1,2 Bis(phenyl­sulfanyl)ethane

organic papers

Acta Cryst.(2005). E61, o2479–o2481 doi:10.1107/S1600536805020192 Awalehet al. _C

14H14S2

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Structure Reports Online

ISSN 1600-5368

1,2-Bis(phenylsulfanyl)ethane

Mohamed Osman Awaleh,* Antonnella Badia and Franc¸ois Brisse

De´partement de Chimie, Universite´ de Montre´al, CP 6128, Succ. Centre-ville, Montre´al, Que´bec, Canada H3C 3J7

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 220 K

Mean(C–C) = 0.002 A˚

Rfactor = 0.036

wRfactor = 0.107

Data-to-parameter ratio = 16.0

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

#2005 International Union of Crystallography

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In the title crystal structure, C14H14S2,L 2

, the molecules lie on crystallographic inversion centers. The phenyl rings are nearly perpendicular to the planar S—C—C—S group of atoms.

Comment

One of the interests of metal–organic polymer coordination is the design of predictable networks with useful properties (Leininger et al., 2000; Holliday & Mirkin, 2001). Linear bifunctional ligands are often used as building blocks for the construction of metal–organic framework materials (MOF) (Carlucciet al., 2002). The S atom is a soft base and has a good ability to coordinate to silver(I), which is a soft acid. The dithiol group affords two coordination sites to metal centers and can be used to construct supramolecular architectures (Blacket al., 1995; Buet al., 2002). We report here the struc-ture of 1,2-bis(phenylsulfanyl)ethane,L2, (I).

The molecular structure of (I) is shown in Fig. 1. There is a crystallographic center of symmetry at the midpoint of the

central C—C bond. Hence, the torsion angle S1—C7—C7i_—

S1i_{is 180[symmetry code: (i) 2x,y, 1z]. The C1—S1—}

C7—C7i torsion angle is 83.9 (2)_{, and thus the aliphatic}

segment (S—CH2—CH2—S) is nearly perpendicular to the

phenyl rings. In contrast, the longer chain molecule

1,10-bis(phenylsulfanyl)decane, L10, is nearly wholly planar

(Awalehet al., 2005). The bond distances and angles inL2are in the normal range (Table 1) (International Tables for Crys-tallography, 1995, Vol. C).

In the crystal packing of (I), illustrated in Fig. 2, there are no

significant – stacking interactions. The S S distance

between adjacent molecules, with a value of 3.5136 (8) A˚ , is slightly less than the sum of the van der Waals radii (3.60 A˚ ; Porterfield, 1994). These short contacts are shown in Fig. 3.

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

Experimental

The title compound was synthesized according to the published procedure of Hartleyet al.(1979). The1_{H NMR spectrum, recorded}

in acetone-d6, confirms the purity of the compound. Compound (I)

was obtained as a crystalline powder from which a needle-like crystal suitable for X-ray analysis was isolated (yield 43%). Analysis, found: C 68.25, H 6.09%; calculated for C14H14S2: C 68.24, H 5.73%.

1

H NMR (acetone-d6 , p.p.m.): 3.14 [s, 4H, –S-(CH2)2-S–], 7.32 (m, 10H,

C6H5–).

Crystal data

C14H14S2

Mr= 246.37

Monoclinic, P2₁=c a= 5.8654 (1) A˚

b= 7.5638 (1) A˚

c= 14.0472 (2) A˚ = 97.600 (1)

V= 617.73 (2) A˚3

Z= 2

Dx= 1.325 Mg m

3

CuKradiation Cell parameters from 4189

reflections = 3.2–72.7 = 3.63 mm1

T= 220 (2) K Needle, colorless 0.320.060.05 mm

Data collection

Bruker SMART 2000 area-detector diffractometer

!scans

Absorption correction: multi-scan (SADABS; Sheldrick,1996)

Tmin= 0.375,Tmax= 0.825 5018 measured reflections

1184 independent reflections 1099 reflections withI> 2(I)

Rint= 0.026

max= 72.7

h=5!6

k=9!9

l=17!16

Refinement

Refinement onF2

R[F2> 2(F2)] = 0.036

wR(F2_{) = 0.107}

S= 1.03 1184 reflections 74 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0794P)2 + 0.1086P]

whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001

max= 0.23 e A˚ 3

min=0.23 e A˚ 3

Extinction correction:SHELXL97

(Sheldrick, 1997)

Extinction coefficient: 0.018 (2)

organic papers

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14H14S2 Acta Cryst.(2005). E61, o2479–o2481

Figure 1

The molecular structure and atomic numbering of (I). Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted. The unlabeled part of the molecule is related by the symmetry transformation (2x,y, 1z).

Figure 2

A crystal packing diagram of (I), viewed along theaaxis. H atoms have been omitted.

Figure 3

Table 1

Selected geometric parameters (A˚ ,_).

S1—C1 1.7667 (15)

S1—C7 1.8123 (16)

C7—C7i

1.515 (3)

C1—S1—C7 105.08 (7) C7i

—C7—S1 112.48 (14)

C1—S1—C7—C7i

83.90 (17)

Symmetry code: (i) 2x;y;1z.

H atoms were placed in calculated positions (C—H = 0.93–0.98 A˚ ) and refined as riding atoms, withUiso(H) = 1.2Ueq(C). A final

veri-fication of possible voids was performed using the VOID routine of thePLATONprogram (Spek, 2003).

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(Maris, 2004).

This work was supported by the Natural Sciences and Engineering Research Council of Canada (FB). MOA thanks

the Programme Canadien de Bourse de la Francophonie and the Organization Internationale de la Francophonie for a graduate scholarship.

References

Awaleh, M. O., Badia, A. & Brisse, F. (2005).Acta Cryst.E61, o2473–o2475. Black, J. R., Champness, N. R., Levason, W. & Reid, G. (1995).J. Chem. Soc.

Dalton Trans.pp. 3439–3445.

Bruker (1997). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (1999).SAINT(Version 6.06) andSMART(Version 5.059). Bruker AXS Inc., Madison, Wisconsin, USA.

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

Inorg. Chem.41, 3477–3482.

Carlucci, L., Ciani, G., Proserpio, D. M. & Rizzato, S. (2002).CrystEngComm, 4, 413–425.

Hartley, F. R., Murray, S. G., Levason, W., Soutter, H. E. & McAuliffe, C. A. (1979).Inorg. Chim. Acta,35, 265–277.

Holliday, B. J. & Mirkin, C. A. (2001).Angew. Chem. Int. Ed.40, 2022–2043. Hou, B.-H., Zhou, L.-N., Yin, Q.-X., Wang, J.-K. & Chen, W. (2005).Acta

Cryst.E61, o2482–o2483.

Leininger, S., Olenyuk, B. & Stang, P. J. (2000).Chem. Rev.100, 853–908. Maris, T. (2004).UdMX.Universite´ de Montre´al, Canada.

Porterfield, W. W. (1994).Inorganic Chemistry: A Unified Approach, p. 168. London: Addison–Wesley.

Sheldrick, G. M. (1996).SADABS. University of Go¨ttingen, Germany. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of

Go¨ttingen, Germany.

Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.

organic papers

Acta Cryst.(2005). E61, o2479–o2481 Awalehet al. _C

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Acta Cryst. (2005). E61, o2479–o2481

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Acta Cryst. (2005). E61, o2479–o2481 [https://doi.org/10.1107/S1600536805020192]

1,2-Bis(phenylsulfanyl)ethane

Mohamed Osman Awaleh, Antonnella Badia and Fran

ç

ois Brisse

1,2-Bis(phenylthio)ethane

Crystal data

C14H14S2

Mr = 246.37 Monoclinic, P21/c Hall symbol: -P 2ybc

a = 5.8654 (1) Å

b = 7.5638 (1) Å

c = 14.0472 (2) Å

β = 97.600 (1)°

V = 617.73 (2) Å3

Z = 2

F(000) = 260

Dx = 1.325 Mg m−3

Cu Kα radiation, λ = 1.54178 Å Cell parameters from 4189 reflections

θ = 3.2–72.7°

µ = 3.63 mm−1

T = 220 K

Needle-like, colorless 0.32 × 0.06 × 0.05 mm

Data collection

Bruker SMART 2000 area-detector diffractometer

Radiation source: X-ray sealed tube Graphite monochromator

Detector resolution: 5.5 pixels mm-1

ω scans

Absorption correction: multi-scan (SADABS; Sheldrick,1996)

Tmin = 0.375, Tmax = 0.825

5018 measured reflections 1184 independent reflections 1099 reflections with I > 2σ(I)

Rint = 0.026

θmax = 72.7°, θmin = 6.4°

h = −5→6

k = −9→9

l = −17→16

Refinement

Refinement on F2 Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.036}

wR(F2_{) = 0.107}

S = 1.03 1184 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) + (0.0794P)2 + 0.1086P] where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001 Δρmax = 0.23 e Å−3 Δρmin = −0.23 e Å−3

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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 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 0.66983 (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₎

U11 _U22 _U33 _U12 _U13 _U23

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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—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)