l-Talitol

Takashita, T.; Horii, Y.; Miyoshi, S.; Ishii, T.

doi:10.1107/S2414314626008667

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 8| August 2026| x260866

https://doi.org/10.1107/S2414314626008667

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L-Talitol

Tomoko Takashita,^a ^* Yoji Horii,^a Shota Miyoshi ^a and Tomohiko Ishii ^a

^aGraduate School of Science for Creative Emergence, Kagawa University, 2217-20 Hayashi-cho, Takamatsu, Kagawa 761-0396, Japan
^*Correspondence e-mail: [email protected]

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 13 August 2026; accepted 20 August 2026; online 25 August 2026)

The title compound, C₆H₁₄O₆, the sugar alcohol corresponding to L-talose, was crystallized from aqueous solution. Colourless block-shaped single crystals suitable for single-crystal X-ray diffraction analysis were obtained. The title compound crystallizes in the monoclinic space group P2₁, with one molecule in the asymmetric unit. In the crystal, all six hydroxy groups act as donors in O—H⋯O hydrogen bonds, forming a three-dimensional hydrogen-bonded network. The crystal structure of its enantiomer, D-altritol (D-talitol), has been reported previously [Kopf et al. (1991 ). Carbohydr. Res. 217, 1–6].

Keywords: crystal structure; hydrogen bonding; rare sugar; sugar alcohol; talitol.

CCDC reference: 2577672

Structure description

L-Talitol is the sugar alcohol corresponding to the rare sugar L-talose. Systematic bioproduction strategies have expanded the availability of rare hexoses and their corresponding sugar alcohols (Izumori, 2002 ). Sugar alcohols possess multiple hydroxy groups and can therefore form extensive intermolecular hydrogen-bonding networks. Elucidation of their molecular conformations and crystal packing is important for understanding their solid-state properties.

The crystal structure of the enantiomer, D-altritol (D-talitol), was reported previously by Kopf et al. (1991; CSD refcode JOJZOX). The present study provides a modern single-crystal structure determination of the corresponding L enantiomer using Cu Kα radiation. Compared with the earlier determination, for which a conventional R value of 0.054 was reported, the present refinement gives a lower value of R₁ = 0.0292 and unit-cell parameters with smaller standard uncertainties. Furthermore, the anomalous-scattering data permitted assessment of the assigned absolute configuration, giving a Flack parameter of 0.07 (16) based on 570 quotients. The present determination therefore provides direct crystallographic characterization of L-talitol and a more precise modern dataset for this enantiomorphic pair.

The title compound, C₆H₁₄O₆ (Fig. 1), adopts an acyclic six-carbon chain structure. Single-crystal X-ray diffraction analysis revealed that it crystallizes in the monoclinic space group P2₁. The asymmetric unit contains one molecule of L-talitol.

Figure 1
Molecular structure of L-talitol, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level, and hydrogen atoms are shown as spheres of arbitrary radii.

In the crystal, all six hydroxy groups act as hydrogen-bond donors (Table 1), all of which are intermolecular interactions. These interactions link the molecules in all three crystallographic directions, producing a three-dimensional hydrogen-bonded network, as illustrated in Fig. 2.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1ⁱ	0.82	2.28	2.9570 (18)	140
O2—H2⋯O4ⁱⁱ	0.82	1.99	2.747 (2)	154
O3—H3⋯O2ⁱⁱⁱ	0.82	1.88	2.700 (2)	174
O4—H4⋯O5^iv	0.82	1.89	2.7027 (19)	174
O5—H5⋯O3^v	0.82	2.05	2.773 (2)	147
O6—H6⋯O6^vi	0.82	2.16	2.9502 (19)	162
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z]$ ; (ii) ; (iii) ; (iv) ; (v) ; (vi) $[-x+2, y-{\script{1\over 2}}, -z+1]$ .

Figure 2
Crystal packing of L-talitol, showing part of the three-dimensional hydrogen-bonded network, with the unit-cell directions indicated. The cyan dashed lines indicate the O⋯O contacts associated with the O—H⋯O hydrogen bonds. The central molecule is shown using a ball-and-stick representation, whereas the surrounding molecules are shown using a capped-stick representation.

Synthesis and crystallization

Commercially available L-talitol [Tokyo Chemical Industry Co., Ltd. (TCI)] was used as received without further purification. The sample was dissolved in water, and the solution was allowed to evaporate slowly at room temperature. Colorless block-shaped single crystals suitable for single-crystal X-ray diffraction analysis were obtained.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The absolute configuration was assigned on the basis of the known configuration of the commercially available L-talitol sample and was further supported by the refined Flack parameter. The Flack parameter was 0.07 (16), determined using 570 quotients of the type [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013 ).

Table 2
Experimental details

Crystal data
Chemical formula	C₆H₁₄O₆
M_r	182.17
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	4.8901 (3), 5.1671 (3), 16.3657 (10)
β (°)	100.136 (4)
V (Å³)	407.07 (4)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	1.17
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	0.711, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4278, 1446, 1399
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.075, 1.08
No. of reflections	1446
No. of parameters	116
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.12
Absolute structure	Flack x determined using 570 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013)
Absolute structure parameter	0.07 (16)
Computer programs: RAPID-AUTO (Rigaku, 2009 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and OLEX2 1.3 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2577672

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314626008667/vm4082sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626008667/vm4082Isup2.hkl

Point-by-point response to the Co-editors comments for the revised data article vm4082 (L-talitol), including a summary of the revisions and CCDC deposition number 2577672. DOI: https://doi.org/10.1107/S2414314626008667/vm4082sup3.docx

checkCIF report

Computing details top

L-Talitol top

Crystal data top

C₆H₁₄O₆	F(000) = 196
M_r = 182.17	D_x = 1.486 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54187 Å
a = 4.8901 (3) Å	Cell parameters from 1932 reflections
b = 5.1671 (3) Å	θ = 5.5–68.2°
c = 16.3657 (10) Å	µ = 1.17 mm⁻¹
β = 100.136 (4)°	T = 296 K
V = 407.07 (4) Å³	Block, clear light colourless
Z = 2	0.1 × 0.1 × 0.1 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	1399 reflections with I > 2σ(I)
ω scans	R_int = 0.059
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	θ_max = 68.2°, θ_min = 5.5°
T_min = 0.711, T_max = 1.000	h = −5→5
4278 measured reflections	k = −6→6
1446 independent reflections	l = −19→19

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0295P)² + 0.0407P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.029	(Δ/σ)_max < 0.001
wR(F²) = 0.075	Δρ_max = 0.20 e Å⁻³
S = 1.08	Δρ_min = −0.12 e Å⁻³
1446 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
116 parameters	Extinction coefficient: 0.027 (4)
1 restraint	Absolute structure: Flack x determined using 570 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: dual	Absolute structure parameter: 0.07 (16)
Hydrogen site location: inferred from neighbouring sites

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All non-hydrogen atoms were refined anisotropically. Hydroxy H atoms were placed in geometrically calculated positions and treated as rotating groups, with O—H = 0.82 Å. C-bound H atoms were placed in calculated positions and refined using riding models, with C—H = 0.98 Å for CH groups and 0.97 Å for CH₂ groups. For all H atoms, U_iso(H) was constrained to 1.2U_eq of the parent C or O atom.

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

	x	y	z	U_iso*/U_eq
O1	0.1487 (4)	0.2244 (3)	0.00353 (9)	0.0387 (5)
H1	0.049895	0.334701	−0.022940	0.046*
O2	0.2665 (3)	−0.0647 (3)	0.14835 (9)	0.0251 (4)
H2	0.351707	−0.178860	0.176956	0.030*
O3	0.8391 (3)	−0.0087 (3)	0.23126 (9)	0.0287 (4)
H3	0.960388	−0.023251	0.202749	0.034*
O4	0.3808 (3)	0.5215 (3)	0.25422 (8)	0.0260 (4)
H4	0.256058	0.531070	0.281637	0.031*
O5	0.9447 (3)	0.5638 (3)	0.33441 (9)	0.0277 (4)
H5	0.849284	0.676689	0.308092	0.033*
O6	0.8543 (4)	0.4580 (4)	0.49996 (9)	0.0400 (5)
H6	0.939124	0.322089	0.511232	0.048*
C1	0.2905 (5)	0.3341 (5)	0.07904 (12)	0.0268 (5)
H1A	0.158245	0.404113	0.110957	0.032*
H1B	0.411851	0.472857	0.067510	0.032*
C2	0.4582 (4)	0.1203 (4)	0.12684 (12)	0.0223 (5)
H2A	0.563950	0.035165	0.088863	0.027*
C3	0.6663 (4)	0.2077 (4)	0.20298 (12)	0.0205 (4)
H3A	0.781593	0.347156	0.186723	0.025*
C4	0.5431 (4)	0.2952 (4)	0.27779 (11)	0.0202 (4)
H4A	0.422927	0.158257	0.293084	0.024*
C5	0.7699 (4)	0.3574 (4)	0.35239 (12)	0.0229 (5)
H5A	0.885797	0.202833	0.364967	0.027*
C6	0.6458 (5)	0.4218 (6)	0.42847 (12)	0.0326 (5)
H6A	0.535703	0.578391	0.418094	0.039*
H6B	0.523187	0.282646	0.438795	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0476 (11)	0.0336 (10)	0.0273 (8)	0.0020 (9)	−0.0144 (7)	0.0010 (7)
O2	0.0235 (8)	0.0178 (7)	0.0326 (8)	0.0016 (6)	0.0010 (6)	0.0039 (6)
O3	0.0253 (8)	0.0309 (9)	0.0311 (8)	0.0116 (7)	0.0082 (6)	0.0070 (7)
O4	0.0250 (8)	0.0290 (9)	0.0250 (7)	0.0096 (7)	0.0073 (6)	0.0054 (6)
O5	0.0195 (7)	0.0287 (9)	0.0336 (8)	0.0001 (7)	0.0007 (6)	0.0071 (7)
O6	0.0508 (11)	0.0401 (10)	0.0238 (7)	0.0001 (9)	−0.0080 (7)	−0.0046 (7)
C1	0.0335 (12)	0.0224 (10)	0.0222 (9)	−0.0014 (10)	−0.0011 (8)	0.0014 (9)
C2	0.0228 (10)	0.0227 (10)	0.0217 (9)	0.0010 (9)	0.0043 (8)	−0.0004 (8)
C3	0.0191 (10)	0.0203 (10)	0.0215 (9)	0.0022 (8)	0.0015 (8)	0.0033 (8)
C4	0.0198 (10)	0.0203 (10)	0.0199 (8)	0.0028 (8)	0.0022 (7)	0.0042 (8)
C5	0.0225 (10)	0.0219 (11)	0.0227 (9)	0.0007 (8)	−0.0004 (8)	0.0028 (8)
C6	0.0327 (13)	0.0417 (13)	0.0222 (10)	−0.0032 (11)	0.0018 (9)	−0.0033 (10)

Geometric parameters (Å, º) top

O1—H1	0.8200	C1—H1B	0.9700
O1—C1	1.424 (2)	C1—C2	1.510 (3)
O2—H2	0.8200	C2—H2A	0.9800
O2—C2	1.425 (3)	C2—C3	1.532 (3)
O3—H3	0.8200	C3—H3A	0.9800
O3—C3	1.429 (2)	C3—C4	1.525 (3)
O4—H4	0.8200	C4—H4A	0.9800
O4—C4	1.428 (3)	C4—C5	1.532 (2)
O5—H5	0.8200	C5—H5A	0.9800
O5—C5	1.429 (2)	C5—C6	1.515 (3)
O6—H6	0.8200	C6—H6A	0.9700
O6—C6	1.423 (2)	C6—H6B	0.9700
C1—H1A	0.9700

C1—O1—H1	109.5	C2—C3—H3A	109.1
C2—O2—H2	109.5	C4—C3—C2	116.15 (16)
C3—O3—H3	109.5	C4—C3—H3A	109.1
C4—O4—H4	109.5	O4—C4—C3	107.77 (14)
C5—O5—H5	109.5	O4—C4—H4A	109.3
C6—O6—H6	109.5	O4—C4—C5	109.48 (17)
O1—C1—H1A	110.3	C3—C4—H4A	109.3
O1—C1—H1B	110.3	C3—C4—C5	111.66 (15)
O1—C1—C2	107.18 (18)	C5—C4—H4A	109.3
H1A—C1—H1B	108.5	O5—C5—C4	111.58 (16)
C2—C1—H1A	110.3	O5—C5—H5A	107.9
C2—C1—H1B	110.3	O5—C5—C6	110.23 (18)
O2—C2—C1	107.33 (17)	C4—C5—H5A	107.9
O2—C2—H2A	107.4	C6—C5—C4	111.25 (17)
O2—C2—C3	111.62 (16)	C6—C5—H5A	107.9
C1—C2—H2A	107.4	O6—C6—C5	111.83 (19)
C1—C2—C3	115.35 (17)	O6—C6—H6A	109.3
C3—C2—H2A	107.4	O6—C6—H6B	109.3
O3—C3—C2	107.65 (16)	C5—C6—H6A	109.3
O3—C3—H3A	109.1	C5—C6—H6B	109.3
O3—C3—C4	105.46 (14)	H6A—C6—H6B	107.9

O1—C1—C2—O2	−65.3 (2)	O5—C5—C6—O6	−60.8 (3)
O1—C1—C2—C3	169.64 (19)	C1—C2—C3—O3	−169.67 (16)
O2—C2—C3—O3	67.5 (2)	C1—C2—C3—C4	72.4 (2)
O2—C2—C3—C4	−50.4 (2)	C2—C3—C4—O4	−64.3 (2)
O3—C3—C4—O4	176.62 (16)	C2—C3—C4—C5	175.45 (19)
O3—C3—C4—C5	56.4 (2)	C3—C4—C5—O5	61.3 (2)
O4—C4—C5—O5	−57.9 (2)	C3—C4—C5—C6	−175.13 (18)
O4—C4—C5—C6	65.6 (2)	C4—C5—C6—O6	174.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1ⁱ	0.82	2.28	2.9570 (18)	140
O2—H2···O4ⁱⁱ	0.82	1.99	2.747 (2)	154
O3—H3···O2ⁱⁱⁱ	0.82	1.88	2.700 (2)	174
O4—H4···O5^iv	0.82	1.89	2.7027 (19)	174
O5—H5···O3^v	0.82	2.05	2.773 (2)	147
O6—H6···O6^vi	0.82	2.16	2.9502 (19)	162

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

Acknowledgements

The authors gratefully acknowledge Professor Genta Sakane (Okayama University of Science) for valuable discussions and technical guidance, and Kei Takeshita (FUSHIMI Pharmaceutical Co., Ltd.) for helpful suggestions. This work was supported by the JST Support for Pioneering Research Initiated by the Next Generation (SPRING) program, Japan.

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