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Volume 69 
Part 2 
Page o239  
February 2013  

Received 24 December 2012
Accepted 4 January 2013
Online 16 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.119
Data-to-parameter ratio = 13.7
Details
Open access

1-Tosyl-4-[2-(trifluoromethyl)benzyl]piperazine

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,bDepartment of Physics, Karnatak University, Dharwad, Karnataka 580 003, India,cDepartment of Studies and Research in Chemistry, UCS, Tumkur University, Tumkur, Karnataka 572 103, India, and dDepartment of Studies and Research in Physics, UCS, Tumkur University, Tumkur, Karnataka 572 103, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

In the crystal structure of the title compound, C19H21F3N2O2S, the piperazine ring adopts a chair conformation. The dihedral angles between the mean plane of the piperazine ring and the tosyl and trifluoromethylphenyl rings are 74.52 (3) and 68.30 (2)°, respectively. The sulfonamide N atom deviates from the plane defined by the three attached atoms by 0.327 (1) Å. The crystal structure is stabilized by weak C-H...[pi] interactions.

Related literature

For the synthesis, characterization and biological activity of piperazine and its derivatives, see: Gan et al. (2009a[Gan, L.-L., Cai, J.-L. & Zhou, C.-H. (2009a). Chin. Pharm. J. 44, 1361-1368.],b[Gan, L.-L., Lu, Y.-H. & Zhou, C.-H. (2009b). Chin. J. Biochem. Pharm. 30, 127-131.])

[Scheme 1]

Experimental

Crystal data
  • C19H21F3N2O2S

  • Mr = 398.44

  • Triclinic, [P \overline 1]

  • a = 9.5044 (3) Å

  • b = 9.8389 (3) Å

  • c = 12.1473 (4) Å

  • [alpha] = 72.036 (1)°

  • [beta] = 77.024 (1)°

  • [gamma] = 62.384 (1)°

  • V = 952.96 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 296 K

  • 0.28 × 0.26 × 0.24 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.942, Tmax = 0.950

  • 18514 measured reflections

  • 3359 independent reflections

  • 2981 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.119

  • S = 1.08

  • 3359 reflections

  • 245 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.53 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the benzene ring of the trifluoromethylphenyl group (C1-C6).

D-H...A D-H H...A D...A D-H...A
C11-H11A...Cgi 0.97 2.84 (1) 3.670 (2) 144
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2548 ).


Acknowledgements

The authors thank Dr S. C. Sharma, Vice Chancellor, Tumkur University, Tumkur, for his constant encouragement. JT thanks DST, New Delhi, for the SCXRD facility under a PURSE Grant (SR/S9/Z-23/2008/11, 2009) at USIC, Karnatak University.

References

Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gan, L.-L., Cai, J.-L. & Zhou, C.-H. (2009a). Chin. Pharm. J. 44, 1361-1368.  [ChemPort]
Gan, L.-L., Lu, Y.-H. & Zhou, C.-H. (2009b). Chin. J. Biochem. Pharm. 30, 127-131.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o239  [ doi:10.1107/S1600536813000317 ]

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