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Volume 69 
Part 11 
Page o1670  
November 2013  

Received 13 October 2013
Accepted 14 October 2013
Online 19 October 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.043
wR = 0.123
Data-to-parameter ratio = 13.5
Details
Open access

Methyl 2-[4-(tri­fluoro­meth­yl)phenyl­sulfan­yl]benzoate

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C15H13F3O2S, the dihedral angle between the benzene rings is 79.5 (1)°. The ester group is twisted by 7.6 (1)° from the mean plane of the adjacent benzene ring. Disorder was modeled over two sites for one F atom of the tri­fluoro­methyl group with an occupancy ratio of 0.54 (6):0.46 (6). In the crystal, mol­ecules are linked via weak C-H...O hydrogen bonds, forming two-dimensional networks lying parallel to (101). The networks are linked via C-H...[pi] inter­actions, leading to the formation of a three-dimensional supra­molecular structure.

Related literature

For general background and pharmacological properties of the neuroleptic agent flupentixol [systematic name: (EZ)-2-[4-[3-[2-(tri­fluoro­meth­yl)thioxanthen-9-yl­idene]prop­yl]pip­era­zin-1-yl]ethanol] and related compounds, see: Ovhed (1976[Ovhed, I. (1976). Curr. Med. Res. Opin. 4, 144-150.]); Robertson & Trimble (1981[Robertson, M. M. & Trimble, M. R. (1981). Practitioner, 225, 761-763.]); Valle-Jones & Swarbrick (1981[Valle-Jones, J. C. & Swarbrick, D. J. (1981). Curr. Med. Res. Opin. 1, 543-549.]); Young et al. (1976[Young, J. P. R., Hughes, W. C. & Lader, M. H. (1976). Br. Med. J. (Clin. Res. Ed.), 1, 1116-1118.]). For related structures, see: Post et al. (1975a[Post, M. L., Kennard, O. & Horn, A. S. (1975a). Acta Cryst. B31, 2724-2726.],b[Post, M. L., Kennard, O., Sheldrick, G. M. & Horn, A. S. (1975b). Acta Cryst. B31, 2366-2368.]); Siddegowda et al. (2011a[Siddegowda, M. S., Butcher, R. J., Akkurt, M., Yathirajan, H. S. & Narayana, B. (2011a). Acta Cryst. E67, o2079-o2080.],b[Siddegowda, M. S., Butcher, R. J., Akkurt, M., Yathirajan, H. S. & Ramesh, A. R. (2011b). Acta Cryst. E67, o2017-o2018.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C15H11F3O2S

  • Mr = 312.30

  • Monoclinic, P 21 /c

  • a = 11.0675 (5) Å

  • b = 8.0429 (3) Å

  • c = 15.6614 (7) Å

  • [beta] = 96.654 (5)°

  • V = 1384.70 (11) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.44 mm-1

  • T = 173 K

  • 0.28 × 0.22 × 0.12 mm

Data collection
  • Agilent Gemini EOS diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.715, Tmax = 1.000

  • 8110 measured reflections

  • 2705 independent reflections

  • 2224 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.123

  • S = 1.03

  • 2705 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2-C7 benzene ring.

D-H...A D-H H...A D...A D-H...A
C15-H15C...O2i 0.96 2.45 3.221 (3) 138
C12-H12...Cgii 0.93 2.70 3.558 (2) 154
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+2, -y, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2658 ).


Acknowledgements

TSY thanks the University of Mysore for research facilities and is also grateful to the Principal, Maharani's Science College for women, Mysore, for giving permission to do research. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ovhed, I. (1976). Curr. Med. Res. Opin. 4, 144-150.  [CrossRef] [ChemPort] [PubMed]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Post, M. L., Kennard, O. & Horn, A. S. (1975a). Acta Cryst. B31, 2724-2726.  [CSD] [CrossRef] [IUCr Journals] [Web of Science]
Post, M. L., Kennard, O., Sheldrick, G. M. & Horn, A. S. (1975b). Acta Cryst. B31, 2366-2368.  [CSD] [CrossRef] [IUCr Journals] [Web of Science]
Robertson, M. M. & Trimble, M. R. (1981). Practitioner, 225, 761-763.  [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Siddegowda, M. S., Butcher, R. J., Akkurt, M., Yathirajan, H. S. & Narayana, B. (2011a). Acta Cryst. E67, o2079-o2080.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Siddegowda, M. S., Butcher, R. J., Akkurt, M., Yathirajan, H. S. & Ramesh, A. R. (2011b). Acta Cryst. E67, o2017-o2018.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Valle-Jones, J. C. & Swarbrick, D. J. (1981). Curr. Med. Res. Opin. 1, 543-549.
Young, J. P. R., Hughes, W. C. & Lader, M. H. (1976). Br. Med. J. (Clin. Res. Ed.), 1, 1116-1118.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1670  [ doi:10.1107/S1600536813028146 ]

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