rac-Carbon­yl{1-[(diphenyl­phosphino)meth­yl]ethanethiol­ato}(triphenyl­phosphine)rhodium(I)

Hernández-Ortega, S.; Morales-Morales, D.

doi:10.1107/S1600536808034284

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page m1465

doi:10.1107/S1600536808034284

Open

access

rac-Carbonyl{1-[(diphenylphosphino)methyl]ethanethiolato}(triphenylphosphine)rhodium(I)

Simón Hernández-Ortega ^a ^* and David Morales-Morales ^a ^*

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México 04510, Mexico
^*Correspondence e-mail: simonho@unam.mx, damor@unam.mx

(Received 24 September 2008; accepted 20 October 2008; online 25 October 2008)

The title compound, [Rh(C₁₅H₁₆PS)(C₁₈H₁₅P)(CO)], was synthesized from the reaction of the ligand rac-[Ph₂PCH₂CH(CH₃)SH] with trans-[Rh(F)(CO)(PPh₃)₂] in a 1:1 molar ratio in toluene. The Rh atom is four-coordinated in a distorted square-planar geometry with the P—S ligand [Ph₂PCH₂CH(CH₃)S] acting as a chelate and the PPh₃ and disordered CO [site occupation factors of 0.61 (5) and 0.39 (5)] ligands completing the coordination.

Related literature

For general background, see: Au-Yeung & Chan (2004 ); Braunstein & Naud (2001 ); Dilworth & Weatley (2000 ); Dilworth et al. (2000 ); Fierro-Arias et al. (2008 ); Gómez-Benítez et al. (2007 ); Morales-Morales et al. (2002 ); Xie & Zhou (2008 ). For related structures, see: Lee et al. (2002 ).

Experimental

Crystal data

[Rh(C₁₅H₁₆PS)(C₁₈H₁₅P)(CO)]
M_r = 652.50
Orthorhombic, P b c a
a = 10.3142 (7) Å
b = 16.865 (1) Å
c = 34.984 (2) Å
V = 6085.5 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.76 mm⁻¹
T = 298 (2) K
0.26 × 0.23 × 0.03 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.827, T_max = 0.978
48521 measured reflections
5573 independent reflections
4152 reflections with I > 2σ(I)
R_int = 0.095

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.108
S = 1.06
5573 reflections
372 parameters
45 restraints
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034284/dn2386sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034284/dn2386Isup2.hkl

checkCIF report

Comment top

In recent years, attention has increasingly been paid to the coordination chemistry of polydentate ligands incorporating both thiolate and tertiary phosphine donor ligands, as their combination is likely to confer unusual structures and reactivities on their metal complexes [Dilworth, et al. 2000, Morales-Morales, et al., 2002]. In the specific case of compounds with platinum group metals these may be suitable species for catalytic screening. Addiconally, the presence of these ligands in their transition metal complexes may render interesting behaviors in solution as these ligands can be capable of full or partial deligation (hemilability), (Dilworth & Weatley, 2000, Braunstein & Naud, 2001) being able to provide important extra coordination sites for incoming substrates during a catalytic process ([Dilworth & Weatley, 2000, Braunstein & Naud, 2001). Moreover, chiral or potentially bidentate ligands have been used extensively to perform asymmetric transformations [Au-Yeung, et al. 2004, & Xie et al., 2008], however the most commonly employed are bidentated phosphines and the use of sulfur containing ligands has been avoided owing to the well known propensity of platinum group metals to sulfur poisoning.

Thus, owing to our continuous interest in the synthesis of transition metal complexes bearing P—S hybrid ligands [Morales-Morales, et al., 2002, Gómez-Benítez, et al., 2007, Fierro-Arias, et al. 2008] we would like to report the crystal structure of the rhodium(I) complex [Rh(Ph₂PCH₂CH(CH₃)S)(PPh₃)(CO)] (I).

The rhodium atom is four-coordinated in a distorted square planar geometry with the P—S ligand [Ph₂PCH₂CH(CH₃)S] acting as a chelate and the PPh₃ and CO ligands completing the coordination sphere (Fig. 1). Similar geometry has been found in a previously reported rhodium complex (Lee et al., 2002). The phenyl ring on the P atoms are essentially planar, these phenyl rings are rotated around the P—C bond, forming the dihedral angles with the coordination plane P1-C34-P2-S1 (Table 1).

Related literature top

For general background, see: Au-Yeung & Chan (2004); Braunstein & Naud (2001); Dilworth & Weatley (2000); Dilworth, et al. (2000); Fierro-Arias et al. (2008); Gómez-Benítez et al. (2007); Morales-Morales et al. (2002); Xie & Zhou (2008). For related structures, see: Lee et al. (2002).

Experimental top

Synthesis of [Rh(Ph₂PCH₂CH(CH₃)S)(PPh₃)(CO)] (1). To a solution of trans-[Rh(F)(CO)(PPh₃)₂] (100 mg, 12 mmol) in toluene (25 ml) 1 equivalent of the ligand rac-[Ph₂PCH₂CH(CH₃)SH] in toluene (10 ml) was added under stirring. The resulting mixture was allowed to stir overnight. After this time, the solvent was taken off under vacuum and the residue recrystallized from a double layer solvent system CH₂Cl₂/MeOH to afford complex 1 as a microcrystalline yellow powder. Yield 87%. ¹H-NMR (300 MHz, CDCl₃), (7.00–8.00 (m, Ph, 25H), 2.90–3.20 (m, CH₂, 2H), 2.40–2.70 (m, CH, 1H), 1.30–1.50 (d, CH₃, 3H); ³¹P-NMR (121 MHz, CDCl₃), (68.21 (dd), 59.86 (dd) 1JRh-P= 133.4 Hz, 2JP-P = 304.2 Hz. Elem. Anal. Calculated for [C₃₄H₃₁OP₂RhS] Calc. %: C: 62.49, H: 4.94. Found %: C: 62.50, H: 4.90. MS-FAB+ [M+] = 653 m/z.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of (I) with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. Disordered atom and hydrogen atoms were omitted for clarity.

rac-Carbonyl{1- [(diphenylphosphino)methyl]ethanethiolato}(triphenylphosphine)rhodium(I) top

Crystal data top

[Rh(C₁₅H₁₆PS)(C₁₈H₁₅P)(CO)]	F(000) = 2672
M_r = 652.50	D_x = 1.424 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7386 reflections
a = 10.3142 (7) Å	θ = 2.3–31.0°
b = 16.865 (1) Å	µ = 0.76 mm⁻¹
c = 34.984 (2) Å	T = 298 K
V = 6085.5 (6) Å³	Prism, yellow
Z = 8	0.26 × 0.23 × 0.03 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5573 independent reflections
Radiation source: fine-focus sealed tube	4152 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.095
Detector resolution: 0.83 pixels mm^-1	θ_max = 25.4°, θ_min = 2.3°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −20→20
T_min = 0.827, T_max = 0.978	l = −42→42
48521 measured reflections

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0403P)² + 6.156P] where P = (F_o² + 2F_c²)/3
5573 reflections	(Δ/σ)_max = 0.001
372 parameters	Δρ_max = 0.65 e Å⁻³
45 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Rh(C₁₅H₁₆PS)(C₁₈H₁₅P)(CO)]	V = 6085.5 (6) Å³
M_r = 652.50	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.3142 (7) Å	µ = 0.76 mm⁻¹
b = 16.865 (1) Å	T = 298 K
c = 34.984 (2) Å	0.26 × 0.23 × 0.03 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5573 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4152 reflections with I > 2σ(I)
T_min = 0.827, T_max = 0.978	R_int = 0.095
48521 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	45 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.06	Δρ_max = 0.65 e Å⁻³
5573 reflections	Δρ_min = −0.49 e Å⁻³
372 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Rh1	0.32255 (3)	0.37305 (2)	0.105932 (9)	0.03228 (11)
C34	0.1592 (15)	0.377 (2)	0.0860 (10)	0.047 (4)	0.61 (5)
O1	0.0553 (7)	0.3812 (17)	0.0750 (4)	0.067 (4)	0.61 (5)
C34A	0.154 (2)	0.363 (3)	0.0902 (18)	0.050 (5)	0.39 (5)
O1A	0.0544 (11)	0.344 (2)	0.0794 (8)	0.068 (5)	0.39 (5)
S1	0.53111 (12)	0.35920 (9)	0.13006 (4)	0.0596 (4)
P1	0.40804 (11)	0.32103 (6)	0.05089 (3)	0.0316 (3)
P2	0.26119 (11)	0.43243 (7)	0.16325 (3)	0.0357 (3)
C1	0.3715 (4)	0.2171 (2)	0.04190 (12)	0.0331 (9)
C2	0.3274 (5)	0.1695 (3)	0.07131 (13)	0.0519 (13)
H2	0.3099	0.1913	0.0952	0.062*
C3	0.3096 (6)	0.0894 (3)	0.06497 (15)	0.0610 (15)
H3	0.2819	0.0573	0.0850	0.073*
C4	0.3320 (5)	0.0561 (3)	0.02980 (15)	0.0555 (14)
H4	0.3186	0.0021	0.0260	0.067*
C5	0.3742 (5)	0.1030 (3)	0.00031 (14)	0.0481 (12)
H5	0.3891	0.0810	−0.0237	0.058*
C6	0.3945 (4)	0.1826 (3)	0.00618 (12)	0.0398 (10)
H6	0.4239	0.2140	−0.0139	0.048*
C7	0.3736 (4)	0.3667 (2)	0.00480 (11)	0.0340 (10)
C8	0.2469 (5)	0.3649 (3)	−0.00953 (13)	0.0435 (11)
H8	0.1823	0.3391	0.0042	0.052*
C9	0.2169 (6)	0.4009 (3)	−0.04367 (14)	0.0540 (13)
H9	0.1326	0.3987	−0.0530	0.065*
C10	0.3106 (7)	0.4400 (3)	−0.06404 (15)	0.0661 (16)
H10	0.2893	0.4650	−0.0869	0.079*
C11	0.4348 (7)	0.4422 (3)	−0.05088 (15)	0.0677 (17)
H11	0.4983	0.4682	−0.0650	0.081*
C12	0.4671 (5)	0.4061 (3)	−0.01658 (14)	0.0542 (13)
H12	0.5521	0.4082	−0.0078	0.065*
C13	0.5832 (4)	0.3222 (3)	0.05573 (12)	0.0400 (11)
H13A	0.6223	0.2877	0.0368	0.048*
H13B	0.6159	0.3755	0.0519	0.048*
C14	0.6172 (5)	0.2934 (3)	0.09580 (13)	0.0489 (12)
H14	0.5864	0.2389	0.0991	0.059*
C15	0.7617 (5)	0.2968 (4)	0.10406 (16)	0.0695 (17)
H15A	0.8064	0.2603	0.0876	0.104*
H15B	0.7770	0.2827	0.1303	0.104*
H15C	0.7930	0.3496	0.0995	0.104*
C16	0.2358 (5)	0.3652 (3)	0.20339 (13)	0.0448 (12)
C17	0.2788 (5)	0.2880 (3)	0.20110 (15)	0.0578 (14)
H17	0.3237	0.2708	0.1796	0.069*
C18	0.2550 (7)	0.2360 (4)	0.23093 (17)	0.0781 (19)
H18	0.2830	0.1837	0.2293	0.094*
C19	0.1906 (6)	0.2614 (4)	0.26265 (18)	0.081 (2)
H19	0.1741	0.2260	0.2824	0.098*
C20	0.1502 (6)	0.3382 (5)	0.26568 (16)	0.080 (2)
H20	0.1097	0.3556	0.2879	0.096*
C21	0.1692 (6)	0.3896 (4)	0.23600 (15)	0.0683 (17)
H21	0.1376	0.4411	0.2376	0.082*
C22	0.3760 (4)	0.5072 (3)	0.17966 (13)	0.0432 (11)
C23	0.4103 (6)	0.5192 (3)	0.21715 (15)	0.0634 (15)
H23	0.3800	0.4849	0.2359	0.076*
C24	0.4899 (7)	0.5821 (4)	0.2272 (2)	0.086 (2)
H24	0.5136	0.5894	0.2526	0.103*
C25	0.5334 (6)	0.6333 (4)	0.2000 (2)	0.086 (2)
H25	0.5826	0.6771	0.2070	0.103*
C26	0.5047 (6)	0.6204 (4)	0.1623 (2)	0.0798 (19)
H26	0.5375	0.6539	0.1436	0.096*
C27	0.4273 (5)	0.5577 (3)	0.15254 (15)	0.0602 (15)
H27	0.4087	0.5489	0.1269	0.072*
C28	0.1079 (4)	0.4881 (3)	0.16297 (12)	0.0382 (10)
C29	0.1033 (5)	0.5697 (3)	0.16278 (13)	0.0495 (12)
H29	0.1800	0.5986	0.1636	0.059*
C30	−0.0137 (6)	0.6091 (3)	0.16137 (16)	0.0634 (15)
H30	−0.0152	0.6643	0.1610	0.076*
C31	−0.1269 (6)	0.5679 (4)	0.16049 (16)	0.0706 (17)
H31	−0.2052	0.5952	0.1594	0.085*
C32	−0.1268 (5)	0.4868 (4)	0.16114 (17)	0.0691 (16)
H32	−0.2043	0.4586	0.1609	0.083*
C33	−0.0086 (5)	0.4475 (3)	0.16212 (15)	0.0576 (14)
H33	−0.0077	0.3924	0.1622	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Rh1	0.03252 (19)	0.0389 (2)	0.02540 (18)	0.00223 (16)	0.00101 (15)	−0.00288 (15)
C34	0.042 (4)	0.076 (10)	0.021 (7)	0.001 (5)	0.000 (4)	−0.009 (6)
O1	0.044 (3)	0.106 (11)	0.052 (4)	−0.004 (4)	−0.013 (3)	0.006 (6)
C34A	0.042 (4)	0.079 (12)	0.028 (10)	−0.011 (6)	0.004 (5)	−0.019 (9)
O1A	0.048 (4)	0.097 (12)	0.057 (8)	−0.022 (6)	−0.009 (5)	−0.013 (9)
S1	0.0400 (7)	0.1022 (12)	0.0366 (7)	0.0153 (7)	−0.0063 (6)	−0.0186 (7)
P1	0.0355 (6)	0.0331 (6)	0.0261 (6)	−0.0007 (5)	0.0030 (5)	−0.0019 (5)
P2	0.0355 (6)	0.0446 (7)	0.0270 (6)	0.0050 (5)	0.0021 (5)	−0.0037 (5)
C1	0.034 (2)	0.033 (2)	0.032 (2)	0.0000 (19)	0.0003 (19)	−0.0014 (18)
C2	0.077 (4)	0.044 (3)	0.034 (3)	−0.005 (3)	0.009 (3)	−0.003 (2)
C3	0.090 (4)	0.039 (3)	0.053 (3)	−0.019 (3)	0.007 (3)	0.007 (2)
C4	0.066 (3)	0.036 (3)	0.064 (3)	−0.008 (3)	−0.014 (3)	−0.007 (2)
C5	0.062 (3)	0.038 (3)	0.044 (3)	−0.001 (2)	−0.001 (2)	−0.008 (2)
C6	0.044 (3)	0.036 (2)	0.039 (2)	0.001 (2)	0.007 (2)	−0.001 (2)
C7	0.047 (2)	0.028 (2)	0.028 (2)	0.003 (2)	0.0034 (19)	−0.0047 (18)
C8	0.055 (3)	0.041 (3)	0.035 (3)	−0.002 (2)	−0.001 (2)	−0.006 (2)
C9	0.072 (4)	0.050 (3)	0.039 (3)	0.011 (3)	−0.012 (3)	−0.005 (2)
C10	0.100 (5)	0.061 (4)	0.038 (3)	0.005 (4)	−0.011 (3)	0.006 (3)
C11	0.100 (5)	0.061 (4)	0.041 (3)	−0.015 (3)	0.017 (3)	0.012 (3)
C12	0.060 (3)	0.060 (3)	0.043 (3)	−0.013 (3)	0.002 (3)	0.009 (2)
C13	0.035 (2)	0.047 (3)	0.038 (3)	0.004 (2)	0.006 (2)	−0.008 (2)
C14	0.044 (3)	0.061 (3)	0.042 (3)	0.001 (3)	0.004 (2)	−0.007 (2)
C15	0.050 (3)	0.088 (4)	0.070 (4)	0.012 (3)	−0.004 (3)	−0.017 (3)
C16	0.045 (3)	0.056 (3)	0.034 (2)	0.008 (2)	0.006 (2)	0.003 (2)
C17	0.065 (4)	0.065 (4)	0.044 (3)	0.010 (3)	0.006 (3)	0.005 (3)
C18	0.105 (5)	0.070 (4)	0.059 (4)	0.016 (4)	0.010 (4)	0.024 (3)
C19	0.082 (5)	0.103 (5)	0.059 (4)	−0.001 (4)	0.007 (3)	0.039 (4)
C20	0.083 (5)	0.112 (6)	0.046 (3)	0.017 (4)	0.022 (3)	0.017 (3)
C21	0.082 (4)	0.080 (4)	0.042 (3)	0.016 (3)	0.021 (3)	0.006 (3)
C22	0.034 (2)	0.054 (3)	0.041 (3)	0.005 (2)	−0.004 (2)	−0.011 (2)
C23	0.074 (4)	0.070 (4)	0.046 (3)	0.007 (3)	−0.013 (3)	−0.011 (3)
C24	0.092 (5)	0.100 (5)	0.066 (4)	−0.009 (4)	−0.029 (4)	−0.027 (4)
C25	0.070 (4)	0.094 (5)	0.094 (5)	−0.024 (4)	−0.007 (4)	−0.040 (4)
C26	0.065 (4)	0.088 (5)	0.086 (5)	−0.025 (4)	0.017 (4)	−0.017 (4)
C27	0.056 (3)	0.079 (4)	0.046 (3)	−0.024 (3)	0.003 (3)	−0.014 (3)
C28	0.038 (3)	0.049 (3)	0.027 (2)	0.009 (2)	−0.001 (2)	−0.007 (2)
C29	0.050 (3)	0.058 (3)	0.041 (3)	0.011 (3)	0.006 (2)	−0.001 (2)
C30	0.076 (4)	0.055 (3)	0.059 (3)	0.024 (3)	−0.004 (3)	−0.008 (3)
C31	0.053 (4)	0.095 (5)	0.064 (4)	0.031 (4)	−0.004 (3)	−0.022 (3)
C32	0.041 (3)	0.093 (5)	0.073 (4)	−0.001 (3)	−0.006 (3)	−0.017 (4)
C33	0.043 (3)	0.064 (4)	0.066 (4)	0.001 (3)	0.003 (3)	−0.012 (3)

Geometric parameters (Å, º) top

Rh1—C34	1.824 (7)	C14—C15	1.519 (7)
Rh1—C34A	1.827 (8)	C14—H14	0.9800
Rh1—P1	2.2922 (11)	C15—H15A	0.9600
Rh1—S1	2.3225 (13)	C15—H15B	0.9600
Rh1—P2	2.3289 (11)	C15—H15C	0.9600
C34—O1	1.141 (8)	C16—C17	1.378 (7)
C34A—O1A	1.145 (11)	C16—C21	1.394 (7)
S1—C14	1.859 (5)	C17—C18	1.385 (7)
P1—C13	1.815 (4)	C17—H17	0.9300
P1—C1	1.820 (4)	C18—C19	1.362 (8)
P1—C7	1.822 (4)	C18—H18	0.9300
P2—C22	1.822 (5)	C19—C20	1.365 (9)
P2—C16	1.824 (5)	C19—H19	0.9300
P2—C28	1.840 (4)	C20—C21	1.367 (8)
C1—C2	1.382 (6)	C20—H20	0.9300
C1—C6	1.399 (6)	C21—H21	0.9300
C2—C3	1.382 (7)	C22—C23	1.374 (7)
C2—H2	0.9300	C22—C27	1.381 (7)
C3—C4	1.372 (7)	C23—C24	1.387 (8)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.371 (7)	C24—C25	1.362 (9)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.374 (6)	C25—C26	1.367 (9)
C5—H5	0.9300	C25—H25	0.9300
C6—H6	0.9300	C26—C27	1.368 (7)
C7—C12	1.390 (6)	C26—H26	0.9300
C7—C8	1.399 (6)	C27—H27	0.9300
C8—C9	1.375 (7)	C28—C29	1.376 (6)
C8—H8	0.9300	C28—C33	1.383 (7)
C9—C10	1.369 (8)	C29—C30	1.379 (7)
C9—H9	0.9300	C29—H29	0.9300
C10—C11	1.362 (8)	C30—C31	1.359 (8)
C10—H10	0.9300	C30—H30	0.9300
C11—C12	1.386 (7)	C31—C32	1.368 (8)
C11—H11	0.9300	C31—H31	0.9300
C12—H12	0.9300	C32—C33	1.388 (7)
C13—C14	1.524 (6)	C32—H32	0.9300
C13—H13A	0.9700	C33—H33	0.9300
C13—H13B	0.9700

C34—Rh1—P1	92.7 (13)	C15—C14—C13	112.9 (4)
C34A—Rh1—P1	94 (2)	C15—C14—S1	108.9 (3)
C34—Rh1—S1	176.0 (12)	C13—C14—S1	107.0 (3)
C34A—Rh1—S1	168.4 (17)	C15—C14—H14	109.3
P1—Rh1—S1	84.87 (4)	C13—C14—H14	109.3
C34—Rh1—P2	93.6 (13)	S1—C14—H14	109.3
C34A—Rh1—P2	92 (2)	C14—C15—H15A	109.5
P1—Rh1—P2	172.88 (4)	C14—C15—H15B	109.5
S1—Rh1—P2	88.97 (4)	H15A—C15—H15B	109.5
O1—C34—Rh1	177 (3)	C14—C15—H15C	109.5
O1A—C34A—Rh1	168 (5)	H15A—C15—H15C	109.5
C14—S1—Rh1	105.56 (16)	H15B—C15—H15C	109.5
C13—P1—C1	103.5 (2)	C17—C16—C21	119.0 (5)
C13—P1—C7	105.8 (2)	C17—C16—P2	119.8 (4)
C1—P1—C7	102.34 (19)	C21—C16—P2	121.2 (4)
C13—P1—Rh1	107.49 (14)	C16—C17—C18	119.8 (5)
C1—P1—Rh1	115.72 (14)	C16—C17—H17	120.1
C7—P1—Rh1	120.42 (14)	C18—C17—H17	120.1
C22—P2—C16	106.3 (2)	C19—C18—C17	120.1 (6)
C22—P2—C28	102.0 (2)	C19—C18—H18	120.0
C16—P2—C28	101.4 (2)	C17—C18—H18	120.0
C22—P2—Rh1	113.09 (16)	C18—C19—C20	120.7 (6)
C16—P2—Rh1	115.75 (16)	C18—C19—H19	119.6
C28—P2—Rh1	116.67 (14)	C20—C19—H19	119.6
C2—C1—C6	118.6 (4)	C19—C20—C21	119.9 (6)
C2—C1—P1	119.9 (3)	C19—C20—H20	120.0
C6—C1—P1	121.3 (3)	C21—C20—H20	120.0
C1—C2—C3	119.5 (4)	C20—C21—C16	120.4 (6)
C1—C2—H2	120.3	C20—C21—H21	119.8
C3—C2—H2	120.3	C16—C21—H21	119.8
C4—C3—C2	121.5 (5)	C23—C22—C27	117.8 (5)
C4—C3—H3	119.3	C23—C22—P2	124.8 (4)
C2—C3—H3	119.3	C27—C22—P2	117.3 (4)
C5—C4—C3	119.4 (5)	C22—C23—C24	120.5 (6)
C5—C4—H4	120.3	C22—C23—H23	119.8
C3—C4—H4	120.3	C24—C23—H23	119.8
C4—C5—C6	120.0 (5)	C25—C24—C23	120.2 (6)
C4—C5—H5	120.0	C25—C24—H24	119.9
C6—C5—H5	120.0	C23—C24—H24	119.9
C5—C6—C1	121.0 (4)	C24—C25—C26	120.1 (6)
C5—C6—H6	119.5	C24—C25—H25	119.9
C1—C6—H6	119.5	C26—C25—H25	119.9
C12—C7—C8	117.7 (4)	C25—C26—C27	119.4 (6)
C12—C7—P1	122.9 (4)	C25—C26—H26	120.3
C8—C7—P1	119.4 (3)	C27—C26—H26	120.3
C9—C8—C7	120.8 (5)	C26—C27—C22	121.9 (5)
C9—C8—H8	119.6	C26—C27—H27	119.1
C7—C8—H8	119.6	C22—C27—H27	119.1
C10—C9—C8	120.4 (5)	C29—C28—C33	117.7 (4)
C10—C9—H9	119.8	C29—C28—P2	122.7 (4)
C8—C9—H9	119.8	C33—C28—P2	119.6 (4)
C11—C10—C9	120.1 (5)	C28—C29—C30	120.8 (5)
C11—C10—H10	120.0	C28—C29—H29	119.6
C9—C10—H10	120.0	C30—C29—H29	119.6
C10—C11—C12	120.4 (5)	C31—C30—C29	120.4 (5)
C10—C11—H11	119.8	C31—C30—H30	119.8
C12—C11—H11	119.8	C29—C30—H30	119.8
C11—C12—C7	120.6 (5)	C30—C31—C32	120.7 (5)
C11—C12—H12	119.7	C30—C31—H31	119.7
C7—C12—H12	119.7	C32—C31—H31	119.7
C14—C13—P1	108.1 (3)	C31—C32—C33	118.6 (6)
C14—C13—H13A	110.1	C31—C32—H32	120.7
P1—C13—H13A	110.1	C33—C32—H32	120.7
C14—C13—H13B	110.1	C28—C33—C32	121.8 (5)
P1—C13—H13B	110.1	C28—C33—H33	119.1
H13A—C13—H13B	108.4	C32—C33—H33	119.1

Experimental details

Crystal data
Chemical formula	[Rh(C₁₅H₁₆PS)(C₁₈H₁₅P)(CO)]
M_r	652.50
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	10.3142 (7), 16.865 (1), 34.984 (2)
V (Å³)	6085.5 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.26 × 0.23 × 0.03

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.827, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	48521, 5573, 4152
R_int	0.095
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.108, 1.06
No. of reflections	5573
No. of parameters	372
No. of restraints	45
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.49

Computer programs: SMART (Bruker, 1999), SAINT-Plus (Bruker, 1999), SHELXTL (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).

Dihedral angle of phenyl rings with the coordination center (P1-S1-P2-C34) (Å). top

Plane	angle
C1-C6	85.4 (1)
C7-C12	56.29 (9)
C16-C21	74.2 (2)
C22-C27	70.4 (1)
C28-C33	68.9 (1)

Acknowledgements

Financial support of this research by CONACYT (F58692) and PAPIIT (IN227008) is gratefully acknowledged.

References

Au-Yeung, T. T. L. & Chan, A. S. C. (2004). Coord. Chem. Rev. 248, 2151–2164. Web of Science CrossRef CAS Google Scholar
Braunstein, P. & Naud, F. (2001). Angew. Chem. Int. Ed. Engl. 40, 680–699. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (1999). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Dilworth, J. R., Morales, D. & Zheng, Y. (2000). J. Chem. Soc. Dalton Trans. pp. 3007–3015. Web of Science CSD CrossRef Google Scholar
Dilworth, J. R. & Weatley, N. (2000). Coord. Chem. Rev. 199, 89–158. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Fierro-Arias, J., Morales-Morales, D. & Hernández-Ortega, S. (2008). Acta Cryst. E64, m1196. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gómez-Benítez, V., Hernández-Ortega, S., Toscano, R. A. & Morales-Morales, D. (2007). Inorg. Chim. Acta, 360, 2128–2138. Google Scholar
Lee, H.-S., Bae, J.-Y., Kim, D.-H., Kim, H. S., Kim, S.-J., Cho, S., Ko, J. & Kang, S. O. (2002). Organometallics, 21, 210–219. Web of Science CSD CrossRef CAS Google Scholar
Morales-Morales, D. S., Rodríguez-Morales, S., Dilworth, J. R., Sousa-Pedrares, A. & Zheng, Y. (2002). Inorg. Chim. Acta, 332, 101–107. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xie, J. H. & Zhou, Q. L. (2008). Acc. Chem. Res. 41, 581–593. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.