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In the title compound, C21H24O11, all substituents of the protected sugar are in equatorial positions, with the exclusive presence of the β-anomer. The glucose ring adopts the stable chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053980/wn2105sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053980/wn2105Isup2.hkl
Contains datablock I

CCDC reference: 634071

Key indicators

  • Single-crystal X-ray study
  • T = 183 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.089
  • Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT432_ALERT_2_C Short Inter X...Y Contact O10 .. C13 .. 2.95 Ang.
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 27.47 From the CIF: _reflns_number_total 2662 Count of symmetry unique reflns 2673 Completeness (_total/calc) 99.59% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: XP.

3-Formylphenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside top
Crystal data top
C21H24O11F(000) = 476
Mr = 452.40Dx = 1.382 Mg m3
Monoclinic, P21Melting point: 125 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 11.126 (2) ÅCell parameters from 3652 reflections
b = 8.0199 (16) Åθ = 2.7–27.5°
c = 12.414 (3) ŵ = 0.11 mm1
β = 101.15 (3)°T = 183 K
V = 1086.8 (4) Å3Needle, colourless
Z = 20.3 × 0.3 × 0.2 mm
Data collection top
Nonius KappaCCD
diffractometer
2100 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 27.5°, θmin = 2.7°
φ and ω scansh = 1214
7838 measured reflectionsk = 1010
2662 independent reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0473P)2 + 0.0368P]
where P = (Fo2 + 2Fc2)/3
2662 reflections(Δ/σ)max < 0.001
293 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
O11.13574 (13)0.2432 (2)0.83708 (12)0.0342 (4)
O21.03573 (14)0.4335 (2)0.64778 (13)0.0348 (4)
O30.77643 (15)0.3777 (2)0.58790 (13)0.0377 (4)
O40.65389 (14)0.4242 (2)0.76636 (15)0.0392 (4)
O50.95708 (13)0.2697 (2)0.89921 (12)0.0320 (4)
O60.86516 (14)0.3290 (3)1.08648 (13)0.0398 (4)
O71.20010 (17)0.4272 (3)1.24659 (15)0.0491 (5)
O81.09519 (18)0.2008 (3)0.57145 (16)0.0507 (5)
O90.68160 (17)0.6290 (3)0.56873 (16)0.0483 (5)
O100.55618 (16)0.1798 (3)0.76575 (18)0.0526 (5)
O110.72819 (16)0.2224 (3)1.17634 (16)0.0610 (6)
C11.03122 (19)0.3429 (3)0.83177 (18)0.0303 (5)
H11.05420.45950.85590.036*
C20.96606 (19)0.3390 (3)0.71205 (19)0.0314 (5)
H20.95860.22110.68540.038*
C30.8390 (2)0.4172 (3)0.69794 (18)0.0319 (5)
H30.84560.54080.70830.038*
C40.77101 (19)0.3407 (4)0.7798 (2)0.0330 (5)
H40.75770.21930.76340.040*
C50.84534 (19)0.3620 (3)0.89566 (19)0.0327 (5)
H50.86450.48260.91050.039*
C60.7842 (2)0.2916 (4)0.98346 (19)0.0367 (6)
H6A0.70310.34410.98060.044*
H6B0.77290.16970.97410.044*
C71.22716 (19)0.2515 (3)0.93029 (19)0.0333 (5)
C81.3389 (2)0.1869 (4)0.9174 (2)0.0408 (6)
H81.34770.13960.84920.049*
C91.4376 (2)0.1915 (4)1.0042 (2)0.0482 (7)
H91.51490.14970.99510.058*
C101.4242 (2)0.2565 (4)1.1037 (2)0.0443 (7)
H101.49240.26071.16300.053*
C111.3113 (2)0.3159 (3)1.1175 (2)0.0362 (6)
C121.2105 (2)0.3151 (3)1.03016 (19)0.0326 (5)
H121.13310.35681.03910.039*
C131.2949 (2)0.3746 (4)1.2264 (2)0.0404 (6)
H131.36410.37081.28480.049*
C141.0959 (2)0.3501 (4)0.57899 (19)0.0350 (6)
C151.1597 (2)0.4686 (4)0.5167 (2)0.0437 (7)
H15A1.20990.40600.47400.066*
H15B1.21230.54280.56820.066*
H15C1.09890.53500.46700.066*
C160.6981 (2)0.4950 (4)0.5328 (2)0.0407 (6)
C170.6349 (3)0.4251 (5)0.4255 (2)0.0618 (9)
H17A0.59550.51560.37850.093*
H17B0.57270.34460.43790.093*
H17C0.69490.36920.38960.093*
C180.5530 (2)0.3272 (4)0.7512 (2)0.0369 (6)
C190.4392 (2)0.4271 (5)0.7153 (3)0.0563 (8)
H19A0.37480.35540.67440.084*
H19B0.45590.51860.66800.084*
H19C0.41210.47280.77980.084*
C200.8245 (2)0.2907 (3)1.1786 (2)0.0368 (6)
C210.9133 (2)0.3430 (4)1.2784 (2)0.0435 (6)
H21A0.89310.45581.29950.065*
H21B0.99640.34211.26280.065*
H21C0.90900.26551.33860.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0263 (8)0.0411 (11)0.0341 (9)0.0030 (8)0.0032 (7)0.0033 (7)
O20.0350 (9)0.0364 (10)0.0337 (9)0.0014 (8)0.0084 (7)0.0004 (8)
O30.0364 (8)0.0383 (11)0.0344 (9)0.0043 (8)0.0034 (7)0.0039 (8)
O40.0247 (8)0.0377 (11)0.0542 (11)0.0045 (8)0.0050 (7)0.0014 (9)
O50.0258 (7)0.0362 (10)0.0338 (8)0.0006 (8)0.0054 (6)0.0011 (7)
O60.0337 (8)0.0515 (12)0.0349 (9)0.0091 (8)0.0086 (7)0.0038 (8)
O70.0475 (11)0.0585 (13)0.0404 (10)0.0050 (10)0.0065 (8)0.0011 (9)
O80.0616 (12)0.0400 (13)0.0571 (12)0.0037 (10)0.0280 (10)0.0063 (9)
O90.0502 (11)0.0407 (12)0.0521 (11)0.0090 (9)0.0056 (9)0.0021 (9)
O100.0322 (10)0.0447 (14)0.0808 (14)0.0009 (9)0.0106 (9)0.0041 (11)
O110.0399 (10)0.0917 (19)0.0525 (11)0.0148 (12)0.0120 (9)0.0080 (12)
C10.0245 (10)0.0314 (13)0.0353 (12)0.0010 (10)0.0061 (9)0.0008 (11)
C20.0289 (11)0.0330 (13)0.0323 (12)0.0014 (11)0.0054 (9)0.0028 (10)
C30.0301 (11)0.0328 (14)0.0300 (12)0.0010 (10)0.0013 (9)0.0046 (10)
C40.0240 (10)0.0340 (14)0.0396 (13)0.0016 (11)0.0022 (9)0.0050 (11)
C50.0252 (10)0.0346 (14)0.0388 (13)0.0000 (10)0.0077 (9)0.0051 (11)
C60.0270 (11)0.0424 (17)0.0411 (13)0.0029 (11)0.0075 (10)0.0020 (11)
C70.0246 (10)0.0364 (14)0.0380 (13)0.0039 (10)0.0037 (9)0.0057 (11)
C80.0298 (12)0.0462 (17)0.0475 (14)0.0037 (12)0.0099 (11)0.0014 (13)
C90.0254 (12)0.0570 (19)0.0617 (18)0.0024 (13)0.0072 (12)0.0093 (15)
C100.0287 (11)0.0493 (17)0.0510 (16)0.0054 (12)0.0021 (11)0.0095 (14)
C110.0299 (11)0.0346 (15)0.0417 (13)0.0068 (11)0.0008 (10)0.0080 (11)
C120.0268 (10)0.0338 (15)0.0363 (12)0.0008 (10)0.0039 (9)0.0047 (10)
C130.0378 (13)0.0435 (17)0.0372 (13)0.0076 (12)0.0002 (11)0.0069 (11)
C140.0333 (12)0.0392 (17)0.0314 (12)0.0017 (12)0.0033 (10)0.0004 (11)
C150.0397 (13)0.0523 (19)0.0403 (14)0.0022 (13)0.0109 (11)0.0093 (12)
C160.0328 (13)0.0453 (18)0.0423 (14)0.0062 (12)0.0030 (11)0.0045 (13)
C170.0589 (18)0.073 (2)0.0444 (17)0.0171 (18)0.0127 (14)0.0006 (16)
C180.0303 (12)0.0422 (17)0.0367 (13)0.0001 (12)0.0030 (10)0.0037 (11)
C190.0300 (13)0.057 (2)0.076 (2)0.0050 (14)0.0028 (13)0.0070 (17)
C200.0309 (12)0.0368 (16)0.0445 (14)0.0044 (11)0.0121 (10)0.0046 (11)
C210.0474 (14)0.0470 (17)0.0371 (14)0.0023 (14)0.0106 (11)0.0012 (13)
Geometric parameters (Å, º) top
O1—C71.387 (3)C7—C81.384 (3)
O1—C11.402 (3)C7—C121.386 (4)
O2—C141.358 (3)C8—C91.383 (4)
O2—C21.432 (3)C8—H80.9500
O3—C161.372 (3)C9—C101.375 (4)
O3—C31.443 (3)C9—H90.9500
O4—C181.349 (3)C10—C111.385 (4)
O4—C41.446 (3)C10—H100.9500
O5—C11.412 (3)C11—C121.401 (3)
O5—C51.440 (3)C11—C131.475 (4)
O6—C201.344 (3)C12—H120.9500
O6—C61.446 (3)C13—H130.9500
O7—C131.207 (3)C14—C151.489 (4)
O8—C141.201 (3)C15—H15A0.9800
O9—C161.192 (4)C15—H15B0.9800
O10—C181.195 (4)C15—H15C0.9800
O11—C201.199 (3)C16—C171.490 (4)
C1—C21.523 (3)C17—H17A0.9800
C1—H11.0000C17—H17B0.9800
C2—C31.526 (3)C17—H17C0.9800
C2—H21.0000C18—C191.491 (4)
C3—C41.509 (4)C19—H19A0.9800
C3—H31.0000C19—H19B0.9800
C4—C51.524 (3)C19—H19C0.9800
C4—H41.0000C20—C211.488 (4)
C5—C61.502 (3)C21—H21A0.9800
C5—H51.0000C21—H21B0.9800
C6—H6A0.9900C21—H21C0.9800
C6—H6B0.9900
C7—O1—C1118.68 (19)C8—C9—H9119.9
C14—O2—C2118.4 (2)C9—C10—C11120.0 (2)
C16—O3—C3117.7 (2)C9—C10—H10120.0
C18—O4—C4117.2 (2)C11—C10—H10120.0
C1—O5—C5111.58 (18)C10—C11—C12120.8 (2)
C20—O6—C6116.78 (18)C10—C11—C13119.9 (2)
O1—C1—O5108.03 (19)C12—C11—C13119.2 (2)
O1—C1—C2105.56 (18)C7—C12—C11117.9 (2)
O5—C1—C2110.35 (17)C7—C12—H12121.0
O1—C1—H1110.9C11—C12—H12121.0
O5—C1—H1110.9O7—C13—C11124.7 (2)
C2—C1—H1110.9O7—C13—H13117.6
O2—C2—C1109.03 (17)C11—C13—H13117.6
O2—C2—C3107.9 (2)O8—C14—O2122.9 (2)
C1—C2—C3111.06 (19)O8—C14—C15126.3 (3)
O2—C2—H2109.6O2—C14—C15110.7 (2)
C1—C2—H2109.6C14—C15—H15A109.5
C3—C2—H2109.6C14—C15—H15B109.5
O3—C3—C4109.59 (19)H15A—C15—H15B109.5
O3—C3—C2106.55 (19)C14—C15—H15C109.5
C4—C3—C2109.2 (2)H15A—C15—H15C109.5
O3—C3—H3110.5H15B—C15—H15C109.5
C4—C3—H3110.5O9—C16—O3124.1 (2)
C2—C3—H3110.5O9—C16—C17126.4 (3)
O4—C4—C3107.0 (2)O3—C16—C17109.4 (3)
O4—C4—C5111.68 (19)C16—C17—H17A109.5
C3—C4—C5109.80 (19)C16—C17—H17B109.5
O4—C4—H4109.5H17A—C17—H17B109.5
C3—C4—H4109.5C16—C17—H17C109.5
C5—C4—H4109.5H17A—C17—H17C109.5
O5—C5—C6107.1 (2)H17B—C17—H17C109.5
O5—C5—C4106.19 (18)O10—C18—O4123.3 (2)
C6—C5—C4113.79 (19)O10—C18—C19125.1 (3)
O5—C5—H5109.9O4—C18—C19111.6 (3)
C6—C5—H5109.9C18—C19—H19A109.5
C4—C5—H5109.9C18—C19—H19B109.5
O6—C6—C5105.76 (18)H19A—C19—H19B109.5
O6—C6—H6A110.6C18—C19—H19C109.5
C5—C6—H6A110.6H19A—C19—H19C109.5
O6—C6—H6B110.6H19B—C19—H19C109.5
C5—C6—H6B110.6O11—C20—O6122.0 (2)
H6A—C6—H6B108.7O11—C20—C21126.5 (2)
C8—C7—C12121.3 (2)O6—C20—C21111.4 (2)
C8—C7—O1114.6 (2)C20—C21—H21A109.5
C12—C7—O1124.1 (2)C20—C21—H21B109.5
C9—C8—C7119.7 (3)H21A—C21—H21B109.5
C9—C8—H8120.1C20—C21—H21C109.5
C7—C8—H8120.1H21A—C21—H21C109.5
C10—C9—C8120.1 (2)H21B—C21—H21C109.5
C10—C9—H9119.9
 

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