[(1,2,5,6-η)-Cyclo­octa-1,5-diene](1-ethyl-4-isobutyl-1,2,4-triazol-5-yl­idene)(tri­phenyl­phosphane)rhodium(I) tetra­fluorido­borate

Lerch, T.G.; Gau, M.; Albert, D.R.; Rajaseelan, E.

doi:10.1107/S2414314624007454

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 8| August 2024| x240745

https://doi.org/10.1107/S2414314624007454

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[(1,2,5,6-η)-Cycloocta-1,5-diene](1-ethyl-4-isobutyl-1,2,4-triazol-5-ylidene)(triphenylphosphane)rhodium(I) tetrafluoridoborate

Timothy G. Lerch,^a Michael Gau,^b Daniel R. Albert ^a and Edward Rajaseelan ^a ^*

^aDepartment of Chemistry, Millersville University, Millersville, PA 17551, USA, and ^bDepartment of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, USA
^*Correspondence e-mail: edward.rajaseelan@millersville.edu

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 26 July 2024; accepted 29 July 2024; online 2 August 2024)

A new, cationic N-heterocyclic carbene Rh^I complex with a tetrafluoridoborate counter-anion, [Rh(C₈H₁₂)(C₈H₁₅N₃)(C₁₈H₁₅P)]BF₄, has been synthesized and structurally characterized. There are two independent ion pairs in the asymmetric unit. Each complex cation exhibits a distorted square-planar conformation around the Rh^I atom. Bond lengths and bond angles are as expected for an Rh–NHC complex. There are several close, non-standard C—H⋯F hydrogen-bonding interactions between the ions. One of the tetrafluoridoborate anions shows statistical disorder of the F atoms.

Keywords: crystal structure; rhodium; N-heterocyclic carbenes; cationic complexes.

CCDC reference: 2374311

Structure description

N-heterocyclic carbene (NHC) complexes of transition metals have been studied extensively in homogeneous catalysis, especially in transfer hydrogenation of unsaturated bonds (Cazin, 2013 ; Diez-González et al., 2009 ; Rovis & Nolan, 2013 ; Ruff et al., 2016 ; Zuo et al., 2014 ). Their catalytic activity in the transfer hydrogenation of ketones and imines has also been studied and reported (Albrecht et al., 2002 ; Gnanamgari et al., 2007 ). The NHC ligands can be tuned both sterically and electronically by having different substituents on the nitrogen atoms (Diez-González & Nolan, 2007 ; Gusev, 2009 ). Many imidazole- and triazole-based NHC rhodium and iridium complexes have been synthesized and structurally characterized (Chianese et al., 2004 ; Herrmann et al., 2006 ; Wang & Lin 1998 ). We continue to synthesize new imidazole- and triazole-based NHC complexes of rhodium and iridium, to study the effect of different substituents on the NHCs and the other ligands coordinating to the metal in transfer hydrogenation reactions (Nichol et al., 2009 , 2010 , 2011 , 2012 ; Idrees et al., 2017a ,b ; Rood et al., 2021 ; Rushlow et al., 2021 ; Newman et al., 2021 ; Castaldi et al., 2021 ; Maynard et al., 2023 ; Lerch et al., 2024a ,b ).

The title complex, [Rh(C₈H₁₂)(C₈H₁₅N₃)(C₁₈H₁₅P)]BF₄ (2), comprises a cationic Rh^I complex and a tetrafluoridoborate counter-anion, with molecular structures illustrated in Fig. 1; there are two independent ion pairs in the asymmetric unit. The coordination sphere around the Rh^I cation, formed by the bidentate COD, NHC, and triphenylphosphane ligands, results in a distorted square-planar conformation, characterized by C_NHC—Rh—P bond angles of 89.6 (2)° for cation A and 89.8 (2)° for cation B. The N—C—N bond angles of the NHC ligand are 102.4 (7) and 103.8 (6)° for cations A and B, respectively. Other selected bond lengths in cations A and B are Rh—C_NHC = 2.030 (8) and 2.043 (8) Å, Rh—P = 2.3211 (18) and 2.3260 (15) Å, respectively.

Figure 1
Molecular structures of the four ions comprising the asymmetric unit of the title salt showing the atom-labeling scheme. Cation A, containing Rh1, is shown on the right. Displacement ellipsoids are drawn at the 50% probability level. Both orientations of the statistically disordered B2-tetrafluoridoborate anion are shown.

Fig. 2 shows a molecular packing diagram of the salt viewed along the a axis, with several close C—H⋯F contacts (likely, non-standard hydrogen-bonding interactions) stabilizing the orientation of the [BF₄]⁻ anions with respect to the Rh^I complex cations. The non-standard hydrogen-bonding interactions are shown as dotted orange lines in Fig. 2 and are summarized in Table 1.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯F3ⁱ	0.95	2.36	3.177 (8)	144
C8—H8C⋯F1	0.98	2.50	3.404 (10)	153
C13—H13⋯F5*	0.95	2.52	3.396 (17)	153
C20—H20⋯F2ⁱⁱ	0.95	2.34	3.291 (9)	178
C16′—H16′⋯F7*	0.95	2.40	3.351 (17)	177
C29′—H29D⋯F8ⁱⁱ	0.99	2.51	3.37 (2)	146
Symmetry codes: (i) ; (ii) .

Figure 2
Molecular packing diagram of the title salt visualized along the a axis with non-standard hydrogen-bonding interactions shown as dotted orange lines.

An overlay of the neutral precursor complex, chlorido[(1,2,5,6-η)-cycloocta-1,5-diene](1-ethyl-4-isobutyl-1,2,4-triazol-5-ylidene)rhodium(I) (1) (Lerch et al., 2024c ), and cation A of the title salt (2) (Fig. 3), shows that in (2) the Rh—C_NHC bond, and hence the entire NHC ligand, is rotated by almost 180° with respect to the remainder of the complex as visualized by the ethyl and isobutyl substituents not overlapping when the C_NHC, Rh, and Cl/P atoms are matched with the neutral complex (1). A similar rotation is observed in complex B. The two cations in the asymmetric-unit exhibit different configurations of the ethyl and isobutyl substituents with cation A showing a syn-configuration and cation B showing an anti-configuration with respect to each other when the C_NHC, Rh, and P atoms are matched between A and B, as seen in Fig. 4.

Figure 3
Overlay of complex A of the salt, shown in red, with previously characterized (Lerch et al., 2024c

) neutral complex (1), showing that the Rh—C_NHC bond has rotated 180° in the synthesis of the cationic complex from the neutral precursor. The overlay is constructed with C_NHC, Rh, and Cl/P atoms matched between the neutral complex (1) and complex A of the title salt (2) with an r.m.s. deviation of 0.029 Å between the matched atoms.

Figure 4
Overlay of complex A, shown in red, with complex B of the title salt showing the difference in orientation of the ethyl and isobutyl substituents with respect to the NHC ligand. The overlay is constructed with C_NHC, Rh, and P atoms matched between the two cations of with an r.m.s. deviation of 0.008 Å between the matched atoms.

Synthesis and crystallization

The synthesis and structure of chlorido[(1,2,5,6-η)-cycloocta-1,5-diene](1-ethyl-4-isobutyl-1,2,4-triazol-5-ylidene)rhodium(I) (1) have been published (Lerch et al. 2024c). All other compounds used in the syntheses, as shown in Fig. 5, were obtained from Sigma-Aldrich and Strem and used as received; all syntheses were performed under a nitrogen atmosphere. NMR spectra were recorded at room temperature in CDCl₃ on a 400 MHz (operating at 100 MHz for ¹H and ¹³C, and 162 MHz for ³¹P) Varian spectrometer and referenced to the residual solvent peak (δ in p.p.m.). The title salt (2) was crystallized by slow diffusion of pentane into a CH₂Cl₂ solution.

Figure 5
Reaction scheme for the synthesis of the title salt (2).

[(1,2,5,6-η)-Cycloocta-1,5-diene](1-ethyl-4-isobutyl-1,2,4-triazol-5-ylidene)(triphenylphosphane)rhodium(I) tetrafluoridoborate (2): Triphenylphosphane (0.097 g, 0.372 mmol) and AgBF₄ (0.072 g, 0.372 mmol) were added to (1) (0.149 g, 0.372 mmol) in CH₂Cl₂ (15 ml). The solution was stirred in the dark for 1.5 h. The resulting mixture was filtered through Celite and the solvent was removed under reduced pressure. The bright-yellow solid product (2) was dried under vacuum. Yield: 0.266 g (100%). ¹H NMR: δ 8.08 (s, 1H, N—C3H—N), 7.48–7.25 (m, 15H, H_aromatic), 4.72 (q, 2H, N—CH₂ of ethyl), 4.47 (d, 2H, N—CH₂ of isobutyl), 4.24 (m, 2H, CH of COD), 4.08 (m, 2H, CH of COD), 2.60 (m, 4H, CH₂ of COD), 2.48 (m, 2H, CH₂ of COD), 2.23 (m, 2H, CH₂ of COD), 2.06 (m, 1H, CH of isobutyl), 1.23 (t, 3H, CH₃ of ethyl), 0.92 (d, 6H, CH₃ of isobutyl). ¹³C NMR: δ 181.43 (d, Rh—C, J_C—Rh = 49.3 Hz), 143.88 (N—C3H—N), 133.47–128.49 (C_aromatic), 95.54, 95.46, 95.18, 95.06 (CH of COD), 55.70 (N—CH₂ of isobutyl), 48.11 (N—CH₂ of ethyl), 30.85, 30.50, 30.48, 30.19 (CH₂ of COD), 29.22 (CH of isobutyl), 19.98 (CH₃ of isobutyl), 13.93 (CH₃ of ethyl).³¹P NMR: δ 25.10 (d, J_Rh—P = 152.77 Hz).

Refinement

Refinement details are summarized in Table 2. One of the tetrafluoridoborate anions shows positional disorder of the F atoms over adjacent sites in a 1:1 ratio. The absolute structure was determined based on differences in Friedel pairs included in the data set (Parsons et al., 2013 ). The maximum and minimum electron density peaks of 2.51 and 1.08 e Å⁻³, respectively, were each located 0.87 Å from the Rh1 atom. Two reflections, i.e. 0 $[\overline{1}]$ 1 and 1 $[\overline{1}]$ 0, were omitted from the final cycles of refinement owing to poor agreement.

Table 2
Experimental details

Crystal data
Chemical formula	[Rh(C₈H₁₂)(C₈H₁₅N₃)(C₁₈H₁₅P)]BF₄
M_r	713.39
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.0296 (3), 10.3718 (3), 18.1424 (4)
α, β, γ (°)	99.270 (2), 93.906 (2), 118.766 (3)
V (Å³)	1609.47 (9)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.63
Crystal size (mm)	0.23 × 0.13 × 0.12

Data collection
Diffractometer	Rigaku XtaLAB Synergy-S
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2024 $[Rigaku OD (2024). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.823, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	46659, 15088, 13740
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.124, 1.03
No. of reflections	15088
No. of parameters	835
No. of restraints	135
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.51, −1.08
Absolute structure	Flack x determined using 5836 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013)
Absolute structure parameter	−0.029 (12)
Computer programs: CrysAlis PRO (Rigaku OD, 2024 $[Rigaku OD (2024). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2374311

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314624007454/tk4108sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624007454/tk4108Isup2.hkl

checkCIF report

Computing details top

[(1,2,5,6-η)-Cycloocta-1,5-diene](1-ethyl-4-isobutyl-1,2,4-triazol-5-ylidene)(triphenylphosphane)rhodium(I) tetrafluoridoborate top

Crystal data top

[Rh(C₈H₁₂)(C₈H₁₅N₃)(C₁₈H₁₅P)]BF₄	Z = 2
M_r = 713.39	F(000) = 736
Triclinic, P1	D_x = 1.472 Mg m⁻³
a = 10.0296 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3718 (3) Å	Cell parameters from 24773 reflections
c = 18.1424 (4) Å	θ = 2.2–28.3°
α = 99.270 (2)°	µ = 0.63 mm⁻¹
β = 93.906 (2)°	T = 100 K
γ = 118.766 (3)°	Block, yellow
V = 1609.47 (9) Å³	0.23 × 0.13 × 0.12 mm

Data collection top

Rigaku XtaLAB Synergy-S diffractometer	13740 reflections with I > 2σ(I)
Detector resolution: 10.0 pixels mm^-1	R_int = 0.047
ω scans	θ_max = 28.3°, θ_min = 2.3°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2024)	h = −13→13
T_min = 0.823, T_max = 1.000	k = −13→13
46659 measured reflections	l = −24→24
15088 independent 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)] = 0.049	w = 1/[σ²(F_o²) + (0.0858P)² + 0.5161P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.124	(Δ/σ)_max = 0.001
S = 1.03	Δρ_max = 2.51 e Å⁻³
15088 reflections	Δρ_min = −1.08 e Å⁻³
835 parameters	Absolute structure: Flack x determined using 5836 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
135 restraints	Absolute structure parameter: −0.029 (12)

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Rh1	0.37193 (4)	0.44291 (4)	1.05195 (2)	0.01839 (12)
P1	0.2676 (2)	0.3571 (2)	0.92393 (10)	0.0209 (4)
N1	0.1208 (7)	0.5098 (7)	1.0896 (3)	0.0287 (12)
N2	0.0659 (7)	0.6073 (7)	1.0954 (3)	0.0297 (12)
N3	0.2903 (8)	0.6987 (7)	1.0545 (3)	0.0276 (12)
C1	0.2574 (9)	0.5596 (9)	1.0644 (4)	0.0250 (16)
C2	0.1698 (7)	0.7192 (8)	1.0741 (4)	0.0281 (14)
H2	0.165092	0.807911	1.071937	0.034*
C3	0.0256 (8)	0.3582 (8)	1.1035 (5)	0.0345 (16)
H3A	0.083615	0.303285	1.098427	0.041*
H3B	−0.069026	0.301672	1.064678	0.041*
C4	−0.0190 (9)	0.3642 (9)	1.1814 (5)	0.0381 (17)
H4A	−0.088158	0.261541	1.187122	0.057*
H4B	−0.071816	0.422936	1.187507	0.057*
H4C	0.073962	0.412030	1.219987	0.057*
C5	0.4182 (8)	0.7952 (9)	1.0209 (4)	0.0312 (15)
H5A	0.381174	0.781082	0.966642	0.037*
H5B	0.496867	0.763687	1.023905	0.037*
C6	0.4922 (8)	0.9587 (8)	1.0579 (4)	0.0327 (15)
H6	0.410132	0.987045	1.060647	0.039*
C7	0.6059 (9)	1.0527 (9)	1.0102 (5)	0.0396 (18)
H7A	0.678330	1.016096	1.000976	0.059*
H7B	0.663184	1.158704	1.037307	0.059*
H7C	0.549224	1.043543	0.961654	0.059*
C8	0.5722 (9)	0.9875 (10)	1.1382 (5)	0.0399 (17)
H8A	0.497170	0.924182	1.167018	0.060*
H8B	0.615963	1.093976	1.162930	0.060*
H8C	0.655018	0.962959	1.136197	0.060*
C9	0.3857 (8)	0.4998 (8)	0.8729 (4)	0.0251 (13)
C10	0.5391 (8)	0.6020 (8)	0.9045 (4)	0.0259 (13)
H10	0.580519	0.595211	0.951506	0.031*
C11	0.6322 (8)	0.7130 (8)	0.8689 (4)	0.0316 (15)
H11	0.737716	0.779861	0.890352	0.038*
C12	0.5703 (10)	0.7264 (9)	0.8008 (4)	0.0371 (17)
H12	0.632014	0.805371	0.777058	0.045*
C13	0.4172 (9)	0.6229 (10)	0.7684 (4)	0.0351 (16)
H13	0.375949	0.629427	0.721327	0.042*
C14	0.3259 (8)	0.5123 (9)	0.8033 (4)	0.0313 (15)
H14	0.221501	0.443304	0.780758	0.038*
C15	0.2629 (7)	0.1842 (8)	0.8756 (4)	0.0262 (13)
C16	0.3457 (9)	0.1843 (10)	0.8164 (4)	0.0366 (17)
H16	0.398519	0.272464	0.797102	0.044*
C17	0.3504 (9)	0.0567 (11)	0.7866 (5)	0.047 (2)
H17	0.407399	0.057897	0.746747	0.057*
C18	0.2734 (10)	−0.0747 (10)	0.8133 (5)	0.047 (2)
H18	0.278777	−0.161938	0.792593	0.056*
C19	0.1903 (10)	−0.0755 (10)	0.8698 (5)	0.0401 (19)
H19	0.136714	−0.164718	0.888261	0.048*
C20	0.1825 (8)	0.0532 (8)	0.9013 (4)	0.0278 (14)
H20	0.122405	0.050244	0.939923	0.033*
C21	0.0720 (8)	0.3266 (8)	0.8986 (4)	0.0243 (14)
C22	−0.0583 (8)	0.1847 (8)	0.8783 (4)	0.0271 (14)
H22	−0.048015	0.097459	0.873023	0.033*
C23	−0.2036 (8)	0.1692 (9)	0.8656 (4)	0.0327 (16)
H23	−0.292064	0.071238	0.852093	0.039*
C24	−0.2216 (8)	0.2935 (10)	0.8723 (4)	0.0342 (16)
H24	−0.321888	0.281275	0.863550	0.041*
C25	−0.0923 (8)	0.4376 (10)	0.8920 (4)	0.0332 (16)
H25	−0.103899	0.524097	0.897197	0.040*
C26	0.0545 (8)	0.4537 (8)	0.9039 (4)	0.0273 (14)
H26	0.143124	0.551656	0.915819	0.033*
C27	0.5324 (10)	0.3584 (9)	1.0335 (5)	0.0249 (9)
H27	0.526628	0.315767	0.979107	0.030*
C28	0.4182 (8)	0.2608 (8)	1.0673 (4)	0.0248 (8)
H28	0.344994	0.161411	1.032437	0.030*
C29	0.4340 (8)	0.2524 (8)	1.1503 (4)	0.0290 (9)
H29A	0.371626	0.145953	1.154031	0.035*
H29B	0.543194	0.286840	1.169527	0.035*
C30	0.3829 (8)	0.3469 (8)	1.2002 (4)	0.0292 (9)
H30A	0.433736	0.370508	1.253181	0.035*
H30B	0.270166	0.286561	1.198645	0.035*
C31	0.4201 (9)	0.4951 (9)	1.1771 (4)	0.0283 (9)
H31	0.368593	0.547936	1.202330	0.034*
C32	0.5541 (8)	0.5877 (8)	1.1532 (4)	0.0286 (9)
H32	0.581468	0.695999	1.163289	0.034*
C33	0.6937 (8)	0.5643 (8)	1.1506 (4)	0.0280 (9)
H33A	0.695674	0.507604	1.189269	0.034*
H33B	0.789246	0.663942	1.163880	0.034*
C34	0.6924 (8)	0.4783 (8)	1.0726 (4)	0.0267 (8)
H34A	0.739640	0.550969	1.040035	0.032*
H34B	0.756311	0.430809	1.079328	0.032*
Rh1'	−0.30754 (4)	0.16819 (4)	0.54548 (2)	0.01794 (12)
P1'	−0.33122 (17)	0.18483 (19)	0.41940 (9)	0.0182 (3)
N1'	−0.5965 (7)	0.1941 (7)	0.5643 (3)	0.0277 (12)
N2'	−0.6483 (7)	0.2947 (8)	0.5817 (4)	0.0350 (14)
N3'	−0.3968 (6)	0.4103 (7)	0.5856 (3)	0.0263 (11)
C1'	−0.4451 (8)	0.2603 (9)	0.5656 (4)	0.0231 (15)
C2'	−0.5245 (8)	0.4232 (9)	0.5937 (4)	0.0323 (15)
H2'	−0.521925	0.516955	0.606750	0.039*
C3'	−0.7094 (8)	0.0336 (9)	0.5485 (4)	0.0318 (15)
H3'A	−0.755330	0.008215	0.594342	0.038*
H3'B	−0.656619	−0.024956	0.536251	0.038*
C4'	−0.8378 (9)	−0.0117 (10)	0.4826 (5)	0.0388 (17)
H4'A	−0.911323	−0.120026	0.474029	0.058*
H4'B	−0.793067	0.010723	0.436718	0.058*
H4'C	−0.891248	0.044967	0.494734	0.058*
C5'	−0.2378 (8)	0.5324 (8)	0.5908 (4)	0.0270 (13)
H5'A	−0.230872	0.577080	0.545979	0.032*
H5'B	−0.168451	0.489484	0.589641	0.032*
C6'	−0.1816 (8)	0.6576 (8)	0.6627 (4)	0.0298 (14)
H6'	−0.257116	0.694491	0.665291	0.036*
C7'	−0.0273 (9)	0.7875 (9)	0.6568 (5)	0.0385 (17)
H7'A	0.050135	0.755519	0.657473	0.058*
H7'B	0.003866	0.872260	0.699807	0.058*
H7'C	−0.035695	0.818915	0.609407	0.058*
C8'	−0.1733 (10)	0.5997 (9)	0.7340 (4)	0.0368 (17)
H8'A	−0.275564	0.517405	0.736632	0.055*
H8'B	−0.138914	0.681962	0.778749	0.055*
H8'C	−0.099948	0.562693	0.732563	0.055*
C9'	−0.3310 (7)	0.3517 (7)	0.3987 (3)	0.0223 (12)
C10'	−0.2087 (8)	0.4634 (7)	0.3730 (4)	0.0259 (13)
H10'	−0.124489	0.450046	0.361608	0.031*
C11'	−0.2089 (8)	0.5946 (8)	0.3640 (4)	0.0305 (15)
H11'	−0.125718	0.669254	0.345831	0.037*
C12'	−0.3316 (9)	0.6160 (8)	0.3818 (4)	0.0324 (15)
H12'	−0.330661	0.706217	0.376793	0.039*
C13'	−0.4533 (8)	0.5063 (8)	0.4064 (4)	0.0283 (14)
H13'	−0.536914	0.520409	0.418097	0.034*
C14'	−0.4544 (8)	0.3744 (8)	0.4143 (4)	0.0243 (13)
H14'	−0.540121	0.298502	0.430423	0.029*
C15'	−0.1893 (8)	0.1649 (7)	0.3684 (3)	0.0224 (12)
C16'	−0.0320 (8)	0.2722 (8)	0.3934 (4)	0.0276 (14)
H16'	−0.002065	0.358709	0.432365	0.033*
C17'	0.0795 (8)	0.2505 (9)	0.3605 (5)	0.0348 (16)
H17'	0.185545	0.322988	0.377386	0.042*
C18'	0.0380 (9)	0.1254 (10)	0.3039 (5)	0.0378 (17)
H18'	0.115320	0.111868	0.282248	0.045*
C19'	−0.1165 (9)	0.0195 (9)	0.2786 (4)	0.0324 (15)
H19'	−0.145555	−0.066225	0.239251	0.039*
C20'	−0.2290 (8)	0.0395 (8)	0.3113 (4)	0.0263 (13)
H20'	−0.334744	−0.034021	0.294311	0.032*
C21'	−0.5153 (6)	0.0283 (7)	0.3674 (3)	0.0194 (11)
C22'	−0.5830 (7)	−0.1071 (8)	0.3910 (4)	0.0270 (13)
H22'	−0.533669	−0.116060	0.434959	0.032*
C23'	−0.7211 (8)	−0.2292 (8)	0.3516 (4)	0.0336 (16)
H23'	−0.764379	−0.321992	0.367477	0.040*
C24'	−0.7962 (8)	−0.2154 (9)	0.2886 (4)	0.0320 (15)
H24'	−0.891240	−0.298811	0.261693	0.038*
C25'	−0.7340 (8)	−0.0826 (8)	0.2652 (4)	0.0292 (14)
H25'	−0.786931	−0.074098	0.222446	0.035*
C26'	−0.5930 (8)	0.0413 (8)	0.3036 (4)	0.0249 (13)
H26'	−0.550025	0.133120	0.286803	0.030*
C27'	−0.0969 (7)	0.1462 (7)	0.5524 (4)	0.0212 (12)
H27'	−0.026273	0.196341	0.517012	0.025*
C28'	−0.2235 (9)	0.0073 (8)	0.5178 (4)	0.0238 (15)
H28'	−0.226223	−0.024195	0.462387	0.029*
C29'	−0.3087 (9)	−0.1220 (8)	0.5551 (4)	0.0287 (15)
H29C	−0.251029	−0.176795	0.557268	0.034*
H29D	−0.411092	−0.192822	0.523498	0.034*
C30'	−0.3314 (8)	−0.0732 (8)	0.6355 (4)	0.0285 (14)
H30C	−0.421029	−0.159097	0.648284	0.034*
H30D	−0.239049	−0.046110	0.671854	0.034*
C31'	−0.3579 (7)	0.0599 (8)	0.6437 (3)	0.0255 (13)
H31'	−0.460695	0.036623	0.657588	0.031*
C32'	−0.2456 (9)	0.2096 (9)	0.6699 (4)	0.0263 (16)
H32'	−0.283070	0.272386	0.699277	0.032*
C33'	−0.0763 (8)	0.2717 (8)	0.6884 (4)	0.0236 (13)
H33C	−0.050708	0.264014	0.740640	0.028*
H33D	−0.022521	0.379961	0.687040	0.028*
C34'	−0.0169 (7)	0.1899 (8)	0.6338 (4)	0.0251 (13)
H34C	0.095348	0.256144	0.636344	0.030*
H34D	−0.032710	0.097768	0.650280	0.030*
F1	0.7916 (6)	0.8417 (6)	1.0710 (4)	0.0515 (13)
F2	0.9662 (7)	1.0421 (6)	1.0313 (4)	0.0536 (14)
F3	1.0502 (8)	0.9503 (8)	1.1177 (3)	0.071 (2)
F4	0.9502 (5)	0.8151 (5)	0.9960 (3)	0.0373 (10)
B1	0.9416 (10)	0.9128 (10)	1.0536 (5)	0.0312 (17)
F5	0.1255 (16)	0.5093 (16)	0.5876 (9)	0.060 (3)	0.5
F5*	0.2022 (19)	0.5151 (17)	0.5939 (9)	0.065 (3)	0.5
F6	0.298 (3)	0.755 (3)	0.6206 (9)	0.040 (3)	0.5
F6*	0.303 (3)	0.762 (3)	0.5970 (11)	0.055 (5)	0.5
F7	0.1238 (17)	0.6497 (17)	0.5094 (8)	0.052 (3)	0.5
F7*	0.0761 (16)	0.5857 (18)	0.5254 (9)	0.058 (3)	0.5
F8	0.320 (2)	0.598 (2)	0.5211 (10)	0.057 (3)	0.5
F8*	0.298 (2)	0.606 (2)	0.4955 (8)	0.056 (4)	0.5
B2	0.2230 (11)	0.6249 (11)	0.5550 (6)	0.0387 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Rh1	0.0198 (2)	0.0243 (3)	0.0178 (2)	0.0156 (2)	0.00022 (18)	0.00819 (19)
P1	0.0199 (8)	0.0294 (9)	0.0187 (8)	0.0159 (7)	0.0008 (6)	0.0082 (7)
N1	0.024 (3)	0.041 (3)	0.025 (3)	0.022 (3)	−0.003 (2)	0.003 (2)
N2	0.029 (3)	0.036 (3)	0.032 (3)	0.024 (3)	0.000 (2)	0.006 (2)
N3	0.036 (3)	0.029 (3)	0.027 (3)	0.024 (3)	0.002 (2)	0.008 (2)
C1	0.027 (4)	0.031 (4)	0.021 (3)	0.017 (3)	0.001 (3)	0.009 (3)
C2	0.024 (3)	0.032 (3)	0.036 (4)	0.021 (3)	0.000 (3)	0.004 (3)
C3	0.016 (3)	0.036 (4)	0.045 (4)	0.009 (3)	0.003 (3)	0.005 (3)
C4	0.033 (4)	0.040 (4)	0.042 (4)	0.017 (3)	0.007 (3)	0.012 (3)
C5	0.023 (3)	0.037 (4)	0.040 (4)	0.018 (3)	0.002 (3)	0.014 (3)
C6	0.026 (3)	0.036 (4)	0.041 (4)	0.019 (3)	0.004 (3)	0.010 (3)
C7	0.029 (4)	0.036 (4)	0.061 (5)	0.017 (3)	0.009 (3)	0.025 (4)
C8	0.036 (4)	0.042 (4)	0.043 (4)	0.022 (4)	0.002 (3)	0.009 (3)
C9	0.026 (3)	0.037 (3)	0.021 (3)	0.020 (3)	0.006 (2)	0.015 (3)
C10	0.029 (3)	0.035 (3)	0.020 (3)	0.020 (3)	0.004 (2)	0.010 (3)
C11	0.028 (3)	0.038 (4)	0.034 (4)	0.018 (3)	0.007 (3)	0.016 (3)
C12	0.052 (5)	0.045 (4)	0.029 (4)	0.030 (4)	0.017 (3)	0.021 (3)
C13	0.043 (4)	0.055 (5)	0.022 (3)	0.033 (4)	0.006 (3)	0.017 (3)
C14	0.028 (3)	0.047 (4)	0.023 (3)	0.020 (3)	0.001 (3)	0.013 (3)
C15	0.021 (3)	0.036 (3)	0.025 (3)	0.020 (3)	−0.004 (2)	0.000 (3)
C16	0.027 (3)	0.052 (5)	0.028 (4)	0.021 (3)	0.001 (3)	−0.001 (3)
C17	0.032 (4)	0.068 (6)	0.039 (4)	0.030 (4)	0.001 (3)	−0.012 (4)
C18	0.037 (4)	0.050 (5)	0.049 (5)	0.028 (4)	−0.012 (4)	−0.016 (4)
C19	0.038 (4)	0.042 (4)	0.041 (4)	0.027 (4)	−0.014 (3)	−0.005 (4)
C20	0.028 (3)	0.031 (3)	0.027 (3)	0.020 (3)	−0.005 (3)	−0.002 (3)
C21	0.023 (3)	0.039 (4)	0.020 (3)	0.022 (3)	0.002 (2)	0.011 (3)
C22	0.025 (3)	0.040 (4)	0.023 (3)	0.020 (3)	0.001 (2)	0.014 (3)
C23	0.019 (3)	0.047 (4)	0.028 (3)	0.012 (3)	0.000 (3)	0.016 (3)
C24	0.028 (3)	0.059 (5)	0.033 (4)	0.032 (3)	0.005 (3)	0.016 (3)
C25	0.030 (3)	0.057 (5)	0.029 (3)	0.033 (3)	0.003 (3)	0.017 (3)
C26	0.028 (3)	0.038 (4)	0.021 (3)	0.021 (3)	−0.002 (2)	0.006 (3)
C27	0.0282 (16)	0.0274 (16)	0.0275 (16)	0.0205 (14)	−0.0028 (14)	0.0085 (14)
C28	0.0288 (16)	0.0275 (16)	0.0270 (16)	0.0208 (13)	−0.0035 (13)	0.0097 (13)
C29	0.0317 (16)	0.0304 (16)	0.0269 (16)	0.0168 (14)	−0.0035 (14)	0.0101 (14)
C30	0.0321 (16)	0.0310 (16)	0.0259 (16)	0.0168 (14)	−0.0036 (14)	0.0103 (14)
C31	0.0314 (16)	0.0301 (16)	0.0259 (16)	0.0178 (14)	−0.0033 (14)	0.0084 (14)
C32	0.0311 (16)	0.0294 (16)	0.0268 (16)	0.0173 (14)	−0.0033 (13)	0.0066 (14)
C33	0.0298 (16)	0.0290 (15)	0.0281 (16)	0.0176 (14)	−0.0035 (13)	0.0077 (14)
C34	0.0286 (16)	0.0283 (16)	0.0283 (16)	0.0187 (14)	−0.0026 (14)	0.0075 (14)
Rh1'	0.0168 (2)	0.0229 (3)	0.0164 (2)	0.0112 (2)	0.00022 (17)	0.00689 (18)
P1'	0.0186 (7)	0.0239 (8)	0.0170 (7)	0.0138 (6)	0.0007 (5)	0.0078 (6)
N1'	0.024 (3)	0.039 (3)	0.027 (3)	0.019 (2)	0.004 (2)	0.011 (3)
N2'	0.029 (3)	0.043 (3)	0.041 (3)	0.024 (3)	0.009 (3)	0.007 (3)
N3'	0.023 (3)	0.032 (3)	0.027 (3)	0.017 (2)	0.002 (2)	0.006 (2)
C1'	0.023 (3)	0.030 (3)	0.017 (3)	0.014 (3)	0.002 (3)	0.008 (3)
C2'	0.027 (3)	0.038 (4)	0.036 (4)	0.022 (3)	0.007 (3)	0.002 (3)
C3'	0.022 (3)	0.040 (4)	0.035 (4)	0.014 (3)	0.005 (3)	0.018 (3)
C4'	0.024 (3)	0.046 (4)	0.042 (4)	0.015 (3)	−0.002 (3)	0.009 (3)
C5'	0.030 (3)	0.029 (3)	0.027 (3)	0.020 (3)	0.000 (3)	0.006 (3)
C6'	0.033 (3)	0.032 (3)	0.030 (3)	0.021 (3)	0.001 (3)	0.006 (3)
C7'	0.032 (4)	0.036 (4)	0.041 (4)	0.014 (3)	−0.006 (3)	0.006 (3)
C8'	0.047 (5)	0.034 (4)	0.033 (4)	0.025 (4)	−0.005 (3)	0.004 (3)
C9'	0.023 (3)	0.025 (3)	0.019 (3)	0.014 (2)	−0.003 (2)	0.005 (2)
C10'	0.026 (3)	0.029 (3)	0.027 (3)	0.016 (3)	0.001 (2)	0.010 (3)
C11'	0.030 (3)	0.026 (3)	0.031 (3)	0.009 (3)	0.001 (3)	0.012 (3)
C12'	0.045 (4)	0.025 (3)	0.029 (3)	0.022 (3)	−0.009 (3)	0.004 (3)
C13'	0.031 (3)	0.032 (3)	0.027 (3)	0.023 (3)	−0.007 (3)	0.002 (3)
C14'	0.026 (3)	0.029 (3)	0.020 (3)	0.015 (3)	0.000 (2)	0.006 (2)
C15'	0.031 (3)	0.029 (3)	0.020 (3)	0.021 (3)	0.007 (2)	0.015 (2)
C16'	0.027 (3)	0.033 (3)	0.029 (3)	0.016 (3)	0.005 (3)	0.017 (3)
C17'	0.026 (3)	0.044 (4)	0.042 (4)	0.020 (3)	0.009 (3)	0.022 (3)
C18'	0.039 (4)	0.055 (5)	0.043 (4)	0.035 (4)	0.021 (3)	0.029 (4)
C19'	0.044 (4)	0.039 (4)	0.030 (3)	0.031 (3)	0.013 (3)	0.013 (3)
C20'	0.029 (3)	0.033 (3)	0.024 (3)	0.019 (3)	0.003 (3)	0.013 (3)
C21'	0.013 (2)	0.024 (3)	0.019 (3)	0.008 (2)	−0.001 (2)	0.004 (2)
C22'	0.023 (3)	0.031 (3)	0.024 (3)	0.011 (3)	−0.001 (2)	0.010 (3)
C23'	0.031 (4)	0.026 (3)	0.037 (4)	0.008 (3)	0.003 (3)	0.012 (3)
C24'	0.025 (3)	0.036 (4)	0.028 (3)	0.011 (3)	−0.002 (3)	0.003 (3)
C25'	0.026 (3)	0.043 (4)	0.023 (3)	0.022 (3)	−0.003 (2)	0.005 (3)
C26'	0.026 (3)	0.033 (3)	0.023 (3)	0.021 (3)	0.000 (2)	0.007 (3)
C27'	0.018 (3)	0.030 (3)	0.023 (3)	0.016 (3)	0.002 (2)	0.013 (3)
C28'	0.030 (4)	0.027 (4)	0.022 (3)	0.020 (3)	0.000 (3)	0.008 (3)
C29'	0.027 (3)	0.020 (3)	0.040 (4)	0.012 (3)	−0.003 (3)	0.013 (3)
C30'	0.027 (3)	0.027 (3)	0.027 (3)	0.009 (3)	0.000 (3)	0.012 (3)
C31'	0.022 (3)	0.037 (3)	0.018 (3)	0.013 (3)	0.002 (2)	0.015 (3)
C32'	0.026 (4)	0.037 (4)	0.014 (3)	0.015 (3)	0.002 (2)	0.006 (3)
C33'	0.021 (3)	0.027 (3)	0.020 (3)	0.010 (3)	−0.001 (2)	0.009 (2)
C34'	0.020 (3)	0.031 (3)	0.025 (3)	0.012 (3)	−0.002 (2)	0.013 (3)
F1	0.043 (3)	0.042 (3)	0.085 (4)	0.026 (2)	0.030 (3)	0.029 (3)
F2	0.071 (4)	0.043 (3)	0.076 (4)	0.042 (3)	0.037 (3)	0.031 (3)
F3	0.085 (4)	0.096 (5)	0.051 (3)	0.076 (4)	−0.032 (3)	−0.020 (3)
F4	0.046 (3)	0.042 (2)	0.034 (2)	0.031 (2)	0.0011 (19)	0.0067 (19)
B1	0.034 (4)	0.037 (4)	0.032 (4)	0.024 (4)	−0.002 (3)	0.014 (3)
F5	0.053 (6)	0.047 (5)	0.070 (6)	0.012 (5)	0.012 (6)	0.029 (4)
F5*	0.076 (7)	0.057 (5)	0.069 (6)	0.034 (6)	0.006 (6)	0.032 (5)
F6	0.036 (5)	0.039 (5)	0.036 (7)	0.015 (4)	−0.012 (6)	0.006 (6)
F6*	0.042 (5)	0.040 (6)	0.068 (10)	0.012 (5)	0.005 (9)	0.003 (9)
F7	0.049 (7)	0.069 (7)	0.050 (6)	0.039 (6)	−0.010 (5)	0.020 (5)
F7*	0.037 (6)	0.072 (7)	0.067 (7)	0.033 (5)	−0.003 (5)	0.001 (6)
F8	0.051 (6)	0.067 (5)	0.078 (8)	0.048 (4)	0.010 (6)	0.019 (6)
F8*	0.044 (6)	0.082 (7)	0.052 (7)	0.032 (5)	0.020 (6)	0.032 (6)
B2	0.033 (3)	0.045 (4)	0.050 (4)	0.027 (3)	0.006 (3)	0.019 (3)

Geometric parameters (Å, º) top

Rh1—P1	2.3211 (18)	P1'—C9'	1.828 (7)
Rh1—C1	2.030 (8)	P1'—C15'	1.824 (7)
Rh1—C27	2.193 (8)	P1'—C21'	1.822 (6)
Rh1—C28	2.204 (6)	N1'—N2'	1.377 (9)
Rh1—C31	2.210 (7)	N1'—C1'	1.328 (9)
Rh1—C32	2.232 (7)	N1'—C3'	1.457 (10)
P1—C9	1.831 (7)	N2'—C2'	1.282 (10)
P1—C15	1.842 (7)	N3'—C1'	1.362 (10)
P1—C21	1.842 (7)	N3'—C2'	1.366 (9)
N1—N2	1.359 (8)	N3'—C5'	1.467 (9)
N1—C1	1.353 (10)	C2'—H2'	0.9500
N1—C3	1.471 (10)	C3'—H3'A	0.9900
N2—C2	1.271 (10)	C3'—H3'B	0.9900
N3—C1	1.363 (10)	C3'—C4'	1.528 (10)
N3—C2	1.384 (9)	C4'—H4'A	0.9800
N3—C5	1.444 (10)	C4'—H4'B	0.9800
C2—H2	0.9500	C4'—H4'C	0.9800
C3—H3A	0.9900	C5'—H5'A	0.9900
C3—H3B	0.9900	C5'—H5'B	0.9900
C3—C4	1.513 (11)	C5'—C6'	1.533 (9)
C4—H4A	0.9800	C6'—H6'	1.0000
C4—H4B	0.9800	C6'—C7'	1.512 (11)
C4—H4C	0.9800	C6'—C8'	1.526 (11)
C5—H5A	0.9900	C7'—H7'A	0.9800
C5—H5B	0.9900	C7'—H7'B	0.9800
C5—C6	1.494 (11)	C7'—H7'C	0.9800
C6—H6	1.0000	C8'—H8'A	0.9800
C6—C7	1.529 (11)	C8'—H8'B	0.9800
C6—C8	1.525 (11)	C8'—H8'C	0.9800
C7—H7A	0.9800	C9'—C10'	1.395 (9)
C7—H7B	0.9800	C9'—C14'	1.405 (9)
C7—H7C	0.9800	C10'—H10'	0.9500
C8—H8A	0.9800	C10'—C11'	1.397 (10)
C8—H8B	0.9800	C11'—H11'	0.9500
C8—H8C	0.9800	C11'—C12'	1.401 (11)
C9—C10	1.391 (10)	C12'—H12'	0.9500
C9—C14	1.413 (9)	C12'—C13'	1.373 (11)
C10—H10	0.9500	C13'—H13'	0.9500
C10—C11	1.379 (10)	C13'—C14'	1.393 (10)
C11—H11	0.9500	C14'—H14'	0.9500
C11—C12	1.402 (10)	C15'—C16'	1.408 (10)
C12—H12	0.9500	C15'—C20'	1.391 (10)
C12—C13	1.394 (12)	C16'—H16'	0.9500
C13—H13	0.9500	C16'—C17'	1.395 (10)
C13—C14	1.363 (11)	C17'—H17'	0.9500
C14—H14	0.9500	C17'—C18'	1.381 (12)
C15—C16	1.402 (10)	C18'—H18'	0.9500
C15—C20	1.384 (11)	C18'—C19'	1.386 (12)
C16—H16	0.9500	C19'—H19'	0.9500
C16—C17	1.371 (12)	C19'—C20'	1.395 (10)
C17—H17	0.9500	C20'—H20'	0.9500
C17—C18	1.392 (15)	C21'—C22'	1.391 (9)
C18—H18	0.9500	C21'—C26'	1.411 (8)
C18—C19	1.363 (13)	C22'—H22'	0.9500
C19—H19	0.9500	C22'—C23'	1.386 (10)
C19—C20	1.406 (11)	C23'—H23'	0.9500
C20—H20	0.9500	C23'—C24'	1.390 (10)
C21—C22	1.385 (10)	C24'—H24'	0.9500
C21—C26	1.401 (10)	C24'—C25'	1.365 (11)
C22—H22	0.9500	C25'—H25'	0.9500
C22—C23	1.385 (9)	C25'—C26'	1.402 (9)
C23—H23	0.9500	C26'—H26'	0.9500
C23—C24	1.372 (12)	C27'—H27'	1.0000
C24—H24	0.9500	C27'—C28'	1.386 (10)
C24—C25	1.394 (12)	C27'—C34'	1.518 (9)
C25—H25	0.9500	C28'—H28'	1.0000
C25—C26	1.396 (9)	C28'—C29'	1.501 (10)
C26—H26	0.9500	C29'—H29C	0.9900
C27—H27	1.0000	C29'—H29D	0.9900
C27—C28	1.376 (11)	C29'—C30'	1.534 (10)
C27—C34	1.505 (11)	C30'—H30C	0.9900
C28—H28	1.0000	C30'—H30D	0.9900
C28—C29	1.524 (9)	C30'—C31'	1.513 (10)
C29—H29A	0.9900	C31'—H31'	1.0000
C29—H29B	0.9900	C31'—C32'	1.383 (10)
C29—C30	1.518 (10)	C32'—H32'	1.0000
C30—H30A	0.9900	C32'—C33'	1.486 (10)
C30—H30B	0.9900	C33'—H33C	0.9900
C30—C31	1.535 (10)	C33'—H33D	0.9900
C31—H31	1.0000	C33'—C34'	1.534 (10)
C31—C32	1.374 (11)	C34'—H34C	0.9900
C32—H32	1.0000	C34'—H34D	0.9900
C32—C33	1.535 (10)	F1—B1	1.407 (11)
C33—H33A	0.9900	F2—B1	1.376 (10)
C33—H33B	0.9900	F3—B1	1.402 (10)
C33—C34	1.542 (10)	F4—B1	1.372 (11)
C34—H34A	0.9900	F5—B2	1.386 (16)
C34—H34B	0.9900	F5*—B2	1.374 (17)
Rh1'—P1'	2.3260 (15)	F6—B2	1.48 (2)
Rh1'—C1'	2.043 (8)	F6*—B2	1.31 (3)
Rh1'—C27'	2.229 (6)	F7—B2	1.394 (15)
Rh1'—C28'	2.211 (7)	F7*—B2	1.367 (16)
Rh1'—C31'	2.216 (6)	F8—B2	1.30 (2)
Rh1'—C32'	2.216 (7)	F8*—B2	1.40 (2)

C1—Rh1—P1	89.6 (2)	C28'—Rh1'—C32'	95.5 (3)
C1—Rh1—C27	168.5 (3)	C31'—Rh1'—P1'	157.09 (18)
C1—Rh1—C28	154.6 (3)	C31'—Rh1'—C27'	86.1 (2)
C1—Rh1—C31	85.6 (3)	C32'—Rh1'—P1'	166.5 (2)
C1—Rh1—C32	95.0 (3)	C32'—Rh1'—C27'	79.8 (3)
C27—Rh1—P1	90.3 (2)	C32'—Rh1'—C31'	36.4 (3)
C27—Rh1—C28	36.5 (3)	C9'—P1'—Rh1'	118.0 (2)
C27—Rh1—C31	96.6 (3)	C15'—P1'—Rh1'	114.5 (2)
C27—Rh1—C32	80.6 (3)	C15'—P1'—C9'	105.8 (3)
C28—Rh1—P1	98.75 (18)	C21'—P1'—Rh1'	109.4 (2)
C28—Rh1—C31	81.3 (3)	C21'—P1'—C9'	103.9 (3)
C28—Rh1—C32	87.1 (3)	C21'—P1'—C15'	103.7 (3)
C31—Rh1—P1	167.8 (2)	N2'—N1'—C3'	117.9 (6)
C31—Rh1—C32	36.0 (3)	C1'—N1'—N2'	113.4 (6)
C32—Rh1—P1	156.0 (2)	C1'—N1'—C3'	128.7 (6)
C9—P1—Rh1	109.1 (2)	C2'—N2'—N1'	103.1 (6)
C9—P1—C15	104.3 (3)	C1'—N3'—C2'	107.2 (6)
C9—P1—C21	103.9 (3)	C1'—N3'—C5'	125.1 (6)
C15—P1—Rh1	116.3 (2)	C2'—N3'—C5'	127.5 (6)
C15—P1—C21	105.9 (3)	N1'—C1'—Rh1'	130.2 (6)
C21—P1—Rh1	116.0 (2)	N1'—C1'—N3'	103.8 (6)
N2—N1—C3	119.7 (6)	N3'—C1'—Rh1'	126.0 (5)
C1—N1—N2	114.8 (6)	N2'—C2'—N3'	112.4 (7)
C1—N1—C3	125.3 (6)	N2'—C2'—H2'	123.8
C2—N2—N1	102.8 (6)	N3'—C2'—H2'	123.8
C1—N3—C2	106.9 (6)	N1'—C3'—H3'A	109.2
C1—N3—C5	125.0 (6)	N1'—C3'—H3'B	109.2
C2—N3—C5	127.7 (6)	N1'—C3'—C4'	112.1 (6)
N1—C1—Rh1	124.4 (6)	H3'A—C3'—H3'B	107.9
N1—C1—N3	102.4 (7)	C4'—C3'—H3'A	109.2
N3—C1—Rh1	133.2 (6)	C4'—C3'—H3'B	109.2
N2—C2—N3	113.1 (6)	C3'—C4'—H4'A	109.5
N2—C2—H2	123.4	C3'—C4'—H4'B	109.5
N3—C2—H2	123.4	C3'—C4'—H4'C	109.5
N1—C3—H3A	109.2	H4'A—C4'—H4'B	109.5
N1—C3—H3B	109.2	H4'A—C4'—H4'C	109.5
N1—C3—C4	111.9 (6)	H4'B—C4'—H4'C	109.5
H3A—C3—H3B	107.9	N3'—C5'—H5'A	108.9
C4—C3—H3A	109.2	N3'—C5'—H5'B	108.9
C4—C3—H3B	109.2	N3'—C5'—C6'	113.5 (6)
C3—C4—H4A	109.5	H5'A—C5'—H5'B	107.7
C3—C4—H4B	109.5	C6'—C5'—H5'A	108.9
C3—C4—H4C	109.5	C6'—C5'—H5'B	108.9
H4A—C4—H4B	109.5	C5'—C6'—H6'	108.1
H4A—C4—H4C	109.5	C7'—C6'—C5'	109.1 (6)
H4B—C4—H4C	109.5	C7'—C6'—H6'	108.1
N3—C5—H5A	108.8	C7'—C6'—C8'	111.6 (6)
N3—C5—H5B	108.8	C8'—C6'—C5'	111.7 (6)
N3—C5—C6	113.7 (6)	C8'—C6'—H6'	108.1
H5A—C5—H5B	107.7	C6'—C7'—H7'A	109.5
C6—C5—H5A	108.8	C6'—C7'—H7'B	109.5
C6—C5—H5B	108.8	C6'—C7'—H7'C	109.5
C5—C6—H6	108.7	H7'A—C7'—H7'B	109.5
C5—C6—C7	109.5 (7)	H7'A—C7'—H7'C	109.5
C5—C6—C8	110.0 (6)	H7'B—C7'—H7'C	109.5
C7—C6—H6	108.7	C6'—C8'—H8'A	109.5
C8—C6—H6	108.7	C6'—C8'—H8'B	109.5
C8—C6—C7	111.3 (6)	C6'—C8'—H8'C	109.5
C6—C7—H7A	109.5	H8'A—C8'—H8'B	109.5
C6—C7—H7B	109.5	H8'A—C8'—H8'C	109.5
C6—C7—H7C	109.5	H8'B—C8'—H8'C	109.5
H7A—C7—H7B	109.5	C10'—C9'—P1'	123.0 (5)
H7A—C7—H7C	109.5	C10'—C9'—C14'	118.1 (6)
H7B—C7—H7C	109.5	C14'—C9'—P1'	118.7 (5)
C6—C8—H8A	109.5	C9'—C10'—H10'	119.7
C6—C8—H8B	109.5	C9'—C10'—C11'	120.7 (6)
C6—C8—H8C	109.5	C11'—C10'—H10'	119.7
H8A—C8—H8B	109.5	C10'—C11'—H11'	120.0
H8A—C8—H8C	109.5	C10'—C11'—C12'	120.0 (6)
H8B—C8—H8C	109.5	C12'—C11'—H11'	120.0
C10—C9—P1	119.0 (5)	C11'—C12'—H12'	120.1
C10—C9—C14	118.6 (6)	C13'—C12'—C11'	119.8 (6)
C14—C9—P1	122.5 (5)	C13'—C12'—H12'	120.1
C9—C10—H10	119.4	C12'—C13'—H13'	119.9
C11—C10—C9	121.2 (6)	C12'—C13'—C14'	120.2 (7)
C11—C10—H10	119.4	C14'—C13'—H13'	119.9
C10—C11—H11	120.2	C9'—C14'—H14'	119.4
C10—C11—C12	119.6 (7)	C13'—C14'—C9'	121.2 (6)
C12—C11—H11	120.2	C13'—C14'—H14'	119.4
C11—C12—H12	120.3	C16'—C15'—P1'	118.5 (5)
C13—C12—C11	119.4 (7)	C20'—C15'—P1'	122.4 (5)
C13—C12—H12	120.3	C20'—C15'—C16'	118.7 (6)
C12—C13—H13	119.6	C15'—C16'—H16'	120.2
C14—C13—C12	120.8 (7)	C17'—C16'—C15'	119.5 (7)
C14—C13—H13	119.6	C17'—C16'—H16'	120.2
C9—C14—H14	119.8	C16'—C17'—H17'	119.5
C13—C14—C9	120.4 (7)	C18'—C17'—C16'	121.0 (7)
C13—C14—H14	119.8	C18'—C17'—H17'	119.5
C16—C15—P1	121.6 (6)	C17'—C18'—H18'	120.1
C20—C15—P1	119.0 (5)	C17'—C18'—C19'	119.9 (7)
C20—C15—C16	119.2 (7)	C19'—C18'—H18'	120.1
C15—C16—H16	120.1	C18'—C19'—H19'	120.2
C17—C16—C15	119.8 (8)	C18'—C19'—C20'	119.6 (7)
C17—C16—H16	120.1	C20'—C19'—H19'	120.2
C16—C17—H17	119.2	C15'—C20'—C19'	121.2 (6)
C16—C17—C18	121.6 (8)	C15'—C20'—H20'	119.4
C18—C17—H17	119.2	C19'—C20'—H20'	119.4
C17—C18—H18	120.7	C22'—C21'—P1'	119.8 (5)
C19—C18—C17	118.6 (8)	C22'—C21'—C26'	118.7 (6)
C19—C18—H18	120.7	C26'—C21'—P1'	121.6 (5)
C18—C19—H19	119.4	C21'—C22'—H22'	119.5
C18—C19—C20	121.2 (9)	C23'—C22'—C21'	121.1 (6)
C20—C19—H19	119.4	C23'—C22'—H22'	119.5
C15—C20—C19	119.6 (7)	C22'—C23'—H23'	120.1
C15—C20—H20	120.2	C22'—C23'—C24'	119.7 (7)
C19—C20—H20	120.2	C24'—C23'—H23'	120.1
C22—C21—P1	123.1 (5)	C23'—C24'—H24'	119.8
C22—C21—C26	118.9 (6)	C25'—C24'—C23'	120.4 (6)
C26—C21—P1	118.0 (5)	C25'—C24'—H24'	119.8
C21—C22—H22	119.8	C24'—C25'—H25'	119.6
C21—C22—C23	120.4 (7)	C24'—C25'—C26'	120.7 (6)
C23—C22—H22	119.8	C26'—C25'—H25'	119.6
C22—C23—H23	119.5	C21'—C26'—H26'	120.3
C24—C23—C22	120.9 (7)	C25'—C26'—C21'	119.4 (6)
C24—C23—H23	119.5	C25'—C26'—H26'	120.3
C23—C24—H24	120.1	Rh1'—C27'—H27'	113.8
C23—C24—C25	119.8 (6)	C28'—C27'—Rh1'	71.1 (4)
C25—C24—H24	120.1	C28'—C27'—H27'	113.8
C24—C25—H25	120.3	C28'—C27'—C34'	125.3 (6)
C24—C25—C26	119.5 (7)	C34'—C27'—Rh1'	111.3 (4)
C26—C25—H25	120.3	C34'—C27'—H27'	113.8
C21—C26—H26	119.8	Rh1'—C28'—H28'	114.0
C25—C26—C21	120.5 (7)	C27'—C28'—Rh1'	72.5 (4)
C25—C26—H26	119.8	C27'—C28'—H28'	114.0
Rh1—C27—H27	113.8	C27'—C28'—C29'	126.0 (6)
C28—C27—Rh1	72.2 (4)	C29'—C28'—Rh1'	108.3 (5)
C28—C27—H27	113.8	C29'—C28'—H28'	114.0
C28—C27—C34	125.9 (7)	C28'—C29'—H29C	108.9
C34—C27—Rh1	109.4 (5)	C28'—C29'—H29D	108.9
C34—C27—H27	113.8	C28'—C29'—C30'	113.5 (6)
Rh1—C28—H28	113.6	H29C—C29'—H29D	107.7
C27—C28—Rh1	71.3 (4)	C30'—C29'—H29C	108.9
C27—C28—H28	113.6	C30'—C29'—H29D	108.9
C27—C28—C29	125.7 (6)	C29'—C30'—H30C	109.1
C29—C28—Rh1	111.5 (5)	C29'—C30'—H30D	109.1
C29—C28—H28	113.6	H30C—C30'—H30D	107.9
C28—C29—H29A	108.9	C31'—C30'—C29'	112.4 (5)
C28—C29—H29B	108.9	C31'—C30'—H30C	109.1
H29A—C29—H29B	107.7	C31'—C30'—H30D	109.1
C30—C29—C28	113.4 (6)	Rh1'—C31'—H31'	113.2
C30—C29—H29A	108.9	C30'—C31'—Rh1'	112.6 (4)
C30—C29—H29B	108.9	C30'—C31'—H31'	113.2
C29—C30—H30A	108.8	C32'—C31'—Rh1'	71.8 (4)
C29—C30—H30B	108.8	C32'—C31'—C30'	125.6 (6)
C29—C30—C31	113.9 (6)	C32'—C31'—H31'	113.2
H30A—C30—H30B	107.7	Rh1'—C32'—H32'	113.8
C31—C30—H30A	108.8	C31'—C32'—Rh1'	71.9 (4)
C31—C30—H30B	108.8	C31'—C32'—H32'	113.8
Rh1—C31—H31	114.6	C31'—C32'—C33'	127.1 (7)
C30—C31—Rh1	106.5 (5)	C33'—C32'—Rh1'	107.9 (5)
C30—C31—H31	114.6	C33'—C32'—H32'	113.8
C32—C31—Rh1	72.9 (4)	C32'—C33'—H33C	109.0
C32—C31—C30	125.2 (7)	C32'—C33'—H33D	109.0
C32—C31—H31	114.6	C32'—C33'—C34'	113.0 (6)
Rh1—C32—H32	113.9	H33C—C33'—H33D	107.8
C31—C32—Rh1	71.1 (4)	C34'—C33'—H33C	109.0
C31—C32—H32	113.9	C34'—C33'—H33D	109.0
C31—C32—C33	125.2 (6)	C27'—C34'—C33'	112.8 (5)
C33—C32—Rh1	110.9 (5)	C27'—C34'—H34C	109.0
C33—C32—H32	113.9	C27'—C34'—H34D	109.0
C32—C33—H33A	108.9	C33'—C34'—H34C	109.0
C32—C33—H33B	108.9	C33'—C34'—H34D	109.0
C32—C33—C34	113.4 (5)	H34C—C34'—H34D	107.8
H33A—C33—H33B	107.7	F2—B1—F1	107.8 (7)
C34—C33—H33A	108.9	F2—B1—F3	109.5 (8)
C34—C33—H33B	108.9	F3—B1—F1	110.0 (8)
C27—C34—C33	112.7 (6)	F4—B1—F1	108.0 (7)
C27—C34—H34A	109.0	F4—B1—F2	110.9 (7)
C27—C34—H34B	109.0	F4—B1—F3	110.5 (6)
C33—C34—H34A	109.0	F5—B2—F6	102.2 (12)
C33—C34—H34B	109.0	F5—B2—F7	104.3 (11)
H34A—C34—H34B	107.8	F5—B2—F8	106.1 (12)
C1'—Rh1'—P1'	89.8 (2)	F6—B2—F5	113.4 (14)
C1'—Rh1'—C27'	159.2 (3)	F6—B2—F7	113.8 (17)
C1'—Rh1'—C28'	163.4 (3)	F6—B2—F8	110.8 (16)
C1'—Rh1'—C31'	93.4 (3)	F7—B2—F6	106.1 (14)
C1'—Rh1'—C32'	87.5 (3)	F7—B2—F5	103.7 (12)
C27'—Rh1'—P1'	98.72 (16)	F7—B2—F8	108.5 (11)
C28'—Rh1'—P1'	90.87 (19)	F8—B2—F5	113.8 (13)
C28'—Rh1'—C27'	36.4 (3)	F8—B2—F6	113.7 (15)
C28'—Rh1'—C31'	79.7 (3)	F8—B2—F7	115.5 (12)

Rh1—P1—C9—C10	24.0 (6)	Rh1'—P1'—C9'—C10'	109.3 (5)
Rh1—P1—C9—C14	−154.5 (6)	Rh1'—P1'—C9'—C14'	−66.0 (5)
Rh1—P1—C15—C16	−116.9 (5)	Rh1'—P1'—C15'—C16'	−62.2 (5)
Rh1—P1—C15—C20	59.3 (6)	Rh1'—P1'—C15'—C20'	110.6 (5)
Rh1—P1—C21—C22	−105.0 (5)	Rh1'—P1'—C21'—C22'	−28.4 (6)
Rh1—P1—C21—C26	71.7 (6)	Rh1'—P1'—C21'—C26'	150.9 (5)
Rh1—C27—C28—C29	−103.6 (7)	Rh1'—C27'—C28'—C29'	−100.2 (7)
Rh1—C27—C34—C33	39.8 (7)	Rh1'—C27'—C34'—C33'	−13.2 (7)
Rh1—C28—C29—C30	11.8 (7)	Rh1'—C28'—C29'—C30'	−40.7 (7)
Rh1—C31—C32—C33	−102.7 (7)	Rh1'—C31'—C32'—C33'	−99.1 (7)
Rh1—C32—C33—C34	13.4 (7)	Rh1'—C32'—C33'—C34'	−42.9 (7)
P1—C9—C10—C11	−179.0 (6)	P1'—C9'—C10'—C11'	−174.7 (5)
P1—C9—C14—C13	178.3 (6)	P1'—C9'—C14'—C13'	173.9 (5)
P1—C15—C16—C17	174.1 (6)	P1'—C15'—C16'—C17'	173.2 (5)
P1—C15—C20—C19	−173.8 (5)	P1'—C15'—C20'—C19'	−173.2 (5)
P1—C21—C22—C23	174.9 (5)	P1'—C21'—C22'—C23'	−178.5 (6)
P1—C21—C26—C25	−174.3 (5)	P1'—C21'—C26'—C25'	179.7 (5)
N1—N2—C2—N3	0.2 (8)	N1'—N2'—C2'—N3'	−0.5 (9)
N2—N1—C1—Rh1	178.5 (5)	N2'—N1'—C1'—Rh1'	179.5 (5)
N2—N1—C1—N3	0.6 (8)	N2'—N1'—C1'—N3'	0.8 (8)
N2—N1—C3—C4	−57.3 (8)	N2'—N1'—C3'—C4'	58.1 (9)
N3—C5—C6—C7	−170.1 (6)	N3'—C5'—C6'—C7'	−171.6 (6)
N3—C5—C6—C8	67.3 (8)	N3'—C5'—C6'—C8'	64.6 (8)
C1—N1—N2—C2	−0.5 (8)	C1'—N1'—N2'—C2'	−0.2 (8)
C1—N1—C3—C4	128.9 (7)	C1'—N1'—C3'—C4'	−123.0 (8)
C1—N3—C2—N2	0.2 (8)	C1'—N3'—C2'—N2'	1.0 (9)
C1—N3—C5—C6	−142.1 (7)	C1'—N3'—C5'—C6'	−134.7 (7)
C2—N3—C1—Rh1	−178.1 (6)	C2'—N3'—C1'—Rh1'	−179.8 (5)
C2—N3—C1—N1	−0.4 (7)	C2'—N3'—C1'—N1'	−1.1 (8)
C2—N3—C5—C6	46.2 (10)	C2'—N3'—C5'—C6'	50.7 (9)
C3—N1—N2—C2	−174.9 (6)	C3'—N1'—N2'—C2'	178.9 (6)
C3—N1—C1—Rh1	−7.4 (10)	C3'—N1'—C1'—Rh1'	0.5 (11)
C3—N1—C1—N3	174.6 (6)	C3'—N1'—C1'—N3'	−178.2 (6)
C5—N3—C1—Rh1	8.7 (11)	C5'—N3'—C1'—Rh1'	4.7 (10)
C5—N3—C1—N1	−173.6 (6)	C5'—N3'—C1'—N1'	−176.5 (6)
C5—N3—C2—N2	173.1 (7)	C5'—N3'—C2'—N2'	176.4 (7)
C9—P1—C15—C16	3.2 (6)	C9'—P1'—C15'—C16'	69.6 (5)
C9—P1—C15—C20	179.4 (5)	C9'—P1'—C15'—C20'	−117.7 (5)
C9—P1—C21—C22	135.3 (6)	C9'—P1'—C21'—C22'	−155.3 (5)
C9—P1—C21—C26	−48.0 (6)	C9'—P1'—C21'—C26'	24.0 (6)
C9—C10—C11—C12	2.1 (11)	C9'—C10'—C11'—C12'	0.9 (10)
C10—C9—C14—C13	−0.2 (11)	C10'—C9'—C14'—C13'	−1.7 (9)
C10—C11—C12—C13	−3.0 (12)	C10'—C11'—C12'—C13'	−1.5 (10)
C11—C12—C13—C14	2.3 (12)	C11'—C12'—C13'—C14'	0.5 (10)
C12—C13—C14—C9	−0.7 (12)	C12'—C13'—C14'—C9'	1.2 (10)
C14—C9—C10—C11	−0.5 (10)	C14'—C9'—C10'—C11'	0.7 (9)
C15—P1—C9—C10	−100.9 (6)	C15'—P1'—C9'—C10'	−20.4 (6)
C15—P1—C9—C14	80.6 (6)	C15'—P1'—C9'—C14'	164.3 (5)
C15—P1—C21—C22	25.7 (6)	C15'—P1'—C21'—C22'	94.3 (6)
C15—P1—C21—C26	−157.6 (5)	C15'—P1'—C21'—C26'	−86.5 (6)
C15—C16—C17—C18	0.4 (12)	C15'—C16'—C17'—C18'	−0.1 (11)
C16—C15—C20—C19	2.6 (10)	C16'—C15'—C20'—C19'	−0.5 (9)
C16—C17—C18—C19	0.9 (12)	C16'—C17'—C18'—C19'	0.4 (11)
C17—C18—C19—C20	−0.5 (12)	C17'—C18'—C19'—C20'	−0.7 (11)
C18—C19—C20—C15	−1.3 (11)	C18'—C19'—C20'—C15'	0.8 (10)
C20—C15—C16—C17	−2.2 (10)	C20'—C15'—C16'—C17'	0.1 (9)
C21—P1—C9—C10	148.3 (6)	C21'—P1'—C9'—C10'	−129.3 (5)
C21—P1—C9—C14	−30.2 (7)	C21'—P1'—C9'—C14'	55.3 (5)
C21—P1—C15—C16	112.5 (6)	C21'—P1'—C15'—C16'	178.6 (5)
C21—P1—C15—C20	−71.2 (6)	C21'—P1'—C15'—C20'	−8.6 (6)
C21—C22—C23—C24	0.5 (10)	C21'—C22'—C23'—C24'	−1.9 (12)
C22—C21—C26—C25	2.5 (10)	C22'—C21'—C26'—C25'	−1.0 (9)
C22—C23—C24—C25	0.1 (11)	C22'—C23'—C24'—C25'	0.4 (12)
C23—C24—C25—C26	0.6 (11)	C23'—C24'—C25'—C26'	0.7 (11)
C24—C25—C26—C21	−2.0 (10)	C24'—C25'—C26'—C21'	−0.4 (10)
C26—C21—C22—C23	−1.8 (10)	C26'—C21'—C22'—C23'	2.2 (10)
C27—C28—C29—C30	93.7 (9)	C27'—C28'—C29'—C30'	40.6 (10)
C28—C27—C34—C33	−41.8 (10)	C28'—C27'—C34'—C33'	−94.6 (8)
C28—C29—C30—C31	−35.6 (8)	C28'—C29'—C30'—C31'	35.4 (8)
C29—C30—C31—Rh1	40.3 (7)	C29'—C30'—C31'—Rh1'	−11.8 (7)
C29—C30—C31—C32	−40.1 (10)	C29'—C30'—C31'—C32'	−95.0 (8)
C30—C31—C32—Rh1	98.4 (7)	C30'—C31'—C32'—Rh1'	105.2 (6)
C30—C31—C32—C33	−4.3 (11)	C30'—C31'—C32'—C33'	6.1 (11)
C31—C32—C33—C34	94.5 (8)	C31'—C32'—C33'—C34'	37.6 (9)
C32—C33—C34—C27	−35.7 (8)	C32'—C33'—C34'—C27'	38.1 (8)
C34—C27—C28—Rh1	101.4 (8)	C34'—C27'—C28'—Rh1'	103.2 (6)
C34—C27—C28—C29	−2.1 (12)	C34'—C27'—C28'—C29'	3.0 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F3ⁱ	0.95	2.36	3.177 (8)	144
C8—H8C···F1	0.98	2.50	3.404 (10)	153
C13—H13···F5*	0.95	2.52	3.396 (17)	153
C20—H20···F2ⁱⁱ	0.95	2.34	3.291 (9)	178
C16′—H16′···F7*	0.95	2.40	3.351 (17)	177
C29′—H29D···F8ⁱⁱ	0.99	2.51	3.37 (2)	146

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

Acknowledgements

TGL was supported in this work by the Millersville University Neimeyer–Hodgson student research grant and student grants for research and creativity activities.

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