Bis(tetra­phenyl­phospho­nium) bis­[N-(2,5-dichloro­phenyl­sulfon­yl)dithio­carbimato(2−)-κ2S,S′]platinate(II)

Guilardi, S.; Flauzino Neto, W.P.; Vieira, L.C.C.; Amin, R.S.; Oliveira, M.R.L.

doi:10.1107/S1600536810003272

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m251

doi:10.1107/S1600536810003272

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Bis(tetraphenylphosphonium) bis[N-(2,5-dichlorophenylsulfonyl)dithiocarbimato(2−)-κ²S,S′]platinate(II)

S. Guilardi,^a ^* Wilson P. Flauzino Neto,^a Lucas C. C. Vieira,^a Raquel S. Amin ^b and Marcelo R. L. Oliveira ^b

^aInstituto de Química – UFU, 38408-100 Uberlândia, MG, Brazil, and ^bDepartamento de Química – UFV, 36571-000 Viçosa, MG, Brazil
^*Correspondence e-mail: sguilardi@yahoo.com.br

(Received 21 January 2010; accepted 26 January 2010; online 3 February 2010)

In the title salt, (C₂₄H₂₀P)₂[Pt(C₇H₃Cl₂NO₂S₃)₂], the Pt^II ion (site symmetry $[\overline{1}]$ ) is coordinated by two S,S′-bidentate N-(2,5-dichlorophenylsulfonyl)dithiocarbimate ligands, resulting in a slightly distorted PtS₄ square-planar geometry. In the crystal, a C—H⋯O interaction is observed, as well as electrostatic attraction between the oppositely charged ions.

Related literature

For other complexes containing a [Pt(RSO₂N=CS₂)]²⁻ unit, see: Amim et al. (2008 ); Oliveira et al. (2003 , 2004 ). For general background to dithiocarbimates, see: Hogarth (2005 ). For reference structural data, see: Allen et al. (1987 ). For further synthetic details, see: Franca et al. (2006 ).

Experimental

Crystal data

(C₂₄H₂₀P)₂[Pt(C₇H₃Cl₂NO₂S₃)₂]
M_r = 1474.3
Triclinic, $[P \overline 1]$
a = 9.6284 (1) Å
b = 10.3409 (2) Å
c = 15.1278 (2) Å
α = 76.951 (1)°
β = 88.353 (1)°
γ = 86.193 (1)°
V = 1463.94 (4) Å³
Z = 1
Mo Kα radiation
μ = 2.90 mm⁻¹
T = 120 K
0.34 × 0.34 × 0.3 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: gaussian (Coppens et al., 1965 ) T_min = 0.439, T_max = 0.477
11423 measured reflections
6536 independent reflections
6483 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.068
S = 1.11
6536 reflections
367 parameters
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −2.58 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Pt—S1	2.3128 (6)
Pt—S2	2.3233 (6)

S1—Pt—S2	74.59 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27⋯O1ⁱ	0.95	2.43	3.111 (4)	128
Symmetry code: (i) x+1, y, z.

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003272/hb5315sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810003272/hb5315Isup2.hkl

checkCIF report

Comment top

We became interested in the syntheses and characterization of Pt(II) complexes with dithiocarbimates due to their potential application as antitumoral. Some platinum- dithiocarbimato-anionic complexes with general formulae [Pt(RSO₂N═CS₂)]^2- (R = aryl groups) have had their structures determined by X-ray diffraction techniques. All of these compounds have the tetrabutylammonium as counter-ion (Amim et al., 2008; Oliveira et al., 2004). Variations in the counter-ions and in the R group can be important to modulate the activity of these compounds favoring the biological application.

The title compound is quite stable at the ambient conditions. The Pt(II) is located at the inversion centre and the PtS₄ fragment has a distorted square-planar geometry due to the bidentate chelation (Figure 1). The Pt—S bond lengths are almost equal but the angles S1—Pt—S2 and S2ⁱ—Pt—S1 are 74.59 (2)° and 105.41 (2)° respectively (Table 1). In the fragment N═ CS₂, the C—S bond lengths are nearly equal and are shorter than C—S single bonds (ca 1.815 Å) ( Allen et al., 1987). The C1═N bond distances [1.310 (3) Å] have a double character. This behavior indicates that the electron density is delocalized over the entire NCS₂ moiety. The S1—C1—N angle is significantly greater than S2—C1—N probably due to the repulsive interaction between the (2,5-Cl₂C₂H₃)SO₂ group and the S1 atom, which are in cis position in relation to the C1—N bond. Similar behavior is observed in the square-planar platinum(II) and nickel(II) complexes of dithiocarbimates (Amim et al., 2008; Oliveira et al., 2004; Oliveira et al., 2003; Franca et al., 2006).

The bond lengths and angles of the tetraphenylphosphonium cations are in agreement with the expected values (Allen et al., 1987). The crystal packing is mainly maintained by ionic bond, but there are weak interactions of the type C—H···O (Table 2).

Related literature top

For other complexes containing a [Pt(RSO₂N═CS₂)^2- unit, see: Amim et al. (2008); Oliveira et al. (2003, 2004). For general background to dithiocarbimates, see: Hogarth (2005). For reference structural data, see: Allen et al. (1987). For further synthetic details, see: Franca et al. (2006).

Experimental top

Potassium 2,5-dichlorophenylsulfonyldithiocarbimate dihydrate was prepared from the sulfonamide using procedures described in the literature (Franca et al., 2006). The title compound was prepared in 1:1 (10 ml) methanol:water mixture from potassium tetrachloroplatinate(II) (0.40 mmol) potassium 2,5-dichlorophenylsulfonyldithiocarbimate dihydrate (0.80 mmol) and tetraphenylphosphonium bromide (0.80 mmol). The reaction mixture was stirred for 1 h at room temperature. The yellow solid obtained was filtered, washed with distilled water, ethyl alcohol and dried under reduced pressure. The title compound is slightly soluble in chloroform and insoluble in water and in most organic solvents. Yellow prisms of (I) were obtained after slow evaporation of solution of the compound in hot chloroform. M.p. 195.2-195.6°C. IR (most important bands, cm^-1): 1409 ν(C═N); 1309 ν_ass(SO₂); 1107 ν_sym(SO₂); 932 ν_ass(CS₂) and 312 ν(NiS).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. View of (I) with displacement ellipsoids drawn at the 30% probability level and H atoms omitted for clarity.

Bis(tetraphenylphosphonium) bis[N-(2,5-dichlorophenylsulfonyl)dithiocarbimato(2-)- κ²S,S']platinate(II) top

Crystal data top

(C₂₄H₂₀P)₂[Pt(C₇H₃Cl₂NO₂S₃)₂]	Z = 1
M_r = 1474.3	F(000) = 736
Triclinic, P1	D_x = 1.672 Mg m⁻³
a = 9.6284 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3409 (2) Å	Cell parameters from 20612 reflections
c = 15.1278 (2) Å	θ = 2.9–27.1°
α = 76.951 (1)°	µ = 2.90 mm⁻¹
β = 88.353 (1)°	T = 120 K
γ = 86.193 (1)°	Prism, yellow
V = 1463.94 (4) Å³	0.34 × 0.34 × 0.3 mm

Data collection top

Nonius KappaCCD diffractometer	6483 reflections with I > 2σ(I)
CCD rotation images, thick slices scans	R_int = 0.029
Absorption correction: gaussian (Coppens et al., 1965)	θ_max = 27.3°, θ_min = 2.9°
T_min = 0.439, T_max = 0.477	h = −12→12
11423 measured reflections	k = −13→13
6536 independent reflections	l = −19→19

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.025	w = 1/[σ²(F_o²) + (0.0373P)² + 0.5896P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.068	(Δ/σ)_max = 0.001
S = 1.11	Δρ_max = 0.69 e Å⁻³
6536 reflections	Δρ_min = −2.58 e Å⁻³
367 parameters

Crystal data top

(C₂₄H₂₀P)₂[Pt(C₇H₃Cl₂NO₂S₃)₂]	γ = 86.193 (1)°
M_r = 1474.3	V = 1463.94 (4) Å³
Triclinic, P1	Z = 1
a = 9.6284 (1) Å	Mo Kα radiation
b = 10.3409 (2) Å	µ = 2.90 mm⁻¹
c = 15.1278 (2) Å	T = 120 K
α = 76.951 (1)°	0.34 × 0.34 × 0.3 mm
β = 88.353 (1)°

Data collection top

Nonius KappaCCD diffractometer	6536 independent reflections
Absorption correction: gaussian (Coppens et al., 1965)	6483 reflections with I > 2σ(I)
T_min = 0.439, T_max = 0.477	R_int = 0.029
11423 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.068	H-atom parameters constrained
S = 1.11	Δρ_max = 0.69 e Å⁻³
6536 reflections	Δρ_min = −2.58 e Å⁻³
367 parameters

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
P	0.48411 (6)	1.00796 (6)	0.28241 (4)	0.01728 (12)
C13	0.5666 (3)	0.7769 (2)	0.40148 (18)	0.0233 (5)
H13	0.5906	0.8339	0.4391	0.028*
C12	0.5927 (3)	0.6407 (3)	0.4298 (2)	0.0271 (5)
H12	0.6346	0.604	0.4868	0.032*
C11	0.5571 (3)	0.5583 (3)	0.3744 (2)	0.0287 (6)
H11	0.5758	0.4649	0.3934	0.034*
C21	0.3060 (3)	1.0340 (3)	0.13883 (19)	0.0267 (5)
H21	0.2428	0.9883	0.1824	0.032*
C10	0.4953 (3)	0.6104 (3)	0.2923 (2)	0.0284 (6)
H10	0.4709	0.5525	0.2554	0.034*
C16	0.1901 (3)	1.0494 (3)	0.47488 (19)	0.0299 (6)
H16	0.144	0.9946	0.5244	0.036*
C18	0.2237 (3)	1.2660 (3)	0.3820 (2)	0.0323 (6)
H18	0.2025	1.3593	0.3688	0.039*
C22	0.2692 (3)	1.0749 (3)	0.0481 (2)	0.0315 (6)
H22	0.1812	1.0557	0.0291	0.038*
C17	0.1609 (3)	1.1857 (3)	0.4552 (2)	0.0337 (7)
H17	0.0971	1.224	0.4925	0.04*
C25	0.5288 (3)	1.1294 (3)	0.10141 (19)	0.0266 (5)
H25	0.618	1.147	0.1196	0.032*
C27	0.7675 (3)	1.0027 (3)	0.2710 (2)	0.0332 (6)
H27	0.7593	0.9226	0.2513	0.04*
C24	0.4903 (3)	1.1720 (3)	0.0114 (2)	0.0329 (6)
H24	0.552	1.2202	−0.0321	0.04*
C29	0.9089 (4)	1.1685 (4)	0.3024 (2)	0.0442 (8)
H29	0.9976	1.2034	0.3029	0.053*
C30	0.7922 (4)	1.2346 (3)	0.3305 (2)	0.0418 (8)
H30	0.8014	1.3137	0.3513	0.05*
C28	0.8976 (3)	1.0525 (4)	0.2736 (2)	0.0434 (8)
H28	0.9785	1.0067	0.2556	0.052*
C26	0.6493 (3)	1.0705 (3)	0.29743 (17)	0.0228 (5)
C20	0.4372 (3)	1.0611 (2)	0.16505 (17)	0.0208 (5)
C14	0.3522 (3)	1.0734 (2)	0.34942 (17)	0.0204 (5)
C15	0.2866 (3)	0.9923 (3)	0.42239 (18)	0.0237 (5)
H15	0.3074	0.8989	0.4363	0.028*
C8	0.5052 (2)	0.8304 (2)	0.31772 (17)	0.0187 (5)
C9	0.4679 (3)	0.7474 (2)	0.26259 (18)	0.0218 (5)
H9	0.4248	0.7833	0.2059	0.026*
C19	0.3180 (3)	1.2109 (3)	0.3275 (2)	0.0274 (5)
H19	0.3591	1.2659	0.2758	0.033*
C31	0.6623 (3)	1.1861 (3)	0.3286 (2)	0.0321 (6)
H31	0.5823	1.2312	0.3483	0.038*
C23	0.3612 (3)	1.1437 (3)	−0.0145 (2)	0.0332 (6)
H23	0.3351	1.172	−0.0763	0.04*
Pt	0	0.5	0.5	0.01621 (5)
S2	0.17449 (6)	0.63059 (6)	0.42652 (4)	0.02153 (13)
S3	0.04993 (7)	0.73789 (6)	0.15524 (4)	0.02273 (13)
S1	−0.07133 (6)	0.57316 (7)	0.35140 (4)	0.02520 (13)
Cl1	−0.37103 (7)	0.44428 (8)	0.10640 (5)	0.03624 (16)
Cl2	0.26814 (7)	0.48922 (8)	0.12924 (5)	0.03452 (15)
C3	−0.1452 (3)	0.5687 (2)	0.13550 (17)	0.0218 (5)
H3	−0.2096	0.6357	0.1487	0.026*
C1	0.0838 (2)	0.6508 (2)	0.32596 (17)	0.0190 (5)
O2	0.1460 (2)	0.7855 (2)	0.08289 (14)	0.0344 (5)
C2	−0.0029 (3)	0.5823 (2)	0.13914 (16)	0.0200 (5)
N	0.1355 (2)	0.7139 (2)	0.24836 (15)	0.0231 (4)
O1	−0.0771 (2)	0.81846 (19)	0.15895 (14)	0.0320 (4)
C4	−0.1928 (3)	0.4572 (3)	0.11257 (17)	0.0242 (5)
C7	0.0896 (3)	0.4807 (2)	0.12334 (17)	0.0226 (5)
C6	0.0405 (3)	0.3690 (3)	0.10070 (18)	0.0281 (6)
H6	0.1045	0.3001	0.0899	0.034*
C5	−0.1009 (3)	0.3578 (3)	0.09378 (18)	0.0278 (5)
H5	−0.1345	0.283	0.0764	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P	0.0190 (3)	0.0156 (3)	0.0170 (3)	−0.0017 (2)	−0.0019 (2)	−0.0028 (2)
C13	0.0228 (12)	0.0221 (12)	0.0251 (13)	−0.0013 (9)	−0.0040 (10)	−0.0052 (10)
C12	0.0237 (13)	0.0235 (12)	0.0300 (14)	0.0033 (10)	−0.0042 (10)	0.0015 (10)
C11	0.0252 (13)	0.0167 (11)	0.0425 (17)	0.0001 (9)	0.0041 (11)	−0.0039 (11)
C21	0.0263 (13)	0.0263 (12)	0.0263 (14)	0.0009 (10)	−0.0058 (10)	−0.0037 (10)
C10	0.0301 (14)	0.0230 (12)	0.0350 (15)	−0.0046 (10)	0.0033 (11)	−0.0123 (11)
C16	0.0266 (14)	0.0403 (15)	0.0214 (13)	0.0049 (11)	−0.0013 (10)	−0.0059 (11)
C18	0.0323 (15)	0.0271 (13)	0.0409 (17)	0.0102 (11)	−0.0124 (13)	−0.0166 (12)
C22	0.0334 (15)	0.0290 (13)	0.0319 (15)	0.0064 (11)	−0.0140 (12)	−0.0074 (12)
C17	0.0296 (14)	0.0446 (16)	0.0313 (15)	0.0132 (12)	−0.0085 (12)	−0.0215 (13)
C25	0.0354 (14)	0.0208 (12)	0.0235 (13)	−0.0068 (10)	−0.0024 (11)	−0.0028 (10)
C27	0.0246 (14)	0.0462 (17)	0.0323 (15)	−0.0081 (12)	0.0029 (11)	−0.0149 (13)
C24	0.0511 (18)	0.0231 (13)	0.0221 (14)	−0.0038 (12)	−0.0017 (12)	0.0009 (10)
C29	0.0392 (17)	0.065 (2)	0.0252 (15)	−0.0321 (16)	−0.0076 (13)	0.0063 (14)
C30	0.057 (2)	0.0319 (15)	0.0364 (17)	−0.0223 (14)	−0.0183 (15)	0.0017 (13)
C28	0.0235 (14)	0.075 (2)	0.0337 (17)	−0.0164 (15)	0.0035 (12)	−0.0135 (16)
C26	0.0240 (12)	0.0259 (12)	0.0180 (12)	−0.0080 (9)	−0.0040 (9)	−0.0014 (9)
C20	0.0266 (12)	0.0166 (10)	0.0188 (12)	−0.0001 (9)	−0.0047 (9)	−0.0032 (9)
C14	0.0217 (12)	0.0182 (11)	0.0215 (12)	0.0018 (9)	−0.0032 (9)	−0.0055 (9)
C15	0.0241 (12)	0.0234 (12)	0.0228 (12)	0.0026 (9)	−0.0023 (10)	−0.0045 (10)
C8	0.0163 (11)	0.0169 (10)	0.0224 (12)	0.0000 (8)	0.0000 (9)	−0.0037 (9)
C9	0.0212 (12)	0.0234 (12)	0.0218 (12)	−0.0026 (9)	−0.0008 (9)	−0.0069 (10)
C19	0.0307 (14)	0.0204 (12)	0.0302 (14)	0.0016 (10)	−0.0061 (11)	−0.0045 (10)
C31	0.0390 (16)	0.0234 (13)	0.0336 (15)	−0.0049 (11)	−0.0122 (12)	−0.0037 (11)
C23	0.0527 (18)	0.0221 (12)	0.0226 (14)	0.0095 (12)	−0.0118 (13)	−0.0028 (10)
Pt	0.01621 (7)	0.01741 (7)	0.01562 (8)	−0.00152 (4)	0.00092 (5)	−0.00498 (5)
S2	0.0196 (3)	0.0272 (3)	0.0181 (3)	−0.0071 (2)	−0.0012 (2)	−0.0041 (2)
S3	0.0290 (3)	0.0199 (3)	0.0184 (3)	−0.0056 (2)	−0.0033 (2)	−0.0008 (2)
S1	0.0198 (3)	0.0374 (3)	0.0174 (3)	−0.0103 (2)	−0.0013 (2)	−0.0013 (3)
Cl1	0.0297 (3)	0.0462 (4)	0.0361 (4)	−0.0153 (3)	0.0007 (3)	−0.0126 (3)
Cl2	0.0233 (3)	0.0450 (4)	0.0312 (4)	0.0054 (3)	−0.0021 (3)	−0.0021 (3)
C3	0.0247 (12)	0.0227 (11)	0.0175 (12)	−0.0010 (9)	−0.0017 (9)	−0.0032 (9)
C1	0.0185 (11)	0.0182 (11)	0.0209 (12)	−0.0019 (8)	0.0003 (9)	−0.0056 (9)
O2	0.0483 (13)	0.0324 (10)	0.0213 (10)	−0.0184 (9)	0.0020 (9)	0.0011 (8)
C2	0.0257 (12)	0.0193 (11)	0.0134 (11)	−0.0018 (9)	−0.0022 (9)	−0.0001 (9)
N	0.0225 (11)	0.0266 (11)	0.0201 (11)	−0.0069 (8)	−0.0011 (8)	−0.0035 (8)
O1	0.0397 (11)	0.0213 (9)	0.0349 (11)	0.0044 (8)	−0.0116 (9)	−0.0063 (8)
C4	0.0267 (13)	0.0275 (12)	0.0176 (12)	−0.0074 (10)	0.0003 (10)	−0.0016 (10)
C7	0.0235 (12)	0.0250 (12)	0.0161 (11)	0.0012 (9)	−0.0009 (9)	0.0015 (9)
C6	0.0395 (15)	0.0215 (12)	0.0206 (13)	0.0047 (10)	0.0029 (11)	−0.0011 (10)
C5	0.0425 (16)	0.0204 (12)	0.0202 (13)	−0.0068 (10)	0.0014 (11)	−0.0030 (10)

Geometric parameters (Å, º) top

P—C8	1.792 (2)	C29—H29	0.95
P—C14	1.794 (3)	C30—C31	1.382 (4)
P—C26	1.795 (3)	C30—H30	0.95
P—C20	1.797 (3)	C28—H28	0.95
C13—C12	1.384 (4)	C26—C31	1.395 (4)
C13—C8	1.394 (4)	C14—C15	1.390 (4)
C13—H13	0.95	C14—C19	1.404 (3)
C12—C11	1.388 (4)	C15—H15	0.95
C12—H12	0.95	C8—C9	1.394 (3)
C11—C10	1.372 (4)	C9—H9	0.95
C11—H11	0.95	C19—H19	0.95
C21—C22	1.390 (4)	C31—H31	0.95
C21—C20	1.400 (4)	C23—H23	0.95
C21—H21	0.95	Pt—S1ⁱ	2.3128 (6)
C10—C9	1.396 (4)	Pt—S1	2.3128 (6)
C10—H10	0.95	Pt—S2ⁱ	2.3233 (6)
C16—C17	1.384 (4)	Pt—S2	2.3233 (6)
C16—C15	1.393 (4)	S2—C1	1.740 (3)
C16—H16	0.95	S3—O2	1.434 (2)
C18—C17	1.376 (5)	S3—O1	1.440 (2)
C18—C19	1.389 (4)	S3—N	1.614 (2)
C18—H18	0.95	S3—C2	1.788 (2)
C22—C23	1.385 (5)	S1—C1	1.735 (2)
C22—H22	0.95	Cl1—C4	1.737 (3)
C17—H17	0.95	Cl2—C7	1.733 (3)
C25—C24	1.386 (4)	C3—C4	1.385 (3)
C25—C20	1.389 (4)	C3—C2	1.391 (4)
C25—H25	0.95	C3—H3	0.95
C27—C28	1.391 (4)	C1—N	1.310 (3)
C27—C26	1.393 (4)	C2—C7	1.390 (3)
C27—H27	0.95	C4—C5	1.385 (4)
C24—C23	1.382 (5)	C7—C6	1.391 (4)
C24—H24	0.95	C6—C5	1.383 (4)
C29—C28	1.377 (5)	C6—H6	0.95
C29—C30	1.383 (6)	C5—H5	0.95

C8—P—C14	110.89 (12)	C15—C14—C19	120.1 (2)
C8—P—C26	106.58 (12)	C15—C14—P	121.79 (18)
C14—P—C26	110.24 (12)	C19—C14—P	118.1 (2)
C8—P—C20	111.91 (11)	C14—C15—C16	119.3 (2)
C14—P—C20	108.34 (12)	C14—C15—H15	120.3
C26—P—C20	108.85 (12)	C16—C15—H15	120.3
C12—C13—C8	120.1 (2)	C9—C8—C13	120.4 (2)
C12—C13—H13	120	C9—C8—P	121.96 (19)
C8—C13—H13	120	C13—C8—P	117.59 (18)
C13—C12—C11	119.5 (3)	C8—C9—C10	118.7 (2)
C13—C12—H12	120.3	C8—C9—H9	120.7
C11—C12—H12	120.3	C10—C9—H9	120.7
C10—C11—C12	120.7 (2)	C18—C19—C14	119.5 (3)
C10—C11—H11	119.7	C18—C19—H19	120.2
C12—C11—H11	119.7	C14—C19—H19	120.2
C22—C21—C20	119.1 (3)	C30—C31—C26	119.6 (3)
C22—C21—H21	120.4	C30—C31—H31	120.2
C20—C21—H21	120.4	C26—C31—H31	120.2
C11—C10—C9	120.7 (2)	C24—C23—C22	121.1 (3)
C11—C10—H10	119.6	C24—C23—H23	119.4
C9—C10—H10	119.6	C22—C23—H23	119.4
C17—C16—C15	120.3 (3)	S1ⁱ—Pt—S1	180
C17—C16—H16	119.8	S1ⁱ—Pt—S2ⁱ	74.59 (2)
C15—C16—H16	119.8	S1—Pt—S2ⁱ	105.41 (2)
C17—C18—C19	120.2 (3)	S1ⁱ—Pt—S2	105.41 (2)
C17—C18—H18	119.9	S1—Pt—S2	74.59 (2)
C19—C18—H18	119.9	S2ⁱ—Pt—S2	180.00 (3)
C23—C22—C21	119.9 (3)	C1—S2—Pt	88.44 (8)
C23—C22—H22	120.1	O2—S3—O1	116.81 (13)
C21—C22—H22	120.1	O2—S3—N	106.59 (12)
C18—C17—C16	120.5 (3)	O1—S3—N	111.58 (12)
C18—C17—H17	119.7	O2—S3—C2	106.56 (12)
C16—C17—H17	119.7	O1—S3—C2	105.50 (12)
C24—C25—C20	120.1 (3)	N—S3—C2	109.57 (11)
C24—C25—H25	119.9	C1—S1—Pt	88.90 (9)
C20—C25—H25	119.9	C4—C3—C2	119.8 (2)
C28—C27—C26	119.8 (3)	C4—C3—H3	120.1
C28—C27—H27	120.1	C2—C3—H3	120.1
C26—C27—H27	120.1	N—C1—S1	130.8 (2)
C23—C24—C25	119.4 (3)	N—C1—S2	121.34 (19)
C23—C24—H24	120.3	S1—C1—S2	107.86 (14)
C25—C24—H24	120.3	C7—C2—C3	119.2 (2)
C28—C29—C30	120.6 (3)	C7—C2—S3	123.7 (2)
C28—C29—H29	119.7	C3—C2—S3	116.91 (18)
C30—C29—H29	119.7	C1—N—S3	121.76 (18)
C31—C30—C29	120.3 (3)	C5—C4—C3	121.1 (2)
C31—C30—H30	119.9	C5—C4—Cl1	120.0 (2)
C29—C30—H30	119.9	C3—C4—Cl1	118.9 (2)
C29—C28—C27	119.8 (3)	C2—C7—C6	120.4 (2)
C29—C28—H28	120.1	C2—C7—Cl2	121.7 (2)
C27—C28—H28	120.1	C6—C7—Cl2	117.9 (2)
C27—C26—C31	119.9 (3)	C5—C6—C7	120.4 (2)
C27—C26—P	117.0 (2)	C5—C6—H6	119.8
C31—C26—P	123.0 (2)	C7—C6—H6	119.8
C25—C20—C21	120.4 (2)	C6—C5—C4	119.0 (2)
C25—C20—P	120.7 (2)	C6—C5—H5	120.5
C21—C20—P	118.9 (2)	C4—C5—H5	120.5

C8—C13—C12—C11	−0.1 (4)	C20—P—C8—C13	168.17 (19)
C13—C12—C11—C10	−0.6 (4)	C13—C8—C9—C10	−1.0 (4)
C12—C11—C10—C9	0.5 (4)	P—C8—C9—C10	176.1 (2)
C20—C21—C22—C23	−1.2 (4)	C11—C10—C9—C8	0.3 (4)
C19—C18—C17—C16	−0.5 (4)	C17—C18—C19—C14	−2.1 (4)
C15—C16—C17—C18	2.0 (4)	C15—C14—C19—C18	3.3 (4)
C20—C25—C24—C23	−1.2 (4)	P—C14—C19—C18	−175.4 (2)
C28—C29—C30—C31	−1.2 (5)	C29—C30—C31—C26	−0.4 (5)
C30—C29—C28—C27	1.3 (5)	C27—C26—C31—C30	1.8 (4)
C26—C27—C28—C29	0.1 (5)	P—C26—C31—C30	−174.1 (2)
C28—C27—C26—C31	−1.6 (5)	C25—C24—C23—C22	0.7 (4)
C28—C27—C26—P	174.5 (3)	C21—C22—C23—C24	0.5 (4)
C8—P—C26—C27	42.3 (2)	S1ⁱ—Pt—S2—C1	177.05 (8)
C14—P—C26—C27	162.7 (2)	S1—Pt—S2—C1	−2.95 (8)
C20—P—C26—C27	−78.6 (2)	S2ⁱ—Pt—S1—C1	−177.05 (8)
C8—P—C26—C31	−141.7 (2)	S2—Pt—S1—C1	2.95 (8)
C14—P—C26—C31	−21.2 (3)	Pt—S1—C1—N	174.9 (2)
C20—P—C26—C31	97.5 (2)	Pt—S1—C1—S2	−4.00 (11)
C24—C25—C20—C21	0.4 (4)	Pt—S2—C1—N	−175.0 (2)
C24—C25—C20—P	−178.8 (2)	Pt—S2—C1—S1	3.98 (11)
C22—C21—C20—C25	0.8 (4)	C4—C3—C2—C7	−2.7 (4)
C22—C21—C20—P	−180.0 (2)	C4—C3—C2—S3	172.41 (19)
C8—P—C20—C25	−112.6 (2)	O2—S3—C2—C7	48.8 (2)
C14—P—C20—C25	124.8 (2)	O1—S3—C2—C7	173.6 (2)
C26—P—C20—C25	4.9 (2)	N—S3—C2—C7	−66.2 (2)
C8—P—C20—C21	68.2 (2)	O2—S3—C2—C3	−126.1 (2)
C14—P—C20—C21	−54.4 (2)	O1—S3—C2—C3	−1.2 (2)
C26—P—C20—C21	−174.3 (2)	N—S3—C2—C3	119.0 (2)
C8—P—C14—C15	4.3 (2)	S1—C1—N—S3	3.5 (3)
C26—P—C14—C15	−113.5 (2)	S2—C1—N—S3	−177.77 (13)
C20—P—C14—C15	127.5 (2)	O2—S3—N—C1	−169.0 (2)
C8—P—C14—C19	−176.98 (19)	O1—S3—N—C1	62.4 (2)
C26—P—C14—C19	65.2 (2)	C2—S3—N—C1	−54.1 (2)
C20—P—C14—C19	−53.8 (2)	C2—C3—C4—C5	0.5 (4)
C19—C14—C15—C16	−1.9 (4)	C2—C3—C4—Cl1	−178.77 (19)
P—C14—C15—C16	176.7 (2)	C3—C2—C7—C6	2.5 (4)
C17—C16—C15—C14	−0.7 (4)	S3—C2—C7—C6	−172.3 (2)
C12—C13—C8—C9	0.9 (4)	C3—C2—C7—Cl2	−178.55 (19)
C12—C13—C8—P	−176.3 (2)	S3—C2—C7—Cl2	6.7 (3)
C14—P—C8—C9	112.1 (2)	C2—C7—C6—C5	−0.1 (4)
C26—P—C8—C9	−127.9 (2)	Cl2—C7—C6—C5	−179.1 (2)
C20—P—C8—C9	−9.0 (2)	C7—C6—C5—C4	−2.1 (4)
C14—P—C8—C13	−70.7 (2)	C3—C4—C5—C6	1.8 (4)
C26—P—C8—C13	49.3 (2)	Cl1—C4—C5—C6	−178.9 (2)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27···O1ⁱⁱ	0.95	2.43	3.111 (4)	128

Symmetry code: (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	(C₂₄H₂₀P)₂[Pt(C₇H₃Cl₂NO₂S₃)₂]
M_r	1474.3
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	9.6284 (1), 10.3409 (2), 15.1278 (2)
α, β, γ (°)	76.951 (1), 88.353 (1), 86.193 (1)
V (Å³)	1463.94 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.90
Crystal size (mm)	0.34 × 0.34 × 0.3

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Gaussian (Coppens et al., 1965)
T_min, T_max	0.439, 0.477
No. of measured, independent and observed [I > 2σ(I)] reflections	11423, 6536, 6483
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.644

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.068, 1.11
No. of reflections	6536
No. of parameters	367
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −2.58

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Pt—S1	2.3128 (6)	Pt—S2	2.3233 (6)

S1—Pt—S2	74.59 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27···O1ⁱ	0.95	2.43	3.111 (4)	128

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors thank Professor Dr Javier Ellena of the Instituto de Física de São Carlos, Universidade de São Paulo, Brazil, for the X-ray data collection. This work has been supported by FAPEMIG and CNPq.

References

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