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The molecular structure of the title compound, C16H18O2S2, adopts the R,S form, and has a center of symmetry at the midpoint of the central C—C bond. All the C and S atoms between two phenyl rings are coplanar; this plane is perpendicular to the planes of the phenyl rings. The two S=O groups lie on opposite sides of that plane and their pseudo-torsion angle (S=O...S=O) is 180°, as required by symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012503/ww6020sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012503/ww6020Isup2.hkl
Contains datablock I

CCDC reference: 193770

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.040
  • wR factor = 0.130
  • Data-to-parameter ratio = 14.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

CELLZ_01 From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C16 H18 N0 O2 S2 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 32.00 32.00 0.00 H 36.00 36.00 0.00 N 2.00 0.00 2.00 O 4.00 4.00 0.00 S 4.00 4.00 0.00 Difference between formula and atom_site contents detected. ALERT: Large difference may be due to a symmetry error - see SYMMG tests

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(R,S)-1,2-bis(benzylsulfinyl)ethane top
Crystal data top
C16H18O2S2Dx = 1.343 Mg m3
Mr = 306.42Melting point: 493-495K K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.933 (6) ÅCell parameters from 2123 reflections
b = 5.312 (2) Åθ = 1.2–25.0°
c = 8.423 (3) ŵ = 0.35 mm1
β = 91.209 (7)°T = 293 K
V = 757.5 (5) Å3Block, colorless
Z = 20.20 × 0.20 × 0.20 mm
F(000) = 324
Data collection top
Bruker CCD area-detector
diffractometer
1333 independent reflections
Radiation source: fine-focus sealed tube994 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
φ and ω scansθmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 2017
Tmin = 0.933, Tmax = 0.933k = 65
2943 measured reflectionsl = 109
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.07P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.007
1333 reflectionsΔρmax = 0.25 e Å3
91 parametersΔρmin = 0.34 e Å3
0 restraintsExtinction correction: SHELXL97
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.25 (3)
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.12405 (4)0.07296 (14)0.96323 (9)0.0396 (3)
O10.11520 (13)0.3441 (4)0.9187 (3)0.0578 (7)
C10.02701 (17)0.0623 (6)0.9415 (4)0.0414 (8)
H1A0.00690.03640.83410.050*
H1B0.02940.24190.96150.050*
C20.16912 (18)0.0874 (6)0.7982 (4)0.0424 (8)
H2A0.15780.26620.80370.051*
H2B0.14720.02330.69890.051*
C30.25711 (17)0.0463 (6)0.8040 (3)0.0377 (7)
C40.3056 (2)0.2107 (6)0.8882 (4)0.0551 (9)
H4A0.28390.34740.94090.066*
C50.3865 (2)0.1709 (8)0.8937 (5)0.0673 (11)
H5A0.41900.28090.95090.081*
C60.4188 (2)0.0259 (8)0.8169 (5)0.0641 (11)
H6A0.47330.04950.82020.077*
C70.3713 (2)0.1909 (7)0.7340 (5)0.0607 (10)
H7A0.39340.32720.68180.073*
C80.29081 (19)0.1546 (6)0.7279 (4)0.0483 (9)
H8A0.25880.26730.67170.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0371 (5)0.0352 (5)0.0466 (5)0.0066 (3)0.0050 (3)0.0019 (4)
O10.0596 (15)0.0297 (12)0.0849 (17)0.0087 (10)0.0193 (13)0.0041 (12)
C10.0398 (18)0.0327 (17)0.0517 (19)0.0073 (13)0.0032 (14)0.0011 (15)
C20.0485 (19)0.0338 (17)0.0452 (18)0.0055 (14)0.0055 (15)0.0055 (14)
C30.0403 (17)0.0341 (17)0.0390 (17)0.0004 (13)0.0057 (13)0.0044 (14)
C40.065 (2)0.042 (2)0.058 (2)0.0069 (17)0.0097 (18)0.0085 (17)
C50.056 (2)0.071 (3)0.075 (3)0.024 (2)0.005 (2)0.002 (2)
C60.036 (2)0.078 (3)0.079 (3)0.0031 (19)0.0041 (19)0.010 (2)
C70.052 (2)0.060 (2)0.071 (2)0.0120 (18)0.0113 (19)0.004 (2)
C80.045 (2)0.0442 (19)0.055 (2)0.0001 (15)0.0017 (16)0.0093 (16)
Geometric parameters (Å, º) top
S1—O11.495 (2)C3—C41.384 (4)
S1—C11.799 (3)C4—C51.387 (5)
S1—C21.813 (3)C4—H4A0.9300
C1—C1i1.511 (6)C5—C61.351 (5)
C1—H1A0.9700C5—H5A0.9300
C1—H1B0.9700C6—C71.372 (5)
C2—C31.506 (4)C6—H6A0.9300
C2—H2A0.9700C7—C81.376 (5)
C2—H2B0.9700C7—H7A0.9300
C3—C81.375 (4)C8—H8A0.9300
O1—S1—C1105.82 (14)C4—C3—C2120.0 (3)
O1—S1—C2107.59 (15)C3—C4—C5119.7 (3)
C1—S1—C297.63 (14)C3—C4—H4A120.1
C1i—C1—S1108.8 (3)C5—C4—H4A120.1
C1i—C1—H1A109.9C6—C5—C4120.8 (3)
S1—C1—H1A109.9C6—C5—H5A119.6
C1i—C1—H1B109.9C4—C5—H5A119.6
S1—C1—H1B109.9C5—C6—C7119.9 (3)
H1A—C1—H1B108.3C5—C6—H6A120.0
C3—C2—S1109.9 (2)C7—C6—H6A120.0
C3—C2—H2A109.7C8—C7—C6120.0 (3)
S1—C2—H2A109.7C8—C7—H7A120.0
C3—C2—H2B109.7C6—C7—H7A120.0
S1—C2—H2B109.7C3—C8—C7120.8 (3)
H2A—C2—H2B108.2C3—C8—H8A119.6
C8—C3—C4118.8 (3)C7—C8—H8A119.6
C8—C3—C2121.2 (3)
O1—S1—C1—C1i63.6 (3)C2—C3—C4—C5179.6 (3)
C2—S1—C1—C1i174.4 (3)C3—C4—C5—C60.4 (6)
O1—S1—C2—C381.0 (2)C4—C5—C6—C70.9 (6)
C1—S1—C2—C3169.7 (2)C5—C6—C7—C80.6 (6)
S1—C2—C3—C890.2 (3)C4—C3—C8—C70.6 (5)
S1—C2—C3—C489.2 (3)C2—C3—C8—C7179.9 (3)
C8—C3—C4—C50.3 (5)C6—C7—C8—C30.1 (6)
Symmetry code: (i) x, y, z+2.
 

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