{(3aR,5S,6R,6aR)-5-[(R)-1,2-Di­hydroxy­eth­yl]-2,2-di­methyl­tetra­hydro­furo[2,3-d][1,3]dioxol-6-yl}methyl methane­sulfonate

Rjabovs, V.¯; Mishnev, A.; Kiselovs, G.; Turks, M.¯

doi:10.1107/S1600536814007387

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 5| May 2014| Pages o524-o525

doi:10.1107/S1600536814007387

Open

access

{(3aR,5S,6R,6aR)-5-[(R)-1,2-Dihydroxyethyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}methyl methanesulfonate

Vitālijs Rjabovs,^a ^* Anatoly Mishnev,^b Glebs Kiselovs ^b and Māris Turks ^a

^aFaculty of Material Science and Applied Chemistry, Riga Technical University, 3 P. Valdena Street, Riga, LV-1007, Latvia, and ^bLatvian Institute of Organic Synthesis, 21 Aizkraukles Street, Riga, LV-1006, Latvia
^*Correspondence e-mail: v.rjabovs@gmail.com

(Received 17 February 2014; accepted 2 April 2014; online 5 April 2014)

In the title compound, C₁₁H₂₀O₈S, the furanose ring has a pseudorotation phase angle equal to 31.3° and assumes a ³T₄ 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, molecules are associated into sheets perpendiculer to the b axis by means of O—H⋯O hydrogen bonds. A few weak C—H⋯O interactions are also observed.

CCDC reference: 995085

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_r = 312.33
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.027
wR(F²) = 0.065
S = 1.03
3185 reflections
187 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1528 Friedel pairs
Absolute structure parameter: 0.00 (5)

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⋯O4^iv	0.96	2.55	3.306 (2)	136
C11—H11C⋯O8ⁱⁱⁱ	0.96	2.44	3.387 (2)	167
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x-1, y, z; (iv) x, y, z-1.

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).

Supporting information

CCDC reference: 995085

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814007387/zp2012sup1.cif

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

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

checkCIF report

Comment top

1,2-O-isopropylidene-3-deoxy-3-mesyloxymethyl-α-D-allofuranose was obtained as the intermediate in the syntheses of 3-C-branched 3-C-deoxy nucleoside analogs (Mikhailopulo et al., 1996) by an acidic hydrolysis of 5,6-isopropylidene protecting group of the corresponding mesylate. Both the title compound and its precursor can be used for the syntheses of different carbohydrate derivatives such as triazole conjugates of 3-C-branched 3-C-deoxy allofuranose (Rjabova et al., 2012) and imino sugars and 1'-aza-C-nucleosides (Filichev & Pedersen, 2001). For review on syntheses and biological properties of imino sugars, see: López et al. (2012). For reviews on syntheses and biological properties of aza-nucleosides, see: Romeo et al. (2010) and Merino (2006). Fig. 1 shows a view of the molecular structure of the title compound. The furanose ring has a pseudorotation phase angle equal to 31.3° and assumes ³T₄ conformation with deviations of 0.297 (4) Å and -0.152 (4) Å for corresponding C atoms. The dioxolane ring adopts envelope conformation. One of the O atoms deviates from the least squares plane formed by four other atoms of the dioxolane ring by 0.405 (2) Å. The dihedral angle betweeen plane fragments of the cycles is 63.53 (8)°. In the crystal by means of O—H···O type hydrogen bonds the molecules are associated in sheets perpendiculer to crystallographic axis b (Fig. 2). A few week C—H···O hydrogen bond interactions have been also detected in the structure (Table 1).

Related literature top

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 top

Single crystals of ((3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl)methyl methanesulfonate were grown from a dichloromethane solution by a slow evaporation at ambient temperature. ¹H-NMR and ¹³C-NMR spectra were recorded at 300 MHz and at 75.5 MHz, respectively. The proton signals for residual non-deuterated solvents (δ 7.26 for CHCl₃) and carbon signals (δ 77.1 for CDCl₃) were used as the internal references for ¹H-NMR and ¹³C-NMR spectra, respectively. Coupling constants are reported in Hz. Analytical thin layer chromatography (TLC) was performed on Kieselgel 60 F254 glass plates precoated with a 0.25 mm thickness of silica gel. 2M aqueous solution of H₂SO₄ (1 ml, 2.0 mmol, 0.5 equiv.) was added to a solution of 1,2,5,6-di-O-isopropylidene-3-deoxy-3-mesyloxymethyl-α-D-allofuranose (1.46 g, 4.1 mmol, 1.0 equiv.) in a mixture of MeOH (11 ml) and DCM (4 ml). The resulting reaction mixture was stirred at 50 °C for 1.5 h (TLC control). The reaction mixture was quenched with saturated aqueous solution of NaHCO₃ (10 ml) and organic solvents were evaporated under reduced pressure. Ethyl acetate (50 ml) was added, the layers were separated, and the organic layer was washed with brine (3 × 10 ml), dried over Na₂SO₄, filtered and evaporated. Crystallization of the crude product from DCM yielded analytically pure mesylate (1.24 g, 96%) as a white solid. M.p. 103–104°C (DCM), R_f=0.16 (hexanes/EtOAc 1:3), ¹H-NMR (CDCl₃, 300 MHz): 1.34 (s, 3H), 1.52 (s, 3H), 2.36 (b.s., 2H), 2.49 (tt, J=9.8 Hz, J=4.8 Hz, 1H), 3.05 (s, 3H), 3.69 (m, 2H), 3.83 (m, 2H), 4.42 (t, J=10.0 Hz, 1H), 4.67 (dd, J=10.0 Hz, J=5.0 Hz, 1H), 4.77 (t, J=4.0 Hz, 1H), 5.83 (d, J=3.6 Hz, 1H), ¹³C-NMR (CDCl₃, 75 MHz): 26.4, 26.7, 37.1, 47.5, 63.7, 66.6, 73.3, 78.8, 80.4, 105.0, 112.4, HRMS: Calculated for C₁₁H₂₀O₈NaS [M+Na]⁺: 335.0777. Found [M+Na]⁺: 335.0736.

Computing details top

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).

Figures top

	Fig. 1. The asymmetric unit of the title compound showing 50% probability displacement ellipsoids and the atom-numbering (hydrogen atoms are shown as small spheres of arbitrary radii)
	Fig. 2. Packing diagram of the title compound viewed down the a axis.

{(3aR,5S,6R,6aR)-5-[(R)-1,2-Dihydroxyethyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}methyl methanesulfonate top

Crystal data top

C₁₁H₂₀O₈S	F(000) = 332
M_r = 312.33	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0319P)² + 0.0938P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.065	(Δ/σ)_max = 0.003
S = 1.03	Δρ_max = 0.16 e Å⁻³
3185 reflections	Δρ_min = −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)

Crystal data top

C₁₁H₂₀O₈S	V = 694.04 (3) Å³
M_r = 312.33	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.5794 (1) Å	µ = 0.27 mm⁻¹
b = 15.6118 (3) Å	T = 293 K
c = 8.0653 (2) Å	0.35 × 0.30 × 0.28 mm
β = 98.913 (1)°

Data collection top

Nonius KappaCCD diffractometer	3005 reflections with I > 2σ(I)
5266 measured reflections	R_int = 0.018
3185 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.065	Δρ_max = 0.16 e Å⁻³
S = 1.03	Δρ_min = −0.21 e Å⁻³
3185 reflections	Absolute structure: Flack (1983), 1528 Friedel pairs
187 parameters	Absolute structure parameter: 0.00 (5)
1 restraint

Special details top

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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···O4^iv	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

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

Hydrogen-bond geometry (Å, º) top

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···O4^iv	0.96	2.55	3.306 (2)	136
C11—H11C···O8ⁱⁱⁱ	0.96	2.44	3.387 (2)	167

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

Acknowledgements

This work was supported by the Latvian Council of Science (grant No 09.1557).

References

Bruker (2004). COLLECT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Filichev, V. V. & Pedersen, E. B. (2001). Tetrahedron, 57, 9163–9168. Web of Science CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
López, O., Merino-Montiel, P., Martos, S. & González-Benjumea, A. (2012). Carbohydr. Chem. 38, 215–262. Google Scholar
Merino, P. (2006). Curr. Med. Chem. 13, 539–545. Web of Science CrossRef PubMed CAS Google Scholar
Mikhailopulo, I. A., Poopeiko, N. O., Tsvetkova, T. M., Marochkin, A. P., Balzarini, J. & De Clercq, E. (1996). Carbohydr. Res. 285, 17-28. CrossRef CAS PubMed Web of Science Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Rjabova, J., Rjabovs, V., Moreno Vargas, A. J., Clavijo, E. M. & Turks, M. (2012). Centr. Eur. J. Chem. 10, 386–394. Web of Science CrossRef CAS Google Scholar
Romeo, G., Chiacchio, U., Corsaro, A. & Merino, P. (2010). Chem. Rev. 110, 3337–3370. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 5| May 2014| Pages o524-o525

doi:10.1107/S1600536814007387

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

{(3aR,5S,6R,6aR)-5-[(R)-1,2-Di­hy­droxy­eth­yl]-2,2-di­methyl­tetra­hydro­furo[2,3-d][1,3]dioxol-6-yl}methyl methane­sulfonate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

{(3aR,5S,6R,6aR)-5-[(R)-1,2-Dihydroxyethyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}methyl methanesulfonate