(3,4-Dihy-droxy-oxolan-2-yl)methyl 4-methyl-benzene-sulfonate.

The racemic title compound, C(12)H(16)O(6)S, possesses a five-membered ring that adopts an envelope-shaped conformation; the two hy-droxy groups occupy quasi-axial positions. Adjacent mol-ecules are linked by O-H⋯O hydrogen bonds to generate a ribbon that runs along the a axis of the ortho-rhom-bic unit cell. The crystal studied was an inversion twin.

Related literature

For the synthesis of the title compound, see: Kapitan & Grazca (2008 ▶); Park et al. (2005 ▶). For the use of xylitol tosyl­ates in the synthesis of bicyclic oxetanes, see: Köll & Oetling (1987 ▶).

Experimental

Crystal data

C12H16O6S

M = 288.31

Orthorhombic,

a = 5.414 (4) Å

b = 10.172 (8) Å

c = 24.080 (18) Å

V = 1326.0 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 173 K

0.50 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.879, T max = 0.949

14329 measured reflections

3154 independent reflections

2333 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.110

S = 1.02

3154 reflections

177 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1174 Friedel pairs

Flack parameter: 0.47 (12)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810044788/ng5055sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044788/ng5055Isup2.hkl

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

C12H16O6S	F(000) = 608
Mr = 288.31	Dx = 1.444 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2ac2ab	Cell parameters from 3862 reflections
a = 5.414 (4) Å	θ = 2.6–23.4°
b = 10.172 (8) Å	µ = 0.26 mm−1
c = 24.080 (18) Å	T = 173 K
V = 1326.0 (17) Å3	Block, colourless
Z = 4	0.50 × 0.30 × 0.20 mm

Bruker APEXII CCD diffractometer	3154 independent reflections
Radiation source: fine-focus sealed tube	2333 reflections with I > 2σ(I)
graphite	Rint = 0.056
φ and ω scans	θmax = 28.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
Tmin = 0.879, Tmax = 0.949	k = −13→13
14329 measured reflections	l = −31→26

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047	w = 1/[σ2(Fo2) + (0.0413P)2 + 0.5008P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.110	(Δ/σ)max = 0.003
S = 1.01	Δρmax = 0.26 e Å−3
3154 reflections	Δρmin = −0.19 e Å−3
177 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0054 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 1174 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.47 (12)

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	0.49846 (15)	0.83391 (7)	0.19055 (3)	0.03938 (19)
O4	0.3443 (4)	0.9149 (2)	0.14690 (8)	0.0403 (5)
O3	−0.1096 (4)	0.7717 (2)	0.02146 (9)	0.0522 (6)
H3	−0.2351	0.7308	0.0104	0.063*
O5	0.6954 (4)	0.9196 (2)	0.20441 (10)	0.0558 (6)
O1	0.1981 (4)	0.9922 (2)	0.03798 (8)	0.0452 (5)
O6	0.5516 (4)	0.7081 (2)	0.16814 (8)	0.0533 (6)
C3	−0.1840 (5)	0.8929 (3)	0.04656 (12)	0.0393 (7)
H3A	−0.3360	0.8827	0.0698	0.047*
C5	0.1566 (5)	0.8449 (3)	0.11540 (12)	0.0397 (6)
H5A	0.0364	0.8031	0.1409	0.048*
H5B	0.2338	0.7755	0.0924	0.048*
O2	−0.3312 (4)	1.1107 (2)	0.02581 (11)	0.0574 (6)
H2	−0.4753	1.0904	0.0355	0.069*
C9	−0.0409 (6)	0.8029 (3)	0.33240 (11)	0.0477 (8)
C11	0.2748 (6)	0.9224 (3)	0.28326 (13)	0.0469 (8)
H11	0.3752	0.9984	0.2793	0.056*
C4	0.0298 (5)	0.9430 (3)	0.07931 (11)	0.0354 (6)
H4	−0.0271	1.0181	0.1029	0.042*
C10	0.1045 (7)	0.9131 (3)	0.32584 (12)	0.0518 (9)
H10	0.0872	0.9842	0.3511	0.062*
C7	0.1562 (6)	0.7062 (3)	0.25310 (12)	0.0431 (7)
H7	0.1760	0.6342	0.2284	0.052*
C2	−0.2121 (6)	0.9991 (3)	0.00288 (13)	0.0429 (7)
H2A	−0.2984	0.9661	−0.0311	0.051*
C6	0.2955 (5)	0.8185 (3)	0.24657 (11)	0.0359 (6)
C12	−0.2297 (8)	0.7949 (4)	0.37844 (14)	0.0703 (11)
H12A	−0.3449	0.7228	0.3708	0.105*
H12B	−0.3211	0.8779	0.3806	0.105*
H12C	−0.1457	0.7788	0.4138	0.105*
C1	0.0535 (5)	1.0362 (3)	−0.00883 (12)	0.0458 (8)
H1A	0.1114	0.9932	−0.0433	0.055*
H1B	0.0689	1.1325	−0.0134	0.055*
C8	−0.0126 (7)	0.6997 (3)	0.29599 (11)	0.0478 (7)
H8	−0.1106	0.6229	0.3004	0.057*

	U11	U22	U33	U12	U13	U23
S1	0.0386 (3)	0.0384 (4)	0.0411 (3)	0.0040 (4)	−0.0029 (4)	0.0060 (3)
O4	0.0423 (11)	0.0401 (11)	0.0385 (10)	0.0032 (10)	−0.0059 (9)	0.0067 (9)
O3	0.0547 (13)	0.0456 (13)	0.0562 (13)	−0.0053 (11)	−0.0067 (12)	−0.0107 (11)
O5	0.0423 (12)	0.0619 (15)	0.0633 (14)	−0.0097 (12)	−0.0080 (11)	0.0074 (12)
O1	0.0308 (11)	0.0596 (14)	0.0452 (12)	−0.0038 (10)	−0.0002 (9)	0.0146 (10)
O6	0.0641 (15)	0.0438 (12)	0.0518 (12)	0.0142 (11)	0.0056 (11)	0.0022 (10)
C3	0.0351 (15)	0.0448 (18)	0.0381 (14)	−0.0006 (14)	0.0023 (13)	0.0003 (13)
C5	0.0376 (15)	0.0412 (16)	0.0404 (14)	−0.0025 (14)	−0.0027 (13)	−0.0007 (14)
O2	0.0416 (12)	0.0519 (14)	0.0788 (16)	0.0049 (11)	0.0027 (13)	0.0074 (12)
C9	0.059 (2)	0.0514 (19)	0.0331 (13)	0.0089 (17)	0.0039 (14)	0.0064 (14)
C11	0.061 (2)	0.0351 (17)	0.0441 (16)	0.0009 (15)	−0.0106 (15)	0.0002 (14)
C4	0.0322 (15)	0.0393 (15)	0.0347 (13)	−0.0035 (13)	0.0008 (12)	0.0030 (11)
C10	0.075 (2)	0.0412 (18)	0.0396 (16)	0.0087 (17)	−0.0040 (16)	−0.0052 (15)
C7	0.0569 (19)	0.0326 (15)	0.0397 (15)	−0.0016 (15)	0.0018 (15)	0.0015 (13)
C2	0.0352 (16)	0.0484 (19)	0.0452 (16)	−0.0016 (14)	−0.0071 (14)	0.0028 (15)
C6	0.0396 (15)	0.0337 (15)	0.0345 (13)	0.0022 (13)	−0.0036 (12)	0.0031 (12)
C12	0.084 (3)	0.076 (3)	0.0504 (19)	0.009 (2)	0.023 (2)	0.001 (2)
C1	0.0361 (18)	0.061 (2)	0.0401 (15)	0.0023 (14)	−0.0006 (13)	0.0114 (15)
C8	0.0600 (18)	0.0426 (16)	0.0407 (14)	−0.0031 (18)	0.0032 (16)	0.0053 (12)

S1—O5	1.417 (2)	C9—C10	1.379 (5)
S1—O6	1.418 (2)	C9—C12	1.510 (4)
S1—O4	1.575 (2)	C11—C10	1.382 (5)
S1—C6	1.747 (3)	C11—C6	1.382 (4)
O4—C5	1.454 (3)	C11—H11	0.9500
O3—C3	1.430 (4)	C4—H4	1.0000
O3—H3	0.8400	C10—H10	0.9500
O1—C4	1.439 (3)	C7—C6	1.378 (4)
O1—C1	1.443 (3)	C7—C8	1.381 (4)
C3—C4	1.491 (4)	C7—H7	0.9500
C3—C2	1.516 (4)	C2—C1	1.513 (4)
C3—H3A	1.0000	C2—H2A	1.0000
C5—C4	1.491 (4)	C12—H12A	0.9800
C5—H5A	0.9900	C12—H12B	0.9800
C5—H5B	0.9900	C12—H12C	0.9800
O2—C2	1.418 (4)	C1—H1A	0.9900
O2—H2	0.8400	C1—H1B	0.9900
C9—C8	1.376 (4)	C8—H8	0.9500
O5—S1—O6	119.47 (15)	C5—C4—H4	108.8
O5—S1—O4	103.55 (13)	C3—C4—H4	108.8
O6—S1—O4	109.01 (12)	C9—C10—C11	121.4 (3)
O5—S1—C6	110.27 (14)	C9—C10—H10	119.3
O6—S1—C6	109.91 (14)	C11—C10—H10	119.3
O4—S1—C6	103.24 (13)	C6—C7—C8	119.2 (3)
C5—O4—S1	117.54 (17)	C6—C7—H7	120.4
C3—O3—H3	109.5	C8—C7—H7	120.4
C4—O1—C1	107.7 (2)	O2—C2—C1	107.8 (3)
O3—C3—C4	107.4 (2)	O2—C2—C3	110.3 (3)
O3—C3—C2	110.4 (2)	C1—C2—C3	102.2 (2)
C4—C3—C2	101.6 (2)	O2—C2—H2A	112.0
O3—C3—H3A	112.3	C1—C2—H2A	112.0
C4—C3—H3A	112.3	C3—C2—H2A	112.0
C2—C3—H3A	112.3	C7—C6—C11	121.1 (3)
O4—C5—C4	107.3 (2)	C7—C6—S1	120.5 (2)
O4—C5—H5A	110.2	C11—C6—S1	118.4 (2)
C4—C5—H5A	110.2	C9—C12—H12A	109.5
O4—C5—H5B	110.2	C9—C12—H12B	109.5
C4—C5—H5B	110.2	H12A—C12—H12B	109.5
H5A—C5—H5B	108.5	C9—C12—H12C	109.5
C2—O2—H2	109.5	H12A—C12—H12C	109.5
C8—C9—C10	118.9 (3)	H12B—C12—H12C	109.5
C8—C9—C12	120.1 (3)	O1—C1—C2	107.0 (2)
C10—C9—C12	121.0 (3)	O1—C1—H1A	110.3
C10—C11—C6	118.4 (3)	C2—C1—H1A	110.3
C10—C11—H11	120.8	O1—C1—H1B	110.3
C6—C11—H11	120.8	C2—C1—H1B	110.3
O1—C4—C5	110.1 (2)	H1A—C1—H1B	108.6
O1—C4—C3	104.2 (2)	C9—C8—C7	120.9 (3)
C5—C4—C3	115.9 (2)	C9—C8—H8	119.5
O1—C4—H4	108.8	C7—C8—H8	119.5
O5—S1—O4—C5	167.5 (2)	C4—C3—C2—C1	36.7 (3)
O6—S1—O4—C5	39.3 (2)	C8—C7—C6—C11	2.2 (4)
C6—S1—O4—C5	−77.5 (2)	C8—C7—C6—S1	−176.4 (2)
S1—O4—C5—C4	177.38 (18)	C10—C11—C6—C7	−2.1 (4)
C1—O1—C4—C5	154.6 (2)	C10—C11—C6—S1	176.5 (2)
C1—O1—C4—C3	29.6 (3)	O5—S1—C6—C7	−152.8 (2)
O4—C5—C4—O1	66.7 (3)	O6—S1—C6—C7	−19.1 (3)
O4—C5—C4—C3	−175.4 (2)	O4—S1—C6—C7	97.1 (3)
O3—C3—C4—O1	74.7 (3)	O5—S1—C6—C11	28.5 (3)
C2—C3—C4—O1	−41.3 (3)	O6—S1—C6—C11	162.3 (2)
O3—C3—C4—C5	−46.5 (3)	O4—S1—C6—C11	−81.6 (2)
C2—C3—C4—C5	−162.5 (2)	C4—O1—C1—C2	−5.7 (3)
C8—C9—C10—C11	0.8 (5)	O2—C2—C1—O1	96.4 (3)
C12—C9—C10—C11	−178.9 (3)	C3—C2—C1—O1	−19.8 (3)
C6—C11—C10—C9	0.6 (5)	C10—C9—C8—C7	−0.7 (5)
O3—C3—C2—O2	168.6 (2)	C12—C9—C8—C7	178.9 (3)
C4—C3—C2—O2	−77.6 (3)	C6—C7—C8—C9	−0.7 (5)
O3—C3—C2—C1	−77.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.84	2.03	2.834 (4)	160
O3—H3···O3ii	0.84	2.17	2.931 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.84	2.03	2.834 (4)	160
O3—H3⋯O3ii	0.84	2.17	2.931 (2)	151

Symmetry codes: (i) ; (ii) .