2-(2-Furylmethyl­ammonio)ethane­sulfonate methanol solvate

Zhong-Xiang Du; Ling-Zhi Wang

doi:10.1107/S1600536809020005

. 2009 Jun 6;65(Pt 7):o1459. doi: 10.1107/S1600536809020005

2-(2-Furylmethylammonio)ethanesulfonate methanol solvate

Zhong-Xiang Du ^a,^*, Ling-Zhi Wang ^b

PMCID: PMC2969461 PMID: 21582763

Abstract

The organic molecule of the title compound, C₇H₁₁NO₄S·CH₃OH, is a zwitterion and its furan ring displays positional disorder [occupancy 0.563 (5):0.437 (5)]. The crystal structure is extended into a three-dimensional supramolecular architecture through intermolecular O—H⋯O and N—H⋯O hydrogen bonds with participation of the methanol solvent molecules.

Related literature

For a number of reduced or unreduced Schiff base complexes derived from taurine, see: Jiang et al. (2004 ▶, 2006 ▶); Li et al. (2005 ▶, 2006a ▶,b ▶, 2007a ▶,b ▶, 2008a ▶,b ▶); Liao et al. (2007 ▶); Zeng et al. (2003 ▶); Zhang et al. (2005 ▶). For the crystal stucture of a similar compound, 2-(2-pyridylmethylammonio) ethanesulfonate dihydrate, see: Li et al. (2006b ▶).

Experimental

Crystal data

C₇H₁₁NO₄S·CH₄O
M _r = 237.27
Monoclinic,
a = 10.729 (10) Å
b = 9.174 (8) Å
c = 11.270 (10) Å
β = 91.964 (10)°
V = 1108.6 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 294 K
0.39 × 0.23 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.894, T _max = 0.946
7971 measured reflections
2056 independent reflections
1675 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.109
S = 1.06
2056 reflections
131 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020005/at2791sup1.cif

e-65-o1459-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020005/at2791Isup2.hkl

e-65-o1459-Isup2.hkl^{(101.1KB, hkl)}

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
N1—H1A⋯O6ⁱ	0.90	1.92	2.767 (3)	156
N1—H1B⋯O2ⁱⁱ	0.90	2.15	2.940 (3)	147
N1—H1B⋯O2ⁱⁱⁱ	0.90	2.39	3.039 (3)	129
O6—H6⋯O4^iv	0.82	1.90	2.720 (3)	175

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 20471026) and the Natural Science Foundation of Henan Province (No. 0311021200).

supplementary crystallographic information

Comment

In the previous literatures, a number of reduced or unreduced Schiff base complexes derived from taurine have been reported (Jiang et al., 2004, 2006; Li et al., 2005, 2006a, 2007a,b, 2008a,b); Liao et al., 2007; Zeng et al., 2003; Zhang et al., 2005), and they have shown novel chain (Li et al., 2007b), cubical (Li et al., 2008a) and isomeric (Li et al., 2008b) structures except for the commonly seen mononuclear or binuclear compounds. Taurine, an amino acid containing sulfur, is indispensable to human beings and has important physiological functions. However, there have been sparse reports on the crystal structures of the corresponding free Schiff base ligands so far. In this paper, we report the crystal structure of a reduced Schiff base from taurine, (I) (Fig. 1).

The H atom of the sulfonic acid group is transferred to the amino N atom, forming the zwitterionic amino acid. This structure is completely similar to that of 2-(2-pyridylmethylammonio)ethanesulfonate dihydrate (Li et al., 2006b), where the H atom of the sulfonic acid group is also transferred to the amino N atom. The difference between them is that the furan ring here is positionally disordered. The two positions of furan ring have a dihedral angle of 180°. Other bond length and angles are in good agreement. Methanol molecules are involved in hydrogen bonds both as donors and acceptors, whereas ammonium acts only as a double donor (Table 1, Fig.2). Fig. 3 shows the crystal packing of (I), with hydrogen bonds as dashed lines in ac plane. The crystal of (I) is stabilized via these intermolecular hydrogen bonding interactions.

Experimental

Furan-2-carbaldehyde (0.96 g, 10 mmol) in MeOH (10 ml) was dropwise added to a solution of 2-aminoethanesulfonic acid (1.25 g, 10 mmol) in methanol (10 ml) containing KOH (0.56 g, 10 mmol). The yellow solution was stirred for about 2 h at room temperature prior to cooling in an ice bath. The intermediate Schiff base that formed was reduced with an excess of KBH₄ (0.79 g, 15 mmol). The yellow colour slowly discharged, and after 3 h the solution was adjusted with concentrated HCl to pH = 6.0. The resulting white solid was filtered off, washed with anhydrous methanol and diethyl ether. The obtained solid was dissolved in a ethanol-methanol mixture (1:1 v/v, 20 ml) and heated. When cooling, colourless granular-shaped crystals were obtained in a yield of 76%. Analysis, found: C 40.42, H 6.37, N 5.85, S 13.55%; C₈H₁₅NO₅S requires: C 40.50, H 6.33, N 5.91, S 13.50%. IR (KBr,ν, cm^-1): 768.7[γ(C═C-H)], 741.0(γCH₂); 1210.1, 1147.5, 1040.8(ν SO₃^-); 1607.6(ν C═C); 3428.4(ν O-H); 3098.8, 3021.3(ν N-H).