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

Sreenivasa, S.; ManojKumar, K.E.; Suchetan, P.A.; Tonannavar, J.; Chavan, Y.; Palakshamurthy, B.S.

doi:10.1107/S1600536812051690

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 (C-C) = 0.004 Å
R = 0.033
wR = 0.092
Data-to-parameter ratio = 10.0
Details

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

S. Sreenivasa,^a ^* K. E. ManojKumar,^a P. A. Suchetan,^b J. Tonannavar,^c Yashshwita Chavan ^c and B. S. Palakshamurthy ^d

^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-HO hydrogen bonds. The structure is further stabilized by weak intermolecular C-HF 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,b). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₈H₁₈F₂N₂O₃S
M_r = 380.40
Monoclinic, P 2₁ /c
a = 17.0456 (4) Å
b = 7.6026 (1) Å
c = 15.5113 (3) Å
= 113.513 (1)°
V = 1843.22 (6) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.942, T_max = 0.958
11988 measured reflections
2359 independent reflections
1930 reflections with I > 2(I)
R_int = 0.023
_max = 22.4°

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.092
S = 1.06
2359 reflections
236 parameters
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4O3ⁱ	0.93	2.58	3.495 (3)	169
C8-H8AO3ⁱⁱ	0.97	2.34	3.255 (3)	157
C10-H10BO1ⁱⁱⁱ	0.97	2.48	3.402 (3)	159
C8-H8BF1^iv	0.97	2.57	3.518 (3)	165
C11-H11AF2^iv	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); 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 (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: 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.
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