1-Isopropyl-4-tosyl­piperazin-1-ium trifluoro­acetate

Li, J.-S.; Yang, D.-W.; Liu, W.-D.

doi:10.1107/S1600536807061570

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o22

https://doi.org/10.1107/S1600536807061570

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1-Isopropyl-4-tosylpiperazin-1-ium trifluoroacetate

Jiang-Sheng Li,^a ^* Dao-Wu Yang ^a and Wei-Dong Liu ^b

^aSchool of Chemical and Environmental Engineering, Changsha University of Science and Technology, Changsha 410076, People's Republic of China, and ^bHunan Research Institute of Chemical Industry, Changsha 410007, People's Republic of China
^*Correspondence e-mail: jansenlee1103@yahoo.com.cn

(Received 20 November 2007; accepted 21 November 2007; online 6 December 2007)

In the title compound, C₁₄H₂₃N₂O₂S⁺·C₂F₃O₂⁻, the piperazine ring adopts a chair conformation. The crystal packing is stabilized by C—H⋯O and N—H⋯O hydrogen bonds between the cation and anion. The F atoms are disordered over two positions; the site occupancy factors are 0.55 (2) and 0.45 (2).

Related literature

For related literature on benzenesulfonamides, see: Yu et al. (2007 ); Xing et al. (2006 , 2005 ).

Experimental

Crystal data

C₁₄H₂₃N₂O₂S⁺·C₂F₃O₂⁻
M_r = 396.42
Monoclinic, P 2₁ /n
a = 11.659 (2) Å
b = 8.4274 (17) Å
c = 19.404 (4) Å
β = 105.87 (3)°
V = 1833.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 113 (2) K
0.10 × 0.08 × 0.02 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.977, T_max = 0.995
10902 measured reflections
3226 independent reflections
2517 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.124
S = 1.03
3226 reflections
270 parameters
43 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4ⁱ	0.902 (11)	1.828 (12)	2.724 (3)	172 (3)
C9—H9A⋯O2ⁱⁱ	0.97	2.52	3.405 (4)	151
C10—H10A⋯O4ⁱⁱ	0.97	2.45	3.357 (4)	155
C2—H2⋯O3ⁱⁱⁱ	0.93	2.58	3.225 (4)	127
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z; (iii) x+1, y-1, z.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997 ); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807061570/bt2629sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807061570/bt2629Isup2.hkl

checkCIF report

Comment top

In the title compound (Fig. 1) both N atoms have a pyramidal arrangement, but the pyramid of the amide is somewhat shallower than that of the protonated N. The protonated piperazin ring adopts a chair conformation.

The crystal packing is stabilized by C—H···O and N—H···O hydrogen bonds (Table 1) between the cation and anion. Weak intermolecular C—H···O hydrogen bonds involving an S=O group as acceptor play an important role in the moleclular packing.

Related literature top

For benzenesulfonamides see: Yu et al. (2007); Xing et al. (2006); Xing et al. (2005).

Experimental top

A solution of 4-methylbenzenesulfonyl chloride (3.28 g, 17 mmol) in CH₂Cl₂ was added dropwise to a mixture of 1-isopropylpiperazine (2.23 g, 82%, 0.14 mmol) and sodium biscarbonate (3.36 g, 40 mmol) in CH₂Cl₂ (30 ml) at room temperature with stirring. After stirring for 4 h followed by filtration, the organic filtrate was rotoevaporated under vacuum. The resulting solid, in a yield of 53.8%, was purified by recrystallization from methanol. Crystals in the form of colourless blocks were grown by evaporation of a trifluoroacetic solution.

Structure description top

For benzenesulfonamides see: Yu et al. (2007); Xing et al. (2006); Xing et al. (2005).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Figures top

Fig. 1. The molecular structure of (I) with the atom-numbering scheme and 30% probability displacement ellipsoids. Only one component of the disordered CF₃ group is shown.

1-Isopropyl-4-tosylpiperazin-1-ium trifluoroacetate top

Crystal data top

C₁₄H₂₃N₂O₂S⁺·C₂F₃O₂⁻	F(000) = 832
M_r = 396.42	D_x = 1.436 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3880 reflections
a = 11.659 (2) Å	θ = 2.2–27.9°
b = 8.4274 (17) Å	µ = 0.23 mm⁻¹
c = 19.404 (4) Å	T = 113 K
β = 105.87 (3)°	Block, colorless
V = 1833.8 (6) Å³	0.10 × 0.08 × 0.02 mm
Z = 4

Data collection top

Rigaku Saturn diffractometer	3226 independent reflections
Radiation source: rotating anode	2517 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.072
ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −13→9
T_min = 0.977, T_max = 0.995	k = −9→10
10902 measured reflections	l = −23→23

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0512P)² + 0.9104P] where P = (F_o² + 2F_c²)/3
3226 reflections	(Δ/σ)_max = 0.003
270 parameters	Δρ_max = 0.40 e Å⁻³
43 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₄H₂₃N₂O₂S⁺·C₂F₃O₂⁻	V = 1833.8 (6) Å³
M_r = 396.42	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.659 (2) Å	µ = 0.23 mm⁻¹
b = 8.4274 (17) Å	T = 113 K
c = 19.404 (4) Å	0.10 × 0.08 × 0.02 mm
β = 105.87 (3)°

Data collection top

Rigaku Saturn diffractometer	3226 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2517 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.995	R_int = 0.072
10902 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	43 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.40 e Å⁻³
3226 reflections	Δρ_min = −0.28 e Å⁻³
270 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	Occ. (<1)
S1	0.63629 (6)	−0.19035 (8)	0.09809 (4)	0.0214 (2)
F1	0.0952 (9)	0.0965 (13)	0.2419 (6)	0.078 (3)	0.55 (2)
F2	0.1367 (11)	0.3388 (12)	0.2544 (5)	0.077 (3)	0.55 (2)
F3	0.2151 (6)	0.1905 (18)	0.1909 (5)	0.070 (3)	0.55 (2)
F1'	0.0745 (9)	0.175 (2)	0.2595 (5)	0.083 (4)	0.45 (2)
F2'	0.1771 (11)	0.3557 (10)	0.2275 (9)	0.077 (4)	0.45 (2)
F3'	0.1949 (11)	0.1212 (15)	0.2000 (6)	0.066 (4)	0.45 (2)
O1	0.63011 (18)	−0.3355 (2)	0.05863 (10)	0.0265 (5)
O2	0.53262 (17)	−0.1320 (2)	0.11580 (10)	0.0275 (5)
O3	−0.0548 (2)	0.3661 (3)	0.14312 (12)	0.0410 (6)
O4	0.00768 (17)	0.1625 (2)	0.08810 (10)	0.0277 (5)
N1	0.6753 (2)	−0.0517 (3)	0.04892 (11)	0.0197 (5)
N2	0.7924 (2)	0.1936 (3)	−0.01082 (12)	0.0183 (5)
C1	0.7539 (2)	−0.2013 (3)	0.17719 (14)	0.0195 (6)
C2	0.8553 (3)	−0.2897 (3)	0.17916 (14)	0.0211 (6)
H2	0.8588	−0.3517	0.1402	0.025*
C3	0.9508 (3)	−0.2842 (4)	0.23978 (15)	0.0254 (7)
H3	1.0186	−0.3440	0.2415	0.030*
C4	0.9472 (3)	−0.1907 (3)	0.29824 (14)	0.0248 (7)
C5	0.8443 (3)	−0.1060 (4)	0.29589 (15)	0.0281 (7)
H5	0.8406	−0.0447	0.3351	0.034*
C6	0.7468 (3)	−0.1113 (3)	0.23611 (15)	0.0258 (7)
H6	0.6776	−0.0556	0.2353	0.031*
C7	1.0535 (3)	−0.1813 (4)	0.36274 (16)	0.0373 (8)
H7A	1.0736	−0.2858	0.3820	0.056*
H7B	1.0348	−0.1150	0.3984	0.056*
H7C	1.1199	−0.1371	0.3490	0.056*
C8	0.6947 (3)	0.1074 (3)	0.08214 (14)	0.0222 (6)
H8A	0.7690	0.1081	0.1200	0.027*
H8B	0.6305	0.1321	0.1033	0.027*
C9	0.6995 (3)	0.2314 (3)	0.02688 (14)	0.0215 (7)
H9A	0.6221	0.2383	−0.0080	0.026*
H9B	0.7169	0.3339	0.0501	0.026*
C10	0.7722 (2)	0.0296 (3)	−0.04174 (14)	0.0201 (6)
H10A	0.8350	0.0033	−0.0639	0.024*
H10B	0.6967	0.0261	−0.0785	0.024*
C11	0.7712 (3)	−0.0907 (3)	0.01589 (14)	0.0213 (6)
H11A	0.7585	−0.1962	−0.0049	0.026*
H11B	0.8474	−0.0898	0.0520	0.026*
C12	0.7963 (3)	0.3177 (3)	−0.06701 (14)	0.0221 (6)
H12	0.7191	0.3189	−0.1033	0.026*
C13	0.8190 (3)	0.4804 (3)	−0.03294 (16)	0.0271 (7)
H13A	0.8896	0.4772	0.0066	0.041*
H13B	0.7522	0.5112	−0.0161	0.041*
H13C	0.8296	0.5558	−0.0677	0.041*
C14	0.8927 (3)	0.2765 (4)	−0.10319 (17)	0.0337 (8)
H14A	0.8996	0.3606	−0.1352	0.051*
H14B	0.8720	0.1797	−0.1298	0.051*
H14C	0.9675	0.2631	−0.0675	0.051*
C15	0.0119 (3)	0.2552 (3)	0.13959 (15)	0.0241 (7)
C16	0.1144 (3)	0.2243 (4)	0.20678 (16)	0.0313 (8)
H2A	0.8653 (14)	0.193 (4)	0.0208 (13)	0.031 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0190 (4)	0.0236 (4)	0.0199 (4)	−0.0031 (3)	0.0026 (3)	0.0009 (3)
F1	0.079 (5)	0.074 (5)	0.064 (4)	−0.015 (3)	−0.010 (3)	0.047 (4)
F2	0.086 (5)	0.073 (5)	0.046 (4)	0.026 (4)	−0.027 (3)	−0.032 (3)
F3	0.028 (3)	0.129 (7)	0.050 (3)	0.014 (4)	0.005 (2)	0.008 (5)
F1'	0.077 (5)	0.139 (9)	0.036 (4)	0.013 (6)	0.019 (3)	0.036 (5)
F2'	0.063 (5)	0.046 (4)	0.085 (7)	−0.023 (3)	−0.040 (4)	−0.008 (4)
F3'	0.062 (6)	0.063 (6)	0.052 (5)	0.044 (4)	−0.021 (4)	−0.016 (4)
O1	0.0317 (13)	0.0237 (11)	0.0212 (10)	−0.0075 (9)	0.0025 (9)	−0.0013 (8)
O2	0.0180 (12)	0.0362 (13)	0.0290 (11)	0.0000 (9)	0.0075 (9)	0.0045 (9)
O3	0.0448 (15)	0.0332 (13)	0.0382 (13)	0.0159 (11)	0.0001 (11)	−0.0083 (11)
O4	0.0216 (12)	0.0312 (12)	0.0270 (11)	0.0039 (9)	0.0012 (9)	−0.0056 (9)
N1	0.0213 (14)	0.0194 (13)	0.0194 (12)	0.0001 (10)	0.0074 (10)	0.0004 (10)
N2	0.0172 (13)	0.0179 (12)	0.0191 (12)	0.0001 (10)	0.0037 (10)	−0.0019 (10)
C1	0.0223 (16)	0.0160 (14)	0.0187 (14)	−0.0008 (11)	0.0031 (12)	0.0019 (11)
C2	0.0250 (17)	0.0199 (15)	0.0186 (14)	−0.0006 (12)	0.0064 (12)	0.0019 (12)
C3	0.0217 (17)	0.0302 (17)	0.0258 (15)	0.0025 (13)	0.0091 (13)	0.0056 (13)
C4	0.0262 (18)	0.0242 (16)	0.0214 (15)	−0.0057 (13)	0.0021 (13)	0.0049 (12)
C5	0.037 (2)	0.0244 (17)	0.0201 (15)	0.0035 (13)	0.0032 (14)	0.0000 (12)
C6	0.0265 (18)	0.0259 (17)	0.0254 (15)	0.0063 (13)	0.0081 (13)	−0.0006 (13)
C7	0.031 (2)	0.046 (2)	0.0276 (17)	−0.0068 (15)	−0.0032 (14)	0.0033 (15)
C8	0.0233 (17)	0.0218 (15)	0.0235 (15)	0.0015 (12)	0.0098 (13)	−0.0025 (12)
C9	0.0202 (17)	0.0208 (15)	0.0249 (15)	0.0036 (12)	0.0085 (12)	−0.0041 (12)
C10	0.0204 (16)	0.0182 (15)	0.0215 (14)	0.0006 (11)	0.0054 (12)	−0.0039 (12)
C11	0.0231 (16)	0.0179 (15)	0.0220 (14)	0.0020 (11)	0.0046 (12)	−0.0017 (12)
C12	0.0234 (16)	0.0193 (15)	0.0221 (15)	0.0009 (12)	0.0038 (12)	0.0056 (12)
C13	0.0293 (18)	0.0233 (16)	0.0295 (16)	0.0040 (13)	0.0096 (13)	0.0055 (13)
C14	0.042 (2)	0.0283 (18)	0.0380 (18)	−0.0016 (14)	0.0228 (16)	0.0014 (14)
C15	0.0239 (18)	0.0234 (16)	0.0246 (15)	−0.0028 (12)	0.0058 (13)	0.0007 (13)
C16	0.032 (2)	0.0311 (19)	0.0285 (17)	−0.0004 (14)	0.0039 (15)	−0.0037 (14)

Geometric parameters (Å, º) top

S1—O2	1.431 (2)	C5—C6	1.385 (4)
S1—O1	1.435 (2)	C5—H5	0.9300
S1—N1	1.649 (2)	C6—H6	0.9300
S1—C1	1.758 (3)	C7—H7A	0.9600
F1—C16	1.326 (6)	C7—H7B	0.9600
F2—C16	1.311 (6)	C7—H7C	0.9600
F3—C16	1.323 (7)	C8—C9	1.509 (4)
F1'—C16	1.302 (7)	C8—H8A	0.9700
F2'—C16	1.327 (7)	C8—H8B	0.9700
F3'—C16	1.312 (7)	C9—H9A	0.9700
O3—C15	1.230 (4)	C9—H9B	0.9700
O4—C15	1.259 (3)	C10—C11	1.512 (4)
N1—C11	1.470 (4)	C10—H10A	0.9700
N1—C8	1.478 (3)	C10—H10B	0.9700
N2—C9	1.498 (3)	C11—H11A	0.9700
N2—C10	1.499 (3)	C11—H11B	0.9700
N2—C12	1.521 (3)	C12—C13	1.514 (4)
N2—H2A	0.902 (11)	C12—C14	1.519 (4)
C1—C2	1.389 (4)	C12—H12	0.9800
C1—C6	1.393 (4)	C13—H13A	0.9600
C2—C3	1.382 (4)	C13—H13B	0.9600
C2—H2	0.9300	C13—H13C	0.9600
C3—C4	1.391 (4)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—C5	1.386 (4)	C14—H14C	0.9600
C4—C7	1.503 (4)	C15—C16	1.531 (4)

O2—S1—O1	119.92 (12)	C11—C10—H10A	109.5
O2—S1—N1	106.25 (12)	N2—C10—H10B	109.5
O1—S1—N1	106.09 (11)	C11—C10—H10B	109.5
O2—S1—C1	108.45 (13)	H10A—C10—H10B	108.1
O1—S1—C1	109.53 (12)	N1—C11—C10	109.5 (2)
N1—S1—C1	105.65 (12)	N1—C11—H11A	109.8
C11—N1—C8	110.4 (2)	C10—C11—H11A	109.8
C11—N1—S1	117.15 (18)	N1—C11—H11B	109.8
C8—N1—S1	115.10 (17)	C10—C11—H11B	109.8
C9—N2—C10	109.7 (2)	H11A—C11—H11B	108.2
C9—N2—C12	111.8 (2)	C13—C12—C14	110.2 (2)
C10—N2—C12	112.3 (2)	C13—C12—N2	110.2 (2)
C9—N2—H2A	109.9 (19)	C14—C12—N2	110.2 (2)
C10—N2—H2A	107 (2)	C13—C12—H12	108.7
C12—N2—H2A	106 (2)	C14—C12—H12	108.7
C2—C1—C6	120.7 (3)	N2—C12—H12	108.7
C2—C1—S1	120.4 (2)	C12—C13—H13A	109.5
C6—C1—S1	118.7 (2)	C12—C13—H13B	109.5
C3—C2—C1	119.2 (3)	H13A—C13—H13B	109.5
C3—C2—H2	120.4	C12—C13—H13C	109.5
C1—C2—H2	120.4	H13A—C13—H13C	109.5
C2—C3—C4	121.0 (3)	H13B—C13—H13C	109.5
C2—C3—H3	119.5	C12—C14—H14A	109.5
C4—C3—H3	119.5	C12—C14—H14B	109.5
C5—C4—C3	118.9 (3)	H14A—C14—H14B	109.5
C5—C4—C7	120.6 (3)	C12—C14—H14C	109.5
C3—C4—C7	120.5 (3)	H14A—C14—H14C	109.5
C6—C5—C4	121.0 (3)	H14B—C14—H14C	109.5
C6—C5—H5	119.5	O3—C15—O4	128.9 (3)
C4—C5—H5	119.5	O3—C15—C16	116.1 (3)
C5—C6—C1	119.1 (3)	O4—C15—C16	115.0 (3)
C5—C6—H6	120.5	F1'—C16—F2	74.1 (6)
C1—C6—H6	120.5	F1'—C16—F3'	106.7 (6)
C4—C7—H7A	109.5	F2—C16—F3'	123.3 (6)
C4—C7—H7B	109.5	F1'—C16—F3	130.1 (6)
H7A—C7—H7B	109.5	F2—C16—F3	107.7 (6)
C4—C7—H7C	109.5	F3'—C16—F3	29.5 (5)
H7A—C7—H7C	109.5	F1'—C16—F1	35.9 (5)
H7B—C7—H7C	109.5	F2—C16—F1	105.3 (5)
N1—C8—C9	110.5 (2)	F3'—C16—F1	75.0 (6)
N1—C8—H8A	109.6	F3—C16—F1	103.4 (5)
C9—C8—H8A	109.6	F1'—C16—F2'	108.3 (6)
N1—C8—H8B	109.6	F2—C16—F2'	35.5 (5)
C9—C8—H8B	109.6	F3'—C16—F2'	103.5 (7)
H8A—C8—H8B	108.1	F3—C16—F2'	78.5 (6)
N2—C9—C8	111.8 (2)	F1—C16—F2'	132.7 (6)
N2—C9—H9A	109.3	F1'—C16—C15	111.1 (5)
C8—C9—H9A	109.3	F2—C16—C15	115.6 (4)
N2—C9—H9B	109.3	F3'—C16—C15	116.1 (5)
C8—C9—H9B	109.3	F3—C16—C15	112.0 (5)
H9A—C9—H9B	107.9	F1—C16—C15	112.0 (4)
N2—C10—C11	110.8 (2)	F2'—C16—C15	110.6 (5)
N2—C10—H10A	109.5

O2—S1—N1—C11	−172.47 (19)	C10—N2—C9—C8	54.2 (3)
O1—S1—N1—C11	−43.8 (2)	C12—N2—C9—C8	179.4 (2)
C1—S1—N1—C11	72.4 (2)	N1—C8—C9—N2	−55.7 (3)
O2—S1—N1—C8	55.2 (2)	C9—N2—C10—C11	−56.1 (3)
O1—S1—N1—C8	−176.13 (19)	C12—N2—C10—C11	178.9 (2)
C1—S1—N1—C8	−59.9 (2)	C8—N1—C11—C10	−60.6 (3)
O2—S1—C1—C2	163.9 (2)	S1—N1—C11—C10	164.97 (18)
O1—S1—C1—C2	31.4 (3)	N2—C10—C11—N1	59.7 (3)
N1—S1—C1—C2	−82.5 (2)	C9—N2—C12—C13	57.2 (3)
O2—S1—C1—C6	−20.4 (3)	C10—N2—C12—C13	−179.0 (2)
O1—S1—C1—C6	−152.9 (2)	C9—N2—C12—C14	179.1 (2)
N1—S1—C1—C6	93.2 (2)	C10—N2—C12—C14	−57.1 (3)
C6—C1—C2—C3	−1.7 (4)	O3—C15—C16—F1'	67.0 (11)
S1—C1—C2—C3	173.9 (2)	O4—C15—C16—F1'	−112.9 (10)
C1—C2—C3—C4	−0.6 (4)	O3—C15—C16—F2	−14.9 (9)
C2—C3—C4—C5	2.0 (4)	O4—C15—C16—F2	165.2 (9)
C2—C3—C4—C7	−177.8 (3)	O3—C15—C16—F3'	−170.9 (9)
C3—C4—C5—C6	−1.1 (4)	O4—C15—C16—F3'	9.3 (10)
C7—C4—C5—C6	178.7 (3)	O3—C15—C16—F3	−138.8 (8)
C4—C5—C6—C1	−1.1 (4)	O4—C15—C16—F3	41.4 (8)
C2—C1—C6—C5	2.5 (4)	O3—C15—C16—F1	105.7 (9)
S1—C1—C6—C5	−173.2 (2)	O4—C15—C16—F1	−74.2 (9)
C11—N1—C8—C9	58.7 (3)	O3—C15—C16—F2'	−53.3 (11)
S1—N1—C8—C9	−165.91 (18)	O4—C15—C16—F2'	126.8 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱ	0.90 (1)	1.83 (1)	2.724 (3)	172 (3)
C9—H9A···O2ⁱⁱ	0.97	2.52	3.405 (4)	151
C10—H10A···O4ⁱⁱ	0.97	2.45	3.357 (4)	155
C2—H2···O3ⁱⁱⁱ	0.93	2.58	3.225 (4)	127

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

Experimental details

Crystal data
Chemical formula	C₁₄H₂₃N₂O₂S⁺·C₂F₃O₂⁻
M_r	396.42
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	11.659 (2), 8.4274 (17), 19.404 (4)
β (°)	105.87 (3)
V (Å³)	1833.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.10 × 0.08 × 0.02

Data collection
Diffractometer	Rigaku Saturn
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.977, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	10902, 3226, 2517
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.124, 1.03
No. of reflections	3226
No. of parameters	270
No. of restraints	43
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.28

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱ	0.902 (11)	1.828 (12)	2.724 (3)	172 (3)
C9—H9A···O2ⁱⁱ	0.97	2.52	3.405 (4)	151
C10—H10A···O4ⁱⁱ	0.97	2.45	3.357 (4)	155
C2—H2···O3ⁱⁱⁱ	0.93	2.58	3.225 (4)	127

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

References

Bruker (1997). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Xing, J.-D., Bai, G.-Y., Zeng, T. & Li, J.-S. (2006). Acta Cryst. E62, o79–o80. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xing, J.-D. & Zeng, T. (2005). Acta Cryst. E61, o4318–o4319. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yu, H.-J. & Li, J.-S. (2007). Acta Cryst. E63, o3766. Web of Science CSD CrossRef IUCr Journals Google Scholar

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