Ammonium 4,4-difluoro-1,3,2-dithia­zetin-2-ide 1,1,3,3-tetra­oxide

Finze, M.; Reiss, G.J.

doi:10.1107/S1600536812024221

organic compounds

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Volume 68| Part 7| July 2012| Pages o1992-o1993

https://doi.org/10.1107/S1600536812024221

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Ammonium 4,4-difluoro-1,3,2-dithiazetin-2-ide 1,1,3,3-tetraoxide

Maik Finze ^a and Guido J. Reiss ^b ^*

^aInstitut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland D-97074, Würzburg, Germany, and ^bInstitut für Anorganische Chemie und Strukturchemie, Lehrstuhl II: Material- und Strukturforschung, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany
^*Correspondence e-mail: reissg@uni-duesseldorf.de

(Received 13 May 2012; accepted 27 May 2012; online 2 June 2012)

The asymmetric unit of the title compound, NH₄⁺·CF₂NO₄S₂⁻, consists of two crystallographically independent ammonium cations and two 4,4-difluoro-1,3,2-dithiazetin-2-ide 1,1,3,3-tetraoxide anions all located in general positions. The S—C—S—N rings of both crystallographically independent anions are almost planar, with the N atom bent out of the plane by 9.82 (5) and 12.82 (4)°. The structure was determined from a crystal twinned by inversion, with refined components in the ratio 0.73 (4):0.27 (4). Anions and cations are connected via hydrogen bonds (N—H⋯O and N—H⋯N) to form a three-dimensional framework. This framework is composed of two different layers parallel to the ab plane, which are built by the ammonium cations on the one hand and the complex cyclic anions on the other.

Related literature

For general aspects of the chemistry of fluorinated sulfonimides and their salts, see: Antoniotti et al. (2010 ); Foropoulos & DesMarteau (1984 ); Popov et al. (2011 ); Vij et al. (1997 ); DesMarteau (1995 ). For the synthesis and chemistry of the title compound, see: Jüschke et al. (1997 ). For related structures, see: DesMarteau et al. (1992 ); Davidson et al. (2003 ). For similar layered ammonium salts, see: Reiss (2002 ); Plizko & Meyer (1998 ); Bucholz & Mattes (1988 ).

Experimental

Crystal data

NH₄⁺·CF₂NO₄S₂⁻
M_r = 210.18
Orthorhombic, P n a 2₁
a = 11.28642 (13) Å
b = 10.98496 (14) Å
c = 10.58826 (12) Å
V = 1312.74 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.82 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.922, T_max = 1.000
25817 measured reflections
3823 independent reflections
3778 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.049
S = 1.00
3823 reflections
227 parameters
9 restraints
All H-atom parameters refined
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 1816 Friedel pairs
Flack parameter: 0.27 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1⋯O1	0.86 (1)	2.11 (2)	2.9044 (17)	153 (2)
N1A—H3⋯N1ⁱ	0.87 (1)	2.20 (1)	3.0395 (19)	165 (2)
N1A—H4⋯O8ⁱⁱ	0.85 (1)	2.13 (1)	2.9657 (17)	166 (2)
N2A—H5⋯O5	0.87 (1)	2.04 (1)	2.8985 (16)	175 (3)
N2A—H6⋯N2ⁱⁱⁱ	0.86 (1)	2.20 (2)	3.0068 (18)	157 (3)
N2A—H7⋯O2^iv	0.86 (1)	2.03 (2)	2.8467 (17)	158 (3)
N2A—H8⋯O7^v	0.86 (1)	2.13 (2)	2.8832 (17)	146 (2)
Symmetry codes: (i) $[-x+1, -y+2, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (v) $[-x+1, -y+1, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2011 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812024221/pk2414sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812024221/pk2414Isup2.hkl

checkCIF report

Comment top

Cyclic sulfonimides of the general formula cyclo-[(F₂C)_n(SO₂)₂NH] and the corresponding anions are relevant because of a number of potential applications in various fields, e.g. electrochemistry and organic chemistry similar to the non-cyclic sulfonimides (R^FSO₂)₂NH (Popov et al., 2011; Antoniotti et al., 2010; Vij et al., 1997; Jüschke et al., 1997; DesMarteau, 1995; DesMarteau et al., 1992; Foropoulos & DesMarteau, 1984). The synthesis of the ammonium salt of the smallest member of the cyclic sulfonimides was first reported almost 20 years ago starting from the disulfonylfluoride FO₂SCF₂SO₂F and ammonia (Jüschke et al., 1997). The conversion of the ammonium salt to result in the potassium and rubidium salt with KOH and Rb₂CO₃, respectively and the crystal structures of these alkali metal salts were described, as well.

The title compound ammonium 4,4-difluoro-1,3,2-dithiazetin-2-ide 1,1,3,3-tetraoxide (Fig. 1) crystallizes in the orthorhombic non-centrosymmetric space group Pna2₁ with two independent cations and anions. The ammonium containing title structure is isotypical to the corresponding potassium salt whereas the rubidium salt crystallizes in the monoclinic space group P2₁/c (Jüschke et al., 1997). The S–C–S–N ring is almost planar and the nitrogen atom is bent out of the plane by 9.82 (5) and 12.82 (4)°, respectively in the two anions. The bond lengths and angles of the cyclic anion in its [NH₄]⁺ and K⁺ salt are very similar, whereas slightly larger deviations are found for the Rb⁺ salt. Medium to weak hydrogen bonds connect the [NH₄]⁺ cations and the cyclic anions to form a three-dimensional framework (Fig. 2). The cyclic anion accepts hydrogen bonds by the oxygen atoms of the SO₂ group and by its amide nitrogen atom. The N—H···N hydrogen bonds are, according to the derived distances weaker than the N—H···O bonds. In general N—H···N hydrogen bonds are rare in structurally related salts. For example in the structure of the ammonium triflamide salt, [NH₄][F₃C—SO₂—N—SO₂—CF₃] no hydrogen bond between the amide nitrogen and the ammonium counter cation are present (Davidson et al., 2003). The title structure can be understood as a layered material. The cations and anions are found in layers perpendicular to the c axis (Fig. 3). The ammonium cations appear ordered as a consequence of their hydrogen bonds. The resulting non-centrosymmetric, layered ammonium salt fits well in the general structural chemistry of ammonium salts with layered structures (e.g. Reiss, 2002; Plizko & Meyer, 1998; Bucholz & Mattes, 1988).

Related literature top

For general aspects on the chemistry of fluorinated sulfonimides and their salts, see: Antoniotti et al. (2010); Foropoulos & DesMarteau (1984); Popov et al. (2011); Vij et al. (1997); DesMarteau (1995). For the synthesis and chemistry of the title compound, see: Jüschke et al. (1997). For related structures, see: DesMarteau et al. (1992); Davidson et al. (2003). For similar layered ammonium salts, see: Reiss (2002); Plizko & Meyer (1998); Bucholz & Mattes (1988).

Experimental top

The title compound was synthesized according to a literature procedure (Jüschke et al., 1997).

Structure description top

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2011); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The asymmetric unit of the title compound, with displacement ellipsoids drawn at the 50% probability level; H atoms are drawn as spheres of arbitrary radius.
	Fig. 2. The asymmetric unit of the title compound positioned in the unit cell; H-atoms are drawn with arbitrary radii; hydrogen bonds shown as broken lines.
	Fig. 3. Layered structure of the title compound with view along [110] (ball and stick type model with arbitrary atom radii; fluorine atoms are omitted for clarity; hydrogen bonds shown as broken lines).

Ammonium 4,4-difluoro-1,3,2-dithiazetin-2-ide 1,1,3,3-tetraoxide top

Crystal data top

NH₄⁺·CF₂NO₄S₂⁻	F(000) = 848
M_r = 210.18	D_x = 2.127 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 21999 reflections
a = 11.28642 (13) Å	θ = 3.2–33.6°
b = 10.98496 (14) Å	µ = 0.82 mm⁻¹
c = 10.58826 (12) Å	T = 100 K
V = 1312.74 (3) Å³	Block, colourless
Z = 8	0.30 × 0.25 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3823 independent reflections
Radiation source: fine-focus sealed tube	3778 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 16.2711 pixels mm^-1	θ_max = 30.0°, θ_min = 3.2°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −15→15
T_min = 0.922, T_max = 1.000	l = −14→14
25817 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.019	All H-atom parameters refined
wR(F²) = 0.049	w = 1/[σ²(F_o²) + (0.027P)² + 0.6P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
3823 reflections	Δρ_max = 0.42 e Å⁻³
227 parameters	Δρ_min = −0.23 e Å⁻³
9 restraints	Absolute structure: Flack (1983), 1816 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.27 (4)

Crystal data top

NH₄⁺·CF₂NO₄S₂⁻	V = 1312.74 (3) Å³
M_r = 210.18	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 11.28642 (13) Å	µ = 0.82 mm⁻¹
b = 10.98496 (14) Å	T = 100 K
c = 10.58826 (12) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3823 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	3778 reflections with I > 2σ(I)
T_min = 0.922, T_max = 1.000	R_int = 0.028
25817 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	All H-atom parameters refined
wR(F²) = 0.049	Δρ_max = 0.42 e Å⁻³
S = 1.00	Δρ_min = −0.23 e Å⁻³
3823 reflections	Absolute structure: Flack (1983), 1816 Friedel pairs
227 parameters	Absolute structure parameter: 0.27 (4)
9 restraints

Special details top

Experimental. Absorption correction: CrysAlisPro, Oxford Diffraction Ltd., Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
S1	0.48379 (3)	0.87892 (3)	0.65469 (3)	0.00949 (7)
S2	0.35058 (3)	0.70690 (3)	0.59946 (3)	0.00899 (7)
O1	0.51045 (10)	0.92154 (11)	0.77958 (11)	0.0153 (2)
O2	0.53141 (10)	0.94654 (10)	0.55027 (12)	0.0180 (2)
O3	0.28692 (10)	0.63106 (11)	0.68639 (12)	0.0188 (2)
O4	0.32923 (10)	0.68643 (11)	0.46733 (11)	0.0141 (2)
C1	0.51223 (12)	0.71376 (13)	0.63358 (13)	0.0101 (3)
F1	0.58461 (8)	0.68458 (9)	0.53906 (9)	0.01534 (18)
F2	0.54517 (8)	0.65524 (9)	0.73788 (9)	0.01670 (18)
N1	0.34538 (11)	0.84878 (11)	0.63851 (13)	0.0126 (2)
S3	0.48620 (3)	0.31465 (3)	0.55319 (3)	0.00837 (6)
S4	0.67564 (3)	0.29184 (3)	0.67001 (3)	0.00808 (6)
O6	0.40654 (9)	0.22416 (10)	0.50504 (11)	0.0135 (2)
O5	0.45653 (9)	0.43993 (9)	0.52553 (10)	0.0129 (2)
O7	0.73598 (9)	0.40480 (10)	0.69468 (10)	0.0126 (2)
O8	0.73416 (9)	0.18093 (10)	0.70717 (11)	0.0128 (2)
F3	0.47997 (8)	0.20036 (8)	0.77901 (9)	0.01355 (17)
F4	0.49019 (8)	0.39790 (9)	0.79297 (9)	0.01288 (17)
N2	0.62391 (11)	0.28395 (11)	0.52747 (12)	0.0104 (2)
C2	0.51915 (12)	0.30127 (13)	0.72413 (14)	0.0095 (2)
N1A	0.72362 (11)	0.99695 (12)	0.91184 (12)	0.0122 (2)
H1	0.6585 (14)	0.9597 (19)	0.895 (3)	0.030 (3)*
H2	0.7758 (17)	0.9398 (16)	0.916 (2)	0.030 (3)*
H3	0.715 (2)	1.034 (2)	0.9834 (15)	0.030 (3)*
H4	0.739 (2)	1.0475 (18)	0.8532 (18)	0.030 (3)*
N2A	0.22203 (11)	0.44588 (12)	0.41410 (12)	0.0132 (2)
H5	0.2919 (14)	0.449 (2)	0.448 (2)	0.041 (4)*
H6	0.201 (2)	0.3720 (13)	0.426 (3)	0.041 (4)*
H7	0.173 (2)	0.496 (2)	0.449 (2)	0.041 (4)*
H8	0.230 (2)	0.461 (2)	0.3348 (12)	0.041 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.00951 (13)	0.00917 (14)	0.00979 (15)	−0.00032 (10)	−0.00095 (11)	−0.00005 (12)
S2	0.00864 (13)	0.00925 (14)	0.00907 (14)	−0.00050 (11)	0.00066 (11)	0.00012 (12)
O1	0.0149 (5)	0.0167 (5)	0.0143 (5)	0.0003 (4)	−0.0040 (4)	−0.0052 (4)
O2	0.0186 (5)	0.0171 (5)	0.0183 (5)	−0.0020 (4)	0.0028 (4)	0.0068 (5)
O3	0.0179 (5)	0.0187 (5)	0.0199 (6)	−0.0036 (4)	0.0056 (4)	0.0072 (4)
O4	0.0128 (5)	0.0177 (5)	0.0117 (5)	0.0013 (4)	−0.0028 (4)	−0.0041 (4)
C1	0.0096 (6)	0.0106 (6)	0.0101 (6)	0.0015 (4)	−0.0002 (4)	−0.0011 (5)
F1	0.0108 (4)	0.0203 (4)	0.0149 (4)	0.0023 (3)	0.0030 (3)	−0.0056 (3)
F2	0.0204 (4)	0.0158 (4)	0.0139 (4)	0.0033 (4)	−0.0070 (4)	0.0036 (3)
N1	0.0098 (5)	0.0098 (5)	0.0183 (6)	0.0008 (4)	−0.0019 (4)	−0.0037 (5)
S3	0.00810 (13)	0.00965 (14)	0.00735 (14)	0.00008 (11)	−0.00006 (11)	−0.00046 (11)
S4	0.00836 (13)	0.00801 (14)	0.00787 (14)	0.00020 (10)	−0.00012 (11)	0.00033 (11)
O6	0.0124 (5)	0.0157 (5)	0.0123 (5)	−0.0035 (4)	−0.0003 (4)	−0.0038 (4)
O5	0.0141 (5)	0.0111 (5)	0.0133 (5)	0.0026 (4)	−0.0019 (4)	0.0013 (4)
O7	0.0142 (4)	0.0115 (5)	0.0122 (5)	−0.0040 (4)	0.0006 (4)	−0.0013 (4)
O8	0.0129 (4)	0.0121 (5)	0.0133 (5)	0.0035 (4)	0.0008 (4)	0.0036 (4)
F3	0.0140 (4)	0.0138 (4)	0.0128 (4)	−0.0027 (3)	0.0018 (3)	0.0048 (3)
F4	0.0151 (4)	0.0135 (4)	0.0100 (4)	0.0037 (3)	0.0004 (3)	−0.0041 (3)
N2	0.0083 (5)	0.0149 (6)	0.0079 (5)	0.0011 (4)	0.0001 (4)	−0.0009 (4)
C2	0.0103 (6)	0.0091 (6)	0.0091 (6)	−0.0001 (4)	0.0004 (5)	0.0002 (5)
N1A	0.0136 (6)	0.0116 (5)	0.0114 (6)	−0.0006 (4)	0.0000 (4)	0.0007 (4)
N2A	0.0113 (5)	0.0150 (6)	0.0133 (6)	−0.0003 (4)	−0.0009 (5)	0.0037 (5)

Geometric parameters (Å, º) top

S1—O1	1.4347 (12)	S4—O7	1.4394 (11)
S1—O2	1.4363 (12)	S4—O8	1.4406 (11)
S1—N1	1.6060 (12)	S4—N2	1.6206 (12)
S1—C1	1.8559 (14)	S4—C2	1.8596 (15)
S2—O3	1.4344 (12)	F3—C2	1.3274 (16)
S2—O4	1.4373 (12)	F4—C2	1.3285 (16)
S2—N1	1.6135 (13)	N1A—H1	0.860 (11)
S2—C1	1.8614 (14)	N1A—H2	0.862 (11)
C1—F2	1.3308 (16)	N1A—H3	0.865 (11)
C1—F1	1.3311 (16)	N1A—H4	0.852 (12)
S3—O6	1.4340 (11)	N2A—H5	0.866 (12)
S3—O5	1.4463 (11)	N2A—H6	0.855 (12)
S3—N2	1.6135 (12)	N2A—H7	0.862 (12)
S3—C2	1.8535 (15)	N2A—H8	0.860 (12)

O1—S1—O2	117.53 (7)	O7—S4—O8	117.55 (7)
O1—S1—N1	111.69 (7)	O7—S4—N2	112.68 (7)
O2—S1—N1	112.86 (7)	O8—S4—N2	111.98 (7)
O1—S1—C1	113.18 (7)	O7—S4—C2	110.21 (6)
O2—S1—C1	110.37 (7)	O8—S4—C2	113.48 (6)
N1—S1—C1	87.36 (6)	N2—S4—C2	87.01 (6)
O3—S2—O4	116.73 (7)	S3—N2—S4	100.29 (7)
O3—S2—N1	112.23 (7)	F3—C2—F4	110.19 (12)
O4—S2—N1	113.23 (7)	F3—C2—S3	115.27 (10)
O3—S2—C1	112.95 (7)	F4—C2—S3	115.03 (10)
O4—S2—C1	111.07 (6)	F3—C2—S4	113.88 (10)
N1—S2—C1	86.95 (6)	F4—C2—S4	116.57 (10)
F2—C1—F1	109.64 (11)	S3—C2—S4	83.92 (6)
F2—C1—S1	114.87 (10)	H1—N1A—H2	104 (2)
F1—C1—S1	115.60 (10)	H1—N1A—H3	108 (2)
F2—C1—S2	114.54 (10)	H2—N1A—H3	112 (2)
F1—C1—S2	116.48 (10)	H1—N1A—H4	110 (2)
S1—C1—S2	83.88 (6)	H2—N1A—H4	112 (2)
S1—N1—S2	101.01 (7)	H3—N1A—H4	111 (2)
O6—S3—O5	116.26 (7)	H5—N2A—H6	103 (3)
O6—S3—N2	113.52 (7)	H5—N2A—H7	113 (3)
O5—S3—N2	112.81 (6)	H6—N2A—H7	112 (3)
O6—S3—C2	114.71 (7)	H5—N2A—H8	108 (2)
O5—S3—C2	108.64 (6)	H6—N2A—H8	111 (3)
N2—S3—C2	87.42 (7)	H7—N2A—H8	111 (2)

N1—S1—C1—S2	6.25 (6)	C2—S3—N2—S4	−9.52 (7)
N1—S2—C1—S1	−6.22 (6)	C2—S4—N2—S3	9.49 (7)
C1—S1—N1—S2	−7.31 (7)	N2—S3—C2—S4	8.20 (6)
C1—S2—N1—S1	7.29 (7)	N2—S4—C2—S3	−8.17 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1···O1	0.86 (1)	2.11 (2)	2.9044 (17)	153 (2)
N1A—H3···N1ⁱ	0.87 (1)	2.20 (1)	3.0395 (19)	165 (2)
N1A—H4···O8ⁱⁱ	0.85 (1)	2.13 (1)	2.9657 (17)	166 (2)
N2A—H5···O5	0.87 (1)	2.04 (1)	2.8985 (16)	175 (3)
N2A—H6···N2ⁱⁱⁱ	0.86 (1)	2.20 (2)	3.0068 (18)	157 (3)
N2A—H7···O2^iv	0.86 (1)	2.03 (2)	2.8467 (17)	158 (3)
N2A—H8···O7^v	0.86 (1)	2.13 (2)	2.8832 (17)	146 (2)

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

Experimental details

Crystal data
Chemical formula	NH₄⁺·CF₂NO₄S₂⁻
M_r	210.18
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	11.28642 (13), 10.98496 (14), 10.58826 (12)
V (Å³)	1312.74 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.82
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.922, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	25817, 3823, 3778
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.049, 1.00
No. of reflections	3823
No. of parameters	227
No. of restraints	9
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.23
Absolute structure	Flack (1983), 1816 Friedel pairs
Absolute structure parameter	0.27 (4)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2011), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1···O1	0.860 (11)	2.112 (16)	2.9044 (17)	153 (2)
N1A—H3···N1ⁱ	0.865 (11)	2.196 (13)	3.0395 (19)	165 (2)
N1A—H4···O8ⁱⁱ	0.852 (12)	2.131 (13)	2.9657 (17)	166 (2)
N2A—H5···O5	0.866 (12)	2.035 (12)	2.8985 (16)	175 (3)
N2A—H6···N2ⁱⁱⁱ	0.855 (12)	2.200 (16)	3.0068 (18)	157 (3)
N2A—H7···O2^iv	0.862 (12)	2.029 (15)	2.8467 (17)	158 (3)
N2A—H8···O7^v	0.860 (12)	2.129 (18)	2.8832 (17)	146 (2)

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

Acknowledgements

This publication was funded by the German Research Foundation (DFG) and the Heinrich-Heine-Universität Düsseldorf under the funding programme Open Access Publishing.

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