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The crystal structure of the title compound, C24H32O10, is stabilized by weak C—H...O hydrogen bonds. The six-membered glucopyranosyl ring adopts a chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024573/lh2114sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024573/lh2114Isup2.hkl
Contains datablock I

CCDC reference: 618977

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.048
  • wR factor = 0.128
  • Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.64 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 27.50 From the CIF: _reflns_number_total 3374 Count of symmetry unique reflns 3402 Completeness (_total/calc) 99.18% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

2,3,4,6-Tetra-O-acetyl-O-(p-tert-butylphenyl)-β-D-glucopyranoside top
Crystal data top
C24H32O10Dx = 1.230 Mg m3
Mr = 480.50Melting point = 411–413 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5849 reflections
a = 8.093 (2) Åθ = 3.7–27.5°
b = 10.932 (4) ŵ = 0.10 mm1
c = 29.318 (11) ÅT = 173 K
V = 2593.8 (15) Å3Block, colourless
Z = 40.14 × 0.12 × 0.08 mm
F(000) = 1024
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
3374 independent reflections
Radiation source: fine-focus sealed tube2317 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ω and φ scansθmax = 27.5°, θmin = 3.7°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1010
Tmin = 0.987, Tmax = 0.992k = 1414
5849 measured reflectionsl = 3738
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)] = 0.048H-atom parameters constrained
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.064P)2 + 0.45P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.004
3374 reflectionsΔρmax = 0.27 e Å3
318 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.012 (2)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.5652 (2)0.96766 (19)0.12280 (7)0.0357 (5)
O20.6020 (3)1.2129 (2)0.11657 (8)0.0465 (6)
O30.7981 (17)1.3574 (16)0.1244 (4)0.087 (3)0.50
O3'0.7583 (18)1.3726 (16)0.1020 (4)0.087 (3)0.50
O40.5564 (2)1.06700 (18)0.00395 (7)0.0330 (5)
O50.4511 (4)1.2566 (3)0.00541 (10)0.0664 (8)
O60.2287 (2)0.96709 (19)0.01897 (7)0.0343 (5)
O70.2047 (3)0.7899 (2)0.01980 (8)0.0524 (6)
O80.2464 (2)0.76002 (18)0.08389 (7)0.0354 (5)
O90.0011 (3)0.8474 (2)0.09916 (9)0.0514 (7)
O100.4367 (2)0.8083 (2)0.15850 (7)0.0391 (5)
C10.6268 (3)1.0173 (3)0.08130 (10)0.0330 (7)
H10.70400.96140.06770.040*
C20.4849 (3)1.0385 (3)0.04782 (10)0.0300 (6)
H20.41811.10470.05890.036*
C30.3766 (3)0.9263 (3)0.04229 (10)0.0297 (7)
H30.43630.86600.02510.036*
C40.3300 (3)0.8752 (3)0.08870 (10)0.0317 (7)
H40.26000.93300.10400.038*
C50.4860 (4)0.8526 (3)0.11604 (10)0.0344 (7)
H50.55730.79400.10170.041*
C60.7163 (4)1.1338 (3)0.09304 (12)0.0410 (8)
H6A0.75361.17380.06580.049*
H6B0.80911.11750.11250.049*
C70.6511 (5)1.3261 (4)0.12562 (16)0.0632 (11)
C80.5256 (6)1.3958 (4)0.15248 (17)0.0776 (14)
H8A0.54351.48380.14820.093*
H8B0.53661.37540.18490.093*
H8C0.41461.37410.14200.093*
C90.5324 (4)1.1811 (3)0.01349 (11)0.0402 (8)
C100.6145 (4)1.1959 (3)0.05834 (12)0.0484 (9)
H10A0.63161.28300.06450.058*
H10B0.54481.16040.08230.058*
H10C0.72151.15390.05790.058*
C110.1524 (4)0.8893 (3)0.01034 (11)0.0388 (8)
C120.0054 (4)0.9436 (3)0.02714 (14)0.0533 (10)
H12A0.01220.93410.06030.064*
H12B0.00891.03070.01930.064*
H12C0.09900.90150.01280.064*
C130.0819 (4)0.7575 (3)0.09222 (10)0.0364 (7)
C140.0208 (5)0.6293 (3)0.09203 (13)0.0527 (9)
H14A0.09940.62900.09600.063*
H14B0.07250.58380.11700.063*
H14C0.04890.59060.06290.063*
C150.5551 (4)0.7567 (3)0.18655 (10)0.0340 (7)
C160.7236 (4)0.7620 (3)0.17865 (11)0.0412 (8)
H160.76240.80360.15190.049*
C170.8298 (4)0.7068 (3)0.20939 (11)0.0431 (8)
H170.94680.70900.20420.052*
C180.7733 (4)0.6469 (3)0.24831 (11)0.0407 (8)
C190.6020 (4)0.6435 (3)0.25486 (12)0.0463 (9)
H190.55800.60310.28130.056*
C200.4954 (4)0.6967 (3)0.22457 (11)0.0435 (8)
H200.37810.69130.22900.052*
C210.8876 (4)0.5848 (4)0.28278 (13)0.0511 (9)
C220.8502 (5)0.6345 (4)0.33105 (13)0.0698 (12)
H22A0.92020.59240.35340.084*
H22B0.73370.62000.33840.084*
H22C0.87300.72250.33200.084*
C231.0680 (4)0.6075 (5)0.27326 (16)0.0775 (15)
H23A1.13520.56670.29650.093*
H23B1.08990.69560.27390.093*
H23C1.09630.57490.24310.093*
C240.8550 (6)0.4496 (4)0.28294 (17)0.0755 (13)
H24A0.92440.41030.30610.091*
H24B0.88110.41560.25290.091*
H24C0.73840.43470.29000.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0365 (10)0.0395 (12)0.0312 (11)0.0042 (10)0.0002 (9)0.0008 (10)
O20.0489 (13)0.0420 (14)0.0485 (13)0.0095 (11)0.0019 (11)0.0127 (11)
O30.064 (6)0.062 (4)0.135 (10)0.027 (4)0.017 (6)0.025 (8)
O3'0.064 (6)0.062 (4)0.135 (10)0.027 (4)0.017 (6)0.025 (8)
O40.0364 (10)0.0299 (11)0.0326 (11)0.0003 (9)0.0031 (9)0.0023 (9)
O50.0892 (19)0.0372 (14)0.0728 (18)0.0195 (15)0.0224 (16)0.0115 (13)
O60.0325 (10)0.0309 (12)0.0393 (12)0.0001 (9)0.0083 (9)0.0019 (10)
O70.0551 (14)0.0392 (14)0.0629 (16)0.0032 (12)0.0125 (12)0.0189 (12)
O80.0356 (11)0.0294 (12)0.0412 (12)0.0034 (9)0.0060 (9)0.0028 (10)
O90.0349 (12)0.0482 (15)0.0712 (17)0.0017 (12)0.0076 (12)0.0078 (13)
O100.0318 (10)0.0512 (14)0.0341 (11)0.0043 (11)0.0048 (9)0.0105 (10)
C10.0288 (13)0.0366 (17)0.0337 (16)0.0021 (14)0.0003 (12)0.0023 (14)
C20.0303 (14)0.0280 (15)0.0317 (15)0.0021 (13)0.0022 (12)0.0008 (13)
C30.0297 (14)0.0261 (15)0.0332 (15)0.0036 (13)0.0017 (12)0.0041 (13)
C40.0307 (14)0.0284 (16)0.0361 (16)0.0002 (13)0.0020 (13)0.0019 (13)
C50.0307 (15)0.0396 (18)0.0330 (16)0.0004 (14)0.0031 (13)0.0026 (14)
C60.0326 (15)0.048 (2)0.0420 (18)0.0051 (15)0.0019 (15)0.0001 (17)
C70.060 (2)0.046 (2)0.084 (3)0.012 (2)0.010 (2)0.015 (2)
C80.094 (3)0.048 (2)0.091 (3)0.008 (3)0.025 (3)0.020 (2)
C90.0398 (17)0.0362 (19)0.0447 (19)0.0043 (16)0.0039 (15)0.0055 (15)
C100.0488 (18)0.049 (2)0.048 (2)0.0091 (18)0.0031 (17)0.0131 (17)
C110.0411 (17)0.0340 (18)0.0412 (18)0.0057 (15)0.0059 (15)0.0026 (15)
C120.0489 (19)0.044 (2)0.067 (2)0.0018 (18)0.0238 (19)0.0024 (19)
C130.0374 (16)0.0415 (19)0.0302 (15)0.0069 (15)0.0023 (13)0.0016 (15)
C140.056 (2)0.048 (2)0.054 (2)0.0150 (18)0.0050 (19)0.0059 (18)
C150.0327 (14)0.0342 (17)0.0352 (16)0.0003 (14)0.0008 (13)0.0041 (14)
C160.0389 (17)0.047 (2)0.0375 (17)0.0013 (16)0.0048 (14)0.0104 (16)
C170.0352 (16)0.046 (2)0.048 (2)0.0020 (16)0.0006 (15)0.0091 (17)
C180.0455 (18)0.0371 (19)0.0395 (19)0.0057 (16)0.0058 (15)0.0075 (15)
C190.0470 (19)0.052 (2)0.0403 (19)0.0047 (17)0.0054 (16)0.0117 (17)
C200.0360 (16)0.053 (2)0.0413 (18)0.0027 (17)0.0037 (15)0.0095 (16)
C210.0439 (18)0.055 (2)0.055 (2)0.0002 (18)0.0054 (17)0.0196 (19)
C220.066 (3)0.094 (3)0.050 (2)0.000 (3)0.009 (2)0.014 (2)
C230.044 (2)0.111 (4)0.077 (3)0.007 (3)0.003 (2)0.045 (3)
C240.075 (3)0.063 (3)0.089 (3)0.016 (2)0.012 (3)0.028 (3)
Geometric parameters (Å, º) top
O1—C11.423 (3)C10—H10A0.9800
O1—C51.425 (4)C10—H10B0.9800
O2—C71.327 (4)C10—H10C0.9800
O2—C61.442 (4)C11—C121.492 (5)
O3—C71.238 (14)C12—H12A0.9800
O3'—C71.222 (16)C12—H12B0.9800
O4—C91.362 (4)C12—H12C0.9800
O4—C21.445 (3)C13—C141.486 (5)
O5—C91.192 (4)C14—H14A0.9800
O6—C111.357 (4)C14—H14B0.9800
O6—C31.448 (3)C14—H14C0.9800
O7—C111.200 (4)C15—C201.381 (4)
O8—C131.354 (4)C15—C161.385 (4)
O8—C41.437 (4)C16—C171.383 (5)
O9—C131.197 (4)C16—H160.9598
O10—C151.383 (4)C17—C181.393 (4)
O10—C51.394 (4)C17—H170.9599
C1—C61.505 (4)C18—C191.399 (5)
C1—C21.528 (4)C18—C211.529 (5)
C1—H10.9600C19—C201.368 (5)
C2—C31.516 (4)C19—H190.9600
C2—H20.9600C20—H200.9600
C3—C41.518 (4)C21—C241.501 (6)
C3—H30.9600C21—C231.507 (5)
C4—C51.516 (4)C21—C221.546 (6)
C4—H40.9600C22—H22A0.9800
C5—H50.9600C22—H22B0.9800
C6—H6A0.9600C22—H22C0.9800
C6—H6B0.9600C23—H23A0.9800
C7—C81.494 (6)C23—H23B0.9800
C8—H8A0.9800C23—H23C0.9800
C8—H8B0.9800C24—H24A0.9800
C8—H8C0.9800C24—H24B0.9800
C9—C101.482 (5)C24—H24C0.9800
C1—O1—C5112.0 (2)H10B—C10—H10C109.5
C7—O2—C6117.6 (3)O7—C11—O6123.6 (3)
C9—O4—C2118.3 (2)O7—C11—C12125.9 (3)
C11—O6—C3118.8 (2)O6—C11—C12110.5 (3)
C13—O8—C4117.6 (2)C11—C12—H12A109.5
C15—O10—C5118.3 (2)C11—C12—H12B109.5
O1—C1—C6107.2 (2)H12A—C12—H12B109.5
O1—C1—C2110.1 (2)C11—C12—H12C109.5
C6—C1—C2112.3 (3)H12A—C12—H12C109.5
O1—C1—H1109.9H12B—C12—H12C109.5
C6—C1—H1108.7O9—C13—O8123.4 (3)
C2—C1—H1108.7O9—C13—C14126.3 (3)
O4—C2—C3108.1 (2)O8—C13—C14110.2 (3)
O4—C2—C1107.7 (2)C13—C14—H14A109.5
C3—C2—C1112.3 (2)C13—C14—H14B109.5
O4—C2—H2111.4H14A—C14—H14B109.5
C3—C2—H2108.7C13—C14—H14C109.5
C1—C2—H2108.7H14A—C14—H14C109.5
O6—C3—C2106.2 (2)H14B—C14—H14C109.5
O6—C3—C4109.3 (2)C20—C15—O10115.6 (3)
C2—C3—C4110.2 (2)C20—C15—C16119.9 (3)
O6—C3—H3112.3O10—C15—C16124.5 (3)
C2—C3—H3108.7C17—C16—C15119.0 (3)
C4—C3—H3110.0C17—C16—H16122.4
O8—C4—C5107.5 (2)C15—C16—H16118.6
O8—C4—C3110.6 (2)C16—C17—C18122.3 (3)
C5—C4—C3109.1 (2)C16—C17—H17119.9
O8—C4—H4110.2C18—C17—H17117.8
C5—C4—H4110.6C17—C18—C19116.7 (3)
C3—C4—H4108.9C17—C18—C21123.5 (3)
O10—C5—O1108.1 (2)C19—C18—C21119.8 (3)
O10—C5—C4106.9 (2)C20—C19—C18121.6 (3)
O1—C5—C4107.7 (2)C20—C19—H19119.0
O10—C5—H5109.4C18—C19—H19119.3
O1—C5—H5112.3C19—C20—C15120.3 (3)
C4—C5—H5112.2C19—C20—H20120.7
O2—C6—C1108.0 (2)C15—C20—H20119.0
O2—C6—H6A109.1C24—C21—C23109.4 (4)
C1—C6—H6A110.2C24—C21—C18109.4 (3)
O2—C6—H6B109.2C23—C21—C18113.0 (3)
C1—C6—H6B110.8C24—C21—C22108.0 (3)
H6A—C6—H6B109.5C23—C21—C22107.5 (4)
O3'—C7—O2119.1 (9)C18—C21—C22109.3 (3)
O3—C7—O2122.6 (9)C21—C22—H22A109.5
O3'—C7—C8124.7 (9)C21—C22—H22B109.5
O3—C7—C8121.8 (9)H22A—C22—H22B109.5
O2—C7—C8112.2 (3)C21—C22—H22C109.5
C7—C8—H8A109.5H22A—C22—H22C109.5
C7—C8—H8B109.5H22B—C22—H22C109.5
H8A—C8—H8B109.5C21—C23—H23A109.5
C7—C8—H8C109.5C21—C23—H23B109.5
H8A—C8—H8C109.5H23A—C23—H23B109.5
H8B—C8—H8C109.5C21—C23—H23C109.5
O5—C9—O4122.6 (3)H23A—C23—H23C109.5
O5—C9—C10125.8 (3)H23B—C23—H23C109.5
O4—C9—C10111.6 (3)C21—C24—H24A109.5
C9—C10—H10A109.5C21—C24—H24B109.5
C9—C10—H10B109.5H24A—C24—H24B109.5
H10A—C10—H10B109.5C21—C24—H24C109.5
C9—C10—H10C109.5H24A—C24—H24C109.5
H10A—C10—H10C109.5H24B—C24—H24C109.5
C5—O1—C1—C6176.6 (2)O1—C1—C6—O256.9 (3)
C5—O1—C1—C261.0 (3)C2—C1—C6—O264.2 (3)
C9—O4—C2—C3124.2 (3)C6—O2—C7—O3'24.7 (8)
C9—O4—C2—C1114.2 (3)C6—O2—C7—O316.9 (9)
O1—C1—C2—O4169.6 (2)C6—O2—C7—C8176.5 (3)
C6—C1—C2—O471.0 (3)C2—O4—C9—O52.2 (4)
O1—C1—C2—C350.7 (3)C2—O4—C9—C10179.5 (2)
C6—C1—C2—C3170.1 (2)C3—O6—C11—O73.6 (5)
C11—O6—C3—C2146.7 (2)C3—O6—C11—C12174.4 (3)
C11—O6—C3—C494.5 (3)C4—O8—C13—O97.1 (4)
O4—C2—C3—O674.6 (3)C4—O8—C13—C14172.1 (3)
C1—C2—C3—O6166.7 (2)C5—O10—C15—C20169.7 (3)
O4—C2—C3—C4167.1 (2)C5—O10—C15—C1610.2 (5)
C1—C2—C3—C448.4 (3)C20—C15—C16—C170.3 (6)
C13—O8—C4—C5133.4 (3)O10—C15—C16—C17179.8 (3)
C13—O8—C4—C3107.6 (3)C15—C16—C17—C180.5 (6)
O6—C3—C4—O871.4 (3)C16—C17—C18—C190.7 (5)
C2—C3—C4—O8172.2 (2)C16—C17—C18—C21179.8 (3)
O6—C3—C4—C5170.6 (2)C17—C18—C19—C200.1 (6)
C2—C3—C4—C554.2 (3)C21—C18—C19—C20179.2 (3)
C15—O10—C5—O177.4 (3)C18—C19—C20—C150.6 (6)
C15—O10—C5—C4166.8 (3)O10—C15—C20—C19179.3 (3)
C1—O1—C5—O10177.2 (2)C16—C15—C20—C190.8 (5)
C1—O1—C5—C467.6 (3)C17—C18—C21—C24115.6 (4)
O8—C4—C5—O1061.2 (3)C19—C18—C21—C2463.5 (5)
C3—C4—C5—O10178.8 (2)C17—C18—C21—C236.6 (6)
O8—C4—C5—O1177.2 (2)C19—C18—C21—C23174.3 (4)
C3—C4—C5—O162.8 (3)C17—C18—C21—C22126.3 (4)
C7—O2—C6—C1172.8 (3)C19—C18—C21—C2254.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O20.962.542.932 (4)104
C2—H2···O50.962.302.702 (4)104
C4—H4···O90.962.302.697 (4)104
C10—H10B···O3i0.982.363.263 (16)154
C10—H10B···O3i0.982.423.241 (17)142
C12—H12B···O5i0.982.383.358 (5)173
C16—H16···O10.962.553.063 (4)114
C16—H16···O9ii0.962.523.368 (4)147
C24—H24C···O10iii0.982.493.303 (5)140
Symmetry codes: (i) x1/2, y+5/2, z; (ii) x+1, y, z; (iii) x+1, y1/2, z+1/2.
 

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