supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2009). E65, o1459    [ doi:10.1107/S1600536809020005 ]

2-(2-Furylmethylammonio)ethanesulfonate methanol solvate

Z.-X. Du and L.-Z. Wang

Abstract top

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.

Comment top

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.

Related literature top

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 top

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).

Refinement top

The H atoms bonded to C and N atoms were positioned geometrically with C—H distance of 0.93–0.97Å and N—H distances of 0.900 Å, and treated as riding atoms, with Uiso(H) = 1.2 or 1.5Ueq(C, N). The O—H hydrogen atom was located in a difference Fourier map and their positional and isotropic displacement parameters were refined; the applied restraint of the O—H distance wasere 0.820 Å, with Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), with displacement ellipsoids drawn at the 15% probability level.
[Figure 2] Fig. 2. The crystal packing of (I), showing hydrogen bonds as dashed lines in bc plane. H atoms on C atoms have been omitted.
[Figure 3] Fig. 3. The crystal packing of (I), showing hydrogen bonds as dashed lines in ac plane. H atoms on C atoms have been omitted.
2-(2-Furylmethylammonio)ethanesulfonate methanol solvate top
Crystal data top
C7H11NO4S·CH4OF(000) = 504
Mr = 237.27Dx = 1.422 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2624 reflections
a = 10.729 (10) Åθ = 2.9–26.3°
b = 9.174 (8) ŵ = 0.29 mm−1
c = 11.27 (1) ÅT = 294 K
β = 91.964 (10)°Granular, colourless
V = 1108.6 (17) Å30.39 × 0.23 × 0.19 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2056 independent reflections
Radiation source: fine-focus sealed tube1675 reflections with I > 2σ(I)
graphiteRint = 0.025
φ and ω scansθmax = 25.5°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→12
Tmin = 0.894, Tmax = 0.946k = −11→11
7971 measured reflectionsl = −13→13
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0435P)2 + 0.7985P]
where P = (Fo2 + 2Fc2)/3
2056 reflections(Δ/σ)max = 0.001
131 parametersΔρmax = 0.34 e Å−3
0 restraintsΔρmin = −0.31 e Å−3
Crystal data top
C7H11NO4S·CH4OV = 1108.6 (17) Å3
Mr = 237.27Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.729 (10) ŵ = 0.29 mm−1
b = 9.174 (8) ÅT = 294 K
c = 11.27 (1) Å0.39 × 0.23 × 0.19 mm
β = 91.964 (10)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2056 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1675 reflections with I > 2σ(I)
Tmin = 0.894, Tmax = 0.946Rint = 0.025
7971 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.109Δρmax = 0.34 e Å−3
S = 1.06Δρmin = −0.31 e Å−3
2056 reflectionsAbsolute structure: ?
131 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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
xyzUiso*/UeqOcc. (<1)
C10.15887 (16)0.40087 (19)1.03366 (18)0.0405 (5)0.563 (5)
C20.06631 (19)0.3384 (3)1.0916 (3)0.0555 (12)0.563 (5)
H20.01900.25921.06500.067*0.563 (5)
C30.0522 (3)0.4135 (4)1.2010 (2)0.0573 (19)0.563 (5)
H3−0.00470.39501.25950.069*0.563 (5)
C40.1395 (4)0.5157 (4)1.1997 (2)0.0619 (14)0.563 (5)
H40.15320.58251.26080.074*0.563 (5)
O10.2068 (3)0.5129 (2)1.0994 (2)0.0578 (9)0.563 (5)
O1'0.0572 (2)0.3157 (3)1.0589 (3)0.0578 (9)0.437 (5)
C1'0.15442 (16)0.40368 (19)1.03098 (18)0.0405 (5)0.437 (5)
C2'0.1761 (2)0.4964 (2)1.11987 (19)0.0555 (12)0.437 (5)
H2'0.23800.56751.12220.067*0.437 (5)
C3'0.0903 (3)0.4705 (4)1.2108 (2)0.0573 (19)0.437 (5)
H3'0.08320.51871.28280.069*0.437 (5)
C4'0.0230 (3)0.3605 (4)1.1674 (3)0.0619 (14)0.437 (5)
H4'−0.04180.31801.20780.074*0.437 (5)
C50.2106 (2)0.3793 (3)0.9149 (2)0.0455 (6)
H5A0.19110.45190.85460.055*
H5B0.16560.28960.89770.055*
C60.3852 (2)0.2834 (3)0.80019 (19)0.0389 (5)
H6A0.37400.36970.75120.047*
H6B0.33720.20490.76350.047*
C70.5215 (2)0.2421 (3)0.80631 (19)0.0385 (5)
H7A0.53160.15090.84910.046*
H7B0.56840.31650.84970.046*
N10.33791 (17)0.3130 (2)0.92132 (16)0.0366 (4)
H1A0.33550.22900.96240.044*
H1B0.39080.37390.96040.044*
O20.51984 (16)0.09645 (19)0.60803 (14)0.0475 (4)
O30.71519 (15)0.2028 (2)0.67984 (16)0.0547 (5)
O40.54838 (17)0.35667 (19)0.59804 (16)0.0541 (5)
S10.58193 (5)0.22288 (6)0.66156 (5)0.03640 (19)
C80.1847 (3)0.9586 (4)0.0474 (3)0.0661 (8)
H8A0.21580.91210.11870.099*
H8B0.15390.8861−0.00750.099*
H8C0.11841.02410.06600.099*
O60.2791 (2)1.0353 (2)−0.0028 (3)0.0841 (8)
H60.32740.9783−0.03340.126*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0334 (12)0.0395 (13)0.0489 (14)0.0009 (10)0.0043 (10)−0.0021 (11)
C20.054 (3)0.057 (3)0.056 (3)−0.021 (2)0.008 (2)−0.008 (2)
C30.053 (3)0.075 (5)0.0450 (19)0.007 (3)0.015 (2)−0.008 (3)
C40.065 (3)0.071 (3)0.051 (2)0.007 (3)0.016 (2)−0.007 (2)
O10.0508 (17)0.0572 (19)0.0662 (18)−0.0150 (15)0.0137 (14)−0.0136 (15)
O1'0.0508 (17)0.0572 (19)0.0662 (18)−0.0150 (15)0.0137 (14)−0.0136 (15)
C1'0.0334 (12)0.0395 (13)0.0489 (14)0.0009 (10)0.0043 (10)−0.0021 (11)
C2'0.054 (3)0.057 (3)0.056 (3)−0.021 (2)0.008 (2)−0.008 (2)
C3'0.053 (3)0.075 (5)0.0450 (19)0.007 (3)0.015 (2)−0.008 (3)
C4'0.065 (3)0.071 (3)0.051 (2)0.007 (3)0.016 (2)−0.007 (2)
C50.0374 (13)0.0510 (15)0.0482 (14)0.0053 (11)0.0042 (10)0.0031 (11)
C60.0411 (12)0.0455 (14)0.0302 (11)−0.0025 (10)0.0026 (9)−0.0033 (10)
C70.0417 (12)0.0456 (13)0.0282 (11)0.0026 (10)0.0018 (9)−0.0035 (10)
N10.0373 (10)0.0374 (10)0.0351 (10)−0.0016 (8)0.0036 (8)−0.0042 (8)
O20.0572 (11)0.0450 (10)0.0400 (9)−0.0009 (8)−0.0020 (8)−0.0118 (7)
O30.0383 (9)0.0731 (13)0.0530 (11)0.0057 (9)0.0040 (8)−0.0093 (9)
O40.0659 (12)0.0465 (11)0.0507 (10)0.0079 (9)0.0144 (9)0.0144 (8)
S10.0405 (3)0.0390 (3)0.0299 (3)0.0022 (2)0.0039 (2)−0.0017 (2)
C80.0571 (17)0.068 (2)0.074 (2)−0.0017 (15)0.0079 (15)0.0062 (16)
O60.0751 (15)0.0432 (11)0.137 (2)0.0023 (11)0.0486 (14)0.0045 (13)
Geometric parameters (Å, °) top
C1—C21.3365 (17)C5—H5A0.9700
C1—O11.3579 (17)C5—H5B0.9700
C1—C51.479 (3)C6—N11.497 (3)
C2—C31.4241 (19)C6—C71.510 (3)
C2—H20.9300C6—H6A0.9700
C3—C41.3255 (17)C6—H6B0.9700
C3—H30.9300C7—S11.785 (3)
C4—O11.3616 (18)C7—H7A0.9700
C4—H40.9300C7—H7B0.9700
O1'—C4'1.3528 (18)N1—H1A0.9000
O1'—C1'1.3636 (18)N1—H1B0.9000
C1'—C2'1.3288 (17)O2—S11.4579 (19)
C1'—C51.476 (3)O3—S11.449 (2)
C2'—C3'1.4210 (18)O4—S11.460 (2)
C2'—H2'0.9300C8—O61.371 (3)
C3'—C4'1.3242 (17)C8—H8A0.9600
C3'—H3'0.9300C8—H8B0.9600
C4'—H4'0.9300C8—H8C0.9600
C5—N11.494 (3)O6—H60.8200
C2—C1—O1109.4N1—C5—H5B96.4
C2—C1—C5133.87 (18)H5A—C5—H5B110.4
O1—C1—C5116.63 (19)N1—C6—C7111.21 (18)
C1—C2—C3108.6N1—C6—H6A109.4
C1—C2—H2125.7C7—C6—H6A109.4
C3—C2—H2125.7N1—C6—H6B109.4
C4—C3—C2103.7C7—C6—H6B109.4
C4—C3—H3128.2H6A—C6—H6B108.0
C2—C3—H3128.2C6—C7—S1111.39 (15)
C3—C4—O1113.0C6—C7—H7A109.3
C3—C4—H4123.5S1—C7—H7A109.3
O1—C4—H4123.5C6—C7—H7B109.3
C1—O1—C4105.4S1—C7—H7B109.3
C4'—O1'—C1'105.2H7A—C7—H7B108.0
C2'—C1'—O1'108.7C5—N1—C6111.57 (17)
C2'—C1'—C5134.33 (19)C5—N1—H1A109.3
O1'—C1'—C5116.98 (18)C6—N1—H1A109.3
C1'—C2'—C3'109.6C5—N1—H1B109.3
C1'—C2'—H2'125.2C6—N1—H1B109.3
C3'—C2'—H2'125.2H1A—N1—H1B108.0
C4'—C3'—C2'102.7O3—S1—O2113.08 (11)
C4'—C3'—H3'128.6O3—S1—O4113.72 (12)
C2'—C3'—H3'128.6O2—S1—O4111.38 (12)
C3'—C4'—O1'113.8O3—S1—C7105.68 (11)
C3'—C4'—H4'123.1O2—S1—C7106.36 (11)
O1'—C4'—H4'123.1O4—S1—C7105.89 (11)
C1'—C5—N1114.81 (19)O6—C8—H8A109.5
C1—C5—N1112.44 (19)O6—C8—H8B109.5
C1'—C5—H5A115.6H8A—C8—H8B109.5
C1—C5—H5A117.6O6—C8—H8C109.5
N1—C5—H5A119.2H8A—C8—H8C109.5
C1'—C5—H5B95.2H8B—C8—H8C109.5
C1—C5—H5B95.5C8—O6—H6109.5
O1—C1—C2—C30.2O1'—C1'—C5—C1−105.89 (12)
C5—C1—C2—C3−175.1 (3)C2'—C1'—C5—N171.6 (3)
C1—C2—C3—C4−0.4O1'—C1'—C5—N1−108.9 (2)
C2—C3—C4—O10.4C2—C1—C5—C1'72.75 (19)
C2—C1—O1—C40.0O1—C1—C5—C1'−102.27 (13)
C5—C1—O1—C4176.2 (2)C2—C1—C5—N1−110.2 (2)
C3—C4—O1—C1−0.3O1—C1—C5—N174.7 (2)
C4'—O1'—C1'—C2'0.0N1—C6—C7—S1−174.72 (15)
C4'—O1'—C1'—C5−179.6 (2)C1'—C5—N1—C6176.54 (19)
O1'—C1'—C2'—C3'−0.2C1—C5—N1—C6176.41 (18)
C5—C1'—C2'—C3'179.3 (3)C7—C6—N1—C5169.8 (2)
C1'—C2'—C3'—C4'0.3C6—C7—S1—O3172.61 (17)
C2'—C3'—C4'—O1'−0.3C6—C7—S1—O2−66.9 (2)
C1'—O1'—C4'—C3'0.2C6—C7—S1—O451.7 (2)
C2'—C1'—C5—C174.6 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O6i0.901.922.767 (3)156
N1—H1B···O2ii0.902.152.940 (3)147
N1—H1B···O2iii0.902.393.039 (3)129
O6—H6···O4iv0.821.902.720 (3)175
Symmetry codes: (i) x, y−1, z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y+1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O6i0.901.922.767 (3)156
N1—H1B···O2ii0.902.152.940 (3)147
N1—H1B···O2iii0.902.393.039 (3)129
O6—H6···O4iv0.821.902.720 (3)175
Symmetry codes: (i) x, y−1, z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y+1/2, −z+1/2.
Acknowledgements top

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

references
References top

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Jiang, Y.-M., Li, J.-M., Xie, F.-Q. & Wang, Y.-F. (2006). Chin. J. Struct. Chem. 25, 767–770.

Jiang, Y.-M., Zeng, J.-L. & Yu, K.-B. (2004). Acta Cryst. C60, m543–m545.

Li, J.-X., Jiang, Y.-M. & Chen, M.-J. (2008a). J. Coord. Chem. 61, 1765–1773.

Li, J.-X., Jiang, Y.-M. & Li, H.-Y. (2006a). Acta Cryst. E62, m2984–m2986.

Li, J.-X., Jiang, Y.-M. & Lian, B.-R. (2008b). J. Chem. Crystallogr. 38, 711–715.

Li, J.-X., Jiang, Y.-M. & Liao, B.-L. (2006b). Acta Cryst. E62, o5609–o5611.

Li, J.-X., Jiang, Y.-M. & Wang, J.-G. (2007a). Acta Cryst. E63, m213–m215.

Li, J.-X., Jiang, Y.-M. & Wang, J.-G. (2007b). Acta Cryst. E63, m601–m603.

Li, J.-M., Jiang, Y.-M., Wang, Y.-F. & Liang, D.-W. (2005). Acta Cryst. E61, m2160–m2162.

Liao, B.-L., Li, J.-X. & Jiang, Y.-M. (2007). Acta Cryst. E63, m1974.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Zeng, J.-L., Jiang, Y.-M. & Yu, K.-B. (2003). Acta Cryst. E59, m1137–m1139.

Zhang, S.-H., Jiang, Y.-M. & Yu, K.-B. (2005). Acta Cryst. E61, m209–m211.