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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.
Supporting information
CCDC reference: 282533
Key indicators
- Single-crystal X-ray study
- T = 220 K
- Mean (C-C)= 0.002 Å
- R factor = 0.036
- wR factor = 0.107
- Data-to-parameter ratio = 16.0
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
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
top
Crystal data top
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) Å3 | 0.32 × 0.06 × 0.05 mm |
Z = 2 | |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0794P)2 + 0.1086P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.018 (2) |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C7i | 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 | C7i—C7—S1 | 112.48 (14) |
C5—C6—C1 | 119.60 (14) | C7i—C7—H7A | 109.1 |
C5—C6—H6 | 120.2 | S1—C7—H7A | 109.1 |
C1—C6—H6 | 120.2 | C7i—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—C7i | 83.90 (17) |
C1—C6—C5—C4 | 0.7 (3) | | |
Symmetry code: (i) −x+2, −y, −z+1. |
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