3,6-Di­hydroxy-2-(11-phenyl­undecan­oyl)­cyclo­hex-2-en-1-one from Virola venosa bark

The structure of the title compound, C₂₃H₃₂O₄, an aryl­alkanone isolated from the petroleum ether fraction of the ethanol extract of the bark of Virola venosa, has been established by NMR spectroscopy and, for the first time, by X-ray structure analysis. Two independent mol­ecules of the same enantiomer are present in the unit cell. Both mol­ecules exhibit an intramolecular hydrogen bond, which can be correlated with a rare signal observed at 18.28 p.p.m. in the ¹H NMR spectrum. The packing, in space group P1, is determined by a pseudo-center of symmetry leading to a short intermolecular contact, which is present in one mol­ecule but does not occur in the other. As a consequence, the O-C-C-O torsion angles [-16.9 (3) and -12.7 (3)°] through the ketone and its adjacent hydroxy group are significantly different in the two mol­ecules.

S1. Comment

Ethnobiological studies carried out in Colombia have shown that native tribes use species of Virola (Myristicaceae plant family) for the treatment of a large variety of sicknesses, such as treatment of mental instability, infected wounds, skin infections, colic and vitiligo (Schultes & Holmstedt, 1971). Virola venosa (Benth.) Warb. (Myristicaceae) is a tropical tree endemic in altitudes between 200 and 1300 m above sea level. The plant reaches an average height of 30 m, with a trunk diameter of 35 cm, and has been reported both in the Brazilian Amazon region, where it is known as `ucuuba-da-mata', and in the Colombian departments Amazonas and Vaupes (Herrera, 1994). Previous publications reveal that blooms, fruits and seeds contain flavanoids, lignanes, arylalkanones and sitosterol. In leaves and roots, alkaloids and stilbenes have been detected (Kato et al., 1992). Studies on bioactivity of species from the Virola plant family showing antimalaria (Lopes et al., 1999), anti-inflammatory (Carvalho et al., 1999), antifungal (Lopes et al., 1999a; Sartorelli et al., 1998) and antileishmanial activities (Barata et al., 2000) have been reported. The sample of the bark of Virola venosa used in the present study was collected in the Amacayacu National Park in Leticia, capital of the Colombian department Amazonas. The isolation and purification of (I) was carried out by means of chromatographic techniques. The compound was crystallized in methanol and its structure was elucidated using NMR techniques, mass spectrometry and IR spectroscopy.

The ¹H-NMR spectrum of (I) shows a rare signal at 18.28 p.p.m., which was interpreted as an intramolecular hydrogen bond. X-ray structure analysis shows that the unit cell contains two independent molecules, both with intramolecular hydrogen bonds. The H atoms involved in hydrogen bonding have been located. In fact, peaks for all 64 H atoms of the two molecules of (I) unambiguously emerged from difference Fourier maps. Both independent molecules (labelled A and B) show sp²-hybridization-related electron delocalization over atoms O6, C6, C1, C7 and O7, and atoms C1, C2 and O2; this delocalization is manifested in both molecules by an average C—C bond length of 1.435 Å (Table 1). In addition, the C2A=O2A and C2B=O2B bond lengths [1.218 (3) and 1.217 (3) Å, respectively] exhibit the properties of regular double bonds, while the C=O bond lengths of the two sp² centers at C6 and C7 are significantly elongated in both molecules (see Fig. 1 and Table 1) and have bond orders that are intermediate between double and single bonds. The strong intramolecular hydrogen bonds between atoms O6A and O7A, and atoms O6B and O7B (Table 2), in which the H atom appears not to be strictly covalently bonded to either O atom, are nearly identical within statistical significance, but in molecule B, the H atom appears to be more localized at atom O6 (see Fig. 1 and Table 2). We attribute the signal at 18.28 p.p.m. in the ¹H NMR spectrum of (I) to the H atom involved in these strong intramolecular hydrogen bonds. In solution, these differences in intramolecular hydrogen bonding disappear, as only a single resonance is observed in this region of the NMR spectrum. This fact is consistent with the possibility that any differences between molecules A and B may be related to the packing in the crystal structure, as discussed below. The cyclohexane-2,6-dione system of (I) shows an envelope-like conformation, similar to that reported for (5R,S,6R,S)-2-acetyl-3,5,6-trihydroxy-5,6- dimethyl-2-cyclohexenone, (II) (Adembri et al., 1988). Like (I), (II) forms a very strong intramolecular hydrogen bond, and these hydrogen bonds are favoured by the presence of conjugated systems in both cases. The least- squares planes through these conjugated systems [HO7(6)···O6—C6—C1—C7—O7] for both molecules of (I) show a maximum deviation of 0.034 (2) Å. Each molecule also contains an additional intramolecular hydrogen bond, between hydroxy atom the O3 and neighboring O2 carbonyl groups (Table 2), but in this case, the hydrogen bonding is more traditional, with atom HO3 in both molecules uniquely bonded to the hydroxy O atom. This bond leads to a lack of protonation at atoms O2A and O2B, the HO3A···O2A and HO3B···O2B distances [1.83 (3) and 1.95 (4) Å] being significantly longer than all other hydrogen bonds present in the two molecules (see Table 2). As a consequence, atoms HO3A and H03B belong to normal alcohol functions bonded to sp³ centers, their signals occurring at 4.04 p.p.m. in the ¹H NMR spectrum. The C—O bond lengths at these sp³ centers [1.416 (3) and 1.403 (4) Å] are typical of single bonds.

The packing in the present structure of (I) features an alternating head-to- tail arrangement (Fig. 2). This is induced by an approximate center of symmetry at the origin. The symmetry breaks down at the chiral atom C3, while the pseudo-center of symmetry extends otherwise throughout the entire packing scheme. A survey of the literature has yielded at least one additional structure where a pseudo-center of symmetry occurs in space group P1 (Olovsson et al., 2001). Consistent with the existence of the approximate center of symmetry in the crystal structure, we have observed that the average absolute value of E*E-1 for (I) is 1.027, clearly consistent with the presence of the pseudo-center.

As anticipated by the presence of approximate symmetry, we have observed that overall the conformations of the two molecules are nearly identical. An exception is the ring O2—C2—C3—O3 torsion angle, which is −16.9 (3)° in molecule A and −12.7 (3)° in molecule B. This small, but significant difference may be related to a close intermolecular contact between molecules A, in which atom O6A is 2.57 Å from H3A, the H atom bonded to C3A in a symmetry-related molecule [symmetry code: x − 1, y, z; Fig. 2]. The fact that this close approach occurs uniquely for only one molecule, but not for the other, clearly shows that the pseudo-center of symmetry at (0, 0, 0) is disrupted by the presence of only one enantiomer of (I). Thus, the analogous H atom, H3B attached to C3B, of the second molecule [symmetry code: x − 1, y, z] points away from atom O6B (see Figs. 1 and 2) and no close approach is possible. It seems likely that this packing difference has an influence on the intramolecular hydrogen bonds between atoms O6 and O7 in both molecules. The close contact removes electron density from atom O6A, and therefore atom HO7A is located closer to atom O7A in molecule A than atom HO6B is to atom O6B in molecule B (see Fig. 1 and 2).

In summary, (I) belongs to the group of arylalkanones or acylaryl-recorcinoles that have been found in several species of Virola (Myristicaceae plant family), for example V. elongata (Kato et al., 1985), V. surinamensis (Blumenthal et al., 1997), V. sebifera (Kato et al., 1985) and V. venosa (Kato et al., 1992), in the last of which this compound has been detected in the fruits. By contrast, this article reports, for the first time, the presence of (I) in the bark of the plant; the hydrogen bonding in (I) has been established.

S2. Experimental

A sample of Virola venosa bark was collected in the Amacayacu National Park in the Colombian Amazon region. The botanical determination was realised by Roberto J. Mejia from the Institute of Science, Universidad Nacional de Colombia. A voucher specimen of the plant has been deposited in the National Herbarium of Colombia, No COL-366258. For the isolation of the compound, the dried and ground bark (1.8 kg) was extracted with ethanol (96%) at ambient temperature. After removal of the solvent, the crude extract (27 g) was treated with petroleum ether (b.p. 233–353 K), yielding, after evaporation of the solvent, a liquid (4.30 g) and a solid phase (6.10 g). The solid phase (5.0 g) was washed with methanol (3 × 2 ml) to afford the dry crude product (380 mg). Flash column chromatography was performed using a mixture of toluene/ethyl acetate (98:2) and silica gel Merck G. The combined fractions containing the compound were evaporated to dryness to yield the pure arylalkanone (184 mg). Crystallization was realised in methanol, yielding colourless geometrically homogeneous needles with a melting point of 325–326 K. The spectroscopic data are more accurate than but in agreement with literature data (Kato et al., 1985).

S3. Refinement

The absolute configuration could not be determined because of the absence of a strong anomalous scatterer in the crystal. Therefore, for the final refinement, 199 Friedel pairs were merged.

Computing details

Data collection: KappaCCD Software (Nonius, 1997); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1998); software used to prepare material for publication: SHELXTL-Plus.

Figures

	Fig. 1. A view of the two molecules of (I) present in the unit cell, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 20% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A packing plot, showing the alternating head-to-tail arrangement of (I) and the shortest intermolecular contact approach. Displacement ellipsoids are drawn at the 20% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry codes: (i) x − 1, y, z; (ii) x + 1, y, z.]

1-(11'-Phenylundecanoyl)-3-hydroxycyclohexane-2,6-dione

Crystal data

C23H32O4	Z = 2
Mr = 372.49	F(000) = 404
Triclinic, P1	Dx = 1.189 Mg m^−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0335 (1) Å	Cell parameters from 17747 reflections
b = 9.4122 (2) Å	θ = 1.0–27.5°
c = 18.7857 (4) Å	µ = 0.08 mm^−1
α = 81.175 (1)°	T = 243 K
β = 89.271 (1)°	Needle, colourless
γ = 80.703 (2)°	0.60 × 0.52 × 0.33 mm
V = 1040.26 (4) Å^3

Data collection

Nonius Kappa CCD diffractometer	4108 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 27.6°, θmin = 2.2°
ϕ and ω scans	h = −7→7
7771 measured reflections	k = −12→12
4803 independent reflections	l = −24→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0647P)^2 + 0.0674P] where P = (Fo^2 + 2Fc^2)/3
4604 reflections	(Δ/σ)max < 0.001
499 parameters	Δρmax = 0.16 e Å^−3
3 restraints	Δρmin = −0.13 e Å^−3

Special details

Experimental. IR (film, cm⁻¹): 3423, 3054, 3027, 2922, 1665, 1547, 1464, 1405, 1105, 755, 725, 704; ¹H NMR (600 MHz, 0.10 M in CDCl3, 298 K): δ 1.31 (12H, m, H-4'-H-9'), 1.62 (4H, m, H-3' and H-10'), 2.38 (1H, m, H-4), 1.81 (1H, qd, J = 6.49, 12.44 and 12.90 Hz, H-4'), 2.59 (2H, t, J = 7.55 Hz, H-11'), 2.78 (2H, dd, J = 11.5 and 4.64 Hz, H-5), 2.98 (1H, ddd, J = 15.61, 8.77 and 6.27 Hz, H-2'), 3.06 (1H, ddd, J = 6.27, 8.77 and 15.61 Hz, H-2''), 4.04 (1H, s, HO3A and HO3B, see text), 4.08 (1H, dd, J = 5.35 and 5.41 Hz, H-3), 7.15–7.28 (5H, m, Ar—H), 18.28 (1H, s, HO7A and HO6B, see text); ¹³C NMR (150 MHz, 0.10 M in CDCl3, 298 K): δ 109.56 (C-1), 195.55 (C-2), 71.57 (C-3), 27.11 (C-4), 31.27 (C-5), 197.90 (C-6), 206.09 (C-1'), 40.25 (C-2'), 24.50 (C-3'), 29.29–29.48 (C-4',5', 6',7',8' and 9'), 31.51 (C-10'), 35.95 (C-11'), 142.91 (C-12'), 128.18 (C-13' and C-17'), 128.36 (C-14' and C-16'), 125.51 (C-15'); EIMS m/z (relative intensity): 372 [M] (82), 183 (77), 91 (100), 69 (42), 55 (44).

Geometry. Mean-plane data from final SHELXL refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 3.1250 (0.0392) x + 7.0776 (0.0110) y + 11.7765 (0.0761) z = 3.9431 (0.0078) * 0.0341 (0.0210) HO7A * −0.0226 (0.0108) O6A * 0.0110 (0.0018) C6A * −0.0071 (0.0044) C1A * 0.0063 (0.0024) C7A * −0.0217 (0.0118) O7A Rms deviation of fitted atoms = 0.0198 − 3.4170 (0.0407) x − 7.0756 (0.0217) y − 10.9971 (0.0702) z = 3.9079 (0.0050) A ngle to previous plane (with approximate e.s.d.) = 3.68 (0.85) * −0.0093 (0.0197) HO6B * 0.0107 (0.0125) O6B * −0.0045 (0.0024) C6B * −0.0013 (0.0052) C1B * 0.0036 (0.0016) C7B * 0.0007 (0.0105) O7B Rms deviation of fitted atoms = 0.0063

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O2A	−0.0405 (4)	0.0075 (2)	0.34116 (13)	0.0662 (6)
O3A	−0.1282 (4)	−0.1524 (3)	0.45876 (12)	0.0723 (6)
HO3A	−0.211 (5)	−0.064 (4)	0.4155 (18)	0.080*
O6A	0.6698 (3)	−0.2753 (2)	0.32062 (12)	0.0629 (5)
O7A	0.5618 (3)	−0.0716 (3)	0.22692 (11)	0.0645 (5)
HO7A	0.648 (6)	−0.165 (4)	0.2648 (19)	0.080*
C1A	0.3227 (4)	−0.1226 (3)	0.32230 (13)	0.0379 (5)
C2A	0.1085 (4)	−0.0955 (3)	0.35867 (12)	0.0421 (5)
C3A	0.0599 (4)	−0.2108 (3)	0.42048 (12)	0.0518 (5)
H3A	0.0205	−0.2941	0.3997	0.062*
C4A	0.2654 (5)	−0.2645 (4)	0.46681 (14)	0.0682 (7)
H4A	0.2314	−0.3354	0.5077	0.082*
H4C	0.3135	−0.1828	0.4858	0.082*
C5A	0.4521 (5)	−0.3351 (3)	0.42284 (16)	0.0579 (7)
H5A	0.5927	−0.3545	0.4508	0.069*
H5C	0.4173	−0.4287	0.4134	0.069*
C6A	0.4837 (4)	−0.2416 (3)	0.35261 (14)	0.0462 (6)
C7A	0.3769 (4)	−0.0362 (3)	0.25714 (13)	0.0426 (5)
C8A	0.2267 (4)	0.0953 (3)	0.21875 (13)	0.0440 (6)
H8A	0.3180	0.1626	0.1923	0.053*
H8C	0.1371	0.1461	0.2539	0.053*
C9A	0.0699 (4)	0.0476 (2)	0.16586 (13)	0.0408 (5)
H9A	0.1607	−0.0014	0.1304	0.049*
H9C	−0.0169	−0.0223	0.1925	0.049*
C10A	−0.0906 (4)	0.1768 (2)	0.12686 (13)	0.0428 (5)
H10A	−0.0033	0.2478	0.1015	0.051*
H10C	−0.1834	0.2242	0.1624	0.051*
C11A	−0.2439 (4)	0.1329 (3)	0.07266 (12)	0.0409 (5)
H11A	−0.1511	0.0900	0.0357	0.049*
H11C	−0.3251	0.0581	0.0976	0.049*
C12A	−0.4131 (5)	0.2600 (3)	0.03609 (13)	0.0438 (5)
H12A	−0.3318	0.3330	0.0094	0.053*
H12C	−0.5014	0.3057	0.0731	0.053*
C13A	−0.5724 (5)	0.2152 (3)	−0.01548 (13)	0.0454 (6)
H13A	−0.6562	0.1441	0.0116	0.055*
H13C	−0.4835	0.1670	−0.0516	0.055*
C14A	−0.7393 (5)	0.3419 (3)	−0.05417 (13)	0.0442 (6)
H14A	−0.8320	0.3883	−0.0183	0.053*
H14C	−0.6560	0.4145	−0.0802	0.053*
C15A	−0.8918 (4)	0.2956 (2)	−0.10704 (13)	0.0452 (6)
H15A	−0.7991	0.2375	−0.1388	0.054*
H15C	−0.9892	0.2331	−0.0801	0.054*
C16A	−1.0375 (4)	0.4222 (2)	−0.15295 (12)	0.0419 (5)
H16A	−0.9417	0.4905	−0.1757	0.050*
H16C	−1.1426	0.4738	−0.1217	0.050*
C17A	−1.1705 (5)	0.3758 (3)	−0.21130 (14)	0.0466 (6)
H17A	−1.0714	0.3057	−0.2356	0.056*
H17C	−1.2914	0.3270	−0.1889	0.056*
C18A	−1.2705 (4)	0.5036 (3)	−0.26626 (12)	0.0395 (5)
C19A	−1.1394 (5)	0.5588 (3)	−0.32165 (14)	0.0493 (6)
H19A	−0.9901	0.5135	−0.3260	0.059*
C20A	−1.2260 (6)	0.6795 (3)	−0.37056 (15)	0.0646 (8)
H20A	−1.1358	0.7161	−0.4079	0.077*
C21A	−1.4444 (6)	0.7460 (3)	−0.36460 (17)	0.0670 (9)
H21A	−1.5035	0.8277	−0.3982	0.080*
C22A	−1.5752 (5)	0.6942 (3)	−0.31029 (19)	0.0656 (8)
H22A	−1.7238	0.7407	−0.3061	0.079*
C23A	−1.4893 (5)	0.5732 (3)	−0.26133 (17)	0.0553 (7)
H23A	−1.5809	0.5376	−0.2241	0.066*
O2B	0.0449 (4)	−0.0104 (2)	−0.33792 (13)	0.0665 (5)
O3B	0.1134 (6)	0.1180 (3)	−0.46606 (14)	0.0900 (8)
HO3B	0.153 (6)	0.044 (4)	−0.435 (2)	0.080*
O6B	−0.6660 (4)	0.2709 (2)	−0.32371 (13)	0.0679 (6)
HO6B	−0.678 (6)	0.203 (4)	−0.2745 (19)	0.080*
O7B	−0.5618 (3)	0.0716 (3)	−0.22691 (11)	0.0616 (5)
C1B	−0.3261 (4)	0.1108 (3)	−0.32518 (12)	0.0396 (5)
C2B	−0.1196 (5)	0.0732 (3)	−0.36372 (13)	0.0465 (6)
C3B	−0.1093 (5)	0.1422 (3)	−0.44265 (12)	0.0575 (6)
H3B	−0.2033	0.0958	−0.4721	0.069*
C4B	−0.2010 (6)	0.3032 (3)	−0.45004 (15)	0.0679 (7)
H4B	−0.1936	0.3482	−0.5005	0.082*
H4D	−0.1098	0.3503	−0.4209	0.082*
C5B	−0.4423 (6)	0.3249 (3)	−0.42520 (17)	0.0657 (8)
H5B	−0.4882	0.4278	−0.4206	0.079*
H5D	−0.5379	0.3027	−0.4625	0.079*
C6B	−0.4836 (5)	0.2337 (3)	−0.35508 (14)	0.0477 (6)
C7B	−0.3787 (4)	0.0301 (3)	−0.25736 (13)	0.0425 (5)
C8B	−0.2298 (4)	−0.1000 (3)	−0.21840 (13)	0.0437 (6)
H8B	−0.1402	−0.1515	−0.2533	0.052*
H8D	−0.3220	−0.1668	−0.1920	0.052*
C9B	−0.0727 (4)	−0.0546 (3)	−0.16542 (12)	0.0410 (5)
H9B	0.0154	0.0148	−0.1918	0.049*
H9D	−0.1630	−0.0053	−0.1299	0.049*
C10B	0.0860 (4)	−0.1843 (2)	−0.12641 (13)	0.0435 (5)
H10B	0.1773	−0.2327	−0.1620	0.052*
H10D	−0.0025	−0.2542	−0.1008	0.052*
C11B	0.2406 (5)	−0.1414 (3)	−0.07293 (13)	0.0419 (5)
H11B	0.1491	−0.0976	−0.0360	0.050*
H11D	0.3226	−0.0674	−0.0982	0.050*
C12B	0.4098 (5)	−0.2694 (3)	−0.03609 (13)	0.0430 (5)
H12B	0.3281	−0.3423	−0.0095	0.052*
H12D	0.4988	−0.3150	−0.0730	0.052*
C13B	0.5678 (4)	−0.2236 (3)	0.01580 (13)	0.0439 (6)
H13B	0.6524	−0.1528	−0.0111	0.053*
H13D	0.4783	−0.1753	0.0518	0.053*
C14B	0.7329 (5)	−0.3513 (3)	0.05447 (13)	0.0442 (6)
H14B	0.8248	−0.3984	0.0186	0.053*
H14D	0.6487	−0.4231	0.0807	0.053*
C15B	0.8870 (4)	−0.3045 (2)	0.10729 (13)	0.0440 (5)
H15B	0.9850	−0.2426	0.0802	0.053*
H15D	0.7950	−0.2460	0.1391	0.053*
C16B	1.0315 (4)	−0.4323 (3)	0.15312 (13)	0.0430 (5)
H16B	1.1353	−0.4846	0.1218	0.052*
H16D	0.9346	−0.4998	0.1761	0.052*
C17B	1.1678 (5)	−0.3855 (3)	0.21184 (14)	0.0488 (6)
H17B	1.2886	−0.3372	0.1891	0.059*
H17D	1.0695	−0.3149	0.2361	0.059*
C18B	1.2680 (4)	−0.5120 (3)	0.26692 (12)	0.0393 (5)
C19B	1.1387 (5)	−0.5677 (3)	0.32247 (14)	0.0481 (6)
H19B	0.9886	−0.5236	0.3264	0.058*
C20B	1.2262 (6)	−0.6869 (3)	0.37218 (14)	0.0579 (7)
H20B	1.1354	−0.7240	0.4092	0.069*
C21B	1.4466 (6)	−0.7513 (3)	0.36747 (17)	0.0633 (8)
H21B	1.5068	−0.8319	0.4014	0.076*
C22B	1.5787 (5)	−0.6970 (4)	0.31271 (19)	0.0648 (8)
H22B	1.7293	−0.7405	0.3093	0.078*
C23B	1.4892 (5)	−0.5789 (3)	0.26306 (16)	0.0508 (6)
H23B	1.5800	−0.5429	0.2258	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2A	0.0541 (12)	0.0554 (11)	0.0751 (13)	0.0136 (9)	0.0123 (10)	0.0093 (10)
O3A	0.0717 (14)	0.0859 (15)	0.0579 (11)	−0.0122 (11)	0.0205 (10)	−0.0081 (10)
O6A	0.0357 (10)	0.0707 (13)	0.0758 (13)	0.0085 (9)	−0.0061 (9)	−0.0081 (11)
O7A	0.0439 (11)	0.0882 (15)	0.0553 (11)	−0.0043 (10)	0.0063 (9)	0.0006 (11)
C1A	0.0328 (11)	0.0403 (11)	0.0392 (11)	−0.0030 (9)	−0.0073 (9)	−0.0040 (9)
C2A	0.0431 (13)	0.0431 (12)	0.0383 (11)	−0.0035 (10)	−0.0019 (9)	−0.0037 (9)
C3A	0.0526 (12)	0.0555 (13)	0.0462 (11)	−0.0092 (10)	0.0018 (9)	−0.0043 (10)
C4A	0.0783 (17)	0.0771 (19)	0.0443 (12)	−0.0142 (14)	−0.0125 (12)	0.0093 (12)
C5A	0.0536 (15)	0.0521 (15)	0.0611 (16)	−0.0020 (12)	−0.0201 (13)	0.0077 (12)
C6A	0.0390 (14)	0.0443 (14)	0.0528 (13)	−0.0021 (11)	−0.0138 (11)	−0.0034 (11)
C7A	0.0397 (14)	0.0480 (14)	0.0402 (12)	−0.0079 (10)	−0.0084 (10)	−0.0054 (11)
C8A	0.0494 (15)	0.0424 (13)	0.0397 (12)	−0.0126 (11)	−0.0127 (11)	0.0015 (10)
C9A	0.0468 (14)	0.0346 (11)	0.0395 (11)	−0.0053 (10)	−0.0087 (10)	−0.0017 (9)
C10A	0.0517 (15)	0.0354 (12)	0.0396 (12)	−0.0039 (10)	−0.0103 (10)	−0.0031 (10)
C11A	0.0500 (14)	0.0331 (11)	0.0370 (11)	−0.0027 (10)	−0.0089 (10)	−0.0008 (9)
C12A	0.0560 (15)	0.0332 (11)	0.0392 (11)	0.0005 (10)	−0.0116 (11)	−0.0030 (9)
C13A	0.0557 (16)	0.0349 (12)	0.0441 (13)	−0.0043 (11)	−0.0103 (12)	−0.0031 (10)
C14A	0.0534 (15)	0.0347 (12)	0.0412 (12)	0.0004 (10)	−0.0101 (11)	−0.0023 (10)
C15A	0.0573 (16)	0.0324 (12)	0.0438 (12)	−0.0036 (11)	−0.0114 (11)	−0.0017 (10)
C16A	0.0509 (14)	0.0326 (11)	0.0399 (11)	−0.0024 (10)	−0.0081 (10)	−0.0022 (9)
C17A	0.0536 (15)	0.0350 (12)	0.0499 (13)	−0.0079 (11)	−0.0118 (12)	−0.0003 (11)
C18A	0.0385 (13)	0.0385 (12)	0.0405 (11)	−0.0016 (9)	−0.0107 (10)	−0.0067 (9)
C19A	0.0507 (16)	0.0501 (14)	0.0444 (13)	−0.0002 (12)	0.0009 (11)	−0.0070 (11)
C20A	0.086 (2)	0.0645 (19)	0.0427 (15)	−0.0159 (17)	0.0010 (15)	−0.0044 (14)
C21A	0.090 (3)	0.0475 (15)	0.0581 (17)	−0.0014 (16)	−0.0382 (17)	0.0003 (13)
C22A	0.0442 (16)	0.0575 (17)	0.089 (2)	0.0087 (13)	−0.0256 (16)	−0.0066 (16)
C23A	0.0398 (15)	0.0591 (16)	0.0653 (17)	−0.0067 (13)	−0.0017 (13)	−0.0055 (14)
O2B	0.0531 (12)	0.0650 (12)	0.0682 (12)	0.0126 (10)	0.0098 (10)	0.0070 (10)
O3B	0.114 (2)	0.0755 (15)	0.0711 (14)	−0.0006 (14)	0.0454 (14)	−0.0019 (12)
O6B	0.0522 (12)	0.0649 (12)	0.0761 (14)	0.0144 (10)	−0.0051 (11)	−0.0025 (11)
O7B	0.0461 (11)	0.0770 (13)	0.0562 (11)	−0.0034 (10)	0.0078 (9)	−0.0001 (10)
C1B	0.0452 (13)	0.0357 (11)	0.0362 (11)	−0.0020 (10)	−0.0087 (10)	−0.0043 (9)
C2B	0.0521 (15)	0.0375 (11)	0.0470 (12)	0.0005 (10)	0.0023 (11)	−0.0057 (10)
C3B	0.0788 (16)	0.0508 (12)	0.0403 (11)	−0.0032 (11)	0.0101 (11)	−0.0068 (9)
C4B	0.093 (2)	0.0475 (13)	0.0540 (14)	0.0008 (13)	0.0085 (14)	0.0068 (11)
C5B	0.080 (2)	0.0506 (16)	0.0547 (16)	0.0067 (14)	−0.0148 (15)	0.0104 (12)
C6B	0.0481 (16)	0.0445 (13)	0.0487 (13)	0.0010 (11)	−0.0108 (12)	−0.0092 (11)
C7B	0.0401 (14)	0.0451 (13)	0.0425 (12)	−0.0086 (10)	−0.0055 (11)	−0.0056 (11)
C8B	0.0519 (15)	0.0384 (12)	0.0408 (12)	−0.0128 (11)	−0.0038 (11)	−0.0005 (10)
C9B	0.0467 (14)	0.0371 (12)	0.0383 (11)	−0.0062 (10)	−0.0052 (10)	−0.0025 (9)
C10B	0.0543 (15)	0.0348 (12)	0.0409 (12)	−0.0070 (11)	−0.0078 (11)	−0.0035 (10)
C11B	0.0522 (15)	0.0345 (12)	0.0368 (11)	−0.0021 (10)	−0.0081 (10)	−0.0031 (9)
C12B	0.0534 (15)	0.0332 (11)	0.0410 (12)	−0.0036 (10)	−0.0094 (11)	−0.0042 (10)
C13B	0.0541 (15)	0.0344 (12)	0.0400 (12)	0.0020 (10)	−0.0132 (11)	−0.0036 (10)
C14B	0.0545 (15)	0.0341 (12)	0.0423 (12)	−0.0013 (11)	−0.0098 (11)	−0.0060 (10)
C15B	0.0498 (14)	0.0357 (12)	0.0440 (12)	−0.0006 (10)	−0.0113 (11)	−0.0045 (10)
C16B	0.0468 (14)	0.0367 (12)	0.0441 (12)	−0.0031 (10)	−0.0099 (10)	−0.0048 (10)
C17B	0.0548 (16)	0.0395 (13)	0.0512 (14)	−0.0051 (11)	−0.0175 (12)	−0.0048 (11)
C18B	0.0372 (13)	0.0397 (12)	0.0414 (12)	−0.0062 (10)	−0.0044 (10)	−0.0069 (10)
C19B	0.0445 (14)	0.0527 (15)	0.0479 (13)	−0.0064 (12)	0.0042 (11)	−0.0120 (11)
C20B	0.081 (2)	0.0556 (16)	0.0367 (13)	−0.0166 (15)	0.0013 (13)	−0.0002 (12)
C21B	0.080 (2)	0.0480 (16)	0.0562 (16)	0.0006 (15)	−0.0280 (16)	−0.0001 (13)
C22B	0.0472 (16)	0.0594 (17)	0.083 (2)	0.0087 (13)	−0.0160 (16)	−0.0131 (16)
C23B	0.0385 (14)	0.0542 (15)	0.0568 (14)	−0.0022 (12)	0.0009 (12)	−0.0052 (12)

Geometric parameters (Å, º)

O2A—C2A	1.218 (3)	O2B—C2B	1.217 (3)
O3A—C3A	1.416 (3)	O3B—C3B	1.403 (4)
O3A—HO3A	1.13 (3)	O3B—HO3B	0.84 (4)
O6A—C6A	1.284 (3)	O6B—C6B	1.266 (4)
O6A—HO7A	1.35 (4)	O6B—HO6B	1.05 (4)
O7A—C7A	1.265 (3)	O7B—C7B	1.270 (3)
O7A—HO7A	1.10 (4)	C1B—C6B	1.420 (3)
C1A—C6A	1.410 (3)	C1B—C7B	1.439 (4)
C1A—C7A	1.427 (4)	C1B—C2B	1.455 (4)
C1A—C2A	1.459 (3)	C2B—C3B	1.530 (3)
C2A—C3A	1.523 (3)	C3B—C4B	1.512 (3)
C3A—C4A	1.497 (3)	C3B—H3B	0.9900
C3A—H3A	0.9900	C4B—C5B	1.515 (5)
C4A—C5A	1.515 (4)	C4B—H4B	0.9800
C4A—H4A	0.9800	C4B—H4D	0.9800
C4A—H4C	0.9800	C5B—C6B	1.499 (4)
C5A—C6A	1.498 (4)	C5B—H5B	0.9800
C5A—H5A	0.9800	C5B—H5D	0.9800
C5A—H5C	0.9800	C7B—C8B	1.493 (3)
C7A—C8A	1.501 (3)	C8B—C9B	1.536 (3)
C8A—C9A	1.543 (3)	C8B—H8B	0.9800
C8A—H8A	0.9800	C8B—H8D	0.9800
C8A—H8C	0.9800	C9B—C10B	1.520 (3)
C9A—C10A	1.523 (3)	C9B—H9B	0.9800
C9A—H9A	0.9800	C9B—H9D	0.9800
C9A—H9C	0.9800	C10B—C11B	1.521 (3)
C10A—C11A	1.529 (3)	C10B—H10B	0.9800
C10A—H10A	0.9800	C10B—H10D	0.9800
C10A—H10C	0.9800	C11B—C12B	1.529 (3)
C11A—C12A	1.522 (3)	C11B—H11B	0.9800
C11A—H11A	0.9800	C11B—H11D	0.9800
C11A—H11C	0.9800	C12B—C13B	1.527 (3)
C12A—C13A	1.523 (3)	C12B—H12B	0.9800
C12A—H12A	0.9800	C12B—H12D	0.9800
C12A—H12C	0.9800	C13B—C14B	1.526 (3)
C13A—C14A	1.526 (3)	C13B—H13B	0.9800
C13A—H13A	0.9800	C13B—H13D	0.9800
C13A—H13C	0.9800	C14B—C15B	1.527 (3)
C14A—C15A	1.520 (3)	C14B—H14B	0.9800
C14A—H14A	0.9800	C14B—H14D	0.9800
C14A—H14C	0.9800	C15B—C16B	1.521 (3)
C15A—C16A	1.518 (3)	C15B—H15B	0.9800
C15A—H15A	0.9800	C15B—H15D	0.9800
C15A—H15C	0.9800	C16B—C17B	1.541 (3)
C16A—C17A	1.523 (3)	C16B—H16B	0.9800
C16A—H16A	0.9800	C16B—H16D	0.9800
C16A—H16C	0.9800	C17B—C18B	1.503 (4)
C17A—C18A	1.510 (3)	C17B—H17B	0.9800
C17A—H17A	0.9800	C17B—H17D	0.9800
C17A—H17C	0.9800	C18B—C19B	1.384 (4)
C18A—C23A	1.384 (4)	C18B—C23B	1.386 (4)
C18A—C19A	1.387 (4)	C19B—C20B	1.382 (4)
C19A—C20A	1.381 (4)	C19B—H19B	0.9400
C19A—H19A	0.9400	C20B—C21B	1.377 (5)
C20A—C21A	1.376 (5)	C20B—H20B	0.9400
C20A—H20A	0.9400	C21B—C22B	1.380 (5)
C21A—C22A	1.361 (5)	C21B—H21B	0.9400
C21A—H21A	0.9400	C22B—C23B	1.378 (4)
C22A—C23A	1.383 (4)	C22B—H22B	0.9400
C22A—H22A	0.9400	C23B—H23B	0.9400
C23A—H23A	0.9400
C3A—O3A—HO3A	99.9 (17)	C3B—O3B—HO3B	95 (3)
C6A—O6A—HO7A	99.6 (15)	C6B—O6B—HO6B	111.5 (19)
C7A—O7A—HO7A	103.5 (18)	C6B—C1B—C7B	117.9 (2)
C6A—C1A—C7A	118.3 (2)	C6B—C1B—C2B	118.9 (2)
C6A—C1A—C2A	118.3 (2)	C7B—C1B—C2B	123.2 (2)
C7A—C1A—C2A	123.5 (2)	O2B—C2B—C1B	124.7 (2)
O2A—C2A—C1A	125.5 (2)	O2B—C2B—C3B	117.6 (2)
O2A—C2A—C3A	117.1 (2)	C1B—C2B—C3B	117.6 (2)
C1A—C2A—C3A	117.3 (2)	O3B—C3B—C4B	111.5 (2)
O3A—C3A—C4A	113.3 (2)	O3B—C3B—C2B	109.3 (2)
O3A—C3A—C2A	109.0 (2)	C4B—C3B—C2B	109.33 (19)
C4A—C3A—C2A	110.1 (2)	O3B—C3B—H3B	108.9
O3A—C3A—H3A	108.1	C4B—C3B—H3B	108.9
C4A—C3A—H3A	108.1	C2B—C3B—H3B	108.9
C2A—C3A—H3A	108.1	C3B—C4B—C5B	109.9 (2)
C3A—C4A—C5A	109.7 (2)	C3B—C4B—H4B	109.7
C3A—C4A—H4A	109.7	C5B—C4B—H4B	109.7
C5A—C4A—H4A	109.7	C3B—C4B—H4D	109.7
C3A—C4A—H4C	109.7	C5B—C4B—H4D	109.7
C5A—C4A—H4C	109.7	H4B—C4B—H4D	108.2
H4A—C4A—H4C	108.2	C6B—C5B—C4B	114.7 (2)
C6A—C5A—C4A	112.3 (2)	C6B—C5B—H5B	108.6
C6A—C5A—H5A	109.1	C4B—C5B—H5B	108.6
C4A—C5A—H5A	109.1	C6B—C5B—H5D	108.6
C6A—C5A—H5C	109.1	C4B—C5B—H5D	108.6
C4A—C5A—H5C	109.1	H5B—C5B—H5D	107.6
H5A—C5A—H5C	107.9	O6B—C6B—C1B	121.4 (3)
O6A—C6A—C1A	120.8 (2)	O6B—C6B—C5B	117.0 (3)
O6A—C6A—C5A	115.9 (2)	C1B—C6B—C5B	121.7 (3)
C1A—C6A—C5A	123.3 (3)	O7B—C7B—C1B	119.0 (3)
O7A—C7A—C1A	119.5 (3)	O7B—C7B—C8B	116.4 (2)
O7A—C7A—C8A	115.4 (2)	C1B—C7B—C8B	124.5 (2)
C1A—C7A—C8A	125.0 (2)	C7B—C8B—C9B	110.76 (19)
C7A—C8A—C9A	109.55 (19)	C7B—C8B—H8B	109.5
C7A—C8A—H8A	109.8	C9B—C8B—H8B	109.5
C9A—C8A—H8A	109.8	C7B—C8B—H8D	109.5
C7A—C8A—H8C	109.8	C9B—C8B—H8D	109.5
C9A—C8A—H8C	109.8	H8B—C8B—H8D	108.1
H8A—C8A—H8C	108.2	C10B—C9B—C8B	112.05 (18)
C10A—C9A—C8A	111.70 (18)	C10B—C9B—H9B	109.2
C10A—C9A—H9A	109.3	C8B—C9B—H9B	109.2
C8A—C9A—H9A	109.3	C10B—C9B—H9D	109.2
C10A—C9A—H9C	109.3	C8B—C9B—H9D	109.2
C8A—C9A—H9C	109.3	H9B—C9B—H9D	107.9
H9A—C9A—H9C	107.9	C9B—C10B—C11B	112.73 (17)
C9A—C10A—C11A	112.73 (17)	C9B—C10B—H10B	109.0
C9A—C10A—H10A	109.0	C11B—C10B—H10B	109.0
C11A—C10A—H10A	109.0	C9B—C10B—H10D	109.0
C9A—C10A—H10C	109.0	C11B—C10B—H10D	109.0
C11A—C10A—H10C	109.0	H10B—C10B—H10D	107.8
H10A—C10A—H10C	107.8	C10B—C11B—C12B	113.44 (18)
C12A—C11A—C10A	113.20 (17)	C10B—C11B—H11B	108.9
C12A—C11A—H11A	108.9	C12B—C11B—H11B	108.9
C10A—C11A—H11A	108.9	C10B—C11B—H11D	108.9
C12A—C11A—H11C	108.9	C12B—C11B—H11D	108.9
C10A—C11A—H11C	108.9	H11B—C11B—H11D	107.7
H11A—C11A—H11C	107.8	C13B—C12B—C11B	112.69 (17)
C11A—C12A—C13A	113.20 (18)	C13B—C12B—H12B	109.1
C11A—C12A—H12A	108.9	C11B—C12B—H12B	109.1
C13A—C12A—H12A	108.9	C13B—C12B—H12D	109.1
C11A—C12A—H12C	108.9	C11B—C12B—H12D	109.1
C13A—C12A—H12C	108.9	H12B—C12B—H12D	107.8
H12A—C12A—H12C	107.8	C14B—C13B—C12B	113.09 (18)
C12A—C13A—C14A	113.93 (18)	C14B—C13B—H13B	109.0
C12A—C13A—H13A	108.8	C12B—C13B—H13B	109.0
C14A—C13A—H13A	108.8	C14B—C13B—H13D	109.0
C12A—C13A—H13C	108.8	C12B—C13B—H13D	109.0
C14A—C13A—H13C	108.8	H13B—C13B—H13D	107.8
H13A—C13A—H13C	107.7	C13B—C14B—C15B	112.60 (18)
C15A—C14A—C13A	113.10 (18)	C13B—C14B—H14B	109.1
C15A—C14A—H14A	109.0	C15B—C14B—H14B	109.1
C13A—C14A—H14A	109.0	C13B—C14B—H14D	109.1
C15A—C14A—H14C	109.0	C15B—C14B—H14D	109.1
C13A—C14A—H14C	109.0	H14B—C14B—H14D	107.8
H14A—C14A—H14C	107.8	C16B—C15B—C14B	113.13 (18)
C16A—C15A—C14A	113.71 (18)	C16B—C15B—H15B	109.0
C16A—C15A—H15A	108.8	C14B—C15B—H15B	109.0
C14A—C15A—H15A	108.8	C16B—C15B—H15D	109.0
C16A—C15A—H15C	108.8	C14B—C15B—H15D	109.0
C14A—C15A—H15C	108.8	H15B—C15B—H15D	107.8
H15A—C15A—H15C	107.7	C15B—C16B—C17B	112.97 (18)
C15A—C16A—C17A	113.33 (18)	C15B—C16B—H16B	109.0
C15A—C16A—H16A	108.9	C17B—C16B—H16B	109.0
C17A—C16A—H16A	108.9	C15B—C16B—H16D	109.0
C15A—C16A—H16C	108.9	C17B—C16B—H16D	109.0
C17A—C16A—H16C	108.9	H16B—C16B—H16D	107.8
H16A—C16A—H16C	107.7	C18B—C17B—C16B	112.52 (19)
C18A—C17A—C16A	112.03 (19)	C18B—C17B—H17B	109.1
C18A—C17A—H17A	109.2	C16B—C17B—H17B	109.1
C16A—C17A—H17A	109.2	C18B—C17B—H17D	109.1
C18A—C17A—H17C	109.2	C16B—C17B—H17D	109.1
C16A—C17A—H17C	109.2	H17B—C17B—H17D	107.8
H17A—C17A—H17C	107.9	C19B—C18B—C23B	117.9 (2)
C23A—C18A—C19A	118.2 (2)	C19B—C18B—C17B	120.4 (2)
C23A—C18A—C17A	121.7 (2)	C23B—C18B—C17B	121.7 (2)
C19A—C18A—C17A	120.0 (2)	C20B—C19B—C18B	121.2 (3)
C20A—C19A—C18A	120.6 (3)	C20B—C19B—H19B	119.4
C20A—C19A—H19A	119.7	C18B—C19B—H19B	119.4
C18A—C19A—H19A	119.7	C21B—C20B—C19B	120.0 (3)
C21A—C20A—C19A	119.9 (3)	C21B—C20B—H20B	120.0
C21A—C20A—H20A	120.0	C19B—C20B—H20B	120.0
C19A—C20A—H20A	120.0	C20B—C21B—C22B	119.8 (3)
C22A—C21A—C20A	120.3 (3)	C20B—C21B—H21B	120.1
C22A—C21A—H21A	119.9	C22B—C21B—H21B	120.1
C20A—C21A—H21A	119.9	C23B—C22B—C21B	119.8 (3)
C21A—C22A—C23A	120.0 (3)	C23B—C22B—H22B	120.1
C21A—C22A—H22A	120.0	C21B—C22B—H22B	120.1
C23A—C22A—H22A	120.0	C22B—C23B—C18B	121.4 (3)
C22A—C23A—C18A	121.0 (3)	C22B—C23B—H23B	119.3
C22A—C23A—H23A	119.5	C18B—C23B—H23B	119.3
C18A—C23A—H23A	119.5
C6A—C1A—C2A—O2A	175.5 (2)	H10A—C10A—C11A—H11C	177.0
C7A—C1A—C2A—O2A	−5.3 (4)	H10C—C10A—C11A—H11A	177.2
C6A—C1A—C2A—C3A	−9.0 (3)	H10C—C10A—C11A—H11C	−65.5
C7A—C1A—C2A—C3A	170.2 (2)	H11A—C11A—C12A—H12A	−60.2
O2A—C2A—C3A—O3A	−16.9 (3)	H11A—C11A—C12A—H12C	−177.5
C1A—C2A—C3A—O3A	167.2 (2)	H11C—C11A—C12A—H12A	−177.5
O2A—C2A—C3A—C4A	−141.8 (3)	H11C—C11A—C12A—H12C	65.2
C1A—C2A—C3A—C4A	42.3 (3)	H12A—C12A—C13A—H13A	−178.6
O3A—C3A—C4A—C5A	175.7 (2)	H12A—C12A—C13A—H13C	64.4
C2A—C3A—C4A—C5A	−61.9 (3)	H12C—C12A—C13A—H13A	−61.3
C3A—C4A—C5A—C6A	49.0 (3)	H12C—C12A—C13A—H13C	−178.3
C7A—C1A—C6A—O6A	−3.2 (3)	H13A—C13A—C14A—H14A	61.1
C2A—C1A—C6A—O6A	176.0 (2)	H13A—C13A—C14A—H14C	178.4
C7A—C1A—C6A—C5A	176.4 (2)	H13C—C13A—C14A—H14A	178.1
C2A—C1A—C6A—C5A	−4.4 (3)	H13C—C13A—C14A—H14C	−64.6
C4A—C5A—C6A—O6A	163.5 (2)	H14A—C14A—C15A—H15A	−172.3
C4A—C5A—C6A—C1A	−16.2 (4)	H14A—C14A—C15A—H15C	−55.2
C6A—C1A—C7A—O7A	2.9 (3)	H14C—C14A—C15A—H15A	70.4
C2A—C1A—C7A—O7A	−176.3 (2)	H14C—C14A—C15A—H15C	−172.6
C6A—C1A—C7A—C8A	−178.80 (19)	H15A—C15A—C16A—H16A	−69.2
C2A—C1A—C7A—C8A	2.0 (3)	H15A—C15A—C16A—H16C	173.5
O7A—C7A—C8A—C9A	90.3 (2)	H15C—C15A—C16A—H16A	173.7
C1A—C7A—C8A—C9A	−88.1 (3)	H15C—C15A—C16A—H16C	56.5
C7A—C8A—C9A—C10A	178.47 (19)	H16A—C16A—C17A—H17A	75.7
C8A—C9A—C10A—C11A	178.5 (2)	H16A—C16A—C17A—H17C	−166.5
C9A—C10A—C11A—C12A	177.1 (2)	H16C—C16A—C17A—H17A	−167.1
C10A—C11A—C12A—C13A	−177.5 (2)	H16C—C16A—C17A—H17C	−49.3
C11A—C12A—C13A—C14A	−178.5 (2)	H17A—C17A—C18A—C19A	−39.9
C12A—C13A—C14A—C15A	178.2 (2)	H17C—C17A—C18A—C19A	−157.7
C13A—C14A—C15A—C16A	−172.4 (2)	H17A—C17A—C18A—C23A	143.2
C14A—C15A—C16A—C17A	173.6 (2)	H17C—C17A—C18A—C23A	25.4
C15A—C16A—C17A—C18A	−166.8 (2)	C17A—C18A—C19A—H19A	2.7
C16A—C17A—C18A—C23A	−95.7 (3)	H19A—C19A—C20A—H20A	−0.1
C16A—C17A—C18A—C19A	81.2 (3)	H19A—C19A—C20A—C21A	179.9
C23A—C18A—C19A—C20A	−0.2 (3)	H20A—C20A—C21A—H21A	0.6
C17A—C18A—C19A—C20A	−177.3 (2)	H20A—C20A—C21A—C22A	−179.4
C18A—C19A—C20A—C21A	−0.1 (4)	H21A—C21A—C22A—H22A	−0.7
C19A—C20A—C21A—C22A	0.6 (4)	H21A—C21A—C22A—C23A	179.3
C20A—C21A—C22A—C23A	−0.7 (4)	H22A—C22A—C23A—H23A	0.4
C21A—C22A—C23A—C18A	0.4 (4)	H22A—C22A—C23A—C18A	−179.6
C19A—C18A—C23A—C22A	0.1 (4)	H23A—C23A—C18A—C17A	−2.9
C17A—C18A—C23A—C22A	177.1 (2)	H23A—C23A—C18A—C19A	−179.9
C6B—C1B—C2B—O2B	165.2 (2)	HO3B—O3B—C3B—H3B	−95.1
C7B—C1B—C2B—O2B	−14.1 (4)	HO3B—O3B—C3B—C2B	24 (3)
C6B—C1B—C2B—C3B	−15.5 (3)	HO3B—O3B—C3B—C4B	145 (2)
C7B—C1B—C2B—C3B	165.1 (2)	H3B—C3B—C4B—H4B	−61.6
O2B—C2B—C3B—O3B	−12.7 (3)	H3B—C3B—C4B—H4D	179.7
C1B—C2B—C3B—O3B	167.9 (2)	H3B—C3B—C2B—O2B	106.1
O2B—C2B—C3B—C4B	−135.0 (3)	H4B—C4B—C5B—H5B	−71.3
C1B—C2B—C3B—C4B	45.7 (3)	H4B—C4B—C5B—H5D	45.4
O3B—C3B—C4B—C5B	179.3 (3)	H4D—C4B—C5B—H5B	47.4
C2B—C3B—C4B—C5B	−59.8 (3)	H4D—C4B—C5B—H5D	164.1
C3B—C4B—C5B—C6B	46.4 (3)	H5B—C5B—C6B—O6B	42.3
C7B—C1B—C6B—O6B	−0.7 (4)	H5D—C5B—C6B—O6B	−74.4
C2B—C1B—C6B—O6B	179.9 (2)	H5B—C5B—C6B—C1B	−138.0
C7B—C1B—C6B—C5B	179.6 (2)	H5D—C5B—C6B—C1B	105.3
C2B—C1B—C6B—C5B	0.2 (4)	C1B—C6B—O6B—HO6B	2 (2)
C4B—C5B—C6B—O6B	164.0 (2)	C5B—C6B—O6B—HO6B	−178 (2)
C4B—C5B—C6B—C1B	−16.3 (4)	O7B—C7B—C8B—H8B	151.6
C6B—C1B—C7B—O7B	−0.2 (3)	O7B—C7B—C8B—H8D	33.3
C2B—C1B—C7B—O7B	179.1 (2)	H8B—C8B—C9B—H9B	63.6
C6B—C1B—C7B—C8B	−179.0 (2)	H8B—C8B—C9B—H9D	−178.6
C2B—C1B—C7B—C8B	0.3 (4)	H8D—C8B—C9B—H9B	−178.1
O7B—C7B—C8B—C9B	−87.5 (3)	H8D—C8B—C9B—H9D	−60.3
C1B—C7B—C8B—C9B	91.3 (3)	H9B—C9B—C10B—H10B	−61.6
C7B—C8B—C9B—C10B	−178.3 (2)	H9B—C9B—C10B—H10D	−179.1
C8B—C9B—C10B—C11B	−179.2 (2)	H9D—C9B—C10B—H10B	−179.3
C9B—C10B—C11B—C12B	−177.0 (2)	H9D—C9B—C10B—H10D	63.2
C10B—C11B—C12B—C13B	178.4 (2)	H10B—C10B—C11B—H11B	−177.1
C11B—C12B—C13B—C14B	178.35 (19)	H10B—C10B—C11B—H11D	65.7
C12B—C13B—C14B—C15B	−178.9 (2)	H10D—C10B—C11B—H11B	−59.6
C13B—C14B—C15B—C16B	172.6 (2)	H10D—C10B—C11B—H11D	−176.8
C14B—C15B—C16B—C17B	−173.8 (2)	H11B—C11B—C12B—H12B	61.0
C15B—C16B—C17B—C18B	167.0 (2)	H11B—C11B—C12B—H12D	178.5
C16B—C17B—C18B—C19B	−80.6 (3)	H11D—C11B—C12B—H12B	178.2
C16B—C17B—C18B—C23B	97.8 (3)	H11D—C11B—C12B—H12D	−64.3
C23B—C18B—C19B—C20B	−0.6 (3)	H12B—C12B—C13B—H13B	178.4
C17B—C18B—C19B—C20B	177.9 (2)	H12B—C12B—C13B—H13D	−64.2
C18B—C19B—C20B—C21B	0.8 (4)	H12D—C12B—C13B—H13B	60.9
C19B—C20B—C21B—C22B	−0.5 (4)	H12D—C12B—C13B—H13D	178.3
C20B—C21B—C22B—C23B	−0.1 (4)	H13B—C13B—C14B—H14B	−61.4
C21B—C22B—C23B—C18B	0.3 (4)	H13B—C13B—C14B—H14D	−179.0
C19B—C18B—C23B—C22B	0.0 (3)	H13D—C13B—C14B—H14B	−178.8
C17B—C18B—C23B—C22B	−178.4 (2)	H13D—C13B—C14B—H14D	63.7
HO3A—O3A—C3A—H3A	−94.0	H14B—C14B—C15B—H15B	55.2
HO3A—O3A—C3A—C2A	23.2 (17)	H14B—C14B—C15B—H15D	172.5
HO3A—O3A—C3A—C4A	146.2 (17)	H14D—C14B—C15B—H15B	172.7
H3A—C3A—C4A—H4A	−64.7	H14D—C14B—C15B—H15D	−70.0
H3A—C3A—C4A—H4C	176.5	H15B—C15B—C16B—H16B	−56.5
H3A—C3A—C2A—O2A	100.4	H15B—C15B—C16B—H16D	−173.8
H4A—C4A—C5A—H5A	−69.2	H15D—C15B—C16B—H16B	−173.8
H4A—C4A—C5A—H5C	48.5	H15D—C15B—C16B—H16D	68.8
H4C—C4A—C5A—H5A	49.6	H16B—C16B—C17B—H17B	49.5
H4C—C4A—C5A—H5C	167.2	H16B—C16B—C17B—H17D	167.1
H5A—C5A—C6A—O6A	42.3	H16D—C16B—C17B—H17B	166.9
H5C—C5A—C6A—O6A	−75.4	H16D—C16B—C17B—H17D	−75.5
H5A—C5A—C6A—C1A	−137.4	H17B—C17B—C18B—C19B	158.2
H5C—C5A—C6A—C1A	105.0	H17D—C17B—C18B—C19B	40.7
C1A—C7A—O7A—HO7A	−4.6 (19)	H17B—C17B—C18B—C23B	−23.4
HO7A—O7A—C7A—C8A	176.9 (18)	H17D—C17B—C18B—C23B	−141.0
HO7A—O7A—C7A—C1A	−4.6 (19)	C17B—C18B—C19B—H19B	−2.1
O7A—C7A—C8A—H8A	−30.3	H19B—C19B—C20B—H20B	0.8
O7A—C7A—C8A—H8C	−149.1	H19B—C19B—C20B—C21B	−179.2
H8A—C8A—C9A—H9A	60.1	H20B—C20B—C21B—H21B	−0.5
H8A—C8A—C9A—H9C	178.0	H20B—C20B—C21B—C22B	179.5
H8C—C8A—C9A—H9A	178.9	H21B—C21B—C22B—H22B	−0.1
H8C—C8A—C9A—H9C	−63.2	H21B—C21B—C22B—C23B	179.9
H9A—C9A—C10A—H10A	−63.8	H22B—C22B—C23B—H23B	0.3
H9A—C9A—C10A—H10C	178.7	H22B—C22B—C23B—C18B	−179.7
H9C—C9A—C10A—H10A	178.3	H23B—C23B—C18B—C17B	1.6
H9C—C9A—C10A—H10C	60.8	H23B—C23B—C18B—C19B	180.0
H10A—C10A—C11A—H11A	59.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3A—HO3A···O2A	1.13 (3)	1.83 (3)	2.576 (3)	119 (2)
O3B—HO3B···O2B	0.84 (4)	1.95 (4)	2.582 (3)	131 (3)
O7A—HO7A···O6A	1.10 (4)	1.35 (4)	2.406 (3)	157 (3)
O6B—HO6B···O7B	1.05 (4)	1.49 (4)	2.413 (3)	143 (3)