1-Tosyl-4-[2-(trifluoro­meth­yl)benz­yl]piperazine

S Sreenivasa; H C Anitha; K E ManojKumar; J Tonannavar; Yenagi Jayashree; P A Suchetan; B S Palakshamurthy

doi:10.1107/S1600536813000317

. 2013 Jan 16;69(Pt 2):o239. doi: 10.1107/S1600536813000317

1-Tosyl-4-[2-(trifluoromethyl)benzyl]piperazine

S Sreenivasa ^a,^*, H C Anitha ^a, K E ManojKumar ^a, J Tonannavar ^b, Yenagi Jayashree ^b, P A Suchetan ^c, B S Palakshamurthy ^d

PMCID: PMC3569772 PMID: 23424518

Abstract

In the crystal structure of the title compound, C₁₉H₂₁F₃N₂O₂S, the piperazine ring adopts a chair conformation. The dihedral angles between the mean plane of the piperazine ring and the tosyl and trifluoromethylphenyl rings are 74.52 (3) and 68.30 (2)°, respectively. The sulfonamide N atom deviates from the plane defined by the three attached atoms by 0.327 (1) Å. The crystal structure is stabilized by weak C—H⋯π interactions.

Related literature

For the synthesis, characterization and biological activity of piperazine and its derivatives, see: Gan et al. (2009a ▶,b ▶)

Experimental

Crystal data

C₁₉H₂₁F₃N₂O₂S
M _r = 398.44
Triclinic,
a = 9.5044 (3) Å
b = 9.8389 (3) Å
c = 12.1473 (4) Å
α = 72.036 (1)°
β = 77.024 (1)°
γ = 62.384 (1)°
V = 952.96 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.28 × 0.26 × 0.24 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.942, T _max = 0.950
18514 measured reflections
3359 independent reflections
2981 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.119
S = 1.08
3359 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.53 e Å⁻³

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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Click here for additional data file.^{(25KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000317/gk2548sup1.cif

e-69-0o239-sup1.cif^{(25KB, cif)}

Click here for additional data file.^{(164.7KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000317/gk2548Isup2.hkl

e-69-0o239-Isup2.hkl^{(164.7KB, hkl)}

Click here for additional data file.^{(7.2KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813000317/gk2548Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the benzene ring of the trifluoromethylphenyl group (C1–C6).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯Cg ⁱ	0.97	2.84 (1)	3.670 (2)	144

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

Numerous piperazine derivatives like aryl amide, sulfonamides, Mannich bases, Schiff bases, thiazolidinones, azetidinones, imidazolinones have shown a wide spectrum of biological activities viz. anti-inflammatory, antibacterial, antimalarial, anticonvulsant, antipyretic, antitumor, anthelmintics, analgesic, antidepressant, antifungal, antitubercular, anticancer, antidiabetic (Gan et al., 2009a,b). Keeping this in mind, we synthesized the title compound and here we report its crystal structure.

Experimental

A mixture of 1-tosylpiperazine (0.01 mmol), potassium carbonate (0.03 mmol) and 2-trifluoromethylbenzyl bromide (0.01 mmol) was added into dry acetonitrile (5 ml). The mixture was stirred at 85°C for 8 h. The reaction was monitored by TLC. Solvent was removed by vacuum distillation and the crude product obtained was purified by column chromatography using 230–400 silica gel and petroleum ether/ethyl acetate as eluent. Single crystals of the title compound were obtained from a mixture of petroleum ether/ethyl acetate (7:3) by slow evaporation technique.