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Volume 64 
Part 6 
Page o1119  
June 2008  

Received 4 May 2008
Accepted 15 May 2008
Online 21 May 2008

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.088
wR = 0.205
Data-to-parameter ratio = 21.8
Details
Open access

1,2-Bis(undecylsulfanyl)benzene

Etsuko Tomiyamaa* and Kazuo Miyamuraa

aDepartment of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan
Correspondence e-mail: j1306709@ed.kagu.tus.ac.jp

In the title compound, C28H50S2, the alkyl chains adopt a fully extended all-trans conformation and each of them is almost perfectly planar. One of the alkyl chains is coplanar with the benzene ring and the other is twisted out of the benzene ring plane; the C-C-S-C torsion angles are 176.4 (2) and 80.8 (3)°. In the crystal structure, an intermolecular S...S interaction [3.2123 (13) Å] links the molecules into a centrosymmetric dimer; dimers are linked through weak C-H...[pi] and C-H...S interactions, forming a column along the a axis.

Related literature

For related literature, see: Alves et al. (2004[Alves, H., Simão, D., Santos, I. C., Gama, V., Henriques, R. T., Novais, H. & Almeida, M. (2004). Eur. J. Inorg. Chem. 6, 1318-1329.]); Huynh et al. (2002[Huynh, H. V., Schulze-Isfort, C., Seidel, W. W., Lugger, T., Frohlich, R., Kataeva, O. & Hahn, F. E. (2002). Chem. Eur. J. 8, 1327-1335.]); Liu et al. (2007[Liu, G.-X., Huang, L.-F. & Ren, X.-M. (2007). Appl. Organomet. Chem. 21 1054-1058.]); Robertson & Cronin (2002[Robertson, N. & Cronin, L. (2002). Coord. Chem. Rev. 227, 93-127.]); Salvatore et al. (2005[Salvatore, R. N., Smith, R. A., Nischwitz, A. K. & Gavin, T. (2005). Tetrahedron Lett. 46, 8931-8935.]); Tomiyama et al. (2007[Tomiyama, E., Tomono, K. & Miyamura, K. (2007). Acta Cryst. E63, m2741.]).

[Scheme 1]

Experimental

Crystal data

  • C28H50S2

  • Mr = 450.80

  • Monoclinic, P 21 /c

  • a = 5.4024 (10) Å

  • b = 16.863 (3) Å

  • c = 29.611 (5) Å

  • [beta] = 91.245 (3)°

  • V = 2696.9 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 100 (1) K

  • 0.55 × 0.11 × 0.10 mm
Data collection

  • Bruker SMART APEX CCD-detector diffractometer

  • Absorption correction: analytical (XPREP; Bruker 2000[Bruker (2000). XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.901, Tmax = 0.991

  • 15683 measured reflections

  • 5958 independent reflections

  • 4452 reflections with I > 2[sigma](I)

  • Rint = 0.086
Refinement

  • R[F2 > 2[sigma](F2)] = 0.087

  • wR(F2) = 0.205

  • S = 1.14

  • 5958 reflections

  • 273 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.75 e Å-3

  • [Delta][rho]min = -0.55 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C18-H18B...S1i 0.99 2.99 3.749 (4) 134
C7-H7A...Cgii 0.99 2.67 3.567 (16) 151
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z. Cg is the centroid of the C1-C6 ring.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97, KENX (Sakai, 2002[Sakai, K. (2002). KENX. Tokyo University of Science, Japan.]), ORTEPIII and Mercury.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2597 ).

References

Alves, H., Simão, D., Santos, I. C., Gama, V., Henriques, R. T., Novais, H. & Almeida, M. (2004). Eur. J. Inorg. Chem. 6, 1318-1329.  [CrossRef]
Bruker (2000). XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Huynh, H. V., Schulze-Isfort, C., Seidel, W. W., Lugger, T., Frohlich, R., Kataeva, O. & Hahn, F. E. (2002). Chem. Eur. J. 8, 1327-1335.  [CrossRef] [ChemPort]
Liu, G.-X., Huang, L.-F. & Ren, X.-M. (2007). Appl. Organomet. Chem. 21 1054-1058.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Robertson, N. & Cronin, L. (2002). Coord. Chem. Rev. 227, 93-127.  [ISI] [CrossRef] [ChemPort]
Sakai, K. (2002). KENX. Tokyo University of Science, Japan.
Salvatore, R. N., Smith, R. A., Nischwitz, A. K. & Gavin, T. (2005). Tetrahedron Lett. 46, 8931-8935.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tomiyama, E., Tomono, K. & Miyamura, K. (2007). Acta Cryst. E63, m2741.  [CrossRef] [details]

Acta Cryst (2008). E64, o1119  [ doi:10.1107/S1600536808014712 ]

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