(2,3-Difluoro­phen­yl)(4-tosyl­piperazin-1-yl)methanone

Sreenivasa, S.; ManojKumar, K.E.; Suchetan, P.A.; Tonannavar, J.; Chavan, Y.; Palakshamurthy, B.S.

doi:10.1107/S1600536812051690

organic compounds

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Volume 69| Part 2| February 2013| Page o185

doi:10.1107/S1600536812051690

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(2,3-Difluorophenyl)(4-tosylpiperazin-1-yl)methanone

S. Sreenivasa,^a ^* K. E. ManojKumar,^a P. A. Suchetan,^b J. Tonannavar,^c Yashshwita Chavan ^c and B. S. Palakshamurthy ^d

^aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, ^bDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, ^cDepartment of Physics, Karnatak University, Dharwad, Karnataka 580 003, India, and ^dDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
^*Correspondence e-mail: drsreenivasa@yahoo.co.in

(Received 19 December 2012; accepted 22 December 2012; online 4 January 2013)

In the title compound, C₁₈H₁₈F₂N₂O₃S, 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 fluorobenzene and sulfonyl rings and the fluorobenzene and piperazine rings are 30.97 (2) and 75.98 (2)°, respectively. In the crystal, molecules are connected to form a tetrameric unit through C—H⋯O hydrogen bonds. The structure is further stabilized by weak intermolecular C—H⋯F interactions, 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_r = 380.40
Monoclinic, P 2₁ /c
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
θ_max = 22.4°

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.092
S = 1.06
2359 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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⋯F1^iv	0.97	2.57	3.518 (3)	165
C11—H11A⋯F2^iv	0.97	2.56	3.296 (3)	133
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y-1, z; (iii) x, y+1, z; (iv) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812051690/sj5290sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812051690/sj5290Isup3.cml

checkCIF report

Comment top

Numerous piperazine derivatives such as aryl amides, sulphonamides, Mannich bases, Schiff's 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 effects (Gan et al., 2009a, 2009b). Keeping this in mind, we synthesized the title compound to study its crystal structure.

The compound crystallizes in monoclinic crystal system and the space group P2₁/c. In the crystal structure, the piperazine ring adopts chair conformation. The dihedral angle between the sulfonyl bound benzene ring and the best fit plane through all six atoms of the piperazine ring is 69.4 (2)°, while those between the fluorobenzene and the sulfonyl rings and the fluorobenzene and the piperazine rings are 30.97 (2)° and 75.98 (2)° respectively. In the crystal structure molecules form a tetrameric unit generating alternate R₂²(22), (C8—H8A···O3, C10—H10B···O1) and inversion related C4—H4···O3 R₂²(10) rings (Bernstein et al.1995). The structure is further stabilized by weak intermolecular C11—H11A···F2 and C8—H8B···F1 interactions.

Related literature top

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 top

1-Tosylpiperazine (0.01 mmol) and triethylamine (0.02 mmol) were dissolved in 10 ml of dichloromethane (CH₂Cl₂). The mixture was cooled to 0°C and 1-propanephosphonic acid anhydride (0.02 mmol) and 2,4-diflurobenzoic acid (0.01 mmol) added. The reaction mixture was stirred at 80°C for 14 h. The reaction was monitored by TLC and the solvent removed yielding the crude product. The crude mass was purified by chromatography on 230–400 silica gel with petroleum ether and ethyl acetate as eluents. Single crystals of the title compound were obtained from slow evaporation of a solution of the compound in petroleum ether and ethyl acetate (1:4).

Computing details top

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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.

(2,3-Difluorophenyl)(4-tosylpiperazin-1-yl)methanone top

Crystal data top

C₁₈H₁₈F₂N₂O₃S	Prism
M_r = 380.40	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	2359 independent reflections
Radiation source: fine-focus sealed tube	1930 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 0.95 pixels mm^-1	θ_max = 22.4°, θ_min = 2.6°
ϕ and ω scans	h = −18→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→7
T_min = 0.942, T_max = 0.958	l = −16→16
11988 measured reflections

Refinement top

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(F_o²) + (0.0494P)² + 0.3661P] where P = (F_o² + 2F_c²)/3
2359 reflections	(Δ/σ)_max = 0.001
236 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³
0 constraints

Crystal data top

C₁₈H₁₈F₂N₂O₃S	V = 1843.22 (6) Å³
M_r = 380.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.0456 (4) Å	µ = 0.22 mm⁻¹
b = 7.6026 (1) Å	T = 298 K
c = 15.5113 (3) Å	0.28 × 0.26 × 0.20 mm
β = 113.513 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2359 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1930 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.958	R_int = 0.023
11988 measured reflections	θ_max = 22.4°

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.06	Δρ_max = 0.15 e Å⁻³
2359 reflections	Δρ_min = −0.23 e Å⁻³
236 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···F1^iv	0.97	2.57	3.518 (3)	165
C11—H11A···F2^iv	0.97	2.56	3.296 (3)	133

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y−1, z; (iii) x, y+1, z; (iv) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈F₂N₂O₃S
M_r	380.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	17.0456 (4), 7.6026 (1), 15.5113 (3)
β (°)	113.513 (1)
V (Å³)	1843.22 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.28 × 0.26 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.942, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	11988, 2359, 1930
R_int	0.023
θ_max (°)	22.4
(sin θ/λ)_max (Å⁻¹)	0.535

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.092, 1.06
No. of reflections	2359
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.23

Computer programs: APEX2 (Bruker, 2009), APEX2 and SAINT-Plus (Bruker, 2009), SAINT-Plus and XPREP (Bruker,2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3ⁱ	0.93	2.58	3.495 (3)	169.3
C8—H8A···O3ⁱⁱ	0.97	2.34	3.255 (3)	156.8
C10—H10B···O1ⁱⁱⁱ	0.97	2.48	3.402 (3)	159.2
C8—H8B···F1^iv	0.97	2.57	3.518 (3)	165.0
C11—H11A···F2^iv	0.97	2.56	3.296 (3)	133.1

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y−1, z; (iii) x, y+1, z; (iv) x, −y+1/2, z+1/2.

Acknowledgements

The authors thank Dr S. C. Sharma, 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.

References

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