metal-organic papers
m1118
Scheibitzet al. [Fe(C5H5)(C12H12P)] doi:10.1107/S1600536807012214 Acta Cryst.(2007). E63, m1118–m1119
Acta Crystallographica Section E Structure Reports
Online
ISSN 1600-5368
3,4-Dimethyl-2-phenyl-1-phosphaferrocene
Matthias Scheibitz, Hans-Wolfram Lerner and Michael Bolte*
Institut fu¨r Anorganische Chemie, J. W. Goethe-Universita¨t Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study T= 173 K
Mean(C–C) = 0.002 A˚ Rfactor = 0.024 wRfactor = 0.064
Data-to-parameter ratio = 23.0
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 13 March 2007 Accepted 15 March 2007
#2007 International Union of Crystallography All rights reserved
The geometric parameters of the title compound,
[Fe(C5H5)(C12H12P)], are in the usual ranges. The dihedral
angle between the two five-membered rings is 5.73 (11)and
the phenyl ring is twisted by 49.65 (5) with respect to the
phosphacyclopentadienyl ring.
Comment
Our group recently reported a synthetic approach to ferro-cene-containing oligomers,e.g.Fc2BH [Fc = (C5H5)Fe(C5H4)],
and polymers,e.g.[-fc-BBr-]n[fc = Fe(C5H4)2] (Scheibitzet al.,
2004; Heilmann et al., 2006). Moreover, we have shown that the related adduct of 3,4-dimethylphosphaferrocene with FcBBr is accessible (Scheibitzet al., 2003). The purpose of this paper is to describe the synthesis of the phosphaferrocene derivatives (I) and (II), and the X-ray crystal structure analysis of 3,4-dimethyl-1-phenylphosphaferrocene, (I). The treatment of [CpFe(CO)2]2 [Cp = C5H5] with
3,4-dimethyl-1-phenyl-phosphole (Scheibitz et al., 2006) in boiling xylene gives a mixture of phosphaferrocene derivatives, (I) and (II), as shown in the scheme.
The geometric parameters of (I) are in the normal ranges (Cambridge Structural Database, Version 5.28, November 2006, updated January 2007;Mogul Version 1.1; Allen, 2002; Brunoet al., 2004). The endocyclic angle at P is significantly smaller than the angles at C in the phosphacyclopentadienyl ring. The dihedral angle between the two five-membered rings is 5.73 (11)and the phenyl ring is twisted by 49.65 (5) with
Experimental
A solution of [CpFe(CO)2]2(2.40 ml, 6.8 mmol) and
3,4-dimethyl-1-phenylphosphole (2.26 g, 12 mmol) in xylene (30 ml) was heated for 15 h under reflux. After removing the solvent, the residue was extracted into hexane. After filtration, the phosphaferrocene deri-vatives (I) and (II) were separated by column chromatography (silica gel 60; solvent hexane) in an argon atmosphere. Single crystals of (I) were obtained from the second hexane fraction by cooling the solu-tion at 279 K for 48 h (yield 22%). The phosphaferrocene derivative, (II), was obtained from the first hexane fraction in 31% yield.
Crystal data
[Fe(C5H5)(C12H12P)]
Mr= 308.13
Orthorhombic,P212121
a= 7.4305 (4) A˚
b= 8.2000 (5) A˚
c= 23.0148 (9) A˚
V= 1402.29 (13) A˚3
Z= 4
MoKradiation
= 1.17 mm 1
T= 173 (2) K 0.480.310.11 mm
Data collection
Stoe IPDS II two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)
Tmin= 0.603,Tmax= 0.882
42005 measured reflections 3998 independent reflections 3898 reflections withI> 2(I)
Rint= 0.051
Refinement
R[F2> 2(F2)] = 0.024
wR(F2) = 0.064
S= 1.06 3998 reflections 174 parameters
H-atom parameters constrained
max= 0.65 e A˚ 3
min= 0.57 e A˚ 3
Absolute structure: Flack (1983), with 1689 Friedel pairs Flack parameter: 0.021 (10)
Table 1
Selected bond angles ().
C5—P1—C2 89.02 (7)
C3—C2—P1 112.89 (11)
C4—C3—C2 111.74 (13)
C5—C4—C3 112.21 (14)
C4—C5—P1 114.09 (11)
H atoms were refined with fixed individual displacement para-meters [Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C)] using a riding model, with
Caromatic—H = 0.98 A˚ and Cmethyl—H = 0.95 A˚ . The methyl groups
were allowed to rotate but not to tip.
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement:
X-AREA; data reduction: X-AREA; program(s) used to solve structure:SHELXS97(Sheldrick, 1997); program(s) used to refine structure:SHELXL97(Sheldrick, 1997); molecular graphics:XPin
SHELXTL-Plus(Sheldrick, 1991); software used to prepare material for publication:SHELXL97.
References
Allen, F. H. (2002).Acta Cryst.B58, 380–388. Blessing, R. H. (1995).Acta Cryst.A51, 33–38.
Bruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E. & Orpen, A. G. (2004).J. Chem. Inf. Comput. Sci.44, 2133–2144.
Flack, H. D. (1983).Acta Cryst.A39, 876–881.
Heilmann, J. B., Scheibitz, M., Qin, J., Sundararaman, A., Ja¨kle, F., Kretz, T., Bolte, M., Lerner, H.-W., Holthausen, M. C. & Wagner, M. (2006).Angew. Chem. Int. Ed.45, 920–925.
Scheibitz, M., Bats, J. W., Bolte, M., Lerner, H.-W. & Wagner, M. (2004).
Organometallics,23, 940–942.
Scheibitz, M., Bats, J. W., Bolte, M. & Wagner, M. (2003).Eur. J. Inorg. Chem.
pp. 2049–2053.
Scheibitz, M., Lerner, H.-W. & Bolte, M. (2006).Acta Cryst.E62, o1476–o1477. Sheldrick, G. M. (1991).SHELXTL-Plus. Release 4.1. Siemens Analytical
X-ray Instruments Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.
[image:2.610.315.566.72.226.2]Stoe & Cie (2001).X-AREA. Stoe & Cie, Darmstadt, Germany.
Figure 1
supporting information
sup-1 Acta Cryst. (2007). E63, m1118–m1119
supporting information
Acta Cryst. (2007). E63, m1118–m1119 [https://doi.org/10.1107/S1600536807012214]
3,4-Dimethyl-2-phenyl-1-phosphaferrocene
Matthias Scheibitz, Hans-Wolfram Lerner and Michael Bolte
3,4-Dimethyl-2-phenyl-1-phosphaferrocene
Crystal data [Fe(C5H5)(C12H12P)] Mr = 308.13
Orthorhombic, P212121 Hall symbol: P 2ac 2ab a = 7.4305 (4) Å b = 8.2000 (5) Å c = 23.0148 (9) Å V = 1402.29 (13) Å3 Z = 4
F(000) = 640 Dx = 1.459 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 65535 reflections θ = 2.6–29.3°
µ = 1.17 mm−1 T = 173 K Plate, red
0.48 × 0.31 × 0.11 mm
Data collection
Stoe IPDS II two-circle diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans
Absorption correction: empirical (using intensity measurements)
(MULABS; Spek, 2003; Blessing, 1995) Tmin = 0.603, Tmax = 0.882
42005 measured reflections 3998 independent reflections 3898 reflections with I > 2σ(I) Rint = 0.051
θmax = 29.8°, θmin = 2.6° h = −10→10
k = −11→11 l = −29→32
Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.024 wR(F2) = 0.064 S = 1.06 3998 reflections 174 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.039P)2 + 0.2803P] where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.002 Δρmax = 0.65 e Å−3 Δρmin = −0.57 e Å−3
Absolute structure: Flack (1983), with 1689 Friedel pairs
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)
x y z Uiso*/Ueq
Fe1 0.34421 (2) 0.65980 (2) 0.869188 (8) 0.02469 (6)
P1 0.61257 (5) 0.66285 (6) 0.820723 (17) 0.03097 (8)
C2 0.52627 (18) 0.47498 (18) 0.84949 (6) 0.0255 (2)
C21 0.63708 (18) 0.36706 (17) 0.88722 (6) 0.0269 (3)
C22 0.6588 (2) 0.20239 (19) 0.87268 (7) 0.0325 (3)
H22 0.5947 0.1587 0.8405 0.039*
C23 0.7726 (2) 0.1018 (2) 0.90453 (8) 0.0367 (3)
H23 0.7859 −0.0095 0.8938 0.044*
C24 0.8664 (2) 0.1625 (2) 0.95163 (7) 0.0377 (3)
H24 0.9454 0.0941 0.9731 0.045*
C25 0.8439 (2) 0.3250 (2) 0.96724 (7) 0.0351 (3)
H25 0.9064 0.3672 1.0000 0.042*
C26 0.7307 (2) 0.4267 (2) 0.93543 (7) 0.0315 (3)
H26 0.7170 0.5376 0.9466 0.038*
C3 0.3496 (2) 0.43660 (16) 0.82822 (6) 0.0262 (2)
C31 0.2433 (2) 0.2886 (2) 0.84538 (8) 0.0340 (3)
H31A 0.1149 0.3160 0.8464 0.051*
H31B 0.2819 0.2518 0.8839 0.051*
H31C 0.2636 0.2014 0.8170 0.051*
C4 0.2833 (2) 0.55988 (19) 0.78977 (7) 0.0296 (3)
C41 0.1030 (2) 0.5524 (2) 0.75990 (8) 0.0396 (4)
H41A 0.0684 0.6620 0.7471 0.059*
H41B 0.0125 0.5106 0.7871 0.059*
H41C 0.1108 0.4799 0.7262 0.059*
C5 0.4076 (2) 0.68999 (19) 0.78269 (7) 0.0319 (3)
H5 0.3830 0.7834 0.7596 0.038*
C11 0.3468 (3) 0.8618 (2) 0.92202 (9) 0.0455 (4)
H11 0.4342 0.9464 0.9215 0.055*
C12 0.3545 (3) 0.7172 (2) 0.95605 (7) 0.0393 (3)
H12 0.4478 0.6884 0.9824 0.047*
C13 0.1985 (2) 0.6235 (2) 0.94380 (7) 0.0351 (3)
H13 0.1688 0.5208 0.9603 0.042*
C14 0.0952 (2) 0.7105 (2) 0.90257 (8) 0.0374 (3)
H14 −0.0163 0.6762 0.8865 0.045*
supporting information
sup-3 Acta Cryst. (2007). E63, m1118–m1119
H15 0.1464 0.9391 0.8628 0.052*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Fe1 0.02392 (9) 0.02287 (9) 0.02729 (9) 0.00009 (7) 0.00130 (7) −0.00091 (7)
P1 0.02586 (16) 0.03254 (17) 0.03451 (18) −0.00345 (14) 0.00388 (13) 0.00354 (16)
C2 0.0241 (6) 0.0255 (6) 0.0270 (6) 0.0020 (5) 0.0010 (5) −0.0017 (5)
C21 0.0228 (5) 0.0300 (6) 0.0279 (6) 0.0014 (5) 0.0014 (5) 0.0009 (5)
C22 0.0314 (7) 0.0331 (7) 0.0329 (7) 0.0030 (5) −0.0007 (6) −0.0035 (5)
C23 0.0345 (7) 0.0306 (7) 0.0450 (9) 0.0056 (6) −0.0015 (7) 0.0010 (6)
C24 0.0303 (7) 0.0418 (8) 0.0410 (8) 0.0016 (7) −0.0033 (6) 0.0117 (7)
C25 0.0293 (6) 0.0441 (8) 0.0320 (6) −0.0019 (7) −0.0039 (5) 0.0015 (6)
C26 0.0276 (6) 0.0331 (7) 0.0336 (7) −0.0030 (5) −0.0002 (6) −0.0020 (6)
C3 0.0259 (6) 0.0249 (6) 0.0280 (6) 0.0009 (5) 0.0000 (5) −0.0036 (5)
C31 0.0321 (7) 0.0287 (6) 0.0412 (8) −0.0037 (6) −0.0028 (6) −0.0031 (6)
C4 0.0291 (6) 0.0319 (7) 0.0278 (6) 0.0012 (5) −0.0015 (5) −0.0021 (5)
C41 0.0351 (8) 0.0448 (9) 0.0388 (8) 0.0030 (7) −0.0098 (6) 0.0004 (7)
C5 0.0348 (7) 0.0337 (8) 0.0273 (6) 0.0006 (6) 0.0012 (5) 0.0046 (5)
C11 0.0480 (9) 0.0321 (8) 0.0563 (10) −0.0064 (8) 0.0133 (8) −0.0177 (7)
C12 0.0375 (8) 0.0486 (9) 0.0320 (7) 0.0034 (7) −0.0005 (7) −0.0137 (6)
C13 0.0361 (7) 0.0365 (8) 0.0327 (7) −0.0005 (6) 0.0103 (6) −0.0019 (6)
C14 0.0264 (7) 0.0465 (9) 0.0393 (8) 0.0047 (6) 0.0076 (6) −0.0047 (7)
C15 0.0474 (9) 0.0329 (8) 0.0495 (9) 0.0142 (7) 0.0092 (7) −0.0003 (7)
Geometric parameters (Å, º)
Fe1—C14 2.0458 (16) C26—H26 0.9500
Fe1—C13 2.0516 (16) C3—C4 1.431 (2)
Fe1—C4 2.0536 (15) C3—C31 1.501 (2)
Fe1—C15 2.0545 (16) C31—H31A 0.9800
Fe1—C11 2.0550 (17) C31—H31B 0.9800
Fe1—C12 2.0551 (16) C31—H31C 0.9800
Fe1—C3 2.0593 (14) C4—C5 1.421 (2)
Fe1—C2 2.0815 (14) C4—C41 1.507 (2)
Fe1—P1 2.2850 (4) C41—H41A 0.9800
P1—C5 1.7705 (17) C41—H41B 0.9800
P1—C2 1.7952 (16) C41—H41C 0.9800
C2—C3 1.436 (2) C5—H5 0.9500
C2—C21 1.488 (2) C11—C15 1.412 (3)
C21—C26 1.398 (2) C11—C12 1.422 (3)
C21—C22 1.400 (2) C11—H11 0.9500
C22—C23 1.390 (2) C12—C13 1.419 (3)
C22—H22 0.9500 C12—H12 0.9500
C23—C24 1.382 (2) C13—C14 1.414 (3)
C23—H23 0.9500 C13—H13 0.9500
C24—C25 1.391 (3) C14—C15 1.417 (3)
C25—C26 1.392 (2) C15—H15 0.9500
C25—H25 0.9500
C14—Fe1—C13 40.37 (7) C25—C26—C21 120.54 (15)
C14—Fe1—C4 102.48 (7) C25—C26—H26 119.7
C13—Fe1—C4 124.82 (7) C21—C26—H26 119.7
C14—Fe1—C15 40.42 (8) C4—C3—C2 111.74 (13)
C13—Fe1—C15 68.00 (7) C4—C3—C31 123.58 (14)
C4—Fe1—C15 112.88 (8) C2—C3—C31 124.65 (13)
C14—Fe1—C11 67.81 (8) C4—C3—Fe1 69.43 (8)
C13—Fe1—C11 68.07 (7) C2—C3—Fe1 70.54 (8)
C4—Fe1—C11 148.25 (8) C31—C3—Fe1 126.02 (11)
C15—Fe1—C11 40.19 (9) C3—C31—H31A 109.5
C14—Fe1—C12 67.78 (7) C3—C31—H31B 109.5
C13—Fe1—C12 40.42 (7) H31A—C31—H31B 109.5
C4—Fe1—C12 164.88 (7) C3—C31—H31C 109.5
C15—Fe1—C12 67.81 (8) H31A—C31—H31C 109.5
C11—Fe1—C12 40.49 (8) H31B—C31—H31C 109.5
C14—Fe1—C3 111.72 (7) C5—C4—C3 112.21 (14)
C13—Fe1—C3 105.34 (6) C5—C4—C41 123.79 (14)
C4—Fe1—C3 40.72 (6) C3—C4—C41 124.00 (14)
C15—Fe1—C3 144.64 (8) C5—C4—Fe1 70.07 (8)
C11—Fe1—C3 170.83 (7) C3—C4—Fe1 69.86 (8)
C12—Fe1—C3 130.41 (7) C41—C4—Fe1 128.17 (12)
C14—Fe1—C2 144.84 (7) C4—C41—H41A 109.5
C13—Fe1—C2 114.81 (6) C4—C41—H41B 109.5
C4—Fe1—C2 70.05 (6) H41A—C41—H41B 109.5
C15—Fe1—C2 174.26 (7) C4—C41—H41C 109.5
C11—Fe1—C2 135.22 (7) H41A—C41—H41C 109.5
C12—Fe1—C2 110.76 (7) H41B—C41—H41C 109.5
C3—Fe1—C2 40.59 (6) C4—C5—P1 114.09 (11)
C14—Fe1—P1 165.98 (6) C4—C5—H5 123.0
C13—Fe1—P1 150.53 (5) P1—C5—H5 123.0
C4—Fe1—P1 76.24 (5) C15—C11—C12 107.95 (17)
C15—Fe1—P1 126.82 (6) C15—C11—Fe1 69.88 (10)
C11—Fe1—P1 105.77 (6) C12—C11—Fe1 69.76 (9)
C12—Fe1—P1 116.09 (6) C15—C11—H11 126.0
C3—Fe1—P1 76.67 (4) C12—C11—H11 126.0
C2—Fe1—P1 48.28 (4) Fe1—C11—H11 125.9
C5—P1—C2 89.02 (7) C13—C12—C11 108.00 (17)
C5—P1—Fe1 59.48 (5) C13—C12—Fe1 69.66 (9)
C2—P1—Fe1 59.92 (5) C11—C12—Fe1 69.75 (10)
C3—C2—C21 125.06 (13) C13—C12—H12 126.0
C3—C2—P1 112.89 (11) C11—C12—H12 126.0
C21—C2—P1 121.85 (10) Fe1—C12—H12 126.2
C3—C2—Fe1 68.88 (8) C14—C13—C12 107.68 (16)
C21—C2—Fe1 131.71 (10) C14—C13—Fe1 69.60 (9)
supporting information
sup-5 Acta Cryst. (2007). E63, m1118–m1119
C26—C21—C22 118.03 (14) C14—C13—H13 126.2
C26—C21—C2 122.02 (13) C12—C13—H13 126.2
C22—C21—C2 119.83 (13) Fe1—C13—H13 125.9
C23—C22—C21 121.08 (15) C13—C14—C15 108.42 (16)
C23—C22—H22 119.5 C13—C14—Fe1 70.03 (9)
C21—C22—H22 119.5 C15—C14—Fe1 70.12 (9)
C24—C23—C22 120.44 (16) C13—C14—H14 125.8
C24—C23—H23 119.8 C15—C14—H14 125.8
C22—C23—H23 119.8 Fe1—C14—H14 125.6
C23—C24—C25 119.16 (15) C11—C15—C14 107.95 (17)
C23—C24—H24 120.4 C11—C15—Fe1 69.92 (9)
C25—C24—H24 120.4 C14—C15—Fe1 69.46 (9)
C24—C25—C26 120.73 (15) C11—C15—H15 126.0
C24—C25—H25 119.6 C14—C15—H15 126.0
C26—C25—H25 119.6 Fe1—C15—H15 126.2
C14—Fe1—P1—C5 −53.2 (2) P1—C2—C3—C4 −1.06 (15)
C13—Fe1—P1—C5 172.78 (11) Fe1—C2—C3—C4 57.17 (10)
C4—Fe1—P1—C5 33.19 (7) C21—C2—C3—C31 6.0 (2)
C15—Fe1—P1—C5 −75.28 (10) P1—C2—C3—C31 −179.15 (12)
C11—Fe1—P1—C5 −114.01 (9) Fe1—C2—C3—C31 −120.92 (14)
C12—Fe1—P1—C5 −156.14 (9) C21—C2—C3—Fe1 126.89 (14)
C3—Fe1—P1—C5 75.12 (7) P1—C2—C3—Fe1 −58.23 (8)
C2—Fe1—P1—C5 108.58 (8) C2—C3—C4—C5 −0.61 (18)
C14—Fe1—P1—C2 −161.8 (2) C31—C3—C4—C5 177.50 (14)
C13—Fe1—P1—C2 64.21 (11) Fe1—C3—C4—C5 57.19 (11)
C4—Fe1—P1—C2 −75.38 (7) C2—C3—C4—C41 179.07 (14)
C15—Fe1—P1—C2 176.15 (9) C31—C3—C4—C41 −2.8 (2)
C11—Fe1—P1—C2 137.42 (8) Fe1—C3—C4—C41 −123.13 (16)
C12—Fe1—P1—C2 95.28 (8) C2—C3—C4—Fe1 −57.80 (10)
C3—Fe1—P1—C2 −33.45 (7) C31—C3—C4—Fe1 120.31 (14)
C5—P1—C2—C3 1.84 (11) C3—C4—C5—P1 2.07 (17)
Fe1—P1—C2—C3 56.59 (9) C41—C4—C5—P1 −177.61 (13)
C5—P1—C2—C21 176.91 (12) Fe1—C4—C5—P1 59.14 (9)
Fe1—P1—C2—C21 −128.33 (13) C2—P1—C5—C4 −2.22 (12)
C5—P1—C2—Fe1 −54.75 (6) Fe1—P1—C5—C4 −57.35 (10)
C3—C2—C21—C26 −135.80 (15) C15—C11—C12—C13 0.32 (19)
P1—C2—C21—C26 49.74 (18) Fe1—C11—C12—C13 −59.37 (11)
Fe1—C2—C21—C26 −43.8 (2) C15—C11—C12—Fe1 59.68 (12)
C3—C2—C21—C22 48.2 (2) C11—C12—C13—C14 −0.17 (19)
P1—C2—C21—C22 −126.24 (14) Fe1—C12—C13—C14 −59.60 (11)
Fe1—C2—C21—C22 140.26 (13) C11—C12—C13—Fe1 59.43 (12)
C26—C21—C22—C23 −1.2 (2) C12—C13—C14—C15 −0.03 (19)
C2—C21—C22—C23 174.97 (15) Fe1—C13—C14—C15 −59.84 (12)
C21—C22—C23—C24 0.3 (3) C12—C13—C14—Fe1 59.81 (11)
C22—C23—C24—C25 0.8 (3) C12—C11—C15—C14 −0.34 (19)
C23—C24—C25—C26 −1.1 (2) Fe1—C11—C15—C14 59.27 (12)
C22—C21—C26—C25 0.9 (2) C13—C14—C15—C11 0.23 (19)
C2—C21—C26—C25 −175.13 (14) Fe1—C14—C15—C11 −59.56 (12)
