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The title compound, di­methyl (−)-(2aR,3R,4R,4aS,5R,7aS,8R,10S,10aR)-3,8,10-tri­hydroxy-4-[(2R,6R)-2-hydroxy-11-methyl-5,7,10-trioxatetra­cyclo­[6.3.1.02,609,11]­dodec-3-en-9-yl]-4-methyl­per­hydro­isobenzo­furano­[5,4,3a-cd]­isobenzofuran-5,10a-di­acetate, C28H36O13, which exhibits higher antifeedant activity than azadirachtin-A, a known potent antifeedant, was isolated from neem kernels. The asymmetric unit of the structure contains two independent mol­ecules, which differ in the conformations of their functional groups and also in the conformations of some of the rings. The relative orientation between the decalin and furan­yl moieties is similar to that observed in the majority of azadirachtin structures, but is different from that in azadirachtin-A. The two symmetry-independent mol­ecules are linked into dimeric units by intermolecular O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102019091/ln1147sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102019091/ln1147Isup2.hkl
Contains datablock I

CCDC reference: 201276

Comment top

At present, due to the harmful effects of synthetic insecticides on humans and the environment, ecofriendly bio-insecticides from Azadirachta indica, widely known as neem, are preferred in pest control. Chemical investigations of different parts of the neem tree have yielded many interesting and structurally varied secondary metabolites which are potent antifeedant and ecdysis inhibitors, and their structures have been studied with a view to understanding the structure-activity relationships. We report here the isolation from neem kernels and the crystal structure of an azadirachtin, azadirachtol, (I), a minor tetranortriterpenoid, which shows higher antifeedant activity than Azadirachtin-A, a known potent antifeedant (Suresh et al., 2002). This is the first report of the isolation of this compound from neem kernels, although an earlier report described the synthesis of this compound through the chemical modification of Azadirachtin-B (Ley et al., 1989). \sch

There are two independent molecules in the asymmetric unit of (I) and their packing within the crystal is stabilized by intra- and intermolecular hydrogen bonds. In both molecules, A and B, intramolecular hydrogen bonds are observed between O1···O3 and O7···O6. In molecule B, there is another intramolecular hydrogen bond observed between O20B···O7B. The two molecules in the asymmetric unit exist as dimers connected via parallel hydrogen bonds between O7A···O6B and O7B···O6A, which generate a graph-set motif (Berstein et al., 1995) of R22(10) (Fig. 1). The dimeric unit is linked into infinite chains along all three axes (Fig. 2).

Atom O3A acts as a hydrogen-bond donor via H3A to O12A at (1 - x, y - 1/2, 3/2 - z), so producing a C(10) chain parallel to [010] generated by the 21 screw axis along (1,y,3/4). Atom O1A acts as a donor via H1A to O13B at (3/2 - x, 1 - y, z - 1/2). Finally, atom O1B acts as a donor via H1B to O20B at (x + 1/2, 1/2 - y, 2 - z), producing a C(11) chain parallel to [100] generated by (x,1/4,1) by a 21 screw axis. The combination of these chains generates a ring with the R55(26) motif. The interior of this ring is occupied by the –COOMe groups at C11 of the molecule at (x - 1/2, 3/2 - y, z) and C4 of the molecule at (x, y, z) (Fig 3). All the hydroxy O atoms, except O20A, take part in the formation of hydrogen bonds. This may be due to steric hinderance in the crystalline state. Other azadirachtins extracted from the same source show different hydrogen-bonding graph-set motifs.

Among the azadirachtins studied earlier, it was reported that Azadirachtin-A possesses maximum antifeedant activity and Azadirachtins-I and H have medium activities (60–80% of azadirachtin-A; Govindachari, Narasimhan et al., 1996). Compound (I) has higher antifeedant activity than Azadirachtin-A (Suresh et al., 2002). The overall conformation of the molecule of (I) defined by the dihedral angle about the C8—C14 bond, viz. C9—C8—C14—O13, shows that the values in the present structure [26.5 (7) and 26.2 (7)° for molecules A and B, respectively] are closer to those for Azadirachtin-H [25.6 (3)°; Govindachari, Geetha Gopalakrishnan et al., 1996] and Azadirachtin-I [23.5 (8)°; Malathi et al., 2002] than that of Azadirachtin-A [-162.1 (6)°; Kabaleeswaran et al., 1994], which indicates that this may not be a factor contributing to the activity of the compound.

The two molecules in the asymmetric unit of (I) differ from each other in the orientations of their functional groups. The C3—C4—C29—O26 dihedral angle, defining the orientation of the carbomethoxy group at C4, is -179.4 (5)° in molecule A and -162.8 (7)° in molecule B. These are closer to the corresponding value observed in Azadirachtin-H [C3—C4—C29—O26 176.8 (3)°], but differ from that observed in Azadirachtin-A [8.0 (11)°]. Another difference observed in the two molecules is in the conformation of the carbomethoxy group at C11 defined by the C9—C11—C12—O27 dihedral angle, which is 128.2 (7)° in molecule A and 170.9 (6)° in molecule B. The corresponding value in Azadirachtin-A (Kabaleeswaran et al., 1994) is 28.4 (11)°. These variations in the orientations of functional groups within chemically equivalent but crystallographically nonequivalent molecules suggest a high flexibility of the functional groups in azadirachtins.

The ring-puckering amplitudes (Cremer & Pople, 1975; values are given in the order molecule A and molecule B) show that rings A [QT = 0.556 (7) and 0.573 (6) Å, θ = 4.6 (6) and 3.2 (7)°, and ϕ2 = -135 (8) and 114 (13)°], B [QT = 0.538 (6) and 0.526 (6) Å, θ = 19.8 (7) and 16.1 (6)°, and ϕ2 = 78 (2) and 70 (2)°] and B' [QT = 0.662 (8) and 0.706 (7) Å, θ = 129.4 (6) and 118.0 (5)°, and ϕ2 = -115.2 (9) and -117.8 (6)°] are in chair, distorted chair and sofa conformations, respectively, in both independent molecules of (I). Rings A' [q2 = 0.446 (8) and 0.450 (7) Å, and ϕ2 = 110.8 (9) and 113.3 (8)°] and C' are in envelope and planar conformations, respectively, in both molecules. The envelope is puckered (Nardelli, 1995) at C16 in both molecules. However, ring F adopts a distorted envelope conformation in molecule A [q2 = 0.390 (6) Å and ϕ2 = 26.3 (9)°], with the apex at C5, and a half-chair conformation in molecule B [q2 = 0.392 (6) Å and ϕ2 = 21.8 (9)°], with atoms C4 and C5 deviating from the least-squares plane defined by atoms C6, O6 and C28 by 0.257 (7) and -0.382 (6) Å, respectively. Similarly, ring G of molecule B is in a half-chair conformation [q2 = 0.349 (6) Å and ϕ2 = 165 (1)°], with atoms C9B and C10B deviating from the least-squares plane defined by atoms C11B, C19B and O19B by -0.235 (6) and 0.346 (6) Å, respectively, while in molecule A, the ring conformation lies between that of an envelope and a half-chair [q2 = 0.342 (6) Å and ϕ2 = 154 (1)°]. The ring-pair fusion configurations are similar to those observed for other azadirachtins (Kabaleeswaran et al., 1994; Govindachari, Geetha Gopalakrishnan et al., 1996; Malathi et al., 2002).

Experimental top

Powdered neem kernels (500 g) were defatted with hexane (1.5 l) and extracted twice with 95% methanol (1 l and 500 ml) at reflux temperature. On removing the solvent under reduced pressure, a brown residue (25 g) was obtained. This enriched azadirachtin fraction was subjected to preparative high-performance liquid chromatography (HPLC) on a Shimpack RP-18 (25 × 5 cm) ODS Please define column, using methanol-water (60:40) as eluent at a flow rate of 20 ml min-1 and a UV detector (215 nm) for preliminary separation of azadirachtins. The peak with a retention time of 20.4 min (1.2 g) was subjected to reseparation using a semipreparative HPLC column [endcapped, Merck, 10 mm, acetonitrile-water (25:75), 2 ml min-1, UV detector (215 nm)]. On solvent evaporation, this separation yielded an unknown compound (13 mg), which was identified to be Azadirachtol, based on one- and two-dimensional NMR data. Compound (I) was crystallized by the hanging-drop vapour-diffusion technique. A stock solution of 1 mg of (I) in 100 µl of methanol was prepared. A single-crystal of size 3 × 1 × 0.15 mm was obtained from a drop containing 10 µl of this solution saturated with 30% methanol-water.

Refinement top

In the absence of suitable anomalous scatters, Friedel equivalents could not be used to determine the absolute structure. Refinement of the Flack parameter (Flack, 1983) led to an inconclusive value (Flack & Bernadinelli, 2000) of -0.3 (4). Therefore, the 434 Friedel equivalents were merged before the final refinement. The enantiomer employed in the refined model was chosen to agree with the accepted configuration of limonoids (Ley et al., 1989). The methyl and hydroxy H atoms were constrained to an ideal geometry (C—H 0.96 Å and O—H 0.82 Å) with Uiso(H) = 1.5Ueq(C, O), but were allowed to rotate freely about the C—C and C—O bonds, respectively. All remaining H atoms were placed in geometrically idealized positions (C—H distances in the range 0.97–0.98 Å) and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C). The atomic coordinates and displacement parameters of the two molecules were refined individually, blocking each molecule in alternate cycles.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. A view of the two independent molecules of (I), with 30% probability displacement ellipsoids and the atomic numbering scheme. Hydrogen bonds are shown as dotted lines; H atoms not involved in these contacts have been omitted for clarity.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the repeat units of the R55(26) rings. For the sake of clarity, H atoms bonded to C atoms have been omitted.
[Figure 3] Fig. 3. A view of the supramolecular structure of (I), showing the R55(26) ring. The molecules labelled with an asterisk (*), dollar sign (add) or hash sign (#) are at the symmetry positions (x, y, z), (x - 1/2, 3/2 - y, z) and (1 - x, y - 1/2, 3/2 - z), respectively.
Dimethyl (-)-(2aR,3R,4R,4aS,5R,7aS,8R,10S,10aR)- 3,8,10-trihydroxy-4-[(2R,6R)-2-hydroxy-11-methyl- 5,7,10-trioxatetracyclo[6.3.1.02,609,11]dodeca-3-en-9-yl]- 4-methylperhydroisobenzofurano[5,4,3a-cd]isobenzofuran-5,10a-diacetate top
Crystal data top
C28H36O13F(000) = 2464
Mr = 580.57Dx = 1.467 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 14.142 (6) Åθ = 15–30°
b = 17.287 (3) ŵ = 0.99 mm1
c = 21.505 (4) ÅT = 293 K
V = 5257 (3) Å3Rod-shaped, colourless
Z = 80.35 × 0.23 × 0.15 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.035
Radiation source: fine-focus sealed tubeθmax = 72.1°, θmin = 4.0°
Graphite monochromatorh = 117
non–profiled ω/2θ scansk = 1521
6108 measured reflectionsl = 2626
5699 independent reflections3 standard reflections every 200 reflections
3087 reflections with I > 2σ(I) intensity decay: 7%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: full with fixed elements per cycleHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.173Calculated w = 1/[σ2(Fo2) + (0.0808P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
5699 reflectionsΔρmax = 0.26 e Å3
748 parametersΔρmin = 0.31 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: 0.00108 (13)
Crystal data top
C28H36O13V = 5257 (3) Å3
Mr = 580.57Z = 8
Orthorhombic, P212121Cu Kα radiation
a = 14.142 (6) ŵ = 0.99 mm1
b = 17.287 (3) ÅT = 293 K
c = 21.505 (4) Å0.35 × 0.23 × 0.15 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.035
6108 measured reflections3 standard reflections every 200 reflections
5699 independent reflections intensity decay: 7%
3087 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.173H-atom parameters constrained
S = 1.04Δρmax = 0.26 e Å3
5699 reflectionsΔρmin = 0.31 e Å3
748 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
O1A0.4522 (4)0.6231 (3)0.7363 (2)0.0454 (12)
H1A0.45590.59180.70780.068*
O3A0.5019 (4)0.4569 (3)0.7267 (2)0.0523 (14)
H3A0.52140.41480.71480.079*
O6A0.6379 (3)0.4569 (2)0.8871 (2)0.0429 (12)
O7A0.6997 (3)0.6008 (3)0.83504 (19)0.0386 (11)
H7A0.73650.56410.83310.058*
O12A0.4065 (4)0.8134 (3)0.7984 (3)0.0698 (18)
O13A0.6026 (4)0.8127 (3)0.8651 (2)0.0545 (15)
O15A0.8008 (4)0.7127 (3)0.9407 (2)0.0610 (16)
O19A0.3547 (4)0.6761 (3)0.9171 (2)0.0528 (14)
O20A0.8631 (4)0.7257 (3)0.7792 (2)0.0605 (15)
H20A0.81280.70330.77320.091*
O21A0.9586 (4)0.7128 (4)0.9167 (3)0.085 (2)
O27A0.2715 (4)0.7625 (3)0.8348 (3)0.0605 (15)
O26A0.4517 (4)0.4209 (3)0.9454 (2)0.0525 (14)
O29A0.3343 (4)0.3971 (3)0.8793 (3)0.0661 (16)
C1A0.3951 (5)0.5922 (4)0.7844 (3)0.0398 (17)
H1A10.33870.62490.78720.048*
C2A0.3608 (5)0.5095 (4)0.7700 (3)0.0400 (17)
H2A10.30920.49750.79810.048*
H2A20.33550.50890.72810.048*
C3A0.4340 (5)0.4458 (4)0.7752 (3)0.0446 (18)
H3A10.40310.39560.76970.053*
C4A0.4832 (5)0.4482 (3)0.8393 (3)0.0339 (15)
C5A0.5177 (5)0.5314 (3)0.8483 (3)0.0331 (15)
H5A0.55540.54140.81090.040*
C6A0.5884 (5)0.5292 (3)0.8983 (3)0.0349 (16)
H6A0.55730.52810.93900.042*
C7A0.6530 (5)0.6000 (3)0.8932 (3)0.0396 (17)
H7A10.70020.59820.92650.048*
C8A0.5893 (5)0.6721 (4)0.9024 (3)0.0361 (16)
C9A0.4986 (5)0.6736 (3)0.8587 (3)0.0335 (16)
H9A0.51760.69360.81790.040*
C10A0.4461 (5)0.5969 (3)0.8488 (3)0.0306 (14)
C11A0.4183 (5)0.7251 (4)0.8837 (3)0.0419 (18)
H11A0.44570.76200.91310.050*
C12A0.3667 (6)0.7708 (4)0.8334 (3)0.0435 (18)
C13A0.6797 (5)0.7787 (4)0.8295 (3)0.0396 (17)
C14A0.6517 (5)0.7448 (3)0.8893 (3)0.0377 (17)
C15A0.7274 (6)0.7715 (5)0.9358 (3)0.056 (2)
H15A0.69900.78140.97660.067*
C16A0.7657 (6)0.8456 (4)0.9082 (4)0.064 (2)
H16A0.82700.85900.92540.076*
H16B0.72240.88850.91390.076*
C17A0.7728 (6)0.8216 (4)0.8405 (3)0.050 (2)
H17A0.78000.86610.81270.060*
C18A0.6557 (6)0.7530 (4)0.7640 (3)0.048 (2)
H18A0.59080.76500.75520.072*
H18B0.66550.69830.76030.072*
H18C0.69580.77960.73490.072*
C19A0.3727 (5)0.5967 (4)0.9010 (3)0.0420 (18)
H19A0.31480.57190.88710.050*
H19B0.39650.56860.93680.050*
C20A0.8592 (5)0.7660 (4)0.8373 (3)0.0430 (18)
C21A0.8646 (6)0.7065 (4)0.8914 (3)0.049 (2)
H21A0.85790.65470.87350.059*
C22A0.9530 (6)0.8074 (5)0.8461 (4)0.059 (2)
H22A0.97310.85010.82340.071*
C23A0.9996 (7)0.7748 (6)0.8891 (4)0.076 (3)
H23A1.05900.79250.90100.091*
C27A0.2181 (6)0.8102 (5)0.7912 (4)0.067 (3)
H27A0.15180.80040.79630.100*
H27B0.23670.79770.74940.100*
H27C0.23090.86380.79920.100*
C26A0.3936 (6)0.3950 (5)0.9962 (4)0.063 (2)
H26A0.42890.39801.03420.094*
H26B0.37460.34250.98900.094*
H26C0.33860.42730.99920.094*
C28A0.5813 (5)0.4068 (4)0.8480 (3)0.0446 (18)
H28A0.57290.35670.86760.054*
H28B0.61190.39930.80800.054*
C29A0.4158 (6)0.4202 (4)0.8882 (4)0.0433 (18)
C30A0.5603 (5)0.6758 (4)0.9713 (3)0.0458 (18)
H30A0.61460.66630.99700.069*
H30B0.51310.63720.97940.069*
H30C0.53510.72600.98040.069*
O1B1.0209 (4)0.2768 (3)0.9476 (3)0.0523 (13)
H1B1.04720.23590.95610.078*
O3B0.9598 (4)0.2896 (3)0.8261 (2)0.0645 (16)
H3B0.96140.27030.86090.097*
O6B0.8503 (3)0.4988 (3)0.85952 (19)0.0416 (12)
O7B0.7905 (3)0.4196 (2)0.96943 (18)0.0346 (11)
H7B0.77490.41360.93300.052*
O12B1.1005 (5)0.2921 (4)1.0817 (3)0.088 (2)
O13B0.9145 (3)0.4080 (3)1.13423 (19)0.0435 (12)
O15B0.7285 (3)0.5378 (2)1.0818 (2)0.0442 (12)
O19B1.1600 (3)0.4699 (3)1.0224 (2)0.0515 (13)
O20B0.6447 (4)0.3530 (3)1.0537 (2)0.0488 (13)
H20B0.69270.35471.03240.073*
O21B0.5707 (4)0.5284 (3)1.1089 (3)0.0716 (18)
O27B1.2152 (4)0.3710 (5)1.1117 (3)0.109 (3)
O26B1.0517 (5)0.5565 (4)0.8337 (3)0.082 (2)
O29B1.1167 (5)0.4748 (4)0.7682 (3)0.097 (2)
C1B1.0908 (5)0.3348 (4)0.9344 (3)0.0399 (17)
H1B11.14760.32460.95910.048*
C2B1.1155 (5)0.3312 (4)0.8654 (3)0.0466 (19)
H2B11.14050.28020.85630.056*
H2B21.16520.36840.85710.056*
C3B1.0320 (6)0.3475 (5)0.8211 (3)0.052 (2)
H3B11.05590.34750.77830.063*
C4B0.9932 (5)0.4290 (4)0.8360 (3)0.0397 (17)
C5B0.9716 (5)0.4306 (4)0.9047 (3)0.0334 (15)
H5B0.92930.38620.91010.040*
C6B0.9078 (5)0.4982 (4)0.9153 (3)0.0320 (15)
H6B0.94500.54590.91790.038*
C7B0.8514 (5)0.4867 (4)0.9747 (3)0.0310 (15)
H7B10.81210.53260.98180.037*
C8B0.9225 (5)0.4780 (4)1.0300 (3)0.0301 (14)
C9B1.0037 (4)0.4169 (4)1.0183 (3)0.0326 (15)
H9B0.97840.36531.02710.039*
C10B1.0495 (5)0.4154 (3)0.9525 (3)0.0310 (15)
C11B1.0913 (5)0.4297 (4)1.0595 (3)0.0431 (18)
H11B1.07350.46281.09460.052*
C12B1.1332 (6)0.3551 (6)1.0849 (4)0.055 (2)
C13B0.8289 (5)0.3763 (4)1.1061 (3)0.0354 (16)
C14B0.8666 (5)0.4538 (3)1.0881 (3)0.0318 (15)
C15B0.8030 (6)0.5124 (4)1.1224 (3)0.0438 (18)
H15B0.84040.55661.13690.053*
C16B0.7638 (6)0.4676 (4)1.1771 (3)0.048 (2)
H16C0.70750.49191.19400.057*
H16D0.81040.46141.20980.057*
C17B0.7411 (5)0.3909 (4)1.1453 (3)0.0462 (19)
H17B0.72990.34931.17540.055*
C18B0.8430 (6)0.2982 (4)1.0763 (3)0.049 (2)
H18D0.80880.25981.09940.074*
H18E0.90910.28551.07640.074*
H18F0.82020.29951.03430.074*
C19B1.1308 (5)0.4730 (4)0.9589 (3)0.0432 (18)
H19C1.18270.45890.93160.052*
H19D1.10990.52480.94820.052*
C20B0.6526 (5)0.4070 (4)1.1043 (3)0.0387 (17)
C21B0.6492 (6)0.4900 (4)1.0779 (3)0.0437 (18)
H21B0.63260.48571.03380.052*
C22B0.5635 (5)0.4042 (5)1.1423 (3)0.049 (2)
H22B0.54050.36091.16300.059*
C23B0.5230 (6)0.4733 (5)1.1417 (4)0.063 (2)
H23B0.46630.48341.16210.075*
C26B1.1074 (7)0.6190 (6)0.8071 (5)0.107 (4)
H26D1.09370.66630.82880.161*
H26E1.09180.62480.76390.161*
H26F1.17340.60720.81120.161*
C27B1.2635 (8)0.3047 (8)1.1404 (6)0.151 (6)
H27D1.32170.32171.15880.226*
H27E1.27650.26651.10920.226*
H27F1.22370.28271.17190.226*
C29B1.0622 (6)0.4874 (5)0.8105 (3)0.053 (2)
C28B0.8938 (5)0.4505 (5)0.8126 (3)0.052 (2)
H28C0.89810.47820.77340.063*
H28D0.85650.40410.80610.063*
C30B0.9617 (5)0.5602 (4)1.0414 (3)0.0402 (17)
H30D0.99700.57671.00570.060*
H30E1.00230.55961.07720.060*
H30F0.91020.59521.04850.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.058 (3)0.042 (3)0.035 (3)0.007 (3)0.000 (3)0.000 (2)
O3A0.056 (3)0.045 (3)0.056 (3)0.004 (3)0.013 (3)0.010 (3)
O6A0.027 (3)0.030 (2)0.071 (3)0.005 (2)0.007 (3)0.001 (2)
O7A0.042 (3)0.035 (3)0.038 (3)0.001 (2)0.000 (2)0.001 (2)
O12A0.056 (4)0.058 (4)0.095 (4)0.002 (3)0.001 (3)0.037 (3)
O13A0.062 (4)0.029 (2)0.072 (4)0.005 (3)0.011 (3)0.003 (2)
O15A0.068 (4)0.073 (4)0.041 (3)0.024 (3)0.008 (3)0.013 (3)
O19A0.069 (4)0.035 (3)0.055 (3)0.019 (3)0.030 (3)0.004 (2)
O20A0.063 (4)0.073 (4)0.046 (3)0.006 (3)0.013 (3)0.023 (3)
O21A0.056 (4)0.122 (6)0.077 (4)0.037 (4)0.022 (3)0.046 (4)
O27A0.041 (3)0.061 (4)0.079 (4)0.005 (3)0.006 (3)0.026 (3)
O26A0.044 (3)0.056 (3)0.057 (3)0.008 (3)0.001 (3)0.014 (3)
O29A0.046 (3)0.081 (4)0.070 (4)0.026 (3)0.001 (3)0.011 (3)
C1A0.055 (5)0.027 (3)0.038 (4)0.011 (3)0.001 (4)0.006 (3)
C2A0.039 (4)0.036 (4)0.045 (4)0.004 (4)0.003 (4)0.002 (3)
C3A0.049 (5)0.028 (3)0.057 (4)0.002 (4)0.003 (4)0.010 (3)
C4A0.033 (4)0.021 (3)0.047 (4)0.002 (3)0.003 (3)0.004 (3)
C5A0.036 (4)0.024 (3)0.039 (3)0.003 (3)0.001 (3)0.002 (3)
C6A0.035 (4)0.024 (3)0.046 (4)0.004 (3)0.006 (3)0.004 (3)
C7A0.055 (5)0.028 (3)0.036 (4)0.003 (4)0.004 (4)0.004 (3)
C8A0.044 (4)0.032 (3)0.032 (3)0.001 (3)0.005 (3)0.004 (3)
C9A0.037 (4)0.023 (3)0.040 (4)0.005 (3)0.003 (3)0.000 (3)
C10A0.034 (4)0.023 (3)0.035 (3)0.004 (3)0.005 (3)0.006 (3)
C11A0.055 (5)0.026 (3)0.045 (4)0.008 (4)0.008 (4)0.007 (3)
C12A0.054 (5)0.021 (3)0.056 (5)0.008 (4)0.006 (4)0.005 (3)
C13A0.051 (5)0.024 (3)0.044 (4)0.003 (3)0.004 (4)0.005 (3)
C14A0.047 (5)0.026 (3)0.041 (4)0.009 (3)0.003 (4)0.006 (3)
C15A0.072 (6)0.056 (5)0.040 (4)0.020 (5)0.007 (4)0.013 (4)
C16A0.067 (6)0.040 (4)0.084 (6)0.024 (4)0.016 (5)0.018 (4)
C17A0.065 (5)0.034 (4)0.052 (5)0.014 (4)0.005 (4)0.004 (4)
C18A0.061 (5)0.038 (4)0.045 (4)0.006 (4)0.000 (4)0.018 (3)
C19A0.047 (5)0.033 (4)0.046 (4)0.013 (4)0.005 (4)0.003 (3)
C20A0.053 (5)0.041 (4)0.035 (4)0.018 (4)0.000 (4)0.006 (3)
C21A0.048 (5)0.053 (5)0.046 (4)0.015 (4)0.005 (4)0.001 (4)
C22A0.076 (6)0.057 (5)0.043 (4)0.032 (5)0.000 (5)0.006 (4)
C23A0.072 (7)0.112 (8)0.045 (5)0.053 (6)0.009 (5)0.000 (5)
C27A0.061 (6)0.064 (6)0.077 (6)0.013 (5)0.016 (5)0.016 (5)
C26A0.074 (6)0.060 (5)0.054 (5)0.008 (5)0.009 (5)0.020 (4)
C28A0.043 (4)0.031 (4)0.060 (4)0.012 (4)0.008 (4)0.002 (3)
C29A0.048 (5)0.026 (3)0.057 (5)0.010 (4)0.002 (4)0.001 (3)
C30A0.057 (5)0.044 (4)0.037 (4)0.005 (4)0.002 (4)0.004 (3)
O1B0.055 (3)0.032 (2)0.071 (3)0.005 (3)0.005 (3)0.007 (3)
O3B0.058 (4)0.063 (4)0.072 (4)0.002 (3)0.016 (3)0.029 (3)
O6B0.041 (3)0.051 (3)0.033 (2)0.008 (3)0.001 (2)0.005 (2)
O7B0.040 (3)0.035 (2)0.029 (2)0.009 (2)0.004 (2)0.002 (2)
O12B0.104 (6)0.064 (4)0.096 (5)0.024 (4)0.028 (4)0.009 (4)
O13B0.048 (3)0.054 (3)0.028 (2)0.002 (3)0.008 (2)0.007 (2)
O15B0.046 (3)0.028 (2)0.059 (3)0.004 (2)0.012 (3)0.008 (2)
O19B0.043 (3)0.065 (3)0.046 (3)0.012 (3)0.009 (3)0.002 (3)
O20B0.054 (3)0.045 (3)0.048 (3)0.005 (3)0.007 (3)0.008 (2)
O21B0.048 (4)0.052 (3)0.115 (5)0.018 (3)0.030 (4)0.007 (3)
O27B0.058 (4)0.146 (7)0.124 (6)0.004 (5)0.045 (4)0.056 (6)
O26B0.086 (5)0.064 (4)0.096 (5)0.018 (4)0.045 (4)0.008 (4)
O29B0.090 (5)0.114 (6)0.088 (5)0.003 (5)0.050 (4)0.005 (4)
C1B0.042 (4)0.040 (4)0.037 (4)0.009 (4)0.002 (3)0.002 (3)
C2B0.043 (5)0.046 (4)0.051 (4)0.005 (4)0.001 (4)0.014 (3)
C3B0.050 (5)0.063 (5)0.043 (4)0.015 (5)0.002 (4)0.017 (4)
C4B0.030 (4)0.055 (4)0.034 (4)0.006 (4)0.006 (3)0.006 (3)
C5B0.039 (4)0.033 (3)0.027 (3)0.004 (3)0.001 (3)0.001 (3)
C6B0.038 (4)0.029 (3)0.029 (3)0.004 (3)0.003 (3)0.000 (3)
C7B0.031 (4)0.029 (3)0.033 (3)0.000 (3)0.001 (3)0.003 (3)
C8B0.028 (4)0.032 (3)0.029 (3)0.001 (3)0.002 (3)0.004 (3)
C9B0.034 (4)0.034 (3)0.030 (3)0.002 (3)0.003 (3)0.005 (3)
C10B0.033 (4)0.032 (3)0.028 (3)0.000 (3)0.005 (3)0.002 (3)
C11B0.044 (4)0.055 (4)0.030 (3)0.008 (4)0.003 (3)0.007 (3)
C12B0.039 (5)0.084 (6)0.043 (4)0.015 (5)0.015 (4)0.010 (5)
C13B0.042 (4)0.030 (3)0.033 (3)0.001 (3)0.001 (3)0.004 (3)
C14B0.040 (4)0.026 (3)0.029 (3)0.006 (3)0.002 (3)0.001 (3)
C15B0.058 (5)0.035 (4)0.038 (4)0.001 (4)0.007 (4)0.006 (3)
C16B0.058 (5)0.056 (5)0.029 (3)0.009 (4)0.005 (4)0.005 (3)
C17B0.064 (5)0.042 (4)0.033 (4)0.001 (4)0.015 (4)0.012 (3)
C18B0.053 (5)0.030 (4)0.065 (5)0.003 (4)0.014 (4)0.005 (3)
C19B0.043 (4)0.041 (4)0.045 (4)0.003 (4)0.007 (4)0.001 (3)
C20B0.052 (5)0.033 (4)0.032 (3)0.005 (4)0.005 (3)0.005 (3)
C21B0.053 (5)0.033 (4)0.045 (4)0.010 (4)0.002 (4)0.003 (3)
C22B0.050 (5)0.052 (5)0.047 (4)0.013 (4)0.018 (4)0.003 (4)
C23B0.047 (5)0.065 (6)0.076 (6)0.002 (5)0.021 (5)0.009 (5)
C26B0.101 (9)0.081 (7)0.141 (10)0.017 (7)0.053 (8)0.025 (7)
C27B0.102 (9)0.174 (14)0.177 (13)0.029 (10)0.064 (9)0.090 (11)
C29B0.053 (5)0.066 (6)0.039 (4)0.015 (5)0.002 (4)0.009 (4)
C28B0.044 (5)0.075 (6)0.037 (4)0.008 (4)0.000 (4)0.005 (4)
C30B0.045 (5)0.032 (3)0.044 (4)0.008 (3)0.005 (4)0.007 (3)
Geometric parameters (Å, º) top
O1A—C1A1.416 (8)O1B—C1B1.435 (8)
O1A—H1A0.8200O1B—H1B0.8200
O3A—C3A1.431 (8)O3B—C3B1.434 (9)
O3A—H3A0.8200O3B—H3B0.8200
O6A—C28A1.449 (8)O6B—C6B1.448 (7)
O6A—C6A1.453 (7)O6B—C28B1.449 (8)
O7A—C7A1.415 (7)O7B—C7B1.451 (7)
O7A—H7A0.8200O7B—H7B0.8200
O12A—C12A1.195 (8)O12B—C12B1.185 (10)
O13A—C13A1.456 (8)O13B—C14B1.438 (7)
O13A—C14A1.460 (8)O13B—C13B1.460 (8)
O15A—C21A1.396 (9)O15B—C21B1.397 (8)
O15A—C15A1.455 (10)O15B—C15B1.437 (8)
O19A—C11A1.429 (8)O19B—C19B1.427 (8)
O19A—C19A1.440 (7)O19B—C11B1.436 (8)
O20A—C20A1.433 (8)O20B—C20B1.438 (7)
O20A—H20A0.8200O20B—H20B0.8200
O21A—C23A1.355 (10)O21B—C23B1.364 (9)
O21A—C21A1.442 (9)O21B—C21B1.456 (8)
O27A—C12A1.354 (9)O27B—C12B1.324 (10)
O27A—C27A1.459 (8)O27B—C27B1.469 (12)
O26A—C29A1.332 (8)O26B—C29B1.304 (10)
O26A—C26A1.437 (8)O26B—C26B1.453 (10)
O29A—C29A1.236 (9)O29B—C29B1.213 (9)
C1A—C2A1.540 (9)C1B—C2B1.524 (9)
C1A—C10A1.564 (9)C1B—C10B1.560 (8)
C1A—H1A10.9800C1B—H1B10.9800
C2A—C3A1.515 (9)C2B—C3B1.544 (10)
C2A—H2A10.9700C2B—H2B10.9700
C2A—H2A20.9700C2B—H2B20.9700
C3A—C4A1.545 (10)C3B—C4B1.546 (10)
C3A—H3A10.9800C3B—H3B10.9800
C4A—C29A1.498 (9)C4B—C29B1.506 (11)
C4A—C5A1.532 (8)C4B—C5B1.510 (9)
C4A—C28A1.573 (9)C4B—C28B1.538 (9)
C5A—C6A1.469 (9)C5B—C6B1.494 (8)
C5A—C10A1.519 (8)C5B—C10B1.529 (9)
C5A—H5A0.9800C5B—H5B0.9800
C6A—C7A1.531 (9)C6B—C7B1.519 (8)
C6A—H6A0.9800C6B—H6B0.9800
C7A—C8A1.551 (9)C7B—C8B1.565 (8)
C7A—H7A10.9800C7B—H7B10.9800
C8A—C30A1.538 (8)C8B—C14B1.536 (8)
C8A—C14A1.561 (9)C8B—C30B1.545 (8)
C8A—C9A1.592 (9)C8B—C9B1.580 (8)
C9A—C10A1.535 (8)C9B—C11B1.540 (9)
C9A—C11A1.539 (9)C9B—C10B1.556 (8)
C9A—H9A0.9800C9B—H9B0.9800
C10A—C19A1.530 (9)C10B—C19B1.528 (9)
C11A—C12A1.525 (9)C11B—C12B1.520 (11)
C11A—H11A0.9800C11B—H11B0.9800
C13A—C14A1.467 (9)C13B—C14B1.493 (8)
C13A—C18A1.515 (9)C13B—C18B1.507 (9)
C13A—C17A1.530 (10)C13B—C17B1.523 (9)
C14A—C15A1.536 (10)C14B—C15B1.542 (9)
C15A—C16A1.513 (10)C15B—C16B1.513 (9)
C15A—H15A0.9800C15B—H15B0.9800
C16A—C17A1.519 (10)C16B—C17B1.526 (10)
C16A—H16A0.9700C16B—H16C0.9700
C16A—H16B0.9700C16B—H16D0.9700
C17A—C20A1.555 (10)C17B—C20B1.556 (10)
C17A—H17A0.9800C17B—H17B0.9800
C18A—H18A0.9600C18B—H18D0.9600
C18A—H18B0.9600C18B—H18E0.9600
C18A—H18C0.9600C18B—H18F0.9600
C19A—H19A0.9700C19B—H19C0.9700
C19A—H19B0.9700C19B—H19D0.9700
C20A—C22A1.519 (10)C20B—C22B1.502 (10)
C20A—C21A1.555 (10)C20B—C21B1.544 (9)
C21A—H21A0.9800C21B—H21B0.9800
C22A—C23A1.266 (11)C22B—C23B1.324 (11)
C22A—H22A0.9300C22B—H22B0.9300
C23A—H23A0.9300C23B—H23B0.9300
C27A—H27A0.9600C26B—H26D0.9600
C27A—H27B0.9600C26B—H26E0.9600
C27A—H27C0.9600C26B—H26F0.9600
C26A—H26A0.9600C27B—H27D0.9600
C26A—H26B0.9600C27B—H27E0.9600
C26A—H26C0.9600C27B—H27F0.9600
C28A—H28A0.9700C28B—H28C0.9700
C28A—H28B0.9700C28B—H28D0.9700
C30A—H30A0.9600C30B—H30D0.9600
C30A—H30B0.9600C30B—H30E0.9600
C30A—H30C0.9600C30B—H30F0.9600
C1A—O1A—H1A109.5C1B—O1B—H1B109.5
C3A—O3A—H3A109.5C3B—O3B—H3B109.5
C28A—O6A—C6A110.1 (5)C6B—O6B—C28B109.5 (5)
C7A—O7A—H7A109.5C7B—O7B—H7B109.5
C13A—O13A—C14A60.4 (4)C14B—O13B—C13B62.0 (4)
C21A—O15A—C15A117.3 (6)C21B—O15B—C15B116.4 (5)
C11A—O19A—C19A109.4 (5)C19B—O19B—C11B110.8 (5)
C20A—O20A—H20A109.5C20B—O20B—H20B109.5
C23A—O21A—C21A106.8 (7)C23B—O21B—C21B107.2 (6)
C12A—O27A—C27A116.1 (6)C12B—O27B—C27B115.4 (9)
C29A—O26A—C26A118.8 (6)C29B—O26B—C26B118.0 (7)
O1A—C1A—C2A112.5 (5)O1B—C1B—C2B108.8 (6)
O1A—C1A—C10A111.3 (6)O1B—C1B—C10B108.4 (5)
C2A—C1A—C10A111.7 (5)C2B—C1B—C10B111.4 (5)
O1A—C1A—H1A1106.9O1B—C1B—H1B1109.4
C2A—C1A—H1A1106.9C2B—C1B—H1B1109.4
C10A—C1A—H1A1106.9C10B—C1B—H1B1109.4
C3A—C2A—C1A116.4 (6)C1B—C2B—C3B114.7 (6)
C3A—C2A—H2A1108.2C1B—C2B—H2B1108.6
C1A—C2A—H2A1108.2C3B—C2B—H2B1108.6
C3A—C2A—H2A2108.2C1B—C2B—H2B2108.6
C1A—C2A—H2A2108.2C3B—C2B—H2B2108.6
H2A1—C2A—H2A2107.3H2B1—C2B—H2B2107.6
O3A—C3A—C2A107.9 (6)O3B—C3B—C2B111.7 (6)
O3A—C3A—C4A110.2 (6)O3B—C3B—C4B111.6 (6)
C2A—C3A—C4A110.7 (5)C2B—C3B—C4B108.1 (6)
O3A—C3A—H3A1109.3O3B—C3B—H3B1108.4
C2A—C3A—H3A1109.3C2B—C3B—H3B1108.4
C4A—C3A—H3A1109.3C4B—C3B—H3B1108.4
C29A—C4A—C5A114.7 (5)C29B—C4B—C5B118.3 (6)
C29A—C4A—C3A109.4 (6)C29B—C4B—C28B108.2 (6)
C5A—C4A—C3A106.3 (5)C5B—C4B—C28B97.6 (5)
C29A—C4A—C28A109.3 (6)C29B—C4B—C3B107.8 (6)
C5A—C4A—C28A97.5 (5)C5B—C4B—C3B106.9 (6)
C3A—C4A—C28A119.4 (5)C28B—C4B—C3B118.4 (6)
C6A—C5A—C10A117.9 (5)C6B—C5B—C4B106.6 (5)
C6A—C5A—C4A106.6 (5)C6B—C5B—C10B117.9 (5)
C10A—C5A—C4A119.2 (6)C4B—C5B—C10B120.6 (6)
C6A—C5A—H5A103.6C6B—C5B—H5B103.0
C10A—C5A—H5A103.6C4B—C5B—H5B103.0
C4A—C5A—H5A103.6C10B—C5B—H5B103.0
O6A—C6A—C5A103.2 (5)O6B—C6B—C5B102.7 (5)
O6A—C6A—C7A112.9 (5)O6B—C6B—C7B113.7 (5)
C5A—C6A—C7A109.4 (5)C5B—C6B—C7B110.1 (5)
O6A—C6A—H6A110.4O6B—C6B—H6B110.0
C5A—C6A—H6A110.4C5B—C6B—H6B110.0
C7A—C6A—H6A110.4C7B—C6B—H6B110.0
O7A—C7A—C6A110.5 (5)O7B—C7B—C6B110.6 (5)
O7A—C7A—C8A112.1 (5)O7B—C7B—C8B111.3 (5)
C6A—C7A—C8A106.7 (6)C6B—C7B—C8B108.4 (5)
O7A—C7A—H7A1109.1O7B—C7B—H7B1108.9
C6A—C7A—H7A1109.1C6B—C7B—H7B1108.9
C8A—C7A—H7A1109.1C8B—C7B—H7B1108.9
C30A—C8A—C7A108.1 (5)C14B—C8B—C30B107.8 (5)
C30A—C8A—C14A107.0 (5)C14B—C8B—C7B108.3 (5)
C7A—C8A—C14A107.2 (5)C30B—C8B—C7B105.2 (5)
C30A—C8A—C9A110.7 (6)C14B—C8B—C9B108.8 (5)
C7A—C8A—C9A113.9 (5)C30B—C8B—C9B112.2 (5)
C14A—C8A—C9A109.6 (5)C7B—C8B—C9B114.2 (5)
C10A—C9A—C11A101.0 (5)C11B—C9B—C10B101.0 (5)
C10A—C9A—C8A117.2 (5)C11B—C9B—C8B113.4 (5)
C11A—C9A—C8A113.5 (5)C10B—C9B—C8B117.4 (5)
C10A—C9A—H9A108.2C11B—C9B—H9B108.2
C11A—C9A—H9A108.2C10B—C9B—H9B108.2
C8A—C9A—H9A108.2C8B—C9B—H9B108.2
C5A—C10A—C19A117.1 (5)C19B—C10B—C5B119.3 (5)
C5A—C10A—C9A108.8 (5)C19B—C10B—C9B102.8 (5)
C19A—C10A—C9A103.2 (5)C5B—C10B—C9B107.9 (5)
C5A—C10A—C1A105.3 (5)C19B—C10B—C1B108.9 (6)
C19A—C10A—C1A109.7 (5)C5B—C10B—C1B104.8 (5)
C9A—C10A—C1A113.0 (5)C9B—C10B—C1B113.5 (5)
O19A—C11A—C12A111.3 (6)O19B—C11B—C12B110.2 (6)
O19A—C11A—C9A107.3 (5)O19B—C11B—C9B107.1 (5)
C12A—C11A—C9A113.8 (6)C12B—C11B—C9B113.5 (6)
O19A—C11A—H11A108.1O19B—C11B—H11B108.6
C12A—C11A—H11A108.1C12B—C11B—H11B108.6
C9A—C11A—H11A108.1C9B—C11B—H11B108.6
O12A—C12A—O27A123.2 (7)O12B—C12B—O27B123.9 (9)
O12A—C12A—C11A122.8 (7)O12B—C12B—C11B127.3 (8)
O27A—C12A—C11A113.9 (6)O27B—C12B—C11B108.8 (8)
O13A—C13A—C14A59.9 (4)O13B—C13B—C14B58.3 (4)
O13A—C13A—C18A116.1 (6)O13B—C13B—C18B113.8 (6)
C14A—C13A—C18A129.6 (6)C14B—C13B—C18B130.3 (6)
O13A—C13A—C17A111.6 (6)O13B—C13B—C17B112.6 (5)
C14A—C13A—C17A106.9 (6)C14B—C13B—C17B106.6 (5)
C18A—C13A—C17A118.5 (6)C18B—C13B—C17B119.5 (6)
O13A—C14A—C13A59.7 (4)O13B—C14B—C13B59.7 (4)
O13A—C14A—C15A108.8 (5)O13B—C14B—C8B117.9 (6)
C13A—C14A—C15A105.3 (6)C13B—C14B—C8B129.7 (5)
O13A—C14A—C8A116.3 (6)O13B—C14B—C15B107.8 (5)
C13A—C14A—C8A129.2 (6)C13B—C14B—C15B105.0 (5)
C15A—C14A—C8A121.2 (6)C8B—C14B—C15B120.7 (5)
O15A—C15A—C16A111.4 (7)O15B—C15B—C16B111.1 (6)
O15A—C15A—C14A109.5 (6)O15B—C15B—C14B109.8 (5)
C16A—C15A—C14A104.4 (6)C16B—C15B—C14B104.5 (5)
O15A—C15A—H15A110.5O15B—C15B—H15B110.5
C16A—C15A—H15A110.5C16B—C15B—H15B110.5
C14A—C15A—H15A110.5C14B—C15B—H15B110.5
C15A—C16A—C17A99.7 (6)C15B—C16B—C17B100.0 (5)
C15A—C16A—H16A111.8C15B—C16B—H16C111.8
C17A—C16A—H16A111.8C17B—C16B—H16C111.8
C15A—C16A—H16B111.8C15B—C16B—H16D111.8
C17A—C16A—H16B111.8C17B—C16B—H16D111.8
H16A—C16A—H16B109.6H16C—C16B—H16D109.5
C16A—C17A—C13A102.9 (6)C13B—C17B—C16B102.8 (6)
C16A—C17A—C20A105.2 (7)C13B—C17B—C20B111.8 (5)
C13A—C17A—C20A111.7 (6)C16B—C17B—C20B105.5 (6)
C16A—C17A—H17A112.1C13B—C17B—H17B112.1
C13A—C17A—H17A112.1C16B—C17B—H17B112.1
C20A—C17A—H17A112.1C20B—C17B—H17B112.1
C13A—C18A—H18A109.5C13B—C18B—H18D109.5
C13A—C18A—H18B109.5C13B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C13A—C18A—H18C109.5C13B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
O19A—C19A—C10A107.1 (5)O19B—C19B—C10B106.1 (5)
O19A—C19A—H19A110.3O19B—C19B—H19C110.5
C10A—C19A—H19A110.3C10B—C19B—H19C110.5
O19A—C19A—H19B110.3O19B—C19B—H19D110.5
C10A—C19A—H19B110.3C10B—C19B—H19D110.5
H19A—C19A—H19B108.5H19C—C19B—H19D108.7
O20A—C20A—C22A107.7 (6)O20B—C20B—C22B109.0 (6)
O20A—C20A—C21A109.2 (6)O20B—C20B—C21B108.8 (5)
C22A—C20A—C21A100.1 (6)C22B—C20B—C21B101.7 (6)
O20A—C20A—C17A111.7 (6)O20B—C20B—C17B112.1 (6)
C22A—C20A—C17A113.0 (6)C22B—C20B—C17B111.1 (5)
C21A—C20A—C17A114.5 (6)C21B—C20B—C17B113.6 (6)
O15A—C21A—O21A107.7 (6)O15B—C21B—O21B108.3 (5)
O15A—C21A—C20A119.1 (7)O15B—C21B—C20B120.2 (6)
O21A—C21A—C20A106.1 (6)O21B—C21B—C20B106.3 (6)
O15A—C21A—H21A107.8O15B—C21B—H21B107.1
O21A—C21A—H21A107.8O21B—C21B—H21B107.1
C20A—C21A—H21A107.8C20B—C21B—H21B107.1
C23A—C22A—C20A109.6 (7)C23B—C22B—C20B109.2 (7)
C23A—C22A—H22A125.2C23B—C22B—H22B125.4
C20A—C22A—H22A125.2C20B—C22B—H22B125.4
C22A—C23A—O21A116.7 (8)C22B—C23B—O21B114.9 (7)
C22A—C23A—H23A121.7C22B—C23B—H23B122.6
O21A—C23A—H23A121.7O21B—C23B—H23B122.6
O27A—C27A—H27A109.5O26B—C26B—H26D109.5
O27A—C27A—H27B109.5O26B—C26B—H26E109.5
H27A—C27A—H27B109.5H26D—C26B—H26E109.5
O27A—C27A—H27C109.5O26B—C26B—H26F109.5
H27A—C27A—H27C109.5H26D—C26B—H26F109.5
H27B—C27A—H27C109.5H26E—C26B—H26F109.5
O26A—C26A—H26A109.5O27B—C27B—H27D109.5
O26A—C26A—H26B109.5O27B—C27B—H27E109.5
H26A—C26A—H26B109.5H27D—C27B—H27E109.5
O26A—C26A—H26C109.5O27B—C27B—H27F109.5
H26A—C26A—H26C109.5H27D—C27B—H27F109.5
H26B—C26A—H26C109.5H27E—C27B—H27F109.5
O6A—C28A—C4A106.5 (5)O29B—C29B—O26B121.6 (9)
O6A—C28A—H28A110.4O29B—C29B—C4B124.4 (8)
C4A—C28A—H28A110.4O26B—C29B—C4B113.7 (7)
O6A—C28A—H28B110.4O6B—C28B—C4B107.4 (6)
C4A—C28A—H28B110.4O6B—C28B—H28C110.2
H28A—C28A—H28B108.6C4B—C28B—H28C110.2
O29A—C29A—O26A120.1 (7)O6B—C28B—H28D110.2
O29A—C29A—C4A126.1 (7)C4B—C28B—H28D110.2
O26A—C29A—C4A113.8 (6)H28C—C28B—H28D108.5
C8A—C30A—H30A109.5C8B—C30B—H30D109.5
C8A—C30A—H30B109.5C8B—C30B—H30E109.5
H30A—C30A—H30B109.5H30D—C30B—H30E109.5
C8A—C30A—H30C109.5C8B—C30B—H30F109.5
H30A—C30A—H30C109.5H30D—C30B—H30F109.5
H30B—C30A—H30C109.5H30E—C30B—H30F109.5
O1A—C1A—C2A—C3A73.7 (7)O1B—C1B—C2B—C3B61.4 (8)
C10A—C1A—C2A—C3A52.4 (8)C10B—C1B—C2B—C3B58.0 (8)
C1A—C2A—C3A—O3A67.5 (7)C1B—C2B—C3B—O3B64.5 (8)
C1A—C2A—C3A—C4A53.2 (8)C1B—C2B—C3B—C4B58.6 (8)
O3A—C3A—C4A—C29A168.2 (5)O3B—C3B—C4B—C29B162.4 (6)
C2A—C3A—C4A—C29A72.5 (7)C2B—C3B—C4B—C29B74.4 (7)
O3A—C3A—C4A—C5A67.5 (6)O3B—C3B—C4B—C5B69.5 (7)
C2A—C3A—C4A—C5A51.9 (7)C2B—C3B—C4B—C5B53.8 (8)
O3A—C3A—C4A—C28A41.3 (7)O3B—C3B—C4B—C28B39.3 (8)
C2A—C3A—C4A—C28A160.6 (6)C2B—C3B—C4B—C28B162.5 (6)
C29A—C4A—C5A—C6A76.2 (7)C29B—C4B—C5B—C6B75.5 (7)
C3A—C4A—C5A—C6A162.8 (5)C28B—C4B—C5B—C6B39.9 (7)
C28A—C4A—C5A—C6A39.2 (6)C3B—C4B—C5B—C6B162.8 (6)
C29A—C4A—C5A—C10A60.4 (8)C29B—C4B—C5B—C10B62.6 (9)
C3A—C4A—C5A—C10A60.6 (7)C28B—C4B—C5B—C10B178.0 (6)
C28A—C4A—C5A—C10A175.8 (6)C3B—C4B—C5B—C10B59.1 (8)
C28A—O6A—C6A—C5A18.9 (7)C28B—O6B—C6B—C5B15.1 (7)
C28A—O6A—C6A—C7A136.9 (6)C28B—O6B—C6B—C7B134.0 (6)
C10A—C5A—C6A—O6A174.7 (5)C4B—C5B—C6B—O6B35.7 (7)
C4A—C5A—C6A—O6A37.5 (6)C10B—C5B—C6B—O6B175.1 (5)
C10A—C5A—C6A—C7A64.9 (7)C4B—C5B—C6B—C7B157.1 (5)
C4A—C5A—C6A—C7A157.9 (5)C10B—C5B—C6B—C7B63.5 (7)
O6A—C6A—C7A—O7A54.6 (7)O6B—C6B—C7B—O7B51.6 (7)
C5A—C6A—C7A—O7A59.7 (7)C5B—C6B—C7B—O7B63.0 (7)
O6A—C6A—C7A—C8A176.8 (5)O6B—C6B—C7B—C8B173.8 (5)
C5A—C6A—C7A—C8A62.5 (7)C5B—C6B—C7B—C8B59.2 (6)
O7A—C7A—C8A—C30A167.2 (6)O7B—C7B—C8B—C14B49.5 (6)
C6A—C7A—C8A—C30A71.7 (7)C6B—C7B—C8B—C14B171.3 (5)
O7A—C7A—C8A—C14A52.1 (7)O7B—C7B—C8B—C30B164.6 (5)
C6A—C7A—C8A—C14A173.2 (5)C6B—C7B—C8B—C30B73.7 (6)
O7A—C7A—C8A—C9A69.3 (7)O7B—C7B—C8B—C9B71.9 (6)
C6A—C7A—C8A—C9A51.8 (7)C6B—C7B—C8B—C9B49.8 (7)
C30A—C8A—C9A—C10A81.6 (7)C14B—C8B—C9B—C11B80.5 (6)
C7A—C8A—C9A—C10A40.5 (8)C30B—C8B—C9B—C11B38.7 (7)
C14A—C8A—C9A—C10A160.6 (5)C7B—C8B—C9B—C11B158.3 (5)
C30A—C8A—C9A—C11A35.6 (7)C14B—C8B—C9B—C10B162.2 (5)
C7A—C8A—C9A—C11A157.7 (5)C30B—C8B—C9B—C10B78.5 (7)
C14A—C8A—C9A—C11A82.1 (6)C7B—C8B—C9B—C10B41.1 (7)
C6A—C5A—C10A—C19A68.4 (8)C6B—C5B—C10B—C19B67.2 (8)
C4A—C5A—C10A—C19A63.3 (8)C4B—C5B—C10B—C19B66.3 (8)
C6A—C5A—C10A—C9A48.0 (7)C6B—C5B—C10B—C9B49.4 (7)
C4A—C5A—C10A—C9A179.8 (6)C4B—C5B—C10B—C9B177.1 (6)
C6A—C5A—C10A—C1A169.4 (6)C6B—C5B—C10B—C1B170.6 (5)
C4A—C5A—C10A—C1A58.8 (7)C4B—C5B—C10B—C1B55.9 (8)
C11A—C9A—C10A—C5A158.3 (5)C11B—C9B—C10B—C19B34.1 (6)
C8A—C9A—C10A—C5A34.5 (7)C8B—C9B—C10B—C19B89.7 (6)
C11A—C9A—C10A—C19A33.2 (6)C11B—C9B—C10B—C5B161.0 (5)
C8A—C9A—C10A—C19A90.6 (6)C8B—C9B—C10B—C5B37.2 (7)
C11A—C9A—C10A—C1A85.2 (6)C11B—C9B—C10B—C1B83.3 (6)
C8A—C9A—C10A—C1A151.0 (5)C8B—C9B—C10B—C1B152.9 (6)
O1A—C1A—C10A—C5A77.2 (6)O1B—C1B—C10B—C19B161.9 (5)
C2A—C1A—C10A—C5A49.6 (7)C2B—C1B—C10B—C19B78.4 (7)
O1A—C1A—C10A—C19A156.0 (5)O1B—C1B—C10B—C5B69.4 (6)
C2A—C1A—C10A—C19A77.2 (7)C2B—C1B—C10B—C5B50.3 (7)
O1A—C1A—C10A—C9A41.5 (7)O1B—C1B—C10B—C9B48.1 (7)
C2A—C1A—C10A—C9A168.3 (5)C2B—C1B—C10B—C9B167.8 (6)
C19A—O19A—C11A—C12A109.0 (6)C19B—O19B—C11B—C12B114.7 (6)
C19A—O19A—C11A—C9A16.2 (7)C19B—O19B—C11B—C9B9.3 (7)
C10A—C9A—C11A—O19A31.0 (7)C10B—C9B—C11B—O19B27.2 (6)
C8A—C9A—C11A—O19A95.3 (6)C8B—C9B—C11B—O19B99.2 (6)
C10A—C9A—C11A—C12A92.6 (7)C10B—C9B—C11B—C12B94.7 (6)
C8A—C9A—C11A—C12A141.0 (6)C8B—C9B—C11B—C12B138.9 (6)
C27A—O27A—C12A—O12A0.9 (11)C27B—O27B—C12B—O12B2.3 (14)
C27A—O27A—C12A—C11A174.9 (6)C27B—O27B—C12B—C11B178.3 (9)
O19A—C11A—C12A—O12A177.5 (6)O19B—C11B—C12B—O12B128.6 (9)
C9A—C11A—C12A—O12A56.0 (9)C9B—C11B—C12B—O12B8.5 (12)
O19A—C11A—C12A—O27A6.7 (9)O19B—C11B—C12B—O27B50.8 (8)
C9A—C11A—C12A—O27A128.2 (7)C9B—C11B—C12B—O27B170.9 (6)
C14A—O13A—C13A—C18A122.5 (7)C14B—O13B—C13B—C18B124.0 (6)
C14A—O13A—C13A—C17A97.6 (6)C14B—O13B—C13B—C17B96.1 (6)
C13A—O13A—C14A—C15A97.1 (6)C13B—O13B—C14B—C8B121.8 (6)
C13A—O13A—C14A—C8A121.9 (6)C13B—O13B—C14B—C15B97.2 (6)
C18A—C13A—C14A—O13A100.4 (8)C18B—C13B—C14B—O13B95.6 (8)
C17A—C13A—C14A—O13A105.5 (6)C17B—C13B—C14B—O13B106.7 (5)
O13A—C13A—C14A—C15A103.2 (6)O13B—C13B—C14B—C8B102.7 (8)
C18A—C13A—C14A—C15A156.5 (8)C18B—C13B—C14B—C8B7.2 (12)
C17A—C13A—C14A—C15A2.4 (7)C17B—C13B—C14B—C8B150.6 (7)
O13A—C13A—C14A—C8A100.7 (8)O13B—C13B—C14B—C15B102.2 (5)
C18A—C13A—C14A—C8A0.3 (12)C18B—C13B—C14B—C15B162.3 (7)
C17A—C13A—C14A—C8A153.8 (7)C17B—C13B—C14B—C15B4.5 (7)
C30A—C8A—C14A—O13A93.6 (7)C30B—C8B—C14B—O13B95.7 (6)
C7A—C8A—C14A—O13A150.6 (6)C7B—C8B—C14B—O13B150.9 (5)
C9A—C8A—C14A—O13A26.5 (7)C9B—C8B—C14B—O13B26.2 (7)
C30A—C8A—C14A—C13A164.7 (7)C30B—C8B—C14B—C13B168.2 (7)
C7A—C8A—C14A—C13A79.5 (9)C7B—C8B—C14B—C13B78.5 (8)
C9A—C8A—C14A—C13A44.7 (9)C9B—C8B—C14B—C13B46.2 (9)
C30A—C8A—C14A—C15A42.4 (9)C30B—C8B—C14B—C15B40.1 (8)
C7A—C8A—C14A—C15A73.4 (7)C7B—C8B—C14B—C15B73.3 (7)
C9A—C8A—C14A—C15A162.4 (6)C9B—C8B—C14B—C15B162.0 (6)
C21A—O15A—C15A—C16A40.2 (8)C21B—O15B—C15B—C16B31.8 (8)
C21A—O15A—C15A—C14A74.7 (7)C21B—O15B—C15B—C14B83.2 (7)
O13A—C14A—C15A—O15A156.5 (5)O13B—C14B—C15B—O15B157.7 (5)
C13A—C14A—C15A—O15A93.9 (6)C13B—C14B—C15B—O15B95.3 (6)
C8A—C14A—C15A—O15A64.7 (8)C8B—C14B—C15B—O15B62.6 (8)
O13A—C14A—C15A—C16A37.2 (8)O13B—C14B—C15B—C16B38.6 (7)
C13A—C14A—C15A—C16A25.5 (8)C13B—C14B—C15B—C16B23.9 (7)
C8A—C14A—C15A—C16A176.0 (6)C8B—C14B—C15B—C16B178.2 (6)
O15A—C15A—C16A—C17A75.5 (8)O15B—C15B—C16B—C17B76.0 (7)
C14A—C15A—C16A—C17A42.6 (8)C14B—C15B—C16B—C17B42.3 (7)
C15A—C16A—C17A—C13A43.6 (8)O13B—C13B—C17B—C16B31.1 (7)
C15A—C16A—C17A—C20A73.6 (8)C14B—C13B—C17B—C16B30.9 (7)
O13A—C13A—C17A—C16A34.5 (8)C18B—C13B—C17B—C16B168.5 (6)
C14A—C13A—C17A—C16A29.2 (7)O13B—C13B—C17B—C20B143.8 (5)
C18A—C13A—C17A—C16A173.4 (6)C14B—C13B—C17B—C20B81.8 (7)
O13A—C13A—C17A—C20A147.0 (6)C18B—C13B—C17B—C20B78.8 (8)
C14A—C13A—C17A—C20A83.3 (7)C15B—C16B—C17B—C13B44.6 (7)
C18A—C13A—C17A—C20A74.2 (8)C15B—C16B—C17B—C20B72.6 (7)
C11A—O19A—C19A—C10A6.0 (7)C11B—O19B—C19B—C10B13.5 (7)
C5A—C10A—C19A—O19A144.9 (6)C5B—C10B—C19B—O19B149.5 (5)
C9A—C10A—C19A—O19A25.4 (7)C9B—C10B—C19B—O19B30.2 (6)
C1A—C10A—C19A—O19A95.3 (6)C1B—C10B—C19B—O19B90.4 (6)
C16A—C17A—C20A—O20A167.7 (6)C13B—C17B—C20B—O20B45.5 (7)
C13A—C17A—C20A—O20A56.7 (8)C16B—C17B—C20B—O20B156.5 (5)
C16A—C17A—C20A—C22A70.7 (7)C13B—C17B—C20B—C22B167.7 (6)
C13A—C17A—C20A—C22A178.3 (6)C16B—C17B—C20B—C22B81.3 (7)
C16A—C17A—C20A—C21A43.0 (7)C13B—C17B—C20B—C21B78.3 (7)
C13A—C17A—C20A—C21A68.0 (8)C16B—C17B—C20B—C21B32.7 (7)
C15A—O15A—C21A—O21A125.6 (7)C15B—O15B—C21B—O21B109.3 (6)
C15A—O15A—C21A—C20A4.9 (9)C15B—O15B—C21B—C20B13.0 (9)
C23A—O21A—C21A—O15A120.3 (7)C23B—O21B—C21B—O15B139.3 (6)
C23A—O21A—C21A—C20A8.2 (9)C23B—O21B—C21B—C20B8.9 (8)
O20A—C20A—C21A—O15A133.2 (7)O20B—C20B—C21B—O15B113.8 (7)
C22A—C20A—C21A—O15A113.9 (7)C22B—C20B—C21B—O15B131.2 (6)
C17A—C20A—C21A—O15A7.2 (9)C17B—C20B—C21B—O15B11.7 (9)
O20A—C20A—C21A—O21A105.2 (7)O20B—C20B—C21B—O21B122.9 (6)
C22A—C20A—C21A—O21A7.6 (8)C22B—C20B—C21B—O21B7.9 (7)
C17A—C20A—C21A—O21A128.7 (7)C17B—C20B—C21B—O21B111.6 (7)
O20A—C20A—C22A—C23A109.3 (8)O20B—C20B—C22B—C23B119.3 (7)
C21A—C20A—C22A—C23A4.7 (9)C21B—C20B—C22B—C23B4.5 (8)
C17A—C20A—C22A—C23A126.9 (8)C17B—C20B—C22B—C23B116.7 (8)
C20A—C22A—C23A—O21A0.3 (12)C20B—C22B—C23B—O21B1.0 (10)
C21A—O21A—C23A—C22A5.6 (12)C21B—O21B—C23B—C22B6.4 (10)
C6A—O6A—C28A—C4A6.0 (7)C26B—O26B—C29B—O29B0.1 (13)
C29A—C4A—C28A—O6A92.7 (6)C26B—O26B—C29B—C4B173.1 (7)
C5A—C4A—C28A—O6A26.8 (6)C5B—C4B—C29B—O29B145.5 (8)
C3A—C4A—C28A—O6A140.4 (6)C28B—C4B—C29B—O29B104.9 (9)
C26A—O26A—C29A—O29A0.5 (10)C3B—C4B—C29B—O29B24.2 (10)
C26A—O26A—C29A—C4A179.8 (6)C5B—C4B—C29B—O26B41.5 (9)
C5A—C4A—C29A—O29A120.8 (8)C28B—C4B—C29B—O26B68.0 (8)
C3A—C4A—C29A—O29A1.5 (9)C3B—C4B—C29B—O26B162.8 (7)
C28A—C4A—C29A—O29A131.0 (7)C6B—O6B—C28B—C4B10.1 (7)
C5A—C4A—C29A—O26A60.1 (8)C29B—C4B—C28B—O6B93.1 (7)
C3A—C4A—C29A—O26A179.4 (5)C5B—C4B—C28B—O6B30.1 (7)
C28A—C4A—C29A—O26A48.2 (7)C3B—C4B—C28B—O6B144.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7A—H7A···O6A0.822.592.865 (6)101
O1A—H1A···O3A0.822.452.964 (7)121
O7B—H7B···O6B0.822.412.860 (6)116
O7A—H7A···O6B0.822.052.813 (5)156
O7B—H7B···O6A0.822.302.864 (5)127
O20B—H20B···O7B0.822.242.977 (6)150
O3B—H3B···O1B0.822.052.760 (8)145
O1A—H1A···O13Bi0.822.422.943 (5)122
O3A—H3A···O12Aii0.822.052.850 (7)166
O1B—H1B···O20Biii0.822.072.846 (7)157
Symmetry codes: (i) x+3/2, y+1, z1/2; (ii) x+1, y1/2, z+3/2; (iii) x+1/2, y+1/2, z+2.

Experimental details

Crystal data
Chemical formulaC28H36O13
Mr580.57
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)14.142 (6), 17.287 (3), 21.505 (4)
V3)5257 (3)
Z8
Radiation typeCu Kα
µ (mm1)0.99
Crystal size (mm)0.35 × 0.23 × 0.15
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6108, 5699, 3087
Rint0.035
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.173, 1.04
No. of reflections5699
No. of parameters748
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.31

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97 and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7A—H7A···O6A0.822.592.865 (6)101
O1A—H1A···O3A0.822.452.964 (7)121
O7B—H7B···O6B0.822.412.860 (6)116
O7A—H7A···O6B0.822.052.813 (5)156
O7B—H7B···O6A0.822.302.864 (5)127
O20B—H20B···O7B0.822.242.977 (6)150
O3B—H3B···O1B0.822.052.760 (8)145
O1A—H1A···O13Bi0.822.422.943 (5)122
O3A—H3A···O12Aii0.822.052.850 (7)166
O1B—H1B···O20Biii0.822.072.846 (7)157
Symmetry codes: (i) x+3/2, y+1, z1/2; (ii) x+1, y1/2, z+3/2; (iii) x+1/2, y+1/2, z+2.
 

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