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The six-membered sugar ring of the title compound, C21H26O11, adopts a chair conformation. The crystal structure is stabilized by inter­molecular C—H...O hydrogen bonds and van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018988/ac2021sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018988/ac2021Isup2.hkl
Contains datablock I

CCDC reference: 610678

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.043
  • wR factor = 0.105
  • Data-to-parameter ratio = 7.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.74 PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
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 25.01 From the CIF: _reflns_number_total 2261 Count of symmetry unique reflns 2262 Completeness (_total/calc) 99.96% 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 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-β-D-galactopyranoside top
Crystal data top
C21H26O11F(000) = 480
Mr = 454.42Dx = 1.310 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1048 reflections
a = 11.935 (3) Åθ = 2.3–22.3°
b = 5.7061 (14) ŵ = 0.11 mm1
c = 17.873 (4) ÅT = 298 K
β = 108.884 (3)°Block, colorless
V = 1151.7 (5) Å30.40 × 0.18 × 0.05 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
2261 independent reflections
Radiation source: fine-focus sealed tube1837 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.959, Tmax = 0.995k = 56
6093 measured reflectionsl = 1821
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0463P)2 + 0.1697P]
where P = (Fo2 + 2Fc2)/3
2261 reflections(Δ/σ)max < 0.001
292 parametersΔρmax = 0.14 e Å3
1 restraintΔρmin = 0.14 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
O10.77686 (19)0.6275 (5)0.28380 (13)0.0445 (6)
O20.9015 (2)0.2391 (6)0.36858 (15)0.0649 (8)
O30.9183 (2)0.0210 (6)0.46505 (16)0.0682 (8)
O40.6447 (2)0.7491 (5)0.38798 (13)0.0481 (7)
O50.6311 (3)0.5183 (7)0.48502 (17)0.0849 (11)
O60.4419 (2)0.8018 (5)0.26628 (14)0.0515 (7)
O70.3482 (3)0.5001 (7)0.29902 (17)0.0756 (9)
O80.5103 (2)0.8032 (5)0.12844 (14)0.0473 (6)
O90.5091 (3)1.1942 (6)0.12999 (19)0.0784 (10)
O100.7623 (2)0.8400 (5)0.17324 (14)0.0510 (7)
O111.1608 (3)0.6532 (7)0.0905 (2)0.0827 (10)
C10.7051 (3)0.6755 (7)0.20548 (19)0.0421 (9)
H1A0.68860.53200.17370.050*
C20.5914 (3)0.7886 (7)0.20757 (18)0.0411 (8)
H2A0.60820.94630.23010.049*
C30.5301 (3)0.6462 (7)0.2547 (2)0.0424 (9)
H3A0.49020.51230.22270.051*
C40.6137 (3)0.5564 (7)0.33311 (19)0.0433 (9)
H4A0.57400.43430.35380.052*
C50.7235 (3)0.4541 (7)0.31925 (19)0.0437 (9)
H5A0.69880.32220.28250.052*
C60.8152 (3)0.3688 (8)0.3925 (2)0.0582 (11)
H6A0.85270.50020.42560.070*
H6B0.77930.26870.42230.070*
C70.9459 (3)0.0471 (8)0.4104 (2)0.0542 (11)
C81.0338 (4)0.0681 (10)0.3790 (3)0.0797 (16)
H8A1.05550.21790.40400.120*
H8B1.10310.02870.38990.120*
H8C0.99950.08940.32290.120*
C90.6453 (3)0.7063 (8)0.4628 (2)0.0508 (10)
C100.6675 (4)0.9229 (9)0.5115 (2)0.0724 (13)
H10A0.65580.89100.56120.109*
H10B0.61371.04340.48410.109*
H10C0.74750.97410.52080.109*
C110.3561 (4)0.7084 (10)0.2903 (2)0.0576 (12)
C120.2760 (4)0.8893 (11)0.3034 (3)0.0853 (16)
H12A0.20260.81790.30220.128*
H12B0.26101.00560.26250.128*
H12C0.31220.96190.35390.128*
C130.4742 (3)1.0157 (8)0.0973 (2)0.0505 (10)
C140.3855 (4)0.9915 (10)0.0167 (2)0.0736 (14)
H14A0.36121.14420.00500.110*
H14B0.31780.90680.02020.110*
H14C0.42030.90780.01680.110*
C150.8615 (3)0.7692 (8)0.1543 (2)0.0450 (9)
C160.9228 (3)0.5660 (8)0.1774 (2)0.0595 (11)
H16A0.89770.45800.20760.071*
C171.0225 (4)0.5190 (9)0.1561 (2)0.0617 (11)
H17A1.06340.37920.17180.074*
C181.0610 (3)0.6772 (9)0.1123 (2)0.0583 (11)
C190.9979 (4)0.8800 (9)0.0884 (3)0.0653 (12)
H19A1.02200.98720.05750.078*
C200.8994 (3)0.9261 (8)0.1097 (2)0.0585 (11)
H20A0.85811.06520.09370.070*
C211.2198 (4)0.4370 (11)0.1031 (3)0.0843 (17)
H21A1.28670.44500.08460.127*
H21B1.16670.31670.07480.127*
H21C1.24640.40130.15860.127*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0455 (13)0.0524 (17)0.0354 (13)0.0022 (12)0.0128 (11)0.0000 (12)
O20.0665 (17)0.079 (2)0.0570 (16)0.0261 (17)0.0302 (14)0.0187 (16)
O30.0696 (18)0.073 (2)0.0651 (18)0.0180 (17)0.0256 (15)0.0153 (18)
O40.0620 (15)0.0488 (17)0.0384 (13)0.0040 (13)0.0229 (12)0.0014 (12)
O50.153 (3)0.062 (2)0.0534 (17)0.012 (2)0.0517 (19)0.0068 (18)
O60.0491 (14)0.0521 (17)0.0585 (16)0.0038 (14)0.0249 (13)0.0001 (14)
O70.075 (2)0.083 (3)0.083 (2)0.008 (2)0.0444 (17)0.007 (2)
O80.0553 (15)0.0443 (16)0.0377 (13)0.0034 (13)0.0086 (11)0.0005 (13)
O90.109 (3)0.045 (2)0.071 (2)0.0074 (19)0.0146 (19)0.0011 (17)
O100.0581 (14)0.0482 (17)0.0561 (16)0.0024 (13)0.0315 (13)0.0070 (13)
O110.0637 (19)0.095 (3)0.107 (3)0.002 (2)0.0518 (19)0.009 (2)
C10.0481 (19)0.045 (2)0.0347 (18)0.0021 (18)0.0151 (16)0.0015 (17)
C20.0490 (19)0.039 (2)0.0336 (18)0.0008 (18)0.0107 (15)0.0016 (17)
C30.0441 (19)0.039 (2)0.046 (2)0.0020 (17)0.0177 (16)0.0045 (17)
C40.050 (2)0.040 (2)0.042 (2)0.0046 (18)0.0188 (17)0.0032 (17)
C50.054 (2)0.039 (2)0.0402 (19)0.0032 (18)0.0194 (16)0.0031 (17)
C60.067 (2)0.064 (3)0.050 (2)0.019 (2)0.027 (2)0.010 (2)
C70.039 (2)0.070 (3)0.047 (2)0.012 (2)0.0049 (18)0.004 (2)
C80.059 (2)0.103 (5)0.073 (3)0.034 (3)0.016 (2)0.000 (3)
C90.063 (2)0.055 (3)0.043 (2)0.004 (2)0.0277 (19)0.004 (2)
C100.104 (3)0.067 (3)0.057 (3)0.006 (3)0.042 (3)0.013 (2)
C110.053 (2)0.080 (4)0.043 (2)0.000 (2)0.0202 (19)0.002 (2)
C120.071 (3)0.111 (4)0.088 (3)0.018 (3)0.046 (3)0.008 (3)
C130.063 (2)0.048 (3)0.046 (2)0.007 (2)0.0244 (18)0.001 (2)
C140.083 (3)0.080 (4)0.051 (2)0.018 (3)0.012 (2)0.007 (3)
C150.047 (2)0.052 (2)0.0373 (19)0.006 (2)0.0159 (16)0.0018 (19)
C160.066 (2)0.057 (3)0.065 (3)0.005 (2)0.034 (2)0.012 (2)
C170.062 (2)0.059 (3)0.070 (3)0.008 (2)0.030 (2)0.003 (3)
C180.049 (2)0.071 (3)0.058 (2)0.010 (2)0.022 (2)0.013 (2)
C190.065 (3)0.071 (3)0.069 (3)0.012 (3)0.034 (2)0.013 (3)
C200.060 (2)0.060 (3)0.056 (2)0.002 (2)0.021 (2)0.010 (2)
C210.060 (3)0.110 (5)0.088 (3)0.006 (3)0.030 (2)0.022 (3)
Geometric parameters (Å, º) top
O1—C11.412 (4)C7—C81.493 (6)
O1—C51.431 (4)C8—H8A0.9600
O2—C71.335 (5)C8—H8B0.9600
O2—C61.441 (4)C8—H8C0.9600
O3—C71.193 (5)C9—C101.486 (6)
O4—C91.357 (4)C10—H10A0.9600
O4—C41.440 (4)C10—H10B0.9600
O5—C91.175 (5)C10—H10C0.9600
O6—C111.342 (5)C11—C121.476 (7)
O6—C31.442 (4)C12—H12A0.9600
O7—C111.206 (6)C12—H12B0.9600
O8—C131.346 (5)C12—H12C0.9600
O8—C21.434 (4)C13—C141.492 (5)
O9—C131.181 (5)C14—H14A0.9600
O10—C11.391 (4)C14—H14B0.9600
O10—C151.391 (4)C14—H14C0.9600
O11—C181.375 (5)C15—C161.362 (6)
O11—C211.402 (7)C15—C201.370 (5)
C1—C21.514 (5)C16—C171.387 (5)
C1—H1A0.9800C16—H16A0.9300
C2—C31.517 (5)C17—C181.368 (6)
C2—H2A0.9800C17—H17A0.9300
C3—C41.523 (5)C18—C191.372 (7)
C3—H3A0.9800C19—C201.374 (6)
C4—C51.526 (5)C19—H19A0.9300
C4—H4A0.9800C20—H20A0.9300
C5—C61.490 (5)C21—H21A0.9600
C5—H5A0.9800C21—H21B0.9600
C6—H6A0.9700C21—H21C0.9600
C6—H6B0.9700
C1—O1—C5111.0 (2)O5—C9—O4122.8 (4)
C7—O2—C6116.6 (3)O5—C9—C10125.4 (3)
C9—O4—C4116.9 (3)O4—C9—C10111.8 (4)
C11—O6—C3118.0 (3)C9—C10—H10A109.5
C13—O8—C2118.9 (3)C9—C10—H10B109.5
C1—O10—C15118.4 (3)H10A—C10—H10B109.5
C18—O11—C21118.6 (4)C9—C10—H10C109.5
O10—C1—O1108.7 (3)H10A—C10—H10C109.5
O10—C1—C2106.7 (3)H10B—C10—H10C109.5
O1—C1—C2108.6 (3)O7—C11—O6122.2 (4)
O10—C1—H1A110.9O7—C11—C12125.9 (4)
O1—C1—H1A110.9O6—C11—C12111.9 (5)
C2—C1—H1A110.9C11—C12—H12A109.5
O8—C2—C1108.9 (3)C11—C12—H12B109.5
O8—C2—C3106.6 (3)H12A—C12—H12B109.5
C1—C2—C3112.5 (3)C11—C12—H12C109.5
O8—C2—H2A109.6H12A—C12—H12C109.5
C1—C2—H2A109.6H12B—C12—H12C109.5
C3—C2—H2A109.6O9—C13—O8123.9 (3)
O6—C3—C2104.8 (3)O9—C13—C14125.7 (4)
O6—C3—C4111.5 (3)O8—C13—C14110.4 (4)
C2—C3—C4113.7 (3)C13—C14—H14A109.5
O6—C3—H3A108.9C13—C14—H14B109.5
C2—C3—H3A108.9H14A—C14—H14B109.5
C4—C3—H3A108.9C13—C14—H14C109.5
O4—C4—C3108.5 (3)H14A—C14—H14C109.5
O4—C4—C5110.9 (3)H14B—C14—H14C109.5
C3—C4—C5108.7 (3)C16—C15—C20119.1 (4)
O4—C4—H4A109.6C16—C15—O10126.1 (4)
C3—C4—H4A109.6C20—C15—O10114.8 (4)
C5—C4—H4A109.6C15—C16—C17120.4 (4)
O1—C5—C6108.0 (3)C15—C16—H16A119.8
O1—C5—C4109.6 (3)C17—C16—H16A119.8
C6—C5—C4114.0 (3)C18—C17—C16120.4 (5)
O1—C5—H5A108.3C18—C17—H17A119.8
C6—C5—H5A108.3C16—C17—H17A119.8
C4—C5—H5A108.3C17—C18—C19118.9 (4)
O2—C6—C5107.4 (3)C17—C18—O11125.4 (5)
O2—C6—H6A110.2C19—C18—O11115.7 (4)
C5—C6—H6A110.2C18—C19—C20120.5 (4)
O2—C6—H6B110.2C18—C19—H19A119.8
C5—C6—H6B110.2C20—C19—H19A119.8
H6A—C6—H6B108.5C15—C20—C19120.7 (4)
O3—C7—O2124.1 (4)C15—C20—H20A119.6
O3—C7—C8125.3 (4)C19—C20—H20A119.6
O2—C7—C8110.6 (4)O11—C21—H21A109.5
C7—C8—H8A109.5O11—C21—H21B109.5
C7—C8—H8B109.5H21A—C21—H21B109.5
H8A—C8—H8B109.5O11—C21—H21C109.5
C7—C8—H8C109.5H21A—C21—H21C109.5
H8A—C8—H8C109.5H21B—C21—H21C109.5
H8B—C8—H8C109.5
C15—O10—C1—O171.9 (4)C3—C4—C5—C6177.5 (3)
C15—O10—C1—C2171.1 (3)C7—O2—C6—C5141.9 (3)
C5—O1—C1—O10178.5 (3)O1—C5—C6—O268.5 (4)
C5—O1—C1—C265.8 (4)C4—C5—C6—O2169.3 (3)
C13—O8—C2—C1117.8 (3)C6—O2—C7—O30.1 (6)
C13—O8—C2—C3120.6 (3)C6—O2—C7—C8179.9 (4)
O10—C1—C2—O872.3 (3)C4—O4—C9—O56.2 (6)
O1—C1—C2—O8170.8 (3)C4—O4—C9—C10174.7 (3)
O10—C1—C2—C3169.8 (3)C3—O6—C11—O73.1 (6)
O1—C1—C2—C352.8 (4)C3—O6—C11—C12177.2 (3)
C11—O6—C3—C2165.0 (3)C2—O8—C13—O93.3 (5)
C11—O6—C3—C471.6 (4)C2—O8—C13—C14176.8 (3)
O8—C2—C3—O673.9 (3)C1—O10—C15—C1613.1 (5)
C1—C2—C3—O6166.8 (3)C1—O10—C15—C20168.3 (3)
O8—C2—C3—C4164.2 (3)C20—C15—C16—C170.2 (6)
C1—C2—C3—C444.9 (4)O10—C15—C16—C17178.3 (4)
C9—O4—C4—C3136.8 (3)C15—C16—C17—C180.5 (6)
C9—O4—C4—C5103.8 (4)C16—C17—C18—C191.4 (6)
O6—C3—C4—O443.0 (4)C16—C17—C18—O11177.4 (4)
C2—C3—C4—O475.2 (4)C21—O11—C18—C1710.2 (6)
O6—C3—C4—C5163.7 (3)C21—O11—C18—C19171.0 (4)
C2—C3—C4—C545.6 (4)C17—C18—C19—C201.6 (6)
C1—O1—C5—C6165.9 (3)O11—C18—C19—C20177.3 (4)
C1—O1—C5—C469.3 (3)C16—C15—C20—C190.0 (6)
O4—C4—C5—O163.0 (3)O10—C15—C20—C19178.6 (4)
C3—C4—C5—O156.3 (4)C18—C19—C20—C150.9 (6)
O4—C4—C5—C658.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O90.982.292.713 (5)105
C4—H4A···O50.982.272.664 (4)103
C4—H4A···O70.982.583.044 (5)109
C6—H6B···O30.972.292.666 (5)102
C16—H16A···O10.932.482.987 (4)115
C3—H3A···O9i0.982.523.364 (5)145
C10—H10A···O7ii0.962.593.479 (5)154
C10—H10C···O3iii0.962.543.370 (5)145
C21—H21C···O7iv0.962.473.356 (6)153
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1/2, z+1; (iii) x, y+1, z; (iv) x+1, y, z.
 

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