(-)-epi-Inosose-2

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.

S1. Comment

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

S2. Experimental

Crystals of (I) were grown from an aqueous ethanol solution.

S3. Refinement

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).

Computing details

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.

(-)-2L-(2,3,4,6/5)–2,3,4,5,6-pentahydroxycyclohexanone

Crystal data

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) Å^3	0.7 × 0.4 × 0.15 mm
Z = 4

Data collection

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

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0417P)^2 + 0.0965P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.024	(Δ/σ)max < 0.001
wR(F^2) = 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+0.001xFc^2λ^3/sin(2θ)]^-1/4
298 parameters	Extinction coefficient: 0.027 (5)
All H-atom parameters refined

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O53^i	0.76 (3)	2.09 (3)	2.856 (2)	177 (3)
O3—H3···O54^i	0.84 (3)	1.96 (3)	2.786 (2)	166 (3)
O4—H4···O53^ii	0.73 (3)	2.49 (3)	3.123 (2)	145 (3)
O5—H5···O56^iii	0.82 (3)	1.97 (3)	2.785 (2)	173 (4)
O6—H6···O4^iv	0.76 (3)	2.10 (3)	2.828 (2)	163 (3)
O52—H52···O3^v	0.85 (4)	2.04 (4)	2.856 (2)	161 (3)
O53—H53···O51^v	0.81 (3)	2.06 (3)	2.845 (2)	164 (3)
O54—H54···O55^vi	0.83 (3)	1.94 (3)	2.767 (2)	172 (2)
O55—H55···O6^vii	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.