Three new enanti­omerically pure ferrocenylphosphole compounds

The absolute configurations of three new enanti­omerically pure ferrocenylphosphole compounds, namely (2S,4S,S_Fc)-4-methoxy­methyl-2-[2-(9-thioxo-9[lambda]⁵-phosphafluoren-9-yl)­ferro­cenyl]-1,3-dioxane, [Fe(C₅H₅)(C₂₃H₂₂O₃PS)], (III), (S_Fc)-[2-(9-thioxo-9[lambda]⁵-phosphafluoren-9-yl)ferrocenyl]methanol, [Fe(C₅H₅)(C₁₈H₁₄OPS)], (V), and (S_Fc)-diphenyl[2-(9-thioxo-9[lambda]⁵-phosphafluoren-9-yl]ferrocenylmethyl]phosphine, [Fe(C₅H₅)(C₃₀H₂₃P₂)], (VIII), have been unambiguously established. All three ligands contain a planar chiral ferrocene group, bearing a dibenzo­phos­phole and either a dioxane, a methanol or a diphenyl­phosphino­methane group on the same cyclopentadienyl. In compound (V), the occurrence of O-H...S and C-H...S hydrogen bonds results in the formation of a two-dimensional network parallel to (001). The geometry of the ferrocene frameworks agrees with related reported structures.

S1. Comment

Considerable efforts have been devoted to the development of new chiral ligands owing to the growing importance of transition metal-catalysed asymmetric synthesis (Ojima, 2000; Jacobsen et al., 1999; Noyori, 1994). Among these chiral ligands, ferrocene-containing ligands are among the most interesting because of their stability, the easy introduction of planar chirality and the special electronic and stereoproperties of the ferrocene skeleton (Togni & Hayashi, 1995; Borman, 1996; Togni, 1996; Atkinson et al., 2004). Among the chiral ferrocene-based ligands, enantiopure 1,2-disubstituted ferrocene derivatives, especially ferrocenyldiphosphine ligands, have played a dominant role (Colacot, 2003; Tang et al., 2003; Barbaro et al., 2004). Typical examples are TRAP ligands (Sawamura et al., 1996; Kuwano et al., 1999, 2000), and the diphosphine Josiphos ligands (Blaser et al., 2002), in particular the industrially important Xyliphos (Blaser, 2002), Taniaphos (Lotz et al., 2002; Spindler et al., 2004) or Walphos-type ligands (Sturm et al., 2003). Common characteristics of these ligands include the ferrocenylethyl backbone and the presence of both planar and central chiralities. Little attention has been paid to ligands based on the ferrocenylmethyl backbone or, more generally, to ferrocenes possessing planar chirality as their only element of chirality. Thus, we have recently investigated the family of 1,2-disubstituted planar chiral ferrocenes by the introduction of a phosphole group, leading to planar chiral ferrocenyl phosphole amine ligands (Lopez Cortés et al., 2006). We report here the structural characterization of three enantiomerically pure ferrocenyl derivatives containing the dibenzophosphole moiety, (III), (V) and (VIII).

A molecular view of compound (III) is shown in Fig. 1. As expected, the phosphole ring is planar, with the largest deviation being 0.068 (2) Å for atom C112. Atom P1 deviates slightly by 0.204 (2) Å from the Cp ring to which it is attached, whereas atom S1 is endo with respect to this Cp ring by 1.026 (3) Å. The dibenzyl phosphole and the Cp rings are nearly perpendicular, making a dihedral angle of 88.21 (5)°. The dioxane ring is distorted and the puckering parameters (Cremer & Pople, 1975) show that its conformation is close to that of a chair: the θ and ϕ angles calculated for the atom sequence C21/O21/C22/C23/C24/O22 are 175.4 (2)° and 133 (2)°, respectively. Owing to steric hindrance, the dioxane ring is twisted with respect to the Cp ring, with C3—C2—C21—O21 and C3—C2—C21—O22 torsion angles of −5.0 (3) and 115.8 (2)°, respectively. The two Cp rings are nearly eclipsed, with a twisted angle of only 3.5°.

A molecular view of alcohol (V) is shown in Fig. 2. As previously noticed, the dibenzyl phosphole is roughly planar, with the largest deviation being 0.109 (2) Å for atom C14, and it makes a dihedral angle of 87.34 (7)° with the Cp ring to which it is attached. Atom P1 is nearly coplanar with the Cp ring, deviating by only 0.088 (2) Å. Atom S1 is endo by 1.333 (3) Å with respect to this Cp ring. An interesting feature is the occurrence of an O—H···S intermolecular hydrogen bond linking the molecules to form a chain developing parallel to the a axis. It is worth pointing out that, in the related compound (SFc)-[2-(3,4-dimethyl-1-thio-1H-1λ5-phosphol-1-yl)ferrocenyl]methanol (Mourgues et al., 2003), the O—H···S interaction is only intramolecular. Moreover, in (V) the chains are interconnected by weak C—H···S hydrogen bonds to form a two-dimensional network parallel to (001) (Table 1, Fig. 3). The two Cp rings are twisted with respect to each other by 13.9°. This larger value compared with compound (III) [Please check - was originally (I)] might be related to the occurrence of the hydrogen bond. The alcohol group is twisted with respect to the Cp plane, with a C3—C2—C21—O21 torsion angle of 103.1 (3)°. A similar conformation of the alcohol group has been found in the related compound rac-2-(diphenylthiophosphoryl)ferrocenylmethanol (Stepnicka & Císarová, 2002). However, the O—H···S hydrogen bonds in that compound resulted in the formation of pseudo dimer through an inversion centre.

A molecular view of complex (VIII) is shown in Fig. 4. As already observed in free phosphole ligands (Tissot et al., 2000; Ogasawara et al., 2001; Hydrio et al., 2002; Melaimi et al., 2002), the P atom is located slightly above the butadiene fragment [0.129 (5) Å]. Atom P1 is roughly in the plane of the Cp ring, with a deviation from the mean plane of 0.09 (1) Å. Atom P2 is oriented exo with respect to the Cp ring and is located 1.62 (1) Å above it. The two Cp rings are perfectly eclipsed, with a twist angle of 0.5°. The two phenyl rings make a dihedral angle of 65.7 (2)°. It is interesting to note that the lone pairs of the two P atoms are in the correct arrangement for chelating on a metal precursor.

In all three compounds, the geometry within the ferrocene frameworks is roughly identical (Table 2) and agrees with that of related compounds found in the Cambridge Structural Database (CSD; Version 5.27; Allen, 2002). For these three compounds, the refinement of the Flack parameter (Flack, 1983; Bernardinelli & Flack, 1985) allowed the determination of the absolute configuration.

S2. Experimental

Compounds (III), (V) and (VIII) were synthesized according to procedure reported by Lopez Cortés et al. (2006). The scheme gives an outline of the synthesis, with steps as follows. (i) t-BuLi, 195 K to room temperature; 1-cyanophosphole, 243 K; S₈, CH₂Cl₂, room temperature. (ii) H⁺, H₂O/CH₂Cl₂, reflux. (iii) NaBH₄, room temperature. (iv) AcCl/NEt₃, 273 K to room temperature, CH₂Cl₂. (v) R₂PH, toluene, reflux, S₈, CH₂Cl₂, room temperature. (vi) P(NMe₂)₃, toluene reflux. Intermediate products (IV), (VI) and (VII) were obtained as oils, whereas crystals of (III), (V) and (VIII) suitable for X-ray analyses were obtained by slow diffusion of pentane into dichloromethane solutions.

S3. Refinement

All H atoms were positioned geometrically and treated as riding on their parent atoms, with C—H = 0.93 (C_aromatic) or 0.96 Å (C_methyl) and O—H = 0.82 Å, and with U_iso(H) = 1.2U_eq(C_aromatic,O) or 1.5U_eq(C_methyl).

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003) for (III); IPDS Software (Stoe & Cie, 2000) for (V), (VIII). Cell refinement: CrysAlis RED (Oxford Diffraction, 2003) for (III); IPDS Software for (V), (VIII). Data reduction: CrysAlis RED for (III); X-RED (Stoe & Cie, 1996) for (V), (VIII). For all compounds, program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) for (III), (VIII); ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003) for (V). For all compounds, software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. The molecular structure of compound (III), with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 2. The molecular structure of compound (V), with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 3. A packing view for compound (V), showing the O—H···S and C—H···S hydrogen-bonding interactions (dashed lines) resulting in the formation of a two-dimensional network parallel to (001). [Symmetry codes: (i) x − 1, y, z; (ii) −x + 2, y + 1/2, −z + 1.]
	Fig. 4. The molecular structure of compound (VIII), with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.

(III) (2S,4S,SFc)-4-(methoxymethyl)-2-[(2-dibenzo-1-thio-1H-1λ⁵– phosphol-1-yl)ferrocenyl]-1,3-dioxane

Crystal data

[Fe(C5H5)(C23H22O3PS)]	F(000) = 552
Mr = 530.38	Dx = 1.470 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3139 reflections
a = 7.4885 (7) Å	θ = 3.6–31.6°
b = 9.5175 (8) Å	µ = 0.81 mm^−1
c = 16.8193 (13) Å	T = 180 K
β = 91.067 (7)°	Prism, yellow
V = 1198.53 (18) Å^3	0.36 × 0.28 × 0.22 mm
Z = 2

Data collection

Oxford XCALIBUR diffractometer	4045 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 28.3°, θmin = 3.2°
Detector resolution: 8.2632 pixels mm^-1	h = −9→9
ω and ϕ scans	k = −12→10
10617 measured reflections	l = −22→22
4383 independent reflections

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)] = 0.027	H-atom parameters constrained
wR(F^2) = 0.066	w = 1/[σ^2(Fo^2) + (0.0401P)^2 + 0.0522P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.002
4383 reflections	Δρmax = 0.33 e Å^−3
308 parameters	Δρmin = −0.33 e Å^−3
1 restraint	Absolute structure: Flack (1983), with 1249 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (1)

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	0.80570 (4)	0.53939 (3)	0.734270 (16)	0.01884 (8)
P1	0.78732 (7)	0.90456 (6)	0.73444 (3)	0.01810 (11)
S1	0.71485 (8)	0.94431 (7)	0.84217 (3)	0.02705 (13)
O21	1.1755 (2)	0.59496 (16)	0.88366 (9)	0.0248 (3)
O22	1.1587 (2)	0.83298 (16)	0.85032 (9)	0.0207 (3)
O26	1.1561 (2)	1.12476 (18)	0.90846 (11)	0.0324 (4)
C1	0.8935 (2)	0.7384 (2)	0.71717 (11)	0.0175 (4)
C2	1.0154 (3)	0.6636 (2)	0.76842 (12)	0.0186 (4)
C3	1.0785 (2)	0.5440 (3)	0.72635 (11)	0.0212 (4)
H3	1.1603	0.4758	0.7464	0.025*
C4	0.9979 (3)	0.5443 (3)	0.64908 (11)	0.0226 (4)
H4	1.0169	0.4765	0.6086	0.027*
C5	0.8842 (3)	0.6633 (2)	0.64289 (12)	0.0211 (4)
H5	0.8140	0.6889	0.5975	0.025*
C6	0.5659 (3)	0.5491 (3)	0.79046 (14)	0.0326 (5)
H6	0.5052	0.6317	0.8065	0.039*
C7	0.5457 (3)	0.4804 (3)	0.71572 (16)	0.0326 (5)
H7	0.4704	0.5098	0.6728	0.039*
C8	0.6579 (3)	0.3600 (3)	0.71654 (17)	0.0346 (6)
H8	0.6704	0.2946	0.6743	0.041*
C9	0.7475 (4)	0.3546 (3)	0.79086 (16)	0.0364 (6)
H9	0.8304	0.2847	0.8077	0.044*
C10	0.6918 (4)	0.4729 (3)	0.83655 (15)	0.0354 (6)
H10	0.7325	0.4961	0.8888	0.042*
C11	0.9308 (3)	1.0287 (2)	0.68432 (11)	0.0217 (4)
C12	0.8615 (3)	1.0586 (2)	0.60804 (12)	0.0264 (5)
C13	0.6847 (3)	0.9947 (2)	0.59147 (13)	0.0283 (5)
C14	0.6202 (3)	0.9148 (2)	0.65512 (13)	0.0254 (5)
C21	1.0668 (3)	0.7033 (2)	0.85227 (11)	0.0198 (4)
H21	0.9570	0.7130	0.8848	0.024*
C22	1.2274 (3)	0.6261 (3)	0.96438 (13)	0.0282 (5)
H22A	1.3104	0.5527	0.9844	0.034*
H22B	1.1205	0.6255	0.9982	0.034*
C23	1.3174 (3)	0.7683 (3)	0.96985 (13)	0.0263 (5)
H23A	1.4344	0.7645	0.9435	0.032*
H23B	1.3385	0.7934	1.0264	0.032*
C24	1.1999 (3)	0.8790 (2)	0.92996 (13)	0.0222 (4)
H24	1.0862	0.8869	0.9599	0.027*
C25	1.2861 (3)	1.0227 (3)	0.92612 (13)	0.0246 (4)
H25A	1.3452	1.0446	0.9778	0.029*
H25B	1.3781	1.0232	0.8846	0.029*
C26	1.2296 (4)	1.2612 (3)	0.9035 (2)	0.0498 (8)
H26A	1.2827	1.2873	0.9551	0.075*
H26B	1.1352	1.3283	0.8891	0.075*
H26C	1.3219	1.2626	0.8630	0.075*
C111	1.0897 (3)	1.0856 (2)	0.71198 (14)	0.0271 (5)
H111	1.1333	1.0652	0.7641	0.033*
C112	1.1853 (4)	1.1740 (3)	0.66158 (15)	0.0331 (5)
H112	1.2947	1.2147	0.6794	0.040*
C113	1.1200 (4)	1.2021 (3)	0.58569 (14)	0.0365 (6)
H113	1.1869	1.2608	0.5516	0.044*
C114	0.9589 (4)	1.1464 (3)	0.55817 (14)	0.0343 (6)
H114	0.9155	1.1677	0.5061	0.041*
C411	0.4531 (3)	0.8537 (3)	0.65205 (16)	0.0325 (6)
H411	0.4105	0.8016	0.6960	0.039*
C412	0.3481 (4)	0.8699 (3)	0.58340 (18)	0.0413 (7)
H412	0.2317	0.8302	0.5806	0.050*
C413	0.4137 (4)	0.9439 (4)	0.51907 (16)	0.0450 (7)
H413	0.3433	0.9508	0.4717	0.054*
C414	0.5787 (4)	1.0077 (3)	0.52262 (15)	0.0403 (7)
H414	0.6202	1.0601	0.4786	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.01991 (14)	0.01598 (14)	0.02068 (14)	−0.00138 (13)	0.00213 (10)	−0.00135 (13)
P1	0.0208 (3)	0.0151 (3)	0.0183 (2)	0.0016 (2)	0.00039 (19)	−0.00107 (19)
S1	0.0278 (3)	0.0289 (3)	0.0247 (3)	0.0030 (2)	0.0073 (2)	−0.0050 (2)
O21	0.0307 (8)	0.0182 (8)	0.0252 (8)	0.0048 (7)	−0.0057 (6)	0.0007 (6)
O22	0.0221 (7)	0.0180 (7)	0.0217 (7)	−0.0021 (6)	−0.0017 (6)	−0.0016 (6)
O26	0.0296 (9)	0.0194 (8)	0.0483 (10)	0.0000 (7)	−0.0029 (7)	−0.0039 (7)
C1	0.0169 (9)	0.0171 (11)	0.0187 (8)	−0.0016 (8)	0.0025 (7)	−0.0015 (8)
C2	0.0166 (9)	0.0172 (10)	0.0221 (10)	−0.0018 (8)	0.0028 (7)	0.0002 (8)
C3	0.0176 (8)	0.0195 (10)	0.0267 (9)	0.0021 (10)	0.0043 (7)	−0.0002 (10)
C4	0.0242 (9)	0.0201 (10)	0.0239 (9)	−0.0008 (10)	0.0073 (7)	−0.0048 (10)
C5	0.0261 (10)	0.0199 (10)	0.0175 (9)	0.0003 (9)	0.0030 (8)	−0.0019 (8)
C6	0.0284 (11)	0.0276 (13)	0.0425 (12)	−0.0055 (11)	0.0195 (9)	−0.0065 (12)
C7	0.0218 (11)	0.0338 (13)	0.0421 (14)	−0.0064 (10)	0.0012 (9)	−0.0016 (11)
C8	0.0321 (13)	0.0232 (12)	0.0486 (15)	−0.0115 (10)	0.0062 (11)	−0.0104 (11)
C9	0.0381 (14)	0.0244 (13)	0.0468 (16)	−0.0074 (11)	0.0065 (12)	0.0121 (11)
C10	0.0418 (14)	0.0384 (15)	0.0263 (12)	−0.0125 (12)	0.0120 (11)	0.0043 (10)
C11	0.0297 (10)	0.0133 (9)	0.0223 (9)	0.0034 (10)	0.0074 (7)	−0.0028 (9)
C12	0.0376 (12)	0.0188 (12)	0.0230 (9)	0.0095 (10)	0.0056 (8)	0.0005 (8)
C13	0.0376 (12)	0.0222 (11)	0.0251 (11)	0.0147 (10)	−0.0025 (9)	−0.0043 (8)
C14	0.0278 (11)	0.0201 (11)	0.0283 (11)	0.0096 (9)	−0.0032 (8)	−0.0043 (9)
C21	0.0185 (9)	0.0192 (11)	0.0217 (9)	−0.0002 (8)	−0.0004 (7)	0.0011 (8)
C22	0.0368 (13)	0.0234 (12)	0.0243 (11)	0.0014 (10)	−0.0058 (9)	0.0026 (9)
C23	0.0292 (12)	0.0272 (12)	0.0224 (10)	0.0022 (9)	−0.0046 (9)	−0.0040 (8)
C24	0.0212 (10)	0.0213 (11)	0.0240 (10)	−0.0007 (9)	0.0005 (8)	−0.0031 (9)
C25	0.0227 (9)	0.0237 (12)	0.0272 (10)	0.0002 (10)	−0.0017 (8)	−0.0046 (9)
C26	0.0553 (19)	0.0220 (14)	0.071 (2)	−0.0053 (12)	−0.0172 (15)	−0.0002 (13)
C111	0.0338 (11)	0.0186 (10)	0.0291 (11)	−0.0012 (9)	0.0051 (9)	−0.0014 (9)
C112	0.0405 (14)	0.0198 (11)	0.0396 (13)	−0.0039 (10)	0.0139 (11)	−0.0017 (10)
C113	0.0539 (15)	0.0185 (12)	0.0379 (12)	−0.0003 (11)	0.0230 (11)	0.0029 (10)
C114	0.0532 (16)	0.0256 (13)	0.0245 (11)	0.0126 (12)	0.0116 (11)	0.0054 (9)
C411	0.0273 (12)	0.0275 (13)	0.0422 (14)	0.0073 (10)	−0.0073 (10)	−0.0072 (10)
C412	0.0347 (14)	0.0339 (14)	0.0546 (18)	0.0091 (11)	−0.0171 (12)	−0.0157 (13)
C413	0.0492 (16)	0.0455 (16)	0.0394 (14)	0.0234 (14)	−0.0210 (12)	−0.0128 (13)
C414	0.0537 (16)	0.0393 (18)	0.0275 (12)	0.0203 (13)	−0.0083 (11)	−0.0027 (11)

Geometric parameters (Å, º)

Fe1—C1	2.028 (2)	C9—H9	0.9500
Fe1—C5	2.033 (2)	C10—H10	0.9500
Fe1—C10	2.035 (2)	C11—C111	1.380 (3)
Fe1—C2	2.039 (2)	C11—C12	1.404 (3)
Fe1—C7	2.045 (2)	C12—C114	1.399 (3)
Fe1—C6	2.047 (2)	C12—C13	1.479 (3)
Fe1—C4	2.0502 (19)	C13—C414	1.397 (3)
Fe1—C9	2.050 (2)	C13—C14	1.406 (3)
Fe1—C3	2.0503 (19)	C14—C411	1.380 (3)
Fe1—C8	2.053 (2)	C21—H21	1.0000
P1—C1	1.796 (2)	C22—C23	1.514 (3)
P1—C14	1.815 (2)	C22—H22A	0.9900
P1—C11	1.815 (2)	C22—H22B	0.9900
P1—S1	1.9384 (7)	C23—C24	1.521 (3)
O21—C21	1.410 (3)	C23—H23A	0.9900
O21—C22	1.436 (3)	C23—H23B	0.9900
O22—C21	1.414 (3)	C24—C25	1.514 (3)
O22—C24	1.437 (3)	C24—H24	1.0000
O26—C25	1.403 (3)	C25—H25A	0.9900
O26—C26	1.413 (3)	C25—H25B	0.9900
C1—C2	1.433 (3)	C26—H26A	0.9800
C1—C5	1.440 (3)	C26—H26B	0.9800
C2—C3	1.425 (3)	C26—H26C	0.9800
C2—C21	1.503 (3)	C111—C112	1.401 (3)
C3—C4	1.423 (3)	C111—H111	0.9500
C3—H3	0.9500	C112—C113	1.384 (4)
C4—C5	1.420 (3)	C112—H112	0.9500
C4—H4	0.9500	C113—C114	1.389 (4)
C5—H5	0.9500	C113—H113	0.9500
C6—C10	1.410 (4)	C114—H114	0.9500
C6—C7	1.423 (4)	C411—C412	1.394 (4)
C6—H6	0.9500	C411—H411	0.9500
C7—C8	1.421 (4)	C412—C413	1.389 (5)
C7—H7	0.9500	C412—H412	0.9500
C8—C9	1.409 (4)	C413—C414	1.377 (4)
C8—H8	0.9500	C413—H413	0.9500
C9—C10	1.430 (4)	C414—H414	0.9500
C1—Fe1—C5	41.55 (8)	C8—C7—H7	126.0
C1—Fe1—C10	123.53 (10)	C6—C7—H7	126.0
C5—Fe1—C10	162.01 (10)	Fe1—C7—H7	125.8
C1—Fe1—C2	41.28 (8)	C9—C8—C7	108.0 (2)
C5—Fe1—C2	69.20 (8)	C9—C8—Fe1	69.80 (14)
C10—Fe1—C2	105.94 (10)	C7—C8—Fe1	69.39 (14)
C1—Fe1—C7	123.04 (10)	C9—C8—H8	126.0
C5—Fe1—C7	109.38 (10)	C7—C8—H8	126.0
C10—Fe1—C7	68.33 (11)	Fe1—C8—H8	126.4
C2—Fe1—C7	158.15 (10)	C8—C9—C10	108.0 (2)
C1—Fe1—C6	108.24 (10)	C8—C9—Fe1	70.05 (14)
C5—Fe1—C6	126.26 (10)	C10—C9—Fe1	68.95 (14)
C10—Fe1—C6	40.42 (11)	C8—C9—H9	126.0
C2—Fe1—C6	121.43 (9)	C10—C9—H9	126.0
C7—Fe1—C6	40.69 (10)	Fe1—C9—H9	126.6
C1—Fe1—C4	69.27 (9)	C6—C10—C9	107.9 (2)
C5—Fe1—C4	40.69 (9)	C6—C10—Fe1	70.25 (13)
C10—Fe1—C4	155.30 (11)	C9—C10—Fe1	70.08 (13)
C2—Fe1—C4	68.71 (8)	C6—C10—H10	126.0
C7—Fe1—C4	125.34 (9)	C9—C10—H10	126.0
C6—Fe1—C4	162.74 (9)	Fe1—C10—H10	125.2
C1—Fe1—C9	159.97 (10)	C111—C11—C12	122.0 (2)
C5—Fe1—C9	156.28 (10)	C111—C11—P1	127.81 (17)
C10—Fe1—C9	40.97 (11)	C12—C11—P1	110.13 (16)
C2—Fe1—C9	122.38 (10)	C114—C12—C11	118.7 (2)
C7—Fe1—C9	67.99 (11)	C114—C12—C13	127.5 (2)
C6—Fe1—C9	68.19 (12)	C11—C12—C13	113.77 (19)
C4—Fe1—C9	120.13 (10)	C414—C13—C14	118.8 (2)
C1—Fe1—C3	69.19 (9)	C414—C13—C12	127.8 (2)
C5—Fe1—C3	68.66 (9)	C14—C13—C12	113.44 (19)
C10—Fe1—C3	119.69 (10)	C411—C14—C13	121.5 (2)
C2—Fe1—C3	40.80 (9)	C411—C14—P1	128.12 (19)
C7—Fe1—C3	160.58 (9)	C13—C14—P1	110.32 (17)
C6—Fe1—C3	155.91 (9)	O21—C21—O22	111.66 (15)
C4—Fe1—C3	40.61 (8)	O21—C21—C2	107.65 (17)
C9—Fe1—C3	105.61 (11)	O22—C21—C2	108.30 (16)
C1—Fe1—C8	158.68 (10)	O21—C21—H21	109.7
C5—Fe1—C8	122.35 (10)	O22—C21—H21	109.7
C10—Fe1—C8	68.36 (12)	C2—C21—H21	109.7
C2—Fe1—C8	158.89 (10)	O21—C22—C23	110.73 (19)
C7—Fe1—C8	40.57 (11)	O21—C22—H22A	109.5
C6—Fe1—C8	68.25 (11)	C23—C22—H22A	109.5
C4—Fe1—C8	107.50 (10)	O21—C22—H22B	109.5
C9—Fe1—C8	40.15 (12)	C23—C22—H22B	109.5
C3—Fe1—C8	122.91 (10)	H22A—C22—H22B	108.1
C1—P1—C14	103.27 (10)	C22—C23—C24	109.85 (18)
C1—P1—C11	103.30 (9)	C22—C23—H23A	109.7
C14—P1—C11	91.70 (10)	C24—C23—H23A	109.7
C1—P1—S1	117.10 (7)	C22—C23—H23B	109.7
C14—P1—S1	118.40 (8)	C24—C23—H23B	109.7
C11—P1—S1	119.05 (7)	H23A—C23—H23B	108.2
C21—O21—C22	110.34 (16)	O22—C24—C25	108.65 (18)
C21—O22—C24	109.91 (16)	O22—C24—C23	108.21 (18)
C25—O26—C26	112.30 (19)	C25—C24—C23	113.66 (18)
C2—C1—C5	107.14 (18)	O22—C24—H24	108.7
C2—C1—P1	128.27 (15)	C25—C24—H24	108.7
C5—C1—P1	124.28 (16)	C23—C24—H24	108.7
C2—C1—Fe1	69.80 (12)	O26—C25—C24	109.88 (17)
C5—C1—Fe1	69.41 (12)	O26—C25—H25A	109.7
P1—C1—Fe1	130.85 (10)	C24—C25—H25A	109.7
C3—C2—C1	108.17 (17)	O26—C25—H25B	109.7
C3—C2—C21	125.81 (19)	C24—C25—H25B	109.7
C1—C2—C21	126.02 (19)	H25A—C25—H25B	108.2
C3—C2—Fe1	70.01 (12)	O26—C26—H26A	109.5
C1—C2—Fe1	68.92 (11)	O26—C26—H26B	109.5
C21—C2—Fe1	126.31 (14)	H26A—C26—H26B	109.5
C4—C3—C2	108.23 (19)	O26—C26—H26C	109.5
C4—C3—Fe1	69.69 (11)	H26A—C26—H26C	109.5
C2—C3—Fe1	69.19 (11)	H26B—C26—H26C	109.5
C4—C3—H3	125.9	C11—C111—C112	118.6 (2)
C2—C3—H3	125.9	C11—C111—H111	120.7
Fe1—C3—H3	126.8	C112—C111—H111	120.7
C5—C4—C3	108.20 (19)	C113—C112—C111	119.9 (3)
C5—C4—Fe1	68.99 (11)	C113—C112—H112	120.1
C3—C4—Fe1	69.70 (10)	C111—C112—H112	120.1
C5—C4—H4	125.9	C112—C113—C114	121.5 (2)
C3—C4—H4	125.9	C112—C113—H113	119.2
Fe1—C4—H4	127.0	C114—C113—H113	119.2
C4—C5—C1	108.27 (18)	C113—C114—C12	119.2 (2)
C4—C5—Fe1	70.32 (12)	C113—C114—H114	120.4
C1—C5—Fe1	69.04 (11)	C12—C114—H114	120.4
C4—C5—H5	125.9	C14—C411—C412	118.8 (3)
C1—C5—H5	125.9	C14—C411—H411	120.6
Fe1—C5—H5	126.3	C412—C411—H411	120.6
C10—C6—C7	108.0 (3)	C413—C412—C411	119.9 (3)
C10—C6—Fe1	69.33 (13)	C413—C412—H412	120.0
C7—C6—Fe1	69.57 (12)	C411—C412—H412	120.0
C10—C6—H6	126.0	C414—C413—C412	121.3 (2)
C7—C6—H6	126.0	C414—C413—H413	119.3
Fe1—C6—H6	126.7	C412—C413—H413	119.3
C8—C7—C6	108.0 (2)	C413—C414—C13	119.5 (3)
C8—C7—Fe1	70.04 (14)	C413—C414—H414	120.3
C6—C7—Fe1	69.74 (13)	C13—C414—H414	120.3
C3—C2—C21—O22	115.8 (2)	C3—C2—C21—O21	−5.0 (3)

(V) (SFc)-[2-(2-dibenzo-1-thio-1H-1λ⁵-phosphol-1-yl)ferrocenyl]methanol

Crystal data

[Fe(C5H5)(C18H14OPS)]	F(000) = 444
Mr = 430.26	Dx = 1.539 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 8000 reflections
a = 7.1110 (13) Å	θ = 2.6–26.1°
b = 12.862 (3) Å	µ = 1.02 mm^−1
c = 10.223 (2) Å	T = 180 K
β = 96.73 (2)°	Needle, yellow
V = 928.6 (3) Å^3	0.48 × 0.13 × 0.12 mm
Z = 2

Data collection

Stoe IPDS diffractometer	3619 independent reflections
Radiation source: fine-focus sealed tube	3380 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ϕ scans	θmax = 26.1°, θmin = 2.6°
Absorption correction: multi-scan (Blessing, 1995)	h = −8→8
Tmin = 0.598, Tmax = 0.873	k = −15→15
9253 measured reflections	l = −12→12

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)] = 0.026	H-atom parameters constrained
wR(F^2) = 0.061	w = 1/[σ^2(Fo^2) + (0.0359P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.001
3619 reflections	Δρmax = 0.36 e Å^−3
245 parameters	Δρmin = −0.25 e Å^−3
1 restraint	Absolute structure: Flack (1983), with 1722 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.015 (12)

Special details

Experimental. The data were collected on a Stoe Imaging Plate Diffraction System (IPDS). The crystal-to-detector distance was 70 mm. 167 frames (3 min per frame) were obtained with 0 < ϕ < 250.5° and with the crystals rotated through 1.5° in ϕ. Coverage of the unique set was over 98.5% complete to at least 26.08°. Crystal decay was monitored by measuring 200 reflections per frame.

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	0.95509 (4)	0.27803 (2)	1.10011 (3)	0.01710 (9)
P1	0.98411 (8)	0.25396 (4)	0.76524 (6)	0.01874 (13)
S1	1.10129 (9)	0.11644 (5)	0.76488 (7)	0.02777 (15)
O21	0.5810 (3)	0.08178 (15)	0.8284 (2)	0.0341 (4)
H21	0.4845	0.1161	0.8318	0.051*
C1	0.8638 (3)	0.2824 (2)	0.9048 (2)	0.0186 (4)
C2	0.7467 (3)	0.2122 (2)	0.9715 (2)	0.0210 (5)
C3	0.6672 (3)	0.2727 (2)	1.0687 (2)	0.0256 (5)
H3	0.5869	0.2475	1.1269	0.031*
C4	0.7295 (3)	0.3765 (2)	1.0628 (3)	0.0248 (5)
H4	0.6973	0.4309	1.1159	0.030*
C5	0.8502 (3)	0.38368 (19)	0.9617 (2)	0.0207 (5)
H5	0.9099	0.4436	0.9368	0.025*
C6	1.2154 (4)	0.2088 (2)	1.1316 (3)	0.0255 (5)
H6	1.2771	0.1743	1.0689	0.031*
C7	1.2297 (4)	0.3160 (2)	1.1619 (3)	0.0244 (6)
H7	1.3025	0.3644	1.1228	0.029*
C8	1.1129 (3)	0.3367 (2)	1.2630 (3)	0.0254 (5)
H8	1.0957	0.4010	1.3015	0.030*
C9	1.0276 (4)	0.2419 (2)	1.2943 (2)	0.0260 (5)
H9	0.9445	0.2331	1.3572	0.031*
C10	1.0901 (4)	0.1629 (2)	1.2138 (3)	0.0260 (5)
H10	1.0556	0.0932	1.2144	0.031*
C11	0.8150 (3)	0.2916 (2)	0.6268 (2)	0.0207 (5)
C12	0.8729 (3)	0.38479 (18)	0.5721 (2)	0.0206 (5)
C13	1.0609 (3)	0.42100 (19)	0.6312 (2)	0.0205 (5)
C14	1.1390 (3)	0.36087 (18)	0.7384 (2)	0.0201 (5)
C21	0.7096 (4)	0.0997 (2)	0.9451 (3)	0.0295 (6)
H21A	0.8286	0.0650	0.9361	0.035*
H21B	0.6576	0.0692	1.0199	0.035*
C111	0.6443 (3)	0.24475 (19)	0.5808 (2)	0.0251 (5)
H111	0.6080	0.1827	0.6172	0.030*
C112	0.5291 (3)	0.2923 (2)	0.4797 (3)	0.0299 (6)
H112	0.4146	0.2616	0.4472	0.036*
C113	0.5833 (4)	0.3854 (2)	0.4262 (3)	0.0298 (6)
H113	0.5043	0.4170	0.3588	0.036*
C114	0.7537 (4)	0.4316 (2)	0.4726 (3)	0.0272 (5)
H114	0.7882	0.4942	0.4368	0.033*
C411	1.3197 (3)	0.3800 (2)	0.8003 (3)	0.0229 (5)
H411	1.3714	0.3385	0.8698	0.027*
C412	1.4224 (4)	0.4626 (2)	0.7562 (3)	0.0273 (6)
H412	1.5433	0.4771	0.7970	0.033*
C413	1.3446 (4)	0.5227 (2)	0.6521 (3)	0.0290 (6)
H413	1.4141	0.5779	0.6241	0.035*
C414	1.1655 (4)	0.5031 (2)	0.5879 (3)	0.0252 (5)
H414	1.1160	0.5440	0.5171	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.01541 (14)	0.02014 (16)	0.01570 (15)	0.00009 (13)	0.00159 (11)	−0.00024 (14)
P1	0.0213 (3)	0.0188 (3)	0.0156 (3)	0.0015 (2)	0.0001 (2)	−0.0002 (2)
S1	0.0319 (3)	0.0214 (3)	0.0294 (3)	0.0068 (3)	0.0010 (3)	−0.0043 (3)
O21	0.0310 (10)	0.0322 (10)	0.0377 (11)	−0.0085 (8)	−0.0024 (8)	−0.0063 (9)
C1	0.0179 (9)	0.0208 (10)	0.0161 (10)	0.0013 (10)	−0.0017 (8)	−0.0004 (11)
C2	0.0172 (11)	0.0238 (13)	0.0214 (12)	−0.0024 (10)	−0.0004 (9)	0.0007 (10)
C3	0.0160 (9)	0.0378 (13)	0.0232 (11)	−0.0026 (12)	0.0024 (8)	−0.0015 (13)
C4	0.0207 (11)	0.0283 (13)	0.0248 (13)	0.0062 (10)	0.0002 (10)	−0.0076 (11)
C5	0.0217 (11)	0.0185 (11)	0.0207 (12)	0.0016 (9)	−0.0024 (10)	0.0011 (10)
C6	0.0185 (12)	0.0352 (15)	0.0228 (13)	0.0051 (11)	0.0018 (10)	0.0009 (12)
C7	0.0169 (11)	0.0308 (13)	0.0245 (14)	−0.0010 (9)	−0.0011 (10)	0.0015 (11)
C8	0.0238 (13)	0.0282 (13)	0.0223 (13)	0.0027 (10)	−0.0052 (10)	−0.0046 (11)
C9	0.0268 (12)	0.0343 (14)	0.0168 (11)	0.0018 (10)	0.0026 (9)	0.0004 (10)
C10	0.0292 (13)	0.0231 (13)	0.0246 (13)	0.0015 (10)	−0.0019 (11)	0.0035 (11)
C11	0.0249 (10)	0.0207 (12)	0.0164 (10)	0.0050 (10)	0.0019 (8)	−0.0015 (10)
C12	0.0240 (11)	0.0235 (11)	0.0152 (11)	0.0031 (9)	0.0059 (9)	−0.0009 (10)
C13	0.0235 (11)	0.0212 (11)	0.0177 (12)	0.0044 (10)	0.0063 (9)	−0.0018 (10)
C14	0.0245 (12)	0.0196 (12)	0.0166 (12)	0.0023 (9)	0.0034 (9)	−0.0021 (9)
C21	0.0312 (13)	0.0268 (14)	0.0292 (14)	−0.0068 (11)	−0.0010 (11)	0.0038 (11)
C111	0.0300 (12)	0.0246 (12)	0.0205 (12)	−0.0021 (9)	0.0013 (10)	−0.0036 (10)
C112	0.0260 (11)	0.0359 (15)	0.0260 (12)	0.0012 (11)	−0.0043 (10)	−0.0057 (12)
C113	0.0270 (13)	0.0381 (14)	0.0225 (13)	0.0059 (11)	−0.0048 (10)	0.0016 (12)
C114	0.0322 (13)	0.0285 (13)	0.0211 (13)	0.0047 (11)	0.0039 (10)	0.0039 (11)
C411	0.0212 (11)	0.0268 (12)	0.0199 (12)	0.0021 (9)	−0.0009 (10)	0.0005 (10)
C412	0.0235 (12)	0.0289 (12)	0.0299 (15)	−0.0014 (10)	0.0046 (11)	−0.0032 (12)
C413	0.0313 (14)	0.0252 (13)	0.0324 (15)	−0.0032 (10)	0.0127 (11)	0.0003 (12)
C414	0.0282 (13)	0.0247 (12)	0.0234 (14)	0.0021 (10)	0.0056 (10)	0.0031 (10)

Geometric parameters (Å, º)

Fe1—C1	2.027 (2)	C7—H7	0.9300
Fe1—C3	2.036 (2)	C8—C9	1.415 (4)
Fe1—C5	2.039 (2)	C8—H8	0.9300
Fe1—C7	2.040 (3)	C9—C10	1.412 (4)
Fe1—C8	2.040 (3)	C9—H9	0.9300
Fe1—C4	2.044 (3)	C10—H10	0.9300
Fe1—C9	2.045 (3)	C11—C111	1.387 (3)
Fe1—C6	2.045 (3)	C11—C12	1.405 (3)
Fe1—C2	2.046 (2)	C12—C114	1.383 (4)
Fe1—C10	2.050 (3)	C12—C13	1.476 (4)
P1—C1	1.785 (2)	C13—C414	1.393 (4)
P1—C14	1.803 (2)	C13—C14	1.402 (3)
P1—C11	1.812 (2)	C14—C411	1.386 (4)
P1—S1	1.9555 (9)	C21—H21A	0.9700
O21—C21	1.434 (3)	C21—H21B	0.9700
O21—H21	0.8200	C111—C112	1.384 (4)
C1—C5	1.435 (4)	C111—H111	0.9300
C1—C2	1.452 (3)	C112—C113	1.390 (4)
C2—C3	1.430 (3)	C112—H112	0.9300
C2—C21	1.490 (4)	C113—C114	1.382 (4)
C3—C4	1.410 (4)	C113—H113	0.9300
C3—H3	0.9300	C114—H114	0.9300
C4—C5	1.421 (4)	C411—C412	1.394 (4)
C4—H4	0.9300	C411—H411	0.9300
C5—H5	0.9300	C412—C413	1.378 (4)
C6—C7	1.414 (4)	C412—H412	0.9300
C6—C10	1.422 (4)	C413—C414	1.386 (4)
C6—H6	0.9300	C413—H413	0.9300
C7—C8	1.425 (4)	C414—H414	0.9300
C1—Fe1—C3	69.24 (9)	C4—C5—Fe1	69.84 (14)
C1—Fe1—C5	41.33 (10)	C1—C5—Fe1	68.87 (13)
C3—Fe1—C5	68.49 (11)	C4—C5—H5	125.9
C1—Fe1—C7	118.89 (10)	C1—C5—H5	125.9
C3—Fe1—C7	164.85 (11)	Fe1—C5—H5	126.9
C5—Fe1—C7	108.35 (11)	C7—C6—C10	108.0 (2)
C1—Fe1—C8	151.15 (11)	C7—C6—Fe1	69.53 (16)
C3—Fe1—C8	125.99 (10)	C10—C6—Fe1	69.87 (15)
C5—Fe1—C8	116.19 (10)	C7—C6—H6	126.0
C7—Fe1—C8	40.88 (11)	C10—C6—H6	126.0
C1—Fe1—C4	69.23 (10)	Fe1—C6—H6	126.2
C3—Fe1—C4	40.44 (11)	C6—C7—C8	108.0 (2)
C5—Fe1—C4	40.73 (10)	C6—C7—Fe1	69.96 (16)
C7—Fe1—C4	127.67 (11)	C8—C7—Fe1	69.58 (14)
C8—Fe1—C4	105.51 (11)	C6—C7—H7	126.0
C1—Fe1—C9	167.90 (11)	C8—C7—H7	126.0
C3—Fe1—C9	106.26 (10)	Fe1—C7—H7	126.0
C5—Fe1—C9	148.77 (10)	C9—C8—C7	107.7 (2)
C7—Fe1—C9	68.30 (11)	C9—C8—Fe1	69.92 (15)
C8—Fe1—C9	40.52 (11)	C7—C8—Fe1	69.54 (15)
C4—Fe1—C9	115.15 (11)	C9—C8—H8	126.1
C1—Fe1—C6	110.27 (10)	C7—C8—H8	126.1
C3—Fe1—C6	152.25 (11)	Fe1—C8—H8	126.0
C5—Fe1—C6	130.56 (11)	C10—C9—C8	108.4 (2)
C7—Fe1—C6	40.51 (11)	C10—C9—Fe1	70.03 (15)
C8—Fe1—C6	68.39 (11)	C8—C9—Fe1	69.56 (15)
C4—Fe1—C6	167.15 (11)	C10—C9—H9	125.8
C9—Fe1—C6	68.15 (11)	C8—C9—H9	125.8
C1—Fe1—C2	41.76 (10)	Fe1—C9—H9	126.2
C3—Fe1—C2	41.01 (10)	C9—C10—C6	107.9 (2)
C5—Fe1—C2	69.59 (10)	C9—C10—Fe1	69.63 (15)
C7—Fe1—C2	153.28 (10)	C6—C10—Fe1	69.49 (15)
C8—Fe1—C2	164.83 (10)	C9—C10—H10	126.0
C4—Fe1—C2	69.09 (10)	C6—C10—H10	126.0
C9—Fe1—C2	127.66 (10)	Fe1—C10—H10	126.4
C6—Fe1—C2	119.66 (11)	C111—C11—C12	121.4 (2)
C1—Fe1—C10	130.76 (11)	C111—C11—P1	128.54 (19)
C3—Fe1—C10	117.44 (11)	C12—C11—P1	109.88 (18)
C5—Fe1—C10	169.60 (10)	C114—C12—C11	118.7 (2)
C7—Fe1—C10	68.25 (11)	C114—C12—C13	127.7 (2)
C8—Fe1—C10	68.18 (11)	C11—C12—C13	113.6 (2)
C4—Fe1—C10	149.14 (11)	C414—C13—C14	119.3 (2)
C9—Fe1—C10	40.34 (10)	C414—C13—C12	126.9 (2)
C6—Fe1—C10	40.63 (11)	C14—C13—C12	113.8 (2)
C2—Fe1—C10	108.73 (11)	C411—C14—C13	121.3 (2)
C1—P1—C14	108.90 (12)	C411—C14—P1	128.0 (2)
C1—P1—C11	103.48 (10)	C13—C14—P1	110.28 (18)
C14—P1—C11	92.23 (11)	O21—C21—C2	112.9 (2)
C1—P1—S1	115.52 (9)	O21—C21—H21A	109.0
C14—P1—S1	114.94 (8)	C2—C21—H21A	109.0
C11—P1—S1	118.96 (9)	O21—C21—H21B	109.0
C21—O21—H21	109.5	C2—C21—H21B	109.0
C5—C1—C2	107.7 (2)	H21A—C21—H21B	107.8
C5—C1—P1	124.86 (19)	C112—C111—C11	118.6 (2)
C2—C1—P1	127.1 (2)	C112—C111—H111	120.7
C5—C1—Fe1	69.80 (13)	C11—C111—H111	120.7
C2—C1—Fe1	69.84 (13)	C111—C112—C113	120.5 (2)
P1—C1—Fe1	130.82 (11)	C111—C112—H112	119.8
C3—C2—C1	106.4 (2)	C113—C112—H112	119.8
C3—C2—C21	125.4 (2)	C114—C113—C112	120.5 (2)
C1—C2—C21	128.2 (2)	C114—C113—H113	119.7
C3—C2—Fe1	69.10 (13)	C112—C113—H113	119.7
C1—C2—Fe1	68.41 (12)	C113—C114—C12	120.2 (2)
C21—C2—Fe1	128.15 (18)	C113—C114—H114	119.9
C4—C3—C2	109.5 (2)	C12—C114—H114	119.9
C4—C3—Fe1	70.12 (14)	C14—C411—C412	118.7 (2)
C2—C3—Fe1	69.88 (13)	C14—C411—H411	120.6
C4—C3—H3	125.2	C412—C411—H411	120.6
C2—C3—H3	125.2	C413—C412—C411	120.0 (2)
Fe1—C3—H3	126.3	C413—C412—H412	120.0
C3—C4—C5	108.2 (2)	C411—C412—H412	120.0
C3—C4—Fe1	69.44 (14)	C412—C413—C414	121.8 (2)
C5—C4—Fe1	69.42 (14)	C412—C413—H413	119.1
C3—C4—H4	125.9	C414—C413—H413	119.1
C5—C4—H4	125.9	C413—C414—C13	118.9 (2)
Fe1—C4—H4	126.8	C413—C414—H414	120.6
C4—C5—C1	108.2 (2)	C13—C414—H414	120.6
C3—C2—C21—O21	103.5 (3)	C1—C2—C21—O21	−75.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21···S1^i	0.82	2.73	3.426 (2)	144
C114—H114···S1^ii	0.93	2.78	3.633 (3)	153

Symmetry codes: (i) x−1, y, z; (ii) −x+2, y+1/2, −z+1.

(VIII) (SFc)-diphenylphosphino-[2-(2-dibenzo-1H-1λ⁵-phospholyl)ferrocen-1- yl]methane

Crystal data

[Fe(C5H5)(C30H23P2)]	F(000) = 1176
Mr = 566.36	Dx = 1.369 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8000 reflections
a = 10.9693 (10) Å	θ = 2.1–26.1°
b = 11.0436 (10) Å	µ = 0.69 mm^−1
c = 22.678 (2) Å	T = 180 K
V = 2747.2 (4) Å^3	Prism, yellow
Z = 4	0.2 × 0.12 × 0.1 mm

Data collection

Stoe IPDS diffractometer	5395 independent reflections
Radiation source: fine-focus sealed tube	3205 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.145
ϕ scans	θmax = 26.1°, θmin = 2.1°
Absorption correction: multi-scan (Blessing, 1995)	h = −13→13
Tmin = 0.852, Tmax = 0.894	k = −13→13
22007 measured reflections	l = −27→27

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)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.0476P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max = 0.004
5395 reflections	Δρmax = 0.97 e Å^−3
343 parameters	Δρmin = −0.47 e Å^−3
0 restraints	Absolute structure: Flack (1983), with 2333 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (3)

Special details

Experimental. The data were collected on a Stoe Imaging Plate Diffraction System (IPDS). The crystal-to-detector distance was 70 mm. 179 frames (5 min per frame) were obtained with 0 < ϕ < 250.6° and with the crystals oscillated through 1.4° in ϕ. Coverage of the unique set was over 99.4% complete to at least 26.06°. Crystal decay was monitored by measuring 200 reflections per frame.

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	0.78911 (8)	0.88531 (7)	0.46301 (4)	0.0263 (2)
P1	0.62209 (16)	0.82877 (15)	0.33563 (8)	0.0348 (4)
P2	0.76292 (14)	0.49338 (13)	0.37331 (7)	0.0314 (4)
C1	0.6596 (5)	0.8045 (5)	0.4121 (3)	0.0278 (14)
C2	0.7485 (5)	0.7162 (5)	0.4324 (3)	0.0267 (13)
C3	0.7465 (6)	0.7179 (5)	0.4958 (3)	0.0319 (15)
H3	0.7938	0.6699	0.5205	0.038*
C4	0.6601 (6)	0.8056 (5)	0.5139 (3)	0.0348 (16)
H4	0.6420	0.8256	0.5528	0.042*
C5	0.6055 (5)	0.8581 (5)	0.4633 (3)	0.0323 (14)
H5	0.5450	0.9171	0.4634	0.039*
C6	0.9671 (6)	0.9196 (5)	0.4426 (3)	0.0354 (16)
H6	1.0204	0.8664	0.4240	0.042*
C7	0.9487 (6)	0.9291 (5)	0.5036 (3)	0.0368 (16)
H7	0.9880	0.8835	0.5324	0.044*
C8	0.8605 (6)	1.0197 (6)	0.5139 (3)	0.0387 (16)
H8	0.8315	1.0442	0.5506	0.046*
C9	0.8234 (5)	1.0671 (5)	0.4582 (3)	0.0349 (15)
H9	0.7659	1.1276	0.4519	0.042*
C10	0.8908 (5)	1.0048 (5)	0.4140 (3)	0.0300 (14)
H10	0.8856	1.0177	0.3736	0.036*
C11	0.5585 (6)	0.9812 (6)	0.3312 (3)	0.0360 (15)
C12	0.4327 (6)	0.9794 (6)	0.3202 (3)	0.0388 (16)
C13	0.3809 (6)	0.8549 (6)	0.3212 (3)	0.0359 (15)
C14	0.4690 (6)	0.7654 (5)	0.3307 (3)	0.0346 (15)
C21	0.8310 (6)	0.6416 (5)	0.3945 (3)	0.0331 (15)
H21A	0.9066	0.6272	0.4155	0.040*
H21B	0.8502	0.6868	0.3590	0.040*
C111	0.6198 (7)	1.0916 (5)	0.3314 (3)	0.0404 (15)
H111	0.7035	1.0931	0.3380	0.048*
C112	0.5581 (8)	1.1986 (6)	0.3222 (3)	0.0452 (19)
H112	0.5993	1.2721	0.3238	0.054*
C113	0.4332 (8)	1.1957 (7)	0.3103 (3)	0.049 (2)
H113	0.3917	1.2677	0.3032	0.059*
C114	0.3699 (7)	1.0861 (6)	0.3091 (3)	0.0469 (18)
H114	0.2868	1.0846	0.3010	0.056*
C211	0.7625 (5)	0.4160 (4)	0.4447 (3)	0.0298 (14)
C212	0.6541 (5)	0.3681 (5)	0.4649 (3)	0.0346 (14)
H212	0.5855	0.3707	0.4408	0.041*
C213	0.6454 (6)	0.3158 (6)	0.5208 (3)	0.0417 (17)
H213	0.5715	0.2845	0.5339	0.050*
C214	0.7461 (7)	0.3110 (6)	0.5561 (3)	0.0442 (18)
H214	0.7406	0.2774	0.5936	0.053*
C215	0.8568 (6)	0.3561 (5)	0.5361 (3)	0.0404 (15)
H215	0.9256	0.3514	0.5599	0.049*
C216	0.8650 (6)	0.4082 (5)	0.4804 (3)	0.0347 (15)
H216	0.9394	0.4379	0.4671	0.042*
C221	0.8944 (6)	0.4230 (5)	0.3373 (3)	0.0281 (13)
C222	0.9589 (6)	0.4865 (6)	0.2933 (3)	0.0382 (16)
H222	0.9373	0.5656	0.2840	0.046*
C223	1.0547 (7)	0.4309 (6)	0.2639 (3)	0.0424 (17)
H223	1.0979	0.4743	0.2357	0.051*
C224	1.0869 (6)	0.3127 (6)	0.2758 (3)	0.0394 (16)
H224	1.1506	0.2765	0.2553	0.047*
C225	1.0245 (6)	0.2485 (6)	0.3181 (3)	0.0417 (18)
H225	1.0462	0.1691	0.3268	0.050*
C226	0.9276 (6)	0.3044 (5)	0.3478 (3)	0.0367 (16)
H226	0.8842	0.2600	0.3757	0.044*
C411	0.4343 (6)	0.6449 (6)	0.3326 (3)	0.0419 (17)
H411	0.4927	0.5850	0.3383	0.050*
C412	0.3123 (7)	0.6131 (7)	0.3260 (3)	0.0533 (19)
H412	0.2885	0.5324	0.3279	0.064*
C413	0.2263 (7)	0.7043 (7)	0.3164 (3)	0.0531 (19)
H413	0.1449	0.6832	0.3115	0.064*
C414	0.2588 (6)	0.8233 (7)	0.3141 (3)	0.0490 (18)
H414	0.2002	0.8827	0.3079	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0289 (4)	0.0225 (4)	0.0276 (4)	−0.0013 (4)	−0.0009 (4)	0.0000 (4)
P1	0.0337 (9)	0.0381 (9)	0.0327 (9)	−0.0017 (7)	−0.0058 (8)	0.0026 (8)
P2	0.0344 (10)	0.0249 (7)	0.0351 (8)	0.0005 (6)	−0.0047 (8)	0.0015 (6)
C1	0.024 (3)	0.024 (3)	0.036 (4)	0.005 (2)	0.001 (3)	0.001 (2)
C2	0.024 (3)	0.031 (3)	0.025 (3)	−0.004 (2)	0.004 (3)	0.001 (2)
C3	0.032 (4)	0.029 (3)	0.034 (4)	−0.005 (3)	0.002 (3)	0.008 (3)
C4	0.040 (4)	0.037 (4)	0.028 (3)	−0.008 (3)	0.003 (3)	−0.003 (3)
C5	0.030 (3)	0.034 (3)	0.034 (3)	0.003 (2)	−0.002 (3)	−0.003 (3)
C6	0.039 (4)	0.026 (3)	0.042 (4)	0.005 (3)	0.003 (3)	−0.003 (3)
C7	0.043 (4)	0.035 (3)	0.033 (4)	0.000 (3)	−0.009 (3)	0.004 (3)
C8	0.041 (4)	0.039 (4)	0.036 (4)	−0.001 (3)	−0.001 (3)	−0.006 (3)
C9	0.037 (4)	0.025 (3)	0.043 (4)	0.001 (2)	−0.007 (3)	−0.001 (3)
C10	0.035 (4)	0.022 (3)	0.033 (3)	0.002 (3)	−0.003 (3)	0.001 (2)
C11	0.044 (4)	0.046 (4)	0.018 (3)	−0.001 (3)	−0.005 (3)	0.004 (3)
C12	0.040 (4)	0.049 (4)	0.028 (4)	0.007 (3)	−0.009 (3)	0.004 (3)
C13	0.027 (3)	0.051 (4)	0.029 (4)	0.000 (3)	−0.003 (3)	0.001 (3)
C14	0.040 (4)	0.037 (3)	0.027 (3)	0.002 (3)	0.000 (3)	−0.002 (3)
C21	0.037 (4)	0.024 (3)	0.038 (4)	0.003 (2)	0.003 (3)	0.001 (3)
C111	0.042 (4)	0.038 (4)	0.041 (4)	0.003 (3)	−0.005 (3)	0.011 (3)
C112	0.062 (5)	0.042 (4)	0.031 (4)	−0.001 (3)	0.000 (4)	0.012 (3)
C113	0.068 (6)	0.052 (5)	0.028 (4)	0.013 (4)	−0.004 (4)	0.003 (3)
C114	0.052 (4)	0.058 (5)	0.031 (4)	0.016 (4)	−0.009 (4)	0.004 (3)
C211	0.030 (3)	0.022 (3)	0.038 (3)	0.001 (2)	−0.005 (3)	−0.005 (2)
C212	0.032 (3)	0.032 (3)	0.040 (3)	0.002 (2)	0.007 (3)	−0.004 (3)
C213	0.040 (4)	0.039 (4)	0.046 (5)	0.002 (3)	0.015 (4)	−0.005 (3)
C214	0.057 (5)	0.042 (4)	0.034 (4)	0.003 (3)	0.007 (3)	0.003 (3)
C215	0.044 (4)	0.048 (4)	0.030 (3)	0.007 (3)	−0.005 (4)	0.000 (3)
C216	0.033 (3)	0.032 (3)	0.039 (4)	−0.003 (3)	−0.001 (3)	0.003 (3)
C221	0.042 (4)	0.023 (3)	0.020 (3)	−0.006 (2)	−0.007 (3)	0.000 (2)
C222	0.055 (4)	0.029 (3)	0.031 (4)	−0.003 (3)	0.004 (3)	0.005 (3)
C223	0.053 (4)	0.043 (4)	0.032 (4)	−0.011 (3)	0.012 (4)	0.000 (3)
C224	0.040 (4)	0.045 (4)	0.033 (4)	0.004 (3)	0.004 (3)	−0.008 (3)
C225	0.047 (5)	0.031 (3)	0.047 (5)	0.004 (3)	0.000 (4)	−0.006 (3)
C226	0.051 (4)	0.020 (3)	0.039 (4)	−0.007 (3)	0.006 (3)	−0.002 (3)
C411	0.038 (4)	0.049 (4)	0.039 (4)	−0.007 (3)	−0.011 (3)	0.005 (3)
C412	0.051 (5)	0.067 (4)	0.042 (4)	−0.023 (4)	−0.014 (4)	0.004 (4)
C413	0.041 (5)	0.075 (5)	0.043 (4)	−0.014 (4)	−0.006 (4)	0.007 (4)
C414	0.036 (4)	0.066 (5)	0.045 (4)	−0.002 (3)	−0.009 (3)	−0.001 (4)

Geometric parameters (Å, º)

Fe1—C4	2.027 (6)	C13—C14	1.400 (9)
Fe1—C1	2.036 (6)	C14—C411	1.384 (9)
Fe1—C5	2.036 (6)	C21—H21A	0.9700
Fe1—C7	2.037 (7)	C21—H21B	0.9700
Fe1—C8	2.037 (6)	C111—C112	1.378 (9)
Fe1—C2	2.042 (5)	C111—H111	0.9300
Fe1—C6	2.042 (7)	C112—C113	1.396 (10)
Fe1—C9	2.046 (5)	C112—H112	0.9300
Fe1—C3	2.046 (5)	C113—C114	1.396 (10)
Fe1—C10	2.054 (6)	C113—H113	0.9300
P1—C1	1.803 (6)	C114—H114	0.9300
P1—C14	1.823 (7)	C211—C212	1.380 (8)
P1—C11	1.825 (7)	C211—C216	1.388 (8)
P2—C221	1.830 (6)	C212—C213	1.398 (9)
P2—C211	1.831 (6)	C212—H212	0.9300
P2—C21	1.862 (6)	C213—C214	1.365 (9)
C1—C5	1.432 (9)	C213—H213	0.9300
C1—C2	1.454 (8)	C214—C215	1.389 (9)
C2—C3	1.437 (8)	C214—H214	0.9300
C2—C21	1.496 (8)	C215—C216	1.389 (9)
C3—C4	1.417 (8)	C215—H215	0.9300
C3—H3	0.9300	C216—H216	0.9300
C4—C5	1.417 (9)	C221—C226	1.381 (8)
C4—H4	0.9300	C221—C222	1.409 (8)
C5—H5	0.9300	C222—C223	1.387 (9)
C6—C7	1.403 (9)	C222—H222	0.9300
C6—C10	1.416 (8)	C223—C224	1.379 (9)
C6—H6	0.9300	C223—H223	0.9300
C7—C8	1.411 (9)	C224—C225	1.374 (9)
C7—H7	0.9300	C224—H224	0.9300
C8—C9	1.428 (9)	C225—C226	1.402 (9)
C8—H8	0.9300	C225—H225	0.9300
C9—C10	1.421 (9)	C226—H226	0.9300
C9—H9	0.9300	C411—C412	1.391 (9)
C10—H10	0.9300	C411—H411	0.9300
C11—C111	1.392 (9)	C412—C413	1.396 (11)
C11—C12	1.402 (9)	C412—H412	0.9300
C12—C114	1.388 (9)	C413—C414	1.363 (10)
C12—C13	1.488 (9)	C413—H413	0.9300
C13—C414	1.393 (9)	C414—H414	0.9300
C4—Fe1—C1	69.2 (2)	C9—C8—Fe1	69.9 (3)
C4—Fe1—C5	40.8 (3)	C7—C8—H8	126.0
C1—Fe1—C5	41.2 (2)	C9—C8—H8	126.0
C4—Fe1—C7	116.5 (3)	Fe1—C8—H8	126.0
C1—Fe1—C7	163.8 (2)	C10—C9—C8	107.3 (5)
C5—Fe1—C7	152.1 (3)	C10—C9—Fe1	70.0 (3)
C4—Fe1—C8	105.2 (3)	C8—C9—Fe1	69.2 (3)
C1—Fe1—C8	155.3 (2)	C10—C9—H9	126.3
C5—Fe1—C8	119.1 (3)	C8—C9—H9	126.3
C7—Fe1—C8	40.5 (2)	Fe1—C9—H9	126.0
C4—Fe1—C2	69.1 (2)	C6—C10—C9	107.9 (5)
C1—Fe1—C2	41.8 (2)	C6—C10—Fe1	69.3 (4)
C5—Fe1—C2	69.5 (2)	C9—C10—Fe1	69.4 (3)
C7—Fe1—C2	124.0 (2)	C6—C10—H10	126.1
C8—Fe1—C2	160.6 (2)	C9—C10—H10	126.1
C4—Fe1—C6	151.3 (3)	Fe1—C10—H10	126.8
C1—Fe1—C6	128.3 (2)	C111—C11—C12	119.2 (6)
C5—Fe1—C6	166.9 (3)	C111—C11—P1	128.6 (5)
C7—Fe1—C6	40.2 (3)	C12—C11—P1	111.9 (5)
C8—Fe1—C6	68.0 (3)	C114—C12—C11	120.6 (7)
C2—Fe1—C6	107.5 (2)	C114—C12—C13	126.7 (6)
C4—Fe1—C9	125.8 (3)	C11—C12—C13	112.7 (6)
C1—Fe1—C9	121.9 (2)	C414—C13—C14	120.3 (6)
C5—Fe1—C9	109.1 (2)	C414—C13—C12	126.7 (6)
C7—Fe1—C9	68.5 (2)	C14—C13—C12	113.0 (6)
C8—Fe1—C9	40.9 (3)	C411—C14—C13	119.5 (6)
C2—Fe1—C9	156.9 (3)	C411—C14—P1	128.4 (5)
C6—Fe1—C9	68.3 (2)	C13—C14—P1	112.0 (5)
C4—Fe1—C3	40.7 (2)	C2—C21—P2	112.9 (4)
C1—Fe1—C3	69.6 (2)	C2—C21—H21A	109.0
C5—Fe1—C3	68.9 (2)	P2—C21—H21A	109.0
C7—Fe1—C3	104.3 (2)	C2—C21—H21B	109.0
C8—Fe1—C3	122.7 (3)	P2—C21—H21B	109.0
C2—Fe1—C3	41.2 (2)	H21A—C21—H21B	107.8
C6—Fe1—C3	117.9 (2)	C112—C111—C11	120.9 (7)
C9—Fe1—C3	161.5 (3)	C112—C111—H111	119.6
C4—Fe1—C10	165.0 (2)	C11—C111—H111	119.6
C1—Fe1—C10	110.7 (2)	C111—C112—C113	119.5 (7)
C5—Fe1—C10	129.3 (2)	C111—C112—H112	120.3
C7—Fe1—C10	68.0 (3)	C113—C112—H112	120.3
C8—Fe1—C10	68.3 (2)	C112—C113—C114	120.8 (7)
C2—Fe1—C10	121.5 (2)	C112—C113—H113	119.6
C6—Fe1—C10	40.5 (2)	C114—C113—H113	119.6
C9—Fe1—C10	40.6 (2)	C12—C114—C113	119.0 (7)
C3—Fe1—C10	154.3 (2)	C12—C114—H114	120.5
C1—P1—C14	102.2 (3)	C113—C114—H114	120.5
C1—P1—C11	106.1 (3)	C212—C211—C216	118.7 (6)
C14—P1—C11	89.9 (3)	C212—C211—P2	118.3 (5)
C221—P2—C211	101.4 (3)	C216—C211—P2	122.9 (5)
C221—P2—C21	99.9 (3)	C211—C212—C213	121.2 (6)
C211—P2—C21	100.6 (3)	C211—C212—H212	119.4
C5—C1—C2	107.4 (5)	C213—C212—H212	119.4
C5—C1—P1	128.7 (4)	C214—C213—C212	119.5 (6)
C2—C1—P1	123.8 (4)	C214—C213—H213	120.3
C5—C1—Fe1	69.4 (3)	C212—C213—H213	120.3
C2—C1—Fe1	69.3 (3)	C213—C214—C215	120.2 (6)
P1—C1—Fe1	129.8 (3)	C213—C214—H214	119.9
C3—C2—C1	107.3 (5)	C215—C214—H214	119.9
C3—C2—C21	126.2 (5)	C214—C215—C216	120.1 (6)
C1—C2—C21	126.4 (5)	C214—C215—H215	119.9
C3—C2—Fe1	69.6 (3)	C216—C215—H215	119.9
C1—C2—Fe1	68.9 (3)	C211—C216—C215	120.2 (6)
C21—C2—Fe1	124.5 (4)	C211—C216—H216	119.9
C4—C3—C2	108.0 (6)	C215—C216—H216	119.9
C4—C3—Fe1	68.9 (3)	C226—C221—C222	117.5 (6)
C2—C3—Fe1	69.2 (3)	C226—C221—P2	122.2 (5)
C4—C3—H3	126.0	C222—C221—P2	120.0 (4)
C2—C3—H3	126.0	C223—C222—C221	120.1 (6)
Fe1—C3—H3	127.4	C223—C222—H222	120.0
C3—C4—C5	109.1 (6)	C221—C222—H222	120.0
C3—C4—Fe1	70.4 (3)	C224—C223—C222	121.2 (6)
C5—C4—Fe1	69.9 (4)	C224—C223—H223	119.4
C3—C4—H4	125.4	C222—C223—H223	119.4
C5—C4—H4	125.4	C225—C224—C223	119.8 (6)
Fe1—C4—H4	125.8	C225—C224—H224	120.1
C4—C5—C1	108.2 (5)	C223—C224—H224	120.1
C4—C5—Fe1	69.2 (3)	C224—C225—C226	119.1 (6)
C1—C5—Fe1	69.4 (3)	C224—C225—H225	120.4
C4—C5—H5	125.9	C226—C225—H225	120.4
C1—C5—H5	125.9	C221—C226—C225	122.3 (6)
Fe1—C5—H5	127.0	C221—C226—H226	118.9
C7—C6—C10	108.5 (6)	C225—C226—H226	118.9
C7—C6—Fe1	69.7 (4)	C14—C411—C412	120.3 (7)
C10—C6—Fe1	70.2 (4)	C14—C411—H411	119.9
C7—C6—H6	125.8	C412—C411—H411	119.9
C10—C6—H6	125.8	C411—C412—C413	119.0 (7)
Fe1—C6—H6	125.9	C411—C412—H412	120.5
C6—C7—C8	108.3 (6)	C413—C412—H412	120.5
C6—C7—Fe1	70.1 (4)	C414—C413—C412	121.6 (7)
C8—C7—Fe1	69.7 (4)	C414—C413—H413	119.2
C6—C7—H7	125.8	C412—C413—H413	119.2
C8—C7—H7	125.8	C413—C414—C13	119.3 (7)
Fe1—C7—H7	125.9	C413—C414—H414	120.4
C7—C8—C9	108.0 (6)	C13—C414—H414	120.4
C7—C8—Fe1	69.7 (4)