1-(3,4-Di-fluoro-benz-yl)-4-(4-methyl-phenyl-sulfon-yl)piperazine.

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 di-fluoro-benzene rings are 74.96 and 86.16°, respectively. In the crystal, mol-ecules are stacked along the a axis through weak C-H⋯O and C-H⋯F inter-actions.

Related literature

For similar structures, see: Sreenivasa et al. (2013a ▶,b ▶,c ▶).

Experimental

Crystal data

C18H20F2N2O2S

M = 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

θmax = 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

Δρmax = 0.19 e Å−3

Δρmin = −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.

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

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

Click here for additional data file.

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

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

C18H20F2N2O2S	prism
Mr = 366.42	Dx = 1.350 Mg m−3
Monoclinic, P21/c	Melting point: 501 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.6680 (2) Å	Cell parameters from 227 reflections
b = 36.0404 (8) Å	θ = 2.3–22.8°
c = 7.6093 (2) Å	µ = 0.21 mm−1
β = 99.728 (2)°	T = 298 K
V = 1802.35 (8) Å3	Prism, colourless
Z = 4	0.28 × 0.24 × 0.20 mm
F(000) = 768

Bruker APEXII diffractometer	2434 independent reflections
Radiation source: fine-focus sealed tube	1910 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 1.03 pixels mm-1	θmax = 22.8°, θmin = 2.3°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −39→37
Tmin = 0.943, Tmax = 0.959	l = −7→8
9583 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0512P)2 + 0.6421P] where P = (Fo2 + 2Fc2)/3
2434 reflections	(Δ/σ)max = 0.028
227 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.25 e Å−3
32 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	−0.3654 (5)	0.51803 (9)	0.7226 (4)	0.0763 (8)
C2	−0.4516 (5)	0.48860 (11)	0.7956 (4)	0.0850 (9)
H2	−0.5880	0.4901	0.8070	0.102*
C3	−0.3451 (5)	0.45692 (9)	0.8529 (4)	0.0761 (8)
H3	−0.4088	0.4376	0.9028	0.091*
C4	−0.1454 (4)	0.45409 (7)	0.8359 (3)	0.0598 (7)
C5	−0.0564 (4)	0.48283 (9)	0.7599 (4)	0.0821 (9)
H5	0.0790	0.4811	0.7455	0.099*
C6	−0.1666 (6)	0.51438 (9)	0.7045 (4)	0.0870 (9)
H6	−0.1034	0.5336	0.6535	0.104*
C7	−0.4821 (6)	0.55287 (10)	0.6662 (5)	0.1135 (13)
H7A	−0.4283	0.5729	0.7431	0.170*
H7B	−0.6229	0.5492	0.6742	0.170*
H7C	−0.4697	0.5587	0.5455	0.170*
C8	−0.2454 (4)	0.36712 (8)	0.6955 (4)	0.0737 (8)
H8A	−0.3419	0.3850	0.6347	0.088*
H8B	−0.2926	0.3592	0.8033	0.088*
C9	−0.2310 (5)	0.33415 (7)	0.5761 (4)	0.0738 (8)
H9A	−0.1406	0.3157	0.6400	0.089*
H9B	−0.3644	0.3230	0.5431	0.089*
C10	0.0484 (4)	0.36109 (8)	0.4655 (4)	0.0734 (8)
H10A	0.1008	0.3680	0.3587	0.088*
H10B	0.1392	0.3427	0.5292	0.088*
C11	0.0404 (4)	0.39451 (7)	0.5809 (4)	0.0680 (7)
H11A	0.1762	0.4046	0.6154	0.082*
H11B	−0.0443	0.4134	0.5148	0.082*
C12	−0.1536 (5)	0.31498 (8)	0.2910 (4)	0.0801 (9)
H12A	−0.0854	0.2938	0.3529	0.096*
H12B	−0.0773	0.3224	0.1990	0.096*
C13	−0.3660 (4)	0.30386 (8)	0.2051 (3)	0.0629 (7)
C14	−0.4280 (5)	0.26741 (8)	0.2015 (4)	0.0737 (8)
H14	−0.3405	0.2492	0.2572	0.088*
C15	−0.6186 (5)	0.25787 (8)	0.1158 (4)	0.0759 (8)
C16	−0.7479 (5)	0.28422 (10)	0.0346 (4)	0.0772 (8)
C17	−0.6903 (5)	0.32020 (9)	0.0356 (4)	0.0834 (9)
H17	−0.7788	0.3381	−0.0212	0.100*
C18	−0.4993 (5)	0.33006 (8)	0.1215 (4)	0.0729 (8)
H18	−0.4596	0.3548	0.1231	0.088*
N1	−0.0432 (3)	0.38434 (6)	0.7410 (3)	0.0646 (6)
N2	−0.1548 (3)	0.34542 (6)	0.4167 (3)	0.0627 (6)
O1	0.2056 (3)	0.42331 (6)	0.9324 (3)	0.0918 (7)
O2	−0.0916 (4)	0.39768 (6)	1.0463 (2)	0.0989 (7)
F1	−0.6798 (3)	0.22224 (5)	0.1108 (3)	0.1225 (8)
F2	−0.9357 (3)	0.27392 (6)	−0.0489 (3)	0.1200 (7)
S1	−0.00612 (12)	0.41390 (2)	0.90583 (9)	0.0734 (3)

	U11	U22	U33	U12	U13	U23
C1	0.080 (2)	0.089 (2)	0.0536 (17)	0.0093 (19)	−0.0063 (15)	−0.0117 (15)
C2	0.0544 (19)	0.114 (3)	0.086 (2)	0.001 (2)	0.0093 (16)	−0.022 (2)
C3	0.074 (2)	0.087 (2)	0.0703 (19)	−0.0205 (18)	0.0190 (15)	−0.0075 (16)
C4	0.0567 (18)	0.0677 (18)	0.0527 (15)	−0.0136 (13)	0.0024 (12)	−0.0043 (13)
C5	0.0567 (18)	0.077 (2)	0.114 (3)	−0.0079 (16)	0.0178 (17)	0.0131 (18)
C6	0.092 (3)	0.071 (2)	0.099 (2)	−0.0020 (18)	0.0179 (19)	0.0170 (17)
C7	0.128 (3)	0.116 (3)	0.082 (2)	0.047 (2)	−0.023 (2)	−0.014 (2)
C8	0.082 (2)	0.079 (2)	0.0601 (17)	−0.0242 (16)	0.0110 (15)	0.0036 (15)
C9	0.084 (2)	0.0610 (17)	0.0711 (19)	−0.0216 (15)	−0.0014 (15)	0.0047 (14)
C10	0.0626 (19)	0.076 (2)	0.0795 (19)	−0.0024 (15)	0.0056 (14)	0.0011 (16)
C11	0.0652 (18)	0.0661 (18)	0.0705 (18)	−0.0125 (14)	0.0051 (14)	0.0079 (14)
C12	0.073 (2)	0.077 (2)	0.086 (2)	0.0074 (16)	0.0020 (16)	−0.0156 (17)
C13	0.0687 (19)	0.0607 (18)	0.0582 (16)	0.0072 (15)	0.0069 (13)	−0.0111 (13)
C14	0.086 (2)	0.0618 (19)	0.0689 (18)	0.0114 (16)	0.0011 (16)	−0.0066 (14)
C15	0.093 (2)	0.0558 (19)	0.080 (2)	−0.0109 (18)	0.0167 (18)	−0.0134 (15)
C16	0.066 (2)	0.087 (2)	0.075 (2)	−0.0040 (18)	−0.0003 (15)	−0.0177 (17)
C17	0.082 (2)	0.079 (2)	0.083 (2)	0.0152 (18)	−0.0043 (17)	−0.0005 (17)
C18	0.078 (2)	0.0592 (18)	0.0782 (19)	0.0012 (15)	0.0042 (16)	−0.0011 (15)
N1	0.0693 (15)	0.0594 (13)	0.0599 (13)	−0.0137 (11)	−0.0038 (11)	0.0045 (10)
N2	0.0631 (15)	0.0628 (14)	0.0602 (13)	−0.0042 (11)	0.0047 (11)	−0.0009 (11)
O1	0.0685 (14)	0.0894 (15)	0.1015 (16)	−0.0033 (11)	−0.0311 (11)	−0.0102 (12)
O2	0.148 (2)	0.0899 (15)	0.0536 (12)	−0.0194 (13)	0.0032 (12)	0.0131 (11)
F1	0.1360 (18)	0.0734 (13)	0.154 (2)	−0.0270 (12)	0.0134 (14)	−0.0162 (12)
F2	0.0804 (14)	0.1292 (17)	0.1398 (18)	−0.0121 (11)	−0.0119 (12)	−0.0334 (13)
S1	0.0845 (6)	0.0688 (5)	0.0590 (5)	−0.0099 (4)	−0.0110 (4)	0.0051 (4)

C1—C6	1.362 (4)	C10—H10A	0.9700
C1—C2	1.368 (4)	C10—H10B	0.9700
C1—C7	1.501 (4)	C11—N1	1.469 (3)
C2—C3	1.376 (4)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—C4	1.363 (4)	C12—N2	1.457 (3)
C3—H3	0.9300	C12—C13	1.510 (4)
C4—C5	1.369 (4)	C12—H12A	0.9700
C4—S1	1.754 (3)	C12—H12B	0.9700
C5—C6	1.381 (4)	C13—C14	1.376 (4)
C5—H5	0.9300	C13—C18	1.377 (4)
C6—H6	0.9300	C14—C15	1.371 (4)
C7—H7A	0.9600	C14—H14	0.9300
C7—H7B	0.9600	C15—F1	1.346 (3)
C7—H7C	0.9600	C15—C16	1.359 (4)
C8—N1	1.472 (3)	C16—C17	1.352 (4)
C8—C9	1.508 (4)	C16—F2	1.356 (3)
C8—H8A	0.9700	C17—C18	1.377 (4)
C8—H8B	0.9700	C17—H17	0.9300
C9—N2	1.450 (3)	C18—H18	0.9300
C9—H9A	0.9700	N1—S1	1.632 (2)
C9—H9B	0.9700	O1—S1	1.432 (2)
C10—N2	1.457 (3)	O2—S1	1.419 (2)
C10—C11	1.497 (4)
C6—C1—C2	116.7 (3)	N1—C11—C10	110.0 (2)
C6—C1—C7	121.2 (3)	N1—C11—H11A	109.7
C2—C1—C7	122.1 (3)	C10—C11—H11A	109.7
C1—C2—C3	122.8 (3)	N1—C11—H11B	109.7
C1—C2—H2	118.6	C10—C11—H11B	109.7
C3—C2—H2	118.6	H11A—C11—H11B	108.2
C4—C3—C2	119.5 (3)	N2—C12—C13	112.0 (2)
C4—C3—H3	120.3	N2—C12—H12A	109.2
C2—C3—H3	120.3	C13—C12—H12A	109.2
C3—C4—C5	118.9 (3)	N2—C12—H12B	109.2
C3—C4—S1	120.5 (2)	C13—C12—H12B	109.2
C5—C4—S1	120.5 (2)	H12A—C12—H12B	107.9
C4—C5—C6	120.4 (3)	C14—C13—C18	118.5 (3)
C4—C5—H5	119.8	C14—C13—C12	121.2 (3)
C6—C5—H5	119.8	C18—C13—C12	120.2 (3)
C1—C6—C5	121.7 (3)	C15—C14—C13	120.0 (3)
C1—C6—H6	119.2	C15—C14—H14	120.0
C5—C6—H6	119.2	C13—C14—H14	120.0
C1—C7—H7A	109.5	F1—C15—C16	119.2 (3)
C1—C7—H7B	109.5	F1—C15—C14	120.3 (3)
H7A—C7—H7B	109.5	C16—C15—C14	120.5 (3)
C1—C7—H7C	109.5	C17—C16—F2	120.3 (3)
H7A—C7—H7C	109.5	C17—C16—C15	120.6 (3)
H7B—C7—H7C	109.5	F2—C16—C15	119.1 (3)
N1—C8—C9	109.0 (2)	C16—C17—C18	119.3 (3)
N1—C8—H8A	109.9	C16—C17—H17	120.3
C9—C8—H8A	109.9	C18—C17—H17	120.3
N1—C8—H8B	109.9	C17—C18—C13	121.0 (3)
C9—C8—H8B	109.9	C17—C18—H18	119.5
H8A—C8—H8B	108.3	C13—C18—H18	119.5
N2—C9—C8	110.5 (2)	C11—N1—C8	111.8 (2)
N2—C9—H9A	109.6	C11—N1—S1	116.43 (17)
C8—C9—H9A	109.6	C8—N1—S1	118.03 (18)
N2—C9—H9B	109.6	C9—N2—C12	112.3 (2)
C8—C9—H9B	109.6	C9—N2—C10	109.7 (2)
H9A—C9—H9B	108.1	C12—N2—C10	110.5 (2)
N2—C10—C11	109.7 (2)	O2—S1—O1	120.16 (13)
N2—C10—H10A	109.7	O2—S1—N1	106.38 (12)
C11—C10—H10A	109.7	O1—S1—N1	106.30 (13)
N2—C10—H10B	109.7	O2—S1—C4	108.02 (14)
C11—C10—H10B	109.7	O1—S1—C4	107.81 (12)
H10A—C10—H10B	108.2	N1—S1—C4	107.58 (11)
C6—C1—C2—C3	1.5 (5)	C14—C13—C18—C17	−0.1 (4)
C7—C1—C2—C3	−178.0 (3)	C12—C13—C18—C17	177.0 (3)
C1—C2—C3—C4	−0.6 (4)	C10—C11—N1—C8	−56.5 (3)
C2—C3—C4—C5	−0.8 (4)	C10—C11—N1—S1	163.77 (18)
C2—C3—C4—S1	−179.4 (2)	C9—C8—N1—C11	55.7 (3)
C3—C4—C5—C6	1.2 (4)	C9—C8—N1—S1	−165.23 (18)
S1—C4—C5—C6	179.8 (2)	C8—C9—N2—C12	−175.5 (2)
C2—C1—C6—C5	−1.1 (5)	C8—C9—N2—C10	61.1 (3)
C7—C1—C6—C5	178.4 (3)	C13—C12—N2—C9	70.2 (3)
C4—C5—C6—C1	−0.2 (5)	C13—C12—N2—C10	−166.9 (2)
N1—C8—C9—N2	−57.8 (3)	C11—C10—N2—C9	−60.8 (3)
N2—C10—C11—N1	58.1 (3)	C11—C10—N2—C12	174.7 (2)
N2—C12—C13—C14	−129.4 (3)	C11—N1—S1—O2	−177.66 (19)
N2—C12—C13—C18	53.5 (4)	C8—N1—S1—O2	45.1 (2)
C18—C13—C14—C15	0.0 (4)	C11—N1—S1—O1	−48.5 (2)
C12—C13—C14—C15	−177.1 (3)	C8—N1—S1—O1	174.31 (19)
C13—C14—C15—F1	179.6 (3)	C11—N1—S1—C4	66.8 (2)
C13—C14—C15—C16	−0.3 (4)	C8—N1—S1—C4	−70.4 (2)
F1—C15—C16—C17	−179.3 (3)	C3—C4—S1—O2	−28.3 (3)
C14—C15—C16—C17	0.6 (5)	C5—C4—S1—O2	153.0 (2)
F1—C15—C16—F2	0.2 (4)	C3—C4—S1—O1	−159.6 (2)
C14—C15—C16—F2	−179.9 (3)	C5—C4—S1—O1	21.8 (3)
F2—C16—C17—C18	179.8 (3)	C3—C4—S1—N1	86.1 (2)
C15—C16—C17—C18	−0.7 (5)	C5—C4—S1—N1	−92.5 (2)
C16—C17—C18—C13	0.4 (5)

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

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

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