3,4-O-(2,3-Dimethoxy-butane-2,3-di-yl)-S-(4-methyl-phen-yl)-1-thia-α-d-manno-pyran-oside.

In the title mol-ecule, C(19)H(28)O(7)S, the six-membered manno-pyran-oside and dioxane rings both display typical chair conformations. In the crystal structure, the hydr-oxy groups are involved in inter-molecular hydrogen bonds, which link the mol-ecules into chains extended along the b axis.

Related literature

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

Experimental

Crystal data

C19H28O7S

M = 400.47

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.099

S = 1.08

4843 reflections

257 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 2274 Friedel pairs

Flack parameter: 0.00 (9)

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 ▶).

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

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

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

C19H28O7S	F(000) = 428
Mr = 400.47	Dx = 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

Rigaku Saturn diffractometer	4843 independent reflections
Radiation source: rotating anode	4168 reflections with I > 2σ(I)
confocal	Rint = 0.037
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 2.0°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −13→13
Tmin = 0.940, Tmax = 0.966	l = −13→13
11384 measured reflections

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(Fo2) + (0.0477P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.26 e Å−3
4843 reflections	Δρmin = −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	Flack parameter: 0.00 (9)

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	0.08382 (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*

	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)

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)

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)

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) ; (ii) .