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The molecular structure of the title compound, C15H16O2S2, adopts the R,R form. The dihedral angle between the two phenyl rings is 17.4 (2)° and the torsion angle between the two S=O groups is 69.3 (3)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801006134/tk6014sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801006134/tk6014Isup2.hkl
Contains datablock I

CCDC reference: 165658

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.044
  • wR factor = 0.127
  • Data-to-parameter ratio = 16.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry





Comment top

Bis-sulfoxides are of considerable interest because of the potential antitumor activity of their PtII complexes. Bis-sulfoxide complexes of PtII are normally cis and their antitumor activity depends on the chirality of the ligands (Farrell et al., 1990). There are three isomers with different chirality in bis-sulfoxides, meso, (+)-rac and (-)-rac (Greene et al., 1971). Although the stereoisomers can be characterized by NMR spectroscopy, their molecular structures are less well studied (Cattalini et al., 1979). In the present paper, we report the crystal structure of the title compound, namely (R,R)-1,3-bis(phenylsulfinyl)propane, (I).

The molecular structure shown in Fig. 1 has the R,R conformation. The dihedral angle between the two phenyl rings is 17.4 (2)° and the torsion angle between the two SO groups is 69.3 (3)°. A similar situation has been found in the structure of (R,R)-1,2-bis(phenylsulphinyl)propane (Cattalini et al., 1979) and there is a close agreement between their geometric parameters.

Experimental top

Compound (I) was prepared according to a reported procedure and was characterized by NMR, IR and elemental analyses, giving results consistent with those in the literature (Zhang et al., 1997). Colorless single crystals of title compound suitable for X-ray diffraction were obtained by slow diffusion of acetone into the chloroform solution of (I).

Refinement top

The C-bound H atoms were placed in 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.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT1000 (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976).

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) view of the title compound with 30% probability ellipsoids.
(R,R)-1,3-Bis(phenylsulfinyl)propane top
Crystal data top
C15H16O2S2F(000) = 616
Mr = 292.40Dx = 1.360 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.444 (4) ÅCell parameters from 6382 reflections
b = 15.580 (7) Åθ = 2.3–26.4°
c = 11.579 (6) ŵ = 0.37 mm1
β = 110.333 (9)°T = 293 K
V = 1428.4 (12) Å3Prism, colorless
Z = 40.30 × 0.25 × 0.20 mm
Data collection top
Bruker SMART1000
diffractometer
2469 reflections with I > 2.0σ(I)
ω scansRint = 0.026
Absorption correction: multi-scan
[SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)]
θmax = 26.4°
Tmin = 0.898, Tmax = 0.930h = 105
6457 measured reflectionsk = 1919
2910 independent reflectionsl = 1314
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.0643P)2 + 0.4887P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.044(Δ/σ)max < 0.001
wR(F2) = 0.127Δρmax = 0.75 e Å3
S = 1.1Δρmin = 0.33 e Å3
2910 reflectionsExtinction correction: SHELXL
172 parametersExtinction coefficient: none
H-atom parameters constrained
Crystal data top
C15H16O2S2V = 1428.4 (12) Å3
Mr = 292.40Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.444 (4) ŵ = 0.37 mm1
b = 15.580 (7) ÅT = 293 K
c = 11.579 (6) Å0.30 × 0.25 × 0.20 mm
β = 110.333 (9)°
Data collection top
Bruker SMART1000
diffractometer
2910 independent reflections
Absorption correction: multi-scan
[SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)]
2469 reflections with I > 2.0σ(I)
Tmin = 0.898, Tmax = 0.930Rint = 0.026
6457 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044172 parameters
wR(F2) = 0.127H-atom parameters constrained
S = 1.1Δρmax = 0.75 e Å3
2910 reflectionsΔρmin = 0.33 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
S10.19396 (7)0.49357 (4)0.64233 (6)0.04923 (19)
S20.17564 (7)0.20652 (4)0.92388 (5)0.04758 (18)
O10.1274 (2)0.53952 (13)0.7282 (2)0.0707 (5)
O20.3138 (2)0.25460 (15)1.01900 (16)0.0664 (5)
C10.1477 (3)0.38109 (14)0.6490 (2)0.0471 (5)
H1A0.03150.37090.59700.056*
H1B0.21940.34830.61550.056*
C20.1729 (3)0.34836 (14)0.77723 (19)0.0442 (5)
H2A0.08940.37400.80680.053*
H2B0.28400.36480.83280.053*
C30.1559 (3)0.25154 (14)0.7760 (2)0.0425 (5)
H3A0.24190.22660.74850.051*
H3B0.04660.23580.71690.051*
C40.4196 (3)0.48892 (13)0.71527 (19)0.0408 (5)
C50.4976 (3)0.52420 (14)0.8307 (2)0.0467 (5)
H5A0.43310.54680.87420.056*
C60.6720 (3)0.52572 (17)0.8812 (2)0.0567 (6)
H6A0.72450.54910.95910.068*
C70.7682 (3)0.49309 (18)0.8173 (3)0.0614 (7)
H7A0.88540.49480.85130.074*
C80.6899 (4)0.4580 (2)0.7029 (3)0.0670 (7)
H8A0.75510.43550.65980.080*
C90.5164 (3)0.45543 (17)0.6507 (2)0.0568 (6)
H9A0.46470.43150.57300.068*
C100.0204 (3)0.24329 (13)0.93378 (18)0.0374 (4)
C110.1700 (3)0.20647 (18)0.8589 (2)0.0558 (6)
H11A0.16950.16530.80080.067*
C120.3198 (3)0.2315 (2)0.8715 (3)0.0688 (8)
H12A0.42120.20730.82170.083*
C130.3189 (3)0.2925 (2)0.9579 (3)0.0616 (7)
H13A0.42020.31010.96530.074*
C140.1694 (3)0.32731 (16)1.0331 (2)0.0545 (6)
H14A0.16980.36791.09190.065*
C150.0186 (3)0.30252 (14)1.0221 (2)0.0451 (5)
H15A0.08290.32561.07370.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0463 (3)0.0439 (3)0.0541 (3)0.0021 (2)0.0132 (3)0.0005 (2)
S20.0412 (3)0.0527 (3)0.0479 (3)0.0103 (2)0.0143 (2)0.0089 (2)
O10.0570 (11)0.0607 (11)0.1000 (15)0.0043 (9)0.0344 (11)0.0182 (10)
O20.0348 (8)0.1077 (16)0.0470 (9)0.0017 (9)0.0018 (7)0.0049 (10)
C10.0513 (13)0.0453 (12)0.0420 (11)0.0124 (10)0.0130 (10)0.0056 (9)
C20.0482 (12)0.0450 (11)0.0409 (11)0.0049 (9)0.0172 (10)0.0058 (9)
C30.0426 (11)0.0440 (11)0.0436 (11)0.0019 (9)0.0185 (9)0.0033 (9)
C40.0458 (11)0.0349 (10)0.0438 (11)0.0027 (8)0.0180 (9)0.0006 (8)
C50.0552 (13)0.0419 (11)0.0475 (12)0.0059 (10)0.0236 (10)0.0066 (9)
C60.0597 (15)0.0524 (13)0.0525 (13)0.0107 (11)0.0126 (12)0.0018 (11)
C70.0466 (13)0.0606 (15)0.0747 (18)0.0003 (11)0.0180 (13)0.0101 (13)
C80.0617 (16)0.0756 (18)0.0764 (19)0.0090 (14)0.0403 (15)0.0015 (14)
C90.0642 (15)0.0626 (15)0.0493 (13)0.0008 (12)0.0268 (12)0.0078 (11)
C100.0377 (10)0.0392 (10)0.0351 (10)0.0010 (8)0.0126 (8)0.0052 (8)
C110.0478 (13)0.0690 (16)0.0489 (13)0.0133 (11)0.0146 (11)0.0132 (11)
C120.0387 (13)0.109 (2)0.0545 (15)0.0146 (14)0.0107 (11)0.0021 (15)
C130.0478 (14)0.0857 (19)0.0610 (15)0.0143 (13)0.0312 (12)0.0225 (14)
C140.0677 (16)0.0529 (13)0.0548 (14)0.0031 (11)0.0363 (13)0.0032 (11)
C150.0499 (12)0.0467 (11)0.0403 (11)0.0086 (9)0.0175 (10)0.0015 (9)
Geometric parameters (Å, º) top
S1—O11.485 (2)C5—C61.383 (4)
S1—C41.798 (2)C6—C71.372 (4)
S1—C11.803 (2)C7—C81.372 (4)
S2—O21.497 (2)C8—C91.377 (4)
S2—C101.793 (2)C10—C151.374 (3)
S2—C31.804 (2)C10—C111.384 (3)
C1—C21.513 (3)C11—C121.379 (4)
C2—C31.515 (3)C12—C131.378 (4)
C4—C51.382 (3)C13—C141.372 (4)
C4—C91.387 (3)C14—C151.378 (3)
O1—S1—C4106.91 (11)C7—C6—C5120.6 (2)
O1—S1—C1107.57 (12)C6—C7—C8119.4 (3)
C4—S1—C198.66 (11)C7—C8—C9121.1 (2)
O2—S2—C10107.09 (11)C8—C9—C4119.3 (2)
O2—S2—C3107.17 (11)C15—C10—C11121.1 (2)
C10—S2—C398.83 (10)C15—C10—S2119.41 (17)
C2—C1—S1114.27 (15)C11—C10—S2119.31 (18)
C1—C2—C3110.23 (17)C12—C11—C10119.2 (2)
C2—C3—S2113.64 (15)C13—C12—C11119.9 (2)
C5—C4—C9119.9 (2)C14—C13—C12120.3 (2)
C5—C4—S1120.61 (17)C13—C14—C15120.4 (2)
C9—C4—S1119.26 (18)C10—C15—C14119.1 (2)
C4—C5—C6119.7 (2)

Experimental details

Crystal data
Chemical formulaC15H16O2S2
Mr292.40
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)8.444 (4), 15.580 (7), 11.579 (6)
β (°) 110.333 (9)
V3)1428.4 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.37
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker SMART1000
diffractometer
Absorption correctionMulti-scan
[SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)]
Tmin, Tmax0.898, 0.930
No. of measured, independent and
observed [I > 2.0σ(I)] reflections
6457, 2910, 2469
Rint0.026
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.127, 1.1
No. of reflections2910
No. of parameters172
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.75, 0.33

Computer programs: SMART (Bruker, 1998), SMART, SAINT1000 (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).

 

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