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Volume 69 
Part 5 
Page o782  
May 2013  

Received 29 March 2013
Accepted 13 April 2013
Online 24 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.109
Data-to-parameter ratio = 15.8
Details
Open access

An unknown solvate of 1-(2,4-dichlorobenzyl)-4-[(4-methylphenyl)sulfonyl]piperazine

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,bCenter for Advanced Materials and Department of Chemistry, Tumkur University Tumkur, Karnataka 572103, India,cDepartment of Studies and Research 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 eDepartment of Physics, Karnatak University, Dharwad, Karnataka 580 003, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

In the title compound, C18H20Cl2N2O2S, the piperazine ring adopts a chair conformation. The dihedral angle between the sulfonyl-bound benzene ring and the best-fit plane through the six non-H atoms of the piperazine ring is 72.22 (12)°; those between the dichlorobenzene ring and the sulfonyl and piperazine rings are 2.44 (13) and 74.16 (2)°, respectively. In the crystal, molecules are connected through weak C-H...O interactions into a hexameric unit generating a R66(60) motif in the ab plane. The molecules are also connected into C(4) chains through weak C-H...N interactions. The solvent used to grow the crystal was a mixture of dichloromethane and methanol, but the resulting electron density was uninterpretable. The solvent contribution to the scattering was removed with the SQUEEZE routine in PLATON [Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). Acta Cryst. D65, 148-155]. The formula mass and unit-cell characteristics do not take into account the disordered solvent.

Related literature

For similar structures, see: Sreenivasa et al. (2013a[Sreenivasa, S., Anitha, H. C., ManojKumar, K. E., Tonannavar, J., Jayashree, Y., Suchetan, P. A. & Palakshamurthy, B. S. (2013a). Acta Cryst. E69, o239.],b[Sreenivasa, S., ManojKumar, K. E., Suchetan, P. A., Tonannavar, J., Chavan, Y. & Palakshamurthy, B. S. (2013b). Acta Cryst. E69, o185.]).

[Scheme 1]

Experimental

Crystal data
  • C18H20Cl2N2O2S

  • Mr = 399.32

  • Trigonal, [R \overline 3]

  • a = 28.2896 (5) Å

  • c = 13.3041 (3) Å

  • V = 9220.8 (3) Å3

  • Z = 18

  • Mo K[alpha] radiation

  • [mu] = 0.43 mm-1

  • T = 296 K

  • 0.31 × 0.23 × 0.19 mm

Data collection
  • Bruker APEXII diffractometer

  • 15194 measured reflections

  • 3596 independent reflections

  • 2637 reflections with I > 2[sigma](I)

  • Rint = 0.033

  • 3608 standard reflections every 22 reflections intensity decay: 1.0%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.109

  • S = 0.95

  • 3596 reflections

  • 227 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C18-H18...O2i 0.93 2.70 3.575 (3) 157
C17-H17...N2ii 0.93 2.70 3.485 (3) 143
Symmetry codes: (i) [y+{\script{1\over 3}}, -x+y+{\script{2\over 3}}, -z+{\script{5\over 3}}]; (ii) [-x+y+{\script{2\over 3}}, -x+{\script{1\over 3}}, z+{\script{1\over 3}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, 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: TK5213 ).


Acknowledgements

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

References

Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
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.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Sreenivasa, S., Anitha, H. C., ManojKumar, K. E., Tonannavar, J., Jayashree, Y., Suchetan, P. A. & Palakshamurthy, B. S. (2013a). Acta Cryst. E69, o239.  [CSD] [CrossRef] [details]
Sreenivasa, S., ManojKumar, K. E., Suchetan, P. A., Tonannavar, J., Chavan, Y. & Palakshamurthy, B. S. (2013b). Acta Cryst. E69, o185.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o782  [ doi:10.1107/S160053681301012X ]

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