(R)-2-[(R)-2,2-Dimethyl-1,3-dioxolan-4-yl]-1,3-oxathio-lan-5-one.

In the title compound, C(8)H(12)O(4)S, the two five-membered rings both adopt envelope conformations. In the crystal, weak C-H⋯O inter-actions link neighbouring mol-ecules.

Related literature

The title compound is a precursor for the preparation of an important nucleoside drug. For applications of nucleosides in the fields of biology, drugs and chemistry, see: Goodyear et al. (2005 ▶); Simons (2001 ▶); Vittori et al. (2006 ▶).

Experimental

Crystal data

C8H12O4S

M = 204.24

Monoclinic,

a = 6.5528 (13) Å

b = 9.4029 (19) Å

c = 7.9240 (16) Å

β = 106.60 (3)°

V = 467.89 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.50 × 0.20 × 0.15 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.859, T max = 0.952

1941 measured reflections

1705 independent reflections

1275 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.129

S = 1.01

1705 reflections

119 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 593 Friedel pairs

Flack parameter: −0.01 (13)

Data collection: RAPID-AUTO (Rigaku/MSC, 2005 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902039X/wn2324sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902039X/wn2324Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H12O4S	F(000) = 216
Mr = 204.24	Dx = 1.450 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 6.5528 (13) Å	Cell parameters from 1941 reflections
b = 9.4029 (19) Å	θ = 2.7–27.5°
c = 7.9240 (16) Å	µ = 0.33 mm−1
β = 106.60 (3)°	T = 293 K
V = 467.89 (16) Å3	Block, colourless
Z = 2	0.50 × 0.20 × 0.15 mm

Rigaku Saturn CCD area-detector diffractometer	1705 independent reflections
Radiation source: fine-focus sealed tube	1275 reflections with I > 2σ(I)
graphite	Rint = 0.056
Detector resolution: 10.00 pixels mm-1	θmax = 27.5°, θmin = 2.7°
Ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −12→11
Tmin = 0.859, Tmax = 0.952	l = −10→10
1941 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.088P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.129	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.24 e Å−3
1705 reflections	Δρmin = −0.20 e Å−3
119 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.102 (15)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 593 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.01 (13)

Experimental. 1H NMR(CDCl3,P.P.M.): 1.41 (d, 6 H), 3.58(d, 4 H), 3.77 (d, 1 H), 3.92 (dd, 1 H), 4.12 (dd, 1 H), 4.35 (m, 1 H), 5.45(d, 1 H).

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
S1	0.57296 (17)	0.19608 (12)	0.31212 (10)	0.0733 (4)
O1	0.7766 (4)	0.0255 (3)	0.5605 (3)	0.0514 (6)
O2	1.1103 (4)	0.0457 (3)	0.5630 (4)	0.0734 (8)
O3	0.8026 (4)	0.1607 (2)	0.9331 (3)	0.0560 (6)
O4	0.7352 (4)	0.2936 (2)	0.6920 (3)	0.0482 (5)
C1	0.8546 (6)	0.1980 (5)	0.3737 (4)	0.0612 (9)
H1A	0.9049	0.1803	0.2718	0.073*
H1B	0.9075	0.2899	0.4225	0.073*
C2	0.9307 (6)	0.0859 (4)	0.5061 (4)	0.0502 (8)
C3	0.5800 (5)	0.1011 (4)	0.5101 (4)	0.0509 (8)
H3	0.4622	0.0328	0.4851	0.061*
C4	0.5669 (5)	0.1947 (4)	0.6584 (4)	0.0486 (7)
H4	0.4302	0.2451	0.6269	0.058*
C5	0.5987 (5)	0.1192 (5)	0.8312 (4)	0.0567 (9)
H5A	0.4914	0.1477	0.8871	0.068*
H5B	0.5915	0.0169	0.8144	0.068*
C6	0.8418 (5)	0.2954 (4)	0.8756 (4)	0.0486 (8)
C7	1.0731 (6)	0.3117 (5)	0.9004 (6)	0.0742 (11)
H7A	1.1010	0.4044	0.8614	0.111*
H7B	1.1201	0.2405	0.8330	0.111*
H7C	1.1483	0.3006	1.0228	0.111*
C8	0.7487 (7)	0.4089 (5)	0.9608 (5)	0.0743 (12)
H8A	0.7778	0.5000	0.9182	0.111*
H8B	0.8106	0.4046	1.0861	0.111*
H8C	0.5975	0.3954	0.9332	0.111*

	U11	U22	U33	U12	U13	U23
S1	0.0745 (6)	0.0908 (9)	0.0459 (4)	−0.0108 (6)	0.0034 (4)	0.0026 (5)
O1	0.0541 (13)	0.0404 (12)	0.0659 (14)	−0.0020 (10)	0.0269 (11)	−0.0011 (11)
O2	0.0606 (17)	0.0628 (18)	0.107 (2)	0.0052 (14)	0.0402 (16)	−0.0045 (16)
O3	0.0649 (15)	0.0446 (14)	0.0563 (12)	0.0047 (11)	0.0139 (10)	0.0108 (11)
O4	0.0566 (12)	0.0465 (12)	0.0411 (10)	−0.0113 (11)	0.0132 (9)	0.0000 (9)
C1	0.082 (2)	0.053 (2)	0.0589 (18)	−0.012 (2)	0.0367 (17)	−0.0009 (17)
C2	0.059 (2)	0.0397 (17)	0.0597 (18)	−0.0016 (15)	0.0293 (16)	−0.0084 (14)
C3	0.0457 (16)	0.0508 (19)	0.0557 (17)	−0.0117 (15)	0.0134 (14)	−0.0050 (16)
C4	0.0389 (14)	0.0522 (19)	0.0563 (15)	−0.0025 (15)	0.0163 (12)	0.0032 (17)
C5	0.0558 (19)	0.060 (2)	0.062 (2)	−0.0076 (17)	0.0287 (17)	0.0027 (16)
C6	0.0548 (19)	0.0429 (18)	0.0453 (16)	0.0041 (15)	0.0100 (14)	0.0022 (13)
C7	0.058 (2)	0.065 (3)	0.088 (3)	−0.0082 (19)	0.004 (2)	−0.004 (2)
C8	0.106 (3)	0.057 (2)	0.063 (2)	0.015 (2)	0.027 (2)	−0.0093 (18)

S1—C1	1.769 (4)	C3—H3	0.9800
S1—C3	1.795 (4)	C4—C5	1.504 (5)
O1—C2	1.333 (4)	C4—H4	0.9800
O1—C3	1.425 (4)	C5—H5A	0.9700
O2—C2	1.195 (4)	C5—H5B	0.9700
O3—C6	1.395 (4)	C6—C8	1.483 (5)
O3—C5	1.405 (4)	C6—C7	1.480 (5)
O4—C4	1.408 (4)	C7—H7A	0.9600
O4—C6	1.423 (4)	C7—H7B	0.9600
C1—C2	1.470 (5)	C7—H7C	0.9600
C1—H1A	0.9700	C8—H8A	0.9600
C1—H1B	0.9700	C8—H8B	0.9600
C3—C4	1.490 (5)	C8—H8C	0.9600
C1—S1—C3	89.97 (16)	O3—C5—C4	104.7 (3)
C2—O1—C3	113.9 (3)	O3—C5—H5A	110.8
C6—O3—C5	107.4 (3)	C4—C5—H5A	110.8
C4—O4—C6	109.3 (2)	O3—C5—H5B	110.8
C2—C1—S1	107.7 (3)	C4—C5—H5B	110.8
C2—C1—H1A	110.2	H5A—C5—H5B	108.9
S1—C1—H1A	110.2	O3—C6—O4	103.9 (3)
C2—C1—H1B	110.2	O3—C6—C8	111.5 (3)
S1—C1—H1B	110.2	O4—C6—C8	109.2 (3)
H1A—C1—H1B	108.5	O3—C6—C7	109.1 (3)
O2—C2—O1	119.9 (3)	O4—C6—C7	108.8 (3)
O2—C2—C1	126.4 (3)	C8—C6—C7	113.8 (4)
O1—C2—C1	113.7 (3)	C6—C7—H7A	109.5
O1—C3—C4	109.0 (3)	C6—C7—H7B	109.5
O1—C3—S1	106.8 (2)	H7A—C7—H7B	109.5
C4—C3—S1	113.7 (3)	C6—C7—H7C	109.5
O1—C3—H3	109.1	H7A—C7—H7C	109.5
C4—C3—H3	109.1	H7B—C7—H7C	109.5
S1—C3—H3	109.1	C6—C8—H8A	109.5
O4—C4—C3	108.7 (2)	C6—C8—H8B	109.5
O4—C4—C5	104.0 (3)	H8A—C8—H8B	109.5
C3—C4—C5	114.5 (3)	C6—C8—H8C	109.5
O4—C4—H4	109.8	H8A—C8—H8C	109.5
C3—C4—H4	109.8	H8B—C8—H8C	109.5
C5—C4—H4	109.8
C3—S1—C1—C2	19.2 (3)	S1—C3—C4—O4	−57.3 (3)
C3—O1—C2—O2	168.2 (3)	O1—C3—C4—C5	−54.1 (3)
C3—O1—C2—C1	−13.0 (4)	S1—C3—C4—C5	−173.1 (2)
S1—C1—C2—O2	171.1 (3)	C6—O3—C5—C4	28.4 (3)
S1—C1—C2—O1	−7.6 (4)	O4—C4—C5—O3	−11.8 (4)
C2—O1—C3—C4	−96.1 (3)	C3—C4—C5—O3	106.7 (3)
C2—O1—C3—S1	27.2 (3)	C5—O3—C6—O4	−33.7 (3)
C1—S1—C3—O1	−26.0 (3)	C5—O3—C6—C8	83.8 (3)
C1—S1—C3—C4	94.2 (3)	C5—O3—C6—C7	−149.6 (3)
C6—O4—C4—C3	−130.9 (3)	C4—O4—C6—O3	25.9 (3)
C6—O4—C4—C5	−8.5 (3)	C4—O4—C6—C8	−93.2 (4)
O1—C3—C4—O4	61.7 (3)	C4—O4—C6—C7	142.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O3i	0.97	2.58	3.428 (4)	146
C1—H1B···O2ii	0.97	2.41	3.306 (6)	153
C3—H3···O2iii	0.98	2.55	3.265 (4)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O3i	0.97	2.58	3.428 (4)	146
C1—H1B⋯O2ii	0.97	2.41	3.306 (6)	153
C3—H3⋯O2iii	0.98	2.55	3.265 (4)	129

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