organic papers allo-inositol o2578 Bonnet et al. C 6 H 12 O 6 doi: /s Acta Cryst. (2006). E62, o2578 o2579 Comment Experimental

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1 organic papers Acta Crystallographica Section E Structure Reports Online ISSN allo-inositol Arnaud Bonnet, a William Jones a and W. D. Samuel Motherwell b * a The Pfizer Institute for Pharmaceutical Materials Science, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, England, and b The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, England Correspondence motherwell@ccdc.cam.ac.uk Key indicators Single-crystal X-ray study T = 180 K Mean (C C) = Å R factor = wr factor = Data-to-parameter ratio = 12.5 In the crystal structure of the title compound, C 6 H 12 O 6, 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 (C 6 H 12 O 6 ), 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. Received 22 May 2006 Accepted 26 May 2006 For details of how these key indicators were automatically derived from the article, see 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)]. # 2006 International Union of Crystallography All rights reserved Crystal data C 6 H 12 O 6 M r = Monoclinic, P2 1 =n a = (2) Å b = (6) Å c = (6) Å = (3) V = (6) Å 3 Z =4 D x = Mg m 3 Mo K radiation = 0.15 mm 1 T = 180 (2) K Block, colourless mm o2578 Bonnet et al. C 6 H 12 O 6 doi: /s

2 organic papers Refinement Refinement on F 2 R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 130 parameters H atoms treated by a mixture of independent and constrained refinement w = 1/[ 2 (F o 2 ) + (0.0508P) P] where P =(F o 2 +2F c 2 )/3 (/) max = max = 0.31 e Å 3 min = 0.46 e Å 3 Table 1 Hydrogen-bond geometry (Å, ). D HA D H HA DA D HA Figure 1 The molecular structure of allo-inositol. Displacement ellipsoids are drawn at the 50% probability level. O1 H1O2 i 0.82 (2) 1.95 (2) (14) 174 (2) O2 H2O5 ii 0.82 (2) 1.91 (2) (14) 179 (2) O3 H3O6 iii 0.85 (2) 1.90 (2) (13) 171 (2) O4 H4O3 iv 0.84 (2) 1.93 (2) (14) 164 (2) O5 H5O2 v 0.86 (2) 2.12 (2) (14) 152 (2) O6 H6O1 vi 0.82 (2) 2.05 (2) (13) 158 (2) Symmetry codes: (i) x þ 1; y; z þ 1; (ii) x 1 2 ; y þ 1 2 ; z þ 1 2 ; (iii) x þ 1 2 ; y þ 1 2 ; z þ 1 2 ; (iv) x; y þ 1; z þ 1; (v) x 1 2 ; y þ 1 2 ; z 1 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) Å 2 ]; 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) Å 2 ] 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. 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. Figure 2 Packing diagram for allo-inositol, viewed along the a axis. The dashed lines show OO contacts for hydrogen bonds. Data collection Nonius KappaCCD diffractometer thin slice! and scans Absorption correction: multi-scan (SORTAV; Blessing, 1995) T min = 0.896, T max = measured reflections 1627 independent reflections 1387 reflections with I > 2(I) R int = max = 27.4 References Allen, F. H. (2002). Acta Cryst. B58, Altomare, A., Burla, M. C., Camalli, G., Cascarano, G., Giacovazzo, C., Guagliardi, A. & Polidori, G. (1994). J. Appl. Cryst. 27, Blessing, R. H. (1995). Acta Cryst. A51, Bonnet, A., Motherwell, W. D. S., Chisholm, J. A. & Jones, W. (2005). CrystEngComm, 7, Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 279, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp New York: Academic Press. Podeschwa, M., Plettenburg, O., Van Brocke, J., Block, O., Adelt, S. & Altenbach, H. (2003). Eur. J. Org. Chem. pp Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Tschamber, T., Backenstrass, F., Fritz, H. & Streith, J. (1992). Helv. Chim. Acta, 75, Bonnet et al. C 6 H 12 O 6 o2579

3 supporting information [ allo-inositol Arnaud Bonnet, William Jones and W. D. Samuel Motherwell hexahydroxycyclohexane Crystal data C 6 H 12 O 6 M r = Monoclinic, P2 1 /n Hall symbol: -P 2yn a = (2) Å b = (6) Å c = (6) Å β = (3) V = (6) Å 3 Z = 4 Data collection Nonius KappaCCD diffractometer Radiation source: fine-focus sealed tube thin slice ω and φ scans Absorption correction: multi-scan (SORTAV; Blessing, 1995) T min = 0.896, T max = measured reflections Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 130 parameters 6 restraints Primary atom site location: structure-invariant direct methods F(000) = 384 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from 8271 reflections θ = µ = 0.15 mm 1 T = 180 K Block, colourless mm 1627 independent reflections 1387 reflections with I > 2σ(I) R int = θ max = 27.4, θ min = 3.6 h = 6 6 k = l = Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H atoms treated by a mixture of independent and constrained refinement w = 1/[σ 2 (F o2 ) + (0.0508P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max = Δρ max = 0.31 e Å 3 Δρ min = 0.46 e Å 3 Special details 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. sup-1

4 Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 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 (Å 2 ) x y z U iso */U eq O (18) (9) (7) (2) H (4) (16) (15) (2)* C (3) (11) (10) (3) H1A (15)* O (2) (8) (7) (2) H (4) (18) (16) (2)* C (2) (11) (9) (3) H2A (15)* O (2) (8) (7) (3) H (4) (18) (15) (2)* C (3) (11) (9) (3) H3A (15)* O (19) (9) (8) (2) H (4) (16) (16) (2)* C (3) (12) (10) (3) H4A (15)* O (2) (9) (7) (2) H (4) (17) (16) (2)* C (3) (12) (10) (3) H5A (15)* O (19) (9) (7) (2) H (4) (17) (15) (2)* C (3) (12) (9) (3) H6A (15)* Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 O (5) (5) (5) (4) (4) (4) C (6) (6) (6) (5) (5) (4) O (5) (5) (4) (4) (3) (3) C (6) (6) (6) (5) (4) (4) O (5) (5) (5) (4) (4) (4) C (6) (6) (6) (5) (5) (4) O (5) (5) (5) (4) (4) (4) C (6) (6) (6) (5) (5) (5) O (5) (6) (5) (4) (4) (4) C (6) (7) (6) (5) (5) (5) O (5) (5) (5) (4) (3) (4) C (6) (7) (6) (5) (5) (5) sup-2

5 Geometric parameters (Å, º) O1 C (15) C3 H3A O1 H (17) O4 C (15) C1 C (17) O4 H (17) C1 C (17) C4 C (18) C1 H1A C4 H4A O2 C (15) O5 C (15) O2 H (18) O5 H (18) C2 C (18) C5 C (18) C2 H2A C5 H5A O3 C (15) O6 C (16) O3 H (18) O6 H (17) C3 C (17) C6 H6A C1 O1 H (15) C4 O4 H (15) O1 C1 C (10) O4 C4 C (10) O1 C1 C (10) O4 C4 C (10) C2 C1 C (10) C5 C4 C (10) O1 C1 H1A O4 C4 H4A C2 C1 H1A C5 C4 H4A C6 C1 H1A C3 C4 H4A C2 O2 H (15) C5 O5 H (14) O2 C2 C (10) O5 C5 C (10) O2 C2 C (10) O5 C5 C (10) C1 C2 C (10) C4 C5 C (10) O2 C2 H2A O5 C5 H5A C1 C2 H2A C4 C5 H5A C3 C2 H2A C6 C5 H5A C3 O3 H (14) C6 O6 H (15) O3 C3 C (10) O6 C6 C (10) O3 C3 C (10) O6 C6 C (10) C2 C3 C (10) C1 C6 C (10) O3 C3 H3A O6 C6 H6A C2 C3 H3A C1 C6 H6A C4 C3 H3A C5 C6 H6A O1 C1 C2 O (12) O4 C4 C5 O (13) C6 C1 C2 O (10) C3 C4 C5 O (10) O1 C1 C2 C (13) O4 C4 C5 C (13) C6 C1 C2 C (14) C3 C4 C5 C (14) O2 C2 C3 O (13) O1 C1 C6 O (10) C1 C2 C3 O (10) C2 C1 C6 O (13) O2 C2 C3 C (10) O1 C1 C6 C (12) C1 C2 C3 C (13) C2 C1 C6 C (14) O3 C3 C4 O (13) O5 C5 C6 O (13) C2 C3 C4 O (13) C4 C5 C6 O (13) O3 C3 C4 C (10) O5 C5 C6 C (10) sup-3

6 C2 C3 C4 C (13) C4 C5 C6 C (14) Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A O1 H1 O2 i 0.82 (2) 1.95 (2) (14) 174 (2) O2 H2 O5 ii 0.82 (2) 1.91 (2) (14) 179 (2) O3 H3 O6 iii 0.85 (2) 1.90 (2) (13) 171 (2) O4 H4 O3 iv 0.84 (2) 1.93 (2) (14) 164 (2) O5 H5 O2 v 0.86 (2) 2.12 (2) (14) 152 (2) O6 H6 O1 vi 0.82 (2) 2.05 (2) (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. sup-4