[η⁶-1-Chloro-2-(pyrrolidin-1-yl)­benzene](η⁵-cyclo­penta­dien­yl)iron(II) hexa­fluoridophosphate and (η⁵-cyclo­penta­dien­yl){2-[η⁶-2-(pyrrolidin-1-yl)­phen­yl]phenol}iron(II) hexa­fluorido­phosphate

In the complex salt [η⁶-1-chloro-2-(pyrrolidin-1-yl)­ben­zene](η⁵-cyclo­penta­dien­yl)iron(II) hexa­fluorido­phosphate, [Fe(C₅H₅)(C₁₀H₁₂ClN)]PF₆, (I), the complexed cyclo­penta­dienyl and benzene rings are almost parallel, with a dihedral angle between their planes of 2.3 (3)°. In a related complex salt, (η⁵-cyclo­penta­dien­yl){2-[η⁶-2-(pyrrolidin-1-yl)phen­yl]phenol}iron(II) hexa­fluoridophosphate, [Fe(C₅H₅)(C₁₆H₁₇NO)]PF₆, (II), the analogous angle is 5.4 (1)°. In both complexes, the aromatic C atom bound to the pyrrolidine N atom is located out of the plane defined by the remaining five ring C atoms. The dihedral angles between the plane of these five ring atoms and a plane defined by the N-bound aromatic C atom and two neighboring C atoms are 9.7 (8) and 5.6 (2)° for (I) and (II), respectively.

S1. Comment

[(η⁵-Cyclopentadienyl)(η⁶-o-chloro-N-pyrrolidinylbenzene)iron(II)] hexafluoridophosphate, along with similar m- and p-chloro-N-butylamino- and di-N-butylamino-, chloro-N-pyrrolidino- and di-N-pyrrolidino-, and some chlorocyanobenzene complexes with a cyclopentadienyliron(II) moiety, were reported in the study of nucleophilic aromatic mono- and di-substitution reactions using o-, m- and p-dichlorobenzene FeCp complexes (Lee et al., 1989) with amines and the cyanide anion. [(η⁵-Cyclopentadienyl)(η⁶-o-N-pyrrolidinyl-o'-hydroxybiphenyl)iron(II)] hexafluoridophosphate was obtained in another nucleophilic substitution reaction, a ring-opening reaction of a furan ring in dibenzofuran facilitated by η⁶-complexation with an FeCp moiety (Lee et al., 1983). Having previously observed a distortion of the FeCp-complexed benzene ring, which resulted from the o-dipyrrolidinyl substitution of benzene (Jenkins et al., 2009), we resolved to take a closer look at FeCp complexes of related o-disubstituted benzenes in which one of the substituents is a pyrrolidinyl group, and the second one may exert either steric hindrance or a significant electronic influence.

The ORTEP view of the chloropyrrolidinyl, (I), and pyrrolidinylbiphenyl, (II), complexes is shown in Figs. 1 and 2, respectively. The Fe ion is located at distances of 1.644 (4) and 1.663 (1) Å from the Cp plane, and 1.554 (4) and 1.557 (1) Å from the phenyl ring plane, respectively, for both complexes. These values are close to those reported in the literature for similar complexes (see, for example, Piórko et al., 1995; Fuentealba et al., 2007; Manzur et al., 2007, 2009; Hendsbee et al., 2010, and literature cited therein).

In the chloropyrrolidinyl complex, (I), the benzene and Cp rings are nearly parallel with a dihedral angle of 2.3 (3)°, while in the pyrrolidinylbiphenyl complex, (II), this angle is larger, reaching 5.4 (1)°. This second value is among the largest reported from our work, along with the value 5.34 (13)° given previously by Jenkins et al. (2009). This value is also similar to 5.4° reported for the hexaethylbenzene–CpFe complex (Dubois et al., 1989), although lower than the value 7° reported for the 1,1'-trimethylenebenzene–CpFe cation (Nesmeyanov et al., 1977). No standard uncertainties were provided by these authors in their reports.

For (I) the Fe–phenyl-ring C-atom distance averages at 2.098 Å, while the distances towards the quaternary carbon atoms are 2.085 (10) and 2.237 (8) Å for Fe—C1 (bonding Cl) and Fe—C2 (bonding N), respectively. For (II) the similar values are 2.107 Å for an average, and 2.139 (3) and 2.218 (3) Å for Fe—C1 (bonding C of the second ring) and Fe—C2 (bonding N), respectively. The values for the Fe—C2 distance, which carries an N-pyrrolidinyl substituent in both complexes, are among the largest reported for similar complexes, along with the value 2.252 (2) Å reported earlier for one of the quaternary ring carbon atoms of a dipyrrolidinyl complex (Jenkins et al., 2009). The other reports on the Fe—C_quat of similar value came from examination of the structure of an Fe(Me₅Cp) phenoxide–water complex, with an Fe–quaternary C bonding oxygen distance of 2.269 (9) Å (Moulines et al., 1995; Djakovitch et al., 1996), a p-methylphenylhydrazine FeCp fragment in a tungsten complex at 2.24 (1) Å (Ishii et al., 1994), and for N'-isopropylidene hydrazone of p-methylphenylhydrazine at 2.201 (5) Å (Manzur et al., 2000). Most of the hydrazones for many of both Cp and pentamethylCp complexes examined in a series of studies by Carrillo and coworkers (see, for example, Fuentealba et al., 2007; Manzur et al., 2000, 2007, 2009) have an Fe–quaternary C bonding N distance shorter than that found in our work.

The distance of the pyrrolidinyl nitrogen atom from the C1–C6 phenyl-ring plane is 0.099 (13) and 0.034 (4) Å, respectively, for complexes (I) and (II) [ok as edited?]. Both nitrogen atoms appear to be elevated above the respective plane of the complexed ring. These values and long Fe—C2 distances prompted examination of additional selected angles and planes to discern possible deformations of a complexed aromatic ring. Examination of the angles (Fe–quaternary C–bonded atom of substituent X) [Fe—C_quat—X where X is the bonded substituent] for two different substituents revealed that this angle has quite different values in the studied complexes. It was expected that a longer Fe–N-bonded quaternary carbon distance may be reflected in a smaller Fe—C2—N1 angle. For (II) the respective values were 135.4 (2)° for Fe—C1—C7, and 133.8 (2)° for Fe—C2—N1, which is in agreement with the expected order. For (I), however, these values were 133.1 (5)° for Fe—C1—Cl and 135.2 (6)° for Fe—C2—N1, thus the expectations were not substantiated in the case of this complex. As the nitrogen atoms are found above the complexed phenyl-ring plane in both complexes, dihedral angles between the planes formed by each quaternary carbon atom and its direct neighbors in a ring versus planes of other ring carbon atoms were also examined. For (I) a plane centered at the C1 carbon and defined by C2—C1—C6 atoms intersects a plane C2—C3—C4—C5—C6 at a dihedral angle 6.4 (5)°, and a plane made of non-quaternary carbon atoms C3—C4—C5—C6 at 5.1 (6)°, thus essentially this angle is the same. A plane based upon carbon atoms C1—C2— C3, centered upon C2 which is an N-bonding carbon atom, intersects a plane of atoms C3—C4—C5—C6—C1 at 9.7 (8)°, and the plane defined by non-quaternary ring carbon atoms C3—C4—C5—C6 at 10.2 (9)°. For (II) the respective values for similar angles between planes are as follows: C2—C1—C6 and C2—C3—C4—C5—C6 angle 2.8 (2)°; C2—C1—C6 and C3—C4—C5—C6 angle 2.5 (2)°; C1—C2—C3 and C3—C4—C5—C6—C1 at 5.6 (2)°; and, finally, C1—C2—C3 and C3—C4—C5—C6 at 6.2 (2)°. These numbers seem to suggest that a longer Fe—C2 distance and larger dihedral angle between the planes C1—C2—C3 and a plane defined by the ring carbons excluding C2 observed for (I) may be the result of the electronic influence of the chlorine neighbor and, for (II), steric crowding exerted by the second, directly linked phenyl ring. Similar values, 6.0 (5)° and 7.1 (6)°, have been reported for phenylhydrazine complexes studied by Manzur et al. (2000). The pyrrolidinyl ring of (I) in the solid state adopted a twisted conformation with carbon atoms C12 and C13 (C13 is further away from the o-chloro substituent) located below and above, respectively, the plane defined by the remaining three atoms. A similar picture is observed for (II), with carbon atoms C22 and C23 (C23 is further away from the second ring of biphenyl skeleton) located below and above, respectively, the plane of the atoms C21—N1—C24. Bond lengths in the pyrrolidinyl rings of both complexes are similar and in line with literature values (Allen et al., 1987). Nitrogen atoms in both complexes show similar bond lengths toward aromatic ring carbon atoms C2 [1.343 (11) Å for (I) and 1.356 (4) Å for (II)], and toward methylene carbon atoms of pyrrolidinyl rings [range 1.476 (4)–1.484 (12) Å]. The C2—N1 bond length in each complex, which is in agreement with the C_ar—planar N_sp² bond length (Allen et al., 1987), implies that depyramidalization of the N atom takes effect in both complexes. This suggestion is corroborated by the geometry around the N atom – the sum of angles is close to 360° in each complex [358.4 (9) and 357.1 (4)°, respectively, in (I) and (II) [ok as edited?]], and this may, as discussed by Manzur et al. (2000), result from a partial delocalization of the N1 lone pair of electrons toward the complexed phenyl ring.

The average C—C bond length for the complexed phenyl ring of (I) is 1.410 Å. For (II) this average is 1.419 Å and a bond between quaternary carbon atoms C1—C2 [1.441 (4) Å] is slightly longer than the average. In (I) the C1—Cl bond length and the Fe—C1 distance, 1.728 (10) and 2.085 (10) Å, respectively, are similar to values reported for the same bonds in an o-dichlorobenzene FeCp complex (Crane, 2003). The second phenyl ring in the structure of (II) shows no unusual features, and a bond between the rings at C1—C7 has a length of 1.491 (4) Å, which is in agreement with literature data (Allen et al., 1987). The plane of this second ring is tilted at 74.9 (3)° against the plane of the complexed ring.

Related literature

For related literature, see: Allen et al. (1987); Crane (2003); Djakovitch et al. (1996); Dubois et al. (1989); Fuentealba et al. (2007); Hendsbee et al. (2010); Ishii et al. (1994); Jenkins et al. (2009); Lee et al. (1983, 1989); Manzur et al. (2000, 2007, 2009); Moulines et al. (1995); Nesmeyanov et al. (1977); Piórko et al. (1995); Spek (2009).

S2. Experimental

The title compounds were prepared following methods described in the literature. [(η⁵-Cyclopentadienyl)(η⁶-o-chloro-N-pyrrolidinylbenzene) iron(II)] hexafluoridophosphate was prepared from (o-dichlorobenzene)FeCp PF₆ in reaction with pyrrolidine according to the method of Lee et al. (1989). The [(η⁵-C₅H₅)(η⁶-o-N-pyrrolidinyl-o'- hydroxybiphenyl)iron] hexafluoridophosphate was prepared in a ring opening of dibenzofuran in a reaction of (dibenzofuran) FeCp PF₆ with pyrrolidine as described by Lee et al. (1983). In both cases the best crystals used for data collection were grown by cooling a solution of each complex in a mixture of acetone, diethyl ether and dichloromethane at 280 K for an extended period of time. It should be noted that, despite our countless crystallization attempts under different conditions, the quality of the chloropyrrolidinyl complex crystals was not as good as for the pyrridinylbiphenyl complex, and this affected both our results and their analysis.

S3. Refinement

For [(η⁵-cyclopentadienyl)(η⁶-o-chloro-N-pyrrolidinylbenzene)iron(II)] hexafluoridophosphate the H atoms were placed in geometrically idealized positions with C—H distances of 1.00 Å for all complexed, uncomplexed aromatic and Cp protons, and 0.99 Å for aliphatic protons, and constrained to ride on their parent C atoms with U_iso(H) = 1.2U_eq(C). The structure contains two molecules of a single enantiomer in the unit cell, and the structure itself was refined as an enantiomeric mixture using TWIN and BASF commands (BASF = 0.358). A warning was generated by PLATON (Spek, 2009); ADDSYM indicated P21/m pseudo-symmetry. The pseudo-inversion symmetry indicated is not present as crystallographic symmetry, as a complete overlap of the two molecules is not formed upon application of the proposed inversion symmetry element. Additionally, an extensive search for the cell of apparently higher symmetry was attempted using CELL_NOW with a total of 4399 reflections indexed and a minimum [I/σ(I)] value of 1.75 for the spots harvested. The search for a larger cell was unsuccessful and therefore the pseudo-symmetry warning was ignored and refinement was completed in space group P21. Three outlying reflections with h, k, l values (4,0,0), (4,-1,-1), and (4,0,2) were omitted from the refinement using the OMIT command. This complex contains a cyclopentadienyl (Cp) ring which is π-bonded to a Fe atom, and the thermal motion of this Cp ring resulted in unsatisfactory anisotropic displacement parameters for atoms C1–C6 (coordinated aromatic ring) and atoms C21–C25 (complexed Cp). This was resolved through use of the restraints applied to the refinement of these atoms: the U_ij components of these atoms were restrained to be equal to within 0.001 Ų and their anisotropic displacement parameters were restrained to be equal to within 0.02 Ų. For the [(η⁵-C₅H₅)(η⁶-o-N-pyrrolidinyl-o'-hydroxybiphenyl)iron] hexafluoridophosphate the H atoms were placed in geometrically idealized positions with C—H distances of 1.0 Å for all complexed, uncomplexed aromatic and Cp protons, 0.99 Å for aliphatic protons, and 0.84 Å for R—O—H protons. Protons were constrained to ride on the parent C atom with U_iso(H) = 1.2U_eq(C) for the aromatic, Cp and aliphatic protons, and U_iso(H) = 1.5U_eq (O) for R—O—H protons.

Computing details

For both compounds, data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. View of the cation showing the labeling of non-H atoms of (o-chloro-N-pyrrolidinylbenzene) FeCp PF6 complex with displacement ellipsoids shown at 50% probability levels. Hydrogen atoms are omitted for clarity.
	Fig. 2. View of the cation showing the labeling of non-H atoms of (o-N-pyrrolidinyl-o'-hydroxybiphenyl) FeCp PF6 complex with displacement ellipsoids shown at 50% probability levels. Hydrogen atoms are omitted for clarity.

(I) [η⁶-1-Chloro-2-(pyrrolidin-1-yl)benzene](η⁵-cyclopentadienyl)iron(II) hexafluoridophosphate

Crystal data

[Fe(C5H5)(C10H12ClN)]PF6	F(000) = 452
Mr = 447.57	Dx = 1.800 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4368 reflections
a = 7.000 (2) Å	θ = 0.5–0.8°
b = 13.401 (4) Å	µ = 1.23 mm^−1
c = 8.805 (3) Å	T = 100 K
β = 95.183 (4)°	Plate, orange
V = 822.6 (4) Å^3	0.24 × 0.20 × 0.15 mm
Z = 2

Data collection

Bruker APEXII CCD diffractometer	2880 independent reflections
Radiation source: fine-focus sealed tube	2553 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
ϕ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −8→8
Tmin = 0.522, Tmax = 0.746	k = −15→15
7536 measured reflections	l = −10→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.081	H-atom parameters constrained
wR(F^2) = 0.206	w = 1/[σ^2(Fo^2) + (0.0848P)^2 + 8.2992P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2880 reflections	Δρmax = 1.89 e Å^−3
227 parameters	Δρmin = −1.12 e Å^−3
507 restraints	Absolute structure: Flack (1983), 1374 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.36 (5)

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 (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.91533 (18)	0.75779 (9)	0.53024 (15)	0.0205 (3)
C1	0.6598 (14)	0.6771 (7)	0.5177 (11)	0.0211 (4)
C2	0.6209 (11)	0.7545 (8)	0.4082 (10)	0.0211 (4)
C3	0.6892 (14)	0.8507 (7)	0.4600 (11)	0.0211 (4)
C4	0.7497 (13)	0.8719 (7)	0.6117 (11)	0.0211 (4)
C5	0.7738 (13)	0.7949 (7)	0.7184 (11)	0.0212 (4)
C6	0.7265 (14)	0.6970 (7)	0.6696 (11)	0.0212 (4)
H3	0.7101	0.9025	0.3815	0.025*
H4	0.8116	0.9378	0.6369	0.025*
H5	0.8476	0.8066	0.8195	0.025*
H6	0.7703	0.6399	0.7371	0.025*
Cl1	0.6057 (4)	0.55268 (16)	0.4851 (3)	0.0308 (6)
N1	0.5490 (10)	0.7411 (6)	0.2630 (9)	0.0229 (17)
C11	0.5404 (17)	0.6456 (7)	0.1773 (11)	0.029 (2)
H11A	0.4257	0.6064	0.1977	0.035*
H11B	0.6567	0.6049	0.2036	0.035*
C12	0.529 (2)	0.6809 (10)	0.0081 (13)	0.042 (3)
H12A	0.6580	0.6915	−0.0263	0.051*
H12B	0.4574	0.6326	−0.0606	0.051*
C13	0.4210 (17)	0.7779 (11)	0.0169 (12)	0.042 (3)
H13A	0.2829	0.7656	0.0256	0.050*
H13B	0.4350	0.8195	−0.0744	0.050*
C14	0.5143 (17)	0.8280 (8)	0.1602 (12)	0.032 (3)
H14A	0.6356	0.8616	0.1407	0.039*
H14B	0.4269	0.8770	0.2020	0.039*
C21	1.1141 (13)	0.6545 (7)	0.4948 (11)	0.0213 (4)
H21	1.0934	0.5806	0.4916	0.026*
C22	1.0850 (13)	0.7245 (7)	0.3609 (12)	0.0212 (4)
H22	1.0423	0.7067	0.2528	0.025*
C23	1.1333 (14)	0.8199 (7)	0.4191 (11)	0.0212 (4)
H23	1.1263	0.8837	0.3600	0.025*
C24	1.1891 (14)	0.8101 (7)	0.5708 (11)	0.0212 (4)
H24	1.2253	0.8677	0.6397	0.025*
C25	1.1787 (14)	0.7096 (7)	0.6224 (12)	0.0212 (4)
H25	1.2126	0.6841	0.7281	0.025*
P1	0.9812 (4)	0.99521 (19)	0.0244 (3)	0.0242 (6)
F1	0.8990 (11)	1.0087 (5)	0.1850 (7)	0.0436 (17)
F2	1.1952 (10)	1.0018 (5)	0.1046 (8)	0.0449 (18)
F3	1.0658 (10)	0.9805 (5)	−0.1339 (8)	0.0411 (17)
F4	0.7737 (10)	0.9866 (5)	−0.0536 (9)	0.050 (2)
F5	0.9791 (11)	1.1130 (5)	0.0040 (9)	0.0446 (19)
F6	0.9838 (9)	0.8770 (4)	0.0486 (7)	0.0341 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0192 (5)	0.0146 (6)	0.0278 (6)	−0.0012 (5)	0.0023 (4)	0.0012 (5)
C1	0.0197 (6)	0.0153 (6)	0.0284 (7)	−0.0011 (6)	0.0024 (5)	0.0011 (6)
C2	0.0197 (6)	0.0153 (6)	0.0283 (7)	−0.0011 (6)	0.0024 (5)	0.0011 (6)
C3	0.0197 (6)	0.0153 (6)	0.0284 (7)	−0.0011 (6)	0.0024 (5)	0.0011 (6)
C4	0.0198 (6)	0.0153 (6)	0.0283 (7)	−0.0011 (6)	0.0024 (5)	0.0011 (6)
C5	0.0198 (6)	0.0154 (6)	0.0284 (7)	−0.0011 (6)	0.0024 (5)	0.0011 (6)
C6	0.0198 (6)	0.0154 (6)	0.0284 (7)	−0.0011 (6)	0.0024 (5)	0.0011 (6)
Cl1	0.0391 (15)	0.0108 (12)	0.0418 (16)	−0.0043 (10)	−0.0007 (12)	0.0005 (11)
N1	0.019 (4)	0.021 (4)	0.028 (4)	0.003 (3)	0.005 (3)	0.000 (4)
C11	0.049 (7)	0.018 (5)	0.021 (5)	−0.008 (5)	0.008 (5)	−0.010 (4)
C12	0.063 (9)	0.041 (8)	0.021 (6)	0.021 (6)	−0.001 (5)	−0.005 (5)
C13	0.034 (6)	0.065 (10)	0.026 (5)	0.000 (6)	−0.001 (4)	0.006 (6)
C14	0.036 (6)	0.031 (6)	0.030 (6)	0.014 (5)	0.001 (5)	0.005 (5)
C21	0.0199 (6)	0.0154 (6)	0.0285 (7)	−0.0010 (6)	0.0024 (5)	0.0011 (6)
C22	0.0198 (6)	0.0155 (6)	0.0284 (7)	−0.0010 (6)	0.0024 (5)	0.0011 (6)
C23	0.0198 (6)	0.0154 (6)	0.0284 (7)	−0.0011 (6)	0.0024 (5)	0.0012 (6)
C24	0.0198 (6)	0.0155 (6)	0.0284 (7)	−0.0010 (6)	0.0024 (5)	0.0012 (6)
C25	0.0198 (6)	0.0154 (6)	0.0285 (7)	−0.0011 (6)	0.0023 (5)	0.0011 (6)
P1	0.0314 (14)	0.0117 (13)	0.0283 (14)	−0.0015 (10)	−0.0041 (11)	−0.0030 (10)
F1	0.072 (5)	0.026 (3)	0.032 (3)	−0.007 (3)	0.003 (3)	−0.003 (3)
F2	0.039 (4)	0.018 (3)	0.072 (5)	0.009 (3)	−0.024 (3)	−0.006 (3)
F3	0.052 (4)	0.028 (4)	0.045 (4)	−0.004 (3)	0.014 (3)	−0.008 (3)
F4	0.049 (4)	0.017 (3)	0.075 (5)	−0.006 (3)	−0.037 (4)	0.003 (3)
F5	0.063 (5)	0.015 (3)	0.053 (4)	−0.002 (3)	−0.005 (4)	−0.001 (3)
F6	0.043 (4)	0.008 (3)	0.048 (4)	0.007 (2)	−0.012 (3)	−0.004 (3)

Geometric parameters (Å, º)

Fe1—C1	2.085 (10)	C11—H11A	0.9900
Fe1—C2	2.237 (8)	C11—H11B	0.9900
Fe1—C3	2.064 (10)	C12—H12A	0.9900
Fe1—C4	2.085 (10)	C12—H12B	0.9900
Fe1—C5	2.067 (10)	C13—C12	1.508 (17)
Fe1—C6	2.052 (10)	C13—H13A	0.9900
Fe1—C21	2.008 (9)	C13—H13B	0.9900
Fe1—C22	2.038 (10)	C14—C13	1.524 (17)
Fe1—C23	2.061 (10)	C14—H14A	0.9900
Fe1—C24	2.041 (10)	C14—H14B	0.9900
Fe1—C25	2.051 (10)	C21—H21	1.0000
C1—C2	1.425 (14)	C22—C21	1.506 (13)
C3—C2	1.435 (14)	C22—H22	1.0000
C3—H3	1.0000	C23—C22	1.407 (13)
C3—C4	1.394 (14)	C23—H23	1.0000
C4—H4	1.0000	C23—C24	1.364 (14)
C5—C4	1.395 (13)	C24—H24	1.0000
C5—H5	1.0000	C25—C24	1.425 (12)
C6—C5	1.411 (12)	C25—H25	1.0000
C6—H6	1.0000	C25—C21	1.386 (14)
C1—C6	1.402 (14)	P1—F1	1.585 (7)
Cl1—C1	1.728 (10)	P1—F2	1.600 (7)
N1—C2	1.344 (11)	P1—F3	1.575 (7)
N1—C11	1.484 (12)	P1—F4	1.554 (7)
N1—C14	1.482 (13)	P1—F5	1.588 (7)
C11—C12	1.558 (15)	P1—F6	1.599 (6)
Fe1—C3—H3	118.0	C21—Fe1—C4	167.0 (4)
Fe1—C4—H4	118.7	C21—Fe1—C5	132.9 (4)
Fe1—C5—H5	120.3	C21—Fe1—C6	108.2 (4)
Fe1—C6—H6	118.7	C21—Fe1—C22	43.7 (4)
Fe1—C21—H21	125.9	C21—Fe1—C23	69.6 (4)
Fe1—C22—H22	127.2	C21—Fe1—C24	67.1 (4)
Fe1—C23—H23	126.1	C21—Fe1—C25	39.9 (4)
Fe1—C24—H24	123.6	C21—C25—Fe1	68.4 (6)
Fe1—C25—H25	127.2	C21—C25—C24	105.5 (9)
C1—C2—C3	113.7 (8)	C21—C22—Fe1	67.1 (5)
C1—Fe1—C2	38.3 (4)	C21—C22—H22	127.2
C1—C2—Fe1	65.1 (5)	C21—C25—H25	127.2
C1—C6—C5	121.1 (9)	C22—Fe1—C1	113.7 (4)
C1—C6—Fe1	71.5 (6)	C22—Fe1—C2	102.5 (4)
C1—C6—H6	118.7	C22—Fe1—C3	113.2 (4)
C2—C1—Cl1	124.3 (7)	C22—Fe1—C4	142.3 (4)
C2—C1—Fe1	76.6 (5)	C22—Fe1—C5	173.0 (4)
C2—C3—Fe1	77.2 (5)	C22—Fe1—C6	143.1 (4)
C2—C3—H3	118.0	C22—Fe1—C23	40.2 (4)
C2—N1—C11	126.4 (9)	C22—Fe1—C24	66.6 (4)
C2—N1—C14	120.2 (9)	C22—Fe1—C25	70.0 (4)
C3—Fe1—C1	70.5 (4)	C22—C21—Fe1	69.2 (5)
C3—Fe1—C2	38.7 (4)	C22—C23—Fe1	69.0 (6)
C3—Fe1—C4	39.3 (4)	C22—C23—H23	126.1
C3—C2—Fe1	64.1 (5)	C22—C21—H21	125.9
C3—C4—Fe1	69.6 (5)	C23—Fe1—C1	148.5 (4)
C3—C4—H4	118.7	C23—Fe1—C2	118.0 (4)
C3—Fe1—C23	101.2 (4)	C23—Fe1—C4	109.0 (4)
C4—Fe1—C1	84.1 (4)	C23—C22—Fe1	70.8 (6)
C4—Fe1—C2	70.3 (4)	C23—C22—C21	105.7 (8)
C4—C3—C2	123.5 (9)	C23—C22—H22	127.2
C4—C3—Fe1	71.2 (6)	C23—C24—Fe1	71.4 (6)
C4—C5—C6	118.2 (9)	C23—C24—C25	112.7 (9)
C4—C5—Fe1	71.1 (6)	C23—C24—H24	123.6
C4—C3—H3	118.0	C24—Fe1—C1	167.1 (4)
C4—C5—H5	120.3	C24—Fe1—C2	154.2 (4)
C5—Fe1—C1	72.3 (4)	C24—Fe1—C3	121.9 (4)
C5—Fe1—C2	84.4 (4)	C24—Fe1—C4	103.3 (4)
C5—Fe1—C3	71.6 (4)	C24—Fe1—C5	106.7 (4)
C5—Fe1—C4	39.3 (4)	C24—Fe1—C6	132.6 (4)
C5—Fe1—C23	135.4 (4)	C24—Fe1—C23	38.8 (4)
C5—Fe1—C25	103.7 (4)	C24—Fe1—C25	40.8 (3)
C5—C4—Fe1	69.6 (5)	C24—C25—Fe1	69.3 (6)
C5—C6—Fe1	70.5 (6)	C24—C25—H25	127.2
C5—C4—C3	120.2 (9)	C24—C23—C22	107.9 (9)
C5—C4—H4	118.7	C24—C23—Fe1	69.8 (6)
C5—C6—H6	118.7	C24—C23—H23	126.1
C6—Fe1—C1	39.6 (4)	C25—Fe1—C1	126.4 (4)
C6—Fe1—C2	70.4 (4)	C25—Fe1—C2	160.1 (4)
C6—Fe1—C3	84.3 (4)	C25—Fe1—C3	161.1 (4)
C6—Fe1—C4	71.2 (4)	C25—Fe1—C4	127.1 (4)
C6—Fe1—C5	40.1 (3)	C25—Fe1—C23	68.7 (4)
C6—Fe1—C23	171.4 (4)	C25—C24—Fe1	70.0 (6)
C6—Fe1—C25	104.1 (4)	C25—C21—Fe1	71.7 (6)
C6—C1—Fe1	68.9 (5)	C25—C21—C22	108.3 (8)
C6—C1—C2	122.3 (9)	C25—C21—H21	125.9
C6—C1—Cl1	113.0 (7)	C25—C24—H24	123.6
C6—C5—Fe1	69.4 (6)	N1—C2—Fe1	135.2 (6)
C6—C5—H5	120.3	N1—C2—C1	125.3 (9)
Cl1—C1—Fe1	133.1 (5)	N1—C2—C3	120.5 (9)
H11A—C11—H11B	109.1	N1—C11—C12	102.8 (8)
C11—C12—H12A	111.5	N1—C11—H11A	111.2
C11—C12—H12B	111.5	N1—C11—H11B	111.2
H12A—C12—H12B	109.3	N1—C14—C13	101.1 (9)
C12—C11—H11A	111.2	N1—C14—H14A	111.5
C12—C11—H11B	111.2	N1—C14—H14B	111.5
C12—C13—C14	104.1 (9)	F1—P1—F5	89.2 (4)
C12—C13—H13A	110.9	F1—P1—F6	89.7 (4)
C12—C13—H13B	110.9	F1—P1—F2	90.0 (4)
C13—C12—C11	101.3 (9)	F2—P1—F6	89.8 (3)
C13—C12—H12A	111.5	F3—P1—F5	91.4 (4)
C13—C12—H12B	111.5	F3—P1—F6	89.6 (4)
C13—C14—H14A	111.5	F3—P1—F2	89.2 (4)
C13—C14—H14B	111.5	F3—P1—F1	179.0 (4)
H13A—C13—H13B	109.0	F4—P1—F3	90.6 (4)
C14—C13—H13A	110.9	F4—P1—F1	90.1 (5)
C14—C13—H13B	110.9	F4—P1—F5	91.4 (4)
C14—N1—C11	111.8 (8)	F4—P1—F2	178.9 (4)
H14A—C14—H14B	109.4	F4—P1—F6	89.1 (3)
C21—Fe1—C1	103.7 (4)	F5—P1—F6	178.8 (4)
C21—Fe1—C2	122.2 (4)	F5—P1—F2	89.6 (4)
C21—Fe1—C3	153.2 (4)

(II) (η⁵-cyclopentadienyl){2-[η⁶-2-(pyrrolidin-1-yl)phenyl]phenol}iron(II) hexafluoridophosphate

Crystal data

[Fe(C5H5)(C16H17NO)]PF6	F(000) = 1032
Mr = 505.22	Dx = 1.674 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4370 reflections
a = 10.9764 (11) Å	θ = 2.9–24.9°
b = 9.4221 (10) Å	µ = 0.90 mm^−1
c = 19.393 (2) Å	T = 100 K
β = 91.608 (1)°	Block, brown
V = 2004.8 (4) Å^3	0.33 × 0.30 × 0.28 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	3451 independent reflections
Radiation source: fine-focus sealed tube	2720 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ϕ and ω scans	θmax = 24.9°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
Tmin = 0.691, Tmax = 0.745	k = −11→11
9910 measured reflections	l = −19→22

Refinement

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 0.85	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
3451 reflections	(Δ/σ)max < 0.001
281 parameters	Δρmax = 0.60 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.49533 (4)	0.19729 (4)	0.19044 (2)	0.01588 (16)
C1	0.3646 (3)	0.1834 (3)	0.26993 (15)	0.0161 (6)
C2	0.4026 (3)	0.0401 (3)	0.25601 (15)	0.0180 (6)
C3	0.4084 (3)	0.0005 (3)	0.18487 (15)	0.0206 (7)
H3	0.4579	−0.0845	0.1728	0.025*
C4	0.3660 (3)	0.0897 (3)	0.13090 (16)	0.0215 (7)
H4	0.3847	0.0645	0.0822	0.026*
C5	0.3239 (3)	0.2273 (3)	0.14553 (16)	0.0213 (7)
H5	0.3121	0.2978	0.1074	0.026*
C6	0.3253 (3)	0.2725 (3)	0.21433 (15)	0.0184 (6)
H6	0.3164	0.3763	0.2236	0.022*
C7	0.3529 (3)	0.2451 (3)	0.34022 (15)	0.0173 (6)
C8	0.2562 (3)	0.2022 (3)	0.38040 (15)	0.0184 (6)
O1	0.18164 (19)	0.0968 (2)	0.35416 (11)	0.0253 (5)
H1	0.1138	0.1007	0.3730	0.038*
C9	0.2380 (3)	0.2636 (3)	0.44431 (15)	0.0220 (7)
H9	0.1724	0.2330	0.4716	0.026*
C10	0.3152 (3)	0.3693 (3)	0.46806 (15)	0.0228 (7)
H10	0.3028	0.4111	0.5119	0.027*
C11	0.4105 (3)	0.4150 (3)	0.42868 (15)	0.0240 (7)
H11	0.4636	0.4879	0.4451	0.029*
C12	0.4278 (3)	0.3529 (3)	0.36454 (15)	0.0210 (7)
H12	0.4924	0.3853	0.3370	0.025*
N1	0.4419 (2)	−0.0535 (2)	0.30488 (12)	0.0198 (6)
C21	0.4754 (3)	−0.0197 (3)	0.37728 (15)	0.0243 (7)
H21A	0.4022	−0.0144	0.4058	0.029*
H21B	0.5199	0.0716	0.3806	0.029*
C22	0.5577 (3)	−0.1437 (3)	0.39999 (18)	0.0298 (8)
H22A	0.6443	−0.1226	0.3915	0.036*
H22B	0.5485	−0.1653	0.4495	0.036*
C23	0.5120 (3)	−0.2656 (3)	0.35507 (19)	0.0315 (8)
H23A	0.4363	−0.3069	0.3732	0.038*
H23B	0.5743	−0.3410	0.3518	0.038*
C24	0.4881 (3)	−0.1948 (3)	0.28565 (18)	0.0259 (7)
H24A	0.5640	−0.1869	0.2595	0.031*
H24B	0.4266	−0.2480	0.2577	0.031*
C31	0.6567 (3)	0.2581 (4)	0.23864 (17)	0.0255 (7)
H31	0.6735	0.2610	0.2896	0.031*
C32	0.6095 (3)	0.3712 (3)	0.19759 (16)	0.0232 (7)
H32	0.5870	0.4677	0.2145	0.028*
C33	0.5993 (3)	0.3232 (3)	0.12884 (17)	0.0241 (7)
H33	0.5686	0.3801	0.0884	0.029*
C34	0.6392 (3)	0.1800 (3)	0.12681 (17)	0.0255 (7)
H34	0.6429	0.1188	0.0848	0.031*
C35	0.6758 (3)	0.1403 (3)	0.19478 (17)	0.0268 (7)
H35	0.7089	0.0457	0.2093	0.032*
P2	0.65847 (8)	0.73081 (9)	0.06508 (4)	0.0237 (2)
F1	0.6155 (3)	0.6100 (3)	0.01285 (12)	0.0644 (7)
F2	0.74912 (16)	0.62375 (19)	0.10345 (10)	0.0313 (5)
F3	0.5652 (2)	0.8390 (3)	0.02847 (12)	0.0546 (7)
F4	0.7001 (2)	0.8531 (2)	0.11736 (11)	0.0578 (7)
F5	0.5540 (2)	0.6833 (3)	0.11673 (13)	0.0626 (8)
F6	0.76073 (19)	0.7797 (2)	0.01392 (11)	0.0426 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0136 (3)	0.0174 (2)	0.0166 (3)	−0.00013 (16)	0.00057 (18)	0.00130 (16)
C1	0.0113 (15)	0.0182 (14)	0.0188 (15)	−0.0019 (11)	0.0014 (12)	−0.0011 (11)
C2	0.0111 (15)	0.0194 (14)	0.0236 (16)	−0.0029 (12)	0.0009 (12)	0.0009 (12)
C3	0.0191 (16)	0.0191 (14)	0.0239 (16)	−0.0021 (12)	0.0042 (13)	−0.0026 (12)
C4	0.0162 (16)	0.0273 (16)	0.0210 (16)	−0.0063 (13)	0.0004 (12)	−0.0018 (13)
C5	0.0143 (16)	0.0303 (17)	0.0194 (16)	−0.0025 (13)	0.0011 (13)	0.0031 (13)
C6	0.0124 (15)	0.0213 (15)	0.0215 (16)	−0.0001 (12)	0.0028 (12)	0.0015 (12)
C7	0.0191 (16)	0.0162 (13)	0.0167 (15)	0.0042 (12)	0.0003 (12)	0.0036 (11)
C8	0.0168 (16)	0.0161 (14)	0.0221 (16)	0.0011 (12)	−0.0002 (13)	0.0020 (12)
O1	0.0200 (12)	0.0283 (11)	0.0280 (12)	−0.0084 (10)	0.0067 (9)	−0.0053 (9)
C9	0.0217 (18)	0.0253 (16)	0.0192 (17)	0.0023 (14)	0.0043 (13)	0.0024 (13)
C10	0.0292 (18)	0.0218 (15)	0.0172 (15)	0.0032 (14)	0.0009 (13)	0.0009 (12)
C11	0.0302 (18)	0.0201 (15)	0.0213 (16)	−0.0033 (14)	−0.0052 (14)	0.0012 (12)
C12	0.0235 (17)	0.0204 (15)	0.0192 (16)	−0.0038 (13)	0.0005 (13)	0.0041 (12)
N1	0.0185 (14)	0.0162 (12)	0.0246 (14)	0.0010 (10)	0.0009 (11)	0.0022 (10)
C21	0.0249 (17)	0.0215 (15)	0.0264 (17)	0.0029 (13)	−0.0025 (14)	0.0059 (13)
C22	0.0229 (18)	0.0301 (17)	0.0361 (19)	0.0050 (15)	−0.0034 (15)	0.0103 (15)
C23	0.0230 (19)	0.0207 (16)	0.051 (2)	0.0038 (14)	0.0041 (16)	0.0097 (15)
C24	0.0234 (18)	0.0180 (15)	0.0366 (19)	0.0019 (13)	0.0052 (15)	0.0031 (13)
C31	0.0180 (17)	0.0322 (17)	0.0261 (17)	−0.0069 (14)	−0.0017 (14)	0.0039 (14)
C32	0.0196 (16)	0.0234 (16)	0.0269 (17)	−0.0070 (13)	0.0040 (13)	0.0004 (13)
C33	0.0178 (17)	0.0266 (16)	0.0284 (18)	−0.0044 (13)	0.0061 (14)	0.0047 (13)
C34	0.0181 (17)	0.0303 (17)	0.0287 (18)	−0.0010 (14)	0.0106 (14)	0.0007 (14)
C35	0.0135 (16)	0.0305 (17)	0.0366 (19)	0.0025 (14)	0.0021 (14)	0.0082 (15)
P2	0.0211 (5)	0.0293 (5)	0.0207 (5)	0.0021 (4)	−0.0002 (4)	0.0053 (3)
F1	0.095 (2)	0.0546 (15)	0.0423 (14)	−0.0369 (14)	−0.0245 (13)	0.0029 (11)
F2	0.0291 (11)	0.0252 (10)	0.0395 (11)	0.0080 (8)	−0.0026 (9)	0.0048 (8)
F3	0.0384 (13)	0.0706 (16)	0.0548 (15)	0.0169 (12)	−0.0003 (11)	0.0388 (12)
F4	0.107 (2)	0.0299 (11)	0.0353 (13)	0.0136 (13)	−0.0129 (13)	−0.0045 (9)
F5	0.0326 (13)	0.095 (2)	0.0611 (16)	0.0190 (13)	0.0215 (12)	0.0473 (14)
F6	0.0356 (13)	0.0529 (13)	0.0398 (13)	−0.0070 (10)	0.0071 (10)	0.0121 (10)

Geometric parameters (Å, º)

Fe1—C1	2.139 (3)	C12—H12	0.9500
Fe1—C2	2.218 (3)	C7—C12	1.382 (4)
Fe1—C3	2.086 (3)	C2—N1	1.356 (4)
Fe1—C4	2.070 (3)	N1—C24	1.476 (4)
Fe1—C5	2.070 (3)	N1—C21	1.476 (4)
Fe1—C6	2.061 (3)	C21—C22	1.533 (4)
Fe1—C31	2.061 (3)	C21—H21A	0.9900
Fe1—C32	2.066 (3)	C21—H21B	0.9900
Fe1—C33	2.053 (3)	C23—C22	1.518 (5)
Fe1—C34	2.038 (3)	C22—H22A	0.9900
Fe1—C35	2.051 (3)	C22—H22B	0.9900
C2—C1	1.441 (4)	C23—H23A	0.9900
C3—C2	1.432 (4)	C23—H23B	0.9900
C3—H3	1.0000	C24—C23	1.519 (5)
C3—C4	1.411 (4)	C24—H24A	0.9900
C4—H4	1.0000	C24—H24B	0.9900
C4—C5	1.407 (4)	C32—C31	1.419 (5)
C5—H5	1.0000	C31—H31	1.0000
C6—C5	1.400 (4)	C32—H32	1.0000
C6—H6	1.0000	C33—C32	1.409 (4)
C6—C1	1.424 (4)	C33—H33	1.0000
C1—C7	1.491 (4)	C34—C33	1.420 (4)
C7—C8	1.394 (4)	C34—H34	1.0000
C8—O1	1.375 (3)	C34—C35	1.417 (5)
O1—H1	0.8400	C35—H35	1.0000
C8—C9	1.388 (4)	C35—C31	1.418 (5)
C9—H9	0.9500	P2—F1	1.587 (2)
C9—C10	1.379 (4)	P2—F2	1.5873 (19)
C10—H10	0.9500	P2—F3	1.597 (2)
C11—C10	1.381 (4)	P2—F4	1.593 (2)
C11—H11	0.9500	P2—F5	1.607 (2)
C12—C11	1.392 (4)	P2—F6	1.587 (2)
Fe1—C3—H3	118.3	C22—C21—H21A	111.0
Fe1—C4—H4	119.1	C22—C21—H21B	111.0
Fe1—C5—H5	120.0	H22A—C22—H22B	109.1
Fe1—C6—H6	118.0	C23—C22—C21	103.2 (3)
Fe1—C31—H31	126.0	C23—C22—H22A	111.1
Fe1—C32—H32	126.0	C23—C22—H22B	111.1
Fe1—C33—H33	125.8	H23A—C23—H23B	109.1
Fe1—C34—H34	126.1	C23—C24—H24A	111.2
Fe1—C35—H35	126.0	C23—C24—H24B	111.2
C1—Fe1—C2	38.56 (10)	C24—C23—H23A	111.2
C1—C2—Fe1	67.75 (16)	C24—C23—H23B	111.2
C1—C6—Fe1	73.16 (17)	H24A—C24—H24B	109.1
C1—C6—H6	118.0	C24—N1—C21	110.9 (2)
C2—C1—Fe1	73.70 (16)	C31—Fe1—C1	105.99 (12)
C2—C1—C7	124.7 (3)	C31—Fe1—C2	109.17 (12)
C2—C3—Fe1	75.62 (17)	C31—Fe1—C3	131.05 (12)
C2—N1—C21	126.2 (2)	C31—Fe1—C4	163.06 (13)
C2—N1—C24	121.0 (3)	C31—Fe1—C5	155.82 (13)
C3—C2—C1	116.4 (3)	C31—Fe1—C32	40.23 (13)
C2—C3—H3	118.3	C31—C32—Fe1	69.69 (17)
C3—Fe1—C1	70.60 (11)	C31—C32—H32	126.0
C3—Fe1—C2	38.72 (11)	C31—C35—C34	108.0 (3)
C3—C2—Fe1	65.66 (16)	C31—C35—Fe1	70.18 (18)
C3—C4—Fe1	70.78 (16)	C31—C35—H35	126.0
C3—C4—H4	119.1	C32—Fe1—C1	114.73 (11)
C4—C3—C2	122.5 (3)	C32—Fe1—C2	141.15 (12)
C4—C3—H3	118.3	C32—Fe1—C3	169.82 (12)
C4—Fe1—C1	84.75 (11)	C32—Fe1—C4	146.25 (12)
C4—Fe1—C2	70.98 (11)	C32—Fe1—C5	117.56 (12)
C4—Fe1—C3	39.68 (11)	C32—C31—Fe1	70.08 (18)
C4—Fe1—C5	39.74 (12)	C32—C31—H31	126.0
C4—C3—Fe1	69.54 (16)	C32—C33—C34	108.4 (3)
C4—C5—Fe1	70.13 (17)	C32—C33—Fe1	70.49 (17)
C4—C5—H5	120.0	C32—C33—H33	125.8
C5—Fe1—C1	72.04 (11)	C33—Fe1—C1	148.20 (11)
C5—Fe1—C2	84.60 (11)	C33—Fe1—C2	172.40 (12)
C5—Fe1—C3	71.97 (12)	C33—Fe1—C3	138.10 (12)
C5—C4—Fe1	70.13 (17)	C33—Fe1—C4	110.02 (12)
C5—C4—C3	120.1 (3)	C33—Fe1—C5	100.94 (12)
C5—C4—H4	119.1	C33—Fe1—C6	116.98 (12)
C5—C6—Fe1	70.54 (17)	C33—Fe1—C31	67.56 (13)
C5—C6—C1	122.5 (3)	C33—Fe1—C32	40.02 (12)
C5—C6—H6	118.0	C33—C32—C31	107.9 (3)
C6—Fe1—C1	39.59 (11)	C33—C32—Fe1	69.50 (17)
C6—Fe1—C2	70.59 (11)	C33—C32—H32	126.0
C6—Fe1—C3	84.34 (12)	C33—C34—H34	126.1
C6—Fe1—C4	71.48 (12)	C34—Fe1—C1	168.03 (12)
C6—Fe1—C5	39.62 (12)	C34—Fe1—C2	132.04 (11)
C6—Fe1—C31	125.08 (13)	C34—Fe1—C3	104.98 (12)
C6—Fe1—C32	105.30 (12)	C34—Fe1—C4	98.86 (13)
C6—C1—Fe1	67.25 (16)	C34—Fe1—C5	117.82 (13)
C6—C1—C2	119.6 (3)	C34—Fe1—C6	152.32 (13)
C6—C1—C7	115.5 (2)	C34—Fe1—C31	68.05 (13)
C6—C5—Fe1	69.83 (18)	C34—Fe1—C32	67.98 (13)
C6—C5—C4	118.5 (3)	C34—Fe1—C33	40.63 (12)
C6—C5—H5	120.0	C34—Fe1—C35	40.56 (13)
C7—C1—Fe1	135.4 (2)	C34—C33—Fe1	69.11 (17)
C7—C12—C11	121.3 (3)	C34—C33—H33	125.8
C7—C12—H12	119.4	C34—C35—Fe1	69.20 (18)
C8—C7—C1	119.0 (3)	C34—C35—H35	126.0
C8—C9—H9	120.1	C35—Fe1—C1	128.36 (12)
C8—O1—H1	109.5	C35—Fe1—C2	105.05 (12)
C9—C8—C7	120.6 (3)	C35—Fe1—C3	102.07 (12)
C9—C10—H10	119.7	C35—Fe1—C4	122.75 (13)
C10—C9—C8	119.8 (3)	C35—Fe1—C5	156.61 (13)
C10—C9—H9	120.1	C35—Fe1—C6	163.74 (13)
C10—C11—C12	119.2 (3)	C35—Fe1—C31	40.34 (13)
C10—C11—H11	120.4	C35—Fe1—C32	67.77 (13)
C11—C10—C9	120.6 (3)	C35—Fe1—C33	67.88 (13)
C11—C10—H10	119.7	C35—C31—C32	108.0 (3)
C12—C7—C1	122.2 (3)	C35—C31—Fe1	69.48 (18)
C12—C7—C8	118.5 (3)	C35—C31—H31	126.0
C12—C11—H11	120.4	C35—C34—C33	107.7 (3)
C11—C12—H12	119.4	C35—C34—Fe1	70.25 (18)
N1—C2—Fe1	133.8 (2)	C33—C34—Fe1	70.26 (17)
N1—C2—C3	118.8 (3)	C35—C34—H34	126.1
N1—C2—C1	124.5 (3)	F1—P2—F2	90.85 (12)
N1—C21—C22	103.8 (2)	F1—P2—F3	89.90 (15)
N1—C21—H21A	111.0	F1—P2—F4	179.30 (15)
N1—C21—H21B	111.0	F1—P2—F5	89.63 (15)
N1—C24—C23	102.9 (3)	F1—P2—F6	90.68 (13)
N1—C24—H24A	111.2	F2—P2—F3	178.37 (12)
N1—C24—H24B	111.2	F2—P2—F4	89.79 (11)
O1—C8—C9	122.2 (3)	F2—P2—F5	88.83 (11)
O1—C8—C7	117.2 (3)	F3—P2—F5	89.73 (12)
C21—C22—H22A	111.1	F4—P2—F3	89.45 (13)
C21—C22—H22B	111.1	F4—P2—F5	90.11 (15)
H21A—C21—H21B	109.0	F6—P2—F2	91.85 (11)
C22—C23—C24	102.9 (3)	F6—P2—F3	89.59 (12)
C22—C23—H23A	111.2	F6—P2—F4	89.58 (13)
C22—C23—H23B	111.2	F6—P2—F5	179.25 (13)