Bis(μ-diethyl sulfide-κ2S:S)bis­[(biphenyl-2,2′-di­yl)platinum(ll)]

Rillema, D.P.; Moore, C.; Jehan, A.

doi:10.1107/S2414314616007896

metal-organic compounds

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ISSN: 2414-3146

Volume 1| Part 5| May 2016| x160789

doi:10.1107/S2414314616007896

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Bis(μ-diethyl sulfide-κ²S:S)bis[(biphenyl-2,2′-diyl)platinum(ll)]

D. Paul Rillema,^a ^* Curtis Moore ^b and Ali Jehan ^a

^aDepartment of Chemistry, Wichita State University, Wichita, KS 67260, USA, and ^bCrystallographic Laboratory, University of California, San Diego, La Jolla, CA 92093, USA
^*Correspondence e-mail: paul.rillema@wichita.edu

Edited by M. Zeller, Purdue University, USA (Received 11 May 2016; accepted 13 May 2016; online 20 May 2016)

The C₄S₂ donor set in the title compound, [Pt(C₁₂H₈){(C₂H₅)₂S}]₂, defines a distorted square-planar geometry about the two Pt^II atoms, with very small deviations from planarity. The bidentate nature of the biphenyl dianionic ligand results in C—Pt—C bond angles of 80.9 (2) and 81.2 (2)°; the S—Pt—S bond angles are 78.08 (5) and 78.09 (5)°. The average Pt—C bond length is 2.023 Å [range 2.016 (5)–2.028 (6) Å] and the average of Pt—S bond length is 2.3790 Å [range 2.3742 (14)–2.3837 (14) Å].

Keywords: crystal structure; platinum(II) biphenyl diethyl sulfide dimer; intermediate complex.

CCDC reference: 1479776

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Chemical scheme

Structure description

We are interested in preparing Pt^II complexes containing the biphenyl dianion with diimine ligands due to their excited state emission properties (Rillema et al., 2015 ). [Pt(C₁₂H₈){(C₂H₅)₂S}]₂ (Fig. 1) is a synthetic intermediate. The bidentate nature of the 2,2′-biphenyl ligand gave C—Pt—C bite angles of 80.9 (2) and 81.2 (2)°, as expected from previous studies (Rillema et al., 2013 ), but the S—Pt—S angles of 78.08 (5) and 78.09 (5)° for the square-planar biphenyl–Pt^II units bridged by sulfur ligands was ∼2° less than what had been found for a similar diethyl sulfide-bridged platinum(II) complex with four 4-fluorophenyl groups in place of the two bidentate biphenyl ligands (Escola et al., 2014 ). Substitution of the bridging sulfur ligands with Br gave Br—Pt—Br angles of 83.0 (1)° and Pt—C bond lengths of 2.01 (2) and 2.01 (2) Å for the bis{(μ₂-bromido)[(2,2′-η²)-4,4′-bis(trifluoromethyl)biphenyl]platinum(II)} anion (Brune et al., 1991 ).

Figure 1
The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids. H atoms have been omitted for clarity.

Synthesis and crystallization

The title compound was synthesized according to previously published procedures (Gilman & Gaj, 1957 ; Gardner et al., 1973 ). X-ray quality crystals were obtained by recrystallization from benzene.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	[Pt₂(C₁₂H₈)₂(C₄H₁₀S)₂]
M_r	874.91
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	19.2938 (15), 7.8839 (6), 19.6969 (17)
β (°)	109.639 (5)
V (Å³)	2821.8 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	10.07
Crystal size (mm)	0.05 × 0.02 × 0.01

Data collection
Diffractometer	Bruker APEXII Ultra
Absorption correction	Multi-scan (SADABS; Bruker, 2015 )
T_min, T_max	0.018, 0.048
No. of measured, independent and observed [I > 2σ(I)] reflections	39433, 6763, 5668
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.066, 1.10
No. of reflections	6763
No. of parameters	329
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.93, −1.80
Computer programs: APEX2 (Bruker, 2012 ), SAINT (Bruker, 2012 ), SHELXT (Sheldrick, 2015a ), SHELXL2015 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1479776

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616007896/zl4008sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616007896/zl4008Isup2.hkl

checkCIF report

Experimental top

The title compound was synthesized according to previously published procedures (Gilman & Gaj, 1957; Gardner et al., 1973). X-ray quality crystals were obtained by recrystallization from benzene.

Structure description top

We are interested in preparing Pt^II complexes containing the biphenyl dianion with diimine ligands due to their excited state emission properties (Rillema et al., 2015). [Pt(C₁₂H₁₀)((C₂H₅)₂S)]₂ is a synthetic intermediate. The bidentate nature of the 2,2'-biphenyl ligand gave C—Pt—C bite angles of 81.9 (2) and 81.2 (2)°, as expected from previous studies (Rillema et al., 2013), but the S—Pt—S angles of 78.08 (5) and 78.09 (5)° for the square-planar biphenyl–Pt^II units bridged by sulfur ligands was ~2° less than what had been found for a similarly diethyl sulfide-bridged platinum(II) complex with four 4-fluorophenyl groups in place of the two bidentate biphenyl ligands (Escola et al., 2014). Substitution of the bridging sulfur ligands with Br gave Br—Pt—Br angles of 83.0 (1)° and Pt—C bond lenghts of 2.01 (2) and 2.01 (2) Å for the bis{(µ₂-bromo)2,2'-η²-[4,4'-bis(trifluoromethyl)biphenyl]platinum(II)} anion (Brune et al., 1991).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids. H atoms have been omitted for clarity.

Bis(µ-diethyl sulfide-κ²S:S)bis[(biphenyl-2,2'-diyl)platinum(ll)] top

Crystal data top

[Pt₂(C₁₂H₁₀)₂(C₄H₈S)₂]	F(000) = 1664
M_r = 874.91	D_x = 2.059 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 19.2938 (15) Å	Cell parameters from 9904 reflections
b = 7.8839 (6) Å	θ = 2.2–28.3°
c = 19.6969 (17) Å	µ = 10.07 mm⁻¹
β = 109.639 (5)°	T = 100 K
V = 2821.8 (4) Å³	Rod, yellow
Z = 4	0.05 × 0.02 × 0.01 mm

Data collection top

Bruker APEXII Ultra diffractometer	6763 independent reflections
Radiation source: Micro Focus Rotating Anode, Bruker TXS	5668 reflections with I > 2σ(I)
Double Bounce Multilayer Mirrors monochromator	R_int = 0.052
Detector resolution: 7.9 pixels mm^-1	θ_max = 28.3°, θ_min = 2.8°
ω and φ scans	h = −23→25
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −10→10
T_min = 0.018, T_max = 0.048	l = −26→26
39433 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0141P)² + 15.5401P] where P = (F_o² + 2F_c²)/3
6763 reflections	(Δ/σ)_max = 0.001
329 parameters	Δρ_max = 1.93 e Å⁻³
0 restraints	Δρ_min = −1.80 e Å⁻³

Crystal data top

[Pt₂(C₁₂H₁₀)₂(C₄H₈S)₂]	V = 2821.8 (4) Å³
M_r = 874.91	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 19.2938 (15) Å	µ = 10.07 mm⁻¹
b = 7.8839 (6) Å	T = 100 K
c = 19.6969 (17) Å	0.05 × 0.02 × 0.01 mm
β = 109.639 (5)°

Data collection top

Bruker APEXII Ultra diffractometer	6763 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2015)	5668 reflections with I > 2σ(I)
T_min = 0.018, T_max = 0.048	R_int = 0.052
39433 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.066	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0141P)² + 15.5401P] where P = (F_o² + 2F_c²)/3
6763 reflections	Δρ_max = 1.93 e Å⁻³
329 parameters	Δρ_min = −1.80 e Å⁻³

Special details top

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

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

	x	y	z	U_iso*/U_eq
Pt1	1.06321 (2)	0.28426 (3)	0.22858 (2)	0.01920 (6)
Pt2	0.92032 (2)	0.59665 (3)	0.22827 (2)	0.01973 (6)
S1	0.96358 (8)	0.43818 (17)	0.14799 (7)	0.0201 (3)
S2	1.02012 (8)	0.44260 (17)	0.30952 (7)	0.0209 (3)
C1	1.1019 (3)	0.1619 (7)	0.1581 (3)	0.0205 (11)
C2	1.1493 (3)	0.1631 (7)	0.2996 (3)	0.0198 (11)
C3	0.8333 (3)	0.7156 (7)	0.1570 (3)	0.0216 (12)
C4	0.8827 (3)	0.7209 (7)	0.2990 (3)	0.0210 (11)
C5	1.0705 (3)	0.1585 (7)	0.0830 (3)	0.0230 (12)
H5	1.0250	0.2150	0.0607	0.028*
C6	1.1040 (3)	0.0741 (7)	0.0399 (3)	0.0234 (12)
H6	1.0818	0.0746	−0.0110	0.028*
C7	1.1697 (3)	−0.0101 (7)	0.0720 (3)	0.0250 (13)
H7	1.1932	−0.0667	0.0431	0.030*
C8	1.2013 (3)	−0.0117 (7)	0.1466 (3)	0.0248 (12)
H8	1.2462	−0.0708	0.1686	0.030*
C9	1.1680 (3)	0.0720 (7)	0.1893 (3)	0.0204 (11)
C10	1.1955 (3)	0.0738 (7)	0.2690 (3)	0.0207 (12)
C11	1.2586 (3)	−0.0065 (7)	0.3120 (3)	0.0244 (12)
H11	1.2890	−0.0643	0.2903	0.029*
C12	1.2781 (3)	−0.0034 (7)	0.3867 (3)	0.0263 (13)
H12	1.3220	−0.0568	0.4163	0.032*
C13	1.2327 (3)	0.0781 (7)	0.4172 (3)	0.0264 (13)
H13	1.2445	0.0776	0.4681	0.032*
C14	1.1696 (3)	0.1612 (7)	0.3741 (3)	0.0249 (12)
H14	1.1395	0.2182	0.3964	0.030*
C15	0.8112 (3)	0.7139 (7)	0.0820 (3)	0.0227 (12)
H15	0.8405	0.6553	0.0593	0.027*
C16	0.7473 (3)	0.7956 (7)	0.0391 (3)	0.0241 (12)
H16	0.7338	0.7915	−0.0120	0.029*
C17	0.7035 (3)	0.8824 (7)	0.0704 (3)	0.0259 (13)
H17	0.6594	0.9356	0.0412	0.031*
C18	0.7250 (3)	0.8909 (7)	0.1456 (3)	0.0257 (13)
H18	0.6963	0.9538	0.1676	0.031*
C19	0.7881 (3)	0.8078 (7)	0.1883 (3)	0.0221 (12)
C20	0.8163 (3)	0.8089 (7)	0.2682 (3)	0.0231 (12)
C21	0.7823 (3)	0.8892 (7)	0.3106 (3)	0.0259 (13)
H21	0.7366	0.9452	0.2885	0.031*
C22	0.8140 (3)	0.8894 (8)	0.3854 (3)	0.0280 (13)
H22	0.7900	0.9433	0.4146	0.034*
C23	0.8807 (4)	0.8101 (7)	0.4164 (3)	0.0284 (13)
H23	0.9036	0.8122	0.4672	0.034*
C24	0.9149 (3)	0.7269 (7)	0.3742 (3)	0.0257 (13)
H24	0.9610	0.6731	0.3968	0.031*
C25	0.9924 (3)	0.5681 (7)	0.0864 (3)	0.0239 (12)
H25A	1.0208	0.4980	0.0633	0.029*
H25B	0.9485	0.6125	0.0481	0.029*
C26	1.0396 (4)	0.7150 (8)	0.1260 (3)	0.0321 (14)
H26A	1.0111	0.7857	0.1480	0.048*
H26B	1.0548	0.7833	0.0919	0.048*
H26C	1.0832	0.6710	0.1637	0.048*
C27	0.8930 (3)	0.3033 (7)	0.0872 (3)	0.0252 (13)
H27A	0.8484	0.3715	0.0631	0.030*
H27B	0.9111	0.2565	0.0496	0.030*
C28	0.8738 (4)	0.1596 (9)	0.1285 (4)	0.0356 (15)
H28A	0.9175	0.0893	0.1505	0.053*
H28B	0.8348	0.0903	0.0954	0.053*
H28C	0.8567	0.2060	0.1662	0.053*
C29	1.0927 (3)	0.5749 (7)	0.3692 (3)	0.0246 (12)
H29A	1.0747	0.6306	0.4052	0.030*
H29B	1.1356	0.5036	0.3953	0.030*
C30	1.1156 (4)	0.7083 (8)	0.3256 (4)	0.0370 (16)
H30A	1.1325	0.6527	0.2895	0.055*
H30B	1.1555	0.7770	0.3577	0.055*
H30C	1.0734	0.7814	0.3013	0.055*
C31	0.9904 (3)	0.3146 (8)	0.3714 (3)	0.0266 (13)
H31A	1.0338	0.2640	0.4084	0.032*
H31B	0.9642	0.3865	0.3960	0.032*
C32	0.9399 (4)	0.1756 (9)	0.3296 (4)	0.0429 (18)
H32A	0.8964	0.2264	0.2940	0.064*
H32B	0.9247	0.1045	0.3628	0.064*
H32C	0.9660	0.1059	0.3047	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.02093 (11)	0.01524 (10)	0.02032 (11)	0.00053 (8)	0.00548 (8)	0.00055 (8)
Pt2	0.02191 (11)	0.01607 (10)	0.02061 (11)	0.00074 (8)	0.00635 (8)	0.00018 (8)
S1	0.0227 (7)	0.0160 (7)	0.0206 (7)	0.0007 (5)	0.0059 (6)	0.0004 (5)
S2	0.0231 (7)	0.0184 (7)	0.0206 (7)	0.0011 (5)	0.0066 (6)	0.0007 (5)
C1	0.025 (3)	0.016 (3)	0.021 (3)	−0.002 (2)	0.007 (2)	0.002 (2)
C2	0.021 (3)	0.018 (3)	0.020 (3)	−0.003 (2)	0.006 (2)	0.001 (2)
C3	0.026 (3)	0.016 (3)	0.022 (3)	−0.004 (2)	0.007 (2)	−0.001 (2)
C4	0.023 (3)	0.016 (3)	0.024 (3)	−0.001 (2)	0.008 (2)	0.002 (2)
C5	0.028 (3)	0.015 (3)	0.025 (3)	0.002 (2)	0.008 (2)	0.002 (2)
C6	0.030 (3)	0.017 (3)	0.023 (3)	−0.002 (2)	0.009 (2)	0.000 (2)
C7	0.031 (3)	0.019 (3)	0.029 (3)	−0.001 (2)	0.014 (3)	−0.003 (2)
C8	0.026 (3)	0.018 (3)	0.030 (3)	0.004 (2)	0.010 (3)	0.001 (2)
C9	0.023 (3)	0.013 (3)	0.026 (3)	−0.003 (2)	0.009 (2)	−0.001 (2)
C10	0.030 (3)	0.013 (3)	0.021 (3)	−0.005 (2)	0.010 (2)	0.000 (2)
C11	0.023 (3)	0.017 (3)	0.033 (3)	0.002 (2)	0.009 (3)	0.002 (2)
C12	0.027 (3)	0.018 (3)	0.029 (3)	0.003 (2)	0.003 (3)	0.006 (2)
C13	0.033 (3)	0.018 (3)	0.024 (3)	−0.002 (2)	0.005 (3)	0.001 (2)
C14	0.026 (3)	0.018 (3)	0.030 (3)	−0.001 (2)	0.009 (3)	0.000 (2)
C15	0.027 (3)	0.016 (3)	0.026 (3)	0.000 (2)	0.009 (2)	0.001 (2)
C16	0.026 (3)	0.020 (3)	0.024 (3)	−0.003 (2)	0.006 (2)	0.000 (2)
C17	0.023 (3)	0.020 (3)	0.031 (3)	0.003 (2)	0.004 (3)	0.003 (2)
C18	0.027 (3)	0.021 (3)	0.028 (3)	0.005 (2)	0.007 (3)	−0.002 (2)
C19	0.022 (3)	0.015 (3)	0.028 (3)	−0.002 (2)	0.006 (2)	−0.003 (2)
C20	0.024 (3)	0.017 (3)	0.029 (3)	0.000 (2)	0.011 (2)	0.000 (2)
C21	0.024 (3)	0.021 (3)	0.035 (3)	0.003 (2)	0.013 (3)	0.001 (3)
C22	0.034 (3)	0.025 (3)	0.029 (3)	−0.002 (3)	0.016 (3)	−0.004 (3)
C23	0.040 (4)	0.022 (3)	0.024 (3)	−0.001 (3)	0.012 (3)	0.001 (2)
C24	0.030 (3)	0.020 (3)	0.026 (3)	0.005 (2)	0.009 (3)	0.001 (2)
C25	0.033 (3)	0.018 (3)	0.023 (3)	−0.001 (2)	0.012 (3)	0.000 (2)
C26	0.040 (4)	0.027 (3)	0.031 (3)	−0.011 (3)	0.014 (3)	0.000 (3)
C27	0.025 (3)	0.020 (3)	0.027 (3)	−0.005 (2)	0.005 (2)	−0.005 (2)
C28	0.037 (4)	0.033 (4)	0.034 (4)	−0.010 (3)	0.009 (3)	0.000 (3)
C29	0.024 (3)	0.022 (3)	0.021 (3)	−0.001 (2)	−0.001 (2)	−0.005 (2)
C30	0.039 (4)	0.028 (3)	0.037 (4)	−0.006 (3)	0.003 (3)	0.004 (3)
C31	0.028 (3)	0.027 (3)	0.026 (3)	0.002 (2)	0.010 (3)	0.004 (2)
C32	0.060 (5)	0.029 (4)	0.045 (4)	−0.013 (3)	0.026 (4)	−0.006 (3)

Geometric parameters (Å, º) top

Pt1—S1	2.3742 (14)	C16—H16	0.9500
Pt1—S2	2.3837 (14)	C16—C17	1.383 (8)
Pt1—C1	2.028 (6)	C17—H17	0.9500
Pt1—C2	2.016 (5)	C17—C18	1.400 (8)
Pt2—S1	2.3759 (14)	C18—H18	0.9500
Pt2—S2	2.3816 (14)	C18—C19	1.390 (8)
Pt2—C3	2.021 (6)	C19—C20	1.482 (8)
Pt2—C4	2.027 (6)	C20—C21	1.378 (8)
S1—C25	1.812 (6)	C21—H21	0.9500
S1—C27	1.823 (6)	C21—C22	1.394 (8)
S2—C29	1.823 (6)	C22—H22	0.9500
S2—C31	1.816 (6)	C22—C23	1.374 (9)
C1—C5	1.396 (8)	C23—H23	0.9500
C1—C9	1.407 (8)	C23—C24	1.387 (8)
C2—C10	1.419 (8)	C24—H24	0.9500
C2—C14	1.386 (8)	C25—H25A	0.9900
C3—C15	1.394 (8)	C25—H25B	0.9900
C3—C19	1.425 (8)	C25—C26	1.517 (8)
C4—C20	1.403 (8)	C26—H26A	0.9800
C4—C24	1.401 (8)	C26—H26B	0.9800
C5—H5	0.9500	C26—H26C	0.9800
C5—C6	1.397 (8)	C27—H27A	0.9900
C6—H6	0.9500	C27—H27B	0.9900
C6—C7	1.381 (8)	C27—C28	1.510 (8)
C7—H7	0.9500	C28—H28A	0.9800
C7—C8	1.390 (8)	C28—H28B	0.9800
C8—H8	0.9500	C28—H28C	0.9800
C8—C9	1.386 (8)	C29—H29A	0.9900
C9—C10	1.478 (7)	C29—H29B	0.9900
C10—C11	1.381 (8)	C29—C30	1.514 (8)
C11—H11	0.9500	C30—H30A	0.9800
C11—C12	1.393 (8)	C30—H30B	0.9800
C12—H12	0.9500	C30—H30C	0.9800
C12—C13	1.376 (8)	C31—H31A	0.9900
C13—H13	0.9500	C31—H31B	0.9900
C13—C14	1.392 (8)	C31—C32	1.512 (9)
C14—H14	0.9500	C32—H32A	0.9800
C15—H15	0.9500	C32—H32B	0.9800
C15—C16	1.396 (8)	C32—H32C	0.9800

S1—Pt1—S2	78.08 (5)	C16—C17—H17	120.4
C1—Pt1—S1	100.76 (16)	C16—C17—C18	119.2 (5)
C1—Pt1—S2	176.78 (16)	C18—C17—H17	120.4
C2—Pt1—S1	177.46 (16)	C17—C18—H18	119.8
C2—Pt1—S2	100.11 (16)	C19—C18—C17	120.4 (5)
C2—Pt1—C1	80.9 (2)	C19—C18—H18	119.8
S1—Pt2—S2	78.09 (5)	C3—C19—C20	113.7 (5)
C3—Pt2—S1	100.21 (16)	C18—C19—C3	121.2 (5)
C3—Pt2—S2	176.99 (16)	C18—C19—C20	125.1 (5)
C3—Pt2—C4	81.2 (2)	C4—C20—C19	114.4 (5)
C4—Pt2—S1	177.17 (16)	C21—C20—C4	121.1 (6)
C4—Pt2—S2	100.35 (16)	C21—C20—C19	124.4 (5)
Pt1—S1—Pt2	102.14 (5)	C20—C21—H21	119.6
C25—S1—Pt1	112.0 (2)	C20—C21—C22	120.8 (6)
C25—S1—Pt2	113.82 (19)	C22—C21—H21	119.6
C25—S1—C27	102.7 (3)	C21—C22—H22	120.6
C27—S1—Pt1	113.5 (2)	C23—C22—C21	118.8 (6)
C27—S1—Pt2	113.1 (2)	C23—C22—H22	120.6
Pt2—S2—Pt1	101.69 (5)	C22—C23—H23	119.6
C29—S2—Pt1	111.5 (2)	C22—C23—C24	120.9 (6)
C29—S2—Pt2	114.43 (19)	C24—C23—H23	119.6
C31—S2—Pt1	114.6 (2)	C4—C24—H24	119.4
C31—S2—Pt2	111.6 (2)	C23—C24—C4	121.1 (6)
C31—S2—C29	103.5 (3)	C23—C24—H24	119.4
C5—C1—Pt1	127.2 (4)	S1—C25—H25A	109.5
C5—C1—C9	117.4 (5)	S1—C25—H25B	109.5
C9—C1—Pt1	115.3 (4)	H25A—C25—H25B	108.1
C10—C2—Pt1	115.4 (4)	C26—C25—S1	110.7 (4)
C14—C2—Pt1	127.8 (4)	C26—C25—H25A	109.5
C14—C2—C10	116.7 (5)	C26—C25—H25B	109.5
C15—C3—Pt2	128.2 (4)	C25—C26—H26A	109.5
C15—C3—C19	116.7 (5)	C25—C26—H26B	109.5
C19—C3—Pt2	115.0 (4)	C25—C26—H26C	109.5
C20—C4—Pt2	115.3 (4)	H26A—C26—H26B	109.5
C24—C4—Pt2	127.5 (4)	H26A—C26—H26C	109.5
C24—C4—C20	117.2 (5)	H26B—C26—H26C	109.5
C1—C5—H5	119.1	S1—C27—H27A	109.6
C1—C5—C6	121.8 (5)	S1—C27—H27B	109.6
C6—C5—H5	119.1	H27A—C27—H27B	108.1
C5—C6—H6	120.2	C28—C27—S1	110.4 (4)
C7—C6—C5	119.5 (5)	C28—C27—H27A	109.6
C7—C6—H6	120.2	C28—C27—H27B	109.6
C6—C7—H7	120.1	C27—C28—H28A	109.5
C6—C7—C8	119.8 (5)	C27—C28—H28B	109.5
C8—C7—H7	120.1	C27—C28—H28C	109.5
C7—C8—H8	119.7	H28A—C28—H28B	109.5
C9—C8—C7	120.7 (5)	H28A—C28—H28C	109.5
C9—C8—H8	119.7	H28B—C28—H28C	109.5
C1—C9—C10	114.2 (5)	S2—C29—H29A	109.7
C8—C9—C1	120.7 (5)	S2—C29—H29B	109.7
C8—C9—C10	125.1 (5)	H29A—C29—H29B	108.2
C2—C10—C9	113.7 (5)	C30—C29—S2	109.8 (4)
C11—C10—C2	121.1 (5)	C30—C29—H29A	109.7
C11—C10—C9	125.1 (5)	C30—C29—H29B	109.7
C10—C11—H11	119.7	C29—C30—H30A	109.5
C10—C11—C12	120.6 (5)	C29—C30—H30B	109.5
C12—C11—H11	119.7	C29—C30—H30C	109.5
C11—C12—H12	120.5	H30A—C30—H30B	109.5
C13—C12—C11	119.0 (5)	H30A—C30—H30C	109.5
C13—C12—H12	120.5	H30B—C30—H30C	109.5
C12—C13—H13	119.7	S2—C31—H31A	109.9
C12—C13—C14	120.5 (6)	S2—C31—H31B	109.9
C14—C13—H13	119.7	H31A—C31—H31B	108.3
C2—C14—C13	121.9 (6)	C32—C31—S2	109.1 (4)
C2—C14—H14	119.0	C32—C31—H31A	109.9
C13—C14—H14	119.0	C32—C31—H31B	109.9
C3—C15—H15	119.0	C31—C32—H32A	109.5
C3—C15—C16	122.1 (5)	C31—C32—H32B	109.5
C16—C15—H15	119.0	C31—C32—H32C	109.5
C15—C16—H16	119.8	H32A—C32—H32B	109.5
C17—C16—C15	120.4 (5)	H32A—C32—H32C	109.5
C17—C16—H16	119.8	H32B—C32—H32C	109.5

Experimental details

Crystal data
Chemical formula	[Pt₂(C₁₂H₁₀)₂(C₄H₈S)₂]
M_r	874.91
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	19.2938 (15), 7.8839 (6), 19.6969 (17)
β (°)	109.639 (5)
V (Å³)	2821.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	10.07
Crystal size (mm)	0.05 × 0.02 × 0.01

Data collection
Diffractometer	Bruker APEXII Ultra
Absorption correction	Multi-scan (SADABS; Bruker, 2015)
T_min, T_max	0.018, 0.048
No. of measured, independent and observed [I > 2σ(I)] reflections	39433, 6763, 5668
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.066, 1.10
No. of reflections	6763
No. of parameters	329
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0141P)² + 15.5401P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.93, −1.80

Computer programs: APEX2 (Bruker, 2013), SAINT (Bruker, 2012), SHELXT (Sheldrick, 2015a), SHELXL2015 (Sheldrick, 2015b), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

We are grateful for support from the National Science Foundation (EPSCoR), the Wichita State University Office of Research Administration, and the Department of Energy.

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