The crystal structures of two novel polymorphs of bis­(oxonium) ethane-1,2-di­sulfonate

Mazurek, J.; Fernandez-Casares, A.

doi:10.1107/S2056989019013367

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Volume 75| Part 11| November 2019| Pages 1586-1589

https://doi.org/10.1107/S2056989019013367

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The crystal structures of two novel polymorphs of bis(oxonium) ethane-1,2-disulfonate

Jaroslaw Mazurek ^a ^* and Ana Fernandez-Casares ^a

^aArdena, Solid State Research Services, Meibergdreef 31, 1105 AZ Amsterdam, The Netherlands
^*Correspondence e-mail: jaroslaw.mazurek@ardena.com

Edited by A. J. Lough, University of Toronto, Canada (Received 3 September 2019; accepted 30 September 2019; online 3 October 2019)

Two novel crystal forms of bis(oxonium) ethane-1,2-disulfonate, 2H₃O⁻·C₂H₄O₆S₂²⁻, are reported. Polymorph II has monoclinic (P2₁/n) symmetry, while the symmetry of form III is triclinic (P $[\overline{1}]$ ). Both structures display extensive networks of O—H⋯O hydrogen bonds. While this network in Form II is similar to that observed for the previously reported Form I [Mootz & Wunderlich (1970 ). Acta Cryst. B26, 1820–1825; Sartori et al. (1994 ). Z. Naturforsch. 49, 1467–1472] and extends in all directions, in Form III it differs significantly, forming layers parallel to the ab plane. The sulfonate molecule in all three forms adopts a nearly identical geometry. The other observed differences between the forms, apart from the hydrogen-bonding network, are observed in the crystal density and packing index.

Keywords: crystal structure; polymorphism; oxonium cation; sulfonate anions.

CCDC references: 1956689; 1956690; 1956689; 1956690

1. Chemical context

Sulfonic acids are commonly used in salt formation in the pharmaceutical industry, especially for poorly or non soluble in water drugs (Neau & Loka, 2018 ). Salts of ethane-1,2-disulfonic acid account for 0.38% of all the FDA-approved commercially marketed salts (Steele & Talbir, 2016 ) and therefore its toxicology, dosage (Saal & Becker, 2013 ) and various physico-chemical properties are widely studied (Black et al., 2007 ; Elder et al., 2010 ). In our laboratory, ethane-1,2-disulfonic acid is commonly used in the salt screening for increasing solubility as well as improving the crystallinity of various researched active pharmaceutical ingredients (APIs).

2. Structural commentary

The sulfonate anion in all polymorphs, including the previously determined form (Mootz & Wunderlich, 1970, refcode HOEDSO; Sartori et al., 1994, refcode HOEDSO01) has a nearly identical geometry. In all cases, the center of the C—C bond is located on an inversion center, and the C—S and C—O distances in all cases are within 3σ. The sulfonate group adopts the geometry of an open umbrella with the C—S—O bond angles of 106.51 (6), 105.82 (6), 107.23 (6)° for Form II (Fig. 1) and 106.16 (11), 106.21 (10), 107.20 (12)° for Form III (Fig. 2). The values of all O—S—O angles are above 110° [112.91 (7), 111.48 (7), 112.37 (7)° for Form II and 111.31 (11), 113.45 (11), 112.00 (12)° for Form III]. In this way, the molecular symmetry of the sulfonate group becomes slightly distorted C_3V. In all crystals, the oxonium cations have a pyramidal geometry with slightly elongated O—H distances for one H atom. This is most likely an effect of the fast exchange of a proton (H atom) between the sulfonate group and the water molecules.

Figure 1
The molecular structure of an anion–cation pair of Form II, with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and hydrogen bonds are shown in torquoise. Unlabelled atoms are related to labelled ones by the symmetry operator (−x + 1, −y + 1, −z + 1).

Figure 2
The molecular structure of anion cation pair of Form III, with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and hydrogen bonds are shown in torquoise. Unlabelled atoms are related to labelled ones by the symmetry operator (−x + 1, −y + 1, −z + 1).

The biggest differences between forms are observed in the density of the crystal, as well as in the packing coefficient (Kitajgorodskij, 1973 ). The lowest values of both parameters are attributed to Form III (1.60 g cm⁻³ and 0.67, respectively), which suggests that this polymorph is the least stable. Form II presented here has a slightly better packing index than previously reported for Form I (Mootz & Wunderlich, 1970; Sartori et al., 1994) 0.75 versus 0.73. On the other hand, the density is lower: 1.78 versus 1.82 g cm⁻³, respectively.

3. Supramolecular features

The hydrogen bonds between the oxonium cations and sulfonate anions in the crystal of Form II (Table 1, Fig. 3) extend in all directions forming a three-dimensional network similar to that observed for Form I (Mootz & Wunderlich, 1970; Sartori et al., 1994). However, contrary to the previously reported form, where the hydrogen-bond network is built from alternate anion–cations layers, in Form II such layers could not be distinguished. The supramolecular behaviour of Form III is significantly different. In this case (Table 2 and Fig. 4), the anion–cation hydrogen-bond network forms separate layers parallel to the ab plane built from sulfonate anions surrounded by oxonium cations with no interactions between the planes.

Table 1
Hydrogen-bond geometry (Å, °) for Form II

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H63⋯O2	0.99 (2)	2.62 (2)	3.1795 (17)	116 (2)
O6—H61⋯O2ⁱ	1.00 (2)	2.02 (3)	2.9312 (16)	150 (3)
O6—H62⋯O3	1.06 (2)	1.92 (3)	2.9141 (16)	154 (3)
O6—H61⋯O3ⁱⁱ	1.00 (2)	2.60 (3)	2.9857 (16)	103 (2)
O6—H63⋯O1ⁱⁱⁱ	0.99 (2)	2.14 (2)	3.0266 (18)	148 (2)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+2, -z+1; (iii) x+1, y, z.

Table 2
Hydrogen-bond geometry (Å, °) for Form III

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H61⋯O1ⁱ	1.07 (4)	1.93 (4)	2.991 (3)	170 (4)
O6—H62⋯O2ⁱⁱ	1.02 (4)	2.52 (3)	3.002 (3)	108 (2)
O6—H62⋯O3	1.02 (4)	1.97 (4)	2.945 (3)	158 (3)
O6—H63⋯O1ⁱⁱⁱ	1.02 (4)	1.89 (4)	2.899 (3)	173 (3)
Symmetry codes: (i) x, y-1, z; (ii) x-1, y, z; (iii) x-1, y-1, z.

Figure 3
The crystal packing of Form II, viewed along the a axis. The ethane-1,2-disulfonate dianions are coloured in green, while oxonium cations are red and hydrogen bonds are shown in torquoise.

Figure 4
The crystal packing of Form III, viewed along the a axis. The ethane-1,2-disulfonate dianions are coloured in green, while oxonium cations are red and hydrogen bonds are shown in turquoise.

4. Database survey

As mentioned above, the crystal structure of a different polymorphic form of oxonium ethane-1,2-disulfonate has been previously reported (Mootz, & Wunderlich, 1970, refcode HOEDSO; Sartori et al., 1994, refcode HOEDSO01). Apart from these structures, there are 12 hits for ethane-1,2-disulfonate salts in the Cambridge Structural Database (CSD, Version 5.40; ConQuest 2.02; Groom et al., 2016 ), one of which is disordered. The geometry of the sulfonate group in all of the anions is nearly the same, with slightly distorted C_3v molecular symmetry for the open-umbrella geometry. The average values of the C—S—O and O—S—O bond angles are very close to those reported in this paper: 105.9±0.8 and 112.8±0.9°, respectively.

5. Synthesis and crystallization

Both crystals were obtained from an aqueous solution during unsuccessful salt formation with an unnamed free base (API) in water. Firstly, columnar crystals of Form III that appeared to be unstable were grown from the thick oil and within time transformed into prismatic crystals of Form II.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All H atoms were found in difference-Fourier maps and refined with isotropic displacement parameters. The DFIX 0.98 0.03 O6 H61, O6 H62 and O6 H63 instruction in SHELXL2014/7 (Sheldrick, 2015b ) was used to restrain the oxonium O—H distance in Form II. All of the oxonium H atoms in Form III were refined independently without any restraints.

Table 3
Experimental details

	Form II	Form III
Crystal data
Chemical formula	2H₃O⁺·C₂H₄O₆S₂²⁻	2H₃O⁺·C₂H₄O₆S₂²⁻
M_r	226.22	226.22
Crystal system, space group	Monoclinic, P2₁/n	Triclinic, P $[\overline{1}]$
Temperature (K)	296	296
a, b, c (Å)	5.8050 (3), 8.3566 (6), 8.7433 (6)	5.0371 (3), 5.5424 (2), 8.8188 (4)
α, β, γ (°)	90, 95.148 (4), 90	98.426 (5), 104.511 (3), 91.663 (4)
V (Å³)	422.43 (5)	235.22 (2)
Z	2	1
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	0.64	0.58
Crystal size (mm)	0.45 × 0.32 × 0.23	0.30 × 0.12 × 0.11

Data collection
Diffractometer	Bruker KappaCCD	Bruker KappaCCD
Absorption correction	Gaussian integration (Coppens, 1970 )	Gaussian integration (Coppens, 1970)
T_min, T_max	0.748, 0.907	0.813, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	17906, 1848, 1768	7504, 1708, 1192
R_int	0.075	0.131
(sin θ/λ)_max (Å⁻¹)	0.806	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.121, 1.04	0.058, 0.163, 1.04
No. of reflections	1848	1708
No. of parameters	76	76
No. of restraints	3	0
H-atom treatment	All H-atom parameters refined	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.93	0.66, −0.67
Computer programs: COLLECT (Hooft, 1998 ), HKL SCALEPACK and DENZO (Otwinowski & Minor, 1997 ), SHELXT (Sheldrick, 2015a ), SHELXL2014/7 (Sheldrick, 2015b), Mercury (Macrae et al., 2008 ) and enCIFer (Allen et al., 2004 ).

Supporting information

CCDC references: 1956689; 1956690; 1956689; 1956690

Crystal structure: contains datablocks I, II. DOI: https://doi.org/10.1107/S2056989019013367/lh5920sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019013367/lh5920Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989019013367/lh5920IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989019013367/lh5920Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989019013367/lh5920IIsup5.cml

checkCIF report

Computing details top

For both structures, data collection: COLLECT (Hooft, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Bis(oxonium) ethane-1,2-disulfonate (I) top

Crystal data top

2H₃O⁺·C₂H₄O₆S₂²⁻	F(000) = 236
M_r = 226.22	D_x = 1.778 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.8050 (3) Å	Cell parameters from 11538 reflections
b = 8.3566 (6) Å	θ = 1.0–35.0°
c = 8.7433 (6) Å	µ = 0.64 mm⁻¹
β = 95.148 (4)°	T = 296 K
V = 422.43 (5) Å³	Prism, pale yellow
Z = 2	0.45 × 0.32 × 0.23 mm

Data collection top

Bruker KappaCCD diffractometer	1848 independent reflections
Radiation source: fine-focus sealed tube	1768 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	R_int = 0.075
Detector resolution: 9 pixels mm^-1	θ_max = 34.9°, θ_min = 3.4°
CCD scans	h = −9→9
Absorption correction: integration Gaussian integration (Coppens, 1970)	k = −13→13
T_min = 0.748, T_max = 0.907	l = −14→14
17906 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)] = 0.041	All H-atom parameters refined
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.0797P)² + 0.1864P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.026
1848 reflections	Δρ_max = 0.62 e Å⁻³
76 parameters	Δρ_min = −0.93 e Å⁻³
3 restraints	Extinction correction: SHELXL-2014/7 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: difference Fourier map	Extinction coefficient: 0.20 (2)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
O1	0.03777 (17)	0.61584 (15)	0.29236 (14)	0.0319 (2)
O2	0.4298 (2)	0.65073 (13)	0.21941 (13)	0.0302 (2)
O3	0.30307 (19)	0.79554 (12)	0.43552 (13)	0.0308 (2)
S4	0.27802 (4)	0.64978 (3)	0.34467 (3)	0.01890 (13)
C5	0.3753 (2)	0.48838 (15)	0.46678 (14)	0.0231 (2)
H5A	0.270 (5)	0.476 (3)	0.541 (3)	0.043 (6)*
H5B	0.360 (4)	0.393 (3)	0.404 (2)	0.025 (5)*
O6	0.7708 (2)	0.90258 (15)	0.39286 (16)	0.0363 (3)
H61	0.822 (6)	1.009 (3)	0.357 (4)	0.066 (9)*
H62	0.588 (4)	0.889 (4)	0.383 (4)	0.067 (9)*
H63	0.797 (4)	0.795 (3)	0.350 (3)	0.041 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0219 (4)	0.0345 (5)	0.0373 (5)	−0.0002 (3)	−0.0079 (4)	0.0012 (4)
O2	0.0341 (5)	0.0339 (5)	0.0238 (4)	0.0083 (4)	0.0096 (4)	0.0055 (3)
O3	0.0333 (5)	0.0227 (4)	0.0362 (5)	0.0020 (3)	0.0025 (4)	−0.0081 (4)
S4	0.01863 (17)	0.01917 (17)	0.01865 (17)	0.00184 (7)	0.00025 (10)	0.00054 (7)
C5	0.0218 (4)	0.0231 (5)	0.0234 (5)	−0.0027 (3)	−0.0032 (3)	0.0061 (4)
O6	0.0307 (5)	0.0320 (5)	0.0452 (6)	−0.0022 (4)	−0.0012 (4)	0.0000 (5)

Geometric parameters (Å, º) top

O1—S4	1.4561 (10)	C5—H5A	0.94 (3)
O2—S4	1.4658 (11)	C5—H5B	0.97 (2)
O3—S4	1.4544 (10)	O6—H61	1.00 (2)
S4—C5	1.7804 (11)	O6—H62	1.06 (2)
C5—C5ⁱ	1.523 (2)	O6—H63	0.99 (2)

O3—S4—O1	112.37 (7)	S4—C5—H5A	108.0 (16)
O3—S4—O2	111.48 (7)	C5ⁱ—C5—H5B	110.7 (12)
O1—S4—O2	112.91 (7)	S4—C5—H5B	106.3 (12)
O3—S4—C5	107.23 (6)	H5A—C5—H5B	105 (2)
O1—S4—C5	106.51 (6)	H61—O6—H62	113 (3)
O2—S4—C5	105.82 (6)	H61—O6—H63	129 (2)
C5ⁱ—C5—S4	111.82 (11)	H62—O6—H63	93 (2)
C5ⁱ—C5—H5A	114.1 (17)

O3—S4—C5—C5ⁱ	−57.98 (14)	O2—S4—C5—C5ⁱ	61.12 (14)
O1—S4—C5—C5ⁱ	−178.48 (12)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H63···O2	0.99 (2)	2.62 (2)	3.1795 (17)	116 (2)
O6—H61···O2ⁱⁱ	1.00 (2)	2.02 (3)	2.9312 (16)	150 (3)
O6—H62···O3	1.06 (2)	1.92 (3)	2.9141 (16)	154 (3)
O6—H61···O3ⁱⁱⁱ	1.00 (2)	2.60 (3)	2.9857 (16)	103 (2)
O6—H63···O1^iv	0.99 (2)	2.14 (2)	3.0266 (18)	148 (2)

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

Bis(oxonium) ethane-1,2-disulfonate (II) top

Crystal data top

2H₃O⁺·C₂H₄O₆S₂²⁻	Z = 1
M_r = 226.22	F(000) = 118
Triclinic, P1	D_x = 1.597 Mg m⁻³
a = 5.0371 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 5.5424 (2) Å	Cell parameters from 4728 reflections
c = 8.8188 (4) Å	θ = 1.0–32.6°
α = 98.426 (5)°	µ = 0.57 mm⁻¹
β = 104.511 (3)°	T = 296 K
γ = 91.663 (4)°	Columnar, colorless
V = 235.22 (2) Å³	0.30 × 0.12 × 0.11 mm

Data collection top

Bruker KappaCCD diffractometer	1708 independent reflections
Radiation source: fine-focus sealed tube	1192 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	R_int = 0.131
Detector resolution: 9 pixels mm^-1	θ_max = 32.6°, θ_min = 2.4°
CCD scans	h = −7→6
Absorption correction: integration Gaussian integration (Coppens, 1970)	k = −8→8
T_min = 0.813, T_max = 0.947	l = −11→13
7504 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)] = 0.058	All H-atom parameters refined
wR(F²) = 0.163	w = 1/[σ²(F_o²) + (0.0869P)² + 0.0186P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.016
1708 reflections	Δρ_max = 0.66 e Å⁻³
76 parameters	Δρ_min = −0.67 e Å⁻³
0 restraints	Extinction correction: SHELXL-2014/7 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: difference Fourier map	Extinction coefficient: 0.19 (3)

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.6030 (4)	0.9888 (3)	0.7642 (2)	0.0387 (4)
O2	0.6622 (4)	0.5760 (3)	0.8252 (2)	0.0378 (4)
O3	0.2119 (4)	0.6995 (4)	0.7086 (3)	0.0417 (5)
S4	0.50463 (11)	0.73087 (9)	0.72171 (6)	0.0267 (2)
C5	0.5533 (5)	0.6324 (4)	0.5302 (3)	0.0290 (5)
H5A	0.473 (7)	0.750 (6)	0.459 (4)	0.043 (8)*
H5B	0.737 (7)	0.654 (6)	0.526 (4)	0.054 (9)*
O6	0.1360 (5)	0.2554 (4)	0.8443 (3)	0.0477 (5)
H61	0.318 (10)	0.173 (8)	0.827 (5)	0.083 (13)*
H62	0.113 (7)	0.415 (6)	0.798 (5)	0.049 (9)*
H63	−0.056 (8)	0.173 (6)	0.822 (5)	0.057 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0405 (11)	0.0264 (8)	0.0464 (10)	−0.0019 (7)	0.0115 (8)	−0.0030 (7)
O2	0.0425 (11)	0.0396 (9)	0.0301 (8)	0.0109 (8)	0.0059 (7)	0.0062 (7)
O3	0.0235 (9)	0.0476 (10)	0.0538 (11)	0.0009 (7)	0.0125 (8)	0.0028 (8)
S4	0.0229 (3)	0.0261 (3)	0.0297 (3)	0.0012 (2)	0.0060 (2)	0.0014 (2)
C5	0.0289 (12)	0.0297 (11)	0.0271 (10)	−0.0025 (9)	0.0059 (9)	0.0034 (8)
O6	0.0415 (13)	0.0454 (11)	0.0535 (12)	0.0046 (9)	0.0092 (10)	0.0046 (9)

Geometric parameters (Å, º) top

O1—S4	1.4625 (17)	C5—H5A	0.99 (3)
O2—S4	1.4509 (18)	C5—H5B	0.94 (4)
O3—S4	1.4532 (19)	O6—H61	1.07 (4)
S4—C5	1.777 (2)	O6—H62	1.02 (4)
C5—C5ⁱ	1.519 (4)	O6—H63	1.02 (4)

O2—S4—O3	112.00 (12)	S4—C5—H5A	109.0 (18)
O2—S4—O1	113.45 (11)	C5ⁱ—C5—H5B	110 (2)
O3—S4—O1	111.31 (11)	S4—C5—H5B	113 (2)
O2—S4—C5	106.21 (10)	H5A—C5—H5B	98 (3)
O3—S4—C5	107.20 (12)	H61—O6—H62	111 (3)
O1—S4—C5	106.16 (11)	H61—O6—H63	127 (3)
C5ⁱ—C5—S4	111.0 (2)	H62—O6—H63	107 (3)
C5ⁱ—C5—H5A	114.8 (19)

O2—S4—C5—C5ⁱ	61.3 (3)	O1—S4—C5—C5ⁱ	−177.6 (2)
O3—S4—C5—C5ⁱ	−58.6 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H61···O1ⁱⁱ	1.07 (4)	1.93 (4)	2.991 (3)	170 (4)
O6—H62···O2ⁱⁱⁱ	1.02 (4)	2.52 (3)	3.002 (3)	108 (2)
O6—H62···O3	1.02 (4)	1.97 (4)	2.945 (3)	158 (3)
O6—H63···O1^iv	1.02 (4)	1.89 (4)	2.899 (3)	173 (3)

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

References

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Volume 75| Part 11| November 2019| Pages 1586-1589

https://doi.org/10.1107/S2056989019013367

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

The crystal structures of two novel polymorphs of bis­­(oxonium) ethane-1,2-di­sulfonate

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

References

research communications

The crystal structures of two novel polymorphs of bis(oxonium) ethane-1,2-disulfonate

3. Supramolecular features