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Volume 69 
Part 2 
Page o306  
February 2013  

Received 22 January 2013
Accepted 23 January 2013
Online 31 January 2013

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Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.005 Å
R = 0.055
wR = 0.143
Data-to-parameter ratio = 17.1
Details
Open access

1,3-Bis[(tert-butylsulfanyl)methyl]-2,4,6-trimethylbenzene

Evelyn Paz-Morales,a Manuel Basauri-Molina,a Juan Manuel Germán-Acacio,b Reyna Reyes-Martíneza and David Morales-Moralesa*

aInstituto de Química, Universidad Nacional Autónoma de México, Circuito exterior, Ciudad Universitaria, México, D.F., 04510, México, and bCiencias Básicas e Ingeniería, Recursos de la Tierra, Universidad Autónoma, Metropolitana. Av. Hidalgo Poniente, La Estación Lerma, Lerma de Villada Estado de México, CP 52006, México
Correspondence e-mail: damor@unam.mx

The complete molecule of the title compound, C19H32S2, is generated by crystallorgaphic twofold symmetry, with three C atoms lying on the axis. The Car-C-S-C (ar = aromatic) torsion angle is 156.2 (2) °. In the crystal, the molecules are linked by very weak C-H...S interactions, generating [001] chains.

Related literature

For pincer complexes, see: Morales-Morales et al. (2007[Morales-Morales, D. & Jensen, C. M. (2007). Editors. The Chemistry of Pincer Compounds. Amsterdam: Elsevier.]); Morales-Morales (2004[Morales-Morales, D. (2004). Rev. Soc. Quim. Mex. 48, 338-346.]); Serrano-Becerra & Morales-Morales (2009[Serrano-Becerra, J. M. & Morales-Morales, D. (2009). Curr. Org. Synth. 6, 169-192.]). For uses of SCS pincer complexes in catalysis, see: Morales-Morales et al. (2007[Morales-Morales, D. & Jensen, C. M. (2007). Editors. The Chemistry of Pincer Compounds. Amsterdam: Elsevier.]); Singleton (2003[Singleton, J. T. (2003). Tetrahedron, 59, 1837-1857.]). For the structure of the pincer SCS ligand 1,3-bis[(naphthalen-2-ylsufanyl)methyl]benzene, see: Padilla-Mata et al. (2012[Padilla-Mata, E., German-Acacio, J. M., García-Eleno, M. A., Reyes-Martínez, R. & Morales-Morales, D. (2012). Acta Cryst. E68, o1429.]).

[Scheme 1]

Experimental

Crystal data

  • C19H32S2

  • Mr = 324.57

  • Monoclinic, C 2/c

  • a = 14.870 (4) Å

  • b = 14.233 (3) Å

  • c = 9.245 (2) Å

  • [beta] = 103.693 (4)°

  • V = 1901.1 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 298 K

  • 0.34 × 0.09 × 0.06 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • 10088 measured reflections

  • 1743 independent reflections

  • 1022 reflections with I > 2[sigma](I)

  • Rint = 0.084
Refinement

  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.143

  • S = 0.93

  • 1743 reflections

  • 102 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10A...S1i 0.96 3.11 3.980 (5) 151
Symmetry code: (i) [x, -y+1, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7031 ).

Acknowledgements

EP-M and RR-M (postdoctoral agreements No. 290662 and 290586 UNAM) would like to thank CONACYT for scholarships. The financial support of this research by CONACYT (CB2010-154732) and DGAPA-UNAM (IN201711) is gratefully acknowledged. JMG-A would like to thank the Universidad Autónoma Metropolitana, Unidad Lerma, for financial support. DM-M acknowledges Dr Simón Hernández-Ortega for technical assistance.

References

Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Morales-Morales, D. (2004). Rev. Soc. Quim. Mex. 48, 338-346.  [ChemPort]
Morales-Morales, D. & Jensen, C. M. (2007). Editors. The Chemistry of Pincer Compounds. Amsterdam: Elsevier.
Padilla-Mata, E., German-Acacio, J. M., García-Eleno, M. A., Reyes-Martínez, R. & Morales-Morales, D. (2012). Acta Cryst. E68, o1429.  [CrossRef] [details]
Serrano-Becerra, J. M. & Morales-Morales, D. (2009). Curr. Org. Synth. 6, 169-192.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singleton, J. T. (2003). Tetrahedron, 59, 1837-1857.  [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2013). E69, o306  [ doi:10.1107/S1600536813002249 ]

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