Polymorphic forms of lupane triterpenoid betulonic aldehyde (betulonal)

The lupane triterpenoid betulonic aldehyde [also known as betulonal; systematic name: lup-20(29)-en-28-al-3-one, C₃₀H₄₆O₂] is a product of betulin oxidation. Crystals were obtained from hexane [form (I)] and dimethyl sulfoxide [form (II)] solutions. Forms (I) and (II) are both ortho­rhom­bic. The molecular geometric parameters in the two forms are similar, but the structures are different with respect to the crystal packing. Polymorph (I) contains two independent mol­ecules in the asymmetric unit, while polymorph (II) contains only one mol­ecule, which has a disordered aldehyde group [the disorder ratio is 0.769 (4):0.231 (4)]. In each mol­ecule, the six-membered rings have chair conformations, whereas the cyclo­pentane ring in each molecule adopts an envelope conformation. All the rings in the lupane nucleus are trans-fused. The extended structures of both polymorphs are stabilized by weak inter­molecular C—H...O and van der Waals inter­actions. Weak intra­molecular C—H...O inter­actions are also observed.

S1. Introduction

Betulonic aldehyde [lup-20 (29)-en-28-al-3-one] (1), also known as betulonal, is a naturally occurring penta­cyclic triterpene of the lupane type. Betulonal was isolated for the first time in 1966 from the white birch bark (Betula pendula) by extraction with cyclo­hexane (Rimpler et al., 1966). Betulonal has already been identified in the outer bark of Betula nigra (Hua et al., 1991), Betula platyphylla (Kochergina et al., 1986), Betula alleghaniensis (Lavoie & Stevanovic, 2005), Betula pubescens (Abyshev et al., 2007), in the root bark of Maytenus cuzcoina (Núñez et al., 2005), in the leaves of Quercus suber (Monaco & Previtera, 1984), in the ground aerial parts of Boronia gracilipes (Ahsan et al., 1995) and in Chios mastic gum (Dabos et al., 2010). The content of betulonic aldehyde in different plant species is rather low and does not exceed 0.05%. Therefore, it seems that a more efficient method for obtaining the compound consists in a synthesis based on betulin oxidation. In the literature one can find several methods, such as Swern, Jones (Barthel et al., 2008), Oppenauer (Krasutsky & Munshi, 2006) oxidation and the application of pyridinium chloro­chromate (PCC; Hata et al., 2002; Sun et al., 1998; Yli-Kauhaluoma et al., 2010) or pyridinium dichromate (PDC; Dabos et al., 2010).

Oxidation of betulin has a great impact on its biological activity. It was stated that the presence of a carbonyl group at carbon C28 is necessary for high cytotoxicity. Moreover, oxidation of the hy­droxy group at carbon C3 also results in a higher cytotoxicity of the derivatives (for atom and ring numbering see Scheme). Oxidation of betulin (position C3 and/or at C28) affects its binding to topoisomerases I/II (Csuk et al., 2012).

Betulone aldehyde shows in vitro cytotoxic activity against different human cancer lines, viz. MCF7 (breast), NCI-H460 (lung), SF-268 (central nervous system, CNS) and bladder (Saxena & Rathnam, 2009). Betulonal causes melanogenesis in mouse B16 2F2 cells assessed as intra­cellular melanin content and inhibited B16 2F2 cell proliferation by induction of apoptosis (Hata et al., 2002). In addition, betulonal shows anti­viral activity against SFV infected in BHK cells, cytotoxicity against human HuH7 cells (Pohjala et al., 2009), anti-HIV activity in acutely infected H9 lymphocytes (Sun et al., 1998), cytotoxicity against human epidermoid carcinoma of the mouth (KB) cell line, cytotoxicity against cultured human melanoma (MEL-2) cell line (Kim et al., 1998) and anti­leishmanial activity against Leishmania donovani axenic amastigotes (Alakurtti et al., 2010).

This work is a continuation of our earlier studies on determination of the structure of betulin derivatives (Boryczka, Michalik et al., 2012; Boryczka, Bębenek et al., 2012; Boryczka et al., 2013). Until now, the crystal structure of betulonal has not been reported. Betulonic aldehyde was obtained by oxidation of naturally occurring betulin using pyridinium chloro­chromate (PCC) (Yli-Kauhaluoma et al., 2010).

S2. Experimental

S2.1. Synthesis of betulonic aldehyde, (1)

Betulonic aldehyde, (1), was synthesized according to the method of Yli-Kauhaluoma et al. (2010). A mixture of betulin (200 mg, 0.45 mmol), pyridinium chloro­chromate (PCC; 585 mg, 2.72 mmol) and dry di­chloro­methane (5 ml) was stirred at room temperature for 2 h. The reaction mixture was dissolved in di­ethyl ether (10 ml) and filtered through alumina. The filtrate was washed with water, 5% hydro­chloric acid, again with water and dried over Na₂SO₄. The solvent was evaporated in vacuum and the crude product was crystallized from hexane giving 135 mg (68%) of (1). Crystals of (1) suitable for single-crystal X-ray structure analysis were obtained by slow evaporation of hexane [for polymorph (I)] or di­methyl sulfoxide [for polymorph (II)] solution at room temperature.

S2.2. Analysis of betulonic aldehyde, (1)

R_F = 0.74 (silica gel, di­chloro­methane–ethanol, 20:1 v/v), m.p. 433–435 K (literature 436–439 K; Barthel et al., 2008). ¹H NMR (600 MHz, CDCl₃): δ 0.93 (s, 3H, CH₃, H23), 0.96 (s, 3H, CH₃, H24), 0.99 (s, 3H, CH₃, H25), 1.02 (s, 3H, CH₃, H26), 1.07 (s, 3H, CH₃, H27), 1.08–2.11 (22H, CH₂, CH), 1.70 (s, 3H, CH₃, H30), 2.44 (m, 2H, H2), 2.87 (dt, 1H, H19), 4.63 (br s, 1H, H29), 4.76 (br s, 1H, H29), 9.67 (s, 1H, CHO). ¹³C NMR (150 MHz, CDCl₃): δ 14.19 (C27), 15.73 (C25), 15.95 (C26), 19.01 (C30), 19.61 (C6), 21.02 (C24), 21.28 (C11), 25.55 (C12), 26.61 (C23), 28.80 (C22), 29.15 (C21), 29.86 (C15), 33.17 (C16), 33.64 (C7), 34.12 (C2), 36.90 (C10), 38.76 (C13), 39.64 (C1), 40.78 (C8), 42.61 (C14), 47.32 (C4), 47.48 (C19), 47.98 (C18), 49.83 (C9), 54.97 (C5), 59.31 (C17), 110.20 (C29), 149.65 (C20), 206.49 (C28), 217.94 (C3). IR (KBr, cm^-1): ν 3071–2863 (CH₂, CH₃), 1731 (C═O from CHO), 1703 (C═ O), 1644 (C═C), 1451 (CH₃), 871 (═C—H).

S2.3. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. In polymorph (II), the difference Fourier maps showed the presence of two partially occupied rotamers at atom C28. The PART option in SHELXL (Sheldrick, 2008) was used in order to separate the partially occupied moieties; site-occupation factors for the two alternative positions refined to 0.769 (4) and 0.231 (4). For the disordered part of the molecule, restrained refinement was applied using the SADI and SAME instructions in SHELXL (Sheldrick, 2008). H atoms were treated as riding atoms in geometrically idealized positions fixing the C—H bond lengths at 0.95, 1.00, 0.99, 0.95 and 0.98 Å for aromatic CH, methine CH, methyl­ene CH₂, terminal methyl­ene CH₂ and methyl CH₃ atoms, respectively, and with U_iso(H) = 1.5U_eq(C) for methyl H atoms or 1.2U_eq(C) otherwise.

The structure of betulin contains chiral atoms. Previous studies on other triterpene derivatives of the lupane type have shown that these atoms present the following configurations: C3(S), C5(R), C8(R), C9(S), C10(R), C13(R), C14(R), C17(R) and C19(R) for lupeol (Corrêa et al., 2009), and C3(S), C5(R), C8(R), C9(S), C10(R), C13(R), C14(R), C17(S) and C19(R) for 3-acetyl­betulinic acid (Suleimen et al., 2013). Because of the absence of a heavy atom (>Si), the absolute structure of betulonic aldehyde was determined by comparison as follows: C5(R), C8(R), C9(S), C10(R), C13(R), C14(R), C17(S), C18(R) and C19(R).

S3. Results and discussion

Polymorphism may be defined as the ability of a compound to exist in various crystalline forms in which the molecules have different arrangements (packing polymorphism) and/or conformations (conformational polymorphism) in the crystal lattice (Grant, 1999). Forms (I) and (II) of Betulonic aldehyde, (1), both crystallize in the orthorhombic P2₁2₁2₁ space group. The unit cell of polymorph (I) contains eight molecules of (1) (Z' = 2), while polymorph (II) contains only four molecules (Z' = 1).

The asymmetric unit of polymorph (I) contains two independent molecules, viz. (IA) and (IB) (Fig. 1). A similar crystal arrangement was also observed for betulonic alcohol (Boryczka, Bębenek et al., 2012).

In contrast, the asymmetric unit of polymorph (II) consists of only one type of molecule, as shown in Fig. 2.

These structures have different arrangements in the unit cell and they can be regarded as packing polymorphs. In the polymorph (I), the molecules form two-dimensional (ab plane) layers. Fig. 3 shows schematically a packing diagram of polymorph (I) viewed parallel to the a axis. One may see that the molecules are arranged in an ABAB order along the c axis.

The molecules of polymorph (II) reveal a different alignment to that in form (I) (Fig. 4). In this case, they are packed along the c axis in a zigzag fashion parallel to the bc plane.

The geometric parameters of betulonal in both crystal forms are similar. All bond lengths and angles show typical values. The six-membered rings have chair conformations, while the cyclo­pentane ring adopts an envelope conformation. Atom C17 is displaced from the C18/C19/C21/C22 plane by about 0.665 Å in (IA), 0.652 Å in (IB) and 0.649 Å in (II). The C17—C18—C19—C21 and C19—C21—C22—C17 torsion angles are 27.2 (1) and -26.0 (1)° in (IA), 26.7 (1) and -25.4 (1)° in (IB), and 28.3 (1) and -23.4 (1)° in (II), respectively. This is confirmed by the Cremer and Pople parameters (Table 2; Cremer & Pople, 1975). The appropriate calculations were made using PLATON (Spek, 2009).

All the ring junctions in the lupane nucleus are trans-fused. Similar ring conformations were also described for other derivatives of betulin, for example, 3,28-di­acet­oxy-29-bromo­betulin (Ding et al., 2009), 20 (29)-lupene-3β,28β-di­acetate (Mohamed et al., 2006), betulin ethanol solvate (Drebushchak et al., 2010), betulin DMSO solvate (Boryczka, Michalik et al., 2012) and betulinic acid DMSO solvate (Boryczka, Bębenek et al., 2012). In all molecules, (IA), (IB) and (II), the cyclo­hexanone ring A has a chair conformation, like in crystal structures of betulonic alcohol (Boryczka et al., 2013), but different from betulonic acid DMSO and betulonic acid DMF solvates crystal structures, where it adopts the twisted-boat conformation (Boryczka, Jastrzębska et al., 2012). The methyl groups at atoms C24, C25, C26 and C27 occupy the axial positions, while the methyl group at C23 is equatorial. The selected torsion angles describing molecules conformations of the polymorph (I) and (II) are presented in Table 3.

In the polymorph (I), molecules (IA) and (IB) have different orientations of the isopropenyl group (Table 3). The C29—C20—C19—C21 torsion angle describes the orientation of the isopropenyl group and is -99.0 (1)° for (IA) and 93.8 (2)° for (IB). In the case of the molecules in polymorph (II), the orientation of the isopropenyl group is similar to that in molecule (IB). The corresponding torsion angle is 99.5 (1)°.

In all studied cases, the aldehyde group is attached to atom C17 of ring D in an axial orientation. Additionally, in the polymorph (II), two rotamers are observed. The occupancies of the two disordered rotamers are 0.769 (4) and 0.231 (4). Because there is no steric hindrance, the carbonyl group may rotate along the C17—C28 single bond. The values of the torsion angles C18—C17—C28—O2A and C18—C17—C28—O2B in both alternative orientations are -11.7 (2) and +136.5 (4)° for the higher and lower occupancy fragments, respectively. The value of this torsion angle in form (I) is -7.7 (2)° for molecule (IA) and -15.7 (2)° for molecule (IB).

The molecular structure is stabilized only by weak inter­molecular C—H···O hydrogen bonds (Fig. 5) and van der Waals inter­actions. In polymorph (I), weak intra­molecular C—H···O hydrogen bonds are also observed, namely C13—H13···O2 and C19—H19···O2 (Table 4). The absence of such inter­actions in polymorph (II) is associated with the existence of a disorder of axially oriented aldehyde group.

Related literature

For related literature, see: Abyshev et al. (2007); Ahsan et al. (1995); Alakurtti et al. (2010); Barthel et al. (2008); Boryczka et al. (2013); Boryczka, Bębenek, Jastrzębska, Kusz & Zubko (2012); Boryczka, Jastrzębska, Bębenek, Kusz, Zubko, Kadela & Michalik (2012); Boryczka, Michalik, Jastrzębska, Kusz, Zubko & Bębenek (2012); Corrêa et al. (2009); Cremer & Pople (1975); Csuk et al. (2012); Dabos et al. (2010); Ding et al. (2009); Drebushchak (2010); Grant (1999); Hata et al. (2002); Hua et al. (1991); Kim et al. (1998); Kochergina et al. (1986); Krasutsky & Munshi (2006); Lavoie & Stevanovic (2005); Mohamed (2006); Monaco & Previtera (1984); Núñez et al. (2005); Pohjala et al. (2009); Rimpler et al. (1966); Saxena & Rathnam (2009); Sheldrick (2008); Spek (2009); Suleimen et al. (2013); Sun et al. (1998); Yli-Kauhaluoma, Allakurti, Minkkinen, Sarcerdoti-Sierra, Jaffe & Heiska (2010).

Computing details

For both compounds, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006) and PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures

	Fig. 1. Molecular fitting of the two crystallographically independent molecules (IA) and (IB) of polymorph (I) of betulonal.
	Fig. 2. Molecular view of polymorph (II) with only one of the disordered part for the clarity. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 3. (a) Two-dimensional (ab plane) layers of (IA) and (IB) of polymorph (I) and (b) packing diagram of the polymorph (I) viewed parallel to the a axis.
	Fig. 4. (a) The zig zag chain of molecules of polymorph (II) parallel to the bc plane and (b) packing diagram of the polymorph (II) viewed parallel to the b axis.
	Fig. 5. The C—H···O interaction (dashed line) between two independent molecules in polymorph (I) of betulonal. Displacement ellipsoids are drawn at the 50% probability level.

(I_polymorph) Lup-20 (29)-en-28-al-3-one

Crystal data

C30H46O2	F(000) = 1936
Mr = 438.67	Dx = 1.156 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 27663 reflections
a = 9.3905 (2) Å	θ = 2.8–38.4°
b = 19.1080 (3) Å	µ = 0.07 mm^−1
c = 28.0829 (5) Å	T = 100 K
V = 5039.02 (16) Å^3	Polyhedron, colourless
Z = 8	0.48 × 0.38 × 0.17 mm

Data collection

Agilent SuperNova diffractometer with an Atlas detector	16765 independent reflections
Radiation source: Agilent SuperNova (Mo) X-ray Source	15731 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 10.4498 pixels mm^-1	θmax = 31.5°, θmin = 2.1°
ω scans	h = −9→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −28→28
Tmin = 0.757, Tmax = 1.000	l = −41→41
61016 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0392P)^2 + 1.7207P] where P = (Fo^2 + 2Fc^2)/3
16765 reflections	(Δ/σ)max = 0.001
589 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.32 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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 (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.85059 (11)	0.69260 (6)	0.28904 (4)	0.0346 (2)
O2A	−0.12294 (10)	0.48113 (5)	0.13731 (3)	0.02278 (17)
C1A	0.48485 (13)	0.65916 (6)	0.28732 (4)	0.0198 (2)
H1A	0.3961	0.6770	0.3020	0.024*
H1B	0.5129	0.6162	0.3047	0.024*
C2A	0.60225 (13)	0.71417 (7)	0.29323 (5)	0.0237 (2)
H2A	0.5684	0.7594	0.2803	0.028*
H2B	0.6223	0.7207	0.3276	0.028*
C3A	0.73772 (13)	0.69348 (6)	0.26811 (4)	0.0209 (2)
C4A	0.72473 (12)	0.67264 (6)	0.21567 (4)	0.01625 (19)
C5A	0.59916 (11)	0.61908 (5)	0.21168 (4)	0.01348 (17)
H5A	0.6317	0.5777	0.2306	0.016*
C6A	0.57781 (11)	0.59044 (6)	0.16118 (4)	0.01549 (19)
H6A	0.5318	0.6265	0.1411	0.019*
H6B	0.6715	0.5791	0.1470	0.019*
C7A	0.48485 (11)	0.52469 (6)	0.16230 (4)	0.01528 (18)
H7A	0.5360	0.4876	0.1800	0.018*
H7B	0.4708	0.5080	0.1293	0.018*
C8A	0.33796 (11)	0.53582 (5)	0.18549 (3)	0.01227 (17)
C9A	0.35892 (11)	0.57281 (5)	0.23471 (4)	0.01291 (17)
H9A	0.4120	0.5381	0.2546	0.015*
C10A	0.45470 (11)	0.64015 (5)	0.23485 (4)	0.01393 (18)
C11A	0.21573 (12)	0.58293 (6)	0.26048 (4)	0.01634 (19)
H11A	0.2340	0.6018	0.2927	0.020*
H11B	0.1584	0.6179	0.2429	0.020*
C12A	0.12975 (12)	0.51523 (6)	0.26493 (4)	0.01627 (18)
H12A	0.1784	0.4833	0.2874	0.020*
H12B	0.0345	0.5261	0.2781	0.020*
C13A	0.11247 (11)	0.47863 (5)	0.21695 (4)	0.01283 (17)
H13A	0.0639	0.5125	0.1952	0.015*
C14A	0.26152 (11)	0.46257 (5)	0.19472 (4)	0.01287 (17)
C15A	0.24443 (12)	0.42091 (6)	0.14747 (4)	0.01638 (19)
H15A	0.2064	0.4529	0.1228	0.020*
H15B	0.3398	0.4053	0.1368	0.020*
C16A	0.14645 (12)	0.35667 (6)	0.15068 (4)	0.01722 (19)
H16A	0.1350	0.3355	0.1187	0.021*
H16B	0.1893	0.3212	0.1720	0.021*
C17A	0.00108 (12)	0.37897 (5)	0.16999 (4)	0.01492 (18)
C18A	0.01897 (11)	0.41320 (5)	0.21914 (4)	0.01384 (17)
H18A	0.0697	0.3786	0.2398	0.017*
C19A	−0.13404 (12)	0.41959 (6)	0.23861 (4)	0.01601 (18)
H19A	−0.1750	0.4650	0.2275	0.019*
C20A	−0.15194 (13)	0.41507 (6)	0.29202 (4)	0.0211 (2)
C21A	−0.21630 (13)	0.35836 (6)	0.21337 (4)	0.0200 (2)
H21A	−0.2548	0.3254	0.2373	0.024*
H21B	−0.2965	0.3771	0.1944	0.024*
C22A	−0.10858 (12)	0.32098 (6)	0.18079 (4)	0.0187 (2)
H22A	−0.1547	0.3041	0.1513	0.022*
H22B	−0.0635	0.2809	0.1973	0.022*
C23A	0.86466 (12)	0.63801 (6)	0.20059 (5)	0.0215 (2)
H23A	0.9440	0.6701	0.2067	0.032*
H23B	0.8609	0.6268	0.1666	0.032*
H23C	0.8787	0.5949	0.2189	0.032*
C24A	0.70647 (13)	0.73995 (6)	0.18567 (5)	0.0212 (2)
H24A	0.6267	0.7674	0.1982	0.032*
H24B	0.6873	0.7273	0.1525	0.032*
H24C	0.7939	0.7678	0.1873	0.032*
C25A	0.38168 (12)	0.70347 (6)	0.21100 (4)	0.0190 (2)
H25A	0.2794	0.7025	0.2180	0.028*
H25B	0.3963	0.7013	0.1765	0.028*
H25C	0.4230	0.7469	0.2234	0.028*
C26A	0.24841 (12)	0.58089 (6)	0.15092 (4)	0.01676 (19)
H26A	0.3080	0.6182	0.1376	0.025*
H26B	0.1682	0.6017	0.1682	0.025*
H26C	0.2123	0.5514	0.1251	0.025*
C27A	0.34952 (12)	0.41476 (6)	0.22802 (4)	0.0179 (2)
H27A	0.2953	0.3721	0.2349	0.027*
H27B	0.3697	0.4396	0.2578	0.027*
H27C	0.4393	0.4023	0.2124	0.027*
C28A	−0.06833 (12)	0.42438 (6)	0.13232 (4)	0.01764 (19)
H28A	−0.0689	0.4059	0.1009	0.021*
C29A	−0.2500 (2)	0.45599 (9)	0.31380 (6)	0.0402 (4)
H29A	−0.2658	0.4516	0.3471	0.048*
H29B	−0.3030	0.4890	0.2958	0.048*
C30A	−0.06771 (19)	0.36332 (11)	0.31850 (5)	0.0431 (4)
H30A	−0.1003	0.3617	0.3516	0.065*
H30B	0.0331	0.3766	0.3176	0.065*
H30C	−0.0796	0.3171	0.3039	0.065*
O1B	0.35987 (14)	0.72259 (6)	−0.03456 (4)	0.0390 (3)
O2B	0.86757 (13)	1.22125 (6)	0.08376 (4)	0.0392 (3)
C1B	0.48022 (14)	0.89774 (7)	−0.04388 (4)	0.0225 (2)
H1C	0.4621	0.9388	−0.0645	0.027*
H1D	0.5723	0.8770	−0.0537	0.027*
C2B	0.36168 (16)	0.84372 (7)	−0.05166 (5)	0.0288 (3)
H2C	0.2683	0.8665	−0.0464	0.035*
H2D	0.3648	0.8274	−0.0851	0.035*
C3B	0.37393 (13)	0.78151 (7)	−0.01910 (5)	0.0241 (2)
C4B	0.39942 (13)	0.79578 (6)	0.03374 (5)	0.0211 (2)
C5B	0.51126 (12)	0.85573 (6)	0.03949 (4)	0.01744 (19)
H5B	0.6028	0.8348	0.0282	0.021*
C6B	0.54008 (14)	0.87601 (7)	0.09123 (4)	0.0225 (2)
H6C	0.5438	0.8333	0.1112	0.027*
H6D	0.4617	0.9059	0.1031	0.027*
C7B	0.68136 (13)	0.91555 (7)	0.09522 (4)	0.0220 (2)
H7C	0.7597	0.8840	0.0855	0.026*
H7D	0.6971	0.9285	0.1289	0.026*
C8B	0.68740 (12)	0.98235 (6)	0.06445 (4)	0.01613 (19)
C9B	0.63310 (11)	0.96564 (6)	0.01306 (4)	0.01476 (18)
H9B	0.7081	0.9346	−0.0008	0.018*
C10B	0.49165 (12)	0.92242 (6)	0.00828 (4)	0.01687 (19)
C11B	0.63604 (12)	1.03157 (6)	−0.01820 (4)	0.01823 (19)
H11C	0.6018	1.0197	−0.0505	0.022*
H11D	0.5707	1.0670	−0.0047	0.022*
C12B	0.78629 (12)	1.06248 (6)	−0.02159 (4)	0.0175 (2)
H12C	0.8490	1.0294	−0.0388	0.021*
H12D	0.7829	1.1066	−0.0400	0.021*
C13B	0.84825 (11)	1.07692 (6)	0.02782 (4)	0.01520 (18)
H13B	0.7841	1.1118	0.0434	0.018*
C14B	0.84699 (12)	1.00995 (6)	0.05981 (4)	0.01564 (18)
C15B	0.90957 (13)	1.02858 (7)	0.10937 (4)	0.0221 (2)
H15C	0.8413	1.0594	0.1261	0.027*
H15D	0.9185	0.9850	0.1282	0.027*
C16B	1.05551 (14)	1.06508 (7)	0.10816 (4)	0.0232 (2)
H16C	1.0838	1.0787	0.1408	0.028*
H16D	1.1283	1.0325	0.0955	0.028*
C17B	1.04716 (13)	1.12965 (6)	0.07683 (4)	0.0207 (2)
C18B	0.99732 (12)	1.10943 (6)	0.02674 (4)	0.01688 (19)
H18B	1.0637	1.0722	0.0152	0.020*
C19B	1.02510 (13)	1.17460 (6)	−0.00417 (4)	0.0210 (2)
H19B	0.9392	1.2054	−0.0025	0.025*
C20B	1.06024 (13)	1.16199 (7)	−0.05607 (4)	0.0233 (2)
C21B	1.15153 (16)	1.21296 (8)	0.02179 (5)	0.0314 (3)
H21C	1.2352	1.2165	0.0005	0.038*
H21D	1.1227	1.2607	0.0314	0.038*
C22B	1.18741 (15)	1.16837 (8)	0.06588 (5)	0.0294 (3)
H22C	1.2163	1.1983	0.0930	0.035*
H22D	1.2650	1.1349	0.0588	0.035*
C23B	0.45652 (16)	0.72842 (7)	0.05665 (5)	0.0297 (3)
H23D	0.3929	0.6894	0.0490	0.045*
H23E	0.4611	0.7344	0.0913	0.045*
H23F	0.5520	0.7185	0.0443	0.045*
C24B	0.25303 (15)	0.81165 (8)	0.05645 (6)	0.0322 (3)
H24D	0.2080	0.8507	0.0396	0.048*
H24E	0.2661	0.8242	0.0900	0.048*
H24F	0.1922	0.7701	0.0542	0.048*
C25B	0.35842 (13)	0.96599 (7)	0.02002 (5)	0.0258 (2)
H25D	0.3719	1.0141	0.0088	0.039*
H25E	0.3431	0.9662	0.0545	0.039*
H25F	0.2753	0.9454	0.0042	0.039*
C26B	0.59273 (14)	1.03780 (7)	0.08953 (4)	0.0238 (2)
H26D	0.4956	1.0196	0.0928	0.036*
H26E	0.5911	1.0808	0.0705	0.036*
H26F	0.6316	1.0480	0.1212	0.036*
C27B	0.94512 (13)	0.95281 (6)	0.03836 (4)	0.0201 (2)
H27D	1.0443	0.9687	0.0395	0.030*
H27E	0.9177	0.9440	0.0052	0.030*
H27F	0.9354	0.9095	0.0568	0.030*
C28B	0.95536 (15)	1.18356 (7)	0.10169 (5)	0.0272 (3)
H28B	0.9684	1.1882	0.1351	0.033*
C29B	1.11820 (16)	1.10286 (8)	−0.07333 (5)	0.0305 (3)
H29C	1.1409	1.0994	−0.1062	0.037*
H29D	1.1365	1.0646	−0.0526	0.037*
C30B	1.0317 (2)	1.22168 (10)	−0.08822 (6)	0.0428 (4)
H30D	1.0668	1.2107	−0.1202	0.064*
H30E	1.0805	1.2635	−0.0762	0.064*
H30F	0.9290	1.2305	−0.0895	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0277 (5)	0.0455 (6)	0.0307 (5)	−0.0028 (4)	−0.0097 (4)	−0.0107 (4)
O2A	0.0255 (4)	0.0208 (4)	0.0221 (4)	0.0010 (3)	−0.0042 (3)	0.0000 (3)
C1A	0.0213 (5)	0.0216 (5)	0.0165 (5)	−0.0062 (4)	0.0021 (4)	−0.0066 (4)
C2A	0.0243 (5)	0.0244 (5)	0.0224 (5)	−0.0076 (5)	0.0020 (4)	−0.0097 (4)
C3A	0.0218 (5)	0.0182 (5)	0.0227 (5)	−0.0054 (4)	−0.0016 (4)	−0.0041 (4)
C4A	0.0150 (4)	0.0142 (4)	0.0196 (5)	−0.0017 (4)	0.0001 (4)	−0.0024 (4)
C5A	0.0132 (4)	0.0126 (4)	0.0146 (4)	−0.0004 (3)	0.0007 (3)	−0.0007 (3)
C6A	0.0152 (4)	0.0162 (4)	0.0150 (4)	−0.0020 (4)	0.0030 (4)	−0.0017 (3)
C7A	0.0150 (4)	0.0155 (4)	0.0153 (4)	−0.0016 (4)	0.0036 (4)	−0.0041 (3)
C8A	0.0134 (4)	0.0128 (4)	0.0106 (4)	0.0003 (3)	0.0003 (3)	−0.0009 (3)
C9A	0.0146 (4)	0.0126 (4)	0.0116 (4)	−0.0005 (3)	0.0010 (3)	−0.0017 (3)
C10A	0.0149 (4)	0.0131 (4)	0.0139 (4)	−0.0007 (3)	0.0015 (3)	−0.0028 (3)
C11A	0.0169 (4)	0.0166 (4)	0.0155 (4)	−0.0024 (4)	0.0039 (4)	−0.0058 (4)
C12A	0.0181 (5)	0.0185 (5)	0.0121 (4)	−0.0037 (4)	0.0028 (4)	−0.0032 (3)
C13A	0.0141 (4)	0.0130 (4)	0.0113 (4)	−0.0015 (3)	0.0019 (3)	−0.0014 (3)
C14A	0.0150 (4)	0.0115 (4)	0.0121 (4)	0.0003 (3)	0.0009 (3)	−0.0016 (3)
C15A	0.0170 (5)	0.0159 (4)	0.0163 (4)	−0.0017 (4)	0.0037 (4)	−0.0057 (4)
C16A	0.0183 (5)	0.0148 (4)	0.0186 (5)	−0.0016 (4)	0.0030 (4)	−0.0062 (4)
C17A	0.0164 (4)	0.0134 (4)	0.0149 (4)	−0.0020 (4)	0.0017 (4)	−0.0026 (3)
C18A	0.0153 (4)	0.0131 (4)	0.0131 (4)	−0.0011 (3)	0.0019 (3)	−0.0008 (3)
C19A	0.0163 (4)	0.0150 (4)	0.0167 (4)	−0.0026 (4)	0.0036 (4)	−0.0012 (4)
C20A	0.0223 (5)	0.0237 (5)	0.0175 (5)	−0.0084 (4)	0.0056 (4)	−0.0020 (4)
C21A	0.0192 (5)	0.0205 (5)	0.0204 (5)	−0.0059 (4)	0.0044 (4)	−0.0035 (4)
C22A	0.0204 (5)	0.0152 (4)	0.0206 (5)	−0.0038 (4)	0.0019 (4)	−0.0034 (4)
C23A	0.0139 (5)	0.0207 (5)	0.0299 (6)	−0.0004 (4)	−0.0005 (4)	−0.0037 (4)
C24A	0.0199 (5)	0.0166 (5)	0.0271 (6)	−0.0015 (4)	0.0013 (4)	0.0023 (4)
C25A	0.0179 (5)	0.0139 (4)	0.0251 (5)	0.0016 (4)	0.0020 (4)	−0.0011 (4)
C26A	0.0189 (5)	0.0165 (4)	0.0148 (4)	−0.0015 (4)	−0.0028 (4)	0.0022 (4)
C27A	0.0186 (5)	0.0140 (4)	0.0211 (5)	0.0010 (4)	−0.0015 (4)	0.0020 (4)
C28A	0.0179 (5)	0.0209 (5)	0.0141 (4)	−0.0033 (4)	−0.0001 (4)	−0.0010 (4)
C29A	0.0548 (10)	0.0387 (8)	0.0273 (7)	−0.0072 (7)	0.0195 (7)	−0.0083 (6)
C30A	0.0405 (8)	0.0677 (12)	0.0212 (6)	−0.0057 (8)	0.0040 (6)	0.0151 (7)
O1B	0.0471 (6)	0.0281 (5)	0.0418 (6)	−0.0068 (5)	−0.0093 (5)	−0.0029 (4)
O2B	0.0459 (6)	0.0415 (6)	0.0302 (5)	0.0197 (5)	−0.0122 (5)	−0.0171 (4)
C1B	0.0245 (6)	0.0249 (5)	0.0180 (5)	−0.0071 (5)	−0.0041 (4)	0.0042 (4)
C2B	0.0302 (6)	0.0302 (6)	0.0261 (6)	−0.0115 (5)	−0.0087 (5)	0.0055 (5)
C3B	0.0169 (5)	0.0260 (6)	0.0294 (6)	−0.0040 (4)	−0.0004 (5)	0.0034 (5)
C4B	0.0176 (5)	0.0212 (5)	0.0246 (6)	0.0002 (4)	0.0037 (4)	0.0058 (4)
C5B	0.0155 (5)	0.0196 (5)	0.0172 (5)	0.0020 (4)	0.0023 (4)	0.0033 (4)
C6B	0.0248 (6)	0.0266 (6)	0.0162 (5)	0.0000 (5)	0.0048 (4)	0.0057 (4)
C7B	0.0247 (5)	0.0284 (6)	0.0127 (4)	−0.0012 (5)	−0.0010 (4)	0.0045 (4)
C8B	0.0170 (4)	0.0208 (5)	0.0106 (4)	0.0025 (4)	0.0018 (3)	−0.0002 (4)
C9B	0.0140 (4)	0.0194 (5)	0.0109 (4)	0.0013 (4)	0.0004 (3)	0.0012 (3)
C10B	0.0144 (4)	0.0196 (5)	0.0165 (4)	0.0012 (4)	0.0003 (4)	0.0030 (4)
C11B	0.0174 (5)	0.0224 (5)	0.0149 (4)	−0.0019 (4)	−0.0037 (4)	0.0038 (4)
C12B	0.0179 (5)	0.0222 (5)	0.0122 (4)	−0.0031 (4)	−0.0024 (4)	0.0004 (4)
C13B	0.0160 (4)	0.0189 (5)	0.0107 (4)	0.0015 (4)	−0.0018 (3)	−0.0014 (3)
C14B	0.0166 (4)	0.0194 (5)	0.0109 (4)	0.0028 (4)	−0.0015 (3)	−0.0016 (3)
C15B	0.0252 (6)	0.0296 (6)	0.0116 (4)	0.0021 (5)	−0.0049 (4)	−0.0009 (4)
C16B	0.0239 (5)	0.0284 (6)	0.0173 (5)	0.0031 (5)	−0.0083 (4)	−0.0032 (4)
C17B	0.0215 (5)	0.0239 (5)	0.0167 (5)	0.0010 (4)	−0.0057 (4)	−0.0063 (4)
C18B	0.0170 (5)	0.0191 (5)	0.0146 (4)	0.0008 (4)	−0.0025 (4)	−0.0039 (4)
C19B	0.0212 (5)	0.0205 (5)	0.0213 (5)	−0.0022 (4)	−0.0034 (4)	−0.0016 (4)
C20B	0.0168 (5)	0.0325 (6)	0.0205 (5)	−0.0062 (5)	−0.0031 (4)	0.0032 (5)
C21B	0.0343 (7)	0.0314 (7)	0.0286 (6)	−0.0133 (6)	−0.0070 (5)	−0.0040 (5)
C22B	0.0247 (6)	0.0328 (7)	0.0307 (7)	−0.0054 (5)	−0.0099 (5)	−0.0075 (5)
C23B	0.0305 (6)	0.0238 (6)	0.0349 (7)	−0.0007 (5)	0.0001 (6)	0.0100 (5)
C24B	0.0207 (6)	0.0321 (7)	0.0437 (8)	−0.0026 (5)	0.0120 (6)	0.0042 (6)
C25B	0.0157 (5)	0.0252 (6)	0.0366 (7)	0.0040 (4)	0.0013 (5)	0.0052 (5)
C26B	0.0227 (5)	0.0282 (6)	0.0207 (5)	0.0032 (5)	0.0068 (4)	−0.0054 (4)
C27B	0.0173 (5)	0.0201 (5)	0.0229 (5)	0.0027 (4)	0.0003 (4)	−0.0022 (4)
C28B	0.0329 (6)	0.0286 (6)	0.0200 (5)	0.0030 (5)	−0.0063 (5)	−0.0105 (5)
C29B	0.0311 (7)	0.0378 (7)	0.0227 (6)	−0.0018 (6)	0.0081 (5)	−0.0018 (5)
C30B	0.0465 (9)	0.0514 (10)	0.0304 (7)	0.0128 (8)	0.0004 (7)	0.0126 (7)

Geometric parameters (Å, º)

O1A—C3A	1.2122 (16)	O1B—C3B	1.2140 (17)
O2A—C28A	1.2077 (14)	O2B—C28B	1.2049 (17)
C1A—C2A	1.5322 (16)	C1B—C2B	1.5336 (18)
C1A—C10A	1.5438 (15)	C1B—C10B	1.5426 (16)
C1A—H1A	0.9900	C1B—H1C	0.9900
C1A—H1B	0.9900	C1B—H1D	0.9900
C2A—C3A	1.5074 (17)	C2B—C3B	1.5041 (18)
C2A—H2A	0.9900	C2B—H2C	0.9900
C2A—H2B	0.9900	C2B—H2D	0.9900
C3A—C4A	1.5302 (16)	C3B—C4B	1.5278 (18)
C4A—C23A	1.5310 (16)	C4B—C23B	1.5355 (17)
C4A—C24A	1.5472 (16)	C4B—C24B	1.5455 (18)
C4A—C5A	1.5653 (14)	C4B—C5B	1.5625 (17)
C5A—C6A	1.5334 (15)	C5B—C6B	1.5278 (17)
C5A—C10A	1.5574 (14)	C5B—C10B	1.5576 (15)
C5A—H5A	1.0000	C5B—H5B	1.0000
C6A—C7A	1.5301 (15)	C6B—C7B	1.5308 (18)
C6A—H6A	0.9900	C6B—H6C	0.9900
C6A—H6B	0.9900	C6B—H6D	0.9900
C7A—C8A	1.5402 (14)	C7B—C8B	1.5426 (16)
C7A—H7A	0.9900	C7B—H7C	0.9900
C7A—H7B	0.9900	C7B—H7D	0.9900
C8A—C26A	1.5465 (15)	C8B—C26B	1.5520 (16)
C8A—C9A	1.5647 (14)	C8B—C9B	1.5634 (15)
C8A—C14A	1.5943 (14)	C8B—C14B	1.5940 (16)
C9A—C11A	1.5392 (15)	C9B—C11B	1.5358 (15)
C9A—C10A	1.5700 (14)	C9B—C10B	1.5698 (15)
C9A—H9A	1.0000	C9B—H9B	1.0000
C10A—C25A	1.5436 (15)	C10B—C25B	1.5385 (16)
C11A—C12A	1.5300 (15)	C11B—C12B	1.5325 (16)
C11A—H11A	0.9900	C11B—H11C	0.9900
C11A—H11B	0.9900	C11B—H11D	0.9900
C12A—C13A	1.5267 (14)	C12B—C13B	1.5298 (14)
C12A—H12A	0.9900	C12B—H12C	0.9900
C12A—H12B	0.9900	C12B—H12D	0.9900
C13A—C18A	1.5290 (14)	C13B—C18B	1.5318 (16)
C13A—C14A	1.5629 (14)	C13B—C14B	1.5636 (15)
C13A—H13A	1.0000	C13B—H13B	1.0000
C14A—C27A	1.5466 (15)	C14B—C27B	1.5505 (15)
C14A—C15A	1.5558 (14)	C14B—C15B	1.5521 (15)
C15A—C16A	1.5366 (15)	C15B—C16B	1.5380 (18)
C15A—H15A	0.9900	C15B—H15C	0.9900
C15A—H15B	0.9900	C15B—H15D	0.9900
C16A—C17A	1.5293 (15)	C16B—C17B	1.5174 (18)
C16A—H16A	0.9900	C16B—H16C	0.9900
C16A—H16B	0.9900	C16B—H16D	0.9900
C17A—C28A	1.5156 (16)	C17B—C28B	1.5139 (18)
C17A—C18A	1.5367 (14)	C17B—C18B	1.5321 (15)
C17A—C22A	1.5428 (15)	C17B—C22B	1.5416 (19)
C18A—C19A	1.5422 (15)	C18B—C19B	1.5401 (16)
C18A—H18A	1.0000	C18B—H18B	1.0000
C19A—C20A	1.5117 (16)	C19B—C20B	1.5138 (18)
C19A—C21A	1.5709 (15)	C19B—C21B	1.5743 (17)
C19A—H19A	1.0000	C19B—H19B	1.0000
C20A—C29A	1.354 (2)	C20B—C29B	1.344 (2)
C20A—C30A	1.469 (2)	C20B—C30B	1.479 (2)
C21A—C22A	1.5396 (16)	C21B—C22B	1.540 (2)
C21A—H21A	0.9900	C21B—H21C	0.9900
C21A—H21B	0.9900	C21B—H21D	0.9900
C22A—H22A	0.9900	C22B—H22C	0.9900
C22A—H22B	0.9900	C22B—H22D	0.9900
C23A—H23A	0.9800	C23B—H23D	0.9800
C23A—H23B	0.9800	C23B—H23E	0.9800
C23A—H23C	0.9800	C23B—H23F	0.9800
C24A—H24A	0.9800	C24B—H24D	0.9800
C24A—H24B	0.9800	C24B—H24E	0.9800
C24A—H24C	0.9800	C24B—H24F	0.9800
C25A—H25A	0.9800	C25B—H25D	0.9800
C25A—H25B	0.9800	C25B—H25E	0.9800
C25A—H25C	0.9800	C25B—H25F	0.9800
C26A—H26A	0.9800	C26B—H26D	0.9800
C26A—H26B	0.9800	C26B—H26E	0.9800
C26A—H26C	0.9800	C26B—H26F	0.9800
C27A—H27A	0.9800	C27B—H27D	0.9800
C27A—H27B	0.9800	C27B—H27E	0.9800
C27A—H27C	0.9800	C27B—H27F	0.9800
C28A—H28A	0.9500	C28B—H28B	0.9500
C29A—H29A	0.9500	C29B—H29C	0.9500
C29A—H29B	0.9500	C29B—H29D	0.9500
C30A—H30A	0.9800	C30B—H30D	0.9800
C30A—H30B	0.9800	C30B—H30E	0.9800
C30A—H30C	0.9800	C30B—H30F	0.9800
C2A—C1A—C10A	113.38 (9)	C2B—C1B—C10B	113.06 (10)
C2A—C1A—H1A	108.9	C2B—C1B—H1C	109.0
C10A—C1A—H1A	108.9	C10B—C1B—H1C	109.0
C2A—C1A—H1B	108.9	C2B—C1B—H1D	109.0
C10A—C1A—H1B	108.9	C10B—C1B—H1D	109.0
H1A—C1A—H1B	107.7	H1C—C1B—H1D	107.8
C3A—C2A—C1A	112.12 (10)	C3B—C2B—C1B	112.94 (11)
C3A—C2A—H2A	109.2	C3B—C2B—H2C	109.0
C1A—C2A—H2A	109.2	C1B—C2B—H2C	109.0
C3A—C2A—H2B	109.2	C3B—C2B—H2D	109.0
C1A—C2A—H2B	109.2	C1B—C2B—H2D	109.0
H2A—C2A—H2B	107.9	H2C—C2B—H2D	107.8
O1A—C3A—C2A	120.96 (12)	O1B—C3B—C2B	120.49 (13)
O1A—C3A—C4A	122.19 (12)	O1B—C3B—C4B	122.00 (12)
C2A—C3A—C4A	116.83 (10)	C2B—C3B—C4B	117.48 (11)
C3A—C4A—C23A	108.08 (10)	C3B—C4B—C23B	108.19 (11)
C3A—C4A—C24A	108.44 (9)	C3B—C4B—C24B	107.24 (11)
C23A—C4A—C24A	107.68 (10)	C23B—C4B—C24B	107.59 (11)
C3A—C4A—C5A	107.41 (9)	C3B—C4B—C5B	109.66 (9)
C23A—C4A—C5A	110.14 (9)	C23B—C4B—C5B	109.67 (10)
C24A—C4A—C5A	114.90 (9)	C24B—C4B—C5B	114.29 (10)
C6A—C5A—C10A	111.40 (8)	C6B—C5B—C10B	110.40 (9)
C6A—C5A—C4A	113.46 (8)	C6B—C5B—C4B	113.78 (9)
C10A—C5A—C4A	117.21 (8)	C10B—C5B—C4B	117.53 (9)
C6A—C5A—H5A	104.4	C6B—C5B—H5B	104.5
C10A—C5A—H5A	104.4	C10B—C5B—H5B	104.5
C4A—C5A—H5A	104.4	C4B—C5B—H5B	104.5
C7A—C6A—C5A	110.41 (9)	C5B—C6B—C7B	110.38 (9)
C7A—C6A—H6A	109.6	C5B—C6B—H6C	109.6
C5A—C6A—H6A	109.6	C7B—C6B—H6C	109.6
C7A—C6A—H6B	109.6	C5B—C6B—H6D	109.6
C5A—C6A—H6B	109.6	C7B—C6B—H6D	109.6
H6A—C6A—H6B	108.1	H6C—C6B—H6D	108.1
C6A—C7A—C8A	113.97 (8)	C6B—C7B—C8B	113.53 (10)
C6A—C7A—H7A	108.8	C6B—C7B—H7C	108.9
C8A—C7A—H7A	108.8	C8B—C7B—H7C	108.9
C6A—C7A—H7B	108.8	C6B—C7B—H7D	108.9
C8A—C7A—H7B	108.8	C8B—C7B—H7D	108.9
H7A—C7A—H7B	107.7	H7C—C7B—H7D	107.7
C7A—C8A—C26A	107.36 (8)	C7B—C8B—C26B	106.83 (9)
C7A—C8A—C9A	108.86 (8)	C7B—C8B—C9B	109.64 (9)
C26A—C8A—C9A	111.80 (8)	C26B—C8B—C9B	111.81 (9)
C7A—C8A—C14A	110.54 (8)	C7B—C8B—C14B	110.74 (9)
C26A—C8A—C14A	110.25 (8)	C26B—C8B—C14B	110.47 (9)
C9A—C8A—C14A	108.03 (8)	C9B—C8B—C14B	107.39 (8)
C11A—C9A—C8A	111.23 (8)	C11B—C9B—C8B	110.75 (9)
C11A—C9A—C10A	113.35 (8)	C11B—C9B—C10B	113.44 (9)
C8A—C9A—C10A	116.39 (8)	C8B—C9B—C10B	117.54 (9)
C11A—C9A—H9A	104.9	C11B—C9B—H9B	104.5
C8A—C9A—H9A	104.9	C8B—C9B—H9B	104.5
C10A—C9A—H9A	104.9	C10B—C9B—H9B	104.5
C25A—C10A—C1A	108.14 (9)	C25B—C10B—C1B	108.20 (10)
C25A—C10A—C5A	114.09 (9)	C25B—C10B—C5B	114.72 (9)
C1A—C10A—C5A	107.45 (9)	C1B—C10B—C5B	107.00 (9)
C25A—C10A—C9A	112.75 (9)	C25B—C10B—C9B	112.65 (9)
C1A—C10A—C9A	107.48 (8)	C1B—C10B—C9B	107.52 (9)
C5A—C10A—C9A	106.63 (8)	C5B—C10B—C9B	106.40 (8)
C12A—C11A—C9A	113.15 (9)	C12B—C11B—C9B	111.60 (9)
C12A—C11A—H11A	108.9	C12B—C11B—H11C	109.3
C9A—C11A—H11A	108.9	C9B—C11B—H11C	109.3
C12A—C11A—H11B	108.9	C12B—C11B—H11D	109.3
C9A—C11A—H11B	108.9	C9B—C11B—H11D	109.3
H11A—C11A—H11B	107.8	H11C—C11B—H11D	108.0
C13A—C12A—C11A	111.78 (8)	C13B—C12B—C11B	111.31 (9)
C13A—C12A—H12A	109.3	C13B—C12B—H12C	109.4
C11A—C12A—H12A	109.3	C11B—C12B—H12C	109.4
C13A—C12A—H12B	109.3	C13B—C12B—H12D	109.4
C11A—C12A—H12B	109.3	C11B—C12B—H12D	109.4
H12A—C12A—H12B	107.9	H12C—C12B—H12D	108.0
C12A—C13A—C18A	113.58 (8)	C12B—C13B—C18B	113.75 (9)
C12A—C13A—C14A	110.32 (8)	C12B—C13B—C14B	111.75 (9)
C18A—C13A—C14A	111.70 (8)	C18B—C13B—C14B	110.50 (9)
C12A—C13A—H13A	107.0	C12B—C13B—H13B	106.8
C18A—C13A—H13A	107.0	C18B—C13B—H13B	106.8
C14A—C13A—H13A	107.0	C14B—C13B—H13B	106.8
C27A—C14A—C15A	105.59 (8)	C27B—C14B—C15B	106.55 (9)
C27A—C14A—C13A	110.67 (8)	C27B—C14B—C13B	110.40 (9)
C15A—C14A—C13A	110.41 (8)	C15B—C14B—C13B	108.94 (9)
C27A—C14A—C8A	112.10 (8)	C27B—C14B—C8B	110.95 (9)
C15A—C14A—C8A	110.91 (8)	C15B—C14B—C8B	111.01 (9)
C13A—C14A—C8A	107.20 (8)	C13B—C14B—C8B	108.95 (8)
C16A—C15A—C14A	114.85 (9)	C16B—C15B—C14B	114.93 (10)
C16A—C15A—H15A	108.6	C16B—C15B—H15C	108.5
C14A—C15A—H15A	108.6	C14B—C15B—H15C	108.5
C16A—C15A—H15B	108.6	C16B—C15B—H15D	108.5
C14A—C15A—H15B	108.6	C14B—C15B—H15D	108.5
H15A—C15A—H15B	107.5	H15C—C15B—H15D	107.5
C17A—C16A—C15A	109.44 (9)	C17B—C16B—C15B	109.60 (10)
C17A—C16A—H16A	109.8	C17B—C16B—H16C	109.8
C15A—C16A—H16A	109.8	C15B—C16B—H16C	109.8
C17A—C16A—H16B	109.8	C17B—C16B—H16D	109.8
C15A—C16A—H16B	109.8	C15B—C16B—H16D	109.8
H16A—C16A—H16B	108.2	H16C—C16B—H16D	108.2
C28A—C17A—C16A	107.20 (9)	C28B—C17B—C16B	108.38 (11)
C28A—C17A—C18A	115.49 (9)	C28B—C17B—C18B	114.90 (10)
C16A—C17A—C18A	109.84 (9)	C16B—C17B—C18B	110.07 (9)
C28A—C17A—C22A	105.15 (9)	C28B—C17B—C22B	104.59 (10)
C16A—C17A—C22A	117.74 (9)	C16B—C17B—C22B	117.51 (11)
C18A—C17A—C22A	101.66 (8)	C18B—C17B—C22B	101.47 (10)
C13A—C18A—C17A	112.01 (8)	C13B—C18B—C17B	111.30 (9)
C13A—C18A—C19A	118.99 (8)	C13B—C18B—C19B	119.59 (9)
C17A—C18A—C19A	104.49 (8)	C17B—C18B—C19B	105.18 (9)
C13A—C18A—H18A	106.9	C13B—C18B—H18B	106.7
C17A—C18A—H18A	106.9	C17B—C18B—H18B	106.7
C19A—C18A—H18A	106.9	C19B—C18B—H18B	106.7
C20A—C19A—C18A	116.79 (10)	C20B—C19B—C18B	116.80 (10)
C20A—C19A—C21A	110.52 (9)	C20B—C19B—C21B	110.83 (10)
C18A—C19A—C21A	103.84 (8)	C18B—C19B—C21B	104.08 (10)
C20A—C19A—H19A	108.5	C20B—C19B—H19B	108.3
C18A—C19A—H19A	108.5	C18B—C19B—H19B	108.3
C21A—C19A—H19A	108.5	C21B—C19B—H19B	108.3
C29A—C20A—C30A	121.76 (13)	C29B—C20B—C30B	120.09 (13)
C29A—C20A—C19A	119.39 (13)	C29B—C20B—C19B	124.68 (12)
C30A—C20A—C19A	118.75 (11)	C30B—C20B—C19B	115.18 (13)
C22A—C21A—C19A	106.90 (9)	C22B—C21B—C19B	106.24 (11)
C22A—C21A—H21A	110.3	C22B—C21B—H21C	110.5
C19A—C21A—H21A	110.3	C19B—C21B—H21C	110.5
C22A—C21A—H21B	110.3	C22B—C21B—H21D	110.5
C19A—C21A—H21B	110.3	C19B—C21B—H21D	110.5
H21A—C21A—H21B	108.6	H21C—C21B—H21D	108.7
C21A—C22A—C17A	102.83 (8)	C21B—C22B—C17B	103.83 (10)
C21A—C22A—H22A	111.2	C21B—C22B—H22C	111.0
C17A—C22A—H22A	111.2	C17B—C22B—H22C	111.0
C21A—C22A—H22B	111.2	C21B—C22B—H22D	111.0
C17A—C22A—H22B	111.2	C17B—C22B—H22D	111.0
H22A—C22A—H22B	109.1	H22C—C22B—H22D	109.0
C4A—C23A—H23A	109.5	C4B—C23B—H23D	109.5
C4A—C23A—H23B	109.5	C4B—C23B—H23E	109.5
H23A—C23A—H23B	109.5	H23D—C23B—H23E	109.5
C4A—C23A—H23C	109.5	C4B—C23B—H23F	109.5
H23A—C23A—H23C	109.5	H23D—C23B—H23F	109.5
H23B—C23A—H23C	109.5	H23E—C23B—H23F	109.5
C4A—C24A—H24A	109.5	C4B—C24B—H24D	109.5
C4A—C24A—H24B	109.5	C4B—C24B—H24E	109.5
H24A—C24A—H24B	109.5	H24D—C24B—H24E	109.5
C4A—C24A—H24C	109.5	C4B—C24B—H24F	109.5
H24A—C24A—H24C	109.5	H24D—C24B—H24F	109.5
H24B—C24A—H24C	109.5	H24E—C24B—H24F	109.5
C10A—C25A—H25A	109.5	C10B—C25B—H25D	109.5
C10A—C25A—H25B	109.5	C10B—C25B—H25E	109.5
H25A—C25A—H25B	109.5	H25D—C25B—H25E	109.5
C10A—C25A—H25C	109.5	C10B—C25B—H25F	109.5
H25A—C25A—H25C	109.5	H25D—C25B—H25F	109.5
H25B—C25A—H25C	109.5	H25E—C25B—H25F	109.5
C8A—C26A—H26A	109.5	C8B—C26B—H26D	109.5
C8A—C26A—H26B	109.5	C8B—C26B—H26E	109.5
H26A—C26A—H26B	109.5	H26D—C26B—H26E	109.5
C8A—C26A—H26C	109.5	C8B—C26B—H26F	109.5
H26A—C26A—H26C	109.5	H26D—C26B—H26F	109.5
H26B—C26A—H26C	109.5	H26E—C26B—H26F	109.5
C14A—C27A—H27A	109.5	C14B—C27B—H27D	109.5
C14A—C27A—H27B	109.5	C14B—C27B—H27E	109.5
H27A—C27A—H27B	109.5	H27D—C27B—H27E	109.5
C14A—C27A—H27C	109.5	C14B—C27B—H27F	109.5
H27A—C27A—H27C	109.5	H27D—C27B—H27F	109.5
H27B—C27A—H27C	109.5	H27E—C27B—H27F	109.5
O2A—C28A—C17A	128.00 (10)	O2B—C28B—C17B	127.14 (12)
O2A—C28A—H28A	116.0	O2B—C28B—H28B	116.4
C17A—C28A—H28A	116.0	C17B—C28B—H28B	116.4
C20A—C29A—H29A	120.0	C20B—C29B—H29C	120.0
C20A—C29A—H29B	120.0	C20B—C29B—H29D	120.0
H29A—C29A—H29B	120.0	H29C—C29B—H29D	120.0
C20A—C30A—H30A	109.5	C20B—C30B—H30D	109.5
C20A—C30A—H30B	109.5	C20B—C30B—H30E	109.5
H30A—C30A—H30B	109.5	H30D—C30B—H30E	109.5
C20A—C30A—H30C	109.5	C20B—C30B—H30F	109.5
H30A—C30A—H30C	109.5	H30D—C30B—H30F	109.5
H30B—C30A—H30C	109.5	H30E—C30B—H30F	109.5
C10A—C1A—C2A—C3A	−53.72 (14)	C10B—C1B—C2B—C3B	−54.38 (16)
C1A—C2A—C3A—O1A	−127.02 (13)	C1B—C2B—C3B—O1B	−134.51 (14)
C1A—C2A—C3A—C4A	51.89 (15)	C1B—C2B—C3B—C4B	47.49 (17)
O1A—C3A—C4A—C23A	11.74 (16)	O1B—C3B—C4B—C23B	20.42 (17)
C2A—C3A—C4A—C23A	−167.16 (10)	C2B—C3B—C4B—C23B	−161.61 (12)
O1A—C3A—C4A—C24A	−104.73 (14)	O1B—C3B—C4B—C24B	−95.37 (15)
C2A—C3A—C4A—C24A	76.37 (12)	C2B—C3B—C4B—C24B	82.60 (14)
O1A—C3A—C4A—C5A	130.55 (12)	O1B—C3B—C4B—C5B	140.00 (13)
C2A—C3A—C4A—C5A	−48.35 (13)	C2B—C3B—C4B—C5B	−42.03 (14)
C3A—C4A—C5A—C6A	−177.14 (9)	C3B—C4B—C5B—C6B	177.75 (10)
C23A—C4A—C5A—C6A	−59.66 (12)	C23B—C4B—C5B—C6B	−63.58 (13)
C24A—C4A—C5A—C6A	62.13 (12)	C24B—C4B—C5B—C6B	57.32 (14)
C3A—C4A—C5A—C10A	50.77 (12)	C3B—C4B—C5B—C10B	46.50 (13)
C23A—C4A—C5A—C10A	168.24 (9)	C23B—C4B—C5B—C10B	165.17 (10)
C24A—C4A—C5A—C10A	−69.97 (12)	C24B—C4B—C5B—C10B	−73.94 (14)
C10A—C5A—C6A—C7A	−61.19 (11)	C10B—C5B—C6B—C7B	−64.26 (12)
C4A—C5A—C6A—C7A	163.94 (9)	C4B—C5B—C6B—C7B	161.08 (10)
C5A—C6A—C7A—C8A	57.11 (12)	C5B—C6B—C7B—C8B	58.00 (13)
C6A—C7A—C8A—C26A	71.19 (11)	C6B—C7B—C8B—C26B	74.00 (12)
C6A—C7A—C8A—C9A	−50.00 (11)	C6B—C7B—C8B—C9B	−47.33 (13)
C6A—C7A—C8A—C14A	−168.51 (8)	C6B—C7B—C8B—C14B	−165.65 (9)
C7A—C8A—C9A—C11A	−177.93 (8)	C7B—C8B—C9B—C11B	179.22 (9)
C26A—C8A—C9A—C11A	63.63 (11)	C26B—C8B—C9B—C11B	60.93 (12)
C14A—C8A—C9A—C11A	−57.85 (10)	C14B—C8B—C9B—C11B	−60.40 (11)
C7A—C8A—C9A—C10A	50.20 (11)	C7B—C8B—C9B—C10B	46.59 (12)
C26A—C8A—C9A—C10A	−68.24 (11)	C26B—C8B—C9B—C10B	−71.70 (12)
C14A—C8A—C9A—C10A	170.28 (8)	C14B—C8B—C9B—C10B	166.97 (9)
C2A—C1A—C10A—C25A	−70.27 (12)	C2B—C1B—C10B—C25B	−68.67 (13)
C2A—C1A—C10A—C5A	53.32 (12)	C2B—C1B—C10B—C5B	55.44 (13)
C2A—C1A—C10A—C9A	167.74 (9)	C2B—C1B—C10B—C9B	169.40 (10)
C6A—C5A—C10A—C25A	−67.26 (11)	C6B—C5B—C10B—C25B	−66.26 (13)
C4A—C5A—C10A—C25A	65.77 (12)	C4B—C5B—C10B—C25B	66.51 (14)
C6A—C5A—C10A—C1A	172.88 (8)	C6B—C5B—C10B—C1B	173.72 (10)
C4A—C5A—C10A—C1A	−54.10 (12)	C4B—C5B—C10B—C1B	−53.51 (12)
C6A—C5A—C10A—C9A	57.89 (11)	C6B—C5B—C10B—C9B	59.00 (11)
C4A—C5A—C10A—C9A	−169.09 (9)	C4B—C5B—C10B—C9B	−168.22 (9)
C11A—C9A—C10A—C25A	−59.02 (12)	C11B—C9B—C10B—C25B	−57.10 (12)
C8A—C9A—C10A—C25A	71.87 (11)	C8B—C9B—C10B—C25B	74.32 (12)
C11A—C9A—C10A—C1A	60.06 (11)	C11B—C9B—C10B—C1B	62.02 (12)
C8A—C9A—C10A—C1A	−169.06 (9)	C8B—C9B—C10B—C1B	−166.56 (9)
C11A—C9A—C10A—C5A	175.03 (8)	C11B—C9B—C10B—C5B	176.38 (9)
C8A—C9A—C10A—C5A	−54.09 (11)	C8B—C9B—C10B—C5B	−52.20 (12)
C8A—C9A—C11A—C12A	52.78 (12)	C8B—C9B—C11B—C12B	58.67 (12)
C10A—C9A—C11A—C12A	−173.82 (9)	C10B—C9B—C11B—C12B	−166.65 (9)
C9A—C11A—C12A—C13A	−52.00 (12)	C9B—C11B—C12B—C13B	−54.95 (12)
C11A—C12A—C13A—C18A	−176.23 (9)	C11B—C12B—C13B—C18B	−178.73 (9)
C11A—C12A—C13A—C14A	57.49 (11)	C11B—C12B—C13B—C14B	55.29 (12)
C12A—C13A—C14A—C27A	59.71 (11)	C12B—C13B—C14B—C27B	63.93 (11)
C18A—C13A—C14A—C27A	−67.62 (11)	C18B—C13B—C14B—C27B	−63.82 (11)
C12A—C13A—C14A—C15A	176.25 (9)	C12B—C13B—C14B—C15B	−179.39 (9)
C18A—C13A—C14A—C15A	48.92 (11)	C18B—C13B—C14B—C15B	52.86 (11)
C12A—C13A—C14A—C8A	−62.82 (10)	C12B—C13B—C14B—C8B	−58.15 (11)
C18A—C13A—C14A—C8A	169.85 (8)	C18B—C13B—C14B—C8B	174.11 (8)
C7A—C8A—C14A—C27A	59.81 (11)	C7B—C8B—C14B—C27B	57.46 (12)
C26A—C8A—C14A—C27A	178.35 (9)	C26B—C8B—C14B—C27B	175.62 (9)
C9A—C8A—C14A—C27A	−59.21 (10)	C9B—C8B—C14B—C27B	−62.22 (11)
C7A—C8A—C14A—C15A	−57.95 (11)	C7B—C8B—C14B—C15B	−60.82 (12)
C26A—C8A—C14A—C15A	60.60 (11)	C26B—C8B—C14B—C15B	57.33 (12)
C9A—C8A—C14A—C15A	−176.96 (8)	C9B—C8B—C14B—C15B	179.50 (9)
C7A—C8A—C14A—C13A	−178.55 (8)	C7B—C8B—C14B—C13B	179.20 (9)
C26A—C8A—C14A—C13A	−60.01 (10)	C26B—C8B—C14B—C13B	−62.64 (11)
C9A—C8A—C14A—C13A	62.43 (10)	C9B—C8B—C14B—C13B	59.53 (11)
C27A—C14A—C15A—C16A	69.90 (11)	C27B—C14B—C15B—C16B	67.05 (13)
C13A—C14A—C15A—C16A	−49.76 (12)	C13B—C14B—C15B—C16B	−52.06 (13)
C8A—C14A—C15A—C16A	−168.44 (9)	C8B—C14B—C15B—C16B	−172.04 (10)
C14A—C15A—C16A—C17A	54.84 (12)	C14B—C15B—C16B—C17B	54.64 (13)
C15A—C16A—C17A—C28A	67.87 (11)	C15B—C16B—C17B—C28B	69.38 (12)
C15A—C16A—C17A—C18A	−58.33 (11)	C15B—C16B—C17B—C18B	−57.04 (13)
C15A—C16A—C17A—C22A	−173.96 (9)	C15B—C16B—C17B—C22B	−172.44 (10)
C12A—C13A—C18A—C17A	178.55 (9)	C12B—C13B—C18B—C17B	174.10 (10)
C14A—C13A—C18A—C17A	−55.90 (11)	C14B—C13B—C18B—C17B	−59.26 (12)
C12A—C13A—C18A—C19A	56.38 (12)	C12B—C13B—C18B—C19B	51.11 (13)
C14A—C13A—C18A—C19A	−178.07 (9)	C14B—C13B—C18B—C19B	177.75 (9)
C28A—C17A—C18A—C13A	−60.62 (12)	C28B—C17B—C18B—C13B	−61.25 (14)
C16A—C17A—C18A—C13A	60.74 (11)	C16B—C17B—C18B—C13B	61.42 (12)
C22A—C17A—C18A—C13A	−173.83 (9)	C22B—C17B—C18B—C13B	−173.42 (10)
C28A—C17A—C18A—C19A	69.49 (11)	C28B—C17B—C18B—C19B	69.67 (13)
C16A—C17A—C18A—C19A	−169.15 (9)	C16B—C17B—C18B—C19B	−167.67 (10)
C22A—C17A—C18A—C19A	−43.72 (10)	C22B—C17B—C18B—C19B	−42.51 (12)
C13A—C18A—C19A—C20A	−85.01 (12)	C13B—C18B—C19B—C20B	−84.91 (13)
C17A—C18A—C19A—C20A	149.15 (9)	C17B—C18B—C19B—C20B	149.16 (10)
C13A—C18A—C19A—C21A	153.06 (9)	C13B—C18B—C19B—C21B	152.58 (10)
C17A—C18A—C19A—C21A	27.22 (10)	C17B—C18B—C19B—C21B	26.65 (12)
C18A—C19A—C20A—C29A	142.65 (12)	C18B—C19B—C20B—C29B	−25.16 (18)
C21A—C19A—C20A—C29A	−98.98 (14)	C21B—C19B—C20B—C29B	93.76 (15)
C18A—C19A—C20A—C30A	−40.80 (16)	C18B—C19B—C20B—C30B	157.26 (12)
C21A—C19A—C20A—C30A	77.58 (14)	C21B—C19B—C20B—C30B	−83.81 (15)
C20A—C19A—C21A—C22A	−126.59 (11)	C20B—C19B—C21B—C22B	−126.91 (12)
C18A—C19A—C21A—C22A	−0.58 (12)	C18B—C19B—C21B—C22B	−0.55 (14)
C19A—C21A—C22A—C17A	−25.95 (12)	C19B—C21B—C22B—C17B	−25.39 (14)
C28A—C17A—C22A—C21A	−78.26 (10)	C28B—C17B—C22B—C21B	−78.30 (12)
C16A—C17A—C22A—C21A	162.49 (10)	C16B—C17B—C22B—C21B	161.51 (11)
C18A—C17A—C22A—C21A	42.48 (11)	C18B—C17B—C22B—C21B	41.48 (13)
C16A—C17A—C28A—O2A	−130.43 (12)	C16B—C17B—C28B—O2B	−139.26 (16)
C18A—C17A—C28A—O2A	−7.66 (17)	C18B—C17B—C28B—O2B	−15.7 (2)
C22A—C17A—C28A—O2A	103.51 (13)	C22B—C17B—C28B—O2B	94.63 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13A—H13A···O2A	1.00	2.47	3.1452 (13)	125
C13B—H13B···O2B	1.00	2.50	3.1792 (15)	125
C19A—H19A···O2A	1.00	2.60	3.0801 (14)	110
C19B—H19B···O2B	1.00	2.53	3.0134 (17)	109
C22A—H22A···O2B^i	0.99	2.48	3.3325 (15)	144

Symmetry code: (i) x−1, y−1, z.

(II_polymorph) Lup-20 (29)-en-28-al-3-one

Crystal data

C30H46O2	F(000) = 968
Mr = 438.67	Dx = 1.178 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 15750 reflections
a = 10.3987 (2) Å	θ = 2.5–38.4°
b = 13.8559 (3) Å	µ = 0.07 mm^−1
c = 17.1632 (2) Å	T = 100 K
V = 2472.93 (8) Å^3	Plate, colourless
Z = 4	0.30 × 0.26 × 0.10 mm

Data collection

Agilent SuperNova diffractometer with an Atlas detector	7855 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	7535 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.020
Detector resolution: 10.4498 pixels mm^-1	θmax = 31.0°, θmin = 2.3°
ω scans	h = −14→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −19→20
Tmin = 0.917, Tmax = 1.000	l = −22→24
24511 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0426P)^2 + 0.7618P] where P = (Fo^2 + 2Fc^2)/3
7855 reflections	(Δ/σ)max = 0.001
305 parameters	Δρmax = 0.35 e Å^−3
2 restraints	Δρmin = −0.21 e Å^−3

Special details

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.32 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.58894 (10)	−0.03494 (8)	1.14232 (6)	0.0364 (2)
C1	0.74851 (11)	0.16505 (8)	1.06364 (6)	0.01888 (19)
H1A	0.8084	0.2166	1.0803	0.023*
H1B	0.6611	0.1932	1.0617	0.023*
C2	0.75044 (12)	0.08385 (9)	1.12463 (6)	0.0228 (2)
H2A	0.8403	0.0627	1.1331	0.027*
H2B	0.7171	0.1090	1.1747	0.027*
C3	0.67054 (12)	−0.00148 (9)	1.09977 (6)	0.0222 (2)
C4	0.69646 (11)	−0.04233 (8)	1.01828 (6)	0.01937 (19)
C5	0.69810 (10)	0.04404 (7)	0.95983 (5)	0.01485 (17)
H5	0.6087	0.0705	0.9611	0.018*
C6	0.71914 (11)	0.01291 (7)	0.87504 (6)	0.01699 (18)
H6A	0.8105	−0.0049	0.8673	0.020*
H6B	0.6658	−0.0446	0.8636	0.020*
C7	0.68320 (10)	0.09459 (7)	0.81931 (5)	0.01604 (18)
H7A	0.5898	0.1073	0.8239	0.019*
H7B	0.7002	0.0732	0.7652	0.019*
C8	0.75668 (9)	0.18961 (7)	0.83405 (5)	0.01263 (16)
C9	0.75119 (10)	0.21465 (7)	0.92288 (5)	0.01345 (16)
H9	0.6585	0.2288	0.9334	0.016*
C10	0.78640 (10)	0.13146 (7)	0.98091 (5)	0.01434 (17)
C11	0.82145 (11)	0.31032 (7)	0.93930 (6)	0.01823 (19)
H11A	0.8121	0.3266	0.9952	0.022*
H11B	0.9142	0.3019	0.9284	0.022*
C12	0.76985 (11)	0.39402 (7)	0.89024 (6)	0.01748 (18)
H12A	0.6810	0.4093	0.9070	0.021*
H12B	0.8236	0.4519	0.8993	0.021*
C13	0.76983 (9)	0.37005 (7)	0.80322 (6)	0.01386 (16)
H13	0.8611	0.3568	0.7883	0.017*
C14	0.69209 (9)	0.27551 (7)	0.78683 (5)	0.01271 (16)
C15	0.69300 (10)	0.25305 (7)	0.69814 (6)	0.01672 (18)
H15A	0.7809	0.2332	0.6829	0.020*
H15B	0.6349	0.1978	0.6882	0.020*
C16	0.65136 (11)	0.33790 (8)	0.64658 (6)	0.01951 (19)
H16A	0.6604	0.3201	0.5910	0.023*
H16B	0.5599	0.3534	0.6566	0.023*
C17	0.73431 (10)	0.42539 (7)	0.66427 (6)	0.01795 (18)
C18	0.72268 (10)	0.45247 (7)	0.75083 (6)	0.01516 (17)
H18	0.6290	0.4611	0.7619	0.018*
C19	0.78504 (10)	0.55314 (7)	0.75692 (6)	0.01768 (18)
H19	0.8796	0.5447	0.7652	0.021*
C20	0.73410 (11)	0.62069 (8)	0.81885 (7)	0.0216 (2)
C21	0.76329 (11)	0.59846 (8)	0.67393 (7)	0.0216 (2)
H21A	0.7083	0.6566	0.6777	0.026*
H21B	0.8466	0.6172	0.6504	0.026*
C22	0.69701 (12)	0.52073 (8)	0.62404 (7)	0.0226 (2)
H22A	0.7288	0.5224	0.5697	0.027*
H22B	0.6026	0.5297	0.6239	0.027*
C23	0.58740 (13)	−0.11220 (9)	0.99805 (7)	0.0267 (2)
H23A	0.5782	−0.1599	1.0398	0.040*
H23B	0.6073	−0.1452	0.9490	0.040*
H23C	0.5069	−0.0762	0.9924	0.040*
C24	0.82287 (12)	−0.10070 (8)	1.02012 (7)	0.0245 (2)
H24A	0.8097	−0.1603	1.0498	0.037*
H24B	0.8904	−0.0621	1.0450	0.037*
H24C	0.8488	−0.1167	0.9668	0.037*
C25	0.93129 (10)	0.10783 (8)	0.98129 (6)	0.01824 (19)
H25A	0.9806	0.1670	0.9721	0.027*
H25B	0.9502	0.0609	0.9401	0.027*
H25C	0.9552	0.0805	1.0319	0.027*
C26	0.89673 (10)	0.17365 (8)	0.80668 (6)	0.01716 (18)
H26A	0.9278	0.1114	0.8261	0.026*
H26B	0.9514	0.2255	0.8270	0.026*
H26C	0.8998	0.1739	0.7496	0.026*
C27	0.54934 (10)	0.28884 (8)	0.80948 (6)	0.01746 (18)
H27A	0.5162	0.3482	0.7858	0.026*
H27B	0.5419	0.2932	0.8663	0.026*
H27C	0.4994	0.2336	0.7907	0.026*
C28	0.87024 (12)	0.40434 (9)	0.63657 (7)	0.0274 (2)
C29	0.62078 (12)	0.61221 (9)	0.85442 (8)	0.0276 (2)
H29A	0.5936	0.6601	0.8904	0.033*
H29B	0.5672	0.5583	0.8438	0.033*
C30	0.82068 (14)	0.70538 (10)	0.83473 (10)	0.0352 (3)
H30A	0.7801	0.7479	0.8732	0.053*
H30B	0.8351	0.7412	0.7863	0.053*
H30C	0.9032	0.6822	0.8550	0.053*
O2A	0.96717 (11)	0.41684 (9)	0.66528 (7)	0.0267 (3)	0.769 (3)
H2AO	0.8662	0.3763	0.5770	0.032*	0.769 (3)
O2B	0.92433 (18)	0.3506 (3)	0.5993 (2)	0.0393 (13)	0.231 (3)
H2BO	0.9291	0.4458	0.6774	0.047*	0.231 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0393 (6)	0.0459 (6)	0.0240 (4)	−0.0136 (5)	0.0046 (4)	0.0053 (4)
C1	0.0242 (5)	0.0204 (4)	0.0120 (4)	−0.0002 (4)	−0.0007 (4)	−0.0024 (3)
C2	0.0300 (6)	0.0259 (5)	0.0125 (4)	−0.0026 (4)	−0.0023 (4)	0.0002 (4)
C3	0.0248 (5)	0.0261 (5)	0.0158 (4)	−0.0019 (4)	−0.0033 (4)	0.0052 (4)
C4	0.0240 (5)	0.0189 (4)	0.0152 (4)	−0.0037 (4)	−0.0042 (4)	0.0038 (3)
C5	0.0174 (4)	0.0151 (4)	0.0120 (4)	−0.0020 (3)	−0.0026 (3)	0.0009 (3)
C6	0.0238 (5)	0.0135 (4)	0.0136 (4)	−0.0013 (4)	−0.0030 (3)	0.0002 (3)
C7	0.0220 (5)	0.0139 (4)	0.0122 (4)	−0.0021 (3)	−0.0034 (3)	−0.0001 (3)
C8	0.0141 (4)	0.0128 (4)	0.0111 (3)	0.0005 (3)	0.0002 (3)	−0.0010 (3)
C9	0.0156 (4)	0.0133 (4)	0.0115 (4)	−0.0003 (3)	−0.0006 (3)	−0.0013 (3)
C10	0.0172 (4)	0.0146 (4)	0.0112 (4)	−0.0004 (3)	−0.0017 (3)	−0.0012 (3)
C11	0.0233 (5)	0.0155 (4)	0.0159 (4)	−0.0026 (4)	−0.0040 (4)	−0.0020 (3)
C12	0.0221 (5)	0.0134 (4)	0.0169 (4)	−0.0020 (4)	−0.0004 (3)	−0.0020 (3)
C13	0.0141 (4)	0.0121 (4)	0.0153 (4)	0.0006 (3)	0.0003 (3)	0.0002 (3)
C14	0.0126 (4)	0.0124 (4)	0.0131 (4)	0.0006 (3)	0.0002 (3)	−0.0003 (3)
C15	0.0207 (4)	0.0158 (4)	0.0137 (4)	0.0014 (4)	−0.0014 (4)	0.0000 (3)
C16	0.0252 (5)	0.0181 (4)	0.0153 (4)	0.0025 (4)	−0.0029 (4)	0.0011 (3)
C17	0.0196 (5)	0.0168 (4)	0.0175 (4)	0.0028 (4)	0.0018 (4)	0.0027 (3)
C18	0.0139 (4)	0.0132 (4)	0.0183 (4)	0.0010 (3)	0.0005 (3)	0.0014 (3)
C19	0.0151 (4)	0.0141 (4)	0.0239 (5)	0.0000 (3)	0.0008 (4)	0.0025 (3)
C20	0.0211 (5)	0.0150 (4)	0.0285 (5)	0.0013 (4)	0.0005 (4)	−0.0009 (4)
C21	0.0202 (5)	0.0175 (4)	0.0272 (5)	0.0006 (4)	−0.0001 (4)	0.0067 (4)
C22	0.0270 (6)	0.0188 (4)	0.0221 (5)	0.0029 (4)	−0.0011 (4)	0.0058 (4)
C23	0.0321 (6)	0.0246 (5)	0.0233 (5)	−0.0109 (5)	−0.0060 (4)	0.0068 (4)
C24	0.0305 (6)	0.0196 (5)	0.0234 (5)	0.0009 (4)	−0.0080 (4)	0.0038 (4)
C25	0.0166 (4)	0.0199 (5)	0.0182 (4)	−0.0002 (4)	−0.0034 (3)	−0.0001 (4)
C26	0.0155 (4)	0.0203 (5)	0.0157 (4)	0.0045 (3)	0.0022 (3)	0.0013 (3)
C27	0.0132 (4)	0.0175 (4)	0.0217 (4)	0.0010 (3)	0.0010 (3)	0.0007 (4)
C28	0.0278 (6)	0.0217 (5)	0.0325 (6)	0.0061 (4)	0.0128 (5)	0.0076 (5)
C29	0.0261 (6)	0.0197 (5)	0.0369 (6)	0.0006 (4)	0.0068 (5)	−0.0046 (5)
C30	0.0308 (6)	0.0257 (6)	0.0490 (8)	−0.0048 (5)	0.0039 (6)	−0.0127 (6)
O2A	0.0210 (5)	0.0291 (6)	0.0300 (6)	0.0004 (4)	0.0052 (4)	0.0005 (5)
O2B	0.038 (3)	0.041 (3)	0.039 (3)	0.008 (2)	0.0146 (19)	0.000 (2)

Geometric parameters (Å, º)

O1—C3	1.2117 (15)	C16—H16A	0.9900
C1—C2	1.5370 (15)	C16—H16B	0.9900
C1—C10	1.5452 (14)	C17—C28	1.5196 (16)
C1—H1A	0.9900	C17—C18	1.5370 (14)
C1—H1B	0.9900	C17—C22	1.5403 (15)
C2—C3	1.5068 (17)	C18—C19	1.5418 (14)
C2—H2A	0.9900	C18—H18	1.0000
C2—H2B	0.9900	C19—C20	1.5121 (15)
C3—C4	1.5326 (15)	C19—C21	1.5730 (15)
C4—C23	1.5310 (16)	C19—H19	1.0000
C4—C24	1.5436 (17)	C20—C29	1.3324 (17)
C4—C5	1.5617 (14)	C20—C30	1.5039 (17)
C5—C6	1.5335 (14)	C21—C22	1.5388 (16)
C5—C10	1.5625 (14)	C21—H21A	0.9900
C5—H5	1.0000	C21—H21B	0.9900
C6—C7	1.5282 (13)	C22—H22A	0.9900
C6—H6A	0.9900	C22—H22B	0.9900
C6—H6B	0.9900	C23—H23A	0.9800
C7—C8	1.5431 (13)	C23—H23B	0.9800
C7—H7A	0.9900	C23—H23C	0.9800
C7—H7B	0.9900	C24—H24A	0.9800
C8—C26	1.5461 (14)	C24—H24B	0.9800
C8—C9	1.5646 (13)	C24—H24C	0.9800
C8—C14	1.5889 (13)	C25—H25A	0.9800
C9—C11	1.5395 (14)	C25—H25B	0.9800
C9—C10	1.5668 (13)	C25—H25C	0.9800
C9—H9	1.0000	C26—H26A	0.9800
C10—C25	1.5419 (15)	C26—H26B	0.9800
C11—C12	1.5304 (15)	C26—H26C	0.9800
C11—H11A	0.9900	C27—H27A	0.9800
C11—H11B	0.9900	C27—H27B	0.9800
C12—C13	1.5300 (14)	C27—H27C	0.9800
C12—H12A	0.9900	C28—O2B	1.1320 (19)
C12—H12B	0.9900	C28—O2A	1.1353 (17)
C13—C18	1.5341 (13)	C28—H2AO	1.0937
C13—C14	1.5648 (13)	C28—H2BO	1.0937
C13—H13	1.0000	C29—H29A	0.9500
C14—C27	1.5455 (14)	C29—H29B	0.9500
C14—C15	1.5537 (13)	C30—H30A	0.9800
C15—C16	1.5339 (14)	C30—H30B	0.9800
C15—H15A	0.9900	C30—H30C	0.9800
C15—H15B	0.9900	O2A—H2BO	0.6003
C16—C17	1.5185 (15)	O2B—H2AO	0.7987
C2—C1—C10	113.70 (9)	C17—C16—H16A	109.7
C2—C1—H1A	108.8	C15—C16—H16A	109.7
C10—C1—H1A	108.8	C17—C16—H16B	109.7
C2—C1—H1B	108.8	C15—C16—H16B	109.7
C10—C1—H1B	108.8	H16A—C16—H16B	108.2
H1A—C1—H1B	107.7	C16—C17—C28	108.22 (9)
C3—C2—C1	111.98 (9)	C16—C17—C18	110.09 (8)
C3—C2—H2A	109.2	C28—C17—C18	114.99 (9)
C1—C2—H2A	109.2	C16—C17—C22	116.87 (9)
C3—C2—H2B	109.2	C28—C17—C22	104.98 (9)
C1—C2—H2B	109.2	C18—C17—C22	101.77 (8)
H2A—C2—H2B	107.9	C13—C18—C17	111.08 (8)
O1—C3—C2	121.04 (11)	C13—C18—C19	119.95 (8)
O1—C3—C4	122.13 (11)	C17—C18—C19	104.68 (8)
C2—C3—C4	116.82 (9)	C13—C18—H18	106.8
C23—C4—C3	108.07 (10)	C17—C18—H18	106.8
C23—C4—C24	107.70 (9)	C19—C18—H18	106.8
C3—C4—C24	108.94 (9)	C20—C19—C18	117.41 (9)
C23—C4—C5	110.30 (8)	C20—C19—C21	109.82 (9)
C3—C4—C5	107.77 (9)	C18—C19—C21	103.84 (8)
C24—C4—C5	113.91 (9)	C20—C19—H19	108.5
C6—C5—C4	113.31 (8)	C18—C19—H19	108.5
C6—C5—C10	110.73 (8)	C21—C19—H19	108.5
C4—C5—C10	116.85 (8)	C29—C20—C30	121.01 (11)
C6—C5—H5	104.9	C29—C20—C19	125.27 (10)
C4—C5—H5	104.9	C30—C20—C19	113.62 (10)
C10—C5—H5	104.9	C22—C21—C19	106.79 (8)
C7—C6—C5	110.54 (8)	C22—C21—H21A	110.4
C7—C6—H6A	109.5	C19—C21—H21A	110.4
C5—C6—H6A	109.5	C22—C21—H21B	110.4
C7—C6—H6B	109.5	C19—C21—H21B	110.4
C5—C6—H6B	109.5	H21A—C21—H21B	108.6
H6A—C6—H6B	108.1	C21—C22—C17	103.77 (9)
C6—C7—C8	114.09 (8)	C21—C22—H22A	111.0
C6—C7—H7A	108.7	C17—C22—H22A	111.0
C8—C7—H7A	108.7	C21—C22—H22B	111.0
C6—C7—H7B	108.7	C17—C22—H22B	111.0
C8—C7—H7B	108.7	H22A—C22—H22B	109.0
H7A—C7—H7B	107.6	C4—C23—H23A	109.5
C7—C8—C26	107.13 (8)	C4—C23—H23B	109.5
C7—C8—C9	109.33 (7)	H23A—C23—H23B	109.5
C26—C8—C9	111.23 (8)	C4—C23—H23C	109.5
C7—C8—C14	110.25 (7)	H23A—C23—H23C	109.5
C26—C8—C14	110.51 (7)	H23B—C23—H23C	109.5
C9—C8—C14	108.39 (7)	C4—C24—H24A	109.5
C11—C9—C8	110.61 (8)	C4—C24—H24B	109.5
C11—C9—C10	113.96 (8)	H24A—C24—H24B	109.5
C8—C9—C10	116.60 (7)	C4—C24—H24C	109.5
C11—C9—H9	104.8	H24A—C24—H24C	109.5
C8—C9—H9	104.8	H24B—C24—H24C	109.5
C10—C9—H9	104.8	C10—C25—H25A	109.5
C25—C10—C1	108.01 (8)	C10—C25—H25B	109.5
C25—C10—C5	114.24 (8)	H25A—C25—H25B	109.5
C1—C10—C5	107.25 (8)	C10—C25—H25C	109.5
C25—C10—C9	112.78 (8)	H25A—C25—H25C	109.5
C1—C10—C9	107.64 (8)	H25B—C25—H25C	109.5
C5—C10—C9	106.61 (7)	C8—C26—H26A	109.5
C12—C11—C9	112.67 (8)	C8—C26—H26B	109.5
C12—C11—H11A	109.1	H26A—C26—H26B	109.5
C9—C11—H11A	109.1	C8—C26—H26C	109.5
C12—C11—H11B	109.1	H26A—C26—H26C	109.5
C9—C11—H11B	109.1	H26B—C26—H26C	109.5
H11A—C11—H11B	107.8	C14—C27—H27A	109.5
C13—C12—C11	111.87 (8)	C14—C27—H27B	109.5
C13—C12—H12A	109.2	H27A—C27—H27B	109.5
C11—C12—H12A	109.2	C14—C27—H27C	109.5
C13—C12—H12B	109.2	H27A—C27—H27C	109.5
C11—C12—H12B	109.2	H27B—C27—H27C	109.5
H12A—C12—H12B	107.9	O2B—C28—O2A	84.54 (16)
C12—C13—C18	114.24 (8)	O2B—C28—C17	139.95 (13)
C12—C13—C14	110.94 (8)	O2A—C28—C17	131.36 (11)
C18—C13—C14	110.65 (8)	O2A—C28—H2AO	119.6
C12—C13—H13	106.9	C17—C28—H2AO	109.0
C18—C13—H13	106.9	O2B—C28—H2BO	115.4
C14—C13—H13	106.9	C17—C28—H2BO	102.7
C27—C14—C15	106.04 (8)	H2AO—C28—H2BO	143.7
C27—C14—C13	110.54 (8)	C20—C29—H29A	120.0
C15—C14—C13	109.92 (8)	C20—C29—H29B	120.0
C27—C14—C8	111.54 (8)	H29A—C29—H29B	120.0
C15—C14—C8	110.31 (7)	C20—C30—H30A	109.5
C13—C14—C8	108.48 (7)	C20—C30—H30B	109.5
C16—C15—C14	114.21 (8)	H30A—C30—H30B	109.5
C16—C15—H15A	108.7	C20—C30—H30C	109.5
C14—C15—H15A	108.7	H30A—C30—H30C	109.5
C16—C15—H15B	108.7	H30B—C30—H30C	109.5
C14—C15—H15B	108.7	C28—O2A—H2BO	70.6
H15A—C15—H15B	107.6	C28—O2B—H2AO	66.4
C17—C16—C15	109.64 (9)
C10—C1—C2—C3	−53.38 (13)	C18—C13—C14—C15	51.86 (10)
C1—C2—C3—O1	−127.94 (12)	C12—C13—C14—C8	−59.58 (10)
C1—C2—C3—C4	51.27 (14)	C18—C13—C14—C8	172.54 (8)
O1—C3—C4—C23	11.49 (16)	C7—C8—C14—C27	58.23 (10)
C2—C3—C4—C23	−167.70 (10)	C26—C8—C14—C27	176.47 (8)
O1—C3—C4—C24	−105.26 (13)	C9—C8—C14—C27	−61.40 (10)
C2—C3—C4—C24	75.54 (12)	C7—C8—C14—C15	−59.34 (10)
O1—C3—C4—C5	130.68 (12)	C26—C8—C14—C15	58.90 (10)
C2—C3—C4—C5	−48.51 (13)	C9—C8—C14—C15	−178.97 (8)
C23—C4—C5—C6	−60.46 (12)	C7—C8—C14—C13	−179.78 (8)
C3—C4—C5—C6	−178.22 (9)	C26—C8—C14—C13	−61.54 (9)
C24—C4—C5—C6	60.78 (12)	C9—C8—C14—C13	60.59 (9)
C23—C4—C5—C10	168.98 (9)	C27—C14—C15—C16	67.83 (11)
C3—C4—C5—C10	51.22 (12)	C13—C14—C15—C16	−51.68 (11)
C24—C4—C5—C10	−69.78 (12)	C8—C14—C15—C16	−171.26 (8)
C4—C5—C6—C7	164.34 (9)	C14—C15—C16—C17	55.20 (12)
C10—C5—C6—C7	−62.11 (11)	C15—C16—C17—C28	68.06 (11)
C5—C6—C7—C8	56.80 (11)	C15—C16—C17—C18	−58.38 (11)
C6—C7—C8—C26	72.23 (10)	C15—C16—C17—C22	−173.78 (9)
C6—C7—C8—C9	−48.42 (11)	C12—C13—C18—C17	176.08 (9)
C6—C7—C8—C14	−167.47 (8)	C14—C13—C18—C17	−57.87 (10)
C7—C8—C9—C11	−178.86 (8)	C12—C13—C18—C19	53.70 (12)
C26—C8—C9—C11	63.03 (10)	C14—C13—C18—C19	179.75 (8)
C14—C8—C9—C11	−58.66 (10)	C16—C17—C18—C13	61.43 (11)
C7—C8—C9—C10	48.79 (11)	C28—C17—C18—C13	−61.10 (11)
C26—C8—C9—C10	−69.32 (11)	C22—C17—C18—C13	−173.96 (8)
C14—C8—C9—C10	168.99 (8)	C16—C17—C18—C19	−167.72 (8)
C2—C1—C10—C25	−70.17 (11)	C28—C17—C18—C19	69.75 (10)
C2—C1—C10—C5	53.41 (11)	C22—C17—C18—C19	−43.11 (10)
C2—C1—C10—C9	167.78 (9)	C13—C18—C19—C20	−84.84 (12)
C6—C5—C10—C25	−66.47 (10)	C17—C18—C19—C20	149.70 (9)
C4—C5—C10—C25	65.28 (11)	C13—C18—C19—C21	153.75 (9)
C6—C5—C10—C1	173.87 (8)	C17—C18—C19—C21	28.30 (10)
C4—C5—C10—C1	−54.38 (11)	C18—C19—C20—C29	−18.72 (17)
C6—C5—C10—C9	58.80 (10)	C21—C19—C20—C29	99.53 (13)
C4—C5—C10—C9	−169.45 (8)	C18—C19—C20—C30	164.97 (10)
C11—C9—C10—C25	−58.61 (11)	C21—C19—C20—C30	−76.78 (13)
C8—C9—C10—C25	72.20 (11)	C20—C19—C21—C22	−129.22 (10)
C11—C9—C10—C1	60.44 (11)	C18—C19—C21—C22	−2.87 (11)
C8—C9—C10—C1	−168.76 (8)	C19—C21—C22—C17	−23.41 (11)
C11—C9—C10—C5	175.24 (8)	C16—C17—C22—C21	160.53 (9)
C8—C9—C10—C5	−53.95 (11)	C28—C17—C22—C21	−79.58 (10)
C8—C9—C11—C12	55.36 (11)	C18—C17—C22—C21	40.59 (10)
C10—C9—C11—C12	−170.96 (8)	C16—C17—C28—O2B	13.0 (4)
C9—C11—C12—C13	−53.50 (12)	C18—C17—C28—O2B	136.5 (4)
C11—C12—C13—C18	−178.32 (9)	C22—C17—C28—O2B	−112.5 (4)
C11—C12—C13—C14	55.78 (11)	C16—C17—C28—O2A	−135.26 (15)
C12—C13—C14—C27	63.02 (10)	C18—C17—C28—O2A	−11.72 (19)
C18—C13—C14—C27	−64.86 (10)	C22—C17—C28—O2A	99.24 (16)
C12—C13—C14—C15	179.73 (8)