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Volume 69 
Part 11 
Page o1704  
November 2013  

Received 13 October 2013
Accepted 20 October 2013
Online 26 October 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.054
wR = 0.155
Data-to-parameter ratio = 12.5
Details
Open access

2-[4-(Tri­fluoro­meth­yl)phenyl­sulfan­yl]benzoic acid

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, C14H9F3O2S, the dihedral angle between the mean planes of the benzene rings is 88.7 (2)°. The carb­oxy­lic acid group is twisted by 13.6 (7)° from the mean plane of its attached aromatic ring. One of the F atoms of the tri­fluoro­methyl group is disordered over two sites in a 0.61 (7):0.39 (7) ratio. In the crystal, inversion dimers linked by pairs of O-H...O hydrogen bonds generate R22(8) loops. Weak C-H...F inter­actions are also observed.

Related literature

For background to the neuroleptic agent flupentixol (systematic name: (EZ)-2-[4-[3-[2-(tri­fluoro­meth­yl)thio­xan­then-9-yl­idene]prop­yl]piperazin-1-yl]ethanol), see: Young et al. (1976[Young, J. P. R., Hughes, W. C. & Lader, M. H. (1976). Br. Med. J. 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.]).

[Scheme 1]

Experimental

Crystal data
  • C14H9F3O2S

  • Mr = 298.28

  • Triclinic, [P \overline 1]

  • a = 7.3071 (5) Å

  • b = 8.0790 (7) Å

  • c = 11.3878 (11) Å

  • [alpha] = 82.678 (8)°

  • [beta] = 83.642 (7)°

  • [gamma] = 72.309 (7)°

  • V = 633.41 (10) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 2.63 mm-1

  • T = 173 K

  • 0.24 × 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 = 0.848, Tmax = 1.000

  • 3701 measured reflections

  • 2419 independent reflections

  • 2049 reflections with I > 2[sigma](I)

  • Rint = 0.038

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

  • wR(F2) = 0.155

  • S = 1.04

  • 2419 reflections

  • 193 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.71 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O1i 0.82 1.86 2.677 (3) 175
C6-H6...F3ii 0.93 2.59 3.319 (10) 136
C6-H6...F3Aii 0.93 2.50 3.294 (16) 144
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+2, -y+1, -z+2.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); data reduction: CrysAlis RED; 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: HB7150 ).


Acknowledgements

TSY thanks University of Mysore for research facilities and is also grateful to the Principal, Maharani's Science College for Women, Mysore, for giving permission to undertake 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.
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]
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]
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]
Young, J. P. R., Hughes, W. C. & Lader, M. H. (1976). Br. Med. J. 1, 1116-1118.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1704  [ doi:10.1107/S1600536813028778 ]

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