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

Sreenivasa, S.; Anitha, H.C.; ManojKumar, K.E.; Tonannavar, J.; Jayashree, Y.; Suchetan, P.A.; Palakshamurthy, B.S.

doi:10.1107/S1600536813000317

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 (C-C) = 0.003 Å
R = 0.042
wR = 0.119
Data-to-parameter ratio = 13.7
Details

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

S. Sreenivasa,^a ^* H. C. Anitha,^a K. E. ManojKumar,^a J. Tonannavar,^b Yenagi Jayashree,^b P. A. Suchetan ^c and B. S. Palakshamurthy ^d

^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,b)

Experimental

Crystal data

C₁₉H₂₁F₃N₂O₂S
M_r = 398.44
Triclinic, $[P \overline 1]$
a = 9.5044 (3) Å
b = 9.8389 (3) Å
c = 12.1473 (4) Å
= 72.036 (1)°
= 77.024 (1)°
= 62.384 (1)°
V = 952.96 (5) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.942, T_max = 0.950
18514 measured reflections
3359 independent reflections
2981 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.119
S = 1.08
3359 reflections
245 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C11-H11ACgⁱ	0.97	2.84 (1)	3.670 (2)	144
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); 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.
Gan, L.-L., Cai, J.-L. & Zhou, C.-H. (2009a). Chin. Pharm. J. 44, 1361-1368.
Gan, L.-L., Lu, Y.-H. & Zhou, C.-H. (2009b). Chin. J. Biochem. Pharm. 30, 127-131.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds