cis-Bis-[2-(diphenyl-phosphino)benzene-thiolato-κP,S]palladium(II).

The title compound, [Pd(C(18)H(14)PS)(2)], was synthesized by the reaction of (Ph(2)PC(6)H(4)SH) with [PdCl(2)(NCC(6)H(5))(2)] in a 2:1 molar ratio in the presence of a slight excess of NEt(3 )as base in dichloro-methane. The compound crystallizes with the Pd(II) atom on a twofold rotation axis. The palladium center has a slightly distorted square-planar environment, with the two P-S chelating ligands adopting a cis configuration. The present structure is a pseudo-polymorph of [Pd(C(18)H(14)PS)(2)]·CH(2)Cl(2).

Related literature

For related literature, see: Andreasen et al. (1999 ▶); Braunstein & Naud (2001 ▶); Real et al. (2000 ▶); Canseco-Gonzalez et al. (2003 ▶, 2004 ▶); Dilworth & Weatley (2000 ▶); Dilworth et al. (2000 ▶); Gómez-Benítez et al. (2003 ▶, 2007a ▶,b ▶); Morales-Morales et al. (2002a ▶,b ▶); Ortner et al. (2000 ▶); Ríos-Moreno et al. (2005 ▶); Taguchi et al. (1999 ▶).

Experimental

Crystal data

[Pd(C18H14PS)2]

M = 693.04

Trigonal,

a = 9.306 (1) Å

c = 30.069 (8) Å

V = 2255.2 (7) Å3

Z = 3

Mo Kα radiation

μ = 0.89 mm−1

T = 298 (2) K

0.16 × 0.07 × 0.04 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.877, T max = 0.967

18737 measured reflections

2749 independent reflections

1811 reflections with I > 2σ(I)

R int = 0.113

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.084

S = 0.82

2749 reflections

186 parameters

H-atom parameters constrained

Δρmax = 1.40 e Å−3

Δρmin = −0.31 e Å−3

Absolute structure: Flack (1983 ▶), 1113 Friedel Pairs

Flack parameter: −0.05 (6)

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808026718/bt2741sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026718/bt2741Isup2.hkl

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

[Pd(C18H14PS)2]	Z = 3
Mr = 693.04	F000 = 1056
Trigonal, P3221	Dx = 1.531 Mg m−3
Hall symbol: P 32 2"	Mo Kα radiation λ = 0.71073 Å
a = 9.306 (1) Å	Cell parameters from 2935 reflections
b = 9.306 (1) Å	θ = 2.5–19.9º
c = 30.069 (8) Å	µ = 0.89 mm−1
α = 90º	T = 298 (2) K
β = 90º	Prism, yellow
γ = 120º	0.16 × 0.07 × 0.04 mm
V = 2255.2 (7) Å3

Bruker SMART APEX CCD area-detector diffractometer	2749 independent reflections
Radiation source: fine-focus sealed tube	1811 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.113
Detector resolution: 0.83 pixels mm-1	θmax = 25.3º
T = 298(2) K	θmin = 2.0º
ω scans	h = −11→11
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	k = −11→11
Tmin = 0.877, Tmax = 0.967	l = −36→36
18737 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046	w = 1/[σ2(Fo2) + (0.025P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.084	(Δ/σ)max = 0.001
S = 0.82	Δρmax = 1.40 e Å−3
2749 reflections	Δρmin = −0.31 e Å−3
186 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1113 Friedel Pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.05 (6)

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
Pd	0.48559 (7)	0.48559 (7)	0.0000	0.0377 (2)
P1	0.2993 (2)	0.3605 (2)	0.05647 (6)	0.0399 (5)
S1	0.6481 (2)	0.6901 (2)	0.05082 (7)	0.0592 (6)
C1	0.5327 (8)	0.6409 (8)	0.0997 (2)	0.0408 (18)
C2	0.3770 (9)	0.4982 (8)	0.1037 (2)	0.0397 (18)
C3	0.2892 (10)	0.4667 (9)	0.1433 (2)	0.060 (2)
H3	0.1854	0.3719	0.1458	0.072*
C4	0.3528 (12)	0.5730 (12)	0.1790 (2)	0.072 (3)
H4	0.2918	0.5509	0.2051	0.086*
C5	0.5077 (12)	0.7126 (11)	0.1757 (3)	0.069 (3)
H5	0.5526	0.7837	0.1999	0.083*
C6	0.5958 (10)	0.7467 (9)	0.1367 (2)	0.059 (2)
H6	0.6995	0.8419	0.1347	0.070*
C7	0.2670 (9)	0.1641 (8)	0.0782 (2)	0.0457 (19)
C8	0.1239 (11)	0.0432 (10)	0.0973 (3)	0.076 (3)
H8	0.0317	0.0570	0.0987	0.091*
C9	0.1143 (15)	−0.0996 (12)	0.1145 (3)	0.095 (3)
H9	0.0142	−0.1808	0.1265	0.114*
C10	0.2415 (15)	−0.1239 (12)	0.1144 (3)	0.083 (3)
H10	0.2336	−0.2182	0.1275	0.100*
C11	0.3848 (12)	−0.0089 (12)	0.0949 (3)	0.085 (3)
H11	0.4754	−0.0254	0.0939	0.102*
C12	0.3967 (11)	0.1320 (11)	0.0765 (2)	0.064 (2)
H12	0.4949	0.2079	0.0625	0.077*
C13	0.0948 (8)	0.3330 (8)	0.0457 (2)	0.0414 (19)
C14	0.0640 (11)	0.4611 (12)	0.0535 (2)	0.064 (2)
H14	0.1450	0.5570	0.0673	0.076*
C15	−0.0844 (10)	0.4507 (12)	0.0413 (3)	0.065 (3)
H15	−0.1031	0.5386	0.0465	0.078*
C16	−0.2044 (12)	0.3062 (16)	0.0212 (3)	0.094 (4)
H16	−0.3033	0.2980	0.0118	0.113*
C17	−0.1781 (11)	0.1752 (13)	0.0151 (3)	0.105 (3)
H17	−0.2609	0.0766	0.0029	0.125*
C18	−0.0297 (10)	0.1907 (11)	0.0272 (3)	0.080 (3)
H18	−0.0127	0.1014	0.0228	0.096*

	U11	U22	U33	U12	U13	U23
Pd	0.0332 (3)	0.0332 (3)	0.0451 (4)	0.0155 (4)	−0.0016 (2)	0.0016 (2)
P1	0.0406 (11)	0.0357 (12)	0.0438 (12)	0.0193 (9)	−0.0009 (9)	0.0022 (9)
S1	0.0476 (13)	0.0509 (13)	0.0634 (14)	0.0129 (10)	−0.0031 (10)	−0.0121 (11)
C1	0.051 (5)	0.038 (4)	0.042 (4)	0.029 (4)	−0.011 (4)	−0.002 (3)
C2	0.050 (5)	0.041 (4)	0.037 (4)	0.029 (4)	−0.002 (4)	0.000 (3)
C3	0.094 (7)	0.061 (5)	0.034 (5)	0.046 (5)	−0.007 (5)	−0.002 (4)
C4	0.105 (8)	0.091 (7)	0.038 (5)	0.064 (7)	0.003 (5)	0.005 (5)
C5	0.105 (8)	0.067 (6)	0.048 (6)	0.053 (6)	−0.025 (5)	−0.019 (5)
C6	0.057 (6)	0.057 (5)	0.062 (5)	0.029 (5)	−0.010 (5)	−0.018 (4)
C7	0.050 (5)	0.035 (5)	0.042 (4)	0.014 (4)	0.003 (3)	0.002 (3)
C8	0.073 (6)	0.046 (6)	0.111 (7)	0.033 (5)	0.040 (5)	0.031 (5)
C9	0.119 (10)	0.055 (7)	0.103 (8)	0.038 (7)	0.040 (8)	0.039 (6)
C10	0.138 (9)	0.044 (6)	0.069 (6)	0.046 (7)	−0.023 (6)	0.000 (5)
C11	0.096 (8)	0.079 (8)	0.100 (8)	0.059 (7)	−0.039 (6)	−0.006 (6)
C12	0.046 (6)	0.064 (6)	0.082 (6)	0.027 (4)	−0.004 (5)	0.011 (5)
C13	0.040 (4)	0.039 (5)	0.040 (4)	0.016 (4)	0.010 (3)	0.003 (3)
C14	0.063 (6)	0.071 (7)	0.060 (5)	0.036 (5)	0.014 (5)	0.023 (5)
C15	0.056 (5)	0.096 (8)	0.065 (6)	0.055 (6)	0.005 (4)	0.012 (5)
C16	0.068 (7)	0.185 (13)	0.059 (6)	0.085 (9)	0.018 (5)	0.027 (7)
C17	0.053 (6)	0.153 (10)	0.119 (7)	0.060 (7)	−0.031 (6)	−0.039 (7)
C18	0.059 (6)	0.095 (8)	0.095 (7)	0.045 (6)	−0.012 (5)	−0.021 (6)

Pd—P1i	2.2861 (18)	C8—C9	1.386 (10)
Pd—P1	2.2861 (18)	C8—H8	0.9300
Pd—S1	2.316 (2)	C9—C10	1.312 (10)
Pd—S1i	2.316 (2)	C9—H9	0.9300
P1—C2	1.805 (7)	C10—C11	1.358 (11)
P1—C7	1.818 (7)	C10—H10	0.9300
P1—C13	1.818 (7)	C11—C12	1.375 (10)
S1—C1	1.740 (7)	C11—H11	0.9300
C1—C2	1.398 (8)	C12—H12	0.9300
C1—C6	1.405 (8)	C13—C18	1.367 (9)
C2—C3	1.390 (9)	C13—C14	1.379 (9)
C3—C4	1.376 (9)	C14—C15	1.384 (9)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.379 (11)	C15—C16	1.386 (11)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.374 (9)	C16—C17	1.369 (12)
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.364 (10)
C7—C8	1.368 (9)	C17—H17	0.9300
C7—C12	1.382 (8)	C18—H18	0.9300
P1i—Pd—P1	101.33 (9)	C7—C8—C9	121.0 (9)
P1i—Pd—S1	171.41 (7)	C7—C8—H8	119.5
P1—Pd—S1	86.90 (7)	C9—C8—H8	119.5
P1i—Pd—S1i	86.90 (7)	C10—C9—C8	122.2 (11)
P1—Pd—S1i	171.41 (7)	C10—C9—H9	118.9
S1—Pd—S1i	85.00 (11)	C8—C9—H9	118.9
C2—P1—C7	103.7 (3)	C9—C10—C11	118.7 (11)
C2—P1—C13	105.1 (3)	C9—C10—H10	120.6
C7—P1—C13	106.7 (3)	C11—C10—H10	120.6
C2—P1—Pd	106.9 (2)	C10—C11—C12	120.3 (10)
C7—P1—Pd	118.7 (2)	C10—C11—H11	119.9
C13—P1—Pd	114.4 (2)	C12—C11—H11	119.9
C1—S1—Pd	106.1 (2)	C11—C12—C7	122.0 (9)
C2—C1—C6	117.9 (7)	C11—C12—H12	119.0
C2—C1—S1	122.3 (5)	C7—C12—H12	119.0
C6—C1—S1	119.8 (6)	C18—C13—C14	117.7 (7)
C3—C2—C1	119.7 (6)	C18—C13—P1	122.0 (6)
C3—C2—P1	122.7 (6)	C14—C13—P1	120.2 (6)
C1—C2—P1	117.6 (6)	C13—C14—C15	121.8 (10)
C4—C3—C2	121.3 (8)	C13—C14—H14	119.1
C4—C3—H3	119.3	C15—C14—H14	119.1
C2—C3—H3	119.3	C14—C15—C16	118.3 (10)
C3—C4—C5	119.5 (8)	C14—C15—H15	120.8
C3—C4—H4	120.2	C16—C15—H15	120.8
C5—C4—H4	120.2	C17—C16—C15	120.4 (9)
C6—C5—C4	120.0 (7)	C17—C16—H16	119.8
C6—C5—H5	120.0	C15—C16—H16	119.8
C4—C5—H5	120.0	C18—C17—C16	119.5 (10)
C5—C6—C1	121.5 (7)	C18—C17—H17	120.3
C5—C6—H6	119.2	C16—C17—H17	120.3
C1—C6—H6	119.2	C17—C18—C13	122.2 (8)
C8—C7—C12	115.7 (8)	C17—C18—H18	118.9
C8—C7—P1	125.5 (6)	C13—C18—H18	118.9
C12—C7—P1	118.8 (6)
P1i—Pd—P1—C2	−177.7 (2)	S1—C1—C6—C5	179.5 (6)
S1—Pd—P1—C2	4.8 (2)	C2—P1—C7—C8	89.7 (7)
S1i—Pd—P1—C2	−14.7 (6)	C13—P1—C7—C8	−21.0 (8)
P1i—Pd—P1—C7	65.6 (2)	Pd—P1—C7—C8	−152.0 (6)
S1—Pd—P1—C7	−111.9 (3)	C2—P1—C7—C12	−89.0 (7)
S1i—Pd—P1—C7	−131.4 (5)	C13—P1—C7—C12	160.3 (6)
P1i—Pd—P1—C13	−61.9 (2)	Pd—P1—C7—C12	29.3 (7)
S1—Pd—P1—C13	120.6 (3)	C12—C7—C8—C9	1.4 (12)
S1i—Pd—P1—C13	101.1 (5)	P1—C7—C8—C9	−177.3 (7)
P1i—Pd—S1—C1	−167.4 (5)	C7—C8—C9—C10	1.8 (16)
P1—Pd—S1—C1	−4.1 (2)	C8—C9—C10—C11	−3.2 (18)
S1i—Pd—S1—C1	173.0 (2)	C9—C10—C11—C12	1.5 (16)
Pd—S1—C1—C2	2.5 (6)	C10—C11—C12—C7	1.8 (14)
Pd—S1—C1—C6	−177.4 (5)	C8—C7—C12—C11	−3.1 (12)
C6—C1—C2—C3	1.0 (10)	P1—C7—C12—C11	175.7 (6)
S1—C1—C2—C3	−178.9 (5)	C2—P1—C13—C18	−150.7 (6)
C6—C1—C2—P1	−178.5 (5)	C7—P1—C13—C18	−40.9 (7)
S1—C1—C2—P1	1.6 (8)	Pd—P1—C13—C18	92.5 (6)
C7—P1—C2—C3	−58.1 (6)	C2—P1—C13—C14	33.4 (6)
C13—P1—C2—C3	53.8 (6)	C7—P1—C13—C14	143.1 (5)
Pd—P1—C2—C3	175.7 (5)	Pd—P1—C13—C14	−83.5 (6)
C7—P1—C2—C1	121.4 (6)	C18—C13—C14—C15	−3.0 (11)
C13—P1—C2—C1	−126.8 (5)	P1—C13—C14—C15	173.1 (6)
Pd—P1—C2—C1	−4.9 (6)	C13—C14—C15—C16	0.7 (12)
C1—C2—C3—C4	−0.3 (11)	C14—C15—C16—C17	2.4 (14)
P1—C2—C3—C4	179.1 (6)	C15—C16—C17—C18	−3.0 (14)
C2—C3—C4—C5	−0.9 (11)	C16—C17—C18—C13	0.5 (14)
C3—C4—C5—C6	1.5 (12)	C14—C13—C18—C17	2.4 (12)
C4—C5—C6—C1	−0.8 (11)	P1—C13—C18—C17	−173.6 (6)
C2—C1—C6—C5	−0.4 (10)

Pd—P1	2.2861 (18)
Pd—S1	2.316 (2)

P1i—Pd—P1	101.33 (9)
P1i—Pd—S1	171.41 (7)
P1—Pd—S1	86.90 (7)
S1—Pd—S1i	85.00 (11)

Symmetry code: (i) .