Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801006134/tk6014sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801006134/tk6014Isup2.hkl |
CCDC reference: 165658
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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).
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.
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).
Fig. 1. ORTEPII (Johnson, 1976) view of the title compound with 30% probability ellipsoids. |
C15H16O2S2 | F(000) = 616 |
Mr = 292.40 | Dx = 1.360 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.444 (4) Å | Cell parameters from 6382 reflections |
b = 15.580 (7) Å | θ = 2.3–26.4° |
c = 11.579 (6) Å | µ = 0.37 mm−1 |
β = 110.333 (9)° | T = 293 K |
V = 1428.4 (12) Å3 | Prism, colorless |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
Bruker SMART1000 diffractometer | 2469 reflections with I > 2.0σ(I) |
ω scans | Rint = 0.026 |
Absorption correction: multi-scan [SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)] | θmax = 26.4° |
Tmin = 0.898, Tmax = 0.930 | h = −10→5 |
6457 measured reflections | k = −19→19 |
2910 independent reflections | l = −13→14 |
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) = 0.127 | Δρmax = 0.75 e Å−3 |
S = 1.1 | Δρmin = −0.33 e Å−3 |
2910 reflections | Extinction correction: SHELXL |
172 parameters | Extinction coefficient: none |
H-atom parameters constrained |
C15H16O2S2 | V = 1428.4 (12) Å3 |
Mr = 292.40 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.444 (4) Å | µ = 0.37 mm−1 |
b = 15.580 (7) Å | T = 293 K |
c = 11.579 (6) Å | 0.30 × 0.25 × 0.20 mm |
β = 110.333 (9)° |
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 = 0.930 | Rint = 0.026 |
6457 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 172 parameters |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.1 | Δρmax = 0.75 e Å−3 |
2910 reflections | Δρmin = −0.33 e Å−3 |
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 |
x | y | z | Uiso*/Ueq | ||
S1 | 0.19396 (7) | 0.49357 (4) | 0.64233 (6) | 0.04923 (19) | |
S2 | 0.17564 (7) | 0.20652 (4) | 0.92388 (5) | 0.04758 (18) | |
O1 | 0.1274 (2) | 0.53952 (13) | 0.7282 (2) | 0.0707 (5) | |
O2 | 0.3138 (2) | 0.25460 (15) | 1.01900 (16) | 0.0664 (5) | |
C1 | 0.1477 (3) | 0.38109 (14) | 0.6490 (2) | 0.0471 (5) | |
H1A | 0.0315 | 0.3709 | 0.5970 | 0.056* | |
H1B | 0.2194 | 0.3483 | 0.6155 | 0.056* | |
C2 | 0.1729 (3) | 0.34836 (14) | 0.77723 (19) | 0.0442 (5) | |
H2A | 0.0894 | 0.3740 | 0.8068 | 0.053* | |
H2B | 0.2840 | 0.3648 | 0.8328 | 0.053* | |
C3 | 0.1559 (3) | 0.25154 (14) | 0.7760 (2) | 0.0425 (5) | |
H3A | 0.2419 | 0.2266 | 0.7485 | 0.051* | |
H3B | 0.0466 | 0.2358 | 0.7169 | 0.051* | |
C4 | 0.4196 (3) | 0.48892 (13) | 0.71527 (19) | 0.0408 (5) | |
C5 | 0.4976 (3) | 0.52420 (14) | 0.8307 (2) | 0.0467 (5) | |
H5A | 0.4331 | 0.5468 | 0.8742 | 0.056* | |
C6 | 0.6720 (3) | 0.52572 (17) | 0.8812 (2) | 0.0567 (6) | |
H6A | 0.7245 | 0.5491 | 0.9591 | 0.068* | |
C7 | 0.7682 (3) | 0.49309 (18) | 0.8173 (3) | 0.0614 (7) | |
H7A | 0.8854 | 0.4948 | 0.8513 | 0.074* | |
C8 | 0.6899 (4) | 0.4580 (2) | 0.7029 (3) | 0.0670 (7) | |
H8A | 0.7551 | 0.4355 | 0.6598 | 0.080* | |
C9 | 0.5164 (3) | 0.45543 (17) | 0.6507 (2) | 0.0568 (6) | |
H9A | 0.4647 | 0.4315 | 0.5730 | 0.068* | |
C10 | −0.0204 (3) | 0.24329 (13) | 0.93378 (18) | 0.0374 (4) | |
C11 | −0.1700 (3) | 0.20647 (18) | 0.8589 (2) | 0.0558 (6) | |
H11A | −0.1695 | 0.1653 | 0.8008 | 0.067* | |
C12 | −0.3198 (3) | 0.2315 (2) | 0.8715 (3) | 0.0688 (8) | |
H12A | −0.4212 | 0.2073 | 0.8217 | 0.083* | |
C13 | −0.3189 (3) | 0.2925 (2) | 0.9579 (3) | 0.0616 (7) | |
H13A | −0.4202 | 0.3101 | 0.9653 | 0.074* | |
C14 | −0.1694 (3) | 0.32731 (16) | 1.0331 (2) | 0.0545 (6) | |
H14A | −0.1698 | 0.3679 | 1.0919 | 0.065* | |
C15 | −0.0186 (3) | 0.30252 (14) | 1.0221 (2) | 0.0451 (5) | |
H15A | 0.0829 | 0.3256 | 1.0737 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0463 (3) | 0.0439 (3) | 0.0541 (3) | −0.0021 (2) | 0.0132 (3) | 0.0005 (2) |
S2 | 0.0412 (3) | 0.0527 (3) | 0.0479 (3) | 0.0103 (2) | 0.0143 (2) | 0.0089 (2) |
O1 | 0.0570 (11) | 0.0607 (11) | 0.1000 (15) | 0.0043 (9) | 0.0344 (11) | −0.0182 (10) |
O2 | 0.0348 (8) | 0.1077 (16) | 0.0470 (9) | 0.0017 (9) | 0.0018 (7) | 0.0049 (10) |
C1 | 0.0513 (13) | 0.0453 (12) | 0.0420 (11) | −0.0124 (10) | 0.0130 (10) | −0.0056 (9) |
C2 | 0.0482 (12) | 0.0450 (11) | 0.0409 (11) | −0.0049 (9) | 0.0172 (10) | −0.0058 (9) |
C3 | 0.0426 (11) | 0.0440 (11) | 0.0436 (11) | 0.0019 (9) | 0.0185 (9) | −0.0033 (9) |
C4 | 0.0458 (11) | 0.0349 (10) | 0.0438 (11) | −0.0027 (8) | 0.0180 (9) | 0.0006 (8) |
C5 | 0.0552 (13) | 0.0419 (11) | 0.0475 (12) | −0.0059 (10) | 0.0236 (10) | −0.0066 (9) |
C6 | 0.0597 (15) | 0.0524 (13) | 0.0525 (13) | −0.0107 (11) | 0.0126 (12) | −0.0018 (11) |
C7 | 0.0466 (13) | 0.0606 (15) | 0.0747 (18) | −0.0003 (11) | 0.0180 (13) | 0.0101 (13) |
C8 | 0.0617 (16) | 0.0756 (18) | 0.0764 (19) | 0.0090 (14) | 0.0403 (15) | 0.0015 (14) |
C9 | 0.0642 (15) | 0.0626 (15) | 0.0493 (13) | 0.0008 (12) | 0.0268 (12) | −0.0078 (11) |
C10 | 0.0377 (10) | 0.0392 (10) | 0.0351 (10) | −0.0010 (8) | 0.0126 (8) | 0.0052 (8) |
C11 | 0.0478 (13) | 0.0690 (16) | 0.0489 (13) | −0.0133 (11) | 0.0146 (11) | −0.0132 (11) |
C12 | 0.0387 (13) | 0.109 (2) | 0.0545 (15) | −0.0146 (14) | 0.0107 (11) | −0.0021 (15) |
C13 | 0.0478 (14) | 0.0857 (19) | 0.0610 (15) | 0.0143 (13) | 0.0312 (12) | 0.0225 (14) |
C14 | 0.0677 (16) | 0.0529 (13) | 0.0548 (14) | 0.0031 (11) | 0.0363 (13) | 0.0032 (11) |
C15 | 0.0499 (12) | 0.0467 (11) | 0.0403 (11) | −0.0086 (9) | 0.0175 (10) | −0.0015 (9) |
S1—O1 | 1.485 (2) | C5—C6 | 1.383 (4) |
S1—C4 | 1.798 (2) | C6—C7 | 1.372 (4) |
S1—C1 | 1.803 (2) | C7—C8 | 1.372 (4) |
S2—O2 | 1.497 (2) | C8—C9 | 1.377 (4) |
S2—C10 | 1.793 (2) | C10—C15 | 1.374 (3) |
S2—C3 | 1.804 (2) | C10—C11 | 1.384 (3) |
C1—C2 | 1.513 (3) | C11—C12 | 1.379 (4) |
C2—C3 | 1.515 (3) | C12—C13 | 1.378 (4) |
C4—C5 | 1.382 (3) | C13—C14 | 1.372 (4) |
C4—C9 | 1.387 (3) | C14—C15 | 1.378 (3) |
O1—S1—C4 | 106.91 (11) | C7—C6—C5 | 120.6 (2) |
O1—S1—C1 | 107.57 (12) | C6—C7—C8 | 119.4 (3) |
C4—S1—C1 | 98.66 (11) | C7—C8—C9 | 121.1 (2) |
O2—S2—C10 | 107.09 (11) | C8—C9—C4 | 119.3 (2) |
O2—S2—C3 | 107.17 (11) | C15—C10—C11 | 121.1 (2) |
C10—S2—C3 | 98.83 (10) | C15—C10—S2 | 119.41 (17) |
C2—C1—S1 | 114.27 (15) | C11—C10—S2 | 119.31 (18) |
C1—C2—C3 | 110.23 (17) | C12—C11—C10 | 119.2 (2) |
C2—C3—S2 | 113.64 (15) | C13—C12—C11 | 119.9 (2) |
C5—C4—C9 | 119.9 (2) | C14—C13—C12 | 120.3 (2) |
C5—C4—S1 | 120.61 (17) | C13—C14—C15 | 120.4 (2) |
C9—C4—S1 | 119.26 (18) | C10—C15—C14 | 119.1 (2) |
C4—C5—C6 | 119.7 (2) |
Experimental details
Crystal data | |
Chemical formula | C15H16O2S2 |
Mr | 292.40 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 8.444 (4), 15.580 (7), 11.579 (6) |
β (°) | 110.333 (9) |
V (Å3) | 1428.4 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.37 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART1000 diffractometer |
Absorption correction | Multi-scan [SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)] |
Tmin, Tmax | 0.898, 0.930 |
No. of measured, independent and observed [I > 2.0σ(I)] reflections | 6457, 2910, 2469 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.127, 1.1 |
No. of reflections | 2910 |
No. of parameters | 172 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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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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 S═O 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.