Dehydration of raffinose penta­hydrate: structures of raffinose 5-, 4.433-, 4.289- and 4.127-hydrate at 93 K

Raffinose [or O-α-D-galacto­pyranosyl-(1→6)-α-D-gluco­pyranosyl-(1→2)-β-D-fructo­furan­oside] penta­hydrate, C₁₈H₃₂O₁₆·5H₂O, (I), and three lower hydrates, namely the 4.433-, (II), 4.289-, (III), and 4.127-hydrated, (IV), forms, obtained in the course of the dehydration of (I), have been studied. The unit cells in the space group P2₁2₁2₁ are of similar dimensions for all the crystals. The conformation of the raffinose mol­ecules remains almost the same across the four crystal structures. The raffinose mol­ecules are linked into a three-dimensional hydrogen-bonded network involving all the –OH groups, the ring and glycosidic O atoms, and the water mol­ecules. Six water sites were identified in the structures of (II), (III) and (IV), of which W1, W4 and W6 (W = water) are partially occupied with their populations coupled. W1, W4 and one of the –OH groups of the galactose ring form an infinite hydrogen-bonding chain around a 2₁ axis parallel to the a axis (denoted chain A), and W6 and the same –OH group form a similar chain (chain A′) disordered with chain A. The occupancy ratio of chain A to chain A′ for N-hydrates (N is a hydration number between 4 and 5) is (N − 4):(5 − N). The transformation of chain A to chain A′ as part of the dehydration process has little effect on the rest of the structure. Thus, the dehydration proceeds without significant impact on the crystal structure.

S1. Introduction

Most of the common mono- and oligosaccharides exist in one or more stable anhydrous crystalline forms, e.g. sucrose, while others crystallize from solution as hydrates, where the degree of hydration depends on the stereochemical details of the sugar. Thus, the most stable form at ordinary temperatures of the disaccharide α,α-trehalose is a dihydrate (T2W), whereas the β,β-isomer crystallizes as T4W. As is the case for inorganic salts, lower hydrates or anhydrous forms can sometimes be produced by a carefully controlled dehydration of the higher hydrate form. The penta­hydrate appears to be the maximum observed hydration state in the case of sugars, and it is more than likely that new hydration states of mono- and oligosaccharides yet remain to be discovered. For mannitol, a linear hexitol, which had for a long time been believed to be anhydrous, a monohydrate of limited stability was recently discovered in a drying process, during which the hydrate decomposed to the anhydrous crystal with the release of the single solvent water molecule. This release of water caused damage to the material being dried (Yu et al., 1999). Dehydration of crystalline hydrates may also result in polymorphic changes to the solid material, accompanied by major changes in some of its physical properties.

Raffinose, or O-α-D-galacto­pyran­osyl-(1 →6)-α-D-gluco­pyran­osyl-(1 → 2)-β-D-fructo­furan­oside, is a tris­accharide which is used as a stabilizer in food, pharmaceutical and particularly biopharmaceutical processing. To assess the potential use of raffinose, an improved understanding of its solid-state properties and inter­actions with residual water, as well as its structural information, are required.

Crystalline raffinose normally exists in the penta­hydrate form (abbreviated hereafter as R5W). The crystal structure has been determined at room temperature by Berman (1970) and at 119 K by Jeffrey & Huang (1990). The Phase Rule [Does this need a reference?] suggests that, upon dehydration, several lower crystalline hydrate states might be formed prior to the crystallization of an anhydrous form. However, previous experimental studies of the controlled dehydration of R5W have led to the conclusion that none of the theoretically possible lower states could be achieved. Instead, the crystal collapsed into an amorphous hydrated form (Saleki-Gerhardt et al., 1995; Kajiwara & Franks, 1997; Kajiwara et al., 1999; Hogan & Buckton, 2001; Kajiwara et al., 2002; Cheng & Lin, 2006; Bates et al., 2007). Thus, no such lower hydrated crystal structure forms have actually been positively identified. The aim of this study was to obtain crystal structure information for raffinose tetra­hydrate (R4W), which might shed new light on changes in the sugar–sugar and sugar–water hydrogen-bonding patterns during the controlled removal of water.

Three versions of lower hydrated raffinose crystals obtained by dehydration of R5W are reported here. Structure refinement showed them to be the 4.433-, (II), 4.289-, (III), and 4.127-hydrated, (IV), forms. Though the structure of R5W has already been reported (Berman, 1970; Jeffrey & Huang, 1990), the structure at 93 K, (I), has been redetermined for comparison with those of the lower water content at the same temperature. The atom-numbering scheme and coordinate origin adopted in the previous reports are used in the present study. The dehydration process of (I) deduced from the comparative study of the four crystal structures is described here.

S2. Experimental

S2.1. Synthesis and crystallization

Raffinose penta­hydrate was purchased from Sigma and single crystals were obtained by slow evaporation of an aqueous solution. After suitable crystals for X-ray study of (I) had been selected, the remainder was ground and sieved to a fraction between 250 and 300 µm mesh size. The sieved crystals, divided into several lots, were dried over saturated KOH solution at 313 K for a maximum of 10 d and then stored in dry liquid paraffin. Good-quality crystals were selected from three different lots. The equilibrium relative humidity of KOH at 313 K is 6.26±0.35% (Greenspan, 1977).

S2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms bonded to O atoms, except those on O1W and O4W in (IV), were located initially in difference maps, and were then refined as riding on their parent atoms. The initial positions of the H atoms on O1W and O4W in (IV) were taken from those in (I) and (II). The mean O—H bond lengths of the hy­droxy groups and the water molecules are, respectively, 0.94 and 0.94 Å for (I), 0.94 and 0.94 Å for (II), 0.93 and 0.94 Å for (III), and 0.93 and 0.94 Å for (IV). All H atoms bonded to tertiary (C—H = 1.00 Å) and secondary (C—H = 0.99 Å) C atoms were located at geometrically idealized positions and were refined using a riding model. U_iso(H) values of 1.2U_eq(parent) were applied for all H atoms.

The absolute configurations of raffinose deduced from the Flack parameters (Parsons et al., 2013) agree well with those already proposed. Reflections with |I_o - I_c| > 10σ(I_o) were omitted at the last stage of least-squares refinement; the numbers of reflections are, respectively, 3, 2 and 2 for (II), (III) and (IV).

S3. Results and discussion

A perspective view of (II) is shown in Fig. 1, which is almost the same as those of (III) and (IV). Six water O atoms, labelled O1W to O6W, are located in (II), (III) and (IV) instead of the five water molecules in (I), the structure of which is similar excluding the absent O6W atom. The O1W···O4W(x + 1, y, z), O1W···O6W(x + 1/2, -y + 1/2, -z) and O4W···O6W distances are 2.843 (12), 2.411 (10) and 1.117 (12) Å, respectively. These values suggest that O1W and O4W might be disordered together with O6W. In order to confirm this, the occupancies of all the water O atoms were refined. The results are shown in Table 2. The occupancies (occ) of O1W, O4W and O6W in (II), (III) and (IV) are significantly smaller than 1.0 and are related to each other as occ(O1W) = occ(O4W), occ(O1W)+occ(O6W) = 1.0 and occ(O4W)+occ(O6W) = 1.0 within 2 s.u.'s, while the remainder occupations are approximately equal to 1.0. With the disorder model thus confirmed, the final least-squares refinements of (II), (III) and (IV) were carried out with the restraints occ(O4W) = occ(O1W) and occ(O6W) = 1.0 - occ(O1W). The refinements were successful and all the parameters converged well. In the process of dehydration, (II) → (III) → (IV), occ(O1W) decreases. The hydration numbers of each crystal are accordingly 4.00+occ(O1W).

The raffinose molecules link, with almost the same conformation in all four crystal forms, into a three-dimensional hydrogen-bonding network composed of all the hy­droxy groups, the ring and glycosidic O atoms and the water molecules. The six water molecules are denoted hereafter W1–W6 and their symmetrically generated sites are shown using the symmetry codes presented in the caption of Fig. 2. The hydrogen-bonding system constructed in R5W has been reported in detail by Jeffrey & Huang (1990); the network can be resolved with four infinite chains, three of which are formed around 2₁ axes extending along the a, b and c axes, respectively (abbreviated as 2₁[a] etc.). The three chains are named here as chain A (red lines in Fig. 2), chain B (brown) and chain C (green). The fourth chain (chain A'', blue), composed of the O atoms not related by 2₁[a], extends parallel to the a axis. In (II), (III) and (IV), one more chain (chain A', black) similar to chain A is formed: chain A is composed of W1, W4 and O2', which is one of the hy­droxy groups of the galactose ring, viz. ···O2'···W4(W1A)···O2'F···, while chain A' is composed of W6 and O2', viz. ···O2'···W6···O2'F···. Since W1 and W4 are disordered with W6 as described above, chain A is disordered over chain A' with an occupancy ratio of occ(O1W):occ(O6W) [What is the ratio numerically?]. The dehydration process of R5W to R4W may be inter­preted as the process in the transformation of chain A to chain A'.

Drawings of parts of the hydrogen-bonding network, viewed down the a axis for (II), are shown in Figs. 2 and 3, respectively. Hydrogen bonds making up the respective chains are presented in Table 3. Chains B and C inter­sect at W3, and one half-period of chain B and that of chain C are alternately linked to form a helical chain (chain H) around 2₁[a], as shown in Fig. 3, viz. ···(chain B)···W3N···(chain C)···W3···(chain B)···W3K···(chain C)···W3E···(chain B)···W3M···(chain C)···. Chains A'' and B are connected by sharing W2···W5 (blue and brown lines).

Two raffinose molecules, shown by dark-yellow lines in Fig. 3, are related by 2₁[a] and linked by O3'···O6''E. The linkage of the molecules is extended helically along with chain H, and a columnar structure is formed around 2₁[a]. The principle of the structures of all the crystals may be described as a two-dimensional arrangement of the columns. In (II), (III) and (IV), W1, W4 and W6 are included and disordered in the tunnel formed inside the column. Chain A is bridged to the column by W1E···W2E, W1E···O6'G, W4F···O5F and W4F···O6F (red dotted lines in Fig. 3), and chain A' is bridged by W6F···W2, W6F···O5F and W6F···O6F (black dotted lines).

We assume by inspection of Figs. 2 and 3 that the transformation of chain A to chain A' is initiated by release of W1E and by successively occurring transfer of W4F to the site of W6F, which is only 1.117 (12) Å from W4F, and one half-period of chain A', viz. O2'D···W6F···O2'F, is formed. This results in the release of W1, because W6F approaches W1 at a distance of 2.411 (10) Å, and then chain A' may be extended to some extent. As a result, chains A and A' are randomly included in the columns with a probability ratio of (N - 4):(5 - N) (N is the hydration number). The rearrangement of the water molecules, followed by changes in the bridges of chains A and A' to the column, takes place in a limited location, so that the effects on the crystal structure are small.

The values of R[F²>2σ(F²)] and wR(F²) tend to become larger as the value of |occ(chain A) - occ(chain A')| is reduced from 1.0 to 0.0, i.e. (I) → (IV) → (III) → (II) (Table 1). The averaged bond precisions for C—C in (II) and (III) of 0.006 Å are large, as flagged by checkCIF, while those for (I) and (IV) are 0.004 Å. The structure of (IV) has been determined with a similar accuracy as for (I), in spite of having the longest dehydration time of the lower hydrates. As the crystal of R4W may be obtained by continuous dehydration of (IV), the structure is presumed to be an analogue of (IV), where the transformation of chain A to chain A' is completed.

It has been revealed by the present study that raffinose crystals with a hydration number between 4 and 5 can be obtained by moderate dehydration of R5W. During dehydration, the transformation of chain A to chain A' has occurred, but no remarkable changes in the other portion of the structure are observed.

In the unpublished hydrogen bond tables, there are some highly unusual entries. For instance, for (III), one of the angles is given as 1644° and the H—A distance is quoted to 3 d.p.s (all other entries are to 2 d.p.s), while for (IV) one of the angles is given as 1494° and another H—A distance is quoted to 3 d.p.s. Please check and advise.

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998) for (I), (II); RAPID-AUTO (Rigaku, 1998) for (III), (IV). Cell refinement: PROCESS-AUTO (Rigaku, 1998) for (I), (II); RAPID-AUTO (Rigaku, 1998) for (III), (IV). Data reduction: PROCESS-AUTO (Rigaku, 1998) for (I), (II); RAPID-AUTO (Rigaku, 1998) for (III), (IV). For all compounds, program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015). Molecular graphics: CrystalStructure (Rigaku & Rigaku Americas Corporation, 2014) and ORTEPII (Johnson, 1976) for (I), (II); CrystalStructure (Rigaku, 2010) and ORTEPII (Johnson, 1976) for (III), (IV). Software used to prepare material for publication: CrystalStructure (Rigaku & Rigaku Americas Corporation, 2014) for (I), (II); CrystalStructure (Rigaku, 2010) for (III), (IV).

Figures

	Fig. 1. A perspective view of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 70% probability level, and those of the water molecules are shown in blue. Those of (III) and (IV) are almost the same [Symmetry code: (*) x - 1, y, z.] [Very poor quality; can a higher resolution version be provided?]
	Fig. 2. Part of the hydrogen-bonding network in (II), composed of chain A (shown by red lines), chain A' (black), chain A'' (blue), chain B (brown) and chain C (green). Chain A is disordered with chain A'. W1 in chain A is bound to W2 and O6'C (red dotted lines), and W6F in chain A' bound to W2 (black dotted line). W2···W5 (brown curved and blue straight lines) is shared by chains B and C. Red, brown and green arrows represent 21[a], 21[b] and 21[c], respectively. All H atoms have been omitted for clarity. [Symmetry codes: (A) x - 1, y, z; (B) x, y - 1, z; (C) x + 1, y - 1, z; (D) x + 1, y, z; (E) x - 1/2, -y + 1/2, -z; (F) x + 1/2, -y + 1/2, -z; (G) x + 1/2, -y + 3/2, -z; (H) x + 3/2, -y + 1/2, -z; (I) -x + 2, y - 1/2, -z + 1/2; (J) -x, y - 1/2, -z + 1/2; (K) -x + 1, y - 1/2, -z + 1/2; (L) -x + 1/2, -y, z - 1/2; (M) -x + 1/2, -y + 1, z - 1/2; (N) x + 3/2, -y + 1, z - 1/2.] [The figure would benefit from being at a higher resolution; can a revised version be provided?]
	Fig. 3. Part of a projection of the packing of (II), viewed down the a axis. Raffinose molecules are drawn with dark-yellow lines. For chain A', the positions of W6 (black circles), W6···O5 and W6···O6 (black dotted lines) are only shown for clarity. [The figure would benefit from being at a higher resolution; can a revised version be provided?]

(I) O-α-D-Galactopyranosyl-(1 → 6)-α-D-glucopyranosyl-(1 → 2)-β-D-fructofuranose pentahydrate

Crystal data

C18H32O16·5H2O	F(000) = 1272.00
Mr = 594.52	Dx = 1.525 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2ac 2ab	Cell parameters from 23501 reflections
a = 8.88472 (16) Å	θ = 4.1–68.2°
b = 12.2592 (2) Å	µ = 1.25 mm^−1
c = 23.7676 (7) Å	T = 93 K
V = 2588.74 (10) Å^3	Block, colourless
Z = 4	0.17 × 0.08 × 0.04 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	4506 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.028
ω scans	θmax = 68.2°, θmin = 4.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.749, Tmax = 0.951	k = −14→14
29755 measured reflections	l = −28→28
4746 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.036P)^2 + 1.3257P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
4745 reflections	Δρmax = 0.21 e Å^−3
353 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Absolute structure: Flack x parameter determined using 1851 quotients [(I^+) -(I^-)]/[(I^+) + (I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (5)
Secondary atom site location: difference Fourier map

Special details

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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2770 (3)	0.3180 (2)	0.14248 (11)	0.0142 (6)
H1	0.2961	0.2415	0.1297	0.017*
C2	0.3914 (3)	0.3940 (2)	0.11538 (11)	0.0138 (6)
H2	0.3798	0.3870	0.0737	0.017*
C3	0.3593 (3)	0.5131 (2)	0.13070 (11)	0.0147 (6)
H3	0.3762	0.5239	0.1719	0.018*
C4	0.1964 (3)	0.5416 (2)	0.11636 (11)	0.0131 (5)
H4	0.1834	0.5416	0.0746	0.016*
C5	0.0888 (3)	0.4594 (2)	0.14239 (11)	0.0134 (6)
H5	0.0957	0.4652	0.1843	0.016*
C6	−0.0723 (3)	0.4781 (2)	0.12510 (11)	0.0148 (6)
H6A	−0.1379	0.4219	0.1423	0.018*
H6B	−0.1064	0.5506	0.1382	0.018*
C1'	−0.2237 (3)	0.5059 (2)	0.04481 (11)	0.0141 (6)
H1'	−0.3043	0.4680	0.0667	0.017*
C2'	−0.2348 (3)	0.4723 (2)	−0.01695 (11)	0.0135 (5)
H2'	−0.3387	0.4908	−0.0300	0.016*
C3'	−0.1249 (3)	0.5375 (2)	−0.05324 (11)	0.0144 (6)
H3'	−0.0196	0.5171	−0.0428	0.017*
C4'	−0.1472 (3)	0.6597 (2)	−0.04307 (11)	0.0144 (6)
H4'	−0.0656	0.7000	−0.0632	0.017*
C5'	−0.1329 (3)	0.6833 (2)	0.01961 (11)	0.0147 (6)
H5'	−0.0296	0.6631	0.0327	0.018*
C6'	−0.1656 (3)	0.8017 (2)	0.03527 (12)	0.0169 (6)
H6'A	−0.2649	0.8229	0.0199	0.020*
H6'B	−0.1702	0.8084	0.0767	0.020*
C1''	0.3843 (3)	0.2114 (2)	0.27478 (11)	0.0151 (6)
H1''A	0.4693	0.1880	0.2507	0.018*
H1''B	0.4159	0.2772	0.2958	0.018*
C2''	0.2493 (3)	0.2386 (2)	0.23816 (11)	0.0138 (6)
C3''	0.1086 (3)	0.2740 (2)	0.27000 (11)	0.0147 (6)
H3''	0.1026	0.2329	0.3063	0.018*
C4''	−0.0176 (3)	0.2366 (2)	0.23148 (11)	0.0146 (6)
H4''	−0.0217	0.2873	0.1986	0.018*
C5''	0.0453 (3)	0.1280 (2)	0.21129 (11)	0.0147 (6)
H5''	0.0218	0.0701	0.2396	0.018*
C6''	−0.0081 (3)	0.0916 (2)	0.15376 (12)	0.0168 (6)
H6''A	−0.1195	0.0913	0.1532	0.020*
H6''B	0.0267	0.1447	0.1252	0.020*
O1	0.2998 (2)	0.32480 (15)	0.20110 (7)	0.0129 (4)
O2	0.5411 (2)	0.36138 (15)	0.12906 (8)	0.0156 (4)
H2O	0.5632	0.3795	0.1667	0.019*
O3	0.4545 (2)	0.58567 (15)	0.09989 (8)	0.0155 (4)
H3O	0.5380	0.6052	0.1204	0.019*
O4	0.1566 (2)	0.64569 (15)	0.13806 (8)	0.0156 (4)
H4O	0.1913	0.7072	0.1169	0.019*
O5	0.1284 (2)	0.35025 (15)	0.12608 (8)	0.0133 (4)
O6	−0.0817 (2)	0.47217 (15)	0.06490 (7)	0.0142 (4)
O2'	−0.2156 (2)	0.35771 (16)	−0.02408 (8)	0.0175 (4)
H2'O	−0.1176	0.3414	−0.0089	0.021*
O3'	−0.1478 (2)	0.51480 (16)	−0.11138 (7)	0.0167 (4)
H3'O	−0.0846	0.4578	−0.1202	0.020*
O4'	−0.2890 (2)	0.69603 (15)	−0.06447 (8)	0.0171 (4)
H4'O	−0.3658	0.6656	−0.0417	0.020*
O5'	−0.2429 (2)	0.62084 (15)	0.05020 (8)	0.0141 (4)
O6'	−0.0529 (2)	0.87410 (15)	0.01399 (8)	0.0156 (4)
H6'O	−0.0557	0.8796	−0.0253	0.019*
O1''	0.3476 (2)	0.12672 (15)	0.31328 (8)	0.0163 (4)
H1''O	0.3204	0.0657	0.2924	0.020*
O2''	0.2076 (2)	0.14385 (15)	0.20846 (8)	0.0143 (4)
O3''	0.1134 (2)	0.38724 (15)	0.28161 (8)	0.0166 (4)
H3''O	0.0480	0.4112	0.3099	0.020*
O4''	−0.1634 (2)	0.23174 (16)	0.25579 (8)	0.0165 (4)
H4''O	−0.1484	0.2037	0.2910	0.020*
O6''	0.0460 (2)	−0.01510 (15)	0.13906 (8)	0.0178 (4)
H6''O	0.1522	−0.0089	0.1343	0.021*
O1W	0.7962 (2)	0.08467 (17)	0.03555 (8)	0.0220 (5)
H1WA	0.8676	0.1429	0.0312	0.026*
H1WB	0.8535	0.0227	0.0344	0.026*
O2W	0.5883 (2)	0.13507 (16)	0.12048 (8)	0.0199 (4)
H2WA	0.5708	0.2152	0.1193	0.024*
H2WB	0.6542	0.1257	0.0923	0.036 (10)*
O3W	0.6478 (2)	0.41603 (16)	0.23318 (8)	0.0194 (4)
H3WA	0.5733	0.4260	0.2629	0.023*
H3WB	0.7135	0.3659	0.2491	0.023*
O4W	0.0175 (2)	0.25088 (16)	0.02445 (8)	0.0193 (4)
H4WA	0.0463	0.2993	0.0542	0.023*
H4WB	0.1068	0.2169	0.0195	0.023*
O5W	0.6019 (2)	0.00096 (17)	0.21743 (9)	0.0230 (5)
H5WA	0.5942	0.0479	0.1872	0.028*
H5WB	0.6998	−0.0228	0.2236	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0147 (14)	0.0159 (14)	0.0118 (13)	0.0026 (11)	−0.0027 (11)	0.0010 (11)
C2	0.0134 (13)	0.0153 (13)	0.0127 (13)	0.0016 (11)	−0.0004 (10)	0.0003 (10)
C3	0.0171 (14)	0.0149 (13)	0.0121 (12)	−0.0030 (11)	−0.0002 (11)	0.0001 (11)
C4	0.0150 (14)	0.0123 (13)	0.0121 (12)	0.0014 (11)	−0.0006 (10)	0.0012 (10)
C5	0.0146 (14)	0.0130 (13)	0.0126 (13)	0.0002 (11)	0.0005 (11)	−0.0003 (10)
C6	0.0152 (14)	0.0172 (13)	0.0122 (13)	0.0008 (11)	0.0027 (10)	0.0005 (11)
C1'	0.0142 (14)	0.0125 (13)	0.0156 (13)	−0.0015 (11)	−0.0007 (11)	0.0016 (11)
C2'	0.0142 (14)	0.0109 (13)	0.0154 (13)	−0.0001 (11)	−0.0014 (11)	0.0008 (11)
C3'	0.0142 (14)	0.0161 (13)	0.0128 (12)	0.0013 (11)	−0.0011 (11)	−0.0021 (11)
C4'	0.0123 (13)	0.0151 (13)	0.0159 (13)	0.0023 (11)	0.0004 (11)	0.0012 (11)
C5'	0.0149 (14)	0.0141 (13)	0.0151 (13)	−0.0024 (11)	0.0022 (11)	0.0027 (11)
C6'	0.0159 (14)	0.0150 (14)	0.0198 (14)	−0.0007 (11)	0.0038 (11)	−0.0019 (11)
C1''	0.0160 (14)	0.0145 (13)	0.0148 (13)	−0.0007 (11)	−0.0007 (11)	0.0021 (11)
C2''	0.0170 (14)	0.0120 (13)	0.0124 (13)	−0.0024 (11)	0.0009 (11)	0.0011 (11)
C3''	0.0175 (14)	0.0126 (13)	0.0140 (13)	0.0009 (11)	0.0008 (11)	0.0027 (11)
C4''	0.0134 (14)	0.0153 (14)	0.0152 (13)	0.0000 (11)	0.0003 (11)	0.0035 (11)
C5''	0.0128 (13)	0.0148 (14)	0.0165 (13)	−0.0020 (11)	−0.0003 (11)	0.0028 (11)
C6''	0.0185 (15)	0.0140 (13)	0.0179 (14)	−0.0011 (12)	−0.0003 (11)	0.0007 (11)
O1	0.0155 (10)	0.0114 (9)	0.0119 (9)	−0.0019 (7)	−0.0004 (7)	0.0015 (7)
O2	0.0147 (9)	0.0171 (10)	0.0151 (9)	0.0015 (8)	−0.0015 (8)	0.0002 (8)
O3	0.0148 (10)	0.0166 (10)	0.0152 (9)	−0.0058 (8)	−0.0008 (8)	0.0031 (8)
O4	0.0185 (10)	0.0108 (9)	0.0173 (9)	0.0004 (8)	0.0025 (8)	0.0003 (8)
O5	0.0120 (9)	0.0130 (9)	0.0149 (9)	0.0005 (8)	−0.0013 (7)	−0.0012 (7)
O6	0.0139 (10)	0.0173 (10)	0.0114 (9)	0.0014 (8)	−0.0017 (7)	−0.0006 (8)
O2'	0.0161 (10)	0.0145 (9)	0.0218 (10)	−0.0013 (8)	−0.0038 (8)	−0.0012 (8)
O3'	0.0187 (10)	0.0180 (10)	0.0134 (9)	0.0033 (8)	−0.0005 (8)	−0.0027 (8)
O4'	0.0168 (10)	0.0166 (10)	0.0177 (10)	0.0021 (8)	−0.0008 (8)	0.0023 (8)
O5'	0.0134 (10)	0.0127 (9)	0.0163 (9)	0.0001 (8)	0.0014 (8)	0.0011 (8)
O6'	0.0168 (9)	0.0144 (9)	0.0158 (9)	−0.0036 (8)	0.0001 (8)	0.0012 (8)
O1''	0.0182 (10)	0.0154 (9)	0.0152 (9)	0.0006 (8)	−0.0029 (8)	0.0031 (8)
O2''	0.0137 (9)	0.0138 (10)	0.0156 (9)	−0.0007 (8)	0.0002 (7)	−0.0016 (8)
O3''	0.0187 (10)	0.0119 (9)	0.0192 (10)	−0.0003 (8)	0.0044 (8)	−0.0028 (8)
O4''	0.0132 (10)	0.0201 (10)	0.0161 (9)	0.0007 (8)	0.0011 (8)	0.0038 (8)
O6''	0.0173 (10)	0.0163 (10)	0.0199 (10)	−0.0022 (8)	0.0034 (8)	−0.0039 (8)
O1W	0.0212 (11)	0.0202 (10)	0.0245 (11)	0.0007 (9)	0.0008 (9)	−0.0012 (9)
O2W	0.0218 (10)	0.0174 (10)	0.0205 (10)	−0.0003 (9)	0.0024 (8)	0.0017 (8)
O3W	0.0210 (11)	0.0200 (10)	0.0171 (9)	0.0009 (9)	0.0003 (8)	0.0001 (8)
O4W	0.0185 (10)	0.0179 (10)	0.0216 (10)	0.0033 (8)	−0.0030 (8)	−0.0030 (9)
O5W	0.0180 (10)	0.0255 (11)	0.0255 (11)	0.0025 (9)	0.0000 (9)	0.0076 (9)

Geometric parameters (Å, º)

C1—C2	1.522 (4)	C4—H4	1.00
C1—O1	1.410 (3)	C5—H5	1.00
C1—O5	1.433 (3)	C6—H6A	0.99
C2—C3	1.532 (4)	C6—H6B	0.99
C2—O2	1.426 (3)	C1'—H1'	1.00
C3—C4	1.527 (4)	C2'—H2'	1.00
C3—O3	1.429 (3)	C3'—H3'	1.00
C4—C5	1.520 (4)	C4'—H4'	1.00
C4—O4	1.422 (3)	C5'—H5'	1.00
C5—C6	1.507 (4)	C6'—H6'A	0.99
C5—O5	1.437 (3)	C6'—H6'B	0.99
C6—O6	1.435 (3)	C1''—H1''A	0.99
C1'—C2'	1.528 (4)	C1''—H1''B	0.99
C1'—O6	1.411 (3)	C3''—H3''	1.00
C1'—O5'	1.425 (3)	C4''—H4''	1.00
C2'—C3'	1.528 (4)	C5''—H5''	1.00
C2'—O2'	1.426 (3)	C6''—H6''A	0.99
C3'—C4'	1.529 (4)	C6''—H6''B	0.99
C3'—O3'	1.424 (3)	O2—H2O	0.94
C4'—C5'	1.523 (4)	O3—H3O	0.92
C4'—O4'	1.430 (3)	O4—H4O	0.96
C5'—C6'	1.526 (4)	O2'—H2'O	0.96
C5'—O5'	1.439 (3)	O3'—H3'O	0.92
C6'—O6'	1.430 (3)	O4'—H4'O	0.95
C1''—C2''	1.519 (4)	O6'—H6'O	0.94
C1''—O1''	1.422 (3)	O1''—H1''O	0.93
C2''—C3''	1.525 (4)	O3''—H3''O	0.94
C2''—O1	1.447 (3)	O4''—H4''O	0.91
C2''—O2''	1.409 (3)	O6''—H6''O	0.95
C3''—C4''	1.518 (4)	O1W—H1WA	0.96
C3''—O3''	1.416 (3)	O1W—H1WB	0.92
C4''—C5''	1.522 (4)	O2W—H2WA	0.99
C4''—O4''	1.419 (3)	O2W—H2WB	0.90
C5''—C6''	1.515 (4)	O3W—H3WA	0.98
C5''—O2''	1.457 (3)	O3W—H3WB	0.93
C6''—O6''	1.437 (3)	O4W—H4WA	0.96
C1—H1	1.00	O4W—H4WB	0.90
C2—H2	1.00	O5W—H5WA	0.92
C3—H3	1.00	O5W—H5WB	0.93
C2—C1—O1	106.6 (2)	H4—C4—O4	109
C2—C1—O5	109.4 (2)	C4—C5—H5	109
O1—C1—O5	112.6 (2)	H5—C5—C6	109
C1—C2—C3	111.0 (2)	H5—C5—O5	109
C1—C2—O2	110.8 (2)	C5—C6—H6A	110
C3—C2—O2	112.8 (2)	C5—C6—H6B	110
C2—C3—C4	110.0 (2)	H6A—C6—H6B	108
C2—C3—O3	111.2 (2)	H6A—C6—O6	110
C4—C3—O3	107.7 (2)	H6B—C6—O6	110
C3—C4—C5	110.7 (2)	H1'—C1'—C2'	109
C3—C4—O4	111.1 (2)	H1'—C1'—O6	109
C5—C4—O4	106.9 (2)	H1'—C1'—O5'	109
C4—C5—C6	112.7 (2)	C1'—C2'—H2'	107
C4—C5—O5	110.7 (2)	H2'—C2'—C3'	107
C6—C5—O5	107.5 (2)	H2'—C2'—O2'	107
C5—C6—O6	108.6 (2)	C2'—C3'—H3'	109
C2'—C1'—O6	107.7 (2)	H3'—C3'—C4'	109
C2'—C1'—O5'	110.2 (2)	H3'—C3'—O3'	109
O6—C1'—O5'	111.5 (2)	C3'—C4'—H4'	108
C1'—C2'—C3'	111.1 (2)	H4'—C4'—C5'	108
C1'—C2'—O2'	111.9 (2)	H4'—C4'—O4'	108
C3'—C2'—O2'	111.8 (2)	C4'—C5'—H5'	110
C2'—C3'—C4'	109.9 (2)	H5'—C5'—C6'	110
C2'—C3'—O3'	110.7 (2)	H5'—C5'—O5'	110
C4'—C3'—O3'	109.0 (2)	C5'—C6'—H6'A	109
C3'—C4'—C5'	109.3 (2)	C5'—C6'—H6'B	109
C3'—C4'—O4'	111.3 (2)	H6'A—C6'—H6'B	108
C5'—C4'—O4'	111.2 (2)	H6'A—C6'—O6'	109
C4'—C5'—C6'	113.8 (2)	H6'B—C6'—O6'	109
C4'—C5'—O5'	109.7 (2)	H1''A—C1''—H1''B	108
C6'—C5'—O5'	104.7 (2)	H1''A—C1''—C2''	110
C5'—C6'—O6'	111.8 (2)	H1''A—C1''—O1''	110
C2''—C1''—O1''	110.4 (2)	H1''B—C1''—C2''	110
C1''—C2''—C3''	115.2 (2)	H1''B—C1''—O1''	110
C1''—C2''—O1	105.3 (2)	C2''—C3''—H3''	109
C1''—C2''—O2''	108.3 (2)	H3''—C3''—C4''	109
C3''—C2''—O1	110.4 (2)	H3''—C3''—O3''	109
C3''—C2''—O2''	105.5 (2)	C3''—C4''—H4''	108
O1—C2''—O2''	112.2 (2)	H4''—C4''—C5''	108
C2''—C3''—C4''	102.7 (2)	H4''—C4''—O4''	108
C2''—C3''—O3''	110.5 (2)	C4''—C5''—H5''	109
C4''—C3''—O3''	115.9 (2)	H5''—C5''—C6''	109
C3''—C4''—C5''	100.5 (2)	H5''—C5''—O2''	109
C3''—C4''—O4''	116.2 (2)	C5''—C6''—H6''A	109
C5''—C4''—O4''	115.3 (2)	C5''—C6''—H6''B	109
C4''—C5''—C6''	115.3 (2)	H6''A—C6''—H6''B	108
C4''—C5''—O2''	105.2 (2)	H6''A—C6''—O6''	109
C6''—C5''—O2''	107.9 (2)	H6''B—C6''—O6''	109
C5''—C6''—O6''	112.5 (2)	C2—O2—H2O	110
C1—O1—C2''	120.9 (2)	C3—O3—H3O	111
C1—O5—C5	114.2 (2)	C4—O4—H4O	116
C6—O6—C1'	112.01 (19)	C2'—O2'—H2'O	106
C1'—O5'—C5'	113.5 (2)	C3'—O3'—H3'O	106
C2''—O2''—C5''	110.3 (2)	C4'—O4'—H4'O	108
H1—C1—C2	109	C6'—O6'—H6'O	112
H1—C1—O1	109	C1''—O1''—H1''O	108
H1—C1—O5	109	C3''—O3''—H3''O	115
C1—C2—H2	107	C4''—O4''—H4''O	105
H2—C2—C3	107	C6''—O6''—H6''O	107
H2—C2—O2	107	H1WA—O1W—H1WB	104
C2—C3—H3	109	H2WA—O2W—H2WB	102
H3—C3—C4	109	H3WA—O3W—H3WB	102
H3—C3—O3	109	H4WA—O4W—H4WB	98
C3—C4—H4	109	H5WA—O5W—H5WB	113
H4—C4—C5	109
C2—C1—O1—C2''	−158.51 (17)	C2'—C3'—C4'—O4'	−68.4 (3)
O1—C1—C2—C3	−65.8 (2)	O3'—C3'—C4'—C5'	176.36 (18)
O1—C1—C2—O2	60.3 (2)	O3'—C3'—C4'—O4'	53.1 (3)
C2—C1—O5—C5	−60.2 (2)	C3'—C4'—C5'—C6'	−175.39 (19)
O5—C1—C2—C3	56.3 (3)	C3'—C4'—C5'—O5'	−58.5 (3)
O5—C1—C2—O2	−177.67 (18)	O4'—C4'—C5'—C6'	−52.1 (3)
O1—C1—O5—C5	58.2 (2)	O4'—C4'—C5'—O5'	64.7 (3)
O5—C1—O1—C2''	81.6 (2)	C4'—C5'—C6'—O6'	−67.9 (3)
C1—C2—C3—C4	−53.6 (3)	C4'—C5'—O5'—C1'	62.4 (2)
C1—C2—C3—O3	−172.78 (19)	C6'—C5'—O5'—C1'	−175.18 (17)
O2—C2—C3—C4	−178.54 (18)	O5'—C5'—C6'—O6'	172.35 (19)
O2—C2—C3—O3	62.3 (3)	O1''—C1''—C2''—C3''	58.1 (3)
C2—C3—C4—C5	52.2 (3)	O1''—C1''—C2''—O1	−179.95 (18)
C2—C3—C4—O4	170.87 (19)	O1''—C1''—C2''—O2''	−59.7 (3)
O3—C3—C4—C5	173.53 (17)	C1''—C2''—C3''—C4''	−150.5 (2)
O3—C3—C4—O4	−67.8 (2)	C1''—C2''—C3''—O3''	85.3 (3)
C3—C4—C5—C6	−174.79 (18)	C1''—C2''—O1—C1	129.89 (19)
C3—C4—C5—O5	−54.4 (3)	C1''—C2''—O2''—C5''	133.85 (19)
O4—C4—C5—C6	64.1 (2)	C3''—C2''—O1—C1	−105.2 (2)
O4—C4—C5—O5	−175.54 (18)	O1—C2''—C3''—C4''	90.3 (2)
C4—C5—C6—O6	58.3 (3)	O1—C2''—C3''—O3''	−33.8 (3)
C4—C5—O5—C1	59.7 (2)	C3''—C2''—O2''—C5''	10.0 (2)
C6—C5—O5—C1	−176.85 (17)	O2''—C2''—C3''—C4''	−31.2 (2)
O5—C5—C6—O6	−63.9 (2)	O2''—C2''—C3''—O3''	−155.36 (19)
C5—C6—O6—C1'	−170.50 (17)	O1—C2''—O2''—C5''	−110.3 (2)
C2'—C1'—O6—C6	−167.23 (17)	O2''—C2''—O1—C1	12.3 (3)
O6—C1'—C2'—C3'	−67.8 (2)	C2''—C3''—C4''—C5''	38.8 (2)
O6—C1'—C2'—O2'	58.0 (3)	C2''—C3''—C4''—O4''	163.9 (2)
C2'—C1'—O5'—C5'	−59.6 (2)	O3''—C3''—C4''—C5''	159.41 (19)
O5'—C1'—C2'—C3'	54.0 (3)	O3''—C3''—C4''—O4''	−75.5 (3)
O5'—C1'—C2'—O2'	179.81 (19)	C3''—C4''—C5''—C6''	−152.2 (2)
O6—C1'—O5'—C5'	60.0 (2)	C3''—C4''—C5''—O2''	−33.5 (2)
O5'—C1'—O6—C6	71.7 (2)	O4''—C4''—C5''—C6''	82.0 (3)
C1'—C2'—C3'—C4'	−52.9 (3)	O4''—C4''—C5''—O2''	−159.22 (19)
C1'—C2'—C3'—O3'	−173.37 (19)	C4''—C5''—C6''—O6''	−175.5 (2)
O2'—C2'—C3'—C4'	−178.63 (18)	C4''—C5''—O2''—C2''	15.2 (2)
O2'—C2'—C3'—O3'	60.9 (3)	C6''—C5''—O2''—C2''	138.72 (19)
C2'—C3'—C4'—C5'	54.8 (3)	O2''—C5''—C6''—O6''	67.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3W	0.94	1.81	2.733 (3)	167
O3—H3O···O1′′^i	0.92	1.89	2.758 (3)	156
O4—H4O···O4′^ii	0.96	1.73	2.657 (3)	162
O2′—H2′O···O4W	0.96	1.82	2.708 (3)	153
O3′—H3′O···O2W^iii	0.92	1.91	2.797 (3)	161
O4′—H4′O···O6′^iv	0.95	1.85	2.771 (3)	162
O6′—H6′O···O3^iv	0.94	1.83	2.752 (3)	170
O1′′—H1′′O···O3W^v	0.93	1.95	2.809 (3)	152
O3′′—H3′′O···O6′′^vi	0.94	1.73	2.645 (3)	166
O4′′—H4′′O···O4^vii	0.91	1.83	2.735 (3)	169
O6′′—H6′′O···O3′^viii	0.95	1.86	2.799 (3)	168
O1W—H1WA···O4W^ix	0.96	1.88	2.844 (3)	176
O1W—H1WB···O6′^x	0.92	2.06	2.954 (3)	165
O2W—H2WA···O2	0.99	1.83	2.813 (3)	171
O2W—H2WB···O1W	0.90	1.91	2.805 (3)	172
O3W—H3WA···O5W^i	0.98	1.87	2.717 (3)	144
O3W—H3WB···O4′′^ix	0.93	1.98	2.865 (3)	158
O4W—H4WA···O5	0.96	1.96	2.879 (3)	160
O4W—H4WA···O6	0.96	2.42	3.010 (3)	120
O4W—H4WB···O2′^viii	0.90	1.83	2.719 (3)	169
O5W—H5WA···O2W	0.92	1.91	2.833 (3)	175
O5W—H5WB···O3′′^v	0.93	2.00	2.888 (3)	160

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1/2, −y+3/2, −z; (iii) x−1/2, −y+1/2, −z; (iv) x−1/2, −y+3/2, −z; (v) −x+1, y−1/2, −z+1/2; (vi) −x, y+1/2, −z+1/2; (vii) −x, y−1/2, −z+1/2; (viii) x+1/2, −y+1/2, −z; (ix) x+1, y, z; (x) x+1, y−1, z.

(II) O-α-D-Galactopyranosyl-(1 → 6)-α-D-glucopyranosyl-(1 → 2)-β-D-fructofuranose 4.433-hydrate

Crystal data

C18H32O16·4.433H2O	F(000) = 1249.20
Mr = 584.26	Dx = 1.497 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2ac 2ab	Cell parameters from 23307 reflections
a = 8.91348 (16) Å	θ = 4.1–68.2°
b = 12.2915 (2) Å	µ = 1.22 mm^−1
c = 23.6567 (7) Å	T = 93 K
V = 2591.84 (10) Å^3	Block, colourless
Z = 4	0.15 × 0.12 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	4568 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.028
ω scans	θmax = 68.2°, θmin = 4.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.707, Tmax = 0.864	k = −14→14
29137 measured reflections	l = −27→28
4743 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0082P)^2 + 4.6616P] where P = (Fo^2 + 2Fc^2)/3
S = 1.19	(Δ/σ)max < 0.001
4740 reflections	Δρmax = 0.27 e Å^−3
362 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Absolute structure: Flack x parameter determined using 1899 quotients [(I^+) - (I^-)]/[(I^+) + (I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (4)
Secondary atom site location: difference Fourier map

Special details

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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2789 (5)	0.3220 (4)	0.14196 (19)	0.0163 (9)
H1	0.2987	0.2461	0.1286	0.020*
C2	0.3949 (5)	0.3996 (4)	0.11615 (19)	0.0172 (9)
H2	0.3860	0.3940	0.0741	0.021*
C3	0.3605 (5)	0.5173 (4)	0.13253 (19)	0.0175 (9)
H3	0.3757	0.5266	0.1741	0.021*
C4	0.1997 (5)	0.5459 (4)	0.1176 (2)	0.0179 (9)
H4	0.1880	0.5472	0.0756	0.021*
C5	0.0917 (5)	0.4636 (3)	0.14269 (18)	0.0163 (9)
H5	0.0984	0.4674	0.1848	0.020*
C6	−0.0696 (5)	0.4820 (4)	0.12524 (17)	0.0156 (9)
H6A	−0.1350	0.4264	0.1428	0.019*
H6B	−0.1034	0.5546	0.1380	0.019*
C1'	−0.2215 (5)	0.5069 (4)	0.04490 (19)	0.0175 (9)
H1'	−0.3005	0.4694	0.0677	0.021*
C2'	−0.2353 (5)	0.4717 (3)	−0.01677 (19)	0.0172 (9)
H2'	−0.3397	0.4887	−0.0294	0.021*
C3'	−0.1277 (5)	0.5360 (3)	−0.05433 (18)	0.0168 (9)
H3'	−0.0222	0.5157	−0.0445	0.020*
C4'	−0.1491 (5)	0.6587 (4)	−0.04472 (19)	0.0180 (9)
H4'	−0.0685	0.6984	−0.0657	0.022*
C5'	−0.1326 (5)	0.6838 (3)	0.01781 (19)	0.0171 (9)
H5'	−0.0293	0.6634	0.0305	0.021*
C6'	−0.1625 (5)	0.8019 (4)	0.0326 (2)	0.0198 (10)
H6'A	−0.2597	0.8246	0.0161	0.024*
H6'B	−0.1698	0.8096	0.0742	0.024*
C1''	0.3797 (5)	0.2120 (3)	0.27357 (19)	0.0172 (9)
H1''A	0.4639	0.1880	0.2493	0.021*
H1''B	0.4129	0.2768	0.2950	0.021*
C2''	0.2466 (5)	0.2415 (3)	0.23698 (19)	0.0162 (9)
C3''	0.1052 (5)	0.2776 (3)	0.2689 (2)	0.0179 (9)
H3''	0.0982	0.2361	0.3052	0.021*
C4''	−0.0197 (5)	0.2403 (4)	0.2295 (2)	0.0187 (10)
H4''	−0.0228	0.2915	0.1967	0.022*
C5''	0.0417 (5)	0.1323 (4)	0.20865 (19)	0.0183 (9)
H5''	0.0182	0.0745	0.2370	0.022*
C6''	−0.0110 (5)	0.0956 (4)	0.1511 (2)	0.0201 (10)
H6''A	−0.1220	0.0966	0.1500	0.024*
H6''B	0.0260	0.1471	0.1221	0.024*
O1	0.2984 (3)	0.3273 (2)	0.20075 (12)	0.0147 (6)
O2	0.5429 (3)	0.3671 (3)	0.13107 (13)	0.0191 (7)
H2O	0.5654	0.3922	0.1696	0.023*
O3	0.4567 (3)	0.5912 (3)	0.10272 (13)	0.0207 (7)
H3O	0.5394	0.6158	0.1236	0.025*
O4	0.1581 (3)	0.6492 (2)	0.14038 (13)	0.0188 (7)
H4O	0.1796	0.7034	0.1197	0.023*
O5	0.1318 (3)	0.3548 (2)	0.12470 (12)	0.0164 (6)
O6	−0.0793 (3)	0.4748 (2)	0.06457 (12)	0.0158 (6)
O2'	−0.2139 (3)	0.3575 (2)	−0.02263 (13)	0.0198 (7)
H2'O	−0.1280	0.3322	−0.0098	0.024*
O3'	−0.1536 (4)	0.5124 (2)	−0.11259 (12)	0.0192 (7)
H3'O	−0.0851	0.4585	−0.1215	0.023*
O4'	−0.2912 (4)	0.6939 (2)	−0.06579 (13)	0.0191 (7)
H4'O	−0.3828	0.6706	−0.0445	0.023*
O5'	−0.2413 (3)	0.6225 (2)	0.04962 (12)	0.0161 (6)
O6'	−0.0462 (3)	0.8711 (3)	0.01191 (13)	0.0200 (7)
H6'O	−0.0538	0.8870	−0.0291	0.024*
O1''	0.3412 (3)	0.1268 (2)	0.31215 (12)	0.0187 (7)
H1''O	0.3281	0.0612	0.2970	0.022*
O2''	0.2037 (3)	0.1481 (2)	0.20632 (13)	0.0186 (7)
O3''	0.1120 (3)	0.3896 (2)	0.28114 (13)	0.0187 (7)
H3''O	0.0531	0.4120	0.3121	0.022*
O4''	−0.1660 (3)	0.2367 (3)	0.25380 (14)	0.0214 (7)
H4''O	−0.1561	0.2077	0.2876	0.026*
O6''	0.0410 (4)	−0.0115 (2)	0.13788 (13)	0.0203 (7)
H6''O	0.1449	−0.0014	0.1298	0.024*
O1W	0.7963 (10)	0.0857 (7)	0.0361 (4)	0.036 (3)	0.433 (8)
H1WA	0.8675	0.1438	0.0317	0.043*	0.433 (8)
H1WB	0.8534	0.0239	0.0349	0.043*	0.433 (8)
O2W	0.5840 (4)	0.1418 (3)	0.11853 (14)	0.0239 (7)
H2WA	0.5871	0.2169	0.1262	0.029*
H2WB	0.6363	0.1524	0.0853	0.029*
O3W	0.6462 (4)	0.4195 (3)	0.23571 (13)	0.0226 (7)
H3WA	0.5680	0.4378	0.2605	0.027*
H3WB	0.7182	0.3727	0.2518	0.027*
O4W	0.0168 (9)	0.2513 (7)	0.0246 (4)	0.030 (2)	0.433 (8)
H4WA	0.0454	0.2997	0.0544	0.036*	0.433 (8)
H4WB	0.1058	0.2175	0.0196	0.036*	0.433 (8)
O5W	0.6031 (4)	0.0004 (3)	0.21357 (15)	0.0281 (8)
H5WA	0.6197	0.0527	0.1901	0.034*
H5WB	0.6952	−0.0363	0.2190	0.034*
O6W	0.0899 (7)	0.3106 (4)	0.0018 (2)	0.0183 (16)	0.567 (8)
H6WA	0.1471	0.2404	0.0030	0.022*	0.567 (8)
H6WB	0.0816	0.3428	0.0379	0.022*	0.567 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.015 (2)	0.015 (2)	0.019 (2)	0.0017 (18)	−0.0002 (18)	−0.0002 (18)
C2	0.013 (2)	0.020 (2)	0.018 (2)	0.0013 (18)	0.0018 (18)	0.0029 (18)
C3	0.018 (2)	0.019 (2)	0.016 (2)	−0.0014 (19)	0.0025 (18)	0.0030 (18)
C4	0.017 (2)	0.018 (2)	0.019 (2)	0.0024 (18)	0.0002 (18)	−0.0020 (18)
C5	0.018 (2)	0.014 (2)	0.016 (2)	0.0004 (18)	−0.0021 (18)	0.0023 (18)
C6	0.016 (2)	0.018 (2)	0.013 (2)	0.0031 (17)	0.0013 (17)	0.0011 (17)
C1'	0.017 (2)	0.012 (2)	0.024 (2)	−0.0002 (18)	0.0026 (19)	0.0046 (18)
C2'	0.014 (2)	0.015 (2)	0.023 (2)	0.0012 (17)	−0.0022 (19)	0.0003 (19)
C3'	0.014 (2)	0.019 (2)	0.017 (2)	0.0013 (18)	−0.0021 (18)	−0.0003 (18)
C4'	0.014 (2)	0.017 (2)	0.023 (2)	0.0000 (18)	0.0020 (19)	0.0037 (19)
C5'	0.016 (2)	0.014 (2)	0.022 (2)	−0.0002 (17)	−0.0005 (19)	0.0037 (18)
C6'	0.018 (2)	0.016 (2)	0.025 (2)	0.0012 (18)	0.0023 (19)	−0.0010 (18)
C1''	0.017 (2)	0.013 (2)	0.021 (2)	−0.0013 (17)	−0.0011 (19)	0.0014 (18)
C2''	0.017 (2)	0.011 (2)	0.021 (2)	−0.0024 (18)	0.0011 (18)	0.0002 (18)
C3''	0.018 (2)	0.013 (2)	0.022 (2)	−0.0028 (18)	0.0026 (19)	−0.0002 (18)
C4''	0.017 (2)	0.019 (2)	0.020 (2)	−0.0045 (19)	0.0022 (19)	−0.0001 (19)
C5''	0.013 (2)	0.020 (2)	0.022 (2)	−0.0041 (19)	0.0022 (18)	0.0010 (19)
C6''	0.021 (2)	0.014 (2)	0.024 (3)	−0.0010 (19)	0.0008 (19)	0.0010 (19)
O1	0.0137 (15)	0.0132 (14)	0.0171 (15)	−0.0018 (12)	0.0007 (12)	−0.0010 (12)
O2	0.0152 (15)	0.0204 (16)	0.0218 (16)	0.0028 (14)	0.0020 (13)	−0.0011 (14)
O3	0.0144 (15)	0.0195 (16)	0.0280 (18)	−0.0039 (13)	−0.0006 (14)	0.0065 (14)
O4	0.0216 (16)	0.0111 (14)	0.0235 (16)	−0.0001 (13)	0.0029 (14)	0.0020 (13)
O5	0.0135 (15)	0.0156 (15)	0.0200 (16)	0.0013 (13)	−0.0006 (12)	0.0003 (13)
O6	0.0148 (16)	0.0177 (15)	0.0147 (15)	0.0015 (12)	−0.0008 (12)	0.0033 (12)
O2'	0.0167 (15)	0.0143 (15)	0.0285 (18)	−0.0012 (13)	−0.0029 (13)	−0.0015 (14)
O3'	0.0210 (16)	0.0172 (15)	0.0195 (16)	0.0032 (13)	0.0018 (13)	−0.0038 (13)
O4'	0.0179 (16)	0.0175 (16)	0.0219 (17)	0.0033 (13)	−0.0004 (13)	0.0029 (13)
O5'	0.0136 (15)	0.0146 (15)	0.0203 (15)	−0.0010 (12)	0.0036 (13)	0.0017 (13)
O6'	0.0181 (15)	0.0196 (16)	0.0224 (16)	−0.0036 (13)	−0.0029 (13)	0.0020 (14)
O1''	0.0218 (16)	0.0140 (15)	0.0203 (16)	0.0003 (13)	−0.0001 (13)	0.0010 (13)
O2''	0.0169 (15)	0.0135 (15)	0.0253 (17)	−0.0012 (13)	0.0014 (13)	−0.0055 (13)
O3''	0.0208 (16)	0.0133 (15)	0.0219 (16)	0.0001 (12)	0.0058 (13)	−0.0017 (12)
O4''	0.0139 (16)	0.0245 (17)	0.0259 (17)	0.0002 (13)	0.0047 (14)	0.0036 (14)
O6''	0.0182 (16)	0.0180 (16)	0.0247 (17)	−0.0026 (13)	0.0033 (14)	−0.0030 (13)
O1W	0.032 (5)	0.023 (4)	0.052 (6)	0.000 (4)	0.000 (4)	0.001 (4)
O2W	0.0233 (17)	0.0225 (16)	0.0259 (17)	−0.0034 (15)	0.0025 (14)	−0.0004 (14)
O3W	0.0197 (17)	0.0222 (17)	0.0257 (17)	0.0024 (14)	0.0009 (14)	0.0026 (14)
O4W	0.024 (5)	0.022 (4)	0.045 (5)	0.002 (4)	−0.008 (4)	−0.006 (4)
O5W	0.0203 (17)	0.0260 (18)	0.038 (2)	0.0021 (15)	0.0001 (16)	0.0106 (16)
O6W	0.024 (3)	0.018 (3)	0.013 (3)	0.007 (3)	−0.002 (2)	−0.005 (2)

Geometric parameters (Å, º)

C1—C2	1.533 (6)	C5—H5	1.00
C1—O1	1.403 (5)	C6—H6A	0.99
C1—O5	1.431 (5)	C6—H6B	0.99
C2—C3	1.529 (6)	C1'—H1'	1.00
C2—O2	1.423 (5)	C2'—H2'	1.00
C3—C4	1.518 (6)	C3'—H3'	1.00
C3—O3	1.434 (5)	C4'—H4'	1.00
C4—C5	1.517 (6)	C5'—H5'	1.00
C4—O4	1.429 (5)	C6'—H6'A	0.99
C5—C6	1.513 (6)	C6'—H6'B	0.99
C5—O5	1.448 (5)	C1''—H1''A	0.99
C6—O6	1.441 (5)	C1''—H1''B	0.99
C1'—C2'	1.527 (6)	C3''—H3''	1.00
C1'—O6	1.407 (5)	C4''—H4''	1.00
C1'—O5'	1.436 (5)	C5''—H5''	1.00
C2'—C3'	1.527 (6)	C6''—H6''A	0.99
C2'—O2'	1.423 (5)	C6''—H6''B	0.99
C3'—C4'	1.538 (6)	O2—H2O	0.98
C3'—O3'	1.427 (5)	O3—H3O	0.99
C4'—C5'	1.518 (6)	O4—H4O	0.85
C4'—O4'	1.428 (5)	O2'—H2'O	0.88
C5'—C6'	1.518 (6)	O3'—H3'O	0.93
C5'—O5'	1.440 (5)	O4'—H4'O	1.00
C6'—O6'	1.428 (6)	O6'—H6'O	0.99
C1''—C2''	1.513 (6)	O1''—H1''O	0.89
C1''—O1''	1.430 (5)	O3''—H3''O	0.94
C2''—C3''	1.535 (6)	O4''—H4''O	0.88
C2''—O1	1.435 (5)	O6''—H6''O	0.95
C2''—O2''	1.411 (5)	O1W—H1WA	0.96
C3''—C4''	1.522 (7)	O1W—H1WB	0.91
C3''—O3''	1.408 (5)	O2W—H2WA	0.94
C4''—C5''	1.518 (7)	O2W—H2WB	0.92
C4''—O4''	1.426 (6)	O3W—H3WA	0.94
C5''—C6''	1.511 (7)	O3W—H3WB	0.94
C5''—O2''	1.458 (5)	O4W—H4WA	0.96
C6''—O6''	1.429 (6)	O4W—H4WB	0.90
C1—H1	1.00	O5W—H5WA	0.86
C2—H2	1.00	O5W—H5WB	0.95
C3—H3	1.00	O6W—H6WA	1.00
C4—H4	1.00	O6W—H6WB	0.94
C2—C1—O1	106.4 (3)	H4—C4—O4	109
C2—C1—O5	109.2 (3)	C4—C5—H5	109
O1—C1—O5	112.5 (3)	H5—C5—C6	109
C1—C2—C3	110.7 (4)	H5—C5—O5	109
C1—C2—O2	110.6 (4)	C5—C6—H6A	110
C3—C2—O2	112.9 (4)	C5—C6—H6B	110
C2—C3—C4	110.4 (4)	H6A—C6—H6B	108
C2—C3—O3	110.8 (4)	H6A—C6—O6	110
C4—C3—O3	107.7 (3)	H6B—C6—O6	110
C3—C4—C5	110.7 (4)	H1'—C1'—C2'	109
C3—C4—O4	111.3 (4)	H1'—C1'—O6	109
C5—C4—O4	106.3 (3)	H1'—C1'—O5'	109
C4—C5—C6	113.4 (4)	C1'—C2'—H2'	108
C4—C5—O5	110.1 (3)	H2'—C2'—C3'	108
C6—C5—O5	107.0 (3)	H2'—C2'—O2'	108
C5—C6—O6	108.6 (3)	C2'—C3'—H3'	109
C2'—C1'—O6	108.0 (3)	H3'—C3'—C4'	109
C2'—C1'—O5'	110.2 (3)	H3'—C3'—O3'	109
O6—C1'—O5'	111.3 (3)	C3'—C4'—H4'	108
C1'—C2'—C3'	111.0 (4)	H4'—C4'—C5'	108
C1'—C2'—O2'	111.2 (3)	H4'—C4'—O4'	108
C3'—C2'—O2'	111.7 (4)	C4'—C5'—H5'	109
C2'—C3'—C4'	110.1 (4)	H5'—C5'—C6'	109
C2'—C3'—O3'	110.8 (3)	H5'—C5'—O5'	109
C4'—C3'—O3'	108.8 (3)	C5'—C6'—H6'A	109
C3'—C4'—C5'	109.3 (4)	C5'—C6'—H6'B	109
C3'—C4'—O4'	110.8 (3)	H6'A—C6'—H6'B	108
C5'—C4'—O4'	111.4 (4)	H6'A—C6'—O6'	109
C4'—C5'—C6'	113.7 (4)	H6'B—C6'—O6'	109
C4'—C5'—O5'	109.8 (3)	H1''A—C1''—H1''B	108
C6'—C5'—O5'	105.2 (3)	H1''A—C1''—C2''	110
C5'—C6'—O6'	111.3 (4)	H1''A—C1''—O1''	110
C2''—C1''—O1''	110.7 (4)	H1''B—C1''—C2''	110
C1''—C2''—C3''	115.6 (4)	H1''B—C1''—O1''	110
C1''—C2''—O1	105.4 (3)	C2''—C3''—H3''	109
C1''—C2''—O2''	108.1 (3)	H3''—C3''—C4''	109
C3''—C2''—O1	110.2 (3)	H3''—C3''—O3''	109
C3''—C2''—O2''	105.4 (3)	C3''—C4''—H4''	108
O1—C2''—O2''	112.2 (3)	H4''—C4''—C5''	108
C2''—C3''—C4''	102.2 (4)	H4''—C4''—O4''	108
C2''—C3''—O3''	110.4 (4)	C4''—C5''—H5''	109
C4''—C3''—O3''	116.8 (4)	H5''—C5''—C6''	109
C3''—C4''—C5''	101.5 (4)	H5''—C5''—O2''	109
C3''—C4''—O4''	115.6 (4)	C5''—C6''—H6''A	109
C5''—C4''—O4''	115.7 (4)	C5''—C6''—H6''B	109
C4''—C5''—C6''	116.3 (4)	H6''A—C6''—H6''B	108
C4''—C5''—O2''	104.7 (3)	H6''A—C6''—O6''	109
C6''—C5''—O2''	108.3 (4)	H6''B—C6''—O6''	109
C5''—C6''—O6''	111.8 (4)	C2—O2—H2O	109
C1—O1—C2''	121.2 (3)	C3—O3—H3O	115
C1—O5—C5	113.7 (3)	C4—O4—H4O	115
C6—O6—C1'	111.5 (3)	C2'—O2'—H2'O	116
C1'—O5'—C5'	113.2 (3)	C3'—O3'—H3'O	105
C2''—O2''—C5''	110.9 (3)	C4'—O4'—H4'O	117
H1—C1—C2	110	C6'—O6'—H6'O	114
H1—C1—O1	110	C1''—O1''—H1''O	116
H1—C1—O5	110	C3''—O3''—H3''O	115
C1—C2—H2	107	C4''—O4''—H4''O	107
H2—C2—C3	107	C6''—O6''—H6''O	104
H2—C2—O2	107	H1WA—O1W—H1WB	104
C2—C3—H3	109	H2WA—O2W—H2WB	91
H3—C3—C4	109	H3WA—O3W—H3WB	114
H3—C3—O3	109	H4WA—O4W—H4WB	99
C3—C4—H4	109	H5WA—O5W—H5WB	107
H4—C4—C5	109	H6WA—O6W—H6WB	112
C2—C1—O1—C2''	−158.9 (3)	C2'—C3'—C4'—O4'	−68.7 (4)
O1—C1—C2—C3	−65.7 (4)	O3'—C3'—C4'—C5'	176.1 (3)
O1—C1—C2—O2	60.2 (4)	O3'—C3'—C4'—O4'	52.9 (4)
C2—C1—O5—C5	−60.7 (4)	C3'—C4'—C5'—C6'	−175.9 (3)
O5—C1—C2—C3	56.0 (4)	C3'—C4'—C5'—O5'	−58.5 (4)
O5—C1—C2—O2	−178.2 (3)	O4'—C4'—C5'—C6'	−53.1 (4)
O1—C1—O5—C5	57.2 (4)	O4'—C4'—C5'—O5'	64.3 (4)
O5—C1—O1—C2''	81.6 (4)	C4'—C5'—C6'—O6'	−70.2 (5)
C1—C2—C3—C4	−53.3 (4)	C4'—C5'—O5'—C1'	62.6 (4)
C1—C2—C3—O3	−172.6 (3)	C6'—C5'—O5'—C1'	−174.7 (3)
O2—C2—C3—C4	−177.9 (3)	O5'—C5'—C6'—O6'	169.7 (3)
O2—C2—C3—O3	62.9 (4)	O1''—C1''—C2''—C3''	57.6 (4)
C2—C3—C4—C5	52.9 (5)	O1''—C1''—C2''—O1	179.6 (3)
C2—C3—C4—O4	170.9 (3)	O1''—C1''—C2''—O2''	−60.2 (4)
O3—C3—C4—C5	174.0 (3)	C1''—C2''—C3''—C4''	−149.5 (3)
O3—C3—C4—O4	−68.0 (4)	C1''—C2''—C3''—O3''	85.5 (4)
C3—C4—C5—C6	−175.1 (3)	C1''—C2''—O1—C1	128.7 (3)
C3—C4—C5—O5	−55.3 (4)	C1''—C2''—O2''—C5''	133.6 (3)
O4—C4—C5—C6	63.9 (4)	C3''—C2''—O1—C1	−106.0 (4)
O4—C4—C5—O5	−176.3 (3)	O1—C2''—C3''—C4''	91.1 (3)
C4—C5—C6—O6	59.8 (4)	O1—C2''—C3''—O3''	−33.9 (5)
C4—C5—O5—C1	60.8 (4)	C3''—C2''—O2''—C5''	9.5 (4)
C6—C5—O5—C1	−175.6 (3)	O2''—C2''—C3''—C4''	−30.2 (4)
O5—C5—C6—O6	−61.8 (4)	O2''—C2''—C3''—O3''	−155.2 (3)
C5—C6—O6—C1'	−171.3 (3)	O1—C2''—O2''—C5''	−110.6 (3)
C2'—C1'—O6—C6	−166.7 (3)	O2''—C2''—O1—C1	11.2 (5)
O6—C1'—C2'—C3'	−67.5 (4)	C2''—C3''—C4''—C5''	38.4 (4)
O6—C1'—C2'—O2'	57.4 (4)	C2''—C3''—C4''—O4''	164.3 (3)
C2'—C1'—O5'—C5'	−59.9 (4)	O3''—C3''—C4''—C5''	159.0 (3)
O5'—C1'—C2'—C3'	54.2 (4)	O3''—C3''—C4''—O4''	−75.1 (5)
O5'—C1'—C2'—O2'	179.2 (3)	C3''—C4''—C5''—C6''	−152.8 (3)
O6—C1'—O5'—C5'	59.9 (4)	C3''—C4''—C5''—O2''	−33.4 (4)
O5'—C1'—O6—C6	72.3 (4)	O4''—C4''—C5''—C6''	81.3 (5)
C1'—C2'—C3'—C4'	−52.6 (4)	O4''—C4''—C5''—O2''	−159.3 (3)
C1'—C2'—C3'—O3'	−173.0 (3)	C4''—C5''—C6''—O6''	−174.1 (3)
O2'—C2'—C3'—C4'	−177.3 (3)	C4''—C5''—O2''—C2''	15.3 (4)
O2'—C2'—C3'—O3'	62.3 (4)	C6''—C5''—O2''—C2''	140.0 (3)
C2'—C3'—C4'—C5'	54.5 (4)	O2''—C5''—C6''—O6''	68.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3W	0.98	1.76	2.719 (4)	166
O3—H3O···O1′′^i	0.94	1.86	2.737 (4)	155
O4—H4O···O4′^ii	0.85	1.81	2.652 (4)	170
O2′—H2′O···O4W	0.88	1.82	2.680 (9)	164
O2′—H2′O···O6W	0.88	1.98	2.829 (7)	162
O3′—H3′O···O2W^iii	0.93	1.95	2.846 (4)	163
O4′—H4′O···O6′^iv	1.00	1.73	2.726 (4)	176
O6′—H6′O···O3^iv	0.99	1.77	2.751 (4)	173
O1′′—H1′′O···O3W^v	0.89	1.92	2.791 (4)	166
O3′′—H3′′O···O6′′^vi	0.94	1.73	2.647 (4)	164
O4′′—H4′′O···O4^vii	0.88	1.85	2.725 (4)	174
O6′′—H6′′O···O3′^viii	0.95	1.85	2.787 (5)	168
O1W—H1WA···O4W^ix	0.96	1.88	2.843 (12)	176
O1W—H1WB···O6′^x	0.91	2.15	3.041 (9)	165
O2W—H2WA···O2	0.94	1.89	2.809 (5)	164
O2W—H2WB···O1W	0.92	2.02	2.803 (9)	142
O2W—H2WB···O6W^viii	0.92	2.15	2.907 (6)	139
O3W—H3WA···O5W^i	0.94	1.82	2.714 (5)	160
O3W—H3WB···O4′′^ix	0.94	1.97	2.835 (5)	153
O4W—H4WA···O5	0.96	1.95	2.876 (9)	161
O4W—H4WA···O6	0.96	2.43	3.029 (9)	120
O4W—H4WB···O2′^viii	0.90	1.85	2.748 (9)	170
O5W—H5WA···O2W	0.86	2.04	2.847 (5)	155
O5W—H5WB···O3′′^v	0.95	1.95	2.884 (5)	172
O6W—H6WA···O2′^viii	1.00	1.79	2.752 (6)	160
O6W—H6WB···O5	0.94	2.11	2.981 (6)	153
O6W—H6WB···O6	0.94	2.26	2.924 (6)	127

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1/2, −y+3/2, −z; (iii) x−1/2, −y+1/2, −z; (iv) x−1/2, −y+3/2, −z; (v) −x+1, y−1/2, −z+1/2; (vi) −x, y+1/2, −z+1/2; (vii) −x, y−1/2, −z+1/2; (viii) x+1/2, −y+1/2, −z; (ix) x+1, y, z; (x) x+1, y−1, z.

(III) O-α-D-Galactopyranosyl-(1 → 6)-α-D-glucopyranosyl-(1 → 2)-β-D-fructofuranose 4.289-hydrate

Crystal data

C18H32O16·4.289H2O	F(000) = 1243.60
Mr = 581.73	Dx = 1.491 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2ac 2ab	Cell parameters from 21962 reflections
a = 8.91926 (16) Å	θ = 3.6–68.3°
b = 12.3038 (2) Å	µ = 1.21 mm^−1
c = 23.6118 (7) Å	T = 93 K
V = 2591.18 (10) Å^3	Block, colourless
Z = 4	0.18 × 0.14 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	4541 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.033
ω scans	θmax = 68.2°, θmin = 3.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.634, Tmax = 0.865	k = −14→14
23231 measured reflections	l = −28→28
4729 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0318P)^2 + 3.4655P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
4727 reflections	Δρmax = 0.26 e Å^−3
362 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Absolute structure: Flack x parameter determined using 1873 quotients [(I^+) - (I^-)]/[(I^+) + (I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (5)
Secondary atom site location: difference Fourier map

Special details

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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2796 (4)	0.3239 (3)	0.14163 (17)	0.0195 (8)
H1	0.2998	0.2483	0.1281	0.023*
C2	0.3958 (4)	0.4014 (3)	0.11638 (17)	0.0201 (8)
H2	0.3877	0.3963	0.0742	0.024*
C3	0.3616 (4)	0.5188 (3)	0.13295 (16)	0.0203 (8)
H3	0.3765	0.5277	0.1747	0.024*
C4	0.2000 (4)	0.5477 (3)	0.11797 (17)	0.0199 (8)
H4	0.1887	0.5495	0.0758	0.024*
C5	0.0931 (4)	0.4652 (3)	0.14235 (16)	0.0197 (8)
H5	0.0998	0.4684	0.1846	0.024*
C6	−0.0684 (4)	0.4832 (3)	0.12526 (16)	0.0192 (8)
H6A	−0.1333	0.4277	0.1431	0.023*
H6B	−0.1023	0.5559	0.1380	0.023*
C1'	−0.2206 (4)	0.5078 (3)	0.04494 (17)	0.0191 (8)
H1'	−0.2994	0.4706	0.0680	0.023*
C2'	−0.2349 (4)	0.4715 (3)	−0.01685 (17)	0.0201 (8)
H2'	−0.3395	0.4880	−0.0294	0.024*
C3'	−0.1285 (4)	0.5362 (3)	−0.05481 (16)	0.0196 (8)
H3'	−0.0229	0.5164	−0.0451	0.024*
C4'	−0.1497 (4)	0.6581 (3)	−0.04554 (17)	0.0205 (8)
H4'	−0.0694	0.6976	−0.0667	0.025*
C5'	−0.1329 (4)	0.6833 (3)	0.01743 (17)	0.0198 (8)
H5'	−0.0296	0.6628	0.0300	0.024*
C6'	−0.1610 (5)	0.8017 (3)	0.03202 (17)	0.0213 (8)
H6'A	−0.2577	0.8249	0.0154	0.026*
H6'B	−0.1684	0.8096	0.0737	0.026*
C1''	0.3779 (5)	0.2119 (3)	0.27346 (17)	0.0210 (8)
H1''A	0.4623	0.1880	0.2493	0.025*
H1''B	0.4109	0.2765	0.2951	0.025*
C2''	0.2456 (4)	0.2419 (3)	0.23659 (17)	0.0193 (8)
C3''	0.1049 (4)	0.2786 (3)	0.26855 (17)	0.0200 (8)
H3''	0.0975	0.2370	0.3048	0.024*
C4''	−0.0205 (4)	0.2420 (3)	0.22897 (17)	0.0210 (8)
H4''	−0.0235	0.2931	0.1961	0.025*
C5''	0.0404 (4)	0.1336 (3)	0.20816 (17)	0.0215 (8)
H5''	0.0169	0.0759	0.2366	0.026*
C6''	−0.0116 (5)	0.0971 (3)	0.15034 (17)	0.0231 (9)
H6''A	−0.1225	0.0988	0.1490	0.028*
H6''B	0.0266	0.1482	0.1213	0.028*
O1	0.2982 (3)	0.3283 (2)	0.20057 (11)	0.0189 (6)
O2	0.5433 (3)	0.3687 (2)	0.13153 (12)	0.0222 (6)
H2O	0.5650	0.3960	0.1676	0.027*
O3	0.4573 (3)	0.5926 (2)	0.10359 (12)	0.0226 (6)
H3O	0.5287	0.6165	0.1289	0.027*
O4	0.1585 (3)	0.6503 (2)	0.14068 (11)	0.0218 (6)
H4O	0.1646	0.7080	0.1120	0.026*
O5	0.1329 (3)	0.3563 (2)	0.12413 (11)	0.0188 (6)
O6	−0.0784 (3)	0.4755 (2)	0.06446 (11)	0.0196 (6)
O2'	−0.2134 (3)	0.3571 (2)	−0.02218 (12)	0.0222 (6)
H2'O	−0.1255	0.3383	−0.0121	0.027*
O3'	−0.1546 (3)	0.5116 (2)	−0.11291 (11)	0.0223 (6)
H3'O	−0.1044	0.4466	−0.1226	0.027*
O4'	−0.2920 (3)	0.6933 (2)	−0.06622 (12)	0.0213 (6)
H4'O	−0.3684	0.6648	−0.0418	0.026*
O5'	−0.2403 (3)	0.6223 (2)	0.04945 (11)	0.0194 (6)
O6'	−0.0442 (3)	0.8700 (2)	0.01133 (11)	0.0230 (6)
H6'O	−0.0533	0.8994	−0.0263	0.028*
O1''	0.3392 (3)	0.1271 (2)	0.31163 (11)	0.0224 (6)
H1''O	0.3356	0.0606	0.2946	0.027*
O2''	0.2023 (3)	0.1494 (2)	0.20552 (12)	0.0210 (6)
O3''	0.1119 (3)	0.3904 (2)	0.28091 (11)	0.0222 (6)
H3''O	0.0582	0.4061	0.3119	0.027*
O4''	−0.1666 (3)	0.2381 (2)	0.25323 (12)	0.0237 (6)
H4''O	−0.1548	0.2047	0.2880	0.028*
O6''	0.0395 (3)	−0.0105 (2)	0.13749 (12)	0.0238 (6)
H6''O	0.1421	−0.0058	0.1295	0.029*
O1W	0.7954 (18)	0.0864 (12)	0.0368 (7)	0.064 (5)	0.289 (9)
H1WA	0.8665	0.1443	0.0325	0.076*	0.289 (9)
H1WB	0.8525	0.0245	0.0357	0.076*	0.289 (9)
O2W	0.5829 (3)	0.1441 (2)	0.11788 (12)	0.0268 (6)
H2WA	0.5694	0.2201	0.1269	0.032*
H2WB	0.5986	0.1488	0.0765	0.032*
O3W	0.6458 (3)	0.4207 (2)	0.23649 (12)	0.0249 (6)
H3WB	0.7178	0.3734	0.2526	0.030*
H3WA	0.5657	0.4396	0.2607	0.030*
O4W	0.0179 (17)	0.2524 (12)	0.0253 (7)	0.059 (5)	0.289 (9)
H4WA	0.0465	0.3007	0.0552	0.070*	0.289 (9)
H4WB	0.1069	0.2186	0.0203	0.070*	0.289 (9)
O5W	0.6040 (3)	0.0005 (3)	0.21237 (13)	0.0307 (7)
H5WB	0.6926	−0.0310	0.2159	0.037*
H5WA	0.6212	0.0494	0.1855	0.037*
O6W	0.0900 (4)	0.3109 (3)	0.00182 (16)	0.0185 (12)	0.711 (9)
H6WA	0.1473	0.2408	0.0029	0.022*	0.711 (9)
H6WB	0.0818	0.3430	0.0379	0.022*	0.711 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0177 (18)	0.018 (2)	0.0224 (19)	0.0035 (16)	−0.0001 (16)	−0.0006 (16)
C2	0.0160 (18)	0.024 (2)	0.0205 (19)	0.0017 (16)	0.0004 (15)	0.0010 (16)
C3	0.0215 (19)	0.021 (2)	0.0188 (18)	0.0002 (16)	0.0025 (16)	0.0034 (16)
C4	0.0204 (19)	0.019 (2)	0.0202 (18)	0.0022 (16)	−0.0011 (16)	−0.0015 (16)
C5	0.0204 (19)	0.020 (2)	0.0187 (18)	0.0026 (17)	−0.0009 (16)	−0.0006 (16)
C6	0.0186 (19)	0.019 (2)	0.0196 (19)	0.0025 (15)	0.0011 (15)	−0.0009 (16)
C1'	0.0173 (18)	0.0132 (19)	0.027 (2)	0.0008 (15)	0.0032 (17)	0.0039 (16)
C2'	0.0153 (18)	0.019 (2)	0.026 (2)	−0.0001 (15)	−0.0014 (16)	−0.0009 (17)
C3'	0.0151 (19)	0.018 (2)	0.026 (2)	−0.0001 (15)	−0.0035 (16)	−0.0010 (16)
C4'	0.0160 (17)	0.019 (2)	0.027 (2)	0.0006 (16)	0.0002 (16)	0.0032 (16)
C5'	0.0180 (19)	0.016 (2)	0.026 (2)	0.0001 (15)	−0.0003 (17)	−0.0006 (16)
C6'	0.021 (2)	0.018 (2)	0.025 (2)	0.0017 (16)	0.0016 (16)	−0.0007 (16)
C1''	0.021 (2)	0.018 (2)	0.024 (2)	−0.0005 (16)	0.0011 (17)	0.0007 (16)
C2''	0.021 (2)	0.015 (2)	0.0221 (19)	−0.0014 (16)	0.0023 (16)	−0.0009 (16)
C3''	0.0200 (19)	0.018 (2)	0.0225 (19)	−0.0008 (16)	0.0019 (17)	0.0005 (16)
C4''	0.0179 (19)	0.022 (2)	0.0227 (19)	−0.0018 (17)	0.0024 (16)	0.0012 (17)
C5''	0.0176 (18)	0.022 (2)	0.025 (2)	−0.0034 (17)	0.0004 (16)	0.0033 (17)
C6''	0.025 (2)	0.018 (2)	0.026 (2)	0.0000 (17)	0.0001 (16)	−0.0001 (17)
O1	0.0190 (13)	0.0160 (14)	0.0218 (13)	−0.0006 (11)	−0.0010 (11)	0.0002 (11)
O2	0.0179 (13)	0.0233 (15)	0.0254 (14)	0.0025 (12)	0.0008 (11)	−0.0011 (12)
O3	0.0177 (13)	0.0226 (15)	0.0275 (14)	−0.0046 (12)	−0.0009 (12)	0.0049 (12)
O4	0.0242 (14)	0.0158 (14)	0.0254 (14)	0.0009 (12)	0.0025 (12)	0.0005 (11)
O5	0.0162 (13)	0.0181 (14)	0.0222 (13)	0.0012 (11)	−0.0001 (11)	−0.0005 (11)
O6	0.0158 (13)	0.0231 (15)	0.0197 (13)	0.0015 (11)	−0.0009 (11)	0.0031 (11)
O2'	0.0191 (13)	0.0170 (14)	0.0306 (15)	−0.0022 (12)	−0.0019 (12)	−0.0011 (12)
O3'	0.0236 (14)	0.0207 (14)	0.0226 (14)	0.0031 (12)	0.0011 (12)	−0.0021 (11)
O4'	0.0207 (14)	0.0199 (15)	0.0234 (14)	0.0025 (11)	−0.0010 (12)	0.0032 (11)
O5'	0.0168 (13)	0.0186 (14)	0.0227 (13)	−0.0001 (11)	0.0016 (11)	0.0019 (11)
O6'	0.0212 (13)	0.0232 (15)	0.0247 (14)	−0.0043 (12)	−0.0019 (12)	0.0015 (12)
O1''	0.0261 (14)	0.0185 (14)	0.0226 (14)	0.0027 (12)	0.0003 (12)	0.0002 (11)
O2''	0.0201 (13)	0.0166 (14)	0.0264 (14)	−0.0018 (11)	0.0013 (11)	−0.0023 (12)
O3''	0.0230 (14)	0.0184 (15)	0.0253 (14)	0.0001 (11)	0.0059 (11)	−0.0021 (11)
O4''	0.0184 (14)	0.0239 (15)	0.0289 (15)	0.0012 (12)	0.0032 (12)	0.0036 (12)
O6''	0.0215 (13)	0.0210 (15)	0.0290 (15)	−0.0028 (12)	0.0049 (12)	−0.0041 (12)
O1W	0.074 (11)	0.031 (8)	0.087 (12)	−0.004 (7)	0.012 (9)	0.003 (7)
O2W	0.0287 (15)	0.0229 (15)	0.0287 (15)	−0.0008 (13)	0.0011 (12)	−0.0001 (12)
O3W	0.0229 (14)	0.0236 (15)	0.0281 (15)	0.0012 (12)	0.0003 (12)	0.0019 (12)
O4W	0.048 (9)	0.038 (8)	0.090 (12)	−0.008 (7)	−0.001 (8)	−0.010 (8)
O5W	0.0222 (14)	0.0312 (17)	0.0388 (17)	0.0026 (13)	0.0012 (13)	0.0101 (14)
O6W	0.021 (2)	0.019 (2)	0.0152 (19)	0.0098 (18)	−0.0035 (15)	−0.0024 (15)

Geometric parameters (Å, º)

C1—C2	1.530 (6)	C5—H5	1.00
C1—O1	1.403 (5)	C6—H6A	0.99
C1—O5	1.429 (5)	C6—H6B	0.99
C2—C3	1.527 (6)	C1'—H1'	1.00
C2—O2	1.422 (5)	C2'—H2'	1.00
C3—C4	1.526 (6)	C3'—H3'	1.00
C3—O3	1.427 (5)	C4'—H4'	1.00
C4—C5	1.507 (6)	C5'—H5'	1.00
C4—O4	1.420 (5)	C6'—H6'A	0.99
C5—C6	1.512 (5)	C6'—H6'B	0.99
C5—O5	1.451 (5)	C1''—H1''A	0.99
C6—O6	1.441 (5)	C1''—H1''B	0.99
C1'—C2'	1.531 (6)	C3''—H3''	1.00
C1'—O6	1.407 (5)	C4''—H4''	1.00
C1'—O5'	1.424 (5)	C5''—H5''	1.00
C2'—C3'	1.529 (5)	C6''—H6''A	0.99
C2'—O2'	1.426 (5)	C6''—H6''B	0.99
C3'—C4'	1.526 (5)	O2—H2O	0.94
C3'—O3'	1.424 (5)	O3—H3O	0.92
C4'—C5'	1.526 (6)	O4—H4O	0.98
C4'—O4'	1.427 (5)	O2'—H2'O	0.85
C5'—C6'	1.517 (5)	O3'—H3'O	0.95
C5'—O5'	1.433 (5)	O4'—H4'O	0.96
C6'—O6'	1.425 (5)	O6'—H6'O	0.96
C1''—C2''	1.512 (6)	O1''—H1''O	0.91
C1''—O1''	1.421 (5)	O3''—H3''O	0.90
C2''—C3''	1.533 (6)	O4''—H4''O	0.93
C2''—O1	1.440 (5)	O6''—H6''O	0.94
C2''—O2''	1.408 (5)	O1W—H1WA	0.96
C3''—C4''	1.525 (6)	O1W—H1WB	0.92
C3''—O3''	1.408 (5)	O2W—H2WA	0.97
C4''—C5''	1.521 (6)	O2W—H2WB	0.99
C4''—O4''	1.424 (5)	O3W—H3WB	0.95
C5''—C6''	1.510 (6)	O3W—H3WA	0.94
C5''—O2''	1.459 (5)	O4W—H4WA	0.96
C6''—O6''	1.433 (5)	O4W—H4WB	0.90
C1—H1	1.00	O5W—H5WB	0.88
C2—H2	1.00	O5W—H5WA	0.89
C3—H3	1.00	O6W—H6WA	1.00
C4—H4	1.00	O6W—H6WB	0.94
C2—C1—O1	106.4 (3)	H4—C4—O4	109
C2—C1—O5	109.5 (3)	C4—C5—H5	108
O1—C1—O5	112.6 (3)	H5—C5—C6	108
C1—C2—C3	110.7 (3)	H5—C5—O5	108
C1—C2—O2	110.7 (3)	C5—C6—H6A	110
C3—C2—O2	112.8 (3)	C5—C6—H6B	110
C2—C3—C4	110.5 (3)	H6A—C6—H6B	108
C2—C3—O3	111.0 (3)	H6A—C6—O6	110
C4—C3—O3	107.7 (3)	H6B—C6—O6	110
C3—C4—C5	110.6 (3)	H1'—C1'—C2'	109
C3—C4—O4	111.5 (3)	H1'—C1'—O6	109
C5—C4—O4	106.8 (3)	H1'—C1'—O5'	109
C4—C5—C6	113.7 (3)	C1'—C2'—H2'	107
C4—C5—O5	110.7 (3)	H2'—C2'—C3'	107
C6—C5—O5	106.8 (3)	H2'—C2'—O2'	107
C5—C6—O6	108.4 (3)	C2'—C3'—H3'	109
C2'—C1'—O6	107.7 (3)	H3'—C3'—C4'	109
C2'—C1'—O5'	110.5 (3)	H3'—C3'—O3'	109
O6—C1'—O5'	111.5 (3)	C3'—C4'—H4'	109
C1'—C2'—C3'	110.8 (3)	H4'—C4'—C5'	109
C1'—C2'—O2'	111.2 (3)	H4'—C4'—O4'	109
C3'—C2'—O2'	112.3 (3)	C4'—C5'—H5'	109
C2'—C3'—C4'	110.5 (3)	H5'—C5'—C6'	109
C2'—C3'—O3'	110.6 (3)	H5'—C5'—O5'	109
C4'—C3'—O3'	109.1 (3)	C5'—C6'—H6'A	109
C3'—C4'—C5'	109.1 (3)	C5'—C6'—H6'B	109
C3'—C4'—O4'	111.1 (3)	H6'A—C6'—H6'B	108
C5'—C4'—O4'	111.0 (3)	H6'A—C6'—O6'	109
C4'—C5'—C6'	113.6 (3)	H6'B—C6'—O6'	109
C4'—C5'—O5'	110.0 (3)	H1''A—C1''—H1''B	108
C6'—C5'—O5'	105.8 (3)	H1''A—C1''—C2''	109
C5'—C6'—O6'	111.5 (3)	H1''A—C1''—O1''	109
C2''—C1''—O1''	110.8 (3)	H1''B—C1''—C2''	109
C1''—C2''—C3''	115.3 (3)	H1''B—C1''—O1''	109
C1''—C2''—O1	105.5 (3)	C2''—C3''—H3''	109
C1''—C2''—O2''	108.5 (3)	H3''—C3''—C4''	109
C3''—C2''—O1	109.9 (3)	H3''—C3''—O3''	109
C3''—C2''—O2''	105.6 (3)	C3''—C4''—H4''	108
O1—C2''—O2''	112.2 (3)	H4''—C4''—C5''	108
C2''—C3''—C4''	102.3 (3)	H4''—C4''—O4''	108
C2''—C3''—O3''	110.7 (3)	C4''—C5''—H5''	109
C4''—C3''—O3''	116.6 (3)	H5''—C5''—C6''	109
C3''—C4''—C5''	101.2 (3)	H5''—C5''—O2''	109
C3''—C4''—O4''	115.8 (3)	C5''—C6''—H6''A	109
C5''—C4''—O4''	115.3 (3)	C5''—C6''—H6''B	109
C4''—C5''—C6''	116.3 (3)	H6''A—C6''—H6''B	108
C4''—C5''—O2''	104.5 (3)	H6''A—C6''—O6''	109
C6''—C5''—O2''	107.8 (3)	H6''B—C6''—O6''	109
C5''—C6''—O6''	111.7 (3)	C2—O2—H2O	109
C1—O1—C2''	121.2 (3)	C3—O3—H3O	108
C1—O5—C5	113.3 (3)	C4—O4—H4O	112
C6—O6—C1'	111.3 (3)	C2'—O2'—H2'O	112
C1'—O5'—C5'	113.4 (3)	C3'—O3'—H3'O	110
C2''—O2''—C5''	110.9 (3)	C4'—O4'—H4'O	108
H1—C1—C2	109	C6'—O6'—H6'O	118
H1—C1—O1	109	C1''—O1''—H1''O	113
H1—C1—O5	109	C3''—O3''—H3''O	111
C1—C2—H2	107	C4''—O4''—H4''O	106
H2—C2—C3	107	C6''—O6''—H6''O	108
H2—C2—O2	107	H1WA—O1W—H1WB	105
C2—C3—H3	109	H2WA—O2W—H2WB	101
H3—C3—C4	109	H3WB—O3W—H3WA	116
H3—C3—O3	109	H4WA—O4W—H4WB	99
C3—C4—H4	109	H5WB—O5W—H5WA	102
H4—C4—C5	109	H6WA—O6W—H6WB	112
C2—C1—O1—C2''	−158.8 (2)	C2'—C3'—C4'—O4'	−68.6 (4)
O1—C1—C2—C3	−65.8 (4)	O3'—C3'—C4'—C5'	176.0 (3)
O1—C1—C2—O2	60.1 (4)	O3'—C3'—C4'—O4'	53.2 (4)
C2—C1—O5—C5	−60.5 (4)	C3'—C4'—C5'—C6'	−176.6 (3)
O5—C1—C2—C3	56.1 (4)	C3'—C4'—C5'—O5'	−58.2 (4)
O5—C1—C2—O2	−178.0 (3)	O4'—C4'—C5'—C6'	−53.8 (4)
O1—C1—O5—C5	57.7 (4)	O4'—C4'—C5'—O5'	64.6 (4)
O5—C1—O1—C2''	81.2 (4)	C4'—C5'—C6'—O6'	−70.2 (4)
C1—C2—C3—C4	−52.9 (4)	C4'—C5'—O5'—C1'	62.5 (3)
C1—C2—C3—O3	−172.3 (3)	C6'—C5'—O5'—C1'	−174.4 (2)
O2—C2—C3—C4	−177.6 (3)	O5'—C5'—C6'—O6'	169.1 (3)
O2—C2—C3—O3	63.0 (4)	O1''—C1''—C2''—C3''	58.1 (4)
C2—C3—C4—C5	52.3 (4)	O1''—C1''—C2''—O1	179.5 (3)
C2—C3—C4—O4	171.0 (3)	O1''—C1''—C2''—O2''	−60.1 (4)
O3—C3—C4—C5	173.7 (3)	C1''—C2''—C3''—C4''	−149.6 (3)
O3—C3—C4—O4	−67.6 (4)	C1''—C2''—C3''—O3''	85.5 (4)
C3—C4—C5—C6	−175.2 (3)	C1''—C2''—O1—C1	128.8 (3)
C3—C4—C5—O5	−55.0 (4)	C1''—C2''—O2''—C5''	132.8 (3)
O4—C4—C5—C6	63.3 (4)	C3''—C2''—O1—C1	−106.4 (3)
O4—C4—C5—O5	−176.5 (3)	O1—C2''—C3''—C4''	91.4 (3)
C4—C5—C6—O6	60.8 (4)	O1—C2''—C3''—O3''	−33.5 (4)
C4—C5—O5—C1	60.7 (3)	C3''—C2''—O2''—C5''	8.7 (4)
C6—C5—O5—C1	−175.1 (2)	O2''—C2''—C3''—C4''	−29.9 (3)
O5—C5—C6—O6	−61.6 (4)	O2''—C2''—C3''—O3''	−154.7 (3)
C5—C6—O6—C1'	−170.9 (3)	O1—C2''—O2''—C5''	−111.1 (3)
C2'—C1'—O6—C6	−166.4 (2)	O2''—C2''—O1—C1	10.9 (4)
O6—C1'—C2'—C3'	−68.4 (4)	C2''—C3''—C4''—C5''	38.4 (3)
O6—C1'—C2'—O2'	57.2 (4)	C2''—C3''—C4''—O4''	163.8 (3)
C2'—C1'—O5'—C5'	−59.8 (3)	O3''—C3''—C4''—C5''	159.3 (3)
O5'—C1'—C2'—C3'	53.6 (4)	O3''—C3''—C4''—O4''	−75.3 (4)
O5'—C1'—C2'—O2'	179.2 (3)	C3''—C4''—C5''—C6''	−152.6 (3)
O6—C1'—O5'—C5'	60.0 (4)	C3''—C4''—C5''—O2''	−33.9 (4)
O5'—C1'—O6—C6	72.2 (3)	O4''—C4''—C5''—C6''	81.7 (4)
C1'—C2'—C3'—C4'	−52.1 (4)	O4''—C4''—C5''—O2''	−159.6 (3)
C1'—C2'—C3'—O3'	−173.1 (3)	C4''—C5''—C6''—O6''	−173.9 (3)
O2'—C2'—C3'—C4'	−177.1 (3)	C4''—C5''—O2''—C2''	16.3 (4)
O2'—C2'—C3'—O3'	62.0 (4)	C6''—C5''—O2''—C2''	140.6 (3)
C2'—C3'—C4'—C5'	54.1 (4)	O2''—C5''—C6''—O6''	69.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3W	0.94	1.80	2.718 (4)	164
O3—H3O···O1′′^i	0.92	1.84	2.735 (4)	164
O4—H4O···O4′^ii	0.98	1.67	2.644 (4)	170
O2′—H2′O···O4W	0.85	1.88	2.678 (15)	156
O2′—H2′O···O6W	0.85	1.98	2.823 (5)	171
O3′—H3′O···O2W^iii	0.95	2.01	2.859 (4)	148
O4′—H4′O···O6′^iv	0.96	1.78	2.710 (4)	163
O6′—H6′O···O3^iv	0.96	1.83	2.752 (4)	159
O1′′—H1′′O···O3W^v	0.91	1.88	2.785 (4)	172
O3′′—H3′′O···O6′′^vi	0.90	1.80	2.650 (4)	158
O4′′—H4′′O···O4^vii	0.93	1.81	2.729 (4)	171
O6′′—H6′′O···O3′^viii	0.94	1.86	2.789 (4)	174
O1W—H1WA···O4W^ix	0.96	1.90	2.86 (2)	176
O1W—H1WB···O6′^x	0.92	2.19	3.083 (15)	164
O2W—H2WA···O2	0.97	1.85	2.804 (4)	171
O2W—H2WB···O1W	0.99	2.13	2.785 (16)	122
O2W—H2WB···O6W^viii	0.99	1.92	2.881 (5)	164
O3W—H3WB···O4′′^ix	0.95	1.96	2.829 (4)	152
O3W—H3WA···O5W^i	0.94	1.81	2.717 (4)	162
O4W—H4WA···O5	0.96	1.93	2.851 (16)	162
O4W—H4WA···O6	0.96	2.43	3.021 (15)	120
O4W—H4WB···O2′^viii	0.90	1.85	2.750 (15)	171
O5W—H5WB···O3′′^v	0.88	2.00	2.878 (4)	176
O5W—H5WA···O2W	0.89	2.01	2.852 (4)	159
O6W—H6WA···O2′^viii	1.00	1.79	2.753 (5)	160
O6W—H6WB···O5	0.94	2.09	2.966 (5)	154
O6W—H6WB···O6	0.94	2.26	2.923 (5)	127

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1/2, −y+3/2, −z; (iii) x−1/2, −y+1/2, −z; (iv) x−1/2, −y+3/2, −z; (v) −x+1, y−1/2, −z+1/2; (vi) −x, y+1/2, −z+1/2; (vii) −x, y−1/2, −z+1/2; (viii) x+1/2, −y+1/2, −z; (ix) x+1, y, z; (x) x+1, y−1, z.

(IV) O-α-D-Galactopyranosyl-(1 → 6)-α-D-glucopyranosyl-(1 → 2)-β-D-fructofuranose 4.127-hydrate

Crystal data

C18H32O16·4.127H2O	F(000) = 1237.20
Mr = 578.84	Dx = 1.480 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2ac 2ab	Cell parameters from 13668 reflections
a = 8.93444 (16) Å	θ = 4.1–68.2°
b = 12.3196 (2) Å	µ = 1.20 mm^−1
c = 23.6037 (4) Å	T = 93 K
V = 2598.03 (9) Å^3	Block, colourless
Z = 4	0.21 × 0.15 × 0.07 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	4509 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.055
ω scans	θmax = 68.2°, θmin = 5.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.702, Tmax = 0.919	k = −14→14
30344 measured reflections	l = −28→28
4752 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.0435P)^2 + 0.8903P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
4750 reflections	Δρmax = 0.19 e Å^−3
362 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Absolute structure: Flack x parameter determined using 1859 quotients [(I^+) - (I^-)]/[(I^+) + (I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (5)
Secondary atom site location: difference Fourier map

Special details

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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2801 (3)	0.3249 (2)	0.14146 (12)	0.0198 (6)
H1	0.3002	0.2494	0.1278	0.024*
C2	0.3965 (3)	0.4020 (2)	0.11648 (12)	0.0200 (6)
H2	0.3891	0.3969	0.0743	0.024*
C3	0.3617 (3)	0.5199 (2)	0.13313 (11)	0.0195 (6)
H3	0.3763	0.5287	0.1749	0.023*
C4	0.2004 (3)	0.5484 (2)	0.11817 (12)	0.0201 (6)
H4	0.1896	0.5504	0.0760	0.024*
C5	0.0930 (3)	0.4654 (2)	0.14220 (12)	0.0196 (6)
H5	0.0993	0.4681	0.1845	0.024*
C6	−0.0674 (3)	0.4837 (2)	0.12504 (11)	0.0206 (6)
H6A	−0.1325	0.4285	0.1430	0.025*
H6B	−0.1009	0.5563	0.1377	0.025*
C1'	−0.2203 (3)	0.5079 (2)	0.04490 (12)	0.0204 (6)
H1'	−0.2988	0.4708	0.0680	0.025*
C2'	−0.2349 (3)	0.4714 (2)	−0.01677 (12)	0.0206 (6)
H2'	−0.3394	0.4878	−0.0293	0.025*
C3'	−0.1285 (3)	0.5355 (2)	−0.05497 (12)	0.0211 (6)
H3'	−0.0230	0.5158	−0.0453	0.025*
C4'	−0.1501 (3)	0.6577 (2)	−0.04598 (12)	0.0211 (6)
H4'	−0.0703	0.6972	−0.0674	0.025*
C5'	−0.1326 (3)	0.6833 (2)	0.01707 (12)	0.0210 (6)
H5'	−0.0295	0.6627	0.0295	0.025*
C6'	−0.1604 (4)	0.8017 (2)	0.03186 (13)	0.0225 (6)
H6'A	−0.2568	0.8252	0.0152	0.027*
H6'B	−0.1675	0.8095	0.0735	0.027*
C1''	0.3773 (4)	0.2120 (2)	0.27342 (12)	0.0216 (6)
H1''A	0.4617	0.1884	0.2492	0.026*
H1''B	0.4102	0.2762	0.2953	0.026*
C2''	0.2450 (3)	0.2425 (2)	0.23646 (12)	0.0200 (6)
C3''	0.1045 (3)	0.2786 (2)	0.26851 (12)	0.0206 (6)
H3''	0.0970	0.2370	0.3048	0.025*
C4''	−0.0213 (3)	0.2431 (2)	0.22878 (12)	0.0209 (6)
H4''	−0.0241	0.2945	0.1960	0.025*
C5''	0.0398 (3)	0.1347 (2)	0.20774 (12)	0.0210 (6)
H5''	0.0165	0.0770	0.2362	0.025*
C6''	−0.0122 (4)	0.0977 (2)	0.14988 (12)	0.0234 (7)
H6''A	−0.1230	0.0995	0.1485	0.028*
H6''B	0.0261	0.1484	0.1208	0.028*
O1	0.2984 (2)	0.32896 (15)	0.20058 (8)	0.0200 (4)
O2	0.5435 (2)	0.36981 (16)	0.13194 (8)	0.0226 (4)
H2O	0.5528	0.3898	0.1682	0.027*
O3	0.4580 (2)	0.59366 (16)	0.10396 (8)	0.0227 (4)
H3O	0.5409	0.6061	0.1282	0.027*
O4	0.1587 (2)	0.65105 (16)	0.14086 (8)	0.0224 (4)
H4O	0.1722	0.7033	0.1134	0.027*
O5	0.1340 (2)	0.35743 (15)	0.12373 (8)	0.0196 (4)
O6	−0.0780 (2)	0.47600 (15)	0.06452 (8)	0.0205 (4)
O2'	−0.2128 (2)	0.35648 (16)	−0.02197 (9)	0.0237 (5)
H2'O	−0.1218	0.3428	−0.0110	0.028*
O3'	−0.1555 (2)	0.51088 (16)	−0.11316 (8)	0.0242 (5)
H3'O	−0.1051	0.4467	−0.1225	0.029*
O4'	−0.2926 (2)	0.69259 (16)	−0.06645 (8)	0.0226 (5)
H4'O	−0.3723	0.6655	−0.0419	0.027*
O5'	−0.2398 (2)	0.62229 (15)	0.04929 (8)	0.0205 (4)
O6'	−0.0429 (2)	0.86956 (16)	0.01105 (8)	0.0241 (4)
H6'O	−0.0542	0.8707	−0.0295	0.029*
O1''	0.3383 (2)	0.12694 (16)	0.31129 (8)	0.0240 (4)
H1''O	0.3377	0.0632	0.2941	0.029*
O2''	0.2013 (2)	0.15015 (16)	0.20504 (8)	0.0210 (4)
O3''	0.1112 (2)	0.39068 (16)	0.28071 (8)	0.0241 (5)
H3''O	0.0554	0.4092	0.3120	0.029*
O4''	−0.1668 (2)	0.23872 (17)	0.25298 (9)	0.0243 (5)
H4''O	−0.1630	0.2046	0.2858	0.029*
O6''	0.0387 (3)	−0.00996 (16)	0.13734 (8)	0.0251 (5)
H6''O	0.1446	−0.0059	0.1268	0.030*
O1W	0.793 (4)	0.085 (2)	0.0359 (14)	0.089 (12)	0.127 (8)
H1WA	0.8646	0.1390	0.0319	0.106*	0.127 (8)
H1WB	0.8506	0.0230	0.0349	0.106*	0.127 (8)
O2W	0.5820 (2)	0.14541 (17)	0.11764 (9)	0.0278 (5)
H2WA	0.5799	0.2228	0.1236	0.033*
H2WB	0.6054	0.1517	0.0782	0.033*
O3W	0.6459 (2)	0.42167 (17)	0.23703 (9)	0.0266 (5)
H3WA	0.5693	0.4347	0.2628	0.032*
H3WB	0.7036	0.3670	0.2544	0.032*
O4W	0.022 (3)	0.255 (2)	0.0229 (14)	0.074 (10)	0.127 (8)
H4WA	0.0511	0.3030	0.0530	0.089*	0.127 (8)
H4WB	0.1111	0.2210	0.0180	0.089*	0.127 (8)
O5W	0.6047 (3)	0.00019 (18)	0.21153 (10)	0.0338 (5)
H5WA	0.6215	0.0459	0.1818	0.041*
H5WB	0.7031	−0.0342	0.2135	0.041*
O6W	0.0900 (3)	0.3109 (2)	0.00179 (10)	0.0247 (8)	0.873 (8)
H6WA	0.1471	0.2409	0.0029	0.030*	0.873 (8)
H6WB	0.0817	0.3430	0.0379	0.030*	0.873 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0192 (15)	0.0176 (13)	0.0224 (14)	0.0019 (12)	−0.0006 (11)	0.0003 (11)
C2	0.0175 (15)	0.0210 (14)	0.0216 (13)	−0.0002 (12)	−0.0012 (11)	0.0017 (11)
C3	0.0218 (16)	0.0181 (13)	0.0184 (13)	0.0001 (12)	0.0010 (11)	0.0016 (11)
C4	0.0231 (16)	0.0163 (13)	0.0209 (13)	0.0004 (12)	−0.0010 (11)	−0.0004 (11)
C5	0.0235 (16)	0.0162 (13)	0.0192 (13)	0.0028 (12)	0.0002 (11)	0.0000 (11)
C6	0.0207 (16)	0.0206 (14)	0.0205 (14)	0.0005 (12)	0.0015 (11)	−0.0003 (11)
C1'	0.0190 (15)	0.0156 (13)	0.0266 (15)	0.0000 (12)	−0.0002 (12)	0.0029 (11)
C2'	0.0183 (15)	0.0165 (14)	0.0269 (14)	0.0006 (11)	−0.0026 (12)	0.0003 (12)
C3'	0.0188 (16)	0.0195 (14)	0.0249 (14)	0.0020 (12)	−0.0034 (12)	0.0001 (12)
C4'	0.0185 (15)	0.0200 (14)	0.0247 (14)	0.0003 (12)	−0.0014 (12)	0.0029 (12)
C5'	0.0200 (16)	0.0181 (14)	0.0250 (15)	−0.0008 (12)	0.0015 (12)	0.0012 (11)
C6'	0.0229 (16)	0.0199 (14)	0.0248 (14)	0.0012 (12)	0.0020 (12)	0.0015 (11)
C1''	0.0236 (17)	0.0182 (13)	0.0230 (14)	−0.0012 (12)	−0.0002 (12)	0.0004 (11)
C2''	0.0219 (16)	0.0149 (13)	0.0232 (14)	−0.0028 (12)	0.0003 (12)	−0.0001 (11)
C3''	0.0236 (16)	0.0158 (13)	0.0225 (14)	0.0011 (12)	0.0013 (12)	0.0027 (11)
C4''	0.0179 (15)	0.0214 (14)	0.0235 (14)	−0.0002 (12)	0.0026 (12)	0.0031 (12)
C5''	0.0176 (15)	0.0200 (14)	0.0255 (14)	−0.0013 (12)	0.0015 (12)	0.0031 (12)
C6''	0.0262 (17)	0.0166 (14)	0.0274 (15)	−0.0009 (13)	−0.0003 (12)	−0.0002 (12)
O1	0.0225 (11)	0.0160 (9)	0.0215 (10)	−0.0010 (8)	−0.0012 (8)	0.0013 (8)
O2	0.0191 (11)	0.0219 (10)	0.0268 (10)	0.0010 (9)	0.0000 (8)	−0.0006 (8)
O3	0.0204 (11)	0.0211 (10)	0.0266 (10)	−0.0044 (9)	−0.0007 (9)	0.0045 (8)
O4	0.0272 (11)	0.0149 (9)	0.0250 (10)	0.0016 (9)	0.0031 (9)	−0.0001 (8)
O5	0.0179 (10)	0.0164 (9)	0.0246 (10)	−0.0004 (8)	−0.0020 (8)	0.0008 (8)
O6	0.0180 (11)	0.0215 (10)	0.0219 (10)	0.0015 (8)	−0.0014 (8)	0.0006 (8)
O2'	0.0240 (11)	0.0156 (10)	0.0313 (11)	−0.0016 (9)	−0.0029 (9)	−0.0007 (8)
O3'	0.0270 (12)	0.0221 (10)	0.0234 (10)	0.0029 (9)	0.0007 (9)	−0.0018 (8)
O4'	0.0228 (11)	0.0198 (10)	0.0252 (10)	0.0008 (8)	−0.0011 (8)	0.0035 (8)
O5'	0.0199 (11)	0.0179 (10)	0.0236 (10)	−0.0003 (8)	0.0020 (8)	0.0014 (8)
O6'	0.0247 (11)	0.0224 (10)	0.0252 (10)	−0.0055 (9)	−0.0013 (9)	0.0011 (8)
O1''	0.0282 (12)	0.0195 (10)	0.0244 (10)	0.0022 (9)	−0.0007 (9)	0.0010 (8)
O2''	0.0205 (11)	0.0166 (9)	0.0260 (10)	−0.0017 (8)	0.0009 (8)	−0.0017 (8)
O3''	0.0275 (12)	0.0174 (10)	0.0273 (11)	0.0006 (9)	0.0046 (9)	−0.0029 (8)
O4''	0.0207 (11)	0.0241 (10)	0.0280 (11)	0.0009 (9)	0.0031 (9)	0.0045 (9)
O6''	0.0249 (11)	0.0217 (10)	0.0287 (11)	−0.0029 (9)	0.0041 (9)	−0.0042 (8)
O1W	0.11 (3)	0.039 (14)	0.12 (3)	−0.007 (16)	0.00 (2)	0.012 (15)
O2W	0.0327 (13)	0.0215 (10)	0.0291 (11)	−0.0008 (10)	−0.0002 (9)	0.0006 (9)
O3W	0.0265 (12)	0.0244 (11)	0.0289 (11)	0.0002 (9)	0.0008 (9)	0.0005 (9)
O4W	0.056 (18)	0.058 (17)	0.11 (2)	−0.011 (15)	0.007 (16)	−0.019 (18)
O5W	0.0280 (12)	0.0317 (12)	0.0416 (13)	0.0025 (10)	0.0019 (10)	0.0113 (10)
O6W	0.0293 (16)	0.0223 (14)	0.0224 (13)	0.0097 (12)	−0.0023 (10)	−0.0018 (10)

Geometric parameters (Å, º)

C1—C2	1.527 (4)	C5—H5	1.00
C1—O1	1.406 (3)	C6—H6A	0.99
C1—O5	1.428 (4)	C6—H6B	0.99
C2—C3	1.537 (4)	C1'—H1'	1.00
C2—O2	1.419 (4)	C2'—H2'	1.00
C3—C4	1.524 (4)	C3'—H3'	1.00
C3—O3	1.428 (3)	C4'—H4'	1.00
C4—C5	1.513 (4)	C5'—H5'	1.00
C4—O4	1.423 (3)	C6'—H6'A	0.99
C5—C6	1.506 (4)	C6'—H6'B	0.99
C5—O5	1.447 (3)	C1''—H1''A	0.99
C6—O6	1.435 (3)	C1''—H1''B	0.99
C1'—C2'	1.529 (4)	C3''—H3''	1.00
C1'—O6	1.409 (4)	C4''—H4''	1.00
C1'—O5'	1.424 (3)	C5''—H5''	1.00
C2'—C3'	1.530 (4)	C6''—H6''A	0.99
C2'—O2'	1.435 (3)	C6''—H6''B	0.99
C3'—C4'	1.532 (4)	O2—H2O	0.90
C3'—O3'	1.427 (3)	O3—H3O	0.95
C4'—C5'	1.529 (4)	O4—H4O	0.92
C4'—O4'	1.428 (4)	O2'—H2'O	0.87
C5'—C6'	1.519 (4)	O3'—H3'O	0.94
C5'—O5'	1.436 (4)	O4'—H4'O	0.98
C6'—O6'	1.429 (4)	O6'—H6'O	0.96
C1''—C2''	1.516 (4)	O1''—H1''O	0.88
C1''—O1''	1.421 (3)	O3''—H3''O	0.92
C2''—C3''	1.532 (4)	O4''—H4''O	0.88
C2''—O1	1.442 (3)	O6''—H6''O	0.98
C2''—O2''	1.413 (3)	O1W—H1WA	0.92
C3''—C4''	1.528 (4)	O1W—H1WB	0.92
C3''—O3''	1.412 (3)	O2W—H2WA	0.96
C4''—C5''	1.525 (4)	O2W—H2WB	0.96
C4''—O4''	1.421 (4)	O3W—H3WA	0.93
C5''—C6''	1.513 (4)	O3W—H3WB	0.94
C5''—O2''	1.457 (4)	O4W—H4WA	0.96
C6''—O6''	1.434 (4)	O4W—H4WB	0.91
C1—H1	1.00	O5W—H5WA	0.91
C2—H2	1.00	O5W—H5WB	0.98
C3—H3	1.00	O6W—H6WA	1.00
C4—H4	1.00	O6W—H6WB	0.94
C2—C1—O1	106.3 (2)	H4—C4—O4	109
C2—C1—O5	109.6 (2)	C4—C5—H5	108
O1—C1—O5	112.8 (2)	H5—C5—C6	108
C1—C2—C3	110.6 (2)	H5—C5—O5	108
C1—C2—O2	110.9 (2)	C5—C6—H6A	110
C3—C2—O2	112.7 (2)	C5—C6—H6B	110
C2—C3—C4	110.5 (2)	H6A—C6—H6B	108
C2—C3—O3	110.9 (2)	H6A—C6—O6	110
C4—C3—O3	108.1 (2)	H6B—C6—O6	110
C3—C4—C5	110.9 (2)	H1'—C1'—C2'	109
C3—C4—O4	111.4 (2)	H1'—C1'—O6	109
C5—C4—O4	107.1 (2)	H1'—C1'—O5'	109
C4—C5—C6	113.7 (2)	C1'—C2'—H2'	108
C4—C5—O5	110.4 (2)	H2'—C2'—C3'	108
C6—C5—O5	107.3 (2)	H2'—C2'—O2'	108
C5—C6—O6	108.7 (2)	C2'—C3'—H3'	109
C2'—C1'—O6	107.9 (2)	H3'—C3'—C4'	109
C2'—C1'—O5'	110.5 (2)	H3'—C3'—O3'	109
O6—C1'—O5'	111.3 (2)	C3'—C4'—H4'	109
C1'—C2'—C3'	110.9 (2)	H4'—C4'—C5'	109
C1'—C2'—O2'	111.1 (2)	H4'—C4'—O4'	109
C3'—C2'—O2'	112.0 (2)	C4'—C5'—H5'	109
C2'—C3'—C4'	110.3 (2)	H5'—C5'—C6'	109
C2'—C3'—O3'	110.7 (2)	H5'—C5'—O5'	109
C4'—C3'—O3'	108.7 (2)	C5'—C6'—H6'A	109
C3'—C4'—C5'	109.0 (2)	C5'—C6'—H6'B	109
C3'—C4'—O4'	111.2 (2)	H6'A—C6'—H6'B	108
C5'—C4'—O4'	111.0 (2)	H6'A—C6'—O6'	109
C4'—C5'—C6'	113.9 (2)	H6'B—C6'—O6'	109
C4'—C5'—O5'	109.8 (2)	H1''A—C1''—H1''B	108
C6'—C5'—O5'	105.8 (2)	H1''A—C1''—C2''	110
C5'—C6'—O6'	111.3 (3)	H1''A—C1''—O1''	109
C2''—C1''—O1''	110.7 (2)	H1''B—C1''—C2''	110
C1''—C2''—C3''	115.3 (2)	H1''B—C1''—O1''	110
C1''—C2''—O1	105.3 (2)	C2''—C3''—H3''	109
C1''—C2''—O2''	108.5 (2)	H3''—C3''—C4''	109
C3''—C2''—O1	110.3 (2)	H3''—C3''—O3''	109
C3''—C2''—O2''	105.4 (2)	C3''—C4''—H4''	108
O1—C2''—O2''	112.2 (2)	H4''—C4''—C5''	108
C2''—C3''—C4''	102.5 (2)	H4''—C4''—O4''	108
C2''—C3''—O3''	110.5 (2)	C4''—C5''—H5''	109
C4''—C3''—O3''	115.9 (2)	H5''—C5''—C6''	109
C3''—C4''—C5''	100.8 (2)	H5''—C5''—O2''	109
C3''—C4''—O4''	115.9 (2)	C5''—C6''—H6''A	109
C5''—C4''—O4''	115.2 (2)	C5''—C6''—H6''B	109
C4''—C5''—C6''	116.6 (2)	H6''A—C6''—H6''B	108
C4''—C5''—O2''	104.7 (2)	H6''A—C6''—O6''	109
C6''—C5''—O2''	107.7 (2)	H6''B—C6''—O6''	109
C5''—C6''—O6''	111.6 (2)	C2—O2—H2O	104
C1—O1—C2''	121.2 (2)	C3—O3—H3O	106
C1—O5—C5	113.6 (2)	C4—O4—H4O	108
C6—O6—C1'	111.6 (2)	C2'—O2'—H2'O	107
C1'—O5'—C5'	113.5 (2)	C3'—O3'—H3'O	109
C2''—O2''—C5''	110.9 (2)	C4'—O4'—H4'O	110
H1—C1—C2	109	C6'—O6'—H6'O	106
H1—C1—O1	109	C1''—O1''—H1''O	112
H1—C1—O5	109	C3''—O3''—H3''O	113
C1—C2—H2	107	C4''—O4''—H4''O	110
H2—C2—C3	107	C6''—O6''—H6''O	108
H2—C2—O2	107	H1WA—O1W—H1WB	102
C2—C3—H3	109	H2WA—O2W—H2WB	94
H3—C3—C4	109	H3WA—O3W—H3WB	104
H3—C3—O3	109	H4WA—O4W—H4WB	98
C3—C4—H4	109	H5WA—O5W—H5WB	99
H4—C4—C5	109	H6WA—O6W—H6WB	112
C2—C1—O1—C2''	−158.89 (19)	C2'—C3'—C4'—O4'	−68.2 (3)
O1—C1—C2—C3	−66.2 (3)	O3'—C3'—C4'—C5'	175.9 (2)
O1—C1—C2—O2	59.6 (3)	O3'—C3'—C4'—O4'	53.3 (3)
C2—C1—O5—C5	−61.1 (3)	C3'—C4'—C5'—C6'	−176.7 (2)
O5—C1—C2—C3	56.0 (3)	C3'—C4'—C5'—O5'	−58.3 (3)
O5—C1—C2—O2	−178.23 (19)	O4'—C4'—C5'—C6'	−54.0 (3)
O1—C1—O5—C5	57.2 (3)	O4'—C4'—C5'—O5'	64.4 (3)
O5—C1—O1—C2''	81.0 (3)	C4'—C5'—C6'—O6'	−70.4 (3)
C1—C2—C3—C4	−52.5 (3)	C4'—C5'—O5'—C1'	62.6 (3)
C1—C2—C3—O3	−172.3 (2)	C6'—C5'—O5'—C1'	−174.12 (19)
O2—C2—C3—C4	−177.28 (18)	O5'—C5'—C6'—O6'	168.9 (2)
O2—C2—C3—O3	62.9 (3)	O1''—C1''—C2''—C3''	58.0 (3)
C2—C3—C4—C5	51.9 (3)	O1''—C1''—C2''—O1	179.73 (19)
C2—C3—C4—O4	171.1 (2)	O1''—C1''—C2''—O2''	−60.0 (3)
O3—C3—C4—C5	173.41 (18)	C1''—C2''—C3''—C4''	−149.8 (2)
O3—C3—C4—O4	−67.4 (3)	C1''—C2''—C3''—O3''	86.1 (3)
C3—C4—C5—C6	−175.35 (19)	C1''—C2''—O1—C1	128.8 (2)
C3—C4—C5—O5	−54.8 (3)	C1''—C2''—O2''—C5''	132.7 (2)
O4—C4—C5—C6	62.9 (3)	C3''—C2''—O1—C1	−106.3 (2)
O4—C4—C5—O5	−176.51 (19)	O1—C2''—C3''—C4''	91.2 (2)
C4—C5—C6—O6	61.4 (3)	O1—C2''—C3''—O3''	−32.9 (3)
C4—C5—O5—C1	60.7 (3)	C3''—C2''—O2''—C5''	8.7 (3)
C6—C5—O5—C1	−174.90 (17)	O2''—C2''—C3''—C4''	−30.1 (2)
O5—C5—C6—O6	−60.9 (3)	O2''—C2''—C3''—O3''	−154.2 (2)
C5—C6—O6—C1'	−171.33 (18)	O1—C2''—O2''—C5''	−111.4 (2)
C2'—C1'—O6—C6	−166.35 (18)	O2''—C2''—O1—C1	10.9 (3)
O6—C1'—C2'—C3'	−68.0 (3)	C2''—C3''—C4''—C5''	38.7 (2)
O6—C1'—C2'—O2'	57.1 (3)	C2''—C3''—C4''—O4''	163.7 (2)
C2'—C1'—O5'—C5'	−59.8 (3)	O3''—C3''—C4''—C5''	159.1 (2)
O5'—C1'—C2'—C3'	53.8 (3)	O3''—C3''—C4''—O4''	−75.9 (3)
O5'—C1'—C2'—O2'	179.0 (2)	C3''—C4''—C5''—C6''	−153.0 (2)
O6—C1'—O5'—C5'	60.1 (3)	C3''—C4''—C5''—O2''	−34.1 (2)
O5'—C1'—O6—C6	72.3 (2)	O4''—C4''—C5''—C6''	81.5 (3)
C1'—C2'—C3'—C4'	−52.5 (3)	O4''—C4''—C5''—O2''	−159.6 (2)
C1'—C2'—C3'—O3'	−172.8 (2)	C4''—C5''—C6''—O6''	−173.5 (2)
O2'—C2'—C3'—C4'	−177.1 (2)	C4''—C5''—O2''—C2''	16.4 (2)
O2'—C2'—C3'—O3'	62.5 (3)	C6''—C5''—O2''—C2''	141.11 (19)
C2'—C3'—C4'—C5'	54.4 (3)	O2''—C5''—C6''—O6''	69.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3W	0.90	1.87	2.720 (3)	159
O3—H3O···O1′′^i	0.95	1.81	2.735 (3)	165
O4—H4O···O4′^ii	0.92	1.72	2.643 (3)	175
O2′—H2′O···O4W	0.87	1.86	2.66 (3)	152
O2′—H2′O···O6W	0.87	1.96	2.819 (4)	172
O3′—H3′O···O2W^iii	0.94	2.02	2.867 (3)	149
O4′—H4′O···O6′^iv	0.98	1.74	2.701 (3)	166
O6′—H6′O···O3^iv	0.96	1.82	2.752 (3)	164
O1′′—H1′′O···O3W^v	0.88	1.90	2.778 (3)	174
O3′′—H3′′O···O6′′^vi	0.92	1.77	2.652 (3)	160
O4′′—H4′′O···O4^vii	0.88	1.85	2.730 (3)	172
O6′′—H6′′O···O3′^viii	0.98	1.82	2.791 (3)	170
O1W—H1WA···O4W^ix	0.92	2.02	2.94 (4)	180
O1W—H1WB···O6′^x	0.92	2.19	3.09 (3)	165
O2W—H2WA···O2	0.96	1.85	2.806 (3)	171
O2W—H2WB···O1W	0.96	2.12	2.80 (3)	127
O2W—H2WB···O6W^viii	0.96	1.95	2.871 (3)	161
O3W—H3WA···O5W^i	0.93	1.85	2.725 (3)	155
O3W—H3WB···O4′′^ix	0.94	1.96	2.832 (3)	153
O4W—H4WA···O5	0.96	1.95	2.87 (3)	162
O4W—H4WA···O6	0.96	2.44	3.02 (3)	119
O4W—H4WB···O2′^viii	0.91	1.84	2.74 (3)	169
O5W—H5WA···O2W	0.91	1.98	2.855 (3)	160
O5W—H5WB···O3′′^v	0.98	1.91	2.880 (3)	176
O6W—H6WA···O2′^viii	1.00	1.79	2.754 (3)	160
O6W—H6WB···O5	0.94	2.09	2.961 (3)	154
O6W—H6WB···O6	0.94	2.26	2.929 (3)	127

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1/2, −y+3/2, −z; (iii) x−1/2, −y+1/2, −z; (iv) x−1/2, −y+3/2, −z; (v) −x+1, y−1/2, −z+1/2; (vi) −x, y+1/2, −z+1/2; (vii) −x, y−1/2, −z+1/2; (viii) x+1/2, −y+1/2, −z; (ix) x+1, y, z; (x) x+1, y−1, z.