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The X-ray crystal structure of the title compound, C25H28O8, has been determined. In the structure, both the terminal five-membered rings (A and F) are planar. The fused five-membered rings C and E are in envelope conformations, and ring B is in a slightly distorted half-chair conformation. The six-membered ring D is in a slightly distorted sofa conformation. The structure is stabilized by O—H...O hydrogen bonds and C—H...O inter- and intramolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801000733/cf6030sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801000733/cf6030Isup2.hkl
Contains datablock I

CCDC reference: 159722

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.033
  • wR factor = 0.092
  • Data-to-parameter ratio = 8.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 69.93 From the CIF: _reflns_number_total 2417 Count of symmetry unique reflns 2488 Completeness (_total/calc) 97.15% 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 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.

Comment top

The molecular structure of tricoccin R6, (I), is shown in Fig. 1. The bond geometry conforms to expectations. The puckering parameters evaluated using PARST97 (Nardelli, 1995) show that (i) both the terminal five-membered rings (A and F) are planar, (ii) the fused five-membered ring B is in a slightly distorted half-chair conformation, and rings C and E are in envelope conformations [q2 = 0.334 (2) Å, ϕ2 = -119.7 (4)° for ring B, q2 = 0.440 (2) Å, ϕ2 = -134.7 (3)° for ring C, and q2 = 0.129 (2) Å, ϕ2 = 151.2 (11)° for ring E]. The six-membered ring D has a slightly distorted sofa conformation [q2 = 0.369 (3), q3 = 0.364 (3), QT = 0.519 (2) Å, ϕ2 = 63.0 (4)°]. Fig. 2 shows the packing diagram of the molecules. The structure is stabilized by intermolecular O—H···O hydrogen bonds and C—H—O inter- and intramolecular interactions (see Table 1).

Experimental top

The title compound was isolated from Cneorum tricoccin L., a shrub native to coastal areas of the western Mediterranean with hairless leaves, yellow blossoms and red fruits (Herz et al., 1983). It was crystallized from ethanol/acetone.

Refinement top

The data set contains no Friedel pairs.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SDP (Frenz, 1978); data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1998); software used to prepare material for publication: SHELXL97 and PARST97 (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed along the b axis.
(I) top
Crystal data top
C25H28O8Dx = 1.325 Mg m3
Mr = 456.47Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 7.224 (2) Åθ = 20–30°
b = 15.521 (2) ŵ = 0.82 mm1
c = 20.404 (1) ÅT = 293 K
V = 2287.8 (7) Å3Needle, colourless
Z = 40.25 × 0.25 × 0.20 mm
F(000) = 968
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 69.9°, θmin = 3.6°
Graphite monochromatorh = 08
ω/2θ scansk = 018
2417 measured reflectionsl = 024
2417 independent reflections3 standard reflections every 120 min
2171 reflections with I > 2σ(I) intensity decay: <1%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033 w = 1/[σ2(Fo2) + (0.0539P)2 + 0.3026P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.092(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.19 e Å3
2417 reflectionsΔρmin = 0.17 e Å3
303 parametersExtinction correction: SHELXL07, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0078 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.2 (2)
Crystal data top
C25H28O8V = 2287.8 (7) Å3
Mr = 456.47Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 7.224 (2) ŵ = 0.82 mm1
b = 15.521 (2) ÅT = 293 K
c = 20.404 (1) Å0.25 × 0.25 × 0.20 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.000
2417 measured reflections3 standard reflections every 120 min
2417 independent reflections intensity decay: <1%
2171 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.092Δρmax = 0.19 e Å3
S = 1.04Δρmin = 0.17 e Å3
2417 reflectionsAbsolute structure: Flack (1983)
303 parametersAbsolute structure parameter: 0.2 (2)
0 restraints
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
C10.0011 (4)0.44829 (18)0.91298 (12)0.0514 (6)
H10.08840.41470.93470.062*
C20.0661 (5)0.43112 (18)0.85488 (13)0.0582 (7)
H20.03170.38490.82860.070*
C30.2029 (5)0.49599 (17)0.83820 (12)0.0576 (7)
C40.3046 (4)0.58439 (16)1.03575 (12)0.0522 (6)
C50.1881 (4)0.51129 (15)1.00390 (10)0.0421 (5)
H50.09540.49421.03640.051*
C60.3230 (4)0.43608 (14)0.99777 (11)0.0427 (5)
H6A0.25930.38131.00190.051*
H6B0.38790.43770.95620.051*
C70.4547 (4)0.45026 (14)1.05433 (11)0.0408 (5)
C80.6596 (3)0.34735 (13)1.10470 (10)0.0355 (5)
C90.5305 (3)0.39130 (15)1.15372 (10)0.0396 (5)
H90.59050.44321.17100.047*
C100.0822 (4)0.52963 (15)0.93978 (11)0.0445 (5)
C110.4825 (4)0.33158 (17)1.20975 (11)0.0469 (6)
H11A0.42790.27901.19280.056*
H11B0.39310.35901.23840.056*
C120.6596 (4)0.31011 (19)1.24852 (11)0.0518 (6)
H12A0.68000.35551.28040.062*
H12B0.63840.25721.27270.062*
C130.8365 (3)0.29927 (14)1.20829 (10)0.0372 (5)
C140.8410 (3)0.32540 (13)1.13677 (10)0.0357 (5)
C150.9635 (4)0.26286 (16)1.10388 (11)0.0441 (5)
O161.0349 (3)0.20671 (11)1.14794 (8)0.0543 (5)
C170.9415 (4)0.21545 (14)1.21156 (10)0.0417 (5)
H170.85130.16861.21550.050*
C180.9432 (4)0.37711 (14)1.18752 (10)0.0406 (5)
H18A1.07720.37341.18790.049*
H18B0.89350.43311.19910.049*
C190.0644 (5)0.6001 (2)0.94640 (15)0.0669 (8)
H19A0.00580.65330.95840.100*
H19B0.15190.58410.97960.100*
H19C0.12740.60720.90530.100*
C201.0822 (3)0.20472 (14)1.26463 (11)0.0414 (5)
C211.1910 (5)0.13015 (17)1.27584 (14)0.0588 (7)
H211.19090.07981.25110.071*
C221.1283 (4)0.26077 (17)1.31191 (12)0.0503 (6)
H221.07860.31581.31630.060*
C231.2935 (5)0.14616 (19)1.32873 (16)0.0681 (8)
H231.37810.10791.34690.082*
O241.2571 (3)0.22641 (13)1.35249 (9)0.0662 (6)
O251.0044 (3)0.25932 (14)1.04679 (8)0.0633 (6)
O260.5807 (3)0.26671 (11)1.08654 (7)0.0492 (4)
H260.55990.26651.04700.074*
O270.3774 (2)0.41558 (11)1.11359 (8)0.0493 (4)
C280.3810 (6)0.65439 (18)0.99111 (18)0.0801 (11)
H28A0.47120.68771.01450.120*
H28B0.28180.69120.97710.120*
H28C0.43800.62840.95350.120*
C290.2061 (6)0.6227 (3)1.09453 (17)0.0929 (13)
H29A0.18450.57841.12650.139*
H29B0.09000.64681.08090.139*
H29C0.28160.66711.11350.139*
C300.6516 (3)0.41203 (15)1.04874 (11)0.0422 (5)
H30A0.66930.38381.00680.051*
H30B0.74500.45641.05400.051*
O310.4710 (3)0.54090 (10)1.05931 (8)0.0506 (4)
O320.2099 (3)0.55420 (10)0.88795 (8)0.0519 (5)
O330.3017 (4)0.50316 (15)0.79069 (10)0.0880 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0454 (14)0.0577 (15)0.0513 (13)0.0012 (12)0.0097 (12)0.0012 (11)
C20.0699 (18)0.0536 (14)0.0509 (14)0.0031 (15)0.0113 (15)0.0073 (12)
C30.085 (2)0.0476 (13)0.0404 (12)0.0124 (15)0.0016 (14)0.0050 (10)
C40.0616 (15)0.0431 (12)0.0518 (13)0.0092 (13)0.0173 (13)0.0084 (11)
C50.0481 (13)0.0423 (12)0.0359 (10)0.0025 (11)0.0040 (11)0.0025 (9)
C60.0530 (14)0.0347 (10)0.0405 (11)0.0000 (11)0.0110 (11)0.0019 (9)
C70.0464 (13)0.0373 (11)0.0387 (11)0.0018 (10)0.0062 (11)0.0041 (9)
C80.0409 (12)0.0371 (10)0.0285 (9)0.0033 (10)0.0042 (9)0.0004 (8)
C90.0400 (12)0.0466 (12)0.0321 (10)0.0032 (10)0.0028 (10)0.0032 (9)
C100.0500 (14)0.0450 (12)0.0386 (11)0.0064 (12)0.0053 (11)0.0028 (9)
C110.0436 (13)0.0609 (15)0.0361 (11)0.0058 (12)0.0078 (10)0.0085 (11)
C120.0503 (14)0.0744 (16)0.0306 (10)0.0073 (14)0.0034 (11)0.0076 (11)
C130.0433 (12)0.0420 (11)0.0263 (9)0.0028 (10)0.0035 (9)0.0001 (8)
C140.0420 (12)0.0392 (10)0.0260 (9)0.0022 (10)0.0003 (9)0.0009 (8)
C150.0516 (14)0.0482 (12)0.0325 (10)0.0086 (12)0.0049 (11)0.0062 (10)
O160.0690 (12)0.0543 (10)0.0397 (8)0.0241 (10)0.0051 (9)0.0084 (7)
C170.0511 (13)0.0381 (11)0.0359 (11)0.0004 (11)0.0052 (11)0.0008 (9)
C180.0433 (12)0.0394 (11)0.0389 (11)0.0012 (11)0.0057 (10)0.0048 (9)
C190.0720 (19)0.0659 (17)0.0626 (16)0.0297 (17)0.0152 (16)0.0024 (14)
C200.0440 (12)0.0425 (11)0.0378 (11)0.0012 (11)0.0032 (11)0.0081 (9)
C210.0704 (18)0.0452 (13)0.0610 (16)0.0073 (14)0.0120 (16)0.0076 (11)
C220.0542 (15)0.0527 (13)0.0441 (12)0.0013 (13)0.0103 (12)0.0048 (10)
C230.070 (2)0.0601 (16)0.0739 (19)0.0127 (17)0.0188 (18)0.0142 (15)
O240.0727 (13)0.0695 (12)0.0564 (10)0.0022 (11)0.0275 (11)0.0063 (10)
O250.0757 (13)0.0805 (13)0.0338 (8)0.0208 (12)0.0058 (9)0.0108 (8)
O260.0654 (11)0.0465 (9)0.0357 (8)0.0133 (9)0.0100 (8)0.0013 (7)
O270.0399 (8)0.0663 (10)0.0418 (8)0.0062 (9)0.0021 (7)0.0143 (8)
C280.097 (3)0.0426 (14)0.101 (2)0.0143 (17)0.037 (2)0.0130 (15)
C290.087 (2)0.107 (3)0.086 (2)0.030 (2)0.024 (2)0.054 (2)
C300.0431 (12)0.0481 (12)0.0353 (10)0.0009 (11)0.0013 (10)0.0075 (10)
O310.0581 (11)0.0396 (8)0.0541 (9)0.0007 (8)0.0170 (9)0.0033 (7)
O320.0704 (12)0.0416 (8)0.0438 (8)0.0012 (9)0.0013 (9)0.0082 (7)
O330.131 (2)0.0753 (13)0.0579 (12)0.0085 (16)0.0324 (15)0.0096 (10)
Geometric parameters (Å, º) top
C1—C21.309 (4)C12—H12B0.970
C1—C101.501 (4)C13—C181.494 (3)
C1—H10.930C13—C171.507 (3)
C2—C31.452 (4)C13—C141.515 (3)
C2—H20.930C14—C151.475 (3)
C3—O331.209 (3)C14—C181.504 (3)
C3—O321.360 (3)C15—O251.203 (3)
C4—O311.460 (3)C15—O161.354 (3)
C4—C291.516 (4)O16—C171.469 (3)
C4—C281.521 (4)C17—C201.494 (3)
C4—C51.555 (3)C17—H170.980
C5—C61.526 (3)C18—H18A0.970
C5—C101.542 (3)C18—H18B0.970
C5—H50.980C19—H19A0.960
C6—C71.512 (3)C19—H19B0.960
C6—H6A0.970C19—H19C0.960
C6—H6B0.970C20—C221.341 (3)
C7—O311.415 (3)C20—C211.418 (3)
C7—O271.437 (3)C21—C231.332 (4)
C7—C301.546 (4)C21—H210.930
C8—O261.424 (3)C22—O241.355 (3)
C8—C141.504 (3)C22—H220.930
C8—C301.521 (3)C23—O241.362 (4)
C8—C91.528 (3)C23—H230.930
C9—O271.427 (3)O26—H260.820
C9—C111.512 (3)C28—H28A0.960
C9—H90.980C28—H28B0.960
C10—O321.455 (3)C28—H28C0.960
C10—C191.528 (4)C29—H29A0.960
C11—C121.541 (4)C29—H29B0.960
C11—H11A0.970C29—H29C0.960
C11—H11B0.970C30—H30A0.970
C12—C131.528 (3)C30—H30B0.970
C12—H12A0.970
C2—C1—C10110.6 (3)C18—C13—C12119.6 (2)
C2—C1—H1124.7C17—C13—C12119.5 (2)
C10—C1—H1124.7C14—C13—C12120.4 (2)
C1—C2—C3108.9 (2)C15—C14—C18111.7 (2)
C1—C2—H2125.6C15—C14—C8118.29 (18)
C3—C2—H2125.6C18—C14—C8127.33 (19)
O33—C3—O32121.0 (3)C15—C14—C13105.96 (18)
O33—C3—C2130.8 (3)C18—C14—C1359.34 (14)
O32—C3—C2108.1 (2)C8—C14—C13117.5 (2)
O31—C4—C29107.9 (2)O25—C15—O16121.3 (2)
O31—C4—C28103.2 (3)O25—C15—C14128.2 (2)
C29—C4—C28111.3 (3)O16—C15—C14110.48 (18)
O31—C4—C5104.23 (18)C15—O16—C17110.62 (17)
C29—C4—C5111.3 (3)O16—C17—C20108.5 (2)
C28—C4—C5117.9 (2)O16—C17—C13105.76 (17)
C6—C5—C10112.87 (18)C20—C17—C13118.06 (19)
C6—C5—C4104.30 (19)O16—C17—H17108.0
C10—C5—C4119.2 (2)C20—C17—H17108.0
C6—C5—H5106.6C13—C17—H17108.0
C10—C5—H5106.6C13—C18—C1460.70 (14)
C4—C5—H5106.6C13—C18—H18A117.7
C7—C6—C5103.17 (18)C14—C18—H18A117.7
C7—C6—H6A111.1C13—C18—H18B117.7
C5—C6—H6A111.1C14—C18—H18B117.7
C7—C6—H6B111.1H18A—C18—H18B114.8
C5—C6—H6B111.1C10—C19—H19A109.5
H6A—C6—H6B109.1C10—C19—H19B109.5
O31—C7—O27110.14 (19)H19A—C19—H19B109.5
O31—C7—C6104.60 (18)C10—C19—H19C109.5
O27—C7—C6110.07 (19)H19A—C19—H19C109.5
O31—C7—C30108.1 (2)H19B—C19—H19C109.5
O27—C7—C30106.03 (17)C22—C20—C21106.0 (2)
C6—C7—C30117.8 (2)C22—C20—C17128.2 (2)
O26—C8—C14105.23 (17)C21—C20—C17125.8 (2)
O26—C8—C30111.68 (17)C23—C21—C20106.7 (3)
C14—C8—C30120.60 (19)C23—C21—H21126.7
O26—C8—C9108.57 (19)C20—C21—H21126.7
C14—C8—C9110.38 (16)C20—C22—O24110.8 (2)
C30—C8—C9100.00 (17)C20—C22—H22124.6
O27—C9—C11114.72 (19)O24—C22—H22124.6
O27—C9—C8102.44 (16)C21—C23—O24110.6 (3)
C11—C9—C8111.17 (19)C21—C23—H23124.7
O27—C9—H9109.4O24—C23—H23124.7
C11—C9—H9109.4C22—O24—C23106.0 (2)
C8—C9—H9109.4C8—O26—H26109.5
O32—C10—C1102.12 (18)C9—O27—C7106.29 (17)
O32—C10—C19108.4 (2)C4—C28—H28A109.5
C1—C10—C19110.9 (2)C4—C28—H28B109.5
O32—C10—C5110.5 (2)H28A—C28—H28B109.5
C1—C10—C5110.65 (19)C4—C28—H28C109.5
C19—C10—C5113.6 (2)H28A—C28—H28C109.5
C9—C11—C12109.3 (2)H28B—C28—H28C109.5
C9—C11—H11A109.8C4—C29—H29A109.5
C12—C11—H11A109.8C4—C29—H29B109.5
C9—C11—H11B109.8H29A—C29—H29B109.5
C12—C11—H11B109.8C4—C29—H29C109.5
H11A—C11—H11B108.3H29A—C29—H29C109.5
C13—C12—C11116.26 (17)H29B—C29—H29C109.5
C13—C12—H12A108.2C8—C30—C7103.46 (19)
C11—C12—H12A108.2C8—C30—H30A111.1
C13—C12—H12B108.2C7—C30—H30A111.1
C11—C12—H12B108.2C8—C30—H30B111.1
H12A—C12—H12B107.4C7—C30—H30B111.1
C18—C13—C17116.8 (2)H30A—C30—H30B109.0
C18—C13—C1459.95 (14)C7—O31—C4111.55 (19)
C17—C13—C14105.25 (18)C3—O32—C10110.2 (2)
C10—C1—C2—C32.0 (3)C8—C14—C15—O2545.0 (4)
C1—C2—C3—O33177.4 (3)C13—C14—C15—O25179.3 (3)
C1—C2—C3—O322.0 (3)C18—C14—C15—O1660.4 (3)
O31—C4—C5—C613.5 (2)C8—C14—C15—O16136.7 (2)
C29—C4—C5—C6129.6 (2)C13—C14—C15—O162.4 (3)
C28—C4—C5—C6100.1 (3)O25—C15—O16—C17170.9 (3)
O31—C4—C5—C10140.6 (2)C14—C15—O16—C1710.7 (3)
C29—C4—C5—C10103.4 (3)C15—O16—C17—C20142.1 (2)
C28—C4—C5—C1026.9 (4)C15—O16—C17—C1314.5 (3)
C10—C5—C6—C7160.3 (2)C18—C13—C17—O1651.5 (2)
C4—C5—C6—C729.4 (2)C14—C13—C17—O1612.2 (2)
C5—C6—C7—O3135.1 (2)C12—C13—C17—O16151.3 (2)
C5—C6—C7—O2783.2 (2)C18—C13—C17—C2070.2 (3)
C5—C6—C7—C30155.1 (2)C14—C13—C17—C20133.8 (2)
O26—C8—C9—O2771.4 (2)C12—C13—C17—C2087.0 (3)
C14—C8—C9—O27173.78 (17)C17—C13—C18—C1492.8 (2)
C30—C8—C9—O2745.7 (2)C12—C13—C18—C14110.1 (2)
O26—C8—C9—C1151.6 (2)C15—C14—C18—C1396.2 (2)
C14—C8—C9—C1163.2 (2)C8—C14—C18—C13102.8 (2)
C30—C8—C9—C11168.69 (19)O16—C17—C20—C22121.1 (3)
C2—C1—C10—O321.2 (3)C13—C17—C20—C220.9 (4)
C2—C1—C10—C19114.1 (3)O16—C17—C20—C2160.9 (3)
C2—C1—C10—C5118.8 (3)C13—C17—C20—C21178.8 (2)
C6—C5—C10—O3262.4 (3)C22—C20—C21—C230.3 (3)
C4—C5—C10—O3260.5 (3)C17—C20—C21—C23178.1 (3)
C6—C5—C10—C150.0 (3)C21—C20—C22—O240.6 (3)
C4—C5—C10—C1172.9 (2)C17—C20—C22—O24177.6 (2)
C6—C5—C10—C19175.5 (2)C20—C21—C23—O240.2 (4)
C4—C5—C10—C1961.6 (3)C20—C22—O24—C230.7 (3)
O27—C9—C11—C12179.6 (2)C21—C23—O24—C220.5 (4)
C8—C9—C11—C1263.9 (3)C11—C9—O27—C7163.94 (19)
C9—C11—C12—C1336.9 (3)C8—C9—O27—C743.4 (2)
C11—C12—C13—C1881.8 (3)O31—C7—O27—C993.8 (2)
C11—C12—C13—C17121.6 (2)C6—C7—O27—C9151.35 (19)
C11—C12—C13—C1411.3 (4)C30—C7—O27—C922.9 (2)
O26—C8—C14—C1546.8 (2)O26—C8—C30—C783.8 (2)
C30—C8—C14—C1580.4 (3)C14—C8—C30—C7151.90 (19)
C9—C8—C14—C15163.8 (2)C9—C8—C30—C730.9 (2)
O26—C8—C14—C18153.3 (2)O31—C7—C30—C8124.71 (19)
C30—C8—C14—C1879.4 (3)O27—C7—C30—C86.6 (2)
C9—C8—C14—C1836.3 (3)C6—C7—C30—C8117.1 (2)
O26—C8—C14—C1382.3 (2)O27—C7—O31—C490.2 (2)
C30—C8—C14—C13150.39 (19)C6—C7—O31—C428.0 (3)
C9—C8—C14—C1334.6 (3)C30—C7—O31—C4154.34 (19)
C18—C13—C14—C15106.1 (2)C29—C4—O31—C7109.4 (3)
C17—C13—C14—C156.3 (3)C28—C4—O31—C7132.6 (2)
C12—C13—C14—C15145.0 (2)C5—C4—O31—C78.9 (3)
C17—C13—C14—C18112.5 (2)O33—C3—O32—C10178.3 (3)
C12—C13—C14—C18108.8 (2)C2—C3—O32—C101.2 (3)
C18—C13—C14—C8119.1 (2)C1—C10—O32—C30.1 (3)
C17—C13—C14—C8128.4 (2)C19—C10—O32—C3117.2 (2)
C12—C13—C14—C810.3 (3)C5—C10—O32—C3117.7 (2)
C18—C14—C15—O25117.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C28—H28C···O320.962.412.894 (4)111
O26—H26···O25i0.822.002.805 (2)169
C23—H23···O31ii0.932.433.283 (3)152
Symmetry codes: (i) x1/2, y+1/2, z+2; (ii) x+2, y1/2, z+5/2.

Experimental details

Crystal data
Chemical formulaC25H28O8
Mr456.47
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)7.224 (2), 15.521 (2), 20.404 (1)
V3)2287.8 (7)
Z4
Radiation typeCu Kα
µ (mm1)0.82
Crystal size (mm)0.25 × 0.25 × 0.20
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2417, 2417, 2171
Rint0.000
(sin θ/λ)max1)0.609
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.092, 1.04
No. of reflections2417
No. of parameters303
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.17
Absolute structureFlack (1983)
Absolute structure parameter0.2 (2)

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), SDP (Frenz, 1978), CAD-4 Software, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Johnson & Burnett, 1998), SHELXL97 and PARST97 (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C28—H28C···O320.962.412.894 (4)110.5
O26—H26···O25i0.822.002.805 (2)168.6
C23—H23···O31ii0.932.433.283 (3)151.7
Symmetry codes: (i) x1/2, y+1/2, z+2; (ii) x+2, y1/2, z+5/2.
 

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