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Volume 69 
Part 7 
Page o1179  
July 2013  

Received 3 June 2013
Accepted 13 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.005 Å
R = 0.045
wR = 0.114
Data-to-parameter ratio = 10.7
Details
Open access

1-(3,4-Difluorobenzyl)-4-(4-methylphenylsulfonyl)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, 572 103, India,cDepartment of Studies and Research in Physics, U.C.S. Tumkur University, Tumkur Karnataka 572 103, India, and dDepartment of Physics, Karnatak University, Dharwad, Karnataka 580 003, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

In the title compound, C18H20F2N2O2S, the central piperazine ring adopts a chair conformation. The dihedral angle between the two benzene rings is 40.20°, whereas those between the piperazine ring (considering the best fit plane through all the non-H atoms) and the sulfonyl-bound benzene and difluorobenzene rings are 74.96 and 86.16°, respectively. In the crystal, molecules are stacked along the a axis through weak C-H...O and C-H...F interactions.

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.],c[Sreenivasa, S., ManojKumar, K. E., Anitha, H. C., Suchetan, P. A., Palakshamurthy, B. S., Jayashree, Y. & Tonannavar, J. (2013c). Acta Cryst. E69, o782.]).

[Scheme 1]

Experimental

Crystal data
  • C18H20F2N2O2S

  • Mr = 366.42

  • Monoclinic, P 21 /c

  • a = 6.6680 (2) Å

  • b = 36.0404 (8) Å

  • c = 7.6093 (2) Å

  • [beta] = 99.728 (2)°

  • V = 1802.35 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 298 K

  • 0.28 × 0.24 × 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 = 0.943, Tmax = 0.959

  • 9583 measured reflections

  • 2434 independent reflections

  • 1910 reflections with I > 2[sigma](I)

  • Rint = 0.025

  • [theta]max = 22.8°

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.114

  • S = 1.02

  • 2434 reflections

  • 227 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 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
C3-H3...O1i 0.93 2.67 3.380 (4) 134
C7-H7A...O1ii 0.96 2.66 3.400 (4) 134
C10-H10B...F1iii 0.97 2.66 3.585 (3) 160
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+1, -z+2; (iii) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

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: SJ5330 ).


Acknowledgements

The authors thank Dr S. C. Sharma, Ex-Vice Chancellor, Tumkur University, for his constant encouragement. JT also thanks the DST, New Delhi, for the SCXRD facility under the 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.
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]
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] [IUCr Journals]
Sreenivasa, S., ManojKumar, K. E., Anitha, H. C., Suchetan, P. A., Palakshamurthy, B. S., Jayashree, Y. & Tonannavar, J. (2013c). Acta Cryst. E69, o782.  [CrossRef] [IUCr Journals]
Sreenivasa, S., ManojKumar, K. E., Suchetan, P. A., Tonannavar, J., Chavan, Y. & Palakshamurthy, B. S. (2013b). Acta Cryst. E69, o185.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1179  [ doi:10.1107/S1600536813016462 ]

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