1,2 Bis(phenyl­sulfan­yl)ethane

organic papers

o2482

14H14S2 doi:10.1107/S1600536805020908 Acta Cryst.(2005). E61, o2482–o2483

Acta Crystallographica Section E Structure Reports

Online

ISSN 1600-5368

1,2-Bis(phenylsulfanyl)ethane

Bao-Hong Hou,aLi-Na Zhou,a Qiu-Xiang Yin,aJing-Kang Wanga and Wei Chena,b*

a_{The State Research Center of Industrialization}

for Crystallization Technology, Tianjin University, Tianjin 300072, People’s Republic of China, andb_{Tianjin Economic and}

Technological Development Area, Tianjin, People’s Republic of China

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 293 K

Mean(C–C) = 0.003 A˚

Rfactor = 0.042

wRfactor = 0.131

Data-to-parameter ratio = 19.2

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2005 International Union of Crystallography

Printed in Great Britain – all rights reserved

In the title compound, C14H14S2, there is a centre of inversion at the mid-point of the central C—C bond. Excluding H atoms, the molecule adopts an anti conformation, with a planar –S– CH2–CH2–S– spacer unit. The dihedral angle between the phenyl ring and the S—C—C—S chain is 84.52 (18)_.

Comment

Many complexes of bis(thioether) ligands with transition metal ions, such as silver(I) (Blacket al., 1995), palladium(II) (Errington et al., 1980) and platinum(II) (Murray & Hartley, 1981), have been characterized and have interesting struc-tures. In contrast, the structures of the free ligands have been much less studied. In the present paper, we report the crystal structure of the title compound, a bis(thioether) ligand, viz. 1,2-bis(phenylsulfanyl)ethane (bpte), (I).

The bpte molecule has a centre of inversion at the mid-point of the central C1—C1Abond; symmetry code: (A) 1x,y,

z; Fig. 1]. Excluding H atoms, the molecule adopts an anti conformation (Goodgame et al., 1999), with a planar spacer unit (S1—C1—C1A—S1A). The S—C bond distances and C— S—C angles are comparable to those observed in an analogous compound, 1,4-bis(phenylsulfanyl)butane (Chenet al., 2005). The S1 S1A non-bonded distance is 4.4223 (16) A˚ . The phenyl ring makes a dihedral angle of 84.52 (18) with the plane of the spacer unit (S1—C1—C1A—S1A).

In the crystal structure of the silver(I) nitrate complex with bpte, (II) (Shao et al., 1991), the ligand adopts a different geometry; the orientation of one phenyl group of bpte with respect to the spacer plane is similar to that in the title

Received 8 June 2005 Accepted 30 June 2005 Online 9 July 2005

Figure 1

compound, but the other phenyl group is twisted about the S—Cphenyl bond. There is no centre of symmetry and the phenyl rings are inclined to each other by 63.4_{. A similar}

torsion can also be found in the PdCl2complex with bpte, (III) (Wanget al., 1992).

The S—C bond length and S S non-bonded distance in free bpte are slightly shorter than those in complexes (II) and (III), and other analogous bis(thioethers) and corresponding complexes (Buet al., 2002).

Another determination of the title compound is reported in the preceding paper (Awalehet al., 2005).

Experimental

1,2-Bis(phenylsulfanyl)ethane (bpte) was prepared according to a reported procedure (Shao et al., 1991) and the product was char-acterized by NMR. Colourless single crystals of the title compound, suitable for X-ray diffraction, were obtained by slow evaporation at room temperature of a solution in chloroform.1H NMR (CDCl3): 3.02 (t, 4 H), 7.36 (m, 10 H).

Crystal data

C14H14S2

Mr= 246.39

Monoclinic,P21=c

a= 5.8389 (12) A˚

b= 7.6865 (15) A˚

c= 14.124 (3) A˚

= 97.90 (3)

V= 627.9 (2) A˚3

Z= 2

Dx= 1.303 Mg m

3

MoKradiation Cell parameters from 5725

reflections

= 3.0–27.5 = 0.39 mm1

T= 293 (2) K Needle, colourless 0.800.230.10 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer

!scans

Absorption correction: multi-scan (ABSCOR; Higashi, 1995)

Tmin= 0.745,Tmax= 0.961

5725 measured reflections

1418 independent reflections 1180 reflections withI> 2(I)

Rint= 0.058 max= 27.5

h=6!7

k=9!9

l=18!18

Refinement

Refinement onF2 R[F2_{> 2(F}2_{)] = 0.042}

wR(F2) = 0.131

S= 1.03 1418 reflections 74 parameters

H-atom parameters constrained

w= 1/[2

(Fo2) + (0.0735P)2

+ 0.1339P]

whereP= (Fo2+ 2Fc2)/3

(/)max< 0.001

max= 0.48 e A˚ 3

min=0.28 e A˚ 3

Extinction correction:SHELXL97

Extinction coefficient: 0.059 (13)

Table 1

Selected geometric parameters (A˚ ,_).

S1—C2 1.7609 (17) S1—C1 1.825 (2)

C2—S1—C1 105.15 (9)

All H atoms were positioned geometrically, with Csp2_{—H = 0.93 A˚} and Csp3—H = 0.97 A˚ ; they were constrained to ride on their parent atoms, withUiso(H) = 1.2Ueq(C).

Data collection:RAPID-AUTO (Rigaku, 2004); cell refinement:

RAPID-AUTO; data reduction:RAPID-AUTO; program(s) used to solve structure: SHELXS97(Sheldrick, 1997); program(s) used to refine structure:SHELXL97(Sheldrick, 1997); molecular graphics:

ORTEPII (Johnson, 1976); software used to prepare material for publication:CrystalStructure(Rigaku, 2004).

We gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 20206022).

References

Awaleh, M. O., Badia, A. & Brisse, F. (2005). Acta Cryst. E61, o2479– o2480.

Black, J. R., Champness, N. R., Levason, W. & Reid, G. (1995).J. Chem. Soc. Chem. Commun.pp. 1277–1278.

Bu, X.-H., Chen, W., Hou, W.-F., Du, M., Zhang, R.-H. & Brisse, F. (2002).

Inorg. Chem.41, 3477–3482.

Chen, W., Hou, B.-H., Zhou, L.-N., Wang, J.-K. & Li H. (2005).Acta Cryst.E61, o1890–o1891.

Errington, J., McDonald, W. S. & Shaw, B. L. (1980).J. Chem. Soc. Dalton Trans.pp. 2309–2315.

Goodgame, D. M. L., Grachvogel, D. A., Hussain, I., White, A. J. P. & Williams, D. J. (1999).Inorg. Chem.38, 2057–2063.

Higashi, T. (1995).ABSCOR. Rigaku Corporation, Tokyo, Japan.

Johnson, C. K. (1976).ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.

Murray, S. G. & Hartley, F. R. (1981).Chem. Rev.81, 365–414.

Rigaku. (2004). RAPID AUTO andCrystalStructure. Rigaku/MSC Inc., 9009 New Trails Drive, The Woodlands, TX 77381-5209, USA.

Shao, P.-X., Yao, X.-K., Wang, H.-G., Wang, W.-H., Liu, B., Li, M., Luo, L.-W. & Xu D.-H. (1991).Chem. J. Chin. Univ.12, 143–147.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.

supporting information

sup-1 Acta Cryst. (2005). E61, o2482–o2483

supporting information

Acta Cryst. (2005). E61, o2482–o2483 [https://doi.org/10.1107/S1600536805020908]

1,2-Bis(phenylsulfanyl)ethane

Bao-Hong Hou, Li-Na Zhou, Qiu-Xiang Yin, Jing-Kang Wang and Wei Chen

1,2-bis(phenylsulfanyl)ethane

Crystal data

C14H14S2 Mr = 246.39 Monoclinic, P21/c

Hall symbol: -P 2ybc

a = 5.8389 (12) Å

b = 7.6865 (15) Å

c = 14.124 (3) Å

β = 97.90 (3)°

V = 627.9 (2) Å3 Z = 2

F(000) = 260

Dx = 1.303 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 5725 reflections

θ = 3.0–27.5°

µ = 0.39 mm−1 T = 293 K Needle, colorless 0.80 × 0.23 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer

Radiation source: rotating anode Graphite monochromator

ω scans

Absorption correction: multi-scan (ABSCOR; Higashi, 1995)

Tmin = 0.745, Tmax = 0.961

5725 measured reflections 1418 independent reflections 1180 reflections with I > 2σ(I)

Rint = 0.058

θmax = 27.5°, θmin = 3.0° h = −6→7

k = −9→9

l = −18→18

Refinement

Refinement on F2

Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.042} wR(F2_{) = 0.131} S = 1.03 1418 reflections 74 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2_(F

o2) + (0.0735P)2 + 0.1339P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001

Δρmax = 0.48 e Å−3

Δρmin = −0.28 e Å−3

Extinction correction: SHELXL97, Fc*_{=kFc[1+0.001xFc}2_λ3_/sin(2θ)]-1/4

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 F}2_,

conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

S1 0.82869 (8) 0.07821 (8) 0.08636 (3) 0.0597 (3)

C1 0.6091 (3) −0.0518 (3) 0.01381 (14) 0.0574 (5)

H2A 0.6685 −0.0906 −0.0435 0.069*

H2B 0.5743 −0.1540 0.0495 0.069*

C2 0.7676 (3) 0.0563 (2) 0.20445 (12) 0.0426 (4)

C3 0.5774 (3) −0.0280 (3) 0.23236 (13) 0.0526 (5)

H6A 0.4668 −0.0775 0.1866 0.063*

C4 0.5528 (4) −0.0383 (3) 0.32789 (14) 0.0582 (5)

H4A 0.4259 −0.0961 0.3461 0.070*

C5 0.7124 (4) 0.0353 (3) 0.39639 (14) 0.0626 (5)

H5A 0.6942 0.0280 0.4606 0.075*

C6 0.8993 (4) 0.1200 (3) 0.36909 (15) 0.0683 (6)

H7A 1.0083 0.1702 0.4152 0.082*

C7 0.9276 (3) 0.1314 (3) 0.27418 (14) 0.0554 (5)

H3A 1.0548 0.1899 0.2567 0.066*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

S1 0.0474 (3) 0.0904 (5) 0.0429 (3) −0.0134 (2) 0.0117 (2) −0.0026 (2)

C1 0.0568 (11) 0.0718 (12) 0.0446 (10) 0.0078 (9) 0.0109 (8) −0.0094 (8)

C2 0.0400 (9) 0.0471 (8) 0.0407 (9) 0.0019 (7) 0.0053 (6) −0.0008 (6)

C3 0.0514 (10) 0.0626 (11) 0.0438 (9) −0.0124 (9) 0.0067 (7) −0.0045 (8)

C4 0.0639 (12) 0.0599 (10) 0.0535 (11) −0.0083 (10) 0.0181 (9) 0.0047 (8)

C5 0.0802 (14) 0.0698 (12) 0.0380 (9) 0.0040 (11) 0.0084 (9) 0.0014 (8)

C6 0.0719 (14) 0.0801 (14) 0.0484 (11) −0.0084 (11) −0.0076 (9) −0.0107 (10)

C7 0.0474 (10) 0.0631 (11) 0.0543 (11) −0.0094 (8) 0.0019 (8) −0.0032 (8)

supporting information

sup-3 Acta Cryst. (2005). E61, o2482–o2483

C2—C3 1.389 (2) C6—H7A 0.9300

C3—C4 1.379 (3) C7—H3A 0.9300

C2—S1—C1 105.15 (9) C5—C4—C3 120.99 (18)

C1i_{—C1—S1 111.06 (18) C5—C4—H4A 119.5}

C1i_{—C1—H2A 109.4 C3—C4—H4A 119.5}

S1—C1—H2A 109.4 C4—C5—C6 119.22 (18)

C1i_{—C1—H2B 109.4 C4—C5—H5A 120.4}

S1—C1—H2B 109.4 C6—C5—H5A 120.4

H2A—C1—H2B 108.0 C5—C6—C7 120.75 (19)

C7—C2—C3 118.66 (17) C5—C6—H7A 119.6

C7—C2—S1 115.38 (14) C7—C6—H7A 119.6

C3—C2—S1 125.96 (14) C6—C7—C2 120.40 (18)

C4—C3—C2 119.97 (17) C6—C7—H3A 119.8

C4—C3—H6A 120.0 C2—C7—H3A 119.8

C2—C3—H6A 120.0

C2—S1—C1—C1i _{85.4 (2) C3—C4—C5—C6 −0.2 (3)}

C1—S1—C2—C7 173.98 (14) C4—C5—C6—C7 0.0 (3)

C1—S1—C2—C3 −5.93 (18) C5—C6—C7—C2 −0.4 (3)

C7—C2—C3—C4 −1.1 (3) C3—C2—C7—C6 0.9 (3)

S1—C2—C3—C4 178.82 (15) S1—C2—C7—C6 −178.97 (16)

C2—C3—C4—C5 0.7 (3)