1,1′-Bis(4-bromo­phen­yl)-3,3′-di­phenyl­ferrocene

Peloquin, A.J.; Smith, M.B.; Balaich, G.J.; Iacono, S.T.

doi:10.1107/S2414314619004875

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 4| April 2019| x190487

https://doi.org/10.1107/S2414314619004875

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1,1′-Bis(4-bromophenyl)-3,3′-diphenylferrocene

Andrew J. Peloquin,^a Madelyn B. Smith,^a Gary J. Balaich ^a and Scott T. Iacono ^a ^*

^aDepartment of Chemistry & Chemistry Research Center, United States Air Force Academy, Colorado Springs, CO 80840, USA
^*Correspondence e-mail: scott.iacono@usafa.edu

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 3 April 2019; accepted 9 April 2019; online 25 April 2019)

In the title compound, [Fe(C₁₇H₁₂Br)₂], the Fe^II atom is sandwiched between the eclipsed five-membered rings, with Fe⋯ring centroid distances of 1.649 (3) and 1.652 (3) Å. In one of the ligands, the Br atom is disordered over two locations [site occupancies = 0.839 (2) and 0.161 (2)].

Keywords: crystal structure; ferrocene.

CCDC reference: 1849488

Structure description

Substituted ferrocenes have been investigated for their applications in molecular machines (Muraoka et al., 2003 ), as arylation catalysts (Schmiel & Butenschön, 2017 ), and to moderate the burning rates of composited solid propellants (Liu et al., 2015 ). In an effort to provide a structurally simple starting material for further diversification, the title ferrocene complex, with each cyclopentadienyl ligand bearing a phenyl and 4-bromophenyl susbstituent at its 1 and 3 positions, was synthesized.

The title compound (Fig. 1) crystallizes in the orthorhombic space group Pna2₁ with one molecule per asymmetric unit. The compound consists of two 1-(4-bromophenyl)-3-phenylcyclopentadienyl ligands with the Fe^II atom sandwiched between the cyclopentadienyl ligands. The distances between the cyclopentadienyl centroids and the Fe^II atom are 1.649 (3) and 1.652 (3) Å: the five-membered rings are almost eclipsed. The phenyl substituents are twisted slightly with respect to the cyclopentadienyl cores, with deviations of the ring planes ranging from 10.5 (3) to 19.6 (3)°. The main disorder component of Br1 and Br1′ both lie at the same end of the molecule.

Figure 1
The molecular structure of the title compound. Displacement ellipsoids are shown at the 50% probability level. Only the primary disorder component for Br1 and associated H atoms is shown.

Synthesis and crystallization

The title compound was synthesized following a modified literature procedure (Peloquin et al., 2012 ). A solution of 3-(4-bromophenyl)-cyclopent-2-en-1-one (43.40 g, 183.0 mmol) in THF (500 ml) under N₂ was added dropwise over 15 min to vigorously stirred PhMgCl in THF (2.0 M, 119.0 ml, 238.0 mmol) under N₂. The resulting brown reaction mixture was allowed to stir at room temperature for 15 h under N₂, exposed to air, and the THF was removed by rotary vacuum to give a brown residue. The brown residue was taken up and vigorously stirred in a mixture of water (300 ml) and Et₂O (500 ml). Addition of 1 M H₂SO₄ (61.3 ml, 61.3 mmol) resulted in a brown Et₂O layer and a clear water layer, which was stirred for an additional 5 min. The brown Et₂O layer was separated and washed sequentially with saturated NaHCO₃ (3 × 200 ml), water (2 × 200 ml), and saturated brine (200 ml). The organic layer was dried over anhydrous Na₂SO₄, filtered, and concentrated under vacuum to afford a golden-colored oil, which was recrystallized by dissolving in boiling hot absolute ethanol (300 ml) and cooling (268 K). Vacuum filtration, washing with cold absolute ethanol (20 ml), and vacuum drying afforded the target compound as yellow crystalline flakes (45.7 g, 84%). ¹H NMR (500 MHz, CDCl₃): δ 7.61–7.35 (m, 10H), 6.64 (d, 1H, J = 5.5 Hz), 3.56 (d, 2H, J = 17 Hz).

Metallation was accomplished via a modified literature procedure (Hosono et al., 2013 ). To a solution of 1-(4-bromophenyl)-3-phenyl-cyclopentadiene (4.80 g, 16.2 mmol) in THF (100 ml) at 273 K, KOt-Bu (2.13 g, 19.0 mmol) was added and the mixture was allowed to gradually warm to room temperature and stir for 7 h. The resulting reddish-brown solution was added via cannula transfer to a suspension of FeCl₂ (2.02 g, 15.9 mmol) in THF (50 ml) at 273 K. After stirring at room temperature under N₂ for 18 hrs, 500 ml of water was added to the reaction mixture. The mixture was extracted with CH₂Cl₂ (2 × 250 ml), dried over MgSO₄, and evaporated to dryness under reduced pressure. The resulting solid was recrystallized from Et₂O solution to yield the target product as an orange solid (2.104 g, 40%). Crystals suitable for X-ray diffraction were obtained by layering a saturated dichloromethane solution with acetonitrile. ¹H NMR (500 MHz, CDCl₃): δ 7.26–7.16 (m, 12H), 7.01 (d, 2H, J = 9.0 Hz), 6.95 (d, 2H, J = 8.0 Hz), 4.72 (br s, 2H), 4.50 (br d, 2H, J = 10 Hz), 4.43 (br s, 2H).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. Atom Br1 is disordered over two positions, bound to C9 and C15, with a refined occupancy of 0.839 (2) at the C9 position.

Table 1
Experimental details

Crystal data
Chemical formula	[Fe(C₁₇H₁₂Br)₂]
M_r	648.20
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	24.2914 (17), 14.3317 (10), 7.5014 (5)
V (Å³)	2611.5 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	3.66
Crystal size (mm)	0.19 × 0.14 × 0.08

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2017 )
T_min, T_max	0.50, 0.75
No. of measured, independent and observed [I > 2σ(I)] reflections	53974, 6454, 5283
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.103, 1.07
No. of reflections	6454
No. of parameters	344
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.44, −0.77
Absolute structure	Flack x determined using 2036 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.052 (6)
Computer programs: APEX3 and SAINT (Bruker, 2017), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae, et al., 2008 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1849488

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314619004875/hb4292sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619004875/hb4292Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2017); cell refinement: SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae, et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

(I) top

Crystal data top

[Fe(C₁₇H₁₂Br)₂]	D_x = 1.649 Mg m⁻³
M_r = 648.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 7252 reflections
a = 24.2914 (17) Å	θ = 2.2–22.9°
b = 14.3317 (10) Å	µ = 3.66 mm⁻¹
c = 7.5014 (5) Å	T = 100 K
V = 2611.5 (3) Å³	Plate, translucent orange
Z = 4	0.19 × 0.14 × 0.08 mm
F(000) = 1296

Data collection top

Bruker SMART APEX CCD diffractometer	6454 independent reflections
Radiation source: fine focus sealed tube	5283 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
Detector resolution: 8.3333 pixels mm^-1	θ_max = 28.3°, θ_min = 2.2°
ω scans	h = −32→32
Absorption correction: multi-scan (SADABS; Bruker, 2017)	k = −19→19
T_min = 0.50, T_max = 0.75	l = −9→9
53974 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.046	w = 1/[σ²(F_o²) + (0.0333P)² + 3.9647P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.103	(Δ/σ)_max = 0.001
S = 1.07	Δρ_max = 1.44 e Å⁻³
6454 reflections	Δρ_min = −0.77 e Å⁻³
344 parameters	Absolute structure: Flack x determined using 2036 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
6 restraints	Absolute structure parameter: 0.052 (6)
Primary atom site location: dual

Special details top

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.

Refinement. Bromine atom Br1 was modeled across two positions, bound to C9 and C15, with final refined occupancy of 0.83925 at the C9 position. An attempt to bring the Br1A-C9 bond length (1.561) to a more reasonable length was made using DFIX, but the small occupancy of the C15 site limited the effectiveness of this method. The final Flack parameter 0.052 applies only to the smaller disordered part (the main disordered part is not chiral). The main disordered part is not chiral, and any amount of chiral product would have been formed as a racemic mixture during synthesis.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.66063 (4)	0.92233 (6)	0.17341 (14)	0.0445 (3)	0.839 (2)
Br1A	0.51480 (18)	0.0149 (3)	0.1444 (7)	0.0477 (17)	0.161 (2)
Br1'	0.77282 (3)	0.88889 (5)	0.61250 (11)	0.04133 (18)
Fe1	0.59400 (3)	0.45241 (6)	0.60272 (13)	0.02673 (19)
C1	0.5686 (2)	0.5472 (5)	0.4128 (8)	0.0302 (15)
C2	0.5808 (3)	0.4582 (5)	0.3366 (8)	0.0281 (14)
H2	0.608217	0.446759	0.248916	0.034*
C3	0.5452 (3)	0.3885 (5)	0.4131 (8)	0.0307 (15)
C4	0.5123 (2)	0.4359 (5)	0.5433 (9)	0.0290 (14)
H4	0.485344	0.407651	0.617479	0.035*
C5	0.5263 (2)	0.5305 (5)	0.5434 (9)	0.0336 (16)
H5	0.510318	0.576675	0.618071	0.04*
C6	0.5919 (2)	0.6370 (5)	0.3646 (8)	0.0280 (14)
C7	0.6411 (3)	0.6440 (5)	0.2692 (9)	0.0332 (15)
H7	0.660541	0.588559	0.239819	0.04*
C8	0.6623 (3)	0.7281 (5)	0.2167 (10)	0.0387 (17)
H8	0.696148	0.731057	0.153696	0.046*
C9	0.6336 (3)	0.8084 (5)	0.2568 (10)	0.0405 (17)
H9	0.647462	0.866911	0.217657	0.049*	0.161 (2)
C10	0.5849 (3)	0.8054 (5)	0.3533 (10)	0.0397 (17)
H10	0.565861	0.8613	0.382097	0.048*
C11	0.5646 (3)	0.7206 (5)	0.4065 (9)	0.0351 (16)
H11	0.531359	0.718346	0.472983	0.042*
C12	0.5403 (3)	0.2908 (5)	0.3615 (8)	0.0331 (15)
C13	0.4930 (3)	0.2384 (6)	0.4070 (10)	0.0418 (18)
H13	0.465195	0.266712	0.47761	0.05*
C14	0.4862 (3)	0.1486 (6)	0.3527 (12)	0.054 (2)
H14	0.453349	0.115966	0.381278	0.065*
C15	0.5274 (3)	0.1046 (6)	0.2552 (12)	0.052 (2)
H15	0.522978	0.041609	0.218143	0.062*	0.839 (2)
C16	0.5750 (3)	0.1529 (5)	0.2123 (10)	0.0421 (18)
H16	0.603479	0.122737	0.147555	0.051*
C17	0.5810 (3)	0.2440 (6)	0.2629 (9)	0.0365 (16)
H17	0.61364	0.276524	0.23057	0.044*
C1'	0.6620 (3)	0.5083 (5)	0.7288 (8)	0.0295 (14)
C2'	0.6750 (2)	0.4217 (5)	0.6481 (8)	0.0287 (14)
H2'	0.702109	0.412482	0.558641	0.034*
C3'	0.6406 (2)	0.3497 (5)	0.7226 (8)	0.0278 (14)
C4'	0.6055 (3)	0.3955 (5)	0.8476 (8)	0.0284 (14)
H4'	0.577765	0.365716	0.916606	0.034*
C5'	0.6180 (3)	0.4907 (5)	0.8532 (8)	0.0291 (14)
H5'	0.600468	0.535922	0.926426	0.035*
C6'	0.6879 (2)	0.5988 (5)	0.6958 (8)	0.0299 (14)
C7'	0.7369 (2)	0.6062 (5)	0.5964 (11)	0.0348 (14)
H7'	0.752997	0.551791	0.546345	0.042*
C8'	0.7620 (3)	0.6925 (5)	0.5709 (9)	0.0379 (18)
H8'	0.795343	0.697049	0.505082	0.045*
C9'	0.7382 (3)	0.7706 (5)	0.6419 (8)	0.0351 (16)
C10'	0.6895 (3)	0.7662 (5)	0.7365 (9)	0.0371 (16)
H10'	0.673468	0.821246	0.784335	0.044*
C11'	0.6646 (3)	0.6810 (5)	0.7603 (9)	0.0352 (16)
H11'	0.630518	0.678081	0.822461	0.042*
C12'	0.6427 (2)	0.2504 (5)	0.6802 (8)	0.0311 (14)
C13'	0.6021 (3)	0.1888 (5)	0.7454 (10)	0.0403 (17)
H13'	0.572269	0.212889	0.813014	0.048*
C14'	0.6050 (3)	0.0925 (6)	0.7123 (13)	0.052 (2)
H14'	0.577072	0.052326	0.757026	0.062*
C15'	0.6481 (3)	0.0558 (5)	0.6151 (13)	0.0493 (18)
H15'	0.650562	−0.009517	0.595725	0.059*
C16'	0.6878 (4)	0.1156 (6)	0.5457 (10)	0.048 (2)
H16'	0.717118	0.091094	0.476041	0.057*
C17'	0.6849 (3)	0.2106 (5)	0.5778 (9)	0.0360 (17)
H17'	0.712463	0.250117	0.528919	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0512 (5)	0.0259 (4)	0.0565 (6)	−0.0057 (4)	0.0129 (4)	0.0011 (4)
Br1A	0.042 (3)	0.042 (3)	0.058 (4)	−0.0072 (19)	−0.005 (2)	−0.006 (2)
Br1'	0.0317 (3)	0.0501 (4)	0.0422 (4)	−0.0068 (3)	0.0022 (4)	0.0074 (4)
Fe1	0.0192 (4)	0.0440 (5)	0.0170 (3)	0.0062 (3)	0.0000 (4)	0.0042 (5)
C1	0.020 (3)	0.051 (4)	0.020 (3)	0.009 (3)	−0.002 (2)	0.005 (3)
C2	0.021 (3)	0.046 (4)	0.017 (3)	0.008 (3)	0.000 (2)	0.003 (3)
C3	0.023 (3)	0.049 (4)	0.020 (3)	0.006 (3)	−0.002 (2)	0.007 (3)
C4	0.019 (3)	0.045 (4)	0.023 (3)	0.001 (3)	0.002 (2)	0.006 (3)
C5	0.019 (3)	0.061 (5)	0.021 (3)	0.014 (3)	0.000 (2)	0.006 (3)
C6	0.022 (3)	0.045 (4)	0.018 (3)	0.011 (3)	−0.005 (2)	0.002 (3)
C7	0.026 (3)	0.047 (4)	0.027 (3)	0.003 (3)	0.004 (3)	0.005 (3)
C8	0.026 (3)	0.055 (4)	0.035 (4)	0.006 (3)	0.001 (3)	0.006 (3)
C9	0.039 (4)	0.046 (4)	0.036 (4)	0.000 (3)	−0.002 (3)	0.009 (3)
C10	0.035 (4)	0.044 (4)	0.040 (4)	0.009 (3)	−0.003 (3)	0.002 (3)
C11	0.033 (4)	0.044 (4)	0.029 (3)	0.002 (3)	0.003 (3)	0.003 (3)
C12	0.030 (4)	0.047 (4)	0.022 (3)	0.004 (3)	−0.005 (3)	0.005 (3)
C13	0.027 (3)	0.060 (5)	0.038 (4)	0.000 (3)	−0.002 (3)	0.006 (4)
C14	0.038 (4)	0.057 (5)	0.068 (6)	−0.011 (4)	−0.002 (4)	−0.006 (5)
C15	0.048 (5)	0.055 (5)	0.052 (5)	−0.010 (4)	−0.005 (4)	−0.010 (4)
C16	0.048 (4)	0.045 (4)	0.034 (4)	0.006 (4)	0.002 (3)	−0.007 (3)
C17	0.027 (3)	0.054 (5)	0.029 (4)	0.004 (3)	0.003 (3)	0.007 (3)
C1'	0.021 (3)	0.046 (4)	0.022 (3)	0.002 (3)	−0.005 (2)	0.002 (3)
C2'	0.018 (3)	0.050 (4)	0.017 (3)	0.008 (3)	−0.001 (2)	−0.001 (3)
C3'	0.022 (3)	0.044 (4)	0.017 (3)	0.004 (3)	−0.002 (2)	0.004 (3)
C4'	0.025 (3)	0.043 (4)	0.017 (3)	0.004 (3)	−0.002 (2)	0.007 (3)
C5'	0.025 (3)	0.044 (4)	0.018 (3)	0.003 (3)	0.000 (2)	0.001 (3)
C6'	0.021 (3)	0.051 (4)	0.018 (3)	0.005 (3)	−0.003 (2)	0.004 (3)
C7'	0.028 (3)	0.045 (4)	0.031 (3)	0.006 (3)	0.002 (3)	0.002 (4)
C8'	0.023 (3)	0.058 (5)	0.032 (5)	0.004 (3)	0.001 (3)	0.011 (3)
C9'	0.029 (3)	0.050 (4)	0.026 (4)	−0.003 (3)	−0.002 (3)	0.004 (3)
C10'	0.031 (4)	0.047 (4)	0.034 (4)	0.003 (3)	0.006 (3)	−0.005 (3)
C11'	0.027 (3)	0.046 (4)	0.033 (4)	−0.002 (3)	0.011 (3)	−0.001 (3)
C12'	0.026 (3)	0.048 (4)	0.020 (3)	0.008 (3)	−0.004 (3)	0.005 (3)
C13'	0.040 (4)	0.047 (4)	0.034 (4)	0.005 (3)	0.007 (3)	−0.001 (3)
C14'	0.051 (5)	0.044 (5)	0.061 (6)	0.002 (4)	0.012 (4)	0.000 (4)
C15'	0.058 (4)	0.046 (4)	0.044 (4)	0.006 (4)	0.001 (5)	0.003 (4)
C16'	0.055 (5)	0.051 (5)	0.037 (4)	0.018 (4)	−0.001 (4)	−0.007 (4)
C17'	0.028 (3)	0.054 (4)	0.025 (4)	0.004 (3)	−0.001 (3)	0.007 (3)

Geometric parameters (Å, º) top

Br1—C9	1.868 (8)	C14—C15	1.391 (12)
Br1A—C15	1.561 (9)	C14—H14	0.95
Br1'—C9'	1.906 (7)	C15—C16	1.385 (11)
Fe1—C2	2.023 (6)	C15—H15	0.95
Fe1—C4'	2.029 (6)	C16—C17	1.367 (11)
Fe1—C5	2.039 (6)	C16—H16	0.95
Fe1—C5'	2.042 (6)	C17—H17	0.95
Fe1—C2'	2.044 (5)	C1'—C2'	1.417 (9)
Fe1—C4	2.048 (6)	C1'—C5'	1.441 (9)
Fe1—C3'	2.063 (6)	C1'—C6'	1.463 (9)
Fe1—C1	2.063 (6)	C2'—C3'	1.439 (9)
Fe1—C1'	2.064 (6)	C2'—H2'	0.95
Fe1—C3	2.066 (7)	C3'—C4'	1.427 (9)
C1—C2	1.429 (10)	C3'—C12'	1.459 (9)
C1—C5	1.440 (9)	C4'—C5'	1.398 (9)
C1—C6	1.452 (10)	C4'—H4'	0.95
C2—C3	1.441 (9)	C5'—H5'	0.95
C2—H2	0.95	C6'—C11'	1.394 (9)
C3—C4	1.434 (9)	C6'—C7'	1.409 (9)
C3—C12	1.457 (10)	C7'—C8'	1.391 (10)
C4—C5	1.397 (10)	C7'—H7'	0.95
C4—H4	0.95	C8'—C9'	1.369 (10)
C5—H5	0.95	C8'—H8'	0.95
C6—C7	1.396 (9)	C9'—C10'	1.380 (9)
C6—C11	1.405 (9)	C10'—C11'	1.375 (10)
C7—C8	1.367 (10)	C10'—H10'	0.95
C7—H7	0.95	C11'—H11'	0.95
C8—C9	1.379 (10)	C12'—C17'	1.404 (9)
C8—H8	0.95	C12'—C13'	1.411 (10)
C9—C10	1.388 (10)	C13'—C14'	1.404 (11)
C9—H9	0.95	C13'—H13'	0.95
C10—C11	1.370 (10)	C14'—C15'	1.379 (11)
C10—H10	0.95	C14'—H14'	0.95
C11—H11	0.95	C15'—C16'	1.393 (12)
C12—C17	1.406 (9)	C15'—H15'	0.95
C12—C13	1.414 (10)	C16'—C17'	1.384 (11)
C13—C14	1.360 (12)	C16'—H16'	0.95
C13—H13	0.95	C17'—H17'	0.95

C2—Fe1—C4'	158.6 (3)	C9—C10—H10	120.5
C2—Fe1—C5	68.5 (3)	C10—C11—C6	121.4 (6)
C4'—Fe1—C5	121.9 (3)	C10—C11—H11	119.3
C2—Fe1—C5'	160.4 (3)	C6—C11—H11	119.3
C4'—Fe1—C5'	40.2 (3)	C17—C12—C13	116.4 (7)
C5—Fe1—C5'	106.5 (3)	C17—C12—C3	122.7 (6)
C2—Fe1—C2'	109.0 (2)	C13—C12—C3	120.9 (6)
C4'—Fe1—C2'	68.3 (2)	C14—C13—C12	122.0 (7)
C5—Fe1—C2'	158.6 (3)	C14—C13—H13	119.0
C5'—Fe1—C2'	68.3 (2)	C12—C13—H13	119.0
C2—Fe1—C4	68.7 (3)	C13—C14—C15	120.0 (8)
C4'—Fe1—C4	106.5 (3)	C13—C14—H14	120.0
C5—Fe1—C4	40.0 (3)	C15—C14—H14	120.0
C5'—Fe1—C4	120.5 (3)	C16—C15—C14	119.7 (8)
C2'—Fe1—C4	160.7 (3)	C16—C15—Br1A	116.9 (7)
C2—Fe1—C3'	123.1 (3)	C14—C15—Br1A	120.8 (7)
C4'—Fe1—C3'	40.8 (2)	C16—C15—H15	120.2
C5—Fe1—C3'	158.4 (3)	C14—C15—H15	120.2
C5'—Fe1—C3'	68.5 (3)	C17—C16—C15	120.2 (7)
C2'—Fe1—C3'	41.0 (3)	C17—C16—H16	119.9
C4—Fe1—C3'	123.0 (3)	C15—C16—H16	119.9
C2—Fe1—C1	40.9 (3)	C16—C17—C12	121.7 (7)
C4'—Fe1—C1	158.6 (3)	C16—C17—H17	119.2
C5—Fe1—C1	41.1 (2)	C12—C17—H17	119.2
C5'—Fe1—C1	122.9 (3)	C2'—C1'—C5'	106.8 (6)
C2'—Fe1—C1	123.0 (3)	C2'—C1'—C6'	127.5 (6)
C4—Fe1—C1	68.6 (3)	C5'—C1'—C6'	125.8 (6)
C3'—Fe1—C1	159.2 (2)	C2'—C1'—Fe1	69.0 (3)
C2—Fe1—C1'	124.2 (3)	C5'—C1'—Fe1	68.6 (4)
C4'—Fe1—C1'	68.4 (3)	C6'—C1'—Fe1	127.6 (4)
C5—Fe1—C1'	122.2 (3)	C1'—C2'—C3'	109.4 (5)
C5'—Fe1—C1'	41.1 (2)	C1'—C2'—Fe1	70.6 (3)
C2'—Fe1—C1'	40.4 (3)	C3'—C2'—Fe1	70.2 (3)
C4—Fe1—C1'	156.9 (3)	C1'—C2'—H2'	125.3
C3'—Fe1—C1'	68.8 (3)	C3'—C2'—H2'	125.3
C1—Fe1—C1'	107.5 (3)	Fe1—C2'—H2'	125.5
C2—Fe1—C3	41.2 (3)	C4'—C3'—C2'	105.8 (6)
C4'—Fe1—C3	121.6 (3)	C4'—C3'—C12'	127.7 (6)
C5—Fe1—C3	68.3 (3)	C2'—C3'—C12'	126.4 (6)
C5'—Fe1—C3	156.4 (3)	C4'—C3'—Fe1	68.3 (3)
C2'—Fe1—C3	124.8 (3)	C2'—C3'—Fe1	68.8 (3)
C4—Fe1—C3	40.8 (3)	C12'—C3'—Fe1	128.2 (4)
C3'—Fe1—C3	107.4 (3)	C5'—C4'—C3'	109.8 (6)
C1—Fe1—C3	69.2 (3)	C5'—C4'—Fe1	70.4 (4)
C1'—Fe1—C3	161.2 (3)	C3'—C4'—Fe1	70.9 (3)
C2—C1—C5	105.8 (6)	C5'—C4'—H4'	125.1
C2—C1—C6	127.6 (6)	C3'—C4'—H4'	125.1
C5—C1—C6	126.6 (6)	Fe1—C4'—H4'	125.2
C2—C1—Fe1	68.0 (4)	C4'—C5'—C1'	108.2 (6)
C5—C1—Fe1	68.5 (4)	C4'—C5'—Fe1	69.4 (4)
C6—C1—Fe1	129.7 (4)	C1'—C5'—Fe1	70.3 (4)
C1—C2—C3	109.6 (6)	C4'—C5'—H5'	125.9
C1—C2—Fe1	71.0 (4)	C1'—C5'—H5'	125.9
C3—C2—Fe1	70.9 (3)	Fe1—C5'—H5'	126.0
C1—C2—H2	125.2	C11'—C6'—C7'	117.6 (6)
C3—C2—H2	125.2	C11'—C6'—C1'	121.0 (6)
Fe1—C2—H2	124.4	C7'—C6'—C1'	121.4 (6)
C4—C3—C2	106.1 (6)	C8'—C7'—C6'	120.7 (6)
C4—C3—C12	126.2 (6)	C8'—C7'—H7'	119.7
C2—C3—C12	127.6 (6)	C6'—C7'—H7'	119.7
C4—C3—Fe1	68.9 (4)	C9'—C8'—C7'	119.1 (6)
C2—C3—Fe1	67.8 (4)	C9'—C8'—H8'	120.4
C12—C3—Fe1	131.0 (5)	C7'—C8'—H8'	120.4
C5—C4—C3	108.9 (6)	C8'—C9'—C10'	121.7 (6)
C5—C4—Fe1	69.7 (4)	C8'—C9'—Br1'	119.7 (5)
C3—C4—Fe1	70.3 (4)	C10'—C9'—Br1'	118.6 (5)
C5—C4—H4	125.5	C11'—C10'—C9'	119.0 (7)
C3—C4—H4	125.5	C11'—C10'—H10'	120.5
Fe1—C4—H4	126.1	C9'—C10'—H10'	120.5
C4—C5—C1	109.6 (6)	C10'—C11'—C6'	121.7 (6)
C4—C5—Fe1	70.4 (4)	C10'—C11'—H11'	119.1
C1—C5—Fe1	70.4 (3)	C6'—C11'—H11'	119.1
C4—C5—H5	125.2	C17'—C12'—C13'	116.5 (7)
C1—C5—H5	125.2	C17'—C12'—C3'	122.7 (6)
Fe1—C5—H5	125.7	C13'—C12'—C3'	120.8 (6)
C7—C6—C11	117.2 (6)	C14'—C13'—C12'	121.3 (7)
C7—C6—C1	121.7 (6)	C14'—C13'—H13'	119.3
C11—C6—C1	121.0 (6)	C12'—C13'—H13'	119.3
C8—C7—C6	122.1 (7)	C15'—C14'—C13'	120.3 (8)
C8—C7—H7	118.9	C15'—C14'—H14'	119.8
C6—C7—H7	118.9	C13'—C14'—H14'	119.8
C7—C8—C9	118.9 (7)	C14'—C15'—C16'	119.4 (8)
C7—C8—H8	120.6	C14'—C15'—H15'	120.3
C9—C8—H8	120.6	C16'—C15'—H15'	120.3
C8—C9—C10	121.2 (7)	C17'—C16'—C15'	120.3 (7)
C8—C9—Br1	118.7 (6)	C17'—C16'—H16'	119.8
C10—C9—Br1	120.1 (6)	C15'—C16'—H16'	119.8
C8—C9—H9	119.4	C16'—C17'—C12'	122.2 (7)
C10—C9—H9	119.4	C16'—C17'—H17'	118.9
C11—C10—C9	119.1 (7)	C12'—C17'—H17'	118.9
C11—C10—H10	120.5

Funding information

Funding for this research was provided by: Air Force Office of Scientific Research.

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