Ethane-1,2-diaminium 4,4′-sulfonyl­dibenzoate

Graham Smith; Urs D Wermuth

doi:10.1107/S1600536811041274

. 2011 Oct 12;67(Pt 11):o2966. doi: 10.1107/S1600536811041274

Ethane-1,2-diaminium 4,4′-sulfonyldibenzoate

Graham Smith ^a,^*, Urs D Wermuth ^a

PMCID: PMC3247372 PMID: 22219990

Abstract

In the title salt, C₂H₁₀N₂ ²⁺·C₁₄H₈O₆S²⁻, both the ethylenediaminium cations and the 4,4′-sulfonyldibenzoate dianions have crystallographic twofold rotational symmetry. They are interlinked by aminium N—H⋯O_carboxylate hydrogen-bonding associations, giving sheets parallel to (101) and are further linked along [010], forming a three-dimensional structure.

Related literature

For the structure of 4,4′-sulfonyldibenzoic acid, see: Lian et al. (2007 ▶). For the structures of some metal complexes of the acid, see: Bannerjee et al. (2009 ▶); Jiao (2010 ▶); Pan et al. (2007 ▶); Wu et al. (2007 ▶); Zhuang & Jin (2007 ▶).

Experimental

Crystal data

C₂H₁₀N₂ ²⁺·C₁₄H₈O₆S²⁻
M _r = 366.39
Monoclinic,
a = 15.2860 (8) Å
b = 4.8436 (2) Å
c = 11.9803 (6) Å
β = 111.812 (6)°
V = 823.51 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 200 K
0.35 × 0.25 × 0.08 mm

Data collection

Oxford Diffraction Gemini-S CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.98, T _max = 0.99
5062 measured reflections
1607 independent reflections
1290 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.098
S = 1.05
1607 reflections
114 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within WinGX (Farrugia, 1999 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041274/lh5347sup1.cif

e-67-o2966-sup1.cif^{(15.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041274/lh5347Isup2.hkl

e-67-o2966-Isup2.hkl^{(77.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811041274/lh5347Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H11A⋯O42ⁱ	0.89	1.87	2.760 (2)	174
N1A—H12A⋯O41ⁱⁱ	0.89	1.88	2.740 (2)	163
N1A—H13A⋯O42	0.89	1.93	2.798 (2)	164

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors acknowledge financial support from the Australian Reseach Council and the Faculty of Science and Technology and the University Library, Queensland University of Technology.

supplementary crystallographic information

Comment

The structure of the diprotic acid 4,4'-sulfonyldibenzoic acid (SDBA) is known (Lian et al., 2007) and although some metal complexes with SDBA alone have been reported, e.g. with Li (Bannerjee et al., 2009), Zn (Pan et al., 2007; Zhuang & Jin, 2007) and Cd (Jiao, 2010), most structures have been with mixed ligands including this acid (Wu et al., 2007). No structures of compounds of SDBA with Lewis bases are known. Our 1:1 stoichiometric reaction of this acid with ethylenediamine gave the the title compound C₂H₁₀N₂²⁺ C₁₄H₈O₆S^2-, and the structure is reported here. In this structure (Fig. 1), both the ethylenediaminium cations and the 4,4'-sulfonyldibenzoate dianions have crystallographic twofold rotational symmetry. In contrast, the two substituted ring systems of the parent molecule are mirror related (Lian et al., 2007). With the present salt, the central C1—S1—C1ⁱ bond angle is 104.90 (8)Å [for symmetry code (i), see Fig. 1], while the carboxyl group (defined by atoms C4–C41–O41–O42) lies slightly out of the plane of the benzene ring [dihedral angle 19.31 (9)°]. The ethylenediamine cation is essentially planar [torsion angle N1A—C1A—C1Aⁱⁱ—N1Aⁱⁱ, 171.97 (14)°]. For symmetry code (ii), see also Fig. 1.

Intermolecular cation aminium N—H···O_carboxyl hydrogen bonds (Table 1) interlink the SDBA dianions into sheets lying in the (101) planes, as well as down the b axis, forming a three-dimensional structure (Fig. 2). The sulfonyl O atoms are involved in inter-species C—H···O associations [C2—H2···O1^v, 3.200 (2) Å: symmetry code (v) -x + 2, -y + 1, -z + 1]. as well as in S—O···Cg interactions [minimum S1—O1···Cg(ring C1^viii–C6^viii) = 3.5409 (13) Å; S—O···Cg angle, 90.61 (5)°: symmetry code (viii) -x + 2, y + 1, -z + 3/2].

Experimental

The title compound was synthesized by heating together for 10 min under reflux, 1 mmol quantities of 4,4'-sulfonyldibenzoic acid and ethylenediamine in 50 ml of 50% ethanol–water. After evaporation of the solvent the non-crystalline product was recrystallized from a 50% methanol–isopropyl alcohol solution giving thin colourless crystal plates from which a specimen was cleaved for the X-ray analysis..