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In the title compound, C31H34O8, the three benzene rings are nearly perpendicular to each other. The six-membered mannopyranoside ring displays a typical chair conformation. Inter­molecular C—H...O hydrogen bonding helps to stabilize the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023501/xu2242sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023501/xu2242Isup2.hkl
Contains datablock I

CCDC reference: 651485

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.053
  • wR factor = 0.089
  • Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.04 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.47 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10 PLAT432_ALERT_2_C Short Inter X...Y Contact O8 .. C30 .. 2.99 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 25.00 From the CIF: _reflns_number_total 2627 Count of symmetry unique reflns 2627 Completeness (_total/calc) 100.00% 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 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 5 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 4 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

Comment top

The title compound, 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside, (I), is obtained from methyl-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside with acetic anhydride, acetic acid and concentrated sulfuric acid in ice bath yields 90% as a white solid.

The title compound is a derivative of mannopyranoside, and the six-membered ring has a chair conformation. All five hydroxyl groups are substituted by three benzyloxy groups and two acetoxy groups respectively. The dihedral angles of three benzene rings are 94.4 (2)° (A/B), 103.9 (2)° (A/C), and 110.8 (2)° (B/C). The weak C–H···O hydrogen bonding helps to stabilize the crystal structure (Table 1).

Related literature top

For synthesis, see Tennant-Eyles et al., 2000.

Experimental top

The title compound was synthesized according to the procedure of Tennant-Eyles et al. (2000). The compound was crystallized from hexane/ethyl acetate solution (4:1, v/v) to yield colorless block-like crystals after a week at room temperature.

Refinement top

All H-atoms were refined using a riding model with C—H = 0.93 Å and Uiso=1.2Ueq(C) for aromatic, 0.98 Å and Uiso = 1.2Ueq (C) for CH, 0.97 Å and Uiso = 1.2Ueq(C) for CH2, 0.96 Å and Uiso = 1.5Ueq(C) for CH3. In the absence of significant anomalous dispersion effects, Freidel pairs were merged.

Structure description top

The title compound, 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside, (I), is obtained from methyl-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside with acetic anhydride, acetic acid and concentrated sulfuric acid in ice bath yields 90% as a white solid.

The title compound is a derivative of mannopyranoside, and the six-membered ring has a chair conformation. All five hydroxyl groups are substituted by three benzyloxy groups and two acetoxy groups respectively. The dihedral angles of three benzene rings are 94.4 (2)° (A/B), 103.9 (2)° (A/C), and 110.8 (2)° (B/C). The weak C–H···O hydrogen bonding helps to stabilize the crystal structure (Table 1).

For synthesis, see Tennant-Eyles et al., 2000.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by circles of arbitrary size.
[Figure 2] Fig. 2. The molecular packing of (I) viewed along the c axis. Dashed lines indicate hydrogen bonding interactions.
1,5-Di-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside top
Crystal data top
C31H34O8Dx = 1.191 Mg m3
Mr = 534.58Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3Cell parameters from 16963 reflections
Hall symbol: R 3θ = 2.4–25.0°
a = 24.001 (3) ŵ = 0.09 mm1
c = 13.441 (3) ÅT = 298 K
V = 6705.5 (19) Å3Block, colorless
Z = 90.50 × 0.45 × 0.25 mm
F(000) = 2556
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
1277 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.056
Graphite monochromatorθmax = 25.0°, θmin = 2.4°
Detector resolution: 10.00 pixels mm-1h = 2828
Ω scansk = 2826
16963 measured reflectionsl = 1315
2627 independent 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)] = 0.053H-atom parameters constrained
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.0156P)2 + 0.731P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2627 reflectionsΔρmax = 0.26 e Å3
319 parametersΔρmin = 0.19 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00248 (10)
Crystal data top
C31H34O8Z = 9
Mr = 534.58Mo Kα radiation
Trigonal, R3µ = 0.09 mm1
a = 24.001 (3) ÅT = 298 K
c = 13.441 (3) Å0.50 × 0.45 × 0.25 mm
V = 6705.5 (19) Å3
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
1277 reflections with I > 2σ(I)
16963 measured reflectionsRint = 0.056
2627 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0531 restraint
wR(F2) = 0.089H-atom parameters constrained
S = 1.03Δρmax = 0.26 e Å3
2627 reflectionsΔρmin = 0.19 e Å3
319 parameters
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
O10.8308 (2)0.89609 (18)0.0017 (3)0.0589 (11)
O20.7086 (2)0.8907 (2)0.0209 (3)0.0832 (14)
O30.6777 (4)0.9119 (4)0.1583 (6)0.169 (3)
O40.71440 (19)0.72464 (19)0.0247 (3)0.0593 (11)
O50.8332 (2)0.7232 (2)0.0228 (3)0.0640 (12)
O60.9087 (2)0.8540 (2)0.0925 (3)0.0690 (13)
O70.86749 (18)0.88162 (18)0.1512 (3)0.0562 (11)
O80.9173 (2)0.9883 (2)0.1794 (4)0.0791 (14)
C10.7701 (3)0.8374 (3)0.0044 (4)0.0516 (16)
H1A0.75130.82820.06240.062*
C20.7752 (3)0.7796 (3)0.0409 (4)0.0506 (16)
H2A0.78510.78410.11220.061*
C30.8278 (3)0.7760 (3)0.0153 (4)0.0547 (17)
H3A0.81520.76750.08550.066*
C40.8894 (3)0.8393 (3)0.0087 (4)0.0570 (17)
H4A0.92320.83730.04700.068*
C50.8803 (3)0.8924 (3)0.0467 (5)0.0568 (17)
H5A0.92050.93320.03740.068*
C60.7279 (3)0.8491 (3)0.0724 (5)0.0680 (19)
H6A0.69020.80860.09000.082*
H6B0.75100.86970.13300.082*
C70.6824 (4)0.9177 (5)0.0706 (7)0.105 (3)
C80.6651 (5)0.9575 (4)0.0146 (7)0.128 (3)
H8A0.63910.96850.05500.192*
H8B0.64120.93450.04330.192*
H8C0.70330.99600.00550.192*
C90.6919 (3)0.6800 (3)0.1058 (5)0.077 (2)
H9A0.68830.70040.16580.092*
H9B0.72120.66400.11830.092*
C100.6280 (2)0.6269 (3)0.0754 (4)0.0682 (19)
C110.5738 (3)0.6333 (3)0.0843 (4)0.125 (3)
H11A0.57740.67060.11160.150*
C120.5143 (2)0.5841 (4)0.0526 (5)0.160 (4)
H12A0.47800.58840.05860.192*
C130.5090 (3)0.5284 (3)0.0118 (4)0.132 (4)
H13A0.46910.49550.00940.158*
C140.5631 (4)0.5220 (3)0.0028 (4)0.144 (4)
H14A0.55960.48470.02440.173*
C150.6227 (3)0.5712 (3)0.0346 (4)0.105 (3)
H15A0.65890.56690.02860.126*
C160.8486 (4)0.6916 (4)0.0499 (5)0.094 (2)
H16A0.88830.72230.08240.113*
H16B0.81490.67410.09980.113*
C170.8561 (2)0.63855 (18)0.0072 (3)0.0570 (17)
C180.8460 (2)0.6219 (2)0.0929 (3)0.0638 (17)
H18A0.83230.64310.13570.077*
C190.8564 (2)0.5736 (2)0.1290 (3)0.0689 (18)
H19A0.84970.56240.19600.083*
C200.8769 (2)0.54193 (18)0.0651 (4)0.076 (2)
H20A0.88390.50960.08930.091*
C210.8870 (2)0.5586 (2)0.0350 (4)0.081 (2)
H21A0.90070.53740.07780.097*
C220.8766 (2)0.6069 (2)0.0712 (2)0.0679 (19)
H22A0.88340.61800.13810.082*
C230.9567 (4)0.8403 (5)0.1229 (6)0.111 (3)
H23A0.99620.86630.08610.133*
H23B0.94290.79530.11200.133*
C240.9667 (4)0.8558 (4)0.2296 (4)0.097 (3)
C251.0186 (3)0.9125 (4)0.2651 (6)0.131 (3)
H25A1.04790.94260.22070.157*
C261.0267 (3)0.9240 (3)0.3668 (7)0.176 (5)
H26A1.06150.96190.39050.212*
C270.9830 (5)0.8790 (5)0.4332 (4)0.169 (5)
H27A0.98850.88670.50130.203*
C280.9311 (4)0.8223 (4)0.3978 (5)0.165 (5)
H28A0.90190.79220.44220.198*
C290.9230 (3)0.8108 (3)0.2960 (6)0.140 (4)
H29A0.88830.77290.27230.169*
C300.8914 (3)0.9350 (4)0.2107 (5)0.0642 (19)
C310.8804 (4)0.9152 (4)0.3171 (5)0.089 (2)
H31A0.91090.95000.35780.134*
H31B0.83750.90440.33580.134*
H31C0.88560.87840.32640.134*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.066 (3)0.048 (3)0.062 (3)0.027 (3)0.005 (2)0.001 (2)
O20.113 (4)0.092 (4)0.078 (3)0.076 (3)0.025 (3)0.018 (3)
O30.139 (7)0.125 (7)0.106 (5)0.086 (6)0.054 (5)0.036 (5)
O40.062 (3)0.053 (3)0.049 (3)0.019 (2)0.004 (2)0.011 (2)
O50.097 (3)0.066 (3)0.048 (3)0.055 (3)0.009 (2)0.000 (2)
O60.065 (3)0.084 (3)0.063 (3)0.041 (3)0.014 (2)0.000 (2)
O70.059 (3)0.051 (3)0.051 (2)0.021 (2)0.002 (2)0.007 (2)
O80.068 (3)0.057 (3)0.100 (4)0.022 (3)0.002 (3)0.012 (3)
C10.060 (4)0.054 (4)0.043 (3)0.030 (4)0.001 (3)0.004 (3)
C20.058 (4)0.048 (4)0.044 (4)0.025 (4)0.003 (3)0.002 (3)
C30.065 (5)0.051 (4)0.052 (4)0.031 (4)0.005 (3)0.005 (3)
C40.059 (4)0.059 (5)0.049 (4)0.027 (4)0.001 (3)0.002 (3)
C50.055 (4)0.051 (4)0.060 (5)0.024 (3)0.006 (4)0.001 (3)
C60.083 (5)0.074 (5)0.061 (4)0.049 (4)0.017 (4)0.017 (4)
C70.143 (8)0.133 (8)0.082 (7)0.101 (7)0.046 (6)0.037 (6)
C80.141 (7)0.129 (6)0.112 (7)0.116 (6)0.023 (6)0.028 (6)
C90.068 (4)0.067 (4)0.079 (5)0.021 (4)0.002 (4)0.019 (4)
C100.091 (5)0.084 (5)0.077 (4)0.026 (4)0.004 (4)0.021 (4)
C110.092 (6)0.114 (6)0.160 (8)0.044 (5)0.012 (5)0.013 (6)
C120.131 (6)0.131 (7)0.170 (7)0.069 (5)0.021 (5)0.033 (6)
C130.119 (7)0.115 (7)0.080 (6)0.003 (5)0.027 (5)0.022 (5)
C140.141 (9)0.102 (7)0.102 (6)0.026 (6)0.024 (7)0.002 (5)
C150.120 (6)0.076 (5)0.097 (6)0.031 (5)0.028 (5)0.011 (5)
C160.094 (7)0.080 (5)0.062 (5)0.056 (5)0.010 (4)0.011 (4)
C170.065 (4)0.054 (4)0.055 (4)0.032 (4)0.010 (3)0.005 (3)
C180.086 (5)0.063 (4)0.061 (5)0.051 (4)0.004 (4)0.001 (4)
C190.078 (5)0.066 (5)0.070 (4)0.041 (4)0.002 (4)0.005 (4)
C200.084 (5)0.071 (5)0.088 (6)0.051 (4)0.004 (4)0.006 (5)
C210.091 (6)0.096 (6)0.063 (5)0.053 (5)0.007 (4)0.014 (4)
C220.082 (5)0.075 (5)0.062 (4)0.050 (4)0.012 (4)0.003 (4)
C230.080 (6)0.132 (7)0.084 (5)0.064 (5)0.015 (5)0.007 (5)
C240.092 (6)0.133 (7)0.085 (6)0.041 (5)0.030 (5)0.008 (6)
C250.106 (8)0.131 (9)0.162 (11)0.063 (8)0.026 (7)0.002 (8)
C260.135 (9)0.153 (9)0.160 (9)0.073 (7)0.036 (8)0.032 (8)
C270.151 (15)0.162 (13)0.105 (8)0.061 (12)0.044 (10)0.058 (10)
C280.189 (9)0.157 (8)0.101 (8)0.072 (7)0.027 (7)0.021 (6)
C290.199 (11)0.153 (10)0.066 (6)0.084 (9)0.044 (7)0.007 (6)
C300.047 (4)0.066 (5)0.078 (5)0.028 (4)0.008 (4)0.015 (4)
C310.110 (6)0.104 (6)0.057 (5)0.055 (5)0.019 (4)0.023 (4)
Geometric parameters (Å, º) top
O1—C51.396 (7)C12—H12A0.9300
O1—C11.434 (7)C13—C141.3900
O2—C71.291 (9)C13—H13A0.9300
O2—C61.469 (7)C14—C151.3900
O3—C71.186 (9)C14—H14A0.9300
O4—C21.411 (6)C15—H15A0.9300
O4—C91.431 (7)C16—C171.487 (7)
O5—C161.395 (7)C16—H16A0.9700
O5—C31.433 (7)C16—H16B0.9700
O6—C231.409 (8)C17—C181.3900
O6—C41.423 (6)C17—C221.3900
O7—C301.369 (7)C18—C191.3900
O7—C51.433 (6)C18—H18A0.9300
O8—C301.186 (7)C19—C201.3900
C1—C61.490 (8)C19—H19A0.9300
C1—C21.534 (7)C20—C211.3900
C1—H1A0.9800C20—H20A0.9300
C2—C31.509 (8)C21—C221.3900
C2—H2A0.9800C21—H21A0.9300
C3—C41.501 (8)C22—H22A0.9300
C3—H3A0.9800C23—C241.472 (9)
C4—C51.488 (8)C23—H23A0.9700
C4—H4A0.9800C23—H23B0.9700
C5—H5A0.9800C24—C251.3900
C6—H6A0.9700C24—C291.3900
C6—H6B0.9700C25—C261.3900
C7—C81.430 (11)C25—H25A0.9300
C8—H8A0.9600C26—C271.3900
C8—H8B0.9600C26—H26A0.9300
C8—H8C0.9600C27—C281.3900
C9—C101.479 (7)C27—H27A0.9300
C9—H9A0.9700C28—C291.3900
C9—H9B0.9700C28—H28A0.9300
C10—C111.3900C29—H29A0.9300
C10—C151.3900C30—C311.490 (9)
C11—C121.3900C31—H31A0.9600
C11—H11A0.9300C31—H31B0.9600
C12—C131.3900C31—H31C0.9600
C5—O1—C1115.4 (4)C12—C13—C14120.0
C7—O2—C6119.7 (6)C12—C13—H13A120.0
C2—O4—C9114.1 (5)C14—C13—H13A120.0
C16—O5—C3113.4 (4)C15—C14—C13120.0
C23—O6—C4114.9 (5)C15—C14—H14A120.0
C30—O7—C5116.9 (5)C13—C14—H14A120.0
O1—C1—C6106.5 (5)C14—C15—C10120.0
O1—C1—C2113.3 (5)C14—C15—H15A120.0
C6—C1—C2110.1 (5)C10—C15—H15A120.0
O1—C1—H1A109.0O5—C16—C17111.9 (5)
C6—C1—H1A109.0O5—C16—H16A109.2
C2—C1—H1A109.0C17—C16—H16A109.2
O4—C2—C3111.9 (5)O5—C16—H16B109.2
O4—C2—C1106.4 (5)C17—C16—H16B109.2
C3—C2—C1109.8 (5)H16A—C16—H16B107.9
O4—C2—H2A109.6C18—C17—C22120.0
C3—C2—H2A109.6C18—C17—C16122.7 (4)
C1—C2—H2A109.6C22—C17—C16117.2 (4)
O5—C3—C4113.1 (5)C19—C18—C17120.0
O5—C3—C2108.6 (5)C19—C18—H18A120.0
C4—C3—C2110.1 (5)C17—C18—H18A120.0
O5—C3—H3A108.3C18—C19—C20120.0
C4—C3—H3A108.3C18—C19—H19A120.0
C2—C3—H3A108.3C20—C19—H19A120.0
O6—C4—C5106.5 (5)C21—C20—C19120.0
O6—C4—C3109.9 (5)C21—C20—H20A120.0
C5—C4—C3110.6 (5)C19—C20—H20A120.0
O6—C4—H4A109.9C20—C21—C22120.0
C5—C4—H4A109.9C20—C21—H21A120.0
C3—C4—H4A109.9C22—C21—H21A120.0
O1—C5—O7110.8 (5)C21—C22—C17120.0
O1—C5—C4112.9 (5)C21—C22—H22A120.0
O7—C5—C4107.0 (5)C17—C22—H22A120.0
O1—C5—H5A108.7O6—C23—C24105.8 (6)
O7—C5—H5A108.7O6—C23—H23A110.6
C4—C5—H5A108.7C24—C23—H23A110.6
O2—C6—C1108.3 (5)O6—C23—H23B110.6
O2—C6—H6A110.0C24—C23—H23B110.6
C1—C6—H6A110.0H23A—C23—H23B108.7
O2—C6—H6B110.0C25—C24—C29120.0
C1—C6—H6B110.0C25—C24—C23122.3 (7)
H6A—C6—H6B108.4C29—C24—C23117.7 (7)
O3—C7—O2119.9 (8)C26—C25—C24120.0
O3—C7—C8123.9 (9)C26—C25—H25A120.0
O2—C7—C8116.0 (8)C24—C25—H25A120.0
C7—C8—H8A109.5C25—C26—C27120.0
C7—C8—H8B109.5C25—C26—H26A120.0
H8A—C8—H8B109.5C27—C26—H26A120.0
C7—C8—H8C109.5C28—C27—C26120.0
H8A—C8—H8C109.5C28—C27—H27A120.0
H8B—C8—H8C109.5C26—C27—H27A120.0
O4—C9—C10106.0 (5)C27—C28—C29120.0
O4—C9—H9A110.5C27—C28—H28A120.0
C10—C9—H9A110.5C29—C28—H28A120.0
O4—C9—H9B110.5C28—C29—C24120.0
C10—C9—H9B110.5C28—C29—H29A120.0
H9A—C9—H9B108.7C24—C29—H29A120.0
C11—C10—C15120.0O8—C30—O7123.5 (7)
C11—C10—C9120.3 (6)O8—C30—C31126.8 (7)
C15—C10—C9119.7 (6)O7—C30—C31109.8 (6)
C10—C11—C12120.0C30—C31—H31A109.5
C10—C11—H11A120.0C30—C31—H31B109.5
C12—C11—H11A120.0H31A—C31—H31B109.5
C13—C12—C11120.0C30—C31—H31C109.5
C13—C12—H12A120.0H31A—C31—H31C109.5
C11—C12—H12A120.0H31B—C31—H31C109.5
C5—O1—C1—C6171.0 (5)O4—C9—C10—C1180.9 (6)
C5—O1—C1—C249.9 (6)O4—C9—C10—C1597.0 (5)
C9—O4—C2—C3103.7 (6)C15—C10—C11—C120.0
C9—O4—C2—C1136.4 (5)C9—C10—C11—C12177.9 (5)
O1—C1—C2—O4171.0 (5)C10—C11—C12—C130.0
C6—C1—C2—O469.9 (6)C11—C12—C13—C140.0
O1—C1—C2—C349.7 (6)C12—C13—C14—C150.0
C6—C1—C2—C3168.7 (5)C13—C14—C15—C100.0
C16—O5—C3—C492.8 (7)C11—C10—C15—C140.0
C16—O5—C3—C2144.7 (6)C9—C10—C15—C14177.9 (5)
O4—C2—C3—O564.3 (6)C3—O5—C16—C17178.0 (5)
C1—C2—C3—O5177.8 (5)O5—C16—C17—C182.6 (8)
O4—C2—C3—C4171.3 (5)O5—C16—C17—C22174.8 (4)
C1—C2—C3—C453.4 (6)C22—C17—C18—C190.0
C23—O6—C4—C5140.2 (6)C16—C17—C18—C19177.4 (5)
C23—O6—C4—C399.9 (7)C17—C18—C19—C200.0
O5—C3—C4—O661.1 (7)C18—C19—C20—C210.0
C2—C3—C4—O660.6 (6)C19—C20—C21—C220.0
O5—C3—C4—C5178.4 (5)C20—C21—C22—C170.0
C2—C3—C4—C556.7 (7)C18—C17—C22—C210.0
C1—O1—C5—O767.4 (6)C16—C17—C22—C21177.5 (5)
C1—O1—C5—C452.6 (7)C4—O6—C23—C24177.2 (6)
C30—O7—C5—O191.6 (6)O6—C23—C24—C25101.6 (7)
C30—O7—C5—C4144.9 (5)O6—C23—C24—C2980.1 (7)
O6—C4—C5—O163.7 (6)C29—C24—C25—C260.0
C3—C4—C5—O155.7 (7)C23—C24—C25—C26178.3 (6)
O6—C4—C5—O7174.1 (4)C24—C25—C26—C270.0
C3—C4—C5—O766.5 (6)C25—C26—C27—C280.0
C7—O2—C6—C1166.6 (7)C26—C27—C28—C290.0
O1—C1—C6—O273.5 (6)C27—C28—C29—C240.0
C2—C1—C6—O2163.3 (5)C25—C24—C29—C280.0
C6—O2—C7—O34.6 (14)C23—C24—C29—C28178.4 (6)
C6—O2—C7—C8180.0 (7)C5—O7—C30—O85.9 (9)
C2—O4—C9—C10179.4 (5)C5—O7—C30—C31173.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23A···O1i0.972.533.496 (9)175
Symmetry code: (i) y+2, xy+1, z.

Experimental details

Crystal data
Chemical formulaC31H34O8
Mr534.58
Crystal system, space groupTrigonal, R3
Temperature (K)298
a, c (Å)24.001 (3), 13.441 (3)
V3)6705.5 (19)
Z9
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.50 × 0.45 × 0.25
Data collection
DiffractometerRigaku R-AXIS RAPID IP
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
16963, 2627, 1277
Rint0.056
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.089, 1.03
No. of reflections2627
No. of parameters319
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.19

Computer programs: DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23A···O1i0.972.533.496 (9)175
Symmetry code: (i) y+2, xy+1, z.
 

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