1,1-Di(9-fluorenyl)­ethyl acetate, a by-­product from the acetyl­ation of 9-fluorenyl­lithium

The preparation of sp-9-acetyl­fluorene from the reaction of 9-­fluorenyl­lithium with acetyl chloride also provided 9-(1-acetoxy­ethyl­idene)­fluorene (`di­acetyl­fluorene') and 1,1-di(9-fluorenyl)­ethanol, (II), as by-products recently characterized by X-ray analysis. A third by-product, 1,1-di(9-fluorenyl)­ethyl acetate, (III), C₃₀H₂₄O₂, has now been unequivocally identified for the first time, and emanates from the acetyl­ation of the oxy­anion of (II). In the asymmetric unit, compound (III) exists as two almost identical structures which differ slightly, but significantly, in conformation. Neither possesses the significant fluorene-ring bowing or the perpendicularity of the two ring planes exhibited by (II). The angle between the least-squares planes of the two fluorene rings of (III) is 58.45 (9) and 60.95 (10)°, respectively, for the two conformations, and their corresponding bonding parameters also differ slightly in a number of instances.

S1. Comment

Although the acetylation of 9-metalated fluorenes with acetyl chloride and related reagents has received much attention (e.g. Naik et al., 1988; Rouzaud et al., 1965; Scherf & Brown, 1961; Greenhow et al., 1953; Von & Wagner, 1944; Miller & Bachman, 1935), the results have been controversial, mainly because of inadequate structure identification of the products. Moreover, difficulties in their separation and purification also led to discrepancies in the reported melting points. In light of this situation and the important stereochemistry associated with 9-substituted fluorenes, we undertook a re-examination of the reaction of 9-fluorenyllithium with acetyl chloride in tetrahydrofuran. This study afforded the definitive characterization of the major product, sp-9-acetylfluorene, (I) (Meyers et al., 2000), and two byproducts, 9-(1-acetoxyethylidene)fluorene (Robinson et al., 2000), and 1,1-bis(9-fluorenyl)ethanol, (II) (Meyers et al., 2001). A third byproduct, only slightly less polar than (II) and present in very small amounts, was detected by TLC and separated via flash chromatography. There was insufficient material to obtain a definitive NMR spectrum, but the ¹H NMR spectrum of the separated material indicated that it contained (II) and another difluorenyl compound similar to (II). A single-crystal was selected from the mass and submitted to X-ray analysis, which indicated this compound to be 1,1-bis(9-fluorenyl)ethyl acetate, (III). Subsequently, larger amounts of (III) were synthesized directly by the acetylation of isolated (II) with acetic anhydride and DMAP as well as with acetyl chloride and pyridine. ¹H and ¹³C NMR as well as an additional X-ray analysis unequivocally confirmed the suggested structure. As illustrated in the Scheme, a reasonable pathway leading to (III) in the acetylation involves nucleophilic attack of the 9-fluorenyllithium on initially formed (I) to provide the oxyanion of (II), which is subsequently either protonated to form (II) or acetylated with residual acetyl chloride to form (III). While, as already noted, (III) has not been previously identified as a product in the acetylation of 9-fluorenyl anion, Von & Wagner (1944) reported that the major product in this reaction, (I), `deteriorated rapidly on storage with conversion to dimeric acetylfluorene.' They suggested no structure for this dimer, and provided only elemental analysis and molecular weight, both of which are identical to those of (III). They noted that their dimer did not react with phenylhydrazine, which also would apply to (III). However, they reported a melting point of 520–521 K (corrected) for their dimer, while (III) melts sharply at 441.5–443 K (corrected). In light of the sharp difference in melting points and mode of formation of the two products, it is reasonable to assume that the Von & Wagner dimer and (III) are not the same. \sch

The X-ray structure of (III) with the atom numbering for the two molecules in the asymmetric unit is illustrated in Fig. 1. The structure reveals two almost identical molecules which differ slightly, but significantly, in conformation and is a not-too-common example of the concurrent co-crystallization of more than one molecular conformation. Differences between the two molecules in the asymmetric unit are manifested in their geometric parameters. Table 1 illustrates the largest differences in the geometric parameters between molecules 1 and 2. Note that equivalent torsion angles about one of the two bonds that join the two fluorene rings of each molecule (the C9X—C10 bond in molecule 1 and the C9Z—C10' bond in molecule 2) generally differ by 7–8 degrees. These significant torsional differences are associated with all of the significant bond-angle variations listed in Table 1 which range from 5 to 8 σ. By contrast, smaller differences are observed between equivalent torsion angles about the C9—C10 and C9Y—C10' bonds, which are the other bonds connecting the two fluorene rings in the respective molecules.

Chemically, compound (III), a di-9-fluorenyl alcohol, differs only slightly from its acetate ester (II). However, significant conformational differences are apparent in their crystal structures. For example, while the two fluorene rings of (II) are normal to each other, those in (III) deviate from perpendicularity by 31.55 (9) (molecule 1) and 29.05 (10)° (molecule 2). In addition, the significant bowing of one of the fluorene rings of (II) has been suggested to emanate from its intermolecular interactions in the packing structure (Meyers et al., 2001). Such bowing is much less obvious in (III). While all of the fluorene rings of (III) are reasonably flat, the two on the right side (Fig. 1) are significantly flatter (χ² values of 1517 and 753 for molecules 1 and 2, respectively) than those on the left (χ² values of 4811 and 7415 for molecules 1 and 2, respectively). Complete least-squares plane data for all of the fluorene rings can be found in the CIF.

Related literature

For related literature, see: Greenhow et al. (1953); Meyers et al. (2000, 2001); Miller & Bachman (1935); Naik et al. (1988); Robinson et al. (2000); Rouzaud et al. (1965); Scherf & Brown (1961); Sheldrick (1997); Von & Wagner (1944).

S2. Experimental

Compound (III) was isolated by flash chromatography as one of the byproducts in our preparation of (I) from the reaction of 9-fluorenyllithium with acetyl chloride in THF under argon (Meyers et al., 2000; Meyers et al., 2001; Robinson et al., 2000). It was also prepared directly from (II) via treatment with acetic anhydride and DMAP, or acetyl chloride and pyridine. Chromatographically (TLC and column) it was slightly less polar than (II); m.p. 441.5–443 K (corr.). ¹H NMR: δ 1.67 (s, 3 H), 2.25 (s, 3 H), 4.87 (s, 2 H), 7.01 (m, 4 H), 7.16 (ddd, 2 H, J = 7.5, 1.2 Hz), 7.26 (dd, 2 H, J = 7.5 Hz), 7.35 (dd, 2 H, J = 7.5 Hz), 7.59 (d, 2 H, J = 7.5 Hz), 7.64 (d, 2 H, J = 7.5 Hz), 7.68 (d, 2H, J = 7.5 Hz); ¹³C NMR: δ 20.92, 22.82, 54.52, 89.53, 119.53, 119.57, 126.24, 126.40, 126.80, 126.85, 127.29, 127.43, 141.93, 142.02, 142.66, 143.52, 169.89. Von & Wagner (1944) reported m.p. 520–521 K for `dimeric 9-acetylfluorene', same m.w. and elemental analysis as (III).

S3. Refinement

The rotational orientations of the methyl groups were refined by the circular Fourier methods available in SHELXL97 (Sheldrick, 1997). All H atoms were riding.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: PROCESS in TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: MITHRIL (Gilmore, 1984); program(s) used to refine structure: TEXSAN and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: TEXSAN, SHELXL97 and PLATON (Spek, 2000).

Figures

Fig. 1. The molecular structure and atom-numbering scheme for (III) with displacement ellipsoids at the 50% probablilty level. Although both molecules reside in the asymmetric unit, they have been rotated relative to each other for clarity and to emphasize the fact that they are nearly identical.

1,1-Di(9-fluorenyl)ethyl Acetate

Crystal data

C30H24O2	F(000) = 880
Mr = 416.49	Dx = 1.260 Mg m^−3
Triclinic, P1	Melting point = 441.5–443 K
a = 13.211 (3) Å	Mo Kα radiation, λ = 0.71069 Å
b = 19.044 (3) Å	Cell parameters from 25 reflections
c = 9.5505 (12) Å	θ = 10.0–11.3°
α = 98.852 (11)°	µ = 0.08 mm^−1
β = 108.115 (14)°	T = 296 K
γ = 74.565 (14)°	Irregular fragment, colorless
V = 2194.7 (6) Å^3	0.43 × 0.41 × 0.27 mm
Z = 4

Data collection

Rigaku AFC-5S diffractometer	Rint = 0.033
Radiation source: sealed tube	θmax = 25.0°, θmin = 1.8°
Graphite monochromator	h = 0→15
ω scans	k = −21→22
8103 measured reflections	l = −11→10
7737 independent reflections	3 standard reflections every 100 reflections
2792 reflections with I > 2σ(I)	intensity decay: 0.5%

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.046P)^2] where P = (Fo^2 + 2Fc^2)/3
7737 reflections	(Δ/σ)max < 0.001
581 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

Geometry. SELECTED LEAST SQUARES PLANES

Definitions: Sigref - R·M·S-Error of the Contributing Atoms Sigpln - Sqrt(Sum(j=1:N)(D(j)**2/(N-3)) Chisq - Chi-Squared = Sum(j=1:N)(D(j)**2)/Sigref**2

——-Plane 1———-

Atoms Distance From Defining Plane (Angstroms) Plane with s.u.

C1 0.047 (4) C2 0.072 (4) C3 0.009 (4) C4 - 0.042 (4) C4a -0.054 (4) C4b -0.047 (4) C5 0.014 (4) C6 0.042 (4) C7 0.045 (4) C8 0.005 (4) C8a -0.037 (4) C9 - 0.012 (3) C9a -0.042 (4)

Sigref 0.004 Sigpln 0.046 Chisq 1516.9 ===========================

——-Plane 2———-

Atoms Distance From Defining Plane (Angstroms) Plane with s.u.

C1X -0.023 (4) C2X -0.082 (4) C3X -0.075 (4) C4X -0.007 (4) C4aX 0.075 (3) C4bX 0.075 (3) C5X 0.076 (4) C6X 0.004 (4) C7X -0.109 (4) C8X -0.107 (4) C8aX 0.012 (3) C9X 0.089 (3) C9aX 0.071 (3)

Sigref 0.004 Sigpln 0.081 Chisq 4810.9 Plane 1 - Plane 2 A ngle: 58.45 (9) °. ===========================

——-Plane 3———-

Atoms Distance From Defining Plane (Angstroms) Plane with s.u.

C1Y -0.025 (4) C2Y -0.052 (4) C3Y -0.023 (4) C4Y 0.014 (4) C4aY 0.038 (4) C4bY 0.027 (4) C5Y 0.015 (4) C6Y -0.011 (4) C7Y -0.038 (6) C8Y -0.039 (4) C8aY 0.013 (4) C9Y 0.031 (4) C9aY 0.049 (4)

Sigref 0.004 Sigpln 0.036 Chisq 753.0 ===========================

——-Plane 4———-

Atoms Distance From Defining Plane (Angstroms) Plane with s.u.

C1Z 0.121 (4) C2Z 0.147 (4) C3Z 0.031 (4) C4Z -0.083 (4) C4AZ -0.105 (4) C4BZ -0.107 (4) C5Z -0.037 (4) C6Z 0.083 (5) C7Z 0.143 (5) C8Z 0.056 (4) C8aZ -0.081 (4) C9Z -0.127 (3) C9aZ -0.040 (4)

Sigref 0.004 Sigpln 0.111 Chisq 7415.0 Plane 3 - Plane 4 A ngle: 60.95 (10) °. ===========================

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

	x	y	z	Uiso*/Ueq
O1	0.71889 (17)	0.12752 (12)	0.5857 (2)	0.0484 (6)
O2	0.8552 (3)	0.18119 (14)	0.7233 (3)	0.0788 (9)
C1	1.0024 (3)	−0.06952 (19)	0.7725 (4)	0.0525 (10)
C2	1.0739 (3)	−0.1371 (2)	0.7933 (4)	0.0637 (11)
C3	1.0822 (3)	−0.1876 (2)	0.6751 (5)	0.0670 (11)
C4	1.0216 (3)	−0.1710 (2)	0.5328 (4)	0.0590 (10)
C4a	0.9503 (3)	−0.10268 (18)	0.5114 (4)	0.0450 (9)
C4b	0.8809 (3)	−0.07008 (19)	0.3745 (4)	0.0455 (9)
C5	0.8694 (3)	−0.0973 (2)	0.2282 (4)	0.0544 (10)
C6	0.8000 (3)	−0.0545 (2)	0.1186 (4)	0.0617 (11)
C7	0.7440 (3)	0.0152 (2)	0.1506 (4)	0.0617 (11)
C8	0.7561 (3)	0.0436 (2)	0.2968 (4)	0.0511 (9)
C8a	0.8252 (3)	0.00064 (18)	0.4090 (3)	0.0411 (8)
C9	0.8584 (2)	0.01863 (17)	0.5760 (3)	0.0391 (8)
C9a	0.9385 (3)	−0.05232 (18)	0.6314 (4)	0.0435 (9)
C10	0.7649 (3)	0.05483 (17)	0.6474 (3)	0.0412 (8)
C11	0.8037 (3)	0.06241 (18)	0.8148 (3)	0.0516 (10)
C12	0.7692 (4)	0.1835 (2)	0.6315 (5)	0.0611 (11)
C13	0.7017 (4)	0.2489 (2)	0.5500 (5)	0.0973 (16)
C1X	0.7363 (3)	−0.1196 (2)	0.6153 (4)	0.0568 (10)
C2X	0.7298 (3)	−0.1809 (2)	0.6727 (5)	0.0672 (11)
C3X	0.6599 (3)	−0.1745 (2)	0.7585 (4)	0.0683 (12)
C4X	0.5960 (3)	−0.1071 (2)	0.7882 (4)	0.0587 (10)
C4aX	0.6038 (3)	−0.04626 (19)	0.7336 (3)	0.0450 (9)
C4bX	0.5413 (3)	0.02913 (19)	0.7418 (3)	0.0448 (9)
C5X	0.4619 (3)	0.0611 (2)	0.8141 (4)	0.0571 (10)
C6X	0.4100 (3)	0.1334 (2)	0.7987 (4)	0.0669 (11)
C7X	0.4338 (3)	0.1731 (2)	0.7094 (4)	0.0641 (11)
C8X	0.5134 (3)	0.14158 (19)	0.6369 (4)	0.0562 (10)
C8aX	0.5690 (3)	0.06982 (19)	0.6553 (3)	0.0438 (9)
C9X	0.6614 (2)	0.02274 (17)	0.5945 (3)	0.0414 (8)
C9aX	0.6741 (3)	−0.05194 (18)	0.6471 (3)	0.0426 (8)
H1	0.9972	−0.0357	0.8528	0.063*
H2	1.1170	−0.1486	0.8880	0.076*
H3	1.1291	−0.2335	0.6913	0.080*
H4	1.0284	−0.2048	0.4530	0.071*
H5	0.9082	−0.1438	0.2053	0.065*
H6	0.7904	−0.0728	0.0204	0.074*
H7	0.6978	0.0435	0.0741	0.074*
H8	0.7183	0.0907	0.3187	0.061*
H9	0.9030	0.0545	0.5937	0.047*
H11a	0.0674	0.5894	0.6345	0.075*
H11b	0.1845	0.5415	0.6373	0.075*
H11c	0.1651	0.6268	0.6626	0.075*
H13a	−0.0648	0.7865	0.9222	0.100*
H13b	0.0567	0.7677	1.0218	0.100*
H13c	−0.0315	0.7345	1.0494	0.100*
H1X	0.7823	−0.1244	0.5561	0.068*
H2X	0.7729	−0.2264	0.6533	0.081*
H3X	0.6560	−0.2157	0.7960	0.082*
H4X	0.5481	−0.1026	0.8444	0.070*
H5X	0.4442	0.0339	0.8723	0.069*
H6X	0.3582	0.1556	0.8490	0.080*
H7X	0.3964	0.2216	0.6974	0.077*
H8X	0.5289	0.1687	0.5764	0.067*
H9X	0.6360	0.0198	0.4863	0.050*
O1'	0.12445 (18)	0.65076 (11)	0.9159 (2)	0.0476 (6)
O2'	−0.0483 (2)	0.66597 (13)	0.7639 (3)	0.0662 (7)
C1Y	0.1088 (3)	0.4215 (2)	0.6675 (4)	0.0624 (11)
C2Y	0.1275 (3)	0.3466 (2)	0.6300 (5)	0.0731 (12)
C3Y	0.1702 (3)	0.2975 (2)	0.7383 (6)	0.0764 (13)
C4Y	0.1937 (3)	0.3219 (2)	0.8857 (5)	0.0720 (12)
C4aY	0.1750 (3)	0.3967 (2)	0.9241 (4)	0.0541 (10)
C4bY	0.1882 (3)	0.4373 (2)	1.0689 (4)	0.0578 (10)
C5Y	0.2252 (3)	0.4124 (2)	1.2094 (5)	0.0731 (12)
C6Y	0.2286 (4)	0.4628 (3)	1.3300 (5)	0.0902 (15)
C7Y	0.1949 (4)	0.5364 (3)	1.3113 (4)	0.0860 (14)
C8Y	0.1567 (3)	0.5622 (2)	1.1711 (4)	0.0718 (12)
C8aY	0.1552 (3)	0.5115 (2)	1.0498 (4)	0.0538 (10)
C9Y	0.1185 (3)	0.52425 (18)	0.8858 (3)	0.0475 (9)
C9aY	0.1348 (3)	0.44644 (18)	0.8144 (4)	0.0500 (9)
C10'	0.1705 (3)	0.57971 (17)	0.8445 (3)	0.0441 (8)
C11'	0.1445 (3)	0.58480 (17)	0.6796 (3)	0.0499 (9)
C12'	0.0178 (3)	0.68522 (19)	0.8713 (4)	0.0512 (9)
C13'	−0.0077 (3)	0.74911 (19)	0.9754 (4)	0.0665 (11)
C1Z	0.3819 (3)	0.4375 (2)	0.8194 (4)	0.0645 (11)
C2Z	0.4523 (3)	0.3959 (2)	0.7395 (5)	0.0763 (13)
C3Z	0.5096 (3)	0.4290 (2)	0.6825 (5)	0.0786 (13)
C4Z	0.5003 (3)	0.5029 (2)	0.7056 (4)	0.0662 (11)
C4aZ	0.4307 (3)	0.54449 (19)	0.7853 (4)	0.0486 (9)
C4bZ	0.4127 (3)	0.62182 (19)	0.8354 (4)	0.0537 (10)
C5Z	0.4642 (3)	0.6745 (2)	0.8210 (5)	0.0754 (12)
C6Z	0.4407 (4)	0.7428 (2)	0.8911 (6)	0.0913 (15)
C7Z	0.3686 (4)	0.7587 (2)	0.9745 (5)	0.0866 (14)
C8Z	0.3158 (3)	0.7073 (2)	0.9881 (4)	0.0691 (12)
C8aZ	0.3371 (3)	0.6379 (2)	0.9169 (4)	0.0503 (9)
C9Z	0.2960 (3)	0.57069 (18)	0.9191 (3)	0.0469 (9)
C9aZ	0.3683 (3)	0.51251 (19)	0.8398 (4)	0.0469 (9)
H1Y	0.0792	0.4542	0.5943	0.075*
H2Y	0.1111	0.3293	0.5309	0.088*
H3Y	0.1832	0.2475	0.7113	0.092*
H4Y	0.2216	0.2889	0.9583	0.086*
H5Y	0.2472	0.3626	1.2219	0.088*
H6Y	0.2539	0.4469	1.4247	0.108*
H7Y	0.1978	0.5696	1.3939	0.103*
H8Y	0.1328	0.6121	1.1592	0.086*
H9Y	0.0394	0.5450	0.8600	0.057*
H11d	0.8731	0.0756	0.8464	0.077*
H11e	0.8114	0.0168	0.8524	0.077*
H11f	0.7511	0.0997	0.8515	0.077*
H13d	0.6320	0.2637	0.5702	0.146*
H13e	0.6910	0.2369	0.4458	0.146*
H13f	0.7388	0.2881	0.5815	0.146*
H1Z	0.3441	0.4148	0.8591	0.077*
H2Z	0.4605	0.3456	0.7247	0.092*
H3Z	0.5553	0.4009	0.6275	0.094*
H4Z	0.5403	0.5249	0.6681	0.079*
H5Z	0.5135	0.6634	0.7650	0.091*
H6Z	0.4739	0.7785	0.8819	0.110*
H7Z	0.3548	0.8050	1.0229	0.104*
H8Z	0.2665	0.7192	1.0444	0.083*
H9Z	0.3134	0.5590	1.0216	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0443 (15)	0.0496 (15)	0.0521 (15)	−0.0121 (12)	0.0156 (12)	0.0000 (12)
O2	0.080 (2)	0.076 (2)	0.083 (2)	−0.0425 (18)	0.0159 (18)	−0.0143 (16)
C1	0.051 (2)	0.060 (2)	0.042 (2)	−0.013 (2)	0.0079 (19)	−0.0005 (19)
C2	0.053 (3)	0.075 (3)	0.059 (3)	−0.011 (2)	0.010 (2)	0.016 (2)
C3	0.062 (3)	0.059 (3)	0.082 (3)	−0.008 (2)	0.022 (3)	0.017 (3)
C4	0.060 (3)	0.056 (3)	0.067 (3)	−0.018 (2)	0.029 (2)	−0.008 (2)
C4a	0.039 (2)	0.051 (2)	0.050 (2)	−0.0159 (18)	0.0172 (18)	−0.0005 (19)
C4b	0.044 (2)	0.061 (2)	0.039 (2)	−0.0227 (19)	0.0178 (18)	−0.0036 (19)
C5	0.060 (3)	0.066 (2)	0.046 (2)	−0.025 (2)	0.027 (2)	−0.010 (2)
C6	0.073 (3)	0.088 (3)	0.037 (2)	−0.038 (3)	0.023 (2)	−0.007 (2)
C7	0.062 (3)	0.094 (3)	0.039 (2)	−0.035 (2)	0.011 (2)	0.011 (2)
C8	0.049 (2)	0.061 (2)	0.048 (2)	−0.0178 (19)	0.0159 (19)	0.006 (2)
C8a	0.036 (2)	0.056 (2)	0.038 (2)	−0.0174 (18)	0.0143 (17)	0.0006 (18)
C9	0.036 (2)	0.052 (2)	0.0334 (19)	−0.0169 (17)	0.0134 (16)	−0.0036 (16)
C9a	0.037 (2)	0.054 (2)	0.042 (2)	−0.0147 (17)	0.0136 (18)	−0.0003 (18)
C10	0.043 (2)	0.045 (2)	0.038 (2)	−0.0157 (17)	0.0136 (16)	−0.0009 (16)
C11	0.047 (2)	0.072 (3)	0.038 (2)	−0.0183 (19)	0.0153 (17)	−0.0078 (18)
C12	0.062 (3)	0.059 (3)	0.072 (3)	−0.020 (2)	0.036 (2)	−0.010 (2)
C13	0.096 (4)	0.048 (3)	0.159 (5)	−0.009 (3)	0.056 (3)	0.013 (3)
O1'	0.0439 (15)	0.0533 (15)	0.0410 (13)	−0.0074 (12)	0.0126 (11)	−0.0038 (11)
O2'	0.0474 (16)	0.0666 (18)	0.0666 (18)	−0.0059 (14)	0.0021 (14)	−0.0057 (15)
C1X	0.042 (2)	0.064 (3)	0.069 (3)	−0.020 (2)	0.021 (2)	−0.007 (2)
C2X	0.056 (3)	0.050 (2)	0.094 (3)	−0.014 (2)	0.021 (2)	0.003 (2)
C3X	0.061 (3)	0.065 (3)	0.082 (3)	−0.019 (2)	0.012 (2)	0.024 (2)
C4X	0.055 (3)	0.069 (3)	0.057 (2)	−0.019 (2)	0.016 (2)	0.012 (2)
C4aX	0.040 (2)	0.057 (2)	0.040 (2)	−0.0184 (18)	0.0081 (17)	0.0035 (18)
C4bX	0.035 (2)	0.063 (2)	0.038 (2)	−0.0187 (19)	0.0082 (17)	−0.0023 (18)
C5X	0.049 (2)	0.075 (3)	0.054 (2)	−0.020 (2)	0.021 (2)	0.006 (2)
C6X	0.050 (3)	0.078 (3)	0.075 (3)	−0.016 (2)	0.027 (2)	−0.009 (2)
C7X	0.042 (2)	0.060 (3)	0.086 (3)	−0.008 (2)	0.018 (2)	0.001 (2)
C8X	0.043 (2)	0.060 (3)	0.067 (3)	−0.013 (2)	0.012 (2)	0.012 (2)
C8aX	0.035 (2)	0.055 (2)	0.041 (2)	−0.0147 (18)	0.0056 (17)	0.0048 (18)
C9X	0.038 (2)	0.057 (2)	0.0331 (19)	−0.0185 (17)	0.0092 (16)	0.0022 (16)
C9aX	0.035 (2)	0.052 (2)	0.041 (2)	−0.0149 (18)	0.0092 (17)	−0.0016 (17)
C10'	0.045 (2)	0.044 (2)	0.040 (2)	−0.0031 (17)	0.0148 (17)	0.0019 (17)
C11'	0.057 (2)	0.052 (2)	0.036 (2)	−0.0080 (19)	0.0116 (18)	0.0023 (17)
C12'	0.045 (2)	0.052 (2)	0.056 (2)	−0.005 (2)	0.018 (2)	0.006 (2)
C13'	0.059 (3)	0.070 (3)	0.068 (3)	−0.008 (2)	0.029 (2)	−0.011 (2)
C1Y	0.055 (3)	0.056 (3)	0.059 (3)	−0.008 (2)	−0.002 (2)	0.002 (2)
C2Y	0.066 (3)	0.067 (3)	0.070 (3)	−0.015 (2)	0.001 (2)	−0.004 (2)
C3Y	0.060 (3)	0.050 (3)	0.108 (4)	−0.013 (2)	0.008 (3)	0.006 (3)
C4Y	0.060 (3)	0.067 (3)	0.089 (4)	−0.020 (2)	0.010 (2)	0.021 (3)
C4aY	0.042 (2)	0.054 (3)	0.067 (3)	−0.0114 (19)	0.014 (2)	0.012 (2)
C4bY	0.050 (2)	0.077 (3)	0.057 (3)	−0.016 (2)	0.023 (2)	0.019 (2)
C5Y	0.065 (3)	0.093 (3)	0.074 (3)	−0.016 (3)	0.029 (3)	0.030 (3)
C6Y	0.087 (4)	0.134 (5)	0.061 (3)	−0.014 (3)	0.030 (3)	0.042 (3)
C7Y	0.104 (4)	0.117 (4)	0.047 (3)	−0.025 (3)	0.033 (3)	0.011 (3)
C8Y	0.086 (3)	0.087 (3)	0.054 (3)	−0.018 (3)	0.036 (2)	0.010 (2)
C8aY	0.050 (2)	0.070 (3)	0.047 (2)	−0.016 (2)	0.0191 (19)	0.008 (2)
C9Y	0.041 (2)	0.055 (2)	0.042 (2)	−0.0073 (18)	0.0093 (17)	0.0056 (18)
C9aY	0.044 (2)	0.051 (2)	0.051 (2)	−0.0115 (19)	0.0068 (19)	0.005 (2)
C1Z	0.046 (2)	0.063 (3)	0.086 (3)	−0.006 (2)	0.021 (2)	0.018 (2)
C2Z	0.057 (3)	0.048 (3)	0.116 (4)	0.001 (2)	0.029 (3)	0.000 (3)
C3Z	0.066 (3)	0.073 (3)	0.095 (3)	0.000 (3)	0.040 (3)	−0.009 (3)
C4Z	0.063 (3)	0.070 (3)	0.075 (3)	−0.007 (2)	0.037 (2)	0.009 (2)
C4aZ	0.043 (2)	0.054 (2)	0.047 (2)	−0.0038 (19)	0.0145 (18)	0.0077 (19)
C4bZ	0.049 (2)	0.056 (3)	0.053 (2)	−0.013 (2)	0.010 (2)	0.0032 (19)
C5Z	0.070 (3)	0.064 (3)	0.101 (4)	−0.018 (2)	0.036 (3)	0.004 (3)
C6Z	0.073 (3)	0.067 (3)	0.139 (4)	−0.025 (3)	0.034 (3)	0.000 (3)
C7Z	0.058 (3)	0.066 (3)	0.125 (4)	−0.023 (3)	0.019 (3)	−0.024 (3)
C8Z	0.049 (3)	0.075 (3)	0.071 (3)	−0.013 (2)	0.011 (2)	−0.016 (2)
C8aZ	0.044 (2)	0.061 (2)	0.042 (2)	−0.0106 (19)	0.0111 (18)	−0.0025 (19)
C9Z	0.041 (2)	0.063 (2)	0.034 (2)	−0.0076 (19)	0.0104 (17)	0.0065 (17)
C9aZ	0.041 (2)	0.050 (2)	0.045 (2)	−0.0017 (18)	0.0090 (17)	0.0113 (18)

Geometric parameters (Å, º)

O1—C12	1.350 (4)	C4aZ—C9aZ	1.397 (4)
O1'—C12'	1.349 (4)	C4b—C8a	1.396 (4)
O1—C10	1.488 (4)	C4bX—C8aX	1.397 (4)
O1'—C10'	1.484 (3)	C4bY—C8aY	1.386 (5)
O2—C12	1.194 (4)	C4bZ—C8aZ	1.394 (4)
O2'—C12'	1.202 (4)	C9—C10	1.546 (4)
C1—C2	1.379 (4)	C9Y—C10'	1.557 (4)
C1X—C2X	1.396 (5)	C9X—C10	1.556 (4)
C1Y—C2Y	1.390 (5)	C9Z—C10'	1.561 (4)
C1Z—C2Z	1.392 (5)	C10—C11	1.515 (4)
C2—C3	1.378 (5)	C10'—C11'	1.516 (4)
C2Y—C3Y	1.385 (5)	C12'—C13'	1.483 (4)
C2X—C3X	1.386 (5)	C12—C13	1.492 (5)
C2Z—C3Z	1.372 (5)	C11'—H11a	0.9600
C3—C4	1.381 (5)	C11'—H11b	0.9600
C3X—C4X	1.379 (5)	C11'—H11c	0.9600
C3Y—C4Y	1.377 (5)	C11—H11d	0.9600
C3Z—C4Z	1.369 (5)	C11—H11e	0.9600
C4—C4a	1.389 (4)	C11—H11f	0.9600
C4X—C4aX	1.381 (4)	C13'—H13a	0.9600
C4Y—C4aY	1.389 (5)	C13'—H13b	0.9600
C4Z—C4aZ	1.384 (4)	C13'—H13c	0.9600
C4a—C4b	1.461 (4)	C13—H13d	0.9600
C4aX—C4bX	1.457 (4)	C13—H13e	0.9600
C4aY—C4bY	1.461 (5)	C13—H13f	0.9600
C4aZ—C4bZ	1.457 (4)	C8Z—H8Z	0.9300
C4b—C5	1.389 (4)	C1X—H1X	0.9300
C4bX—C5X	1.389 (4)	C1—H1	0.9300
C4bY—C5Y	1.389 (5)	C7Z—H7Z	0.9300
C4bZ—C5Z	1.396 (5)	C6Z—H6Z	0.9300
C5—C6	1.368 (5)	C6Y—H6Y	0.9300
C5X—C6X	1.372 (5)	C3—H3	0.9300
C5Y—C6Y	1.378 (5)	C3X—H3X	0.9300
C5Z—C6Z	1.372 (5)	C5Z—H5Z	0.9300
C6—C7	1.376 (5)	C4Z—H4Z	0.9300
C6X—C7X	1.376 (5)	C4—H4	0.9300
C6Y—C7Y	1.375 (6)	C4X—H4X	0.9300
C6Z—C7Z	1.370 (6)	C2X—H2X	0.9300
C7—C8	1.395 (4)	C2—H2	0.9300
C7X—C8X	1.390 (5)	C8Y—H8Y	0.9300
C7Y—C8Y	1.392 (5)	C7Y—H7Y	0.9300
C7Z—C8Z	1.386 (5)	C5Y—H5Y	0.9300
C8—C8a	1.384 (4)	C5—H5	0.9300
C8X—C8aX	1.378 (4)	C5X—H5X	0.9300
C8Z—C8aZ	1.391 (5)	C4Y—H4Y	0.9300
C8Y—C8aY	1.388 (5)	C6—H6	0.9300
C8a—C9	1.527 (4)	C3Z—H3Z	0.9300
C8aX—C9X	1.526 (4)	C7—H7	0.9300
C8aY—C9Y	1.526 (4)	C8X—H8X	0.9300
C8aZ—C9Z	1.524 (4)	C1Y—H1Y	0.9300
C9—C9a	1.528 (4)	C8—H8	0.9300
C9X—C9aX	1.531 (4)	C1Z—H1Z	0.9300
C9Y—C9aY	1.523 (4)	C2Z—H2Z	0.9300
C9Z—C9aZ	1.531 (4)	C2Y—H2Y	0.9300
C9a—C1	1.385 (4)	C6X—H6X	0.9300
C9aX—C1X	1.378 (4)	C9Y—H9Y	0.9800
C9aY—C1Y	1.377 (4)	C9—H9	0.9800
C9aZ—C1Z	1.381 (5)	C9X—H9X	0.9800
C4a—C9a	1.397 (4)	C9Z—H9Z	0.9800
C4aX—C9aX	1.398 (4)	C7X—H7X	0.9300
C4aY—C9aY	1.404 (4)	C3Y—H3Y	0.9300
C12—O1—C10	123.0 (3)	C9—C10—C9X	116.8 (2)
C12'—O1'—C10'	122.6 (3)	C9Y—C10'—C9Z	115.2 (3)
C1—C2—C3	120.6 (4)	O1—C12—C13	109.9 (4)
C1X—C2X—C3X	120.7 (4)	O1'—C12'—C13'	110.6 (3)
C1Y—C2Y—C3Y	120.8 (4)	O2—C12—C13	124.8 (4)
C1Z—C2Z—C3Z	120.2 (4)	O2'—C12'—C13'	124.5 (3)
C2—C3—C4	120.8 (4)	C6Y—C5Y—H5Y	120.6
C2X—C3X—C4X	119.9 (4)	C3X—C4X—H4X	120.3
C2Y—C3Y—C4Y	120.6 (4)	C4aX—C4X—H4X	120.3
C2Z—C3Z—C4Z	120.7 (4)	C4bY—C5Y—H5Y	120.6
C3—C4—C4a	118.7 (4)	C3Z—C4Z—H4Z	120.4
C3X—C4X—C4aX	119.4 (4)	C4aZ—C4Z—H4Z	120.4
C3Y—C4Y—C4aY	119.0 (4)	C6—C5—H5	120.6
C3Z—C4Z—C4aZ	119.2 (4)	C4b—C5—H5	120.6
C4—C4a—C4b	130.0 (3)	C6X—C5X—H5X	120.4
C4X—C4aX—C4bX	129.8 (3)	C4bX—C5X—H5X	120.4
C4Y—C4aY—C4bY	130.7 (4)	C3Y—C4Y—H4Y	120.5
C4Z—C4aZ—C4bZ	130.2 (3)	C4aY—C4Y—H4Y	120.5
C4—C4a—C9a	120.7 (3)	C5—C6—H6	119.4
C4X—C4aX—C9aX	121.2 (3)	C7—C6—H6	119.4
C4Y—C4aY—C9aY	120.4 (4)	C4Z—C3Z—H3Z	119.6
C4Z—C4aZ—C9aZ	121.1 (3)	C2Z—C3Z—H3Z	119.6
C9a—C4a—C4b	109.2 (3)	C5X—C6X—H6X	119.7
C9aX—C4aX—C4bX	108.8 (3)	C7X—C6X—H6X	119.7
C9aY—C4aY—C4bY	108.9 (3)	C4Y—C3Y—H3Y	119.7
C9aZ—C4aZ—C4bZ	108.6 (3)	C2Y—C3Y—H3Y	119.7
C4a—C4b—C5	130.3 (3)	C6—C7—H7	119.8
C4aX—C4bX—C5X	130.0 (3)	C8—C7—H7	119.8
C4aY—C4bY—C5Y	130.2 (4)	C6X—C7X—H7X	119.7
C4aZ—C4bZ—C5Z	129.7 (4)	C8X—C7X—H7X	119.7
C5—C4b—C8a	120.6 (3)	C3Z—C2Z—H2Z	119.9
C5X—C4bX—C8aX	120.8 (3)	C3Y—C2Y—H2Y	119.6
C5Y—C4bY—C8aY	120.7 (4)	C1Y—C2Y—H2Y	119.6
C5Z—C4bZ—C8aZ	121.3 (3)	C1Z—C2Z—H2Z	119.9
C8a—C4b—C4a	109.0 (3)	C8aX—C8X—H8X	120.2
C8aX—C4bX—C4aX	109.2 (3)	C7X—C8X—H8X	120.2
C8aY—C4bY—C4aY	109.1 (3)	C9aY—C1Y—H1Y	120.5
C8aZ—C4bZ—C4aZ	108.9 (3)	C2Y—C1Y—H1Y	120.5
C4b—C5—C6	118.9 (4)	C10'—C11'—H11a	109.5
C4bX—C5X—C6X	119.1 (4)	C10'—C11'—H11b	109.5
C4bY—C5Y—C6Y	118.9 (4)	H11a—C11'—H11b	109.5
C4bZ—C5Z—C6Z	118.8 (4)	C10'—C11'—H11c	109.5
C5—C6—C7	121.3 (3)	H11a—C11'—H11c	109.5
C5X—C6X—C7X	120.5 (4)	H11b—C11'—H11c	109.5
C5Y—C6Y—C7Y	120.5 (4)	C10—C11—H11d	109.5
C5Z—C6Z—C7Z	120.5 (4)	C10—C11—H11e	109.5
C6—C7—C8	120.5 (4)	H11d—C11—H11e	109.5
C6X—C7X—C8X	120.7 (4)	C10—C11—H11f	109.5
C6Y—C7Y—C8Y	121.4 (4)	H11d—C11—H11f	109.5
C6Z—C7Z—C8Z	121.3 (4)	H11e—C11—H11f	109.5
C7—C8—C8a	118.9 (3)	C12'—C13'—H13a	109.5
C7X—C8X—C8aX	119.6 (3)	C12'—C13'—H13b	109.5
C7Y—C8Y—C8aY	118.1 (4)	H13a—C13'—H13b	109.5
C7Z—C8Z—C8aZ	119.4 (4)	C12'—C13'—H13c	109.5
C8—C8a—C9	130.1 (3)	H13a—C13'—H13c	109.5
C8X—C8aX—C9X	130.7 (3)	H13b—C13'—H13c	109.5
C8Y—C8aY—C9Y	129.2 (3)	C12—C13—H13d	109.5
C8Z—C8aZ—C9Z	130.4 (3)	C12—C13—H13e	109.5
C8—C8a—C4b	119.9 (3)	H13d—C13—H13e	109.5
C8X—C8aX—C4bX	119.3 (3)	C12—C13—H13f	109.5
C8Y—C8aY—C4bY	120.4 (3)	H13d—C13—H13f	109.5
C8Z—C8aZ—C4bZ	118.7 (4)	H13e—C13—H13f	109.5
C4b—C8a—C9	109.9 (3)	C9aX—C1X—H1X	120.3
C4bX—C8aX—C9X	110.1 (3)	C2X—C1X—H1X	120.3
C4bY—C8aY—C9Y	110.4 (3)	C8aY—C8Y—H8Y	120.9
C4bZ—C8aZ—C9Z	110.8 (3)	C7Y—C8Y—H8Y	120.9
C8a—C9—C9a	102.1 (3)	C7Z—C8Z—H8Z	120.3
C8aX—C9X—C9aX	101.6 (2)	C8aZ—C8Z—H8Z	120.3
C8aY—C9Y—C9aY	101.9 (3)	C6Y—C7Y—H7Y	119.3
C8aZ—C9Z—C9aZ	100.8 (3)	C8Y—C7Y—H7Y	119.3
C9—C9a—C1	130.6 (3)	C2—C1—H1	120.2
C9X—C9aX—C1X	130.5 (3)	C9a—C1—H1	120.2
C9Y—C9aY—C1Y	130.0 (3)	C6Z—C7Z—H7Z	119.3
C9Z—C9aZ—C1Z	131.0 (3)	C8Z—C7Z—H7Z	119.3
C1—C9a—C4a	119.4 (3)	C3X—C2X—H2X	119.6
C1X—C9aX—C4aX	119.3 (3)	C1X—C2X—H2X	119.6
C1Y—C9aY—C4aY	120.0 (3)	C3—C2—H2	119.7
C1Z—C9aZ—C4aZ	118.5 (3)	C1—C2—H2	119.7
C4a—C9a—C9	109.7 (3)	C7Z—C6Z—H6Z	119.7
C4aX—C9aX—C9X	110.1 (3)	C5Z—C6Z—H6Z	119.7
C4aY—C9aY—C9Y	109.7 (3)	C2—C3—H3	119.6
C4aZ—C9aZ—C9Z	110.5 (3)	C4—C3—H3	119.6
C8a—C9—C10	116.8 (3)	C4X—C3X—H3X	120.0
C8aY—C9Y—C10'	114.7 (3)	C2X—C3X—H3X	120.0
C8aX—C9X—C10	111.7 (3)	C7Y—C6Y—H6Y	119.7
C8aZ—C9Z—C10'	113.7 (3)	C5Y—C6Y—H6Y	119.7
C9a—C1—C2	119.6 (3)	C6Z—C5Z—H5Z	120.6
C9aX—C1X—C2X	119.5 (3)	C3—C4—H4	120.7
C9aY—C1Y—C2Y	119.1 (4)	C4a—C4—H4	120.7
C9aZ—C1Z—C2Z	120.1 (4)	C4bZ—C5Z—H5Z	120.6
C9a—C9—C10	119.8 (3)	C8a—C8—H8	120.6
C9aX—C9X—C10	116.2 (3)	C7—C8—H8	120.6
C9aZ—C9Z—C10'	114.2 (3)	C9aZ—C1Z—H1Z	120.0
C9aY—C9Y—C10'	119.4 (3)	C2Z—C1Z—H1Z	120.0
O1—C10—C11	111.3 (2)	C8aX—C9X—H9X	109.0
O1'—C10'—C11'	110.3 (2)	C9aX—C9X—H9X	109.0
O2—C12—O1	125.2 (4)	C10—C9X—H9X	109.0
O2'—C12'—O1'	124.8 (3)	C8a—C9—H9	105.6
O1—C10—C9	104.0 (2)	C9a—C9—H9	105.6
O1—C10—C9X	100.3 (2)	C10—C9—H9	105.6
O1'—C10'—C9Z	101.9 (2)	C9aY—C9Y—H9Y	106.6
O1'—C10'—C9Y	104.3 (2)	C8aY—C9Y—H9Y	106.6
C11—C10—C9	113.3 (3)	C10'—C9Y—H9Y	106.6
C11'—C10'—C9Y	114.1 (3)	C8aZ—C9Z—H9Z	109.3
C11—C10—C9X	110.1 (3)	C9aZ—C9Z—H9Z	109.3
C11'—C10'—C9Z	110.1 (3)	C10'—C9Z—H9Z	109.3
C9aX—C9X—C10—O1	−175.8 (2)	C7Y—C8Y—C8aY—C4bY	1.7 (6)
C9aZ—C9Z—C10'—O1'	−164.6 (3)	C7X—C8X—C8aX—C4bX	2.6 (5)
C9aX—C9X—C10—C11	−58.4 (3)	C7Z—C8Z—C8aZ—C4bZ	1.0 (6)
C9aZ—C9Z—C10'—C11'	−47.5 (4)	C5—C4b—C8a—C8	1.4 (5)
C9aX—C9X—C10—C9	72.6 (3)	C5Y—C4bY—C8aY—C8Y	−1.2 (6)
C9aZ—C9Z—C10'—C9Y	83.3 (3)	C5X—C4bX—C8aX—C8X	−2.8 (5)
C8aX—C9X—C10—O1	−59.9 (3)	C5Z—C4bZ—C8aZ—C8Z	−1.9 (5)
C8aZ—C9Z—C10'—O1'	−49.6 (3)	C4a—C4b—C8a—C8	178.4 (3)
C8aX—C9X—C10—C11	57.5 (3)	C4aY—C4bY—C8aY—C8Y	178.1 (3)
C8aZ—C9Z—C10'—C11'	67.4 (3)	C4aX—C4bX—C8aX—C8X	174.8 (3)
C8aX—C9X—C10—C9	−171.5 (3)	C4aZ—C4bZ—C8aZ—C8Z	173.7 (3)
C8aZ—C9Z—C10'—C9Y	−161.8 (3)	C5—C4b—C8a—C9	−176.0 (3)
C1—C2—C3—C4	2.0 (6)	C5Y—C4bY—C8aY—C9Y	−180.0 (3)
C1X—C2X—C3X—C4X	−0.2 (6)	C5X—C4bX—C8aX—C9X	177.5 (3)
C1Y—C2Y—C3Y—C4Y	0.9 (6)	C5Z—C4bZ—C8aZ—C9Z	−178.2 (3)
C1Z—C2Z—C3Z—C4Z	1.3 (7)	C4a—C4b—C8a—C9	1.0 (4)
C2—C3—C4—C4a	−1.3 (6)	C4aY—C4bY—C8aY—C9Y	−0.8 (4)
C2X—C3X—C4X—C4aX	−1.0 (6)	C4aX—C4bX—C8aX—C9X	−4.9 (4)
C2Y—C3Y—C4Y—C4aY	−0.7 (6)	C4aZ—C4bZ—C8aZ—C9Z	−2.6 (4)
C2Z—C3Z—C4Z—C4aZ	−1.1 (6)	C4b—C8a—C9—C9a	−1.3 (3)
C3—C4—C4a—C4b	177.1 (3)	C4bY—C8aY—C9Y—C9aY	0.4 (4)
C3X—C4X—C4aX—C4bX	175.8 (3)	C4bX—C8aX—C9X—C9aX	5.1 (3)
C3Z—C4Z—C4aZ—C4bZ	174.3 (4)	C4bZ—C8aZ—C9Z—C9aZ	5.4 (4)
C3Y—C4Y—C4aY—C4bY	177.4 (4)	C8—C8a—C9—C10	49.0 (5)
C4—C4a—C4b—C5	−2.2 (6)	C8Y—C8aY—C9Y—C10'	51.1 (5)
C4Y—C4aY—C4bY—C5Y	1.2 (7)	C8X—C8aX—C9X—C10	60.8 (4)
C4X—C4aX—C4bX—C5X	4.5 (6)	C8Z—C8aZ—C9Z—C10'	66.9 (5)
C4Z—C4aZ—C4bZ—C5Z	−2.7 (7)	C4b—C8a—C9—C10	−134.0 (3)
C4a—C4b—C5—C6	−178.2 (3)	C4bY—C8aY—C9Y—C10'	−130.2 (3)
C4aY—C4bY—C5Y—C6Y	−179.1 (4)	C4bX—C8aX—C9X—C10	−119.5 (3)
C4aX—C4bX—C5X—C6X	−176.5 (3)	C4bZ—C8aZ—C9Z—C10'	−117.3 (3)
C4aZ—C4bZ—C5Z—C6Z	−173.4 (4)	C2—C1—C9a—C4a	−2.4 (5)
C4b—C5—C6—C7	1.6 (5)	C2Y—C1Y—C9aY—C4aY	−2.9 (5)
C4bY—C5Y—C6Y—C7Y	0.7 (7)	C2X—C1X—C9aX—C4aX	−1.4 (5)
C4bX—C5X—C6X—C7X	1.9 (6)	C2Z—C1Z—C9aZ—C4aZ	−3.3 (5)
C4bZ—C5Z—C6Z—C7Z	0.5 (7)	C4b—C4a—C9a—C1	−175.6 (3)
C5—C6—C7—C8	−0.6 (6)	C4bY—C4aY—C9aY—C1Y	−175.9 (3)
C5Y—C6Y—C7Y—C8Y	−0.1 (7)	C4bX—C4aX—C9aX—C1X	−175.6 (3)
C5X—C6X—C7X—C8X	−2.1 (6)	C4bZ—C4aZ—C9aZ—C1Z	−173.0 (3)
C5Z—C6Z—C7Z—C8Z	−1.4 (7)	C4—C4a—C9a—C1	3.1 (5)
C6—C7—C8—C8a	0.0 (5)	C4Y—C4aY—C9aY—C1Y	3.1 (5)
C6Y—C7Y—C8Y—C8aY	−1.2 (7)	C4X—C4aX—C9aX—C1X	0.3 (5)
C6X—C7X—C8X—C8aX	−0.2 (6)	C4Z—C4aZ—C9aZ—C1Z	3.5 (5)
C6Z—C7Z—C8Z—C8aZ	0.6 (7)	C4—C4a—C9a—C9	178.1 (3)
C7—C8—C8a—C9	176.4 (3)	C4Y—C4aY—C9aY—C9Y	178.3 (3)
C7Y—C8Y—C8aY—C9Y	−179.7 (4)	C4X—C4aX—C9aX—C9X	176.7 (3)
C7X—C8X—C8aX—C9X	−177.7 (3)	C4Z—C4aZ—C9aZ—C9Z	−178.2 (3)
C7Z—C8Z—C8aZ—C9Z	176.5 (4)	C4b—C4a—C9a—C9	−0.6 (4)
C8—C8a—C9—C9a	−178.3 (3)	C4bY—C4aY—C9aY—C9Y	−0.7 (4)
C8Y—C8aY—C9Y—C9aY	−178.4 (4)	C4bX—C4aX—C9aX—C9X	0.8 (4)
C8X—C8aX—C9X—C9aX	−174.6 (3)	C4bZ—C4aZ—C9aZ—C9Z	5.3 (4)
C8Z—C8aZ—C9Z—C9aZ	−170.4 (3)	C4a—C9a—C9—C8a	1.1 (3)
C8a—C9—C9a—C1	175.4 (3)	C4aY—C9aY—C9Y—C8aY	0.2 (4)
C8aY—C9Y—C9aY—C1Y	174.8 (4)	C4aX—C9aX—C9X—C8aX	−3.5 (3)
C8aX—C9X—C9aX—C1X	172.4 (3)	C4aZ—C9aZ—C9Z—C8aZ	−6.4 (3)
C8aZ—C9Z—C9aZ—C1Z	171.6 (4)	C1—C9a—C9—C10	−53.7 (5)
C9—C9a—C1—C2	−176.2 (3)	C1Y—C9aY—C9Y—C10'	−57.6 (5)
C9Y—C9aY—C1Y—C2Y	−177.0 (4)	C1X—C9aX—C9X—C10	−66.1 (4)
C9X—C9aX—C1X—C2X	−177.0 (3)	C1Z—C9aZ—C9Z—C10'	−66.1 (5)
C9Z—C9aZ—C1Z—C2Z	178.8 (3)	C4a—C9a—C9—C10	132.1 (3)
C9a—C1—C2—C3	−0.1 (5)	C4aY—C9aY—C9Y—C10'	127.8 (3)
C9aY—C1Y—C2Y—C3Y	0.9 (6)	C4aX—C9aX—C9X—C10	118.0 (3)
C9aX—C1X—C2X—C3X	1.4 (5)	C4aZ—C9aZ—C9Z—C10'	115.9 (3)
C9aZ—C1Z—C2Z—C3Z	0.9 (6)	C8a—C9—C10—O1	−65.9 (3)
C9a—C4a—C4—C3	−1.3 (5)	C8aY—C9Y—C10'—O1'	−66.8 (3)
C9aY—C4aY—C4Y—C3Y	−1.2 (6)	C8a—C9—C10—C11	173.1 (3)
C9aX—C4aX—C4X—C3X	0.9 (5)	C8aY—C9Y—C10'—C11'	172.8 (3)
C9aZ—C4aZ—C4Z—C3Z	−1.3 (6)	C12—O1—C10—C11	46.6 (4)
C9a—C4a—C4b—C8a	−0.2 (4)	C12'—O1'—C10'—C11'	54.6 (4)
C9aY—C4aY—C4bY—C8aY	0.9 (4)	C12—O1—C10—C9	−75.6 (3)
C9aX—C4aX—C4bX—C8aX	2.5 (4)	C12'—O1'—C10'—C9Y	−68.3 (3)
C9aZ—C4aZ—C4bZ—C8aZ	−1.7 (4)	C12—O1—C10—C9X	163.1 (3)
C9a—C4a—C4b—C5	176.4 (3)	C12'—O1'—C10'—C9Z	171.5 (3)
C9aY—C4aY—C4bY—C5Y	−180.0 (4)	C9a—C9—C10—O1	169.9 (2)
C9aX—C4aX—C4bX—C5X	179.9 (3)	C9aY—C9Y—C10'—O1'	171.8 (3)
C9aZ—C4aZ—C4bZ—C5Z	173.4 (4)	C9a—C9—C10—C11	48.9 (4)
C4—C4a—C4b—C8a	−178.8 (3)	C9aY—C9Y—C10'—C11'	51.4 (4)
C4Y—C4aY—C4bY—C8aY	−177.9 (4)	C10—O1—C12—O2	1.1 (5)
C4X—C4aX—C4bX—C8aX	−172.9 (3)	C10'—O1'—C12'—O2'	−6.4 (5)
C4Z—C4aZ—C4bZ—C8aZ	−177.8 (4)	C10—O1—C12—C13	−179.2 (3)
C8a—C4b—C5—C6	−2.0 (5)	C10'—O1'—C12'—C13'	172.0 (3)
C8aY—C4bY—C5Y—C6Y	−0.1 (6)	C9a—C9—C10—C9X	−80.6 (4)
C8aX—C4bX—C5X—C6X	0.6 (5)	C9aY—C9Y—C10'—C9Z	−77.5 (4)
C8aZ—C4bZ—C5Z—C6Z	1.2 (6)	C8a—C9—C10—C9X	43.5 (4)
C7—C8—C8a—C4b	−0.4 (5)	C8aY—C9Y—C10'—C9Z	44.0 (4)