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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): m971–m972.
Published online 2010 July 21. doi:  10.1107/S1600536810027364
PMCID: PMC3007205

Bis(tetra­phenyl­phospho­nium) bis­[N-(phenyl­sulfon­yl)dithio­carbimato-κ2 S,S′]platinate(II) monohydrate

Abstract

The asymmetric unit of the title compound, (C24H20P)2[Pt(C7H5NO2S3)2]·H2O, consists of two tetra­phenyl­phospho­nium cations, two half bis­[N-(phenyl­sulfon­yl)dithio­carbim­ato]platinate(II) dianions and one water mol­ecule. The anions are completed by crystallographic inversion symmetry associated with the central PtII ion. The PtII ion is doubly S,S′-chelated by two symmetry-related phenyl­sulfonyl­dithio­carbimate ligands, forming a slightly distorted square-planar configuration. Besides the electrostatic attraction between oppositely charged ions in the crystal packing, intra­molecular C—H(...)O and several inter­molecular C—H(...)O, C—H(...)N and O—H(...)O hydrogen-bonding inter­actions between the cations, anions and water mol­ecules are observed.

Related literature

For general background to Pt complexes, see: Faraglia et al. (2001 [triangle]). Dithio­carbimatoplatinate(II) complexes with tetra­butyl­ammonium counter cations were reported by Amim et al. (2008 [triangle]); Oliveira et al. (2004 [triangle]) and with tetra­phenyl­phospho­nium by Guilardi et al. (2010 [triangle]). For the structures of related dithio­carbimates, see: Oliveira et al. (2003 [triangle]); Franca et al. (2006 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m971-scheme1.jpg

Experimental

Crystal data

  • (C24H20P)2[Pt(C7H5NO2S3)2]·H2O
  • M r = 1354.45
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m971-efi1.jpg
  • a = 9.2972 (1) Å
  • b = 13.6482 (3) Å
  • c = 24.4279 (5) Å
  • α = 105.440 (1)°
  • β = 90.916 (1)°
  • γ = 107.777 (1)°
  • V = 2829.11 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 2.81 mm−1
  • T = 120 K
  • 0.62 × 0.23 × 0.16 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: Gaussian (Becker & Coppens, 1974 [triangle]) T min = 0.275, T max = 0.662
  • 20391 measured reflections
  • 10825 independent reflections
  • 9007 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.026
  • wR(F 2) = 0.063
  • S = 1.03
  • 10825 reflections
  • 706 parameters
  • H-atom parameters constrained
  • Δρmax = 0.53 e Å−3
  • Δρmin = −1.41 e Å−3

Data collection: COLLECT (Nonius, 2000 [triangle]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027364/wm2374sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027364/wm2374Isup2.hkl

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

Acknowledgments

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 was supported by FAPEMIG and CNPq.

supplementary crystallographic information

Comment

The interest in platinum(II) complexes containing S donors has increased in recent years, with the aim of synthesizing anti-tumor drugs having reduced toxicity with respect to cis-platin (Faraglia et al., 2001). The structures of anionic platinum-dithiocarbimato complexes with general formula [Pt(RSO2N═CS2)]2- (R = aryl groups) have been determined by X-ray diffraction techniques. Some of them have the tetrabutylammonium cation as counter ion (Amim et al., 2008; Oliveira et al., 2004), but only one has the tetraphenylphosphonium as counter ion (Guilardi et al., 2010). Variations in the counter ions and in the R groups may be important to modulate the activity of these compounds favoring the biological application.

The two Pt(II) atoms in the title compound are located at inversion centres. In the unit cell there are two anions, four cations and two water molecules (Figs. 1, 2). The Pt(II) atoms are coordinated by the four sulfur atoms of the two N-(phenylsulfonyldithiocarbimato) ligands within a distorted square-planar configuration (the bite angles S1—Pt—S2 are smaller than 90°). The four Pt—S bond lengths are almost equal (Table 1). In the fragment N═CS2, the C—S bond lengths are nearly equal and are shorter than typical C—S single bonds (ca 1.815 Å; Allen et al., 1987). The C1—N distances reveal a double bonding 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 (–C6H5)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 other dithiocarbimates (Amim et al., 2008; Oliveira et al., 2003, 2004; Franca et al., 2006; Guilardi et al., 2010).

The bond lengths and angles of the tetraphenylphosphonium cations are in agreement with the expected values (Allen et al., 1987).

The crystal packing is made up of discrete oppositely charged units which interact mainly by ionic forces. Moreover, there are two intramolecular (C—H···O) and several intermolecular hydrogen bonding interactions involving the cations, anions and water molecules (C—H···O and C—H···N) (Table 2). Classical hydrogen bonding of the form O—H···O take place between water molecules and anions (Table 2).

The values of bond lengths and angles of the compound under study and its correlative described in the literature with a counter-ion [Bu4N]+ (Bu is butyl) do not vary significantly (Oliveira et al., 2004). The observed differences are the result of interactions present in the crystal packing of both compounds mainly due to the presence of water molecule of crystallization in the title compound.

Experimental

The title compound was prepared in water (5 ml) from potassium tetrachloridoplatinate(II) (0.36 mmol), potassium phenylsulfonyldithiocarbimate dihydrate (0.72 mmol) and tetraphenylphosphonium bromide (0.72 mmol). The potassium phenylsulfonyldithiocarbimate dihydrate was prepared from the sulfonamide using procedures described in the literature (Franca et al., 2006). The reaction mixture was stirred for 1 h at room temperature. The yellow solid obtained was filtered, washed with distilled water and dried under reduced pressure. The title compound is soluble in dimethylsulfoxide, slightly soluble in chloroform and insoluble in water and in most organic solvents. Suitable crystals of the title compound were obtained after slow evaporation of a hot chloroform solution. IR spectrum: (most important bands, cm-1): 1394 ν(C═N); 1281 νass(SO2); 1142 νsym(SO2); 935 νass(CS2) and 308 ν(PtS).

Refinement

All H atoms were fixed geometrically and allowed to ride on their parent atoms, with C—H distances of 0.95Å and O—H distances of 0.85 Å, with Uiso(H) = 1.2 Ueq(C) and Uiso(H) = 1.5 Ueq(O).

Figures

Fig. 1.
ORTEP view of the asymmetric unit of (I), showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
Fig. 2.
Part of the crystal packing of the structure of (I).

Crystal data

(C24H20P)2[Pt(C7H5NO2S3)2]·H2OZ = 2
Mr = 1354.45F(000) = 1364
Triclinic, P1Dx = 1.59 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2972 (1) ÅCell parameters from 45459 reflections
b = 13.6482 (3) Åθ = 2.9–26.0°
c = 24.4279 (5) ŵ = 2.81 mm1
α = 105.440 (1)°T = 120 K
β = 90.916 (1)°Prism, yellow
γ = 107.777 (1)°0.62 × 0.23 × 0.16 mm
V = 2829.11 (9) Å3

Data collection

Nonius KappaCCD diffractometer9007 reflections with I > 2σ(I)
ω–scan CCD rotation images, thick slicesRint = 0.025
Absorption correction: gaussian (Becker & Coppens, 1974)θmax = 26.0°, θmin = 3.0°
Tmin = 0.275, Tmax = 0.662h = −11→11
20391 measured reflectionsk = −16→16
10825 independent reflectionsl = −29→29

Refinement

Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.026w = 1/[σ2(Fo2) + (0.0261P)2 + 1.8705P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.063(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.53 e Å3
10825 reflectionsΔρmin = −1.41 e Å3
706 parameters

Special details

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.

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

xyzUiso*/Ueq
S11−0.06940 (9)0.41599 (6)0.40357 (3)0.02706 (17)
S120.11144 (9)0.36578 (6)0.47859 (3)0.03094 (18)
C130.1860 (3)0.4189 (2)0.28919 (13)0.0287 (7)
H130.26870.40350.30420.034*
C110.0398 (3)0.3352 (2)0.40783 (12)0.0230 (6)
C140.2089 (4)0.5150 (3)0.27555 (14)0.0384 (8)
H140.30780.56590.28120.046*
C120.0412 (3)0.3465 (2)0.28049 (12)0.0235 (6)
C17−0.0809 (3)0.3676 (2)0.25841 (13)0.0300 (7)
H17−0.18020.31710.25280.036*
C150.0863 (4)0.5357 (3)0.25371 (14)0.0386 (8)
H150.10170.60170.24490.046*
S130.00917 (8)0.22849 (6)0.30179 (3)0.02565 (16)
O120.1052 (3)0.17106 (17)0.27112 (9)0.0366 (5)
O11−0.1508 (2)0.17218 (17)0.29224 (10)0.0385 (6)
N110.0747 (3)0.26262 (18)0.36796 (10)0.0247 (5)
C16−0.0564 (4)0.4629 (3)0.24468 (14)0.0362 (8)
H16−0.13880.47770.22890.043*
Pt100.50.50.02010 (5)
Pt20.50.500.02475 (5)
S230.81532 (9)0.71226 (6)0.20011 (3)0.03114 (18)
S220.74019 (9)0.62887 (6)0.02179 (3)0.03132 (18)
S210.55254 (9)0.54490 (6)0.09806 (3)0.03022 (18)
N210.8306 (3)0.70654 (19)0.13353 (11)0.0283 (6)
C240.6123 (3)0.9395 (2)0.24646 (13)0.0318 (7)
H240.63811.01430.25090.038*
O210.7619 (3)0.60907 (18)0.21057 (10)0.0414 (6)
O220.9592 (2)0.78453 (19)0.23015 (10)0.0439 (6)
C230.7164 (3)0.8871 (2)0.22877 (13)0.0295 (7)
H230.81440.9260.22150.035*
C210.7242 (3)0.6380 (2)0.09349 (13)0.0261 (7)
C270.5358 (4)0.7204 (2)0.23234 (13)0.0318 (7)
H270.50960.64540.22730.038*
C250.4697 (4)0.8828 (3)0.25768 (14)0.0349 (8)
H250.39820.91870.27020.042*
C220.6780 (3)0.7776 (2)0.22156 (13)0.0272 (7)
C260.4324 (4)0.7733 (3)0.25046 (14)0.0349 (8)
H260.33490.73430.2580.042*
C210−0.2462 (4)0.1953 (3)−0.09500 (15)0.0411 (8)
H210−0.17790.1939−0.12350.049*
C226−0.0696 (3)0.3418 (2)0.09037 (12)0.0242 (6)
C223−0.5993 (4)0.2340 (3)0.19218 (17)0.0524 (10)
H223−0.67690.23610.21690.063*
C212−0.4956 (4)0.1878 (3)−0.06802 (16)0.0481 (10)
H212−0.5970.1835−0.0780.058*
C224−0.5065 (4)0.3283 (3)0.18381 (15)0.0429 (9)
H224−0.52040.39470.20270.051*
C214−0.1701 (3)0.1090 (2)0.07698 (13)0.0263 (7)
C218−0.1441 (4)−0.0645 (3)0.03479 (15)0.0364 (8)
H218−0.1581−0.1250.00260.044*
C215−0.1079 (4)0.1098 (3)0.12944 (14)0.0319 (7)
H215−0.09870.16840.16220.038*
C2300.1913 (3)0.4415 (3)0.12371 (14)0.0343 (8)
H2300.28760.44560.13960.041*
C2290.1726 (4)0.5298 (3)0.11077 (14)0.0348 (8)
H2290.25580.59430.11790.042*
C221−0.4678 (4)0.1330 (3)0.12952 (17)0.0474 (10)
H221−0.45450.06610.11120.057*
C213−0.4499 (3)0.1948 (3)−0.01252 (15)0.0355 (8)
H213−0.51970.19410.01550.043*
C222−0.5809 (4)0.1374 (3)0.16531 (19)0.0579 (11)
H222−0.64610.07330.17130.069*
C216−0.0595 (4)0.0258 (3)0.13409 (15)0.0380 (8)
H216−0.01240.02840.16950.046*
C219−0.1879 (3)0.0214 (2)0.02941 (14)0.0300 (7)
H219−0.22990.0203−0.00650.036*
C211−0.3956 (4)0.1871 (3)−0.10865 (16)0.0448 (9)
H211−0.42910.1809−0.14670.054*
C2280.0331 (4)0.5243 (3)0.08742 (15)0.0352 (8)
H2280.02050.58480.07830.042*
C225−0.3934 (3)0.3257 (3)0.14790 (14)0.0335 (7)
H225−0.32960.39030.14190.04*
C227−0.0881 (3)0.4307 (2)0.07732 (14)0.0307 (7)
H227−0.18420.4270.06140.037*
C217−0.0801 (4)−0.0623 (3)0.08676 (16)0.0390 (8)
H217−0.0502−0.12130.09010.047*
C29−0.1983 (4)0.2055 (3)−0.03956 (14)0.0353 (8)
H29−0.09520.2143−0.02930.042*
C28−0.3011 (3)0.2029 (2)0.00162 (13)0.0268 (7)
C2310.0711 (3)0.3476 (2)0.11373 (13)0.0274 (7)
H2310.08440.28720.12280.033*
P2−0.22894 (8)0.22070 (6)0.07315 (3)0.02458 (17)
C220−0.3733 (3)0.2275 (2)0.12047 (13)0.0282 (7)
P10.52139 (8)0.78466 (6)0.44818 (3)0.01989 (16)
C190.6271 (3)0.7986 (2)0.55702 (13)0.0248 (6)
H190.71030.78130.53970.03*
C1230.9266 (3)1.0561 (2)0.42403 (14)0.0288 (7)
H1231.01221.11160.41930.035*
C1130.3828 (3)0.8245 (2)0.54829 (13)0.0247 (6)
H1130.30050.82650.52550.03*
C180.5073 (3)0.8035 (2)0.52317 (12)0.0209 (6)
C1140.3486 (3)0.7857 (2)0.41446 (12)0.0208 (6)
C1210.7655 (3)0.9723 (2)0.48515 (12)0.0226 (6)
H1210.74010.97070.52250.027*
C1180.2102 (3)0.8672 (3)0.36694 (13)0.0292 (7)
H1180.20810.92410.35170.035*
C1250.7165 (3)0.8958 (2)0.38297 (13)0.0262 (7)
H1250.65640.8430.35030.031*
C1270.4674 (3)0.5708 (2)0.43920 (13)0.0287 (7)
H1270.40430.58210.46890.034*
C1160.0808 (3)0.7009 (3)0.38610 (14)0.0334 (7)
H116−0.01030.6440.38450.04*
C1100.6239 (3)0.8188 (2)0.61522 (13)0.0283 (7)
H1100.70610.81760.63830.034*
C1190.3457 (3)0.8693 (2)0.39263 (12)0.0248 (6)
H1190.43590.92750.39530.03*
C1220.8882 (3)1.0545 (2)0.47799 (13)0.0269 (7)
H1220.94571.10970.51040.032*
C1290.5729 (4)0.4536 (3)0.37321 (16)0.0389 (8)
H1290.5820.38440.35780.047*
C1200.6793 (3)0.8918 (2)0.43786 (12)0.0212 (6)
C1240.8414 (3)0.9773 (2)0.37678 (14)0.0302 (7)
H1240.86870.97910.33970.036*
C1110.4991 (4)0.8411 (2)0.63990 (13)0.0308 (7)
H1110.49660.85540.68010.037*
C1120.3796 (3)0.8426 (2)0.60664 (13)0.0290 (7)
H1120.29410.85610.62390.035*
C1300.6522 (4)0.5373 (3)0.35300 (16)0.0418 (9)
H1300.71540.52550.32340.05*
C1150.2154 (3)0.7011 (2)0.41123 (13)0.0288 (7)
H1150.21720.6440.42620.035*
C1170.0783 (3)0.7833 (3)0.36323 (13)0.0322 (7)
H117−0.01380.78190.34510.039*
C1310.6405 (3)0.6386 (2)0.37554 (15)0.0348 (8)
H1310.69550.69620.36140.042*
C1260.5483 (3)0.6559 (2)0.41880 (12)0.0234 (6)
C1280.4798 (4)0.4700 (2)0.41595 (15)0.0353 (8)
H1280.4240.41180.42940.042*
OW0.1927 (3)0.9828 (2)0.24598 (14)0.0654 (8)
H1W0.16161.03620.25870.098*
H2W0.11660.92620.24030.098*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S110.0321 (4)0.0306 (4)0.0206 (4)0.0183 (3)−0.0002 (3)0.0015 (3)
S120.0449 (5)0.0327 (4)0.0234 (4)0.0256 (4)0.0034 (3)0.0062 (3)
C130.0295 (17)0.0304 (17)0.0269 (17)0.0086 (13)0.0040 (13)0.0103 (14)
C110.0257 (15)0.0201 (15)0.0240 (16)0.0067 (12)0.0061 (12)0.0083 (12)
C140.043 (2)0.0314 (18)0.035 (2)0.0007 (15)0.0058 (16)0.0134 (15)
C120.0289 (16)0.0242 (16)0.0186 (16)0.0107 (13)0.0060 (12)0.0053 (12)
C170.0314 (17)0.0303 (17)0.0265 (17)0.0121 (14)0.0044 (13)0.0024 (14)
C150.060 (2)0.0267 (18)0.0317 (19)0.0149 (16)0.0049 (16)0.0115 (15)
S130.0331 (4)0.0189 (4)0.0239 (4)0.0072 (3)0.0073 (3)0.0055 (3)
O120.0575 (15)0.0304 (12)0.0294 (13)0.0245 (11)0.0175 (11)0.0081 (10)
O110.0365 (13)0.0307 (12)0.0357 (14)−0.0053 (10)0.0027 (10)0.0076 (10)
N110.0356 (14)0.0202 (13)0.0230 (14)0.0133 (11)0.0086 (11)0.0083 (11)
C160.047 (2)0.0385 (19)0.0269 (18)0.0214 (16)0.0003 (15)0.0074 (15)
Pt10.02270 (9)0.01875 (8)0.02005 (9)0.00908 (6)0.00353 (6)0.00460 (6)
Pt20.02283 (9)0.02280 (9)0.02672 (10)0.00679 (7)0.00329 (7)0.00452 (7)
S230.0321 (4)0.0295 (4)0.0315 (5)0.0098 (3)−0.0047 (3)0.0087 (3)
S220.0271 (4)0.0309 (4)0.0303 (4)0.0032 (3)0.0060 (3)0.0065 (3)
S210.0274 (4)0.0310 (4)0.0282 (4)0.0040 (3)0.0033 (3)0.0080 (3)
N210.0243 (13)0.0267 (14)0.0327 (15)0.0083 (11)0.0017 (11)0.0065 (12)
C240.0392 (19)0.0214 (16)0.0281 (18)0.0044 (14)−0.0017 (14)0.0025 (13)
O210.0512 (14)0.0353 (13)0.0449 (15)0.0173 (11)0.0005 (11)0.0196 (11)
O220.0341 (13)0.0461 (15)0.0435 (15)0.0053 (11)−0.0129 (11)0.0093 (12)
C230.0308 (17)0.0260 (16)0.0259 (17)0.0008 (13)−0.0005 (13)0.0075 (13)
C210.0276 (16)0.0253 (16)0.0305 (18)0.0160 (13)0.0046 (13)0.0074 (13)
C270.0406 (19)0.0233 (16)0.0256 (18)0.0028 (14)0.0020 (14)0.0059 (14)
C250.042 (2)0.0318 (18)0.0280 (18)0.0122 (15)0.0036 (14)0.0032 (14)
C220.0346 (17)0.0225 (16)0.0220 (16)0.0061 (13)−0.0022 (13)0.0060 (13)
C260.0354 (19)0.0322 (18)0.0323 (19)0.0028 (14)0.0102 (14)0.0099 (15)
C2100.054 (2)0.043 (2)0.031 (2)0.0189 (17)0.0100 (16)0.0155 (16)
C2260.0238 (16)0.0275 (16)0.0226 (16)0.0099 (12)0.0068 (12)0.0072 (13)
C2230.045 (2)0.063 (3)0.057 (3)0.023 (2)0.0304 (19)0.023 (2)
C2120.037 (2)0.054 (2)0.053 (3)0.0080 (17)−0.0110 (18)0.023 (2)
C2240.042 (2)0.050 (2)0.046 (2)0.0256 (18)0.0173 (17)0.0158 (18)
C2140.0250 (16)0.0267 (16)0.0297 (18)0.0079 (12)0.0066 (13)0.0123 (14)
C2180.0398 (19)0.0285 (17)0.041 (2)0.0125 (15)0.0131 (15)0.0078 (15)
C2150.0382 (18)0.0301 (17)0.0277 (18)0.0098 (14)0.0037 (14)0.0100 (14)
C2300.0252 (17)0.043 (2)0.037 (2)0.0088 (14)0.0053 (14)0.0162 (16)
C2290.0288 (18)0.0300 (18)0.041 (2)0.0052 (14)0.0094 (14)0.0073 (15)
C2210.049 (2)0.033 (2)0.059 (3)0.0096 (16)0.0254 (19)0.0147 (18)
C2130.0267 (17)0.0395 (19)0.040 (2)0.0072 (14)0.0009 (14)0.0151 (16)
C2220.052 (2)0.045 (2)0.077 (3)0.0085 (19)0.038 (2)0.023 (2)
C2160.0354 (19)0.042 (2)0.044 (2)0.0117 (15)0.0034 (15)0.0259 (18)
C2190.0304 (17)0.0313 (17)0.0295 (18)0.0100 (14)0.0058 (13)0.0101 (14)
C2110.052 (2)0.044 (2)0.034 (2)0.0053 (17)−0.0069 (17)0.0168 (17)
C2280.0340 (19)0.0284 (17)0.048 (2)0.0139 (14)0.0114 (15)0.0140 (16)
C2250.0315 (18)0.0385 (19)0.037 (2)0.0165 (15)0.0076 (14)0.0149 (16)
C2270.0243 (16)0.0318 (18)0.040 (2)0.0117 (13)0.0083 (14)0.0139 (15)
C2170.0386 (19)0.037 (2)0.055 (2)0.0194 (15)0.0149 (17)0.0261 (18)
C290.0371 (19)0.041 (2)0.0307 (19)0.0160 (15)0.0038 (14)0.0112 (15)
C280.0278 (16)0.0237 (16)0.0294 (17)0.0072 (12)0.0016 (13)0.0096 (13)
C2310.0282 (17)0.0321 (17)0.0260 (17)0.0122 (13)0.0059 (13)0.0120 (14)
P20.0243 (4)0.0257 (4)0.0249 (4)0.0090 (3)0.0046 (3)0.0078 (3)
C2200.0257 (16)0.0327 (17)0.0282 (17)0.0105 (13)0.0063 (13)0.0104 (14)
P10.0186 (4)0.0179 (4)0.0238 (4)0.0060 (3)0.0019 (3)0.0070 (3)
C190.0228 (15)0.0202 (15)0.0320 (18)0.0076 (12)0.0023 (12)0.0078 (13)
C1230.0225 (16)0.0243 (16)0.041 (2)0.0058 (12)0.0000 (13)0.0145 (14)
C1130.0229 (15)0.0261 (16)0.0297 (17)0.0095 (12)0.0043 (12)0.0135 (13)
C180.0219 (15)0.0165 (14)0.0244 (16)0.0068 (11)0.0026 (11)0.0052 (12)
C1140.0199 (14)0.0224 (15)0.0202 (15)0.0092 (11)0.0012 (11)0.0037 (12)
C1210.0243 (15)0.0213 (15)0.0234 (16)0.0084 (12)0.0010 (12)0.0072 (12)
C1180.0330 (18)0.0355 (18)0.0281 (18)0.0173 (14)0.0050 (13)0.0165 (14)
C1250.0258 (16)0.0272 (16)0.0249 (17)0.0074 (13)0.0001 (12)0.0078 (13)
C1270.0330 (17)0.0258 (16)0.0282 (18)0.0105 (13)0.0017 (13)0.0082 (14)
C1160.0220 (16)0.0328 (18)0.040 (2)0.0036 (13)−0.0026 (13)0.0074 (15)
C1100.0341 (17)0.0229 (16)0.0284 (18)0.0102 (13)−0.0051 (13)0.0072 (13)
C1190.0258 (16)0.0246 (15)0.0254 (17)0.0094 (12)0.0053 (12)0.0079 (13)
C1220.0254 (16)0.0199 (15)0.0351 (19)0.0068 (12)−0.0036 (13)0.0087 (13)
C1290.0340 (19)0.0239 (17)0.055 (2)0.0138 (14)−0.0060 (16)0.0003 (16)
C1200.0186 (14)0.0203 (15)0.0272 (17)0.0081 (11)0.0031 (12)0.0086 (12)
C1240.0273 (16)0.0344 (18)0.0334 (19)0.0097 (14)0.0059 (13)0.0174 (15)
C1110.047 (2)0.0239 (16)0.0237 (17)0.0139 (14)0.0058 (14)0.0074 (13)
C1120.0341 (17)0.0274 (17)0.0313 (18)0.0146 (13)0.0104 (14)0.0122 (14)
C1300.0305 (18)0.0304 (19)0.059 (2)0.0108 (15)0.0156 (16)0.0020 (17)
C1150.0248 (16)0.0244 (16)0.0355 (19)0.0040 (12)−0.0011 (13)0.0106 (14)
C1170.0277 (17)0.044 (2)0.0272 (18)0.0173 (15)−0.0040 (13)0.0076 (15)
C1310.0270 (17)0.0262 (17)0.048 (2)0.0075 (13)0.0122 (15)0.0062 (15)
C1260.0203 (15)0.0207 (15)0.0271 (17)0.0067 (12)−0.0022 (12)0.0033 (12)
C1280.043 (2)0.0222 (17)0.040 (2)0.0086 (14)−0.0025 (15)0.0102 (15)
OW0.0456 (15)0.0403 (15)0.120 (3)0.0208 (12)0.0086 (15)0.0302 (16)

Geometric parameters (Å, °)

S11—C111.732 (3)C221—C2221.383 (5)
S11—Pt12.3111 (7)C221—C2201.397 (4)
S12—C111.736 (3)C221—H2210.95
S12—Pt12.3171 (7)C213—C281.385 (4)
C13—C121.378 (4)C213—H2130.95
C13—C141.394 (4)C222—H2220.95
C13—H130.95C216—C2171.390 (5)
C11—N111.314 (4)C216—H2160.95
C14—C151.386 (5)C219—H2190.95
C14—H140.95C211—H2110.95
C12—C171.387 (4)C228—C2271.380 (4)
C12—S131.764 (3)C228—H2280.95
C17—C161.382 (4)C225—C2201.399 (4)
C17—H170.95C225—H2250.95
C15—C161.365 (5)C227—H2270.95
C15—H150.95C217—H2170.95
S13—O111.433 (2)C29—C281.399 (4)
S13—O121.452 (2)C29—H290.95
S13—N111.611 (3)C28—P21.789 (3)
C16—H160.95C231—H2310.95
Pt1—S11i2.3111 (7)P2—C2201.793 (3)
Pt1—S12i2.3171 (7)P1—C181.793 (3)
Pt2—S21ii2.3130 (8)P1—C1141.800 (3)
Pt2—S212.3130 (8)P1—C1201.804 (3)
Pt2—S22ii2.3299 (7)P1—C1261.808 (3)
Pt2—S222.3299 (7)C19—C1101.377 (4)
S23—O211.437 (2)C19—C181.404 (4)
S23—O221.442 (2)C19—H190.95
S23—N211.618 (3)C123—C1221.375 (4)
S23—C221.780 (3)C123—C1241.381 (4)
S22—C211.735 (3)C123—H1230.95
S21—C211.737 (3)C113—C1121.383 (4)
N21—C211.314 (4)C113—C181.390 (4)
C24—C231.382 (4)C113—H1130.95
C24—C251.389 (4)C114—C1191.388 (4)
C24—H240.95C114—C1151.396 (4)
C23—C221.387 (4)C121—C1221.385 (4)
C23—H230.95C121—C1201.393 (4)
C27—C261.382 (4)C121—H1210.95
C27—C221.384 (4)C118—C1171.382 (4)
C27—H270.95C118—C1191.387 (4)
C25—C261.388 (4)C118—H1180.95
C25—H250.95C125—C1241.384 (4)
C26—H260.95C125—C1201.401 (4)
C210—C291.376 (5)C125—H1250.95
C210—C2111.387 (5)C127—C1281.382 (4)
C210—H2100.95C127—C1261.396 (4)
C226—C2311.390 (4)C127—H1270.95
C226—C2271.391 (4)C116—C1151.384 (4)
C226—P21.794 (3)C116—C1171.388 (4)
C223—C2221.370 (5)C116—H1160.95
C223—C2241.382 (5)C110—C1111.394 (4)
C223—H2230.95C110—H1100.95
C212—C2111.371 (5)C119—H1190.95
C212—C2131.384 (5)C122—H1220.95
C212—H2120.95C129—C1301.375 (5)
C224—C2251.383 (4)C129—C1281.383 (5)
C224—H2240.95C129—H1290.95
C214—C2191.393 (4)C124—H1240.95
C214—C2151.394 (4)C111—C1121.374 (4)
C214—P21.793 (3)C111—H1110.95
C218—C2171.383 (5)C112—H1120.95
C218—C2191.388 (4)C130—C1311.384 (4)
C218—H2180.95C130—H1300.95
C215—C2161.382 (4)C115—H1150.95
C215—H2150.95C117—H1170.95
C230—C2311.378 (4)C131—C1261.388 (4)
C230—C2291.382 (4)C131—H1310.95
C230—H2300.95C128—H1280.95
C229—C2281.381 (4)OW—H1W0.85
C229—H2290.95OW—H2W0.85
C11—S11—Pt188.30 (10)C218—C219—H219120.1
C11—S12—Pt188.00 (10)C214—C219—H219120.1
C12—C13—C14118.9 (3)C212—C211—C210121.0 (3)
C12—C13—H13120.6C212—C211—H211119.5
C14—C13—H13120.6C210—C211—H211119.5
N11—C11—S11131.0 (2)C227—C228—C229120.0 (3)
N11—C11—S12120.4 (2)C227—C228—H228120
S11—C11—S12108.57 (16)C229—C228—H228120
C15—C14—C13119.5 (3)C224—C225—C220119.6 (3)
C15—C14—H14120.2C224—C225—H225120.2
C13—C14—H14120.2C220—C225—H225120.2
C13—C12—C17121.3 (3)C228—C227—C226120.1 (3)
C13—C12—S13119.1 (2)C228—C227—H227120
C17—C12—S13119.4 (2)C226—C227—H227120
C16—C17—C12119.2 (3)C218—C217—C216120.2 (3)
C16—C17—H17120.4C218—C217—H217119.9
C12—C17—H17120.4C216—C217—H217119.9
C16—C15—C14121.1 (3)C210—C29—C28120.1 (3)
C16—C15—H15119.5C210—C29—H29119.9
C14—C15—H15119.5C28—C29—H29119.9
O11—S13—O12116.04 (14)C213—C28—C29120.2 (3)
O11—S13—N11112.57 (13)C213—C28—P2122.1 (2)
O12—S13—N11104.85 (13)C29—C28—P2117.4 (2)
O11—S13—C12107.86 (14)C230—C231—C226119.7 (3)
O12—S13—C12107.06 (13)C230—C231—H231120.2
N11—S13—C12108.09 (13)C226—C231—H231120.2
C11—N11—S13123.0 (2)C28—P2—C214110.42 (14)
C15—C16—C17120.1 (3)C28—P2—C220110.60 (14)
C15—C16—H16120C214—P2—C220107.18 (14)
C17—C16—H16120C28—P2—C226105.17 (14)
S11i—Pt1—S11180C214—P2—C226110.64 (14)
S11i—Pt1—S12i74.95 (3)C220—P2—C226112.87 (14)
S11—Pt1—S12i105.05 (3)C221—C220—C225119.8 (3)
S11i—Pt1—S12105.05 (3)C221—C220—P2119.2 (2)
S11—Pt1—S1274.95 (3)C225—C220—P2121.0 (2)
S12i—Pt1—S12180C18—P1—C114109.44 (13)
S21ii—Pt2—S21180.00 (4)C18—P1—C120109.39 (13)
S21ii—Pt2—S22ii74.22 (3)C114—P1—C120109.50 (13)
S21—Pt2—S22ii105.78 (3)C18—P1—C126107.80 (13)
S21ii—Pt2—S22105.78 (3)C114—P1—C126109.72 (13)
S21—Pt2—S2274.22 (3)C120—P1—C126110.96 (13)
S22ii—Pt2—S22180.00 (4)C110—C19—C18120.1 (3)
O21—S23—O22116.76 (14)C110—C19—H19119.9
O21—S23—N21113.99 (14)C18—C19—H19119.9
O22—S23—N21105.31 (14)C122—C123—C124120.2 (3)
O21—S23—C22107.20 (14)C122—C123—H123119.9
O22—S23—C22106.57 (14)C124—C123—H123119.9
N21—S23—C22106.34 (13)C112—C113—C18119.5 (3)
C21—S22—Pt288.79 (10)C112—C113—H113120.2
C21—S21—Pt289.30 (11)C18—C113—H113120.2
C21—N21—S23120.9 (2)C113—C18—C19119.8 (3)
C23—C24—C25120.0 (3)C113—C18—P1121.6 (2)
C23—C24—H24120C19—C18—P1118.6 (2)
C25—C24—H24120C119—C114—C115120.1 (3)
C24—C23—C22120.0 (3)C119—C114—P1121.3 (2)
C24—C23—H23120C115—C114—P1118.7 (2)
C22—C23—H23120C122—C121—C120120.3 (3)
N21—C21—S22121.6 (2)C122—C121—H121119.8
N21—C21—S21130.8 (2)C120—C121—H121119.8
S22—C21—S21107.60 (17)C117—C118—C119120.6 (3)
C26—C27—C22119.5 (3)C117—C118—H118119.7
C26—C27—H27120.3C119—C118—H118119.7
C22—C27—H27120.3C124—C125—C120119.4 (3)
C26—C25—C24119.6 (3)C124—C125—H125120.3
C26—C25—H25120.2C120—C125—H125120.3
C24—C25—H25120.2C128—C127—C126119.5 (3)
C27—C22—C23120.4 (3)C128—C127—H127120.2
C27—C22—S23120.4 (2)C126—C127—H127120.2
C23—C22—S23119.2 (2)C115—C116—C117120.3 (3)
C27—C26—C25120.6 (3)C115—C116—H116119.8
C27—C26—H26119.7C117—C116—H116119.8
C25—C26—H26119.7C19—C110—C111119.4 (3)
C29—C210—C211119.0 (3)C19—C110—H110120.3
C29—C210—H210120.5C111—C110—H110120.3
C211—C210—H210120.5C118—C119—C114119.6 (3)
C231—C226—C227119.8 (3)C118—C119—H119120.2
C231—C226—P2122.2 (2)C114—C119—H119120.2
C227—C226—P2117.9 (2)C123—C122—C121120.0 (3)
C222—C223—C224120.8 (3)C123—C122—H122120
C222—C223—H223119.6C121—C122—H122120
C224—C223—H223119.6C130—C129—C128120.1 (3)
C211—C212—C213120.5 (3)C130—C129—H129120
C211—C212—H212119.8C128—C129—H129120
C213—C212—H212119.8C121—C120—C125119.3 (3)
C223—C224—C225119.9 (3)C121—C120—P1119.6 (2)
C223—C224—H224120C125—C120—P1121.1 (2)
C225—C224—H224120C123—C124—C125120.6 (3)
C219—C214—C215119.6 (3)C123—C124—H124119.7
C219—C214—P2121.8 (2)C125—C124—H124119.7
C215—C214—P2118.6 (2)C112—C111—C110120.6 (3)
C217—C218—C219120.3 (3)C112—C111—H111119.7
C217—C218—H218119.8C110—C111—H111119.7
C219—C218—H218119.8C111—C112—C113120.6 (3)
C216—C215—C214120.4 (3)C111—C112—H112119.7
C216—C215—H215119.8C113—C112—H112119.7
C214—C215—H215119.8C129—C130—C131120.3 (3)
C231—C230—C229120.5 (3)C129—C130—H130119.8
C231—C230—H230119.8C131—C130—H130119.8
C229—C230—H230119.8C116—C115—C114119.7 (3)
C228—C229—C230120.1 (3)C116—C115—H115120.2
C228—C229—H229120C114—C115—H115120.2
C230—C229—H229120C118—C117—C116119.7 (3)
C222—C221—C220119.6 (3)C118—C117—H117120.1
C222—C221—H221120.2C116—C117—H117120.1
C220—C221—H221120.2C130—C131—C126119.8 (3)
C212—C213—C28119.1 (3)C130—C131—H131120.1
C212—C213—H213120.5C126—C131—H131120.1
C28—C213—H213120.5C131—C126—C127119.8 (3)
C223—C222—C221120.3 (3)C131—C126—P1122.3 (2)
C223—C222—H222119.8C127—C126—P1117.9 (2)
C221—C222—H222119.8C127—C128—C129120.4 (3)
C215—C216—C217119.7 (3)C127—C128—H128119.8
C215—C216—H216120.1C129—C128—H128119.8
C217—C216—H216120.1H1W—OW—H2W107.7
C218—C219—C214119.7 (3)
Pt1—S11—C11—N11−174.7 (3)C29—C28—P2—C214−67.0 (3)
Pt1—S11—C11—S123.68 (13)C213—C28—P2—C220−0.7 (3)
Pt1—S12—C11—N11174.9 (2)C29—C28—P2—C220174.5 (2)
Pt1—S12—C11—S11−3.67 (13)C213—C28—P2—C226−122.9 (3)
C12—C13—C14—C150.1 (5)C29—C28—P2—C22652.4 (3)
C14—C13—C12—C170.2 (4)C219—C214—P2—C28−2.5 (3)
C14—C13—C12—S13−176.1 (2)C215—C214—P2—C28178.8 (2)
C13—C12—C17—C160.3 (4)C219—C214—P2—C220118.1 (3)
S13—C12—C17—C16176.5 (2)C215—C214—P2—C220−60.6 (3)
C13—C14—C15—C16−0.8 (5)C219—C214—P2—C226−118.5 (2)
C13—C12—S13—O11175.5 (2)C215—C214—P2—C22662.8 (3)
C17—C12—S13—O11−0.8 (3)C231—C226—P2—C28−130.5 (2)
C13—C12—S13—O12−58.9 (3)C227—C226—P2—C2846.7 (3)
C17—C12—S13—O12124.7 (2)C231—C226—P2—C214−11.2 (3)
C13—C12—S13—N1153.5 (3)C227—C226—P2—C214166.0 (2)
C17—C12—S13—N11−122.8 (2)C231—C226—P2—C220108.9 (3)
S11—C11—N11—S13−3.3 (4)C227—C226—P2—C220−73.9 (3)
S12—C11—N11—S13178.56 (15)C222—C221—C220—C2250.4 (6)
O11—S13—N11—C11−68.1 (3)C222—C221—C220—P2−179.1 (3)
O12—S13—N11—C11164.8 (2)C224—C225—C220—C2210.1 (5)
C12—S13—N11—C1150.9 (3)C224—C225—C220—P2179.5 (3)
C14—C15—C16—C171.3 (5)C28—P2—C220—C22189.8 (3)
C12—C17—C16—C15−1.0 (5)C214—P2—C220—C221−30.6 (3)
C11—S11—Pt1—S12i177.30 (9)C226—P2—C220—C221−152.7 (3)
C11—S11—Pt1—S12−2.70 (9)C28—P2—C220—C225−89.6 (3)
C11—S12—Pt1—S11i−177.30 (9)C214—P2—C220—C225149.9 (3)
C11—S12—Pt1—S112.70 (9)C226—P2—C220—C22527.9 (3)
S21ii—Pt2—S22—C21178.15 (10)C112—C113—C18—C191.3 (4)
S21—Pt2—S22—C21−1.85 (10)C112—C113—C18—P1−177.5 (2)
S22ii—Pt2—S21—C21−178.15 (9)C110—C19—C18—C113−2.6 (4)
S22—Pt2—S21—C211.85 (9)C110—C19—C18—P1176.3 (2)
O21—S23—N21—C2143.2 (3)C114—P1—C18—C113−5.1 (3)
O22—S23—N21—C21172.5 (2)C120—P1—C18—C113114.9 (2)
C22—S23—N21—C21−74.7 (3)C126—P1—C18—C113−124.3 (2)
C25—C24—C23—C220.8 (5)C114—P1—C18—C19176.1 (2)
S23—N21—C21—S22−178.76 (15)C120—P1—C18—C19−63.9 (2)
S23—N21—C21—S211.4 (4)C126—P1—C18—C1956.9 (2)
Pt2—S22—C21—N21−177.4 (2)C18—P1—C114—C119111.1 (2)
Pt2—S22—C21—S212.49 (13)C120—P1—C114—C119−8.8 (3)
Pt2—S21—C21—N21177.4 (3)C126—P1—C114—C119−130.8 (2)
Pt2—S21—C21—S22−2.51 (13)C18—P1—C114—C115−68.0 (3)
C23—C24—C25—C26−0.7 (5)C120—P1—C114—C115172.1 (2)
C26—C27—C22—C23−0.1 (5)C126—P1—C114—C11550.1 (3)
C26—C27—C22—S23178.2 (2)C18—C19—C110—C1111.8 (4)
C24—C23—C22—C27−0.4 (5)C117—C118—C119—C1140.4 (5)
C24—C23—C22—S23−178.8 (2)C115—C114—C119—C118−0.9 (4)
O21—S23—C22—C27−13.4 (3)P1—C114—C119—C118180.0 (2)
O22—S23—C22—C27−139.1 (3)C124—C123—C122—C1211.5 (4)
N21—S23—C22—C27108.9 (3)C120—C121—C122—C123−0.9 (4)
O21—S23—C22—C23165.0 (2)C122—C121—C120—C125−1.0 (4)
O22—S23—C22—C2339.3 (3)C122—C121—C120—P1179.3 (2)
N21—S23—C22—C23−72.7 (3)C124—C125—C120—C1212.3 (4)
C22—C27—C26—C250.2 (5)C124—C125—C120—P1−177.9 (2)
C24—C25—C26—C270.1 (5)C18—P1—C120—C121−0.8 (3)
C222—C223—C224—C2250.0 (6)C114—P1—C120—C121119.1 (2)
C219—C214—C215—C2162.0 (5)C126—P1—C120—C121−119.7 (2)
P2—C214—C215—C216−179.2 (2)C18—P1—C120—C125179.4 (2)
C231—C230—C229—C228−0.3 (5)C114—P1—C120—C125−60.7 (3)
C211—C212—C213—C281.1 (5)C126—P1—C120—C12560.6 (3)
C224—C223—C222—C2210.4 (7)C122—C123—C124—C1250.0 (4)
C220—C221—C222—C223−0.6 (7)C120—C125—C124—C123−1.9 (4)
C214—C215—C216—C217−3.2 (5)C19—C110—C111—C1120.3 (4)
C217—C218—C219—C214−1.3 (5)C110—C111—C112—C113−1.6 (4)
C215—C214—C219—C2180.3 (4)C18—C113—C112—C1110.8 (4)
P2—C214—C219—C218−178.4 (2)C128—C129—C130—C1310.5 (5)
C213—C212—C211—C210−1.2 (6)C117—C116—C115—C1141.2 (5)
C29—C210—C211—C212−0.7 (5)C119—C114—C115—C1160.1 (4)
C230—C229—C228—C2270.4 (5)P1—C114—C115—C116179.2 (2)
C223—C224—C225—C220−0.3 (5)C119—C118—C117—C1160.9 (5)
C229—C228—C227—C226−0.3 (5)C115—C116—C117—C118−1.7 (5)
C231—C226—C227—C2280.2 (5)C129—C130—C131—C1260.0 (5)
P2—C226—C227—C228−177.1 (2)C130—C131—C126—C127−0.2 (5)
C219—C218—C217—C2160.1 (5)C130—C131—C126—P1−177.4 (3)
C215—C216—C217—C2182.2 (5)C128—C127—C126—C131−0.2 (4)
C211—C210—C29—C282.7 (5)C128—C127—C126—P1177.1 (2)
C212—C213—C28—C290.9 (5)C18—P1—C126—C131−143.9 (3)
C212—C213—C28—P2176.0 (3)C114—P1—C126—C13197.0 (3)
C210—C29—C28—C213−2.8 (5)C120—P1—C126—C131−24.1 (3)
C210—C29—C28—P2−178.2 (3)C18—P1—C126—C12738.9 (3)
C229—C230—C231—C2260.1 (5)C114—P1—C126—C127−80.2 (3)
C227—C226—C231—C230−0.1 (4)C120—P1—C126—C127158.7 (2)
P2—C226—C231—C230177.1 (2)C126—C127—C128—C1290.7 (5)
C213—C28—P2—C214117.8 (3)C130—C129—C128—C127−0.9 (5)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
OW—H1W···O12iii0.852.012.845 (3)166
OW—H2W···O22iv0.851.992.831 (4)172
C16—H16···O21iv0.952.393.230 (4)148
C17—H17···O110.952.52.889 (4)105
C24—H24···O11v0.952.393.154 (4)137
C25—H25···OW0.952.463.303 (4)149
C27—H27···O210.952.562.926 (4)103
C110—H110···N11vi0.952.583.371 (4)141
C112—H112···O11i0.952.513.292 (4)139
C123—H123···N11v0.952.613.385 (4)139

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2374).

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