Bis(2-hy­droxy­ethanaminium) naphthalene-1,5-disulfonate

Cong Wang; Sheng Li Yang

doi:10.1107/S1600536811023269

. 2011 Jun 30;67(Pt 7):o1847. doi: 10.1107/S1600536811023269

Bis(2-hydroxyethanaminium) naphthalene-1,5-disulfonate

Cong Wang ^a, Sheng Li Yang ^a,^*

PMCID: PMC3151963 PMID: 21837212

Abstract

In the crystal structure of the title compound, 2C₂H₈NO⁺·C₁₀H₆O₆S₂ ²⁻, the anion lies on an inversion centre. The components are held together by O—H⋯O hydrogen bond, forming a 2:1 aggregate. The aggregates are further connected by N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Gao et al. (2005 ▶); Li & Chai (2007 ▶); Russell et al. (1997 ▶); Sakwa & Wheeler (2003 ▶); Wang et al. (2008 ▶); Zhang et al. (2005 ▶).

Experimental

Crystal data

2C₂H₈NO⁺·C₁₀H₆O₆S₂ ²⁻
M _r = 410.48
Monoclinic,
a = 9.7946 (14) Å
b = 8.9011 (13) Å
c = 10.4050 (16) Å
β = 104.334 (2)°
V = 878.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 293 K
0.42 × 0.34 × 0.30 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.855, T _max = 0.898
4721 measured reflections
1718 independent reflections
1625 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.080
S = 1.04
1718 reflections
122 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023269/is2725sup1.cif

e-67-o1847-sup1.cif^{(14.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023269/is2725Isup2.hkl

e-67-o1847-Isup2.hkl^{(82.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811023269/is2725Isup3.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
O4—H4′⋯O2	0.835 (10)	2.041 (10)	2.840 (2)	160 (2)
N1—H1A⋯O4ⁱ	0.89	2.13	2.934 (2)	149
N1—H1B⋯O1ⁱⁱ	0.89	1.90	2.766 (2)	164
N1—H1C⋯O3ⁱⁱⁱ	0.89	1.96	2.837 (2)	168
C3—H3⋯O1^iv	0.93	2.41	3.270 (2)	154
C5—H5⋯O2^v	0.93	2.55	3.459 (2)	167

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

supplementary crystallographic information

Comment

Several supramolecular structures of naphthalene-1,5-disulfonate have been reported previously (Russell et al., 1997; Zhang et al., 2005; Gao et al., 2005; Wang et al., 2008). As an extension of research, we report here the synthesis and structure of the title compound, (I) (Table 1 & Fig. 1).

The naphthalene-1,5-disulfonate anion is linked to the ethanolaminium cation by O2—H4'···O4 hydrogen bond (Fig. 1 & Table 1). The crystal structure is further built by N—H···O and C—H···O hydrogen bonds. (Fig. 2 & Table 1). Due to steric hindrance of sulfonate, the nearest centroid separation between naphthalene rings is of 5.264 (3) Å, suggesting no π–π stacking. The arrangement of naphthalene rings is very similar to those observed in previous cases (Sakwa & Wheeler, 2003; Li & Chai, 2007; Wang et al., 2008), but is different from that in bis(oxonium monohydrate) naphthalene-1,5-disulfonate, which shows a partial π–π stacking.

Experimental

Naphthalene-1,5-disulfonic acid (5.1 g) and ethanolamine (1.2 g) in a molar ratio of 1:1 were mixed and dissolved in sufficient ethanol by heating to 373 K, at which point a clear solution resulted. The system was then cooled slowly to room temperature. Crystals of (I) (4.7 g) were formed, collected and washed with ethanol.