(R,S)-1,2-Bis­(benzyl­sulfinyl)­ethane

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.

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

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

Crystal data

C16H18O2S2	Dx = 1.343 Mg m^−3
Mr = 306.42	Melting point: 493-495K K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.933 (6) Å	Cell parameters from 2123 reflections
b = 5.312 (2) Å	θ = 1.2–25.0°
c = 8.423 (3) Å	µ = 0.35 mm^−1
β = 91.209 (7)°	T = 293 K
V = 757.5 (5) Å^3	Block, colorless
Z = 2	0.20 × 0.20 × 0.20 mm
F(000) = 324

Data collection

Bruker CCD area-detector diffractometer	1333 independent reflections
Radiation source: fine-focus sealed tube	994 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −20→17
Tmin = 0.933, Tmax = 0.933	k = −6→5
2943 measured reflections	l = −10→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.07P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.007
1333 reflections	Δρmax = 0.25 e Å^−3
91 parameters	Δρmin = −0.34 e Å^−3
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.25 (3)

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.

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.12405 (4)	0.07296 (14)	0.96323 (9)	0.0396 (3)
O1	0.11520 (13)	0.3441 (4)	0.9187 (3)	0.0578 (7)
C1	0.02701 (17)	−0.0623 (6)	0.9415 (4)	0.0414 (8)
H1A	0.0069	−0.0364	0.8341	0.050*
H1B	0.0294	−0.2419	0.9615	0.050*
C2	0.16912 (18)	−0.0874 (6)	0.7982 (4)	0.0424 (8)
H2A	0.1578	−0.2662	0.8037	0.051*
H2B	0.1472	−0.0233	0.6989	0.051*
C3	0.25711 (17)	−0.0463 (6)	0.8040 (3)	0.0377 (7)
C4	0.3056 (2)	−0.2107 (6)	0.8882 (4)	0.0551 (9)
H4A	0.2839	−0.3474	0.9409	0.066*
C5	0.3865 (2)	−0.1709 (8)	0.8937 (5)	0.0673 (11)
H5A	0.4190	−0.2809	0.9509	0.081*
C6	0.4188 (2)	0.0259 (8)	0.8169 (5)	0.0641 (11)
H6A	0.4733	0.0495	0.8202	0.077*
C7	0.3713 (2)	0.1909 (7)	0.7340 (5)	0.0607 (10)
H7A	0.3934	0.3272	0.6818	0.073*
C8	0.29081 (19)	0.1546 (6)	0.7279 (4)	0.0483 (9)
H8A	0.2588	0.2673	0.6717	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0371 (5)	0.0352 (5)	0.0466 (5)	−0.0066 (3)	0.0050 (3)	−0.0019 (4)
O1	0.0596 (15)	0.0297 (12)	0.0849 (17)	−0.0087 (10)	0.0193 (13)	−0.0041 (12)
C1	0.0398 (18)	0.0327 (17)	0.0517 (19)	−0.0073 (13)	0.0032 (14)	−0.0011 (15)
C2	0.0485 (19)	0.0338 (17)	0.0452 (18)	−0.0055 (14)	0.0055 (15)	−0.0055 (14)
C3	0.0403 (17)	0.0341 (17)	0.0390 (17)	0.0004 (13)	0.0057 (13)	−0.0044 (14)
C4	0.065 (2)	0.042 (2)	0.058 (2)	0.0069 (17)	0.0097 (18)	0.0085 (17)
C5	0.056 (2)	0.071 (3)	0.075 (3)	0.024 (2)	−0.005 (2)	0.002 (2)
C6	0.036 (2)	0.078 (3)	0.079 (3)	0.0031 (19)	0.0041 (19)	−0.010 (2)
C7	0.052 (2)	0.060 (2)	0.071 (2)	−0.0120 (18)	0.0113 (19)	0.004 (2)
C8	0.045 (2)	0.0442 (19)	0.055 (2)	0.0001 (15)	−0.0017 (16)	0.0093 (16)

Geometric parameters (Å, º)

S1—O1	1.495 (2)	C3—C4	1.384 (4)
S1—C1	1.799 (3)	C4—C5	1.387 (5)
S1—C2	1.813 (3)	C4—H4A	0.9300
C1—C1^i	1.511 (6)	C5—C6	1.351 (5)
C1—H1A	0.9700	C5—H5A	0.9300
C1—H1B	0.9700	C6—C7	1.372 (5)
C2—C3	1.506 (4)	C6—H6A	0.9300
C2—H2A	0.9700	C7—C8	1.376 (5)
C2—H2B	0.9700	C7—H7A	0.9300
C3—C8	1.375 (4)	C8—H8A	0.9300
O1—S1—C1	105.82 (14)	C4—C3—C2	120.0 (3)
O1—S1—C2	107.59 (15)	C3—C4—C5	119.7 (3)
C1—S1—C2	97.63 (14)	C3—C4—H4A	120.1
C1^i—C1—S1	108.8 (3)	C5—C4—H4A	120.1
C1^i—C1—H1A	109.9	C6—C5—C4	120.8 (3)
S1—C1—H1A	109.9	C6—C5—H5A	119.6
C1^i—C1—H1B	109.9	C4—C5—H5A	119.6
S1—C1—H1B	109.9	C5—C6—C7	119.9 (3)
H1A—C1—H1B	108.3	C5—C6—H6A	120.0
C3—C2—S1	109.9 (2)	C7—C6—H6A	120.0
C3—C2—H2A	109.7	C8—C7—C6	120.0 (3)
S1—C2—H2A	109.7	C8—C7—H7A	120.0
C3—C2—H2B	109.7	C6—C7—H7A	120.0
S1—C2—H2B	109.7	C3—C8—C7	120.8 (3)
H2A—C2—H2B	108.2	C3—C8—H8A	119.6
C8—C3—C4	118.8 (3)	C7—C8—H8A	119.6
C8—C3—C2	121.2 (3)
O1—S1—C1—C1^i	−63.6 (3)	C2—C3—C4—C5	−179.6 (3)
C2—S1—C1—C1^i	−174.4 (3)	C3—C4—C5—C6	−0.4 (6)
O1—S1—C2—C3	81.0 (2)	C4—C5—C6—C7	0.9 (6)
C1—S1—C2—C3	−169.7 (2)	C5—C6—C7—C8	−0.6 (6)
S1—C2—C3—C8	−90.2 (3)	C4—C3—C8—C7	0.6 (5)
S1—C2—C3—C4	89.2 (3)	C2—C3—C8—C7	179.9 (3)
C8—C3—C4—C5	−0.3 (5)	C6—C7—C8—C3	−0.1 (6)

Symmetry code: (i) −x, −y, −z+2.