1,2-Bis(phenyl­sulfanyl)ethane

In the title crystal structure, C₁₄H₁₄S₂, L², the mol­ecules lie on crystallographic inversion centers. The phen­yl rings are nearly perpendicular to the planar S-C-C-S group of atoms.

Key indicators

• Single-crystal X-ray study
• T = 220 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.036
• wR factor = 0.107
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: UdMX (local program; Author and date?).

1,2-Bis(phenylthio)ethane

Crystal data

C14H14S2	F(000) = 260
Mr = 246.37	Dx = 1.325 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 4189 reflections
a = 5.8654 (1) Å	θ = 3.2–72.7°
b = 7.5638 (1) Å	µ = 3.63 mm^−1
c = 14.0472 (2) Å	T = 220 K
β = 97.600 (1)°	Needle-like, colorless
V = 617.73 (2) Å^3	0.32 × 0.06 × 0.05 mm
Z = 2

Data collection

Bruker SMART 2000 area-detector diffractometer	1184 independent reflections
Radiation source: X-ray sealed tube	1099 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 5.5 pixels mm^-1	θmax = 72.7°, θmin = 6.4°
ω scans	h = −5→6
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	k = −9→9
Tmin = 0.375, Tmax = 0.825	l = −17→16
5018 measured reflections

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)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0794P)^2 + 0.1086P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1184 reflections	Δρmax = 0.23 e Å^−3
74 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (2)

Special details

Experimental. X-ray crystallographic data for I were collected from a single-crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 2 K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu—Kα radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8 Å resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis.

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	0.66983 (6)	0.07504 (6)	0.41416 (3)	0.0399 (2)
C1	0.7328 (3)	0.05351 (17)	0.29514 (11)	0.0307 (4)
C4	0.7900 (3)	0.0336 (2)	0.10185 (12)	0.0453 (4)
H4	0.8092	0.0265	0.0366	0.054*
C6	0.9244 (3)	−0.0306 (2)	0.26748 (11)	0.0374 (4)
H6	1.0358	−0.0806	0.3140	0.045*
C5	0.9501 (3)	−0.0404 (2)	0.17069 (12)	0.0417 (4)
H5	1.0788	−0.0985	0.1520	0.050*
C2	0.5714 (3)	0.1287 (2)	0.22523 (12)	0.0403 (4)
H2	0.4421	0.1866	0.2433	0.048*
C3	0.6005 (3)	0.1185 (2)	0.12942 (13)	0.0477 (5)
H3	0.4908	0.1697	0.0826	0.057*
C7	0.8901 (3)	−0.0522 (2)	0.48666 (12)	0.0375 (4)
H7A	0.8315	−0.0905	0.5455	0.045*
H7B	0.9244	−0.1582	0.4511	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0319 (3)	0.0569 (3)	0.0319 (3)	0.00648 (14)	0.00862 (18)	0.00177 (14)
C1	0.0303 (8)	0.0315 (7)	0.0304 (7)	−0.0021 (5)	0.0041 (6)	0.0009 (5)
C4	0.0596 (11)	0.0477 (9)	0.0287 (8)	−0.0031 (8)	0.0067 (7)	−0.0018 (7)
C6	0.0368 (9)	0.0417 (8)	0.0335 (8)	0.0068 (6)	0.0038 (6)	0.0025 (6)
C5	0.0472 (10)	0.0416 (8)	0.0385 (9)	0.0053 (7)	0.0138 (7)	−0.0027 (6)
C2	0.0349 (9)	0.0446 (9)	0.0406 (9)	0.0056 (6)	0.0015 (6)	0.0020 (7)
C3	0.0496 (11)	0.0540 (10)	0.0369 (9)	0.0046 (8)	−0.0044 (7)	0.0062 (7)
C7	0.0354 (9)	0.0461 (8)	0.0317 (7)	−0.0028 (6)	0.0072 (6)	0.0070 (6)

Geometric parameters (Å, º)

S1—C1	1.7667 (15)	C6—H6	0.94
S1—C7	1.8123 (16)	C5—H5	0.94
C1—C6	1.391 (2)	C2—C3	1.381 (2)
C1—C2	1.392 (2)	C2—H2	0.94
C4—C5	1.375 (2)	C3—H3	0.94
C4—C3	1.383 (3)	C7—C7^i	1.515 (3)
C4—H4	0.94	C7—H7A	0.98
C6—C5	1.390 (2)	C7—H7B	0.98
C1—S1—C7	105.08 (7)	C3—C2—C1	120.32 (16)
C6—C1—C2	119.27 (15)	C3—C2—H2	119.8
C6—C1—S1	125.75 (12)	C1—C2—H2	119.8
C2—C1—S1	114.98 (12)	C2—C3—C4	120.41 (16)
C5—C4—C3	119.46 (16)	C2—C3—H3	119.8
C5—C4—H4	120.3	C4—C3—H3	119.8
C3—C4—H4	120.3	C7^i—C7—S1	112.48 (14)
C5—C6—C1	119.60 (14)	C7^i—C7—H7A	109.1
C5—C6—H6	120.2	S1—C7—H7A	109.1
C1—C6—H6	120.2	C7^i—C7—H7B	109.1
C4—C5—C6	120.94 (16)	S1—C7—H7B	109.1
C4—C5—H5	119.5	H7A—C7—H7B	107.8
C6—C5—H5	119.5
C7—S1—C1—C6	−5.28 (15)	C6—C1—C2—C3	0.5 (2)
C7—S1—C1—C2	174.47 (12)	S1—C1—C2—C3	−179.25 (13)
C2—C1—C6—C5	−0.9 (2)	C1—C2—C3—C4	0.0 (3)
S1—C1—C6—C5	178.87 (12)	C5—C4—C3—C2	−0.2 (3)
C3—C4—C5—C6	−0.2 (3)	C1—S1—C7—C7^i	83.90 (17)
C1—C6—C5—C4	0.7 (3)

Symmetry code: (i) −x+2, −y, −z+1.