research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Crystal structure of potassium (1R)-D-ribit-1-yl­sulfonate

aSchool of Chemistry, University of East Anglia, Norwich NR4 7TJ, England
*Correspondence e-mail: a.haines@uea.ac.uk, d.l.hughes@uea.ac.uk

Edited by J. Simpson, University of Otago, New Zealand (Received 9 September 2014; accepted 15 October 2014; online 24 October 2014)

The title compound, K+·C5H11O8S [systematic name: potassium (1R,2R,3R,4R)-1,2,3,4,5-penta­hydroxy­pentane-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 hy­droxy­methyl group, form an essentially all-trans chain; the C atom of the hy­droxy­methyl 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 inter­molecular O—H⋯O hydrogen bonding, a three-dimensional bonding network exists in the crystal structure.

1. Chemical context

Addition compounds formed between carbonyl compounds and the bis­ulfite anion have found use in purification of liquid aldehydes when, as is often the case, the adduct is crystalline, in facilitating cyano­hydrin formation, and also in conferring required water solubility to certain hydro­phobic compounds (Clayden et al., 2012[Clayden, J. P., Greeves, N. & Warren, S. (2012). Organic Chemistry, 2nd ed., pp. 138-140. Oxford University Press.]). Less well known is the fact that aldoses, despite existing preferentially in the hemiacetal form, can react with the bis­ulfite anion to give open-chain adducts which, as chiral hy­droxy­sulfonic acids, have potentially useful but largely unexplored applications in synthesis. The know­ledge of such compounds was initially centred on the their possible role in the stabilization of food stuffs (Gehman & Osman, 1954[Gehman, H. & Osman, E. M. (1954). Adv. Food Res. 5, 53-96.]) (note: nearly all wines are labelled `contains sulfites') and evidence for their acyclic nature was first provided by Ingles (1959[Ingles, D. L. (1959). Aust. J. Chem. 12, 97-101.]), who prepared such adducts from D-glucose, D-galactose, D-mannose, L-arabinose and L-rhamnose. However, conclusive proof for their acyclic structure awaited X-ray studies, initially by Cole et al. (2001[Cole, E. R., Craig, D. C., Fitzpatrick, L. J., Hibbert, D. B. & Stevens, J. D. (2001). Carbohydr. Res. 335, 1-10.]) who reported the crystal structures of D-glucose- and D-mannose-derived potassium sulfonates, and later we studied the sodium sulfon­ate derived from D-glucose (Haines & Hughes, 2012[Haines, A. H. & Hughes, D. L. (2012). Acta Cryst. E68, m377-m378.]) and the potassium sulfonate from D-galactose (Haines & Hughes, 2010[Haines, A. H. & Hughes, D. L. (2010). Carbohydr. Res. 345, 2705-2708.]) by X-ray crystallography. The crystal structure of the potassium bis­ulfite adduct of de­hydro-L-ascorbic acid, first prepared by Ingles (1959[Ingles, D. L. (1959). Aust. J. Chem. 12, 97-101.]), has also been reported (Haines & Hughes, 2013[Haines, A. H. & Hughes, D. L. (2013). Acta Cryst. E69, m7-m8.]).

C-Sulfonic acid derivatives of carbohydrates have been prepared at non-glycosidic atoms by the radical-mediated addition of the bis­ulfite ion to methyl 6-de­oxy­hexo­pyran­osid-5-enes (e.g. in the synthesis of 6-sulfoquinovose; Lehmann & Benson, 1964[Lehmann, J. & Benson, A. A. (1964). J. Am. Chem. Soc. 86, 4469-4472.]), by tri­fluoro­methane­sulfonate-mediated nucleo­philic displacement reactions with the bis­ulfite ion (Lipták et al., 2004[Lipták, A., Balla, E., Jánossy, L., Sajtos, F. & Szilágyi, L. (2004). Tetrahedron Lett. 45, 839-842.]) or by oxidation of a thio­acetyl substituent on a protected glycose (Lipták et al., 2004[Lipták, A., Balla, E., Jánossy, L., Sajtos, F. & Szilágyi, L. (2004). Tetrahedron Lett. 45, 839-842.]). Although oxidation of C1-thio­esters of protected aldoses affords a route to C1-sulfonic acids, the facile preparation of the bis­ulfite adducts of certain aldoses provides an attractive route to chiral hy­droxy­sulfonic acids, which merit further exploration as possible synthetic inter­mediates.

[Scheme 1]

Preparation of aldose adducts requires reaction at high concentrations, with the bis­ulfite anion produced in situ by hydrolysis of the corresponding metabisulfite. Obtaining suitable material for X-ray crystallography is not always straightforward, either in the initiation of crystallization or in isolating crystals of suitable quality. We report here the preparation in crystalline form of the hitherto unknown potassium bis­ulfite adduct from D-ribose, (1), and its solid-state structure.

2. Structural commentary

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[link]), 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[link]); 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[link], 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[Haines, A. H. & Hughes, D. L. (2010). Carbohydr. Res. 345, 2705-2708.]), D-glucose bis­ulfite (Cole et al. 2001[Cole, E. R., Craig, D. C., Fitzpatrick, L. J., Hibbert, D. B. & Stevens, J. D. (2001). Carbohydr. Res. 335, 1-10.]; Haines & Hughes, 2012[Haines, A. H. & Hughes, D. L. (2012). Acta Cryst. E68, m377-m378.]) and de­hydro-L-ascorbic acid bis­ulfite (Haines & Hughes, 2013[Haines, A. H. & Hughes, D. L. (2013). Acta Cryst. E69, m7-m8.]) adducts, the potassium ion is, respectively, six-, seven-, and eight-coordinate.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1O⋯O12i 0.83 (3) 1.89 (3) 2.6980 (14) 165 (2)
O2—H2O⋯O5ii 0.77 (2) 2.34 (3) 2.9111 (14) 132 (2)
O3—H3O⋯O2iii 0.79 (2) 2.10 (2) 2.8596 (14) 162 (2)
O4—H4O⋯O5i 0.83 (3) 1.95 (3) 2.7779 (14) 175 (3)
O5—H5O⋯O13iv 0.88 (2) 1.99 (2) 2.8432 (14) 161.7 (18)
Symmetry codes: (i) x-1, y, z; (ii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iii) [-x, y-{\script{1\over 2}}, -z+1]; (iv) x, y, z-1.
[Figure 1]
Figure 1
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 + [{1\over 2}], −z + 1; (ii) x − 1, y, z − 1; (iii) −x + 1, y + [{1\over 2}], −z + 1; (iv) −x, y + [{1\over 2}], −z; (v) x, y, z − 1; (vi) x, y, z + 1; (vii) −x, y − [{1\over 2}], −z; (viii) x + 1, y, z + 1; (ix) −x + 1, y − [{1\over 2}], −z + 1; (x) −x, y − [{1\over 2}], −z + 1; (xi) x − 1, y, z; (xii) x + 1, y, z.
[Figure 2]
Figure 2
View approximately along the a axis, showing the hydrogen-bonding contacts and all the K—O coordination bonds. Symmetry codes as in Fig. 1[link].

Fig. 3[link], a view down the c axis, indicates the parallel alignment of the open-chain ions and Fig. 4[link] illustrates a section parallel to the ab plane showing the linking of the potassium ions in that plane.

[Figure 3]
Figure 3
View along the c axis, showing the parallel alignment of the open-chain ions and the inter­ionic inter­actions. Symmetry codes as in Fig. 1[link].
[Figure 4]
Figure 4
A section parallel to the ab plane around z = 0, showing the linking of the potassium ions in that plane; the connections are made through coordination bonds involving the sulfonate groups and the hydroxyl groups of O1 and O4. Symmetry codes as in Fig. 1[link].

High-resolution mass spectrometry in negative-ion mode identified the anion at m/z 231.0187 but the base peak was at m/z 213.0082, representing loss of water from the parent ion. A large peak was also observed at 299.0987 for C10H19O10, which corresponds to the ion of the product formed by reaction between (1) and D-ribose with displacement of potassium bis­ulfite; in the aqueous solution used for MS analysis, some decomposition of (1) to afford D-ribose undoubtedly occurs and this is supported by NMR data on the aqueous solution reported below.

The 1H NMR spectrum of (1) in D2O indicates considerable stability of the adduct in aqueous solution, with the species α-furan­ose, β-furan­ose, β-pyran­ose, α-pyran­ose, and bis­ulfite adduct, identified by their H-1 resonances, present in the % ratios of 3.6:6.2:10.9:5.1:74.2, which changed only marginally after 18 days. A complete assignment of the spectrum for (1) and consideration of derived coupling constants indicated overall similarity of the conformation in the crystalline state and in solution. Notably, J1,2 was close to zero and assuming Newman projection angles of 120° and using measured torsional angles, a Karplus relationship suggests a value of about 0.3 Hz. The value J2,3 = 8.6 Hz is in accord with an anti­periplanar arrangement of H2 and H3, whereas J3,4 = 4.6 Hz is consistent with the synclinal disposition of H3 and H4, resulting from a gauche arrangement for C2—C3—C4—C5.

The 13C NMR spectrum confirmed the presence of the four ring forms of D-ribose as indicated by their C1 signals and the major peak for C1 in the adduct at δC 82.25 was accompanied by a much smaller peak at δC 84.19 which suggests the presence in solution of the diastereoisomer of (1) having the S-configuration at C1.

3. Supra­molecular features

A three-dimensional network exists in the crystal structure through the coordination of each potassium cation (overall seven coordinate) to six different ribose bis­ulfite residues and through extensive hydrogen bonding between hy­droxy hydrogens and oxygen atoms of hydroxyl groups or those on sulfur. Although the addition of the sulfite anion to C1 of the ribose moiety can theoretically afford two isomers, only the R-diastereomer was present in the crystal studied.

4. Synthesis, crystallization and spectroscopic analysis

Water (0.5 ml) was added to potassium metabisulfite (0.37 g), which did not dissolve completely even on warming but which appeared to change its crystalline form as it underwent hydrolysis to yield potassium hydrogen sulfite. To this suspension was added a solution of D-ribose (0.5 g) in water (0.35 ml), leading to immediate and complete solution of the reaction mixture. Seed crystals were obtained by complete evaporation of a small proportion of the solution, and these were added to the bulk of the solution which was then stored at 277 K, leading to the formation of large, well-separated crystals. The syrupy nature of the mother liquor required its removal with a Pasteur pipette, after which the crystals were dried by pressing between filter papers, to give potassium (1R)-D-ribit-1-yl­sulfonate, m.p. 396–400 K (with decomposition); [α]D −6.1 (15 min.) (c, 0.81 in 9:1 H2O:HOAc).

1H NMR (D2O, 400 MHz, reference Me3COH at δH 1.24): δ 5.37 (d, J1,2 = 3.8 Hz, H-1 of α-furan­ose), 5.24 (d, J1,2 = 1.8 Hz, H-1 of β-furan­ose), 4.92 (d, J1,2 = 6.5 Hz, H-1 of β-pyran­ose), 4.85 (d, J1,2 = 1.8 Hz, H-1 of α-pyran­ose); signals for acyclic sulfonate: δH 4.67 (s, H-1), 4.18 (d, J2,3 = 8.6 Hz, H-2), 3.94 (ddd, J3,4 = 4.6, J4,5a = 3.1, J4,5b = 7.4 Hz, H-4), 3.82 (dd, J5a,5b = −11.9 Hz, H-5a), 3.77 (dd, H-3), 3.69 (dd, H-5b). 13C NMR (D2O, 100 MHz, reference Me3COH at δC 30.29): δ 101.55 (C1, β-furan­ose), 96.89 (C1, α-furan­ose), 94.43 (C1, β-pyran­ose), 94.15 (C1, α-pyran­ose); signals for adduct: 82.25 (C1), 73.23, 71.88, 70.61 (C2, C3, C4), 62.56 (C5). A small but significant peak was observed at δC 84.19.

Integration of the various signals for H-1 in the 1H NMR spectrum, 5 minutes after sample dissolution, indicated the species α-furan­ose, β-furan­ose, β-pyran­ose, α-pyran­ose, bis­ulfite adduct were present in the % ratios of 3.6:6.2:10.9:5.1:74.2. Re-measurement after 18 days, gave these % ratios as 1.5:2.6:16.2:8.7:70.9.

HRESMS (negative-ion mode, measured in H2O/MeOH, solution) gave an expected peak at m/z 231.0187 ([C5H11O8S]), the base peak at 213.0082 ([C5H11O8S−H2O]) and a significant peak at 299.0987 ([C10H19O10]). The last peak corresponds to the ion of the product formed by reaction between the bis­ulfite adduct and D-ribose with displacement of potassium bis­ulfite.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Hydrogen atoms bound to the carbon atoms were included in idealized positions (with C—H distances of 0.98 and 0.97 Å for methyne and methylene groups respectively) and their Uiso values were set to ride on the Ueq values of the parent atoms; hydroxyl hydrogen atoms were located in difference maps and were refined freely.

Table 2
Experimental details

Crystal data
Chemical formula K+·C5H11O8S
Mr 270.30
Crystal system, space group Monoclinic, P21
Temperature (K) 140
a, b, c (Å) 5.36167 (8), 9.01474 (14), 9.78623 (17)
β (°) 102.8138 (16)
V3) 461.23 (1)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.83
Crystal size (mm) 0.22 × 0.22 × 0.12
 
Data collection
Diffractometer Oxford Diffraction Xcalibur 3/Sapphire3 CCD
Absorption correction Multi-scan (CrysAlis PRO; Oxford Diffraction, 2011[Oxford Diffraction (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.])
Tmin, Tmax 0.874, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections 8864, 2690, 2632
Rint 0.023
(sin θ/λ)max−1) 0.703
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.021, 0.053, 1.05
No. of reflections 2690
No. of parameters 156
No. of restraints 1
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.43, −0.22
Absolute structure Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1264 Friedel pairs
Absolute structure parameter −0.01 (3)
Computer programs: CrysAlis PRO (Oxford Diffraction, 2011[Oxford Diffraction (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]), SHELXS97 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]), ORTEP-3 for Windows and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Chemical context top

Addition compounds formed between carbonyl compounds and the bis­ulfite anion have found use in purification of liquid aldehydes when, as is often the case, the adduct is crystalline, in facilitating cyano­hydrin formation, and also in conferring required water solubility to certain hydro­phobic compounds (Clayden et al., 2012). Less well known is the fact that aldoses, despite existing preferentially in the hemiacetal form, can react with the bis­ulfite anion to give open-chain adducts which, as chiral hy­droxy­sulfonic acids, have potentially useful but largely unexplored applications in synthesis. The knowledge of such compounds was initially centred on the their possible role in the stabilization of food stuffs (Gehman & Osman, 1954) (note: nearly all wines are labelled `contains sulfites') and evidence for their acyclic nature was first provided by Ingles (1959), who prepared such adducts from D-glucose, D-galactose, D-mannose, L-arabinose and L-rhamnose. However, conclusive proof for their acyclic structure awaited X-ray studies, initially by Cole et al. (2001) who reported the solid-state structures of D-glucose- and D-mannose-derived potassium sulfonates, and later we studied the sodium sulfonate derived from D-glucose (Haines & Hughes, 2012) and the potassium sulfonate from D-galactose (Haines & Hughes, 2010) by X-ray crystallography. The solid-state structure of the potassium bis­ulfite adduct of de­hydro-L-ascorbic acid, first prepared by Ingles (1959), has also been reported (Haines & Hughes, 2013).

C-Sulfonic acid derivatives of carbohydrates have been prepared at non-glycosidic centres by the radical-mediated addition of the bis­ulfite ion to methyl 6-de­oxy­hexo­pyran­osid-5-enes (e.g. in the synthesis of 6-sulfoquinovose; Lehmann & Benson, 1964), by tri­fluoro­methane­sulfonate-mediated nucleophilic displacement reactions with the bis­ulfite ion (Lipták et al., 2004) or by oxidation of a thio­acetyl substituent on a protected glycose (Lipták et al., 2004). Although oxidation of C1-thio­esters of protected aldoses affords a route to C1-sulfonic acids, the facile preparation of the bis­ulfite adducts of certain aldoses provides an attractive route to chiral hy­droxy­sulfonic acids, which merit further exploration as possible synthetic inter­mediates.

Preparation of aldose adducts requires reaction at high concentrations, with the bis­ulfite anion produced in situ by hydrolysis of the corresponding metabisulfite. Obtaining suitable material for X-ray crystallography is not always straightforward, either in the initiation of crystallization or in isolating crystals of suitable quality. We report here the preparation in crystalline form of the hitherto unknown potassium bis­ulfite adduct from D-ribose, (1), and its solid-state structure.

Structural commentary top

\ Addition of a concentrated solution of D-ribose to a half-molar equivalent of potassium metabisulfite, suspended in a small amount of water, led to immediate solution and after seeding with material obtained by evaporation of a small amount of solution to dryness, large crystals of compound (1) gradually formed on storage at 277 K for several days, with m.p. 296–400 K (with decomposition).

X-ray analysis showed an anion with 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 gauche 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 a catholic taste in such coordinated situations – 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.

Fig. 3, a view down the c axis, indicates the parallel alignment of the open-chain ions and Fig. 4 illustrates a section parallel to the ab plane showing the linking of the potassium ions in that plane. Tables containing atomic parameters, molecular dimensions (bond lengths and angles and torsion angles) are included in the Supporting Information.

Spectroscopic investigations top

High-resolution mass spectrometry in negative-ion mode identified the anion at m/z 231.0187 but the base peak was at m/z 213.0082, representing loss of water from the parent ion. A large peak was also observed at 299.0987 for C10H19O10, which corresponds to the ion of the product formed by reaction between (1) and D-ribose with displacement of potassium bis­ulfite; in the aqueous solution used for MS analysis, some decomposition of (1) to afford D-ribose undoubtedly occurs and this is supported by NMR data on the aqueous solution reported below.

The 1H NMR spectrum of (1) in D2O indicates considerable stability of the adduct in aqueous solution, with the species α-furan­ose, β-furan­ose, β-pyran­ose, α-pyran­ose, and bis­ulfite adduct, identified by their H-1 resonances, present in the % ratios of 3.6:6.2:10.9:5.1:74.2, which changed only marginally after 18 days. A complete assignment of the spectrum for (1) and consideration of derived coupling constants indicated overall similarity of the conformation in the crystalline state and in solution. Notably, J1,2 was close to zero and assuming Newman projection angles of 120° and using measured torsional angles, a Karplus relationship suggests a value of about 0.3 Hz. The value J2,3 = 8.6 Hz is in accord with an anti­periplanar arrangement of H2 and H3, whereas J3,4 = 4.6 Hz is consistent with the synclinal disposition of H3 and H4, resulting from a gauche arrangement for C2—C3—C4—C5.

The 13C NMR spectrum confirmed the presence of the four ring forms of D-ribose as indicated by their C1 signals and the major peak for C1 in the adduct at δC 82.25 was accompanied by a much smaller peak at δC 84.19 which suggests the presence in solution of the diastereoisomer of (1) having the (S)-configuration at C1.

Supra­molecular features top

A three-dimensional network exists in the crystal structure through the coordination of each potassium cation (overall seven coordinate) to six different ribose bis­ulfite residues and through extensive hydrogen bonding between hy­droxy hydrogens and oxygen atoms of hydroxyl groups or those on sulfur. Although the addition of the sulfite anion to C1 of the ribose moiety can theoretically afford two isomers, only the R-diastereomer is present in the crystal studied.

Synthesis and crystallization of compound (1) top

Water (0.5 ml) was added to potassium metabisulfite (0.37 g), which did not dissolve completely even on warming but which appeared to change its crystalline form as it underwent hydrolysis to yield potassium hydrogen sulfite. To this suspension was added a solution of D-ribose (0.5 g) in water (0.35 ml), leading to immediate and complete solution of the reaction mixture. Seed crystals were obtained by complete evaporation of a small proportion of the solution, and these were added to the bulk of the solution which was then stored at 277 K, leading to the formation of large, well-separated crystals. The syrupy nature of the mother liquor required its removal with a Pasteur pipette, after which the crystals were dried by pressing between filter papers, to give potassium (1R)-D-ribit-1-yl­sulfonate, m.p. 296–400 K (with decomposition); [α]D -6.1 (15 min.) (c, 0.81 in 9:1 H2O:HOAc). 1H NMR (D2O, 400 MHz, reference Me3COH at δH 1.24): δ 5.37 (d, J1,2 = 3.8 Hz, H-1 of α-furan­ose), 5.24 (d, J1,2 = 1.8 Hz, H-1 of β-furan­ose), 4.92 (d, J1,2 = 6.5 Hz, H-1 of β-pyran­ose), 4.85 (d, J1,2 = 1.8 Hz, H-1 of α-pyran­ose); signals for acyclic sulfonate: δH 4.67 (s, H-1), 4.18 (d, J2,3 = 8.6 Hz, H-2), 3.94 (ddd, J3,4 = 4.6, J4,5a = 3.1, J4,5b = 7.4 Hz, H-4), 3.82 (dd, J5a,5b = -11.9 Hz, H-5a), 3.77 (dd, H-3), 3.69 (dd, H-5b). 13C NMR (D2O, 100 MHz, reference Me3COH at δC 30.29): δ 101.55 (C1, β-furan­ose), 96.89 (C1, α-furan­ose), 94.43 (C1, β-pyran­ose), 94.15 (C1, α-pyran­ose); signals for adduct: 82.25 (C1), 73,23, 71.88, 70.61 (C2, C3, C4), 62.56 (C5). A small but significant peak was observed at δC 84.19.

Integration of the various signals for H-1 in the 1H NMR spectrum, 5 minutes after sample dissolution, indicated the species α-furan­ose, β-furan­ose, β-pyran­ose, α-pyran­ose, bis­ulfite adduct were present in the % ratios of 3.6:6.2:10.9:5.1:74.2. Re-measurement after 18 days, gave these % ratios as 1.5:2.6:16.2:8.7:70.9.

HRESMS (negative ion mode, measured in H2O/MeOH, solution) gave an expected peak at m/z 231.0187 ([C5H11O8S1]-), the base peak at 213.0082 ([C5H11O8S – H2O] -) and a significant peak at 299.0987 ([C10H19O10]-). The last peak corresponds to the ion of the product formed by reaction between the bis­ulfite adduct and D-ribose with displacement of potassium bis­ulfite.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The non-hydrogen atoms were refined with anisotropic thermal parameters. Hydrogen atoms bound to the carbon atoms were included in idealized positions (with C—H distances of 0.98 and 0.97Å for methyne and methyl­ene groups respectively) and their Uiso values were set to ride on the Ueq values of the parent atoms; hydroxyl hydrogen atoms were located in difference maps and were refined freely.

Related literature top

For related literature, see: Clayden et al. (2012); Cole et al. (2001); Gehman & Osman (1954); Haines & Hughes (2010, 2012, 2013); Ingles (1959); Lehmann & Benson (1964); Lipták et al. (2004).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2011); cell refinement: CrysAlis PRO (Oxford Diffraction, 2011); data reduction: CrysAlis PRO (Oxford Diffraction, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 2012).

Figures top
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 + 1/2, -z + 1; (ii) x - 1, y, z - 1; (iii) -x + 1, y + 1/2, -z + 1; (iv) -x, y + 1/2, -z; (v) x, y, z - 1; (vi) x, y, z + 1; (vii) -x, y - 1/2, -z; (viii) x + 1, y, z + 1; (ix) -x + 1, y - 1/2, -z + 1; (x) -x, y - 1/2, -z + 1; (xi) x - 1, y, z; (xii) x + 1, y, z.

View approximately along the a axis, showing the hydrogen-bonding contacts and all the K—O coordination bonds.

View along the c axis, showing the parallel alignment of the open-chain ions and the interionic interactions.

A section parallel to the ab plane around z = 0, showing the linking of the potassium ions in that plane; the connections are made through coordination bonds involving the sulfonate groups and the hydroxyl groups of O1 and O4.
Potassium (1R,2R,3R,4R)-1,2,3,4,5-pentahydroxypentane-1-sulfonate top
Crystal data top
K+·C5H11O8SF(000) = 280
Mr = 270.30Dx = 1.946 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 5.36167 (8) ÅCell parameters from 6553 reflections
b = 9.01474 (14) Åθ = 3.1–32.4°
c = 9.78623 (17) ŵ = 0.83 mm1
β = 102.8138 (16)°T = 140 K
V = 461.23 (1) Å3Plate, colourless
Z = 20.22 × 0.22 × 0.12 mm
Data collection top
Oxford Diffraction Xcalibur 3/Sapphire3 CCD
diffractometer
2690 independent reflections
Radiation source: Enhance (Mo) X-ray Source2632 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 16.0050 pixels mm-1θmax = 30.0°, θmin = 3.1°
Thin–slice ϕ and ω scansh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2011)
k = 1212
Tmin = 0.874, Tmax = 1.00l = 1313
8864 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.053 w = 1/[σ2(Fo2) + (0.0318P)2 + 0.0276P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2690 reflectionsΔρmax = 0.43 e Å3
156 parametersΔρmin = 0.22 e Å3
1 restraintAbsolute structure: Flack (1983), 1264 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (3)
Crystal data top
K+·C5H11O8SV = 461.23 (1) Å3
Mr = 270.30Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.36167 (8) ŵ = 0.83 mm1
b = 9.01474 (14) ÅT = 140 K
c = 9.78623 (17) Å0.22 × 0.22 × 0.12 mm
β = 102.8138 (16)°
Data collection top
Oxford Diffraction Xcalibur 3/Sapphire3 CCD
diffractometer
2690 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2011)
2632 reflections with I > 2σ(I)
Tmin = 0.874, Tmax = 1.00Rint = 0.023
8864 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.021H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.053Δρmax = 0.43 e Å3
S = 1.05Δρmin = 0.22 e Å3
2690 reflectionsAbsolute structure: Flack (1983), 1264 Friedel pairs
156 parametersAbsolute structure parameter: 0.01 (3)
1 restraint
Special details top

Experimental. Absorption correction: CrysAlisPro RED, Oxford Diffraction Ltd., Version 1.171.33.55 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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*/Ueq
K0.00261 (5)0.45609 (3)0.05055 (3)0.01553 (7)
C10.2210 (2)0.19926 (14)0.68818 (13)0.0093 (2)
H10.19560.09320.66790.011*
C20.3088 (2)0.27375 (14)0.56579 (14)0.0096 (2)
H20.49020.25280.57140.012*
C30.1458 (2)0.21199 (15)0.42818 (13)0.0101 (2)
H30.03410.21680.43410.012*
C40.1759 (2)0.30205 (16)0.30071 (14)0.0114 (2)
H40.12050.40360.31420.014*
C50.4444 (2)0.31169 (16)0.27422 (14)0.0120 (2)
H5A0.44180.37910.19670.014*
H5B0.55690.35390.35640.014*
O10.01482 (18)0.26253 (12)0.69708 (11)0.0141 (2)
O20.26721 (19)0.42953 (10)0.56585 (11)0.01250 (19)
O30.2107 (2)0.05973 (11)0.41598 (12)0.0157 (2)
O40.01062 (18)0.24575 (13)0.17548 (10)0.0159 (2)
O50.54900 (19)0.17312 (11)0.24301 (11)0.01340 (19)
S0.44130 (5)0.22060 (3)0.85556 (3)0.00909 (7)
O110.48670 (19)0.37852 (11)0.87973 (11)0.0165 (2)
O120.67445 (18)0.13911 (12)0.84780 (11)0.01367 (19)
O130.30566 (18)0.15410 (12)0.95421 (11)0.0155 (2)
H1O0.095 (4)0.211 (3)0.743 (2)0.031 (6)*
H2O0.388 (4)0.464 (3)0.611 (2)0.030 (6)*
H3O0.087 (4)0.010 (3)0.410 (2)0.027 (6)*
H4O0.122 (5)0.221 (3)0.199 (3)0.046 (7)*
H5O0.460 (4)0.149 (2)0.159 (2)0.013 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
K0.01277 (12)0.01544 (13)0.01879 (14)0.00082 (11)0.00440 (10)0.00328 (11)
C10.0088 (5)0.0103 (6)0.0087 (5)0.0003 (4)0.0018 (4)0.0003 (4)
C20.0093 (5)0.0087 (5)0.0112 (6)0.0001 (4)0.0028 (4)0.0016 (4)
C30.0091 (5)0.0113 (6)0.0100 (5)0.0005 (4)0.0027 (4)0.0003 (5)
C40.0106 (5)0.0138 (6)0.0098 (6)0.0011 (4)0.0023 (4)0.0016 (5)
C50.0105 (5)0.0118 (6)0.0139 (6)0.0003 (4)0.0033 (4)0.0003 (5)
O10.0078 (4)0.0192 (5)0.0157 (5)0.0023 (3)0.0037 (4)0.0052 (4)
O20.0153 (4)0.0079 (5)0.0134 (4)0.0027 (3)0.0014 (4)0.0001 (3)
O30.0184 (5)0.0084 (4)0.0216 (5)0.0032 (4)0.0076 (4)0.0020 (4)
O40.0092 (4)0.0279 (6)0.0102 (4)0.0016 (4)0.0014 (3)0.0024 (4)
O50.0114 (4)0.0154 (5)0.0136 (5)0.0017 (3)0.0033 (4)0.0007 (4)
S0.00795 (12)0.01038 (14)0.00897 (13)0.00016 (10)0.00192 (9)0.00056 (11)
O110.0176 (5)0.0121 (5)0.0182 (5)0.0016 (4)0.0005 (4)0.0026 (4)
O120.0090 (4)0.0165 (5)0.0159 (5)0.0024 (3)0.0037 (3)0.0031 (4)
O130.0133 (5)0.0230 (5)0.0112 (5)0.0024 (4)0.0047 (4)0.0029 (4)
Geometric parameters (Å, º) top
K—O13i2.7383 (10)C4—C51.5210 (17)
K—O11ii2.7873 (10)C4—H40.9800
K—O12iii2.8519 (10)C5—O51.4297 (17)
K—O4iv2.8775 (12)C5—H5A0.9700
K—O42.9065 (11)C5—H5B0.9700
K—O11v2.9115 (11)O1—Kvi3.0085 (11)
K—O1v3.0085 (11)O1—H1O0.83 (3)
K—O13v3.1654 (11)O2—H2O0.77 (2)
K—O12ii3.3874 (11)O3—H3O0.79 (2)
K—Sv3.4412 (4)O4—Kvii2.8775 (12)
K—Sii3.6306 (4)O4—H4O0.83 (3)
K—Kiv4.6161 (1)O5—H5O0.88 (2)
C1—O11.4071 (15)S—O111.4547 (10)
C1—C21.5355 (17)S—O131.4601 (10)
C1—S1.8048 (13)S—O121.4664 (10)
C1—H10.9800S—Kvi3.4412 (4)
C2—O21.4220 (15)S—Kviii3.6306 (4)
C2—C31.5380 (18)O11—Kviii2.7873 (10)
C2—H20.9800O11—Kvi2.9115 (10)
C3—O31.4275 (16)O12—Kix2.8519 (10)
C3—C41.5266 (18)O12—Kviii3.3874 (11)
C3—H30.9800O13—Kx2.7383 (10)
C4—O41.4364 (16)O13—Kvi3.1654 (11)
O13i—K—O11ii66.78 (3)O1—C1—C2107.84 (10)
O13i—K—O12iii72.73 (3)O1—C1—S108.47 (9)
O11ii—K—O12iii137.05 (3)C2—C1—S114.15 (8)
O13i—K—O4iv66.10 (3)O1—C1—H1108.8
O11ii—K—O4iv101.19 (3)C2—C1—H1108.8
O12iii—K—O4iv74.01 (3)S—C1—H1108.8
O13i—K—O494.10 (3)O2—C2—C1110.87 (10)
O11ii—K—O482.47 (3)O2—C2—C3107.40 (10)
O12iii—K—O486.77 (3)C1—C2—C3108.16 (10)
O4iv—K—O4155.53 (3)O2—C2—H2110.1
O13i—K—O11v151.02 (3)C1—C2—H2110.1
O11ii—K—O11v140.38 (4)C3—C2—H2110.1
O12iii—K—O11v82.34 (3)O3—C3—C4111.78 (10)
O4iv—K—O11v93.30 (3)O3—C3—C2108.63 (10)
O4—K—O11v99.10 (3)C4—C3—C2112.36 (11)
O13i—K—O1v138.55 (3)O3—C3—H3108.0
O11ii—K—O1v78.76 (3)C4—C3—H3108.0
O12iii—K—O1v144.12 (3)C2—C3—H3108.0
O4iv—K—O1v100.61 (3)O4—C4—C5107.64 (10)
O4—K—O1v103.82 (3)O4—C4—C3110.62 (11)
O11v—K—O1v62.31 (3)C5—C4—C3116.45 (11)
O13i—K—O13v154.51 (2)O4—C4—H4107.2
O11ii—K—O13v105.44 (3)C5—C4—H4107.2
O12iii—K—O13v104.88 (3)C3—C4—H4107.2
O4iv—K—O13v138.67 (3)O5—C5—C4114.67 (11)
O4—K—O13v60.45 (3)O5—C5—H5A108.6
O11v—K—O13v46.81 (3)C4—C5—H5A108.6
O1v—K—O13v55.64 (3)O5—C5—H5B108.6
O13i—K—O12ii109.70 (3)C4—C5—H5B108.6
O11ii—K—O12ii45.08 (3)H5A—C5—H5B107.6
O12iii—K—O12ii152.63 (2)C1—O1—Kvi114.91 (7)
O4iv—K—O12ii132.73 (3)C1—O1—H1O112.8 (16)
O4—K—O12ii65.93 (3)Kvi—O1—H1O78.7 (17)
O11v—K—O12ii99.24 (3)C2—O2—H2O106.9 (18)
O1v—K—O12ii49.47 (3)C3—O3—H3O109.5 (17)
O13v—K—O12ii60.68 (2)C4—O4—Kvii129.46 (8)
O13i—K—Sv174.03 (2)C4—O4—K108.72 (8)
O11ii—K—Sv118.68 (2)Kvii—O4—K105.89 (3)
O12iii—K—Sv101.37 (2)C4—O4—H4O105.4 (17)
O4iv—K—Sv113.59 (2)Kvii—O4—H4O86.0 (19)
O4—K—Sv84.56 (2)K—O4—H4O121.3 (18)
O11v—K—Sv24.72 (2)C5—O5—H5O104.9 (12)
O1v—K—Sv47.283 (18)O11—S—O13112.59 (6)
O13v—K—Sv25.091 (18)O11—S—O12112.64 (6)
O12ii—K—Sv75.077 (17)O13—S—O12112.57 (6)
O13i—K—Sii86.48 (2)O11—S—C1107.71 (6)
O11ii—K—Sii21.47 (2)O13—S—C1103.57 (6)
O12iii—K—Sii148.83 (2)O12—S—C1107.07 (6)
O4iv—K—Sii118.82 (2)O11—S—Kvi56.81 (4)
O4—K—Sii71.50 (2)O13—S—Kvi66.83 (4)
O11v—K—Sii122.16 (2)O12—S—Kvi164.56 (4)
O1v—K—Sii65.17 (2)C1—S—Kvi87.68 (4)
O13v—K—Sii83.965 (19)O11—S—Kviii44.54 (4)
O12ii—K—Sii23.797 (17)O13—S—Kviii125.40 (4)
Sv—K—Sii98.572 (10)O12—S—Kviii68.76 (4)
O13i—K—Kiv42.00 (2)C1—S—Kviii129.12 (4)
O11ii—K—Kiv104.16 (2)Kvi—S—Kviii98.572 (10)
O12iii—K—Kiv46.97 (2)S—O11—Kviii113.98 (5)
O4iv—K—Kiv37.27 (2)S—O11—Kvi98.48 (5)
O4—K—Kiv118.27 (2)Kviii—O11—Kvi140.38 (4)
O11v—K—Kiv109.44 (2)S—O12—Kix130.30 (6)
O1v—K—Kiv137.88 (2)S—O12—Kviii87.44 (5)
O13v—K—Kiv149.78 (2)Kix—O12—Kviii95.05 (3)
O12ii—K—Kiv149.228 (19)S—O13—Kx157.30 (6)
Sv—K—Kiv134.152 (11)S—O13—Kvi88.08 (5)
Sii—K—Kiv125.527 (10)Kx—O13—Kvi102.63 (3)
O1—C1—C2—O242.80 (13)Sv—K—O4—Kvii43.60 (2)
S—C1—C2—O277.80 (11)Sii—K—O4—Kvii57.34 (2)
O1—C1—C2—C374.71 (12)Kiv—K—O4—Kvii178.39 (2)
S—C1—C2—C3164.69 (8)O1—C1—S—O1164.93 (10)
O2—C2—C3—O3171.93 (10)C2—C1—S—O1155.31 (10)
C1—C2—C3—O368.35 (12)O1—C1—S—O1354.54 (10)
O2—C2—C3—C447.73 (13)C2—C1—S—O13174.78 (9)
C1—C2—C3—C4167.44 (10)O1—C1—S—O12173.69 (9)
O3—C3—C4—O460.64 (13)C2—C1—S—O1266.06 (10)
C2—C3—C4—O4176.92 (10)O1—C1—S—Kvi10.95 (8)
O3—C3—C4—C562.64 (15)C2—C1—S—Kvi109.29 (9)
C2—C3—C4—C559.80 (15)O1—C1—S—Kviii110.12 (8)
O4—C4—C5—O560.95 (15)C2—C1—S—Kviii10.12 (11)
C3—C4—C5—O563.86 (15)O13—S—O11—Kviii118.13 (6)
C2—C1—O1—Kvi110.24 (9)O12—S—O11—Kviii10.48 (8)
S—C1—O1—Kvi13.85 (10)C1—S—O11—Kviii128.31 (6)
C5—C4—O4—Kvii67.79 (13)Kvi—S—O11—Kviii156.73 (7)
C3—C4—O4—Kvii60.45 (13)O13—S—O11—Kvi38.60 (6)
C5—C4—O4—K63.02 (11)O12—S—O11—Kvi167.21 (5)
C3—C4—O4—K168.74 (7)C1—S—O11—Kvi74.95 (6)
O13i—K—O4—C475.17 (8)Kviii—S—O11—Kvi156.73 (7)
O11ii—K—O4—C4141.09 (8)O11—S—O12—Kix102.32 (8)
O12iii—K—O4—C42.76 (8)O13—S—O12—Kix26.30 (10)
O4iv—K—O4—C440.59 (8)C1—S—O12—Kix139.47 (7)
O11v—K—O4—C478.94 (8)Kvi—S—O12—Kix58.2 (2)
O1v—K—O4—C4142.50 (7)Kviii—S—O12—Kix94.45 (7)
O13v—K—O4—C4106.36 (8)O11—S—O12—Kviii7.87 (6)
O12ii—K—O4—C4175.06 (8)O13—S—O12—Kviii120.76 (5)
Sv—K—O4—C498.99 (7)C1—S—O12—Kviii126.08 (5)
Sii—K—O4—C4160.07 (8)Kvi—S—O12—Kviii36.23 (17)
Kiv—K—O4—C439.02 (8)O11—S—O13—Kx153.72 (15)
O13i—K—O4—Kvii142.24 (3)O12—S—O13—Kx77.63 (17)
O11ii—K—O4—Kvii76.33 (3)C1—S—O13—Kx37.66 (17)
O12iii—K—O4—Kvii145.35 (3)Kvi—S—O13—Kx119.12 (16)
O4iv—K—O4—Kvii176.82 (4)Kviii—S—O13—Kx156.92 (13)
O11v—K—O4—Kvii63.64 (3)O11—S—O13—Kvi34.60 (6)
O1v—K—O4—Kvii0.08 (3)O12—S—O13—Kvi163.25 (5)
O13v—K—O4—Kvii36.23 (3)C1—S—O13—Kvi81.46 (5)
O12ii—K—O4—Kvii32.47 (3)Kviii—S—O13—Kvi83.96 (4)
Symmetry codes: (i) x, y+1/2, z+1; (ii) x1, y, z1; (iii) x+1, y+1/2, z+1; (iv) x, y+1/2, z; (v) x, y, z1; (vi) x, y, z+1; (vii) x, y1/2, z; (viii) x+1, y, z+1; (ix) x+1, y1/2, z+1; (x) x, y1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O12xi0.83 (3)1.89 (3)2.6980 (14)165 (2)
O2—H2O···O5iii0.77 (2)2.34 (3)2.9111 (14)132 (2)
O3—H3O···O2x0.79 (2)2.10 (2)2.8596 (14)162 (2)
O4—H4O···O5xi0.83 (3)1.95 (3)2.7779 (14)175 (3)
O5—H5O···O13v0.88 (2)1.99 (2)2.8432 (14)161.7 (18)
Symmetry codes: (iii) x+1, y+1/2, z+1; (v) x, y, z1; (x) x, y1/2, z+1; (xi) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O12i0.83 (3)1.89 (3)2.6980 (14)165 (2)
O2—H2O···O5ii0.77 (2)2.34 (3)2.9111 (14)132 (2)
O3—H3O···O2iii0.79 (2)2.10 (2)2.8596 (14)162 (2)
O4—H4O···O5i0.83 (3)1.95 (3)2.7779 (14)175 (3)
O5—H5O···O13iv0.88 (2)1.99 (2)2.8432 (14)161.7 (18)
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1/2, z+1; (iii) x, y1/2, z+1; (iv) x, y, z1.

Experimental details

Crystal data
Chemical formulaK+·C5H11O8S
Mr270.30
Crystal system, space groupMonoclinic, P21
Temperature (K)140
a, b, c (Å)5.36167 (8), 9.01474 (14), 9.78623 (17)
β (°) 102.8138 (16)
V3)461.23 (1)
Z2
Radiation typeMo Kα
µ (mm1)0.83
Crystal size (mm)0.22 × 0.22 × 0.12
Data collection
DiffractometerOxford Diffraction Xcalibur 3/Sapphire3 CCD
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2011)
Tmin, Tmax0.874, 1.00
No. of measured, independent and
observed [I > 2σ(I)] reflections
8864, 2690, 2632
Rint0.023
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.021, 0.053, 1.05
No. of reflections2690
No. of parameters156
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.43, 0.22
Absolute structureFlack (1983), 1264 Friedel pairs
Absolute structure parameter0.01 (3)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2011), SHELXS97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 2012).

 

Acknowledgements

We thank the EPSRC National Mass Spectrometry Service Facility (NMSF), Swansea, for determination of the low- and high-resolution spectra.

References

First citationClayden, J. P., Greeves, N. & Warren, S. (2012). Organic Chemistry, 2nd ed., pp. 138–140. Oxford University Press.  Google Scholar
First citationCole, E. R., Craig, D. C., Fitzpatrick, L. J., Hibbert, D. B. & Stevens, J. D. (2001). Carbohydr. Res. 335, 1–10.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationGehman, H. & Osman, E. M. (1954). Adv. Food Res. 5, 53–96.  CrossRef PubMed CAS Web of Science Google Scholar
First citationHaines, A. H. & Hughes, D. L. (2010). Carbohydr. Res. 345, 2705–2708.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationHaines, A. H. & Hughes, D. L. (2012). Acta Cryst. E68, m377–m378.  CSD CrossRef IUCr Journals Google Scholar
First citationHaines, A. H. & Hughes, D. L. (2013). Acta Cryst. E69, m7–m8.  CSD CrossRef IUCr Journals Google Scholar
First citationIngles, D. L. (1959). Aust. J. Chem. 12, 97–101.  CAS Google Scholar
First citationJohnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
First citationLehmann, J. & Benson, A. A. (1964). J. Am. Chem. Soc. 86, 4469–4472.  CrossRef CAS Web of Science Google Scholar
First citationLipták, A., Balla, E., Jánossy, L., Sajtos, F. & Szilágyi, L. (2004). Tetrahedron Lett. 45, 839–842.  Google Scholar
First citationOxford Diffraction (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds