α-D,l-Sorbose

Taguchi, H.; Sogo, K.; Ishii, T.; Yoshihara, A.; Fukada, K.

doi:10.1107/S2414314618001141

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 1| January 2018| x180114

https://doi.org/10.1107/S2414314618001141

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α-D,L-Sorbose

Hiroaki Taguchi,^a Kouta Sogo,^a Tomohiko Ishii,^a ^* Akihide Yoshihara ^b and Kazuhiro Fukada ^c

^aDepartment of Advanced Materials Science, Faculty of Engineering, Kagawa University, 2217-20 Hayashi-cho, Takamatsu, Kagawa 761-0396, Japan, ^bRare Sugar Research Center, Kagawa University, 2393 Ikenobe, Kagawa 761-0795, Japan, and ^cDepartment of Applied Biological Science, Faculty of Agriculture, Kagawa University, 2393 Ikenobe, Kagawa 761-0795, Japan
^*Correspondence e-mail: tishii@eng.kagawa-u.ac.jp

Edited by H. Ishida, Okayama University, Japan (Received 8 January 2018; accepted 18 January 2018; online 31 January 2018)

The racemic title compound, C₆H₁₂O₆, consisting of C-4 epimers of psicose, was crystallized from an aqueous solution of an equimolar mixture of D- and L-sorboses. It was confirmed that D-sorbose (or L-sorbose) formed α-pyranose with a ⁴C₁ (or ¹C₄) conformation where the anomer position was designated as carbon-1. The asymmetric unit comprises two crystallographically independent molecules. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming a three-dimensional framework. The unit-cell volume of the title racemic α-D,L-sorbose is 1450.86 (6) Å³ (Z = 8), which is about 41 Å³ smaller than that of twice the amount of chiral α-L-sorbose [V = 745.942 Å³ (Z = 4)].

Keywords: crystal structure; hydrogen bonding; racemic compound; rare sugar.

CCDC reference: 1812905

Structure description

D- and L-sorboses are classified as rare sugars. L-Sorbose is the first L-form hexose found in nature (Nordenson et al., 1979 ). In this study, we aimed to create a racemic single crystal including both D- and L-sorbose in a 1:1 ratio. There are two independent sorbose molecules, A and B, in the asymmetric unit (Fig. 1). Therefore, there are a total of eight sorbose molecules (four L- and four D-forms) in the unit cell.

Figure 1
An ORTEP view of the title compound, molecule A (left) and molecule B (right), with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radii.

In the crystal, the D- and L-sorbose molecules are linked weakly, as well as the strong homo-chiral D–D (and L–L) links, via O—H⋯O hydrogen bonds (Table 1), forming a three-dimensional network (Fig. 2). The crystal structure of the title compound with two independent molecules in the asymmetric unit in space group P2₁/a (Z = 8) is significantly different from the structures previously reported by us, viz. racemic β-D,L-allose (P2₁/c, Z = 4; Ishii, Senoo et al., 2015a ), β-D,L-psicose (Pna2₁, Z = 4; Ishii, Sakane et al., 2015 ) and β-D,L-fructose (P $[\overline{1}]$ , Z = 2; Ishii, Senoo et al., 2015b ), where each asymmetric unit consists of one molecule.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O4ⁱ	0.82	2.37	3.174 (3)	167
O2—H2A⋯O5ⁱⁱ	0.82	1.96	2.757 (2)	164
O3—H3A⋯O10	0.82	1.99	2.807 (2)	172
O4—H4A⋯O6ⁱⁱⁱ	0.82	2.11	2.917 (2)	170
O5—H5A⋯O2^iv	0.82	2.30	2.875 (2)	128
O5—H5A⋯O3^iv	0.82	2.10	2.8683 (18)	156
O7—H7A⋯O9ⁱ	0.82	2.14	2.915 (2)	159
O7—H7A⋯O10ⁱ	0.82	2.52	3.047 (3)	123
O8—H8A⋯O11^v	0.82	2.00	2.814 (2)	169
O9—H9A⋯O4^vi	0.82	1.93	2.747 (2)	172
O10—H10A⋯O12ⁱⁱⁱ	0.82	2.25	3.051 (2)	165
O11—H11A⋯O8^iv	0.82	2.41	2.976 (2)	127
O11—H11A⋯O9^iv	0.82	2.28	3.060 (2)	158
Symmetry codes: (i) x, y+1, z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z]$ ; (iii) x, y-1, z; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (v) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+1]$ ; (vi) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Figure 2
A packing diagram of the title compound viewed down the b axis, showing the hydrogen-bonding network (dotted lines). In this figure, D and L denote the D- and L-forms, respectively.

Synthesis and crystallization

L-Sorbose was purchased from Wako Pure Chemical Industries. D-Sorbose was prepared by microbial oxidation of galactitol to D-tagatose followed by enzymatic epimerization using D-tagatose 3-epimerase (Khan et al., 1992 ; Itoh et al., 1995 ). L-Sorbose and D-sorbose were each dissolved in hot water to give a 30 wt% solution and the solutions were mixed in equal volume. Single crystals were obtained from the mixed solution by keeping it at 20°C.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₆H₁₂O₆
M_r	180.16
Crystal system, space group	Monoclinic, P2₁/a
Temperature (K)	296
a, b, c (Å)	12.8152 (3), 6.29489 (13), 18.9482 (4)
β (°)	108.3472 (12)
V (Å³)	1450.86 (6)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	1.31
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Rigaku, 1995 )
T_min, T_max	0.728, 0.877
No. of measured, independent and observed [F² > 2.0σ(F²)] reflections	24139, 2658, 2161
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.120, 1.08
No. of reflections	2658
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.29
Computer programs: RAPID-AUTO (Rigaku, 2009 ), SIR2011 (Burla et al., 2012 ), SHELXL2013 (Sheldrick, 2015 ) and CrystalStructure (Rigaku, 2014 ).

Structural data

CCDC reference: 1812905

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314618001141/is4024sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618001141/is4024Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618001141/is4024Isup3.cml

checkCIF report

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2009); cell refinement: RAPID-AUTO (Rigaku, 2009); data reduction: RAPID-AUTO (Rigaku, 2009); program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: CrystalStructure (Rigaku, 2014); software used to prepare material for publication: CrystalStructure (Rigaku, 2014).

α-D,L-Sorbose top

Crystal data top

C₆H₁₂O₆	F(000) = 768.00
M_r = 180.16	D_x = 1.649 Mg m⁻³
Monoclinic, P2₁/a	Cu Kα radiation, λ = 1.54187 Å
a = 12.8152 (3) Å	Cell parameters from 15393 reflections
b = 6.29489 (13) Å	θ = 3.6–68.3°
c = 18.9482 (4) Å	µ = 1.31 mm⁻¹
β = 108.3472 (12)°	T = 296 K
V = 1450.86 (6) Å³	Block, colorless
Z = 8	0.10 × 0.10 × 0.10 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2161 reflections with F² > 2.0σ(F²)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.051
ω scans	θ_max = 68.3°, θ_min = 4.9°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −15→15
T_min = 0.728, T_max = 0.877	k = −7→7
24139 measured reflections	l = −22→22
2658 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.055P)² + 0.7784P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2658 reflections	Δρ_max = 0.57 e Å⁻³
228 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Extinction correction: SHELXL2013 (Sheldrick, 2015)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0027 (4)
Secondary atom site location: difference Fourier map

Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

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 sigma(F²) is used only for calculating R-factor (gt).

H atoms were positioned geometrically (C—H = 0.98 or 0.97 Å, and O—H = 0.82 Å) and refined using as riding with U_iso(H) = 1.2U_eq(C or O), allowing for free rotation of the OH groups.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.22822 (19)	0.7791 (3)	0.22185 (11)	0.0629 (6)
O2	0.14999 (12)	0.4920 (2)	0.04746 (8)	0.0319 (4)
O3	0.18382 (11)	0.2570 (3)	0.17113 (8)	0.0338 (4)
O4	0.39585 (13)	0.0849 (3)	0.17903 (8)	0.0385 (4)
O5	0.47216 (12)	0.2681 (3)	0.05987 (8)	0.0404 (4)
O6	0.30811 (11)	0.6926 (2)	0.10091 (8)	0.0294 (4)
O7	0.02816 (17)	0.8374 (3)	0.28347 (10)	0.0547 (5)
O8	0.09763 (13)	0.5097 (3)	0.44959 (8)	0.0345 (4)
O9	0.02314 (12)	0.2877 (3)	0.31816 (9)	0.0368 (4)
O10	0.23099 (15)	0.1206 (3)	0.31891 (9)	0.0433 (4)
O11	0.41443 (12)	0.2925 (3)	0.43820 (8)	0.0386 (4)
O12	0.21295 (11)	0.7176 (2)	0.40376 (8)	0.0295 (4)
C1	0.16229 (19)	0.7191 (4)	0.15089 (13)	0.0380 (5)
C2	0.22188 (16)	0.5705 (3)	0.11388 (10)	0.0246 (4)
C3	0.27148 (15)	0.3795 (3)	0.16199 (11)	0.0239 (4)
C4	0.34130 (16)	0.2480 (3)	0.12745 (11)	0.0265 (5)
C5	0.42487 (16)	0.3835 (4)	0.10693 (11)	0.0274 (5)
C6	0.37037 (17)	0.5755 (4)	0.06332 (12)	0.0318 (5)
C7	0.02122 (18)	0.7524 (4)	0.35030 (13)	0.0365 (5)
C8	0.11366 (16)	0.5985 (3)	0.38604 (11)	0.0252 (4)
C9	0.12015 (16)	0.4150 (3)	0.33493 (11)	0.0256 (4)
C10	0.21984 (16)	0.2770 (3)	0.37048 (11)	0.0266 (4)
C11	0.32302 (16)	0.4106 (3)	0.39376 (11)	0.0268 (5)
C12	0.30878 (16)	0.5961 (4)	0.44065 (12)	0.0320 (5)
H3A	0.20162	0.20895	0.21349	0.0405*
H9B	0.12621	0.47356	0.28846	0.0307*
H11A	0.44627	0.23745	0.4115	0.0463*
H10B	0.21093	0.20623	0.4143	0.0319*
H8A	0.0954	0.60463	0.47871	0.0414*
H5B	0.48263	0.4284	0.15205	0.0329*
H2A	0.11709	0.59116	0.02195	0.0383*
H6A	0.42617	0.66733	0.05503	0.0381*
H6B	0.32208	0.53027	0.01517	0.0381*
H9A	−0.02006	0.32465	0.27811	0.0442*
H11B	0.33855	0.46362	0.34947	0.0321*
H5A	0.53459	0.2308	0.08379	0.0485*
H4B	0.29326	0.18044	0.08229	0.0318*
H4A	0.3784	−0.032	0.15987	0.0462*
H3B	0.31745	0.42981	0.21083	0.0287*
H10A	0.22195	0.00214	0.334	0.0519*
H12A	0.30313	0.54341	0.48742	0.0384*
H12B	0.37304	0.68699	0.45164	0.0384*
H7A	0.04068	0.96523	0.28858	0.0657*
H7C	−0.04858	0.67955	0.34064	0.0438*
H7B	0.02309	0.8675	0.38472	0.0438*
H1C	0.13966	0.84507	0.1204	0.0456*
H1B	0.09662	0.64956	0.1545	0.0456*
H1A	0.27758	0.85718	0.2184	0.0755*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0933 (16)	0.0493 (13)	0.0544 (11)	−0.0043 (11)	0.0348 (11)	−0.0184 (10)
O2	0.0312 (8)	0.0310 (9)	0.0263 (7)	0.0003 (6)	−0.0014 (6)	0.0014 (6)
O3	0.0312 (8)	0.0350 (9)	0.0338 (8)	−0.0052 (7)	0.0082 (6)	0.0102 (7)
O4	0.0426 (9)	0.0250 (9)	0.0381 (9)	0.0065 (7)	−0.0013 (7)	0.0029 (7)
O5	0.0260 (8)	0.0569 (11)	0.0355 (9)	0.0092 (8)	0.0055 (6)	−0.0126 (8)
O6	0.0308 (8)	0.0237 (8)	0.0363 (8)	−0.0023 (6)	0.0143 (6)	0.0013 (6)
O7	0.0706 (12)	0.0396 (11)	0.0503 (11)	0.0128 (10)	0.0138 (9)	0.0158 (9)
O8	0.0441 (9)	0.0336 (9)	0.0306 (8)	0.0027 (7)	0.0186 (7)	0.0023 (7)
O9	0.0317 (8)	0.0305 (9)	0.0390 (9)	−0.0099 (7)	−0.0021 (6)	0.0024 (7)
O10	0.0629 (11)	0.0260 (9)	0.0445 (10)	0.0004 (8)	0.0221 (8)	−0.0111 (7)
O11	0.0311 (8)	0.0520 (11)	0.0333 (8)	0.0158 (7)	0.0112 (6)	0.0034 (7)
O12	0.0252 (7)	0.0241 (8)	0.0370 (8)	−0.0021 (6)	0.0066 (6)	−0.0042 (6)
C1	0.0465 (13)	0.0292 (13)	0.0444 (13)	0.0053 (10)	0.0231 (11)	0.0009 (10)
C2	0.0252 (10)	0.0223 (11)	0.0259 (10)	−0.0023 (8)	0.0076 (8)	−0.0008 (8)
C3	0.0252 (10)	0.0221 (11)	0.0220 (9)	−0.0038 (8)	0.0039 (8)	−0.0002 (8)
C4	0.0254 (10)	0.0252 (11)	0.0230 (10)	0.0015 (8)	−0.0007 (8)	−0.0019 (8)
C5	0.0224 (9)	0.0339 (13)	0.0231 (10)	0.0020 (9)	0.0030 (8)	−0.0054 (9)
C6	0.0283 (11)	0.0375 (13)	0.0315 (11)	0.0032 (9)	0.0123 (9)	0.0040 (10)
C7	0.0319 (11)	0.0285 (13)	0.0475 (14)	0.0044 (9)	0.0103 (10)	0.0052 (10)
C8	0.0247 (10)	0.0230 (11)	0.0283 (10)	−0.0012 (8)	0.0087 (8)	0.0019 (8)
C9	0.0288 (10)	0.0229 (11)	0.0230 (10)	−0.0054 (8)	0.0051 (8)	0.0016 (8)
C10	0.0352 (11)	0.0238 (11)	0.0224 (10)	0.0009 (9)	0.0115 (8)	−0.0006 (8)
C11	0.0266 (10)	0.0313 (12)	0.0231 (10)	0.0042 (9)	0.0089 (8)	0.0007 (8)
C12	0.0244 (10)	0.0361 (13)	0.0319 (11)	0.0000 (9)	0.0037 (8)	−0.0093 (9)

Geometric parameters (Å, º) top

O1—C1	1.396 (3)	O1—H1A	0.820
O2—C2	1.395 (2)	O2—H2A	0.820
O3—C3	1.418 (3)	O3—H3A	0.820
O4—C4	1.438 (2)	O4—H4A	0.820
O5—C5	1.425 (3)	O5—H5A	0.820
O6—C2	1.429 (3)	O7—H7A	0.820
O6—C6	1.430 (3)	O8—H8A	0.820
O7—C7	1.403 (3)	O9—H9A	0.820
O8—C8	1.400 (3)	O10—H10A	0.820
O9—C9	1.428 (3)	O11—H11A	0.820
O10—C10	1.426 (3)	C1—H1C	0.970
O11—C11	1.419 (2)	C1—H1B	0.970
O12—C8	1.423 (2)	C3—H3B	0.980
O12—C12	1.429 (2)	C4—H4B	0.980
C1—C2	1.512 (3)	C5—H5B	0.980
C2—C3	1.522 (3)	C6—H6A	0.970
C3—C4	1.511 (3)	C6—H6B	0.970
C4—C5	1.513 (3)	C7—H7C	0.970
C5—C6	1.506 (3)	C7—H7B	0.970
C7—C8	1.515 (3)	C9—H9B	0.980
C8—C9	1.526 (3)	C10—H10B	0.980
C9—C10	1.516 (3)	C11—H11B	0.980
C10—C11	1.511 (3)	C12—H12A	0.970
C11—C12	1.513 (3)	C12—H12B	0.970

C2—O6—C6	113.05 (16)	C8—O8—H8A	109.471
C8—O12—C12	113.61 (15)	C9—O9—H9A	109.472
O1—C1—C2	111.89 (19)	C10—O10—H10A	109.479
O2—C2—O6	111.22 (16)	C11—O11—H11A	109.476
O2—C2—C1	110.54 (16)	O1—C1—H1C	109.244
O2—C2—C3	107.06 (16)	O1—C1—H1B	109.242
O6—C2—C1	106.13 (17)	C2—C1—H1C	109.230
O6—C2—C3	109.14 (15)	C2—C1—H1B	109.231
C1—C2—C3	112.80 (18)	H1C—C1—H1B	107.914
O3—C3—C2	107.78 (15)	O3—C3—H3B	108.924
O3—C3—C4	110.78 (16)	C2—C3—H3B	108.914
C2—C3—C4	111.47 (18)	C4—C3—H3B	108.910
O4—C4—C3	108.92 (17)	O4—C4—H4B	108.731
O4—C4—C5	110.20 (16)	C3—C4—H4B	108.728
C3—C4—C5	111.47 (17)	C5—C4—H4B	108.740
O5—C5—C4	110.39 (18)	O5—C5—H5B	109.860
O5—C5—C6	106.31 (18)	C4—C5—H5B	109.868
C4—C5—C6	110.49 (17)	C6—C5—H5B	109.864
O6—C6—C5	112.05 (19)	O6—C6—H6A	109.207
O7—C7—C8	112.6 (2)	O6—C6—H6B	109.204
O8—C8—O12	111.70 (15)	C5—C6—H6A	109.202
O8—C8—C7	109.51 (19)	C5—C6—H6B	109.203
O8—C8—C9	107.19 (16)	H6A—C6—H6B	107.889
O12—C8—C7	106.49 (16)	O7—C7—H7C	109.070
O12—C8—C9	108.98 (18)	O7—C7—H7B	109.069
C7—C8—C9	113.04 (16)	C8—C7—H7C	109.076
O9—C9—C8	110.39 (18)	C8—C7—H7B	109.068
O9—C9—C10	109.27 (16)	H7C—C7—H7B	107.828
C8—C9—C10	110.99 (15)	O9—C9—H9B	108.714
O10—C10—C9	110.08 (15)	C8—C9—H9B	108.713
O10—C10—C11	108.49 (19)	C10—C9—H9B	108.709
C9—C10—C11	110.40 (17)	O10—C10—H10B	109.288
O11—C11—C10	111.40 (17)	C9—C10—H10B	109.283
O11—C11—C12	106.60 (15)	C11—C10—H10B	109.285
C10—C11—C12	110.17 (18)	O11—C11—H11B	109.539
O12—C12—C11	111.71 (15)	C10—C11—H11B	109.544
C1—O1—H1A	109.482	C12—C11—H11B	109.542
C2—O2—H2A	109.473	O12—C12—H12A	109.276
C3—O3—H3A	109.469	O12—C12—H12B	109.277
C4—O4—H4A	109.472	C11—C12—H12A	109.279
C5—O5—H5A	109.470	C11—C12—H12B	109.283
C7—O7—H7A	109.468	H12A—C12—H12B	107.938

C2—O6—C6—C5	−60.30 (17)	C3—C4—C5—O5	−166.84 (13)
C6—O6—C2—O2	−57.58 (18)	C3—C4—C5—C6	−49.53 (19)
C6—O6—C2—C1	−177.85 (12)	O5—C5—C6—O6	173.00 (14)
C6—O6—C2—C3	60.32 (17)	C4—C5—C6—O6	53.2 (2)
C8—O12—C12—C11	59.7 (2)	O7—C7—C8—O8	−176.16 (15)
C12—O12—C8—O8	58.4 (2)	O7—C7—C8—O12	62.9 (2)
C12—O12—C8—C7	177.90 (15)	O7—C7—C8—C9	−56.7 (2)
C12—O12—C8—C9	−59.9 (2)	O8—C8—C9—O9	56.92 (18)
O1—C1—C2—O2	172.38 (18)	O8—C8—C9—C10	−64.39 (19)
O1—C1—C2—O6	−66.9 (2)	O12—C8—C9—O9	177.97 (13)
O1—C1—C2—C3	52.6 (2)	O12—C8—C9—C10	56.6 (2)
O2—C2—C3—O3	−57.0 (2)	C7—C8—C9—O9	−63.8 (2)
O2—C2—C3—C4	64.77 (19)	C7—C8—C9—C10	174.84 (17)
O6—C2—C3—O3	−177.49 (14)	O9—C9—C10—O10	64.2 (2)
O6—C2—C3—C4	−55.71 (18)	O9—C9—C10—C11	−176.02 (15)
C1—C2—C3—O3	64.81 (19)	C8—C9—C10—O10	−173.79 (16)
C1—C2—C3—C4	−173.42 (14)	C8—C9—C10—C11	−54.0 (2)
O3—C3—C4—O4	−66.54 (17)	O10—C10—C11—O11	−69.2 (2)
O3—C3—C4—C5	171.66 (12)	O10—C10—C11—C12	172.67 (13)
C2—C3—C4—O4	173.44 (13)	C9—C10—C11—O11	170.05 (16)
C2—C3—C4—C5	51.64 (18)	C9—C10—C11—C12	52.0 (2)
O4—C4—C5—O5	72.10 (18)	O11—C11—C12—O12	−175.14 (16)
O4—C4—C5—C6	−170.59 (14)	C10—C11—C12—O12	−54.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4ⁱ	0.82	2.37	3.174 (3)	167
O2—H2A···O5ⁱⁱ	0.82	1.96	2.757 (2)	164
O3—H3A···O10	0.82	1.99	2.807 (2)	172
O4—H4A···O6ⁱⁱⁱ	0.82	2.11	2.917 (2)	170
O5—H5A···O2^iv	0.82	2.30	2.875 (2)	128
O5—H5A···O3^iv	0.82	2.10	2.8683 (18)	156
O7—H7A···O9ⁱ	0.82	2.14	2.915 (2)	159
O7—H7A···O10ⁱ	0.82	2.52	3.047 (3)	123
O8—H8A···O11^v	0.82	2.00	2.814 (2)	169
O9—H9A···O4^vi	0.82	1.93	2.747 (2)	172
O10—H10A···O12ⁱⁱⁱ	0.82	2.25	3.051 (2)	165
O11—H11A···O8^iv	0.82	2.41	2.976 (2)	127
O11—H11A···O9^iv	0.82	2.28	3.060 (2)	158

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

Acknowledgements

The authors are sincerely grateful to Professor Genta Sakane (Okayama University of Science) for excellent discussions and useful technical advice.

Funding information

The authors are grateful for Grants-in-Aid for Rare Sugar Research from Kagawa University.

References

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