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In the crystal structure of the title compound, C24H26O9, mol­ecules are linked by O—H...O hydrogen bonds, creating a chain of hydrogen-bonded mol­ecules in the c-axis direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015255/wn2133sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015255/wn2133Isup2.hkl
Contains datablock I

CCDC reference: 647465

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.090
  • Data-to-parameter ratio = 9.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.65 Ratio
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.67 Ratio PLAT413_ALERT_2_C Short Inter XH3 .. XHn H3 .. H62F .. 2.12 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 27.48 From the CIF: _reflns_number_total 2879 Count of symmetry unique reflns 2885 Completeness (_total/calc) 99.79% 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 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 6 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 1 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: SMART (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Benzyl 4,6-diacetyl-2-O-benzoyl-β-D-glucopyranoside top
Crystal data top
C24H26O9F(000) = 968
Mr = 458.45Dx = 1.379 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7859 reflections
a = 9.5277 (5) Åθ = 2.7–27.5°
b = 9.8517 (5) ŵ = 0.11 mm1
c = 23.5217 (14) ÅT = 100 K
V = 2207.8 (2) Å3Prism, colourless
Z = 40.5 × 0.45 × 0.42 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2827 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
thin–slice ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 1212
Tmin = 0.948, Tmax = 0.956k = 1212
30372 measured reflectionsl = 3030
2879 independent reflections
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.09H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0382P)2 + 1.2139P]
where P = (Fo2 + 2Fc2)/3
2879 reflections(Δ/σ)max = 0.001
301 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.21 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*/UeqOcc. (<1)
C40.7957 (2)0.2633 (2)0.99278 (8)0.0129 (4)
H40.69910.2281.00050.015*
O40.87049 (16)0.28282 (15)1.04573 (6)0.0163 (3)
C410.8007 (2)0.2598 (2)1.09486 (9)0.0191 (4)
O410.68594 (18)0.2105 (2)1.09702 (7)0.0330 (5)
C420.8853 (3)0.3041 (3)1.14536 (10)0.0272 (5)
H42A0.97520.34151.13240.041*0.5
H42B0.90260.2261.17020.041*0.5
H42C0.83350.37381.16640.041*0.5
H42D0.83230.2861.18030.041*0.5
H42E0.9050.40151.14250.041*0.5
H42F0.9740.25371.14630.041*0.5
O30.69548 (17)0.48513 (15)0.99555 (6)0.0165 (3)
H3A0.710 (4)0.561 (4)0.9849 (15)0.05*
C30.7875 (2)0.40150 (19)0.96380 (8)0.0127 (4)
H30.8830.44360.96330.015*
C20.7377 (2)0.38022 (19)0.90306 (8)0.0136 (4)
H20.6430.33670.90250.016*
O20.73421 (15)0.51040 (15)0.87487 (6)0.0145 (3)
C210.6063 (2)0.5589 (2)0.86008 (9)0.0156 (4)
O210.49732 (17)0.50245 (19)0.87059 (9)0.0298 (4)
C220.6171 (2)0.6910 (2)0.83013 (8)0.0148 (4)
C230.7429 (2)0.7621 (3)0.82747 (11)0.0267 (5)
H230.82640.72390.84270.032*
C240.7453 (3)0.8894 (3)0.80229 (16)0.0462 (9)
H240.83040.93960.80110.055*
C250.6241 (3)0.9441 (3)0.77887 (13)0.0387 (7)
H250.6271.03110.76150.046*
C260.5003 (3)0.8732 (3)0.78070 (10)0.0242 (5)
H260.41810.910.76390.029*
C270.4956 (2)0.7475 (2)0.80724 (9)0.0186 (4)
H270.40920.69980.80980.022*
C10.8450 (2)0.2912 (2)0.87336 (8)0.0141 (4)
H10.94140.32990.87780.017*
O10.81173 (15)0.27710 (16)0.81637 (6)0.0165 (3)
C110.9279 (2)0.2247 (2)0.78396 (9)0.0196 (4)
H11A0.94270.12770.79310.024*
H11B1.01460.2750.79370.024*
C120.8963 (2)0.2404 (2)0.72180 (8)0.0161 (4)
C170.8786 (2)0.3697 (2)0.69894 (9)0.0190 (4)
H170.88210.44670.72320.023*
C160.8561 (3)0.3873 (3)0.64133 (10)0.0251 (5)
H160.8460.4760.6260.03*
C150.8483 (3)0.2748 (3)0.60606 (10)0.0290 (6)
H150.83240.28660.56650.035*
C140.8634 (3)0.1450 (3)0.62814 (10)0.0263 (5)
H140.85690.06820.60390.032*
C130.8883 (2)0.1280 (2)0.68597 (9)0.0194 (4)
H130.89990.03930.70110.023*
O50.83694 (16)0.16039 (14)0.89928 (6)0.0158 (3)
C50.8794 (2)0.15944 (19)0.95777 (8)0.0130 (4)
H50.98160.18190.96020.016*
C60.8567 (2)0.0151 (2)0.97819 (9)0.0152 (4)
H6A0.91140.04930.95470.018*
H6B0.88690.00571.01830.018*
C610.6675 (2)0.1403 (2)0.96603 (8)0.0138 (4)
C620.5124 (2)0.1518 (2)0.95902 (10)0.0211 (5)
H62A0.47050.06090.95940.032*0.5
H62B0.47350.20560.99030.032*0.5
H62C0.49130.19630.92280.032*0.5
H62D0.48640.24760.95560.032*0.5
H62E0.48340.10290.92470.032*0.5
H62F0.46560.11220.99220.032*0.5
O60.70826 (15)0.01182 (15)0.97288 (7)0.0179 (3)
O610.74823 (17)0.23569 (15)0.96684 (7)0.0202 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C40.0144 (9)0.0115 (9)0.0127 (9)0.0022 (8)0.0012 (7)0.0005 (7)
O40.0192 (7)0.0157 (7)0.0141 (7)0.0013 (6)0.0027 (6)0.0000 (6)
C410.0234 (10)0.0188 (10)0.0152 (9)0.0106 (9)0.0003 (8)0.0011 (8)
O410.0197 (8)0.0572 (13)0.0221 (8)0.0000 (9)0.0037 (7)0.0107 (9)
C420.0352 (13)0.0274 (12)0.0190 (10)0.0121 (11)0.0046 (10)0.0039 (9)
O30.0215 (7)0.0096 (6)0.0184 (7)0.0017 (6)0.0047 (6)0.0021 (6)
C30.0138 (9)0.0109 (9)0.0135 (9)0.0004 (7)0.0032 (8)0.0012 (7)
C20.0145 (9)0.0099 (9)0.0164 (9)0.0010 (8)0.0006 (8)0.0021 (7)
O20.0147 (7)0.0110 (7)0.0178 (6)0.0016 (6)0.0006 (6)0.0033 (6)
C210.0156 (9)0.0129 (9)0.0182 (9)0.0023 (8)0.0022 (8)0.0027 (8)
O210.0169 (8)0.0194 (8)0.0532 (11)0.0021 (7)0.0056 (8)0.0103 (9)
C220.0175 (10)0.0160 (9)0.0110 (8)0.0040 (8)0.0015 (8)0.0011 (7)
C230.0170 (10)0.0293 (12)0.0339 (12)0.0036 (10)0.0015 (9)0.0169 (11)
C240.0192 (12)0.0427 (17)0.077 (2)0.0042 (12)0.0041 (14)0.0379 (16)
C250.0273 (13)0.0359 (14)0.0528 (17)0.0075 (12)0.0063 (12)0.0320 (13)
C260.0228 (12)0.0289 (12)0.0208 (11)0.0109 (10)0.0014 (9)0.0064 (10)
C270.0176 (10)0.0200 (11)0.0184 (10)0.0021 (9)0.0013 (8)0.0036 (9)
C10.0145 (9)0.0137 (9)0.0142 (9)0.0001 (8)0.0002 (8)0.0002 (7)
O10.0159 (7)0.0194 (7)0.0141 (7)0.0031 (6)0.0012 (6)0.0026 (6)
C110.0185 (10)0.0228 (11)0.0175 (10)0.0069 (9)0.0013 (8)0.0010 (9)
C120.0142 (9)0.0192 (10)0.0148 (9)0.0002 (9)0.0019 (8)0.0004 (8)
C170.0146 (10)0.0193 (10)0.0230 (11)0.0004 (9)0.0023 (8)0.0007 (9)
C160.0262 (12)0.0237 (11)0.0254 (11)0.0052 (10)0.0045 (10)0.0090 (9)
C150.0313 (13)0.0419 (14)0.0138 (10)0.0079 (12)0.0010 (9)0.0024 (10)
C140.0283 (12)0.0301 (13)0.0204 (11)0.0012 (11)0.0008 (10)0.0083 (10)
C130.0211 (11)0.0161 (10)0.0211 (10)0.0008 (9)0.0034 (9)0.0011 (8)
O50.0220 (8)0.0105 (7)0.0149 (7)0.0012 (6)0.0017 (6)0.0014 (5)
C50.0142 (9)0.0103 (8)0.0145 (9)0.0008 (8)0.0006 (8)0.0011 (7)
C60.0119 (9)0.0114 (9)0.0221 (10)0.0012 (8)0.0005 (8)0.0013 (8)
C610.0189 (10)0.0134 (9)0.0091 (8)0.0013 (8)0.0036 (7)0.0004 (7)
C620.0184 (10)0.0179 (10)0.0270 (11)0.0025 (9)0.0022 (9)0.0068 (9)
O60.0143 (7)0.0110 (7)0.0283 (8)0.0004 (6)0.0014 (6)0.0005 (6)
O610.0223 (7)0.0113 (7)0.0270 (8)0.0009 (6)0.0009 (7)0.0016 (6)
Geometric parameters (Å, º) top
C4—O41.448 (2)C1—O11.384 (2)
C4—C31.525 (3)C1—O51.427 (2)
C4—C51.536 (3)C1—H11
C4—H41O1—C111.440 (2)
O4—C411.352 (3)C11—C121.501 (3)
C41—O411.197 (3)C11—H11A0.99
C41—C421.500 (3)C11—H11B0.99
C42—H42A0.98C12—C131.393 (3)
C42—H42B0.98C12—C171.393 (3)
C42—H42C0.98C17—C161.383 (3)
C42—H42D0.98C17—H170.95
C42—H42E0.98C16—C151.387 (4)
C42—H42F0.98C16—H160.95
O3—C31.416 (2)C15—C141.387 (4)
O3—H3A0.80 (4)C15—H150.95
C3—C21.520 (3)C14—C131.391 (3)
C3—H31C14—H140.95
C2—O21.444 (2)C13—H130.95
C2—C11.517 (3)O5—C51.434 (2)
C2—H21C5—C61.516 (3)
O2—C211.354 (3)C5—H51
C21—O211.204 (3)C6—O61.445 (2)
C21—C221.484 (3)C6—H6A0.99
C22—C231.390 (3)C6—H6B0.99
C22—C271.393 (3)C61—O611.214 (3)
C23—C241.388 (4)C61—O61.333 (3)
C23—H230.95C61—C621.491 (3)
C24—C251.388 (4)C62—H62A0.98
C24—H240.95C62—H62B0.98
C25—C261.371 (4)C62—H62C0.98
C25—H250.95C62—H62D0.98
C26—C271.388 (3)C62—H62E0.98
C26—H260.95C62—H62F0.98
C27—H270.95
O4—C4—C3106.91 (16)O5—C1—C2106.80 (16)
O4—C4—C5107.12 (15)O1—C1—H1110.5
C3—C4—C5112.43 (16)O5—C1—H1110.5
O4—C4—H4110.1C2—C1—H1110.5
C3—C4—H4110.1C1—O1—C11111.87 (16)
C5—C4—H4110.1O1—C11—C12108.93 (17)
C41—O4—C4118.09 (16)O1—C11—H11A109.9
O41—C41—O4123.6 (2)C12—C11—H11A109.9
O41—C41—C42125.1 (2)O1—C11—H11B109.9
O4—C41—C42111.3 (2)C12—C11—H11B109.9
C41—C42—H42A109.5H11A—C11—H11B108.3
C41—C42—H42B109.5C13—C12—C17119.12 (19)
H42A—C42—H42B109.5C13—C12—C11121.2 (2)
C41—C42—H42C109.5C17—C12—C11119.63 (19)
H42A—C42—H42C109.5C16—C17—C12120.8 (2)
H42B—C42—H42C109.5C16—C17—H17119.6
C41—C42—H42D109.5C12—C17—H17119.6
H42A—C42—H42D141.1C17—C16—C15119.6 (2)
H42B—C42—H42D56.3C17—C16—H16120.2
H42C—C42—H42D56.3C15—C16—H16120.2
C41—C42—H42E109.5C14—C15—C16120.5 (2)
H42A—C42—H42E56.3C14—C15—H15119.8
H42B—C42—H42E141.1C16—C15—H15119.8
H42C—C42—H42E56.3C15—C14—C13119.7 (2)
H42D—C42—H42E109.5C15—C14—H14120.2
C41—C42—H42F109.5C13—C14—H14120.2
H42A—C42—H42F56.3C14—C13—C12120.3 (2)
H42B—C42—H42F56.3C14—C13—H13119.8
H42C—C42—H42F141.1C12—C13—H13119.8
H42D—C42—H42F109.5C1—O5—C5113.61 (15)
H42E—C42—H42F109.5O5—C5—C6105.65 (16)
C3—O3—H3A106 (3)O5—C5—C4111.30 (16)
O3—C3—C2112.51 (17)C6—C5—C4112.35 (16)
O3—C3—C4108.40 (15)O5—C5—H5109.1
C2—C3—C4108.24 (15)C6—C5—H5109.1
O3—C3—H3109.2C4—C5—H5109.1
C2—C3—H3109.2O6—C6—C5106.55 (16)
C4—C3—H3109.2O6—C6—H6A110.4
O2—C2—C1108.54 (16)C5—C6—H6A110.4
O2—C2—C3108.44 (15)O6—C6—H6B110.4
C1—C2—C3107.60 (16)C5—C6—H6B110.4
O2—C2—H2110.7H6A—C6—H6B108.6
C1—C2—H2110.7O61—C61—O6123.26 (19)
C3—C2—H2110.7O61—C61—C62124.8 (2)
C21—O2—C2116.88 (16)O6—C61—C62111.94 (18)
O21—C21—O2124.12 (19)C61—C62—H62A109.5
O21—C21—C22124.2 (2)C61—C62—H62B109.5
O2—C21—C22111.67 (18)H62A—C62—H62B109.5
C23—C22—C27119.88 (19)C61—C62—H62C109.5
C23—C22—C21121.53 (19)H62A—C62—H62C109.5
C27—C22—C21118.5 (2)H62B—C62—H62C109.5
C24—C23—C22119.2 (2)C61—C62—H62D109.5
C24—C23—H23120.4H62A—C62—H62D141.1
C22—C23—H23120.4H62B—C62—H62D56.3
C25—C24—C23120.5 (3)H62C—C62—H62D56.3
C25—C24—H24119.8C61—C62—H62E109.5
C23—C24—H24119.8H62A—C62—H62E56.3
C26—C25—C24120.3 (2)H62B—C62—H62E141.1
C26—C25—H25119.8H62C—C62—H62E56.3
C24—C25—H25119.8H62D—C62—H62E109.5
C25—C26—C27119.8 (2)C61—C62—H62F109.5
C25—C26—H26120.1H62A—C62—H62F56.3
C27—C26—H26120.1H62B—C62—H62F56.3
C26—C27—C22120.2 (2)H62C—C62—H62F141.1
C26—C27—H27119.9H62D—C62—H62F109.5
C22—C27—H27119.9H62E—C62—H62F109.5
O1—C1—O5108.11 (16)C61—O6—C6118.02 (16)
O1—C1—C2110.45 (16)
C3—C4—O4—C41115.95 (19)C3—C2—C1—O1175.06 (16)
C5—C4—O4—C41123.32 (19)O2—C2—C1—O5175.24 (15)
C4—O4—C41—O418.3 (3)C3—C2—C1—O567.61 (19)
C4—O4—C41—C42171.60 (18)O5—C1—O1—C1178.8 (2)
O4—C4—C3—O369.48 (19)C2—C1—O1—C11164.72 (17)
C5—C4—C3—O3173.25 (16)C1—O1—C11—C12167.83 (18)
O4—C4—C3—C2168.22 (16)O1—C11—C12—C13119.2 (2)
C5—C4—C3—C250.9 (2)O1—C11—C12—C1762.7 (3)
O3—C3—C2—O262.1 (2)C13—C12—C17—C161.2 (3)
C4—C3—C2—O2178.15 (15)C11—C12—C17—C16176.9 (2)
O3—C3—C2—C1179.32 (16)C12—C17—C16—C151.3 (4)
C4—C3—C2—C160.9 (2)C17—C16—C15—C140.3 (4)
C1—C2—O2—C21130.39 (18)C16—C15—C14—C130.7 (4)
C3—C2—O2—C21113.00 (19)C15—C14—C13—C120.8 (4)
C2—O2—C21—O212.4 (3)C17—C12—C13—C140.2 (3)
C2—O2—C21—C22178.41 (15)C11—C12—C13—C14177.9 (2)
O21—C21—C22—C23169.1 (2)O1—C1—O5—C5175.61 (15)
O2—C21—C22—C2310.0 (3)C2—C1—O5—C565.5 (2)
O21—C21—C22—C277.1 (3)C1—O5—C5—C6177.24 (16)
O2—C21—C22—C27173.77 (19)C1—O5—C5—C455.0 (2)
C27—C22—C23—C240.5 (4)O4—C4—C5—O5164.12 (15)
C21—C22—C23—C24175.7 (3)C3—C4—C5—O547.0 (2)
C22—C23—C24—C251.4 (5)O4—C4—C5—C677.6 (2)
C23—C24—C25—C260.5 (5)C3—C4—C5—C6165.22 (17)
C24—C25—C26—C271.4 (5)O5—C5—C6—O661.88 (19)
C25—C26—C27—C222.4 (3)C4—C5—C6—O659.7 (2)
C23—C22—C27—C261.4 (3)O61—C61—O6—C63.7 (3)
C21—C22—C27—C26177.67 (19)C62—C61—O6—C6177.87 (18)
O2—C2—C1—O157.9 (2)C5—C6—O6—C61153.82 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O61i0.80 (4)2.08 (4)2.876 (3)174 (4)
Symmetry code: (i) x, y+1, z.
 

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