1-Tosyl-4-[2-(trifluoro-meth-yl)benz-yl]piperazine.

In the crystal structure of the title compound, C(19)H(21)F(3)N(2)O(2)S, the piperazine ring adopts a chair conformation. The dihedral angles between the mean plane of the piperazine ring and the tosyl and trifluoro-methyl-phenyl 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 inter-actions.

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 = 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

Δρmax = 0.18 e Å−3

Δρmin = −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.

Click here for additional data file.

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

Click here for additional data file.

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

Click here for additional data file.

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

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

C19H21F3N2O2S	F(000) = 416
Mr = 398.44	prism
Triclinic, P1	Dx = 1.389 Mg m−3
Hall symbol: -P 1	Melting point: 455 K
a = 9.5044 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8389 (3) Å	Cell parameters from 3359 reflections
c = 12.1473 (4) Å	θ = 1.8–25.0°
α = 72.036 (1)°	µ = 0.22 mm−1
β = 77.024 (1)°	T = 296 K
γ = 62.384 (1)°	Prism, colourless
V = 952.96 (5) Å3	0.28 × 0.26 × 0.24 mm
Z = 2

Bruker APEXII diffractometer	2981 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
Tmin = 0.942, Tmax = 0.950	l = −14→14
18514 measured reflections	2981 standard reflections every 3359 reflections
3359 independent reflections	intensity decay: 0.6%

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0669P)2 + 0.2061P] where P = (Fo2 + 2Fc2)/3
3359 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.53 e Å−3
0 constraints

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	−0.1973 (2)	0.79085 (19)	1.04506 (16)	0.0524 (4)
H1	−0.1413	0.8051	0.9723	0.063*
C2	−0.3565 (2)	0.8200 (2)	1.0527 (2)	0.0650 (5)
H2	−0.4054	0.8512	0.9852	0.078*
C3	−0.4417 (2)	0.8030 (2)	1.1589 (2)	0.0692 (6)
H3	−0.5494	0.8269	1.1637	0.083*
C4	−0.3681 (2)	0.7507 (2)	1.25786 (19)	0.0601 (5)
H4	−0.4258	0.7382	1.3301	0.072*
C5	−0.2083 (2)	0.71618 (19)	1.25148 (15)	0.0484 (4)
C6	−0.12093 (19)	0.74094 (18)	1.14417 (14)	0.0446 (4)
C7	−0.1307 (2)	0.6477 (3)	1.36242 (17)	0.0662 (5)
C8	0.0483 (2)	0.7240 (3)	1.13458 (15)	0.0570 (4)
H8A	0.0465	0.8048	1.1654	0.068*
H8B	0.1120	0.6221	1.1819	0.068*
C9	0.1988 (2)	0.5868 (2)	0.98362 (15)	0.0533 (4)
H9A	0.1208	0.5447	0.9957	0.064*
H9B	0.2835	0.5124	1.0328	0.064*
C10	0.2667 (2)	0.6058 (2)	0.85784 (15)	0.0512 (4)
H10A	0.3190	0.5041	0.8378	0.061*
H10B	0.1818	0.6756	0.8079	0.061*
C11	0.3078 (2)	0.8246 (2)	0.87272 (15)	0.0549 (4)
H11A	0.2231	0.8998	0.8237	0.066*
H11B	0.3862	0.8658	0.8617	0.066*
C12	0.2407 (2)	0.8003 (2)	0.99864 (16)	0.0572 (4)
H12A	0.3265	0.7275	1.0473	0.069*
H12B	0.1908	0.9000	1.0213	0.069*
C13	0.39911 (19)	0.7588 (2)	0.60451 (14)	0.0494 (4)
C14	0.3464 (2)	0.6848 (2)	0.55409 (16)	0.0586 (5)
H14	0.3724	0.5776	0.5826	0.070*
C15	0.2560 (2)	0.7693 (3)	0.46208 (17)	0.0650 (5)
H15	0.2211	0.7187	0.4284	0.078*
C16	0.2156 (2)	0.9293 (3)	0.41834 (15)	0.0607 (5)
C17	0.2694 (2)	1.0018 (2)	0.46948 (16)	0.0623 (5)
H17	0.2440	1.1088	0.4407	0.075*
C18	0.3601 (2)	0.9183 (2)	0.56233 (16)	0.0564 (4)
H18	0.3947	0.9687	0.5964	0.068*
C19	0.1146 (3)	1.0231 (4)	0.3176 (2)	0.0932 (8)
H19A	0.0038	1.0616	0.3464	0.140*
H19B	0.1364	0.9567	0.2665	0.140*
H19C	0.1394	1.1108	0.2758	0.140*
N1	0.12372 (17)	0.73734 (17)	1.01560 (12)	0.0492 (3)
N2	0.38211 (16)	0.67220 (16)	0.84130 (12)	0.0482 (3)
O1	0.58136 (16)	0.48817 (17)	0.72513 (13)	0.0758 (4)
O2	0.60748 (16)	0.7253 (2)	0.72858 (12)	0.0771 (4)
F1	−0.05597 (17)	0.7266 (2)	1.37482 (11)	0.0944 (5)
F2	−0.23300 (18)	0.6445 (2)	1.45635 (11)	0.1050 (5)
F3	−0.02138 (19)	0.49998 (18)	1.36833 (12)	0.1020 (5)
S1	0.51074 (5)	0.65163 (6)	0.72555 (4)	0.05661 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0562 (10)	0.0455 (9)	0.0529 (10)	−0.0191 (8)	−0.0149 (8)	−0.0053 (7)
C2	0.0602 (11)	0.0482 (10)	0.0846 (14)	−0.0144 (9)	−0.0344 (11)	−0.0076 (9)
C3	0.0427 (10)	0.0585 (11)	0.1037 (17)	−0.0164 (9)	−0.0127 (11)	−0.0198 (11)
C4	0.0473 (10)	0.0564 (10)	0.0756 (13)	−0.0231 (8)	0.0041 (9)	−0.0199 (9)
C5	0.0462 (9)	0.0456 (9)	0.0517 (9)	−0.0183 (7)	−0.0002 (7)	−0.0144 (7)
C6	0.0433 (8)	0.0414 (8)	0.0475 (9)	−0.0150 (7)	−0.0060 (7)	−0.0121 (7)
C7	0.0612 (12)	0.0861 (15)	0.0477 (10)	−0.0313 (11)	0.0032 (9)	−0.0172 (10)
C8	0.0502 (10)	0.0831 (13)	0.0427 (9)	−0.0317 (9)	−0.0003 (7)	−0.0193 (9)
C9	0.0600 (10)	0.0541 (10)	0.0493 (9)	−0.0324 (9)	0.0011 (8)	−0.0084 (7)
C10	0.0595 (10)	0.0490 (9)	0.0479 (9)	−0.0269 (8)	0.0021 (8)	−0.0139 (7)
C11	0.0650 (11)	0.0588 (10)	0.0516 (10)	−0.0377 (9)	−0.0018 (8)	−0.0115 (8)
C12	0.0670 (11)	0.0690 (11)	0.0508 (10)	−0.0406 (10)	0.0005 (8)	−0.0199 (8)
C13	0.0414 (8)	0.0590 (10)	0.0397 (8)	−0.0213 (8)	0.0039 (7)	−0.0068 (7)
C14	0.0609 (11)	0.0564 (10)	0.0553 (10)	−0.0245 (9)	0.0012 (8)	−0.0146 (8)
C15	0.0638 (12)	0.0822 (14)	0.0566 (11)	−0.0333 (11)	−0.0024 (9)	−0.0254 (10)
C16	0.0500 (10)	0.0817 (14)	0.0409 (9)	−0.0236 (9)	−0.0002 (7)	−0.0119 (9)
C17	0.0643 (12)	0.0602 (11)	0.0505 (10)	−0.0255 (9)	−0.0038 (9)	−0.0002 (8)
C18	0.0604 (11)	0.0619 (11)	0.0494 (10)	−0.0326 (9)	−0.0038 (8)	−0.0068 (8)
C19	0.0775 (15)	0.124 (2)	0.0571 (13)	−0.0275 (15)	−0.0203 (11)	−0.0076 (13)
N1	0.0514 (8)	0.0605 (8)	0.0421 (7)	−0.0291 (7)	0.0010 (6)	−0.0160 (6)
N2	0.0475 (8)	0.0526 (8)	0.0414 (7)	−0.0232 (6)	−0.0020 (6)	−0.0054 (6)
O1	0.0583 (8)	0.0634 (8)	0.0647 (9)	−0.0005 (7)	0.0021 (6)	−0.0076 (6)
O2	0.0539 (8)	0.1138 (12)	0.0621 (8)	−0.0461 (8)	−0.0073 (6)	−0.0008 (8)
F1	0.0980 (10)	0.1560 (14)	0.0594 (8)	−0.0745 (10)	−0.0026 (7)	−0.0361 (8)
F2	0.0923 (10)	0.1675 (15)	0.0502 (7)	−0.0651 (10)	0.0168 (7)	−0.0202 (8)
F3	0.1030 (11)	0.0919 (10)	0.0645 (8)	−0.0078 (8)	−0.0260 (7)	0.0014 (7)
S1	0.0409 (3)	0.0670 (3)	0.0460 (3)	−0.0177 (2)	−0.00155 (18)	−0.0027 (2)

C1—C6	1.384 (2)	C11—N2	1.464 (2)
C1—C2	1.390 (3)	C11—C12	1.510 (2)
C1—H1	0.9300	C11—H11A	0.9700
C2—C3	1.368 (3)	C11—H11B	0.9700
C2—H2	0.9300	C12—N1	1.456 (2)
C3—C4	1.364 (3)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.384 (2)	C13—C14	1.381 (3)
C4—H4	0.9300	C13—C18	1.382 (3)
C5—C6	1.398 (2)	C13—S1	1.7625 (17)
C5—C7	1.496 (3)	C14—C15	1.369 (3)
C6—C8	1.519 (2)	C14—H14	0.9300
C7—F2	1.325 (2)	C15—C16	1.386 (3)
C7—F1	1.328 (3)	C15—H15	0.9300
C7—F3	1.329 (3)	C16—C17	1.383 (3)
C8—N1	1.458 (2)	C16—C19	1.510 (3)
C8—H8A	0.9700	C17—C18	1.378 (3)
C8—H8B	0.9700	C17—H17	0.9300
C9—N1	1.451 (2)	C18—H18	0.9300
C9—C10	1.510 (2)	C19—H19A	0.9600
C9—H9A	0.9700	C19—H19B	0.9600
C9—H9B	0.9700	C19—H19C	0.9600
C10—N2	1.468 (2)	N2—S1	1.6391 (14)
C10—H10A	0.9700	O2—S1	1.4223 (15)
C10—H10B	0.9700	S1—O1	1.4282 (15)
C6—C1—C2	120.91 (18)	N2—C11—H11B	110.0
C6—C1—H1	119.5	C12—C11—H11B	110.0
C2—C1—H1	119.5	H11A—C11—H11B	108.4
C3—C2—C1	120.35 (18)	N1—C12—C11	110.19 (14)
C3—C2—H2	119.8	N1—C12—H12A	109.6
C1—C2—H2	119.8	C11—C12—H12A	109.6
C4—C3—C2	119.77 (18)	N1—C12—H12B	109.6
C4—C3—H3	120.1	C11—C12—H12B	109.6
C2—C3—H3	120.1	H12A—C12—H12B	108.1
C3—C4—C5	120.43 (18)	C14—C13—C18	120.00 (17)
C3—C4—H4	119.8	C14—C13—S1	120.06 (14)
C5—C4—H4	119.8	C18—C13—S1	119.91 (14)
C4—C5—C6	120.86 (17)	C15—C14—C13	119.93 (18)
C4—C5—C7	118.11 (16)	C15—C14—H14	120.0
C6—C5—C7	121.01 (15)	C13—C14—H14	120.0
C1—C6—C5	117.53 (15)	C14—C15—C16	121.02 (18)
C1—C6—C8	120.23 (15)	C14—C15—H15	119.5
C5—C6—C8	122.15 (15)	C16—C15—H15	119.5
F2—C7—F1	105.93 (17)	C17—C16—C15	118.43 (18)
F2—C7—F3	106.64 (18)	C17—C16—C19	120.4 (2)
F1—C7—F3	106.07 (18)	C15—C16—C19	121.1 (2)
F2—C7—C5	113.14 (17)	C18—C17—C16	121.17 (18)
F1—C7—C5	113.06 (17)	C18—C17—H17	119.4
F3—C7—C5	111.48 (16)	C16—C17—H17	119.4
N1—C8—C6	113.17 (14)	C17—C18—C13	119.45 (17)
N1—C8—H8A	108.9	C17—C18—H18	120.3
C6—C8—H8A	108.9	C13—C18—H18	120.3
N1—C8—H8B	108.9	C16—C19—H19A	109.5
C6—C8—H8B	108.9	C16—C19—H19B	109.5
H8A—C8—H8B	107.8	H19A—C19—H19B	109.5
N1—C9—C10	110.58 (13)	C16—C19—H19C	109.5
N1—C9—H9A	109.5	H19A—C19—H19C	109.5
C10—C9—H9A	109.5	H19B—C19—H19C	109.5
N1—C9—H9B	109.5	C9—N1—C12	109.73 (14)
C10—C9—H9B	109.5	C9—N1—C8	111.63 (14)
H9A—C9—H9B	108.1	C12—N1—C8	111.32 (13)
N2—C10—C9	108.49 (13)	C11—N2—C10	111.46 (13)
N2—C10—H10A	110.0	C11—N2—S1	118.22 (11)
C9—C10—H10A	110.0	C10—N2—S1	116.83 (11)
N2—C10—H10B	110.0	O2—S1—O1	120.28 (9)
C9—C10—H10B	110.0	O2—S1—N2	106.27 (8)
H10A—C10—H10B	108.4	O1—S1—N2	106.46 (8)
N2—C11—C12	108.27 (14)	O2—S1—C13	108.64 (8)
N2—C11—H11A	110.0	O1—S1—C13	107.92 (9)
C12—C11—H11A	110.0	N2—S1—C13	106.48 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···Cgi	0.97	2.84 (1)	3.670 (2)	144

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

Symmetry code: (i) .