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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Oct 27;68(Pt 11):m1408–m1409. doi: 10.1107/S1600536812043528

Di-μ-carbonyl-bis­[bis­(triphenyl­phos­phane)rhodium(0)](Rh—Rh) acetone disolvate1

Petia G Gueorguieva a,‡, Scott A Laneman a,§, George G Stanley a, Frank R Fronczek a,*, Steven F Watkins a
PMCID: PMC3515148  PMID: 23284375

Abstract

The dirhodium complex, [Rh2(C18H15P)4(CO)2]·2(CH3)2CO, has crystallographic twofold symmetry and the Rh—Rh distance is 2.6266 (8) Å. The four atoms proximate to each Rh atom [Rh—P = 2.3222 (7) and 2.3283 (8) Å, and Rh—C = 1.961 (3) and 2.045 (3) Å] form a distorted tetra­hedron with large deviations from the putative tetra­hedral angles [r.m.s. deviation = 23 (1)°]. The six angles more closely approximate those of a trigonal bipyramid [r.m.s. deviation = 14 (1)°] with one missing equatorial ligand. The two bridging carbonyl ligands are much more linearly coordinated to one Rh [Rh—C O = 151.0 (2)°] than to the other [127.0 (2)°], and the two Rh2CO planes form a dihedral angle of 45.43 (5)°. The two acetone solvent mol­ecules are disordered, and their estimated scattering contribution was subtracted from the observed diffraction data using the SQUEEZE routine in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155].

Related literature  

For other dirhodium complex structures, see CCDC Refcode QAFHEM: Dzik et al. (2010 ▶), YOSMEZ: Okazaki et al. (2009 ▶), DEFJII: Douglas et al. (2005 ▶), TPCDRH10: Singh et al. (1973 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For the use of SQUEEZE, see: Spek (2009 ▶).graphic file with name e-68-m1408-scheme1.jpg

Experimental  

Crystal data  

  • [Rh2(C18H15P)4(CO)2]·2C3H6O

  • M r = 1427.16

  • Monoclinic, Inline graphic

  • a = 23.535 (3) Å

  • b = 13.0758 (11) Å

  • c = 24.650 (2) Å

  • β = 115.67 (2)°

  • V = 6837.1 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.63 mm−1

  • T = 298 K

  • 0.38 × 0.38 × 0.23 mm

Data collection  

  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.797, T max = 0.869

  • 6874 measured reflections

  • 6718 independent reflections

  • 5170 reflections with I > 2σ(I)

  • R int = 0.026

  • 3 standard reflections every 3 reflections intensity decay: 4.0%

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.032

  • wR(F 2) = 0.082

  • S = 1.03

  • 6718 reflections

  • 370 parameters

  • H-atom parameters constrained

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.27 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and SQUEEZE in PLATON (Spek, 2009 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Click here for additional data file. (27.7KB, cif)

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043528/lh5542sup1.cif

e-68-m1408-sup1.cif (27.7KB, cif)
Click here for additional data file. (387.8KB, hkl)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043528/lh5542Isup2.hkl

e-68-m1408-Isup2.hkl (387.8KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The purchase of the diffractometer was made possible by a National Science Foundation chemical instrumentation grant, which we gratefully acknowledge. Improvements to the LSU X-ray Crystallography Facility were supported by grant No. LEQSF(1196–97)-ENH-TR-10, administered by the Louisiana Board of Regents.

supplementary crystallographic information

Comment

The dirhodium complex (I), (Rh(CO)(PPh3)2)2, is a precursor for HRh(CO)2(PPh3)2, a hydroformylation catalyst. A less precise crystal structure of I, as the dichloromethane solvate, was reported by Singh et al. (1973). In both solvates, the complex lies on a crystallographic twofold axis, with Rh—Rh = 2.6266 (8) Å (Singh et al.: 2.630 (1) Å). The four atoms proximate to Rh (Rh—P1 = 2.3222 (7), Rh—P2 = 2.3283 (8), Rh—C40 = 1.961 (3), Rh—C40' = 2.045 (3) Å) form a distorted tetrahedron, but the six angles deviate markedly from the ideal tetrahedral angle (δr.m.s. = 23 (1)°). The angles approximate more closely those of a trigonal bipyramid (δr.m.s. = 14 (1)°), with P1 and C40 in axial and P2 and C40' in equatorial positions, wth one equatorial position vacant. The two bridging carbonyl ligands do not lie in the same plane, the two Rh2CO planes forming a dihedral angle of 45.43 (5)°. Furthermore, each carbonyl is asymmetrically coordinated to the two Rh atoms, with a Rh—C distance of 1.961 (3) Å and Rh—C≡O angle 151.0 (2)° to one Rh, 2.045 (3) Å and 127.0 (2)° to the other. This asymmetric carbonyl bridging is also seen in the DCM solvate structure (Singh et al., 1973).

Experimental

Rh2(CO)2(PPh3)4 was synthesized from Rh(acac)(CO)2 and excess triphenylphosphine under hydroformylation conditions, with acetone as solvent: A small autoclave was charged with a solution of Rh(acac)(CO)2 (0.010 g), PPh3 (9.750 g), and 1-hexene 7.883 g) in acetone (40 ml) while inside a glovebox. The autoclave was sealed, removed from the glovebox, and placed in a heating mantle. The headspace of the autoclave was purged with syn gas (1:1 H2:CO, 3 x 60psig purges), and pressurized to 60psig with syn gas. The vessel was heated to 80°C and the syn gas pressure was adjusted to 80psig. After 18 h, the vessel was depressurized and purged with nitrogen (3x 60psig). The reaction mixture was analyzed with 1H NMR: 91% aldehydes, 6.7% olefin isomerization, 2.2% 1-hexene. The n/i ratio of the aldehydes were 13.6. The reaction mixture slowly concentrated upon sitting in a glove box to afford a few red crystals of (I).

Refinement

Each cavity (estimated volume 288 Å3) associated with a dirhodium molecule contains two disordered acetone molecules, for which no reasonable model could be developed. Therefore, the observed structure amplitudes were modified by PLATON/SQUEEZE (Spek, 2009) to subtract the scattering contribution of the electron density found in each cavity.

All H atoms were placed in calculated positions, with C(sp3)—H = 0.96 Å, Uiso(H) = 1.5Ueq(C), and C(sp2)—H = 0.93 Å, Uiso(H) = 1.2Ueq(C), and thereafter allowed to ride the attached C atom.

Figures

Fig. 1.

Fig. 1.

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View of (I) (50% probability displacement ellipsoids). Unlabeled atoms are related by the symmetry operator (-x+2, y, -z+3/2).

Crystal data

[Rh2(C18H15P)4(CO)2]·2C3H6O F(000) = 2936
Mr = 1427.16 Dx = 1.386 Mg m−3
Monoclinic, C2/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc Cell parameters from 25 reflections
a = 23.535 (3) Å θ = 2.6–27.5°
b = 13.0758 (11) Å µ = 0.63 mm−1
c = 24.650 (2) Å T = 298 K
β = 115.67 (2)° Prism, red
V = 6837.1 (16) Å3 0.38 × 0.38 × 0.23 mm
Z = 4
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Data collection

Enraf–Nonius CAD-4 diffractometer 5170 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.026
Graphite monochromator θmax = 26.0°, θmin = 1.8°
θ/2θ scans h = 0→28
Absorption correction: ψ scan (North et al., 1968) k = 0→16
Tmin = 0.797, Tmax = 0.869 l = −30→27
6874 measured reflections 3 standard reflections every 3 reflections
6718 independent reflections intensity decay: 4.0%
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082 H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0423P)2 + 0.3727P] where P = (Fo2 + 2Fc2)/3
6718 reflections (Δ/σ)max = 0.003
370 parameters Δρmax = 0.39 e Å−3
0 restraints Δρmin = −0.27 e Å−3
0 constraints
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Special details

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

x y z Uiso*/Ueq
P1 0.88187 (3) −0.11053 (5) 0.72824 (3) 0.03726 (16)
C1 0.81798 (13) −0.0719 (2) 0.74770 (11) 0.0410 (6)
C2 0.80127 (16) 0.0298 (2) 0.74235 (14) 0.0549 (8)
H2 0.8229 0.0768 0.73 0.066*
C3 0.7526 (2) 0.0623 (3) 0.75522 (17) 0.0752 (11)
H3 0.7419 0.1313 0.7518 0.09*
C4 0.71999 (19) −0.0065 (3) 0.77297 (17) 0.0768 (11)
H4 0.6865 0.0155 0.7804 0.092*
C5 0.73669 (16) −0.1068 (3) 0.77967 (14) 0.0621 (9)
H5 0.7148 −0.1534 0.792 0.075*
C6 0.78618 (15) −0.1396 (2) 0.76812 (13) 0.0524 (7)
H6 0.7983 −0.2079 0.7741 0.063*
C7 0.84532 (13) −0.19569 (19) 0.66282 (12) 0.0411 (6)
C8 0.87874 (15) −0.2110 (2) 0.62867 (14) 0.0547 (8)
H8 0.9177 −0.1797 0.6398 0.066*
C9 0.85363 (17) −0.2730 (3) 0.57799 (15) 0.0671 (10)
H9 0.8756 −0.2824 0.5548 0.081*
C10 0.79721 (18) −0.3200 (3) 0.56208 (15) 0.0706 (10)
H10 0.7811 −0.3625 0.5285 0.085*
C11 0.76397 (18) −0.3051 (3) 0.59513 (16) 0.0694 (10)
H11 0.7249 −0.3363 0.5835 0.083*
C12 0.78835 (15) −0.2437 (2) 0.64586 (13) 0.0560 (8)
H12 0.7659 −0.2349 0.6686 0.067*
C13 0.92309 (13) −0.2033 (2) 0.78900 (12) 0.0436 (6)
C14 0.93637 (16) −0.3018 (2) 0.77782 (15) 0.0613 (9)
H14 0.9245 −0.3234 0.7384 0.074*
C15 0.96749 (18) −0.3687 (3) 0.82533 (18) 0.0770 (11)
H15 0.9769 −0.4345 0.8174 0.092*
C16 0.98448 (17) −0.3396 (3) 0.88318 (17) 0.0736 (11)
H16 1.0041 −0.3856 0.9146 0.088*
C17 0.97239 (17) −0.2422 (3) 0.89466 (15) 0.0717 (10)
H17 0.9847 −0.2213 0.9342 0.086*
C18 0.94185 (15) −0.1738 (3) 0.84792 (14) 0.0585 (8)
H18 0.934 −0.1074 0.8564 0.07*
P2 0.86831 (3) 0.09673 (5) 0.62360 (3) 0.03564 (16)
C19 0.88124 (12) 0.2359 (2) 0.63031 (12) 0.0401 (6)
C20 0.90876 (14) 0.2779 (2) 0.68686 (13) 0.0521 (8)
H20 0.9236 0.2352 0.7203 0.063*
C21 0.91480 (16) 0.3830 (2) 0.69503 (15) 0.0636 (9)
H21 0.9334 0.4101 0.7337 0.076*
C22 0.89343 (16) 0.4465 (2) 0.64633 (17) 0.0654 (9)
H22 0.8971 0.517 0.6518 0.079*
C23 0.86680 (18) 0.4065 (3) 0.58989 (17) 0.0717 (10)
H23 0.8526 0.4499 0.5567 0.086*
C24 0.86062 (16) 0.3016 (2) 0.58135 (14) 0.0593 (8)
H24 0.8425 0.275 0.5425 0.071*
C25 0.78347 (12) 0.0915 (2) 0.60350 (11) 0.0398 (6)
C26 0.74864 (14) 0.1729 (2) 0.60884 (13) 0.0523 (7)
H26 0.7679 0.2362 0.6214 0.063*
C27 0.68550 (16) 0.1614 (3) 0.59578 (16) 0.0680 (9)
H27 0.6628 0.2171 0.5995 0.082*
C28 0.65644 (16) 0.0694 (3) 0.57752 (16) 0.0685 (10)
H28 0.6143 0.0619 0.5697 0.082*
C29 0.68964 (15) −0.0129 (3) 0.57065 (15) 0.0597 (8)
H29 0.6696 −0.0755 0.5574 0.072*
C30 0.75280 (14) −0.0021 (2) 0.58356 (13) 0.0470 (7)
H30 0.775 −0.0577 0.5789 0.056*
C31 0.86728 (13) 0.0638 (2) 0.55073 (12) 0.0414 (6)
C32 0.81587 (15) 0.0855 (2) 0.49619 (12) 0.0545 (8)
H32 0.7809 0.1187 0.4962 0.065*
C33 0.81608 (19) 0.0587 (3) 0.44229 (14) 0.0676 (10)
H33 0.7815 0.0745 0.4063 0.081*
C34 0.8669 (2) 0.0088 (3) 0.44120 (16) 0.0728 (11)
H34 0.8673 −0.0083 0.4047 0.087*
C35 0.9171 (2) −0.0156 (3) 0.49460 (19) 0.0835 (12)
H35 0.9514 −0.0503 0.4942 0.1*
C36 0.91725 (16) 0.0110 (3) 0.54926 (15) 0.0639 (9)
H36 0.9513 −0.007 0.5851 0.077*
Rh1 0.941218 (9) 0.013747 (14) 0.708963 (9) 0.03409 (7)
C40 1.01769 (13) 0.0593 (2) 0.70298 (12) 0.0435 (7)
O40 1.04318 (10) 0.09216 (19) 0.67507 (10) 0.0660 (6)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
P1 0.0398 (4) 0.0314 (3) 0.0343 (3) −0.0018 (3) 0.0101 (3) −0.0004 (3)
C1 0.0425 (15) 0.0420 (16) 0.0325 (13) −0.0010 (12) 0.0106 (12) −0.0010 (11)
C2 0.072 (2) 0.0469 (18) 0.0517 (18) 0.0104 (15) 0.0326 (16) 0.0081 (14)
C3 0.094 (3) 0.064 (2) 0.081 (3) 0.031 (2) 0.051 (2) 0.015 (2)
C4 0.075 (3) 0.101 (3) 0.071 (2) 0.027 (2) 0.048 (2) 0.016 (2)
C5 0.063 (2) 0.078 (2) 0.0519 (19) −0.0085 (18) 0.0311 (17) 0.0064 (17)
C6 0.0587 (19) 0.0476 (17) 0.0506 (17) −0.0074 (14) 0.0234 (15) −0.0024 (14)
C7 0.0443 (15) 0.0309 (13) 0.0369 (14) 0.0001 (11) 0.0071 (12) −0.0004 (11)
C8 0.0515 (18) 0.0554 (19) 0.0513 (18) 0.0051 (15) 0.0169 (15) −0.0078 (14)
C9 0.074 (2) 0.068 (2) 0.0511 (19) 0.0114 (19) 0.0190 (17) −0.0148 (17)
C10 0.080 (3) 0.056 (2) 0.0483 (19) 0.0008 (19) 0.0029 (18) −0.0171 (16)
C11 0.072 (2) 0.059 (2) 0.063 (2) −0.0199 (18) 0.0158 (19) −0.0109 (17)
C12 0.061 (2) 0.0533 (19) 0.0499 (17) −0.0183 (15) 0.0205 (15) −0.0082 (14)
C13 0.0429 (15) 0.0394 (15) 0.0425 (15) 0.0003 (12) 0.0129 (13) 0.0071 (12)
C14 0.067 (2) 0.0473 (18) 0.0561 (19) 0.0123 (16) 0.0140 (16) 0.0040 (15)
C15 0.081 (3) 0.049 (2) 0.079 (3) 0.0132 (19) 0.014 (2) 0.0149 (19)
C16 0.063 (2) 0.067 (2) 0.073 (3) 0.0084 (18) 0.0131 (19) 0.035 (2)
C17 0.071 (2) 0.084 (3) 0.0462 (19) 0.000 (2) 0.0128 (17) 0.0166 (18)
C18 0.067 (2) 0.0502 (18) 0.0500 (18) −0.0006 (16) 0.0172 (16) 0.0045 (14)
P2 0.0333 (3) 0.0350 (4) 0.0313 (3) 0.0018 (3) 0.0071 (3) 0.0008 (3)
C19 0.0349 (14) 0.0352 (14) 0.0426 (15) 0.0018 (11) 0.0097 (11) 0.0019 (11)
C20 0.0530 (18) 0.0422 (16) 0.0472 (17) 0.0042 (14) 0.0087 (14) −0.0011 (13)
C21 0.067 (2) 0.0438 (18) 0.062 (2) −0.0012 (16) 0.0106 (16) −0.0124 (15)
C22 0.066 (2) 0.0346 (16) 0.087 (3) −0.0006 (15) 0.025 (2) −0.0032 (17)
C23 0.088 (3) 0.0410 (18) 0.075 (2) 0.0024 (17) 0.025 (2) 0.0164 (17)
C24 0.072 (2) 0.0459 (18) 0.0479 (18) −0.0008 (16) 0.0146 (16) 0.0047 (14)
C25 0.0343 (14) 0.0432 (15) 0.0334 (13) 0.0033 (11) 0.0067 (11) 0.0032 (11)
C26 0.0454 (17) 0.0526 (18) 0.0557 (18) 0.0042 (14) 0.0188 (15) −0.0013 (14)
C27 0.051 (2) 0.075 (2) 0.082 (2) 0.0142 (18) 0.0320 (19) 0.0062 (19)
C28 0.0387 (17) 0.086 (3) 0.076 (2) −0.0043 (18) 0.0207 (17) 0.012 (2)
C29 0.0460 (17) 0.060 (2) 0.064 (2) −0.0115 (15) 0.0156 (15) 0.0076 (16)
C30 0.0418 (15) 0.0487 (17) 0.0435 (15) −0.0005 (13) 0.0118 (12) 0.0039 (12)
C31 0.0430 (15) 0.0404 (15) 0.0372 (14) −0.0042 (12) 0.0141 (12) −0.0014 (11)
C32 0.062 (2) 0.0548 (18) 0.0376 (15) 0.0089 (15) 0.0132 (14) 0.0042 (13)
C33 0.092 (3) 0.063 (2) 0.0361 (16) −0.003 (2) 0.0164 (17) 0.0008 (15)
C34 0.096 (3) 0.081 (3) 0.051 (2) −0.026 (2) 0.040 (2) −0.0163 (18)
C35 0.071 (3) 0.111 (3) 0.080 (3) −0.006 (2) 0.044 (2) −0.027 (2)
C36 0.0499 (18) 0.085 (3) 0.0538 (19) 0.0008 (17) 0.0195 (15) −0.0136 (17)
Rh1 0.03109 (11) 0.03049 (11) 0.03132 (11) −0.00057 (8) 0.00472 (8) 0.00033 (8)
C40 0.0425 (16) 0.0366 (14) 0.0378 (14) −0.0003 (12) 0.0047 (12) 0.0054 (12)
O40 0.0493 (13) 0.0884 (17) 0.0531 (13) −0.0058 (12) 0.0154 (11) 0.0280 (12)
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Geometric parameters (Å, º)

P1—C1 1.836 (3) P2—Rh1 2.3283 (8)
P1—C7 1.838 (3) C19—C20 1.372 (4)
P1—C13 1.843 (3) C19—C24 1.386 (4)
P1—Rh1 2.3222 (7) C20—C21 1.387 (4)
C1—C2 1.376 (4) C20—H20 0.93
C1—C6 1.387 (4) C21—C22 1.364 (5)
C2—C3 1.382 (5) C21—H21 0.93
C2—H2 0.93 C22—C23 1.359 (5)
C3—C4 1.372 (5) C22—H22 0.93
C3—H3 0.93 C23—C24 1.386 (4)
C4—C5 1.359 (5) C23—H23 0.93
C4—H4 0.93 C24—H24 0.93
C5—C6 1.382 (4) C25—C26 1.384 (4)
C5—H5 0.93 C25—C30 1.397 (4)
C6—H6 0.93 C26—C27 1.386 (4)
C7—C12 1.372 (4) C26—H26 0.93
C7—C8 1.393 (4) C27—C28 1.361 (5)
C8—C9 1.389 (4) C27—H27 0.93
C8—H8 0.93 C28—C29 1.383 (5)
C9—C10 1.358 (5) C28—H28 0.93
C9—H9 0.93 C29—C30 1.386 (4)
C10—C11 1.366 (5) C29—H29 0.93
C10—H10 0.93 C30—H30 0.93
C11—C12 1.384 (4) C31—C36 1.377 (4)
C11—H11 0.93 C31—C32 1.394 (4)
C12—H12 0.93 C32—C33 1.376 (4)
C13—C18 1.378 (4) C32—H32 0.93
C13—C14 1.381 (4) C33—C34 1.373 (5)
C14—C15 1.389 (4) C33—H33 0.93
C14—H14 0.93 C34—C35 1.372 (6)
C15—C16 1.358 (5) C34—H34 0.93
C15—H15 0.93 C35—C36 1.390 (5)
C16—C17 1.361 (5) C35—H35 0.93
C16—H16 0.93 C36—H36 0.93
C17—C18 1.388 (4) Rh1—C40 1.961 (3)
C17—H17 0.93 Rh1—C40i 2.045 (3)
C18—H18 0.93 Rh1—Rh1i 2.6266 (8)
P2—C31 1.837 (3) C40—O40 1.173 (3)
P2—C25 1.838 (3) C40—Rh1i 2.045 (3)
P2—C19 1.841 (3)
C1—P1—C7 105.72 (13) C20—C19—P2 118.3 (2)
C1—P1—C13 99.86 (13) C24—C19—P2 123.5 (2)
C7—P1—C13 101.28 (12) C19—C20—C21 121.2 (3)
C1—P1—Rh1 119.62 (9) C19—C20—H20 119.4
C7—P1—Rh1 109.80 (9) C21—C20—H20 119.4
C13—P1—Rh1 118.38 (9) C22—C21—C20 120.0 (3)
C2—C1—C6 118.3 (3) C22—C21—H21 120
C2—C1—P1 118.2 (2) C20—C21—H21 120
C6—C1—P1 123.4 (2) C23—C22—C21 119.8 (3)
C1—C2—C3 120.4 (3) C23—C22—H22 120.1
C1—C2—H2 119.8 C21—C22—H22 120.1
C3—C2—H2 119.8 C22—C23—C24 120.5 (3)
C4—C3—C2 120.3 (3) C22—C23—H23 119.7
C4—C3—H3 119.8 C24—C23—H23 119.7
C2—C3—H3 119.8 C19—C24—C23 120.4 (3)
C5—C4—C3 120.0 (3) C19—C24—H24 119.8
C5—C4—H4 120 C23—C24—H24 119.8
C3—C4—H4 120 C26—C25—C30 118.0 (3)
C4—C5—C6 120.0 (3) C26—C25—P2 124.4 (2)
C4—C5—H5 120 C30—C25—P2 117.6 (2)
C6—C5—H5 120 C25—C26—C27 121.0 (3)
C5—C6—C1 120.8 (3) C25—C26—H26 119.5
C5—C6—H6 119.6 C27—C26—H26 119.5
C1—C6—H6 119.6 C28—C27—C26 120.5 (3)
C12—C7—C8 118.9 (3) C28—C27—H27 119.8
C12—C7—P1 124.7 (2) C26—C27—H27 119.8
C8—C7—P1 116.4 (2) C27—C28—C29 119.9 (3)
C9—C8—C7 119.7 (3) C27—C28—H28 120
C9—C8—H8 120.1 C29—C28—H28 120
C7—C8—H8 120.1 C28—C29—C30 119.9 (3)
C10—C9—C8 120.4 (3) C28—C29—H29 120
C10—C9—H9 119.8 C30—C29—H29 120
C8—C9—H9 119.8 C29—C30—C25 120.6 (3)
C9—C10—C11 120.3 (3) C29—C30—H30 119.7
C9—C10—H10 119.9 C25—C30—H30 119.7
C11—C10—H10 119.9 C36—C31—C32 118.1 (3)
C10—C11—C12 120.1 (3) C36—C31—P2 119.6 (2)
C10—C11—H11 120 C32—C31—P2 122.2 (2)
C12—C11—H11 120 C33—C32—C31 121.0 (3)
C7—C12—C11 120.6 (3) C33—C32—H32 119.5
C7—C12—H12 119.7 C31—C32—H32 119.5
C11—C12—H12 119.7 C34—C33—C32 120.5 (3)
C18—C13—C14 118.4 (3) C34—C33—H33 119.7
C18—C13—P1 119.2 (2) C32—C33—H33 119.7
C14—C13—P1 122.5 (2) C35—C34—C33 119.1 (3)
C13—C14—C15 120.1 (3) C35—C34—H34 120.4
C13—C14—H14 120 C33—C34—H34 120.4
C15—C14—H14 120 C34—C35—C36 120.8 (4)
C16—C15—C14 121.1 (3) C34—C35—H35 119.6
C16—C15—H15 119.4 C36—C35—H35 119.6
C14—C15—H15 119.4 C31—C36—C35 120.4 (3)
C15—C16—C17 119.2 (3) C31—C36—H36 119.8
C15—C16—H16 120.4 C35—C36—H36 119.8
C17—C16—H16 120.4 C40—Rh1—C40i 87.93 (14)
C16—C17—C18 120.7 (3) C40—Rh1—P1 151.76 (8)
C16—C17—H17 119.7 C40i—Rh1—P1 92.09 (9)
C18—C17—H17 119.7 C40—Rh1—P2 97.56 (8)
C13—C18—C17 120.6 (3) C40i—Rh1—P2 130.38 (8)
C13—C18—H18 119.7 P1—Rh1—P2 103.76 (3)
C17—C18—H18 119.7 C40—Rh1—Rh1i 50.44 (8)
C31—P2—C25 100.08 (12) C40i—Rh1—Rh1i 47.66 (8)
C31—P2—C19 104.56 (13) P1—Rh1—Rh1i 111.635 (19)
C25—P2—C19 100.32 (12) P2—Rh1—Rh1i 144.50 (2)
C31—P2—Rh1 117.82 (9) O40—C40—Rh1 151.0 (2)
C25—P2—Rh1 121.02 (9) O40—C40—Rh1i 127.0 (2)
C19—P2—Rh1 110.55 (8) Rh1—C40—Rh1i 81.90 (11)
C20—C19—C24 118.0 (3)
C7—P1—C1—C2 −115.7 (2) Rh1—P2—C25—C26 107.8 (2)
C13—P1—C1—C2 139.5 (2) C31—P2—C25—C30 61.5 (2)
Rh1—P1—C1—C2 8.7 (3) C19—P2—C25—C30 168.5 (2)
C7—P1—C1—C6 65.1 (3) Rh1—P2—C25—C30 −69.8 (2)
C13—P1—C1—C6 −39.7 (3) C30—C25—C26—C27 1.1 (4)
Rh1—P1—C1—C6 −170.5 (2) P2—C25—C26—C27 −176.5 (2)
C6—C1—C2—C3 −2.1 (5) C25—C26—C27—C28 0.2 (5)
P1—C1—C2—C3 178.6 (3) C26—C27—C28—C29 −1.4 (6)
C1—C2—C3—C4 −0.6 (6) C27—C28—C29—C30 1.3 (5)
C2—C3—C4—C5 1.9 (6) C28—C29—C30—C25 0.0 (5)
C3—C4—C5—C6 −0.5 (6) C26—C25—C30—C29 −1.1 (4)
C4—C5—C6—C1 −2.2 (5) P2—C25—C30—C29 176.6 (2)
C2—C1—C6—C5 3.5 (4) C25—P2—C31—C36 −148.2 (3)
P1—C1—C6—C5 −177.3 (2) C19—P2—C31—C36 108.3 (3)
C1—P1—C7—C12 −18.3 (3) Rh1—P2—C31—C36 −14.9 (3)
C13—P1—C7—C12 85.5 (3) C25—P2—C31—C32 28.3 (3)
Rh1—P1—C7—C12 −148.6 (2) C19—P2—C31—C32 −75.2 (3)
C1—P1—C7—C8 161.5 (2) Rh1—P2—C31—C32 161.6 (2)
C13—P1—C7—C8 −94.8 (2) C36—C31—C32—C33 −2.6 (5)
Rh1—P1—C7—C8 31.2 (2) P2—C31—C32—C33 −179.1 (3)
C12—C7—C8—C9 0.8 (4) C31—C32—C33—C34 0.7 (5)
P1—C7—C8—C9 −179.0 (2) C32—C33—C34—C35 1.1 (6)
C7—C8—C9—C10 −1.0 (5) C33—C34—C35—C36 −1.0 (6)
C8—C9—C10—C11 1.3 (6) C32—C31—C36—C35 2.7 (5)
C9—C10—C11—C12 −1.4 (6) P2—C31—C36—C35 179.3 (3)
C8—C7—C12—C11 −1.0 (5) C34—C35—C36—C31 −1.0 (6)
P1—C7—C12—C11 178.8 (2) C1—P1—Rh1—C40 158.53 (19)
C10—C11—C12—C7 1.3 (5) C7—P1—Rh1—C40 −79.1 (2)
C1—P1—C13—C18 −53.5 (3) C13—P1—Rh1—C40 36.5 (2)
C7—P1—C13—C18 −161.9 (3) C1—P1—Rh1—C40i 69.02 (13)
Rh1—P1—C13—C18 78.1 (3) C7—P1—Rh1—C40i −168.58 (12)
C1—P1—C13—C14 126.8 (3) C13—P1—Rh1—C40i −53.06 (13)
C7—P1—C13—C14 18.5 (3) C1—P1—Rh1—P2 −63.55 (10)
Rh1—P1—C13—C14 −101.5 (3) C7—P1—Rh1—P2 58.85 (9)
C18—C13—C14—C15 0.5 (5) C13—P1—Rh1—P2 174.37 (11)
P1—C13—C14—C15 −179.9 (3) C1—P1—Rh1—Rh1i 113.74 (9)
C13—C14—C15—C16 1.1 (6) C7—P1—Rh1—Rh1i −123.86 (9)
C14—C15—C16—C17 −2.0 (6) C13—P1—Rh1—Rh1i −8.34 (11)
C15—C16—C17—C18 1.4 (6) C31—P2—Rh1—C40 59.88 (13)
C14—C13—C18—C17 −1.1 (5) C25—P2—Rh1—C40 −176.87 (13)
P1—C13—C18—C17 179.3 (3) C19—P2—Rh1—C40 −60.21 (13)
C16—C17—C18—C13 0.2 (5) C31—P2—Rh1—C40i 153.61 (15)
C31—P2—C19—C20 −154.4 (2) C25—P2—Rh1—C40i −83.14 (15)
C25—P2—C19—C20 102.2 (2) C19—P2—Rh1—C40i 33.52 (15)
Rh1—P2—C19—C20 −26.6 (3) C31—P2—Rh1—P1 −101.46 (10)
C31—P2—C19—C24 30.4 (3) C25—P2—Rh1—P1 21.78 (11)
C25—P2—C19—C24 −73.0 (3) C19—P2—Rh1—P1 138.45 (10)
Rh1—P2—C19—C24 158.1 (2) C31—P2—Rh1—Rh1i 82.89 (11)
C24—C19—C20—C21 1.2 (5) C25—P2—Rh1—Rh1i −153.87 (10)
P2—C19—C20—C21 −174.3 (3) C19—P2—Rh1—Rh1i −37.21 (11)
C19—C20—C21—C22 −0.3 (5) C40i—Rh1—C40—O40 −150.3 (5)
C20—C21—C22—C23 −0.6 (6) P1—Rh1—C40—O40 119.1 (5)
C21—C22—C23—C24 0.6 (6) P2—Rh1—C40—O40 −19.8 (5)
C20—C19—C24—C23 −1.2 (5) Rh1i—Rh1—C40—O40 177.3 (6)
P2—C19—C24—C23 174.0 (3) C40i—Rh1—C40—Rh1i 32.40 (14)
C22—C23—C24—C19 0.3 (6) P1—Rh1—C40—Rh1i −58.2 (2)
C31—P2—C25—C26 −120.9 (3) P2—Rh1—C40—Rh1i 162.88 (6)
C19—P2—C25—C26 −13.9 (3)
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Symmetry code: (i) −x+2, y, −z+3/2.

Footnotes

1

CAS 47921–72–2, 48246–55–5.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5542).

References

  1. Allen, F. H. (2002). Acta Cryst. B58, 380–388. [DOI] [PubMed]
  2. Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.
  3. Douglas, S., Lowe, J. P., Mahon, M. F., Warren, J. E. & Whittlesey, M. K. (2005). J. Organomet. Chem. 690, 5027–5035.
  4. Dzik, W. I., Creusen, C., de Gelder, R., Peters, T. P. J., Smits, J. M. M. & de Bruin, B. (2010). Organometallics, 29, 1629–1641.
  5. Enraf–Nonius (1994). CAD-4 EXPRESS Enraf–Nonius, Delft, The Netherlands.
  6. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
  7. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
  8. Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  9. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  10. Okazaki, M., Hayashi, A., Fu, C. F., Liu, S. T. & Ozawa, F. (2009). Organometallics, 28, 902–908.
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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Click here for additional data file. (27.7KB, cif)

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043528/lh5542sup1.cif

e-68-m1408-sup1.cif (27.7KB, cif)
Click here for additional data file. (387.8KB, hkl)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043528/lh5542Isup2.hkl

e-68-m1408-Isup2.hkl (387.8KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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