Related literature {#sec1}
==================

For related literature, see: Abboud *et al.* (1991[@bb2]); Crane (2003[@bb4]); Hanson (1982[@bb5]); Koray *et al.* (1985[@bb6]); Marcén *et al.* (2002[@bb7]); Piórko *et al.* (1989[@bb8], 1994[@bb9]).

Experimental {#sec2}
============

 {#sec2.1}

### Crystal data {#sec2.1.1}

\[Fe(C~5~H~5~)(C~15~H~20~O~4~)\]PF~6~*M* *~r~* = 530.22Triclinic,*a* = 10.1075 (5) Å*b* = 10.6731 (5) Å*c* = 11.4797 (6) Åα = 100.396 (1)°β = 111.854 (1)°γ = 99.100 (1)°*V* = 1095.56 (9) Å^3^*Z* = 2Mo *K*α radiationμ = 0.84 mm^−1^*T* = 223 (2) K0.40 × 0.38 × 0.10 mm

### Data collection {#sec2.1.2}

Bruker SMART CCD area-detector diffractometerAbsorption correction: multi-scan (*SADABS*; Bruker, 1998[@bb3]) *T* ~min~ = 0.688, *T* ~max~ = 0.9208715 measured reflections4253 independent reflections3283 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.016

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.029*wR*(*F* ^2^) = 0.070*S* = 0.954253 reflections343 parameters30 restraintsH-atom parameters constrainedΔρ~max~ = 0.27 e Å^−3^Δρ~min~ = −0.26 e Å^−3^

 {#d5e457}

Data collection: *SMART* (Bruker, 1998[@bb3]); cell refinement: *SAINT* (Bruker, 1998[@bb3]); data reduction: *SAINT* and *SHELXTL* (Sheldrick, 2008[@bb10]); program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb10]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb10]); molecular graphics: *SHELXTL*; software used to prepare material for publication: *SHELXTL*.

Supplementary Material
======================

Crystal structure: contains datablocks I, global. DOI: [10.1107/S1600536808030523/rt2022sup1.cif](http://dx.doi.org/10.1107/S1600536808030523/rt2022sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536808030523/rt2022Isup2.hkl](http://dx.doi.org/10.1107/S1600536808030523/rt2022Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?rt2022&file=rt2022sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?rt2022sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?rt2022&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [RT2022](http://scripts.iucr.org/cgi-bin/sendsup?rt2022)).

The authors thank Saint Mary's University for financial support.

Comment
=======

The title compound, along with other diethyl alkylarylmalonates complexed with a cyclopentadienyliron(II) moiety, were reported as intermediates in the syntheses of alkyl (substituted aryl)malonates (Piórko *et al.*, 1989). The *ORTEP* drawing of the title compound is shown in Fig. 1. The two aromatic rings are not quite coplanar, with a dihedral angle of 4.10(0.14)° between the plane formed by C11--C16 and C21--C25 which is not significantly different from the value 3.0 (4)° reported for the most similar structure of 1,1-di(2-propenyl)-3-butenylbenzene FeCp complex (Marcén *et al.*, 2002). The Fe ion is located at distances of 1.6661 (9)Å from the Cp and 1.5360 (8)Å from the phenyl ring; such values are typical of those found in the literature for similar complexes (see for example Abboud *et al.*, 1991; Piórko *et al.*, 1994; Marcén *et al.*, 2002; Crane 2003). The distance for Fe1---C11 at 2.1179 (19) Å, where C11 is the quaternary carbon in the phenyl ring, is the longest among the distances Fe to C atoms of this ring. Again, this is in agreement with the literature data for the similar FeCp complexed aromatic C atoms containing alkyl groups (see for example Hanson 1982; Koray *et al.*, 1985; Piórko *et al.*, 1994; Marcén *et al.*, 2002). The PF~6~^-^ anion shows some rotational disorder, as reported for systems of this kind. A view along a side of the unit cell (Fig. 2) indicates π--π stacking arrangement of the aromatic rings, with a centroid to centroid distance of 3.85 Å. The rings are oriented in a face to face arrangement, and while this almost direct overlap is uncommon for unsubstituted arene rings, the ester functionality on the ring alters the electronics of the system, making it possible for the rings to interact; the functional group on one ring is on the opposite side of that on the next ring.

Experimental {#experimental}
============

The title compound was prepared following the method of Piórko *et al.* (1989). A crystal used for data collection was grown by slow evaporation of solvents from a solution of the complex in acetone--diethyl ether--dichloromethane mixture at 280 K.

Refinement {#refinement}
==========

The H atoms were placed in geometrically idealized positions with C---H distances of 0.93 Å (aromatic), 0.96 Å (methyl) and 0.97 Å (methylene) and constrained to ride on the parent C atom with Uiso(H) = 1.2Ueq(C) for aromatic and methylene, and Uiso(H) = 1.5Ueq(C) for methyl protons. Then F atoms of the PF~6~ anion were found to be disordered over two sites and were refined with a 50:50 occupancy. The F atoms were anisotropically refined and F1, F2, F3, F4 and F4\' restrained using the ISOR command.

Figures
=======

![View of the cation and anion showing the labelling of non-H atoms with the thermal ellipsoids shown at 50% probability levels.](e-64-m1360-fig1){#Fap1}

![The packing diagram for the molecule.](e-64-m1360-fig2){#Fap2}

Crystal data {#tablewrapcrystaldatalong}
============

  --------------------------------------- ---------------------------------------
  \[Fe(C~5~H~5~)(C~15~H~20~O~4~)\]PF~6~   *Z* = 2
  *M~r~* = 530.22                         *F*(000) = 544
  Triclinic, *P*1                         *D*~x~ = 1.607 Mg m^−3^
  Hall symbol: -P 1                       Mo *K*α radiation, λ = 0.71073 Å
  *a* = 10.1075 (5) Å                     Cell parameters from 3863 reflections
  *b* = 10.6731 (5) Å                     θ = 2.2--28.0°
  *c* = 11.4797 (6) Å                     µ = 0.84 mm^−1^
  α = 100.396 (1)°                        *T* = 223 K
  β = 111.854 (1)°                        Plate, yellow
  γ = 99.100 (1)°                         0.40 × 0.38 × 0.10 mm
  *V* = 1095.56 (9) Å^3^                  
  --------------------------------------- ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  ---------------------------------------------------------- --------------------------------------
  Bruker SMART CCD area-detector diffractometer              4253 independent reflections
  Radiation source: fine-focus sealed tube                   3283 reflections with *I* \> 2σ(*I*)
  graphite                                                   *R*~int~ = 0.016
  φ and ω scans                                              θ~max~ = 26.0°, θ~min~ = 2.0°
  Absorption correction: multi-scan (SADABS; Bruker, 1998)   *h* = −12→12
  *T*~min~ = 0.688, *T*~max~ = 0.920                         *k* = −13→13
  8715 measured reflections                                  *l* = −14→14
  ---------------------------------------------------------- --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- -------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.029   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.070                  H-atom parameters constrained
  *S* = 0.95                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0326*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  4253 reflections                      (Δ/σ)~max~ = 0.001
  343 parameters                        Δρ~max~ = 0.27 e Å^−3^
  30 restraints                         Δρ~min~ = −0.26 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Geometry. All e.s.d.\'s 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 *F*^2^ against ALL reflections. The weighted *R*-factor *wR* and goodness of fit *S* are based on *F*^2^, conventional *R*-factors *R* are based on *F*, with *F* set to zero for negative *F*^2^. The threshold expression of *F*^2^ \> σ(*F*^2^) is used only for calculating *R*-factors(gt) *etc* and is not relevant to the choice of reflections for refinement. *R*-factors based on *F*^2^ 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 (Å^2^) {#tablewrapcoords}
==================================================================================================

  ------ -------------- -------------- -------------- -------------------- ------------
         *x*            *y*            *z*            *U*~iso~\*/*U*~eq~   Occ. (\<1)
  Fe1    0.81979 (3)    0.78170 (3)    0.69683 (3)    0.02689 (10)         
  O1     0.92832 (15)   0.74047 (14)   1.12205 (13)   0.0373 (4)           
  O2     0.72028 (15)   0.60360 (14)   1.09549 (13)   0.0346 (3)           
  O3     0.53949 (16)   0.50483 (14)   0.74158 (14)   0.0403 (4)           
  O4     0.76727 (15)   0.48640 (13)   0.85723 (13)   0.0329 (3)           
  C1     0.7101 (2)     0.68946 (18)   0.91843 (18)   0.0254 (4)           
  C2     0.5722 (2)     0.7343 (2)     0.9184 (2)     0.0334 (5)           
  H2A    0.5192         0.7499         0.8336         0.040\*              
  H2B    0.5072         0.6627         0.9286         0.040\*              
  C3     0.6033 (3)     0.8579 (2)     1.0241 (2)     0.0445 (6)           
  H3A    0.5114         0.8797         1.0167         0.067\*              
  H3B    0.6660         0.9301         1.0140         0.067\*              
  H3C    0.6524         0.8427         1.1088         0.067\*              
  C4     0.8028 (2)     0.68215 (18)   1.05709 (18)   0.0272 (4)           
  C5     0.7890 (2)     0.5919 (2)     1.2283 (2)     0.0407 (6)           
  H5A    0.7138         0.5746         1.2618         0.049\*              
  H5B    0.8601         0.6748         1.2840         0.049\*              
  C6     0.8652 (3)     0.4835 (3)     1.2322 (3)     0.0620 (7)           
  H6A    0.9108         0.4775         1.3211         0.093\*              
  H6B    0.9401         0.5010         1.1995         0.093\*              
  H6C    0.7944         0.4012         1.1785         0.093\*              
  C7     0.6602 (2)     0.54987 (19)   0.82816 (19)   0.0282 (4)           
  C8     0.7289 (3)     0.3497 (2)     0.7801 (2)     0.0420 (6)           
  H8A    0.8186         0.3242         0.7823         0.050\*              
  H8B    0.6654         0.3425         0.6894         0.050\*              
  C9     0.6513 (3)     0.2591 (2)     0.8327 (3)     0.0582 (7)           
  H9A    0.6259         0.1697         0.7801         0.087\*              
  H9B    0.5623         0.2843         0.8302         0.087\*              
  H9C    0.7152         0.2647         0.9217         0.087\*              
  C11    0.8062 (2)     0.78164 (18)   0.87652 (17)   0.0249 (4)           
  C12    0.9415 (2)     0.75755 (19)   0.87999 (18)   0.0279 (4)           
  H12A   0.9593         0.6699         0.8862         0.034\*              
  C13    1.0319 (2)     0.8405 (2)     0.84251 (19)   0.0336 (5)           
  H13A   1.1117         0.8099         0.8248         0.040\*              
  C14    0.9897 (2)     0.9497 (2)     0.8011 (2)     0.0383 (5)           
  H14A   1.0406         0.9946         0.7556         0.046\*              
  C15    0.8563 (2)     0.9749 (2)     0.7967 (2)     0.0359 (5)           
  H15A   0.8151         1.0369         0.7474         0.043\*              
  C16    0.7640 (2)     0.89045 (19)   0.83243 (19)   0.0309 (5)           
  H16A   0.6604         0.8955         0.8072         0.037\*              
  C21    0.6282 (2)     0.6578 (2)     0.55586 (19)   0.0400 (6)           
  H21A   0.5383         0.6247         0.5679         0.048\*              
  C22    0.7449 (3)     0.5962 (2)     0.57124 (19)   0.0391 (5)           
  H22A   0.7514         0.5127         0.5964         0.047\*              
  C23    0.8518 (3)     0.6756 (2)     0.5459 (2)     0.0400 (5)           
  H23A   0.9460         0.6571         0.5494         0.048\*              
  C24    0.7992 (3)     0.7845 (2)     0.5129 (2)     0.0409 (6)           
  H24A   0.8502         0.8562         0.4892         0.049\*              
  C25    0.6604 (2)     0.7735 (2)     0.5190 (2)     0.0407 (6)           
  H25A   0.5973         0.8359         0.5002         0.049\*              
  P1     0.27016 (7)    0.85459 (6)    0.57865 (6)    0.04155 (16)         
  F1     0.4244 (5)     0.9355 (6)     0.6910 (5)     0.1004 (17)          0.50
  F2     0.1990 (10)    0.9654 (8)     0.6111 (6)     0.116 (2)            0.50
  F3     0.1268 (7)     0.7640 (9)     0.4775 (7)     0.133 (3)            0.50
  F4     0.3508 (9)     0.7418 (6)     0.5589 (7)     0.090 (2)            0.50
  F5     0.2264 (15)    0.8121 (18)    0.6816 (17)    0.101 (4)            0.50
  F6     0.2812 (16)    0.8822 (15)    0.4546 (10)    0.093 (4)            0.50
  F1\'   0.3536 (9)     0.9989 (5)     0.6502 (5)     0.110 (2)            0.50
  F2\'   0.1219 (6)     0.9002 (7)     0.5286 (9)     0.124 (3)            0.50
  F3\'   0.1751 (10)    0.7108 (5)     0.4937 (8)     0.114 (3)            0.50
  F4\'   0.4077 (7)     0.8045 (9)     0.6140 (8)     0.117 (3)            0.50
  F5\'   0.2616 (16)    0.8132 (17)    0.7044 (17)    0.094 (4)            0.50
  F6\'   0.3100 (15)    0.9107 (15)    0.4735 (12)    0.095 (4)            0.50
  ------ -------------- -------------- -------------- -------------------- ------------

Atomic displacement parameters (Å^2^) {#tablewrapadps}
=====================================

  ------ -------------- -------------- -------------- -------------- -------------- --------------
         *U*^11^        *U*^22^        *U*^33^        *U*^12^        *U*^13^        *U*^23^
  Fe1    0.02888 (17)   0.02541 (16)   0.02465 (16)   0.00237 (12)   0.01130 (13)   0.00567 (12)
  O1     0.0332 (8)     0.0393 (9)     0.0293 (8)     −0.0006 (7)    0.0056 (7)     0.0093 (7)
  O2     0.0352 (8)     0.0418 (9)     0.0270 (8)     0.0043 (7)     0.0130 (7)     0.0137 (6)
  O3     0.0341 (9)     0.0373 (9)     0.0345 (8)     0.0006 (7)     0.0040 (7)     0.0037 (7)
  O4     0.0325 (8)     0.0245 (7)     0.0371 (8)     0.0050 (6)     0.0130 (7)     0.0019 (6)
  C1     0.0249 (10)    0.0262 (10)    0.0235 (10)    0.0047 (8)     0.0094 (8)     0.0054 (8)
  C2     0.0274 (11)    0.0367 (12)    0.0403 (12)    0.0089 (9)     0.0164 (10)    0.0139 (10)
  C3     0.0476 (14)    0.0437 (14)    0.0568 (15)    0.0192 (11)    0.0337 (13)    0.0143 (12)
  C4     0.0329 (12)    0.0235 (10)    0.0261 (10)    0.0081 (9)     0.0134 (9)     0.0047 (8)
  C5     0.0439 (14)    0.0546 (15)    0.0271 (11)    0.0096 (11)    0.0167 (10)    0.0170 (11)
  C6     0.0710 (19)    0.0593 (18)    0.0575 (17)    0.0261 (15)    0.0182 (15)    0.0290 (14)
  C7     0.0313 (11)    0.0275 (11)    0.0270 (11)    0.0029 (9)     0.0142 (10)    0.0093 (9)
  C8     0.0458 (14)    0.0253 (11)    0.0517 (14)    0.0059 (10)    0.0225 (12)    −0.0001 (10)
  C9     0.0716 (19)    0.0321 (13)    0.0714 (18)    0.0060 (13)    0.0327 (16)    0.0140 (12)
  C11    0.0264 (10)    0.0234 (10)    0.0199 (10)    0.0023 (8)     0.0080 (8)     0.0003 (8)
  C12    0.0265 (10)    0.0276 (11)    0.0231 (10)    0.0026 (9)     0.0074 (9)     0.0011 (8)
  C13    0.0266 (11)    0.0370 (12)    0.0311 (11)    −0.0005 (9)    0.0115 (9)     0.0025 (9)
  C14    0.0428 (13)    0.0317 (12)    0.0343 (12)    −0.0063 (10)   0.0180 (10)    0.0024 (9)
  C15    0.0490 (14)    0.0232 (11)    0.0347 (12)    0.0048 (10)    0.0184 (11)    0.0069 (9)
  C16    0.0359 (12)    0.0263 (11)    0.0302 (11)    0.0065 (9)     0.0149 (10)    0.0049 (9)
  C21    0.0368 (12)    0.0421 (13)    0.0248 (11)    −0.0083 (10)   0.0055 (10)    0.0014 (10)
  C22    0.0531 (15)    0.0299 (12)    0.0247 (11)    0.0028 (11)    0.0115 (10)    0.0010 (9)
  C23    0.0485 (14)    0.0438 (14)    0.0281 (11)    0.0094 (11)    0.0195 (11)    0.0038 (10)
  C24    0.0517 (14)    0.0430 (14)    0.0260 (11)    0.0026 (11)    0.0169 (11)    0.0106 (10)
  C25    0.0405 (13)    0.0451 (14)    0.0278 (12)    0.0082 (11)    0.0054 (10)    0.0098 (10)
  P1     0.0377 (3)     0.0473 (4)     0.0485 (4)     0.0136 (3)     0.0237 (3)     0.0180 (3)
  F1     0.071 (3)      0.096 (4)      0.083 (3)      −0.021 (3)     0.000 (2)      0.010 (3)
  F2     0.172 (6)      0.136 (5)      0.119 (4)      0.127 (5)      0.091 (4)      0.072 (4)
  F3     0.054 (3)      0.188 (8)      0.092 (3)      −0.041 (4)     0.000 (3)      0.012 (6)
  F4     0.135 (6)      0.066 (3)      0.111 (4)      0.054 (3)      0.083 (4)      0.025 (2)
  F5     0.093 (6)      0.147 (9)      0.090 (7)      0.001 (5)      0.072 (6)      0.040 (5)
  F6     0.160 (9)      0.083 (5)      0.040 (3)      0.023 (5)      0.043 (4)      0.028 (3)
  F1\'   0.151 (6)      0.071 (3)      0.065 (3)      −0.050 (3)     0.040 (3)      −0.009 (2)
  F2\'   0.053 (3)      0.114 (5)      0.228 (8)      0.046 (3)      0.057 (4)      0.077 (5)
  F3\'   0.171 (9)      0.036 (2)      0.119 (5)      0.006 (3)      0.057 (5)      0.007 (2)
  F4\'   0.067 (4)      0.197 (8)      0.148 (6)      0.084 (4)      0.061 (4)      0.112 (5)
  F5\'   0.124 (8)      0.140 (9)      0.081 (6)      0.080 (8)      0.068 (6)      0.077 (6)
  F6\'   0.099 (5)      0.107 (8)      0.129 (8)      0.032 (5)      0.076 (6)      0.081 (7)
  ------ -------------- -------------- -------------- -------------- -------------- --------------

Geometric parameters (Å, °) {#tablewrapgeomlong}
===========================

  ------------------ ------------- ------------------ -------------
  Fe1---C21          2.050 (2)     C9---H9A           0.9700
  Fe1---C24          2.050 (2)     C9---H9B           0.9700
  Fe1---C25          2.052 (2)     C9---H9C           0.9700
  Fe1---C23          2.053 (2)     C11---C16          1.413 (3)
  Fe1---C22          2.063 (2)     C11---C12          1.418 (3)
  Fe1---C15          2.072 (2)     C12---C13          1.406 (3)
  Fe1---C16          2.073 (2)     C12---H12A         0.9900
  Fe1---C13          2.077 (2)     C13---C14          1.405 (3)
  Fe1---C14          2.078 (2)     C13---H13A         0.9900
  Fe1---C12          2.0906 (19)   C14---C15          1.400 (3)
  Fe1---C11          2.1179 (19)   C14---H14A         0.9900
  O1---C4            1.196 (2)     C15---C16          1.415 (3)
  O2---C4            1.334 (2)     C15---H15A         0.9900
  O2---C5            1.459 (2)     C16---H16A         0.9900
  O3---C7            1.203 (2)     C21---C25          1.405 (3)
  O4---C7            1.336 (2)     C21---C22          1.409 (3)
  O4---C8            1.470 (2)     C21---H21A         0.9900
  C1---C11           1.536 (3)     C22---C23          1.416 (3)
  C1---C7            1.538 (3)     C22---H22A         0.9900
  C1---C4            1.541 (3)     C23---C24          1.408 (3)
  C1---C2            1.543 (3)     C23---H23A         0.9900
  C2---C3            1.522 (3)     C24---C25          1.418 (3)
  C2---H2A           0.9800        C24---H24A         0.9900
  C2---H2B           0.9800        C25---H25A         0.9900
  C3---H3A           0.9700        P1---F4\'          1.508 (5)
  C3---H3B           0.9700        P1---F3            1.510 (6)
  C3---H3C           0.9700        P1---F5            1.523 (12)
  C5---C6            1.486 (3)     P1---F2            1.538 (5)
  C5---H5A           0.9800        P1---F1\'          1.541 (4)
  C5---H5B           0.9800        P1---F6            1.544 (11)
  C6---H6A           0.9700        P1---F2\'          1.582 (5)
  C6---H6B           0.9700        P1---F4            1.586 (6)
  C6---H6C           0.9700        P1---F1            1.586 (4)
  C8---C9            1.496 (3)     P1---F6\'          1.589 (13)
  C8---H8A           0.9800        P1---F3\'          1.590 (6)
  C8---H8B           0.9800        P1---F5\'          1.612 (14)
                                                      
  C21---Fe1---C24    67.56 (9)     C12---C13---Fe1    70.81 (11)
  C21---Fe1---C25    40.06 (9)     C14---C13---H13A   119.0
  C24---Fe1---C25    40.45 (9)     C12---C13---H13A   119.0
  C21---Fe1---C23    67.69 (9)     Fe1---C13---H13A   119.0
  C24---Fe1---C23    40.14 (9)     C15---C14---C13    119.4 (2)
  C25---Fe1---C23    67.79 (9)     C15---C14---Fe1    70.05 (12)
  C21---Fe1---C22    40.07 (9)     C13---C14---Fe1    70.18 (12)
  C24---Fe1---C22    67.35 (9)     C15---C14---H14A   119.4
  C25---Fe1---C22    67.37 (9)     C13---C14---H14A   119.4
  C23---Fe1---C22    40.24 (9)     Fe1---C14---H14A   119.4
  C21---Fe1---C15    128.85 (9)    C14---C15---C16    120.4 (2)
  C24---Fe1---C15    106.60 (9)    C14---C15---Fe1    70.53 (12)
  C25---Fe1---C15    101.40 (9)    C16---C15---Fe1    70.08 (11)
  C23---Fe1---C15    140.10 (9)    C14---C15---H15A   118.8
  C22---Fe1---C15    168.30 (9)    C16---C15---H15A   118.8
  C21---Fe1---C16    106.85 (9)    Fe1---C15---H15A   118.8
  C24---Fe1---C16    134.61 (9)    C11---C16---C15    120.80 (19)
  C25---Fe1---C16    105.35 (9)    C11---C16---Fe1    72.02 (11)
  C23---Fe1---C16    173.11 (9)    C15---C16---Fe1    70.00 (12)
  C22---Fe1---C16    137.62 (9)    C11---C16---H16A   118.8
  C15---Fe1---C16    39.93 (8)     C15---C16---H16A   118.8
  C21---Fe1---C13    158.75 (9)    Fe1---C16---H16A   118.8
  C24---Fe1---C13    116.55 (9)    C25---C21---C22    108.4 (2)
  C25---Fe1---C13    154.37 (9)    C25---C21---Fe1    70.08 (12)
  C23---Fe1---C13    101.40 (9)    C22---C21---Fe1    70.47 (12)
  C22---Fe1---C13    120.09 (9)    C25---C21---H21A   125.8
  C15---Fe1---C13    71.43 (9)     C22---C21---H21A   125.8
  C16---Fe1---C13    85.11 (8)     Fe1---C21---H21A   125.8
  C21---Fe1---C14    160.63 (9)    C21---C22---C23    108.0 (2)
  C24---Fe1---C14    98.94 (9)     C21---C22---Fe1    69.46 (12)
  C25---Fe1---C14    120.80 (9)    C23---C22---Fe1    69.50 (12)
  C23---Fe1---C14    111.53 (9)    C21---C22---H22A   126.0
  C22---Fe1---C14    148.93 (9)    C23---C22---H22A   126.0
  C15---Fe1---C14    39.42 (9)     Fe1---C22---H22A   126.0
  C16---Fe1---C14    72.10 (8)     C24---C23---C22    107.7 (2)
  C13---Fe1---C14    39.53 (8)     C24---C23---Fe1    69.82 (12)
  C21---Fe1---C12    127.06 (8)    C22---C23---Fe1    70.26 (12)
  C24---Fe1---C12    149.64 (9)    C24---C23---H23A   126.1
  C25---Fe1---C12    166.15 (8)    C22---C23---H23A   126.1
  C23---Fe1---C12    115.23 (9)    Fe1---C23---H23A   126.1
  C22---Fe1---C12    105.62 (8)    C23---C24---C25    108.2 (2)
  C15---Fe1---C12    84.63 (8)     C23---C24---Fe1    70.05 (12)
  C16---Fe1---C12    71.27 (8)     C25---C24---Fe1    69.87 (12)
  C13---Fe1---C12    39.44 (8)     C23---C24---H24A   125.9
  C14---Fe1---C12    71.60 (8)     C25---C24---H24A   125.9
  C21---Fe1---C11    106.11 (8)    Fe1---C24---H24A   125.9
  C24---Fe1---C11    170.92 (8)    C21---C25---C24    107.7 (2)
  C25---Fe1---C11    130.58 (8)    C21---C25---Fe1    69.87 (12)
  C23---Fe1---C11    144.91 (9)    C24---C25---Fe1    69.68 (12)
  C22---Fe1---C11    112.43 (8)    C21---C25---H25A   126.2
  C15---Fe1---C11    71.85 (8)     C24---C25---H25A   126.2
  C16---Fe1---C11    39.38 (7)     Fe1---C25---H25A   126.2
  C13---Fe1---C11    71.79 (8)     F4\'---P1---F3     118.9 (5)
  C14---Fe1---C11    85.47 (8)     F4\'---P1---F5     95.7 (6)
  C12---Fe1---C11    39.38 (7)     F3---P1---F5       87.7 (8)
  C4---O2---C5       116.62 (16)   F4\'---P1---F2     146.6 (5)
  C7---O4---C8       116.15 (16)   F3---P1---F2       94.2 (4)
  C11---C1---C7      110.06 (15)   F5---P1---F2       79.9 (7)
  C11---C1---C4      108.78 (15)   F4\'---P1---F1\'   94.2 (4)
  C7---C1---C4       107.62 (15)   F3---P1---F1\'     145.1 (5)
  C11---C1---C2      113.56 (16)   F5---P1---F1\'     100.5 (8)
  C7---C1---C2       108.40 (16)   F2---P1---F1\'     54.9 (3)
  C4---C1---C2       108.24 (16)   F4\'---P1---F6     91.8 (7)
  C3---C2---C1       114.76 (17)   F3---P1---F6       80.5 (6)
  C3---C2---H2A      108.6         F5---P1---F6       168.0 (8)
  C1---C2---H2A      108.6         F2---P1---F6       98.8 (6)
  C3---C2---H2B      108.6         F1\'---P1---F6     88.2 (6)
  C1---C2---H2B      108.6         F4\'---P1---F2\'   174.9 (4)
  H2A---C2---H2B     107.6         F3---P1---F2\'     57.2 (4)
  C2---C3---H3A      109.5         F5---P1---F2\'     87.5 (6)
  C2---C3---H3B      109.5         F2---P1---F2\'     37.9 (3)
  H3A---C3---H3B     109.5         F1\'---P1---F2\'   89.1 (4)
  C2---C3---H3C      109.5         F6---P1---F2\'     84.4 (7)
  H3A---C3---H3C     109.5         F4\'---P1---F4     29.7 (3)
  H3B---C3---H3C     109.5         F3---P1---F4       89.2 (4)
  O1---C4---O2       124.96 (18)   F5---P1---F4       96.3 (7)
  O1---C4---C1       125.52 (18)   F2---P1---F4       174.8 (3)
  O2---C4---C1       109.49 (16)   F1\'---P1---F4     122.9 (4)
  O2---C5---C6       110.53 (19)   F6---P1---F4       85.6 (7)
  O2---C5---H5A      109.5         F2\'---P1---F4     146.1 (4)
  C6---C5---H5A      109.5         F4\'---P1---F1     56.3 (3)
  O2---C5---H5B      109.5         F3---P1---F1       173.4 (4)
  C6---C5---H5B      109.5         F5---P1---F1       88.5 (7)
  H5A---C5---H5B     108.1         F2---P1---F1       90.4 (4)
  C5---C6---H6A      109.5         F1\'---P1---F1     41.1 (3)
  C5---C6---H6B      109.5         F6---P1---F1       103.5 (6)
  H6A---C6---H6B     109.5         F2\'---P1---F1     127.9 (4)
  C5---C6---H6C      109.5         F4---P1---F1       85.9 (3)
  H6A---C6---H6C     109.5         F4\'---P1---F6\'   88.7 (6)
  H6B---C6---H6C     109.5         F3---P1---F6\'     93.0 (6)
  O3---C7---O4       124.71 (18)   F5---P1---F6\'     174.6 (8)
  O3---C7---C1       123.51 (18)   F2---P1---F6\'     94.7 (6)
  O4---C7---C1       111.77 (16)   F1\'---P1---F6\'   75.9 (6)
  O4---C8---C9       110.54 (18)   F6---P1---F6\'     12.9 (10)
  O4---C8---H8A      109.5         F2\'---P1---F6\'   88.3 (6)
  C9---C8---H8A      109.5         F4---P1---F6\'     89.0 (6)
  O4---C8---H8B      109.5         F1---P1---F6\'     91.3 (6)
  C9---C8---H8B      109.5         F4\'---P1---F3\'   89.7 (4)
  H8A---C8---H8B     108.1         F3---P1---F3\'     30.1 (4)
  C8---C9---H9A      109.5         F5---P1---F3\'     82.8 (8)
  C8---C9---H9B      109.5         F2---P1---F3\'     122.1 (4)
  H9A---C9---H9B     109.5         F1\'---P1---F3\'   174.5 (4)
  C8---C9---H9C      109.5         F6---P1---F3\'     87.9 (6)
  H9A---C9---H9C     109.5         F2\'---P1---F3\'   86.8 (4)
  H9B---C9---H9C     109.5         F4---P1---F3\'     60.5 (3)
  C16---C11---C12    117.94 (18)   F1---P1---F3\'     143.9 (4)
  C16---C11---C1     122.20 (17)   F6\'---P1---F3\'   100.4 (6)
  C12---C11---C1     119.85 (17)   F4\'---P1---F5\'   84.6 (5)
  C16---C11---Fe1    68.60 (11)    F3---P1---F5\'     98.0 (7)
  C12---C11---Fe1    69.27 (11)    F5---P1---F5\'     12.5 (10)
  C1---C11---Fe1     133.56 (12)   F2---P1---F5\'     86.2 (6)
  C13---C12---C11    121.08 (19)   F1\'---P1---F5\'   95.7 (7)
  C13---C12---Fe1    69.75 (12)    F6---P1---F5\'     174.9 (9)
  C11---C12---Fe1    71.34 (11)    F2\'---P1---F5\'   99.0 (5)
  C13---C12---H12A   118.5         F4---P1---F5\'     89.5 (6)
  C11---C12---H12A   118.5         F1---P1---F5\'     77.6 (7)
  Fe1---C12---H12A   118.5         F6\'---P1---F5\'   168.9 (8)
  C14---C13---C12    120.31 (19)   F3\'---P1---F5\'   88.4 (8)
  C14---C13---Fe1    70.29 (12)                       
  ------------------ ------------- ------------------ -------------

###### Selected geometric parameters (Å)

  ----------- -------------
  Fe1---C15   2.072 (2)
  Fe1---C16   2.073 (2)
  Fe1---C13   2.077 (2)
  Fe1---C14   2.078 (2)
  Fe1---C12   2.0906 (19)
  Fe1---C11   2.1179 (19)
  Fe1---C21   2.050 (2)
  Fe1---C24   2.050 (2)
  Fe1---C25   2.052(2)
  Fe1---C23   2.053 (2)
  Fe1---C22   2.063 (2)
  ----------- -------------
