(η5-Cyclo­penta­dien­yl)[(1,2,3,4,4a,12a-η)-naphtho­[2,3-b][1,4]benzodioxine]iron(II) hexa­fluoridophosphate

Hendsbee, A.D.; Masuda, J.D.; Piórko, A.

doi:10.1107/S1600536810033179

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page m1154

https://doi.org/10.1107/S1600536810033179

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(η⁵-Cyclopentadienyl)[(1,2,3,4,4a,12a-η)-naphtho[2,3-b][1,4]benzodioxine]iron(II) hexafluoridophosphate

Arthur D. Hendsbee,^a Jason D. Masuda ^a and Adam Piórko ^a ^*

^aDepartment of Chemistry, Saint Mary's University, Halifax, Nova Scotia, Canada B3H 3C3
^*Correspondence e-mail: adam.piorko@smu.ca

(Received 10 August 2010; accepted 17 August 2010; online 21 August 2010)

At 296 (2) K, both complexed rings in the iron(II) complex cation of the title salt, [Fe(C₅H₅)(C₁₆H₁₀O₂)]PF₆, are almost parallel [dihedral angle between planes = 2.4 (3)°]. The quaternary C atoms of the complexed arene ring are located at the longest distance from the Fe atom, with Fe—C distances of 2.112 (4) and 2.105 (3) Å, which are slightly longer than the average Fe—C distance for this ring (2.083 Å). The Fe ion is located 1.660 (1) and 1.543 (1) Å, respectively, from the cyclopentadienyl and the complexed arene ring.

Related literature

For the synthesis of the title compound and related structures, see Sutherland et al. (1982 , 1988 ). For the crystal structures of similar polycyclic {(η⁵-Cp) (η⁶-arene) Fe(II)}⁺ salts, see Piórko et al. (1995 ); Benites et al. (1996 , 1999 ); Decken (2004 ); Zanello et al. (2009 ) and literature cited therein; Asiri et al. (2010 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₆H₁₀O₂)]PF₆
M_r = 500.15
Monoclinic, P 2₁ /c
a = 15.3216 (13) Å
b = 8.9296 (8) Å
c = 14.6559 (12) Å
β = 106.417 (1)°
V = 1923.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.94 mm⁻¹
T = 296 K
0.35 × 0.29 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2010 ) T_min = 0.576, T_max = 0.746
12307 measured reflections
3372 independent reflections
2360 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.115
S = 1.01
3372 reflections
318 parameters
10 restraints
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.38 e Å⁻³

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810033179/si2288sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033179/si2288Isup2.hkl

checkCIF report

Comment top

The title compound, along with similar polycyclic aromatic O-, S-, and N-containing heterocycles complexed with a cyclopentadienyliron(II) moiety, was reported from the study on nucleophilic aromatic di-substitution reactions using 1,2-dichlorobenzene FeCp complex (Sutherland et al., 1988), which was an extension of an earlier study on the same reaction leading to synthesis of heterocyclic systems related to 9,10-dihydroanthracene and containing two heteroatoms at the 9,10-positions (Sutherland et al., 1982).

The ORTEP of the title compound is shown in Figure 1. The planes of the coordinated arene ring and Cp ring are nearly parallel, with an angle of 2.4 (3)° between them, and this value is typically reported for benzodioxine–Fe–Cp complexes (see Piórko et al., 1995, and references therein) and for arene–Fe–Cp complexes, in general (see for example Benites et al., 1996; Benites et al., 1999; Decken, 2004; Zanello et al., 2009).

The Fe ion is located at the distances 1.660 (1)Å from the Cp ring and 1.543 (1)Å from the complexed arene ring, and these values are close to those reported in the literature for similar complexes (see for example Piórko et al., 1995; Benites et al., 1999; Decken, 2004, and literature cited therein).

In a complexed arene ring, the C–C bond lengths are found within the narrow range from 1.391 (6) to 1.409 (5) Å. Both oxygen atoms show similar bond lengths toward complexed arene ring carbon atoms [1.363 (4)Å and 1.362 (4) Å] and these appear to be shorter than similar bonds toward an uncomplexed ring [both at 1.389 (4) Å]. Similar trends have been reported for other dibenzodioxine complexes (see Piórko et al., 1995). Of the C–C bonds in the uncomplexed fused carbocyclic rings of the heterocycle three appear to be markedly shorter [range 1.348 (6) to 1.356 (5) Å], one of intermediate length [1.373 (6) Å], and remaining seven appear to be longer [the range from 1.396 (7) to 1.423 (5) Å]. Some of the angles in the structure of a heterocycle appear to be distorted with angles C4a–O5–C5a and C11a–O12–C12a [116.7 (3) and 116.2 (3)°, respectively] and angles C6–C6a–C7 and C10–C10a–C11 [122.0 (4) and 122.2 (4)°, respectively, showing the largest deviations from an idealized trigonal geometry. The distribution of both the bond lengths and angles for the naphtho-moiety of this heterocycle are similar to the values reported for the naphthalene moiety of the naphthalene-2,3-diol in complex with 4-aminoantipyrine, with angles being less severely distorted from idealized geometry than those reported in the cited work (Asiri et al., 2010).

Related literature top

For the synthesis of the title compound and related structures, see Sutherland et al. (1982, 1988). For the crystal structures of similar polycyclic {(η⁵-Cp) (η⁶-arene) Fe(II)}⁺ salts, see Piórko et al. (1995); Benites et al. (1996, 1999); Decken (2004); Zanello et al. (2009) and literature cited therein; Asiri et al. (2010).

Experimental top

The title complex was prepared following the procedure of Sutherland et al. (1988). A crystal used for data collection was grown by slow evaporation of solvents from a solution of the complex in acetone-diethyl ether-dichloromethane mixture at 280 K.

Structure description top

For the synthesis of the title compound and related structures, see Sutherland et al. (1982, 1988). For the crystal structures of similar polycyclic {(η⁵-Cp) (η⁶-arene) Fe(II)}⁺ salts, see Piórko et al. (1995); Benites et al. (1996, 1999); Decken (2004); Zanello et al. (2009) and literature cited therein; Asiri et al. (2010).

Computing details top

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

Figures top

Fig. 1. View of the complex showing the labelling of non-H atoms with the displacement ellipsoids shown at 50% probability levels.

(η⁵-Cyclopentadienyl)[(1,2,3,4,4a,12a-η)-naphtho[2,3- b][1,4]benzodioxine]iron(II) hexafluoridophosphate top

Crystal data top

[Fe(C₅H₅)(C₁₆H₁₀O₂)]PF₆	F(000) = 1008
M_r = 500.15	D_x = 1.727 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2735 reflections
a = 15.3216 (13) Å	θ = 2.7–22.8°
b = 8.9296 (8) Å	µ = 0.94 mm⁻¹
c = 14.6559 (12) Å	T = 296 K
β = 106.417 (1)°	Block, green
V = 1923.4 (3) Å³	0.35 × 0.29 × 0.17 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3372 independent reflections
Radiation source: fine-focus sealed tube	2360 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
φ and ω scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2010)	h = −18→18
T_min = 0.576, T_max = 0.746	k = −10→7
12307 measured reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0615P)² + 0.6855P] where P = (F_o² + 2F_c²)/3
3372 reflections	(Δ/σ)_max < 0.001
318 parameters	Δρ_max = 0.39 e Å⁻³
10 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₆H₁₀O₂)]PF₆	V = 1923.4 (3) Å³
M_r = 500.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.3216 (13) Å	µ = 0.94 mm⁻¹
b = 8.9296 (8) Å	T = 296 K
c = 14.6559 (12) Å	0.35 × 0.29 × 0.17 mm
β = 106.417 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3372 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2010)	2360 reflections with I > 2σ(I)
T_min = 0.576, T_max = 0.746	R_int = 0.035
12307 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	10 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.01	Δρ_max = 0.39 e Å⁻³
3372 reflections	Δρ_min = −0.38 e Å⁻³
318 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Fe1	0.16289 (3)	0.26572 (5)	0.26515 (3)	0.04229 (18)
C1	0.1824 (3)	0.0364 (4)	0.2519 (3)	0.0590 (10)
H1	0.1483	−0.0343	0.2799	0.071*
C2	0.1398 (3)	0.0996 (5)	0.1626 (3)	0.0702 (12)
H2	0.0772	0.0710	0.1293	0.084*
C3	0.1777 (3)	0.2252 (5)	0.1324 (3)	0.0700 (12)
H3	0.1408	0.2827	0.0782	0.084*
C4	0.2580 (3)	0.2887 (5)	0.1898 (3)	0.0627 (11)
H4	0.2763	0.3889	0.1752	0.075*
C4A	0.3014 (2)	0.2225 (4)	0.2783 (2)	0.0524 (9)
O5	0.37912 (17)	0.2877 (3)	0.33276 (19)	0.0654 (7)
C11	0.4064 (2)	0.0586 (4)	0.5466 (2)	0.0507 (9)
H11	0.3785	−0.0222	0.5670	0.061*
C6	0.4885 (2)	0.2990 (4)	0.4823 (3)	0.0601 (10)
H6	0.5157	0.3786	0.4598	0.072*
C5A	0.4136 (2)	0.2335 (4)	0.4248 (3)	0.0507 (9)
C6A	0.5258 (2)	0.2478 (4)	0.5763 (3)	0.0583 (10)
C10A	0.4838 (2)	0.1264 (4)	0.6094 (2)	0.0534 (9)
C10	0.5215 (3)	0.0752 (5)	0.7038 (3)	0.0711 (12)
H10	0.4945	−0.0042	0.7268	0.085*
C7	0.6054 (3)	0.3126 (6)	0.6385 (3)	0.0814 (14)
H7	0.6340	0.3917	0.6173	0.098*
C8	0.6396 (3)	0.2606 (6)	0.7278 (4)	0.0885 (15)
H8	0.6918	0.3041	0.7675	0.106*
C9	0.5979 (3)	0.1423 (7)	0.7616 (3)	0.0829 (14)
H9	0.6220	0.1087	0.8237	0.099*
O12	0.29927 (16)	0.0364 (3)	0.39696 (17)	0.0591 (7)
C11A	0.3728 (2)	0.1115 (4)	0.4568 (2)	0.0474 (8)
C12A	0.2627 (2)	0.0985 (4)	0.3096 (2)	0.0508 (9)
C15	0.0678 (3)	0.4333 (4)	0.2353 (3)	0.0624 (10)
H15	0.0418	0.4804	0.1731	0.075*
C16	0.1460 (3)	0.4808 (4)	0.3056 (3)	0.0635 (10)
H16	0.1842	0.5667	0.3010	0.076*
C13	0.0896 (3)	0.2764 (5)	0.3621 (3)	0.0658 (11)
H13	0.0812	0.1949	0.4036	0.079*
C14	0.0335 (3)	0.3075 (5)	0.2704 (3)	0.0636 (10)
H14	−0.0209	0.2509	0.2367	0.076*
C17	0.1598 (3)	0.3829 (5)	0.3837 (3)	0.0673 (12)
H17	0.2091	0.3891	0.4431	0.081*
P1	0.14134 (7)	0.71338 (11)	0.01907 (6)	0.0534 (3)
F6	0.1339 (2)	0.7270 (3)	0.12317 (14)	0.1027 (10)
F5	0.1492 (2)	0.7032 (4)	−0.08442 (13)	0.1125 (11)
F1	0.0591 (9)	0.8194 (19)	−0.0190 (13)	0.151 (7)	0.49 (2)
F4	0.2020 (9)	0.8540 (11)	0.0478 (10)	0.099 (4)	0.49 (2)
F3	0.2262 (9)	0.613 (2)	0.0594 (8)	0.119 (5)	0.49 (2)
F2	0.0843 (16)	0.5689 (16)	−0.0101 (14)	0.171 (7)	0.49 (2)
F4A	0.0861 (10)	0.8595 (11)	−0.0107 (10)	0.108 (4)	0.51 (2)
F3A	0.2313 (9)	0.802 (2)	0.0361 (11)	0.149 (6)	0.51 (2)
F2A	0.1942 (15)	0.5649 (16)	0.0482 (15)	0.165 (7)	0.51 (2)
F1A	0.0482 (7)	0.634 (2)	0.0012 (11)	0.119 (5)	0.51 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0490 (3)	0.0417 (3)	0.0325 (3)	0.0032 (2)	0.00559 (19)	−0.0020 (2)
C1	0.066 (2)	0.042 (2)	0.061 (2)	0.0015 (18)	0.0035 (19)	−0.0074 (18)
C2	0.081 (3)	0.066 (3)	0.049 (2)	0.014 (2)	−0.004 (2)	−0.020 (2)
C3	0.089 (3)	0.083 (3)	0.0362 (19)	0.023 (3)	0.013 (2)	−0.004 (2)
C4	0.077 (3)	0.069 (3)	0.051 (2)	0.016 (2)	0.031 (2)	0.0117 (19)
C4A	0.052 (2)	0.053 (2)	0.053 (2)	0.0079 (18)	0.0169 (17)	0.0044 (17)
O5	0.0552 (15)	0.0659 (19)	0.0713 (17)	−0.0065 (13)	0.0116 (13)	0.0257 (14)
C11	0.0431 (19)	0.051 (2)	0.059 (2)	0.0058 (17)	0.0171 (17)	0.0088 (17)
C6	0.050 (2)	0.043 (2)	0.083 (3)	−0.0032 (17)	0.011 (2)	0.0063 (19)
C5A	0.0469 (19)	0.043 (2)	0.062 (2)	0.0027 (16)	0.0143 (17)	0.0099 (17)
C6A	0.045 (2)	0.052 (3)	0.073 (3)	0.0043 (18)	0.0101 (18)	−0.0073 (19)
C10A	0.0417 (19)	0.063 (3)	0.053 (2)	0.0115 (17)	0.0093 (17)	−0.0078 (18)
C10	0.059 (2)	0.097 (4)	0.058 (2)	0.014 (2)	0.017 (2)	0.000 (2)
C7	0.060 (3)	0.072 (3)	0.096 (4)	−0.004 (2)	−0.004 (2)	−0.010 (3)
C8	0.067 (3)	0.097 (4)	0.085 (3)	0.001 (3)	−0.005 (3)	−0.026 (3)
C9	0.063 (3)	0.119 (4)	0.058 (3)	0.017 (3)	0.003 (2)	−0.014 (3)
O12	0.0536 (14)	0.0509 (16)	0.0604 (15)	−0.0074 (12)	−0.0039 (12)	0.0155 (12)
C11A	0.0402 (18)	0.045 (2)	0.054 (2)	0.0021 (15)	0.0078 (16)	0.0021 (16)
C12A	0.056 (2)	0.041 (2)	0.052 (2)	0.0061 (17)	0.0087 (17)	0.0007 (16)
C15	0.060 (2)	0.055 (3)	0.069 (2)	0.019 (2)	0.014 (2)	0.007 (2)
C16	0.071 (3)	0.045 (2)	0.080 (3)	0.001 (2)	0.030 (2)	−0.017 (2)
C13	0.074 (3)	0.079 (3)	0.051 (2)	−0.002 (2)	0.029 (2)	−0.003 (2)
C14	0.052 (2)	0.066 (3)	0.072 (3)	0.000 (2)	0.014 (2)	−0.007 (2)
C17	0.074 (3)	0.079 (3)	0.047 (2)	0.006 (2)	0.0152 (19)	−0.020 (2)
P1	0.0587 (6)	0.0512 (6)	0.0445 (5)	0.0020 (5)	0.0052 (4)	0.0036 (4)
F6	0.118 (2)	0.131 (3)	0.0626 (16)	0.0151 (18)	0.0325 (16)	0.0094 (15)
F5	0.163 (3)	0.120 (3)	0.0552 (15)	0.042 (2)	0.0322 (17)	0.0069 (15)
F1	0.066 (6)	0.242 (18)	0.118 (8)	0.079 (8)	−0.017 (5)	0.026 (11)
F4	0.137 (9)	0.065 (5)	0.092 (5)	−0.039 (5)	0.030 (7)	−0.004 (4)
F3	0.133 (8)	0.154 (10)	0.059 (5)	0.108 (8)	0.009 (5)	0.012 (6)
F2	0.236 (14)	0.096 (9)	0.143 (10)	−0.088 (10)	−0.011 (12)	−0.016 (7)
F4A	0.168 (12)	0.062 (5)	0.103 (8)	0.041 (5)	0.051 (8)	0.021 (4)
F3A	0.067 (5)	0.273 (18)	0.095 (7)	−0.068 (8)	0.004 (4)	0.017 (9)
F2A	0.256 (15)	0.100 (8)	0.171 (15)	0.100 (9)	0.115 (12)	0.081 (8)
F1A	0.101 (6)	0.137 (10)	0.123 (6)	−0.074 (7)	0.036 (5)	−0.029 (8)

Geometric parameters (Å, º) top

Fe1—C17	2.040 (4)	C5A—C11A	1.402 (5)
Fe1—C14	2.040 (4)	C6A—C10A	1.414 (5)
Fe1—C15	2.048 (4)	C6A—C7	1.423 (5)
Fe1—C13	2.047 (4)	C10A—C10	1.417 (5)
Fe1—C16	2.048 (4)	C10—C9	1.373 (6)
Fe1—C3	2.053 (4)	C10—H10	0.9300
Fe1—C2	2.070 (4)	C7—C8	1.348 (6)
Fe1—C4	2.072 (4)	C7—H7	0.9300
Fe1—C1	2.086 (4)	C8—C9	1.396 (7)
Fe1—C12A	2.105 (3)	C8—H8	0.9300
Fe1—C4A	2.112 (4)	C9—H9	0.9300
C1—C12A	1.396 (5)	O12—C12A	1.362 (4)
C1—C2	1.406 (5)	O12—C11A	1.389 (4)
C1—H1	0.9800	C15—C14	1.398 (5)
C2—C3	1.391 (6)	C15—C16	1.407 (5)
C2—H2	0.9800	C15—H15	0.9800
C3—C4	1.400 (6)	C16—C17	1.407 (6)
C3—H3	0.9800	C16—H16	0.9800
C4—C4A	1.409 (5)	C13—C14	1.403 (5)
C4—H4	0.9800	C13—C17	1.403 (5)
C4A—O5	1.363 (4)	C13—H13	0.9800
C4A—C12A	1.394 (5)	C14—H14	0.9800
O5—C5A	1.389 (4)	C17—H17	0.9800
C11—C11A	1.356 (5)	P1—F4	1.549 (2)
C11—C10A	1.415 (5)	P1—F1	1.548 (2)
C11—H11	0.9300	P1—F2	1.549 (2)
C6—C5A	1.350 (5)	P1—F3	1.550 (2)
C6—C6A	1.410 (5)	P1—F5	1.5575 (16)
C6—H6	0.9300	P1—F6	1.5664 (17)

C17—Fe1—C14	67.49 (16)	C4—C4A—Fe1	68.8 (2)
C17—Fe1—C15	67.71 (16)	C4A—O5—C5A	116.7 (3)
C14—Fe1—C15	40.00 (15)	C11A—C11—C10A	120.0 (3)
C17—Fe1—C13	40.16 (15)	C11A—C11—H11	120.0
C14—Fe1—C13	40.16 (15)	C10A—C11—H11	120.0
C15—Fe1—C13	67.51 (17)	C5A—C6—C6A	120.5 (4)
C17—Fe1—C16	40.26 (16)	C5A—C6—H6	119.8
C14—Fe1—C16	67.26 (17)	C6A—C6—H6	119.8
C15—Fe1—C16	40.18 (15)	C6—C5A—O5	118.6 (3)
C13—Fe1—C16	67.41 (17)	C6—C5A—C11A	120.6 (3)
C17—Fe1—C3	158.83 (19)	O5—C5A—C11A	120.8 (3)
C14—Fe1—C3	115.88 (17)	C6—C6A—C10A	119.1 (3)
C15—Fe1—C3	100.87 (17)	C6—C6A—C7	122.0 (4)
C13—Fe1—C3	153.49 (18)	C10A—C6A—C7	118.9 (4)
C16—Fe1—C3	119.78 (18)	C11—C10A—C6A	118.9 (3)
C17—Fe1—C2	161.04 (19)	C11—C10A—C10	122.2 (4)
C14—Fe1—C2	100.97 (17)	C6A—C10A—C10	118.9 (4)
C15—Fe1—C2	113.79 (16)	C9—C10—C10A	120.2 (5)
C13—Fe1—C2	121.53 (18)	C9—C10—H10	119.9
C16—Fe1—C2	150.78 (17)	C10A—C10—H10	119.9
C3—Fe1—C2	39.42 (16)	C8—C7—C6A	120.7 (5)
C17—Fe1—C4	126.30 (18)	C8—C7—H7	119.7
C14—Fe1—C4	147.06 (16)	C6A—C7—H7	119.7
C15—Fe1—C4	112.27 (16)	C7—C8—C9	120.9 (4)
C13—Fe1—C4	166.28 (17)	C7—C8—H8	119.6
C16—Fe1—C4	103.14 (17)	C9—C8—H8	119.6
C3—Fe1—C4	39.66 (17)	C10—C9—C8	120.5 (4)
C2—Fe1—C4	71.66 (18)	C10—C9—H9	119.7
C17—Fe1—C1	128.39 (16)	C8—C9—H9	119.7
C14—Fe1—C1	110.46 (17)	C12A—O12—C11A	116.2 (3)
C15—Fe1—C1	144.04 (16)	C11—C11A—O12	117.5 (3)
C13—Fe1—C1	103.38 (17)	C11—C11A—C5A	120.9 (3)
C16—Fe1—C1	168.65 (15)	O12—C11A—C5A	121.5 (3)
C3—Fe1—C1	71.46 (17)	O12—C12A—C4A	122.2 (3)
C2—Fe1—C1	39.54 (14)	O12—C12A—C1	117.8 (3)
C4—Fe1—C1	84.65 (17)	C4A—C12A—C1	120.0 (3)
C17—Fe1—C12A	106.86 (15)	O12—C12A—Fe1	130.5 (2)
C14—Fe1—C12A	138.34 (16)	C4A—C12A—Fe1	71.0 (2)
C15—Fe1—C12A	174.54 (14)	C1—C12A—Fe1	69.8 (2)
C13—Fe1—C12A	108.15 (16)	C14—C15—C16	107.6 (4)
C16—Fe1—C12A	135.72 (15)	C14—C15—Fe1	69.7 (2)
C3—Fe1—C12A	84.45 (15)	C16—C15—Fe1	69.9 (2)
C2—Fe1—C12A	71.12 (14)	C14—C15—H15	126.2
C4—Fe1—C12A	71.10 (14)	C16—C15—H15	126.2
C1—Fe1—C12A	38.90 (13)	Fe1—C15—H15	126.2
C17—Fe1—C4A	106.32 (15)	C15—C16—C17	108.1 (4)
C14—Fe1—C4A	172.93 (14)	C15—C16—Fe1	69.9 (2)
C15—Fe1—C4A	142.10 (16)	C17—C16—Fe1	69.6 (2)
C13—Fe1—C4A	132.83 (15)	C15—C16—H16	126.0
C16—Fe1—C4A	110.57 (15)	C17—C16—H16	126.0
C3—Fe1—C4A	71.14 (16)	Fe1—C16—H16	126.0
C2—Fe1—C4A	84.02 (16)	C14—C13—C17	107.7 (4)
C4—Fe1—C4A	39.33 (14)	C14—C13—Fe1	69.6 (2)
C1—Fe1—C4A	70.26 (15)	C17—C13—Fe1	69.6 (2)
C12A—Fe1—C4A	38.60 (13)	C14—C13—H13	126.1
C12A—C1—C2	120.2 (4)	C17—C13—H13	126.1
C12A—C1—Fe1	71.3 (2)	Fe1—C13—H13	126.1
C2—C1—Fe1	69.6 (2)	C15—C14—C13	108.6 (4)
C12A—C1—H1	119.1	C15—C14—Fe1	70.3 (2)
C2—C1—H1	119.1	C13—C14—Fe1	70.2 (2)
Fe1—C1—H1	119.1	C15—C14—H14	125.7
C3—C2—C1	119.6 (4)	C13—C14—H14	125.7
C3—C2—Fe1	69.6 (2)	Fe1—C14—H14	125.7
C1—C2—Fe1	70.9 (2)	C13—C17—C16	108.0 (4)
C3—C2—H2	119.3	C13—C17—Fe1	70.2 (2)
C1—C2—H2	119.3	C16—C17—Fe1	70.2 (2)
Fe1—C2—H2	119.3	C13—C17—H17	126.0
C2—C3—C4	120.7 (4)	C16—C17—H17	126.0
C2—C3—Fe1	70.9 (2)	Fe1—C17—H17	126.0
C4—C3—Fe1	70.9 (2)	F4—P1—F1	88.1 (7)
C2—C3—H3	118.9	F4—P1—F2	177.5 (9)
C4—C3—H3	118.9	F1—P1—F2	94.1 (9)
Fe1—C3—H3	118.9	F4—P1—F3	89.4 (7)
C3—C4—C4A	119.3 (4)	F1—P1—F3	177.4 (8)
C3—C4—Fe1	69.5 (2)	F2—P1—F3	88.4 (9)
C4A—C4—Fe1	71.9 (2)	F4—P1—F5	96.1 (5)
C3—C4—H4	119.7	F1—P1—F5	87.9 (7)
C4A—C4—H4	119.7	F2—P1—F5	82.8 (9)
Fe1—C4—H4	119.7	F3—P1—F5	92.9 (5)
O5—C4A—C12A	121.9 (3)	F4—P1—F6	82.8 (5)
O5—C4A—C4	117.8 (3)	F1—P1—F6	91.6 (7)
C12A—C4A—C4	120.1 (4)	F2—P1—F6	98.2 (9)
O5—C4A—Fe1	131.6 (3)	F3—P1—F6	87.5 (5)
C12A—C4A—Fe1	70.4 (2)	F5—P1—F6	178.9 (2)

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₆H₁₀O₂)]PF₆
M_r	500.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	15.3216 (13), 8.9296 (8), 14.6559 (12)
β (°)	106.417 (1)
V (Å³)	1923.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.35 × 0.29 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2010)
T_min, T_max	0.576, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	12307, 3372, 2360
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.115, 1.01
No. of reflections	3372
No. of parameters	318
No. of restraints	10
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.38

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SAINT (Bruker, 2010, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Acknowledgements

The authors would like to thank Saint Mary's University for funding, the Natural Sciences and Engineering Research Council for a Discovery Grant (JDM), the Canadian Foundation for Innovation for a Leaders Opportunity Fund Grant and the Nova Scotia Research and Innovation Trust (JDM). Student funding was provided through the Saint Mary's University Summer Employment Experience Program (ADH).

References

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