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

Padilla-Mata, E.; German-Acacio, J.M.; García-Eleno, M.A.; Reyes-Martínez, R.; Morales-Morales, D.

doi:10.1107/S1600536812015280

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 (C-C) = 0.004 Å
R = 0.054
wR = 0.124
Data-to-parameter ratio = 14.3
Details

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

Esteban Padilla-Mata,^a Juan M. German-Acacio,^b Marco A. García-Eleno,^a Reyna Reyes-Martínez ^a ^* and David Morales-Morales ^a

^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-HS and C-H [pi] interactions.

Related literature

For information on pincer compounds, see: Albrecht & Morales-Morales (2009); Arroyo et al. (2003); Morales-Morales (2004, 2008, 2009); Morales-Morales & Jensen (2007).

Experimental

Crystal data

C₂₈H₂₂S₂
M_r = 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 radiation
= 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) T_min = 0.893, T_max = 0.979
7907 measured reflections
1994 independent reflections
1345 reflections with I > 2(I)
R_int = 0.065

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.124
S = 1.02
1994 reflections
139 parameters
H-atom parameters not refined
_max = 0.21 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C5-H5BS1ⁱ	0.97	2.86	3.806 (4)	164
C1-H1Cg1ⁱ	0.93	2.94	3.867 (4)	173
C13-H13Cg2ⁱⁱ	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); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); 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.
Bruker (2007). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Morales-Morales, D. (2004). Rev. Soc. Quim. Mex. 48, 338-346.
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.

organic compounds