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Volume 69 
Part 7 
Page o1112  
July 2013  

Received 30 May 2013
Accepted 7 June 2013
Online 19 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.094
Data-to-parameter ratio = 12.8
Details
Open access

4-(4-Methylphenylsulfonyl)piperazin-1-ium trifluoroacetate

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,bTadimety Aromatics Pvt Ltd, Hirehally Industrial Area, Tumkur, Karnataka 572 168 , India,cDepartment of Studies in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India,dDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and eSoild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

In the title salt, C11H17N2O2S+·CF3COO-, the cation is protonated at the secondary piperazine N atom. The dihedral angle between the benzene ring and the piperazine mean plane is 85.54 (10)°. In the crystal, cations and anions are connected by two types of strong N-H...O hydrogen bonds into chains extending along [101]. The chains are further assembled into (10-1) layers via stacking interactions between benzene rings of the cations [centroid-centroid distance = 3.7319 (13) Å] and a C-H...O interaction involving a piperazine C-H group and a sulfonyl O atom. Another C-H...O interaction between the piperazine ring and the sulfonyl group connects the ions into a three-dimensional network.

Related literature

For the synthesis, characterization and biological activity of piperazine 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.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C11H17N2O2S+·C2F3O2-

  • Mr = 354.35

  • Monoclinic, P 21 /n

  • a = 7.8796 (6) Å

  • b = 22.5891 (15) Å

  • c = 9.4626 (7) Å

  • [beta] = 110.446 (3)°

  • V = 1578.2 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 100 K

  • 0.24 × 0.22 × 0.20 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 = 0.941, Tmax = 0.950

  • 11562 measured reflections

  • 2781 independent reflections

  • 2417 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.094

  • S = 1.04

  • 2781 reflections

  • 217 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.86 e Å-3

  • [Delta][rho]min = -0.55 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H1N2...O4i 0.87 (3) 1.91 (3) 2.782 (2) 174 (2)
C8-H8B...O1ii 0.97 2.45 3.328 (2) 150
C9-H9B...O2iii 0.97 2.43 3.146 (2) 130
N2-H2N2...O3 0.86 (2) 1.86 (2) 2.690 (2) 163 (2)
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y, -z; (iii) x-1, y, z.

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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2578 ).


Acknowledgements

The authors thank Dr S. C. Sharma, Former Vice Chancellor, Tumkur University, Tumkur for his constant encouragement and Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for his help and valuable suggestions. BSPM thanks Dr H. C. Devaraje Gowda, Department of Physics Yuvarajas College (constituent), University of Mysore, for his guidance.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
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]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1112  [ doi:10.1107/S1600536813015900 ]

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