0.0440 (6)
H100.07630.33150.24180.053*
C110.3828 (5)0.3903 (3)0.3413 (2)0.0492 (7)
H110.33180.38550.40960.059*
C120.6162 (5)0.4291 (3)0.3163 (2)0.0494 (7)
H120.74740.45460.36490.059*
C130.6191 (5)0.4234 (3)0.2070 (2)0.0463 (7)
H130.75240.44430.16920.056*
C140.4441 (5)0.0678 (3)0.1292 (2)0.0520 (7)
H140.37900.05480.05940.062*
C150.6824 (5)0.1108 (3)0.1618 (2)0.0477 (7)
H150.80490.13120.11780.057*
C160.7044 (5)0.1177 (3)0.2719 (2)0.0455 (7)
H160.84440.14350.31490.055*
C170.4799 (5)0.0790 (3)0.3063 (2)0.0498 (7)
H170.44360.07480.37670.060*
C180.3203 (5)0.0479 (3)0.2188 (3)0.0503 (7)
H180.15790.01870.21950.060*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0315 (3)0.0357 (3)0.0406 (3)0.00535 (17)0.00559 (16)0.01043 (17)
C10.0399 (15)0.0416 (15)0.0553 (17)0.0084 (12)0.0093 (12)0.0175 (12)
N10.0393 (13)0.0502 (14)0.0516 (14)0.0081 (10)0.0064 (10)0.0159 (11)
C20.0398 (14)0.0418 (16)0.0456 (15)0.0028 (12)0.0052 (11)0.0147 (12)
C30.0395 (14)0.0425 (16)0.0614 (18)0.0096 (12)0.0051 (13)0.0160 (13)
C40.0481 (16)0.0436 (16)0.0538 (17)0.0066 (13)0.0155 (13)0.0100 (13)
C50.0520 (16)0.0393 (16)0.0486 (16)0.0025 (13)0.0053 (12)0.0147 (12)
C60.0414 (15)0.0453 (16)0.0550 (17)0.0041 (12)−0.0011 (12)0.0174 (13)
C70.0376 (14)0.0494 (17)0.0545 (17)0.0081 (12)0.0080 (12)0.0149 (13)
C80.079 (2)0.053 (2)0.0518 (18)−0.002 (2)0.0017 (18)0.0162 (17)
F10.148 (8)0.086 (7)0.061 (4)−0.032 (7)−0.020 (4)0.042 (4)
F20.082 (5)0.202 (12)0.053 (4)0.038 (5)0.032 (3)0.040 (5)
F30.102 (7)0.304 (19)0.065 (5)−0.074 (10)−0.022 (4)0.032 (9)
F1X0.217 (15)0.110 (11)0.062 (5)0.098 (10)−0.029 (7)0.008 (6)
F2X0.39 (3)0.175 (14)0.056 (5)0.198 (16)−0.015 (11)−0.023 (7)
F3X0.126 (9)0.094 (6)0.048 (3)−0.055 (5)0.000 (5)0.015 (3)
C90.0396 (14)0.0378 (14)0.0508 (16)0.0084 (11)0.0056 (12)0.0141 (12)
C100.0394 (14)0.0407 (15)0.0544 (17)0.0117 (12)0.0072 (12)0.0102 (12)
C110.0588 (18)0.0424 (16)0.0493 (17)0.0145 (13)0.0102 (13)0.0100 (13)
C120.0495 (16)0.0392 (15)0.0571 (18)0.0056 (12)−0.0043 (13)0.0060 (13)
C130.0400 (14)0.0403 (15)0.0596 (18)0.0019 (12)0.0045 (12)0.0162 (13)
C140.0546 (17)0.0437 (16)0.0561 (18)0.0146 (13)−0.0041 (14)0.0010 (13)
C150.0458 (16)0.0470 (17)0.0532 (17)0.0145 (13)0.0115 (13)0.0094 (13)
C160.0424 (15)0.0432 (16)0.0544 (17)0.0123 (12)0.0019 (12)0.0140 (12)
C170.0567 (18)0.0427 (16)0.0560 (17)0.0136 (13)0.0108 (14)0.0193 (13)
C180.0386 (15)0.0353 (15)0.076 (2)0.0027 (12)0.0068 (14)0.0112 (13)

Geometric parameters (Å, °)

Fe1—C92.027 (3)C8—F3X1.260 (10)
Fe1—C102.038 (3)C8—F1X1.284 (14)
Fe1—C132.037 (3)C8—F11.288 (11)
Fe1—C152.038 (3)C8—F21.348 (8)
Fe1—C162.039 (3)C8—F31.372 (13)
Fe1—C142.041 (3)F2X—F3X1.44 (4)
Fe1—C172.043 (3)C9—C101.434 (4)
Fe1—C112.049 (3)C9—C131.438 (4)
Fe1—C122.050 (3)C10—C111.412 (4)
Fe1—C182.054 (3)C10—H100.9500
C1—N11.284 (3)C11—C121.424 (4)
C1—C91.446 (4)C11—H110.9500
C1—H10.9500C12—C131.408 (4)
N1—C21.413 (4)C12—H120.9500
C2—C71.388 (4)C13—H130.9500
C2—C31.400 (4)C14—C181.416 (4)
C3—C41.386 (4)C14—C151.420 (4)
C3—H30.9500C14—H140.9500
C4—C51.385 (4)C15—C161.418 (4)
C4—H40.9500C15—H150.9500
C5—C61.387 (4)C16—C171.419 (4)
C5—C81.496 (4)C16—H160.9500
C6—C71.381 (4)C17—C181.404 (4)
C6—H60.9500C17—H170.9500
C7—H70.9500C18—H180.9500
C8—F2X1.213 (12)
C9—Fe1—C1041.32 (11)F1X—C8—F2103.8 (11)
C9—Fe1—C1341.45 (11)F1—C8—F285.3 (10)
C10—Fe1—C1369.23 (11)F2X—C8—F3107 (2)
C9—Fe1—C15119.87 (12)F3X—C8—F338.2 (9)
C10—Fe1—C15155.72 (12)F1X—C8—F377.4 (10)
C13—Fe1—C15106.89 (12)F1—C8—F398.7 (10)
C9—Fe1—C16155.40 (12)F2—C8—F3131.5 (11)
C10—Fe1—C16162.11 (11)F2X—C8—C5116.2 (7)
C13—Fe1—C16120.16 (11)F3X—C8—C5114.9 (5)
C15—Fe1—C1640.69 (12)F1X—C8—C5114.7 (7)
C9—Fe1—C14106.89 (12)F1—C8—C5112.6 (7)
C10—Fe1—C14120.63 (12)F2—C8—C5112.7 (5)
C13—Fe1—C14124.95 (12)F3—C8—C5110.0 (6)
C15—Fe1—C1440.75 (11)C8—F2X—F3X55.8 (11)
C16—Fe1—C1468.29 (12)C8—F3X—F2X52.8 (9)
C9—Fe1—C17161.88 (12)C10—C9—C13107.4 (2)
C10—Fe1—C17125.05 (11)C10—C9—C1128.3 (2)
C13—Fe1—C17155.74 (12)C13—C9—C1124.1 (2)
C15—Fe1—C1768.32 (12)C10—C9—Fe169.78 (15)
C16—Fe1—C1740.68 (11)C13—C9—Fe169.64 (15)
C14—Fe1—C1767.88 (12)C1—C9—Fe1121.78 (19)
C9—Fe1—C1168.69 (12)C11—C10—C9107.8 (2)
C10—Fe1—C1140.42 (12)C11—C10—Fe170.21 (17)
C13—Fe1—C1168.35 (12)C9—C10—Fe168.91 (14)
C15—Fe1—C11162.24 (12)C11—C10—H10126.1
C16—Fe1—C11125.61 (12)C9—C10—H10126.1
C14—Fe1—C11155.91 (13)Fe1—C10—H10126.3
C17—Fe1—C11108.56 (12)C10—C11—C12108.5 (3)
C9—Fe1—C1268.79 (11)C10—C11—Fe169.37 (16)
C10—Fe1—C1268.55 (11)C12—C11—Fe169.71 (16)
C13—Fe1—C1240.31 (12)C10—C11—H11125.7
C15—Fe1—C12124.85 (12)C12—C11—H11125.7
C16—Fe1—C12107.87 (12)Fe1—C11—H11126.8
C14—Fe1—C12161.84 (13)C13—C12—C11108.3 (3)
C17—Fe1—C12121.59 (12)C13—C12—Fe169.33 (16)
C11—Fe1—C1240.65 (12)C11—C12—Fe169.64 (16)
C9—Fe1—C18124.84 (12)C13—C12—H12125.9
C10—Fe1—C18107.73 (11)C11—C12—H12125.9
C13—Fe1—C18162.30 (13)Fe1—C12—H12126.7
C15—Fe1—C1868.31 (12)C12—C13—C9108.0 (2)
C16—Fe1—C1868.09 (11)C12—C13—Fe170.36 (16)
C14—Fe1—C1840.46 (12)C9—C13—Fe168.90 (15)
C17—Fe1—C1840.09 (12)C12—C13—H13126.0
C11—Fe1—C18121.37 (12)C9—C13—H13126.0
C12—Fe1—C18156.31 (13)Fe1—C13—H13126.3
N1—C1—C9123.8 (2)C18—C14—C15108.2 (3)
N1—C1—H1118.1C18—C14—Fe170.27 (16)
C9—C1—H1118.1C15—C14—Fe169.53 (16)
C1—N1—C2118.0 (2)C18—C14—H14125.9
C7—C2—C3118.9 (3)C15—C14—H14125.9
C7—C2—N1117.4 (3)Fe1—C14—H14125.9
C3—C2—N1123.6 (3)C16—C15—C14107.6 (3)
C4—C3—C2120.0 (3)C16—C15—Fe169.69 (16)
C4—C3—H3120.0C14—C15—Fe169.72 (16)
C2—C3—H3120.0C16—C15—H15126.2
C3—C4—C5120.4 (3)C14—C15—H15126.2
C3—C4—H4119.8Fe1—C15—H15126.0
C5—C4—H4119.8C15—C16—C17107.8 (3)
C4—C5—C6120.0 (3)C15—C16—Fe169.62 (17)
C4—C5—C8120.8 (3)C17—C16—Fe169.82 (16)
C6—C5—C8119.2 (3)C15—C16—H16126.1
C7—C6—C5119.7 (3)C17—C16—H16126.1
C7—C6—H6120.2Fe1—C16—H16126.0
C5—C6—H6120.2C18—C17—C16108.5 (3)
C6—C7—C2121.1 (3)C18—C17—Fe170.35 (17)
C6—C7—H7119.4C16—C17—Fe169.50 (16)
C2—C7—H7119.4C18—C17—H17125.8
F2X—C8—F3X71.3 (19)C16—C17—H17125.8
F2X—C8—F1X122.9 (13)Fe1—C17—H17126.0
F3X—C8—F1X108.1 (9)C17—C18—C14107.9 (2)
F2X—C8—F1110.8 (16)C17—C18—Fe169.56 (16)
F3X—C8—F1124.4 (8)C14—C18—Fe169.28 (16)
F1X—C8—F122.1 (12)C17—C18—H18126.0
F2X—C8—F231.8 (15)C14—C18—H18126.0
F3X—C8—F2101.3 (9)Fe1—C18—H18126.7
C9—C1—N1—C2−178.9 (2)C18—Fe1—C12—C11−48.3 (3)
C1—N1—C2—C7−141.5 (3)C11—C12—C13—C9−0.1 (3)
C1—N1—C2—C339.9 (4)Fe1—C12—C13—C958.81 (19)
C7—C2—C3—C41.9 (4)C11—C12—C13—Fe1−58.9 (2)
N1—C2—C3—C4−179.5 (2)C10—C9—C13—C120.1 (3)
C2—C3—C4—C5−0.6 (4)C1—C9—C13—C12−175.0 (3)
C3—C4—C5—C6−0.7 (4)Fe1—C9—C13—C12−59.7 (2)
C3—C4—C5—C8−179.2 (3)C10—C9—C13—Fe159.83 (18)
C4—C5—C6—C70.8 (4)C1—C9—C13—Fe1−115.3 (3)
C8—C5—C6—C7179.3 (3)C9—Fe1—C13—C12119.3 (2)
C5—C6—C7—C20.5 (4)C10—Fe1—C13—C1280.94 (18)
C3—C2—C7—C6−1.8 (4)C15—Fe1—C13—C12−124.41 (18)
N1—C2—C7—C6179.4 (2)C16—Fe1—C13—C12−82.1 (2)
C4—C5—C8—F2X14.3 (19)C14—Fe1—C13—C12−165.50 (16)
C6—C5—C8—F2X−164.2 (19)C17—Fe1—C13—C12−49.8 (3)
C4—C5—C8—F3X94.9 (9)C11—Fe1—C13—C1237.44 (17)
C6—C5—C8—F3X−83.7 (9)C18—Fe1—C13—C12164.2 (3)
C4—C5—C8—F1X−139.0 (12)C10—Fe1—C13—C9−38.38 (16)
C6—C5—C8—F1X42.5 (12)C15—Fe1—C13—C9116.27 (17)
C4—C5—C8—F1−114.9 (8)C16—Fe1—C13—C9158.53 (16)
C6—C5—C8—F166.5 (9)C14—Fe1—C13—C975.2 (2)
C4—C5—C8—F2−20.5 (7)C17—Fe1—C13—C9−169.2 (2)
C6—C5—C8—F2161.0 (6)C11—Fe1—C13—C9−81.87 (18)
C4—C5—C8—F3136.1 (14)C12—Fe1—C13—C9−119.3 (2)
C6—C5—C8—F3−42.5 (14)C18—Fe1—C13—C944.9 (4)
F1X—C8—F2X—F3X−99.9 (19)C9—Fe1—C14—C18−124.34 (17)
F1—C8—F2X—F3X−120.7 (11)C10—Fe1—C14—C18−81.4 (2)
F2—C8—F2X—F3X−160 (2)C13—Fe1—C14—C18−166.32 (17)
F3—C8—F2X—F3X−14.1 (12)C15—Fe1—C14—C18119.2 (3)
C5—C8—F2X—F3X109.2 (9)C16—Fe1—C14—C1881.25 (18)
F1X—C8—F3X—F2X119.5 (12)C17—Fe1—C14—C1837.24 (17)
F1—C8—F3X—F2X102.8 (12)C11—Fe1—C14—C18−48.9 (4)
F2—C8—F3X—F2X10.8 (11)C12—Fe1—C14—C18162.4 (3)
F3—C8—F3X—F2X157.8 (16)C9—Fe1—C14—C15116.43 (18)
C5—C8—F3X—F2X−110.9 (10)C10—Fe1—C14—C15159.34 (17)
N1—C1—C9—C108.2 (4)C13—Fe1—C14—C1574.4 (2)
N1—C1—C9—C13−177.7 (3)C16—Fe1—C14—C15−37.99 (17)
N1—C1—C9—Fe196.6 (3)C17—Fe1—C14—C15−81.99 (19)
C13—Fe1—C9—C10−118.5 (2)C11—Fe1—C14—C15−168.1 (2)
C15—Fe1—C9—C10159.84 (16)C12—Fe1—C14—C1543.1 (4)
C16—Fe1—C9—C10−167.9 (2)C18—Fe1—C14—C15−119.2 (3)
C14—Fe1—C9—C10117.46 (17)C18—C14—C15—C16−0.2 (3)
C17—Fe1—C9—C1047.2 (4)Fe1—C14—C15—C1659.6 (2)
C11—Fe1—C9—C10−37.45 (16)C18—C14—C15—Fe1−59.9 (2)
C12—Fe1—C9—C10−81.22 (17)C9—Fe1—C15—C16160.10 (16)
C18—Fe1—C9—C1076.70 (19)C10—Fe1—C15—C16−166.3 (2)
C10—Fe1—C9—C13118.5 (2)C13—Fe1—C15—C16116.89 (17)
C15—Fe1—C9—C13−81.71 (19)C14—Fe1—C15—C16−118.7 (2)
C16—Fe1—C9—C13−49.5 (3)C17—Fe1—C15—C16−37.88 (17)
C14—Fe1—C9—C13−124.09 (17)C11—Fe1—C15—C1645.3 (4)
C17—Fe1—C9—C13165.6 (3)C12—Fe1—C15—C1676.3 (2)
C11—Fe1—C9—C1381.00 (18)C18—Fe1—C15—C16−81.18 (18)
C12—Fe1—C9—C1337.23 (17)C9—Fe1—C15—C14−81.2 (2)
C18—Fe1—C9—C13−164.85 (17)C10—Fe1—C15—C14−47.6 (3)
C10—Fe1—C9—C1−123.3 (3)C13—Fe1—C15—C14−124.39 (18)
C13—Fe1—C9—C1118.2 (3)C16—Fe1—C15—C14118.7 (2)
C15—Fe1—C9—C136.5 (3)C17—Fe1—C15—C1480.83 (19)
C16—Fe1—C9—C168.8 (3)C11—Fe1—C15—C14164.0 (3)
C14—Fe1—C9—C1−5.9 (2)C12—Fe1—C15—C14−164.95 (18)
C17—Fe1—C9—C1−76.1 (4)C18—Fe1—C15—C1437.54 (18)
C11—Fe1—C9—C1−160.8 (2)C14—C15—C16—C170.0 (3)
C12—Fe1—C9—C1155.5 (2)Fe1—C15—C16—C1759.63 (19)
C18—Fe1—C9—C1−46.6 (3)C14—C15—C16—Fe1−59.7 (2)
C13—C9—C10—C11−0.1 (3)C9—Fe1—C16—C15−45.2 (3)
C1—C9—C10—C11174.8 (3)C10—Fe1—C16—C15161.5 (3)
Fe1—C9—C10—C1159.68 (19)C13—Fe1—C16—C15−80.76 (19)
C13—C9—C10—Fe1−59.74 (18)C14—Fe1—C16—C1538.04 (17)
C1—C9—C10—Fe1115.1 (3)C17—Fe1—C16—C15118.9 (2)
C9—Fe1—C10—C11−119.1 (2)C11—Fe1—C16—C15−164.53 (16)
C13—Fe1—C10—C11−80.61 (18)C12—Fe1—C16—C15−123.09 (17)
C15—Fe1—C10—C11−165.7 (2)C18—Fe1—C16—C1581.77 (18)
C16—Fe1—C10—C1144.4 (4)C9—Fe1—C16—C17−164.1 (2)
C14—Fe1—C10—C11160.21 (17)C10—Fe1—C16—C1742.6 (4)
C17—Fe1—C10—C1177.1 (2)C13—Fe1—C16—C17160.32 (16)
C12—Fe1—C10—C11−37.27 (17)C15—Fe1—C16—C17−118.9 (2)
C18—Fe1—C10—C11117.87 (18)C14—Fe1—C16—C17−80.88 (19)
C13—Fe1—C10—C938.50 (16)C11—Fe1—C16—C1776.6 (2)
C15—Fe1—C10—C9−46.6 (3)C12—Fe1—C16—C17118.00 (18)
C16—Fe1—C10—C9163.6 (3)C18—Fe1—C16—C17−37.15 (18)
C14—Fe1—C10—C9−80.67 (19)C15—C16—C17—C180.3 (3)
C17—Fe1—C10—C9−163.83 (16)Fe1—C16—C17—C1859.8 (2)
C11—Fe1—C10—C9119.1 (2)C15—C16—C17—Fe1−59.5 (2)
C12—Fe1—C10—C981.85 (17)C9—Fe1—C17—C1838.9 (4)
C18—Fe1—C10—C9−123.01 (17)C10—Fe1—C17—C1875.2 (2)
C9—C10—C11—C120.0 (3)C13—Fe1—C17—C18−164.7 (2)
Fe1—C10—C11—C1258.9 (2)C15—Fe1—C17—C18−81.65 (18)
C9—C10—C11—Fe1−58.87 (18)C16—Fe1—C17—C18−119.5 (2)
C9—Fe1—C11—C1038.25 (16)C14—Fe1—C17—C18−37.57 (17)
C13—Fe1—C11—C1082.96 (18)C11—Fe1—C17—C18116.99 (18)
C15—Fe1—C11—C10160.6 (3)C12—Fe1—C17—C18159.84 (17)
C16—Fe1—C11—C10−164.66 (16)C9—Fe1—C17—C16158.5 (3)
C14—Fe1—C11—C10−45.5 (4)C10—Fe1—C17—C16−165.28 (16)
C17—Fe1—C11—C10−122.69 (17)C13—Fe1—C17—C16−45.1 (3)
C12—Fe1—C11—C10120.1 (2)C15—Fe1—C17—C1637.89 (17)
C18—Fe1—C11—C10−80.5 (2)C14—Fe1—C17—C1681.96 (18)
C9—Fe1—C11—C12−81.84 (18)C11—Fe1—C17—C16−123.48 (18)
C10—Fe1—C11—C12−120.1 (2)C12—Fe1—C17—C16−80.6 (2)
C13—Fe1—C11—C12−37.14 (17)C18—Fe1—C17—C16119.5 (3)
C15—Fe1—C11—C1240.5 (4)C16—C17—C18—C14−0.4 (3)
C16—Fe1—C11—C1275.2 (2)Fe1—C17—C18—C1458.8 (2)
C14—Fe1—C11—C12−165.6 (3)C16—C17—C18—Fe1−59.2 (2)
C17—Fe1—C11—C12117.21 (18)C15—C14—C18—C170.4 (3)
C18—Fe1—C11—C12159.45 (17)Fe1—C14—C18—C17−59.0 (2)
C10—C11—C12—C130.1 (3)C15—C14—C18—Fe159.4 (2)
Fe1—C11—C12—C1358.7 (2)C9—Fe1—C18—C17−166.23 (16)
C10—C11—C12—Fe1−58.7 (2)C10—Fe1—C18—C17−123.81 (17)
C9—Fe1—C12—C13−38.26 (17)C13—Fe1—C18—C17159.1 (3)
C10—Fe1—C12—C13−82.77 (18)C15—Fe1—C18—C1781.67 (18)
C15—Fe1—C12—C1374.1 (2)C16—Fe1—C18—C1737.69 (17)
C16—Fe1—C12—C13115.86 (18)C14—Fe1—C18—C17119.5 (2)
C14—Fe1—C12—C1341.2 (4)C11—Fe1—C18—C17−81.6 (2)
C17—Fe1—C12—C13158.37 (17)C12—Fe1—C18—C17−46.9 (3)
C11—Fe1—C12—C13−119.8 (3)C9—Fe1—C18—C1474.3 (2)
C18—Fe1—C12—C13−168.1 (2)C10—Fe1—C18—C14116.72 (18)
C9—Fe1—C12—C1181.58 (18)C13—Fe1—C18—C1439.6 (4)
C10—Fe1—C12—C1137.07 (17)C15—Fe1—C18—C14−37.81 (17)
C13—Fe1—C12—C11119.8 (3)C16—Fe1—C18—C14−81.79 (18)
C15—Fe1—C12—C11−166.04 (16)C17—Fe1—C18—C14−119.5 (2)
C16—Fe1—C12—C11−124.31 (18)C11—Fe1—C18—C14158.89 (17)
C14—Fe1—C12—C11161.0 (3)C12—Fe1—C18—C14−166.4 (2)
C17—Fe1—C12—C11−81.8 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2490).

References

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