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Volume 69 
Part 2 
Pages o285-o286  
February 2013  

Received 9 January 2013
Accepted 17 January 2013
Online 23 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.113
Data-to-parameter ratio = 15.2
Details
Open access

Benzyl 2-(benzylsulfanyl)benzoate

aFaculty of Metallurgy and Technology, University of Montenegro, Cetinjski put bb, 81000 Podgorica, Montenegro,bVinca Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, University of Belgrade, PO Box 522, 11001 Belgrade, Serbia,cFaculty of Medical Sciences, University of Kragujevac, S. Markovica 69, 34000 Kragujevac, Serbia, and dDepartment of Chemistry, Faculty of Science, University of Kragujevac, R. Domanovica 12, 34000 Kragujevac, Serbia
Correspondence e-mail: zorica@ac.me

In the title compound, C21H18O2S, the central aromatic ring makes dihedral angles of 5.86 (12) and 72.02 (6)° with the rings of the terminal O-benzyl and S-benzyl groups, respectively. The dihedral angle between the peripheral phenyl rings is 66.16 (6)°. In the crystal, molecules are linked by pairs of C-H...O hydrogen bonds, forming inversion dimers. These dimers are linked via C-H...[pi] interactions, forming a three-dimensional network.

Related literature

For related structures, see: Radic et al. (2012[Radic, G. P., Glodjovic, V. V., Radojevic, I. D., Stefanovic, O. D., Comic, Lj. R., Ratkovic, Z. R., Valkonen, A., Rissanen, K. & Trifunovic, S. R. (2012). Polyhedron, 31, 69-76.]); Lucena et al. (1996[Lucena, N., Casabó, J., Escriche, L., Sánchez-Castelló, G., Teixidor, F., Kivekäs, R. & Sillanpää, R. (1996). Polyhedron, 15, 3009-3018.]); Sillanpää et al. (1994[Sillanpää, R., Kivekäs, R., Escriche, L., Lucena, N., Teixidor, F. & Casabó, J. (1994). Acta Cryst. C50, 2049-2051.]); Alhadi et al. (2010[Alhadi, A. A., Khaledi, H., Mohd Ali, H. & Olmstead, M. M. (2010). Acta Cryst. E66, o1787.]). For the biological activity of thiosalicylic acid derivatives, see: Bernardelli et al. (2005[Bernardelli, P., Cronin, A. M., Denis, A., Denton, S. M., Jacobelli, H., Kemp, M. I., Lorthiois, E., Rousseau, F., Serradeil-Civit, D. & Vergne, F. (2005). US Patent 20050267095.]); Halaschek-Wiener et al. (2003[Halaschek-Wiener, J., Kloog, Y., Wacheck, V. & Jansen, B. (2003). J. Invest. Dermatol. 120, 109-115.]); Sadao et al. (2000[Sadao, I., Fujio, S., Hidekazu, M. & Keita, K. (2000). Jpn Patent 2000-178188.]).

[Scheme 1]

Experimental

Crystal data
  • C21H18O2S

  • Mr = 334.41

  • Triclinic, [P \overline 1]

  • a = 5.6957 (3) Å

  • b = 12.1117 (11) Å

  • c = 13.0813 (11) Å

  • [alpha] = 72.748 (8)°

  • [beta] = 86.477 (6)°

  • [gamma] = 89.941 (6)°

  • V = 860.04 (12) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 1.74 mm-1

  • T = 293 K

  • 0.11 × 0.10 × 0.05 mm

Data collection
  • Oxford Diffraction Xcalibur Gemini Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2012[Oxford Diffraction (2012). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.944, Tmax = 1.000

  • 5368 measured reflections

  • 3299 independent reflections

  • 2554 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.113

  • S = 1.04

  • 3299 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Geometry of hydrogen bonds and weak C-H...[pi] interactions (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C2-C7, C9-C14 and C16-C21 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C14-H14...O2i 0.93 2.63 3.408 (3) 142
C4-H4...Cg3ii 0.93 3.11 3.846 (3) 137
C13-H13...Cg3i 0.93 2.88 3.653 (3) 141
C18-H18...Cg1iii 0.93 3.20 3.820 (3) 126
C20-H20...Cg2iv 0.93 2.96 3.651 (3) 132
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+2, -y, -z+1; (iii) -x+1, -y, -z+1; (iv) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2012[Oxford Diffraction (2012). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), PLATON (Spek, 2009)[Spek, A. L. (2009). Acta Cryst. D65, 148-155.] and PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5036 ).


Acknowledgements

This work was supported by the Ministry of Education and Science of the Republic of Serbia (Project Nos. 172016, 172034, 172014 and 172035). We thank Professor V. Divjakovic, University of Novi Sad, for help with the X-ray data collection.

References

Alhadi, A. A., Khaledi, H., Mohd Ali, H. & Olmstead, M. M. (2010). Acta Cryst. E66, o1787.  [CSD] [CrossRef] [details]
Bernardelli, P., Cronin, A. M., Denis, A., Denton, S. M., Jacobelli, H., Kemp, M. I., Lorthiois, E., Rousseau, F., Serradeil-Civit, D. & Vergne, F. (2005). US Patent 20050267095.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Halaschek-Wiener, J., Kloog, Y., Wacheck, V. & Jansen, B. (2003). J. Invest. Dermatol. 120, 109-115.  [PubMed] [ChemPort]
Lucena, N., Casabó, J., Escriche, L., Sánchez-Castelló, G., Teixidor, F., Kivekäs, R. & Sillanpää, R. (1996). Polyhedron, 15, 3009-3018.  [CrossRef] [ChemPort] [ISI]
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]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Oxford Diffraction (2012). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Radic, G. P., Glodjovic, V. V., Radojevic, I. D., Stefanovic, O. D., Comic, Lj. R., Ratkovic, Z. R., Valkonen, A., Rissanen, K. & Trifunovic, S. R. (2012). Polyhedron, 31, 69-76.
Sadao, I., Fujio, S., Hidekazu, M. & Keita, K. (2000). Jpn Patent 2000-178188.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sillanpää, R., Kivekäs, R., Escriche, L., Lucena, N., Teixidor, F. & Casabó, J. (1994). Acta Cryst. C50, 2049-2051.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o285-o286   [ doi:10.1107/S1600536813001761 ]

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