{(3aR,5S,6R,6aR)-5-[(R)-1,2-Di-hydroxy-eth-yl]-2,2-di-methyl-tetra-hydro-furo[2,3-d][1,3]dioxol-6-yl}methyl methane-sulfonate.

In the title compound, C11H20O8S, the furan-ose ring has a pseudorotation phase angle equal to 31.3° and assumes a (3) T 4 conformation, with deviations of 0.297 (4) and -0.152 (4) Å for the corresponding C atoms. The dioxolane ring adopts an envelope conformation. One of the O atoms is at the flap and deviates from the least-squares plane formed by the other four ring atoms by 0.405 (2) Å. The dihedral angle between the planar fragments of the rings is 63.53 (8)°. In the crystal, mol-ecules are associated into sheets perpendiculer to the b axis by means of O-H⋯O hydrogen bonds. A few weak C-H⋯O inter-actions are also observed.

Related literature

For the synthesis, properties and applications of the title compound, see: Mikhailopulo et al. (1996 ▶); Rjabova et al. (2012 ▶). Its applications in the synthesis of imino sugars and 1′-aza-C-nucleosides are described by Filichev & Pedersen (2001 ▶). For a review on the syntheses and biological properties of imino sugars, see: López et al. (2012 ▶). For reviews on the synthesies and biological properties of aza-nucleosides, see: Romeo et al. (2010 ▶); Merino (2006 ▶).

Experimental

Crystal data

C11H20O8S

M = 312.33

Monoclinic,

a = 5.5794 (1) Å

b = 15.6118 (3) Å

c = 8.0653 (2) Å

β = 98.913 (1)°

V = 694.04 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.35 × 0.30 × 0.28 mm

Data collection

Nonius KappaCCD diffractometer

5266 measured reflections

3185 independent reflections

3005 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.065

S = 1.03

3185 reflections

187 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1528 Friedel pairs

Absolute structure parameter: 0.00 (5)

Data collection: COLLECT (Bruker, 2004) ▶; cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814007387/zp2012sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007387/zp2012Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814007387/zp2012Isup3.cml

CCDC reference: 995085

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H20O8S	F(000) = 332
Mr = 312.33	Dx = 1.495 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7583 reflections
a = 5.5794 (1) Å	θ = 1.0–27.5°
b = 15.6118 (3) Å	µ = 0.27 mm−1
c = 8.0653 (2) Å	T = 293 K
β = 98.913 (1)°	Prism, colourless
V = 694.04 (3) Å3	0.35 × 0.30 × 0.28 mm
Z = 2

Nonius KappaCCD diffractometer	3005 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
CCD scans	h = −7→6
5266 measured reflections	k = −20→20
3185 independent reflections	l = −10→10

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027	w = 1/[σ2(Fo2) + (0.0319P)2 + 0.0938P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.065	(Δ/σ)max = 0.003
S = 1.03	Δρmax = 0.16 e Å−3
3185 reflections	Δρmin = −0.21 e Å−3
187 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.064 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1528 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (5)

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.

	x	y	z	Uiso*/Ueq
C9	0.0490 (4)	0.33494 (13)	−0.8352 (2)	0.0407 (4)
H9A	0.1797	0.3741	−0.8422	0.061*
H9B	−0.0757	0.3429	−0.9302	0.061*
H9C	0.1083	0.2772	−0.8345	0.061*
C7	−0.0536 (3)	0.35157 (11)	−0.6762 (2)	0.0316 (3)
C8	−0.2632 (4)	0.29425 (14)	−0.6553 (2)	0.0470 (5)
H8A	−0.2092	0.2358	−0.6465	0.071*
H8B	−0.3882	0.3003	−0.7507	0.071*
H8C	−0.3262	0.3100	−0.5554	0.071*
S1	0.60651 (6)	0.22002 (2)	−0.20810 (5)	0.02715 (10)
O4	0.22882 (19)	0.51605 (8)	0.01079 (13)	0.0303 (2)
H41	0.3738	0.5199	0.0049	0.046*
O1	−0.0420 (3)	0.52359 (9)	−0.43022 (15)	0.0465 (4)
O6	0.55516 (19)	0.31615 (7)	−0.26299 (14)	0.0278 (2)
O3	0.1263 (2)	0.34259 (7)	−0.53311 (14)	0.0347 (3)
O5	−0.27358 (19)	0.51658 (8)	−0.01728 (15)	0.0364 (3)
H51	−0.1929	0.5014	0.0716	0.055*
O2	−0.1278 (2)	0.44075 (9)	−0.67350 (16)	0.0396 (3)
O8	0.8446 (2)	0.20376 (8)	−0.24301 (17)	0.0427 (3)
O7	0.5551 (2)	0.20875 (9)	−0.04236 (15)	0.0426 (3)
C10	0.3456 (3)	0.35774 (10)	−0.2075 (2)	0.0284 (3)
H10A	0.3819	0.3718	−0.0891	0.034*
H10B	0.2063	0.3198	−0.2244	0.034*
C3	0.2921 (3)	0.43831 (10)	−0.31045 (18)	0.0247 (3)
H3	0.4270	0.4787	−0.2833	0.030*
C1	0.0500 (3)	0.48807 (11)	−0.5677 (2)	0.0329 (4)
H1	0.1185	0.5329	−0.6313	0.039*
C6	−0.1460 (3)	0.58175 (10)	−0.0923 (2)	0.0335 (4)
H6A	−0.1128	0.6293	−0.0147	0.040*
H6B	−0.2477	0.6028	−0.1925	0.040*
C4	0.0556 (3)	0.48076 (10)	−0.2760 (2)	0.0276 (3)
H4	−0.0583	0.4370	−0.2493	0.033*
C2	0.2447 (3)	0.42291 (10)	−0.49929 (19)	0.0277 (3)
H2	0.3917	0.4282	−0.5511	0.033*
C5	0.0908 (3)	0.54919 (10)	−0.13860 (19)	0.0266 (3)
H5	0.1789	0.5976	−0.1777	0.032*
C11	0.3976 (3)	0.16137 (13)	−0.3475 (3)	0.0445 (4)
H11A	0.4188	0.1014	−0.3237	0.067*
H11B	0.4233	0.1724	−0.4605	0.067*
H11C	0.2358	0.1781	−0.3348	0.067*

	U11	U22	U33	U12	U13	U23
C9	0.0485 (10)	0.0442 (10)	0.0313 (9)	−0.0040 (8)	0.0124 (8)	−0.0070 (8)
C7	0.0347 (8)	0.0323 (8)	0.0268 (7)	0.0030 (7)	0.0017 (6)	−0.0024 (7)
C8	0.0445 (11)	0.0566 (13)	0.0421 (11)	−0.0097 (9)	0.0132 (8)	−0.0093 (9)
S1	0.02425 (17)	0.02403 (17)	0.03312 (19)	0.00244 (15)	0.00429 (13)	0.00247 (17)
O4	0.0234 (5)	0.0375 (6)	0.0295 (6)	0.0003 (5)	0.0024 (4)	−0.0030 (5)
O1	0.0576 (8)	0.0472 (8)	0.0306 (6)	0.0302 (7)	−0.0062 (5)	−0.0066 (6)
O6	0.0260 (5)	0.0252 (5)	0.0333 (6)	0.0046 (4)	0.0078 (4)	0.0031 (5)
O3	0.0438 (7)	0.0268 (6)	0.0298 (6)	0.0021 (5)	−0.0061 (5)	−0.0033 (5)
O5	0.0227 (5)	0.0496 (7)	0.0359 (6)	0.0025 (5)	0.0013 (4)	−0.0006 (6)
O2	0.0408 (7)	0.0384 (7)	0.0356 (7)	0.0089 (5)	−0.0061 (5)	−0.0052 (5)
O8	0.0284 (6)	0.0370 (7)	0.0640 (8)	0.0093 (5)	0.0112 (5)	0.0074 (6)
O7	0.0536 (7)	0.0392 (7)	0.0362 (6)	0.0050 (6)	0.0101 (5)	0.0113 (6)
C10	0.0281 (7)	0.0300 (8)	0.0287 (8)	0.0076 (6)	0.0093 (6)	0.0022 (6)
C3	0.0228 (7)	0.0248 (7)	0.0262 (7)	0.0009 (6)	0.0032 (5)	−0.0018 (6)
C1	0.0379 (9)	0.0309 (8)	0.0283 (8)	0.0032 (7)	0.0003 (7)	0.0005 (7)
C6	0.0300 (8)	0.0307 (8)	0.0387 (9)	0.0062 (6)	0.0019 (7)	−0.0090 (7)
C4	0.0253 (7)	0.0273 (7)	0.0288 (8)	0.0047 (6)	−0.0003 (6)	−0.0037 (6)
C2	0.0293 (8)	0.0271 (7)	0.0270 (7)	0.0010 (6)	0.0050 (6)	0.0016 (6)
C5	0.0250 (7)	0.0242 (7)	0.0302 (8)	0.0000 (6)	0.0029 (6)	−0.0032 (6)
C11	0.0392 (10)	0.0399 (10)	0.0536 (11)	−0.0059 (8)	0.0051 (8)	−0.0139 (9)

C9—C7	1.506 (2)	O5—H51	0.8200
C9—H9A	0.9600	O2—C1	1.413 (2)
C9—H9B	0.9600	C10—C3	1.511 (2)
C9—H9C	0.9600	C10—H10A	0.9700
C7—O3	1.4140 (19)	C10—H10B	0.9700
C7—O2	1.454 (2)	C3—C2	1.524 (2)
C7—C8	1.503 (3)	C3—C4	1.540 (2)
C8—H8A	0.9600	C3—H3	0.9800
C8—H8B	0.9600	C1—C2	1.528 (2)
C8—H8C	0.9600	C1—H1	0.9800
S1—O7	1.4210 (12)	C6—C5	1.515 (2)
S1—O8	1.4226 (12)	C6—H6A	0.9700
S1—O6	1.5782 (11)	C6—H6B	0.9700
S1—C11	1.7480 (18)	C4—C5	1.530 (2)
O4—C5	1.4230 (18)	C4—H4	0.9800
O4—H41	0.8200	C2—H2	0.9800
O1—C1	1.406 (2)	C5—H5	0.9800
O1—C4	1.442 (2)	C11—H11A	0.9600
O6—C10	1.4669 (17)	C11—H11B	0.9600
O3—C2	1.4238 (19)	C11—H11C	0.9600
O5—C6	1.429 (2)
C7—C9—H9A	109.5	C10—C3—H3	109.5
C7—C9—H9B	109.5	C2—C3—H3	109.5
H9A—C9—H9B	109.5	C4—C3—H3	109.5
C7—C9—H9C	109.5	O1—C1—O2	112.02 (14)
H9A—C9—H9C	109.5	O1—C1—C2	107.70 (13)
H9B—C9—H9C	109.5	O2—C1—C2	105.27 (13)
O3—C7—O2	104.53 (12)	O1—C1—H1	110.6
O3—C7—C8	108.42 (14)	O2—C1—H1	110.6
O2—C7—C8	109.89 (15)	C2—C1—H1	110.6
O3—C7—C9	111.26 (14)	O5—C6—C5	112.10 (13)
O2—C7—C9	108.93 (14)	O5—C6—H6A	109.2
C8—C7—C9	113.43 (15)	C5—C6—H6A	109.2
C7—C8—H8A	109.5	O5—C6—H6B	109.2
C7—C8—H8B	109.5	C5—C6—H6B	109.2
H8A—C8—H8B	109.5	H6A—C6—H6B	107.9
C7—C8—H8C	109.5	O1—C4—C5	106.85 (12)
H8A—C8—H8C	109.5	O1—C4—C3	105.29 (12)
H8B—C8—H8C	109.5	C5—C4—C3	114.43 (12)
O7—S1—O8	119.66 (8)	O1—C4—H4	110.0
O7—S1—O6	109.11 (7)	C5—C4—H4	110.0
O8—S1—O6	104.40 (7)	C3—C4—H4	110.0
O7—S1—C11	109.17 (10)	O3—C2—C3	109.51 (12)
O8—S1—C11	109.23 (9)	O3—C2—C1	103.57 (12)
O6—S1—C11	104.11 (8)	C3—C2—C1	105.03 (12)
C5—O4—H41	109.5	O3—C2—H2	112.7
C1—O1—C4	111.21 (12)	C3—C2—H2	112.7
C10—O6—S1	117.00 (10)	C1—C2—H2	112.7
C7—O3—C2	108.57 (12)	O4—C5—C6	106.96 (12)
C6—O5—H51	109.5	O4—C5—C4	110.57 (12)
C1—O2—C7	109.55 (12)	C6—C5—C4	113.18 (12)
O6—C10—C3	107.43 (11)	O4—C5—H5	108.7
O6—C10—H10A	110.2	C6—C5—H5	108.7
C3—C10—H10A	110.2	C4—C5—H5	108.7
O6—C10—H10B	110.2	S1—C11—H11A	109.5
C3—C10—H10B	110.2	S1—C11—H11B	109.5
H10A—C10—H10B	108.5	H11A—C11—H11B	109.5
C10—C3—C2	114.00 (13)	S1—C11—H11C	109.5
C10—C3—C4	111.15 (12)	H11A—C11—H11C	109.5
C2—C3—C4	103.12 (12)	H11B—C11—H11C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O5i	0.82	2.00	2.820 (2)	174
O5—H51···O2ii	0.82	2.24	3.009 (2)	156
O5—H51···O4	0.82	2.49	2.777 (2)	102
C3—H3···O5i	0.98	2.58	3.344 (2)	135
C8—H8C···O6iii	0.96	2.55	3.486 (2)	165
C9—H9A···O4iv	0.96	2.55	3.306 (2)	136
C10—H10A···O4	0.97	2.58	3.160 (2)	118
C11—H11C···O8iii	0.96	2.44	3.387 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H41⋯O5i	0.82	2.00	2.820 (2)	174
O5—H51⋯O2ii	0.82	2.24	3.009 (2)	156
C3—H3⋯O5i	0.98	2.58	3.344 (2)	135
C8—H8C⋯O6iii	0.96	2.55	3.486 (2)	165
C9—H9A⋯O4iv	0.96	2.55	3.306 (2)	136
C11—H11C⋯O8iii	0.96	2.44	3.387 (2)	167

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .