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The title compounds, [(1R,1′R,2R,2′R)-2,2′-bis­(di­phenyl­phos­phanyl)-1,1′-di­cyclo­pentane](η4-norborna­diene)rhodium(I) tetra­fluorido­borate, [Rh(C34H36P2)(C7H8)]BF4, (I), and [(1R,1′R,2R,2′R)-2,2′-bis­(di­phenyl­phosphanyl)-1,1′-di­cyclo­pen­tane][η4-(Z,Z)-cyclo­octa-1,5-diene]rhodium(I) tetra­fluorido­borate di­chloro­methane mono­solvate, [Rh(C34H36P2)(C8H12)]BF4·CH2Cl2, (II), are applied as precatalysts in asymmetric homogeneous hydrogenation, e.g. in the reduction of de­hydro­amino acids, affording excellent enantio­meric excesses [Zhu, Cao, Jiang & Zhang (1997). J. Am. Chem. Soc. 119, 1799–1800].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961401910X/eg3166sup1.cif
Contains datablocks RhBICPnbdBF4, RhBICPcodBF4, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961401910X/eg3166RhBICPnbdBF4sup2.hkl
Contains datablock RhBICPnbdBF4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961401910X/eg3166RhBICPcodBF4sup3.hkl
Contains datablock RhBICPcodBF4

CCDC references: 1020873; 1020874

Introduction top

One of our main inter­ests lies in the field of homogeneous asymmetric catalysis, with a special focus on asymmetric hydrogenation promoted by chiral rhodium bis­phosphine complexes. Relevant ligands in this context are shown in Scheme 1. Besides the well known chiral ligands which form five-membered ring chelates, e.g. DIPAMP {1,2-bis­[(2-meth­oxy­phenyl)(phenyl)­phosphanyl]ethane; Knowles et al., 1972} or ChiraPHOS [(2S,3S)-2,3-bis­(di­phenyl­phosphanyl)butane; Fryzuk & Bosnich, 1977], there are many established ligands which give rise to larger seven-membered-ring chelates, e.g. DIOP [4,5-bis­(di­phenyl­phosphanyl)-2,2-di­methyl-1,3-dioxolane; Kagan & Dang, 1972] or BINAP [2,2'-bis­(di­phenyl­phosphanyl)-1,1'-bi­naphthalene; Miyashita et al., 1980]. While the former possess rather stiff backbones, seven-membered ring chelates are more flexible and can adopt several conformations.

Recently, Zhang et al. [Reference?] developed a novel ligand, BICP [systematic name: 2,2'-bis­(di­phenyl­phosphanyl)-1,1'-bi­cyclo­pentane] (Scheme 1), which is able to coordinate to rhodium affording a seven-membered chelate complex. The authors reported that the resulting chelate has reduced conformational freedom because of the two cyclo­pentane rings in the ligand backbone. Additionally, they calculated (MM2) that the four stereogenic centres in the rhodium–BICP complex di­ctate the orientation of the phenyl groups in alternate sterically hindered and non-hindered quadrants. The preferred conformation adopted by the ligand in the metal complex should be a skewed seven-membered ring (Zhu et al., 1997). Such a conformation should result in higher enanti­oselectivity. However, the first structures of rhodium–BICP complexes (Scheme 2), viz. [Rh(BICP)(nbd)]BF4 (ndb is norbornadiene), (I), and [Rh(BICP)(cod)]BF4 (cod is cyclo­octa-1,5-diene), (II), which we present in this article, suggest that this assumption is not correct.

Experimental top

All manipulations were carried out using standard Schlenk techniques under argon. NMR spectra were recorded on a Bruker ARX-300 spectrometer. Hydrogen consumptions were monitored using the device described by Drexler et al. (2007).

Synthesis and crystallization top

The cationic complexes [Rh(BICP)(nbd)]BF4, (I), and [Rh(BICP)(cod)]BF4, (II), were prepared by reaction of [Rh(diolefin)(acac)] (acac is acetyl­acetate) and BICP, followed by addition of HBF4 to the resulting solution, according to a modification of a previously published procedure (Schrock & Osborn, 1971).

For the preparation of [Rh(BICP)(cod)]BF4, (I), a dry argon-flushed Schlenk tube was charged with Rh(cod)(acac) (97.2 mg, 0.313 mmol) and tetra­hydro­furan (THF, 10 ml). A solution of BICP (158 mg, 0.313 mmol) in THF (10 ml) was added dropwise at 273 K. After stirring for 30 min at room temperature, 39 µl of an 8 M solution of HBF4 in Et2O were added. The resulting mixture was stirred for 1 h. Upon addition of Et2O, complex (I) precipitated. It was filtered off and washed with Et2O. Crystals suitable for X-ray analysis were grown by slow diffusion of n-hexane into a CH2Cl2 solution.

For the preparation of [Rh(BICP)(nbd)]BF4, (II), a dry argon-flushed Schlenk tube was charged with Rh(nbd)(acac) (92.1 mg, 0.313 mmol) and THF (10 ml). A solution of BICP (158 mg, 0.313 mmol) in THF (10 ml) was added dropwise at 273 K. After stirring for 30 min at room temperature, 39 µl of a 8 M solution of HBF4 in Et2O were added. The resulting mixture was stirred for 1 h. Upon addition of Et2O, complex (II) precipitated. It was filtered off and washed with Et2O. Crystals suitable for X-ray analysis were grown by slow diffusion of Et2O into the THF solution.

Spectroscopic analysis: 31P NMR (MeOH-d4, 298 K, 121 MHz, δ, p.p.m.): (I), 26.0 (d, JP—Rh = 141.2 Hz); (II) 28.9 (d, JP—Rh = 150.9 Hz).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms were placed in idealized positions, with C—H = 0.93–0.98 (CH) and 0.97 Å (CH2), and were refined using a riding model, with Uiso(H) = 1.2Ueq(C). The absolute configuration indicators 2R,2'R and 1R,1'R for (I) and (II) were determined using 5782 and 4694 Friedel pairs, resectively, in the refinement. The Flack parameters (Flack, 1983) at convergence were -0.032 (18) for (I) and -0.015 (5) for (II).

The anisotropic displacement parameters of atom C51 and neighbouring C atoms C52 and C55 in (I) were restrained to be more equal in the Uij components.

After refinement of the BF4- anion in (II), residual electron density and large anisotropic displacement parameters for the F atoms indicated an alternative orientation for this group. The occupancy of the alternative orientations was refined and their sum was constrained to unity; refinement converged for a ratio of 0.655 (11):0.345 (11) between the major and minor orientations. The disordered BF4- anion in (II) was constrained by similarity constraints to resemble an ideal tetra­hedron.

Structural commentary top

The title compounds, (I) and (II), crystallize in the noncentrosymmetric space group P21 as red crystals. Compound (I) contains two cations and two anions in the asymmetric unit. The cationic complex of rhodium(I) coordinates to a BICP ligand and a bidentate h2,h2-coordinated norborna-2,5-diene. The unit cell of (II) contains one cation, one anion and a cocrystallized di­chloro­methane molecule per unit cell. The metal centre is coordinated by the BICP and the h2,h2-coordinated cyclo­octa-1,5-diene. The intra­molecular P—Rh—P bite angles are 94.25 (7) and 94.88 (7)° for nbd, and 91.85 (2)° for cod. The dihedral angles between the P/Rh/P and CM/Rh/CM planes (CM is the centroid of the double bond) are 9.5 (2) and 11.2 (2)° for nbd, and 14.2 (1)° for cod. These values and the bond lengths and angles in the coordination environments (Table 2) are in the same ranges as for related rhodium complexes of BINAP (Preetz et al., 2010).

Discussion top

In the three independent cations in (I) and (II), we consistently found that all C atoms should be located in or above the P—Rh—P plane (Fig. 3a and Table 3). This means strong deviations from the ideal skew conformation. Nevertheless, the rhodium–BICP complexes afforded very good enanti­oselectivities in the asymmetric hydrogenation of standard substrates (Zhu et al., 1997). In contrast, in almost all examined X-ray structures of rhodium complexes containing BINAP, a ligand with a less flexible backbone (all sp2 C atoms), we found a skew conformation (Preetz et al., 2010, 2011) (Fig. 3b). In such complexes, the C atoms are arranged symmetrically above and below the P—Rh—P plane (Table 3). However, asymmetric hydrogenation of standard substrates with rhodium–BINAP complexes as catalysts leads to poor enanti­oselectivities (Preetz et al., 2010).

Catalytic hydrogenations of cod and nbd, respectively, with [Rh(BICP)(nbd)]BF4 or [Rh(BICP)(cod)]BF4 have been carried out in MeOH according to Preetz et al. (2008) and Heller et al. (2007). Fig. 4 shows the hydrogen consumption curves for the catalytic hydrogenation of a ca 100-fold excess of cod and nbd. Pseudo-rate constants were determined from the slope of the hydrogen consumption from the linear part of the curve, which represents the hydrogenation of the first double bond of the diolefin. For the hydrogenation of nbd, we obtained 2.225 min-1, and for cod 0.056 min-1. This gives a ratio of k'2nnbd/k'2cod of 39.7. The rate constants are slightly lower than those we found for other seven-membered rhodium complexes (Meißner et al., 2014).

Related literature top

For related literature, see: Drexler et al. (2007); Flack (1983); Fryzuk & Bosnich (1977); Heller et al. (2007); Kagan & Dang (1972); Knowles et al. (1972); Meißner, Alberico, Drexler, Baumann & Heller (2014); Miyashita et al. (1980); Preetz et al. (2008, 2010, 2011); Schrock & Osborn (1971); Zhu et al. (1997).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005) for RhBICPnbdBF4; APEX2 (Bruker, 2009) for RhBICPcodBF4. Cell refinement: X-AREA (Stoe & Cie, 2005) for RhBICPnbdBF4; SAINT (Bruker, 2009) for RhBICPcodBF4. Data reduction: X-RED32 (Stoe & Cie, 2005) for RhBICPnbdBF4; SAINT (Bruker, 2009) for RhBICPcodBF4. For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the cations of [Rh(BICP)(nbd)]BF4, (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omitted for clarity. The relative orientation of the two molecules in the plot does not reflect their true orientation in the asymmetric unit.
[Figure 2] Fig. 2. A view of the cation of [Rh(BICP)(cod)]BF4, (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omitted for clarity.
[Figure 3] Fig. 3. Extract of molecular structures from X-ray diffraction analysis showing the seven-membered chelates of (a) [Rh(BICP)(cod)]BF4, (II) (pronounced deviation from skew conformation), and (b) [Rh(BINAP)(thf)2]BF4 (thf is tetrahydrofuran; skew conformation) (Preetz et al., 2011). The figure was prepared using SCHAKAL (Keller & Pierrard, 1999).
[Figure 4] Fig. 4. Hydrogen consumption for the hydrogenation of a 100-fold excess of cod (red) and nbd (green) {standard conditions: 0.01 mmol [Rh(BICP)(diolefine)]BF4, 1.0 mmol cod or nbd, 15 ml MeOH 298 K and 1.01 bar overall pressure (1 bar = 100000 Pa)}.
(RhBICPnbdBF4) [(1R,1'R,2R,2'R)-2,2'-Bis(diphenylphosphanyl)-1,1'-dicyclopentane](η4-norbornadiene)rhodium(I) tetrafluoroborate top
Crystal data top
[Rh(C34H36P2)(C7H8)]BF4F(000) = 1624
Mr = 788.42Dx = 1.483 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 10.002 (2) ÅCell parameters from 16122 reflections
b = 9.0293 (18) Åθ = 2.0–26.8°
c = 39.251 (8) ŵ = 0.63 mm1
β = 95.17 (3)°T = 200 K
V = 3530.4 (12) Å3Prism, red
Z = 40.34 × 0.28 × 0.25 mm
Data collection top
Stoe IPDS 2
diffractometer
12426 independent reflections
Radiation source: fine-focus sealed tube7748 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.087
Detector resolution: 6.67 pixels mm-1θmax = 25.0°, θmin = 1.6°
rotation method scansh = 1111
Absorption correction: numerical
(X-SHAPE; Stoe & Cie, 2005)
k = 1010
Tmin = 0.453, Tmax = 0.897l = 4645
38678 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0481P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.83(Δ/σ)max = 0.002
12426 reflectionsΔρmax = 2.80 e Å3
883 parametersΔρmin = 1.09 e Å3
13 restraintsAbsolute structure: Flack (1983), with 5782 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (3)
Crystal data top
[Rh(C34H36P2)(C7H8)]BF4V = 3530.4 (12) Å3
Mr = 788.42Z = 4
Monoclinic, P21Mo Kα radiation
a = 10.002 (2) ŵ = 0.63 mm1
b = 9.0293 (18) ÅT = 200 K
c = 39.251 (8) Å0.34 × 0.28 × 0.25 mm
β = 95.17 (3)°
Data collection top
Stoe IPDS 2
diffractometer
12426 independent reflections
Absorption correction: numerical
(X-SHAPE; Stoe & Cie, 2005)
7748 reflections with I > 2σ(I)
Tmin = 0.453, Tmax = 0.897Rint = 0.087
38678 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.103Δρmax = 2.80 e Å3
S = 0.83Δρmin = 1.09 e Å3
12426 reflectionsAbsolute structure: Flack (1983), with 5782 Friedel pairs
883 parametersAbsolute structure parameter: 0.03 (3)
13 restraints
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
xyzUiso*/Ueq
Rh10.18661 (9)0.65107 (6)0.36836 (3)0.0266 (4)
Rh20.30267 (9)0.01815 (6)0.13129 (3)0.0267 (4)
P10.1097 (3)0.7273 (3)0.41955 (7)0.0278 (7)
P20.0173 (3)0.7703 (3)0.33469 (7)0.0265 (6)
P30.3821 (3)0.0920 (3)0.08043 (7)0.0261 (7)
P40.4662 (2)0.1403 (3)0.16557 (6)0.0265 (6)
C10.0943 (10)0.9246 (10)0.4237 (3)0.032 (3)
H10.18670.95380.43110.038*
C20.0158 (11)0.9947 (11)0.4516 (3)0.038 (3)
H2A0.05800.97140.47420.046*
H2B0.07600.95870.44990.046*
C30.0193 (17)1.1637 (13)0.4449 (4)0.056 (4)
H3A0.07001.20580.44460.067*
H3B0.07761.21310.46250.067*
C40.0736 (12)1.1798 (11)0.4100 (3)0.037 (3)
H4A0.16711.20990.41270.044*
H4B0.02281.25400.39650.044*
C50.0596 (9)1.0285 (10)0.3925 (2)0.029 (2)
H50.12761.01810.37620.035*
C60.0811 (10)1.0109 (10)0.3738 (2)0.032 (2)
H60.14591.02350.39090.038*
C70.1144 (13)1.1272 (11)0.3460 (3)0.039 (3)
H7A0.03951.13990.33220.047*
H7B0.13391.22180.35620.047*
C80.2376 (12)1.0694 (11)0.3241 (3)0.041 (3)
H8A0.31821.11800.33050.049*
H8B0.22901.08890.30010.049*
C90.2454 (11)0.9041 (12)0.3304 (3)0.041 (3)
H9A0.24690.85030.30900.049*
H9B0.32610.88000.34120.049*
C100.1169 (10)0.8623 (10)0.3545 (3)0.027 (2)
H100.14650.79340.37160.032*
C110.2231 (11)0.6788 (10)0.4565 (3)0.027 (3)
C120.3420 (10)0.7604 (11)0.4639 (3)0.037 (3)
H120.36040.84030.45010.044*
C130.4320 (11)0.7231 (12)0.4914 (3)0.043 (3)
H130.51030.77790.49580.051*
C140.4072 (12)0.6076 (14)0.5119 (3)0.047 (3)
H140.46750.58490.53060.056*
C150.2924 (10)0.5232 (13)0.5050 (3)0.047 (3)
H150.27610.44280.51890.056*
C160.2018 (11)0.5592 (11)0.4774 (3)0.037 (3)
H160.12510.50180.47290.044*
C170.0444 (10)0.6340 (11)0.4284 (3)0.026 (3)
C180.1097 (12)0.6655 (14)0.4581 (4)0.039 (3)
H180.07540.73790.47330.047*
C190.2262 (11)0.5875 (12)0.4646 (3)0.045 (3)
H190.26700.60420.48460.054*
C200.2804 (11)0.4845 (12)0.4406 (3)0.051 (3)
H200.36030.43680.44410.061*
C210.2165 (10)0.4531 (11)0.4118 (3)0.039 (3)
H210.25020.38100.39650.046*
C220.1020 (10)0.5305 (11)0.4063 (3)0.033 (2)
H220.06140.51120.38630.040*
C230.0807 (10)0.9028 (10)0.3052 (3)0.030 (2)
C240.2079 (10)0.9672 (10)0.3130 (3)0.034 (2)
H240.26260.93500.33200.041*
C250.2510 (12)1.0779 (12)0.2926 (3)0.045 (3)
H250.33531.11950.29800.054*
C260.1740 (14)1.1280 (14)0.2648 (4)0.044 (3)
H260.20361.20630.25210.053*
C270.0503 (12)1.0616 (11)0.2554 (3)0.043 (3)
H270.00011.09140.23550.052*
C280.0021 (11)0.9522 (10)0.2754 (3)0.035 (2)
H280.08180.91060.26940.042*
C290.0683 (11)0.6342 (12)0.3067 (3)0.031 (3)
C300.1788 (9)0.5533 (10)0.3169 (3)0.031 (2)
H300.21610.57860.33700.037*
C310.2317 (10)0.4368 (11)0.2973 (3)0.037 (3)
H310.30640.38680.30390.044*
C320.1761 (11)0.3939 (13)0.2682 (3)0.044 (3)
H320.21040.31240.25590.053*
C330.0678 (11)0.4723 (11)0.2572 (3)0.040 (3)
H330.03100.44510.23720.048*
C340.0167 (11)0.5895 (12)0.2761 (3)0.038 (3)
H340.05500.64170.26850.045*
C350.3088 (10)0.5967 (12)0.3257 (3)0.034 (2)
H350.30070.64730.30350.041*
C360.2341 (10)0.4744 (10)0.3333 (3)0.034 (2)
H360.16610.43090.31670.040*
C370.3215 (9)0.3803 (10)0.3586 (3)0.030 (2)
H370.29610.27610.36060.036*
C380.3230 (11)0.4761 (10)0.3915 (3)0.039 (3)
H380.31560.43450.41430.047*
C390.3978 (10)0.5989 (11)0.3856 (3)0.036 (3)
H390.45030.65350.40380.043*
C400.4421 (11)0.5801 (12)0.3487 (3)0.041 (3)
H400.51790.64080.34280.049*
C410.4603 (10)0.4114 (11)0.3474 (3)0.037 (3)
H41A0.47180.37490.32470.044*
H41B0.53210.37570.36360.044*
C510.3959 (11)0.3065 (12)0.0764 (3)0.035 (2)
H510.30470.33740.06820.042*
C520.4810 (11)0.3575 (10)0.0479 (3)0.039 (3)
H52A0.44090.32980.02540.047*
H52B0.57210.31990.05120.047*
C530.4748 (16)0.5283 (14)0.0540 (4)0.051 (4)
H53A0.56430.57040.05610.061*
H53B0.42230.57620.03510.061*
C540.4091 (12)0.5487 (11)0.0869 (3)0.036 (3)
H54A0.31450.57150.08210.043*
H54B0.45170.62870.10030.043*
C550.4279 (10)0.3961 (10)0.1069 (3)0.031 (2)
H550.35770.38470.12250.037*
C560.5651 (10)0.3805 (11)0.1263 (3)0.032 (2)
H560.63100.39380.10960.039*
C570.5925 (13)0.5020 (11)0.1530 (3)0.036 (3)
H57A0.51620.51390.16640.043*
H57B0.60930.59560.14200.043*
C580.7166 (12)0.4526 (12)0.1759 (3)0.044 (3)
H58A0.70760.47820.19950.052*
H58B0.79680.49950.16880.052*
C590.7239 (11)0.2831 (12)0.1715 (3)0.041 (3)
H59A0.71800.23410.19330.049*
H59B0.80800.25540.16270.049*
C600.6037 (10)0.2374 (10)0.1458 (3)0.033 (2)
H600.63840.16870.12940.040*
C610.2710 (10)0.0427 (11)0.0430 (3)0.029 (3)
C620.1501 (10)0.1202 (10)0.0356 (3)0.036 (3)
H620.12890.19790.04970.043*
C630.0621 (12)0.0829 (13)0.0076 (3)0.047 (3)
H630.01730.13590.00320.056*
C640.0911 (13)0.0325 (15)0.0137 (4)0.051 (3)
H640.03280.05530.03280.062*
C650.2068 (11)0.1133 (14)0.0064 (3)0.049 (3)
H650.22570.19280.02020.058*
C660.2959 (11)0.0757 (11)0.0218 (3)0.040 (3)
H660.37360.13130.02650.048*
C670.5387 (11)0.0008 (11)0.0727 (3)0.029 (3)
C680.5900 (9)0.1046 (10)0.0966 (3)0.031 (2)
H680.54730.12260.11630.037*
C690.7098 (11)0.1833 (11)0.0904 (3)0.044 (3)
H690.74460.25370.10610.053*
C700.7736 (11)0.1558 (11)0.0617 (3)0.046 (3)
H700.85200.20630.05790.055*
C710.7205 (11)0.0528 (13)0.0383 (3)0.045 (3)
H710.76380.03570.01870.053*
C720.6057 (12)0.0258 (12)0.0430 (3)0.036 (3)
H720.57260.09530.02690.043*
C730.3976 (10)0.2754 (11)0.1937 (3)0.032 (2)
C740.2725 (10)0.3388 (10)0.1840 (3)0.032 (2)
H740.22070.30150.16510.038*
C750.2241 (11)0.4564 (11)0.2021 (3)0.038 (3)
H750.14060.49690.19510.046*
C760.2979 (14)0.5134 (13)0.2301 (4)0.048 (4)
H760.26720.59520.24150.057*
C770.4221 (12)0.4456 (12)0.2414 (3)0.044 (3)
H770.47200.48020.26090.053*
C780.4681 (11)0.3291 (11)0.2234 (3)0.036 (3)
H780.54880.28440.23130.044*
C790.5514 (11)0.0102 (12)0.1952 (3)0.033 (3)
C800.4961 (11)0.0329 (11)0.2250 (3)0.035 (3)
H800.41920.01490.23090.042*
C810.5503 (12)0.1422 (12)0.2458 (3)0.043 (3)
H810.51180.16540.26580.052*
C820.6620 (11)0.2187 (11)0.2372 (3)0.043 (3)
H820.69780.29490.25120.051*
C830.7208 (11)0.1804 (11)0.2075 (3)0.042 (3)
H830.79710.22980.20170.051*
C840.6656 (11)0.0696 (10)0.1868 (3)0.036 (3)
H840.70420.04640.16680.044*
C850.1797 (11)0.0375 (12)0.1737 (3)0.035 (3)
H850.18800.01300.19590.042*
C860.2537 (11)0.1596 (10)0.1664 (3)0.033 (2)
H860.32120.20280.18320.040*
C870.1707 (10)0.2530 (11)0.1405 (3)0.035 (2)
H870.19700.35690.13830.042*
C880.1655 (10)0.1565 (10)0.1081 (3)0.036 (3)
H880.17220.19700.08510.043*
C890.0906 (10)0.0322 (13)0.1144 (3)0.040 (3)
H890.03820.02330.09630.048*
C900.0467 (12)0.0514 (13)0.1508 (3)0.043 (3)
H900.02900.00890.15700.052*
C910.0290 (10)0.2222 (13)0.1515 (3)0.045 (3)
H91A0.01640.26010.17410.054*
H91B0.04210.25730.13500.054*
B10.5125 (13)0.0297 (16)0.3946 (4)0.046 (3)
F10.4698 (8)0.0156 (13)0.3601 (2)0.090 (3)
F20.5735 (8)0.0958 (8)0.4075 (2)0.081 (3)
F30.4022 (7)0.0648 (10)0.4122 (2)0.077 (2)
F40.6041 (8)0.1456 (9)0.3975 (3)0.071 (3)
B20.9696 (14)0.3904 (16)0.1064 (4)0.049 (3)
F50.8890 (9)0.5118 (9)0.1004 (3)0.073 (3)
F61.0871 (7)0.4084 (10)0.0911 (2)0.080 (3)
F70.9044 (9)0.2694 (9)0.0926 (3)0.094 (3)
F81.0017 (7)0.3704 (13)0.1408 (2)0.097 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Rh10.0296 (5)0.0254 (7)0.0245 (9)0.0028 (4)0.0013 (5)0.0001 (4)
Rh20.0298 (5)0.0250 (7)0.0251 (9)0.0023 (4)0.0021 (5)0.0003 (4)
P10.0302 (15)0.0250 (14)0.0285 (18)0.0018 (11)0.0040 (13)0.0023 (11)
P20.0285 (14)0.0256 (13)0.0249 (16)0.0018 (11)0.0003 (12)0.0005 (11)
P30.0281 (14)0.0246 (14)0.0253 (17)0.0009 (10)0.0018 (12)0.0011 (11)
P40.0295 (13)0.0242 (13)0.0258 (16)0.0007 (12)0.0017 (11)0.0024 (13)
C10.028 (5)0.021 (5)0.047 (7)0.003 (4)0.005 (5)0.007 (5)
C20.053 (7)0.038 (6)0.024 (6)0.005 (5)0.006 (5)0.002 (5)
C30.104 (12)0.021 (6)0.044 (10)0.009 (6)0.016 (9)0.002 (5)
C40.052 (7)0.022 (6)0.034 (7)0.005 (5)0.009 (5)0.007 (5)
C50.039 (5)0.024 (4)0.025 (5)0.003 (5)0.005 (4)0.008 (5)
C60.045 (6)0.023 (4)0.027 (6)0.009 (5)0.001 (4)0.002 (5)
C70.056 (7)0.021 (6)0.038 (8)0.001 (5)0.009 (6)0.000 (5)
C80.048 (7)0.033 (5)0.039 (7)0.011 (5)0.001 (6)0.006 (5)
C90.039 (6)0.047 (6)0.036 (7)0.005 (5)0.002 (5)0.002 (5)
C100.034 (6)0.020 (5)0.025 (6)0.006 (4)0.004 (5)0.004 (4)
C110.035 (6)0.022 (5)0.025 (7)0.004 (4)0.001 (5)0.004 (5)
C120.039 (6)0.031 (5)0.039 (7)0.006 (5)0.000 (5)0.004 (5)
C130.036 (6)0.041 (6)0.048 (8)0.001 (5)0.012 (6)0.002 (6)
C140.037 (7)0.061 (8)0.042 (8)0.018 (6)0.000 (6)0.007 (7)
C150.040 (6)0.053 (6)0.049 (7)0.014 (6)0.009 (5)0.022 (7)
C160.032 (6)0.038 (6)0.039 (7)0.001 (4)0.000 (5)0.007 (5)
C170.029 (5)0.019 (5)0.028 (7)0.004 (4)0.006 (5)0.007 (4)
C180.037 (7)0.040 (7)0.040 (9)0.001 (5)0.007 (6)0.005 (6)
C190.036 (6)0.046 (6)0.056 (8)0.001 (5)0.017 (6)0.008 (6)
C200.029 (6)0.059 (8)0.064 (9)0.015 (5)0.001 (6)0.021 (6)
C210.030 (6)0.034 (5)0.051 (8)0.008 (4)0.004 (5)0.007 (5)
C220.044 (6)0.035 (5)0.023 (5)0.003 (5)0.010 (5)0.003 (5)
C230.038 (6)0.026 (5)0.026 (6)0.001 (4)0.003 (5)0.003 (4)
C240.036 (6)0.032 (5)0.034 (6)0.004 (4)0.004 (5)0.000 (4)
C250.053 (7)0.040 (6)0.043 (8)0.013 (5)0.015 (6)0.007 (6)
C260.061 (8)0.037 (7)0.036 (8)0.004 (6)0.017 (6)0.008 (6)
C270.059 (7)0.039 (6)0.032 (7)0.006 (5)0.009 (6)0.007 (5)
C280.043 (6)0.030 (5)0.031 (6)0.001 (4)0.003 (5)0.004 (5)
C290.029 (6)0.034 (6)0.028 (7)0.000 (5)0.006 (5)0.000 (5)
C300.025 (5)0.032 (6)0.036 (6)0.000 (4)0.003 (5)0.004 (4)
C310.030 (6)0.035 (5)0.045 (7)0.005 (4)0.005 (5)0.001 (5)
C320.047 (7)0.037 (5)0.047 (7)0.002 (5)0.011 (5)0.017 (5)
C330.043 (7)0.041 (6)0.036 (7)0.002 (5)0.003 (5)0.008 (5)
C340.033 (6)0.047 (6)0.032 (7)0.002 (5)0.000 (5)0.000 (5)
C350.036 (6)0.042 (6)0.025 (6)0.007 (5)0.001 (5)0.004 (5)
C360.032 (6)0.029 (5)0.039 (7)0.010 (4)0.001 (5)0.009 (4)
C370.018 (5)0.029 (5)0.043 (7)0.001 (4)0.007 (5)0.000 (5)
C380.046 (7)0.037 (6)0.035 (7)0.019 (5)0.005 (5)0.004 (5)
C390.036 (6)0.033 (5)0.037 (7)0.002 (5)0.008 (5)0.005 (5)
C400.029 (6)0.045 (6)0.048 (8)0.001 (5)0.008 (5)0.005 (5)
C410.026 (5)0.040 (6)0.044 (7)0.007 (5)0.001 (5)0.001 (5)
C510.033 (5)0.055 (6)0.018 (5)0.000 (5)0.004 (4)0.024 (5)
C520.054 (6)0.036 (6)0.028 (6)0.003 (5)0.007 (5)0.003 (5)
C530.082 (10)0.037 (8)0.034 (9)0.005 (6)0.011 (8)0.007 (6)
C540.047 (7)0.019 (5)0.043 (8)0.003 (5)0.013 (6)0.014 (5)
C550.038 (5)0.025 (5)0.029 (6)0.002 (4)0.004 (4)0.000 (4)
C560.035 (6)0.031 (5)0.030 (6)0.009 (5)0.003 (5)0.003 (5)
C570.055 (7)0.019 (5)0.033 (7)0.008 (5)0.005 (6)0.008 (5)
C580.051 (7)0.040 (6)0.038 (7)0.007 (5)0.004 (6)0.005 (5)
C590.041 (6)0.038 (6)0.041 (7)0.014 (5)0.006 (5)0.001 (5)
C600.030 (5)0.028 (5)0.039 (7)0.001 (4)0.006 (5)0.013 (5)
C610.028 (5)0.029 (6)0.031 (7)0.003 (4)0.005 (5)0.004 (5)
C620.036 (6)0.024 (5)0.046 (7)0.003 (4)0.005 (5)0.007 (4)
C630.035 (6)0.048 (7)0.056 (9)0.001 (5)0.006 (6)0.003 (6)
C640.050 (8)0.062 (8)0.041 (8)0.019 (7)0.002 (6)0.003 (7)
C650.039 (6)0.064 (7)0.043 (8)0.010 (6)0.003 (6)0.032 (6)
C660.033 (6)0.032 (6)0.053 (8)0.000 (4)0.002 (5)0.004 (5)
C670.030 (6)0.023 (5)0.033 (7)0.003 (4)0.003 (5)0.005 (5)
C680.028 (5)0.018 (4)0.045 (7)0.006 (4)0.009 (5)0.004 (5)
C690.044 (7)0.035 (6)0.052 (8)0.015 (5)0.003 (6)0.007 (5)
C700.031 (6)0.046 (7)0.061 (9)0.011 (5)0.006 (6)0.008 (6)
C710.036 (6)0.056 (7)0.045 (8)0.002 (5)0.015 (6)0.007 (6)
C720.045 (7)0.030 (6)0.032 (8)0.004 (5)0.002 (6)0.004 (5)
C730.034 (6)0.033 (5)0.028 (6)0.004 (4)0.003 (5)0.000 (5)
C740.038 (6)0.032 (5)0.026 (6)0.000 (4)0.004 (5)0.002 (4)
C750.037 (6)0.038 (5)0.041 (7)0.005 (5)0.009 (5)0.005 (5)
C760.062 (8)0.036 (6)0.047 (9)0.005 (6)0.019 (7)0.002 (6)
C770.055 (7)0.047 (6)0.031 (7)0.009 (6)0.004 (6)0.004 (5)
C780.033 (6)0.043 (6)0.033 (7)0.006 (4)0.005 (5)0.002 (5)
C790.028 (5)0.034 (6)0.038 (8)0.004 (5)0.003 (5)0.000 (5)
C800.040 (6)0.027 (5)0.038 (7)0.002 (4)0.004 (5)0.009 (5)
C810.055 (7)0.048 (6)0.026 (6)0.007 (5)0.005 (5)0.009 (5)
C820.047 (7)0.033 (5)0.045 (7)0.002 (5)0.010 (6)0.004 (5)
C830.042 (6)0.036 (6)0.048 (8)0.006 (5)0.004 (6)0.000 (5)
C840.042 (6)0.031 (5)0.036 (6)0.001 (5)0.003 (5)0.001 (5)
C850.042 (7)0.036 (6)0.027 (7)0.009 (5)0.006 (5)0.005 (5)
C860.045 (6)0.033 (5)0.022 (6)0.005 (5)0.004 (5)0.009 (4)
C870.038 (6)0.031 (5)0.035 (7)0.001 (4)0.006 (5)0.001 (5)
C880.036 (6)0.033 (6)0.038 (7)0.013 (4)0.006 (5)0.001 (5)
C890.023 (5)0.046 (6)0.049 (8)0.005 (5)0.006 (5)0.003 (6)
C900.039 (7)0.045 (6)0.045 (8)0.002 (5)0.002 (6)0.003 (6)
C910.027 (6)0.049 (6)0.063 (9)0.012 (5)0.015 (5)0.004 (6)
B10.042 (7)0.043 (7)0.051 (9)0.009 (7)0.005 (6)0.007 (7)
F10.061 (5)0.159 (9)0.049 (5)0.003 (6)0.006 (4)0.021 (6)
F20.085 (6)0.043 (4)0.110 (7)0.004 (4)0.013 (5)0.021 (5)
F30.045 (4)0.121 (7)0.066 (6)0.002 (4)0.011 (4)0.010 (5)
F40.067 (6)0.054 (5)0.091 (8)0.021 (5)0.003 (5)0.011 (4)
B20.049 (8)0.049 (8)0.049 (9)0.007 (7)0.006 (7)0.008 (7)
F50.069 (6)0.068 (6)0.079 (8)0.034 (5)0.005 (5)0.012 (5)
F60.045 (4)0.126 (7)0.072 (6)0.003 (5)0.020 (4)0.012 (5)
F70.089 (6)0.053 (5)0.134 (9)0.006 (5)0.015 (6)0.013 (5)
F80.040 (4)0.200 (11)0.050 (5)0.018 (6)0.005 (4)0.034 (6)
Geometric parameters (Å, º) top
Rh1—C362.187 (9)C38—C391.369 (14)
Rh1—C392.210 (10)C38—H380.9800
Rh1—C352.216 (11)C39—C401.561 (16)
Rh1—C382.226 (10)C39—H390.9800
Rh1—P22.317 (3)C40—C411.536 (15)
Rh1—P12.319 (3)C40—H400.9800
Rh2—C862.199 (9)C41—H41A0.9700
Rh2—C892.212 (10)C41—H41B0.9700
Rh2—C852.214 (11)C51—C551.456 (15)
Rh2—C882.230 (10)C51—C521.534 (13)
Rh2—P42.304 (3)C51—H510.9800
Rh2—P32.312 (3)C52—C531.562 (15)
P1—C11.797 (10)C52—H52A0.9700
P1—C111.813 (12)C52—H52B0.9700
P1—C171.818 (10)C53—C541.512 (18)
P2—C291.813 (12)C53—H53A0.9700
P2—C101.813 (10)C53—H53B0.9700
P2—C231.819 (10)C54—C551.587 (14)
P3—C611.817 (12)C54—H54A0.9700
P3—C671.824 (11)C54—H54B0.9700
P3—C511.950 (11)C55—C561.516 (14)
P4—C791.811 (12)C55—H550.9800
P4—C731.820 (10)C56—C571.523 (14)
P4—C601.859 (11)C56—C601.532 (14)
C1—C21.540 (14)C56—H560.9800
C1—C51.558 (13)C57—C581.532 (16)
C1—H10.9800C57—H57A0.9700
C2—C31.549 (15)C57—H57B0.9700
C2—H2A0.9700C58—C591.543 (15)
C2—H2B0.9700C58—H58A0.9700
C3—C41.525 (19)C58—H58B0.9700
C3—H3A0.9700C59—C601.553 (14)
C3—H3B0.9700C59—H59A0.9700
C4—C51.531 (13)C59—H59B0.9700
C4—H4A0.9700C60—H600.9800
C4—H4B0.9700C61—C661.389 (14)
C5—C61.536 (13)C61—C621.404 (14)
C5—H50.9800C62—C631.384 (15)
C6—C71.529 (15)C62—H620.9300
C6—C101.567 (13)C63—C641.383 (18)
C6—H60.9800C63—H630.9300
C7—C81.529 (16)C64—C651.376 (17)
C7—H7A0.9700C64—H640.9300
C7—H7B0.9700C65—C661.399 (15)
C8—C91.517 (16)C65—H650.9300
C8—H8A0.9700C66—H660.9300
C8—H8B0.9700C67—C681.390 (15)
C9—C101.572 (14)C67—C721.417 (17)
C9—H9A0.9700C68—C691.433 (14)
C9—H9B0.9700C68—H680.9300
C10—H100.9800C69—C701.369 (16)
C11—C161.384 (14)C69—H690.9300
C11—C121.407 (14)C70—C711.378 (16)
C12—C131.384 (15)C70—H700.9300
C12—H120.9300C71—C721.376 (16)
C13—C141.353 (16)C71—H710.9300
C13—H130.9300C72—H720.9300
C14—C151.384 (16)C73—C781.396 (14)
C14—H140.9300C73—C741.397 (14)
C15—C161.387 (15)C74—C751.390 (14)
C15—H150.9300C74—H740.9300
C16—H160.9300C75—C761.368 (18)
C17—C221.366 (15)C75—H750.9300
C17—C181.416 (17)C76—C771.419 (17)
C18—C191.404 (16)C76—H760.9300
C18—H180.9300C77—C781.368 (14)
C19—C201.398 (17)C77—H770.9300
C19—H190.9300C78—H780.9300
C20—C211.374 (16)C79—C801.393 (17)
C20—H200.9300C79—C841.414 (15)
C21—C221.376 (14)C80—C811.360 (14)
C21—H210.9300C80—H800.9300
C22—H220.9300C81—C821.380 (15)
C23—C241.407 (14)C81—H810.9300
C23—C281.420 (14)C82—C831.398 (15)
C24—C251.374 (14)C82—H820.9300
C24—H240.9300C83—C841.372 (14)
C25—C261.355 (18)C83—H830.9300
C25—H250.9300C84—H840.9300
C26—C271.394 (17)C85—C861.372 (14)
C26—H260.9300C85—C901.541 (16)
C27—C281.375 (14)C85—H850.9800
C27—H270.9300C86—C871.511 (14)
C28—H280.9300C86—H860.9800
C29—C341.407 (16)C87—C881.541 (14)
C29—C301.413 (15)C87—C911.544 (14)
C30—C311.381 (14)C87—H870.9800
C30—H300.9300C88—C891.384 (14)
C31—C321.368 (16)C88—H880.9800
C31—H310.9300C89—C901.545 (16)
C32—C331.395 (16)C89—H890.9800
C32—H320.9300C90—C911.553 (16)
C33—C341.365 (14)C90—H900.9800
C33—H330.9300C91—H91A0.9700
C34—H340.9300C91—H91B0.9700
C35—C361.381 (14)B1—F21.363 (16)
C35—C401.550 (15)B1—F11.388 (16)
C35—H350.9800B1—F41.388 (15)
C36—C371.522 (14)B1—F31.391 (15)
C36—H360.9800B2—F71.360 (16)
C37—C411.519 (13)B2—F51.369 (15)
C37—C381.551 (14)B2—F81.370 (16)
C37—H370.9800B2—F61.377 (16)
C36—Rh1—C3977.4 (4)C39—C38—H38123.4
C36—Rh1—C3536.6 (4)C37—C38—H38123.4
C39—Rh1—C3566.9 (4)Rh1—C38—H38123.4
C36—Rh1—C3865.1 (4)C38—C39—C40105.8 (9)
C39—Rh1—C3835.9 (4)C38—C39—Rh172.7 (6)
C35—Rh1—C3877.9 (4)C40—C39—Rh194.7 (6)
C36—Rh1—P299.7 (3)C38—C39—H39123.4
C39—Rh1—P2154.5 (3)C40—C39—H39123.4
C35—Rh1—P295.5 (3)Rh1—C39—H39123.4
C38—Rh1—P2162.1 (3)C41—C40—C35100.1 (9)
C36—Rh1—P1150.4 (3)C41—C40—C39100.5 (9)
C39—Rh1—P1100.4 (3)C35—C40—C39103.3 (8)
C35—Rh1—P1165.7 (3)C41—C40—H40116.8
C38—Rh1—P195.5 (3)C35—C40—H40116.8
P2—Rh1—P194.25 (10)C39—C40—H40116.8
C86—Rh2—C8977.1 (4)C37—C41—C4093.4 (8)
C86—Rh2—C8536.2 (4)C37—C41—H41A113.0
C89—Rh2—C8566.2 (4)C40—C41—H41A113.0
C86—Rh2—C8865.0 (4)C37—C41—H41B113.0
C89—Rh2—C8836.3 (4)C40—C41—H41B113.0
C85—Rh2—C8877.5 (4)H41A—C41—H41B110.4
C86—Rh2—P499.8 (3)C55—C51—C52109.6 (9)
C89—Rh2—P4152.3 (3)C55—C51—P3119.8 (7)
C85—Rh2—P494.8 (3)C52—C51—P3113.9 (7)
C88—Rh2—P4162.8 (3)C55—C51—H51103.8
C86—Rh2—P3149.8 (3)C52—C51—H51103.8
C89—Rh2—P3101.2 (3)P3—C51—H51103.8
C85—Rh2—P3166.3 (3)C51—C52—C5398.8 (9)
C88—Rh2—P395.6 (3)C51—C52—H52A112.0
P4—Rh2—P394.88 (10)C53—C52—H52A112.0
C1—P1—C11102.7 (5)C51—C52—H52B112.0
C1—P1—C17111.1 (5)C53—C52—H52B112.0
C11—P1—C17102.4 (5)H52A—C52—H52B109.7
C1—P1—Rh1114.3 (4)C54—C53—C52106.1 (10)
C11—P1—Rh1112.9 (4)C54—C53—H53A110.5
C17—P1—Rh1112.4 (4)C52—C53—H53A110.5
C29—P2—C10104.1 (5)C54—C53—H53B110.5
C29—P2—C23103.4 (5)C52—C53—H53B110.5
C10—P2—C23106.6 (4)H53A—C53—H53B108.7
C29—P2—Rh1108.2 (4)C53—C54—C55105.9 (9)
C10—P2—Rh1120.0 (3)C53—C54—H54A110.5
C23—P2—Rh1113.0 (3)C55—C54—H54A110.5
C61—P3—C67103.0 (5)C53—C54—H54B110.5
C61—P3—C51102.7 (5)C55—C54—H54B110.5
C67—P3—C51112.0 (5)H54A—C54—H54B108.7
C61—P3—Rh2113.3 (4)C51—C55—C56119.0 (9)
C67—P3—Rh2112.2 (4)C51—C55—C5493.9 (8)
C51—P3—Rh2112.9 (3)C56—C55—C54113.1 (9)
C79—P4—C73103.1 (5)C51—C55—H55109.9
C79—P4—C60104.6 (5)C56—C55—H55109.9
C73—P4—C60105.7 (4)C54—C55—H55109.9
C79—P4—Rh2109.4 (4)C55—C56—C57112.2 (9)
C73—P4—Rh2112.8 (3)C55—C56—C60120.4 (8)
C60—P4—Rh2119.7 (3)C57—C56—C60104.1 (9)
C2—C1—C5102.8 (7)C55—C56—H56106.4
C2—C1—P1121.7 (7)C57—C56—H56106.4
C5—C1—P1122.7 (8)C60—C56—H56106.4
C2—C1—H1102.0C56—C57—C58106.2 (9)
C5—C1—H1102.0C56—C57—H57A110.5
P1—C1—H1102.0C58—C57—H57A110.5
C1—C2—C3105.3 (9)C56—C57—H57B110.5
C1—C2—H2A110.7C58—C57—H57B110.5
C3—C2—H2A110.7H57A—C57—H57B108.7
C1—C2—H2B110.7C57—C58—C59105.5 (9)
C3—C2—H2B110.7C57—C58—H58A110.6
H2A—C2—H2B108.8C59—C58—H58A110.6
C4—C3—C2105.2 (10)C57—C58—H58B110.6
C4—C3—H3A110.7C59—C58—H58B110.6
C2—C3—H3A110.7H58A—C58—H58B108.8
C4—C3—H3B110.7C58—C59—C60107.1 (9)
C2—C3—H3B110.7C58—C59—H59A110.3
H3A—C3—H3B108.8C60—C59—H59A110.3
C3—C4—C5107.1 (9)C58—C59—H59B110.3
C3—C4—H4A110.3C60—C59—H59B110.3
C5—C4—H4A110.3H59A—C59—H59B108.6
C3—C4—H4B110.3C56—C60—C59104.2 (8)
C5—C4—H4B110.3C56—C60—P4116.3 (7)
H4A—C4—H4B108.6C59—C60—P4114.3 (8)
C4—C5—C6110.5 (8)C56—C60—H60107.2
C4—C5—C1100.3 (8)C59—C60—H60107.2
C6—C5—C1116.3 (8)P4—C60—H60107.2
C4—C5—H5109.8C66—C61—C62117.2 (10)
C6—C5—H5109.8C66—C61—P3122.8 (8)
C1—C5—H5109.8C62—C61—P3119.8 (8)
C7—C6—C5113.6 (8)C63—C62—C61121.1 (10)
C7—C6—C10102.6 (8)C63—C62—H62119.5
C5—C6—C10118.6 (8)C61—C62—H62119.5
C7—C6—H6107.1C64—C63—C62120.6 (11)
C5—C6—H6107.1C64—C63—H63119.7
C10—C6—H6107.1C62—C63—H63119.7
C6—C7—C8106.2 (8)C65—C64—C63119.5 (12)
C6—C7—H7A110.5C65—C64—H64120.3
C8—C7—H7A110.5C63—C64—H64120.3
C6—C7—H7B110.5C64—C65—C66120.0 (11)
C8—C7—H7B110.5C64—C65—H65120.0
H7A—C7—H7B108.7C66—C65—H65120.0
C9—C8—C7107.2 (9)C61—C66—C65121.6 (10)
C9—C8—H8A110.3C61—C66—H66119.2
C7—C8—H8A110.3C65—C66—H66119.2
C9—C8—H8B110.3C68—C67—C72119.7 (10)
C7—C8—H8B110.3C68—C67—P3117.9 (9)
H8A—C8—H8B108.5C72—C67—P3122.3 (9)
C8—C9—C10106.4 (9)C67—C68—C69118.9 (11)
C8—C9—H9A110.4C67—C68—H68120.5
C10—C9—H9A110.4C69—C68—H68120.5
C8—C9—H9B110.4C70—C69—C68120.6 (10)
C10—C9—H9B110.4C70—C69—H69119.7
H9A—C9—H9B108.6C68—C69—H69119.7
C6—C10—C9103.0 (7)C69—C70—C71119.4 (10)
C6—C10—P2117.0 (7)C69—C70—H70120.3
C9—C10—P2116.7 (7)C71—C70—H70120.3
C6—C10—H10106.4C72—C71—C70122.4 (11)
C9—C10—H10106.4C72—C71—H71118.8
P2—C10—H10106.4C70—C71—H71118.8
C16—C11—C12117.4 (10)C71—C72—C67119.0 (11)
C16—C11—P1123.0 (8)C71—C72—H72120.5
C12—C11—P1119.6 (8)C67—C72—H72120.5
C13—C12—C11120.7 (10)C78—C73—C74117.2 (9)
C13—C12—H12119.7C78—C73—P4123.4 (8)
C11—C12—H12119.7C74—C73—P4119.1 (8)
C14—C13—C12120.7 (11)C75—C74—C73121.2 (10)
C14—C13—H13119.6C75—C74—H74119.4
C12—C13—H13119.6C73—C74—H74119.4
C13—C14—C15120.1 (12)C76—C75—C74120.8 (11)
C13—C14—H14119.9C76—C75—H75119.6
C15—C14—H14119.9C74—C75—H75119.6
C14—C15—C16119.6 (11)C75—C76—C77118.8 (11)
C14—C15—H15120.2C75—C76—H76120.6
C16—C15—H15120.2C77—C76—H76120.6
C11—C16—C15121.4 (11)C78—C77—C76119.8 (11)
C11—C16—H16119.3C78—C77—H77120.1
C15—C16—H16119.3C76—C77—H77120.1
C22—C17—C18117.5 (10)C77—C78—C73122.0 (11)
C22—C17—P1120.8 (9)C77—C78—H78119.0
C18—C17—P1121.7 (9)C73—C78—H78119.0
C19—C18—C17120.0 (12)C80—C79—C84116.3 (10)
C19—C18—H18120.0C80—C79—P4121.4 (8)
C17—C18—H18120.0C84—C79—P4121.6 (10)
C20—C19—C18119.3 (12)C81—C80—C79122.6 (11)
C20—C19—H19120.4C81—C80—H80118.7
C18—C19—H19120.4C79—C80—H80118.7
C21—C20—C19120.7 (10)C80—C81—C82120.4 (11)
C21—C20—H20119.7C80—C81—H81119.8
C19—C20—H20119.7C82—C81—H81119.8
C20—C21—C22118.7 (10)C81—C82—C83119.3 (10)
C20—C21—H21120.6C81—C82—H82120.4
C22—C21—H21120.6C83—C82—H82120.4
C17—C22—C21123.8 (10)C84—C83—C82119.8 (10)
C17—C22—H22118.1C84—C83—H83120.1
C21—C22—H22118.1C82—C83—H83120.1
C24—C23—C28118.3 (9)C83—C84—C79121.6 (11)
C24—C23—P2119.5 (8)C83—C84—H84119.2
C28—C23—P2122.1 (8)C79—C84—H84119.2
C25—C24—C23119.8 (10)C86—C85—C90105.5 (9)
C25—C24—H24120.1C86—C85—Rh271.3 (6)
C23—C24—H24120.1C90—C85—Rh295.2 (7)
C26—C25—C24121.8 (11)C86—C85—H85123.7
C26—C25—H25119.1C90—C85—H85123.7
C24—C25—H25119.1Rh2—C85—H85123.7
C25—C26—C27119.7 (11)C85—C86—C87108.3 (9)
C25—C26—H26120.1C85—C86—Rh272.5 (6)
C27—C26—H26120.1C87—C86—Rh297.2 (6)
C28—C27—C26120.4 (11)C85—C86—H86122.2
C28—C27—H27119.8C87—C86—H86122.2
C26—C27—H27119.8Rh2—C86—H86122.2
C27—C28—C23119.9 (10)C86—C87—C88102.5 (8)
C27—C28—H28120.1C86—C87—C91100.0 (9)
C23—C28—H28120.1C88—C87—C9199.6 (9)
C34—C29—C30116.8 (10)C86—C87—H87117.2
C34—C29—P2121.5 (9)C88—C87—H87117.2
C30—C29—P2121.1 (9)C91—C87—H87117.2
C31—C30—C29120.3 (10)C89—C88—C87106.8 (10)
C31—C30—H30119.9C89—C88—Rh271.1 (6)
C29—C30—H30119.9C87—C88—Rh295.1 (6)
C32—C31—C30121.1 (10)C89—C88—H88123.3
C32—C31—H31119.4C87—C88—H88123.3
C30—C31—H31119.4Rh2—C88—H88123.3
C31—C32—C33120.0 (10)C88—C89—C90106.2 (10)
C31—C32—H32120.0C88—C89—Rh272.6 (6)
C33—C32—H32120.0C90—C89—Rh295.2 (7)
C34—C33—C32119.2 (11)C88—C89—H89123.2
C34—C33—H33120.4C90—C89—H89123.2
C32—C33—H33120.4Rh2—C89—H89123.2
C33—C34—C29122.6 (11)C85—C90—C89103.1 (9)
C33—C34—H34118.7C85—C90—C9199.5 (9)
C29—C34—H34118.7C89—C90—C9199.8 (10)
C36—C35—C40104.5 (9)C85—C90—H90117.2
C36—C35—Rh170.6 (6)C89—C90—H90117.2
C40—C35—Rh194.9 (7)C91—C90—H90117.2
C36—C35—H35124.1C87—C91—C9093.7 (8)
C40—C35—H35124.1C87—C91—H91A113.0
Rh1—C35—H35124.1C90—C91—H91A113.0
C35—C36—C37107.3 (9)C87—C91—H91B113.0
C35—C36—Rh172.9 (6)C90—C91—H91B113.0
C37—C36—Rh198.1 (7)H91A—C91—H91B110.4
C35—C36—H36122.2F2—B1—F1112.0 (12)
C37—C36—H36122.2F2—B1—F4109.0 (10)
Rh1—C36—H36122.2F1—B1—F4107.0 (12)
C41—C37—C36101.2 (8)F2—B1—F3110.7 (11)
C41—C37—C38101.3 (8)F1—B1—F3108.5 (10)
C36—C37—C38101.2 (7)F4—B1—F3109.5 (11)
C41—C37—H37116.8F7—B2—F5108.7 (11)
C36—C37—H37116.8F7—B2—F8110.3 (13)
C38—C37—H37116.8F5—B2—F8111.0 (12)
C39—C38—C37106.1 (9)F7—B2—F6108.6 (11)
C39—C38—Rh171.4 (6)F5—B2—F6110.1 (12)
C37—C38—Rh195.6 (6)F8—B2—F6108.2 (11)
C11—P1—C1—C271.5 (9)C38—C37—C41—C4052.2 (10)
C17—P1—C1—C237.4 (10)C35—C40—C41—C3753.5 (10)
Rh1—P1—C1—C2165.9 (8)C39—C40—C41—C3752.2 (10)
C11—P1—C1—C5153.7 (8)C55—C51—C52—C5339.7 (12)
C17—P1—C1—C597.5 (9)P3—C51—C52—C53177.0 (8)
Rh1—P1—C1—C531.0 (9)C51—C52—C53—C548.4 (13)
C5—C1—C2—C334.2 (12)C52—C53—C54—C5521.2 (13)
P1—C1—C2—C3176.5 (9)C52—C51—C55—C5668.3 (12)
C1—C2—C3—C411.0 (14)P3—C51—C55—C5666.1 (11)
C2—C3—C4—C517.1 (14)C52—C51—C55—C5450.8 (10)
C3—C4—C5—C685.6 (11)P3—C51—C55—C54174.7 (7)
C3—C4—C5—C137.7 (12)C53—C54—C55—C5142.4 (11)
C2—C1—C5—C443.6 (10)C53—C54—C55—C5681.5 (12)
P1—C1—C5—C4174.5 (7)C51—C55—C56—C57168.6 (9)
C2—C1—C5—C675.4 (10)C54—C55—C56—C5759.8 (12)
P1—C1—C5—C666.4 (11)C51—C55—C56—C6068.4 (13)
C4—C5—C6—C760.2 (11)C54—C55—C56—C60177.2 (9)
C1—C5—C6—C7173.5 (9)C55—C56—C57—C58167.0 (9)
C4—C5—C6—C10179.2 (9)C60—C56—C57—C5835.3 (12)
C1—C5—C6—C1065.8 (12)C56—C57—C58—C5921.9 (13)
C5—C6—C7—C8164.9 (9)C57—C58—C59—C600.4 (13)
C10—C6—C7—C835.6 (11)C55—C56—C60—C59161.1 (9)
C6—C7—C8—C919.7 (13)C57—C56—C60—C5934.3 (11)
C7—C8—C9—C104.3 (12)C55—C56—C60—P434.2 (12)
C7—C6—C10—C937.3 (10)C57—C56—C60—P492.6 (9)
C5—C6—C10—C9163.4 (8)C58—C59—C60—C5620.9 (11)
C7—C6—C10—P292.1 (9)C58—C59—C60—P4107.1 (9)
C5—C6—C10—P234.0 (11)C79—P4—C60—C56165.0 (8)
C8—C9—C10—C625.9 (11)C73—P4—C60—C5656.6 (8)
C8—C9—C10—P2103.8 (9)Rh2—P4—C60—C5672.0 (8)
C29—P2—C10—C6166.1 (7)C79—P4—C60—C5943.5 (8)
C23—P2—C10—C657.2 (8)C73—P4—C60—C5965.0 (8)
Rh1—P2—C10—C672.8 (8)Rh2—P4—C60—C59166.4 (6)
C29—P2—C10—C943.5 (9)C67—P3—C61—C6618.4 (11)
C23—P2—C10—C965.4 (8)C51—P3—C61—C66134.9 (10)
Rh1—P2—C10—C9164.6 (6)Rh2—P3—C61—C66103.0 (9)
C1—P1—C11—C16135.2 (9)C67—P3—C61—C62165.5 (9)
C17—P1—C11—C1619.8 (10)C51—P3—C61—C6249.0 (10)
Rh1—P1—C11—C16101.3 (9)Rh2—P3—C61—C6273.1 (9)
C1—P1—C11—C1248.0 (9)C66—C61—C62—C632.2 (16)
C17—P1—C11—C12163.3 (9)P3—C61—C62—C63178.5 (9)
Rh1—P1—C11—C1275.6 (9)C61—C62—C63—C640.3 (18)
C16—C11—C12—C131.2 (16)C62—C63—C64—C651.8 (19)
P1—C11—C12—C13178.2 (9)C63—C64—C65—C661.8 (19)
C11—C12—C13—C140.2 (18)C62—C61—C66—C652.2 (17)
C12—C13—C14—C151.4 (19)P3—C61—C66—C65178.4 (9)
C13—C14—C15—C161.1 (18)C64—C65—C66—C610.2 (18)
C12—C11—C16—C151.5 (16)C61—P3—C67—C68120.5 (9)
P1—C11—C16—C15178.4 (9)C51—P3—C67—C68129.8 (8)
C14—C15—C16—C110.4 (17)Rh2—P3—C67—C681.7 (9)
C1—P1—C17—C22130.2 (9)C61—P3—C67—C7257.3 (10)
C11—P1—C17—C22120.8 (9)C51—P3—C67—C7252.4 (11)
Rh1—P1—C17—C220.7 (10)Rh2—P3—C67—C72179.4 (8)
C1—P1—C17—C1849.6 (11)C72—C67—C68—C690.4 (15)
C11—P1—C17—C1859.4 (10)P3—C67—C68—C69177.4 (8)
Rh1—P1—C17—C18179.1 (8)C67—C68—C69—C700.7 (16)
C22—C17—C18—C192.4 (17)C68—C69—C70—C710.9 (17)
P1—C17—C18—C19177.9 (9)C69—C70—C71—C720.8 (18)
C17—C18—C19—C203.3 (18)C70—C71—C72—C670.5 (18)
C18—C19—C20—C213.7 (17)C68—C67—C72—C710.3 (17)
C19—C20—C21—C223.2 (16)P3—C67—C72—C71177.4 (9)
C18—C17—C22—C211.9 (16)C79—P4—C73—C7841.5 (10)
P1—C17—C22—C21178.3 (8)C60—P4—C73—C7868.0 (9)
C20—C21—C22—C172.4 (16)Rh2—P4—C73—C78159.4 (7)
C29—P2—C23—C24142.0 (8)C79—P4—C73—C74144.0 (8)
C10—P2—C23—C24108.6 (8)C60—P4—C73—C74106.5 (8)
Rh1—P2—C23—C2425.3 (9)Rh2—P4—C73—C7426.1 (9)
C29—P2—C23—C2842.6 (9)C78—C73—C74—C753.7 (14)
C10—P2—C23—C2866.8 (9)P4—C73—C74—C75171.1 (8)
Rh1—P2—C23—C28159.3 (7)C73—C74—C75—C760.1 (16)
C28—C23—C24—C251.9 (14)C74—C75—C76—C773.0 (17)
P2—C23—C24—C25173.7 (8)C75—C76—C77—C782.5 (17)
C23—C24—C25—C260.2 (17)C76—C77—C78—C731.2 (16)
C24—C25—C26—C273.2 (19)C74—C73—C78—C774.3 (15)
C25—C26—C27—C284.3 (18)P4—C73—C78—C77170.4 (8)
C26—C27—C28—C232.2 (16)C73—P4—C79—C8039.7 (10)
C24—C23—C28—C270.8 (14)C60—P4—C79—C80150.0 (9)
P2—C23—C28—C27174.6 (8)Rh2—P4—C79—C8080.6 (10)
C10—P2—C29—C34149.5 (9)C73—P4—C79—C84150.3 (9)
C23—P2—C29—C3438.3 (10)C60—P4—C79—C8439.9 (10)
Rh1—P2—C29—C3481.8 (10)Rh2—P4—C79—C8489.4 (9)
C10—P2—C29—C3039.7 (10)C84—C79—C80—C812.1 (17)
C23—P2—C29—C30150.9 (9)P4—C79—C80—C81172.6 (9)
Rh1—P2—C29—C3089.0 (9)C79—C80—C81—C822.0 (17)
C34—C29—C30—C310.3 (15)C80—C81—C82—C831.5 (16)
P2—C29—C30—C31171.5 (8)C81—C82—C83—C841.2 (16)
C29—C30—C31—C322.3 (16)C82—C83—C84—C791.4 (17)
C30—C31—C32—C332.9 (17)C80—C79—C84—C831.8 (16)
C31—C32—C33—C341.5 (17)P4—C79—C84—C83172.3 (8)
C32—C33—C34—C290.5 (17)C90—C85—C86—C871.7 (11)
C30—C29—C34—C331.1 (16)Rh2—C85—C86—C8792.0 (7)
P2—C29—C34—C33170.0 (8)C90—C85—C86—Rh290.3 (8)
C40—C35—C36—C373.3 (11)C85—C86—C87—C8869.2 (10)
Rh1—C35—C36—C3793.3 (7)Rh2—C86—C87—C884.6 (8)
C40—C35—C36—Rh190.1 (7)C85—C86—C87—C9133.0 (10)
C35—C36—C37—C4132.0 (10)Rh2—C86—C87—C91106.9 (7)
Rh1—C36—C37—C41106.5 (7)C86—C87—C88—C8967.2 (10)
C35—C36—C37—C3872.1 (9)C91—C87—C88—C8935.4 (10)
Rh1—C36—C37—C382.4 (7)C86—C87—C88—Rh24.6 (8)
C41—C37—C38—C3934.1 (10)C91—C87—C88—Rh2107.2 (7)
C36—C37—C38—C3969.9 (10)C87—C88—C89—C900.8 (11)
C41—C37—C38—Rh1106.4 (7)Rh2—C88—C89—C9090.4 (7)
C36—C37—C38—Rh12.4 (7)C87—C88—C89—Rh289.7 (7)
C37—C38—C39—C400.5 (10)C86—C85—C90—C8967.0 (11)
Rh1—C38—C39—C4090.1 (7)Rh2—C85—C90—C895.0 (9)
C37—C38—C39—Rh190.6 (7)C86—C85—C90—C9135.5 (11)
C36—C35—C40—C4136.9 (11)Rh2—C85—C90—C91107.5 (8)
Rh1—C35—C40—C41108.1 (8)C88—C89—C90—C8568.3 (10)
C36—C35—C40—C3966.5 (10)Rh2—C89—C90—C855.0 (9)
Rh1—C35—C40—C394.7 (8)C88—C89—C90—C9133.9 (10)
C38—C39—C40—C4134.5 (10)Rh2—C89—C90—C91107.3 (7)
Rh1—C39—C40—C41107.8 (7)C86—C87—C91—C9051.5 (10)
C38—C39—C40—C3568.6 (10)C88—C87—C91—C9053.1 (10)
Rh1—C39—C40—C354.7 (8)C85—C90—C91—C8752.5 (10)
C36—C37—C41—C4051.7 (10)C89—C90—C91—C8752.7 (10)
(RhBICPcodBF4) [(1R,1'R,2R,2'R)-2,2'-Bis(diphenylphosphanyl)-1,1'-dicyclopentane][η4-(Z,Z)-cycloocta-1,5-diene]rhodium(I) tetrafluoroborate dichloromethane monosolvate top
Crystal data top
[Rh(C34H36P2)(C8H12)]BF4·CH2Cl2F(000) = 916
Mr = 889.39Dx = 1.499 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 10.2285 (2) ÅCell parameters from 9728 reflections
b = 13.9823 (3) Åθ = 2.9–33.4°
c = 14.5131 (4) ŵ = 0.70 mm1
β = 108.2650 (12)°T = 150 K
V = 1971.06 (8) Å3Part of prism, red
Z = 20.38 × 0.34 × 0.16 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
9780 independent reflections
Radiation source: sealed tube9496 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 8.3333 pixels mm-1θmax = 28.3°, θmin = 2.1°
φ and ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
k = 1818
Tmin = 0.670, Tmax = 0.749l = 1919
64265 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.020 w = 1/[σ2(Fo2) + (0.0228P)2 + 0.6524P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.048(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.46 e Å3
9780 reflectionsΔρmin = 0.46 e Å3
524 parametersAbsolute structure: Flack x determined using 4470 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
25 restraintsAbsolute structure parameter: 0.015 (5)
Crystal data top
[Rh(C34H36P2)(C8H12)]BF4·CH2Cl2V = 1971.06 (8) Å3
Mr = 889.39Z = 2
Monoclinic, P21Mo Kα radiation
a = 10.2285 (2) ŵ = 0.70 mm1
b = 13.9823 (3) ÅT = 150 K
c = 14.5131 (4) Å0.38 × 0.34 × 0.16 mm
β = 108.2650 (12)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
9780 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
9496 reflections with I > 2σ(I)
Tmin = 0.670, Tmax = 0.749Rint = 0.034
64265 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.020H-atom parameters constrained
wR(F2) = 0.048Δρmax = 0.46 e Å3
S = 1.04Δρmin = 0.46 e Å3
9780 reflectionsAbsolute structure: Flack x determined using 4470 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
524 parametersAbsolute structure parameter: 0.015 (5)
25 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Rh10.41617 (2)0.24643 (2)0.23220 (2)0.01403 (4)
P10.44955 (6)0.38414 (4)0.15326 (4)0.01486 (11)
P20.32514 (6)0.33385 (4)0.33545 (4)0.01515 (12)
C10.2886 (2)0.44676 (18)0.09159 (18)0.0168 (5)
H10.24500.40520.03400.020*
C20.2935 (3)0.54545 (19)0.0459 (2)0.0240 (5)
H2A0.34110.54220.00380.029*
H2B0.34020.59320.09580.029*
C30.1399 (3)0.5693 (2)0.0001 (2)0.0307 (6)
H3A0.10790.55090.06920.037*
H3B0.12390.63870.00520.037*
C40.0631 (3)0.5114 (2)0.05753 (19)0.0240 (5)
H4A0.00100.46540.01420.029*
H4B0.00940.55470.08590.029*
C50.1737 (2)0.45702 (18)0.13946 (18)0.0182 (5)
H50.13780.39210.14750.022*
C60.2084 (2)0.51101 (18)0.23624 (18)0.0190 (5)
H60.24520.57490.22560.023*
C70.0824 (3)0.5299 (2)0.26988 (19)0.0265 (6)
H7A0.02080.57820.22810.032*
H7B0.02960.47040.26900.032*
C80.1447 (3)0.5672 (3)0.3732 (2)0.0368 (7)
H8A0.08280.55370.41220.044*
H8B0.16000.63710.37290.044*
C90.2820 (3)0.51438 (19)0.41508 (19)0.0225 (5)
H9A0.27430.46520.46220.027*
H9B0.35570.55980.44870.027*
C100.3153 (2)0.46676 (17)0.32827 (17)0.0174 (4)
H100.40820.49030.32960.021*
C110.5253 (3)0.36461 (16)0.05541 (17)0.0176 (4)
C120.4464 (3)0.34150 (18)0.03916 (18)0.0213 (5)
H120.34880.34250.05680.026*
C130.5098 (3)0.31695 (19)0.1077 (2)0.0262 (6)
H130.45520.30170.17200.031*
C140.6517 (3)0.31456 (19)0.0830 (2)0.0281 (6)
H140.69440.29660.12990.034*
C150.7317 (3)0.3384 (2)0.0105 (2)0.0261 (5)
H150.82920.33760.02760.031*
C160.6685 (3)0.36342 (19)0.07889 (19)0.0224 (5)
H160.72370.38000.14270.027*
C170.5785 (3)0.46552 (19)0.2293 (2)0.0196 (5)
C180.6139 (3)0.55152 (19)0.1928 (2)0.0254 (5)
H180.56690.57030.12800.030*
C190.7174 (3)0.6090 (2)0.2516 (2)0.0318 (6)
H190.74150.66700.22680.038*
C200.7860 (3)0.5815 (2)0.3469 (3)0.0352 (7)
H200.85500.62180.38750.042*
C210.7543 (3)0.4965 (2)0.3822 (2)0.0332 (6)
H210.80240.47750.44690.040*
C220.6515 (3)0.4379 (2)0.3232 (2)0.0241 (6)
H220.63120.37860.34760.029*
C230.1518 (2)0.29339 (17)0.32712 (18)0.0176 (5)
C240.0960 (3)0.30752 (19)0.40233 (19)0.0234 (5)
H240.15150.33350.46230.028*
C250.0400 (3)0.2839 (2)0.3901 (2)0.0293 (6)
H250.07710.29400.44160.035*
C260.1221 (2)0.2456 (3)0.30310 (19)0.0303 (5)
H260.21590.23110.29440.036*
C270.0669 (3)0.22856 (18)0.2291 (2)0.0258 (6)
H270.12240.20090.17000.031*
C280.0692 (2)0.2518 (2)0.24073 (16)0.0202 (4)
H280.10670.23930.18970.024*
C290.4253 (3)0.31440 (18)0.46317 (17)0.0188 (5)
C300.4031 (3)0.2339 (2)0.51345 (17)0.0243 (6)
H300.32750.19290.48400.029*
C310.4907 (3)0.2131 (2)0.6064 (2)0.0315 (6)
H310.47440.15830.63990.038*
C320.6012 (3)0.2723 (2)0.6496 (2)0.0374 (8)
H320.66290.25690.71180.045*
C330.6217 (3)0.3540 (2)0.6021 (2)0.0334 (7)
H330.69570.39580.63300.040*
C340.5352 (3)0.3753 (2)0.50993 (19)0.0254 (5)
H340.55030.43170.47810.030*
C350.3424 (3)0.10766 (18)0.28107 (19)0.0219 (5)
H350.27880.11670.32050.026*
C360.4785 (3)0.12082 (18)0.33184 (19)0.0225 (5)
H360.49500.13730.40160.027*
C370.5979 (3)0.0692 (2)0.3135 (2)0.0266 (6)
H37A0.60120.00290.33800.032*
H37B0.68460.10130.35080.032*
C380.5891 (3)0.0663 (2)0.2059 (2)0.0246 (5)
H38A0.68330.06080.20120.029*
H38B0.53730.00840.17580.029*
C390.5198 (3)0.15355 (18)0.14924 (18)0.0206 (5)
H390.57940.18970.11830.025*
C400.3812 (3)0.16018 (18)0.09964 (18)0.0203 (5)
H400.36000.19920.03900.024*
C410.2727 (3)0.0869 (2)0.0978 (2)0.0264 (6)
H41A0.27480.03660.05030.032*
H41B0.18130.11810.07480.032*
C420.2889 (3)0.03933 (19)0.1964 (2)0.0273 (6)
H42A0.19860.01390.19640.033*
H42B0.35320.01530.20510.033*
B10.0439 (9)0.2767 (5)0.8985 (5)0.0265 (18)0.655 (11)
F10.0418 (9)0.2732 (4)0.9927 (4)0.0296 (18)0.655 (11)
F20.0856 (6)0.3668 (3)0.8796 (2)0.0447 (14)0.655 (11)
F30.1349 (4)0.2099 (4)0.8855 (4)0.0404 (11)0.655 (11)
F40.0847 (6)0.2592 (5)0.8351 (7)0.0529 (16)0.655 (11)
B1'0.0096 (12)0.2837 (7)0.8886 (8)0.021 (3)0.345 (11)
F1'0.0293 (16)0.2713 (9)0.9855 (7)0.050 (6)0.345 (11)
F2'0.0189 (16)0.3785 (4)0.8658 (5)0.061 (4)0.345 (11)
F3'0.1247 (8)0.2579 (10)0.8660 (7)0.062 (3)0.345 (11)
F4'0.1010 (10)0.2309 (8)0.8354 (12)0.041 (3)0.345 (11)
C510.0206 (7)0.3922 (4)0.6660 (4)0.0879 (19)
H51A0.05370.35480.62000.106*
H51B0.01580.38070.73220.106*
Cl10.18126 (13)0.35195 (8)0.65983 (7)0.0593 (3)
Cl20.00589 (15)0.51239 (9)0.63875 (12)0.0863 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Rh10.01564 (7)0.01289 (7)0.01393 (7)0.00028 (8)0.00518 (5)0.00058 (8)
P10.0155 (3)0.0143 (3)0.0161 (3)0.0000 (2)0.0069 (2)0.0004 (2)
P20.0151 (3)0.0168 (3)0.0137 (3)0.0004 (2)0.0047 (2)0.0003 (2)
C10.0172 (11)0.0164 (11)0.0175 (11)0.0025 (9)0.0067 (9)0.0036 (9)
C20.0301 (14)0.0199 (12)0.0260 (13)0.0041 (10)0.0142 (11)0.0075 (10)
C30.0354 (15)0.0245 (13)0.0306 (14)0.0082 (11)0.0080 (12)0.0098 (11)
C40.0203 (12)0.0278 (13)0.0219 (12)0.0073 (10)0.0037 (9)0.0032 (10)
C50.0155 (11)0.0190 (11)0.0199 (12)0.0024 (9)0.0054 (9)0.0028 (9)
C60.0198 (11)0.0189 (11)0.0203 (12)0.0032 (9)0.0094 (9)0.0012 (9)
C70.0239 (13)0.0326 (14)0.0259 (13)0.0104 (11)0.0118 (11)0.0045 (11)
C80.0373 (16)0.0470 (18)0.0293 (15)0.0190 (14)0.0151 (13)0.0020 (13)
C90.0243 (12)0.0222 (12)0.0235 (12)0.0002 (10)0.0111 (10)0.0055 (10)
C100.0176 (11)0.0171 (11)0.0189 (11)0.0003 (9)0.0075 (9)0.0022 (9)
C110.0237 (11)0.0129 (10)0.0195 (11)0.0006 (9)0.0118 (9)0.0012 (8)
C120.0257 (12)0.0184 (11)0.0220 (12)0.0006 (10)0.0106 (10)0.0013 (9)
C130.0394 (16)0.0214 (12)0.0204 (12)0.0023 (11)0.0133 (11)0.0014 (10)
C140.0417 (16)0.0227 (12)0.0294 (14)0.0045 (11)0.0249 (13)0.0013 (10)
C150.0259 (13)0.0260 (13)0.0325 (14)0.0034 (10)0.0181 (11)0.0024 (11)
C160.0228 (12)0.0234 (12)0.0241 (12)0.0002 (10)0.0116 (10)0.0001 (10)
C170.0156 (11)0.0203 (12)0.0254 (13)0.0022 (9)0.0103 (10)0.0055 (10)
C180.0244 (13)0.0213 (12)0.0343 (14)0.0020 (10)0.0149 (11)0.0022 (11)
C190.0234 (13)0.0223 (13)0.0552 (19)0.0062 (11)0.0203 (13)0.0072 (13)
C200.0187 (13)0.0304 (15)0.054 (2)0.0030 (11)0.0075 (12)0.0128 (14)
C210.0187 (12)0.0390 (16)0.0363 (16)0.0005 (11)0.0005 (11)0.0095 (13)
C220.0179 (13)0.0254 (13)0.0288 (14)0.0003 (10)0.0067 (11)0.0017 (11)
C230.0158 (11)0.0174 (11)0.0196 (11)0.0010 (9)0.0056 (9)0.0016 (9)
C240.0221 (12)0.0277 (13)0.0222 (12)0.0023 (10)0.0095 (10)0.0014 (10)
C250.0266 (14)0.0338 (13)0.0330 (15)0.0022 (11)0.0172 (12)0.0000 (11)
C260.0186 (10)0.0309 (12)0.0430 (14)0.0019 (16)0.0119 (9)0.0021 (18)
C270.0203 (11)0.0236 (18)0.0295 (12)0.0022 (9)0.0020 (9)0.0018 (10)
C280.0208 (10)0.0188 (10)0.0202 (9)0.0012 (13)0.0055 (8)0.0007 (13)
C290.0180 (11)0.0263 (12)0.0121 (10)0.0017 (9)0.0048 (9)0.0019 (9)
C300.0257 (11)0.0299 (16)0.0179 (10)0.0047 (11)0.0077 (9)0.0035 (11)
C310.0373 (16)0.0401 (15)0.0190 (12)0.0125 (12)0.0116 (12)0.0071 (11)
C320.0346 (15)0.058 (2)0.0164 (12)0.0151 (13)0.0029 (11)0.0017 (12)
C330.0250 (13)0.0476 (18)0.0234 (14)0.0032 (13)0.0016 (11)0.0113 (12)
C340.0216 (12)0.0316 (14)0.0219 (12)0.0006 (11)0.0051 (10)0.0060 (10)
C350.0268 (13)0.0163 (11)0.0262 (13)0.0016 (9)0.0133 (10)0.0061 (10)
C360.0303 (13)0.0185 (11)0.0200 (12)0.0058 (10)0.0098 (10)0.0050 (9)
C370.0275 (15)0.0259 (14)0.0273 (14)0.0078 (11)0.0096 (12)0.0062 (11)
C380.0285 (14)0.0202 (13)0.0275 (14)0.0063 (11)0.0123 (11)0.0017 (10)
C390.0260 (13)0.0171 (11)0.0218 (12)0.0018 (10)0.0118 (10)0.0001 (9)
C400.0277 (13)0.0173 (11)0.0160 (11)0.0009 (10)0.0068 (9)0.0021 (9)
C410.0303 (14)0.0189 (13)0.0262 (14)0.0051 (11)0.0033 (11)0.0035 (11)
C420.0305 (14)0.0188 (12)0.0342 (15)0.0055 (10)0.0123 (12)0.0002 (11)
B10.017 (3)0.033 (4)0.027 (3)0.003 (2)0.004 (2)0.002 (2)
F10.038 (3)0.025 (3)0.022 (3)0.006 (2)0.004 (2)0.0013 (18)
F20.064 (3)0.0354 (18)0.0335 (16)0.0154 (18)0.0143 (16)0.0002 (12)
F30.0322 (18)0.049 (2)0.040 (2)0.0099 (19)0.0124 (15)0.0108 (19)
F40.027 (2)0.070 (4)0.054 (3)0.010 (2)0.002 (2)0.018 (3)
B1'0.012 (7)0.025 (5)0.023 (6)0.002 (4)0.001 (5)0.009 (4)
F1'0.044 (7)0.070 (11)0.052 (9)0.001 (6)0.035 (7)0.009 (6)
F2'0.125 (12)0.022 (3)0.042 (4)0.012 (4)0.036 (5)0.005 (3)
F3'0.033 (4)0.088 (9)0.071 (6)0.020 (5)0.027 (4)0.011 (6)
F4'0.019 (3)0.051 (6)0.041 (5)0.010 (3)0.009 (3)0.024 (4)
C510.131 (5)0.067 (3)0.089 (4)0.026 (3)0.068 (4)0.026 (3)
Cl10.0856 (8)0.0492 (5)0.0404 (5)0.0018 (5)0.0158 (5)0.0047 (4)
Cl20.0818 (9)0.0478 (6)0.1018 (10)0.0025 (6)0.0108 (7)0.0102 (6)
Geometric parameters (Å, º) top
Rh1—C402.203 (2)C21—C221.395 (4)
Rh1—C362.237 (2)C21—H210.9500
Rh1—C392.250 (2)C22—H220.9500
Rh1—C352.274 (2)C23—C241.396 (4)
Rh1—P12.3198 (6)C23—C281.400 (3)
Rh1—P22.3411 (6)C24—C251.385 (4)
P1—C171.828 (3)C24—H240.9500
P1—C11.832 (2)C25—C261.386 (4)
P1—C111.839 (2)C25—H250.9500
P2—C231.829 (2)C26—C271.382 (4)
P2—C291.835 (2)C26—H260.9500
P2—C101.862 (2)C27—C281.388 (3)
C1—C21.538 (3)C27—H270.9500
C1—C51.548 (3)C28—H280.9500
C1—H11.0000C29—C301.398 (4)
C2—C31.539 (4)C29—C341.404 (4)
C2—H2A0.9900C30—C311.396 (4)
C2—H2B0.9900C30—H300.9500
C3—C41.542 (4)C31—C321.382 (5)
C3—H3A0.9900C31—H310.9500
C3—H3B0.9900C32—C331.384 (5)
C4—C51.558 (3)C32—H320.9500
C4—H4A0.9900C33—C341.386 (4)
C4—H4B0.9900C33—H330.9500
C5—C61.535 (3)C34—H340.9500
C5—H51.0000C35—C361.368 (4)
C6—C71.537 (3)C35—C421.517 (4)
C6—C101.564 (3)C35—H351.0000
C6—H61.0000C36—C371.512 (4)
C7—C81.526 (4)C36—H361.0000
C7—H7A0.9900C37—C381.537 (4)
C7—H7B0.9900C37—H37A0.9900
C8—C91.534 (4)C37—H37B0.9900
C8—H8A0.9900C38—C391.517 (4)
C8—H8B0.9900C38—H38A0.9900
C9—C101.554 (3)C38—H38B0.9900
C9—H9A0.9900C39—C401.378 (4)
C9—H9B0.9900C39—H391.0000
C10—H101.0000C40—C411.505 (4)
C11—C121.395 (3)C40—H401.0000
C11—C161.396 (3)C41—C421.539 (4)
C12—C131.390 (4)C41—H41A0.9900
C12—H120.9500C41—H41B0.9900
C13—C141.383 (4)C42—H42A0.9900
C13—H130.9500C42—H42B0.9900
C14—C151.388 (4)B1—F41.370 (7)
C14—H140.9500B1—F31.372 (7)
C15—C161.388 (4)B1—F11.375 (6)
C15—H150.9500B1—F21.385 (6)
C16—H160.9500B1'—F3'1.366 (8)
C17—C221.388 (4)B1'—F1'1.367 (8)
C17—C181.406 (4)B1'—F4'1.369 (8)
C18—C191.388 (4)B1'—F2'1.374 (8)
C18—H180.9500C51—Cl21.728 (5)
C19—C201.395 (5)C51—Cl11.765 (6)
C19—H190.9500C51—H51A0.9900
C20—C211.374 (5)C51—H51B0.9900
C20—H200.9500
C40—Rh1—C3694.02 (9)C20—C19—H19120.0
C40—Rh1—C3936.03 (9)C21—C20—C19120.3 (3)
C36—Rh1—C3978.83 (9)C21—C20—H20119.9
C40—Rh1—C3580.00 (10)C19—C20—H20119.9
C36—Rh1—C3535.28 (10)C20—C21—C22120.0 (3)
C39—Rh1—C3586.13 (9)C20—C21—H21120.0
C40—Rh1—P191.82 (7)C22—C21—H21120.0
C36—Rh1—P1156.16 (7)C17—C22—C21120.7 (3)
C39—Rh1—P192.74 (7)C17—C22—H22119.7
C35—Rh1—P1167.60 (7)C21—C22—H22119.7
C40—Rh1—P2148.93 (7)C24—C23—C28118.6 (2)
C36—Rh1—P294.93 (7)C24—C23—P2122.04 (19)
C39—Rh1—P2173.07 (7)C28—C23—P2119.21 (18)
C35—Rh1—P290.49 (7)C25—C24—C23120.4 (2)
P1—Rh1—P291.85 (2)C25—C24—H24119.8
C17—P1—C1111.44 (12)C23—C24—H24119.8
C17—P1—C1199.20 (11)C24—C25—C26120.4 (3)
C1—P1—C11103.04 (11)C24—C25—H25119.8
C17—P1—Rh1114.12 (9)C26—C25—H25119.8
C1—P1—Rh1112.90 (8)C27—C26—C25119.7 (2)
C11—P1—Rh1114.90 (8)C27—C26—H26120.1
C23—P2—C29104.10 (11)C25—C26—H26120.1
C23—P2—C10105.71 (11)C26—C27—C28120.2 (2)
C29—P2—C10101.99 (11)C26—C27—H27119.9
C23—P2—Rh1111.59 (8)C28—C27—H27119.9
C29—P2—Rh1111.16 (8)C27—C28—C23120.5 (2)
C10—P2—Rh1120.71 (8)C27—C28—H28119.8
C2—C1—C5104.02 (19)C23—C28—H28119.8
C2—C1—P1119.55 (18)C30—C29—C34118.2 (2)
C5—C1—P1121.17 (17)C30—C29—P2121.06 (19)
C2—C1—H1103.1C34—C29—P2120.5 (2)
C5—C1—H1103.1C31—C30—C29120.8 (3)
P1—C1—H1103.1C31—C30—H30119.6
C1—C2—C3102.3 (2)C29—C30—H30119.6
C1—C2—H2A111.3C32—C31—C30120.0 (3)
C3—C2—H2A111.3C32—C31—H31120.0
C1—C2—H2B111.3C30—C31—H31120.0
C3—C2—H2B111.3C31—C32—C33119.9 (3)
H2A—C2—H2B109.2C31—C32—H32120.0
C2—C3—C4106.0 (2)C33—C32—H32120.0
C2—C3—H3A110.5C32—C33—C34120.5 (3)
C4—C3—H3A110.5C32—C33—H33119.8
C2—C3—H3B110.5C34—C33—H33119.8
C4—C3—H3B110.5C33—C34—C29120.6 (3)
H3A—C3—H3B108.7C33—C34—H34119.7
C3—C4—C5107.3 (2)C29—C34—H34119.7
C3—C4—H4A110.2C36—C35—C42124.7 (2)
C5—C4—H4A110.2C36—C35—Rh170.87 (15)
C3—C4—H4B110.2C42—C35—Rh1110.81 (17)
C5—C4—H4B110.2C36—C35—H35114.2
H4A—C4—H4B108.5C42—C35—H35114.2
C6—C5—C1117.8 (2)Rh1—C35—H35114.2
C6—C5—C4111.3 (2)C35—C36—C37125.6 (3)
C1—C5—C4100.04 (19)C35—C36—Rh173.85 (14)
C6—C5—H5109.1C37—C36—Rh1110.08 (17)
C1—C5—H5109.1C35—C36—H36113.4
C4—C5—H5109.1C37—C36—H36113.4
C5—C6—C7113.5 (2)Rh1—C36—H36113.4
C5—C6—C10119.1 (2)C36—C37—C38113.5 (2)
C7—C6—C10103.20 (19)C36—C37—H37A108.9
C5—C6—H6106.8C38—C37—H37A108.9
C7—C6—H6106.8C36—C37—H37B108.9
C10—C6—H6106.8C38—C37—H37B108.9
C8—C7—C6103.7 (2)H37A—C37—H37B107.7
C8—C7—H7A111.0C39—C38—C37113.4 (2)
C6—C7—H7A111.0C39—C38—H38A108.9
C8—C7—H7B111.0C37—C38—H38A108.9
C6—C7—H7B111.0C39—C38—H38B108.9
H7A—C7—H7B109.0C37—C38—H38B108.9
C7—C8—C9105.9 (2)H38A—C38—H38B107.7
C7—C8—H8A110.6C40—C39—C38124.5 (2)
C9—C8—H8A110.6C40—C39—Rh170.13 (14)
C7—C8—H8B110.6C38—C39—Rh1113.11 (17)
C9—C8—H8B110.6C40—C39—H39113.8
H8A—C8—H8B108.7C38—C39—H39113.8
C8—C9—C10106.9 (2)Rh1—C39—H39113.8
C8—C9—H9A110.3C39—C40—C41126.6 (2)
C10—C9—H9A110.3C39—C40—Rh173.84 (15)
C8—C9—H9B110.3C41—C40—Rh1107.76 (17)
C10—C9—H9B110.3C39—C40—H40113.6
H9A—C9—H9B108.6C41—C40—H40113.6
C9—C10—C6104.50 (19)Rh1—C40—H40113.6
C9—C10—P2113.83 (17)C40—C41—C42114.4 (2)
C6—C10—P2116.97 (17)C40—C41—H41A108.6
C9—C10—H10107.0C42—C41—H41A108.6
C6—C10—H10107.0C40—C41—H41B108.6
P2—C10—H10107.0C42—C41—H41B108.6
C12—C11—C16118.5 (2)H41A—C41—H41B107.6
C12—C11—P1122.69 (19)C35—C42—C41112.8 (2)
C16—C11—P1118.51 (19)C35—C42—H42A109.0
C13—C12—C11120.3 (2)C41—C42—H42A109.0
C13—C12—H12119.8C35—C42—H42B109.0
C11—C12—H12119.8C41—C42—H42B109.0
C14—C13—C12120.6 (3)H42A—C42—H42B107.8
C14—C13—H13119.7F4—B1—F3109.7 (5)
C12—C13—H13119.7F4—B1—F1110.5 (5)
C13—C14—C15119.8 (2)F3—B1—F1109.6 (5)
C13—C14—H14120.1F4—B1—F2108.6 (6)
C15—C14—H14120.1F3—B1—F2109.1 (5)
C14—C15—C16119.8 (3)F1—B1—F2109.3 (5)
C14—C15—H15120.1F3'—B1'—F1'110.7 (7)
C16—C15—H15120.1F3'—B1'—F4'110.1 (7)
C15—C16—C11121.1 (2)F1'—B1'—F4'109.9 (7)
C15—C16—H16119.5F3'—B1'—F2'109.3 (7)
C11—C16—H16119.5F1'—B1'—F2'108.8 (7)
C22—C17—C18119.0 (2)F4'—B1'—F2'108.0 (7)
C22—C17—P1119.0 (2)Cl2—C51—Cl1112.4 (3)
C18—C17—P1121.8 (2)Cl2—C51—H51A109.1
C19—C18—C17120.0 (3)Cl1—C51—H51A109.1
C19—C18—H18120.0Cl2—C51—H51B109.1
C17—C18—H18120.0Cl1—C51—H51B109.1
C18—C19—C20120.0 (3)H51A—C51—H51B107.9
C18—C19—H19120.0
C17—P1—C1—C242.8 (2)C11—P1—C17—C1856.0 (2)
C11—P1—C1—C262.6 (2)Rh1—P1—C17—C18178.71 (18)
Rh1—P1—C1—C2172.81 (17)C22—C17—C18—C192.1 (4)
C17—P1—C1—C589.1 (2)P1—C17—C18—C19176.7 (2)
C11—P1—C1—C5165.40 (19)C17—C18—C19—C200.2 (4)
Rh1—P1—C1—C540.9 (2)C18—C19—C20—C211.8 (4)
C5—C1—C2—C342.9 (3)C19—C20—C21—C221.1 (5)
P1—C1—C2—C3178.05 (19)C18—C17—C22—C212.8 (4)
C1—C2—C3—C424.5 (3)P1—C17—C22—C21177.6 (2)
C2—C3—C4—C52.2 (3)C20—C21—C22—C171.3 (4)
C2—C1—C5—C677.3 (3)C29—P2—C23—C2436.3 (2)
P1—C1—C5—C660.9 (3)C10—P2—C23—C2470.7 (2)
C2—C1—C5—C443.4 (2)Rh1—P2—C23—C24156.30 (19)
P1—C1—C5—C4178.45 (18)C29—P2—C23—C28147.4 (2)
C3—C4—C5—C697.6 (2)C10—P2—C23—C28105.6 (2)
C3—C4—C5—C127.6 (3)Rh1—P2—C23—C2827.4 (2)
C1—C5—C6—C7171.5 (2)C28—C23—C24—C252.3 (4)
C4—C5—C6—C756.9 (3)P2—C23—C24—C25174.0 (2)
C1—C5—C6—C1066.7 (3)C23—C24—C25—C260.2 (5)
C4—C5—C6—C10178.7 (2)C24—C25—C26—C271.7 (5)
C5—C6—C7—C8170.4 (2)C25—C26—C27—C281.5 (5)
C10—C6—C7—C840.1 (3)C26—C27—C28—C230.6 (5)
C6—C7—C8—C933.8 (3)C24—C23—C28—C272.5 (4)
C7—C8—C9—C1014.1 (3)P2—C23—C28—C27174.0 (2)
C8—C9—C10—C610.7 (3)C23—P2—C29—C3038.2 (2)
C8—C9—C10—P2118.1 (2)C10—P2—C29—C30148.0 (2)
C5—C6—C10—C9158.0 (2)Rh1—P2—C29—C3082.1 (2)
C7—C6—C10—C931.1 (3)C23—P2—C29—C34148.0 (2)
C5—C6—C10—P231.1 (3)C10—P2—C29—C3438.2 (2)
C7—C6—C10—P295.7 (2)Rh1—P2—C29—C3491.8 (2)
C23—P2—C10—C964.62 (19)C34—C29—C30—C312.1 (4)
C29—P2—C10—C943.9 (2)P2—C29—C30—C31171.8 (2)
Rh1—P2—C10—C9167.68 (14)C29—C30—C31—C320.2 (4)
C23—P2—C10—C657.5 (2)C30—C31—C32—C332.4 (4)
C29—P2—C10—C6166.08 (17)C31—C32—C33—C342.3 (4)
Rh1—P2—C10—C670.19 (19)C32—C33—C34—C290.0 (4)
C17—P1—C11—C12152.6 (2)C30—C29—C34—C332.2 (4)
C1—P1—C11—C1238.0 (2)P2—C29—C34—C33171.8 (2)
Rh1—P1—C11—C1285.3 (2)C42—C35—C36—C370.9 (4)
C17—P1—C11—C1634.0 (2)Rh1—C35—C36—C37103.4 (3)
C1—P1—C11—C16148.6 (2)C42—C35—C36—Rh1102.6 (2)
Rh1—P1—C11—C1688.1 (2)C35—C36—C37—C3847.0 (4)
C16—C11—C12—C130.7 (4)Rh1—C36—C37—C3837.1 (3)
P1—C11—C12—C13172.7 (2)C36—C37—C38—C3932.1 (3)
C11—C12—C13—C140.4 (4)C37—C38—C39—C4092.0 (3)
C12—C13—C14—C151.1 (4)C37—C38—C39—Rh110.9 (3)
C13—C14—C15—C160.8 (4)C38—C39—C40—C414.6 (4)
C14—C15—C16—C110.3 (4)Rh1—C39—C40—C41100.4 (3)
C12—C11—C16—C151.0 (4)C38—C39—C40—Rh1105.0 (2)
P1—C11—C16—C15172.7 (2)C39—C40—C41—C4240.5 (4)
C1—P1—C17—C22133.5 (2)Rh1—C40—C41—C4242.2 (3)
C11—P1—C17—C22118.5 (2)C36—C35—C42—C4191.3 (3)
Rh1—P1—C17—C224.1 (2)Rh1—C35—C42—C4110.7 (3)
C1—P1—C17—C1852.0 (2)C40—C41—C42—C3535.9 (3)

Experimental details

(RhBICPnbdBF4)(RhBICPcodBF4)
Crystal data
Chemical formula[Rh(C34H36P2)(C7H8)]BF4[Rh(C34H36P2)(C8H12)]BF4·CH2Cl2
Mr788.42889.39
Crystal system, space groupMonoclinic, P21Monoclinic, P21
Temperature (K)200150
a, b, c (Å)10.002 (2), 9.0293 (18), 39.251 (8)10.2285 (2), 13.9823 (3), 14.5131 (4)
β (°) 95.17 (3) 108.2650 (12)
V3)3530.4 (12)1971.06 (8)
Z42
Radiation typeMo KαMo Kα
µ (mm1)0.630.70
Crystal size (mm)0.34 × 0.28 × 0.250.38 × 0.34 × 0.16
Data collection
DiffractometerStoe IPDS 2
diffractometer
Bruker APEXII CCD area-detector
diffractometer
Absorption correctionNumerical
(X-SHAPE; Stoe & Cie, 2005)
Multi-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.453, 0.8970.670, 0.749
No. of measured, independent and
observed [I > 2σ(I)] reflections
38678, 12426, 7748 64265, 9780, 9496
Rint0.0870.034
(sin θ/λ)max1)0.5950.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.103, 0.83 0.020, 0.048, 1.04
No. of reflections124269780
No. of parameters883524
No. of restraints1325
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)2.80, 1.090.46, 0.46
Absolute structureFlack (1983), with 5782 Friedel pairsFlack x determined using 4470 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Absolute structure parameter0.03 (3)0.015 (5)

Computer programs: X-AREA (Stoe & Cie, 2005), APEX2 (Bruker, 2009), SAINT (Bruker, 2009), X-RED32 (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected distances and angles of the rhodium–BICP diolefin complexes; CM denotes the centroids of the double bonds of the olefin top
ComplexRh—P (Å)Rh—CM (Å)P—Rh—P (°)CM—Rh—CM (°)
[Rh(BICP)(nbd)]BF4, (I)2.304–2.319 (2)2.090–2.110 (1)94.25 (7), 94.88 (7)69.49 (3), 69.92 (3)
[Rh(BICP)(cod)]BF4, (II)2.320 (1), 2.341 (1)2.117 (1), 2.150 (1)91.85 (2)84.19 (1)
Distances (Å) from the C atoms of the seven-membered metallacycle to the plane through the Rh and P atoms top
ComplexC(P)aC(rb)b
[Rh(BICP)(nbd)]BF4-0.133 (9), 1.364 (9); -0.118 (9), 1.489 (11)2.013 (9), 1.126 (9); 2.009 (9), 1.127 (10)
[Rh(BICP)(cod)]BF4-0.065 (2), 1.495 (2)2.094 (2), 1.211 (2)
[Rh(BINAP)(thf)2]BF4c1.261, -0.8601.027, -0.327
Notes: (a) carbon bonded to phosphorus; (b) carbon bridging the cyclopentanes [Meaning of `rb'?]; (c) Preetz et al. (2011).
 

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