(2,3-Difluoro-phen-yl)(4-tosyl-piperazin-1-yl)methanone.

In the title compound, C(18)H(18)F(2)N(2)O(3)S, 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 fluoro-benzene and sulfonyl rings and the fluoro-benzene and piperazine rings are 30.97 (2) and 75.98 (2)°, respectively. In the crystal, mol-ecules are connected to form a tetra-meric unit through C-H⋯O hydrogen bonds. The structure is further stabilized by weak inter-molecular C-H⋯F inter-actions, 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 = 380.40

Monoclinic,

a = 17.0456 (4) Å

b = 7.6026 (1) Å

c = 15.5113 (3) Å

β = 113.513 (1)°

V = 1843.22 (6) Å3

Z = 4

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.023

θmax = 22.4°

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.092

S = 1.06

2359 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.23 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 (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/S1600536812051690/sj5290sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051690/sj5290Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051690/sj5290Isup3.cml

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

C18H18F2N2O3S	Prism
Mr = 380.40	Dx = 1.371 Mg m−3
Monoclinic, P21/c	Melting point: 457 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.0456 (4) Å	Cell parameters from 2364 reflections
b = 7.6026 (1) Å	θ = 2.6–22.4°
c = 15.5113 (3) Å	µ = 0.22 mm−1
β = 113.513 (1)°	T = 298 K
V = 1843.22 (6) Å3	Prism, colourless
Z = 4	0.28 × 0.26 × 0.20 mm
F(000) = 792

Bruker APEXII CCD diffractometer	2359 independent reflections
Radiation source: fine-focus sealed tube	1930 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 0.95 pixels mm-1	θmax = 22.4°, θmin = 2.6°
φ and ω scans	h = −18→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→7
Tmin = 0.942, Tmax = 0.958	l = −16→16
11988 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.3661P] where P = (Fo2 + 2Fc2)/3
2359 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.23 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	0.56842 (15)	0.1855 (3)	−0.19563 (16)	0.0606 (6)
C2	0.50273 (17)	0.2154 (3)	−0.28076 (15)	0.0652 (6)
C3	0.42103 (17)	0.2278 (3)	−0.28889 (17)	0.0712 (7)
H3	0.3767	0.2486	−0.3470	0.085*
C4	0.40468 (16)	0.2091 (3)	−0.20946 (19)	0.0788 (7)
H4	0.3488	0.2165	−0.2137	0.095*
C5	0.47062 (17)	0.1794 (3)	−0.12370 (17)	0.0710 (7)
H5	0.4587	0.1672	−0.0705	0.085*
C6	0.55410 (14)	0.1675 (3)	−0.11526 (14)	0.0542 (6)
C7	0.62575 (15)	0.1198 (3)	−0.02411 (15)	0.0599 (6)
C8	0.71988 (15)	0.1996 (3)	0.13429 (14)	0.0644 (6)
H8A	0.7369	0.0777	0.1353	0.077*
H8B	0.6944	0.2135	0.1797	0.077*
C9	0.79693 (15)	0.3155 (3)	0.16094 (15)	0.0632 (6)
H9A	0.8364	0.2901	0.2249	0.076*
H9B	0.8260	0.2935	0.1195	0.076*
C10	0.71040 (13)	0.5453 (3)	0.05710 (14)	0.0574 (6)
H10A	0.7382	0.5278	0.0141	0.069*
H10B	0.6938	0.6679	0.0542	0.069*
C11	0.63270 (14)	0.4302 (3)	0.02931 (15)	0.0598 (6)
H11A	0.6015	0.4580	0.0679	0.072*
H11B	0.5954	0.4525	−0.0358	0.072*
C12	0.91357 (14)	0.6645 (3)	0.15849 (14)	0.0584 (6)
C13	0.98919 (15)	0.5691 (3)	0.19152 (16)	0.0659 (6)
H13	1.0022	0.4951	0.2431	0.079*
C14	1.04489 (16)	0.5843 (3)	0.14784 (19)	0.0746 (7)
H14	1.0952	0.5191	0.1702	0.089*
C15	1.02791 (17)	0.6943 (3)	0.07146 (18)	0.0730 (7)
C16	0.95135 (18)	0.7848 (3)	0.03828 (17)	0.0742 (7)
H16	0.9379	0.8565	−0.0143	0.089*
C17	0.89459 (16)	0.7722 (3)	0.08056 (16)	0.0659 (6)
H17	0.8437	0.8354	0.0571	0.079*
C18	1.0916 (2)	0.7155 (4)	0.0280 (2)	0.1021 (10)
H18A	1.0634	0.7612	−0.0346	0.153*
H18B	1.1165	0.6034	0.0256	0.153*
H18C	1.1357	0.7956	0.0651	0.153*
N1	0.65731 (11)	0.2441 (2)	0.04104 (11)	0.0572 (5)
N2	0.76965 (11)	0.5003 (2)	0.15333 (11)	0.0571 (5)
O1	0.65057 (13)	−0.0330 (2)	−0.01083 (11)	0.0937 (6)
O2	0.88639 (11)	0.5727 (2)	0.30408 (10)	0.0772 (5)
O3	0.79753 (10)	0.8085 (2)	0.20235 (11)	0.0740 (5)
F1	0.64895 (9)	0.1741 (2)	−0.19068 (10)	0.0971 (5)
F2	0.52079 (11)	0.2303 (2)	−0.35774 (10)	0.1029 (6)
S1	0.84155 (4)	0.64492 (7)	0.21283 (4)	0.0619 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0636 (15)	0.0573 (14)	0.0623 (15)	0.0075 (12)	0.0267 (13)	0.0050 (11)
C2	0.0869 (18)	0.0589 (15)	0.0500 (14)	0.0087 (13)	0.0274 (14)	0.0016 (10)
C3	0.0761 (18)	0.0625 (16)	0.0607 (15)	0.0060 (13)	0.0122 (13)	−0.0038 (11)
C4	0.0635 (16)	0.0821 (19)	0.087 (2)	0.0011 (14)	0.0268 (16)	−0.0009 (14)
C5	0.0809 (18)	0.0705 (16)	0.0687 (16)	0.0017 (14)	0.0372 (15)	0.0020 (12)
C6	0.0702 (15)	0.0380 (12)	0.0526 (13)	0.0016 (10)	0.0226 (11)	−0.0001 (9)
C7	0.0803 (16)	0.0451 (15)	0.0530 (13)	0.0055 (12)	0.0252 (12)	0.0038 (11)
C8	0.0877 (17)	0.0441 (13)	0.0535 (13)	0.0094 (12)	0.0198 (12)	0.0069 (10)
C9	0.0733 (15)	0.0474 (14)	0.0556 (13)	0.0164 (12)	0.0117 (12)	0.0094 (10)
C10	0.0643 (14)	0.0413 (13)	0.0549 (13)	0.0079 (11)	0.0115 (11)	0.0077 (9)
C11	0.0672 (14)	0.0435 (13)	0.0596 (13)	0.0097 (11)	0.0158 (11)	0.0037 (10)
C12	0.0631 (14)	0.0409 (12)	0.0522 (12)	−0.0002 (11)	0.0031 (11)	−0.0037 (10)
C13	0.0656 (15)	0.0497 (14)	0.0621 (14)	0.0027 (12)	0.0040 (13)	−0.0012 (11)
C14	0.0597 (15)	0.0575 (16)	0.0884 (18)	0.0001 (13)	0.0105 (14)	−0.0153 (14)
C15	0.0815 (18)	0.0529 (15)	0.0763 (17)	−0.0159 (14)	0.0227 (15)	−0.0202 (13)
C16	0.0898 (19)	0.0559 (16)	0.0635 (15)	−0.0092 (14)	0.0163 (15)	−0.0017 (12)
C17	0.0702 (15)	0.0513 (15)	0.0592 (14)	0.0028 (12)	0.0079 (13)	0.0031 (11)
C18	0.109 (2)	0.089 (2)	0.120 (2)	−0.0272 (18)	0.058 (2)	−0.0307 (18)
N1	0.0741 (12)	0.0373 (11)	0.0504 (10)	0.0061 (9)	0.0144 (9)	0.0024 (8)
N2	0.0660 (11)	0.0395 (10)	0.0518 (10)	0.0089 (9)	0.0089 (9)	0.0057 (8)
O1	0.1381 (16)	0.0460 (11)	0.0679 (10)	0.0203 (10)	0.0104 (10)	−0.0024 (8)
O2	0.0933 (12)	0.0732 (11)	0.0470 (8)	0.0107 (9)	0.0088 (8)	0.0031 (7)
O3	0.0833 (11)	0.0487 (9)	0.0760 (10)	0.0128 (8)	0.0169 (9)	−0.0088 (7)
F1	0.0793 (10)	0.1325 (14)	0.0878 (10)	0.0192 (9)	0.0422 (8)	0.0291 (9)
F2	0.1248 (13)	0.1301 (14)	0.0601 (9)	0.0342 (11)	0.0437 (9)	0.0201 (8)
S1	0.0722 (4)	0.0485 (4)	0.0499 (3)	0.0083 (3)	0.0084 (3)	−0.0018 (2)

C1—F1	1.347 (2)	C10—H10A	0.9700
C1—C2	1.367 (3)	C10—H10B	0.9700
C1—C6	1.369 (3)	C11—N1	1.466 (3)
C2—C3	1.351 (3)	C11—H11A	0.9700
C2—F2	1.352 (3)	C11—H11B	0.9700
C3—C4	1.375 (3)	C12—C13	1.387 (3)
C3—H3	0.9300	C12—C17	1.387 (3)
C4—C5	1.375 (3)	C12—S1	1.751 (2)
C4—H4	0.9300	C13—C14	1.374 (3)
C5—C6	1.379 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.383 (4)
C6—C7	1.498 (3)	C14—H14	0.9300
C7—O1	1.225 (3)	C15—C16	1.380 (4)
C7—N1	1.330 (3)	C15—C18	1.497 (4)
C8—N1	1.454 (3)	C16—C17	1.372 (3)
C8—C9	1.496 (3)	C16—H16	0.9300
C8—H8A	0.9700	C17—H17	0.9300
C8—H8B	0.9700	C18—H18A	0.9600
C9—N2	1.470 (3)	C18—H18B	0.9600
C9—H9A	0.9700	C18—H18C	0.9600
C9—H9B	0.9700	N2—S1	1.6311 (17)
C10—N2	1.470 (2)	O2—S1	1.4234 (15)
C10—C11	1.500 (3)	O3—S1	1.4281 (16)
F1—C1—C2	119.3 (2)	C10—C11—H11A	109.5
F1—C1—C6	119.3 (2)	N1—C11—H11B	109.5
C2—C1—C6	121.4 (2)	C10—C11—H11B	109.5
C3—C2—F2	120.1 (2)	H11A—C11—H11B	108.1
C3—C2—C1	121.2 (2)	C13—C12—C17	119.3 (2)
F2—C2—C1	118.7 (2)	C13—C12—S1	120.31 (18)
C2—C3—C4	118.6 (2)	C17—C12—S1	120.34 (18)
C2—C3—H3	120.7	C14—C13—C12	119.8 (2)
C4—C3—H3	120.7	C14—C13—H13	120.1
C3—C4—C5	120.3 (2)	C12—C13—H13	120.1
C3—C4—H4	119.9	C13—C14—C15	121.6 (2)
C5—C4—H4	119.9	C13—C14—H14	119.2
C4—C5—C6	121.1 (2)	C15—C14—H14	119.2
C4—C5—H5	119.4	C16—C15—C14	117.7 (3)
C6—C5—H5	119.4	C16—C15—C18	121.7 (3)
C1—C6—C5	117.3 (2)	C14—C15—C18	120.6 (3)
C1—C6—C7	120.6 (2)	C17—C16—C15	121.9 (2)
C5—C6—C7	121.8 (2)	C17—C16—H16	119.0
O1—C7—N1	122.5 (2)	C15—C16—H16	119.0
O1—C7—C6	119.0 (2)	C16—C17—C12	119.6 (2)
N1—C7—C6	118.36 (19)	C16—C17—H17	120.2
N1—C8—C9	110.67 (17)	C12—C17—H17	120.2
N1—C8—H8A	109.5	C15—C18—H18A	109.5
C9—C8—H8A	109.5	C15—C18—H18B	109.5
N1—C8—H8B	109.5	H18A—C18—H18B	109.5
C9—C8—H8B	109.5	C15—C18—H18C	109.5
H8A—C8—H8B	108.1	H18A—C18—H18C	109.5
N2—C9—C8	109.02 (18)	H18B—C18—H18C	109.5
N2—C9—H9A	109.9	C7—N1—C8	120.31 (17)
C8—C9—H9A	109.9	C7—N1—C11	125.61 (17)
N2—C9—H9B	109.9	C8—N1—C11	114.06 (16)
C8—C9—H9B	109.9	C9—N2—C10	111.79 (16)
H9A—C9—H9B	108.3	C9—N2—S1	117.19 (14)
N2—C10—C11	109.02 (16)	C10—N2—S1	118.30 (13)
N2—C10—H10A	109.9	O2—S1—O3	119.91 (10)
C11—C10—H10A	109.9	O2—S1—N2	106.66 (9)
N2—C10—H10B	109.9	O3—S1—N2	106.31 (9)
C11—C10—H10B	109.9	O2—S1—C12	108.06 (10)
H10A—C10—H10B	108.3	O3—S1—C12	107.97 (10)
N1—C11—C10	110.57 (17)	N2—S1—C12	107.32 (9)
N1—C11—H11A	109.5
F1—C1—C2—C3	180.0 (2)	C15—C16—C17—C12	−0.6 (3)
C6—C1—C2—C3	−0.2 (4)	C13—C12—C17—C16	−1.0 (3)
F1—C1—C2—F2	0.8 (3)	S1—C12—C17—C16	−179.41 (17)
C6—C1—C2—F2	−179.4 (2)	O1—C7—N1—C8	−4.0 (3)
F2—C2—C3—C4	178.9 (2)	C6—C7—N1—C8	172.92 (19)
C1—C2—C3—C4	−0.2 (4)	O1—C7—N1—C11	178.1 (2)
C2—C3—C4—C5	0.4 (4)	C6—C7—N1—C11	−5.1 (3)
C3—C4—C5—C6	−0.1 (4)	C9—C8—N1—C7	127.7 (2)
F1—C1—C6—C5	−179.7 (2)	C9—C8—N1—C11	−54.1 (3)
C2—C1—C6—C5	0.5 (3)	C10—C11—N1—C7	−128.3 (2)
F1—C1—C6—C7	−5.4 (3)	C10—C11—N1—C8	53.6 (2)
C2—C1—C6—C7	174.8 (2)	C8—C9—N2—C10	−60.2 (2)
C4—C5—C6—C1	−0.3 (3)	C8—C9—N2—S1	158.59 (15)
C4—C5—C6—C7	−174.6 (2)	C11—C10—N2—C9	59.8 (2)
C1—C6—C7—O1	−76.6 (3)	C11—C10—N2—S1	−159.43 (14)
C5—C6—C7—O1	97.4 (3)	C9—N2—S1—O2	−44.59 (18)
C1—C6—C7—N1	106.4 (2)	C10—N2—S1—O2	176.77 (15)
C5—C6—C7—N1	−79.5 (3)	C9—N2—S1—O3	−173.63 (15)
N1—C8—C9—N2	55.6 (2)	C10—N2—S1—O3	47.72 (18)
N2—C10—C11—N1	−54.7 (2)	C9—N2—S1—C12	71.02 (17)
C17—C12—C13—C14	1.0 (3)	C10—N2—S1—C12	−67.62 (17)
S1—C12—C13—C14	179.43 (16)	C13—C12—S1—O2	18.83 (19)
C12—C13—C14—C15	0.5 (3)	C17—C12—S1—O2	−162.78 (17)
C13—C14—C15—C16	−2.0 (3)	C13—C12—S1—O3	149.92 (17)
C13—C14—C15—C18	176.9 (2)	C17—C12—S1—O3	−31.70 (19)
C14—C15—C16—C17	2.1 (3)	C13—C12—S1—N2	−95.85 (17)
C18—C15—C16—C17	−176.9 (2)	C17—C12—S1—N2	82.53 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3i	0.93	2.58	3.495 (3)	169
C8—H8A···O3ii	0.97	2.34	3.255 (3)	157
C10—H10B···O1iii	0.97	2.48	3.402 (3)	159
C8—H8B···F1iv	0.97	2.57	3.518 (3)	165
C11—H11A···F2iv	0.97	2.56	3.296 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O3i	0.93	2.58	3.495 (3)	169
C8—H8A⋯O3ii	0.97	2.34	3.255 (3)	157
C10—H10B⋯O1iii	0.97	2.48	3.402 (3)	159
C8—H8B⋯F1iv	0.97	2.57	3.518 (3)	165
C11—H11A⋯F2iv	0.97	2.56	3.296 (3)	133

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