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Crystal structure of potassium (1R)-d-ribit-1-yl-sulfonate.

Haines AH, Hughes DL - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: The title compound, K(+)·C5H11O8S(-) [systematic name: potassium (1R,2R,3R,4R)-1,2,3,4,5-penta-hydroxy-pentane-1-sulfonate], formed by reaction of d-ribose with potassium hydrogen sulfite in water, crystallizes as colourless plates.The anion has an open-chain structure in which the S atom and the C atoms of the sugar chain, excepting that of the hy-droxy-methyl group, form an essentially all-trans chain; the C atom of the hy-droxy-methyl group lies in a gauche relationship with the three contiguous C atoms.Through complex cation coordination (through seven oxygen atoms of six different anions) and inter-molecular O-H⋯O hydrogen bonding, a three-dimensional bonding network exists in the crystal structure.

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Affiliation: School of Chemistry, University of East Anglia, Norwich NR4 7TJ, England.

ABSTRACT
The title compound, K(+)·C5H11O8S(-) [systematic name: potassium (1R,2R,3R,4R)-1,2,3,4,5-penta-hydroxy-pentane-1-sulfonate], formed by reaction of d-ribose with potassium hydrogen sulfite in water, crystallizes as colourless plates. The anion has an open-chain structure in which the S atom and the C atoms of the sugar chain, excepting that of the hy-droxy-methyl group, form an essentially all-trans chain; the C atom of the hy-droxy-methyl group lies in a gauche relationship with the three contiguous C atoms. Through complex cation coordination (through seven oxygen atoms of six different anions) and inter-molecular O-H⋯O hydrogen bonding, a three-dimensional bonding network exists in the crystal structure.

No MeSH data available.


Related in: MedlinePlus

View of a mol­ecule of potassium (1R)-d-ribit-1-yl­sulfonate, indicating the atom-numbering scheme, showing the hydrogen bonds (dashed lines) from the anion and the coordination pattern around the potassium cation. Displacement ellipsoids are drawn at the 50% probability level. Symmetry codes: (i) −x, y + , −z + 1; (ii) x − 1, y, z − 1; (iii) −x + 1, y + , −z + 1; (iv) −x, y + , −z; (v) x, y, z − 1; (vi) x, y, z + 1; (vii) −x, y − , −z; (viii) x + 1, y, z + 1; (ix) −x + 1, y − , −z + 1; (x) −x, y − , −z + 1; (xi) x − 1, y, z; (xii) x + 1, y, z.
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fig1: View of a mol­ecule of potassium (1R)-d-ribit-1-yl­sulfonate, indicating the atom-numbering scheme, showing the hydrogen bonds (dashed lines) from the anion and the coordination pattern around the potassium cation. Displacement ellipsoids are drawn at the 50% probability level. Symmetry codes: (i) −x, y + , −z + 1; (ii) x − 1, y, z − 1; (iii) −x + 1, y + , −z + 1; (iv) −x, y + , −z; (v) x, y, z − 1; (vi) x, y, z + 1; (vii) −x, y − , −z; (viii) x + 1, y, z + 1; (ix) −x + 1, y − , −z + 1; (x) −x, y − , −z + 1; (xi) x − 1, y, z; (xii) x + 1, y, z.

Mentions: The anion has an open-chain structure in which carbons C1 to C4 together with O4, S and O13 form an essentially all-trans chain (Fig. 1 ▶), with the newly formed chiral centre at C1 having the R-configuration. The systematic name for the salt is potassium (1R,2R,3R,4R)-1,2,3,4,5-penta­hydroxy­pentane-1-sulfonate. The torsion angle C2—C3—C4—C5 is indicative of a gauche conformation with C5 pointing out of the all-trans chain. All of the hydroxyl groups form O—H⋯O hydrogen bonds and all, except for the hydrogen bond from O2, have short H⋯O distances with O—H⋯O angles not far from linear (Table 1 ▶); the O2 hydrogen bond is towards the upper limit in terms of H⋯O distance with an angle of 132 (2)° at H2O. The potassium ions are seven-coordinate with K—O bonds to six separate anions; the K—O bond lengths lie in the range of 2.7383 (10) to 3.0085 (11) and are arranged in an approximately penta­gonal–bipyramidal form with O4 and O4iv as the apical atoms. This is shown in Fig. 2 ▶, a view approximately along the a axis, indicating the hydrogen-bonding contacts and the K—O coordinate bonds. Potassium ions can show various coordination numbers in related coordination environments: in the d-galactose bis­ulfite (Haines & Hughes, 2010 ▶), d-glucose bis­ulfite (Cole et al. 2001 ▶; Haines & Hughes, 2012 ▶) and de­hydro-l-ascorbic acid bis­ulfite (Haines & Hughes, 2013 ▶) adducts, the potassium ion is, respectively, six-, seven-, and eight-coordinate.


Crystal structure of potassium (1R)-d-ribit-1-yl-sulfonate.

Haines AH, Hughes DL - Acta Crystallogr Sect E Struct Rep Online (2014)

View of a mol­ecule of potassium (1R)-d-ribit-1-yl­sulfonate, indicating the atom-numbering scheme, showing the hydrogen bonds (dashed lines) from the anion and the coordination pattern around the potassium cation. Displacement ellipsoids are drawn at the 50% probability level. Symmetry codes: (i) −x, y + , −z + 1; (ii) x − 1, y, z − 1; (iii) −x + 1, y + , −z + 1; (iv) −x, y + , −z; (v) x, y, z − 1; (vi) x, y, z + 1; (vii) −x, y − , −z; (viii) x + 1, y, z + 1; (ix) −x + 1, y − , −z + 1; (x) −x, y − , −z + 1; (xi) x − 1, y, z; (xii) x + 1, y, z.
© Copyright Policy - open-access
Related In: Results  -  Collection

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Show All Figures
getmorefigures.php?uid=PMC4257350&req=5

fig1: View of a mol­ecule of potassium (1R)-d-ribit-1-yl­sulfonate, indicating the atom-numbering scheme, showing the hydrogen bonds (dashed lines) from the anion and the coordination pattern around the potassium cation. Displacement ellipsoids are drawn at the 50% probability level. Symmetry codes: (i) −x, y + , −z + 1; (ii) x − 1, y, z − 1; (iii) −x + 1, y + , −z + 1; (iv) −x, y + , −z; (v) x, y, z − 1; (vi) x, y, z + 1; (vii) −x, y − , −z; (viii) x + 1, y, z + 1; (ix) −x + 1, y − , −z + 1; (x) −x, y − , −z + 1; (xi) x − 1, y, z; (xii) x + 1, y, z.
Mentions: The anion has an open-chain structure in which carbons C1 to C4 together with O4, S and O13 form an essentially all-trans chain (Fig. 1 ▶), with the newly formed chiral centre at C1 having the R-configuration. The systematic name for the salt is potassium (1R,2R,3R,4R)-1,2,3,4,5-penta­hydroxy­pentane-1-sulfonate. The torsion angle C2—C3—C4—C5 is indicative of a gauche conformation with C5 pointing out of the all-trans chain. All of the hydroxyl groups form O—H⋯O hydrogen bonds and all, except for the hydrogen bond from O2, have short H⋯O distances with O—H⋯O angles not far from linear (Table 1 ▶); the O2 hydrogen bond is towards the upper limit in terms of H⋯O distance with an angle of 132 (2)° at H2O. The potassium ions are seven-coordinate with K—O bonds to six separate anions; the K—O bond lengths lie in the range of 2.7383 (10) to 3.0085 (11) and are arranged in an approximately penta­gonal–bipyramidal form with O4 and O4iv as the apical atoms. This is shown in Fig. 2 ▶, a view approximately along the a axis, indicating the hydrogen-bonding contacts and the K—O coordinate bonds. Potassium ions can show various coordination numbers in related coordination environments: in the d-galactose bis­ulfite (Haines & Hughes, 2010 ▶), d-glucose bis­ulfite (Cole et al. 2001 ▶; Haines & Hughes, 2012 ▶) and de­hydro-l-ascorbic acid bis­ulfite (Haines & Hughes, 2013 ▶) adducts, the potassium ion is, respectively, six-, seven-, and eight-coordinate.

Bottom Line: The title compound, K(+)·C5H11O8S(-) [systematic name: potassium (1R,2R,3R,4R)-1,2,3,4,5-penta-hydroxy-pentane-1-sulfonate], formed by reaction of d-ribose with potassium hydrogen sulfite in water, crystallizes as colourless plates.The anion has an open-chain structure in which the S atom and the C atoms of the sugar chain, excepting that of the hy-droxy-methyl group, form an essentially all-trans chain; the C atom of the hy-droxy-methyl group lies in a gauche relationship with the three contiguous C atoms.Through complex cation coordination (through seven oxygen atoms of six different anions) and inter-molecular O-H⋯O hydrogen bonding, a three-dimensional bonding network exists in the crystal structure.

View Article: PubMed Central - HTML - PubMed

Affiliation: School of Chemistry, University of East Anglia, Norwich NR4 7TJ, England.

ABSTRACT
The title compound, K(+)·C5H11O8S(-) [systematic name: potassium (1R,2R,3R,4R)-1,2,3,4,5-penta-hydroxy-pentane-1-sulfonate], formed by reaction of d-ribose with potassium hydrogen sulfite in water, crystallizes as colourless plates. The anion has an open-chain structure in which the S atom and the C atoms of the sugar chain, excepting that of the hy-droxy-methyl group, form an essentially all-trans chain; the C atom of the hy-droxy-methyl group lies in a gauche relationship with the three contiguous C atoms. Through complex cation coordination (through seven oxygen atoms of six different anions) and inter-molecular O-H⋯O hydrogen bonding, a three-dimensional bonding network exists in the crystal structure.

No MeSH data available.


Related in: MedlinePlus