Bis[2-(phenyl­sulfan­yl)benzene­thiol­ato]palladium(II)

Shimizu, D.; Takeda, N.; Sasamori, T.; Tokitoh, N.

doi:10.1107/S1600536805041711

Bis[2-(phenylsulfanyl)benzenethiolato]palladium(II)

D. Shimizu, N. Takeda, T. Sasamori and N. Tokitoh

In the title complex, [Pd(C₁₂H₉S₂)₂], the central Pd atom has a slightly distorted cis-planar four-coordinate geometry defined by the two thiolate and the two sulfanyl S atoms from two 2-(phenylsulfanyl)benzenethiolate ligands. The two phenyl groups are on the same side of the PdS₄ plane and indicative of the typical arrangement of intermolecular π-stacking. Moreover, an intermolecular C—H

π stacking interaction links molecules to one another.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041711/xu6091sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041711/xu6091Isup2.hkl Contains datablock I

CCDC reference: 296711

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Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.004 Å
R factor = 0.023
wR factor = 0.057
Data-to-parameter ratio = 13.2

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Alert level C
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.53 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The cleavage of an S—S bond mediated by a transition metal agent is one of the common methods to synthesize a transition metal complex with thiolate ligands. In the course of our studies on the reactivity of acyclic polythioethers possessing a disulfide bond toward low-valent transition metals (Shimizu et al., 2006), we synthesized the title compound, (I), by the reaction of (PhSC₆H₄S)₂ with Pd(PPh₃)₄, and determined its crystal structure.

The molecular structure of (I) is shown in Fig. 1. The central Pd atom has a slightly distorted cis-square planar coordination with the two thiolate S atoms and the two sulfanyl S atoms of the two 2-(phenylsulfanyl)benzenethiolate ligands. The sum of the bond angles around the Pd1 atom is close to 360°. The Pd1—S1 and Pd1—S3 bond lengths of slightly shorter than those of Pd1—S2 and Pd1—S4 (Table 1). The C₆H₄S₂PdS₂C₆H₄ moiety containing the PdS₄ plane is essentially planar with the two phenyl groups on the same side of this plane and perpendicular to it. Moreover, the two phenyl rings are nearly parallel to each other, the centroid-to-centroid separation of 3.6241 (16) Å suggesting a face-to-face π-stacking interaction.

The C4—H3···Cg(C13)ⁱ angle (Cg(C13) is the centroid of the C13–C18ring) of 152° and H···Cg separation of 2.77 Å indicate C—H..π stacking between neighboring benzene rings [symmetry code: (i) 1 − x, −y, −z].

Experimental top

Tetrakis(triphenylphosphine)palladium(0) (133 mg, 0.115 mmol) was added to a benzene solution (10 ml) of bis[2-(phenylsulfanyl)phenyl] disulfide (50 mg, 0.115 mmol) (Figuly et al., 1989) at 298 K. After stirring for 24 h at this temperature, the crude mixture was purified by the recrystallization from a benzene/acetonitrile solution to give single crystals of (I) (47.5 mg, 76%) [m.p. 526.0–527.0 K (decomposition)].

Computing details top

Data collection: CrystalClear (Rigaku, 2004); cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: HKL-2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Yadokari-XG (Wakita, 2005); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The molecular structure of (I), shown with 50% probability displacement ellipsoids. H atoms are represented by circles of arbitrary size.
	Fig. 2. The molecular packing of (I), viewed from the side of the C₆H₄S₂PdS₂C₆H₄ plane. H atoms have been omitted for clarity.

Bis[2-(phenylsulfanyl)benzenethiolato]palladium(II) top

Crystal data top

[Pd(C₁₂H₉S₂)₂]	Z = 2
M_r = 541.02	F(000) = 544
Triclinic, P1	D_x = 1.671 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 6.2910 (1) Å	Cell parameters from 3349 reflections
b = 8.4579 (2) Å	θ = 2.4–25.5°
c = 20.4780 (5) Å	µ = 1.26 mm⁻¹
α = 98.7890 (13)°	T = 153 K
β = 92.7051 (14)°	Prism, purple
γ = 91.2243 (15)°	0.15 × 0.10 × 0.01 mm
V = 1075.16 (4) Å³

Data collection top

Rigaku Saturn diffractometer	3985 independent reflections
Radiation source: fine-focus sealed tube	3587 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 28.57 pixels mm^-1	θ_max = 25.5°, θ_min = 2.4°
ω scans	h = −7→7
Absorption correction: multi-scan (Jacobson, 1998)	k = −10→10
T_min = 0.834, T_max = 0.988	l = −23→24
8083 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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.057	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0172P)² + 0.7132P] where P = (F_o² + 2F_c²)/3
3985 reflections	(Δ/σ)_max < 0.001
302 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Pd(C₁₂H₉S₂)₂]	γ = 91.2243 (15)°
M_r = 541.02	V = 1075.16 (4) Å³
Triclinic, P1	Z = 2
a = 6.2910 (1) Å	Mo Kα radiation
b = 8.4579 (2) Å	µ = 1.26 mm⁻¹
c = 20.4780 (5) Å	T = 153 K
α = 98.7890 (13)°	0.15 × 0.10 × 0.01 mm
β = 92.7051 (14)°

Data collection top

Rigaku Saturn diffractometer	3985 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	3587 reflections with I > 2σ(I)
T_min = 0.834, T_max = 0.988	R_int = 0.021
8083 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.057	H-atom parameters constrained
S = 1.07	Δρ_max = 0.40 e Å⁻³
3985 reflections	Δρ_min = −0.36 e Å⁻³
302 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
Pd1	0.09298 (2)	0.010432 (19)	0.260838 (9)	0.01839 (7)
S1	−0.09629 (9)	−0.14321 (7)	0.17495 (3)	0.02536 (14)
S2	0.38059 (8)	0.00783 (6)	0.19428 (3)	0.01980 (12)
S3	−0.19531 (9)	−0.01241 (7)	0.32324 (3)	0.02638 (14)
S4	0.26925 (8)	0.15710 (7)	0.35326 (3)	0.02128 (13)
C1	0.0795 (4)	−0.1688 (3)	0.11019 (12)	0.0226 (5)
C2	0.0141 (4)	−0.2608 (3)	0.04945 (13)	0.0287 (5)
H1	−0.1245	−0.3092	0.0437	0.034*
C3	0.1495 (4)	−0.2817 (3)	−0.00209 (13)	0.0324 (6)
H2	0.1029	−0.3446	−0.0429	0.039*
C4	0.3537 (4)	−0.2116 (3)	0.00490 (13)	0.0314 (6)
H3	0.4453	−0.2265	−0.0310	0.038*
C5	0.4214 (4)	−0.1210 (3)	0.06405 (13)	0.0270 (5)
H4	0.5602	−0.0729	0.0693	0.032*
C6	0.2848 (4)	−0.1001 (3)	0.11629 (12)	0.0216 (5)
C7	−0.1177 (4)	0.0944 (3)	0.40161 (12)	0.0234 (5)
C8	−0.2570 (4)	0.0998 (3)	0.45323 (13)	0.0308 (6)
H5	−0.3870	0.0390	0.4465	0.037*
C9	−0.2078 (4)	0.1923 (4)	0.51361 (14)	0.0378 (6)
H6	−0.3046	0.1953	0.5480	0.045*
C10	−0.0172 (5)	0.2816 (4)	0.52482 (14)	0.0409 (7)
H7	0.0134	0.3482	0.5661	0.049*
C11	0.1265 (4)	0.2729 (3)	0.47587 (13)	0.0335 (6)
H8	0.2592	0.3299	0.4837	0.040*
C12	0.0752 (4)	0.1795 (3)	0.41470 (12)	0.0245 (5)
C13	0.4267 (3)	0.2037 (3)	0.17394 (12)	0.0215 (5)
C14	0.2664 (4)	0.2829 (3)	0.14441 (14)	0.0301 (6)
H9	0.1294	0.2334	0.1341	0.036*
C15	0.3090 (4)	0.4353 (3)	0.13013 (15)	0.0366 (6)
H10	0.2006	0.4905	0.1098	0.044*
C16	0.5087 (4)	0.5074 (3)	0.14536 (13)	0.0310 (6)
H11	0.5364	0.6123	0.1360	0.037*
C17	0.6673 (4)	0.4269 (3)	0.17411 (14)	0.0326 (6)
H12	0.8045	0.4764	0.1841	0.039*
C18	0.6279 (4)	0.2736 (3)	0.18867 (13)	0.0285 (5)
H13	0.7372	0.2179	0.2084	0.034*
C19	0.3088 (4)	0.3588 (3)	0.33895 (12)	0.0219 (5)
C20	0.1443 (4)	0.4395 (3)	0.31253 (13)	0.0298 (6)
H14	0.0081	0.3886	0.3022	0.036*
C21	0.1801 (4)	0.5952 (3)	0.30123 (14)	0.0338 (6)
H15	0.0681	0.6518	0.2834	0.041*
C22	0.3797 (4)	0.6680 (3)	0.31606 (13)	0.0309 (6)
H16	0.4043	0.7745	0.3082	0.037*
C23	0.5422 (4)	0.5871 (3)	0.34203 (15)	0.0353 (6)
H17	0.6787	0.6378	0.3517	0.042*
C24	0.5082 (4)	0.4314 (3)	0.35423 (14)	0.0314 (6)
H18	0.6199	0.3758	0.3727	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.01733 (9)	0.01634 (10)	0.02147 (11)	−0.00085 (6)	0.00144 (7)	0.00292 (7)
S1	0.0198 (3)	0.0274 (3)	0.0268 (3)	−0.0051 (2)	0.0010 (2)	−0.0017 (3)
S2	0.0181 (3)	0.0194 (3)	0.0221 (3)	−0.0005 (2)	0.0012 (2)	0.0039 (2)
S3	0.0209 (3)	0.0315 (3)	0.0257 (3)	−0.0057 (2)	0.0043 (2)	0.0013 (3)
S4	0.0203 (3)	0.0195 (3)	0.0237 (3)	−0.0004 (2)	−0.0003 (2)	0.0028 (2)
C1	0.0253 (11)	0.0187 (11)	0.0238 (13)	0.0036 (9)	−0.0009 (9)	0.0041 (10)
C2	0.0286 (12)	0.0261 (13)	0.0299 (14)	−0.0019 (10)	−0.0024 (10)	0.0012 (11)
C3	0.0421 (15)	0.0290 (14)	0.0240 (14)	0.0014 (11)	−0.0018 (11)	−0.0009 (11)
C4	0.0371 (14)	0.0310 (14)	0.0257 (14)	0.0031 (11)	0.0054 (11)	0.0018 (11)
C5	0.0268 (12)	0.0257 (12)	0.0291 (14)	0.0013 (10)	0.0043 (10)	0.0058 (11)
C6	0.0246 (11)	0.0172 (11)	0.0233 (13)	0.0035 (9)	−0.0008 (9)	0.0040 (10)
C7	0.0263 (11)	0.0218 (12)	0.0234 (13)	0.0044 (9)	0.0013 (10)	0.0070 (10)
C8	0.0285 (12)	0.0368 (15)	0.0291 (15)	0.0026 (11)	0.0051 (11)	0.0103 (12)
C9	0.0404 (15)	0.0494 (17)	0.0260 (15)	0.0101 (13)	0.0093 (12)	0.0103 (13)
C10	0.0513 (17)	0.0446 (17)	0.0249 (15)	0.0019 (13)	0.0037 (13)	−0.0019 (13)
C11	0.0376 (14)	0.0352 (15)	0.0266 (15)	−0.0038 (11)	−0.0009 (11)	0.0025 (12)
C12	0.0282 (12)	0.0230 (12)	0.0233 (13)	0.0033 (9)	0.0017 (10)	0.0059 (10)
C13	0.0242 (11)	0.0196 (11)	0.0207 (12)	−0.0014 (9)	0.0043 (9)	0.0028 (9)
C14	0.0251 (12)	0.0269 (13)	0.0392 (16)	−0.0002 (10)	−0.0007 (11)	0.0089 (11)
C15	0.0345 (14)	0.0298 (14)	0.0477 (18)	0.0051 (11)	−0.0006 (12)	0.0136 (13)
C16	0.0432 (14)	0.0189 (12)	0.0316 (15)	−0.0020 (10)	0.0054 (12)	0.0049 (11)
C17	0.0332 (13)	0.0289 (14)	0.0346 (16)	−0.0118 (11)	−0.0020 (11)	0.0040 (12)
C18	0.0264 (12)	0.0283 (13)	0.0305 (14)	−0.0026 (10)	−0.0048 (10)	0.0060 (11)
C19	0.0257 (11)	0.0178 (11)	0.0219 (13)	−0.0023 (9)	0.0030 (9)	0.0015 (9)
C20	0.0275 (12)	0.0249 (13)	0.0362 (16)	−0.0036 (10)	−0.0044 (11)	0.0046 (11)
C21	0.0382 (14)	0.0281 (14)	0.0351 (16)	0.0021 (11)	−0.0059 (12)	0.0071 (12)
C22	0.0400 (14)	0.0205 (12)	0.0323 (15)	−0.0047 (10)	0.0050 (11)	0.0045 (11)
C23	0.0277 (13)	0.0314 (14)	0.0456 (18)	−0.0090 (11)	0.0024 (12)	0.0037 (13)
C24	0.0251 (12)	0.0292 (13)	0.0395 (16)	−0.0002 (10)	0.0005 (11)	0.0046 (12)

Geometric parameters (Å, º) top

Pd1—S1	2.2886 (6)	C4—H3	0.9500
Pd1—S2	2.3146 (6)	C5—C6	1.396 (3)
Pd1—S3	2.2888 (6)	C5—H4	0.9500
Pd1—S4	2.3186 (6)	C7—C12	1.391 (3)
Pd1—C22ⁱ	3.735 (3)	C7—C8	1.401 (3)
Pd1—C21ⁱ	3.774 (3)	C8—C9	1.376 (4)
Pd1—C18ⁱⁱ	4.071 (2)	C8—H5	0.9500
Pd1—S3ⁱⁱⁱ	4.6140 (6)	C9—C10	1.394 (4)
Pd1—S2ⁱⁱ	4.6210 (5)	C9—H6	0.9500
Pd1—C13ⁱⁱ	4.887 (2)	C10—C11	1.376 (4)
Pd1—C17ⁱⁱ	4.960 (3)	C10—H7	0.9500
S1—C1	1.758 (2)	C11—C12	1.395 (4)
S1—C5ⁱⁱ	3.729 (3)	C11—H8	0.9500
S1—C16^iv	3.778 (3)	C13—C18	1.386 (3)
S1—C17^iv	3.896 (3)	C13—C14	1.388 (3)
S1—C18ⁱⁱ	3.940 (3)	C14—C15	1.388 (4)
S1—C21ⁱ	4.012 (3)	C14—H9	0.9500
S1—C6ⁱⁱ	4.060 (2)	C15—C16	1.386 (4)
S2—C6	1.785 (2)	C15—H10	0.9500
S2—C13	1.790 (2)	C16—C17	1.379 (4)
S3—C7	1.759 (3)	C16—H11	0.9500
S3—C22^iv	3.743 (3)	C17—C18	1.394 (3)
S3—C23^iv	3.817 (3)	C17—H12	0.9500
S3—C18ⁱⁱ	4.067 (3)	C18—H13	0.9500
S4—C12	1.786 (2)	C19—C24	1.386 (3)
S4—C19	1.789 (2)	C19—C20	1.386 (3)
S4—C8ⁱⁱⁱ	3.619 (3)	C20—C21	1.387 (3)
S4—C7ⁱⁱⁱ	4.003 (2)	C20—H14	0.9500
C1—C6	1.397 (3)	C21—C22	1.387 (4)
C1—C2	1.401 (3)	C21—H15	0.9500
C2—C3	1.380 (4)	C22—C23	1.373 (4)
C2—H1	0.9500	C22—H16	0.9500
C3—C4	1.395 (4)	C23—C24	1.391 (4)
C3—H2	0.9500	C23—H17	0.9500
C4—C5	1.375 (4)	C24—H18	0.9500

S3—Pd1—S1	87.47 (2)	C7—S3—C23^iv	109.92 (9)
S3—Pd1—S2	174.59 (2)	Pd1—S3—C23^iv	123.39 (5)
S1—Pd1—S2	88.72 (2)	C7—S3—C18ⁱⁱ	113.47 (9)
S3—Pd1—S4	88.61 (2)	Pd1—S3—C18ⁱⁱ	73.75 (4)
S1—Pd1—S4	175.66 (2)	C22^iv—S3—C18ⁱⁱ	107.29 (5)
S2—Pd1—S4	95.06 (2)	C23^iv—S3—C18ⁱⁱ	126.23 (6)
S3—Pd1—C22ⁱ	95.27 (4)	C12—S4—C19	101.85 (11)
S1—Pd1—C22ⁱ	94.95 (4)	C12—S4—Pd1	104.55 (8)
S2—Pd1—C22ⁱ	81.22 (4)	C19—S4—Pd1	108.93 (8)
S4—Pd1—C22ⁱ	83.56 (4)	C12—S4—C8ⁱⁱⁱ	100.73 (9)
S3—Pd1—C21ⁱ	80.97 (5)	C19—S4—C8ⁱⁱⁱ	101.85 (9)
S1—Pd1—C21ⁱ	78.68 (4)	Pd1—S4—C8ⁱⁱⁱ	134.58 (5)
S2—Pd1—C21ⁱ	94.51 (4)	C12—S4—C7ⁱⁱⁱ	121.07 (9)
S4—Pd1—C21ⁱ	98.86 (4)	C19—S4—C7ⁱⁱⁱ	94.92 (8)
C22ⁱ—Pd1—C21ⁱ	21.28 (5)	Pd1—S4—C7ⁱⁱⁱ	122.40 (4)
S3—Pd1—C18ⁱⁱ	73.58 (4)	C6—C1—C2	117.6 (2)
S1—Pd1—C18ⁱⁱ	70.27 (4)	C6—C1—S1	122.66 (19)
S2—Pd1—C18ⁱⁱ	108.69 (4)	C2—C1—S1	119.70 (18)
S4—Pd1—C18ⁱⁱ	110.34 (4)	C3—C2—C1	120.6 (2)
C22ⁱ—Pd1—C18ⁱⁱ	161.48 (5)	C3—C2—H1	119.7
C21ⁱ—Pd1—C18ⁱⁱ	140.22 (5)	C1—C2—H1	119.7
S3—Pd1—S3ⁱⁱⁱ	128.16 (2)	C2—C3—C4	121.0 (2)
S1—Pd1—S3ⁱⁱⁱ	128.427 (18)	C2—C3—H2	119.5
S2—Pd1—S3ⁱⁱⁱ	52.398 (16)	C4—C3—H2	119.5
S4—Pd1—S3ⁱⁱⁱ	53.414 (16)	C5—C4—C3	119.5 (2)
C22ⁱ—Pd1—S3ⁱⁱⁱ	51.97 (4)	C5—C4—H3	120.2
C21ⁱ—Pd1—S3ⁱⁱⁱ	73.22 (4)	C3—C4—H3	120.2
C18ⁱⁱ—Pd1—S3ⁱⁱⁱ	146.33 (3)	C4—C5—C6	119.6 (2)
S3—Pd1—S2ⁱⁱ	52.154 (17)	C4—C5—H4	120.2
S1—Pd1—S2ⁱⁱ	49.187 (16)	C6—C5—H4	120.2
S2—Pd1—S2ⁱⁱ	126.97 (2)	C5—C6—C1	121.7 (2)
S4—Pd1—S2ⁱⁱ	128.850 (16)	C5—C6—S2	119.02 (18)
C22ⁱ—Pd1—S2ⁱⁱ	125.74 (4)	C1—C6—S2	119.16 (18)
C21ⁱ—Pd1—S2ⁱⁱ	104.47 (4)	C12—C7—C8	117.6 (2)
C18ⁱⁱ—Pd1—S2ⁱⁱ	35.86 (3)	C12—C7—S3	122.93 (19)
S3ⁱⁱⁱ—Pd1—S2ⁱⁱ	177.284 (11)	C8—C7—S3	119.44 (19)
S3—Pd1—C13ⁱⁱ	64.66 (3)	C9—C8—C7	120.8 (2)
S1—Pd1—C13ⁱⁱ	60.19 (3)	C9—C8—H5	119.6
S2—Pd1—C13ⁱⁱ	116.48 (3)	C7—C8—H5	119.6
S4—Pd1—C13ⁱⁱ	119.52 (3)	C8—C9—C10	120.6 (3)
C22ⁱ—Pd1—C13ⁱⁱ	147.08 (5)	C8—C9—H6	119.7
C21ⁱ—Pd1—C13ⁱⁱ	125.81 (5)	C10—C9—H6	119.7
C18ⁱⁱ—Pd1—C13ⁱⁱ	14.42 (4)	C11—C10—C9	119.7 (3)
S3ⁱⁱⁱ—Pd1—C13ⁱⁱ	160.63 (3)	C11—C10—H7	120.1
S2ⁱⁱ—Pd1—C13ⁱⁱ	21.46 (3)	C9—C10—H7	120.1
S3—Pd1—C17ⁱⁱ	83.42 (4)	C10—C11—C12	119.4 (3)
S1—Pd1—C17ⁱⁱ	79.74 (3)	C10—C11—H8	120.3
S2—Pd1—C17ⁱⁱ	99.69 (3)	C12—C11—H8	120.3
S4—Pd1—C17ⁱⁱ	101.65 (3)	C7—C12—C11	121.8 (2)
C22ⁱ—Pd1—C17ⁱⁱ	174.57 (5)	C7—C12—S4	118.78 (19)
C21ⁱ—Pd1—C17ⁱⁱ	153.81 (5)	C11—C12—S4	119.23 (19)
C18ⁱⁱ—Pd1—C17ⁱⁱ	13.73 (4)	C18—C13—C14	121.1 (2)
S3ⁱⁱⁱ—Pd1—C17ⁱⁱ	132.60 (3)	C18—C13—S2	117.75 (18)
S2ⁱⁱ—Pd1—C17ⁱⁱ	49.58 (3)	C14—C13—S2	121.14 (17)
C13ⁱⁱ—Pd1—C17ⁱⁱ	28.13 (4)	C13—C14—C15	119.1 (2)
C1—S1—Pd1	104.66 (8)	C13—C14—H9	120.5
C1—S1—C5ⁱⁱ	94.48 (9)	C15—C14—H9	120.5
Pd1—S1—C5ⁱⁱ	139.65 (4)	C16—C15—C14	120.4 (2)
C1—S1—C16^iv	107.42 (9)	C16—C15—H10	119.8
Pd1—S1—C16^iv	139.41 (5)	C14—C15—H10	119.8
C5ⁱⁱ—S1—C16^iv	61.05 (6)	C17—C16—C15	120.0 (2)
C1—S1—C17^iv	103.38 (9)	C17—C16—H11	120.0
Pd1—S1—C17^iv	126.37 (5)	C15—C16—H11	120.0
C5ⁱⁱ—S1—C17^iv	81.23 (6)	C16—C17—C18	120.5 (2)
C1—S1—C18ⁱⁱ	111.58 (9)	C16—C17—H12	119.8
Pd1—S1—C18ⁱⁱ	76.58 (4)	C18—C17—H12	119.8
C5ⁱⁱ—S1—C18ⁱⁱ	63.33 (5)	C13—C18—C17	118.9 (2)
C16^iv—S1—C18ⁱⁱ	112.78 (5)	C13—C18—H13	120.5
C17^iv—S1—C18ⁱⁱ	131.05 (5)	C17—C18—H13	120.5
C1—S1—C21ⁱ	101.08 (9)	C24—C19—C20	121.0 (2)
Pd1—S1—C21ⁱ	67.30 (4)	C24—C19—S4	118.39 (18)
C5ⁱⁱ—S1—C21ⁱ	143.34 (6)	C20—C19—S4	120.65 (17)
C16^iv—S1—C21ⁱ	82.57 (6)	C19—C20—C21	119.4 (2)
C17^iv—S1—C21ⁱ	63.01 (6)	C19—C20—H14	120.3
C18ⁱⁱ—S1—C21ⁱ	136.22 (6)	C21—C20—H14	120.3
C1—S1—C6ⁱⁱ	114.55 (8)	C22—C21—C20	119.8 (2)
Pd1—S1—C6ⁱⁱ	127.40 (4)	C22—C21—H15	120.1
C16^iv—S1—C6ⁱⁱ	57.08 (5)	C20—C21—H15	120.1
C17^iv—S1—C6ⁱⁱ	77.44 (5)	C23—C22—C21	120.4 (2)
C18ⁱⁱ—S1—C6ⁱⁱ	57.50 (5)	C23—C22—H16	119.8
C21ⁱ—S1—C6ⁱⁱ	131.80 (5)	C21—C22—H16	119.8
C6—S2—C13	101.52 (11)	C22—C23—C24	120.4 (2)
C6—S2—Pd1	104.64 (8)	C22—C23—H17	119.8
C13—S2—Pd1	109.61 (8)	C24—C23—H17	119.8
C7—S3—Pd1	104.47 (8)	C19—C24—C23	118.9 (2)
C7—S3—C22^iv	117.25 (9)	C19—C24—H18	120.5
Pd1—S3—C22^iv	132.07 (5)	C23—C24—H18	120.5

S3—Pd1—S1—C1	−177.37 (8)	C21ⁱ—Pd1—S4—C12	−85.20 (9)
S2—Pd1—S1—C1	−1.22 (8)	C18ⁱⁱ—Pd1—S4—C12	67.35 (9)
C22ⁱ—Pd1—S1—C1	−82.30 (9)	S3ⁱⁱⁱ—Pd1—S4—C12	−146.53 (8)
C21ⁱ—Pd1—S1—C1	−96.08 (9)	S2ⁱⁱ—Pd1—S4—C12	31.58 (8)
C18ⁱⁱ—Pd1—S1—C1	109.17 (9)	C13ⁱⁱ—Pd1—S4—C12	55.06 (9)
S3ⁱⁱⁱ—Pd1—S1—C1	−38.40 (8)	C17ⁱⁱ—Pd1—S4—C12	78.43 (9)
S2ⁱⁱ—Pd1—S1—C1	143.28 (8)	S3—Pd1—S4—C19	−112.82 (8)
C13ⁱⁱ—Pd1—S1—C1	120.56 (9)	S2—Pd1—S4—C19	71.17 (8)
C17ⁱⁱ—Pd1—S1—C1	98.86 (8)	C22ⁱ—Pd1—S4—C19	151.71 (9)
S3—Pd1—S1—C5ⁱⁱ	66.99 (7)	C21ⁱ—Pd1—S4—C19	166.54 (9)
S2—Pd1—S1—C5ⁱⁱ	−116.86 (7)	C18ⁱⁱ—Pd1—S4—C19	−40.92 (9)
C22ⁱ—Pd1—S1—C5ⁱⁱ	162.06 (8)	S3ⁱⁱⁱ—Pd1—S4—C19	105.21 (8)
C21ⁱ—Pd1—S1—C5ⁱⁱ	148.28 (8)	S2ⁱⁱ—Pd1—S4—C19	−76.69 (8)
C18ⁱⁱ—Pd1—S1—C5ⁱⁱ	−6.47 (7)	C13ⁱⁱ—Pd1—S4—C19	−53.20 (9)
S3ⁱⁱⁱ—Pd1—S1—C5ⁱⁱ	−154.04 (6)	C17ⁱⁱ—Pd1—S4—C19	−29.83 (9)
S2ⁱⁱ—Pd1—S1—C5ⁱⁱ	27.64 (6)	S3—Pd1—S4—C8ⁱⁱⁱ	117.17 (7)
C13ⁱⁱ—Pd1—S1—C5ⁱⁱ	4.92 (7)	S2—Pd1—S4—C8ⁱⁱⁱ	−58.84 (6)
C17ⁱⁱ—Pd1—S1—C5ⁱⁱ	−16.78 (7)	C22ⁱ—Pd1—S4—C8ⁱⁱⁱ	21.70 (7)
S3—Pd1—S1—C16^iv	−36.01 (7)	C21ⁱ—Pd1—S4—C8ⁱⁱⁱ	36.53 (8)
S2—Pd1—S1—C16^iv	140.14 (7)	C18ⁱⁱ—Pd1—S4—C8ⁱⁱⁱ	−170.93 (7)
C22ⁱ—Pd1—S1—C16^iv	59.07 (8)	S3ⁱⁱⁱ—Pd1—S4—C8ⁱⁱⁱ	−24.80 (6)
C21ⁱ—Pd1—S1—C16^iv	45.28 (8)	S2ⁱⁱ—Pd1—S4—C8ⁱⁱⁱ	153.30 (6)
C18ⁱⁱ—Pd1—S1—C16^iv	−109.47 (8)	C13ⁱⁱ—Pd1—S4—C8ⁱⁱⁱ	176.79 (7)
S3ⁱⁱⁱ—Pd1—S1—C16^iv	102.96 (7)	C17ⁱⁱ—Pd1—S4—C8ⁱⁱⁱ	−159.84 (7)
S2ⁱⁱ—Pd1—S1—C16^iv	−75.36 (7)	S3—Pd1—S4—C7ⁱⁱⁱ	138.21 (5)
C13ⁱⁱ—Pd1—S1—C16^iv	−98.08 (7)	S2—Pd1—S4—C7ⁱⁱⁱ	−37.80 (5)
C17ⁱⁱ—Pd1—S1—C16^iv	−119.78 (7)	C22ⁱ—Pd1—S4—C7ⁱⁱⁱ	42.74 (6)
S3—Pd1—S1—C17^iv	−58.06 (6)	C21ⁱ—Pd1—S4—C7ⁱⁱⁱ	57.57 (6)
S2—Pd1—S1—C17^iv	118.09 (6)	C18ⁱⁱ—Pd1—S4—C7ⁱⁱⁱ	−149.88 (6)
C22ⁱ—Pd1—S1—C17^iv	37.02 (7)	S3ⁱⁱⁱ—Pd1—S4—C7ⁱⁱⁱ	−3.76 (4)
C21ⁱ—Pd1—S1—C17^iv	23.23 (7)	S2ⁱⁱ—Pd1—S4—C7ⁱⁱⁱ	174.34 (4)
C18ⁱⁱ—Pd1—S1—C17^iv	−131.51 (7)	C13ⁱⁱ—Pd1—S4—C7ⁱⁱⁱ	−162.17 (5)
S3ⁱⁱⁱ—Pd1—S1—C17^iv	80.91 (6)	C17ⁱⁱ—Pd1—S4—C7ⁱⁱⁱ	−138.80 (5)
S2ⁱⁱ—Pd1—S1—C17^iv	−97.41 (6)	Pd1—S1—C1—C6	−1.3 (2)
C13ⁱⁱ—Pd1—S1—C17^iv	−120.13 (6)	C5ⁱⁱ—S1—C1—C6	142.87 (19)
C17ⁱⁱ—Pd1—S1—C17^iv	−141.82 (8)	C16^iv—S1—C1—C6	−156.09 (18)
S3—Pd1—S1—C18ⁱⁱ	73.46 (4)	C17^iv—S1—C1—C6	−135.09 (18)
S2—Pd1—S1—C18ⁱⁱ	−110.40 (4)	C18ⁱⁱ—S1—C1—C6	79.8 (2)
C22ⁱ—Pd1—S1—C18ⁱⁱ	168.53 (6)	C21ⁱ—S1—C1—C6	−70.5 (2)
C21ⁱ—Pd1—S1—C18ⁱⁱ	154.75 (6)	C6ⁱⁱ—S1—C1—C6	142.79 (19)
S3ⁱⁱⁱ—Pd1—S1—C18ⁱⁱ	−147.57 (4)	Pd1—S1—C1—C2	179.04 (17)
S2ⁱⁱ—Pd1—S1—C18ⁱⁱ	34.11 (4)	C5ⁱⁱ—S1—C1—C2	−36.80 (19)
C13ⁱⁱ—Pd1—S1—C18ⁱⁱ	11.39 (5)	C16^iv—S1—C1—C2	24.2 (2)
C17ⁱⁱ—Pd1—S1—C18ⁱⁱ	−10.31 (5)	C17^iv—S1—C1—C2	45.2 (2)
S3—Pd1—S1—C21ⁱ	−81.29 (5)	C18ⁱⁱ—S1—C1—C2	−99.85 (19)
S2—Pd1—S1—C21ⁱ	94.86 (5)	C21ⁱ—S1—C1—C2	109.84 (19)
C22ⁱ—Pd1—S1—C21ⁱ	13.78 (6)	C6ⁱⁱ—S1—C1—C2	−36.9 (2)
C18ⁱⁱ—Pd1—S1—C21ⁱ	−154.75 (6)	C6—C1—C2—C3	0.0 (3)
S3ⁱⁱⁱ—Pd1—S1—C21ⁱ	57.68 (5)	S1—C1—C2—C3	179.67 (19)
S2ⁱⁱ—Pd1—S1—C21ⁱ	−120.64 (5)	C1—C2—C3—C4	−0.2 (4)
C13ⁱⁱ—Pd1—S1—C21ⁱ	−143.36 (5)	C2—C3—C4—C5	0.2 (4)
C17ⁱⁱ—Pd1—S1—C21ⁱ	−165.06 (5)	C3—C4—C5—C6	−0.1 (4)
S3—Pd1—S1—C6ⁱⁱ	44.84 (5)	C4—C5—C6—C1	−0.1 (4)
S2—Pd1—S1—C6ⁱⁱ	−139.02 (5)	C4—C5—C6—S2	176.27 (18)
C22ⁱ—Pd1—S1—C6ⁱⁱ	139.91 (6)	C2—C1—C6—C5	0.2 (3)
C21ⁱ—Pd1—S1—C6ⁱⁱ	126.13 (6)	S1—C1—C6—C5	−179.51 (18)
C18ⁱⁱ—Pd1—S1—C6ⁱⁱ	−28.62 (6)	C2—C1—C6—S2	−176.22 (17)
S3ⁱⁱⁱ—Pd1—S1—C6ⁱⁱ	−176.19 (4)	S1—C1—C6—S2	4.1 (3)
S2ⁱⁱ—Pd1—S1—C6ⁱⁱ	5.49 (4)	C13—S2—C6—C5	65.0 (2)
C13ⁱⁱ—Pd1—S1—C6ⁱⁱ	−17.23 (5)	Pd1—S2—C6—C5	179.00 (17)
C17ⁱⁱ—Pd1—S1—C6ⁱⁱ	−38.93 (6)	C13—S2—C6—C1	−118.54 (19)
S1—Pd1—S2—C6	2.81 (8)	Pd1—S2—C6—C1	−4.51 (19)
S4—Pd1—S2—C6	−179.31 (8)	Pd1—S3—C7—C12	4.4 (2)
C22ⁱ—Pd1—S2—C6	98.02 (9)	C22^iv—S3—C7—C12	160.08 (17)
C21ⁱ—Pd1—S2—C6	81.36 (8)	C23^iv—S3—C7—C12	138.68 (18)
C18ⁱⁱ—Pd1—S2—C6	−65.84 (8)	C18ⁱⁱ—S3—C7—C12	−73.9 (2)
S3ⁱⁱⁱ—Pd1—S2—C6	146.12 (8)	Pd1—S3—C7—C8	−177.79 (18)
S2ⁱⁱ—Pd1—S2—C6	−30.56 (8)	C22^iv—S3—C7—C8	−22.1 (2)
C13ⁱⁱ—Pd1—S2—C6	−52.67 (8)	C23^iv—S3—C7—C8	−43.5 (2)
C17ⁱⁱ—Pd1—S2—C6	−76.55 (8)	C18ⁱⁱ—S3—C7—C8	103.92 (19)
S1—Pd1—S2—C13	111.00 (8)	C12—C7—C8—C9	2.9 (4)
S4—Pd1—S2—C13	−71.12 (8)	S3—C7—C8—C9	−175.0 (2)
C22ⁱ—Pd1—S2—C13	−153.79 (9)	C7—C8—C9—C10	−0.5 (4)
C21ⁱ—Pd1—S2—C13	−170.45 (9)	C8—C9—C10—C11	−2.3 (4)
C18ⁱⁱ—Pd1—S2—C13	42.35 (9)	C9—C10—C11—C12	2.5 (4)
S3ⁱⁱⁱ—Pd1—S2—C13	−105.69 (8)	C8—C7—C12—C11	−2.7 (4)
S2ⁱⁱ—Pd1—S2—C13	77.63 (8)	S3—C7—C12—C11	175.16 (19)
C13ⁱⁱ—Pd1—S2—C13	55.52 (7)	C8—C7—C12—S4	172.93 (18)
C17ⁱⁱ—Pd1—S2—C13	31.64 (9)	S3—C7—C12—S4	−9.2 (3)
S1—Pd1—S3—C7	179.15 (8)	C10—C11—C12—C7	0.0 (4)
S4—Pd1—S3—C7	1.01 (8)	C10—C11—C12—S4	−175.6 (2)
C22ⁱ—Pd1—S3—C7	84.41 (9)	C19—S4—C12—C7	122.06 (19)
C21ⁱ—Pd1—S3—C7	100.21 (9)	Pd1—S4—C12—C7	8.7 (2)
C18ⁱⁱ—Pd1—S3—C7	−110.68 (9)	C8ⁱⁱⁱ—S4—C12—C7	−133.27 (18)
S3ⁱⁱⁱ—Pd1—S3—C7	39.99 (9)	C7ⁱⁱⁱ—S4—C12—C7	−134.72 (18)
S2ⁱⁱ—Pd1—S3—C7	−143.43 (8)	C19—S4—C12—C11	−62.2 (2)
C13ⁱⁱ—Pd1—S3—C7	−122.84 (9)	Pd1—S4—C12—C11	−175.60 (18)
C17ⁱⁱ—Pd1—S3—C7	−100.89 (8)	C8ⁱⁱⁱ—S4—C12—C11	42.5 (2)
S1—Pd1—S3—C22^iv	28.69 (6)	C7ⁱⁱⁱ—S4—C12—C11	41.0 (2)
S4—Pd1—S3—C22^iv	−149.45 (6)	C6—S2—C13—C18	−125.0 (2)
C22ⁱ—Pd1—S3—C22^iv	−66.05 (6)	Pd1—S2—C13—C18	124.71 (18)
C21ⁱ—Pd1—S3—C22^iv	−50.24 (7)	C6—S2—C13—C14	55.0 (2)
C18ⁱⁱ—Pd1—S3—C22^iv	98.86 (7)	Pd1—S2—C13—C14	−55.3 (2)
S3ⁱⁱⁱ—Pd1—S3—C22^iv	−110.46 (6)	C18—C13—C14—C15	−0.6 (4)
S2ⁱⁱ—Pd1—S3—C22^iv	66.11 (6)	S2—C13—C14—C15	179.4 (2)
C13ⁱⁱ—Pd1—S3—C22^iv	86.71 (7)	C13—C14—C15—C16	−0.2 (4)
C17ⁱⁱ—Pd1—S3—C22^iv	108.65 (7)	C14—C15—C16—C17	0.8 (4)
S1—Pd1—S3—C23^iv	52.87 (6)	C15—C16—C17—C18	−0.6 (4)
S4—Pd1—S3—C23^iv	−125.27 (6)	C14—C13—C18—C17	0.8 (4)
C22ⁱ—Pd1—S3—C23^iv	−41.87 (7)	S2—C13—C18—C17	−179.2 (2)
C21ⁱ—Pd1—S3—C23^iv	−26.07 (7)	C16—C17—C18—C13	−0.2 (4)
C18ⁱⁱ—Pd1—S3—C23^iv	123.04 (7)	C12—S4—C19—C24	116.5 (2)
S3ⁱⁱⁱ—Pd1—S3—C23^iv	−86.28 (6)	Pd1—S4—C19—C24	−133.37 (19)
S2ⁱⁱ—Pd1—S3—C23^iv	90.29 (6)	C8ⁱⁱⁱ—S4—C19—C24	12.7 (2)
C13ⁱⁱ—Pd1—S3—C23^iv	110.89 (6)	C7ⁱⁱⁱ—S4—C19—C24	−6.6 (2)
C17ⁱⁱ—Pd1—S3—C23^iv	132.83 (6)	C12—S4—C19—C20	−64.2 (2)
S1—Pd1—S3—C18ⁱⁱ	−70.17 (4)	Pd1—S4—C19—C20	45.9 (2)
S4—Pd1—S3—C18ⁱⁱ	111.69 (4)	C8ⁱⁱⁱ—S4—C19—C20	−168.0 (2)
C22ⁱ—Pd1—S3—C18ⁱⁱ	−164.91 (5)	C7ⁱⁱⁱ—S4—C19—C20	172.6 (2)
C21ⁱ—Pd1—S3—C18ⁱⁱ	−149.11 (5)	C24—C19—C20—C21	0.0 (4)
S3ⁱⁱⁱ—Pd1—S3—C18ⁱⁱ	150.68 (4)	S4—C19—C20—C21	−179.2 (2)
S2ⁱⁱ—Pd1—S3—C18ⁱⁱ	−32.75 (4)	C19—C20—C21—C22	0.4 (4)
C13ⁱⁱ—Pd1—S3—C18ⁱⁱ	−12.15 (5)	C20—C21—C22—C23	−0.2 (4)
C17ⁱⁱ—Pd1—S3—C18ⁱⁱ	9.79 (5)	C21—C22—C23—C24	−0.4 (4)
S3—Pd1—S4—C12	−4.56 (8)	C20—C19—C24—C23	−0.6 (4)
S2—Pd1—S4—C12	179.43 (8)	S4—C19—C24—C23	178.7 (2)
C22ⁱ—Pd1—S4—C12	−100.02 (9)	C22—C23—C24—C19	0.8 (4)

Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z; (iii) x+1, y, z; (iv) x−1, y−1, z.

Experimental details

Crystal data
Chemical formula	[Pd(C₁₂H₉S₂)₂]
M_r	541.02
Crystal system, space group	Triclinic, P1
Temperature (K)	153
a, b, c (Å)	6.2910 (1), 8.4579 (2), 20.4780 (5)
α, β, γ (°)	98.7890 (13), 92.7051 (14), 91.2243 (15)
V (Å³)	1075.16 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.26
Crystal size (mm)	0.15 × 0.10 × 0.01

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.834, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	8083, 3985, 3587
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.057, 1.07
No. of reflections	3985
No. of parameters	302
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.36

Computer programs: CrystalClear (Rigaku, 2004), HKL-2000 (Otwinowski & Minor, 1997), HKL-2000, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), Yadokari-XG (Wakita, 2005), SHELXL97.

Selected geometric parameters (Å, º) top

Pd1—S1	2.2886 (6)	S2—C6	1.785 (2)
Pd1—S2	2.3146 (6)	S2—C13	1.790 (2)
Pd1—S3	2.2888 (6)	S3—C7	1.759 (3)
Pd1—S4	2.3186 (6)	S4—C12	1.786 (2)
S1—C1	1.758 (2)	S4—C19	1.789 (2)

S3—Pd1—S1	87.47 (2)	C1—S1—Pd1	104.66 (8)
S3—Pd1—S2	174.59 (2)	C6—S2—Pd1	104.64 (8)
S1—Pd1—S2	88.72 (2)	C13—S2—Pd1	109.61 (8)
S3—Pd1—S4	88.61 (2)	C7—S3—Pd1	104.47 (8)
S1—Pd1—S4	175.66 (2)	C12—S4—Pd1	104.55 (8)
S2—Pd1—S4	95.06 (2)	C19—S4—Pd1	108.93 (8)

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		SGML
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Bis[2-(phenyl­sulfan­yl)benzene­thiol­ato]palladium(II)

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Bis[2-(phenylsulfanyl)benzenethiolato]palladium(II)