Tetra­methyl­ammonium tri­fluoro­methane­sulfonate

Bourque, J.L.; Baines, K.M.

doi:10.1107/S2414314616003709

organic compounds

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ISSN: 2414-3146

Volume 1| Part 3| March 2016| x160370

doi:10.1107/S2414314616003709

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Tetramethylammonium trifluoromethanesulfonate

Jeremy L. Bourque ^a ^* and Kim M. Baines ^a

^aDepartment of Chemistry, University of Western Ontario, London, ON, N6A 5B7, Canada
^*Correspondence e-mail: jbourqu5@uwo.ca

Edited by O. Blacque, University of Zürich, Switzerland (Received 2 March 2016; accepted 3 March 2016; online 11 March 2016)

The structure of tetramethylammonium trifluoromethanesulfonate, C₄H₁₂N⁺·CF₃SO₃⁻, was determined at 110 K in the monoclinic space group P2₁/m. The salt, which contains two cations and two anions in the asymmetric unit, has a network structure displaying C—H⋯O hydrogen bonding. Both the cation and the anion lie on special positions (mirror planes).

Keywords: crystal structure; tetraalkylammonium salts; three-dimensional hydrogen bonding; trifluoromethanesulfonate salts.

CCDC reference: 1456956

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Chemical scheme

Structure description

Despite the report of the synthesis of the title compound in the literature (Sarria Toro et al., 2014 ; and others), no structural data has been presented. The title compound has been used in various applications, such as an electrolyte for electrochemical studies and syntheses (Bond et al., 1983 ; Ferraris et al., 1998 ; Li et al., 2002 ; Loveday et al., 1997 ; Ue et al., 1994 ), as a reagent in traditional synthesis (den Hartog et al., 2014 ; Lei et al., 2014 ; Sagl & Martin, 1988 ; Zhang et al., 2014 ), as well as other studies (i.e. Bartoli & Roelens, 2002 ). For structures of other trifluoromethanesulfonate salts of tetraalkylammonium and ammonium cations, see: [NBu₄][O₃SCF₃]: Blake et al. (1993 ); [NBu₄][O₃SCF₃] co-crystals: Leclercq et al. (2007 , 2008 , 2012 ) and [NH₄][O₃SCF₃]: Gänswein & Brauer (1975 ).

The bonding within the individual ions is as expected. The asymmetric unit is composed of two formula units (Fig. 1), with all four of the ions being positioned along a crystallographic mirror plane that is perpendicular to the [010] layer. Individual ions are connected by a three-dimensional network of hydrogen bonds (Table 1 and Fig. 2). The strongest interactions are found between C3 and O4 and C6 and O2. These generate the alternating ion types along the [010] layer. The ions are also connected by hydrogen bonds perpendicular to the [010] layer, in both the [100] and the [001] directions. These hold the ions of the asymmetric unit together along the crystallographic mirror plane. These hydrogen bonds are between C1 and O4, C1 and O3 and C6 and O4. In addition, other short contacts were discerned in the three-dimensional structure, however, it is unclear as to their nature.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O4ⁱ	0.98	2.53	3.4075 (16)	149
C1—H1C⋯O3ⁱⁱ	0.98	2.52	3.4038 (18)	150
C3—H3A⋯O4ⁱ	0.98	2.48	3.3536 (13)	149
C3—H3C⋯O4ⁱⁱⁱ	0.98	2.45	3.3536 (13)	152
C5—H5A⋯O2ⁱ	0.98	2.50	3.3734 (12)	148
C5—H5C⋯O2ⁱⁱⁱ	0.98	2.52	3.3734 (12)	145
C6—H6A⋯O4^iv	0.98	2.56	3.4594 (17)	153
C6—H6B⋯O2ⁱ	0.98	2.47	3.3463 (15)	149
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (ii) x-1, y, z; (iii) -x+1, -y+2, -z+1; (iv) $[x-1, -y+{\script{3\over 2}}, z]$ .

Figure 1
The molecular structure of the title compound, showing the atom-numbering scheme and with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.

Figure 2
Crystal packing of the title compound viewed along the c axis. H atoms have been omitted for clarity.

Synthesis and crystallization

The title compound was synthesized according to literature procedures (Sarria Toro et al., 2014). Single crystals suitable for a diffraction study were serendipitously obtained from an attempted anion exchange reaction. A mixture of a [Ga₂X₂(cryptand-222)]²⁺ dication (Bourque et al., 2015 ) with mixed tetrahalogallate and trifluoromethanesulfonate anions and an excess of the title compound was dissolved in acetonitrile (5 ml) and cooled to −20°C. Single crystals of the title compound were obtained after several days.

Refinement

Crystal data, data collection and refinement details are shown in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₄H₁₂N⁺·CF₃O₃S⁻
M_r	223.22
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	110
a, b, c (Å)	10.216 (3), 8.507 (2), 11.445 (4)
β (°)	101.807 (17)
V (Å³)	973.6 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.36
Crystal size (mm)	0.22 × 0.16 × 0.07

Data collection
Diffractometer	Bruker Kappa-axis APEXII
Absorption correction	Multi-scan (TWINABS; Bruker, 2012 )
T_min, T_max	0.225, 0.438
No. of measured, independent and observed [I > 2σ(I)] reflections	4962, 4962, 3766
(sin θ/λ)_max (Å⁻¹)	0.835

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.106, 1.06
No. of reflections	4962
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.54
Computer programs: APEX2 (Bruker, 2013 ), CELL_NOW (Bruker, 2008 ), SAINT (Bruker, 2013), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), XP in SHELXTL (Sheldrick, 2008 ), cif2tables.py (Boyle, 2008 ).

Structural data

CCDC reference: 1456956

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616003709/zq4003sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616003709/zq4003Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616003709/zq4003Isup3.cml

checkCIF report

Experimental top

The title compound was synthesized according to literature procedures (Sarria Toro et al., 2014). Single crystals suitable for a diffraction study were serendipitously obtained from an attempted anion exchange reaction. A mixture of a [Ga₂X₂(cryptand-222)]²⁺ dication (Bourque et al., 2015) with mixed tetrahalogallate and trifluoromethanesulfonate anions and an excess of the title compound was dissolved in acetonitrile (5 ml) and cooled to −20°C. Single crystals of the title compound were obtained after several days.

Structure description top

Despite the report of the synthesis of the title compound in the literature (Sarria Toro et al., 2014; and others), no structural data has been presented. The title compound has been used in various applications, such as an electrolyte for electrochemical studies and syntheses (Bond et al., 1983; Ferraris et al., 1998; Li et al., 2002; Loveday et al., 1997; Ue et al., 1994), as a reagent in traditional syntheses (den Hartog et al., 2014; Lei et al., 2014; Sagl & Martin, 1988; Zhang et al., 2014), as well as other studies (i.e. Bartoli & Roelens, 2002). For structures of other trifluoromethanesulfonate salts of tetraalkylammonium and ammonium cations, see: [NBu₄][O₃SCF₃]: Blake et al. (1993); [NBu₄][O₃SCF₃] co-crystals: Leclercq et al. (2007, 2008, 2012) and [NH₄][O₃SCF₃]: Gänswein & Brauer (1975).

The bonding within the individual ions is as expected. The asymmetric unit is composed of two formula units (Fig. 1), with all four of the ions being positioned along a crystallographic mirror plane that is perpendicular to the [010] layer. Individual ions are connected by a three-dimensional network of hydrogen bonds (Table 1 and Fig. 2). The strongest interactions are found between C3 and O4 and C6 and O2. These generate the alternating ion types along the [010] layer. The ions are also connected by hydrogen bonds perpendicular to the [010] layer, in both the [100] and the [001] directions. These hold the ions of the asymmetric unit together along the crystallographic mirror plane. These hydrogen bonds are between C1 and O4, C1 and O3 and C6 and O4. In addition, other short contacts were shown in the three-dimensional structure, however, it is unclear as to their nature.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: CELL_NOW (Bruker, 2008); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: cif2tables.py (Boyle, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 2. Crystal packing of the title compound viewed along the c axis. H atoms have been omitted for clarity.

Tetramethylammonium trifluoromethanesulfonate top

Crystal data top

C₄H₁₂N⁺·CF₃O₃S⁻	F(000) = 464
M_r = 223.22	D_x = 1.523 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
a = 10.216 (3) Å	Cell parameters from 7184 reflections
b = 8.507 (2) Å	θ = 3.1–35.8°
c = 11.445 (4) Å	µ = 0.36 mm⁻¹
β = 101.807 (17)°	T = 110 K
V = 973.6 (5) Å³	Plate, colourless
Z = 4	0.22 × 0.16 × 0.07 mm

Data collection top

Bruker Kappa-axis APEXII diffractometer	4962 independent reflections
Radiation source: sealed tube	3766 reflections with I > 2σ(I)
phi and ω scans	θ_max = 36.4°, θ_min = 2.4°
Absorption correction: multi-scan (TWINABS; Bruker, 2012)	h = −17→16
T_min = 0.225, T_max = 0.438	k = 0→14
4962 measured reflections	l = 0→19

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0519P)² + 0.1452P] where P = (F_o² + 2F_c²)/3
4962 reflections	(Δ/σ)_max = 0.001
145 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₄H₁₂N⁺·CF₃O₃S⁻	V = 973.6 (5) Å³
M_r = 223.22	Z = 4
Monoclinic, P2₁/m	Mo Kα radiation
a = 10.216 (3) Å	µ = 0.36 mm⁻¹
b = 8.507 (2) Å	T = 110 K
c = 11.445 (4) Å	0.22 × 0.16 × 0.07 mm
β = 101.807 (17)°

Data collection top

Bruker Kappa-axis APEXII diffractometer	4962 measured reflections
Absorption correction: multi-scan (TWINABS; Bruker, 2012)	4962 independent reflections
T_min = 0.225, T_max = 0.438	3766 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.06	Δρ_max = 0.42 e Å⁻³
4962 reflections	Δρ_min = −0.54 e Å⁻³
145 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. The structural model was fit to the data using full matrix least-squares based on F². The calculated structure factors included corrections for anomalous dispersion from the usual tabulation. The initial indexing indicated the sample crystal was a non-merohedral twin. The twin law was determined to be:

Twin Law,

Sample 1 of 1 Transforms h1.1(1)->h1.2(2)

0.08833 − 0.00004 0.90535

0.00561 − 0.99998 0.00058

1.09590 0.00873 − 0.08833

which corresponds to an approximately −179.7° rotation about the [101] vector in reciprocal space. The data demonstrated that the minor component refined to a normalized occupancy value of 0.02379 (22). Due to the small size of the secondary domain, the larger R₁ value obtained when including all the data, and increased levels of noise observed in the difference map, the structural model was refined using only data from the dominant component of the twin.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	−0.16040 (11)	0.7500	0.59284 (10)	0.01428 (19)
C1	−0.22304 (11)	0.60593 (11)	0.53007 (10)	0.02051 (19)
H1A	−0.3190	0.6053	0.5302	0.031*
H1B	−0.1811	0.5122	0.5714	0.031*
H1C	−0.2101	0.6060	0.4476	0.031*
C2	−0.01370 (14)	0.7500	0.59337 (15)	0.0225 (3)
H2A	0.0293	0.6627	0.6426	0.034*	0.5
H2B	0.0257	0.8496	0.6264	0.034*	0.5
H2C	−0.0001	0.7377	0.5116	0.034*	0.5
C3	−0.17984 (16)	0.7500	0.71906 (13)	0.0205 (3)
H3A	−0.1312	0.6613	0.7623	0.031*	0.5
H3B	−0.2753	0.7400	0.7195	0.031*	0.5
H3C	−0.1458	0.8487	0.7580	0.031*	0.5
C4	0.35549 (17)	0.7500	0.79047 (14)	0.0233 (3)
F1	0.46663 (13)	0.7500	0.87653 (9)	0.0399 (3)
F2	0.28477 (9)	0.62388 (10)	0.80708 (7)	0.0381 (2)
S1	0.39742 (3)	0.7500	0.64268 (3)	0.01368 (7)
O1	0.26921 (11)	0.7500	0.56276 (10)	0.0209 (2)
O2	0.47442 (8)	0.89272 (9)	0.64345 (8)	0.02385 (16)
N2	0.40095 (11)	0.7500	0.20271 (10)	0.01435 (19)
C5	0.37919 (15)	0.7500	0.32830 (12)	0.0183 (2)
H5A	0.4104	0.6501	0.3668	0.027*	0.5
H5B	0.2837	0.7630	0.3275	0.027*	0.5
H5C	0.4293	0.8369	0.3727	0.027*	0.5
C6	0.33803 (11)	0.60648 (11)	0.13956 (9)	0.01936 (18)
H6A	0.2419	0.6067	0.1388	0.029*
H6B	0.3789	0.5124	0.1812	0.029*
H6C	0.3520	0.6062	0.0574	0.029*
C7	0.54785 (14)	0.7500	0.20474 (15)	0.0210 (3)
H7A	0.5885	0.6554	0.2457	0.032*	0.5
H7B	0.5888	0.8435	0.2471	0.032*	0.5
H7C	0.5624	0.7511	0.1227	0.032*	0.5
S2	0.96358 (3)	0.7500	0.22288 (3)	0.01601 (7)
O3	0.84541 (13)	0.7500	0.27165 (12)	0.0369 (3)
O4	1.04184 (10)	0.89119 (11)	0.24164 (9)	0.0366 (2)
C8	0.89895 (18)	0.7500	0.06244 (15)	0.0276 (3)
F3	0.99738 (16)	0.7500	0.00278 (12)	0.0579 (4)
F4	0.82365 (12)	0.62540 (14)	0.02824 (9)	0.0650 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0133 (4)	0.0133 (4)	0.0159 (5)	0.000	0.0022 (4)	0.000
C1	0.0234 (5)	0.0161 (4)	0.0210 (5)	−0.0036 (3)	0.0023 (4)	−0.0028 (3)
C2	0.0132 (6)	0.0275 (7)	0.0273 (7)	0.000	0.0054 (5)	0.000
C3	0.0237 (7)	0.0212 (6)	0.0169 (6)	0.000	0.0045 (5)	0.000
C4	0.0288 (7)	0.0256 (7)	0.0167 (6)	0.000	0.0075 (5)	0.000
F1	0.0435 (7)	0.0592 (8)	0.0139 (5)	0.000	−0.0017 (4)	0.000
F2	0.0503 (5)	0.0366 (4)	0.0330 (4)	−0.0112 (4)	0.0219 (4)	0.0064 (3)
S1	0.01419 (13)	0.01330 (13)	0.01369 (14)	0.000	0.00323 (10)	0.000
O1	0.0156 (4)	0.0273 (5)	0.0183 (5)	0.000	0.0000 (4)	0.000
O2	0.0249 (4)	0.0208 (3)	0.0263 (4)	−0.0082 (3)	0.0063 (3)	−0.0009 (3)
N2	0.0138 (5)	0.0143 (4)	0.0147 (5)	0.000	0.0023 (4)	0.000
C5	0.0220 (6)	0.0191 (6)	0.0142 (6)	0.000	0.0047 (5)	0.000
C6	0.0224 (4)	0.0160 (4)	0.0189 (4)	−0.0023 (3)	0.0025 (3)	−0.0032 (3)
C7	0.0137 (5)	0.0242 (6)	0.0258 (7)	0.000	0.0054 (5)	0.000
S2	0.01404 (14)	0.01859 (15)	0.01491 (15)	0.000	0.00181 (11)	0.000
O3	0.0216 (6)	0.0640 (9)	0.0276 (6)	0.000	0.0107 (5)	0.000
O4	0.0382 (5)	0.0324 (5)	0.0368 (5)	−0.0163 (4)	0.0019 (4)	−0.0090 (4)
C8	0.0267 (8)	0.0349 (8)	0.0180 (7)	0.000	−0.0027 (6)	0.000
F3	0.0515 (8)	0.1044 (12)	0.0205 (5)	0.000	0.0138 (5)	0.000
F4	0.0755 (8)	0.0681 (7)	0.0412 (6)	−0.0331 (6)	−0.0116 (5)	−0.0202 (5)

Geometric parameters (Å, º) top

N1—C1	1.4965 (12)	N2—C6ⁱ	1.4953 (12)
N1—C1ⁱ	1.4965 (12)	N2—C6	1.4954 (12)
N1—C2	1.4974 (18)	N2—C7	1.4960 (18)
N1—C3	1.4979 (19)	N2—C5	1.4988 (18)
C1—H1A	0.9800	C5—H5A	0.9800
C1—H1B	0.9800	C5—H5B	0.9800
C1—H1C	0.9800	C5—H5C	0.9800
C2—H2A	0.9800	C6—H6A	0.9800
C2—H2B	0.9800	C6—H6B	0.9800
C2—H2C	0.9800	C6—H6C	0.9800
C3—H3A	0.9800	C7—H7A	0.9800
C3—H3B	0.9800	C7—H7B	0.9800
C3—H3C	0.9800	C7—H7C	0.9800
C4—F2ⁱ	1.3286 (12)	S2—O3	1.4299 (13)
C4—F2	1.3286 (12)	S2—O4ⁱ	1.4344 (9)
C4—F1	1.342 (2)	S2—O4	1.4344 (9)
C4—S1	1.8279 (16)	S2—C8	1.8198 (18)
S1—O1	1.4360 (12)	C8—F4	1.3210 (14)
S1—O2ⁱ	1.4457 (8)	C8—F4ⁱ	1.3210 (14)
S1—O2	1.4457 (8)	C8—F3	1.326 (2)

C1—N1—C1ⁱ	109.96 (11)	C6ⁱ—N2—C6	109.47 (11)
C1—N1—C2	109.34 (7)	C6ⁱ—N2—C7	109.76 (7)
C1ⁱ—N1—C2	109.35 (7)	C6—N2—C7	109.76 (7)
C1—N1—C3	109.57 (7)	C6ⁱ—N2—C5	109.27 (7)
C1ⁱ—N1—C3	109.57 (7)	C6—N2—C5	109.27 (7)
C2—N1—C3	109.03 (12)	C7—N2—C5	109.29 (11)
N1—C1—H1A	109.5	N2—C5—H5A	109.5
N1—C1—H1B	109.5	N2—C5—H5B	109.5
H1A—C1—H1B	109.5	H5A—C5—H5B	109.5
N1—C1—H1C	109.5	N2—C5—H5C	109.5
H1A—C1—H1C	109.5	H5A—C5—H5C	109.5
H1B—C1—H1C	109.5	H5B—C5—H5C	109.5
N1—C2—H2A	109.5	N2—C6—H6A	109.5
N1—C2—H2B	109.5	N2—C6—H6B	109.5
H2A—C2—H2B	109.5	H6A—C6—H6B	109.5
N1—C2—H2C	109.5	N2—C6—H6C	109.5
H2A—C2—H2C	109.5	H6A—C6—H6C	109.5
H2B—C2—H2C	109.5	H6B—C6—H6C	109.5
N1—C3—H3A	109.5	N2—C7—H7A	109.5
N1—C3—H3B	109.5	N2—C7—H7B	109.5
H3A—C3—H3B	109.5	H7A—C7—H7B	109.5
N1—C3—H3C	109.5	N2—C7—H7C	109.5
H3A—C3—H3C	109.5	H7A—C7—H7C	109.5
H3B—C3—H3C	109.5	H7B—C7—H7C	109.5
F2ⁱ—C4—F2	107.70 (14)	O3—S2—O4ⁱ	115.51 (5)
F2ⁱ—C4—F1	107.34 (9)	O3—S2—O4	115.51 (5)
F2—C4—F1	107.34 (9)	O4ⁱ—S2—O4	113.72 (9)
F2ⁱ—C4—S1	111.69 (8)	O3—S2—C8	103.47 (9)
F2—C4—S1	111.69 (8)	O4ⁱ—S2—C8	103.13 (5)
F1—C4—S1	110.85 (11)	O4—S2—C8	103.13 (5)
O1—S1—O2ⁱ	115.35 (4)	F4—C8—F4ⁱ	106.70 (16)
O1—S1—O2	115.35 (4)	F4—C8—F3	107.72 (11)
O2ⁱ—S1—O2	114.24 (7)	F4ⁱ—C8—F3	107.72 (11)
O1—S1—C4	103.51 (7)	F4—C8—S2	111.60 (10)
O2ⁱ—S1—C4	102.98 (5)	F4ⁱ—C8—S2	111.60 (10)
O2—S1—C4	102.98 (5)	F3—C8—S2	111.27 (13)

F2ⁱ—C4—S1—O1	−60.35 (10)	O3—S2—C8—F4	−59.64 (11)
F2—C4—S1—O1	60.35 (10)	O4ⁱ—S2—C8—F4	61.06 (13)
F1—C4—S1—O1	180.000 (1)	O4—S2—C8—F4	179.65 (11)
F2ⁱ—C4—S1—O2ⁱ	179.18 (9)	O3—S2—C8—F4ⁱ	59.64 (11)
F2—C4—S1—O2ⁱ	−60.13 (11)	O4ⁱ—S2—C8—F4ⁱ	−179.65 (11)
F1—C4—S1—O2ⁱ	59.52 (4)	O4—S2—C8—F4ⁱ	−61.06 (13)
F2ⁱ—C4—S1—O2	60.13 (12)	O3—S2—C8—F3	180.0
F2—C4—S1—O2	−179.18 (9)	O4ⁱ—S2—C8—F3	−59.29 (5)
F1—C4—S1—O2	−59.52 (4)	O4—S2—C8—F3	59.29 (5)

Symmetry code: (i) x, −y+3/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O4ⁱⁱ	0.98	2.53	3.4075 (16)	149
C1—H1C···O3ⁱⁱⁱ	0.98	2.52	3.4038 (18)	150
C3—H3A···O4ⁱⁱ	0.98	2.48	3.3536 (13)	149
C3—H3C···O4^iv	0.98	2.45	3.3536 (13)	152
C5—H5A···O2ⁱⁱ	0.98	2.50	3.3734 (12)	148
C5—H5C···O2^iv	0.98	2.52	3.3734 (12)	145
C6—H6A···O4^v	0.98	2.56	3.4594 (17)	153
C6—H6B···O2ⁱⁱ	0.98	2.47	3.3463 (15)	149

Symmetry codes: (ii) −x+1, y−1/2, −z+1; (iii) x−1, y, z; (iv) −x+1, −y+2, −z+1; (v) x−1, −y+3/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O4ⁱ	0.98	2.53	3.4075 (16)	148.5
C1—H1C···O3ⁱⁱ	0.98	2.52	3.4038 (18)	150.2
C3—H3A···O4ⁱ	0.98	2.48	3.3536 (13)	148.8
C3—H3C···O4ⁱⁱⁱ	0.98	2.45	3.3536 (13)	152.4
C5—H5A···O2ⁱ	0.98	2.50	3.3734 (12)	148.3
C5—H5C···O2ⁱⁱⁱ	0.98	2.52	3.3734 (12)	145.0
C6—H6A···O4^iv	0.98	2.56	3.4594 (17)	152.7
C6—H6B···O2ⁱ	0.98	2.47	3.3463 (15)	149.4

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x−1, y, z; (iii) −x+1, −y+2, −z+1; (iv) x−1, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	C₄H₁₂N⁺·CF₃O₃S⁻
M_r	223.22
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	110
a, b, c (Å)	10.216 (3), 8.507 (2), 11.445 (4)
β (°)	101.807 (17)
V (Å³)	973.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.22 × 0.16 × 0.07

Data collection
Diffractometer	Bruker Kappa-axis APEXII
Absorption correction	Multi-scan (TWINABS; Bruker, 2012)
T_min, T_max	0.225, 0.438
No. of measured, independent and observed [I > 2σ(I)] reflections	4962, 4962, 3766
R_int	?
(sin θ/λ)_max (Å⁻¹)	0.835

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.106, 1.06
No. of reflections	4962
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.54

Computer programs: APEX2 (Bruker, 2013), CELL_NOW (Bruker, 2008), SAINT (Bruker, 2013), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), XP in SHELXTL (Sheldrick, 2008), cif2tables.py (Boyle, 2008).

Acknowledgements

We thank the NSERC (Canada), the NSERC CGS program for a scholarship to JLB, and the University of Western Ontario for financial support. We also thank Dr Paul D. Boyle for aid in the structure refinement.

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