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Volume 69 
Part 2 
Page o185  
February 2013  

Received 19 December 2012
Accepted 22 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.033
wR = 0.092
Data-to-parameter ratio = 10.0
Details
Open access

(2,3-Difluorophenyl)(4-tosylpiperazin-1-yl)methanone

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

In the title compound, C18H18F2N2O3S, the piperazine ring adopts a chair conformation. The dihedral angle between the sulfonyl-bound benzene ring and the best fit plane throught the six non-H atoms of the piperazine ring is 69.4 (2)°, while those between the fluorobenzene and sulfonyl rings and the fluorobenzene and piperazine rings are 30.97 (2) and 75.98 (2)°, respectively. In the crystal, molecules are connected to form a tetrameric unit through C-H...O hydrogen bonds. The structure is further stabilized by weak intermolecular C-H...F interactions, generating C(8) and C(7) chains running along [100].

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.]). 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
  • C18H18F2N2O3S

  • Mr = 380.40

  • Monoclinic, P 21 /c

  • a = 17.0456 (4) Å

  • b = 7.6026 (1) Å

  • c = 15.5113 (3) Å

  • [beta] = 113.513 (1)°

  • V = 1843.22 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 298 K

  • 0.28 × 0.26 × 0.20 mm

Data collection
  • Bruker APEXII CCD 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 = 0.958

  • 11988 measured reflections

  • 2359 independent reflections

  • 1930 reflections with I > 2[sigma](I)

  • Rint = 0.023

  • [theta]max = 22.4°

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.092

  • S = 1.06

  • 2359 reflections

  • 236 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...O3i 0.93 2.58 3.495 (3) 169
C8-H8A...O3ii 0.97 2.34 3.255 (3) 157
C10-H10B...O1iii 0.97 2.48 3.402 (3) 159
C8-H8B...F1iv 0.97 2.57 3.518 (3) 165
C11-H11A...F2iv 0.97 2.56 3.296 (3) 133
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y-1, z; (iii) x, y+1, z; (iv) [x, -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: ORTEP-3 (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: SJ5290 ).


Acknowledgements

The authors thank Dr S. C. Sharma, 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

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
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, o185  [ doi:10.1107/S1600536812051690 ]

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