rac-Carbon-yl{1-[(diphenyl-phosphino)meth-yl]ethanethiol-ato}(triphenyl-phosphine)rhodium(I).

The title compound, [Rh(C(15)H(16)PS)(C(18)H(15)P)(CO)], was synthesized from the reaction of the ligand rac-[Ph(2)PCH(2)CH(CH(3))SH] with trans-[Rh(F)(CO)(PPh(3))(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 [Ph(2)PCH(2)CH(CH(3))S] acting as a chelate and the PPh(3) 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 = 652.50

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.108

S = 1.06

5573 reflections

372 parameters

45 restraints

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −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.

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

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

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

[Rh(C15H16PS)(C18H15P)(CO)]	F(000) = 2672
Mr = 652.50	Dx = 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

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

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(Fo2) + (0.0403P)2 + 6.156P] where P = (Fo2 + 2Fc2)/3
5573 reflections	(Δ/σ)max = 0.001
372 parameters	Δρmax = 0.65 e Å−3
45 restraints	Δρmin = −0.49 e Å−3

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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

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)