1-(3,4-Di­fluoro­benz­yl)-4-(4-methyl­phenyl­sulfon­yl)piperazine

S Sreenivasa; H C Anitha; P A Suchetan; B S Palakshamurthy; J Savanur; J Tonannavar

doi:10.1107/S1600536813016462

. 2013 Jun 29;69(Pt 7):o1179. doi: 10.1107/S1600536813016462

1-(3,4-Difluorobenzyl)-4-(4-methylphenylsulfonyl)piperazine

S Sreenivasa ^a,^*, H C Anitha ^b, P A Suchetan ^b, B S Palakshamurthy ^c, J Savanur ^d, J Tonannavar ^d

PMCID: PMC3770435 PMID: 24046720

Abstract

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 ▶,b ▶,c ▶). graphic file with name e-69-o1179-scheme1.jpg

Experimental

Crystal data

C₁₈H₂₀F₂N₂O₂S
M _r = 366.42
Monoclinic,
a = 6.6680 (2) Å
b = 36.0404 (8) Å
c = 7.6093 (2) Å
β = 99.728 (2)°
V = 1802.35 (8) Å³
Z = 4
Mo Kα radiation
μ = 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 ▶) T _min = 0.943, T _max = 0.959
9583 measured reflections
2434 independent reflections
1910 reflections with I > 2σ(I)
R _int = 0.025
θ_max = 22.8°

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.114
S = 1.02
2434 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.25 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: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813016462/sj5330sup1.cif

e-69-o1179-sup1.cif^{(27.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016462/sj5330Isup2.hkl

e-69-o1179-Isup2.hkl^{(119.6KB, hkl)}

Click here for additional data file.^{(6.7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813016462/sj5330Isup3.cml

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

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

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

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.

supplementary crystallographic information

Comment

As a part of our continued efforts to study the crystal structures of N-(aryl)(4-tosylpiperazin-1-yl)methanone derivatives (Sreenivasa et al., 2013a,b,c), we report herein the crystal structure of the title compound.

The title compound, Fig. 1, crystallizes in the monoclinic crystal system and P2₁/c space group. The piperazine ring in the title compound adopts a chair conformation. The dihedral angle between the two benzene rings is 40.20°, compared to the observed dihedral angles of 72.2 (12)°, 76.86° and 30.97 (2)° respectively in (I), 1-(2,4-dichlorobenzyl)-4-[(4-methyl-phenyl)sulfonyl]-piperazine (Sreenivasa et al., 2013a), (II) 1-tosyl-4-[2-(trifluoromethyl)-benzyl]piperazine (Sreenivasa et al., 2013b) and (III) (2,3-difluorophenyl)(4-tosylpiperazin-1-yl)methanone (Sreenivasa et al., 2013c). Further, the dihedral angles between the piperazine ring (considering the best fit plane through all the non-hydrogen atoms) and the sulfonyl bound benzene and difluorobenzene rings are 74.96° and 86.16° respectively, compared to 74.16 (2)° and 2.44 (13)° in I, 74.36° and 68.29 (3)° in II, and 69.4 (2)° and 75.98 (2)° in III.

In the crystal structure, the molecules are stacked along the a axis through weak C–H···O and C–H···F interactions, Fig. 2.

Experimental

A mixture of 1-tosylpiperazine (0.01 mmol), potassium carbonate (0.03 mmol) and 3,4-difluorobenzyl bromide (0.01 mmol) was added to 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.

Colourless prisms were obtained from a mixture of dichloromethane/methanol (7:3) by slow evaporation.