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In the crystal structure of the title compound, [PtCl2(C15H16O2S2)], the central PtII ion is four-coordinated in a slightly distorted square-planar geometry. The crystal represents the racemate formed by the mol­ecules with the (R,R) and (S,S) configurations of the sulfur chiral centres in the chelate ring. The pseudo-torsion angle between two S=O groups (O=S...S=O) is 165.8 (2)° and the dihedral angle formed by the planes of the two phenyl rings is 146.5 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801006754/ya6021sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801006754/ya6021Isup2.hkl
Contains datablock I

CCDC reference: 165636

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.014 Å
  • R factor = 0.047
  • wR factor = 0.114
  • Data-to-parameter ratio = 15.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.529 Tmax scaled 0.119 Tmin scaled 0.098

Comment top

A number of Pt complexes with monosulfoxide have been isolated and fairly well characterized (Calligaris & Carugo, 1996). It was indicated that the sulfoxide group normally coordinates soft metals (Pt, Pd etc.) via its S atom (Kagan & Ronan 1992). PtII usually bonds to bis(sulfoxides) in a cis-chelate mode which may potentially produce complexes with antitumor activity. There are, however, just a few examples of the complexes of this type which were structurally characterized (Cattalini et al., 1979). In this paper, we report the crystal structure of a new PtII complex with the bis(sulfoxide) ligand, namely cis-[rac-1,3-bis(phenylsulfinyl)propane]dichloroplatinum(II), (I).

The crystal represents the racemate formed by the molecules with the (R,R) and (S,S) configurations of the sulfur chiral centres in the chelate ring. The central PtII atom in the title complex, (I), is four-coordinated with two S-donors of the chelate ligand and two terminal Cl ligands, in a slightly distorted square-planar geometry, as shown in Fig. 1. The chelate ring adopts a distorted chair conformation flattened at the platinum end; the displacements of the Pt1 and C2 atoms from the least-squares plane drawn through the S1/C1/S2/C3 atoms (which holds to within 0.04 Å) are equal to 0.4836 (4) and -0.771 (3) Å, respectively. The C4 and C10 atoms are displaced from this plane by 1.241 (3) and -1.631 (2) Å. The pseudo-torsion angle between two SO groups (O1S1···S2O2) is 165.8 (2)° and the dihedral angle formed by the planes of two phenyl rings is 146.5 (2)°. A number of similar conformational features have been reported for the PtII complex of rac-1,2-bis(phenylsulphinyl)ethane with a five-membered chelate cycle (Cattalini et al., 1979); the bond distances and angles in the latter complex are also in good agreement with those found for (I).

Experimental top

rac-1,3-Bis(phenylsulfinyl)propane (Bpsp) was prepared according to the reported procedure of Zhang et al. (1997). To an aqueous solution of K2PtCl4 (100 mg, 0.24 mmol) under heating was slowly added a chloroform solution of equimolar Bpsp (70.4 mg, 0.24 mmol) with vigorous stirring. The white complex soon precipitated. Colorless single crystals of the title compound suitable for X-ray diffraction were obtained from a dimethylformamide–methane solution by slow evaporation of the solvent. Yield: 87.4 mg (65%). FT—IR data (KBr pellet, cm-1): 1131 (s, SO). Analysis calculated for the title complex: C 32.26, H 2.89%; found: C 32.18, H 2.88%.

Refinement top

The C-bound H atoms were placed in their geometrically calculated positions and included in the final refinement in the riding-model approximation with displacement parameters derived from the atoms to which they were bonded. The Uiso for the H atoms were set to be 1.2Ueq for the parent atom. The highest peak is 1.34 Å from Pt1 and the deepest hole is 0.81 Å from Pt1.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 1998).

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) view of the title complex with 30% probability displacement ellipsoids.
cis-[rac-1,3-Bis(phenylsulfinyl)propane]dichloroplatinum(II) top
Crystal data top
[PtCl2(C15H16O2S2)]F(000) = 1064
Mr = 558.39Dx = 2.105 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.5755 (4) ÅCell parameters from 7023 reflections
b = 21.6570 (12) Åθ = 2.7–25.0°
c = 11.0354 (6) ŵ = 8.51 mm1
β = 103.300 (1)°T = 298 K
V = 1761.94 (17) Å3Prism, colorless
Z = 40.30 × 0.25 × 0.25 mm
Data collection top
Bruker SMART 1000
diffractometer
2798 reflections with I > 2σ(I)
ω scansRint = 0.084
Absorption correction: multi-scan
[SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)]
θmax = 25.0°
Tmin = 0.185, Tmax = 0.225h = 89
7105 measured reflectionsk = 2425
3062 independent reflectionsl = 913
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047 w = 1/[σ2(Fo2) + (0.0646P)2 + 3.6575P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.114(Δ/σ)max = 0.001
S = 1.04Δρmax = 1.51 e Å3
3062 reflectionsΔρmin = 1.94 e Å3
199 parameters
Crystal data top
[PtCl2(C15H16O2S2)]V = 1761.94 (17) Å3
Mr = 558.39Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.5755 (4) ŵ = 8.51 mm1
b = 21.6570 (12) ÅT = 298 K
c = 11.0354 (6) Å0.30 × 0.25 × 0.25 mm
β = 103.300 (1)°
Data collection top
Bruker SMART 1000
diffractometer
3062 independent reflections
Absorption correction: multi-scan
[SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)]
2798 reflections with I > 2σ(I)
Tmin = 0.185, Tmax = 0.225Rint = 0.084
7105 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047199 parameters
wR(F2) = 0.114H-atom parameters constrained
S = 1.04Δρmax = 1.51 e Å3
3062 reflectionsΔρmin = 1.94 e Å3
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. Full-MATRIX

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pt10.66712 (4)0.164140 (11)0.70368 (2)0.03829 (15)
S10.4718 (2)0.24269 (8)0.65150 (15)0.0412 (4)
S20.5251 (3)0.11308 (8)0.83136 (15)0.0424 (4)
Cl10.8204 (3)0.20609 (10)0.5647 (2)0.0655 (6)
Cl20.8760 (3)0.08485 (9)0.7383 (2)0.0553 (5)
O10.3489 (9)0.2361 (3)0.5300 (5)0.0668 (16)
O20.6379 (8)0.0847 (3)0.9427 (5)0.0617 (15)
C10.3355 (11)0.2567 (4)0.7623 (8)0.056 (2)
H1A0.41190.27300.83830.067*
H1B0.24450.28760.72900.067*
C20.2419 (12)0.1986 (4)0.7926 (9)0.060 (2)
H2A0.13660.21020.82350.072*
H2B0.19970.17490.71680.072*
C30.3627 (14)0.1589 (3)0.8870 (9)0.058 (2)
H3A0.28720.13130.92270.070*
H3B0.42790.18520.95350.070*
C40.5894 (11)0.3153 (4)0.6609 (6)0.0456 (16)
C50.5202 (12)0.3572 (4)0.5690 (8)0.057 (2)
H5A0.42410.34710.50290.068*
C60.5994 (17)0.4151 (4)0.5789 (12)0.077 (3)
H6A0.55500.44500.51900.093*
C70.7410 (19)0.4289 (4)0.6748 (13)0.086 (4)
H7A0.79060.46840.68110.103*
C80.8134 (16)0.3844 (6)0.7644 (11)0.090 (4)
H8A0.91510.39340.82700.108*
C90.7330 (18)0.3273 (4)0.7591 (9)0.071 (3)
H9A0.77460.29770.82020.085*
C100.3895 (9)0.0548 (3)0.7417 (6)0.0396 (14)
C110.3520 (12)0.0554 (4)0.6124 (7)0.057 (2)
H11A0.39000.08830.57040.068*
C120.2581 (14)0.0071 (5)0.5474 (9)0.071 (3)
H12A0.23510.00670.46100.086*
C130.1975 (12)0.0411 (4)0.6097 (10)0.068 (2)
H13A0.13280.07360.56540.081*
C140.2341 (14)0.0404 (4)0.7388 (11)0.070 (3)
H14A0.19300.07250.78110.084*
C150.3299 (10)0.0070 (4)0.8043 (8)0.055 (2)
H15A0.35490.00700.89080.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pt10.0531 (2)0.0277 (2)0.0379 (2)0.00753 (9)0.01858 (14)0.00044 (9)
S10.0533 (10)0.0337 (9)0.0365 (8)0.0047 (7)0.0103 (7)0.0031 (7)
S20.0559 (10)0.0362 (9)0.0377 (8)0.0111 (8)0.0165 (7)0.0031 (7)
Cl10.0877 (15)0.0543 (12)0.0693 (12)0.0009 (11)0.0488 (12)0.0168 (10)
Cl20.0668 (12)0.0350 (9)0.0683 (12)0.0050 (8)0.0241 (10)0.0022 (8)
O10.075 (4)0.073 (4)0.045 (3)0.010 (3)0.001 (3)0.011 (3)
O20.065 (3)0.074 (4)0.041 (3)0.018 (3)0.001 (2)0.018 (3)
C10.070 (5)0.042 (4)0.064 (4)0.002 (4)0.031 (4)0.001 (4)
C20.050 (5)0.059 (5)0.079 (6)0.005 (4)0.028 (4)0.009 (4)
C30.085 (6)0.040 (4)0.063 (5)0.011 (4)0.045 (5)0.004 (3)
C40.068 (5)0.038 (4)0.033 (3)0.006 (4)0.016 (3)0.002 (3)
C50.066 (5)0.049 (5)0.063 (5)0.024 (4)0.030 (4)0.016 (4)
C60.095 (8)0.042 (5)0.115 (9)0.013 (5)0.065 (7)0.025 (5)
C70.127 (10)0.038 (5)0.112 (9)0.012 (6)0.066 (9)0.009 (6)
C80.100 (8)0.088 (9)0.086 (7)0.045 (7)0.028 (6)0.035 (7)
C90.109 (8)0.049 (5)0.051 (5)0.026 (5)0.013 (5)0.002 (4)
C100.043 (4)0.029 (3)0.049 (4)0.003 (3)0.013 (3)0.001 (3)
C110.072 (5)0.045 (4)0.052 (4)0.014 (4)0.011 (4)0.005 (4)
C120.085 (6)0.064 (6)0.063 (5)0.024 (5)0.010 (5)0.017 (4)
C130.064 (5)0.049 (5)0.089 (6)0.015 (4)0.015 (5)0.020 (5)
C140.065 (5)0.043 (5)0.105 (7)0.015 (4)0.029 (5)0.010 (5)
C150.060 (5)0.040 (5)0.068 (5)0.009 (3)0.020 (4)0.015 (3)
Geometric parameters (Å, º) top
Pt1—S12.2412 (18)C5—C61.384 (14)
Pt1—S22.2501 (15)C5—H5A0.9300
Pt1—Cl12.3118 (17)C6—C71.355 (16)
Pt1—Cl22.3067 (19)C6—H6A0.9300
S1—O11.453 (6)C7—C81.399 (19)
S1—C11.798 (8)C7—H7A0.9300
S1—C41.798 (8)C8—C91.374 (15)
S2—O21.461 (6)C8—H8A0.9300
S2—C31.795 (9)C9—H9A0.9300
S2—C101.778 (7)C10—C151.376 (10)
C1—C21.519 (12)C10—C111.390 (10)
C1—H1A0.9700C11—C121.371 (11)
C1—H1B0.9700C11—H11A0.9300
C2—C31.491 (14)C12—C131.384 (14)
C2—H2A0.9700C12—H12A0.9300
C2—H2B0.9700C13—C141.388 (14)
C3—H3A0.9700C13—H13A0.9300
C3—H3B0.9700C14—C151.364 (13)
C4—C51.373 (12)C14—H14A0.9300
C4—C91.373 (15)C15—H15A0.9300
S1—Pt1—S298.71 (7)C5—C4—C9123.8 (8)
S1—Pt1—Cl2174.19 (6)C5—C4—S1115.8 (7)
S2—Pt1—Cl286.50 (7)C9—C4—S1120.3 (6)
S1—Pt1—Cl186.21 (7)C4—C5—C6117.1 (10)
S2—Pt1—Cl1173.70 (7)C4—C5—H5A121.4
Cl2—Pt1—Cl188.42 (7)C6—C5—H5A121.4
O1—S1—C4110.0 (4)C7—C6—C5120.8 (10)
O1—S1—C1107.3 (4)C7—C6—H6A119.6
C4—S1—C199.7 (4)C5—C6—H6A119.6
O1—S1—Pt1114.1 (3)C6—C7—C8120.7 (10)
C4—S1—Pt1111.1 (3)C6—C7—H7A119.6
C1—S1—Pt1113.7 (3)C8—C7—H7A119.6
O2—S2—C10108.7 (4)C9—C8—C7119.5 (11)
O2—S2—C3105.0 (4)C9—C8—H8A120.2
C10—S2—C3103.2 (4)C7—C8—H8A120.2
O2—S2—Pt1117.5 (2)C4—C9—C8117.8 (10)
C10—S2—Pt1107.4 (2)C4—C9—H9A121.1
C3—S2—Pt1114.0 (3)C8—C9—H9A121.1
C2—C1—S1112.3 (6)C15—C10—C11120.6 (7)
C2—C1—H1A109.1C15—C10—S2118.0 (6)
S1—C1—H1A109.1C11—C10—S2121.3 (5)
C2—C1—H1B109.1C12—C11—C10119.2 (8)
S1—C1—H1B109.1C12—C11—H11A120.4
H1A—C1—H1B107.9C10—C11—H11A120.4
C3—C2—C1112.9 (8)C11—C12—C13120.5 (9)
C3—C2—H2A109.0C11—C12—H12A119.8
C1—C2—H2A109.0C13—C12—H12A119.8
C3—C2—H2B109.0C12—C13—C14119.4 (8)
C1—C2—H2B109.0C12—C13—H13A120.3
H2A—C2—H2B107.8C14—C13—H13A120.3
C2—C3—S2116.0 (6)C15—C14—C13120.5 (8)
C2—C3—H3A108.3C15—C14—H14A119.7
S2—C3—H3A108.3C13—C14—H14A119.7
C2—C3—H3B108.3C14—C15—C10119.7 (8)
S2—C3—H3B108.3C14—C15—H15A120.1
H3A—C3—H3B107.4C10—C15—H15A120.1

Experimental details

Crystal data
Chemical formula[PtCl2(C15H16O2S2)]
Mr558.39
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)7.5755 (4), 21.6570 (12), 11.0354 (6)
β (°) 103.300 (1)
V3)1761.94 (17)
Z4
Radiation typeMo Kα
µ (mm1)8.51
Crystal size (mm)0.30 × 0.25 × 0.25
Data collection
DiffractometerBruker SMART 1000
diffractometer
Absorption correctionMulti-scan
[SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)]
Tmin, Tmax0.185, 0.225
No. of measured, independent and
observed [I > 2σ(I)] reflections
7105, 3062, 2798
Rint0.084
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.114, 1.04
No. of reflections3062
No. of parameters199
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.51, 1.94

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Bruker, 1998).

Selected geometric parameters (Å, º) top
Pt1—S12.2412 (18)S1—C11.798 (8)
Pt1—S22.2501 (15)S1—C41.798 (8)
Pt1—Cl12.3118 (17)S2—C31.795 (9)
Pt1—Cl22.3067 (19)S2—C101.778 (7)
S1—O11.453 (6)
S1—Pt1—S298.71 (7)S1—Pt1—Cl186.21 (7)
S1—Pt1—Cl2174.19 (6)S2—Pt1—Cl1173.70 (7)
S2—Pt1—Cl286.50 (7)Cl2—Pt1—Cl188.42 (7)
 

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