allo-Inositol

Bonnet, A.; Jones, W.; Motherwell, W.D.S.

doi:10.1107/S1600536806019817

organic compounds

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ISSN: 2056-9890

Volume 62| Part 7| July 2006| Pages o2578-o2579

https://doi.org/10.1107/S1600536806019817

allo-Inositol

Arnaud Bonnet,^a William Jones ^a and W. D. Samuel Motherwell ^b ^*

^aThe Pfizer Institute for Pharmaceutical Materials Science, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, England, and ^bThe Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, England
^*Correspondence e-mail: motherwell@ccdc.cam.ac.uk

(Received 22 May 2006; accepted 26 May 2006; online 9 June 2006)

In the crystal structure of the title compound, C₆H₁₂O₆, molecules adopt a chair conformation. The H atoms were located and their positions refined satisfactorily. The molecules form one intramolecular and 12 intermolecular hydrogen bonds; all hydroxyl groups act as hydrogen-bond donors and acceptors.

Comment

Inositols are isomers of pyranose sugars (C₆H₁₂O₆), and are present in nature and in biological systems (Podeschwa et al., 2003 ). We have reported elsewhere on the hydrogen bonds in crystal structures of some cyclohexanol derivatives (Bonnet et al., 2005 ), and a study of the Cambridge Structural Database (Version 5.27; Allen, 2002 ) reveals that the crystal structures of only five of the nine isomeric inositols have been reported. Here we report the crystal structure of allo-inositol (Fig. 1). Fig. 2 provides a view along the a axis, showing each molecule linked to eight neighbouring molecules by hydrogen bonds.

Figure 1
The molecular structure of allo-inositol. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
Packing diagram for allo-inositol, viewed along the a axis. The dashed lines show O⋯O contacts for hydrogen bonds.

Experimental

allo-Inositol (97%) was obtained from Sigma–Aldrich UK as a crystalline powder, and its purity was confirmed by solution NMR and elemental analysis. Suitable single crystals were obtained by vapour diffusion of acetone into an aqueous solution of the inositol, after a week at room temperature. Elemental analysis gave C 40.10, H 6.66, O 53.24%; expected: C 40.00, H 6.71, O 53.28%. The onset melting temperature was determined using differential scanning calorimetry, and gave a value of 454 K with reproducibility [literature: 583 K, with decomposition (Tschamber et al., 1992 )].

Crystal data

C₆H₁₂O₆
M_r = 180.16
Monoclinic, P 2₁ /n
a = 4.9520 (2) Å
b = 11.3145 (6) Å
c = 12.7326 (6) Å
β = 91.142 (3)°
V = 713.26 (6) Å³
Z = 4
D_x = 1.678 Mg m⁻³
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 180 (2) K
Block, colourless
0.23 × 0.18 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer
thin–slice ω and φ scans
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.896, T_max = 0.975
5743 measured reflections
1627 independent reflections
1387 reflections with I > 2σ(I)
R_int = 0.038
θ_max = 27.4°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.102
S = 1.06
1627 reflections
130 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F_o²) + (0.0508P)² + 0.2778P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.004
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82 (2)	1.95 (2)	2.7695 (14)	174 (2)
O2—H2⋯O5ⁱⁱ	0.82 (2)	1.91 (2)	2.7289 (14)	179 (2)
O3—H3⋯O6ⁱⁱⁱ	0.85 (2)	1.90 (2)	2.7423 (13)	171 (2)
O4—H4⋯O3^iv	0.84 (2)	1.93 (2)	2.7461 (14)	164 (2)
O5—H5⋯O2^v	0.86 (2)	2.12 (2)	2.9014 (14)	152 (2)
O6—H6⋯O1^vi	0.82 (2)	2.05 (2)	2.8248 (13)	158 (2)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x, -y+1, -z+1; (v) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (vi) x-1, y, z.

The O-bound H atoms were all located in a difference map and refined with a common isotropic displacement parameter [0.041 (2) Å²]; O—H distances were restrained to a target value of 0.83 (1) Å. The C-bound H atoms were placed in calculated positions, with C—H = 1.00 Å, and refined as riding with a common isotropic displacement parameter [0.016 (2) Å²]

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: MERCURY (Version 1.4; Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536806019817/wn2031sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806019817/wn2031Isup2.hkl

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Version 1.4; Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

hexahydroxycyclohexane top

Crystal data top

C₆H₁₂O₆	F(000) = 384
M_r = 180.16	D_x = 1.678 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8271 reflections
a = 4.9520 (2) Å	θ = 1.0–27.5°
b = 11.3145 (6) Å	µ = 0.15 mm⁻¹
c = 12.7326 (6) Å	T = 180 K
β = 91.142 (3)°	Block, colourless
V = 713.26 (6) Å³	0.23 × 0.18 × 0.18 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	1387 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.038
thin–slice ω and φ scans	θ_max = 27.4°, θ_min = 3.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −6→6
T_min = 0.896, T_max = 0.975	k = −14→14
5743 measured reflections	l = −16→16
1627 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0508P)² + 0.2778P] where P = (F_o² + 2F_c²)/3
1627 reflections	(Δ/σ)_max = 0.004
130 parameters	Δρ_max = 0.31 e Å⁻³
6 restraints	Δρ_min = −0.46 e Å⁻³

Special details top

Experimental. The –OH hydrogen atoms were all located and their positions were refined satisfactorily.

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 of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
O1	0.58505 (18)	0.10025 (9)	0.42187 (7)	0.0175 (2)
H1	0.622 (4)	0.0302 (16)	0.4147 (15)	0.041 (2)*
C1	0.2986 (3)	0.11545 (11)	0.40831 (10)	0.0144 (3)
H1A	0.2090	0.0363	0.4105	0.0158 (15)*
O2	0.2568 (2)	0.13354 (8)	0.59619 (7)	0.0167 (2)
H2	0.112 (4)	0.1375 (18)	0.6268 (16)	0.041 (2)*
C2	0.1944 (2)	0.19153 (11)	0.49771 (9)	0.0137 (3)
H2A	−0.0064	0.1981	0.4898	0.0158 (15)*
O3	0.2171 (2)	0.38616 (8)	0.57924 (7)	0.0204 (3)
H3	0.306 (4)	0.3661 (18)	0.6344 (15)	0.041 (2)*
C3	0.3147 (3)	0.31563 (11)	0.49478 (9)	0.0148 (3)
H3A	0.5160	0.3103	0.5003	0.0158 (15)*
O4	−0.05263 (19)	0.38676 (9)	0.38074 (8)	0.0201 (2)
H4	−0.100 (4)	0.4524 (16)	0.4050 (16)	0.041 (2)*
C4	0.2332 (3)	0.37526 (12)	0.39100 (10)	0.0160 (3)
H4A	0.3170	0.4556	0.3885	0.0158 (15)*
O5	0.2820 (2)	0.35459 (9)	0.20083 (7)	0.0207 (2)
H5	0.113 (4)	0.3447 (17)	0.1893 (16)	0.041 (2)*
C5	0.3387 (3)	0.30110 (12)	0.30029 (10)	0.0165 (3)
H5A	0.5398	0.2990	0.3089	0.0158 (15)*
O6	−0.03399 (19)	0.16142 (9)	0.26888 (7)	0.0193 (2)
H6	−0.133 (4)	0.1621 (17)	0.3195 (15)	0.041 (2)*
C6	0.2426 (3)	0.17232 (12)	0.30083 (9)	0.0159 (3)
H6A	0.3520	0.1284	0.2484	0.0158 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0142 (5)	0.0162 (5)	0.0222 (5)	0.0024 (4)	0.0009 (4)	0.0007 (4)
C1	0.0140 (6)	0.0132 (6)	0.0159 (6)	0.0000 (5)	0.0007 (5)	0.0002 (4)
O2	0.0184 (5)	0.0189 (5)	0.0128 (4)	0.0022 (4)	0.0018 (3)	0.0023 (3)
C2	0.0139 (6)	0.0142 (6)	0.0130 (6)	0.0005 (5)	−0.0006 (4)	0.0014 (4)
O3	0.0267 (5)	0.0172 (5)	0.0173 (5)	0.0065 (4)	−0.0020 (4)	−0.0041 (4)
C3	0.0164 (6)	0.0126 (6)	0.0154 (6)	0.0015 (5)	−0.0008 (5)	−0.0017 (4)
O4	0.0164 (5)	0.0182 (5)	0.0255 (5)	0.0033 (4)	−0.0027 (4)	−0.0015 (4)
C4	0.0155 (6)	0.0140 (6)	0.0185 (6)	−0.0011 (5)	−0.0009 (5)	0.0016 (5)
O5	0.0198 (5)	0.0247 (6)	0.0176 (5)	−0.0008 (4)	0.0006 (4)	0.0073 (4)
C5	0.0155 (6)	0.0181 (7)	0.0158 (6)	−0.0004 (5)	−0.0004 (5)	0.0037 (5)
O6	0.0167 (5)	0.0248 (5)	0.0162 (5)	−0.0019 (4)	−0.0008 (3)	0.0001 (4)
C6	0.0165 (6)	0.0179 (7)	0.0134 (6)	0.0004 (5)	0.0006 (5)	0.0001 (5)

Geometric parameters (Å, º) top

O1—C1	1.4357 (15)	C3—H3A	1.0000
O1—H1	0.819 (17)	O4—C4	1.4248 (15)
C1—C2	1.5253 (17)	O4—H4	0.839 (17)
C1—C6	1.5325 (17)	C4—C5	1.5281 (18)
C1—H1A	1.0000	C4—H4A	1.0000
O2—C2	1.4432 (15)	O5—C5	1.4265 (15)
O2—H2	0.823 (18)	O5—H5	0.855 (18)
C2—C3	1.5259 (18)	C5—C6	1.5329 (18)
C2—H2A	1.0000	C5—H5A	1.0000
O3—C3	1.4309 (15)	O6—C6	1.4263 (16)
O3—H3	0.853 (18)	O6—H6	0.817 (17)
C3—C4	1.5305 (17)	C6—H6A	1.0000

C1—O1—H1	108.9 (15)	C4—O4—H4	109.2 (15)
O1—C1—C2	109.03 (10)	O4—C4—C5	109.56 (10)
O1—C1—C6	108.58 (10)	O4—C4—C3	111.33 (10)
C2—C1—C6	111.81 (10)	C5—C4—C3	108.80 (10)
O1—C1—H1A	109.1	O4—C4—H4A	109.0
C2—C1—H1A	109.1	C5—C4—H4A	109.0
C6—C1—H1A	109.1	C3—C4—H4A	109.0
C2—O2—H2	102.3 (15)	C5—O5—H5	105.8 (14)
O2—C2—C1	108.79 (10)	O5—C5—C4	111.95 (10)
O2—C2—C3	111.26 (10)	O5—C5—C6	110.59 (10)
C1—C2—C3	111.28 (10)	C4—C5—C6	114.06 (10)
O2—C2—H2A	108.5	O5—C5—H5A	106.6
C1—C2—H2A	108.5	C4—C5—H5A	106.6
C3—C2—H2A	108.5	C6—C5—H5A	106.6
C3—O3—H3	107.1 (14)	C6—O6—H6	111.2 (15)
O3—C3—C2	110.92 (10)	O6—C6—C1	111.98 (10)
O3—C3—C4	108.41 (10)	O6—C6—C5	112.17 (10)
C2—C3—C4	109.30 (10)	C1—C6—C5	110.63 (10)
O3—C3—H3A	109.4	O6—C6—H6A	107.3
C2—C3—H3A	109.4	C1—C6—H6A	107.3
C4—C3—H3A	109.4	C5—C6—H6A	107.3

O1—C1—C2—O2	−59.22 (12)	O4—C4—C5—O5	61.06 (13)
C6—C1—C2—O2	−179.29 (10)	C3—C4—C5—O5	−177.02 (10)
O1—C1—C2—C3	63.71 (13)	O4—C4—C5—C6	−65.47 (13)
C6—C1—C2—C3	−56.37 (14)	C3—C4—C5—C6	56.45 (14)
O2—C2—C3—O3	−58.16 (13)	O1—C1—C6—O6	164.10 (10)
C1—C2—C3—O3	−179.65 (10)	C2—C1—C6—O6	−75.56 (13)
O2—C2—C3—C4	−177.64 (10)	O1—C1—C6—C5	−69.97 (12)
C1—C2—C3—C4	60.87 (13)	C2—C1—C6—C5	50.37 (14)
O3—C3—C4—O4	−59.66 (13)	O5—C5—C6—O6	−53.13 (13)
C2—C3—C4—O4	61.36 (13)	C4—C5—C6—O6	74.11 (13)
O3—C3—C4—C5	179.51 (10)	O5—C5—C6—C1	−178.95 (10)
C2—C3—C4—C5	−59.48 (13)	C4—C5—C6—C1	−51.71 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82 (2)	1.95 (2)	2.7695 (14)	174 (2)
O2—H2···O5ⁱⁱ	0.82 (2)	1.91 (2)	2.7289 (14)	179 (2)
O3—H3···O6ⁱⁱⁱ	0.85 (2)	1.90 (2)	2.7423 (13)	171 (2)
O4—H4···O3^iv	0.84 (2)	1.93 (2)	2.7461 (14)	164 (2)
O5—H5···O2^v	0.86 (2)	2.12 (2)	2.9014 (14)	152 (2)
O6—H6···O1^vi	0.82 (2)	2.05 (2)	2.8248 (13)	158 (2)

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

Acknowledgements

The authors are grateful to Dr John Davies (Department of Chemistry, University of Cambridge) for determining the crystal structure, and Drs A. Trask and L. Fabian for help with CIF preparation. The Pfizer Institute for Pharmaceutical Materials Science is acknowledged for funding the work.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 62| Part 7| July 2006| Pages o2578-o2579

https://doi.org/10.1107/S1600536806019817

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		EndNote
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

allo-Inositol

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds