(Acetyl­acetonato-κ2O,O′)carbon­yl[dicyclo­hex­yl(2,6-diisopropyl­phen­yl)phosphane-κP]rhodium(I)

Davis, W.L.; Mathobela, S.D.; Meijboom, R.

doi:10.1107/S1600536812018831

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m737

doi:10.1107/S1600536812018831

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(Acetylacetonato-κ²O,O′)carbonyl[dicyclohexyl(2,6-diisopropylphenyl)phosphane-κP]rhodium(I)

Wade L. Davis,^a Sfiso D. Mathobela ^a and Reinout Meijboom ^a ^*

^aResearch Center for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg 2006, South Africa
^*Correspondence e-mail: rmeijboom@uj.ac.za

(Received 2 March 2012; accepted 26 April 2012; online 5 May 2012)

In the title compound, [Rh(C₅H₇O₂){C₁₂H₁₇P(C₆H₁₁)₂}(CO)], the Rh^I atom is coordinated by one carbonyl C, one P and two O atoms, forming a slighlty distorted square-planar configuration.

Related literature

For background literature on the catalytic activity of rhodium–phosphine compounds, see Moloy & Wegman (1989 ); Nozaki et al. (1997 ); Ocando-Mavarez et al. (2003 ); Hayashi & Yamasaki (2003 ); Erasmus & Conradie (2011 ). For related rhodium compounds, see: Riihimaki et al. (2003 ); Brink et al. (2007 ); Davis & Meijboom (2011 ).

Experimental

Crystal data

[Rh(C₅H₇O₂)(C₂₄H₃₉P)(CO)]
M_r = 588.55
Monoclinic, C c
a = 16.750 (2) Å
b = 9.7334 (13) Å
c = 19.385 (3) Å
β = 111.669 (3)°
V = 2937.1 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.66 mm⁻¹
T = 100 K
0.29 × 0.23 × 0.22 mm

Data collection

Bruker APEX DUO 4K-CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.553, T_max = 0.746
14224 measured reflections
6007 independent reflections
5516 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.105
S = 1.05
6007 reflections
322 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 1.85 e Å⁻³
Δρ_min = −1.42 e Å⁻³
Absolute structure: Flack (1983 ), 2437 Friedel pairs
Flack parameter: −0.03 (3)

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: publCIF (Westrip, 2010 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812018831/aa2053sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018831/aa2053Isup2.hkl

checkCIF report

Comment top

Transition metal complexes bearing functionalized phosphines are of interest due to their potential catalytic properties (Ocando-Mavarez et al., 2003). These complexes are used with various chiral ligands in the process of highly enantioselective hydroformylation reactions (Nozaki et al., 1997). Studies illustrating the catalytic importance of rhodium(I) square-planar moieties have been conducted on rhodium mono- and di-phosphane complexes containing the symmetrical bidentate ligand, acac (acac = acetylacetonate) (Moloy & Wegman, 1989; Erasmus & Conradie, 2011) as well as rhodium-catalyzed asymmetric 1,4-addition (Hayashi & Yamasaki, 2003). This work is part of an ongoing investigation aimed at determing the steric effects induced by various phosphine ligands on a rhodium(I) metal centre.

The title compound, [Rh(acac)(CO){C₁₂H₁₇P(C₆H₁₁)₂}] (acac = acetylacetonate), crystallizes in the non-centrosymmetric monoclinic space group, C c (Z=4). The Rh(I) atom has a slightly distorted square-planar geometric coordination (see Fig. 1), illustrated by C1—Rh1—P1 and O2—Rh1—O3 angles of 94.54 (1)° and 89.37 (1)°, respectively, deviating from the ideal 90° right angle. A slightly asymmetric coordination of the acac ligand is observed, whereby the Rh1—O2 distance (2.083 (3) Å) is longer than that for Rh1—O3 (2.059 (3) Å), which may be attributed to a trans influence of the phosphane ligand. The steric demand of the phosphane ligand is indicated by the smaller O3—Rh1—P1 angle, (86.64 (9)°), compared to that of the carbonyl ligand, O2—Rh1—C1 (94.97 (1)°). All geometric parameters are similar to previous reported complexes of the general formula [Rh(acac)(CO)L]; L = tertiary phosphane ligand (Davis & Meijboom, 2011; Brink et al., 2007; Riihimaki et al., 2003).

Related literature top

For background literature on the catalytic activity of rhodium–phosphine compounds, see Moloy & Wegman (1989); Nozaki et al. (1997); Ocando-Mavarez et al. (2003); Hayashi & Yamasaki (2003); Erasmus & Conradie (2011). For related rhodium compounds, see: Riihimaki et al. (2003); Brink et al. (2007); Davis & Meijboom (2011).

Experimental top

A solution of [Rh(acac)(CO)₂] (42.2 mg, 0.16 mmol) in acetone (5 ml) was slowly added to a solution of C₁₂H₁₇P(C₆H₁₁)₂ (64.5 mg, 0.18 mmol) in acetone (5 ml). Slow evaporation of the solvent afforded the title compound as yellow crystals. Spectroscopic analysis: ³¹P NMR (CDCl₃, 162 MHz, p.p.m.): 47.5 [d, ¹J(Rh—P)= 165.7 Hz]; IR (CH₂Cl₂) ν(CO): 1959.2 cm^-1.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010) and WinGX (Farrugia, 1999).

Figures top

Fig. 1. Molecular structure of the title compound, showing the atom numbering system. Displacement ellipsoids are drawn at the 50% probability level. For the C atoms in rings; the first digit indicates ring number and the second digit indicates the position of the atom in the ring.

(Acetylacetonato-κ²O,O')carbonyl[dicyclohexyl(2,6- diisopropylphenyl)phosphane-κP]rhodium(I) top

Crystal data top

[Rh(C₅H₇O₂)(C₂₄H₃₉P)(CO)]	F(000) = 1240
M_r = 588.55	D_x = 1.331 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5131 reflections
a = 16.750 (2) Å	θ = 2.5–27.6°
b = 9.7334 (13) Å	µ = 0.66 mm⁻¹
c = 19.385 (3) Å	T = 100 K
β = 111.669 (3)°	Cubic, yellow
V = 2937.1 (7) Å³	0.29 × 0.23 × 0.22 mm
Z = 4

Data collection top

Bruker APEX DUO 4K-CCD diffractometer	6007 independent reflections
Radiation source: sealed tube	5516 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 8.4 pixels mm^-1	θ_max = 28.2°, θ_min = 2.5°
ϕ and ω scans	h = −21→22
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −12→12
T_min = 0.553, T_max = 0.746	l = −25→24
14224 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0588P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
6007 reflections	Δρ_max = 1.85 e Å⁻³
322 parameters	Δρ_min = −1.42 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 2437 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (3)

Crystal data top

[Rh(C₅H₇O₂)(C₂₄H₃₉P)(CO)]	V = 2937.1 (7) Å³
M_r = 588.55	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 16.750 (2) Å	µ = 0.66 mm⁻¹
b = 9.7334 (13) Å	T = 100 K
c = 19.385 (3) Å	0.29 × 0.23 × 0.22 mm
β = 111.669 (3)°

Data collection top

Bruker APEX DUO 4K-CCD diffractometer	6007 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	5516 reflections with I > 2σ(I)
T_min = 0.553, T_max = 0.746	R_int = 0.049
14224 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.105	Δρ_max = 1.85 e Å⁻³
S = 1.05	Δρ_min = −1.42 e Å⁻³
6007 reflections	Absolute structure: Flack (1983), 2437 Friedel pairs
322 parameters	Absolute structure parameter: −0.03 (3)
2 restraints

Special details top

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 2 s/frame. A total of 1125 frames were collected with a frame width of 0.5° covering up to θ = 28.18° with 99.1% completeness accomplished.

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

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

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

	x	y	z	U_iso*/U_eq
Rh1	1.04568 (3)	0.50680 (3)	0.55184 (3)	0.01467 (8)
P1	0.96331 (6)	0.64795 (10)	0.45914 (6)	0.0128 (2)
O1	0.9055 (2)	0.4101 (4)	0.5979 (2)	0.0355 (9)
O3	1.14853 (18)	0.5725 (3)	0.52656 (17)	0.0212 (6)
O2	1.12596 (19)	0.3671 (3)	0.62714 (18)	0.0223 (7)
C1	0.9568 (3)	0.4502 (5)	0.5774 (2)	0.0230 (9)
C31	0.9846 (2)	0.5943 (4)	0.3744 (2)	0.0151 (8)
H2	0.9303	0.6115	0.3309	0.018*
C36	1.0561 (3)	0.6742 (4)	0.3596 (2)	0.0187 (8)
H3A	1.0459	0.7742	0.3609	0.022*
H3B	1.1125	0.6528	0.3987	0.022*
C35	1.0568 (3)	0.6340 (5)	0.2839 (2)	0.0212 (9)
H4A	1.1039	0.6833	0.2753	0.025*
H4B	1.0019	0.6625	0.2449	0.025*
C34	1.0688 (3)	0.4798 (5)	0.2781 (3)	0.0271 (10)
H5A	1.1272	0.4535	0.312	0.033*
H5B	1.0636	0.457	0.2268	0.033*
C33	1.0022 (3)	0.3972 (5)	0.2977 (3)	0.0225 (9)
H6A	0.9442	0.4137	0.2598	0.027*
H6B	1.0149	0.2979	0.2977	0.027*
C32	1.0034 (3)	0.4391 (4)	0.3742 (2)	0.0177 (8)
H7A	1.0603	0.4184	0.4126	0.021*
H7B	0.9595	0.3862	0.3859	0.021*
C11	0.9794 (2)	0.8374 (4)	0.4696 (2)	0.0151 (8)
C12	1.0292 (2)	0.8964 (4)	0.5403 (2)	0.0157 (8)
C7	1.0743 (3)	0.8194 (4)	0.6126 (2)	0.0208 (9)
H10	1.0627	0.7193	0.6019	0.025*
C9	1.1720 (3)	0.8394 (5)	0.6400 (3)	0.0383 (13)
H11A	1.1927	0.8107	0.6011	0.057*
H11B	1.1998	0.7837	0.6845	0.057*
H11C	1.1859	0.9365	0.6518	0.057*
C8	1.0383 (4)	0.8585 (5)	0.6715 (3)	0.0405 (13)
H12A	1.0432	0.958	0.6796	0.061*
H12B	1.0708	0.811	0.718	0.061*
H12C	0.9778	0.8315	0.6548	0.061*
C13	1.0382 (4)	1.0397 (4)	0.5487 (4)	0.0209 (9)
H13	1.0712	1.0772	0.5959	0.025*
C14	0.9997 (3)	1.1268 (5)	0.4895 (3)	0.0245 (10)
H14	1.0064	1.2234	0.4961	0.029*
C15	0.9518 (3)	1.0737 (5)	0.4209 (3)	0.0218 (9)
H15	0.9255	1.1344	0.3805	0.026*
C16	0.9410 (2)	0.9319 (4)	0.4096 (2)	0.0161 (8)
C17	0.8849 (3)	0.8926 (4)	0.3296 (2)	0.0203 (9)
H17	0.885	0.7902	0.3256	0.024*
C19	0.9197 (3)	0.9524 (5)	0.2727 (3)	0.0269 (10)
H18A	0.9139	1.0527	0.2715	0.04*
H18B	0.887	0.9148	0.2234	0.04*
H18C	0.9805	0.9278	0.287	0.04*
C18	0.7919 (3)	0.9396 (5)	0.3118 (3)	0.0273 (10)
H19A	0.7689	0.8945	0.3457	0.041*
H19B	0.7568	0.9148	0.2605	0.041*
H19C	0.7906	1.0394	0.3178	0.041*
C21	0.8441 (2)	0.6307 (4)	0.4276 (2)	0.0165 (8)
H20	0.8194	0.6898	0.3824	0.02*
C22	0.8091 (3)	0.6873 (4)	0.4847 (3)	0.0220 (9)
H21A	0.8251	0.7853	0.4943	0.026*
H21B	0.8353	0.6365	0.532	0.026*
C23	0.7110 (3)	0.6732 (5)	0.4567 (3)	0.0290 (11)
H22A	0.6905	0.7054	0.4956	0.035*
H22B	0.6848	0.7323	0.4125	0.035*
C24	0.6826 (3)	0.5260 (5)	0.4366 (3)	0.0307 (11)
H23A	0.6191	0.521	0.4179	0.037*
H23B	0.7056	0.4676	0.4814	0.037*
C25	0.7146 (3)	0.4728 (5)	0.3773 (3)	0.0282 (11)
H24A	0.6876	0.5266	0.3311	0.034*
H24B	0.6972	0.3756	0.3661	0.034*
C26	0.8128 (3)	0.4839 (4)	0.4030 (3)	0.0216 (9)
H25A	0.8397	0.42	0.4449	0.026*
H25B	0.831	0.4564	0.3619	0.026*
C2	1.2259 (3)	0.5256 (5)	0.5547 (3)	0.0224 (9)
C5	1.2883 (3)	0.5932 (6)	0.5257 (3)	0.0346 (12)
H27A	1.2702	0.576	0.4723	0.052*
H27B	1.3458	0.5551	0.5513	0.052*
H27C	1.2893	0.6924	0.5346	0.052*
C3	1.2540 (3)	0.4204 (5)	0.6063 (2)	0.0245 (10)
H28	1.3128	0.3949	0.6212	0.029*
C4	1.2047 (3)	0.3483 (4)	0.6385 (2)	0.0238 (9)
C6	1.2468 (3)	0.2315 (5)	0.6923 (3)	0.0353 (12)
H30A	1.2111	0.2084	0.7209	0.053*
H30B	1.3038	0.2604	0.7262	0.053*
H30C	1.2523	0.1507	0.6642	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Rh1	0.01337 (12)	0.01245 (13)	0.01730 (13)	−0.00060 (14)	0.00463 (9)	0.00048 (14)
P1	0.0102 (4)	0.0110 (4)	0.0173 (5)	−0.0018 (4)	0.0051 (4)	−0.0003 (4)
O1	0.0222 (16)	0.046 (2)	0.0360 (19)	−0.0074 (16)	0.0083 (15)	0.0175 (16)
O3	0.0128 (14)	0.0242 (16)	0.0269 (16)	0.0011 (12)	0.0076 (12)	0.0011 (13)
O2	0.0182 (15)	0.0164 (14)	0.0269 (17)	0.0012 (12)	0.0020 (13)	0.0057 (12)
C1	0.026 (2)	0.021 (2)	0.019 (2)	−0.0007 (19)	0.0043 (18)	0.0068 (17)
C31	0.0133 (17)	0.0171 (18)	0.0155 (19)	0.0034 (15)	0.0060 (15)	−0.0016 (14)
C36	0.0183 (19)	0.0192 (19)	0.020 (2)	−0.0018 (16)	0.0091 (16)	0.0009 (16)
C35	0.016 (2)	0.029 (2)	0.023 (2)	−0.0042 (18)	0.0127 (17)	−0.0004 (18)
C34	0.022 (2)	0.036 (3)	0.029 (2)	0.0006 (19)	0.016 (2)	−0.0075 (19)
C33	0.021 (2)	0.022 (2)	0.027 (2)	−0.0014 (18)	0.0114 (18)	−0.0071 (17)
C32	0.0127 (17)	0.0171 (19)	0.026 (2)	0.0004 (15)	0.0096 (16)	−0.0027 (17)
C11	0.0090 (18)	0.017 (2)	0.021 (2)	−0.0017 (15)	0.0078 (16)	−0.0016 (16)
C12	0.013 (2)	0.0143 (17)	0.019 (2)	−0.0025 (14)	0.0056 (17)	−0.0003 (15)
C7	0.028 (2)	0.014 (2)	0.016 (2)	0.0003 (18)	0.0030 (17)	0.0014 (16)
C9	0.028 (2)	0.028 (3)	0.042 (3)	−0.005 (2)	−0.008 (2)	0.000 (2)
C8	0.075 (4)	0.029 (3)	0.024 (2)	−0.007 (3)	0.025 (3)	−0.002 (2)
C13	0.020 (2)	0.0188 (17)	0.028 (2)	−0.004 (2)	0.0135 (19)	−0.007 (3)
C14	0.030 (2)	0.0125 (19)	0.036 (3)	0.0042 (18)	0.018 (2)	0.0016 (17)
C15	0.019 (2)	0.017 (2)	0.030 (2)	0.0021 (17)	0.0097 (18)	0.0032 (17)
C16	0.0118 (17)	0.0167 (19)	0.021 (2)	−0.0008 (15)	0.0073 (16)	0.0013 (16)
C17	0.0180 (19)	0.018 (2)	0.022 (2)	0.0019 (16)	0.0035 (16)	0.0009 (16)
C19	0.025 (2)	0.033 (2)	0.022 (2)	0.0050 (19)	0.0070 (19)	0.0047 (19)
C18	0.017 (2)	0.029 (2)	0.030 (2)	0.0018 (18)	0.0011 (18)	0.001 (2)
C21	0.0100 (17)	0.020 (2)	0.0190 (19)	−0.0015 (15)	0.0050 (15)	0.0000 (15)
C22	0.0152 (18)	0.021 (2)	0.031 (2)	−0.0007 (16)	0.0100 (17)	−0.0059 (17)
C23	0.0135 (19)	0.033 (3)	0.043 (3)	−0.0033 (18)	0.0138 (19)	−0.010 (2)
C24	0.019 (2)	0.040 (3)	0.039 (3)	−0.0161 (19)	0.019 (2)	−0.017 (2)
C25	0.015 (2)	0.038 (3)	0.033 (3)	−0.0107 (18)	0.011 (2)	−0.013 (2)
C26	0.017 (2)	0.027 (2)	0.021 (2)	−0.0037 (17)	0.0073 (17)	−0.0056 (16)
C2	0.0127 (19)	0.026 (2)	0.026 (2)	−0.0012 (16)	0.0035 (17)	−0.0091 (17)
C5	0.015 (2)	0.051 (3)	0.039 (3)	0.001 (2)	0.011 (2)	−0.002 (2)
C3	0.0144 (19)	0.026 (2)	0.028 (2)	0.0031 (17)	0.0012 (17)	−0.0081 (18)
C4	0.027 (2)	0.018 (2)	0.019 (2)	0.0032 (17)	0.0005 (17)	−0.0056 (16)
C6	0.027 (2)	0.020 (2)	0.042 (3)	0.0058 (19)	−0.007 (2)	0.001 (2)

Geometric parameters (Å, º) top

Rh1—C1	1.820 (5)	C14—C15	1.374 (7)
Rh1—O3	2.059 (3)	C14—H14	0.95
Rh1—O2	2.083 (3)	C15—C16	1.399 (6)
Rh1—P1	2.2780 (12)	C15—H15	0.95
P1—C11	1.864 (4)	C16—C17	1.536 (6)
P1—C21	1.868 (4)	C17—C18	1.536 (6)
P1—C31	1.879 (4)	C17—C19	1.539 (7)
O1—C1	1.141 (6)	C17—H17	1
O3—C2	1.289 (5)	C19—H18A	0.98
O2—C4	1.268 (5)	C19—H18B	0.98
C31—C36	1.542 (6)	C19—H18C	0.98
C31—C32	1.543 (6)	C18—H19A	0.98
C31—H2	1	C18—H19B	0.98
C36—C35	1.523 (6)	C18—H19C	0.98
C36—H3A	0.99	C21—C22	1.534 (6)
C36—H3B	0.99	C21—C26	1.536 (6)
C35—C34	1.525 (6)	C21—H20	1
C35—H4A	0.99	C22—C23	1.534 (5)
C35—H4B	0.99	C22—H21A	0.99
C34—C33	1.533 (7)	C22—H21B	0.99
C34—H5A	0.99	C23—C24	1.514 (6)
C34—H5B	0.99	C23—H22A	0.99
C33—C32	1.531 (6)	C23—H22B	0.99
C33—H6A	0.99	C24—C25	1.527 (7)
C33—H6B	0.99	C24—H23A	0.99
C32—H7A	0.99	C24—H23B	0.99
C32—H7B	0.99	C25—C26	1.537 (6)
C11—C12	1.435 (5)	C25—H24A	0.99
C11—C16	1.435 (6)	C25—H24B	0.99
C12—C13	1.405 (5)	C26—H25A	0.99
C12—C7	1.522 (6)	C26—H25B	0.99
C7—C8	1.523 (7)	C2—C3	1.387 (7)
C7—C9	1.535 (7)	C2—C5	1.508 (7)
C7—H10	1	C5—H27A	0.98
C9—H11A	0.98	C5—H27B	0.98
C9—H11B	0.98	C5—H27C	0.98
C9—H11C	0.98	C3—C4	1.396 (7)
C8—H12A	0.98	C3—H28	0.95
C8—H12B	0.98	C4—C6	1.527 (6)
C8—H12C	0.98	C6—H30A	0.98
C13—C14	1.380 (8)	C6—H30B	0.98
C13—H13	0.95	C6—H30C	0.98

C1—Rh1—O3	178.09 (18)	C14—C15—C16	121.2 (4)
C1—Rh1—O2	89.60 (17)	C14—C15—H15	119.4
O3—Rh1—O2	89.37 (12)	C16—C15—H15	119.4
C1—Rh1—P1	94.54 (14)	C15—C16—C11	120.8 (4)
O3—Rh1—P1	86.64 (9)	C15—C16—C17	113.5 (3)
O2—Rh1—P1	173.12 (11)	C11—C16—C17	125.6 (4)
C11—P1—C21	102.61 (18)	C16—C17—C18	110.1 (4)
C11—P1—C31	107.71 (19)	C16—C17—C19	112.2 (4)
C21—P1—C31	102.32 (18)	C18—C17—C19	110.4 (4)
C11—P1—Rh1	119.33 (13)	C16—C17—H17	108
C21—P1—Rh1	117.86 (14)	C18—C17—H17	108
C31—P1—Rh1	105.47 (13)	C19—C17—H17	108
C2—O3—Rh1	126.0 (3)	C17—C19—H18A	109.5
C4—O2—Rh1	125.3 (3)	C17—C19—H18B	109.5
O1—C1—Rh1	174.9 (4)	H18A—C19—H18B	109.5
C36—C31—C32	108.7 (3)	C17—C19—H18C	109.5
C36—C31—P1	115.7 (3)	H18A—C19—H18C	109.5
C32—C31—P1	112.3 (3)	H18B—C19—H18C	109.5
C36—C31—H2	106.5	C17—C18—H19A	109.5
C32—C31—H2	106.5	C17—C18—H19B	109.5
P1—C31—H2	106.5	H19A—C18—H19B	109.5
C35—C36—C31	109.4 (3)	C17—C18—H19C	109.5
C35—C36—H3A	109.8	H19A—C18—H19C	109.5
C31—C36—H3A	109.8	H19B—C18—H19C	109.5
C35—C36—H3B	109.8	C22—C21—C26	112.4 (3)
C31—C36—H3B	109.8	C22—C21—P1	112.2 (3)
H3A—C36—H3B	108.2	C26—C21—P1	112.7 (3)
C36—C35—C34	111.9 (4)	C22—C21—H20	106.3
C36—C35—H4A	109.2	C26—C21—H20	106.3
C34—C35—H4A	109.2	P1—C21—H20	106.3
C36—C35—H4B	109.2	C21—C22—C23	110.9 (3)
C34—C35—H4B	109.2	C21—C22—H21A	109.5
H4A—C35—H4B	107.9	C23—C22—H21A	109.5
C35—C34—C33	111.7 (4)	C21—C22—H21B	109.5
C35—C34—H5A	109.3	C23—C22—H21B	109.5
C33—C34—H5A	109.3	H21A—C22—H21B	108.1
C35—C34—H5B	109.3	C24—C23—C22	111.7 (4)
C33—C34—H5B	109.3	C24—C23—H22A	109.3
H5A—C34—H5B	107.9	C22—C23—H22A	109.3
C32—C33—C34	110.5 (4)	C24—C23—H22B	109.3
C32—C33—H6A	109.5	C22—C23—H22B	109.3
C34—C33—H6A	109.5	H22A—C23—H22B	107.9
C32—C33—H6B	109.5	C23—C24—C25	110.5 (4)
C34—C33—H6B	109.5	C23—C24—H23A	109.6
H6A—C33—H6B	108.1	C25—C24—H23A	109.6
C33—C32—C31	109.5 (3)	C23—C24—H23B	109.6
C33—C32—H7A	109.8	C25—C24—H23B	109.6
C31—C32—H7A	109.8	H23A—C24—H23B	108.1
C33—C32—H7B	109.8	C24—C25—C26	111.3 (4)
C31—C32—H7B	109.8	C24—C25—H24A	109.4
H7A—C32—H7B	108.2	C26—C25—H24A	109.4
C12—C11—C16	116.4 (4)	C24—C25—H24B	109.4
C12—C11—P1	120.7 (3)	C26—C25—H24B	109.4
C16—C11—P1	122.9 (3)	H24A—C25—H24B	108
C13—C12—C11	120.5 (4)	C21—C26—C25	111.6 (4)
C13—C12—C7	112.8 (4)	C21—C26—H25A	109.3
C11—C12—C7	126.7 (4)	C25—C26—H25A	109.3
C12—C7—C8	111.6 (4)	C21—C26—H25B	109.3
C12—C7—C9	111.1 (4)	C25—C26—H25B	109.3
C8—C7—C9	112.1 (4)	H25A—C26—H25B	108
C12—C7—H10	107.3	O3—C2—C3	126.0 (5)
C8—C7—H10	107.3	O3—C2—C5	114.5 (4)
C9—C7—H10	107.3	C3—C2—C5	119.5 (4)
C7—C9—H11A	109.5	C2—C5—H27A	109.5
C7—C9—H11B	109.5	C2—C5—H27B	109.5
H11A—C9—H11B	109.5	H27A—C5—H27B	109.5
C7—C9—H11C	109.5	C2—C5—H27C	109.5
H11A—C9—H11C	109.5	H27A—C5—H27C	109.5
H11B—C9—H11C	109.5	H27B—C5—H27C	109.5
C7—C8—H12A	109.5	C2—C3—C4	126.5 (4)
C7—C8—H12B	109.5	C2—C3—H28	116.8
H12A—C8—H12B	109.5	C4—C3—H28	116.8
C7—C8—H12C	109.5	O2—C4—C3	126.8 (4)
H12A—C8—H12C	109.5	O2—C4—C6	114.5 (4)
H12B—C8—H12C	109.5	C3—C4—C6	118.7 (4)
C14—C13—C12	121.1 (5)	C4—C6—H30A	109.5
C14—C13—H13	119.4	C4—C6—H30B	109.5
C12—C13—H13	119.4	H30A—C6—H30B	109.5
C15—C14—C13	119.9 (4)	C4—C6—H30C	109.5
C15—C14—H14	120	H30A—C6—H30C	109.5
C13—C14—H14	120	H30B—C6—H30C	109.5

Experimental details

Crystal data
Chemical formula	[Rh(C₅H₇O₂)(C₂₄H₃₉P)(CO)]
M_r	588.55
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	16.750 (2), 9.7334 (13), 19.385 (3)
β (°)	111.669 (3)
V (Å³)	2937.1 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.66
Crystal size (mm)	0.29 × 0.23 × 0.22

Data collection
Diffractometer	Bruker APEX DUO 4K-CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.553, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	14224, 6007, 5516
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.664

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.105, 1.05
No. of reflections	6007
No. of parameters	322
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.85, −1.42
Absolute structure	Flack (1983), 2437 Friedel pairs
Absolute structure parameter	−0.03 (3)

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2008), SAINT and XPREP (Bruker, 2008), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), publCIF (Westrip, 2010) and WinGX (Farrugia, 1999).

Acknowledgements

Financial assistance from the South African National Research Foundation (SA NRF), the Research Fund of the University of Johannesburg, Sasol and TESP is gratefully acknowledged. H. Phaza is acknowledged for the data collection.

References

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