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The structure of the title compound, C6H10O6, was determined to confirm the position of the keto group in the molecule prepared enantioselectively by a bioconversion from myo-inositol. There are two independent molecules showing similar geometry.
Supporting information
CCDC reference: 156213
Crystals of (I) were grown from an aqueous ethanol solution.
All H atoms were located from difference syntheses and refined isotropically; the O—H and C—H lengths are 0.73 (3)–0.85 (4) and 0.91 (2)–1.01 (2) Å, respectively. The absolute structure was assumed based on the known absolute configuration of the title compound (Posternak, 1946).
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN
(Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-II (Johnson, 1976); software used to prepare material for publication: TEXSAN.
(-)-2
L-(2,3,4,6/5)–2,3,4,5,6-pentahydroxycyclohexanone
top
Crystal data top
C6H10O6 | Dx = 1.696 Mg m−3 |
Mr = 178.14 | Mo Kα radiation, λ = 0.71073 Å |
Monoclinic, P21 | Cell parameters from 25 reflections |
a = 11.197 (2) Å | θ = 13.9–15.0° |
b = 8.932 (2) Å | µ = 0.16 mm−1 |
c = 6.976 (2) Å | T = 298 K |
β = 90.21 (2)° | Prism, colourless |
V = 697.7 (3) Å3 | 0.7 × 0.4 × 0.15 mm |
Z = 4 | |
Data collection top
Rigaku AFC-7R diffractometer | θmax = 30.0°, θmin = 2.5° |
θ–2θ scans | h = 0→16 |
2250 measured reflections | k = 0→13 |
2151 independent reflections | l = −10→10 |
2086 reflections with I > 2σ(I) | 3 standard reflections every 150 reflections |
Rint = 0.005 | intensity decay: none |
Refinement top
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0417P)2 + 0.0965P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.024 | (Δ/σ)max < 0.001 |
wR(F2) = 0.068 | Δρmax = 0.30 e Å−3 |
S = 1.13 | Δρmin = −0.16 e Å−3 |
2151 reflections | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
298 parameters | Extinction coefficient: 0.027 (5) |
All H-atom parameters refined | |
Crystal data top
C6H10O6 | V = 697.7 (3) Å3 |
Mr = 178.14 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 11.197 (2) Å | µ = 0.16 mm−1 |
b = 8.932 (2) Å | T = 298 K |
c = 6.976 (2) Å | 0.7 × 0.4 × 0.15 mm |
β = 90.21 (2)° | |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.005 |
2250 measured reflections | 3 standard reflections every 150 reflections |
2151 independent reflections | intensity decay: none |
2086 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.024 | 298 parameters |
wR(F2) = 0.068 | All H-atom parameters refined |
S = 1.13 | Δρmax = 0.30 e Å−3 |
2151 reflections | Δρmin = −0.16 e Å−3 |
Special details top
Refinement. Refinement was based on F2 against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F2, and conventional R-factor (R) was calculated on F, with F set to zero for negative F2. The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 1.0457 (1) | 0.3579 (2) | 0.3761 (2) | 0.0324 (3) | |
O2 | 0.8261 (1) | 0.4061 (1) | 0.5071 (2) | 0.0242 (2) | |
O3 | 0.6986 (1) | 0.6413 (2) | 0.3049 (2) | 0.0294 (3) | |
O4 | 0.8090 (1) | 0.7696 (2) | −0.0089 (2) | 0.0238 (2) | |
O5 | 0.9848 (1) | 0.5525 (2) | −0.0615 (2) | 0.0249 (2) | |
O6 | 1.18929 (9) | 0.5535 (2) | 0.1883 (2) | 0.0237 (2) | |
O51 | 0.6833 (1) | 0.2921 (1) | 0.0910 (2) | 0.0285 (2) | |
O52 | 0.4601 (1) | 0.2429 (2) | −0.0112 (2) | 0.0324 (3) | |
O53 | 0.3339 (1) | 0.0107 (1) | 0.2045 (2) | 0.0243 (2) | |
O54 | 0.4527 (1) | −0.0782 (1) | 0.5493 (2) | 0.0230 (2) | |
O55 | 0.6301 (1) | 0.1431 (1) | 0.5620 (2) | 0.0213 (2) | |
O56 | 0.82685 (9) | 0.1161 (2) | 0.3082 (2) | 0.0253 (2) | |
C7 | 1.0074 (1) | 0.4828 (2) | 0.3542 (2) | 0.0187 (2) | |
C8 | 0.8841 (1) | 0.5307 (2) | 0.4220 (2) | 0.0180 (2) | |
C9 | 0.8130 (1) | 0.5875 (2) | 0.2481 (2) | 0.0180 (2) | |
C10 | 0.8781 (1) | 0.7153 (2) | 0.1488 (2) | 0.0173 (2) | |
C11 | 1.0015 (1) | 0.6653 (2) | 0.0804 (2) | 0.0185 (2) | |
C12 | 1.0756 (1) | 0.6045 (2) | 0.2491 (2) | 0.0182 (2) | |
C57 | 0.6421 (1) | 0.1728 (2) | 0.1383 (2) | 0.0186 (2) | |
C58 | 0.5168 (1) | 0.1235 (2) | 0.0823 (2) | 0.0203 (3) | |
C59 | 0.4475 (1) | 0.0722 (2) | 0.2611 (2) | 0.0170 (2) | |
C60 | 0.5179 (1) | −0.0408 (2) | 0.3806 (2) | 0.0167 (2) | |
C61 | 0.6409 (1) | 0.0172 (2) | 0.4381 (2) | 0.0167 (2) | |
C62 | 0.7121 (1) | 0.0617 (2) | 0.2592 (2) | 0.0187 (2) | |
H2 | 0.781 (3) | 0.434 (4) | 0.581 (4) | 0.04721 (10)* | |
H3 | 0.663 (2) | 0.565 (3) | 0.345 (4) | 0.03637 (8)* | |
H4 | 0.803 (3) | 0.707 (4) | −0.077 (4) | 0.0486 (1)* | |
H5 | 1.041 (2) | 0.563 (4) | −0.136 (4) | 0.04258 (9)* | |
H6 | 1.182 (2) | 0.472 (3) | 0.160 (4) | 0.03219 (8)* | |
H8 | 0.891 (2) | 0.612 (3) | 0.514 (3) | 0.02305 (6)* | |
H9 | 0.804 (2) | 0.509 (3) | 0.162 (3) | 0.02171 (6)* | |
H10 | 0.883 (2) | 0.803 (3) | 0.240 (3) | 0.02047 (6)* | |
H11 | 1.042 (2) | 0.753 (3) | 0.026 (3) | 0.02184 (6)* | |
H12 | 1.085 (2) | 0.683 (2) | 0.342 (3) | 0.01721 (6)* | |
H52 | 0.402 (3) | 0.212 (5) | −0.077 (5) | 0.0753 (1)* | |
H53 | 0.343 (2) | −0.055 (4) | 0.126 (4) | 0.04038 (9)* | |
H54 | 0.423 (2) | −0.161 (3) | 0.525 (3) | 0.02950 (7)* | |
H55 | 0.681 (2) | 0.126 (4) | 0.642 (4) | 0.04366 (9)* | |
H56 | 0.822 (3) | 0.208 (4) | 0.356 (4) | 0.0517 (1)* | |
H58 | 0.526 (2) | 0.037 (3) | 0.000 (3) | 0.02508 (7)* | |
H59 | 0.429 (2) | 0.157 (3) | 0.341 (3) | 0.01975 (6)* | |
H60 | 0.526 (2) | −0.130 (3) | 0.319 (3) | 0.02068 (6)* | |
H61 | 0.682 (2) | −0.063 (3) | 0.504 (3) | 0.02241 (6)* | |
H62 | 0.718 (2) | −0.033 (3) | 0.188 (3) | 0.02101 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0308 (6) | 0.0247 (6) | 0.0417 (7) | 0.0090 (5) | 0.0066 (5) | 0.0090 (5) |
O2 | 0.0270 (5) | 0.0205 (5) | 0.0252 (5) | 0.0009 (4) | 0.0082 (4) | 0.0062 (4) |
O3 | 0.0178 (5) | 0.0320 (6) | 0.0384 (6) | 0.0050 (5) | 0.0080 (4) | 0.0114 (6) |
O4 | 0.0240 (5) | 0.0256 (6) | 0.0219 (5) | 0.0035 (4) | −0.0030 (4) | 0.0059 (5) |
O5 | 0.0229 (5) | 0.0322 (6) | 0.0196 (4) | 0.0004 (5) | 0.0018 (4) | −0.0048 (4) |
O6 | 0.0135 (4) | 0.0280 (6) | 0.0295 (5) | 0.0001 (4) | −0.0008 (4) | −0.0011 (5) |
O51 | 0.0277 (5) | 0.0249 (6) | 0.0328 (6) | −0.0082 (5) | −0.0018 (4) | 0.0058 (5) |
O52 | 0.0313 (6) | 0.0316 (7) | 0.0344 (6) | −0.0084 (5) | −0.0145 (5) | 0.0160 (5) |
O53 | 0.0185 (4) | 0.0299 (6) | 0.0244 (5) | −0.0059 (4) | −0.0025 (4) | −0.0014 (5) |
O54 | 0.0236 (5) | 0.0247 (6) | 0.0207 (5) | −0.0035 (4) | 0.0058 (4) | 0.0034 (4) |
O55 | 0.0226 (5) | 0.0219 (5) | 0.0195 (5) | 0.0020 (4) | −0.0021 (4) | −0.0040 (4) |
O56 | 0.0134 (4) | 0.0339 (6) | 0.0287 (5) | −0.0012 (4) | 0.0023 (4) | −0.0007 (5) |
C7 | 0.0184 (5) | 0.0211 (6) | 0.0165 (5) | 0.0000 (5) | −0.0019 (4) | 0.0011 (5) |
C8 | 0.0200 (6) | 0.0163 (6) | 0.0176 (5) | 0.0001 (5) | 0.0016 (4) | 0.0014 (5) |
C9 | 0.0160 (5) | 0.0180 (6) | 0.0201 (6) | 0.0010 (5) | 0.0007 (4) | 0.0025 (5) |
C10 | 0.0172 (5) | 0.0157 (6) | 0.0190 (6) | 0.0015 (5) | −0.0002 (4) | 0.0029 (4) |
C11 | 0.0161 (5) | 0.0188 (6) | 0.0206 (6) | −0.0007 (5) | 0.0009 (4) | 0.0022 (5) |
C12 | 0.0145 (5) | 0.0197 (6) | 0.0204 (6) | −0.0003 (5) | −0.0008 (4) | −0.0012 (5) |
C57 | 0.0190 (6) | 0.0222 (7) | 0.0147 (5) | −0.0012 (5) | 0.0024 (4) | −0.0008 (5) |
C58 | 0.0228 (6) | 0.0218 (7) | 0.0163 (5) | −0.0053 (5) | −0.0023 (4) | 0.0035 (5) |
C59 | 0.0163 (5) | 0.0175 (6) | 0.0172 (5) | −0.0025 (5) | −0.0010 (4) | 0.0004 (5) |
C60 | 0.0185 (5) | 0.0162 (6) | 0.0153 (5) | −0.0009 (5) | 0.0035 (4) | 0.0003 (5) |
C61 | 0.0161 (5) | 0.0170 (6) | 0.0171 (5) | 0.0026 (5) | 0.0011 (4) | 0.0006 (5) |
C62 | 0.0153 (5) | 0.0229 (6) | 0.0181 (5) | 0.0004 (5) | 0.0035 (4) | −0.0007 (5) |
Geometric parameters (Å, º) top
O1—C7 | 1.205 (2) | C7—C8 | 1.522 (2) |
O2—C8 | 1.419 (2) | C7—C12 | 1.518 (2) |
O2—H2 | 0.76 (3) | C8—C9 | 1.535 (2) |
O3—C9 | 1.425 (2) | C8—H8 | 0.97 (2) |
O3—H3 | 0.84 (3) | C9—C10 | 1.523 (2) |
O4—C10 | 1.428 (2) | C9—H9 | 0.93 (2) |
O4—H4 | 0.73 (3) | C10—C11 | 1.530 (2) |
O5—C11 | 1.424 (2) | C10—H10 | 1.01 (2) |
O5—H5 | 0.82 (3) | C11—C12 | 1.536 (2) |
O6—C12 | 1.418 (2) | C11—H11 | 0.98 (2) |
O6—H6 | 0.76 (3) | C12—H12 | 0.96 (2) |
O51—C57 | 1.207 (2) | C57—C58 | 1.521 (2) |
O52—C58 | 1.401 (2) | C57—C62 | 1.519 (2) |
O52—H52 | 0.85 (4) | C58—C59 | 1.541 (2) |
O53—C59 | 1.440 (2) | C58—H58 | 0.97 (3) |
O53—H53 | 0.81 (3) | C59—C60 | 1.526 (2) |
O54—C60 | 1.427 (2) | C59—H59 | 0.96 (2) |
O54—H54 | 0.83 (3) | C60—C61 | 1.523 (2) |
O55—C61 | 1.424 (2) | C60—H60 | 0.91 (2) |
O55—H55 | 0.81 (3) | C61—C62 | 1.535 (2) |
O56—C62 | 1.414 (2) | C61—H61 | 0.96 (2) |
O56—H56 | 0.89 (4) | C62—H62 | 0.98 (2) |
| | | |
C8—O2—H2 | 109 (2) | O6—C12—C11 | 111.6 (1) |
C9—O3—H3 | 104 (1) | O6—C12—H12 | 109 (1) |
C10—O4—H4 | 106 (2) | C7—C12—C11 | 110.6 (1) |
C11—O5—H5 | 105 (2) | C7—C12—H12 | 104 (1) |
C12—O6—H6 | 107 (1) | C11—C12—H12 | 108 (1) |
C58—O52—H52 | 110 (3) | O51—C57—C58 | 122.6 (1) |
C59—O53—H53 | 110 (1) | O51—C57—C62 | 122.1 (1) |
C60—O54—H54 | 104 (1) | C58—C57—C62 | 115.3 (1) |
C61—O55—H55 | 102 (2) | O52—C58—C57 | 108.4 (1) |
C62—O56—H56 | 110 (1) | O52—C58—C59 | 112.0 (1) |
O1—C7—C8 | 122.9 (1) | O52—C58—H58 | 112 (1) |
O1—C7—C12 | 123.0 (1) | C57—C58—C59 | 110.2 (1) |
C8—C7—C12 | 114.0 (1) | C57—C58—H58 | 106 (1) |
O2—C8—C7 | 109.1 (1) | C59—C58—H58 | 107 (1) |
O2—C8—C9 | 110.7 (1) | O53—C59—C58 | 109.8 (1) |
O2—C8—H8 | 110 (1) | O53—C59—C60 | 110.6 (1) |
C7—C8—C9 | 108.4 (1) | O53—C59—H59 | 105 (1) |
C7—C8—H8 | 109 (1) | C58—C59—C60 | 112.2 (1) |
C9—C8—H8 | 108 (1) | C58—C59—H59 | 110 (1) |
O3—C9—C8 | 110.8 (1) | C60—C59—H59 | 108 (1) |
O3—C9—C10 | 107.8 (1) | O54—C60—C59 | 109.9 (1) |
O3—C9—H9 | 109 (1) | O54—C60—C61 | 109.1 (1) |
C8—C9—C10 | 111.1 (1) | O54—C60—H60 | 103 (1) |
C8—C9—H9 | 108 (1) | C59—C60—C61 | 112.6 (1) |
C10—C9—H9 | 108 (1) | C59—C60—H60 | 111 (1) |
O4—C10—C9 | 110.3 (1) | C61—C60—H60 | 109 (1) |
O4—C10—C11 | 110.3 (1) | O55—C61—C60 | 110.5 (1) |
O4—C10—H10 | 104 (1) | O55—C61—C62 | 109.5 (1) |
C9—C10—C11 | 111.0 (1) | O55—C61—H61 | 109 (1) |
C9—C10—H10 | 108 (1) | C60—C61—C62 | 110.2 (1) |
C11—C10—H10 | 111 (1) | C60—C61—H61 | 107 (1) |
O5—C11—C10 | 107.9 (1) | C62—C61—H61 | 109 (1) |
O5—C11—C12 | 110.6 (1) | O56—C62—C57 | 112.1 (1) |
O5—C11—H11 | 110 (1) | O56—C62—C61 | 111.5 (1) |
C10—C11—C12 | 110.5 (1) | O56—C62—H62 | 110 (1) |
C10—C11—H11 | 107 (1) | C57—C62—C61 | 110.6 (1) |
C12—C11—H11 | 109 (1) | C57—C62—H62 | 108 (1) |
O6—C12—C7 | 111.6 (1) | C61—C62—H62 | 103 (1) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O53i | 0.76 (3) | 2.09 (3) | 2.856 (2) | 177 (3) |
O3—H3···O54i | 0.84 (3) | 1.96 (3) | 2.786 (2) | 166 (3) |
O4—H4···O53ii | 0.73 (3) | 2.49 (3) | 3.123 (2) | 145 (3) |
O5—H5···O56iii | 0.82 (3) | 1.97 (3) | 2.785 (2) | 173 (4) |
O6—H6···O4iv | 0.76 (3) | 2.10 (3) | 2.828 (2) | 163 (3) |
O52—H52···O3v | 0.85 (4) | 2.04 (4) | 2.856 (2) | 161 (3) |
O53—H53···O51v | 0.81 (3) | 2.06 (3) | 2.845 (2) | 164 (3) |
O54—H54···O55vi | 0.83 (3) | 1.94 (3) | 2.767 (2) | 172 (2) |
O55—H55···O6vii | 0.81 (3) | 1.98 (3) | 2.782 (2) | 170 (3) |
O56—H56···O2 | 0.89 (4) | 2.06 (4) | 2.938 (2) | 170 (3) |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y+1/2, −z; (iii) −x+2, y+1/2, −z; (iv) −x+2, y−1/2, −z; (v) −x+1, y−1/2, −z; (vi) −x+1, y−1/2, −z+1; (vii) −x+2, y−1/2, −z+1. |
Experimental details
Crystal data |
Chemical formula | C6H10O6 |
Mr | 178.14 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 11.197 (2), 8.932 (2), 6.976 (2) |
β (°) | 90.21 (2) |
V (Å3) | 697.7 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.16 |
Crystal size (mm) | 0.7 × 0.4 × 0.15 |
|
Data collection |
Diffractometer | Rigaku AFC-7R diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2250, 2151, 2086 |
Rint | 0.005 |
(sin θ/λ)max (Å−1) | 0.703 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.068, 1.13 |
No. of reflections | 2151 |
No. of parameters | 298 |
No. of restraints | ? |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.30, −0.16 |
Selected bond lengths (Å) topO1—C7 | 1.205 (2) | O51—C57 | 1.207 (2) |
O2—C8 | 1.419 (2) | O52—C58 | 1.401 (2) |
O3—C9 | 1.425 (2) | O53—C59 | 1.440 (2) |
O4—C10 | 1.428 (2) | O54—C60 | 1.427 (2) |
O5—C11 | 1.424 (2) | O55—C61 | 1.424 (2) |
O6—C12 | 1.418 (2) | O56—C62 | 1.414 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O53i | 0.76 (3) | 2.09 (3) | 2.856 (2) | 177 (3) |
O3—H3···O54i | 0.84 (3) | 1.96 (3) | 2.786 (2) | 166 (3) |
O4—H4···O53ii | 0.73 (3) | 2.49 (3) | 3.123 (2) | 145 (3) |
O5—H5···O56iii | 0.82 (3) | 1.97 (3) | 2.785 (2) | 173 (4) |
O6—H6···O4iv | 0.76 (3) | 2.10 (3) | 2.828 (2) | 163 (3) |
O52—H52···O3v | 0.85 (4) | 2.04 (4) | 2.856 (2) | 161 (3) |
O53—H53···O51v | 0.81 (3) | 2.06 (3) | 2.845 (2) | 164 (3) |
O54—H54···O55vi | 0.83 (3) | 1.94 (3) | 2.767 (2) | 172 (2) |
O55—H55···O6vii | 0.81 (3) | 1.98 (3) | 2.782 (2) | 170 (3) |
O56—H56···O2 | 0.89 (4) | 2.06 (4) | 2.938 (2) | 170 (3) |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y+1/2, −z; (iii) −x+2, y+1/2, −z; (iv) −x+2, y−1/2, −z; (v) −x+1, y−1/2, −z; (vi) −x+1, y−1/2, −z+1; (vii) −x+2, y−1/2, −z+1. |
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myo-Inositol has only one axial hydroxyl group and has essentially mirror symmetry. Crystal structures have been reported for myo-inositol (Rabinowitz & Kraut, 1964), myo-inositol dihydrate (Lomer et al., 1963), myo-inositol tetraaquamagnesium dichloride (Blank, 1973) and myo-inositol calcium bromide pentahydrate (Cook & Bugg, 1973). The crystal structure and molecular dynamics analysis of an optically active myo-inositol derivative have been reported recently (Dillen et al., 2000).
The title compound, (I), was prepared enantioselectively by a bioconversion from myo-inositol (Takahashi et al., 2000). \scheme