Mol­ecular structures of the penta­phenyl­cyclo­penta­dienyl iron com­plexes [(C₅Ph₅)Fe(CO)₂R] (R = Me, Ph, iPr and Bu)

The Pd^II-catalysed reaction of [(C₅Ph₅)Fe(CO)₂Br] with Grignard com­pounds RMgX or butyl lithium gave the iron alk­yl/aryl com­plexes [(C₅Ph₅)Fe(CO)₂R] (R = Me, Ph, iPr and Bu) in 59–73% yield, namely, di­carbonyl­meth­yl(η⁵-penta­phenyl­cyclo­penta­dien­yl)iron, [Fe(CH₃)(C₃₅H₂₅)(CO)₂], dicarbon­yl(η⁵-penta­phenyl­cyclo­penta­dien­yl)phenyliron, [Fe(C₆H₅)(C₃₅H₂₅)(CO)₂], dicarbon­yl(isoprop­yl)(η⁵-penta­phenyl­cyclo­penta­dien­yl)iron, [Fe(C₃H₇)(C₃₅H₂₅)(CO)₂], and butyl­dicarbon­yl(η⁵-penta­phenyl­cyclo­penta­dien­yl)iron, [Fe(C₄H₉)(C₃₅H₂₅)(CO)₂]. The crystal structure determinations showed the usual `paddle-wheel' orientation of the phenyl rings, with an average canting angle of ca 50°. The bond parameters are mainly dictated by the steric requirements of the alk­yl/aryl groups and only the phenyl com­plex shows electronic effects.

1. Introduction

Penta­aryl­cyclo­penta­dienyl com­plexes have been known for nearly 60 years. They were studied mainly because the bulky nature of these cyclo­penta­dienyl derivatives gives their com­plexes high kinetic stability, including the formation of stable radicals (Field et al., 2011) or unusual structures in main group or lanthanoid metallocenes (Schulte et al., 2020). Also, several examples of their application as asymmetric catalysts (Ruble et al., 1997; Field et al., 2011) and as mimics for hydrogenase (Hemming et al., 2018) were found. So far (Scifinder, accessed on 12th May 2021), 451 publications describing 723 substances have appeared, an increase of 80% during the last decade. On the other hand, a survey of the Cambridge Structural Database (CSD, Version 5.42, accessed on 5th June, 2021; Groom et al., 2016) showed only 118 entries, of which roughly half (52) contained iron as the central metal atom. Of these, ca 80% (41) were ferrocene derivatives. The mol­ecular structure of the very first penta­phenyl­cyclo­penta­dienyl com­plex, i.e. [(C₅Ph₅)Fe(CO)₂Br] (McVey & Pauson, 1965), was published only 25 years later (Field et al., 1989) and there are only three other structure determinations of mol­ecules containing the [(C₅Ph₅)Fe(CO)₂] moiety in the CSD: MARFET and MARFIX (Hemming et al., 2018), and PUYDES (Carter et al., 2002). A very important subgroup of com­pounds containing the [CpFe(CO)] moiety contains the derived alkyl and aryl com­plexes [CpFe(CO)₂R] (Pannell & Sharma, 2010). These com­pounds were shown to have catalytic properties, for example, in de­hydrogenative couplings (Fukumoto et al., 2015; Argouarch et al., 2012) or, perhaps more importantly, as reagents in photoinduced DNA cleavage (Mohler et al., 2002; Mohler & Shell, 2005). Therefore, it seemed worthwhile to study com­pounds of the type [(C₅Ph₅)Fe(CO)₂R], which might combine the unique properties of the penta­phenyl­cyclo­penta­dienyl moiety with the reactivity of the iron–alkyl and iron–aryl groups. Such com­pounds have been reported before, but were usually only partially characterized (Connelly & Manners, 1989; Brégaint et al., 1990, 1992; Kuksis & Baird, 1994; Kuksis et al., 1996). In particular, no crystal structures have been published. During the course of our studies on the coordination chemistry of perhalogenated cyclo­penta­dienyl com­plexes (Klein-Heßling et al., 2021; Sünkel et al., 2015) we also studied the [(C₅X₅)Fe(CO)₂R] system. In the search for possible synthetic applications for these com­pounds and also for the sake of com­parison, we chose to prepare the alkyl and aryl [(C₅Ph₅)Fe(CO)₂R] derivatives (R = Me, 1, Ph, 2, iPr, 3, and Bu, 4) (Scheme 1). We report here the results of our crystal structure studies.

2. Experimental

2.1. Synthesis and crystallization

The starting material [(C₅Ph₅)Fe(CO)₂Br] was prepared according to the literature from Fe(CO)₅ and C₅Ph₅Br (McVey & Pauson, 1965). The reagents MeMgBr (3.0 M solution in Et₂O), PhMgCl [2.0 M solution in tetra­hydro­furan (THF)], iPrMgCl (1.3 M solution with LiCl in THF) and BuLi (2.5 M solution in hexa­ne), as well as N,N,N′,N′-tetra­methyl­ethylendi­amine (TMEDA) and palladium acetate, were commercial products (Sigma–Aldrich) and were used as provided.

2.1.1. [(C₅Ph₅)Fe(CO)₂Me], (1)

A solution of [(C₅Ph₅)Fe(CO)₂Br] (0.30 g, 0.47 mmol) in THF (12 ml), palladium(II) acetate (0.01 g, 0.05 mmol) and TMEDA (0.07 ml, 0.71 mmol) was treated at 0 °C with an MeMgBr solution (0.24 ml, 0.71 mmol) and stirred for 60 min. After evaporation of the solvent, the residue was redissolved in the minimum amount of petroleum ether and placed on top of a silica-gel chromatography column. Elution with petroleum ether/Et₂O (9:1 v/v) yielded, after evaporation, com­pound 1 as a yellow solid (yield: 0.17 g, 0.30 mmol, 63%). Crystals suitable for X-ray diffraction were obtained by slow evaporation of a petroleum ether solution in a refrigerator at 5 °C.

IR (ATR): ν (CO) 1993, 1941 cm⁻¹. UV–Vis (CH₂Cl₂): λ_max = 369 nm. ¹H NMR (CDCl₃, 400 MHz): δ 7.20–6.90 (m, Ph), 0.62 (s, Me) ppm. ¹³C NMR (CDCl₃, 100.5 MHz): δ 217.8 (CO), 132.2, 131.9, 127.7, 127.5 (4 × Ph), 102.1 (C5), −7.5 (Me) ppm.

2.1.2. [(C₅Ph₅)Fe(CO)₂Ph], (2)

A solution of [(C₅Ph₅)Fe(CO)₂Br] (0.05 g, 0.08 mmol) in THF (10 ml), palladium(II) ace­tate (0.002 g, 0.01 mmol) and TMEDA (0.01 ml, 0.08 mmol) was treated at 0 °C with a PhMgCl solution (0.05 ml, 0.10 mmol) and stirred for 60 min. After evaporation of the solvent, the residue was redissolved in the minimum amount of petroleum ether and placed on top of a silica-gel chromatography column. Elution with petroleum ether/Et₂O (9:1 v/v) yielded, after evaporation, com­pound 2 as a yellow solid (yield: 0.03 g, 0.05 mmol, 59%). Crystals suitable for X-ray diffraction were obtained by slow evaporation of a petroleum ether solution in a refrigerator at 5 °C.

IR (ATR): ν (CO) 2009, 1968 cm⁻¹. UV–Vis (CH₂Cl₂): λ_max = 364 nm. ¹H NMR (CDCl₃, 400 MHz): δ 7.23–6.81 (m, Ph) ppm. ¹³C NMR (CDCl₃, 100.5 MHz): δ 216.5 (CO), 147–123 (35 × Ph), 102.8 (C5) ppm.

2.1.3. [(C₅Ph₅)Fe(CO)₂iPr], (3)

A solution of [(C₅Ph₅)Fe(CO)₂Br] (0.10 g, 0.16 mmol) in THF (10 ml), palladium(II) acetate (0.004 g, 0.02 mmol) and TMEDA (0.02 ml, 0.16 mmol) was treated at 0°C with an iPrMgCl solution (0.18 ml, 0.24 mmol) and stirred for 60 min. After evaporation of the solvent, the residue was redissolved in the minimum amount of petroleum ether and placed on top of a silica-gel chromatography column. Elution with petroleum ether/Et₂O (9:1 v/v) yielded, after evaporation, com­pound 3 as a yellow solid (yield: 0.07 g, 0.12 mmol, 73%). Crystals suitable for X-ray diffraction were obtained by slow evaporation of a petroleum ether solution in a refrigerator at 5 °C.

IR (ATR): ν (CO) 1991, 1939 cm⁻¹. UV–Vis (CH₂Cl₂): λ_max = 367 nm. ¹H NMR (CDCl₃, 400 MHz): δ 7.32–6.85 (m, Ph), 3.07 (m, CHMe₂), 1.46 (m, CHMe₂) ppm.

2.1.4. [(C₅Ph₅)Fe(CO)₂Bu], (4)

A solution of [(C₅Ph₅)Fe(CO)₂Br] (0.05 g, 0.08 mmol) in THF (10 ml), palladium(II) acetate (0.002 g, 0.01 mmol) and TMEDA (0.01 ml, 0.08 mmol) was treated at −30 °C with a BuLi solution (0.04 ml, 0.10 mmol) and stirred for 60 min. After evaporation of the solvent, the residue was redissolved in the minimum amount of petroleum ether and placed on top of a silica-gel chromatography column. Elution with petroleum ether/Et₂O (9:1 v/v) yielded after evaporation com­pound 4 as a yellow solid (yield: 0.03 g, 0.05 mmol, 63%). Crystals suitable for X-ray diffraction were obtained by slow evaporation of a petroleum ether solution in a refrigerator at 5 °C.

IR (ATR): ν (CO) 1993, 1939 cm⁻¹. UV–Vis (CH₂Cl₂): λ_max = 378 nm. ¹H NMR (CDCl₃, 400 MHz): δ 7.22–6.84 (m, Ph), 1.95–0.80 (4 m, Bu) ppm. ¹³C NMR (CDCl₃, 100.5 MHz): δ 218.7 (CO), 132.2, 132.0, 127.7, 127.4 (4 × Ph), 102.3 (C5), 38.5, 28.2, 17.7, 14.1 (4 × Bu) ppm.

2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms on C atoms were calculated in ideal positions riding on their parent atoms, with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C) for aromatic H atoms, and C—H = 0.98 Å and U_iso(H) = 1.5U_eq(C) for methyl H atoms. The methyl groups were allowed to rotate along the C—C bonds to best fit the experimental electron density.

Table 1
Experimental details

Experiments were carried out with Mo Kα radiation using a Bruker D8 Venture diffractometer. Absorption was corrected for by multi-scan methods (SADABS; Krause et al., 2015). H-atom parameters were constrained.

	1	2	3	4
Crystal data
Chemical formula	[Fe(CH3)(C35H25)(CO)2]	[Fe(C6H5)(C35H25)(CO)2]	[Fe(C3H7)(C35H25)(CO)2]	[Fe(C4H9)(C35H25)(CO)2]
Mr	572.45	634.52	600.50	614.53
Crystal system, space group	Orthorhombic, Pbca	Monoclinic, P21/n	Monoclinic, P21/n	Monoclinic, P21/n
Temperature (K)	105	105	110	108
a, b, c (Å)	13.6393 (3), 20.4360 (5), 21.1978 (5)	12.1860 (4), 16.9411 (6), 15.0691 (6)	12.5488 (7), 13.5046 (7), 18.0119 (11)	12.1141 (4), 16.0945 (5), 16.1650 (5)
α, β, γ (°)	90, 90, 90	90, 93.320 (1), 90	90, 93.208 (2), 90	90, 95.706 (1), 90
V (Å^3)	5908.5 (2)	3105.71 (19)	3047.6 (3)	3136.08 (17)
Z	8	4	4	4
μ (mm^−1)	0.54	0.52	0.53	0.52
Crystal size (mm)	0.06 × 0.05 × 0.04	0.08 × 0.02 × 0.02	0.06 × 0.04 × 0.03	0.08 × 0.05 × 0.04
Data collection
Tmin, Tmax	0.718, 0.746	0.669, 0.745	0.719, 0.746	0.832, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	61228, 6765, 5439	31592, 6352, 5025	52953, 6732, 5995	55494, 7202, 6246
Rint	0.053	0.050	0.031	0.041
(sin θ/λ)max (Å^−1)	0.649	0.625	0.641	0.650
Refinement
R[F^2 > 2σ(F^2)], wR(F^2), S	0.035, 0.090, 1.06	0.041, 0.088, 1.04	0.032, 0.088, 1.06	0.033, 0.090, 1.05
No. of reflections	6765	6352	6732	7202
No. of parameters	371	415	390	398
Δρmax, Δρmin (e Å^−3)	0.35, −0.49	0.32, −0.41	0.36, −0.36	0.37, −0.47
Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2011), SHELXT2018 (Sheldrick, 2015a), SHELXL2018 (Sheldrick, 2015b), ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al., 2020) and WinGX (Farrugia, 2012).

3. Results and discussion

The title com­pounds were prepared in medium to good yields from [(C₅Ph₅)Fe(CO)₂Br] and either Grignard reagents RMgX or butyl lithium in the presence of catalytic amounts of Pd(OAc)₂ and TMEDA (Scheme 1).

The synthesis is based on a procedure that was described for the preparation of aryl iron com­plexes [(C₅H₅)Fe(CO)₂Ar] (Yasuda et al., 2008). Compounds 1 and 3 had been prepared before by reaction of [(C₅Ph₅)Fe(CO)₂]₂ with the corresponding alkyl iodides (no yields given; Kuksis et al., 1996) or of [(C₅Ph₅)Fe(CO)₂Br] and MeMgBr (55% yield; Connelly & Manners, 1989).

All four com­pounds, particularly phenyl com­pound 2, showed a pale-blue fluorescence when irradiated at 365 nm.

3.1. Crystal structures

3.1.1. [(C₅Ph₅)Fe(CO)₂Me], 1

Compound 1 crystallizes in the ortho­rhom­bic space group Pbca with one mol­ecule in the asymmetric unit (Fig. 1).

Figure 1 Displacement ellipsoid plot (top view) of com­pound 1, with ellipsoids drawn at the 30% probability level.

The Fe—C(meth­yl) bond eclipses the cyclo­penta­dienyl (Cp) C5—C501 bond, while the Fe1—C6 bond bis­ects the cyclo­penta­dienyl C1—C2 bond. All the phenyl rings are canted in the same way, as usual, with angles between the planes of the cyclo­penta­dienyl and phenyl rings ranging from 37.80 (9) to 58.66 (9)°. The Cp ring is essentially planar, with a sigpln parameter of PLATON, defined as:

of 0.023 (Spek, 2020). Table 2 collects some important bond parameters for com­pounds 1–4, together with the corresponding data from the other four published structures containing the [(C₅Ph₅)Fe(CO)₂] moiety. PLATON analysis of the crystal structure showed that 6.3% of the volume contained solvent-accessible voids. A PLATON cavity plot (see Fig. 2) shows that the dumbbell-shaped voids are arranged in an fcc-type (fcc is face-centred cubic) lattice.

Table 2
Comparison of important bond parameters (Å, °) of com­pounds 1–4 and some related structures from the CSD

	1	2	3	4	SIRMIP	MARFET	MARFIX	PUYDES	HOZWIC	CECKUS01
Fe—Ct (Å)	1.7403 (8)	1.7625 (10)	1.7586 (7)	1.7603 (7)	1.738 (5)	1.7464 (10)	1.7360 (12)/	1.715 (3)	1.730	1.730
							1.7306 (12)
Fe—Cα(R) (Å)	2.073 (2)	2.022 (2)	2.1188 (17)	2.0810 (16)	n.a.	n.a.	n.a.	n.a.	2.069 (10)	2.002 (2)
Fe—C(CO) (Å)	1.751 (2)	1.755 (2)	1.745 (2)	1.755 (2)	1.812 (5)		1.803 (3)	1.714 (6)	1.739 (11)	1.756 (1)
	1.754 (2)	1.760 (2)	1.756 (2)	1.755 (2)	1.786 (5)		1.813 (3)	1.715 (6)	1.751 (11)
C—O (Å)	1.149 (2)	1.152 (3)	1.145 (3)	1.150 (1)	1.052 (6)	1.133 (3)	1.131 (4)/	1.182 (7)	1.153 (13)	1.151 (2)
	1.136 (2)	1.148 (3)	1.148 (2)	1.148 (2)	1.097 (6)	1.137 (4)	1.126 (4)	1.187 (7)	1.139 (14)	1.151 (2)
							1.137 (3)/
							1.132 (4)
IR (νCO, cm^−1)	1993, 1941	2009, 1968	1991, 1939	1993, 1939	2033, 1993*			1872, 1806*	1987, 1933*	1994, 1937*
(Ci,Ph—Cp)av (Å)	0.122	0.188	0.144	0.160	0.15	0.147	0.144/0.145		n.a.	n.a.
(Cp–Ph)av (°)	50.3	48.5	50.6	50.2	58.7	52.3	51.8/51.4	53.4	n.a.	n.a.
[Cα—Fe—Ct—CCp]min	9.35	26.46	5.13	32.19	n.a.	n.a.	n.a.	n.a.	1.44	0.0
Ct—Fe—Cα—Cβ (°)	n.a.	95.8	141.1	167.4	n.a.	n.a.	n.a.	n.a.	179.9	87.5
		79.8	91.8
CSD refcodes: SIRMIP is [(C5Ph5)Fe(CO)2Br] (Field et al., 1989), MARFET is [(C5Ph5)Fe(CO)2FBF3] (Hemming et al., 2018), MARFIX is [(C5Ph5)Fe(CO)2(H2O)]BF4 (Hemming et al., 2018), PUYDES is [PPN][(C5Ph5)Fe(CO)2] (Carter et al., 2002), HOZWIC is [(C5Me5)Fe(CO)2C5H11] (Hill et al., 1999) and CECKUS01 is [(C5Me5)Fe(CO)2Ph] (Kalman et al., 2013). Notes: Ct is the centroid of the cyclo­penta­dienyl ring. (Ci,Ph—Cp)av is the average distance of the phenyl ipso-C atoms from the plane of the Cp ring. (Cp–Ph)av is the average dihedral angle of the five phenyl rings with respect to the plane of the Cp ring, [Cα—Fe—Ct—CCp]min is the smallest torsion angle between the α-alk­yl/aryl C atom, the Fe atom, the centroid of the cyclo­penta­dienyl ring and a Cp-ring C atom. `n.a.' denotes not applicable. The asterisk (*) denotes solution spectra.

Figure 2 PLATON (Spek, 2020) cavity plot of com­pound 1.

When looking at inter­molecular inter­actions in mercury, some `nonclassical' C—H⋯O contacts [for the concept of C—H⋯O contacts, see Desiraju (2005)] appear (Fig. 3). Atom O1 accepts hydrogen bonds from H304 and H305, while atom O2 accepts a hydrogen bond from H104 (see Table 3 for the hydrogen-bond distances).

Table 3
Nonclassical C—H⋯O contacts in 1–4

Compound	Atom pair	Distance (Å)	Symmetry code
1	H504⋯O1	2.597	−x + , −y + 1, z +
	H104⋯O2	2.611	−x + , y − , z
	O1⋯H304	2.703	−x + , y − , z
2	O1⋯H404	2.475	−x + , y − , −z +
3	H14⋯O2	2.694	−x + , y − , −z +
	H56⋯O1	2.430	−x + 1, −y + 2, −z + 1
4	O2⋯H504	2.589	−x + , y − , −z +

Figure 3 The nonclassical C—H⋯O contacts in com­pound 1.

These contacts `join' individual mol­ecules in all directions, leading to the packing shown in Fig. 4.

Figure 4 Packing diagram of com­pound 1, viewed along the crystallographic a axis.

3.1.2. [(C₅Ph₅)Fe(CO)₂Ph], 2

Compound 2 crystallizes in the monoclinic space group P2₁/n with one mol­ecule in the asymmetric unit (Fig. 5 shows a side view).

Figure 5 Displacement ellipsoid plot (side view) of com­pound 2, with ellipsoids drawn at the 30% probability level.

The iron–phenyl bond Fe1—C11 nearly bis­ects the cyclo­penta­dienyl C4—C5 bond. As usual, the phenyl rings exhibit a chiral propeller arrangement (but, of course, in a centrosymmetric space group like P2₁/n, both enanti­omers are present), with inter­planar Cp–Ph angles ranging from 30.41 (12) to 59.17 (12)°. The Cp ring is essentially planar, with sigpln = 0.008. The five ipso-C atoms of the phenyl rings are all situated on the distal side of the Cp ring, with distances from the ring plane ranging from 0.147 (2) to 0.224 (2) Å. The σ-phenyl ring lies approximately perpendicular to the plane containing the Cp ring centroid, the Fe atom and the α-phenyl C atom, with light `bending' at the α-phenyl C atom [Fe1—C11⋯C14 = 174.3 (2)°].

The closest structural `relative' to 2 that can be found in the literature is CECKUS01 [(C₅Me₅)Fe(CO)₂Ph] (Kalman et al., 2013). There, the iron–phenyl bond length is 2.002 (2) Å. As in 2, the σ-phenyl ring is oriented perpendicular to the plane defined by the Cp centroid, the Fe atom and the α-phenyl C atom, with a slight bend at the α-phenyl C atom.

A PLATON (Spek, 2020) analysis of the crystal structure shows solvent-accessible voids of only 22 ų (0.7%). A cavity plot (Fig. 6) shows a `body-centred' arrangement of these small spherical voids (radius 1.28 Å each), that appear to be `sandwiched' by two cyclo­penta­dienyl rings.

Figure 6 PLATON (Spek, 2020) cavity plot of com­pound 2.

As observed for com­pound 1, there are also C—H⋯O contacts in com­pound 2 (Fig. 7). However, here only atom O1 is involved in a contact with H404. The individual mol­ecules are `aligned' by these contacts in the a and b directions (Fig. 8).

Figure 7 The nonclassical C—H⋯O contacts in com­pound 2.

Figure 8 Packing diagram of com­pound 2, viewed along the crystallographic a direction.

3.1.3. [(C₅Ph₅)Fe(CO)₂iPr], 3

Compound 3 also crystallizes in the monoclinic space group P2₁/n with one mol­ecule in the asymmetric unit (Fig. 9 shows a top view).

Figure 9 Displacement ellipsoid plot (top view) of com­pound 3, with ellipsoids drawn at the 30% probability level.

The iron–isopropyl bond Fe—C8 eclipses the exocyclic cyclo­penta­dienyl C2—C21 bond, while the Fe—C6O1 bond bis­ects the cyclo­penta­dienyl C3—C4 bond. Again, all the phenyl rings show a paddle-wheel orientation, with inter­planar angles ranging from 43.72 (8) and 60.94 (8)°. The cyclo­penta­dienyl ring deviates slightly from planarity, with a sigpln parameter of 0.030. All the phenyl-ring ipso-C atoms are located on the distal side of the Cp ring, with distances from the plane ranging from 0.056 (1) to 0.279 (1) Å. PLATON (Spek, 2020) analysis of the crystal structure shows solvent-accessible voids of only 18 ų (0.6%). A cavity plot (Fig. 10) again shows a body-centred arrangement of the small spherical voids (radius 1.26 Å).

Figure 10 PLATON (Spek, 2020) cavity plot of com­pound 3.

There are intra- and inter­molecular C—H⋯O contacts involving both carbonyl O atoms (Fig. 11). By means of these contacts, the individual mol­ecules are connected in all directions (Fig. 12).

Figure 11 The nonclassical C—H⋯O contacts in com­pound 3.

Figure 12 Packing diagram of com­pound 3, viewed along the crystallographic c direction.

3.1.4. [(C₅Ph₅)Fe(CO)₂Bu], 4

Compound 4 also crystallizes in the monoclinic space group P2₁/n, with one mol­ecule in the asymmetric unit (Fig. 13 shows a side view).

Figure 13 Displacement ellipsoid plot (side view) of com­pound 1, with ellipsoids drawn at the 30% probability level.

The iron–butyl bond bis­ects the cyclo­penta­dienyl C4—C5 bond, while both iron–carbonyl bonds, Fe—C6 and Fe—C7, eclipse the exocyclic cyclo­penta­dienyl C1—C101 and C3—C301 bonds, respectively. The C_α—C_β bond of the butyl group only deviates slightly from the plane bis­ecting the Fe(CO)₂ unit. All the phenyl rings adopt a paddle-wheel orientation, with inter­planar angles ranging from 42.85 (8) to 59.68 (7)°. The Cp ring is planar, with a sigpln parameter of 0.017. All phenyl ipso-C atoms are located on the distal side of the Cp ring, with distances from the plane ranging from 0.098 (1) to 0.237 (1) Å. A PLATON analysis (Spek, 2020) of the crystal structure shows essentially no solvent-accessible voids.

The closest structural `relative' of 4 that can be found in the literature is [(C₅Me₅)Fe(CO)₂(n-C₅H₁₁)] (CSD refcode HOZ­WIC; Hill et al., 1999). There, the Fe—C_α(alk­yl) bond has a length of 2.069 (10) Å. Similar to 4, the C_α—C_β bond of the pentyl moiety bis­ects the Fe(CO)₂ moiety, but in contrast to 4, all the C—C bonds of the alkyl group are in a transoid orientation.

As with the other structures reported here, there are also C—H⋯O contacts in com­pound 4, but only atom O2 is involved (see Fig. 14). The individual mol­ecules are connected in the a and b directions via these contacts (Fig. 15).

Figure 14 The nonclassical C—H⋯O contacts in com­pound 4.

Figure 15 Packing diagram of com­pound 4, viewed along the crystallographic a direction.

3.2. Comparison of the structures of 1–4 with each other and with some other [C₅Ph₅] com­plexes

Table 2 collects some important bond parameters of penta­phenyl­cyclo­penta­dienyl com­plexes, including the IR carbonyl stretching frequencies. The Fe—centroid distances (Fe—Ct) fall into three groups. The shortest bond can be found in anionic [(C₅Ph₅)Fe(CO)₂][PPN] (CSD refcode PUY­DES; Carter et al., 2002), with a value of 1.715 Å; a medium bond length of ca 1.74 Å is formed by 1 and the cationoid [(C₅Ph₅)Fe(CO)₂Br] (SIRMIP; Field et al., 1989), [(C₅Ph₅)Fe(CO)₂(FBF₃)] (MARFET; Hemming et al., 2018) and [(C₅Ph₅)Fe(CO)₂(H₂O)]BF₄ (MARFIX; Hemming et al., 2018); and the longest bond of ca 1.76 Å is found for 2–4. The C—O bond lengths of the metal carbonyls can also be divided in three groups. The shortest C—O bonds are found for the bromide com­plex, with a value of 1.07 (3) Å, an inter­mediate bond of 1.14 (1) Å is found for 1–4 and the tetra­fluoro­borate and aqua com­plexes, and the longest bond of 1.185 (3) Å is found for the anionic com­plex. This parallels the information obtained from the IR carbonyl frequencies: the highest ν(CO) value is observed for the bromide com­plex and the lowest frequencies are obtained for the anionic com­plex. Considering bond strengths, apparently the strongest metal–Cp bond and the strongest back donation to the carbonyl ligands is found for the anionic com­plex, which is not unexpected. In addition, the relative order of the C—O bond lengths (shorter/stronger for the cationoid com­plexes in com­parison with the more `neutral' com­plexes) is in agreement with generally accepted bonding concepts. The only deviation from this trend is apparently the rather high ν(CO) frequency observed for phenyl com­pound 2, which is not paralleled in the crystal structure C—O bond length. However, the relative order of the Fe—Ct distances is less dictated by electronic than by steric requirements. This is also reflected in the metal–carbon bond lengths (Fe—C<sub>R</sub>) to the alkyl or aryl residues. While the relatively short Fe—C(phen­yl) bond might indicate some back donation into the aromatic ring system [com­pare the same tendency in the pair Cp*Fe(CO)<sub>2</sub>C<sub>5</sub>H<sub>11</sub>/C<sub>6</sub>H<sub>5</sub>], the other Fe—C<sub>R</sub> bonds are ordered according to the increasing steric demand of the alkyl moiety. The deviation of the phenyl ipso-C atoms from the cyclo­penta­dienyl ring plane is smallest for methyl com­plex 1, largest for phenyl com­plex 2 and inter­mediate for all the other com­pounds of Table 2. The average `canting' angle is smallest for phenyl com­pound 2 and largest for the bromide com­pound. The other com­pounds can be divided into two groups: an angle of 50.4 (2)° is found for 1, 3 and 4, and an angle of 52.4 (10)° is found for the rest. The extrema might be explained by the large size of bromine, forcing the phenyl rings into a more perpendicular orientation with respect to the cyclo­penta­dienyl ring, and on the near perpendicular orientation of the σ-phenyl ring with respect to the plane defined by Ct—Fe—C_α, which forces the other phenyl rings into a `flatter' orientation.

When com­paring the `nonclassical' C—H⋯O inter­actions, it appears that nearly always the para H atom of one phenyl group is involved. The only exception to this `rule' occurs in com­pound 3, where two ortho H atoms are also involved. The observed distances are in the range 2.43–2.70 Å (Table 3). For com­parison, such contacts are also observed in [(C₅Ph₅)Fe(CO)₂Br] (2.69 Å) and in [(C₅Ph₅)Fe(CO)₂(H₂O)]BF₄ (2.534 Å). In the anionic com­plex [PPN][(C₅Ph₅)Fe(CO)₂], only C—H⋯O contacts occur with the phenyl rings of the PPN⁺ cation.

4. Conclusion

Four penta­phenyl­cyclo­penta­dienyl iron alkyl and aryl com­plexes were prepared via a new route and characterized by IR, NMR and UV spectroscopy, and by X-ray crystallography. The mol­ecular structures show the longest distances between the Fe atom and the cyclo­penta­dienyl ring reported so far. The Fe—C(alkyl and ar­yl) bonds and the C—O bonds are in the same ranges as found for other com­pounds of this type. All com­pounds show a pale-blue solid-state fluorescence, which has not been described before for this type of com­pound. The fact that the phenyl com­pound shows a much stronger solid-state fluorescence than the others cannot be derived from the bond parameters. Despite this, all the com­pounds obviously inter­act with light and might be of use for DNA cleavage reactions. This is, however, beyond the scope of this study.

Supporting information

Computing details

For all structures, data collection: APEX2 (Bruker, 2011); cell refinement: APEX2 (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2020) and WinGX (Farrugia, 2012).

Dicarbonylmethyl(η⁵-pentaphenylcyclopentadienyl)iron (compd-1)

Crystal data

[Fe(CH3)(C35H25)(CO)2]	Dx = 1.287 Mg m^−3
Mr = 572.45	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9987 reflections
a = 13.6393 (3) Å	θ = 2.6–27.5°
b = 20.4360 (5) Å	µ = 0.54 mm^−1
c = 21.1978 (5) Å	T = 105 K
V = 5908.5 (2) Å^3	Block, brown
Z = 8	0.06 × 0.05 × 0.04 mm
F(000) = 2384

Data collection

Bruker D8 Venture diffractometer	6765 independent reflections
Radiation source: rotating anode generator, Bruker TXS	5439 reflections with I > 2σ(I)
Detector resolution: 7.391 pixels mm^-1	Rint = 0.053
mix of ω and phi scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −17→17
Tmin = 0.718, Tmax = 0.746	k = −26→26
61228 measured reflections	l = −27→27

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.0342P)^2 + 4.2957P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.002
6765 reflections	Δρmax = 0.35 e Å^−3
371 parameters	Δρmin = −0.49 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.37682 (12)	0.59963 (8)	0.30454 (8)	0.0147 (3)
C2	0.39675 (12)	0.65428 (8)	0.34615 (8)	0.0155 (3)
C3	0.36342 (12)	0.71238 (8)	0.31556 (8)	0.0150 (3)
C4	0.32506 (12)	0.69423 (8)	0.25424 (8)	0.0151 (3)
C5	0.33648 (12)	0.62477 (8)	0.24718 (8)	0.0142 (3)
C6	0.20994 (14)	0.59950 (9)	0.39146 (9)	0.0230 (4)
C7	0.16177 (13)	0.70981 (9)	0.35113 (9)	0.0223 (4)
C10	0.12282 (14)	0.60934 (10)	0.28236 (9)	0.0271 (4)
H10A	0.140202	0.566911	0.263946	0.041*
H10B	0.101259	0.639108	0.248876	0.041*
H10C	0.069641	0.603426	0.312926	0.041*
C101	0.40372 (12)	0.53019 (8)	0.31622 (7)	0.0152 (3)
C102	0.33482 (13)	0.47999 (8)	0.31259 (8)	0.0191 (4)
H102	0.267726	0.490162	0.305614	0.023*
C103	0.36376 (14)	0.41499 (9)	0.31915 (8)	0.0224 (4)
H103	0.316409	0.380977	0.316894	0.027*
C104	0.46177 (15)	0.39992 (9)	0.32897 (8)	0.0229 (4)
H104	0.481612	0.355530	0.332721	0.027*
C105	0.53075 (14)	0.44948 (9)	0.33332 (8)	0.0216 (4)
H105	0.597809	0.439086	0.340131	0.026*
C106	0.50173 (13)	0.51446 (8)	0.32770 (8)	0.0173 (3)
H106	0.548930	0.548388	0.331696	0.021*
C201	0.45262 (12)	0.65138 (8)	0.40618 (8)	0.0162 (3)
C202	0.43646 (13)	0.60253 (9)	0.45131 (8)	0.0195 (4)
H202	0.386610	0.570823	0.444600	0.023*
C203	0.49288 (14)	0.60012 (9)	0.50587 (8)	0.0227 (4)
H203	0.481837	0.566528	0.536023	0.027*
C204	0.56530 (14)	0.64658 (10)	0.51650 (9)	0.0242 (4)
H204	0.603014	0.645203	0.554155	0.029*
C205	0.58241 (13)	0.69495 (9)	0.47204 (9)	0.0233 (4)
H205	0.631990	0.726757	0.479155	0.028*
C206	0.52692 (13)	0.69692 (9)	0.41694 (8)	0.0195 (4)
H206	0.539841	0.729706	0.386281	0.023*
C301	0.36893 (12)	0.77994 (8)	0.34182 (8)	0.0164 (3)
C302	0.34005 (13)	0.79307 (9)	0.40373 (8)	0.0210 (4)
H302	0.314161	0.758830	0.429060	0.025*
C303	0.34877 (14)	0.85577 (9)	0.42876 (9)	0.0258 (4)
H303	0.329104	0.864096	0.470996	0.031*
C304	0.38610 (14)	0.90603 (9)	0.39210 (10)	0.0279 (4)
H304	0.391811	0.948876	0.409092	0.034*
C305	0.41507 (14)	0.89371 (9)	0.33065 (10)	0.0259 (4)
H305	0.440747	0.928148	0.305481	0.031*
C306	0.40665 (13)	0.83090 (9)	0.30562 (9)	0.0208 (4)
H306	0.426855	0.822782	0.263450	0.025*
C401	0.29641 (12)	0.74027 (8)	0.20307 (8)	0.0167 (3)
C402	0.21648 (14)	0.78238 (9)	0.20753 (9)	0.0226 (4)
H402	0.175744	0.781049	0.243862	0.027*
C403	0.19573 (16)	0.82634 (9)	0.15933 (10)	0.0298 (4)
H403	0.141215	0.855020	0.163018	0.036*
C404	0.25409 (16)	0.82852 (10)	0.10599 (9)	0.0302 (4)
H404	0.239837	0.858689	0.073144	0.036*
C405	0.33345 (15)	0.78651 (9)	0.10067 (9)	0.0279 (4)
H405	0.373477	0.787702	0.064005	0.033*
C406	0.35456 (13)	0.74261 (9)	0.14894 (9)	0.0216 (4)
H406	0.409069	0.713954	0.145027	0.026*
C501	0.31740 (12)	0.58676 (8)	0.18883 (8)	0.0150 (3)
C502	0.23958 (13)	0.60131 (8)	0.14830 (8)	0.0180 (3)
H502	0.195688	0.635739	0.158762	0.022*
C503	0.22546 (14)	0.56613 (9)	0.09292 (8)	0.0221 (4)
H503	0.171512	0.576187	0.066277	0.026*
C504	0.28959 (15)	0.51655 (9)	0.07640 (8)	0.0235 (4)
H504	0.279675	0.492483	0.038595	0.028*
C505	0.36850 (14)	0.50215 (9)	0.11537 (8)	0.0216 (4)
H505	0.413369	0.468667	0.103844	0.026*
C506	0.38194 (13)	0.53655 (8)	0.17107 (8)	0.0178 (3)
H506	0.435715	0.525960	0.197659	0.021*
O1	0.18451 (11)	0.56829 (7)	0.43347 (7)	0.0378 (4)
O2	0.10615 (11)	0.74773 (7)	0.36704 (7)	0.0346 (3)
Fe1	0.24425 (2)	0.64866 (2)	0.32754 (2)	0.01420 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0143 (7)	0.0142 (8)	0.0155 (7)	−0.0008 (6)	0.0003 (6)	0.0004 (6)
C2	0.0148 (8)	0.0157 (8)	0.0160 (8)	−0.0024 (6)	0.0015 (6)	0.0005 (6)
C3	0.0141 (8)	0.0141 (8)	0.0168 (8)	−0.0026 (6)	0.0006 (6)	0.0011 (6)
C4	0.0146 (8)	0.0140 (8)	0.0167 (8)	−0.0005 (6)	0.0009 (6)	−0.0002 (6)
C5	0.0131 (7)	0.0143 (7)	0.0153 (8)	−0.0012 (6)	0.0011 (6)	0.0007 (6)
C6	0.0207 (9)	0.0210 (9)	0.0272 (9)	0.0000 (7)	0.0027 (7)	0.0019 (8)
C7	0.0199 (9)	0.0203 (9)	0.0266 (9)	−0.0033 (7)	0.0010 (7)	0.0034 (7)
C10	0.0196 (9)	0.0398 (12)	0.0221 (9)	−0.0078 (8)	0.0002 (7)	−0.0119 (8)
C101	0.0196 (8)	0.0134 (8)	0.0124 (7)	0.0015 (6)	0.0010 (6)	0.0006 (6)
C102	0.0207 (9)	0.0176 (8)	0.0190 (8)	−0.0007 (7)	0.0001 (7)	−0.0008 (7)
C103	0.0310 (10)	0.0140 (8)	0.0221 (9)	−0.0035 (7)	0.0036 (8)	−0.0003 (7)
C104	0.0363 (10)	0.0146 (8)	0.0178 (8)	0.0071 (7)	0.0078 (8)	0.0025 (7)
C105	0.0234 (9)	0.0246 (9)	0.0167 (8)	0.0073 (7)	0.0030 (7)	0.0045 (7)
C106	0.0193 (8)	0.0197 (8)	0.0130 (7)	−0.0006 (7)	0.0010 (7)	0.0019 (7)
C201	0.0160 (8)	0.0160 (8)	0.0165 (8)	0.0027 (7)	−0.0004 (6)	−0.0027 (6)
C202	0.0223 (9)	0.0194 (9)	0.0168 (8)	−0.0010 (7)	0.0014 (7)	−0.0018 (7)
C203	0.0281 (10)	0.0253 (9)	0.0147 (8)	0.0042 (8)	0.0018 (7)	0.0012 (7)
C204	0.0228 (9)	0.0329 (10)	0.0169 (8)	0.0059 (8)	−0.0047 (7)	−0.0050 (8)
C205	0.0205 (9)	0.0243 (9)	0.0250 (9)	0.0008 (7)	−0.0045 (7)	−0.0065 (8)
C206	0.0189 (8)	0.0187 (8)	0.0210 (8)	0.0003 (7)	−0.0022 (7)	−0.0005 (7)
C301	0.0128 (8)	0.0159 (8)	0.0205 (8)	−0.0002 (6)	−0.0034 (6)	−0.0014 (7)
C302	0.0213 (9)	0.0189 (8)	0.0228 (9)	−0.0015 (7)	0.0005 (7)	−0.0022 (7)
C303	0.0249 (9)	0.0241 (9)	0.0284 (10)	0.0016 (8)	−0.0012 (8)	−0.0092 (8)
C304	0.0250 (10)	0.0173 (9)	0.0415 (11)	0.0013 (8)	−0.0071 (9)	−0.0101 (8)
C305	0.0259 (10)	0.0160 (9)	0.0359 (11)	−0.0042 (7)	−0.0044 (8)	0.0016 (8)
C306	0.0199 (9)	0.0182 (8)	0.0243 (9)	−0.0030 (7)	−0.0026 (7)	0.0011 (7)
C401	0.0190 (8)	0.0130 (8)	0.0181 (8)	−0.0031 (7)	−0.0037 (7)	−0.0004 (6)
C402	0.0262 (9)	0.0180 (9)	0.0235 (9)	0.0031 (7)	−0.0006 (7)	0.0005 (7)
C403	0.0343 (11)	0.0197 (9)	0.0355 (11)	0.0068 (8)	−0.0071 (9)	0.0047 (8)
C404	0.0412 (12)	0.0203 (9)	0.0290 (10)	−0.0049 (9)	−0.0111 (9)	0.0113 (8)
C405	0.0335 (11)	0.0267 (10)	0.0234 (9)	−0.0088 (8)	0.0001 (8)	0.0078 (8)
C406	0.0202 (8)	0.0202 (9)	0.0243 (9)	−0.0019 (7)	−0.0005 (7)	0.0026 (7)
C501	0.0163 (8)	0.0138 (7)	0.0149 (8)	−0.0020 (6)	−0.0002 (6)	0.0009 (6)
C502	0.0193 (8)	0.0157 (8)	0.0190 (8)	0.0006 (7)	−0.0013 (7)	0.0004 (6)
C503	0.0238 (9)	0.0241 (9)	0.0183 (8)	−0.0010 (7)	−0.0057 (7)	0.0017 (7)
C504	0.0322 (10)	0.0222 (9)	0.0160 (8)	−0.0011 (8)	−0.0022 (7)	−0.0044 (7)
C505	0.0269 (9)	0.0180 (9)	0.0199 (9)	0.0037 (7)	0.0031 (7)	−0.0032 (7)
C506	0.0189 (8)	0.0173 (8)	0.0172 (8)	0.0007 (7)	−0.0019 (7)	0.0004 (7)
O1	0.0389 (9)	0.0389 (9)	0.0357 (8)	−0.0018 (7)	0.0091 (7)	0.0162 (7)
O2	0.0290 (8)	0.0257 (7)	0.0490 (9)	0.0044 (6)	0.0115 (7)	−0.0048 (7)
Fe1	0.01451 (12)	0.01253 (12)	0.01557 (12)	−0.00121 (9)	0.00088 (9)	−0.00036 (9)

Geometric parameters (Å, º)

C1—C5	1.430 (2)	C203—H203	0.9500
C1—C2	1.449 (2)	C204—C205	1.386 (3)
C1—C101	1.486 (2)	C204—H204	0.9500
C1—Fe1	2.1240 (16)	C205—C206	1.392 (2)
C2—C3	1.427 (2)	C205—H205	0.9500
C2—C201	1.484 (2)	C206—H206	0.9500
C2—Fe1	2.1202 (16)	C301—C306	1.392 (2)
C3—C4	1.450 (2)	C301—C302	1.396 (2)
C3—C301	1.490 (2)	C302—C303	1.392 (2)
C3—Fe1	2.0981 (16)	C302—H302	0.9500
C4—C5	1.436 (2)	C303—C304	1.385 (3)
C4—C401	1.488 (2)	C303—H303	0.9500
C4—Fe1	2.1205 (16)	C304—C305	1.384 (3)
C5—C501	1.484 (2)	C304—H304	0.9500
C5—Fe1	2.1731 (16)	C305—C306	1.394 (2)
C6—O1	1.149 (2)	C305—H305	0.9500
C6—Fe1	1.7506 (19)	C306—H306	0.9500
C7—O2	1.136 (2)	C401—C402	1.392 (2)
C7—Fe1	1.7542 (19)	C401—C406	1.396 (2)
C10—Fe1	2.0751 (18)	C402—C403	1.390 (3)
C10—H10A	0.9800	C402—H402	0.9500
C10—H10B	0.9800	C403—C404	1.384 (3)
C10—H10C	0.9800	C403—H403	0.9500
C101—C102	1.393 (2)	C404—C405	1.386 (3)
C101—C106	1.396 (2)	C404—H404	0.9500
C102—C103	1.393 (2)	C405—C406	1.391 (3)
C102—H102	0.9500	C405—H405	0.9500
C103—C104	1.387 (3)	C406—H406	0.9500
C103—H103	0.9500	C501—C502	1.397 (2)
C104—C105	1.385 (3)	C501—C506	1.403 (2)
C104—H104	0.9500	C502—C503	1.390 (2)
C105—C106	1.391 (2)	C502—H502	0.9500
C105—H105	0.9500	C503—C504	1.384 (3)
C106—H106	0.9500	C503—H503	0.9500
C201—C206	1.395 (2)	C504—C505	1.388 (3)
C201—C202	1.400 (2)	C504—H504	0.9500
C202—C203	1.390 (2)	C505—C506	1.386 (2)
C202—H202	0.9500	C505—H505	0.9500
C203—C204	1.388 (3)	C506—H506	0.9500
C5—C1—C2	108.23 (14)	C303—C302—H302	119.6
C5—C1—C101	125.42 (15)	C301—C302—H302	119.6
C2—C1—C101	126.03 (14)	C304—C303—C302	120.02 (18)
C5—C1—Fe1	72.43 (9)	C304—C303—H303	120.0
C2—C1—Fe1	69.90 (9)	C302—C303—H303	120.0
C101—C1—Fe1	128.48 (12)	C305—C304—C303	119.87 (17)
C3—C2—C1	107.76 (14)	C305—C304—H304	120.1
C3—C2—C201	125.89 (15)	C303—C304—H304	120.1
C1—C2—C201	125.97 (15)	C304—C305—C306	120.14 (18)
C3—C2—Fe1	69.39 (9)	C304—C305—H305	119.9
C1—C2—Fe1	70.18 (9)	C306—C305—H305	119.9
C201—C2—Fe1	131.37 (12)	C301—C306—C305	120.64 (18)
C2—C3—C4	108.03 (14)	C301—C306—H306	119.7
C2—C3—C301	125.80 (15)	C305—C306—H306	119.7
C4—C3—C301	126.16 (14)	C402—C401—C406	118.66 (16)
C2—C3—Fe1	71.06 (9)	C402—C401—C4	123.16 (15)
C4—C3—Fe1	70.74 (9)	C406—C401—C4	118.15 (15)
C301—C3—Fe1	124.67 (12)	C403—C402—C401	120.61 (18)
C5—C4—C3	107.89 (14)	C403—C402—H402	119.7
C5—C4—C401	125.28 (15)	C401—C402—H402	119.7
C3—C4—C401	125.93 (14)	C404—C403—C402	120.30 (19)
C5—C4—Fe1	72.45 (9)	C404—C403—H403	119.8
C3—C4—Fe1	69.07 (9)	C402—C403—H403	119.8
C401—C4—Fe1	132.48 (12)	C403—C404—C405	119.72 (17)
C1—C5—C4	107.96 (14)	C403—C404—H404	120.1
C1—C5—C501	126.04 (14)	C405—C404—H404	120.1
C4—C5—C501	125.83 (15)	C404—C405—C406	120.08 (18)
C1—C5—Fe1	68.72 (9)	C404—C405—H405	120.0
C4—C5—Fe1	68.50 (9)	C406—C405—H405	120.0
C501—C5—Fe1	132.04 (11)	C405—C406—C401	120.62 (17)
O1—C6—Fe1	177.75 (18)	C405—C406—H406	119.7
O2—C7—Fe1	177.60 (17)	C401—C406—H406	119.7
Fe1—C10—H10A	109.5	C502—C501—C506	117.85 (15)
Fe1—C10—H10B	109.5	C502—C501—C5	122.30 (15)
H10A—C10—H10B	109.5	C506—C501—C5	119.76 (15)
Fe1—C10—H10C	109.5	C503—C502—C501	120.96 (16)
H10A—C10—H10C	109.5	C503—C502—H502	119.5
H10B—C10—H10C	109.5	C501—C502—H502	119.5
C102—C101—C106	119.07 (15)	C504—C503—C502	120.32 (16)
C102—C101—C1	121.81 (15)	C504—C503—H503	119.8
C106—C101—C1	119.02 (15)	C502—C503—H503	119.8
C103—C102—C101	120.37 (17)	C503—C504—C505	119.66 (16)
C103—C102—H102	119.8	C503—C504—H504	120.2
C101—C102—H102	119.8	C505—C504—H504	120.2
C104—C103—C102	119.98 (17)	C506—C505—C504	120.12 (16)
C104—C103—H103	120.0	C506—C505—H505	119.9
C102—C103—H103	120.0	C504—C505—H505	119.9
C105—C104—C103	120.13 (16)	C505—C506—C501	121.08 (16)
C105—C104—H104	119.9	C505—C506—H506	119.5
C103—C104—H104	119.9	C501—C506—H506	119.5
C104—C105—C106	119.93 (17)	C6—Fe1—C7	90.96 (9)
C104—C105—H105	120.0	C6—Fe1—C10	85.51 (9)
C106—C105—H105	120.0	C7—Fe1—C10	84.00 (8)
C105—C106—C101	120.48 (16)	C6—Fe1—C3	131.07 (8)
C105—C106—H106	119.8	C7—Fe1—C3	95.11 (7)
C101—C106—H106	119.8	C10—Fe1—C3	143.40 (7)
C206—C201—C202	118.57 (15)	C6—Fe1—C2	98.59 (8)
C206—C201—C2	119.12 (15)	C7—Fe1—C2	122.51 (8)
C202—C201—C2	122.24 (15)	C10—Fe1—C2	152.86 (7)
C203—C202—C201	120.44 (17)	C3—Fe1—C2	39.54 (6)
C203—C202—H202	119.8	C6—Fe1—C4	163.38 (8)
C201—C202—H202	119.8	C7—Fe1—C4	103.26 (7)
C204—C203—C202	120.31 (17)	C10—Fe1—C4	104.29 (7)
C204—C203—H203	119.8	C3—Fe1—C4	40.19 (6)
C202—C203—H203	119.8	C2—Fe1—C4	66.59 (6)
C205—C204—C203	119.82 (17)	C6—Fe1—C1	97.73 (7)
C205—C204—H204	120.1	C7—Fe1—C1	161.34 (7)
C203—C204—H204	120.1	C10—Fe1—C1	113.01 (7)
C204—C205—C206	119.97 (17)	C3—Fe1—C1	66.77 (6)
C204—C205—H205	120.0	C2—Fe1—C1	39.92 (6)
C206—C205—H205	120.0	C4—Fe1—C1	66.20 (6)
C205—C206—C201	120.86 (17)	C6—Fe1—C5	129.24 (7)
C205—C206—H206	119.6	C7—Fe1—C5	139.00 (7)
C201—C206—H206	119.6	C10—Fe1—C5	90.76 (7)
C306—C301—C302	118.59 (16)	C3—Fe1—C5	66.18 (6)
C306—C301—C3	120.39 (15)	C2—Fe1—C5	65.80 (6)
C302—C301—C3	120.98 (15)	C4—Fe1—C5	39.05 (6)
C303—C302—C301	120.73 (17)	C1—Fe1—C5	38.86 (6)
C5—C1—C2—C3	3.22 (18)	C1—C2—C201—C206	131.06 (18)
C101—C1—C2—C3	176.97 (15)	Fe1—C2—C201—C206	−134.30 (15)
Fe1—C1—C2—C3	−59.45 (11)	C3—C2—C201—C202	142.10 (17)
C5—C1—C2—C201	−169.99 (15)	C1—C2—C201—C202	−45.9 (2)
C101—C1—C2—C201	3.8 (3)	Fe1—C2—C201—C202	48.8 (2)
Fe1—C1—C2—C201	127.34 (16)	C206—C201—C202—C203	0.6 (2)
C5—C1—C2—Fe1	62.67 (11)	C2—C201—C202—C203	177.59 (16)
C101—C1—C2—Fe1	−123.58 (17)	C201—C202—C203—C204	0.6 (3)
C1—C2—C3—C4	−1.47 (18)	C202—C203—C204—C205	−1.0 (3)
C201—C2—C3—C4	171.75 (15)	C203—C204—C205—C206	0.1 (3)
Fe1—C2—C3—C4	−61.41 (11)	C204—C205—C206—C201	1.2 (3)
C1—C2—C3—C301	179.55 (15)	C202—C201—C206—C205	−1.5 (3)
C201—C2—C3—C301	−7.2 (3)	C2—C201—C206—C205	−178.60 (16)
Fe1—C2—C3—C301	119.60 (16)	C2—C3—C301—C306	131.01 (18)
C1—C2—C3—Fe1	59.95 (11)	C4—C3—C301—C306	−47.8 (2)
C201—C2—C3—Fe1	−126.83 (16)	Fe1—C3—C301—C306	−138.28 (14)
C2—C3—C4—C5	−0.82 (18)	C2—C3—C301—C302	−46.5 (2)
C301—C3—C4—C5	178.16 (15)	C4—C3—C301—C302	134.67 (18)
Fe1—C3—C4—C5	−62.44 (11)	Fe1—C3—C301—C302	44.2 (2)
C2—C3—C4—C401	−170.37 (15)	C306—C301—C302—C303	0.0 (3)
C301—C3—C4—C401	8.6 (3)	C3—C301—C302—C303	177.59 (16)
Fe1—C3—C4—C401	128.00 (16)	C301—C302—C303—C304	0.2 (3)
C2—C3—C4—Fe1	61.62 (11)	C302—C303—C304—C305	−0.3 (3)
C301—C3—C4—Fe1	−119.40 (17)	C303—C304—C305—C306	0.1 (3)
C2—C1—C5—C4	−3.73 (18)	C302—C301—C306—C305	−0.2 (3)
C101—C1—C5—C4	−177.52 (15)	C3—C301—C306—C305	−177.81 (16)
Fe1—C1—C5—C4	57.33 (11)	C304—C305—C306—C301	0.2 (3)
C2—C1—C5—C501	171.69 (15)	C5—C4—C401—C402	124.51 (19)
C101—C1—C5—C501	−2.1 (3)	C3—C4—C401—C402	−67.7 (2)
Fe1—C1—C5—C501	−127.26 (16)	Fe1—C4—C401—C402	26.1 (2)
C2—C1—C5—Fe1	−61.06 (11)	C5—C4—C401—C406	−57.6 (2)
C101—C1—C5—Fe1	125.15 (17)	C3—C4—C401—C406	110.21 (19)
C3—C4—C5—C1	2.82 (18)	Fe1—C4—C401—C406	−156.05 (13)
C401—C4—C5—C1	172.45 (15)	C406—C401—C402—C403	−0.7 (3)
Fe1—C4—C5—C1	−57.46 (11)	C4—C401—C402—C403	177.19 (17)
C3—C4—C5—C501	−172.61 (15)	C401—C402—C403—C404	0.4 (3)
C401—C4—C5—C501	−3.0 (3)	C402—C403—C404—C405	0.1 (3)
Fe1—C4—C5—C501	127.11 (16)	C403—C404—C405—C406	−0.4 (3)
C3—C4—C5—Fe1	60.28 (11)	C404—C405—C406—C401	0.0 (3)
C401—C4—C5—Fe1	−130.08 (16)	C402—C401—C406—C405	0.5 (3)
C5—C1—C101—C102	−59.9 (2)	C4—C401—C406—C405	−177.50 (16)
C2—C1—C101—C102	127.41 (18)	C1—C5—C501—C502	147.57 (17)
Fe1—C1—C101—C102	35.4 (2)	C4—C5—C501—C502	−37.8 (2)
C5—C1—C101—C106	116.52 (19)	Fe1—C5—C501—C502	54.6 (2)
C2—C1—C101—C106	−56.2 (2)	C1—C5—C501—C506	−36.0 (2)
Fe1—C1—C101—C106	−148.20 (13)	C4—C5—C501—C506	138.64 (17)
C106—C101—C102—C103	−1.2 (2)	Fe1—C5—C501—C506	−128.94 (15)
C1—C101—C102—C103	175.19 (16)	C506—C501—C502—C503	1.4 (2)
C101—C102—C103—C104	−0.4 (3)	C5—C501—C502—C503	177.91 (16)
C102—C103—C104—C105	1.1 (3)	C501—C502—C503—C504	−1.1 (3)
C103—C104—C105—C106	−0.1 (3)	C502—C503—C504—C505	−0.2 (3)
C104—C105—C106—C101	−1.5 (2)	C503—C504—C505—C506	1.1 (3)
C102—C101—C106—C105	2.2 (2)	C504—C505—C506—C501	−0.8 (3)
C1—C101—C106—C105	−174.35 (15)	C502—C501—C506—C505	−0.5 (2)
C3—C2—C201—C206	−40.9 (2)	C5—C501—C506—C505	−177.09 (16)

Dicarbonyl(η⁵-pentaphenylcyclopentadienyl)phenyliron (compd-2)

Crystal data

[Fe(C6H5)(C35H25)(CO)2]	F(000) = 1320
Mr = 634.52	Dx = 1.357 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.1860 (4) Å	Cell parameters from 9920 reflections
b = 16.9411 (6) Å	θ = 2.7–26.4°
c = 15.0691 (6) Å	µ = 0.52 mm^−1
β = 93.320 (1)°	T = 105 K
V = 3105.71 (19) Å^3	Rod, yellow
Z = 4	0.08 × 0.02 × 0.02 mm

Data collection

Bruker D8 Venture diffractometer	6352 independent reflections
Radiation source: rotating anode generator, Bruker TXS	5025 reflections with I > 2σ(I)
Detector resolution: 7.391 pixels mm^-1	Rint = 0.050
mix of ω and phi scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −15→14
Tmin = 0.669, Tmax = 0.745	k = −21→21
31592 measured reflections	l = −18→17

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0255P)^2 + 3.2346P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
6352 reflections	Δρmax = 0.32 e Å^−3
415 parameters	Δρmin = −0.41 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.51430 (17)	0.41526 (12)	0.67825 (14)	0.0151 (4)
C2	0.58867 (16)	0.47964 (12)	0.68908 (14)	0.0146 (4)
C3	0.52471 (17)	0.55089 (12)	0.68962 (14)	0.0141 (4)
C4	0.41025 (16)	0.53041 (12)	0.67969 (13)	0.0136 (4)
C5	0.40380 (16)	0.44551 (12)	0.67353 (14)	0.0137 (4)
C6	0.51341 (19)	0.39573 (14)	0.86803 (16)	0.0219 (5)
C7	0.55900 (19)	0.54035 (13)	0.87419 (15)	0.0217 (5)
C11	0.35145 (18)	0.49501 (13)	0.86829 (15)	0.0198 (5)
C12	0.32867 (19)	0.56776 (14)	0.90712 (16)	0.0234 (5)
H12	0.381951	0.608656	0.906319	0.028*
C13	0.2305 (2)	0.58204 (16)	0.94684 (18)	0.0320 (6)
H13	0.217626	0.632230	0.972376	0.038*
C14	0.1516 (2)	0.52401 (17)	0.94948 (18)	0.0348 (6)
H14	0.083720	0.534105	0.975309	0.042*
C15	0.1732 (2)	0.45034 (15)	0.91363 (17)	0.0294 (6)
H15	0.120005	0.409429	0.915421	0.035*
C16	0.27212 (18)	0.43651 (14)	0.87527 (15)	0.0220 (5)
H16	0.286297	0.385286	0.852966	0.026*
C101	0.54613 (17)	0.33194 (12)	0.65979 (14)	0.0147 (4)
C102	0.50261 (17)	0.29643 (12)	0.58201 (14)	0.0167 (5)
H102	0.449561	0.323825	0.545005	0.020*
C103	0.53606 (18)	0.22142 (13)	0.55815 (15)	0.0200 (5)
H103	0.505680	0.197761	0.505098	0.024*
C104	0.61335 (19)	0.18106 (13)	0.61124 (16)	0.0216 (5)
H104	0.636721	0.129927	0.594607	0.026*
C105	0.6565 (2)	0.21561 (13)	0.68886 (16)	0.0249 (5)
H105	0.708980	0.187730	0.725954	0.030*
C106	0.62367 (18)	0.29089 (13)	0.71289 (15)	0.0206 (5)
H106	0.654432	0.314356	0.765923	0.025*
C201	0.71062 (17)	0.47448 (12)	0.68737 (14)	0.0151 (4)
C202	0.75535 (18)	0.44018 (13)	0.61354 (15)	0.0193 (5)
H202	0.707813	0.418926	0.567380	0.023*
C203	0.86791 (18)	0.43661 (13)	0.60647 (16)	0.0222 (5)
H203	0.897094	0.413373	0.555526	0.027*
C204	0.93826 (18)	0.46697 (13)	0.67376 (16)	0.0228 (5)
H204	1.015591	0.464829	0.668957	0.027*
C205	0.89509 (18)	0.50025 (13)	0.74760 (17)	0.0238 (5)
H205	0.943020	0.520498	0.794103	0.029*
C206	0.78185 (18)	0.50441 (13)	0.75454 (16)	0.0200 (5)
H206	0.753021	0.527848	0.805522	0.024*
C301	0.56873 (17)	0.63255 (12)	0.68749 (14)	0.0146 (4)
C302	0.64470 (17)	0.65157 (13)	0.62483 (14)	0.0165 (5)
H302	0.674713	0.610995	0.590090	0.020*
C303	0.67661 (18)	0.72939 (13)	0.61302 (15)	0.0188 (5)
H303	0.728402	0.741751	0.570357	0.023*
C304	0.63314 (18)	0.78920 (13)	0.66329 (16)	0.0216 (5)
H304	0.653611	0.842563	0.654154	0.026*
C305	0.55957 (18)	0.77044 (13)	0.72698 (16)	0.0222 (5)
H305	0.530776	0.811029	0.762393	0.027*
C306	0.52785 (18)	0.69276 (13)	0.73921 (15)	0.0190 (5)
H306	0.477810	0.680502	0.783259	0.023*
C401	0.31727 (17)	0.58652 (12)	0.66370 (14)	0.0153 (4)
C402	0.32838 (18)	0.64702 (13)	0.60196 (15)	0.0186 (5)
H402	0.396049	0.653287	0.574471	0.022*
C403	0.24202 (19)	0.69811 (13)	0.58019 (16)	0.0231 (5)
H403	0.250745	0.738910	0.537921	0.028*
C404	0.14308 (19)	0.68966 (13)	0.62004 (16)	0.0239 (5)
H404	0.083685	0.724398	0.605023	0.029*
C405	0.13130 (18)	0.63036 (13)	0.68181 (16)	0.0230 (5)
H405	0.063940	0.625152	0.710010	0.028*
C406	0.21712 (17)	0.57817 (13)	0.70314 (15)	0.0185 (5)
H406	0.207461	0.536846	0.744578	0.022*
C501	0.30530 (17)	0.39683 (12)	0.64965 (14)	0.0146 (4)
C502	0.23184 (17)	0.42020 (13)	0.57996 (15)	0.0169 (5)
H502	0.240297	0.470264	0.552794	0.020*
C503	0.14665 (17)	0.37086 (13)	0.55012 (15)	0.0197 (5)
H503	0.097295	0.387236	0.502553	0.024*
C504	0.13320 (18)	0.29777 (14)	0.58938 (16)	0.0230 (5)
H504	0.074776	0.264046	0.568986	0.028*
C505	0.20563 (18)	0.27431 (13)	0.65860 (16)	0.0215 (5)
H505	0.196882	0.224220	0.685638	0.026*
C506	0.29075 (18)	0.32343 (12)	0.68865 (15)	0.0174 (5)
H506	0.339693	0.306823	0.736378	0.021*
O1	0.53289 (15)	0.34343 (10)	0.91514 (12)	0.0311 (4)
O2	0.60742 (14)	0.58192 (10)	0.92221 (11)	0.0295 (4)
Fe1	0.48631 (2)	0.47746 (2)	0.79864 (2)	0.01477 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0144 (10)	0.0148 (10)	0.0161 (11)	0.0000 (9)	0.0009 (9)	0.0003 (8)
C2	0.0136 (10)	0.0135 (10)	0.0165 (11)	−0.0012 (9)	0.0003 (8)	−0.0017 (9)
C3	0.0152 (10)	0.0127 (10)	0.0143 (11)	−0.0010 (8)	0.0013 (8)	0.0003 (8)
C4	0.0147 (10)	0.0124 (10)	0.0139 (10)	−0.0006 (8)	0.0016 (8)	0.0006 (8)
C5	0.0135 (10)	0.0131 (10)	0.0144 (11)	−0.0006 (8)	0.0000 (8)	0.0001 (8)
C6	0.0208 (12)	0.0213 (12)	0.0232 (13)	−0.0036 (10)	−0.0020 (10)	−0.0034 (10)
C7	0.0242 (12)	0.0217 (12)	0.0197 (12)	−0.0001 (10)	0.0047 (10)	0.0023 (10)
C11	0.0205 (11)	0.0217 (12)	0.0171 (11)	−0.0001 (9)	0.0008 (9)	0.0024 (9)
C12	0.0237 (12)	0.0220 (12)	0.0248 (13)	−0.0025 (10)	0.0044 (10)	0.0009 (10)
C13	0.0317 (14)	0.0295 (14)	0.0357 (15)	0.0046 (12)	0.0104 (12)	−0.0049 (12)
C14	0.0288 (13)	0.0394 (15)	0.0379 (15)	0.0009 (12)	0.0169 (12)	0.0025 (13)
C15	0.0246 (13)	0.0322 (14)	0.0318 (14)	−0.0079 (11)	0.0048 (11)	0.0067 (11)
C16	0.0233 (12)	0.0216 (12)	0.0215 (12)	−0.0015 (10)	0.0036 (10)	0.0034 (10)
C101	0.0115 (10)	0.0114 (10)	0.0210 (12)	−0.0015 (8)	0.0007 (9)	0.0005 (9)
C102	0.0155 (10)	0.0158 (11)	0.0187 (11)	0.0004 (9)	−0.0005 (9)	0.0018 (9)
C103	0.0218 (11)	0.0195 (11)	0.0186 (12)	−0.0015 (10)	−0.0004 (9)	−0.0041 (9)
C104	0.0252 (12)	0.0124 (11)	0.0270 (13)	0.0041 (9)	−0.0008 (10)	−0.0014 (9)
C105	0.0269 (13)	0.0164 (11)	0.0301 (14)	0.0063 (10)	−0.0081 (10)	−0.0001 (10)
C106	0.0225 (12)	0.0167 (11)	0.0217 (12)	0.0016 (9)	−0.0054 (10)	−0.0035 (9)
C201	0.0155 (10)	0.0085 (9)	0.0213 (11)	0.0005 (9)	0.0005 (8)	0.0023 (9)
C202	0.0170 (11)	0.0178 (11)	0.0230 (12)	−0.0007 (9)	−0.0006 (9)	−0.0010 (9)
C203	0.0197 (11)	0.0205 (12)	0.0271 (13)	0.0016 (10)	0.0061 (10)	−0.0030 (10)
C204	0.0121 (10)	0.0180 (11)	0.0384 (14)	0.0000 (9)	0.0036 (10)	−0.0012 (10)
C205	0.0152 (11)	0.0219 (12)	0.0339 (14)	−0.0014 (9)	−0.0033 (10)	−0.0052 (10)
C206	0.0177 (11)	0.0172 (11)	0.0250 (12)	−0.0008 (9)	0.0021 (9)	−0.0044 (9)
C301	0.0119 (10)	0.0119 (10)	0.0195 (11)	0.0005 (8)	−0.0028 (8)	0.0001 (8)
C302	0.0143 (10)	0.0167 (11)	0.0182 (11)	0.0013 (9)	−0.0019 (9)	0.0001 (9)
C303	0.0163 (11)	0.0205 (11)	0.0192 (12)	−0.0028 (9)	−0.0022 (9)	0.0047 (9)
C304	0.0216 (12)	0.0117 (11)	0.0304 (13)	−0.0032 (9)	−0.0070 (10)	0.0020 (9)
C305	0.0219 (12)	0.0144 (11)	0.0300 (13)	0.0014 (9)	−0.0002 (10)	−0.0063 (10)
C306	0.0166 (11)	0.0178 (11)	0.0228 (12)	−0.0010 (9)	0.0035 (9)	−0.0017 (9)
C401	0.0147 (10)	0.0104 (10)	0.0205 (11)	−0.0004 (8)	−0.0009 (9)	−0.0039 (9)
C402	0.0153 (11)	0.0166 (11)	0.0240 (12)	−0.0017 (9)	0.0013 (9)	−0.0008 (9)
C403	0.0258 (12)	0.0155 (11)	0.0274 (13)	0.0017 (10)	−0.0035 (10)	0.0031 (10)
C404	0.0188 (11)	0.0173 (11)	0.0345 (14)	0.0062 (9)	−0.0062 (10)	−0.0045 (10)
C405	0.0141 (11)	0.0205 (12)	0.0344 (14)	0.0015 (9)	0.0018 (10)	−0.0063 (10)
C406	0.0164 (11)	0.0162 (11)	0.0231 (12)	−0.0002 (9)	0.0023 (9)	−0.0011 (9)
C501	0.0117 (10)	0.0137 (10)	0.0187 (11)	−0.0006 (8)	0.0044 (8)	−0.0030 (9)
C502	0.0148 (10)	0.0150 (10)	0.0212 (12)	0.0020 (9)	0.0028 (9)	−0.0016 (9)
C503	0.0127 (10)	0.0264 (12)	0.0200 (12)	0.0013 (9)	0.0006 (9)	−0.0055 (10)
C504	0.0157 (11)	0.0238 (12)	0.0295 (13)	−0.0062 (10)	0.0030 (10)	−0.0081 (10)
C505	0.0192 (11)	0.0149 (11)	0.0307 (13)	−0.0037 (9)	0.0052 (10)	−0.0017 (10)
C506	0.0165 (11)	0.0147 (11)	0.0213 (12)	−0.0004 (9)	0.0019 (9)	−0.0001 (9)
O1	0.0411 (11)	0.0209 (9)	0.0303 (10)	0.0000 (8)	−0.0069 (8)	0.0063 (8)
O2	0.0310 (10)	0.0299 (10)	0.0271 (10)	−0.0079 (8)	−0.0020 (8)	−0.0064 (8)
Fe1	0.01461 (15)	0.01271 (15)	0.01687 (16)	−0.00087 (13)	0.00001 (12)	0.00030 (13)

Geometric parameters (Å, º)

C1—C2	1.421 (3)	C201—C202	1.394 (3)
C1—C5	1.439 (3)	C202—C203	1.383 (3)
C1—C101	1.494 (3)	C202—H202	0.9500
C1—Fe1	2.142 (2)	C203—C204	1.388 (3)
C2—C3	1.437 (3)	C203—H203	0.9500
C2—C201	1.490 (3)	C204—C205	1.379 (3)
C2—Fe1	2.126 (2)	C204—H204	0.9500
C3—C4	1.437 (3)	C205—C206	1.392 (3)
C3—C301	1.485 (3)	C205—H205	0.9500
C3—Fe1	2.134 (2)	C206—H206	0.9500
C4—C5	1.443 (3)	C301—C306	1.393 (3)
C4—C401	1.488 (3)	C301—C302	1.398 (3)
C4—Fe1	2.164 (2)	C302—C303	1.389 (3)
C5—C501	1.483 (3)	C302—H302	0.9500
C5—Fe1	2.154 (2)	C303—C304	1.388 (3)
C6—O1	1.151 (3)	C303—H303	0.9500
C6—Fe1	1.755 (2)	C304—C305	1.388 (3)
C7—O2	1.148 (3)	C304—H304	0.9500
C7—Fe1	1.761 (2)	C305—C306	1.387 (3)
C11—C16	1.393 (3)	C305—H305	0.9500
C11—C12	1.399 (3)	C306—H306	0.9500
C11—Fe1	2.023 (2)	C401—C406	1.395 (3)
C12—C13	1.390 (3)	C401—C402	1.396 (3)
C12—H12	0.9500	C402—C403	1.387 (3)
C13—C14	1.377 (4)	C402—H402	0.9500
C13—H13	0.9500	C403—C404	1.385 (3)
C14—C15	1.391 (4)	C403—H403	0.9500
C14—H14	0.9500	C404—C405	1.383 (3)
C15—C16	1.387 (3)	C404—H404	0.9500
C15—H15	0.9500	C405—C406	1.393 (3)
C16—H16	0.9500	C405—H405	0.9500
C101—C106	1.389 (3)	C406—H406	0.9500
C101—C102	1.395 (3)	C501—C506	1.391 (3)
C102—C103	1.388 (3)	C501—C502	1.397 (3)
C102—H102	0.9500	C502—C503	1.387 (3)
C103—C104	1.381 (3)	C502—H502	0.9500
C103—H103	0.9500	C503—C504	1.386 (3)
C104—C105	1.384 (3)	C503—H503	0.9500
C104—H104	0.9500	C504—C505	1.385 (3)
C105—C106	1.391 (3)	C504—H504	0.9500
C105—H105	0.9500	C505—C506	1.385 (3)
C106—H106	0.9500	C505—H505	0.9500
C201—C206	1.390 (3)	C506—H506	0.9500
C2—C1—C5	108.73 (18)	C201—C206—H206	119.8
C2—C1—C101	125.15 (18)	C205—C206—H206	119.8
C5—C1—C101	125.42 (19)	C306—C301—C302	118.78 (19)
C2—C1—Fe1	69.94 (12)	C306—C301—C3	121.92 (19)
C5—C1—Fe1	70.86 (12)	C302—C301—C3	118.92 (19)
C101—C1—Fe1	132.69 (15)	C303—C302—C301	120.4 (2)
C1—C2—C3	107.62 (17)	C303—C302—H302	119.8
C1—C2—C201	125.64 (19)	C301—C302—H302	119.8
C3—C2—C201	126.23 (19)	C304—C303—C302	120.3 (2)
C1—C2—Fe1	71.16 (12)	C304—C303—H303	119.9
C3—C2—Fe1	70.58 (12)	C302—C303—H303	119.9
C201—C2—Fe1	130.00 (15)	C305—C304—C303	119.5 (2)
C4—C3—C2	108.68 (18)	C305—C304—H304	120.2
C4—C3—C301	124.93 (18)	C303—C304—H304	120.2
C2—C3—C301	125.85 (18)	C306—C305—C304	120.4 (2)
C4—C3—Fe1	71.61 (12)	C306—C305—H305	119.8
C2—C3—Fe1	70.00 (12)	C304—C305—H305	119.8
C301—C3—Fe1	130.95 (15)	C305—C306—C301	120.6 (2)
C3—C4—C5	107.23 (17)	C305—C306—H306	119.7
C3—C4—C401	126.03 (18)	C301—C306—H306	119.7
C5—C4—C401	126.03 (18)	C406—C401—C402	118.64 (19)
C3—C4—Fe1	69.34 (12)	C406—C401—C4	122.89 (19)
C5—C4—Fe1	70.08 (12)	C402—C401—C4	118.33 (19)
C401—C4—Fe1	133.19 (15)	C403—C402—C401	120.9 (2)
C1—C5—C4	107.73 (18)	C403—C402—H402	119.5
C1—C5—C501	123.77 (18)	C401—C402—H402	119.5
C4—C5—C501	127.59 (18)	C404—C403—C402	120.0 (2)
C1—C5—Fe1	70.01 (12)	C404—C403—H403	120.0
C4—C5—Fe1	70.87 (12)	C402—C403—H403	120.0
C501—C5—Fe1	133.02 (15)	C405—C404—C403	119.6 (2)
O1—C6—Fe1	178.1 (2)	C405—C404—H404	120.2
O2—C7—Fe1	178.7 (2)	C403—C404—H404	120.2
C16—C11—C12	116.1 (2)	C404—C405—C406	120.7 (2)
C16—C11—Fe1	121.54 (17)	C404—C405—H405	119.6
C12—C11—Fe1	122.23 (17)	C406—C405—H405	119.6
C13—C12—C11	122.0 (2)	C405—C406—C401	120.1 (2)
C13—C12—H12	119.0	C405—C406—H406	120.0
C11—C12—H12	119.0	C401—C406—H406	120.0
C14—C13—C12	120.5 (2)	C506—C501—C502	118.62 (19)
C14—C13—H13	119.7	C506—C501—C5	121.04 (19)
C12—C13—H13	119.7	C502—C501—C5	119.93 (19)
C13—C14—C15	118.8 (2)	C503—C502—C501	120.5 (2)
C13—C14—H14	120.6	C503—C502—H502	119.7
C15—C14—H14	120.6	C501—C502—H502	119.7
C16—C15—C14	120.1 (2)	C504—C503—C502	120.3 (2)
C16—C15—H15	119.9	C504—C503—H503	119.8
C14—C15—H15	119.9	C502—C503—H503	119.8
C15—C16—C11	122.4 (2)	C505—C504—C503	119.5 (2)
C15—C16—H16	118.8	C505—C504—H504	120.3
C11—C16—H16	118.8	C503—C504—H504	120.3
C106—C101—C102	118.76 (19)	C504—C505—C506	120.4 (2)
C106—C101—C1	122.75 (19)	C504—C505—H505	119.8
C102—C101—C1	118.28 (19)	C506—C505—H505	119.8
C103—C102—C101	120.6 (2)	C505—C506—C501	120.7 (2)
C103—C102—H102	119.7	C505—C506—H506	119.7
C101—C102—H102	119.7	C501—C506—H506	119.7
C104—C103—C102	120.3 (2)	C6—Fe1—C7	91.25 (10)
C104—C103—H103	119.9	C6—Fe1—C11	86.40 (10)
C102—C103—H103	119.9	C7—Fe1—C11	88.22 (10)
C103—C104—C105	119.6 (2)	C6—Fe1—C2	112.19 (10)
C103—C104—H104	120.2	C7—Fe1—C2	101.29 (9)
C105—C104—H104	120.2	C11—Fe1—C2	158.62 (8)
C104—C105—C106	120.4 (2)	C6—Fe1—C3	151.22 (10)
C104—C105—H105	119.8	C7—Fe1—C3	91.18 (9)
C106—C105—H105	119.8	C11—Fe1—C3	122.33 (8)
C101—C106—C105	120.4 (2)	C2—Fe1—C3	39.42 (8)
C101—C106—H106	119.8	C6—Fe1—C1	94.75 (9)
C105—C106—H106	119.8	C7—Fe1—C1	138.28 (9)
C206—C201—C202	118.5 (2)	C11—Fe1—C1	133.30 (9)
C206—C201—C2	123.17 (19)	C2—Fe1—C1	38.90 (8)
C202—C201—C2	118.34 (19)	C3—Fe1—C1	65.29 (8)
C203—C202—C201	121.0 (2)	C6—Fe1—C5	112.68 (9)
C203—C202—H202	119.5	C7—Fe1—C5	155.52 (9)
C201—C202—H202	119.5	C11—Fe1—C5	97.99 (8)
C202—C203—C204	120.1 (2)	C2—Fe1—C5	65.78 (8)
C202—C203—H203	120.0	C3—Fe1—C5	65.46 (8)
C204—C203—H203	120.0	C1—Fe1—C5	39.13 (8)
C205—C204—C203	119.5 (2)	C6—Fe1—C4	151.32 (9)
C205—C204—H204	120.2	C7—Fe1—C4	117.39 (9)
C203—C204—H204	120.2	C11—Fe1—C4	92.70 (8)
C204—C205—C206	120.5 (2)	C2—Fe1—C4	65.93 (8)
C204—C205—H205	119.7	C3—Fe1—C4	39.04 (8)
C206—C205—H205	119.7	C1—Fe1—C4	65.42 (8)
C201—C206—C205	120.4 (2)	C5—Fe1—C4	39.05 (8)
C5—C1—C2—C3	−1.0 (2)	C102—C101—C106—C105	−0.3 (3)
C101—C1—C2—C3	169.8 (2)	C1—C101—C106—C105	−175.0 (2)
Fe1—C1—C2—C3	−61.51 (14)	C104—C105—C106—C101	0.7 (4)
C5—C1—C2—C201	−173.3 (2)	C1—C2—C201—C206	−127.2 (2)
C101—C1—C2—C201	−2.5 (3)	C3—C2—C201—C206	61.9 (3)
Fe1—C1—C2—C201	126.2 (2)	Fe1—C2—C201—C206	−32.5 (3)
C5—C1—C2—Fe1	60.51 (15)	C1—C2—C201—C202	54.8 (3)
C101—C1—C2—Fe1	−128.7 (2)	C3—C2—C201—C202	−116.0 (2)
C1—C2—C3—C4	0.4 (2)	Fe1—C2—C201—C202	149.59 (17)
C201—C2—C3—C4	172.6 (2)	C206—C201—C202—C203	−0.7 (3)
Fe1—C2—C3—C4	−61.49 (14)	C2—C201—C202—C203	177.3 (2)
C1—C2—C3—C301	−171.4 (2)	C201—C202—C203—C204	0.4 (3)
C201—C2—C3—C301	0.8 (3)	C202—C203—C204—C205	0.3 (3)
Fe1—C2—C3—C301	126.7 (2)	C203—C204—C205—C206	−0.8 (4)
C1—C2—C3—Fe1	61.88 (14)	C202—C201—C206—C205	0.2 (3)
C201—C2—C3—Fe1	−125.9 (2)	C2—C201—C206—C205	−177.7 (2)
C2—C3—C4—C5	0.4 (2)	C204—C205—C206—C201	0.5 (3)
C301—C3—C4—C5	172.3 (2)	C4—C3—C301—C306	50.4 (3)
Fe1—C3—C4—C5	−60.12 (14)	C2—C3—C301—C306	−139.1 (2)
C2—C3—C4—C401	−170.5 (2)	Fe1—C3—C301—C306	−45.2 (3)
C301—C3—C4—C401	1.5 (3)	C4—C3—C301—C302	−122.5 (2)
Fe1—C3—C4—C401	129.1 (2)	C2—C3—C301—C302	48.1 (3)
C2—C3—C4—Fe1	60.47 (14)	Fe1—C3—C301—C302	141.97 (18)
C301—C3—C4—Fe1	−127.6 (2)	C306—C301—C302—C303	−1.6 (3)
C2—C1—C5—C4	1.2 (2)	C3—C301—C302—C303	171.51 (19)
C101—C1—C5—C4	−169.5 (2)	C301—C302—C303—C304	−0.1 (3)
Fe1—C1—C5—C4	61.16 (14)	C302—C303—C304—C305	1.6 (3)
C2—C1—C5—C501	171.01 (19)	C303—C304—C305—C306	−1.3 (3)
C101—C1—C5—C501	0.3 (3)	C304—C305—C306—C301	−0.4 (3)
Fe1—C1—C5—C501	−129.1 (2)	C302—C301—C306—C305	1.8 (3)
C2—C1—C5—Fe1	−59.94 (15)	C3—C301—C306—C305	−171.0 (2)
C101—C1—C5—Fe1	129.3 (2)	C3—C4—C401—C406	−141.1 (2)
C3—C4—C5—C1	−1.0 (2)	C5—C4—C401—C406	49.8 (3)
C401—C4—C5—C1	169.8 (2)	Fe1—C4—C401—C406	−46.3 (3)
Fe1—C4—C5—C1	−60.61 (14)	C3—C4—C401—C402	43.3 (3)
C3—C4—C5—C501	−170.2 (2)	C5—C4—C401—C402	−125.8 (2)
C401—C4—C5—C501	0.6 (4)	Fe1—C4—C401—C402	138.14 (19)
Fe1—C4—C5—C501	130.1 (2)	C406—C401—C402—C403	0.2 (3)
C3—C4—C5—Fe1	59.65 (14)	C4—C401—C402—C403	176.0 (2)
C401—C4—C5—Fe1	−129.5 (2)	C401—C402—C403—C404	0.2 (3)
C16—C11—C12—C13	−2.8 (3)	C402—C403—C404—C405	0.3 (3)
Fe1—C11—C12—C13	173.10 (19)	C403—C404—C405—C406	−1.2 (3)
C11—C12—C13—C14	0.2 (4)	C404—C405—C406—C401	1.6 (3)
C12—C13—C14—C15	1.5 (4)	C402—C401—C406—C405	−1.0 (3)
C13—C14—C15—C16	−0.7 (4)	C4—C401—C406—C405	−176.6 (2)
C14—C15—C16—C11	−2.1 (4)	C1—C5—C501—C506	47.2 (3)
C12—C11—C16—C15	3.7 (3)	C4—C5—C501—C506	−145.1 (2)
Fe1—C11—C16—C15	−172.21 (18)	Fe1—C5—C501—C506	−46.3 (3)
C2—C1—C101—C106	54.3 (3)	C1—C5—C501—C502	−125.4 (2)
C5—C1—C101—C106	−136.5 (2)	C4—C5—C501—C502	42.2 (3)
Fe1—C1—C101—C106	−40.2 (3)	Fe1—C5—C501—C502	141.03 (18)
C2—C1—C101—C102	−120.3 (2)	C506—C501—C502—C503	−0.4 (3)
C5—C1—C101—C102	48.9 (3)	C5—C501—C502—C503	172.4 (2)
Fe1—C1—C101—C102	145.14 (18)	C501—C502—C503—C504	0.2 (3)
C106—C101—C102—C103	0.1 (3)	C502—C503—C504—C505	−0.1 (3)
C1—C101—C102—C103	174.9 (2)	C503—C504—C505—C506	0.2 (3)
C101—C102—C103—C104	−0.2 (3)	C504—C505—C506—C501	−0.3 (3)
C102—C103—C104—C105	0.6 (3)	C502—C501—C506—C505	0.4 (3)
C103—C104—C105—C106	−0.9 (4)	C5—C501—C506—C505	−172.3 (2)

Dicarbonyl(isopropyl)(η⁵-pentaphenylcyclopentadienyl)iron (compd-3)

Crystal data

[Fe(C3H7)(C35H25)(CO)2]	F(000) = 1256
Mr = 600.50	Dx = 1.309 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.5488 (7) Å	Cell parameters from 9881 reflections
b = 13.5046 (7) Å	θ = 2.7–27.1°
c = 18.0119 (11) Å	µ = 0.53 mm^−1
β = 93.208 (2)°	T = 110 K
V = 3047.6 (3) Å^3	Block, brown
Z = 4	0.06 × 0.04 × 0.03 mm

Data collection

Bruker D8 Venture diffractometer	6732 independent reflections
Radiation source: rotating anode generator, Bruker TXS	5995 reflections with I > 2σ(I)
Detector resolution: 7.391 pixels mm^-1	Rint = 0.031
mix of ω and phi scans	θmax = 27.1°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −15→16
Tmin = 0.719, Tmax = 0.746	k = −17→17
52953 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0377P)^2 + 2.212P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.002
6732 reflections	Δρmax = 0.36 e Å^−3
390 parameters	Δρmin = −0.36 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.34805 (12)	0.66256 (11)	0.45764 (8)	0.0172 (3)
C2	0.34016 (12)	0.65122 (11)	0.53606 (8)	0.0168 (3)
C3	0.43556 (11)	0.69012 (10)	0.57258 (8)	0.0164 (3)
C4	0.50756 (12)	0.71857 (11)	0.51583 (8)	0.0177 (3)
C5	0.45259 (12)	0.70276 (11)	0.44536 (8)	0.0175 (3)
C6	0.41931 (15)	0.90205 (14)	0.56241 (12)	0.0371 (4)
C7	0.33642 (13)	0.88526 (12)	0.43146 (10)	0.0264 (3)
C8	0.21376 (13)	0.84627 (13)	0.54392 (9)	0.0271 (3)
H8	0.193058	0.792073	0.578096	0.032*
C9	0.20660 (18)	0.94269 (16)	0.58861 (13)	0.0450 (5)
H9A	0.226676	0.998732	0.557772	0.067*
H9B	0.255237	0.939047	0.633026	0.067*
H9C	0.133334	0.951793	0.603527	0.067*
C10	0.12829 (15)	0.84813 (17)	0.48138 (11)	0.0395 (5)
H10A	0.057777	0.847803	0.502168	0.059*
H10B	0.135574	0.789650	0.449843	0.059*
H10C	0.136121	0.908130	0.451571	0.059*
C11	0.27332 (11)	0.62098 (11)	0.39884 (8)	0.0177 (3)
C12	0.22872 (13)	0.67774 (13)	0.34035 (8)	0.0240 (3)
H12	0.242070	0.746944	0.338923	0.029*
C13	0.16478 (14)	0.63360 (14)	0.28406 (9)	0.0292 (4)
H13	0.133882	0.673149	0.244902	0.035*
C14	0.14581 (13)	0.53313 (14)	0.28453 (9)	0.0286 (4)
H14	0.103324	0.503327	0.245339	0.034*
C15	0.18898 (13)	0.47583 (13)	0.34239 (9)	0.0259 (3)
H15	0.175767	0.406582	0.343127	0.031*
C16	0.25169 (12)	0.51956 (12)	0.39949 (8)	0.0213 (3)
H16	0.280166	0.479930	0.439413	0.026*
C21	0.25569 (12)	0.59558 (11)	0.57294 (8)	0.0176 (3)
C22	0.14750 (12)	0.60281 (12)	0.55034 (9)	0.0220 (3)
H22	0.125195	0.647807	0.512013	0.026*
C23	0.07219 (13)	0.54420 (13)	0.58384 (9)	0.0265 (3)
H23	−0.001265	0.550464	0.568781	0.032*
C24	0.10369 (14)	0.47687 (13)	0.63893 (9)	0.0278 (4)
H24	0.052165	0.436772	0.661279	0.033*
C25	0.21085 (14)	0.46850 (12)	0.66117 (9)	0.0254 (3)
H25	0.232871	0.422406	0.698804	0.030*
C26	0.28625 (12)	0.52736 (11)	0.62856 (8)	0.0205 (3)
H26	0.359477	0.521144	0.644268	0.025*
C31	0.45797 (12)	0.68718 (11)	0.65463 (8)	0.0178 (3)
C32	0.38537 (13)	0.72724 (12)	0.70234 (9)	0.0229 (3)
H32	0.327198	0.765913	0.682656	0.028*
C33	0.39780 (14)	0.71079 (13)	0.77856 (9)	0.0281 (4)
H33	0.347589	0.737510	0.810663	0.034*
C34	0.48309 (15)	0.65562 (14)	0.80774 (9)	0.0309 (4)
H34	0.490388	0.643078	0.859670	0.037*
C35	0.55793 (14)	0.61865 (13)	0.76118 (9)	0.0277 (4)
H35	0.617740	0.582616	0.781438	0.033*
C36	0.54550 (12)	0.63428 (12)	0.68473 (9)	0.0214 (3)
H36	0.596882	0.608801	0.652977	0.026*
C41	0.62197 (12)	0.74559 (11)	0.52894 (8)	0.0188 (3)
C42	0.69780 (13)	0.69979 (12)	0.48608 (9)	0.0229 (3)
H42	0.674755	0.656376	0.446901	0.027*
C43	0.80646 (14)	0.71711 (14)	0.50019 (10)	0.0306 (4)
H43	0.856918	0.685881	0.470501	0.037*
C44	0.84104 (14)	0.77976 (15)	0.55740 (11)	0.0330 (4)
H44	0.915201	0.790803	0.567513	0.040*
C45	0.76703 (14)	0.82637 (14)	0.59993 (10)	0.0304 (4)
H45	0.790518	0.869962	0.638878	0.036*
C46	0.65853 (13)	0.80939 (12)	0.58562 (9)	0.0242 (3)
H46	0.608495	0.841806	0.614963	0.029*
C51	0.49636 (12)	0.71843 (11)	0.37098 (8)	0.0195 (3)
C52	0.48776 (13)	0.64331 (13)	0.31800 (9)	0.0235 (3)
H52	0.453240	0.582965	0.329230	0.028*
C53	0.52961 (14)	0.65629 (15)	0.24850 (9)	0.0327 (4)
H53	0.524011	0.604592	0.212725	0.039*
C54	0.57922 (15)	0.74423 (16)	0.23160 (10)	0.0373 (4)
H54	0.606519	0.753514	0.183951	0.045*
C55	0.58896 (15)	0.81866 (14)	0.28434 (11)	0.0355 (4)
H55	0.623971	0.878727	0.273037	0.043*
C56	0.54789 (14)	0.80606 (12)	0.35364 (10)	0.0263 (3)
H56	0.554969	0.857566	0.389496	0.032*
O1	0.45705 (14)	0.96355 (12)	0.59890 (13)	0.0716 (6)
O2	0.31839 (11)	0.93700 (10)	0.38174 (8)	0.0387 (3)
Fe1	0.36538 (2)	0.80613 (2)	0.50730 (2)	0.01815 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0199 (7)	0.0161 (7)	0.0159 (7)	−0.0005 (5)	0.0035 (5)	0.0007 (5)
C2	0.0188 (7)	0.0159 (7)	0.0160 (7)	0.0000 (5)	0.0027 (5)	0.0005 (5)
C3	0.0175 (7)	0.0147 (6)	0.0173 (7)	−0.0003 (5)	0.0029 (5)	−0.0011 (5)
C4	0.0196 (7)	0.0156 (7)	0.0181 (7)	−0.0013 (5)	0.0034 (5)	−0.0007 (5)
C5	0.0211 (7)	0.0146 (6)	0.0170 (7)	−0.0010 (5)	0.0037 (5)	−0.0002 (5)
C6	0.0310 (9)	0.0236 (9)	0.0554 (12)	0.0072 (7)	−0.0081 (8)	−0.0090 (8)
C7	0.0264 (8)	0.0225 (8)	0.0314 (9)	0.0008 (6)	0.0095 (7)	0.0025 (7)
C8	0.0271 (8)	0.0293 (8)	0.0258 (8)	0.0048 (7)	0.0096 (6)	0.0038 (7)
C9	0.0496 (12)	0.0383 (11)	0.0489 (12)	0.0103 (9)	0.0192 (10)	−0.0055 (9)
C10	0.0269 (9)	0.0538 (12)	0.0383 (10)	0.0042 (8)	0.0068 (8)	0.0116 (9)
C11	0.0166 (7)	0.0232 (7)	0.0138 (6)	−0.0008 (6)	0.0043 (5)	−0.0010 (6)
C12	0.0285 (8)	0.0266 (8)	0.0170 (7)	0.0010 (6)	0.0017 (6)	0.0008 (6)
C13	0.0301 (9)	0.0409 (10)	0.0162 (7)	0.0057 (7)	−0.0014 (6)	−0.0011 (7)
C14	0.0210 (8)	0.0444 (10)	0.0204 (8)	−0.0014 (7)	0.0017 (6)	−0.0124 (7)
C15	0.0228 (8)	0.0289 (8)	0.0264 (8)	−0.0054 (6)	0.0060 (6)	−0.0094 (7)
C16	0.0205 (7)	0.0241 (8)	0.0195 (7)	−0.0016 (6)	0.0042 (6)	−0.0012 (6)
C21	0.0192 (7)	0.0199 (7)	0.0141 (6)	−0.0040 (6)	0.0050 (5)	−0.0039 (5)
C22	0.0211 (7)	0.0253 (8)	0.0198 (7)	−0.0005 (6)	0.0029 (6)	−0.0028 (6)
C23	0.0186 (7)	0.0323 (9)	0.0293 (8)	−0.0050 (6)	0.0068 (6)	−0.0082 (7)
C24	0.0287 (8)	0.0271 (8)	0.0291 (8)	−0.0095 (7)	0.0145 (7)	−0.0046 (7)
C25	0.0326 (9)	0.0230 (8)	0.0212 (7)	−0.0050 (7)	0.0082 (6)	0.0002 (6)
C26	0.0226 (7)	0.0206 (7)	0.0186 (7)	−0.0034 (6)	0.0037 (6)	−0.0017 (6)
C31	0.0189 (7)	0.0176 (7)	0.0169 (7)	−0.0049 (5)	0.0009 (5)	−0.0018 (5)
C32	0.0243 (8)	0.0247 (8)	0.0199 (7)	0.0007 (6)	0.0016 (6)	−0.0039 (6)
C33	0.0335 (9)	0.0328 (9)	0.0185 (8)	−0.0022 (7)	0.0057 (6)	−0.0059 (7)
C34	0.0400 (10)	0.0355 (9)	0.0165 (7)	−0.0071 (8)	−0.0038 (7)	0.0001 (7)
C35	0.0278 (8)	0.0279 (8)	0.0266 (8)	−0.0024 (7)	−0.0070 (6)	0.0033 (7)
C36	0.0204 (7)	0.0207 (7)	0.0232 (7)	−0.0030 (6)	0.0011 (6)	−0.0020 (6)
C41	0.0197 (7)	0.0179 (7)	0.0189 (7)	−0.0029 (5)	0.0032 (5)	0.0025 (6)
C42	0.0232 (8)	0.0226 (8)	0.0232 (8)	−0.0002 (6)	0.0044 (6)	−0.0010 (6)
C43	0.0221 (8)	0.0376 (10)	0.0328 (9)	0.0006 (7)	0.0089 (7)	−0.0017 (8)
C44	0.0188 (8)	0.0408 (10)	0.0397 (10)	−0.0071 (7)	0.0032 (7)	0.0003 (8)
C45	0.0263 (8)	0.0325 (9)	0.0322 (9)	−0.0092 (7)	0.0003 (7)	−0.0064 (7)
C46	0.0220 (8)	0.0255 (8)	0.0253 (8)	−0.0037 (6)	0.0049 (6)	−0.0032 (6)
C51	0.0190 (7)	0.0221 (7)	0.0178 (7)	0.0014 (6)	0.0046 (5)	0.0032 (6)
C52	0.0245 (8)	0.0269 (8)	0.0194 (7)	0.0003 (6)	0.0049 (6)	−0.0008 (6)
C53	0.0314 (9)	0.0472 (11)	0.0204 (8)	0.0035 (8)	0.0081 (7)	−0.0047 (8)
C54	0.0354 (10)	0.0545 (12)	0.0233 (8)	0.0060 (9)	0.0147 (7)	0.0106 (8)
C55	0.0354 (10)	0.0346 (10)	0.0380 (10)	0.0002 (8)	0.0151 (8)	0.0161 (8)
C56	0.0292 (8)	0.0221 (8)	0.0286 (8)	0.0004 (6)	0.0090 (7)	0.0040 (6)
O1	0.0538 (10)	0.0353 (8)	0.1213 (16)	0.0098 (7)	−0.0354 (10)	−0.0420 (10)
O2	0.0446 (8)	0.0339 (7)	0.0383 (7)	0.0068 (6)	0.0100 (6)	0.0182 (6)
Fe1	0.01987 (12)	0.01597 (11)	0.01882 (12)	−0.00017 (8)	0.00301 (8)	0.00005 (8)

Geometric parameters (Å, º)

C1—C2	1.430 (2)	C22—C23	1.396 (2)
C1—C5	1.448 (2)	C22—H22	0.9500
C1—C11	1.485 (2)	C23—C24	1.387 (3)
C1—Fe1	2.1411 (15)	C23—H23	0.9500
C2—C3	1.433 (2)	C24—C25	1.386 (2)
C2—C21	1.486 (2)	C24—H24	0.9500
C2—Fe1	2.1824 (14)	C25—C26	1.391 (2)
C3—C4	1.453 (2)	C25—H25	0.9500
C3—C31	1.489 (2)	C26—H26	0.9500
C3—Fe1	2.1205 (15)	C31—C36	1.394 (2)
C4—C5	1.426 (2)	C31—C32	1.396 (2)
C4—C41	1.487 (2)	C32—C33	1.391 (2)
C4—Fe1	2.1387 (15)	C32—H32	0.9500
C5—C51	1.491 (2)	C33—C34	1.383 (3)
C5—Fe1	2.1278 (15)	C33—H33	0.9500
C6—O1	1.145 (2)	C34—C35	1.387 (3)
C6—Fe1	1.7453 (19)	C34—H34	0.9500
C7—O2	1.148 (2)	C35—C36	1.393 (2)
C7—Fe1	1.7564 (17)	C35—H35	0.9500
C8—C10	1.511 (3)	C36—H36	0.9500
C8—C9	1.536 (3)	C41—C46	1.394 (2)
C8—Fe1	2.1189 (16)	C41—C42	1.402 (2)
C8—H8	1.0000	C42—C43	1.393 (2)
C9—H9A	0.9800	C42—H42	0.9500
C9—H9B	0.9800	C43—C44	1.384 (3)
C9—H9C	0.9800	C43—H43	0.9500
C10—H10A	0.9800	C44—C45	1.388 (3)
C10—H10B	0.9800	C44—H44	0.9500
C10—H10C	0.9800	C45—C46	1.390 (2)
C11—C12	1.395 (2)	C45—H45	0.9500
C11—C16	1.397 (2)	C46—H46	0.9500
C12—C13	1.391 (2)	C51—C56	1.392 (2)
C12—H12	0.9500	C51—C52	1.393 (2)
C13—C14	1.378 (3)	C52—C53	1.395 (2)
C13—H13	0.9500	C52—H52	0.9500
C14—C15	1.384 (3)	C53—C54	1.383 (3)
C14—H14	0.9500	C53—H53	0.9500
C15—C16	1.391 (2)	C54—C55	1.384 (3)
C15—H15	0.9500	C54—H54	0.9500
C16—H16	0.9500	C55—C56	1.387 (2)
C21—C26	1.399 (2)	C55—H55	0.9500
C21—C22	1.399 (2)	C56—H56	0.9500
C2—C1—C5	107.73 (12)	C25—C26—H26	119.6
C2—C1—C11	126.03 (13)	C21—C26—H26	119.6
C5—C1—C11	125.04 (13)	C36—C31—C32	119.09 (14)
C2—C1—Fe1	72.26 (8)	C36—C31—C3	120.02 (13)
C5—C1—Fe1	69.68 (8)	C32—C31—C3	120.47 (14)
C11—C1—Fe1	133.29 (11)	C33—C32—C31	120.32 (15)
C1—C2—C3	108.18 (12)	C33—C32—H32	119.8
C1—C2—C21	125.90 (13)	C31—C32—H32	119.8
C3—C2—C21	125.36 (13)	C34—C33—C32	120.18 (16)
C1—C2—Fe1	69.13 (8)	C34—C33—H33	119.9
C3—C2—Fe1	68.23 (8)	C32—C33—H33	119.9
C21—C2—Fe1	135.02 (10)	C33—C34—C35	120.00 (15)
C2—C3—C4	108.08 (12)	C33—C34—H34	120.0
C2—C3—C31	123.52 (13)	C35—C34—H34	120.0
C4—C3—C31	127.93 (13)	C34—C35—C36	120.07 (16)
C2—C3—Fe1	72.90 (8)	C34—C35—H35	120.0
C4—C3—Fe1	70.72 (8)	C36—C35—H35	120.0
C31—C3—Fe1	128.27 (10)	C35—C36—C31	120.27 (15)
C5—C4—C3	107.31 (12)	C35—C36—H36	119.9
C5—C4—C41	126.33 (13)	C31—C36—H36	119.9
C3—C4—C41	125.86 (13)	C46—C41—C42	118.05 (14)
C5—C4—Fe1	70.06 (8)	C46—C41—C4	122.90 (14)
C3—C4—Fe1	69.38 (8)	C42—C41—C4	118.90 (13)
C41—C4—Fe1	132.05 (10)	C43—C42—C41	120.87 (15)
C4—C5—C1	108.50 (12)	C43—C42—H42	119.6
C4—C5—C51	126.45 (13)	C41—C42—H42	119.6
C1—C5—C51	124.95 (13)	C44—C43—C42	120.09 (16)
C4—C5—Fe1	70.88 (8)	C44—C43—H43	120.0
C1—C5—Fe1	70.67 (8)	C42—C43—H43	120.0
C51—C5—Fe1	127.17 (10)	C43—C44—C45	119.78 (16)
O1—C6—Fe1	178.22 (17)	C43—C44—H44	120.1
O2—C7—Fe1	179.42 (15)	C45—C44—H44	120.1
C10—C8—C9	108.46 (16)	C44—C45—C46	120.10 (16)
C10—C8—Fe1	112.60 (12)	C44—C45—H45	119.9
C9—C8—Fe1	117.38 (13)	C46—C45—H45	119.9
C10—C8—H8	105.8	C45—C46—C41	121.10 (15)
C9—C8—H8	105.8	C45—C46—H46	119.5
Fe1—C8—H8	105.8	C41—C46—H46	119.5
C8—C9—H9A	109.5	C56—C51—C52	118.97 (14)
C8—C9—H9B	109.5	C56—C51—C5	121.41 (14)
H9A—C9—H9B	109.5	C52—C51—C5	119.60 (14)
C8—C9—H9C	109.5	C51—C52—C53	120.30 (16)
H9A—C9—H9C	109.5	C51—C52—H52	119.8
H9B—C9—H9C	109.5	C53—C52—H52	119.8
C8—C10—H10A	109.5	C54—C53—C52	120.14 (17)
C8—C10—H10B	109.5	C54—C53—H53	119.9
H10A—C10—H10B	109.5	C52—C53—H53	119.9
C8—C10—H10C	109.5	C53—C54—C55	119.75 (16)
H10A—C10—H10C	109.5	C53—C54—H54	120.1
H10B—C10—H10C	109.5	C55—C54—H54	120.1
C12—C11—C16	118.38 (14)	C54—C55—C56	120.37 (17)
C12—C11—C1	122.80 (14)	C54—C55—H55	119.8
C16—C11—C1	118.70 (13)	C56—C55—H55	119.8
C13—C12—C11	120.38 (16)	C55—C56—C51	120.45 (16)
C13—C12—H12	119.8	C55—C56—H56	119.8
C11—C12—H12	119.8	C51—C56—H56	119.8
C14—C13—C12	120.68 (16)	C6—Fe1—C7	92.72 (9)
C14—C13—H13	119.7	C6—Fe1—C8	87.68 (8)
C12—C13—H13	119.7	C7—Fe1—C8	86.34 (7)
C13—C14—C15	119.66 (15)	C6—Fe1—C3	95.58 (8)
C13—C14—H14	120.2	C7—Fe1—C3	160.43 (7)
C15—C14—H14	120.2	C8—Fe1—C3	111.64 (6)
C14—C15—C16	120.05 (16)	C6—Fe1—C5	126.20 (8)
C14—C15—H15	120.0	C7—Fe1—C5	94.67 (7)
C16—C15—H15	120.0	C8—Fe1—C5	145.91 (6)
C15—C16—C11	120.83 (15)	C3—Fe1—C5	66.19 (5)
C15—C16—H16	119.6	C6—Fe1—C4	94.25 (7)
C11—C16—H16	119.6	C7—Fe1—C4	121.85 (7)
C26—C21—C22	118.49 (14)	C8—Fe1—C4	151.54 (6)
C26—C21—C2	118.65 (13)	C3—Fe1—C4	39.90 (5)
C22—C21—C2	122.66 (14)	C5—Fe1—C4	39.06 (5)
C23—C22—C21	120.29 (15)	C6—Fe1—C1	159.51 (7)
C23—C22—H22	119.9	C7—Fe1—C1	102.37 (7)
C21—C22—H22	119.9	C8—Fe1—C1	106.84 (6)
C24—C23—C22	120.56 (15)	C3—Fe1—C1	65.92 (5)
C24—C23—H23	119.7	C5—Fe1—C1	39.65 (5)
C22—C23—H23	119.7	C4—Fe1—C1	66.06 (6)
C25—C24—C23	119.55 (15)	C6—Fe1—C2	129.29 (8)
C25—C24—H24	120.2	C7—Fe1—C2	137.85 (7)
C23—C24—H24	120.2	C8—Fe1—C2	91.53 (6)
C24—C25—C26	120.22 (16)	C3—Fe1—C2	38.87 (5)
C24—C25—H25	119.9	C5—Fe1—C2	65.25 (5)
C26—C25—H25	119.9	C4—Fe1—C2	65.45 (5)
C25—C26—C21	120.88 (15)	C1—Fe1—C2	38.61 (5)
C5—C1—C2—C3	3.86 (16)	C3—C2—C21—C26	−39.4 (2)
C11—C1—C2—C3	171.77 (14)	Fe1—C2—C21—C26	−133.21 (14)
Fe1—C1—C2—C3	−57.12 (10)	C1—C2—C21—C22	−43.9 (2)
C5—C1—C2—C21	−167.83 (14)	C3—C2—C21—C22	145.82 (15)
C11—C1—C2—C21	0.1 (2)	Fe1—C2—C21—C22	52.0 (2)
Fe1—C1—C2—C21	131.19 (15)	C26—C21—C22—C23	1.1 (2)
C5—C1—C2—Fe1	60.98 (10)	C2—C21—C22—C23	175.94 (14)
C11—C1—C2—Fe1	−131.11 (15)	C21—C22—C23—C24	−1.2 (2)
C1—C2—C3—C4	−4.70 (16)	C22—C23—C24—C25	0.5 (2)
C21—C2—C3—C4	167.05 (14)	C23—C24—C25—C26	0.1 (2)
Fe1—C2—C3—C4	−62.37 (10)	C24—C25—C26—C21	−0.1 (2)
C1—C2—C3—C31	−177.34 (13)	C22—C21—C26—C25	−0.5 (2)
C21—C2—C3—C31	−5.6 (2)	C2—C21—C26—C25	−175.52 (14)
Fe1—C2—C3—C31	124.99 (14)	C2—C3—C31—C36	117.57 (16)
C1—C2—C3—Fe1	57.67 (10)	C4—C3—C31—C36	−53.5 (2)
C21—C2—C3—Fe1	−130.58 (14)	Fe1—C3—C31—C36	−148.23 (12)
C2—C3—C4—C5	3.71 (16)	C2—C3—C31—C32	−55.0 (2)
C31—C3—C4—C5	175.93 (14)	C4—C3—C31—C32	133.93 (16)
Fe1—C3—C4—C5	−60.06 (10)	Fe1—C3—C31—C32	39.2 (2)
C2—C3—C4—C41	−168.56 (14)	C36—C31—C32—C33	−2.8 (2)
C31—C3—C4—C41	3.7 (2)	C3—C31—C32—C33	169.79 (14)
Fe1—C3—C4—C41	127.66 (15)	C31—C32—C33—C34	0.8 (3)
C2—C3—C4—Fe1	63.77 (10)	C32—C33—C34—C35	1.6 (3)
C31—C3—C4—Fe1	−124.01 (15)	C33—C34—C35—C36	−2.1 (3)
C3—C4—C5—C1	−1.33 (16)	C34—C35—C36—C31	0.1 (2)
C41—C4—C5—C1	170.90 (14)	C32—C31—C36—C35	2.4 (2)
Fe1—C4—C5—C1	−60.96 (10)	C3—C31—C36—C35	−170.28 (14)
C3—C4—C5—C51	−177.76 (14)	C5—C4—C41—C46	143.76 (16)
C41—C4—C5—C51	−5.5 (2)	C3—C4—C41—C46	−45.4 (2)
Fe1—C4—C5—C51	122.61 (15)	Fe1—C4—C41—C46	48.4 (2)
C3—C4—C5—Fe1	59.63 (10)	C5—C4—C41—C42	−40.9 (2)
C41—C4—C5—Fe1	−128.14 (15)	C3—C4—C41—C42	129.91 (16)
C2—C1—C5—C4	−1.55 (16)	Fe1—C4—C41—C42	−136.26 (13)
C11—C1—C5—C4	−169.61 (14)	C46—C41—C42—C43	0.5 (2)
Fe1—C1—C5—C4	61.09 (10)	C4—C41—C42—C43	−175.09 (15)
C2—C1—C5—C51	174.95 (13)	C41—C42—C43—C44	0.4 (3)
C11—C1—C5—C51	6.9 (2)	C42—C43—C44—C45	−1.0 (3)
Fe1—C1—C5—C51	−122.40 (14)	C43—C44—C45—C46	0.7 (3)
C2—C1—C5—Fe1	−62.64 (10)	C44—C45—C46—C41	0.2 (3)
C11—C1—C5—Fe1	129.30 (15)	C42—C41—C46—C45	−0.7 (2)
C2—C1—C11—C12	130.29 (16)	C4—C41—C46—C45	174.62 (15)
C5—C1—C11—C12	−63.8 (2)	C4—C5—C51—C56	−49.6 (2)
Fe1—C1—C11—C12	30.7 (2)	C1—C5—C51—C56	134.50 (16)
C2—C1—C11—C16	−53.7 (2)	Fe1—C5—C51—C56	43.2 (2)
C5—C1—C11—C16	112.20 (17)	C4—C5—C51—C52	129.03 (17)
Fe1—C1—C11—C16	−153.34 (12)	C1—C5—C51—C52	−46.8 (2)
C16—C11—C12—C13	−0.3 (2)	Fe1—C5—C51—C52	−138.17 (13)
C1—C11—C12—C13	175.70 (14)	C56—C51—C52—C53	−0.4 (2)
C11—C12—C13—C14	−1.0 (3)	C5—C51—C52—C53	−179.12 (15)
C12—C13—C14—C15	1.4 (3)	C51—C52—C53—C54	−0.5 (3)
C13—C14—C15—C16	−0.4 (2)	C52—C53—C54—C55	1.2 (3)
C14—C15—C16—C11	−1.0 (2)	C53—C54—C55—C56	−0.9 (3)
C12—C11—C16—C15	1.3 (2)	C54—C55—C56—C51	0.0 (3)
C1—C11—C16—C15	−174.90 (14)	C52—C51—C56—C55	0.7 (2)
C1—C2—C21—C26	130.93 (16)	C5—C51—C56—C55	179.35 (16)

Butyldicarbonyl(η⁵-pentaphenylcyclopentadienyl)iron (compd-4)

Crystal data

[Fe(C4H9)(C35H25)(CO)2]	F(000) = 1288
Mr = 614.53	Dx = 1.302 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.1141 (4) Å	Cell parameters from 9964 reflections
b = 16.0945 (5) Å	θ = 2.5–27.5°
c = 16.1650 (5) Å	µ = 0.52 mm^−1
β = 95.706 (1)°	T = 108 K
V = 3136.08 (17) Å^3	Block, yellow
Z = 4	0.08 × 0.05 × 0.04 mm

Data collection

Bruker D8 Venture diffractometer	7202 independent reflections
Radiation source: rotating anode generator, Bruker TXS	6246 reflections with I > 2σ(I)
Detector resolution: 7.391 pixels mm^-1	Rint = 0.041
mix of ω and phi scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −15→15
Tmin = 0.832, Tmax = 0.862	k = −20→20
55494 measured reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.0416P)^2 + 1.832P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
7202 reflections	Δρmax = 0.37 e Å^−3
398 parameters	Δρmin = −0.47 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.47579 (11)	0.57025 (8)	0.83402 (8)	0.0131 (3)
C2	0.41324 (11)	0.49455 (8)	0.82891 (8)	0.0131 (3)
C3	0.49011 (11)	0.42693 (8)	0.83398 (8)	0.0131 (3)
C4	0.60059 (11)	0.46044 (8)	0.83961 (8)	0.0133 (3)
C5	0.59232 (11)	0.54974 (8)	0.84196 (8)	0.0136 (3)
C6	0.44862 (13)	0.57507 (10)	0.65645 (9)	0.0213 (3)
C7	0.47165 (12)	0.41992 (9)	0.65795 (9)	0.0188 (3)
C11	0.65229 (12)	0.51767 (10)	0.66507 (9)	0.0205 (3)
H11A	0.676910	0.575884	0.674250	0.025*
H11B	0.710971	0.481877	0.693225	0.025*
C12	0.64900 (15)	0.50065 (12)	0.57212 (10)	0.0308 (4)
H12A	0.586520	0.531874	0.542698	0.037*
H12B	0.635147	0.440720	0.561952	0.037*
C13	0.75680 (16)	0.52532 (15)	0.53626 (12)	0.0402 (5)
H13A	0.747528	0.516468	0.475359	0.048*
H13B	0.770138	0.585331	0.546278	0.048*
C14	0.85757 (17)	0.47728 (17)	0.57283 (14)	0.0495 (6)
H14A	0.872427	0.490479	0.632076	0.074*
H14B	0.921949	0.492711	0.543938	0.074*
H14C	0.843551	0.417572	0.566143	0.074*
C101	0.42810 (11)	0.65501 (8)	0.83848 (8)	0.0140 (3)
C102	0.46705 (12)	0.72134 (9)	0.79390 (9)	0.0188 (3)
H102	0.520362	0.711426	0.755731	0.023*
C103	0.42899 (13)	0.80141 (9)	0.80458 (10)	0.0229 (3)
H103	0.457138	0.846062	0.774470	0.028*
C104	0.34974 (13)	0.81655 (9)	0.85922 (10)	0.0225 (3)
H104	0.324338	0.871556	0.867102	0.027*
C105	0.30788 (12)	0.75098 (9)	0.90220 (9)	0.0202 (3)
H105	0.252455	0.760918	0.938669	0.024*
C106	0.34690 (11)	0.67068 (9)	0.89203 (8)	0.0156 (3)
H106	0.318025	0.626088	0.921799	0.019*
C201	0.29087 (11)	0.48686 (8)	0.82957 (9)	0.0137 (3)
C202	0.24907 (12)	0.44568 (9)	0.89560 (9)	0.0177 (3)
H202	0.298868	0.420759	0.937519	0.021*
C203	0.13555 (12)	0.44061 (9)	0.90089 (10)	0.0211 (3)
H203	0.108167	0.412026	0.946042	0.025*
C204	0.06197 (12)	0.47728 (10)	0.84024 (10)	0.0216 (3)
H204	−0.015679	0.474690	0.844189	0.026*
C205	0.10277 (13)	0.51768 (9)	0.77390 (10)	0.0212 (3)
H205	0.052807	0.542609	0.732101	0.025*
C206	0.21648 (12)	0.52190 (9)	0.76820 (9)	0.0174 (3)
H206	0.243564	0.548932	0.722038	0.021*
C301	0.45953 (11)	0.33829 (8)	0.84401 (8)	0.0140 (3)
C302	0.36941 (12)	0.30272 (9)	0.79632 (9)	0.0180 (3)
H302	0.331793	0.333313	0.751808	0.022*
C303	0.33424 (13)	0.22299 (9)	0.81338 (10)	0.0221 (3)
H303	0.272590	0.199448	0.780661	0.027*
C304	0.38875 (13)	0.17752 (9)	0.87802 (10)	0.0219 (3)
H304	0.364249	0.123118	0.889850	0.026*
C305	0.47916 (13)	0.21192 (9)	0.92524 (9)	0.0202 (3)
H305	0.517052	0.180811	0.969250	0.024*
C306	0.51457 (12)	0.29177 (9)	0.90842 (9)	0.0165 (3)
H306	0.576673	0.314872	0.940976	0.020*
C401	0.70126 (11)	0.40786 (9)	0.85278 (9)	0.0149 (3)
C402	0.71651 (12)	0.34096 (9)	0.80006 (10)	0.0206 (3)
H402	0.668327	0.334006	0.750481	0.025*
C403	0.80175 (13)	0.28462 (10)	0.81983 (11)	0.0270 (4)
H403	0.810627	0.238641	0.784232	0.032*
C404	0.87416 (13)	0.29490 (10)	0.89119 (11)	0.0279 (4)
H404	0.932333	0.256099	0.904443	0.034*
C405	0.86122 (12)	0.36198 (10)	0.94299 (10)	0.0224 (3)
H405	0.911031	0.369512	0.991622	0.027*
C406	0.77527 (11)	0.41846 (9)	0.92390 (9)	0.0165 (3)
H406	0.766971	0.464510	0.959530	0.020*
C501	0.68523 (11)	0.60888 (8)	0.86256 (8)	0.0144 (3)
C502	0.78843 (12)	0.60097 (9)	0.83100 (9)	0.0183 (3)
H502	0.799867	0.557541	0.792982	0.022*
C503	0.87442 (12)	0.65617 (10)	0.85483 (10)	0.0229 (3)
H503	0.943372	0.650880	0.831988	0.027*
C504	0.85986 (13)	0.71883 (10)	0.91175 (10)	0.0241 (3)
H504	0.918531	0.756447	0.927828	0.029*
C505	0.75916 (13)	0.72612 (10)	0.94494 (10)	0.0229 (3)
H505	0.749171	0.768297	0.984633	0.028*
C506	0.67288 (12)	0.67205 (9)	0.92041 (9)	0.0177 (3)
H506	0.604078	0.678017	0.943325	0.021*
O1	0.40743 (11)	0.62256 (8)	0.60997 (7)	0.0335 (3)
O2	0.44211 (10)	0.36770 (7)	0.61268 (7)	0.0286 (3)
Fe1	0.51082 (2)	0.50163 (2)	0.72658 (2)	0.01342 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0131 (6)	0.0145 (6)	0.0120 (6)	0.0004 (5)	0.0021 (5)	0.0011 (5)
C2	0.0133 (6)	0.0136 (6)	0.0124 (6)	0.0002 (5)	0.0008 (5)	0.0013 (5)
C3	0.0129 (6)	0.0141 (6)	0.0121 (6)	0.0000 (5)	−0.0004 (5)	0.0000 (5)
C4	0.0133 (6)	0.0144 (6)	0.0120 (6)	0.0006 (5)	0.0003 (5)	−0.0008 (5)
C5	0.0131 (6)	0.0147 (6)	0.0132 (6)	0.0004 (5)	0.0025 (5)	−0.0005 (5)
C6	0.0244 (8)	0.0227 (7)	0.0170 (7)	0.0030 (6)	0.0028 (6)	−0.0020 (6)
C7	0.0170 (7)	0.0221 (7)	0.0178 (7)	0.0006 (6)	0.0036 (5)	0.0002 (6)
C11	0.0166 (7)	0.0277 (8)	0.0175 (7)	−0.0031 (6)	0.0035 (6)	0.0000 (6)
C12	0.0232 (8)	0.0527 (12)	0.0172 (8)	−0.0049 (7)	0.0055 (6)	0.0000 (7)
C13	0.0342 (10)	0.0622 (13)	0.0266 (9)	−0.0120 (9)	0.0151 (8)	0.0001 (9)
C14	0.0269 (10)	0.0788 (16)	0.0453 (12)	−0.0054 (10)	0.0153 (9)	−0.0118 (11)
C101	0.0122 (6)	0.0137 (6)	0.0153 (6)	0.0007 (5)	−0.0024 (5)	−0.0004 (5)
C102	0.0176 (7)	0.0180 (7)	0.0207 (7)	−0.0002 (6)	0.0020 (6)	0.0030 (6)
C103	0.0265 (8)	0.0146 (7)	0.0268 (8)	−0.0013 (6)	−0.0021 (6)	0.0060 (6)
C104	0.0253 (8)	0.0156 (7)	0.0250 (8)	0.0054 (6)	−0.0063 (6)	−0.0034 (6)
C105	0.0188 (7)	0.0215 (7)	0.0197 (7)	0.0046 (6)	−0.0015 (6)	−0.0048 (6)
C106	0.0146 (6)	0.0166 (7)	0.0151 (6)	0.0007 (5)	−0.0004 (5)	−0.0001 (5)
C201	0.0126 (6)	0.0110 (6)	0.0177 (7)	−0.0001 (5)	0.0017 (5)	−0.0025 (5)
C202	0.0163 (7)	0.0177 (7)	0.0191 (7)	0.0008 (5)	0.0009 (5)	0.0020 (5)
C203	0.0189 (7)	0.0214 (7)	0.0241 (8)	−0.0029 (6)	0.0077 (6)	0.0017 (6)
C204	0.0127 (7)	0.0201 (7)	0.0326 (8)	−0.0004 (6)	0.0050 (6)	−0.0015 (6)
C205	0.0143 (7)	0.0204 (7)	0.0279 (8)	0.0018 (6)	−0.0026 (6)	0.0028 (6)
C206	0.0165 (7)	0.0141 (6)	0.0214 (7)	−0.0002 (5)	0.0014 (6)	0.0020 (5)
C301	0.0130 (6)	0.0136 (6)	0.0155 (6)	0.0004 (5)	0.0022 (5)	−0.0015 (5)
C302	0.0182 (7)	0.0157 (7)	0.0190 (7)	−0.0004 (5)	−0.0032 (5)	0.0002 (5)
C303	0.0221 (8)	0.0184 (7)	0.0244 (8)	−0.0056 (6)	−0.0051 (6)	−0.0018 (6)
C304	0.0273 (8)	0.0132 (7)	0.0247 (8)	−0.0041 (6)	0.0009 (6)	0.0007 (6)
C305	0.0244 (8)	0.0170 (7)	0.0184 (7)	0.0019 (6)	−0.0017 (6)	0.0021 (5)
C306	0.0158 (7)	0.0163 (7)	0.0168 (7)	−0.0005 (5)	−0.0012 (5)	−0.0015 (5)
C401	0.0119 (6)	0.0153 (6)	0.0178 (7)	0.0003 (5)	0.0032 (5)	0.0011 (5)
C402	0.0168 (7)	0.0214 (7)	0.0238 (7)	0.0010 (6)	0.0026 (6)	−0.0050 (6)
C403	0.0203 (8)	0.0216 (8)	0.0402 (10)	0.0056 (6)	0.0084 (7)	−0.0066 (7)
C404	0.0164 (7)	0.0247 (8)	0.0431 (10)	0.0085 (6)	0.0053 (7)	0.0054 (7)
C405	0.0129 (7)	0.0286 (8)	0.0254 (8)	0.0000 (6)	0.0008 (6)	0.0080 (6)
C406	0.0134 (6)	0.0180 (7)	0.0184 (7)	−0.0009 (5)	0.0024 (5)	0.0019 (5)
C501	0.0133 (6)	0.0139 (6)	0.0158 (6)	−0.0007 (5)	−0.0002 (5)	0.0036 (5)
C502	0.0152 (7)	0.0195 (7)	0.0203 (7)	0.0005 (5)	0.0019 (5)	0.0015 (6)
C503	0.0146 (7)	0.0253 (8)	0.0287 (8)	−0.0030 (6)	0.0020 (6)	0.0050 (6)
C504	0.0200 (7)	0.0187 (7)	0.0324 (9)	−0.0067 (6)	−0.0037 (6)	0.0033 (6)
C505	0.0259 (8)	0.0169 (7)	0.0252 (8)	−0.0015 (6)	−0.0013 (6)	−0.0024 (6)
C506	0.0165 (7)	0.0170 (7)	0.0194 (7)	0.0003 (5)	0.0009 (5)	0.0007 (5)
O1	0.0447 (8)	0.0305 (6)	0.0238 (6)	0.0133 (6)	−0.0043 (5)	0.0050 (5)
O2	0.0319 (6)	0.0287 (6)	0.0254 (6)	−0.0058 (5)	0.0033 (5)	−0.0098 (5)
Fe1	0.01263 (11)	0.01467 (11)	0.01291 (11)	0.00076 (7)	0.00095 (7)	−0.00002 (7)

Geometric parameters (Å, º)

C1—C2	1.4328 (19)	C201—C202	1.394 (2)
C1—C5	1.4430 (19)	C202—C203	1.389 (2)
C1—C101	1.4859 (18)	C202—H202	0.9500
C1—Fe1	2.1360 (13)	C203—C204	1.389 (2)
C2—C3	1.4294 (18)	C203—H203	0.9500
C2—C201	1.4887 (19)	C204—C205	1.387 (2)
C2—Fe1	2.1295 (14)	C204—H204	0.9500
C3—C4	1.4373 (18)	C205—C206	1.391 (2)
C3—C301	1.4868 (19)	C205—H205	0.9500
C3—Fe1	2.1467 (13)	C206—H206	0.9500
C4—C5	1.4415 (19)	C301—C302	1.3952 (19)
C4—C401	1.4822 (19)	C301—C306	1.3968 (19)
C4—Fe1	2.1366 (13)	C302—C303	1.388 (2)
C5—C501	1.4863 (19)	C302—H302	0.9500
C5—Fe1	2.1649 (14)	C303—C304	1.388 (2)
C6—O1	1.1502 (19)	C303—H303	0.9500
C6—Fe1	1.7552 (16)	C304—C305	1.387 (2)
C7—O2	1.1480 (19)	C304—H304	0.9500
C7—Fe1	1.7552 (15)	C305—C306	1.390 (2)
C11—C12	1.524 (2)	C305—H305	0.9500
C11—Fe1	2.0812 (15)	C306—H306	0.9500
C11—H11A	0.9900	C401—C406	1.396 (2)
C11—H11B	0.9900	C401—C402	1.397 (2)
C12—C13	1.533 (2)	C402—C403	1.387 (2)
C12—H12A	0.9900	C402—H402	0.9500
C12—H12B	0.9900	C403—C404	1.388 (2)
C13—C14	1.515 (3)	C403—H403	0.9500
C13—H13A	0.9900	C404—C405	1.385 (2)
C13—H13B	0.9900	C404—H404	0.9500
C14—H14A	0.9800	C405—C406	1.394 (2)
C14—H14B	0.9800	C405—H405	0.9500
C14—H14C	0.9800	C406—H406	0.9500
C101—C102	1.396 (2)	C501—C506	1.399 (2)
C101—C106	1.3963 (19)	C501—C502	1.4022 (19)
C102—C103	1.385 (2)	C502—C503	1.394 (2)
C102—H102	0.9500	C502—H502	0.9500
C103—C104	1.389 (2)	C503—C504	1.388 (2)
C103—H103	0.9500	C503—H503	0.9500
C104—C105	1.387 (2)	C504—C505	1.386 (2)
C104—H104	0.9500	C504—H504	0.9500
C105—C106	1.392 (2)	C505—C506	1.387 (2)
C105—H105	0.9500	C505—H505	0.9500
C106—H106	0.9500	C506—H506	0.9500
C201—C206	1.392 (2)
C2—C1—C5	108.52 (12)	C204—C205—H205	119.8
C2—C1—C101	125.27 (12)	C206—C205—H205	119.8
C5—C1—C101	125.97 (12)	C205—C206—C201	120.55 (14)
C2—C1—Fe1	70.13 (8)	C205—C206—H206	119.7
C5—C1—Fe1	71.48 (8)	C201—C206—H206	119.7
C101—C1—Fe1	128.59 (9)	C302—C301—C306	118.76 (13)
C3—C2—C1	107.84 (12)	C302—C301—C3	121.54 (12)
C3—C2—C201	125.44 (12)	C306—C301—C3	119.34 (12)
C1—C2—C201	126.27 (12)	C303—C302—C301	120.54 (13)
C3—C2—Fe1	71.12 (8)	C303—C302—H302	119.7
C1—C2—Fe1	70.62 (8)	C301—C302—H302	119.7
C201—C2—Fe1	129.80 (10)	C304—C303—C302	120.30 (14)
C2—C3—C4	108.37 (12)	C304—C303—H303	119.9
C2—C3—C301	124.66 (12)	C302—C303—H303	119.9
C4—C3—C301	126.42 (12)	C305—C304—C303	119.64 (14)
C2—C3—Fe1	69.82 (8)	C305—C304—H304	120.2
C4—C3—Fe1	70.01 (8)	C303—C304—H304	120.2
C301—C3—Fe1	132.53 (9)	C304—C305—C306	120.24 (14)
C3—C4—C5	108.00 (11)	C304—C305—H305	119.9
C3—C4—C401	122.86 (12)	C306—C305—H305	119.9
C5—C4—C401	128.59 (12)	C305—C306—C301	120.51 (13)
C3—C4—Fe1	70.78 (8)	C305—C306—H306	119.7
C5—C4—Fe1	71.49 (7)	C301—C306—H306	119.7
C401—C4—Fe1	129.91 (10)	C406—C401—C402	118.91 (13)
C4—C5—C1	107.20 (11)	C406—C401—C4	120.03 (12)
C4—C5—C501	126.25 (12)	C402—C401—C4	120.61 (13)
C1—C5—C501	125.86 (12)	C403—C402—C401	120.25 (14)
C4—C5—Fe1	69.36 (7)	C403—C402—H402	119.9
C1—C5—Fe1	69.32 (8)	C401—C402—H402	119.9
C501—C5—Fe1	133.81 (10)	C402—C403—C404	120.52 (15)
O1—C6—Fe1	179.31 (15)	C402—C403—H403	119.7
O2—C7—Fe1	177.45 (14)	C404—C403—H403	119.7
C12—C11—Fe1	120.45 (11)	C405—C404—C403	119.70 (14)
C12—C11—H11A	107.2	C405—C404—H404	120.2
Fe1—C11—H11A	107.2	C403—C404—H404	120.2
C12—C11—H11B	107.2	C404—C405—C406	120.12 (15)
Fe1—C11—H11B	107.2	C404—C405—H405	119.9
H11A—C11—H11B	106.8	C406—C405—H405	119.9
C11—C12—C13	112.75 (15)	C405—C406—C401	120.47 (14)
C11—C12—H12A	109.0	C405—C406—H406	119.8
C13—C12—H12A	109.0	C401—C406—H406	119.8
C11—C12—H12B	109.0	C506—C501—C502	117.87 (13)
C13—C12—H12B	109.0	C506—C501—C5	119.08 (12)
H12A—C12—H12B	107.8	C502—C501—C5	122.90 (13)
C14—C13—C12	113.84 (17)	C503—C502—C501	120.70 (14)
C14—C13—H13A	108.8	C503—C502—H502	119.6
C12—C13—H13A	108.8	C501—C502—H502	119.6
C14—C13—H13B	108.8	C504—C503—C502	120.36 (14)
C12—C13—H13B	108.8	C504—C503—H503	119.8
H13A—C13—H13B	107.7	C502—C503—H503	119.8
C13—C14—H14A	109.5	C505—C504—C503	119.54 (14)
C13—C14—H14B	109.5	C505—C504—H504	120.2
H14A—C14—H14B	109.5	C503—C504—H504	120.2
C13—C14—H14C	109.5	C504—C505—C506	120.23 (14)
H14A—C14—H14C	109.5	C504—C505—H505	119.9
H14B—C14—H14C	109.5	C506—C505—H505	119.9
C102—C101—C106	118.48 (13)	C505—C506—C501	121.28 (14)
C102—C101—C1	121.60 (13)	C505—C506—H506	119.4
C106—C101—C1	119.81 (12)	C501—C506—H506	119.4
C103—C102—C101	120.89 (14)	C6—Fe1—C7	91.40 (7)
C103—C102—H102	119.6	C6—Fe1—C11	85.92 (7)
C101—C102—H102	119.6	C7—Fe1—C11	88.54 (6)
C102—C103—C104	120.13 (14)	C6—Fe1—C2	107.57 (6)
C102—C103—H103	119.9	C7—Fe1—C2	108.35 (6)
C104—C103—H103	119.9	C11—Fe1—C2	157.64 (6)
C105—C104—C103	119.69 (14)	C6—Fe1—C1	94.00 (6)
C105—C104—H104	120.2	C7—Fe1—C1	146.96 (6)
C103—C104—H104	120.2	C11—Fe1—C1	124.33 (6)
C104—C105—C106	120.13 (14)	C2—Fe1—C1	39.25 (5)
C104—C105—H105	119.9	C6—Fe1—C4	155.60 (6)
C106—C105—H105	119.9	C7—Fe1—C4	113.00 (6)
C105—C106—C101	120.64 (13)	C11—Fe1—C4	94.23 (6)
C105—C106—H106	119.7	C2—Fe1—C4	66.04 (5)
C101—C106—H106	119.7	C1—Fe1—C4	65.83 (5)
C206—C201—C202	118.68 (13)	C6—Fe1—C3	145.32 (6)
C206—C201—C2	122.40 (13)	C7—Fe1—C3	92.62 (6)
C202—C201—C2	118.87 (13)	C11—Fe1—C3	128.60 (6)
C203—C202—C201	120.82 (14)	C2—Fe1—C3	39.05 (5)
C203—C202—H202	119.6	C1—Fe1—C3	65.38 (5)
C201—C202—H202	119.6	C4—Fe1—C3	39.21 (5)
C202—C203—C204	120.09 (14)	C6—Fe1—C5	116.45 (6)
C202—C203—H203	120.0	C7—Fe1—C5	152.13 (6)
C204—C203—H203	120.0	C11—Fe1—C5	92.33 (6)
C205—C204—C203	119.47 (14)	C2—Fe1—C5	65.84 (5)
C205—C204—H204	120.3	C1—Fe1—C5	39.20 (5)
C203—C204—H204	120.3	C4—Fe1—C5	39.15 (5)
C204—C205—C206	120.36 (14)	C3—Fe1—C5	65.39 (5)
C5—C1—C2—C3	0.24 (15)	C3—C2—C201—C206	−126.66 (15)
C101—C1—C2—C3	−174.43 (12)	C1—C2—C201—C206	62.0 (2)
Fe1—C1—C2—C3	61.74 (9)	Fe1—C2—C201—C206	−32.30 (19)
C5—C1—C2—C201	172.81 (13)	C3—C2—C201—C202	55.7 (2)
C101—C1—C2—C201	−1.9 (2)	C1—C2—C201—C202	−115.59 (16)
Fe1—C1—C2—C201	−125.70 (14)	Fe1—C2—C201—C202	150.09 (11)
C5—C1—C2—Fe1	−61.50 (9)	C206—C201—C202—C203	−0.9 (2)
C101—C1—C2—Fe1	123.83 (13)	C2—C201—C202—C203	176.79 (13)
C1—C2—C3—C4	−1.79 (15)	C201—C202—C203—C204	−0.4 (2)
C201—C2—C3—C4	−174.44 (13)	C202—C203—C204—C205	1.0 (2)
Fe1—C2—C3—C4	59.62 (9)	C203—C204—C205—C206	−0.3 (2)
C1—C2—C3—C301	170.16 (12)	C204—C205—C206—C201	−1.0 (2)
C201—C2—C3—C301	−2.5 (2)	C202—C201—C206—C205	1.6 (2)
Fe1—C2—C3—C301	−128.42 (13)	C2—C201—C206—C205	−175.99 (13)
C1—C2—C3—Fe1	−61.41 (9)	C2—C3—C301—C302	46.1 (2)
C201—C2—C3—Fe1	125.94 (14)	C4—C3—C301—C302	−143.44 (14)
C2—C3—C4—C5	2.66 (15)	Fe1—C3—C301—C302	−47.69 (19)
C301—C3—C4—C5	−169.11 (12)	C2—C3—C301—C306	−127.07 (15)
Fe1—C3—C4—C5	62.17 (9)	C4—C3—C301—C306	43.4 (2)
C2—C3—C4—C401	174.79 (12)	Fe1—C3—C301—C306	139.19 (12)
C301—C3—C4—C401	3.0 (2)	C306—C301—C302—C303	0.9 (2)
Fe1—C3—C4—C401	−125.71 (13)	C3—C301—C302—C303	−172.28 (14)
C2—C3—C4—Fe1	−59.50 (9)	C301—C302—C303—C304	−0.3 (2)
C301—C3—C4—Fe1	128.72 (14)	C302—C303—C304—C305	−0.4 (2)
C3—C4—C5—C1	−2.48 (15)	C303—C304—C305—C306	0.5 (2)
C401—C4—C5—C1	−174.02 (13)	C304—C305—C306—C301	0.1 (2)
Fe1—C4—C5—C1	59.23 (9)	C302—C301—C306—C305	−0.8 (2)
C3—C4—C5—C501	168.41 (13)	C3—C301—C306—C305	172.50 (13)
C401—C4—C5—C501	−3.1 (2)	C3—C4—C401—C406	−118.24 (15)
Fe1—C4—C5—C501	−129.88 (13)	C5—C4—C401—C406	52.2 (2)
C3—C4—C5—Fe1	−61.71 (9)	Fe1—C4—C401—C406	150.09 (11)
C401—C4—C5—Fe1	126.76 (14)	C3—C4—C401—C402	53.96 (19)
C2—C1—C5—C4	1.39 (15)	C5—C4—C401—C402	−135.63 (15)
C101—C1—C5—C4	176.02 (12)	Fe1—C4—C401—C402	−37.71 (19)
Fe1—C1—C5—C4	−59.25 (9)	C406—C401—C402—C403	2.1 (2)
C2—C1—C5—C501	−169.55 (13)	C4—C401—C402—C403	−170.18 (14)
C101—C1—C5—C501	5.1 (2)	C401—C402—C403—C404	−1.3 (2)
Fe1—C1—C5—C501	129.81 (13)	C402—C403—C404—C405	−0.1 (3)
C2—C1—C5—Fe1	60.64 (9)	C403—C404—C405—C406	0.6 (2)
C101—C1—C5—Fe1	−124.73 (13)	C404—C405—C406—C401	0.3 (2)
Fe1—C11—C12—C13	173.47 (13)	C402—C401—C406—C405	−1.6 (2)
C11—C12—C13—C14	62.4 (2)	C4—C401—C406—C405	170.73 (13)
C2—C1—C101—C102	−138.63 (14)	C4—C5—C501—C506	−131.50 (14)
C5—C1—C101—C102	47.6 (2)	C1—C5—C501—C506	37.7 (2)
Fe1—C1—C101—C102	−46.80 (18)	Fe1—C5—C501—C506	132.89 (13)
C2—C1—C101—C106	45.2 (2)	C4—C5—C501—C502	43.9 (2)
C5—C1—C101—C106	−128.52 (15)	C1—C5—C501—C502	−146.88 (14)
Fe1—C1—C101—C106	137.06 (12)	Fe1—C5—C501—C502	−51.7 (2)
C106—C101—C102—C103	2.2 (2)	C506—C501—C502—C503	−2.0 (2)
C1—C101—C102—C103	−173.98 (13)	C5—C501—C502—C503	−177.41 (13)
C101—C102—C103—C104	−1.0 (2)	C501—C502—C503—C504	1.4 (2)
C102—C103—C104—C105	−0.8 (2)	C502—C503—C504—C505	0.1 (2)
C103—C104—C105—C106	1.4 (2)	C503—C504—C505—C506	−1.1 (2)
C104—C105—C106—C101	−0.2 (2)	C504—C505—C506—C501	0.5 (2)
C102—C101—C106—C105	−1.6 (2)	C502—C501—C506—C505	1.0 (2)
C1—C101—C106—C105	174.65 (13)	C5—C501—C506—C505	176.63 (13)