4-(4-Methyl­phenyl­sulfon­yl)piperazin-1-ium tri­fluoro­acetate

Sreenivasa, S.; Mohan, N.R.; Madhu Chakrapani Rao, T.; Suchetan, P.A.; Palakshamurthy, B.S.; Vijithkumar

doi:10.1107/S1600536813015900

organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1112

https://doi.org/10.1107/S1600536813015900

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4-(4-Methylphenylsulfonyl)piperazin-1-ium trifluoroacetate

S. Sreenivasa,^a ^* N. R. Mohan,^a T. Madhu Chakrapani Rao,^b P. A. Suchetan,^c B. S. Palakshamurthy ^d and Vijithkumar ^e

^aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, ^bTadimety Aromatics Pvt Ltd, Hirehally Industrial Area, Tumkur, Karnataka 572 168 , India, ^cDepartment of Studies in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, ^dDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and ^eSoild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India
^*Correspondence e-mail: drsreenivasa@yahoo.co.in

(Received 30 May 2013; accepted 7 June 2013; online 19 June 2013)

In the title salt, C₁₁H₁₇N₂O₂S⁺·CF₃COO⁻, the cation is protonated at the secondary piperazine N atom. The dihedral angle between the benzene ring and the piperazine mean plane is 85.54 (10)°. In the crystal, cations and anions are connected by two types of strong N—H⋯O hydrogen bonds into chains extending along [101]. The chains are further assembled into (10-1) layers via stacking interactions between benzene rings of the cations [centroid–centroid distance = 3.7319 (13) Å] and a C—H⋯O interaction involving a piperazine C—H group and a sulfonyl O atom. Another C—H⋯O interaction between the piperazine ring and the sulfonyl group connects the ions into a three-dimensional network.

Related literature

For the synthesis, characterization and biological activity of piperazine derivatives, see: Gan et al. (2009a ,b ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₁H₁₇N₂O₂S⁺·C₂F₃O₂⁻
M_r = 354.35
Monoclinic, P 2₁ /n
a = 7.8796 (6) Å
b = 22.5891 (15) Å
c = 9.4626 (7) Å
β = 110.446 (3)°
V = 1578.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 100 K
0.24 × 0.22 × 0.20 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.941, T_max = 0.950
11562 measured reflections
2781 independent reflections
2417 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.094
S = 1.04
2781 reflections
217 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O4ⁱ	0.87 (3)	1.91 (3)	2.782 (2)	174 (2)
C8—H8B⋯O1ⁱⁱ	0.97	2.45	3.328 (2)	150
C9—H9B⋯O2ⁱⁱⁱ	0.97	2.43	3.146 (2)	130
N2—H2N2⋯O3	0.86 (2)	1.86 (2)	2.690 (2)	163 (2)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z; (iii) x-1, y, z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813015900/gk2578sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813015900/gk2578Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813015900/gk2578Isup3.cml

checkCIF report

Comment top

Numerous piperazine derivatives like aryl amide, sulfonamides, Mannich bases, Schiff 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 (Gan et al., 2009a,b). Keeping this in mind, we synthesized the title compound and here we report its crystal structure.

The title molecular salt, C₁₁H₁₇SO₂N₂⁺.CF₃COO^-, crystallizes in monoclinic crystal system and P2₁/n space group. The cation is protonated at the secondary N atom of the piperazine ring (Fig. 1). The piperazine ring adopts a chair conformation and the dihedral angle between the benzene ring and the piperazine ring (considering the mean plane formed by all the non-hydrogen atoms) in the cation is 85.54 (10)^o. In the crystal, the ions are connected by strong N2—H1(N2)···O4 and N2—H2(N2)···O3 hydrogen bonds (Fig. 2, Table 1). The cations are further connected through weak C8—H8B···O1 and C9—H9B···O2 interactions forming chain C(6) and ring R₂²(8) motifs (Bernstein et al.1995) (Fig. 3, Table 1). The crystal structure is further stabilized by aromatic π-π stacking interactions.

Related literature top

For the synthesis, characterization and biological activity of piperazine derivatives, see: Gan et al. (2009a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of tert-butyl 4-[(4-methylphenyl)sulfonyl]piperazine-1-carboxylate (0.002 moles, 1 gram) (1), trifluroacetic acid (TFA) (0.013 moles, 1 ml) in 1,2-dichloroethane (10 ml) was refluxed for 2 h. Reaction mixture was then cooled to room temperature and concentrated to get crude pale yellow colored solid 1-[(4-methylphenyl)sulfonyl]piperazine (2). The crude compound (2) was purified by column chromatography using petroleum ether:/ethyl acetate (7:3) as eluent to get white coloured solid (melting point = 518 K), which was further recrystallized from petroleum ether/ dichloromethane (1:1) to obtain colorless crystals suitable for diffraction studies.

Structure description top

For the synthesis, characterization and biological activity of piperazine derivatives, see: Gan et al. (2009a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995).

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: Mercury (Macrae et al., 2008); 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. Chain of anions and cations connected via N—H···O hydrogen bonds. The hydrogen bonds are shown as dashed lines and the hydrogen atoms not involved in hydrogen bonds are omitted.
	Fig. 3. Molecular packing in the title compound displaying R₂²(10) rings and C(6) chains. Trifluoroacetate ion is omitted for clarity.
	Fig. 4. Aromatic π-π stacking interactions observed in the crystal structure.

4-(4-Methylphenylsulfonyl)piperazin-1-ium trifluoroacetate top

Crystal data top

C₁₁H₁₇N₂O₂S⁺·C₂F₃O₂⁻	prism
M_r = 354.35	D_x = 1.491 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 518 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.8796 (6) Å	Cell parameters from 2417 reflections
b = 22.5891 (15) Å	θ = 1.8–25.0°
c = 9.4626 (7) Å	µ = 0.26 mm⁻¹
β = 110.446 (3)°	T = 100 K
V = 1578.2 (2) Å³	Prism, colourless
Z = 4	0.24 × 0.22 × 0.20 mm
F(000) = 736

Data collection top

Bruker APEXII diffractometer	2781 independent reflections
Radiation source: fine-focus sealed tube	2417 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 1.03 pixels mm^-1	θ_max = 25.0°, θ_min = 1.8°
phi and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −26→24
T_min = 0.941, T_max = 0.950	l = −11→10
11562 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.042P)² + 1.4486P] where P = (F_o² + 2F_c²)/3
2781 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.86 e Å⁻³
1 restraint	Δρ_min = −0.55 e Å⁻³
0 constraints

Crystal data top

C₁₁H₁₇N₂O₂S⁺·C₂F₃O₂⁻	V = 1578.2 (2) Å³
M_r = 354.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8796 (6) Å	µ = 0.26 mm⁻¹
b = 22.5891 (15) Å	T = 100 K
c = 9.4626 (7) Å	0.24 × 0.22 × 0.20 mm
β = 110.446 (3)°

Data collection top

Bruker APEXII diffractometer	2781 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2417 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.950	R_int = 0.030
11562 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.86 e Å⁻³
2781 reflections	Δρ_min = −0.55 e Å⁻³
217 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	0.7630 (2)	0.06870 (8)	0.2940 (2)	0.0153 (4)
C2	0.6839 (3)	0.01633 (9)	0.3194 (2)	0.0183 (4)
H2	0.6086	−0.0057	0.2388	0.022*
C3	0.7192 (3)	−0.00242 (9)	0.4665 (2)	0.0196 (4)
H3	0.6670	−0.0373	0.4841	0.023*
C4	0.8315 (3)	0.03019 (9)	0.5883 (2)	0.0192 (4)
C5	0.9097 (3)	0.08191 (9)	0.5598 (2)	0.0214 (4)
H5	0.9856	0.1038	0.6404	0.026*
C6	0.8771 (3)	0.10158 (9)	0.4140 (2)	0.0198 (4)
H6	0.9307	0.1362	0.3967	0.024*
C7	0.8684 (3)	0.00917 (10)	0.7478 (2)	0.0259 (5)
H7A	0.9878	0.0212	0.8105	0.039*
H7B	0.8600	−0.0332	0.7488	0.039*
H7C	0.7809	0.0261	0.7855	0.039*
C8	0.3628 (2)	0.09780 (8)	0.0749 (2)	0.0167 (4)
H8A	0.3811	0.0860	0.1777	0.020*
H8B	0.3528	0.0623	0.0149	0.020*
C9	0.1909 (3)	0.13368 (9)	0.0128 (2)	0.0171 (4)
H9A	0.1691	0.1438	−0.0917	0.020*
H9B	0.0889	0.1106	0.0168	0.020*
C10	0.3658 (3)	0.22462 (9)	0.1004 (2)	0.0193 (4)
H10A	0.3766	0.2598	0.1617	0.023*
H10B	0.3462	0.2371	−0.0022	0.023*
C11	0.5387 (3)	0.18885 (8)	0.1599 (2)	0.0175 (4)
H11A	0.6391	0.2118	0.1521	0.021*
H11B	0.5646	0.1794	0.2654	0.021*
C12	−0.0777 (3)	0.32181 (9)	0.1546 (2)	0.0218 (5)
C13	−0.1238 (2)	0.30961 (9)	−0.0157 (2)	0.0167 (4)
F1	0.0057 (3)	0.37256 (7)	0.19613 (16)	0.0589 (5)
F2	0.0210 (2)	0.27979 (6)	0.24299 (14)	0.0485 (4)
F3	−0.2294 (2)	0.32421 (8)	0.18855 (15)	0.0523 (4)
N1	0.5186 (2)	0.13357 (7)	0.07164 (17)	0.0146 (3)
N2	0.2087 (2)	0.18872 (7)	0.10346 (19)	0.0162 (4)
O1	0.66600 (18)	0.04597 (6)	0.00690 (15)	0.0202 (3)
O2	0.84473 (18)	0.13710 (6)	0.10568 (15)	0.0213 (3)
O3	−0.05244 (19)	0.26533 (6)	−0.04921 (15)	0.0215 (3)
O4	−0.22722 (19)	0.34645 (6)	−0.10056 (15)	0.0231 (3)
S1	0.70876 (6)	0.09536 (2)	0.10835 (5)	0.01538 (15)
H1N2	0.222 (3)	0.1792 (10)	0.196 (3)	0.029 (6)*
H2N2	0.114 (2)	0.2104 (9)	0.066 (2)	0.021 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0127 (9)	0.0189 (10)	0.0163 (10)	0.0046 (8)	0.0074 (8)	0.0021 (8)
C2	0.0177 (10)	0.0179 (10)	0.0197 (10)	0.0016 (8)	0.0071 (8)	−0.0026 (8)
C3	0.0210 (10)	0.0178 (10)	0.0232 (11)	0.0021 (8)	0.0120 (9)	0.0019 (8)
C4	0.0158 (10)	0.0249 (11)	0.0191 (10)	0.0050 (8)	0.0091 (8)	0.0016 (8)
C5	0.0190 (10)	0.0263 (11)	0.0181 (10)	−0.0031 (8)	0.0053 (8)	−0.0028 (8)
C6	0.0162 (10)	0.0218 (11)	0.0222 (11)	−0.0026 (8)	0.0078 (8)	0.0001 (8)
C7	0.0269 (12)	0.0338 (12)	0.0201 (11)	0.0035 (9)	0.0120 (9)	0.0036 (9)
C8	0.0149 (10)	0.0162 (10)	0.0207 (10)	−0.0021 (8)	0.0084 (8)	−0.0026 (8)
C9	0.0158 (10)	0.0212 (10)	0.0152 (10)	0.0002 (8)	0.0066 (8)	−0.0025 (8)
C10	0.0229 (10)	0.0162 (10)	0.0213 (10)	0.0017 (8)	0.0108 (8)	0.0016 (8)
C11	0.0182 (10)	0.0150 (10)	0.0210 (10)	−0.0004 (8)	0.0089 (8)	−0.0023 (8)
C12	0.0272 (11)	0.0196 (11)	0.0181 (10)	0.0076 (9)	0.0071 (9)	0.0025 (8)
C13	0.0141 (9)	0.0194 (10)	0.0169 (10)	0.0003 (8)	0.0058 (8)	0.0015 (8)
F1	0.0970 (14)	0.0423 (9)	0.0240 (8)	−0.0291 (9)	0.0041 (8)	−0.0078 (6)
F2	0.0775 (11)	0.0456 (9)	0.0158 (7)	0.0377 (8)	0.0080 (7)	0.0068 (6)
F3	0.0497 (9)	0.0871 (12)	0.0294 (8)	0.0198 (9)	0.0253 (7)	0.0013 (8)
N1	0.0143 (8)	0.0145 (8)	0.0172 (8)	0.0000 (6)	0.0080 (7)	−0.0012 (6)
N2	0.0178 (9)	0.0181 (9)	0.0142 (9)	0.0062 (7)	0.0075 (7)	0.0028 (7)
O1	0.0220 (7)	0.0234 (8)	0.0177 (7)	0.0056 (6)	0.0099 (6)	−0.0016 (6)
O2	0.0165 (7)	0.0269 (8)	0.0244 (8)	0.0003 (6)	0.0119 (6)	0.0045 (6)
O3	0.0274 (8)	0.0201 (8)	0.0177 (7)	0.0089 (6)	0.0087 (6)	0.0027 (6)
O4	0.0254 (8)	0.0254 (8)	0.0168 (7)	0.0122 (6)	0.0054 (6)	0.0030 (6)
S1	0.0137 (3)	0.0193 (3)	0.0159 (3)	0.00225 (18)	0.00858 (19)	0.00105 (18)

Geometric parameters (Å, º) top

C1—C6	1.392 (3)	C9—H9B	0.9700
C1—C2	1.397 (3)	C10—N2	1.488 (3)
C1—S1	1.7623 (19)	C10—C11	1.514 (3)
C2—C3	1.387 (3)	C10—H10A	0.9700
C2—H2	0.9300	C10—H10B	0.9700
C3—C4	1.394 (3)	C11—N1	1.480 (2)
C3—H3	0.9300	C11—H11A	0.9700
C4—C5	1.391 (3)	C11—H11B	0.9700
C4—C7	1.510 (3)	C12—F1	1.312 (3)
C5—C6	1.385 (3)	C12—F2	1.323 (2)
C5—H5	0.9300	C12—F3	1.343 (3)
C6—H6	0.9300	C12—C13	1.548 (3)
C7—H7A	0.9600	C13—O3	1.242 (2)
C7—H7B	0.9600	C13—O3	1.242 (2)
C7—H7C	0.9600	C13—O4	1.243 (2)
C8—N1	1.479 (2)	N1—S1	1.6576 (16)
C8—C9	1.510 (3)	N2—H1N2	0.87 (3)
C8—H8A	0.9700	N2—H2N2	0.860 (16)
C8—H8B	0.9700	O1—S1	1.4332 (14)
C9—N2	1.489 (2)	O2—S1	1.4340 (14)
C9—H9A	0.9700

C6—C1—C2	120.75 (18)	N2—C10—H10A	109.6
C6—C1—S1	119.58 (15)	C11—C10—H10A	109.6
C2—C1—S1	119.60 (15)	N2—C10—H10B	109.6
C3—C2—C1	119.12 (18)	C11—C10—H10B	109.6
C3—C2—H2	120.4	H10A—C10—H10B	108.1
C1—C2—H2	120.4	N1—C11—C10	109.58 (15)
C2—C3—C4	121.03 (19)	N1—C11—H11A	109.8
C2—C3—H3	119.5	C10—C11—H11A	109.8
C4—C3—H3	119.5	N1—C11—H11B	109.8
C5—C4—C3	118.68 (18)	C10—C11—H11B	109.8
C5—C4—C7	120.96 (18)	H11A—C11—H11B	108.2
C3—C4—C7	120.36 (19)	F1—C12—F2	108.37 (18)
C6—C5—C4	121.48 (19)	F1—C12—F3	106.73 (18)
C6—C5—H5	119.3	F2—C12—F3	104.68 (17)
C4—C5—H5	119.3	F1—C12—C13	112.23 (17)
C5—C6—C1	118.94 (18)	F2—C12—C13	113.76 (16)
C5—C6—H6	120.5	F3—C12—C13	110.57 (16)
C1—C6—H6	120.5	O3—C13—O4	128.86 (18)
C4—C7—H7A	109.5	O3—C13—O4	128.86 (18)
C4—C7—H7B	109.5	O3—C13—C12	116.54 (16)
H7A—C7—H7B	109.5	O3—C13—C12	116.54 (16)
C4—C7—H7C	109.5	O4—C13—C12	114.60 (17)
H7A—C7—H7C	109.5	C8—N1—C11	112.06 (14)
H7B—C7—H7C	109.5	C8—N1—S1	114.04 (12)
N1—C8—C9	109.67 (15)	C11—N1—S1	114.21 (12)
N1—C8—H8A	109.7	C10—N2—C9	110.79 (15)
C9—C8—H8A	109.7	C10—N2—H1N2	110.0 (15)
N1—C8—H8B	109.7	C9—N2—H1N2	109.2 (16)
C9—C8—H8B	109.7	C10—N2—H2N2	106.9 (15)
H8A—C8—H8B	108.2	C9—N2—H2N2	110.2 (15)
N2—C9—C8	109.43 (15)	H1N2—N2—H2N2	110 (2)
N2—C9—H9A	109.8	O1—S1—O2	120.15 (8)
C8—C9—H9A	109.8	O1—S1—N1	106.33 (8)
N2—C9—H9B	109.8	O2—S1—N1	106.28 (8)
C8—C9—H9B	109.8	O1—S1—C1	108.66 (9)
H9A—C9—H9B	108.2	O2—S1—C1	108.65 (9)
N2—C10—C11	110.41 (16)	N1—S1—C1	105.87 (8)

C6—C1—C2—C3	0.6 (3)	C9—C8—N1—C11	58.60 (19)
S1—C1—C2—C3	−176.24 (14)	C9—C8—N1—S1	−169.70 (12)
C1—C2—C3—C4	0.1 (3)	C10—C11—N1—C8	−57.2 (2)
C2—C3—C4—C5	−0.6 (3)	C10—C11—N1—S1	171.14 (12)
C2—C3—C4—C7	179.94 (18)	C11—C10—N2—C9	−58.0 (2)
C3—C4—C5—C6	0.5 (3)	C8—C9—N2—C10	58.8 (2)
C7—C4—C5—C6	179.90 (18)	O4—C13—O3—O3	0.00 (8)
C4—C5—C6—C1	0.2 (3)	C12—C13—O3—O3	0.00 (7)
C2—C1—C6—C5	−0.7 (3)	C8—N1—S1—O1	52.91 (14)
S1—C1—C6—C5	176.09 (15)	C11—N1—S1—O1	−176.43 (13)
N1—C8—C9—N2	−58.22 (19)	C8—N1—S1—O2	−177.97 (13)
N2—C10—C11—N1	56.2 (2)	C11—N1—S1—O2	−47.32 (14)
F1—C12—C13—O3	117.9 (2)	C8—N1—S1—C1	−62.54 (14)
F2—C12—C13—O3	−5.6 (3)	C11—N1—S1—C1	68.11 (14)
F3—C12—C13—O3	−123.07 (19)	C6—C1—S1—O1	153.58 (15)
F1—C12—C13—O3	117.9 (2)	C2—C1—S1—O1	−29.56 (17)
F2—C12—C13—O3	−5.6 (3)	C6—C1—S1—O2	21.24 (18)
F3—C12—C13—O3	−123.07 (19)	C2—C1—S1—O2	−161.90 (14)
F1—C12—C13—O4	−61.4 (2)	C6—C1—S1—N1	−92.56 (16)
F2—C12—C13—O4	175.05 (18)	C2—C1—S1—N1	84.30 (16)
F3—C12—C13—O4	57.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O4ⁱ	0.87 (3)	1.91 (3)	2.782 (2)	174 (2)
C8—H8B···O1ⁱⁱ	0.97	2.45	3.328 (2)	150
C9—H9B···O2ⁱⁱⁱ	0.97	2.43	3.146 (2)	130
N2—H2N2···O3	0.86 (2)	1.86 (2)	2.690 (2)	163 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₇N₂O₂S⁺·C₂F₃O₂⁻
M_r	354.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.8796 (6), 22.5891 (15), 9.4626 (7)
β (°)	110.446 (3)
V (Å³)	1578.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.24 × 0.22 × 0.20

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.941, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	11562, 2781, 2417
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.094, 1.04
No. of reflections	2781
No. of parameters	217
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.55

Computer programs: APEX2 (Bruker, 2009), APEX2 and SAINT-Plus (Bruker, 2009), SAINT-Plus and XPREP (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O4ⁱ	0.87 (3)	1.91 (3)	2.782 (2)	174 (2)
C8—H8B···O1ⁱⁱ	0.97	2.45	3.328 (2)	149.7
C9—H9B···O2ⁱⁱⁱ	0.97	2.43	3.146 (2)	130.4
N2—H2N2···O3	0.860 (16)	1.857 (17)	2.690 (2)	163 (2)

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

Acknowledgements

The authors thank Dr S. C. Sharma, Former Vice Chancellor, Tumkur University, Tumkur for his constant encouragement and Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for his help and valuable suggestions. BSPM thanks Dr H. C. Devaraje Gowda, Department of Physics Yuvarajas College (constituent), University of Mysore, for his guidance.

References

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