3,4-O-(2,3-Dimethoxy­butane-2,3-di­yl)-S-(4-methyl­phen­yl)-1-thia-α-d-manno­pyran­oside

Xu, F.-F.; Han, D.; Wang, L.-N.; Meng, X.-B.; Li, Z.-J.

doi:10.1107/S1600536808018874

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1367

doi:10.1107/S1600536808018874

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3,4-O-(2,3-Dimethoxybutane-2,3-diyl)-S-(4-methylphenyl)-1-thia-α-D-mannopyranoside

Fei-Fei Xu,^a Dong Han,^a Lin-Na Wang,^a Xiang-Bao Meng ^a and Zhong-Jun Li ^a,^b ^*

^aDepartment of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100083, People's Republic of China, and ^bState Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100083, People's Republic of China
^*Correspondence e-mail: zjli@bjmu.edu.cn

(Received 22 April 2008; accepted 22 June 2008; online 28 June 2008)

In the title molecule, C₁₉H₂₈O₇S, the six-membered mannopyranoside and dioxane rings both display typical chair conformations. In the crystal structure, the hydroxy groups are involved in intermolecular hydrogen bonds, which link the molecules into chains extended along the b axis.

Related literature

For details of the synthesis, see Crich et al. (2000 ).

Experimental

Crystal data

C₁₉H₂₈O₇S
M_r = 400.47
Monoclinic, P 2₁
a = 9.8272 (6) Å
b = 10.3152 (6) Å
c = 10.2585 (6) Å
β = 100.452 (3)°
V = 1022.64 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 113 (2) K
0.32 × 0.26 × 0.18 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.940, T_max = 0.966
11384 measured reflections
4843 independent reflections
4168 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.099
S = 1.08
4843 reflections
257 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 2274 Friedel pairs
Flack parameter: 0.00 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O5ⁱ	0.86 (3)	1.96 (3)	2.788 (2)	161 (2)
O5—H5⋯O7ⁱⁱ	0.80 (2)	2.21 (3)	2.971 (2)	158 (3)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018874/cv2406sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018874/cv2406Isup2.hkl

checkCIF report

Comment top

The skeleton of the title compound, (I) (Figure 1), is a derivative of mannopyranoside and consists of a benzene ring and a bridged ring. Both of the six-membered mannopyranoside ring and the dioxane ring display a typical chair conformation. The two methoxy groups lie in axial bonds of the dioxane ring. The hydroxy groups are involved in the intermolecular hydrogen bonds (Table 1), which link the molecules into chains extended along b axis.

Related literature top

For details of the synthesis, see Crich et al. (2000).

Experimental top

The title compound was synthesized according to the known procedure (Crich et al., 2000). It was obtained from 4-methylphenyl-1-thio-alpha-D-mannopyranoside, and then dissolved in dry methanol followed by addition of butane-2,3-dione, HC(OMe)₃, and camphor-10-sulfonic acid. The reaction mixture was then heated to reflux for 72 h before it was cooled to room temperature and quenched by addition of Et₃N. The reaction mixture was concentrated under vacuum, after column chromatography(hexane-ethyl acetate 1:1) yield 78% as a white solid. The compound was crystallized from hexane-ethyl acetate(1:1) to yield colourless block-like crystals after a week at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (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: CrystalStructure (Rigaku/MSC, 2005).

Figures top

Fig. 1. A view of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by circles of arbitrary size.

3,4-O-(2,3-Dimethoxybutane-2,3-diyl)-S-(4-methylphenyl)-1- thia-α-D-mannopyranoside top

Crystal data top

C₁₉H₂₈O₇S	F(000) = 428
M_r = 400.47	D_x = 1.301 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71070 Å
a = 9.8272 (6) Å	Cell parameters from 3904 reflections
b = 10.3152 (6) Å	θ = 2.0–29.1°
c = 10.2585 (6) Å	µ = 0.20 mm⁻¹
β = 100.452 (3)°	T = 113 K
V = 1022.64 (10) Å³	Block, colourless
Z = 2	0.32 × 0.26 × 0.18 mm

Data collection top

Rigaku Saturn diffractometer	4843 independent reflections
Radiation source: rotating anode	4168 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.037
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 2.0°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −13→13
T_min = 0.940, T_max = 0.966	l = −13→13
11384 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.034	w = 1/[σ²(F_o²) + (0.0477P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.099	(Δ/σ)_max = 0.001
S = 1.08	Δρ_max = 0.26 e Å⁻³
4843 reflections	Δρ_min = −0.22 e Å⁻³
257 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.049 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2274 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (9)

Crystal data top

C₁₉H₂₈O₇S	V = 1022.64 (10) Å³
M_r = 400.47	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.8272 (6) Å	µ = 0.20 mm⁻¹
b = 10.3152 (6) Å	T = 113 K
c = 10.2585 (6) Å	0.32 × 0.26 × 0.18 mm
β = 100.452 (3)°

Data collection top

Rigaku Saturn diffractometer	4843 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	4168 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.966	R_int = 0.037
11384 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.099	Δρ_max = 0.26 e Å⁻³
S = 1.08	Δρ_min = −0.22 e Å⁻³
4843 reflections	Absolute structure: Flack (1983), 2274 Friedel pairs
257 parameters	Absolute structure parameter: 0.00 (9)
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
S1	0.08382 (5)	0.30225 (6)	0.13524 (5)	0.02495 (15)
O1	0.27226 (13)	0.29547 (15)	0.36556 (13)	0.0207 (3)
O2	0.23894 (16)	0.57684 (16)	0.39230 (16)	0.0263 (4)
H2	0.307 (3)	0.630 (3)	0.399 (2)	0.039*
O3	0.40302 (14)	0.62650 (13)	0.19735 (14)	0.0184 (3)
O4	0.57553 (14)	0.40759 (13)	0.24002 (13)	0.0168 (3)
O5	0.53143 (15)	0.23535 (16)	0.52689 (15)	0.0250 (4)
H5	0.469 (3)	0.217 (3)	0.564 (3)	0.038*
O6	0.49654 (18)	0.56405 (14)	0.01322 (15)	0.0219 (3)
O7	0.67376 (13)	0.59510 (13)	0.34562 (13)	0.0174 (3)
C1	0.1677 (2)	0.3749 (2)	0.2940 (2)	0.0210 (5)
H1	0.0945	0.3842	0.3495	0.025*
C2	0.2176 (2)	0.5111 (2)	0.2695 (2)	0.0202 (5)
H2A	0.1446	0.5571	0.2054	0.024*
C3	0.3473 (2)	0.5000 (2)	0.2110 (2)	0.0178 (4)
H3	0.3236	0.4589	0.1214	0.021*
C4	0.4535 (2)	0.4171 (2)	0.2984 (2)	0.0159 (4)
H4	0.4773	0.4565	0.3888	0.019*
C5	0.39550 (19)	0.2825 (2)	0.3079 (2)	0.0176 (5)
H5A	0.3697	0.2451	0.2169	0.021*
C6	0.4911 (2)	0.1905 (2)	0.3936 (2)	0.0216 (5)
H6A	0.4447	0.1055	0.3946	0.026*
H6B	0.5751	0.1777	0.3544	0.026*
C7	0.5249 (2)	0.6230 (2)	0.1397 (2)	0.0170 (4)
C8	0.6343 (2)	0.5312 (2)	0.2214 (2)	0.0171 (4)
C9	0.5733 (2)	0.7621 (2)	0.1354 (2)	0.0247 (5)
H9A	0.6553	0.7655	0.0936	0.037*
H9B	0.5966	0.7962	0.2259	0.037*
H9C	0.4994	0.8147	0.0841	0.037*
C10	0.7551 (2)	0.5036 (2)	0.1524 (2)	0.0228 (5)
H10A	0.8003	0.5852	0.1366	0.034*
H10B	0.7214	0.4604	0.0676	0.034*
H10C	0.8216	0.4471	0.2085	0.034*
C11	0.3820 (2)	0.6183 (2)	−0.0772 (2)	0.0283 (5)
H11A	0.3006	0.6218	−0.0345	0.042*
H11B	0.3616	0.5640	−0.1567	0.042*
H11C	0.4056	0.7060	−0.1021	0.042*
C12	0.7672 (2)	0.5241 (2)	0.4431 (2)	0.0219 (5)
H12A	0.7261	0.4401	0.4583	0.033*
H12B	0.7849	0.5734	0.5262	0.033*
H12C	0.8544	0.5103	0.4117	0.033*
C13	0.0406 (2)	0.1504 (2)	0.1985 (2)	0.0225 (5)
C14	0.1138 (3)	0.0401 (2)	0.1754 (2)	0.0304 (6)
H14	0.1843	0.0459	0.1233	0.036*
C15	0.0847 (2)	−0.0786 (2)	0.2279 (2)	0.0285 (5)
H15	0.1343	−0.1537	0.2100	0.034*
C16	−0.0166 (2)	−0.0890 (2)	0.3067 (2)	0.0235 (5)
C17	−0.0895 (2)	0.0221 (2)	0.3287 (2)	0.0245 (5)
H17	−0.1595	0.0165	0.3813	0.029*
C18	−0.0619 (2)	0.1405 (2)	0.2757 (2)	0.0248 (5)
H18	−0.1129	0.2152	0.2920	0.030*
C19	−0.0438 (2)	−0.2154 (3)	0.3688 (2)	0.0326 (6)
H19A	0.0348	−0.2372	0.4387	0.049*
H19B	−0.0562	−0.2837	0.3012	0.049*
H19C	−0.1279	−0.2082	0.4072	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0249 (3)	0.0269 (3)	0.0218 (3)	−0.0069 (3)	0.0010 (2)	0.0037 (2)
O1	0.0215 (7)	0.0222 (8)	0.0197 (7)	−0.0031 (7)	0.0067 (6)	0.0037 (7)
O2	0.0241 (8)	0.0287 (9)	0.0280 (9)	−0.0042 (7)	0.0097 (7)	−0.0079 (7)
O3	0.0187 (7)	0.0136 (7)	0.0234 (8)	−0.0001 (6)	0.0054 (6)	0.0032 (6)
O4	0.0210 (7)	0.0130 (8)	0.0181 (7)	0.0012 (6)	0.0077 (6)	0.0016 (6)
O5	0.0264 (8)	0.0287 (9)	0.0206 (9)	0.0015 (8)	0.0061 (6)	0.0077 (7)
O6	0.0303 (7)	0.0225 (8)	0.0127 (7)	−0.0012 (6)	0.0031 (6)	0.0015 (6)
O7	0.0200 (7)	0.0169 (8)	0.0141 (7)	0.0003 (6)	−0.0003 (6)	0.0005 (6)
C1	0.0201 (11)	0.0248 (12)	0.0173 (11)	0.0005 (9)	0.0016 (9)	0.0040 (9)
C2	0.0136 (10)	0.0226 (12)	0.0243 (11)	−0.0007 (9)	0.0027 (8)	−0.0011 (9)
C3	0.0214 (11)	0.0125 (10)	0.0209 (11)	0.0009 (9)	0.0075 (9)	0.0034 (8)
C4	0.0185 (10)	0.0156 (11)	0.0143 (10)	0.0007 (9)	0.0046 (8)	0.0014 (8)
C5	0.0188 (10)	0.0176 (12)	0.0166 (10)	−0.0023 (9)	0.0035 (8)	0.0006 (8)
C6	0.0298 (12)	0.0160 (11)	0.0201 (11)	0.0004 (9)	0.0075 (9)	0.0034 (9)
C7	0.0183 (10)	0.0165 (11)	0.0162 (10)	−0.0020 (9)	0.0033 (8)	0.0001 (8)
C8	0.0186 (10)	0.0156 (11)	0.0181 (11)	−0.0012 (9)	0.0063 (9)	0.0009 (9)
C9	0.0268 (11)	0.0184 (12)	0.0291 (12)	−0.0039 (9)	0.0055 (10)	0.0032 (9)
C10	0.0253 (12)	0.0222 (12)	0.0228 (12)	0.0027 (10)	0.0098 (9)	0.0039 (9)
C11	0.0338 (13)	0.0320 (14)	0.0164 (11)	−0.0007 (11)	−0.0027 (10)	0.0086 (10)
C12	0.0245 (11)	0.0217 (12)	0.0170 (11)	0.0041 (10)	−0.0032 (9)	0.0030 (9)
C13	0.0238 (11)	0.0243 (13)	0.0188 (12)	−0.0079 (10)	0.0023 (9)	−0.0004 (9)
C14	0.0384 (14)	0.0312 (14)	0.0251 (13)	−0.0071 (11)	0.0152 (11)	−0.0063 (10)
C15	0.0345 (13)	0.0238 (13)	0.0278 (13)	−0.0040 (11)	0.0078 (10)	−0.0108 (10)
C16	0.0205 (11)	0.0266 (13)	0.0210 (12)	−0.0074 (10)	−0.0029 (9)	−0.0021 (10)
C17	0.0206 (11)	0.0311 (13)	0.0208 (12)	−0.0040 (11)	0.0009 (9)	0.0033 (10)
C18	0.0206 (11)	0.0274 (13)	0.0261 (12)	−0.0037 (10)	0.0037 (9)	−0.0022 (10)
C19	0.0327 (13)	0.0305 (15)	0.0342 (14)	−0.0099 (11)	0.0050 (11)	−0.0009 (11)

Geometric parameters (Å, º) top

S1—C13	1.776 (2)	C7—C8	1.558 (3)
S1—C1	1.845 (2)	C8—C10	1.515 (3)
O1—C1	1.411 (2)	C9—H9A	0.9800
O1—C5	1.447 (2)	C9—H9B	0.9800
O2—C2	1.412 (3)	C9—H9C	0.9800
O2—H2	0.86 (3)	C10—H10A	0.9800
O3—C7	1.429 (2)	C10—H10B	0.9800
O3—C3	1.432 (2)	C10—H10C	0.9800
O4—C8	1.427 (2)	C11—H11A	0.9800
O4—C4	1.438 (2)	C11—H11B	0.9800
O5—C6	1.429 (3)	C11—H11C	0.9800
O5—H5	0.80 (2)	C12—H12A	0.9800
O6—C7	1.414 (2)	C12—H12B	0.9800
O6—C11	1.436 (3)	C12—H12C	0.9800
O7—C8	1.425 (2)	C13—C14	1.390 (3)
O7—C12	1.430 (2)	C13—C18	1.394 (3)
C1—C2	1.525 (3)	C14—C15	1.388 (3)
C1—H1	1.0000	C14—H14	0.9500
C2—C3	1.509 (3)	C15—C16	1.396 (3)
C2—H2A	1.0000	C15—H15	0.9500
C3—C4	1.511 (3)	C16—C17	1.391 (3)
C3—H3	1.0000	C16—C19	1.497 (3)
C4—C5	1.510 (3)	C17—C18	1.384 (3)
C4—H4	1.0000	C17—H17	0.9500
C5—C6	1.502 (3)	C18—H18	0.9500
C5—H5A	1.0000	C19—H19A	0.9800
C6—H6A	0.9900	C19—H19B	0.9800
C6—H6B	0.9900	C19—H19C	0.9800
C7—C9	1.515 (3)

C13—S1—C1	97.68 (10)	O4—C8—C10	105.36 (17)
C1—O1—C5	115.17 (15)	O7—C8—C7	104.43 (15)
C2—O2—H2	111.3 (17)	O4—C8—C7	111.04 (16)
C7—O3—C3	112.44 (15)	C10—C8—C7	112.69 (16)
C8—O4—C4	112.53 (15)	C7—C9—H9A	109.5
C6—O5—H5	106.2 (19)	C7—C9—H9B	109.5
C7—O6—C11	115.22 (17)	H9A—C9—H9B	109.5
C8—O7—C12	115.14 (16)	C7—C9—H9C	109.5
O1—C1—C2	113.28 (17)	H9A—C9—H9C	109.5
O1—C1—S1	112.97 (15)	H9B—C9—H9C	109.5
C2—C1—S1	109.54 (15)	C8—C10—H10A	109.5
O1—C1—H1	106.9	C8—C10—H10B	109.5
C2—C1—H1	106.9	H10A—C10—H10B	109.5
S1—C1—H1	106.9	C8—C10—H10C	109.5
O2—C2—C3	113.08 (17)	H10A—C10—H10C	109.5
O2—C2—C1	107.21 (18)	H10B—C10—H10C	109.5
C3—C2—C1	108.36 (17)	O6—C11—H11A	109.5
O2—C2—H2A	109.4	O6—C11—H11B	109.5
C3—C2—H2A	109.4	H11A—C11—H11B	109.5
C1—C2—H2A	109.4	O6—C11—H11C	109.5
O3—C3—C2	109.57 (17)	H11A—C11—H11C	109.5
O3—C3—C4	109.76 (16)	H11B—C11—H11C	109.5
C2—C3—C4	110.45 (17)	O7—C12—H12A	109.5
O3—C3—H3	109.0	O7—C12—H12B	109.5
C2—C3—H3	109.0	H12A—C12—H12B	109.5
C4—C3—H3	109.0	O7—C12—H12C	109.5
O4—C4—C5	108.48 (16)	H12A—C12—H12C	109.5
O4—C4—C3	109.26 (15)	H12B—C12—H12C	109.5
C5—C4—C3	109.28 (16)	C14—C13—C18	119.2 (2)
O4—C4—H4	109.9	C14—C13—S1	119.62 (17)
C5—C4—H4	109.9	C18—C13—S1	121.16 (18)
C3—C4—H4	109.9	C15—C14—C13	120.4 (2)
O1—C5—C6	107.47 (15)	C15—C14—H14	119.8
O1—C5—C4	107.16 (16)	C13—C14—H14	119.8
C6—C5—C4	114.53 (16)	C14—C15—C16	120.7 (2)
O1—C5—H5A	109.2	C14—C15—H15	119.6
C6—C5—H5A	109.2	C16—C15—H15	119.6
C4—C5—H5A	109.2	C17—C16—C15	118.3 (2)
O5—C6—C5	113.01 (18)	C17—C16—C19	120.8 (2)
O5—C6—H6A	109.0	C15—C16—C19	121.0 (2)
C5—C6—H6A	109.0	C18—C17—C16	121.3 (2)
O5—C6—H6B	109.0	C18—C17—H17	119.3
C5—C6—H6B	109.0	C16—C17—H17	119.3
H6A—C6—H6B	107.8	C17—C18—C13	120.1 (2)
O6—C7—O3	110.48 (16)	C17—C18—H18	120.0
O6—C7—C9	113.07 (18)	C13—C18—H18	120.0
O3—C7—C9	106.22 (16)	C16—C19—H19A	109.5
O6—C7—C8	103.52 (16)	C16—C19—H19B	109.5
O3—C7—C8	109.92 (16)	H19A—C19—H19B	109.5
C9—C7—C8	113.69 (17)	C16—C19—H19C	109.5
O7—C8—O4	110.16 (16)	H19A—C19—H19C	109.5
O7—C8—C10	113.29 (17)	H19B—C19—H19C	109.5

C5—O1—C1—C2	−55.7 (2)	C3—O3—C7—O6	58.6 (2)
C5—O1—C1—S1	69.57 (19)	C3—O3—C7—C9	−178.44 (16)
C13—S1—C1—O1	52.60 (16)	C3—O3—C7—C8	−55.0 (2)
C13—S1—C1—C2	179.90 (15)	C12—O7—C8—O4	56.1 (2)
O1—C1—C2—O2	−71.4 (2)	C12—O7—C8—C10	−61.6 (2)
S1—C1—C2—O2	161.43 (14)	C12—O7—C8—C7	175.43 (16)
O1—C1—C2—C3	50.9 (2)	C4—O4—C8—O7	60.73 (19)
S1—C1—C2—C3	−76.21 (18)	C4—O4—C8—C10	−176.74 (16)
C7—O3—C3—C2	−178.78 (17)	C4—O4—C8—C7	−54.5 (2)
C7—O3—C3—C4	59.8 (2)	O6—C7—C8—O7	174.85 (15)
O2—C2—C3—O3	−56.4 (2)	O3—C7—C8—O7	−67.12 (19)
C1—C2—C3—O3	−175.15 (17)	C9—C7—C8—O7	51.8 (2)
O2—C2—C3—C4	64.6 (2)	O6—C7—C8—O4	−66.44 (19)
C1—C2—C3—C4	−54.1 (2)	O3—C7—C8—O4	51.6 (2)
C8—O4—C4—C5	177.32 (16)	C9—C7—C8—O4	170.49 (16)
C8—O4—C4—C3	58.3 (2)	O6—C7—C8—C10	51.5 (2)
O3—C3—C4—O4	−59.4 (2)	O3—C7—C8—C10	169.51 (17)
C2—C3—C4—O4	179.71 (16)	C9—C7—C8—C10	−71.6 (2)
O3—C3—C4—C5	−177.92 (15)	C1—S1—C13—C14	−107.21 (19)
C2—C3—C4—C5	61.2 (2)	C1—S1—C13—C18	70.17 (19)
C1—O1—C5—C6	−177.40 (17)	C18—C13—C14—C15	0.3 (3)
C1—O1—C5—C4	59.0 (2)	S1—C13—C14—C15	177.77 (18)
O4—C4—C5—O1	−179.39 (14)	C13—C14—C15—C16	−1.2 (4)
C3—C4—C5—O1	−60.3 (2)	C14—C15—C16—C17	1.4 (3)
O4—C4—C5—C6	61.5 (2)	C14—C15—C16—C19	−177.1 (2)
C3—C4—C5—C6	−179.45 (17)	C15—C16—C17—C18	−0.8 (3)
O1—C5—C6—O5	−60.6 (2)	C19—C16—C17—C18	177.7 (2)
C4—C5—C6—O5	58.3 (2)	C16—C17—C18—C13	0.0 (3)
C11—O6—C7—O3	53.1 (2)	C14—C13—C18—C17	0.3 (3)
C11—O6—C7—C9	−65.8 (2)	S1—C13—C18—C17	−177.13 (17)
C11—O6—C7—C8	170.71 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ⁱ	0.86 (3)	1.96 (3)	2.788 (2)	161 (2)
O5—H5···O7ⁱⁱ	0.80 (2)	2.21 (3)	2.971 (2)	158 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₈O₇S
M_r	400.47
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	113
a, b, c (Å)	9.8272 (6), 10.3152 (6), 10.2585 (6)
β (°)	100.452 (3)
V (Å³)	1022.64 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.32 × 0.26 × 0.18

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.940, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	11384, 4843, 4168
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.099, 1.08
No. of reflections	4843
No. of parameters	257
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.22
Absolute structure	Flack (1983), 2274 Friedel pairs
Absolute structure parameter	0.00 (9)

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ⁱ	0.86 (3)	1.96 (3)	2.788 (2)	161 (2)
O5—H5···O7ⁱⁱ	0.80 (2)	2.21 (3)	2.971 (2)	158 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1.

Acknowledgements

We acknowledge financial support from the National Natural Science Foundation of China.

References

Crich, D., Cai, W. L. & Dai, Z. M. (2000). J. Org. Chem. 65, 1291–1297. Web of Science CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan, and MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 7| July 2008| Page o1367

doi:10.1107/S1600536808018874

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

3,4-O-(2,3-Di­meth­oxy­butane-2,3-di­yl)-S-(4-methyl­phen­yl)-1-thia-α-D-manno­pyran­oside

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,4-O-(2,3-Dimethoxybutane-2,3-diyl)-S-(4-methylphenyl)-1-thia-α-D-mannopyranoside