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Volume 68 
Part 5 
Page o1429  
May 2012  

Received 22 March 2012
Accepted 7 April 2012
Online 18 April 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.054
wR = 0.124
Data-to-parameter ratio = 14.3
Details
Open access

1,3-Bis[(naphthalen-2-ylsulfanyl)methyl]benzene

aInstituto de Química, Universidad Nacional Autónoma de México, Circuito exterior, Ciudad Universitaria, México, DF 04510, Mexico, 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, Mexico
Correspondence e-mail: rrm@uaem.mx

Molecules of the title compound, C28H22S2, are located on a crystallographic mirror plane with one half-molecule in the asymmetric unit. The dihedral angle between the phenyl ring and the naphthyl unit is 83.14 (7)°. In the crystal, molecules are interconnected by C-H...S and C-H...[pi] interactions.

Related literature

For information on pincer compounds, see: Albrecht & Morales-Morales (2009[Albrecht, M. & Morales-Morales, D. (2009). Iridium Complexes in Organic Synthesis, pp. 299-323. Germany: Wiley-VCH.]); Arroyo et al. (2003[Arroyo, M., Cervantes, R., Gómez-Benitez, V., López, P., Morales-Morales, D., Torrens, H. & Toscano, R. A. (2003). Synthesis, pp. 1565-1568.]); Morales-Morales (2004[Morales-Morales, D. (2004). Rev. Soc. Quim. Mex. 48, 338-346.], 2008[Morales-Morales, D. (2008). Modern Carbonylation Methods, pp. 20-64. Germany: Wiley-VCH.], 2009[Morales-Morales, D. (2009). Iridium Complexes in Organic Synthesis, pp. 325-344. Germany: Wiley-VCH.]); Morales-Morales & Jensen (2007[Morales-Morales, D. & Jensen, C. M. (2007). Editors. The Chemistry of Pincer Compounds. Amsterdam: Elsevier.]).

[Scheme 1]

Experimental

Crystal data
  • C28H22S2

  • Mr = 422.58

  • Orthorhombic, P n m a

  • a = 8.651 (2) Å

  • b = 41.235 (10) Å

  • c = 6.0517 (14) Å

  • V = 2158.9 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 298 K

  • 0.48 × 0.42 × 0.07 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: analytical (SADABS; Bruker; 2007[Bruker (2007). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.893, Tmax = 0.979

  • 7907 measured reflections

  • 1994 independent reflections

  • 1345 reflections with I > 2[sigma](I)

  • Rint = 0.065

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.124

  • S = 1.02

  • 1994 reflections

  • 139 parameters

  • H-atom parameters not refined

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C4/C2'/C3' and C6-C9/C14/C15 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C5-H5B...S1i 0.97 2.86 3.806 (4) 164
C1-H1...Cg1i 0.93 2.94 3.867 (4) 173
C13-H13...Cg2ii 0.93 2.76 3.503 (3) 138
Symmetry codes: (i) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5855 ).


Acknowledgements

RRM thanks CONACYT for a posdoctoral scholarship (agreement No. 290586-UNAM). Support of this research was provided by CONACYT (grant No. 154732) and PAPIIT (grant No. IN201711). DMM would like acknowledge Dr Ruben A. Toscano for technical assistance.

References

Albrecht, M. & Morales-Morales, D. (2009). Iridium Complexes in Organic Synthesis, pp. 299-323. Germany: Wiley-VCH.
Arroyo, M., Cervantes, R., Gómez-Benitez, V., López, P., Morales-Morales, D., Torrens, H. & Toscano, R. A. (2003). Synthesis, pp. 1565-1568.  [ISI] [CSD] [CrossRef]
Bruker (2007). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Morales-Morales, D. (2004). Rev. Soc. Quim. Mex. 48, 338-346.  [ChemPort]
Morales-Morales, D. (2008). Modern Carbonylation Methods, pp. 20-64. Germany: Wiley-VCH.
Morales-Morales, D. (2009). Iridium Complexes in Organic Synthesis, pp. 325-344. Germany: Wiley-VCH.
Morales-Morales, D. & Jensen, C. M. (2007). Editors. The Chemistry of Pincer Compounds. Amsterdam: Elsevier.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o1429  [ doi:10.1107/S1600536812015280 ]

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