Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229614017379/ku3132sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229614017379/ku3132I_polymorphsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229614017379/ku3132II_polymorphsup3.hkl |
CCDC references: 1016575; 1016576
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).
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.
RF = 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).
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 Uiso(H) = 1.5Ueq(C) for methyl H atoms or 1.2Ueq(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).
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.
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).
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) Å3 | Polyhedron, colourless |
Z = 8 | 0.48 × 0.38 × 0.17 mm |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0392P)2 + 1.7207P] where P = (Fo2 + 2Fc2)/3 |
16765 reflections | (Δ/σ)max = 0.001 |
589 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C30H46O2 | V = 5039.02 (16) Å3 |
Mr = 438.67 | Z = 8 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 9.3905 (2) Å | µ = 0.07 mm−1 |
b = 19.1080 (3) Å | T = 100 K |
c = 28.0829 (5) Å | 0.48 × 0.38 × 0.17 mm |
Agilent SuperNova diffractometer with an Atlas detector | 16765 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | 15731 reflections with I > 2σ(I) |
Tmin = 0.757, Tmax = 1.000 | Rint = 0.029 |
61016 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.30 e Å−3 |
16765 reflections | Δρmin = −0.20 e Å−3 |
589 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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···O2Bi | 0.99 | 2.48 | 3.3325 (15) | 144 |
Symmetry code: (i) x−1, y−1, z. |
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) Å3 | Plate, colourless |
Z = 4 | 0.30 × 0.26 × 0.10 mm |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0426P)2 + 0.7618P] where P = (Fo2 + 2Fc2)/3 |
7855 reflections | (Δ/σ)max = 0.001 |
305 parameters | Δρmax = 0.35 e Å−3 |
2 restraints | Δρmin = −0.21 e Å−3 |
C30H46O2 | V = 2472.93 (8) Å3 |
Mr = 438.67 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 10.3987 (2) Å | µ = 0.07 mm−1 |
b = 13.8559 (3) Å | T = 100 K |
c = 17.1632 (2) Å | 0.30 × 0.26 × 0.10 mm |
Agilent SuperNova diffractometer with an Atlas detector | 7855 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | 7535 reflections with I > 2σ(I) |
Tmin = 0.917, Tmax = 1.000 | Rint = 0.020 |
24511 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 2 restraints |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.35 e Å−3 |
7855 reflections | Δρmin = −0.21 e Å−3 |
305 parameters |
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. |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
Experimental details
(I_polymorph) | (II_polymorph) | |
Crystal data | ||
Chemical formula | C30H46O2 | C30H46O2 |
Mr | 438.67 | 438.67 |
Crystal system, space group | Orthorhombic, P212121 | Orthorhombic, P212121 |
Temperature (K) | 100 | 100 |
a, b, c (Å) | 9.3905 (2), 19.1080 (3), 28.0829 (5) | 10.3987 (2), 13.8559 (3), 17.1632 (2) |
V (Å3) | 5039.02 (16) | 2472.93 (8) |
Z | 8 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.07 | 0.07 |
Crystal size (mm) | 0.48 × 0.38 × 0.17 | 0.30 × 0.26 × 0.10 |
Data collection | ||
Diffractometer | Agilent SuperNova diffractometer with an Atlas detector | Agilent SuperNova diffractometer with an Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2013) | Multi-scan (CrysAlis PRO; Agilent, 2013) |
Tmin, Tmax | 0.757, 1.000 | 0.917, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 61016, 16765, 15731 | 24511, 7855, 7535 |
Rint | 0.029 | 0.020 |
(sin θ/λ)max (Å−1) | 0.735 | 0.725 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.098, 1.02 | 0.036, 0.094, 1.02 |
No. of reflections | 16765 | 7855 |
No. of parameters | 589 | 305 |
No. of restraints | 0 | 2 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.20 | 0.35, −0.21 |
Computer programs: CrysAlis PRO (Agilent, 2013), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006) and PLATON (Spek, 2009), publCIF (Westrip, 2010).
Ring | Molecule | Cremer–Pople parameters |
A | (IA) | Q = 0.5309 Å, θ = 4.71°, φ = 313.17° |
(IB) | Q = 0.5129 Å, θ = 10.86°, φ = 326.34° | |
(II) | Q = 0.5307 Å, θ = 4.74°, φ = 311.5° | |
B | (IA) | Q = 0.5738 Å, θ = 7.43°, φ = 3.96° |
(IB) | Q = 0.5737 Å, θ = 11.24°, φ = 12.07° | |
(II) | Q = 0.5738 Å, θ = 8.83°, φ = 2.3° | |
C | (IA) | Q = 0.6142 Å, θ = 9.69°, φ = 309.15° |
(IB) | Q = 0.6108 Å, θ = 5.99°, φ = 352.32° | |
(II) | Q = 0.6039 Å, θ = 6.65°, φ = 330.0° | |
D | (IA) | Q = 0.5695 Å, θ = 172.95°, φ = 65.23° |
(IB) | Q = 0.5829 Å, θ = 174.9°, φ = 102.06° | |
(II) | Q = 0.5828 Å, θ = 174.38°, φ = 77.8° | |
E | (IA) | q2 = 0.4392 Å, φ2 = 1.25° |
(IB) | q2 = 0.4880 Å, φ2 = 0.73° | |
(II) | q2 = 0.4279 (15) Å, φ2 = 4.3 (2)° |
(IA) | (IB) | (II) | |
O1—C3—C4—C5 | 130.55 (12) | 140.00 (13) | 130.68 (12) |
O1—C3—C4—C23 | -104.7 (2) | -95.5 (2) | -105.3 (2) |
C18—C19—C20—C29 | 142.65 (12) | -25.16 (18) | -18.72 (17) |
C21—C19—C20—C29 | -98.98 (14) | 93.76 (15) | 99.53 (13) |
C18—C19—C20—C30 | -40.80 (16) | 157.26 (12) | 164.97 (10) |
C21—C19—C20—C30 | 77.58 (14) | -83.81 (15) | -76.78 (13) |
C16—C17—C28—O2 | -130.43 (12) | -139.26 (16) | -135.26 (15) (O2A), 13.0 (4) (O2B) |
C22—C17—C28—O2 | 103.51 (13) | 94.63 (17) | 99.24 (16) (O2A), -112.5 (4) (O2B) |
C18—C17—C28—O2 | -7.66 (17) | -15.7 (2) | -11.72 (19) (O2A), 136.5 (4) (O2B) |
C2—C1—C10—C5 | 53.32 (12) | 55.44 (13) | 53.41 (11) |
C4—C5—C10—C1 | -54.10 (12) | -53.51 (12) | -54.38 (11) |
C2—C3—C4—C5 | -48.35 (13) | -42.03 (14) | -48.51 (13) |
C1—C2—C3—C4 | 51.89 (15) | 47.49 (17) | 51.27 (14) |
C17—C18—C19—C21 | 27.22 (10) | 26.65 (12) | 28.30 (10) |
C19—C21—C22—C17 | -25.95 (12) | -25.39 (14) | -23.41 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13A—H13A···O2A | 1.00 | 2.47 | 3.1452 (13) | 124.8 |
C13B—H13B···O2B | 1.00 | 2.50 | 3.1792 (15) | 124.5 |
C19A—H19A···O2A | 1.00 | 2.60 | 3.0801 (14) | 109.6 |
C19B—H19B···O2B | 1.00 | 2.53 | 3.0134 (17) | 109.2 |
C22A—H22A···O2Bi | 0.99 | 2.48 | 3.3325 (15) | 144.3 |
Symmetry code: (i) x−1, y−1, z. |