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In the title compound, C16H20O4S, the epoxide ring is trans to the p-tolyl group and cis to the dioxolane moiety. The furan­ose ring adopts a conformation in which the furan­ose and epoxide O atoms are on the same face of the mol­ecule (EO) and the p-tolyl group adopts the conformation favored by the exo-anomeric effect, gauche to the ring O atom and anti to the ring C atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027266/rz6011sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027266/rz6011Isup2.hkl
Contains datablock I

CCDC reference: 259104

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.033
  • wR factor = 0.079
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.61 mm
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.39 From the CIF: _reflns_number_total 3202 Count of symmetry unique reflns 1841 Completeness (_total/calc) 173.93% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1361 Fraction of Friedel pairs measured 0.739 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL (Bruker, 1997a); software used to prepare material for publication: SHELXTL.

p-tolyl 2,3-anhydro-5,6-O-isopropylidene-1-thio-β-D-talofuranoside top
Crystal data top
C16H20O4SDx = 1.307 Mg m3
Mr = 308.38Melting point: 349 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5599 reflections
a = 9.1248 (7) Åθ = 2.2–25.8°
b = 12.0366 (10) ŵ = 0.22 mm1
c = 14.2666 (11) ÅT = 193 K
V = 1566.9 (2) Å3Rod, colourless
Z = 40.61 × 0.11 × 0.10 mm
F(000) = 656
Data collection top
Bruker PLATFORM/SMART 1000 CCD area-detector
diffractometer
3202 independent reflections
Radiation source: fine-focus sealed tube2780 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 8.192 pixels mm-1θmax = 26.4°, θmin = 2.2°
ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1514
Tmin = 0.878, Tmax = 0.978l = 1717
12110 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.080 w = 1/[σ2(Fo2) + (0.0376P)2 + 0.2041P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3202 reflectionsΔρmax = 0.23 e Å3
191 parametersΔρmin = 0.13 e Å3
0 restraintsAbsolute structure: Flack (1983), 1359 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (7)
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.

Hydrogen atoms were generated in idealized positions (according to the sp2 or sp3 geometries of their parent carbon atoms), and then refined using a riding model with fixed C—H distances (C—H = 0.95–1.00 Å) and with Uiso(H) = 1.2Ueq(C).

Data for compound (I) were collected at 193 K on a Bruker PLATFORM diffractometer equipped with a SMART 1000 CCD area detector. The structure of (I) was solved through use of the direct methods program SHELXS97 (Sheldrick, 1990).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.66025 (5)0.04196 (5)0.31980 (3)0.05176 (15)
O10.46045 (13)0.08484 (11)0.22885 (8)0.0442 (3)
O20.30951 (14)0.07865 (13)0.15432 (9)0.0540 (4)
O50.49340 (14)0.16044 (12)0.01461 (9)0.0540 (4)
O60.26305 (13)0.09677 (12)0.03577 (9)0.0507 (3)
C10.47463 (19)0.01728 (16)0.27763 (13)0.0438 (4)
H10.40320.02080.33070.053*
C20.4400 (2)0.10482 (18)0.20598 (13)0.0483 (5)
H20.47180.18360.21510.058*
C30.44962 (18)0.05148 (17)0.11441 (13)0.0434 (4)
H30.48770.09330.05900.052*
C40.49636 (19)0.06644 (15)0.13180 (12)0.0400 (4)
H40.60520.07110.12450.048*
C50.4270 (2)0.15966 (17)0.07556 (14)0.0483 (5)
H50.44510.23230.10750.058*
C60.2637 (2)0.1467 (2)0.05546 (15)0.0587 (6)
H6A0.21350.21960.05490.070*
H6B0.21610.09780.10230.070*
C70.38294 (19)0.14459 (16)0.08429 (14)0.0439 (4)
C80.3410 (3)0.2552 (2)0.12746 (17)0.0682 (6)
H8A0.30680.30570.07820.082*
H8B0.42650.28760.15880.082*
H8C0.26240.24390.17330.082*
C90.4389 (2)0.0632 (2)0.15481 (15)0.0571 (5)
H9A0.46170.00720.12350.069*
H9B0.36390.05060.20280.069*
H9C0.52770.09280.18430.069*
C100.66366 (17)0.04972 (16)0.41675 (12)0.0417 (4)
C110.5884 (2)0.02508 (18)0.49798 (13)0.0530 (5)
H110.53120.04080.50120.064*
C120.5951 (2)0.0948 (2)0.57448 (15)0.0606 (6)
H120.54160.07630.62940.073*
C130.6773 (2)0.19034 (17)0.57321 (16)0.0550 (5)
C140.7529 (2)0.21488 (18)0.49205 (19)0.0620 (6)
H140.81120.28020.48960.074*
C150.7459 (2)0.14616 (19)0.41369 (16)0.0570 (6)
H150.79750.16550.35820.068*
C160.6843 (3)0.2655 (2)0.65783 (19)0.0822 (8)
H16A0.75040.32780.64490.099*
H16B0.58600.29400.67170.099*
H16C0.72090.22350.71180.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0406 (2)0.0637 (3)0.0509 (3)0.0113 (2)0.0010 (2)0.0017 (3)
O10.0429 (7)0.0457 (8)0.0439 (7)0.0061 (6)0.0064 (6)0.0099 (6)
O20.0426 (7)0.0660 (9)0.0534 (8)0.0132 (6)0.0030 (6)0.0137 (7)
O50.0415 (7)0.0668 (10)0.0538 (8)0.0134 (7)0.0152 (6)0.0082 (7)
O60.0310 (6)0.0677 (9)0.0534 (8)0.0004 (6)0.0033 (6)0.0080 (7)
C10.0335 (9)0.0518 (12)0.0461 (10)0.0020 (8)0.0017 (8)0.0030 (9)
C20.0460 (10)0.0480 (12)0.0511 (11)0.0044 (9)0.0060 (8)0.0048 (9)
C30.0383 (9)0.0459 (11)0.0460 (9)0.0012 (8)0.0065 (8)0.0092 (9)
C40.0324 (8)0.0436 (10)0.0441 (9)0.0018 (7)0.0021 (7)0.0055 (8)
C50.0503 (11)0.0433 (11)0.0511 (11)0.0056 (8)0.0105 (9)0.0070 (9)
C60.0448 (11)0.0795 (16)0.0519 (12)0.0207 (11)0.0061 (9)0.0048 (11)
C70.0343 (9)0.0486 (11)0.0488 (10)0.0003 (8)0.0080 (8)0.0011 (9)
C80.0705 (15)0.0608 (14)0.0732 (15)0.0080 (12)0.0221 (13)0.0043 (12)
C90.0414 (10)0.0704 (14)0.0595 (12)0.0033 (10)0.0006 (9)0.0037 (11)
C100.0340 (8)0.0448 (10)0.0462 (9)0.0027 (8)0.0073 (8)0.0106 (8)
C110.0547 (11)0.0537 (13)0.0507 (11)0.0183 (10)0.0032 (9)0.0063 (10)
C120.0691 (13)0.0665 (15)0.0462 (11)0.0127 (12)0.0027 (10)0.0025 (11)
C130.0571 (12)0.0432 (11)0.0646 (13)0.0058 (9)0.0261 (11)0.0057 (10)
C140.0594 (14)0.0394 (12)0.0871 (17)0.0096 (10)0.0260 (12)0.0160 (12)
C150.0474 (11)0.0594 (13)0.0643 (13)0.0061 (10)0.0019 (10)0.0248 (12)
C160.101 (2)0.0581 (14)0.0875 (18)0.0106 (14)0.0409 (16)0.0123 (13)
Geometric parameters (Å, º) top
S—C101.7697 (19)C7—C91.494 (3)
S—C11.8217 (18)C7—C81.517 (3)
O1—C11.419 (2)C8—H8A0.9800
O1—C41.440 (2)C8—H8B0.9800
O2—C21.435 (2)C8—H8C0.9800
O2—C31.437 (2)C9—H9A0.9800
O5—C51.422 (3)C9—H9B0.9800
O5—C71.428 (2)C9—H9C0.9800
O6—C71.417 (2)C10—C111.379 (3)
O6—C61.433 (2)C10—C151.383 (3)
C1—C21.502 (3)C11—C121.378 (3)
C1—H11.0000C11—H110.9500
C2—C31.458 (3)C12—C131.373 (3)
C2—H21.0000C12—H120.9500
C3—C41.503 (3)C13—C141.380 (3)
C3—H31.0000C13—C161.510 (3)
C4—C51.518 (3)C14—C151.392 (3)
C4—H41.0000C14—H140.9500
C5—C61.525 (3)C15—H150.9500
C5—H51.0000C16—H16A0.9800
C6—H6A0.9900C16—H16B0.9800
C6—H6B0.9900C16—H16C0.9800
C10—S—C199.95 (8)O6—C7—C9109.05 (16)
C1—O1—C4108.52 (13)O5—C7—C9108.36 (15)
C2—O2—C361.02 (11)O6—C7—C8111.11 (17)
C5—O5—C7109.14 (14)O5—C7—C8110.09 (16)
C7—O6—C6105.68 (15)C9—C7—C8112.88 (18)
O1—C1—C2104.76 (14)C7—C8—H8A109.5
O1—C1—S112.84 (12)C7—C8—H8B109.5
C2—C1—S107.83 (13)H8A—C8—H8B109.5
O1—C1—H1110.4C7—C8—H8C109.5
C2—C1—H1110.4H8A—C8—H8C109.5
S—C1—H1110.4H8B—C8—H8C109.5
O2—C2—C359.56 (11)C7—C9—H9A109.5
O2—C2—C1111.74 (16)C7—C9—H9B109.5
C3—C2—C1106.75 (16)H9A—C9—H9B109.5
O2—C2—H2121.0C7—C9—H9C109.5
C3—C2—H2121.0H9A—C9—H9C109.5
C1—C2—H2121.0H9B—C9—H9C109.5
O2—C3—C259.41 (11)C11—C10—C15118.50 (19)
O2—C3—C4113.70 (15)C11—C10—S120.92 (15)
C2—C3—C4106.56 (15)C15—C10—S120.55 (15)
O2—C3—H3120.5C12—C11—C10120.80 (18)
C2—C3—H3120.5C12—C11—H11119.6
C4—C3—H3120.5C10—C11—H11119.6
O1—C4—C3103.86 (15)C13—C12—C11121.6 (2)
O1—C4—C5107.44 (14)C13—C12—H12119.2
C3—C4—C5119.51 (15)C11—C12—H12119.2
O1—C4—H4108.5C12—C13—C14117.6 (2)
C3—C4—H4108.5C12—C13—C16120.9 (2)
C5—C4—H4108.5C14—C13—C16121.4 (2)
O5—C5—C4107.78 (15)C13—C14—C15121.56 (19)
O5—C5—C6104.29 (15)C13—C14—H14119.2
C4—C5—C6115.52 (18)C15—C14—H14119.2
O5—C5—H5109.7C10—C15—C14119.9 (2)
C4—C5—H5109.7C10—C15—H15120.0
C6—C5—H5109.7C14—C15—H15120.0
O6—C6—C5102.58 (15)C13—C16—H16A109.5
O6—C6—H6A111.3C13—C16—H16B109.5
C5—C6—H6A111.3H16A—C16—H16B109.5
O6—C6—H6B111.3C13—C16—H16C109.5
C5—C6—H6B111.3H16A—C16—H16C109.5
H6A—C6—H6B109.2H16B—C16—H16C109.5
O6—C7—O5105.02 (14)
C4—O1—C1—C229.82 (17)O1—C4—C5—C679.6 (2)
C4—O1—C1—S87.21 (14)C3—C4—C5—C638.2 (2)
C10—S—C1—O175.82 (13)C7—O6—C6—C535.7 (2)
C10—S—C1—C2168.97 (13)O5—C5—C6—O623.0 (2)
C3—O2—C2—C197.22 (17)C4—C5—C6—O695.1 (2)
O1—C1—C2—O247.03 (18)C6—O6—C7—O535.10 (19)
S—C1—C2—O2167.45 (12)C6—O6—C7—C9151.05 (16)
O1—C1—C2—C316.26 (18)C6—O6—C7—C883.90 (19)
S—C1—C2—C3104.17 (15)C5—O5—C7—O619.8 (2)
C2—O2—C3—C495.86 (17)C5—O5—C7—C9136.19 (17)
C1—C2—C3—O2105.77 (16)C5—O5—C7—C899.92 (19)
O2—C2—C3—C4108.14 (15)C1—S—C10—C1173.55 (16)
C1—C2—C3—C42.37 (19)C1—S—C10—C15108.51 (16)
C1—O1—C4—C331.17 (16)C15—C10—C11—C120.1 (3)
C1—O1—C4—C5158.71 (14)S—C10—C11—C12177.84 (16)
O2—C3—C4—O143.52 (18)C10—C11—C12—C130.5 (3)
C2—C3—C4—O119.79 (18)C11—C12—C13—C140.4 (3)
O2—C3—C4—C576.1 (2)C11—C12—C13—C16179.6 (2)
C2—C3—C4—C5139.41 (17)C12—C13—C14—C150.5 (3)
C7—O5—C5—C4121.00 (16)C16—C13—C14—C15179.5 (2)
C7—O5—C5—C62.3 (2)C11—C10—C15—C141.0 (3)
O1—C4—C5—O5164.23 (14)S—C10—C15—C14177.02 (15)
C3—C4—C5—O578.0 (2)C13—C14—C15—C101.2 (3)
 

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