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Volume 69 
Part 11 
Page o1625  
November 2013  

Received 24 September 2013
Accepted 30 September 2013
Online 9 October 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.055
wR = 0.170
Data-to-parameter ratio = 17.1
Details
Open access

4-[(4-Methyl­phen­yl)sulfan­yl]butan-2-one

aVinca Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, PO Box 522, University of Belgrade, 11001 Belgrade, Serbia,bFaculty of Metallurgy and Technology, University of Montenegro, Cetinjski put bb, 81000 Podgorica, Montenegro, and cFaculty of Sciences, Department of Chemistry, University of Kragujevac, R. Domanovica 12, 34000 Kragujevac, Serbia
Correspondence e-mail: zorica@ac.me

In the title compound, C11H14OS, all non-H atoms are essentially coplanar, with a mean deviation of 0.023 Å. In the crystal, centrosymmetrically related mol­ecules are weakly connected into dimers by pairs of C-H...O inter­actions. The dimers are further linked along the a axis by weak C-H...[pi] and C-H...S inter­actions.

Related literature

For the physico-chemical properties of organosulfur compounds, see: Page (1999[Page, P. C. B. (1999). Editor. Organosulfur Chemistry, Vols. 1-2. Berlin: Springer.]). For the synthetic procedure, see: Stevanovic et al. (2012[Stevanovic, D., Pejovic, A., Damljanovic, I., Vukicevic, M., Bogdanovic, G. A. & Vukicevic, R. D. (2012). Tetrahedron Lett. 53, 6257-6260.]). For the role of sulfur in hydrogen bonding, see: Francuski et al. (2011[Francuski, B. M., Novakovic, S. B. & Bogdanovic, G. A. (2011). CrystEngComm, 13, 3580-3591.]).

[Scheme 1]

Experimental

Crystal data
  • C11H14OS

  • Mr = 194.28

  • Triclinic, [P \overline 1]

  • a = 7.2703 (11) Å

  • b = 7.3226 (7) Å

  • c = 11.7615 (11) Å

  • [alpha] = 88.232 (8)°

  • [beta] = 79.343 (10)°

  • [gamma] = 61.350 (13)°

  • V = 538.80 (13) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 2.33 mm-1

  • T = 293 K

  • 0.50 × 0.26 × 0.14 mm

Data collection
  • Agilent Gemini S diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Tmin = 0.444, Tmax = 1.000

  • 3254 measured reflections

  • 2052 independent reflections

  • 1731 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.170

  • S = 1.07

  • 2052 reflections

  • 120 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C4-C9 phenyl ring.

D-H...A D-H H...A D...A D-H...A
C10-H10c...O1i 0.96 2.67 3.579 (4) 158
C3-H3a...S1ii 0.97 2.99 3.855 (3) 149
C3-H3b...S1iii 0.97 3.02 3.870 (3) 147
C2-H2a...Cgii 0.97 2.86 3.628 (4) 137
C2-H2b...Cgiv 0.97 2.95 3.678 (4) 133
Symmetry codes: (i) -x+1, -y, -z-1; (ii) -x, -y, -z; (iii) -x+1, -y, -z; (iv) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]); 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 (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: RZ5084 ).


Acknowledgements

This work was supported by the Ministry of Education, Science and Technological Development of the Republic of Serbia (Projects No. 172014, 172035 and 172034).

References

Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Francuski, B. M., Novakovic, S. B. & Bogdanovic, G. A. (2011). CrystEngComm, 13, 3580-3591.  [Web of Science] [CSD] [CrossRef] [ChemPort]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [IUCr Journals]
Page, P. C. B. (1999). Editor. Organosulfur Chemistry, Vols. 1-2. Berlin: Springer.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Stevanovic, D., Pejovic, A., Damljanovic, I., Vukicevic, M., Bogdanovic, G. A. & Vukicevic, R. D. (2012). Tetrahedron Lett. 53, 6257-6260.


Acta Cryst (2013). E69, o1625  [ doi:10.1107/S1600536813026895 ]

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