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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 80| Part 8| August 2024| Pages 857-862
https://doi.org/10.1107/S2056989024006480

Structural determination of oleanane-28,13β-olide and taraxerane-28,14β-olide fluoro­lactonization products from the reaction of oleanolic acid with SelectfluorTM

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Megan A. Eadsforth,a* Linghan Kong,b George Whitehead,a Iñigo J. Vitórica-Yrezábal,c Raymond T. O'Keefe,d Richard A. Bryceb and Roger C. Whiteheada

aDepartment of Chemistry, University of Manchester, Manchester, United Kingdom, bDivision of Pharmacy and Optometry, University of Manchester, Manchester, United Kingdom, cDepartment of Inorganic Chemistry, Faculty of Science, University of Granada, Granada, Spain, and dDivision of Evolution, Infection and Genomics, University of Manchester, Manchester, United Kingdom
*Correspondence e-mail: megan.eadsforth@manchester.ac.uk

Edited by D. R. Manke, University of Massachusetts Dartmouth, USA (Received 12 January 2024; accepted 2 July 2024; online 15 July 2024)

The X-ray crystal structure data of 12-α-fluoro-3β-hy­droxy­olean-28,13β-olide methanol hemisolvate, 2C30H47FO3·CH3OH, (1), and 12-α-fluoro-3β-hy­droxy­taraxer-28,14β-olide methanol hemisolvate, 2C30H47FO3·CH3OH, (2), are described. The fluoro­lactonization of oleanolic acid using SelectfluorTM yielded a mixture of the six-membered δ-lactone (1) and the unusual seven-membered γ-lactone (2) following a 1,2-shift of methyl C-27 from C-14 to C-13.

CCDC references: 2367298; 2367297

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1. Chemical context

Oleanolic acid (OA) and ursolic acid (UA) are penta­cyclic triterpenoids that are found widely in food and plants of the Oleaceae family, such as the olive plant. Similar to many other natural products, these triterpenoids have been found to exhibit a range of pharmacological activities (Sánchez-Quesada et al., 2013[Sánchez-Quesada, C., López-Biedma, A., Warleta, F., Campos, M., Beltrán, G. & Gaforio, J. J. (2013). J. Agric. Food Chem. 61, 12173-12182.]), such as anti­oxidant, anti-inflammatory (Adjei et al., 2021[Adjei, S., Amponsah, I. K., Bekoe, S. O., Harley, B. K., Mensah, K. B., Mensah, A. Y., Baah, M. K. & Fosu-Mensah, G. (2021). Heliyon, 7, e07910. https:/doi.org/10.1016/j.heliyon.2021.e07910]), anti-diabetic (Qian et al., 2010[Qian, S., Hai Li, J., Wei Zhang, Y., Chen, X. & Wu, Y. (2010). J. Asian Nat. Prod. Res. 12, 20-29.]; Tang et al., 2014[Tang, C., Zhu, L., Chen, Y., Qin, R., Mei, Z., Xu, J. & Yang, G. (2014). RSC Adv. 4, 10862-10874.]), and anti-cancer properties (Borella et al., 2019[Borella, R., Forti, L., Gibellini, L., De Gaetano, A., De Biasi, S., Nasi, M., Cossarizza, A. & Pinti, M. (2019). Molecules, 24, 4097.]; Baer-Dubowska et al., 2021[Baer-Dubowska, W., Narożna, M. & Krajka-Kuźniak, V. (2021). Molecules, 26, 4957.]). Previous reports have demonstrated that semi-synthetic derivatives of UA and OA-fluoro­lactones have improved biological activities compared to the parent mol­ecules, demonstrating both anti-apoptotic (Leal et al., 2012[Leal, A. S., Wang, R., Salvador, J. A. R. & Jing, Y. (2012). ChemMedChem, 7, 1635-1646.]) and anti-diabetic properties (Zhong et al., 2019[Zhong, Y. Y., Chen, H. S., Wu, P. P., Zhang, B. J., Yang, Y., Zhu, Q. Y., Zhang, C. G. & Zhao, S. Q. (2019). Eur. J. Med. Chem. 164, 706-716.]). Leal and co-workers report that the reaction of UA with SelectfluorTM at 353 K, in a mixture of nitro­methane and dioxane, results in insertion of fluorine at C-12 with formation of the 28,13β-γ-lactone. The authors report that fluoro­lactonization of UA gives a mixture of α and β-isomers (C-F), with the β-isomer formed as the major product, as characterized by 1H NMR spectroscopy (Leal et al., 2012[Leal, A. S., Wang, R., Salvador, J. A. R. & Jing, Y. (2012). ChemMedChem, 7, 1635-1646.]). Zhong and co-workers (Zhong et al., 2019[Zhong, Y. Y., Chen, H. S., Wu, P. P., Zhang, B. J., Yang, Y., Zhu, Q. Y., Zhang, C. G. & Zhao, S. Q. (2019). Eur. J. Med. Chem. 164, 706-716.]) also report fluoro­lactonization of OA, under these same conditions (Leal et al., 2012[Leal, A. S., Wang, R., Salvador, J. A. R. & Jing, Y. (2012). ChemMedChem, 7, 1635-1646.]), to give fluorination at C-12 and formation of the 28,13β-β-lactone. However, the authors (Zhong et al., 2019[Zhong, Y. Y., Chen, H. S., Wu, P. P., Zhang, B. J., Yang, Y., Zhu, Q. Y., Zhang, C. G. & Zhao, S. Q. (2019). Eur. J. Med. Chem. 164, 706-716.]) do not comment on the stereochemistry at the C—F bond (C-12).

Given the previous reports indicating enhanced pharmacological properties in UA and OA-fluoro­lactone derivatives (Leal et al., 2012[Leal, A. S., Wang, R., Salvador, J. A. R. & Jing, Y. (2012). ChemMedChem, 7, 1635-1646.]; Zhong et al., 2019[Zhong, Y. Y., Chen, H. S., Wu, P. P., Zhang, B. J., Yang, Y., Zhu, Q. Y., Zhang, C. G. & Zhao, S. Q. (2019). Eur. J. Med. Chem. 164, 706-716.]), our research pursuits include the additional functionalization of OA-fluoro­lactones. This exploration aims to unveil alternative biological activities within this class of compounds (Eadsforth, 2022[Eadsforth, M. A. (2022). Expanding the toolbox for studying the splicing mechanism: Development of semi-synthetic triterpene derivatives as novel small molecule inhibitors of pre-mRNA splicing. Thesis, University of Manchester, UK.]). We therefore adopted the same conditions as previously described for UA (Leal et al., 2012[Leal, A. S., Wang, R., Salvador, J. A. R. & Jing, Y. (2012). ChemMedChem, 7, 1635-1646.]) and OA (Zhong et al., 2019[Zhong, Y. Y., Chen, H. S., Wu, P. P., Zhang, B. J., Yang, Y., Zhu, Q. Y., Zhang, C. G. & Zhao, S. Q. (2019). Eur. J. Med. Chem. 164, 706-716.]) for the fluoro­lactonization of OA (see scheme[link]). Inter­estingly, we found that under these conditions a mixture of fluoro­lactone products was formed, including the 28,14β-δ-lactone, which has not previously been characterized (Fig. 1[link]). Herein, we report on the synthesis and crystal structures of the products of the fluoro­lactonization reaction of OA with SelectfluorTM, an electrophilic fluorinating reagent, which leads to rearrangement to a taraxerane core as the major product. Taraxeranes are another class of biologically active penta­cyclic triterpenoid steroids that have been isolated from plants. Taraxeranes are structural isomers of oleanane triterpenoids that are derived bio-synthetically from the rearrangement of the oleanane skeleton following the C-27 methyl shift from C-14 to C-13 (Kuroda et al., 2006[Kuroda, M., Aoshima, T., Haraguchi, M., Young, M. C. M., Sakagami, H. & Mimaki, Y. (2006). J. Nat. Prod. 69, 1606-1610.]; Hu et al., 2012[Hu, J., Shi, X., Chen, J., Huang, H. & Zhao, C. (2012). Fitoterapia, 83, 55-59.]).

[Figure 1]
Figure 1
Proposed mechanism for the formation of oleanolic fluoro­lactone products (1) and (2).

The classical lactonization reaction of oleanane-type triterpenoids, containing a C12=C13 double bond, has been reported to proceed under acidic conditions and involves a 28,13β-lactonization (Cheriti et al., 1994[Cheriti, A., Babadjamian, A. & Balansard, G. (1994). J. Nat. Prod. 57, 1160-1163.]). The reaction of oleanolic acid with bis­muth tri­fluoro­methane­sulfonate, Bi(OTf)3·xH2O, in DCM also results in 28,13β-lactonization, as confirmed by X-ray crystallography (Salvador et al., 2009[Salvador, J. A. R., Pinto, R. M. A., Santos, R. C., Le Roux, C., Beja, A. M. & Paixão, J. A. (2009). Org. Biomol. Chem. 7, 508-517.]; Santos et al., 2010[Santos, R. C., Pinto, R. M. A., Matos Beja, A., Salvador, J. A. R. & Paixão, J. A. (2010). Acta Cryst. E66, o2139-o2140.]). Our observation that fluoro­lactonization of OA with Selectfluor results in the formation of the 28,14β-δ-lactone has not yet been reported. However, our findings parallel previous reports in the literature which report formation of other oleanane-type 28,13β-δ-lactone derivatives under different conditions. For instance, using NMR analysis for characterization, the formation of 12-bromo-3β-hy­droxy­taraxeran-28,14β-olide as a minor product from the reaction of OA with bromine in CCl4 has been reported (Martinez et al., 2015[Martinez, A., Perojil, A., Rivas, F., Medina-O'Donnell, M. & Parra, A. (2015). Tetrahedron, 71, 792-800.]). The formation of 3-O-acetyl-taraxeran-28,14β-olide from the reaction of OA under oxidative conditions (formic acid/hydrogen peroxide at 373 K for several hours) has also been reported and characterized by NMR analysis (Heise et al., 2021[Heise, N., Siewert, B., Ströhl, D., Hoenke, S., Kazakova, O. & Csuk, R. (2021). Steroids, 172, 108853.]). X-ray analysis has also identified 3β-acet­oxy-12α-chloro-14β-isooleanan-28,14β-olide as an unexpected by-product in a POCl3-catalysed Beckmann rearrangement of 3β-acet­oxy-12-hy­droxy­imino­olean-28-olic acid methyl ester (Froelich et al., 2011[Froelich, A., Kowiel, M., Bednarczyk-Cwynar, B., Zaprutko, L. & Gzella, A. K. (2011). Acta Cryst. E67, o679.]).

[Scheme 1]

While the precise mechanism underlying the formation of compound (2) following reaction of OA with SelectfluorTM remains unclear, Martinez and co-workers have previously elucidated a possible mechanism for the formation 12-bromo-3β-hy­droxy­taraxeran-28,14β-olide (Martinez et al., 2015[Martinez, A., Perojil, A., Rivas, F., Medina-O'Donnell, M. & Parra, A. (2015). Tetrahedron, 71, 792-800.]). Following bromination of oleanolic acid with Br2/CCl4, the authors report isolation of 12α-bromo-3β-hy­droxy­olean-28,13β-olide (80%), together with 12α-bromo-3β-hy­droxy­taraxer-14-en-28-oic acid (3%), and 12α-bromo-3β-hy­droxy­olean-28,13β-olide (13%), as minor products when the reaction was maintained for 12 h. The authors propose that formation of 12α-bromo-3β-hy­droxy­taraxer-14-en-28-oic acid could be explained due to traces of HBr in the reaction mixture leading to lactone ring-opening and formation of the C-28 carboxyl group. The subsequent migration of C-27 from C-14 to C-13, via the α-face, followed by elimination of H-15β would install a double bond between C-14 and C-15. Further addition of a proton to the double bond at C-14/C-15 would create a tertiary carbocation formed at C-14, which would be stabilized by the attack of the carboxyl group at C-28 to form 12-α-bromo-3β-hy­droxy­olean-28,13β-olide.

Since acid catalysis is unlikely under the electrophilic fluorinating conditions employed with SelectfluorTM and given that we failed to isolate any inter­mediates containing a C-14=C-15 double bond, we propose that formation of (2) follows a different mechanism to that proposed for the bromo­lactonization of OA (Martinez et al., 2015[Martinez, A., Perojil, A., Rivas, F., Medina-O'Donnell, M. & Parra, A. (2015). Tetrahedron, 71, 792-800.]). We propose that following electrophilic addition of fluorine to the C12=C13 double bond, the tertiary carbocation formed at C-13 can either be stabilized by the intra­molecular nucleophilic attack of the C-28 carboxyl to form (1) or by the Wagner–Meerwein 1,2-shift of C-27 to C-13. This rearrangement would result in a tertiary carbocation at C-14, which can then be stabilized by the nucleophilic attack of the C-28 carboxyl group to form the 28,14β-δ-lactone (2) (Fig. 1[link]).

2. Structural commentary

X-ray analysis of the OA-fluoro­lactonization products identified 3β-hy­droxy-12α-fluoroolean-28,13β-olide methanol hemisolvate (1) and 3β-hy­droxy-12α-fluorotaraxeran-28,14β-olide methanol hemisolvate (2) as the two main products. Both compounds (1) and (2) contain five fused six-membered rings. The X-ray structure of compound (1) revealed that it contains a γ-lactone ring with the C28=O2 carbonyl adjacent to C-17 and the bridging oxygen atom O-1 adjacent to C-13. The ether oxygen atom O-1 at C-13 and the methyl group at C-14 are axial with respect to rings C and D. The fluorine atom at C-12, belonging to ring C, is oriented equatorially and assumes an α-configuration. Rings A–E of the triterpenoid skeleton adopt chair conformations, and rings D and E are cis-fused as in oleanolic acid (Fig. 2[link]). The values of the dihedral angles in (1) confirm the trans configuration of rings A/B, B/C and C/D [−177.9, 172.3, −170.8 (6)°] and the cis configuration of rings D/E [65.1°]. Each six-membered ring adopts a chair conformation with a different degree of distortion, as shown by the Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]) parameters: [ring A: Q = 0.552 Å, θ = 3.8° and φ = 312°; B: Q = 0.547 Å, θ = 166.2° and φ = 4.6°; C: Q = 0.550 Å, θ = 20.4° and φ = 132.3°; D: Q = 0.607 Å, θ = 161.2° and φ = 231.3°; E: Q = 0.570 Å, θ = 177.5° and φ = 247.5°]. The lactone ring adopts an envelope conformation (q = 0.487 and φ = 68.0°) as in agreement with the structure of 3-oxo-18a-olean-28,13β-olide (Santos et al., 2010[Santos, R. C., Pinto, R. M. A., Matos Beja, A., Salvador, J. A. R. & Paixão, J. A. (2010). Acta Cryst. E66, o2139-o2140.]).

[Figure 2]
Figure 2
The mol­ecular structure of (1), showing the atomic labelling scheme. Non-H atoms are drawn as 50% probability displacement ellipsoids and H atoms are drawn as spheres of an arbitrary size. Oxygen atoms are coloured in red, fluorine atom coloured in green.

X-ray analysis confirmed that the unusual major product, compound (2), contains a δ-lactone ring; in (2), the C28=O2 carbonyl is adjacent to C-17 and the bridging oxygen atom O-1 adjacent to C-14 (Fig. 3[link]). The ether oxygen displays a β-configuration, while the methyl group has an α-configuration. The structure shows that the methyl group C-27 has undergone a 1,2-shift from C-14 to C-13, retaining its original axial orientation from oleanolic acid. The fluorine atom at C-12, belonging to ring C, is oriented equatorially and assumes an α-configuration. Rings A, B and E of the triterpenoid skeleton adopt chair conformations [Cremer & Pople, 1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]; puckering parameters: Q = 0.564 Å, θ = 176.8, φ = 241.1, Q = 0.586 Å, θ = 171.8, φ = 358.0, Q = 0.538, Å, θ = 171.6, φ = 20.7, respectively] whilst rings C, D and the δ-lactone group adopt twisted-boat conformations [puckering parameters: Q = 0.738 Å, θ = 93.9°, φ = 157.0°, Q = 0.852 Å, θ = 88.4°, φ = 165.6°, Q = 0.808 Å, θ = 91.7°, φ = 250.2°, respectively], in agreement with the 3β-acet­oxy-12α-chloro-14β-isooleanan-28,14β-olide structure (Froelich et al., 2011[Froelich, A., Kowiel, M., Bednarczyk-Cwynar, B., Zaprutko, L. & Gzella, A. K. (2011). Acta Cryst. E67, o679.]). The values of the dihedral angles in compound (2) confirm the trans configuration of rings A/B, B/C and C/D [−179.3, −179.3, 164.8 (4)°] and the cis configuration of rings D/E [48.0°]. The hy­droxy group at C-3 in both structures (1) and (2) adopts a β-configuration.

[Figure 3]
Figure 3
The mol­ecular structure of (2), showing the atomic labelling scheme. Non-H atoms are drawn as 50% probability displacement ellipsoids and H atoms are drawn as spheres of an arbitrary size. Methanol solvent mol­ecule hydrogen bonding to O-3. Oxygen atoms are coloured in red, fluorine atom coloured in green.

3. Supra­molecular features

In the crystal, two mol­ecules of compound (1) are connected by inter­molecular O—H⋯O hydrogen bonds between O-3 and a bridging mol­ecule of methanol (O3A⋯H13—O13⋯H12—O12) into infinite chains extending along [010] b axis (Fig. 4[link], Table 1[link]). In the crystal structure of (2), the mol­ecules are connected by inter­molecular O—H⋯O hydrogen bonds between O-3 and a mol­ecule of methanol (O4—H4⋯O3) into infinite chains extending along [100] (Fig. 5[link], Table 2[link]).

Table 1
Hydrogen-bond geometry (Å, °) for 1[link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O13—H13⋯O3A 0.82 1.93 2.720 (8) 161
O14—H14⋯O3Di 0.82 1.94 2.714 (9) 157
O3A—H3A⋯O3Cii 0.82 2.03 2.819 (8) 163
O3D—H3D⋯O3Biii 0.82 2.01 2.816 (8) 166
O3B—H3B⋯O14iv 0.82 2.01 2.715 (8) 144
O3C—H3C⋯O13ii 0.82 2.07 2.708 (9) 135
Symmetry codes: (i) [x+1, y-1, z]; (ii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iii) [-x, y+{\script{1\over 2}}, -z]; (iv) [-x+1, y-{\script{1\over 2}}, -z].

Table 2
Hydrogen-bond geometry (Å, °) for 2[link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H3A⋯O3i 0.82 2.12 2.784 (10) 138
O3—H3B⋯O4ii 0.83 1.94 2.695 (6) 152
O4—H4⋯O3i 0.82 1.96 2.695 (6) 149
Symmetry codes: (i) [-x+1, y, -z+{\script{3\over 2}}]; (ii) [x+1, y, z].
[Figure 4]
Figure 4
Expanded view of crystal packing of structure (1) to show hydrogen bonding (dotted lines) to solvent methanol. Oxygen atoms are coloured in red, fluorine atom coloured in green. The hydrogen atoms have been omitted for clarity.
[Figure 5]
Figure 5
Expanded view of crystal packing of structure (2) to show hydrogen bonding (dotted lines) to solvent methanol. Oxygen atoms are coloured in red, fluorine atom coloured in green. The hydrogen atoms have been omitted for clarity.

4. Synthesis and crystallization

Oleanolic acid (300 mg, 0.66 mmol) and SelectfluorTM {1-chloro­methyl-4-fluoro-1,4-diazo­niabi­cyclo­[2.2.2]octane bis­(tetra­fluoro­borate)} (701 mg, 1.98 mmol) were dissolved in a mixture of anhydrous dioxane (4 mL) and nitro­methane (6 mL), under an inert atmosphere, and stirred at 353 K for 4 h. The reaction mixture was then diluted with water (50 mL), extracted with ethyl acetate (3 × 50 mL) and the combined organic extract was washed with brine (3 × 20 mL). The organic phase was then de-emulsified by filtering through a sinter funnel containing a layer of NaCl. The organic phase was dried over anhydrous MgSO4, filtered and evaporated to dryness to afford an off-white solid. 19F NMR analysis of the crude mixture showed the ratio of products (1):(2) to be ∼1:1.25, indicating (2) to be the major isomer formed under these reaction conditions.

The crude product (239 mg, 0.50 mmol, 76%) was then dry-loaded on a silica gel column and purified with gradient elution (10–20%, EtOAc in hexa­ne), to afford products (1) (80 mg, 0.168 mmol, 25%) and (2) (38 mg, 0.080 mmol, 12%) as white crystalline solids. Due to poor separation by silica gel column chromatography, (1) was isolated in greater yield than (2). Recrystallization of (1) by methanol evaporation afforded colourless needle-like crystals suitable for X-ray diffraction analysis. Further purification of (2) by recrystallization in aceto­nitrile, followed by evaporation from methanol provided colourless crystals suitable for X-ray diffraction analysis.

12α-Fluoro-3β-hy­droxy­olean-28,13β-olide methanol hemisolvate (1):

White solid; m.p. 563 K; [α]D22 +43.3 (c 1.00 in DCM). νmax cm−1 ∼3490 w (O—H), 2924m (C—H), 1773 (C=O,γ-lactone); δH (400 MHz, CDCl3) 0.68–0.74 (1 H, m, C5H), 0.75 (3 H, s, C24H3), 0.85 (3 H, s, C25H3), 0.88 (3 H, s, C30H3), 0.97 (7 H, s, C1AH, C23H3 and C29H3), 1.09 (3 H, s, C26H3), 1.21 (3 H, s, C27H3),1.12–2.14 [20 H, m, C(1B, 9H) and C(2, 6, 7, 1, 15, 16, 19, 21, 22)H2], 3.20 (1 H, dd, J 11.3, 4.7, C3H), 4.54 (1 H, dt, 1JC–F 46.6, 2.8, C12HF). δC (101 MHz, CDCl3) 15.5 (C24), 16.1 (C25), 17.8 (C6), 18.1 (d, 4JC–F 8.1, C27), 18.4 (C26), 21.2 (C16), 23.9 (C30), 25.8 (d, 2JC–F 21.5, C11), 27.3 (C2), 27.5 (C15), 27.6 (C22), 28.1 (C23), 31.6 (C20), 33.3 (C29), 33.6 (C(7), 34.2 (C21), 36.5 (C10), 38.6 (C1 & C19 overlapping peaks), 39.0 (C4), 41.8 (d, 3JC–F 1.3, C14), 42.0 (C8), 44.4 (C17), 44.8 (C9), 51.0 (C18), 55.1 (C5), 78.8 (C3), 88.1 (d, 2JC–F 25.9, (C13), 96.8 (d, 1JC–F 171.6, (C12), 179.4 (C28). δF (376 MHz, CDCl3) −180.0 (td, 1JC–F 47.1, 20.4). m/z HR–MS[ESI+] calculated for C30H48FO3 [(M+H)+] 475.3587, found 475.3582.

12-α-Fluoro-3β-hy­droxy­taraxer-28,14β-olide methanol hemisolvate (2):

White needles; m.p. 526 K (charring); [α]D22 +25.7 (c 1.00 in DCM). νmax cm−1 3490 w (O—-H), 2935 m (C—-H), 1737 s (C=O, δ-lactone). δH (400 MHz, CDCl3) 0.76 (1 H, d, J 2.9, C5H), 0.79 (3 H, s, C24H3), 0.88 (3 H, s, C30H3), 0.93 (3 H, s, C25H3), 0.97–1.05 (1 H, m, C1AH), 0.96 (6 H, s, C23H3 and C29H3), 1.13 (3 H, s, C26H3), 1.22 (3 H, d, 4JC–F 2.6, C27H3), 1.14–1.32 (3 H, m, C16AH and C21H2), 1.33–1.46 [4 H, m, C22H2 and (7A, 19A)H], 1.50–1.77 [8 H, m, C2, 6H2 and C(1B, 7B, 11A, 15AH)], 1.82–1.89 (2 H, m, C9, 18H), 1.90–2.05 (2 H, m, C11B, 15BH), 2.09 (1 H, td, J 14.2, 4.4, C19BH), 2.15–2.26 (1 H, m, C16BH), 3.14–3.24 (1 H, m, C3H), 4.65 (1 H, ddd, 1JC–F 50.8, 6.7, 4.1, C12HF). δC (126 MHz, CDCl3) 15.3 (C24), 16.6 (d, 3JC–F 10.9, C27), 17.4 (C25), 19.4 (C6), 19.4 (C26), 22.0 (C16) 24.0 (C30), 25.0 (C15), 26.5 (d, 2JC–F 21.5, C11), 26.9 (C19), 27.3 (C2), 27.9 (C23), 30.7 (C20), 33.3 (C29), 33.6 (C21), 37.1(C22), 37.6 (C10), 37.8 (C7), 38.8 (C1), 39.0 (C4), 39.5 (C17), 43.6 (C8), 45.1 (d, 2JC–F 18.9, C13), 45.5 (C18), 48.8 (d, 3JC–F 2.5, C(9), 55.9 (C5), 78.9 (C3), 90.9 (d, 3JC–F 7.3, C(14), 100.1 (d, 1JC–F 179.5, C12), 178.6 (C28). δF (CDCl3, 376 MHz) −184.6 (ddd, 1JC–F 106, 53, 24). m/z HR–MS [ESI+] calculated for C30H48FO3[(M+H)+] 475.3587, found 475.3582.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. Hydrogen atoms were placed in calculated positions and refined using idealized geometries, except H9 in compound (2), which was allowed to refine freely. Hydrogen isotropic atomic displacement parameters were constrained to ride with the parent atom with an appropriate multiplier for the hybridization. Atomic displacement parameters for C1B–C7B in compound (1) were restrained with a strong isotropic atomic displacement parameter restraint in order to refine chemically sensible atomic displacement parameters.

Table 3
Experimental details

  1 2
Crystal data
Chemical formula 2C30H47FO3·CH4O 2C30H47FO3·0CH4O
Mr 981.39 981.39
Crystal system, space group Monoclinic, P21 Orthorhombic, C2221
Temperature (K) 100 240
a, b, c (Å) 12.4983 (2), 7.17223 (12), 60.3774 (12) 6.6077 (2), 13.8730 (4), 59.326 (2)
α, β, γ (°) 90, 94.1762 (17), 90 90, 90, 90
V (Å3) 5397.90 (17) 5438.3 (3)
Z 4 4
Radiation type Cu Kα Cu Kα
μ (mm−1) 0.64 0.64
Crystal size (mm) 0.42 × 0.24 × 0.05 0.34 × 0.2 × 0.1
 
Data collection
Diffractometer XtaLAB AFC11 (RINC): Kappa single XtaLAB AFC11 (RINC): Kappa single
Absorption correction Multi-scan (CrysAlis PRO; Rigaku OD, 2020[Rigaku OD (2020). CrysAlis PRO. Rigaku Corporation, Wroclaw, Poland.]) Multi-scan (CrysAlis PRO; Rigaku OD, 2020[Rigaku OD (2020). CrysAlis PRO. Rigaku Corporation, Wroclaw, Poland.])
Tmin, Tmax 0.486, 1.000 0.907, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 77709, 21225, 19142 24920, 5184, 4937
Rint 0.074 0.059
(sin θ/λ)max (Å−1) 0.630 0.613
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.098, 0.277, 1.05 0.073, 0.203, 1.09
No. of reflections 21225 5184
No. of parameters 1292 328
No. of restraints 43 0
H-atom treatment H-atom parameters constrained H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.76, −0.54 0.27, −0.29
Absolute structure Flack x determined using 7081 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.]) Refined as an inversion twin
Absolute structure parameter 0.04 (10) 0.5 (5)
Computer programs: CrysAlis PRO (Rigaku OD, 2020[Rigaku OD (2020). CrysAlis PRO. Rigaku Corporation, Wroclaw, Poland.]), SHELXS (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2019/3 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Supporting information

CCDC references: 2367298; 2367297

Crystal structure: contains datablocks 1, 2. DOI: https://doi.org/10.1107/S2056989024006480/yy2009sup1.cif

Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989024006480/yy20091sup2.hkl

Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989024006480/yy20092sup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989024006480/yy20091sup4.mol

Supporting information file. DOI: https://doi.org/10.1107/S2056989024006480/yy20092sup5.mol

checkCIF report


Computing details top

12-α-Fluoro-3β-hydroxyolean-28,13β-olide methanol hemisolvate (1) top
Crystal data top
2C30H47FO3·CH4OF(000) = 2152
Mr = 981.39Dx = 1.208 Mg m−3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
a = 12.4983 (2) ÅCell parameters from 13347 reflections
b = 7.17223 (12) Åθ = 1.5–74.7°
c = 60.3774 (12) ŵ = 0.64 mm−1
β = 94.1762 (17)°T = 100 K
V = 5397.90 (17) Å3Plate, clear colourless
Z = 40.42 × 0.24 × 0.05 mm
Data collection top
XtaLAB AFC11 (RINC): Kappa single
diffractometer		21225 independent reflections
Radiation source: Rotating-anode X-ray tube (dual wavelength)19142 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm-1Rint = 0.074
ω scansθmax = 76.2°, θmin = 2.2°
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2020)		h = −12→15
Tmin = 0.486, Tmax = 1.000k = −8→8
77709 measured reflectionsl = −74→75
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.098 w = 1/[σ2(Fo2) + (0.1319P)2 + 16.8795P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.277(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.76 e Å−3
21225 reflectionsΔρmin = −0.54 e Å−3
1292 parametersAbsolute structure: Flack x determined using 7081 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
43 restraintsAbsolute structure parameter: 0.04 (10)
Primary atom site location: dual
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Data were streaked. this was the best crystal that could be found. Streaking has resulted in prolate atoms as not all intensity for all resflections could be accurately captured. ISOR restraints applied to refine more realistic thermal parameters for these atoms.

Data collection: X-ray diffraction data for compounds (1) and (2) were collected using a dual wavelength Rigaku FR-X rotating anode diffractometer using CuKα (λ = 1.54184 Å) radiation, equipped with an AFC-11 4-circle kappa goniometer, VariMAXTM microfocus optics, a Hypix-6000HE detector and an Oxford Cryosystems 800 plus nitrogen flow gas system, at temperatures of 240K and 100K, respectively. Data were collected and reduced using CrysAlisPro v40. Absorption correction was performed using empirical methods (SCALE3 ABSPACK) based upon symmetry-equivalent reflections combined with measurements at different azimuthal angles.

Crystal structure determination and refinements: The crystal structure was solved and refined against all F2 values using the SHELX and Olex2 suite of programmes. All non-hydrogen atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O130.2010 (5)−0.0663 (9)0.49918 (11)0.0378 (14)
H130.2275880.0368540.4975860.057*
C1210.0913 (7)−0.0603 (13)0.49219 (19)0.044 (2)
H12E0.082825−0.0309470.4763070.066*
H12F0.0559240.0359580.5005690.066*
H12G0.058565−0.1817430.4948240.066*
O140.6992 (5)0.0744 (9)0.00058 (11)0.0399 (14)
H140.723344−0.031516−0.0001190.060*
C1220.5940 (8)0.0669 (16)0.0077 (2)0.051 (3)
H12H0.548650−0.008940−0.0027000.077*
H12I0.5646320.1933670.0082230.077*
H12J0.5958710.0110380.0225450.077*
F1A0.1075 (3)0.4109 (7)0.36114 (8)0.0341 (11)
O1A0.3127 (4)0.7268 (8)0.34616 (9)0.0267 (11)
O2A0.4107 (5)0.8594 (9)0.32041 (10)0.0369 (14)
O3A0.2403 (5)0.2994 (8)0.49106 (9)0.0317 (12)
H3A0.2402700.4004170.4974000.047*
C1A0.1610 (6)0.4831 (11)0.43359 (13)0.0265 (16)
H1AA0.1059290.5754760.4283700.032*
H1AB0.1406970.3615220.4267400.032*
C2A0.1616 (6)0.4656 (12)0.45857 (14)0.0306 (17)
H2AA0.0897910.4245170.4625340.037*
H2AB0.1759150.5894570.4653760.037*
C3A0.2453 (7)0.3281 (11)0.46806 (13)0.0285 (16)
H3AA0.2284760.2055270.4607040.034*
C4A0.3606 (6)0.3830 (11)0.46205 (14)0.0278 (16)
C5A0.3573 (6)0.4112 (11)0.43671 (13)0.0259 (15)
H5A0.3374450.2857400.4304470.031*
C6A0.4679 (6)0.4520 (12)0.42803 (14)0.0316 (17)
H6AA0.4878920.5831110.4313530.038*
H6AB0.5224860.3705880.4358000.038*
C7A0.4670 (6)0.4191 (12)0.40325 (14)0.0307 (17)
H7AA0.4577380.2840000.4003730.037*
H7AB0.5377020.4557310.3982460.037*
C8A0.3794 (5)0.5250 (11)0.38929 (12)0.0237 (15)
C9A0.2697 (6)0.5153 (10)0.40019 (13)0.0233 (15)
H9A0.2457920.3832880.3978700.028*
C10A0.2711 (6)0.5439 (11)0.42576 (13)0.0256 (15)
C11A0.1853 (6)0.6295 (11)0.38662 (13)0.0261 (16)
H11A0.1159430.6148950.3933530.031*
H11B0.2056660.7626880.3878210.031*
C12A0.1692 (5)0.5801 (11)0.36244 (13)0.0258 (15)
H12A0.1278230.6816240.3543320.031*
C13A0.2720 (6)0.5393 (11)0.35072 (12)0.0240 (15)
C14A0.3617 (5)0.4344 (11)0.36511 (12)0.0242 (14)
C15A0.4662 (5)0.4408 (12)0.35280 (14)0.0288 (16)
H15A0.5017420.5624430.3558040.035*
H15B0.5152750.3422200.3589170.035*
C16A0.4488 (6)0.4144 (12)0.32781 (13)0.0293 (16)
H16A0.4359980.2805430.3246430.035*
H16B0.5152280.4507790.3209110.035*
C17A0.3544 (6)0.5279 (11)0.31694 (13)0.0251 (15)
C18A0.2500 (6)0.4707 (12)0.32640 (13)0.0269 (16)
H18A0.1942020.5569450.3195000.032*
C19A0.2145 (6)0.2734 (12)0.31882 (14)0.0321 (17)
H19A0.1451280.2425340.3248420.039*
H19B0.2683850.1809990.3246100.039*
C20A0.2029 (6)0.2639 (14)0.29321 (14)0.0342 (18)
C21A0.3070 (7)0.3285 (13)0.28363 (14)0.0326 (18)
H21A0.2960160.3310420.2672240.039*
H21B0.3642150.2366640.2876760.039*
C22A0.3446 (6)0.5221 (11)0.29183 (14)0.0292 (16)
H22A0.4150220.5508310.2861100.035*
H22B0.2926210.6176540.2860840.035*
C23A0.4336 (8)0.2169 (15)0.46882 (15)0.043 (2)
H23A0.4203540.1773660.4839090.064*
H23B0.5088870.2541610.4683540.064*
H23C0.4182520.1132320.4584940.064*
C24A0.4027 (7)0.5495 (13)0.47614 (14)0.0350 (18)
H24A0.3509240.6521550.4745640.052*
H24B0.4715920.5904230.4710770.052*
H24C0.4122850.5120380.4917680.052*
C25A0.2871 (7)0.7524 (11)0.43231 (13)0.0308 (16)
H25A0.3623710.7870600.4312510.046*
H25B0.2675340.7708590.4475830.046*
H25C0.2413690.8304950.4222250.046*
C26A0.4192 (6)0.7291 (11)0.38877 (13)0.0264 (15)
H26A0.3600220.8103110.3832760.040*
H26B0.4778910.7385270.3789160.040*
H26C0.4448800.7678290.4037950.040*
C27A0.3266 (7)0.2250 (12)0.36667 (13)0.0315 (17)
H27A0.3419440.1802100.3819060.047*
H27B0.3663170.1496000.3565050.047*
H27C0.2494710.2143790.3625790.047*
C28A0.3665 (7)0.7229 (12)0.32693 (13)0.0306 (17)
C29A0.1072 (7)0.3815 (17)0.28368 (16)0.045 (2)
H29A0.0422800.3439980.2906860.068*
H29B0.0968510.3615370.2676080.068*
H29C0.1217190.5137120.2866750.068*
C30A0.1830 (7)0.0579 (14)0.28648 (16)0.040 (2)
H30A0.243136−0.0187070.2925190.060*
H30B0.1766740.0476740.2702550.060*
H30C0.1164620.0142530.2924180.060*
F1D−0.3048 (3)0.5948 (7)0.13742 (8)0.0349 (11)
O1D−0.0917 (4)0.2741 (7)0.15326 (9)0.0266 (11)
O2D0.0232 (5)0.1409 (9)0.17898 (11)0.0374 (14)
O3D−0.2534 (5)0.7097 (9)0.00820 (10)0.0362 (13)
H3D−0.2620680.6098590.0016880.054*
C1D−0.2974 (6)0.5220 (11)0.06531 (14)0.0295 (17)
H1DA−0.3494380.4291490.0701770.035*
H1DB−0.3128910.6426070.0723760.035*
C2D−0.3124 (6)0.5434 (12)0.04016 (14)0.0308 (17)
H2DA−0.3044700.4198320.0331490.037*
H2DB−0.3860130.5886060.0360530.037*
C3D−0.2329 (7)0.6769 (11)0.03126 (14)0.0299 (17)
H3DA−0.2439960.7989510.0387610.036*
C4D−0.1149 (6)0.6204 (11)0.03755 (15)0.0305 (17)
C5D−0.1010 (6)0.5916 (10)0.06285 (13)0.0253 (15)
H5D−0.1161130.7167510.0692220.030*
C6D0.0142 (6)0.5471 (12)0.07181 (14)0.0307 (17)
H6DA0.0305480.4153540.0685220.037*
H6DB0.0647460.6266170.0641680.037*
C7D0.0302 (6)0.5794 (11)0.09662 (13)0.0271 (15)
H7DA0.0240840.7146400.0995620.033*
H7DB0.1037750.5403060.1017860.033*
C8D−0.0501 (5)0.4747 (11)0.11020 (13)0.0236 (15)
C9D−0.1665 (5)0.4859 (10)0.09895 (13)0.0240 (15)
H9D−0.1886480.6179910.1012850.029*
C10D−0.1811 (6)0.4584 (11)0.07331 (13)0.0260 (15)
C11D−0.2445 (6)0.3693 (12)0.11224 (13)0.0289 (16)
H11C−0.3181650.3833270.1052190.035*
H11D−0.2246760.2359710.1113670.035*
C12D−0.2441 (6)0.4251 (12)0.13639 (13)0.0293 (16)
H12D−0.2804140.3254270.1446680.035*
C13D−0.1348 (6)0.4653 (11)0.14831 (12)0.0243 (15)
C14D−0.0531 (6)0.5679 (11)0.13456 (12)0.0246 (15)
C15D0.0583 (6)0.5583 (12)0.14722 (14)0.0300 (17)
H15C0.0911570.4364670.1440740.036*
H15D0.1041500.6565920.1413650.036*
C16D0.0587 (6)0.5819 (12)0.17250 (14)0.0287 (16)
H16C0.0505570.7157990.1759810.034*
H16D0.1288150.5400940.1794240.034*
C17D−0.0317 (6)0.4710 (11)0.18275 (14)0.0268 (15)
C18D−0.1415 (5)0.5336 (11)0.17248 (13)0.0243 (15)
H18D−0.1952590.4511620.1790890.029*
C19D−0.1681 (6)0.7325 (11)0.17957 (13)0.0275 (16)
H19C−0.2403750.7675650.1730890.033*
H19D−0.1155330.8207940.1739500.033*
C20D−0.1650 (6)0.7450 (11)0.20514 (14)0.0296 (16)
C21D−0.0584 (7)0.6705 (12)0.21573 (14)0.0325 (17)
H21C−0.0620960.6676650.2320460.039*
H21D−0.0005090.7582940.2124130.039*
C22D−0.0286 (6)0.4756 (12)0.20785 (14)0.0308 (17)
H22C0.0442140.4424620.2141740.037*
H22D−0.0797200.3829090.2131060.037*
C23D−0.0452 (8)0.7871 (15)0.03123 (15)0.042 (2)
H23D−0.0557910.8913930.0413350.063*
H23E−0.0661780.8254900.0159460.063*
H23F0.0304900.7504370.0323950.063*
C24D−0.0810 (7)0.4530 (14)0.02354 (14)0.0372 (19)
H24D−0.0818790.4898380.0079030.056*
H24E−0.1312170.3496060.0250840.056*
H24F−0.0084990.4133190.0287680.056*
C25D−0.1721 (7)0.2518 (11)0.06663 (13)0.0301 (16)
H25D−0.0962520.2159150.0671320.045*
H25E−0.2048900.2341490.0515370.045*
H25F−0.2092570.1739480.0769780.045*
C26D−0.0116 (6)0.2686 (11)0.11111 (13)0.0278 (16)
H26D−0.0692220.1888120.1158800.042*
H26E0.0514060.2574030.1216920.042*
H26F0.0074580.2297910.0963420.042*
C27D−0.0850 (7)0.7756 (12)0.13252 (13)0.0328 (17)
H27D−0.0450330.8472170.1442120.049*
H27E−0.1620970.7885530.1340880.049*
H27F−0.0679570.8227560.1179490.049*
C28D−0.0278 (6)0.2774 (11)0.17245 (13)0.0279 (16)
C29D−0.2602 (7)0.6442 (14)0.21412 (14)0.0355 (19)
H29D−0.3267620.6860690.2060420.053*
H29E−0.2630410.6723480.2299550.053*
H29F−0.2521230.5094330.2121490.053*
C30D−0.1736 (8)0.9511 (14)0.21128 (15)0.041 (2)
H30D−0.1717140.9636620.2274680.062*
H30E−0.2412171.0019450.2046030.062*
H30F−0.1133071.0198370.2057070.062*
F1B0.4000 (5)−0.3445 (7)0.15133 (9)0.0426 (13)
O1B0.5350 (4)0.0789 (9)0.16920 (10)0.0318 (12)
O2B0.5938 (5)0.2795 (10)0.19574 (12)0.0475 (17)
O3B0.2899 (5)−0.0943 (8)0.02089 (9)0.0337 (13)
H3B0.265729−0.1933740.0159610.051*
C1B0.4070 (6)−0.2236 (10)0.07830 (13)0.0262 (15)
H1BA0.471590−0.2972420.0830820.031*
H1BB0.344093−0.2882910.0837640.031*
C2B0.3952 (6)−0.2193 (10)0.05335 (14)0.0289 (16)
H2BA0.386400−0.3483790.0476870.035*
H2BB0.461563−0.1677230.0477380.035*
C3B0.2989 (6)−0.1015 (10)0.04436 (13)0.0280 (16)
H3BA0.232604−0.1629340.0491640.034*
C4B0.3019 (6)0.0962 (10)0.05378 (13)0.0253 (15)
C5B0.3178 (6)0.0870 (10)0.07943 (13)0.0233 (14)
H5B0.2536960.0182600.0841510.028*
C6B0.3139 (6)0.2769 (10)0.09083 (13)0.0265 (15)
H6BA0.3808460.3461150.0886410.032*
H6BB0.2530550.3499830.0839520.032*
C7B0.3011 (6)0.2558 (10)0.11548 (12)0.0224 (14)
H7BA0.2303700.1985730.1174910.027*
H7BB0.3014380.3812940.1223120.027*
C8B0.3887 (6)0.1368 (10)0.12788 (13)0.0236 (15)
C9B0.4061 (6)−0.0484 (10)0.11484 (13)0.0255 (15)
H9B0.339040−0.1221870.1161920.031*
C10B0.4167 (5)−0.0285 (10)0.08918 (13)0.0226 (14)
C11B0.4952 (7)−0.1645 (11)0.12688 (14)0.0295 (16)
H11E0.500908−0.2846780.1189990.035*
H11F0.564244−0.0979270.1260560.035*
C12B0.4786 (7)−0.2038 (11)0.15101 (14)0.0317 (17)
H12B0.547192−0.2519230.1584430.038*
C13B0.4392 (6)−0.0409 (11)0.16456 (13)0.0252 (15)
C14B0.3523 (6)0.0800 (10)0.15178 (13)0.0231 (14)
C15B0.3331 (6)0.2558 (10)0.16609 (13)0.0266 (15)
H15E0.3895870.3486300.1636080.032*
H15F0.2632600.3116020.1608870.032*
C16B0.3329 (7)0.2183 (11)0.19086 (13)0.0300 (16)
H16E0.2653240.1544480.1938980.036*
H16F0.3350780.3387060.1989000.036*
C17B0.4297 (6)0.0961 (11)0.19992 (13)0.0273 (16)
C18B0.4210 (6)−0.0978 (11)0.18883 (13)0.0246 (15)
H18B0.487769−0.1653790.1942950.030*
C19B0.3286 (6)−0.2131 (11)0.19704 (13)0.0263 (15)
H19E0.327764−0.3383060.1901230.032*
H19F0.259351−0.1513500.1926990.032*
C20B0.3427 (6)−0.2323 (12)0.22277 (13)0.0278 (16)
C21B0.3531 (7)−0.0361 (12)0.23365 (13)0.0306 (17)
H21E0.2835590.0295580.2311900.037*
H21F0.368231−0.0513100.2498730.037*
C22B0.4404 (7)0.0844 (12)0.22476 (14)0.0336 (18)
H22E0.4364110.2114250.2310590.040*
H22F0.5114690.0315690.2296080.040*
C23B0.1903 (7)0.1844 (13)0.04754 (14)0.0329 (18)
H23G0.1698670.1616430.0317990.049*
H23H0.1937390.3190510.0502870.049*
H23I0.1369230.1283140.0566120.049*
C24B0.3866 (7)0.2173 (12)0.04298 (13)0.0312 (17)
H24G0.4572010.1581720.0452990.047*
H24H0.3889540.3413540.0497940.047*
H24I0.3671370.2288710.0270220.047*
C25B0.5278 (6)0.0522 (12)0.08405 (13)0.0287 (16)
H25G0.5429070.0194340.0688390.043*
H25H0.583576−0.0001570.0944850.043*
H25I0.5267350.1881870.0856110.043*
C26B0.4919 (6)0.2590 (11)0.12909 (14)0.0280 (16)
H26G0.4849220.3598640.1398450.042*
H26H0.5015240.3123870.1144240.042*
H26I0.5541730.1818170.1337610.042*
C27B0.2448 (6)−0.0313 (11)0.14986 (13)0.0267 (15)
H27G0.1996610.0135380.1370040.040*
H27H0.207150−0.0131830.1633860.040*
H27I0.259924−0.1642410.1480010.040*
C28B0.5274 (7)0.1642 (13)0.18911 (15)0.0335 (18)
C29B0.4423 (7)−0.3479 (12)0.23034 (13)0.0300 (16)
H29G0.441818−0.3743680.2462540.045*
H29H0.507159−0.2776450.2275270.045*
H29I0.441357−0.4654850.2220530.045*
C30B0.2433 (7)−0.3292 (14)0.23056 (14)0.0348 (18)
H30G0.236527−0.4533720.2238320.052*
H30H0.179432−0.2552360.2260750.052*
H30I0.250135−0.3411220.2467720.052*
F1C0.8093 (5)0.3451 (7)0.34930 (9)0.0401 (12)
O1C0.9292 (4)−0.0814 (8)0.33233 (9)0.0290 (11)
O2C0.9693 (5)−0.2869 (10)0.30602 (11)0.0443 (16)
O3C0.7735 (5)0.1025 (8)0.47955 (10)0.0373 (14)
H3C0.7448350.1956840.4843340.056*
C1C0.8581 (6)0.2275 (10)0.42259 (13)0.0253 (15)
H1CA0.9198430.3008120.4180140.030*
H1CB0.7917650.2918990.4168040.030*
C2C0.8615 (6)0.2244 (11)0.44778 (14)0.0301 (16)
H2CA0.8572940.3536520.4533970.036*
H2CB0.9304790.1702080.4537600.036*
C3C0.7681 (6)0.1090 (10)0.45604 (13)0.0270 (16)
H3CA0.6994550.1722750.4508460.032*
C4C0.7643 (6)−0.0911 (11)0.44686 (13)0.0263 (15)
C5C0.7667 (6)−0.0832 (10)0.42118 (13)0.0229 (14)
H5C0.700307−0.0130800.4160390.028*
C6C0.7541 (6)−0.2720 (11)0.40983 (13)0.0275 (16)
H6CA0.821691−0.3433960.4124340.033*
H6CB0.696456−0.3429640.4164480.033*
C7C0.7273 (6)−0.2526 (10)0.38509 (13)0.0237 (14)
H7CA0.655491−0.1946150.3826190.028*
H7CB0.723265−0.3785000.3783720.028*
C8C0.8084 (6)−0.1354 (10)0.37313 (12)0.0233 (15)
C9C0.8335 (5)0.0512 (10)0.38620 (13)0.0222 (14)
H9C0.7658000.1259740.3845370.027*
C10C0.8612 (5)0.0321 (10)0.41190 (13)0.0231 (15)
C11C0.9166 (6)0.1628 (11)0.37427 (13)0.0272 (16)
H11G0.9295080.2824860.3821860.033*
H11H0.9849730.0926810.3752590.033*
C12C0.8858 (6)0.2035 (10)0.35039 (14)0.0270 (16)
H12C0.9507880.2493480.3433180.032*
C13C0.8370 (6)0.0418 (10)0.33643 (13)0.0255 (15)
C14C0.7566 (5)−0.0762 (10)0.34887 (12)0.0219 (14)
C15C0.7265 (6)−0.2518 (11)0.33461 (13)0.0293 (16)
H15G0.784122−0.3457180.3372190.035*
H15H0.659812−0.3059780.3397320.035*
C16C0.7103 (6)−0.2154 (11)0.31007 (14)0.0284 (16)
H16G0.641649−0.1483420.3068710.034*
H16H0.705509−0.3358000.3020470.034*
C17C0.8045 (6)−0.0963 (12)0.30135 (13)0.0280 (16)
C18C0.8039 (6)0.0962 (11)0.31209 (12)0.0250 (15)
H18C0.8684140.1603010.3068280.030*
C19C0.7089 (6)0.2176 (10)0.30336 (13)0.0247 (15)
H19G0.7156540.3434440.3100640.030*
H19H0.6410370.1616440.3076390.030*
C20C0.7067 (6)0.2333 (11)0.27792 (13)0.0260 (15)
C21C0.7064 (7)0.0383 (11)0.26743 (13)0.0293 (16)
H21G0.638003−0.0242900.2701580.035*
H21H0.7092220.0518220.2511690.035*
C22C0.7990 (7)−0.0860 (12)0.27618 (14)0.0318 (17)
H22G0.789006−0.2128660.2699020.038*
H22H0.867275−0.0356110.2713690.038*
C23C0.6580 (7)−0.1792 (13)0.45274 (14)0.0340 (18)
H23J0.659617−0.3135590.4498060.051*
H23K0.598490−0.1223120.4436720.051*
H23L0.648082−0.1581000.4684960.051*
C24C0.8561 (7)−0.2110 (12)0.45813 (13)0.0296 (16)
H24J0.844558−0.2268630.4738970.044*
H24K0.924979−0.1484230.4566690.044*
H24L0.856925−0.3334310.4509370.044*
C25C0.9747 (6)−0.0491 (12)0.41754 (13)0.0290 (16)
H25J1.001577−0.0072960.4323670.043*
H25K1.023111−0.0059020.4065620.043*
H25L0.971216−0.1856350.4172650.043*
C26C0.9098 (6)−0.2591 (11)0.37235 (13)0.0272 (15)
H26J0.971013−0.1815500.3689170.041*
H26K0.897363−0.3546850.3608530.041*
H26L0.925238−0.3193870.3868040.041*
C27C0.6521 (6)0.0365 (11)0.35039 (13)0.0251 (15)
H27J0.6005060.0016580.3380840.038*
H27K0.6679030.1700550.3495300.038*
H27L0.6214740.0094340.3645340.038*
C28C0.9096 (7)−0.1687 (13)0.31237 (13)0.0317 (18)
C29C0.8062 (7)0.3414 (12)0.27058 (14)0.0314 (17)
H29J0.8090100.4649900.2775270.047*
H29K0.8005260.3552380.2543880.047*
H29L0.8716250.2721530.2752000.047*
C30C0.6067 (7)0.3386 (13)0.26943 (14)0.0323 (17)
H30J0.6090270.4653000.2755230.048*
H30K0.5430200.2739550.2740980.048*
H30L0.6034240.3445920.2531770.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O130.035 (3)0.020 (3)0.058 (4)−0.001 (2)0.005 (3)0.007 (3)
C1210.033 (4)0.019 (4)0.080 (7)−0.004 (3)−0.002 (4)0.007 (4)
O140.037 (3)0.021 (3)0.064 (4)0.007 (3)0.020 (3)0.006 (3)
C1220.042 (5)0.037 (6)0.078 (7)0.000 (4)0.027 (5)0.004 (5)
F1A0.018 (2)0.035 (3)0.051 (3)−0.0109 (19)0.0092 (18)−0.006 (2)
O1A0.030 (3)0.020 (3)0.032 (3)−0.001 (2)0.010 (2)0.000 (2)
O2A0.044 (3)0.027 (3)0.040 (3)−0.011 (3)0.010 (3)0.002 (2)
O3A0.040 (3)0.016 (3)0.040 (3)−0.001 (2)0.009 (2)0.000 (2)
C1A0.015 (3)0.021 (4)0.044 (4)0.000 (3)0.009 (3)−0.002 (3)
C2A0.019 (3)0.024 (4)0.049 (5)0.002 (3)0.007 (3)−0.002 (3)
C3A0.033 (4)0.017 (4)0.036 (4)0.004 (3)0.006 (3)−0.002 (3)
C4A0.022 (4)0.019 (4)0.044 (4)0.001 (3)0.005 (3)−0.003 (3)
C5A0.016 (3)0.016 (4)0.047 (4)0.002 (3)0.006 (3)−0.004 (3)
C6A0.023 (4)0.027 (4)0.044 (5)0.003 (3)0.005 (3)0.006 (3)
C7A0.021 (4)0.025 (4)0.047 (5)0.007 (3)0.007 (3)0.004 (3)
C8A0.011 (3)0.027 (4)0.034 (4)0.002 (3)0.005 (3)0.001 (3)
C9A0.017 (3)0.012 (3)0.042 (4)0.003 (2)0.008 (3)0.001 (3)
C10A0.022 (3)0.019 (4)0.036 (4)−0.003 (3)0.006 (3)0.002 (3)
C11A0.020 (3)0.018 (4)0.041 (4)0.008 (3)0.011 (3)0.004 (3)
C12A0.013 (3)0.019 (4)0.046 (4)−0.003 (3)0.008 (3)0.003 (3)
C13A0.021 (3)0.019 (4)0.033 (4)−0.001 (3)0.009 (3)0.003 (3)
C14A0.017 (3)0.023 (4)0.033 (4)0.000 (3)0.005 (3)0.002 (3)
C15A0.012 (3)0.025 (4)0.051 (5)0.005 (3)0.008 (3)0.001 (3)
C16A0.019 (3)0.025 (4)0.045 (4)0.011 (3)0.011 (3)0.004 (3)
C17A0.017 (3)0.023 (4)0.036 (4)−0.003 (3)0.005 (3)−0.001 (3)
C18A0.020 (3)0.029 (4)0.033 (4)0.003 (3)0.006 (3)0.002 (3)
C19A0.025 (4)0.027 (4)0.045 (5)−0.003 (3)0.007 (3)−0.004 (3)
C20A0.024 (4)0.038 (5)0.041 (5)−0.001 (3)0.007 (3)−0.009 (4)
C21A0.035 (4)0.032 (5)0.032 (4)0.004 (3)0.007 (3)−0.005 (3)
C22A0.028 (4)0.017 (4)0.043 (4)−0.007 (3)0.011 (3)0.000 (3)
C23A0.051 (6)0.042 (5)0.034 (4)0.011 (4)0.003 (4)0.007 (4)
C24A0.033 (4)0.033 (5)0.039 (4)−0.003 (4)0.005 (3)−0.003 (4)
C25A0.036 (4)0.020 (4)0.037 (4)−0.003 (3)0.007 (3)−0.002 (3)
C26A0.022 (3)0.020 (4)0.039 (4)−0.004 (3)0.009 (3)−0.001 (3)
C27A0.036 (4)0.028 (4)0.031 (4)0.009 (3)0.006 (3)0.000 (3)
C28A0.036 (4)0.031 (4)0.025 (4)−0.004 (3)0.007 (3)0.002 (3)
C29A0.026 (4)0.067 (7)0.042 (5)0.015 (4)0.000 (3)−0.012 (5)
C30A0.038 (5)0.035 (5)0.049 (5)−0.009 (4)0.009 (4)−0.012 (4)
F1D0.019 (2)0.036 (3)0.051 (3)0.0130 (19)0.0071 (18)−0.004 (2)
O1D0.027 (3)0.013 (2)0.041 (3)0.000 (2)0.006 (2)0.002 (2)
O2D0.039 (3)0.028 (3)0.046 (3)0.009 (3)0.008 (3)0.003 (3)
O3D0.047 (4)0.024 (3)0.038 (3)0.002 (3)0.007 (3)−0.003 (2)
C1D0.018 (3)0.022 (4)0.050 (5)0.000 (3)0.008 (3)−0.004 (3)
C2D0.024 (4)0.020 (4)0.049 (5)0.002 (3)0.004 (3)0.001 (3)
C3D0.036 (4)0.018 (4)0.036 (4)−0.003 (3)0.008 (3)−0.006 (3)
C4D0.027 (4)0.018 (4)0.048 (5)−0.004 (3)0.010 (3)−0.005 (3)
C5D0.020 (3)0.013 (3)0.044 (4)−0.008 (3)0.013 (3)−0.003 (3)
C6D0.019 (3)0.029 (4)0.045 (5)0.000 (3)0.010 (3)0.002 (3)
C7D0.019 (3)0.019 (4)0.045 (4)0.001 (3)0.009 (3)0.001 (3)
C8D0.016 (3)0.019 (4)0.037 (4)0.000 (3)0.008 (3)0.001 (3)
C9D0.014 (3)0.018 (4)0.041 (4)0.000 (3)0.010 (3)−0.001 (3)
C10D0.020 (3)0.019 (4)0.040 (4)0.003 (3)0.007 (3)0.004 (3)
C11D0.020 (4)0.031 (4)0.036 (4)−0.007 (3)0.003 (3)0.004 (3)
C12D0.015 (3)0.032 (4)0.041 (4)0.005 (3)0.007 (3)0.007 (3)
C13D0.020 (3)0.021 (4)0.031 (4)−0.001 (3)0.005 (3)0.004 (3)
C14D0.019 (3)0.023 (4)0.032 (4)−0.006 (3)0.007 (3)−0.001 (3)
C15D0.013 (3)0.024 (4)0.053 (5)−0.003 (3)0.006 (3)−0.001 (3)
C16D0.017 (3)0.024 (4)0.046 (5)−0.006 (3)0.005 (3)−0.001 (3)
C17D0.020 (3)0.020 (4)0.041 (4)0.001 (3)0.006 (3)−0.001 (3)
C18D0.015 (3)0.022 (4)0.036 (4)−0.005 (3)0.005 (3)0.002 (3)
C19D0.021 (3)0.017 (4)0.045 (4)−0.002 (3)0.008 (3)0.002 (3)
C20D0.026 (4)0.017 (4)0.047 (5)−0.002 (3)0.010 (3)−0.001 (3)
C21D0.035 (4)0.028 (4)0.035 (4)0.001 (3)0.005 (3)−0.005 (3)
C22D0.023 (4)0.022 (4)0.047 (5)0.005 (3)0.001 (3)−0.001 (3)
C23D0.047 (5)0.042 (5)0.038 (5)−0.008 (4)0.011 (4)0.008 (4)
C24D0.035 (4)0.046 (6)0.031 (4)0.007 (4)0.007 (3)−0.002 (4)
C25D0.040 (4)0.017 (4)0.034 (4)−0.005 (3)0.006 (3)−0.002 (3)
C26D0.027 (4)0.024 (4)0.033 (4)−0.004 (3)0.005 (3)−0.005 (3)
C27D0.045 (5)0.024 (4)0.030 (4)−0.003 (3)0.009 (3)0.000 (3)
C28D0.033 (4)0.020 (4)0.032 (4)0.004 (3)0.008 (3)0.003 (3)
C29D0.029 (4)0.045 (5)0.034 (4)−0.003 (4)0.011 (3)−0.001 (4)
C30D0.050 (5)0.037 (5)0.038 (5)0.010 (4)0.013 (4)−0.006 (4)
F1B0.063 (3)0.010 (2)0.058 (3)−0.008 (2)0.026 (3)−0.001 (2)
O1B0.021 (3)0.030 (3)0.044 (3)−0.007 (2)0.004 (2)0.004 (2)
O2B0.039 (4)0.038 (4)0.065 (4)−0.025 (3)−0.003 (3)0.002 (3)
O3B0.047 (3)0.015 (3)0.039 (3)0.001 (2)0.007 (2)−0.004 (2)
C1B0.026 (3)0.009 (3)0.045 (4)0.005 (3)0.007 (3)0.001 (3)
C2B0.033 (4)0.009 (3)0.045 (4)0.001 (3)0.009 (3)−0.003 (3)
C3B0.032 (4)0.011 (3)0.041 (4)0.000 (3)0.005 (3)−0.004 (3)
C4B0.024 (3)0.012 (3)0.041 (4)0.003 (3)0.007 (3)−0.002 (3)
C5B0.019 (3)0.007 (3)0.045 (4)0.001 (2)0.007 (3)−0.002 (3)
C6B0.029 (4)0.009 (3)0.042 (4)0.007 (3)0.004 (3)0.000 (3)
C7B0.021 (3)0.010 (3)0.037 (4)0.008 (2)0.006 (3)−0.002 (3)
C8B0.025 (4)0.010 (3)0.036 (4)0.006 (3)0.004 (3)0.002 (3)
C9B0.024 (3)0.015 (4)0.039 (4)0.003 (3)0.006 (3)−0.001 (3)
C10B0.016 (3)0.012 (3)0.040 (4)0.000 (3)0.008 (3)0.000 (3)
C11B0.034 (4)0.016 (4)0.041 (4)0.004 (3)0.011 (3)−0.001 (3)
C12B0.033 (4)0.017 (4)0.046 (5)0.006 (3)0.009 (3)0.001 (3)
C13B0.024 (4)0.016 (4)0.036 (4)−0.001 (3)0.004 (3)0.000 (3)
C14B0.020 (3)0.010 (3)0.039 (4)0.004 (3)0.005 (3)−0.002 (3)
C15B0.027 (4)0.011 (3)0.041 (4)0.001 (3)0.003 (3)−0.004 (3)
C16B0.036 (4)0.017 (4)0.038 (4)0.001 (3)0.005 (3)−0.004 (3)
C17B0.029 (4)0.014 (4)0.039 (4)−0.003 (3)0.001 (3)−0.001 (3)
C18B0.022 (3)0.017 (4)0.035 (4)0.006 (3)0.005 (3)0.000 (3)
C19B0.025 (4)0.019 (4)0.034 (4)−0.004 (3)0.002 (3)−0.002 (3)
C20B0.030 (4)0.023 (4)0.032 (4)−0.004 (3)0.006 (3)0.002 (3)
C21B0.036 (4)0.026 (4)0.030 (4)0.002 (3)0.005 (3)−0.002 (3)
C22B0.040 (5)0.015 (4)0.046 (5)−0.006 (3)0.000 (3)−0.003 (3)
C23B0.036 (4)0.030 (5)0.033 (4)0.007 (3)0.002 (3)−0.003 (3)
C24B0.038 (4)0.024 (4)0.032 (4)0.002 (3)0.008 (3)0.000 (3)
C25B0.023 (4)0.026 (4)0.038 (4)0.002 (3)0.011 (3)0.001 (3)
C26B0.027 (4)0.013 (4)0.045 (4)−0.002 (3)0.009 (3)0.002 (3)
C27B0.026 (4)0.017 (4)0.038 (4)−0.008 (3)0.009 (3)−0.003 (3)
C28B0.027 (4)0.030 (4)0.042 (5)−0.017 (3)−0.003 (3)0.006 (3)
C29B0.030 (4)0.026 (4)0.034 (4)0.004 (3)0.001 (3)0.003 (3)
C30B0.031 (4)0.041 (5)0.034 (4)−0.001 (4)0.009 (3)0.006 (3)
F1C0.060 (3)0.010 (2)0.049 (3)0.009 (2)−0.005 (2)−0.0015 (19)
O1C0.025 (3)0.028 (3)0.035 (3)0.002 (2)0.009 (2)0.004 (2)
O2C0.045 (4)0.039 (4)0.051 (4)0.028 (3)0.016 (3)0.001 (3)
O3C0.057 (4)0.018 (3)0.038 (3)0.001 (3)0.010 (3)−0.005 (2)
C1C0.021 (3)0.008 (3)0.048 (4)−0.007 (3)0.006 (3)−0.001 (3)
C2C0.028 (4)0.014 (4)0.049 (5)−0.004 (3)0.006 (3)−0.003 (3)
C3C0.032 (4)0.013 (4)0.037 (4)0.003 (3)0.010 (3)−0.002 (3)
C4C0.027 (4)0.014 (4)0.038 (4)−0.005 (3)0.007 (3)0.000 (3)
C5C0.019 (3)0.009 (3)0.042 (4)−0.001 (3)0.005 (3)−0.002 (3)
C6C0.028 (4)0.019 (4)0.037 (4)−0.006 (3)0.011 (3)−0.002 (3)
C7C0.021 (3)0.011 (3)0.041 (4)−0.003 (3)0.008 (3)−0.001 (3)
C8C0.023 (4)0.017 (4)0.031 (4)−0.004 (3)0.008 (3)0.000 (3)
C9C0.016 (3)0.008 (3)0.043 (4)−0.007 (2)0.008 (3)0.000 (3)
C10C0.015 (3)0.009 (3)0.046 (4)−0.005 (2)0.009 (3)−0.005 (3)
C11C0.029 (4)0.016 (4)0.038 (4)−0.009 (3)0.009 (3)0.000 (3)
C12C0.015 (3)0.013 (3)0.054 (5)−0.008 (3)0.007 (3)−0.003 (3)
C13C0.025 (4)0.014 (4)0.038 (4)−0.005 (3)0.008 (3)0.000 (3)
C14C0.020 (3)0.010 (3)0.037 (4)−0.001 (3)0.008 (3)−0.001 (3)
C15C0.031 (4)0.017 (4)0.041 (4)−0.010 (3)0.006 (3)−0.004 (3)
C16C0.030 (4)0.013 (3)0.043 (4)−0.007 (3)0.009 (3)−0.004 (3)
C17C0.029 (4)0.024 (4)0.032 (4)0.000 (3)0.006 (3)−0.001 (3)
C18C0.022 (3)0.024 (4)0.029 (4)−0.004 (3)0.008 (3)−0.004 (3)
C19C0.021 (3)0.010 (3)0.044 (4)0.000 (3)0.009 (3)−0.002 (3)
C20C0.023 (4)0.017 (4)0.038 (4)0.001 (3)0.004 (3)−0.002 (3)
C21C0.038 (4)0.023 (4)0.027 (4)−0.001 (3)0.002 (3)0.000 (3)
C22C0.041 (4)0.017 (4)0.038 (4)0.006 (3)0.010 (3)−0.001 (3)
C23C0.035 (4)0.032 (5)0.037 (4)−0.007 (3)0.009 (3)−0.003 (3)
C24C0.036 (4)0.022 (4)0.031 (4)0.002 (3)0.005 (3)0.001 (3)
C25C0.027 (4)0.026 (4)0.034 (4)0.003 (3)0.000 (3)0.001 (3)
C26C0.030 (4)0.018 (4)0.034 (4)0.001 (3)0.005 (3)0.003 (3)
C27C0.019 (3)0.017 (4)0.040 (4)0.005 (3)0.004 (3)−0.001 (3)
C28C0.033 (4)0.036 (5)0.028 (4)0.012 (3)0.010 (3)0.007 (3)
C29C0.032 (4)0.026 (4)0.037 (4)−0.004 (3)0.007 (3)0.005 (3)
C30C0.028 (4)0.033 (5)0.036 (4)0.008 (3)−0.001 (3)−0.003 (3)
Geometric parameters (Å, º) top
O13—H130.8196C29D—H29E0.9800
O13—C1211.406 (11)C29D—H29F0.9800
C121—H12E0.9800C30D—H30D0.9800
C121—H12F0.9800C30D—H30E0.9800
C121—H12G0.9800C30D—H30F0.9800
O14—H140.8198F1B—C12B1.409 (10)
O14—C1221.413 (11)O1B—C13B1.483 (9)
C122—H12H0.9800O1B—C28B1.358 (11)
C122—H12I0.9800O2B—C28B1.218 (10)
C122—H12J0.9800O3B—H3B0.8198
F1A—C12A1.437 (9)O3B—C3B1.414 (10)
O1A—C13A1.470 (9)C1B—H1BA0.9900
O1A—C28A1.384 (9)C1B—H1BB0.9900
O2A—C28A1.204 (10)C1B—C2B1.503 (11)
O3A—H3A0.8194C1B—C10B1.547 (10)
O3A—C3A1.410 (10)C2B—H2BA0.9900
C1A—H1AA0.9900C2B—H2BB0.9900
C1A—H1AB0.9900C2B—C3B1.537 (11)
C1A—C2A1.513 (11)C3B—H3BA1.0000
C1A—C10A1.551 (10)C3B—C4B1.527 (10)
C2A—H2AA0.9900C4B—C5B1.549 (11)
C2A—H2AB0.9900C4B—C23B1.553 (11)
C2A—C3A1.519 (11)C4B—C24B1.549 (11)
C3A—H3AA1.0000C5B—H5B1.0000
C3A—C4A1.562 (11)C5B—C6B1.528 (10)
C4A—C5A1.540 (11)C5B—C10B1.567 (10)
C4A—C23A1.538 (12)C6B—H6BA0.9900
C4A—C24A1.536 (12)C6B—H6BB0.9900
C5A—H5A1.0000C6B—C7B1.516 (11)
C5A—C6A1.542 (10)C7B—H7BA0.9900
C5A—C10A1.549 (10)C7B—H7BB0.9900
C6A—H6AA0.9900C7B—C8B1.538 (9)
C6A—H6AB0.9900C8B—C9B1.567 (10)
C6A—C7A1.514 (12)C8B—C14B1.597 (10)
C7A—H7AA0.9900C8B—C26B1.557 (10)
C7A—H7AB0.9900C9B—H9B1.0000
C7A—C8A1.533 (10)C9B—C10B1.571 (10)
C8A—C9A1.565 (9)C9B—C11B1.531 (11)
C8A—C14A1.599 (11)C10B—C25B1.556 (10)
C8A—C26A1.548 (11)C11B—H11E0.9900
C9A—H9A1.0000C11B—H11F0.9900
C9A—C10A1.556 (11)C11B—C12B1.513 (12)
C9A—C11A1.526 (10)C12B—H12B1.0000
C10A—C25A1.556 (11)C12B—C13B1.528 (11)
C11A—H11A0.9900C13B—C14B1.551 (10)
C11A—H11B0.9900C13B—C18B1.554 (11)
C11A—C12A1.501 (11)C14B—C15B1.557 (10)
C12A—H12A1.0000C14B—C27B1.561 (10)
C12A—C13A1.540 (9)C15B—H15E0.9900
C13A—C14A1.561 (10)C15B—H15F0.9900
C13A—C18A1.554 (11)C15B—C16B1.520 (11)
C14A—C15A1.549 (9)C16B—H16E0.9900
C14A—C27A1.570 (12)C16B—H16F0.9900
C15A—H15A0.9900C16B—C17B1.560 (11)
C15A—H15B0.9900C17B—C18B1.544 (10)
C15A—C16A1.520 (11)C17B—C22B1.498 (12)
C16A—H16A0.9900C17B—C28B1.507 (11)
C16A—H16B0.9900C18B—H18B1.0000
C16A—C17A1.540 (10)C18B—C19B1.532 (10)
C17A—C18A1.519 (10)C19B—H19E0.9900
C17A—C22A1.513 (11)C19B—H19F0.9900
C17A—C28A1.527 (12)C19B—C20B1.557 (11)
C18A—H18A1.0000C20B—C21B1.555 (11)
C18A—C19A1.542 (12)C20B—C29B1.537 (11)
C19A—H19A0.9900C20B—C30B1.527 (11)
C19A—H19B0.9900C21B—H21E0.9900
C19A—C20A1.544 (12)C21B—H21F0.9900
C20A—C21A1.534 (12)C21B—C22B1.520 (12)
C20A—C29A1.540 (12)C22B—H22E0.9900
C20A—C30A1.547 (13)C22B—H22F0.9900
C21A—H21A0.9900C23B—H23G0.9800
C21A—H21B0.9900C23B—H23H0.9800
C21A—C22A1.536 (12)C23B—H23I0.9800
C22A—H22A0.9900C24B—H24G0.9800
C22A—H22B0.9900C24B—H24H0.9800
C23A—H23A0.9800C24B—H24I0.9800
C23A—H23B0.9800C25B—H25G0.9800
C23A—H23C0.9800C25B—H25H0.9800
C24A—H24A0.9800C25B—H25I0.9800
C24A—H24B0.9800C26B—H26G0.9800
C24A—H24C0.9800C26B—H26H0.9800
C25A—H25A0.9800C26B—H26I0.9800
C25A—H25B0.9800C27B—H27G0.9800
C25A—H25C0.9800C27B—H27H0.9800
C26A—H26A0.9800C27B—H27I0.9800
C26A—H26B0.9800C29B—H29G0.9800
C26A—H26C0.9800C29B—H29H0.9800
C27A—H27A0.9800C29B—H29I0.9800
C27A—H27B0.9800C30B—H30G0.9800
C27A—H27C0.9800C30B—H30H0.9800
C29A—H29A0.9800C30B—H30I0.9800
C29A—H29B0.9800F1C—C12C1.393 (9)
C29A—H29C0.9800O1C—C13C1.488 (9)
C30A—H30A0.9800O1C—C28C1.364 (10)
C30A—H30B0.9800O2C—C28C1.210 (10)
C30A—H30C0.9800O3C—H3C0.8203
F1D—C12D1.438 (9)O3C—C3C1.417 (10)
O1D—C13D1.495 (9)C1C—H1CA0.9900
O1D—C28D1.359 (10)C1C—H1CB0.9900
O2D—C28D1.217 (10)C1C—C2C1.518 (11)
O3D—H3D0.8200C1C—C10C1.544 (10)
O3D—C3D1.417 (10)C2C—H2CA0.9900
C1D—H1DA0.9900C2C—H2CB0.9900
C1D—H1DB0.9900C2C—C3C1.543 (10)
C1D—C2D1.524 (12)C3C—H3CA1.0000
C1D—C10D1.566 (10)C3C—C4C1.538 (11)
C2D—H2DA0.9900C4C—C5C1.554 (11)
C2D—H2DB0.9900C4C—C23C1.536 (11)
C2D—C3D1.507 (11)C4C—C24C1.552 (11)
C3D—H3DA1.0000C5C—H5C1.0000
C3D—C4D1.550 (12)C5C—C6C1.521 (10)
C4D—C5D1.539 (12)C5C—C10C1.577 (9)
C4D—C23D1.543 (12)C6C—H6CA0.9900
C4D—C24D1.545 (12)C6C—H6CB0.9900
C5D—H5D1.0000C6C—C7C1.513 (11)
C5D—C6D1.534 (11)C7C—H7CA0.9900
C5D—C10D1.551 (10)C7C—H7CB0.9900
C6D—H6DA0.9900C7C—C8C1.538 (9)
C6D—H6DB0.9900C8C—C9C1.574 (10)
C6D—C7D1.514 (11)C8C—C14C1.615 (10)
C7D—H7DA0.9900C8C—C26C1.551 (10)
C7D—H7DB0.9900C9C—H9C1.0000
C7D—C8D1.537 (10)C9C—C10C1.571 (11)
C8D—C9D1.562 (10)C9C—C11C1.532 (9)
C8D—C14D1.618 (10)C10C—C25C1.549 (10)
C8D—C26D1.554 (11)C11C—H11G0.9900
C9D—H9D1.0000C11C—H11H0.9900
C9D—C10D1.558 (11)C11C—C12C1.493 (12)
C9D—C11D1.552 (10)C12C—H12C1.0000
C10D—C25D1.542 (11)C12C—C13C1.535 (10)
C11D—H11C0.9900C13C—C14C1.549 (9)
C11D—H11D0.9900C13C—C18C1.548 (11)
C11D—C12D1.512 (11)C14C—C15C1.556 (10)
C12D—H12D1.0000C14C—C27C1.545 (9)
C12D—C13D1.525 (10)C15C—H15G0.9900
C13D—C14D1.548 (9)C15C—H15H0.9900
C13D—C18D1.547 (11)C15C—C16C1.504 (11)
C14D—C15D1.541 (10)C16C—H16G0.9900
C14D—C27D1.544 (12)C16C—H16H0.9900
C15D—H15C0.9900C16C—C17C1.576 (10)
C15D—H15D0.9900C17C—C18C1.525 (11)
C15D—C16D1.535 (12)C17C—C22C1.518 (11)
C16D—H16C0.9900C17C—C28C1.521 (11)
C16D—H16D0.9900C18C—H18C1.0000
C16D—C17D1.547 (10)C18C—C19C1.534 (10)
C17D—C18D1.532 (10)C19C—H19G0.9900
C17D—C22D1.513 (12)C19C—H19H0.9900
C17D—C28D1.524 (11)C19C—C20C1.538 (11)
C18D—H18D1.0000C20C—C21C1.535 (11)
C18D—C19D1.533 (11)C20C—C29C1.557 (10)
C19D—H19C0.9900C20C—C30C1.518 (10)
C19D—H19D0.9900C21C—H21G0.9900
C19D—C20D1.544 (11)C21C—H21H0.9900
C20D—C21D1.531 (12)C21C—C22C1.524 (11)
C20D—C29D1.526 (11)C22C—H22G0.9900
C20D—C30D1.530 (12)C22C—H22H0.9900
C21D—H21C0.9900C23C—H23J0.9800
C21D—H21D0.9900C23C—H23K0.9800
C21D—C22D1.532 (11)C23C—H23L0.9800
C22D—H22C0.9900C24C—H24J0.9800
C22D—H22D0.9900C24C—H24K0.9800
C23D—H23D0.9800C24C—H24L0.9800
C23D—H23E0.9800C25C—H25J0.9800
C23D—H23F0.9800C25C—H25K0.9800
C24D—H24D0.9800C25C—H25L0.9800
C24D—H24E0.9800C26C—H26J0.9800
C24D—H24F0.9800C26C—H26K0.9800
C25D—H25D0.9800C26C—H26L0.9800
C25D—H25E0.9800C27C—H27J0.9800
C25D—H25F0.9800C27C—H27K0.9800
C26D—H26D0.9800C27C—H27L0.9800
C26D—H26E0.9800C29C—H29J0.9800
C26D—H26F0.9800C29C—H29K0.9800
C27D—H27D0.9800C29C—H29L0.9800
C27D—H27E0.9800C30C—H30J0.9800
C27D—H27F0.9800C30C—H30K0.9800
C29D—H29D0.9800C30C—H30L0.9800
C121—O13—H13109.4H29E—C29D—H29F109.5
O13—C121—H12E109.5C20D—C30D—H30D109.5
O13—C121—H12F109.5C20D—C30D—H30E109.5
O13—C121—H12G109.5C20D—C30D—H30F109.5
H12E—C121—H12F109.5H30D—C30D—H30E109.5
H12E—C121—H12G109.5H30D—C30D—H30F109.5
H12F—C121—H12G109.5H30E—C30D—H30F109.5
C122—O14—H14109.6C28B—O1B—C13B108.7 (6)
O14—C122—H12H109.5C3B—O3B—H3B109.4
O14—C122—H12I109.5H1BA—C1B—H1BB107.7
O14—C122—H12J109.5C2B—C1B—H1BA108.8
H12H—C122—H12I109.5C2B—C1B—H1BB108.8
H12H—C122—H12J109.5C2B—C1B—C10B114.0 (6)
H12I—C122—H12J109.5C10B—C1B—H1BA108.8
C28A—O1A—C13A109.6 (6)C10B—C1B—H1BB108.8
C3A—O3A—H3A109.4C1B—C2B—H2BA109.1
H1AA—C1A—H1AB107.8C1B—C2B—H2BB109.1
C2A—C1A—H1AA109.0C1B—C2B—C3B112.5 (6)
C2A—C1A—H1AB109.0H2BA—C2B—H2BB107.8
C2A—C1A—C10A112.8 (6)C3B—C2B—H2BA109.1
C10A—C1A—H1AA109.0C3B—C2B—H2BB109.1
C10A—C1A—H1AB109.0O3B—C3B—C2B112.1 (6)
C1A—C2A—H2AA109.1O3B—C3B—H3BA107.4
C1A—C2A—H2AB109.1O3B—C3B—C4B109.7 (6)
C1A—C2A—C3A112.5 (6)C2B—C3B—H3BA107.4
H2AA—C2A—H2AB107.8C4B—C3B—C2B112.4 (6)
C3A—C2A—H2AA109.1C4B—C3B—H3BA107.4
C3A—C2A—H2AB109.1C3B—C4B—C5B109.3 (6)
O3A—C3A—C2A112.8 (6)C3B—C4B—C23B106.9 (6)
O3A—C3A—H3AA106.6C3B—C4B—C24B111.3 (6)
O3A—C3A—C4A111.9 (7)C5B—C4B—C23B107.9 (6)
C2A—C3A—H3AA106.6C5B—C4B—C24B113.7 (6)
C2A—C3A—C4A111.7 (7)C24B—C4B—C23B107.4 (7)
C4A—C3A—H3AA106.6C4B—C5B—H5B105.0
C5A—C4A—C3A107.8 (6)C4B—C5B—C10B116.0 (6)
C23A—C4A—C3A106.4 (7)C6B—C5B—C4B114.0 (6)
C23A—C4A—C5A109.7 (6)C6B—C5B—H5B105.0
C24A—C4A—C3A110.6 (6)C6B—C5B—C10B110.6 (6)
C24A—C4A—C5A115.6 (7)C10B—C5B—H5B105.0
C24A—C4A—C23A106.4 (7)C5B—C6B—H6BA109.4
C4A—C5A—H5A104.2C5B—C6B—H6BB109.4
C4A—C5A—C6A113.7 (6)H6BA—C6B—H6BB108.0
C4A—C5A—C10A118.2 (6)C7B—C6B—C5B111.2 (6)
C6A—C5A—H5A104.2C7B—C6B—H6BA109.4
C6A—C5A—C10A110.5 (6)C7B—C6B—H6BB109.4
C10A—C5A—H5A104.2C6B—C7B—H7BA108.7
C5A—C6A—H6AA109.4C6B—C7B—H7BB108.7
C5A—C6A—H6AB109.4C6B—C7B—C8B114.2 (6)
H6AA—C6A—H6AB108.0H7BA—C7B—H7BB107.6
C7A—C6A—C5A111.4 (7)C8B—C7B—H7BA108.7
C7A—C6A—H6AA109.4C8B—C7B—H7BB108.7
C7A—C6A—H6AB109.4C7B—C8B—C9B110.3 (6)
C6A—C7A—H7AA108.6C7B—C8B—C14B110.0 (6)
C6A—C7A—H7AB108.6C7B—C8B—C26B105.6 (6)
C6A—C7A—C8A114.8 (6)C9B—C8B—C14B107.3 (6)
H7AA—C7A—H7AB107.5C26B—C8B—C9B110.8 (6)
C8A—C7A—H7AA108.6C26B—C8B—C14B113.0 (6)
C8A—C7A—H7AB108.6C8B—C9B—H9B105.0
C7A—C8A—C9A111.1 (6)C8B—C9B—C10B116.3 (6)
C7A—C8A—C14A110.3 (6)C10B—C9B—H9B105.0
C7A—C8A—C26A105.2 (6)C11B—C9B—C8B110.2 (6)
C9A—C8A—C14A107.4 (6)C11B—C9B—H9B105.0
C26A—C8A—C9A110.1 (6)C11B—C9B—C10B114.0 (6)
C26A—C8A—C14A112.9 (6)C1B—C10B—C5B106.5 (6)
C8A—C9A—H9A104.2C1B—C10B—C9B109.1 (6)
C10A—C9A—C8A117.7 (6)C1B—C10B—C25B107.2 (6)
C10A—C9A—H9A104.2C5B—C10B—C9B107.3 (5)
C11A—C9A—C8A110.1 (6)C25B—C10B—C5B114.8 (6)
C11A—C9A—H9A104.2C25B—C10B—C9B111.7 (6)
C11A—C9A—C10A114.8 (6)C9B—C11B—H11E108.7
C1A—C10A—C9A108.6 (6)C9B—C11B—H11F108.7
C1A—C10A—C25A107.0 (6)H11E—C11B—H11F107.6
C5A—C10A—C1A107.6 (6)C12B—C11B—C9B114.3 (6)
C5A—C10A—C9A107.5 (6)C12B—C11B—H11E108.7
C5A—C10A—C25A114.2 (6)C12B—C11B—H11F108.7
C25A—C10A—C9A111.8 (6)F1B—C12B—C11B107.0 (7)
C9A—C11A—H11A108.3F1B—C12B—H12B108.8
C9A—C11A—H11B108.3F1B—C12B—C13B106.8 (6)
H11A—C11A—H11B107.4C11B—C12B—H12B108.8
C12A—C11A—C9A115.8 (6)C11B—C12B—C13B116.4 (7)
C12A—C11A—H11A108.3C13B—C12B—H12B108.8
C12A—C11A—H11B108.3O1B—C13B—C12B104.9 (6)
F1A—C12A—C11A106.6 (6)O1B—C13B—C14B107.3 (6)
F1A—C12A—H12A109.4O1B—C13B—C18B98.4 (6)
F1A—C12A—C13A106.1 (6)C12B—C13B—C14B113.7 (6)
C11A—C12A—H12A109.4C12B—C13B—C18B112.3 (6)
C11A—C12A—C13A115.7 (6)C14B—C13B—C18B118.1 (6)
C13A—C12A—H12A109.4C13B—C14B—C8B111.0 (6)
O1A—C13A—C12A102.9 (6)C13B—C14B—C15B107.9 (6)
O1A—C13A—C14A107.5 (6)C13B—C14B—C27B108.6 (6)
O1A—C13A—C18A98.8 (6)C15B—C14B—C8B111.1 (6)
C12A—C13A—C14A115.2 (6)C15B—C14B—C27B106.7 (6)
C12A—C13A—C18A113.4 (6)C27B—C14B—C8B111.3 (6)
C18A—C13A—C14A116.3 (6)C14B—C15B—H15E108.6
C13A—C14A—C8A111.0 (6)C14B—C15B—H15F108.6
C13A—C14A—C27A107.6 (6)H15E—C15B—H15F107.6
C15A—C14A—C8A111.1 (6)C16B—C15B—C14B114.5 (6)
C15A—C14A—C13A108.4 (6)C16B—C15B—H15E108.6
C15A—C14A—C27A107.8 (6)C16B—C15B—H15F108.6
C27A—C14A—C8A110.8 (6)C15B—C16B—H16E109.0
C14A—C15A—H15A108.7C15B—C16B—H16F109.0
C14A—C15A—H15B108.7C15B—C16B—C17B112.8 (6)
H15A—C15A—H15B107.6H16E—C16B—H16F107.8
C16A—C15A—C14A114.1 (6)C17B—C16B—H16E109.0
C16A—C15A—H15A108.7C17B—C16B—H16F109.0
C16A—C15A—H15B108.7C18B—C17B—C16B109.0 (6)
C15A—C16A—H16A108.8C22B—C17B—C16B113.1 (7)
C15A—C16A—H16B108.8C22B—C17B—C18B112.5 (6)
C15A—C16A—C17A114.0 (6)C22B—C17B—C28B115.8 (7)
H16A—C16A—H16B107.7C28B—C17B—C16B107.3 (7)
C17A—C16A—H16A108.8C28B—C17B—C18B98.0 (6)
C17A—C16A—H16B108.8C13B—C18B—H18B105.2
C18A—C17A—C16A110.5 (6)C17B—C18B—C13B99.3 (6)
C18A—C17A—C28A99.3 (6)C17B—C18B—H18B105.2
C22A—C17A—C16A114.6 (6)C19B—C18B—C13B127.8 (7)
C22A—C17A—C18A111.1 (6)C19B—C18B—C17B112.2 (6)
C22A—C17A—C28A114.8 (6)C19B—C18B—H18B105.2
C28A—C17A—C16A105.3 (6)C18B—C19B—H19E109.7
C13A—C18A—H18A105.5C18B—C19B—H19F109.7
C17A—C18A—C13A99.9 (6)C18B—C19B—C20B109.7 (6)
C17A—C18A—H18A105.5H19E—C19B—H19F108.2
C17A—C18A—C19A111.8 (6)C20B—C19B—H19E109.7
C19A—C18A—C13A126.8 (7)C20B—C19B—H19F109.7
C19A—C18A—H18A105.5C21B—C20B—C19B109.9 (6)
C18A—C19A—H19A109.7C29B—C20B—C19B112.0 (6)
C18A—C19A—H19B109.7C29B—C20B—C21B108.8 (7)
C18A—C19A—C20A110.0 (7)C30B—C20B—C19B108.1 (6)
H19A—C19A—H19B108.2C30B—C20B—C21B109.1 (7)
C20A—C19A—H19A109.7C30B—C20B—C29B108.8 (7)
C20A—C19A—H19B109.7C20B—C21B—H21E108.8
C19A—C20A—C30A107.9 (8)C20B—C21B—H21F108.8
C21A—C20A—C19A110.1 (7)H21E—C21B—H21F107.7
C21A—C20A—C29A110.5 (8)C22B—C21B—C20B113.9 (6)
C21A—C20A—C30A108.3 (7)C22B—C21B—H21E108.8
C29A—C20A—C19A111.4 (7)C22B—C21B—H21F108.8
C29A—C20A—C30A108.6 (8)C17B—C22B—C21B111.8 (7)
C20A—C21A—H21A108.8C17B—C22B—H22E109.3
C20A—C21A—H21B108.9C17B—C22B—H22F109.3
C20A—C21A—C22A113.6 (7)C21B—C22B—H22E109.3
H21A—C21A—H21B107.7C21B—C22B—H22F109.3
C22A—C21A—H21A108.9H22E—C22B—H22F107.9
C22A—C21A—H21B108.9C4B—C23B—H23G109.5
C17A—C22A—C21A110.4 (6)C4B—C23B—H23H109.5
C17A—C22A—H22A109.6C4B—C23B—H23I109.5
C17A—C22A—H22B109.6H23G—C23B—H23H109.5
C21A—C22A—H22A109.6H23G—C23B—H23I109.5
C21A—C22A—H22B109.6H23H—C23B—H23I109.5
H22A—C22A—H22B108.1C4B—C24B—H24G109.5
C4A—C23A—H23A109.5C4B—C24B—H24H109.5
C4A—C23A—H23B109.5C4B—C24B—H24I109.5
C4A—C23A—H23C109.5H24G—C24B—H24H109.5
H23A—C23A—H23B109.5H24G—C24B—H24I109.5
H23A—C23A—H23C109.5H24H—C24B—H24I109.5
H23B—C23A—H23C109.5C10B—C25B—H25G109.5
C4A—C24A—H24A109.5C10B—C25B—H25H109.5
C4A—C24A—H24B109.5C10B—C25B—H25I109.5
C4A—C24A—H24C109.5H25G—C25B—H25H109.5
H24A—C24A—H24B109.5H25G—C25B—H25I109.5
H24A—C24A—H24C109.5H25H—C25B—H25I109.5
H24B—C24A—H24C109.5C8B—C26B—H26G109.5
C10A—C25A—H25A109.5C8B—C26B—H26H109.5
C10A—C25A—H25B109.5C8B—C26B—H26I109.5
C10A—C25A—H25C109.5H26G—C26B—H26H109.5
H25A—C25A—H25B109.5H26G—C26B—H26I109.5
H25A—C25A—H25C109.5H26H—C26B—H26I109.5
H25B—C25A—H25C109.5C14B—C27B—H27G109.5
C8A—C26A—H26A109.5C14B—C27B—H27H109.5
C8A—C26A—H26B109.5C14B—C27B—H27I109.5
C8A—C26A—H26C109.5H27G—C27B—H27H109.5
H26A—C26A—H26B109.5H27G—C27B—H27I109.5
H26A—C26A—H26C109.5H27H—C27B—H27I109.5
H26B—C26A—H26C109.5O1B—C28B—C17B110.4 (6)
C14A—C27A—H27A109.5O2B—C28B—O1B120.4 (8)
C14A—C27A—H27B109.5O2B—C28B—C17B129.2 (9)
C14A—C27A—H27C109.5C20B—C29B—H29G109.5
H27A—C27A—H27B109.5C20B—C29B—H29H109.5
H27A—C27A—H27C109.5C20B—C29B—H29I109.5
H27B—C27A—H27C109.5H29G—C29B—H29H109.5
O1A—C28A—C17A108.0 (6)H29G—C29B—H29I109.5
O2A—C28A—O1A121.4 (8)H29H—C29B—H29I109.5
O2A—C28A—C17A130.6 (7)C20B—C30B—H30G109.5
C20A—C29A—H29A109.5C20B—C30B—H30H109.5
C20A—C29A—H29B109.5C20B—C30B—H30I109.5
C20A—C29A—H29C109.5H30G—C30B—H30H109.5
H29A—C29A—H29B109.5H30G—C30B—H30I109.5
H29A—C29A—H29C109.5H30H—C30B—H30I109.5
H29B—C29A—H29C109.5C28C—O1C—C13C109.1 (6)
C20A—C30A—H30A109.5C3C—O3C—H3C109.6
C20A—C30A—H30B109.5H1CA—C1C—H1CB107.7
C20A—C30A—H30C109.5C2C—C1C—H1CA108.8
H30A—C30A—H30B109.5C2C—C1C—H1CB108.8
H30A—C30A—H30C109.5C2C—C1C—C10C113.9 (6)
H30B—C30A—H30C109.5C10C—C1C—H1CA108.8
C28D—O1D—C13D109.6 (6)C10C—C1C—H1CB108.8
C3D—O3D—H3D109.5C1C—C2C—H2CA109.3
H1DA—C1D—H1DB107.9C1C—C2C—H2CB109.3
C2D—C1D—H1DA109.1C1C—C2C—C3C111.4 (6)
C2D—C1D—H1DB109.1H2CA—C2C—H2CB108.0
C2D—C1D—C10D112.4 (6)C3C—C2C—H2CA109.3
C10D—C1D—H1DA109.1C3C—C2C—H2CB109.3
C10D—C1D—H1DB109.1O3C—C3C—C2C111.1 (7)
C1D—C2D—H2DA109.1O3C—C3C—H3CA107.9
C1D—C2D—H2DB109.1O3C—C3C—C4C109.2 (6)
H2DA—C2D—H2DB107.8C2C—C3C—H3CA107.9
C3D—C2D—C1D112.5 (7)C4C—C3C—C2C112.8 (6)
C3D—C2D—H2DA109.1C4C—C3C—H3CA107.9
C3D—C2D—H2DB109.1C3C—C4C—C5C108.9 (6)
O3D—C3D—C2D112.3 (7)C3C—C4C—C24C110.9 (6)
O3D—C3D—H3DA106.2C23C—C4C—C3C107.8 (6)
O3D—C3D—C4D112.6 (6)C23C—C4C—C5C109.0 (6)
C2D—C3D—H3DA106.2C23C—C4C—C24C107.2 (7)
C2D—C3D—C4D112.8 (7)C24C—C4C—C5C113.0 (6)
C4D—C3D—H3DA106.2C4C—C5C—H5C104.6
C5D—C4D—C3D108.4 (6)C4C—C5C—C10C116.3 (6)
C5D—C4D—C23D108.9 (7)C6C—C5C—C4C114.1 (6)
C5D—C4D—C24D115.0 (7)C6C—C5C—H5C104.6
C23D—C4D—C3D106.3 (7)C6C—C5C—C10C111.2 (6)
C23D—C4D—C24D106.6 (7)C10C—C5C—H5C104.6
C24D—C4D—C3D111.3 (7)C5C—C6C—H6CA109.3
C4D—C5D—H5D104.5C5C—C6C—H6CB109.3
C4D—C5D—C10D117.2 (6)H6CA—C6C—H6CB107.9
C6D—C5D—C4D114.4 (6)C7C—C6C—C5C111.8 (6)
C6D—C5D—H5D104.5C7C—C6C—H6CA109.3
C6D—C5D—C10D110.2 (6)C7C—C6C—H6CB109.3
C10D—C5D—H5D104.5C6C—C7C—H7CA108.7
C5D—C6D—H6DA109.3C6C—C7C—H7CB108.7
C5D—C6D—H6DB109.3C6C—C7C—C8C114.0 (6)
H6DA—C6D—H6DB107.9H7CA—C7C—H7CB107.6
C7D—C6D—C5D111.7 (6)C8C—C7C—H7CA108.7
C7D—C6D—H6DA109.3C8C—C7C—H7CB108.7
C7D—C6D—H6DB109.3C7C—C8C—C9C110.1 (6)
C6D—C7D—H7DA108.7C7C—C8C—C14C109.6 (6)
C6D—C7D—H7DB108.7C7C—C8C—C26C105.7 (6)
C6D—C7D—C8D114.1 (6)C9C—C8C—C14C106.4 (6)
H7DA—C7D—H7DB107.6C26C—C8C—C9C111.7 (6)
C8D—C7D—H7DA108.7C26C—C8C—C14C113.5 (6)
C8D—C7D—H7DB108.7C8C—C9C—H9C105.7
C7D—C8D—C9D111.5 (6)C10C—C9C—C8C116.3 (6)
C7D—C8D—C14D110.0 (6)C10C—C9C—H9C105.7
C7D—C8D—C26D105.7 (6)C11C—C9C—C8C109.0 (6)
C9D—C8D—C14D106.9 (5)C11C—C9C—H9C105.7
C26D—C8D—C9D109.9 (6)C11C—C9C—C10C113.7 (6)
C26D—C8D—C14D112.9 (6)C1C—C10C—C5C106.6 (5)
C8D—C9D—H9D104.3C1C—C10C—C9C108.8 (6)
C10D—C9D—C8D117.7 (6)C1C—C10C—C25C107.4 (6)
C10D—C9D—H9D104.3C9C—C10C—C5C106.2 (5)
C11D—C9D—C8D110.4 (6)C25C—C10C—C5C115.0 (6)
C11D—C9D—H9D104.3C25C—C10C—C9C112.5 (6)
C11D—C9D—C10D114.4 (6)C9C—C11C—H11G108.6
C5D—C10D—C1D107.9 (6)C9C—C11C—H11H108.6
C5D—C10D—C9D107.1 (6)H11G—C11C—H11H107.5
C9D—C10D—C1D108.0 (6)C12C—C11C—C9C114.9 (6)
C25D—C10D—C1D106.5 (7)C12C—C11C—H11G108.6
C25D—C10D—C5D115.1 (6)C12C—C11C—H11H108.6
C25D—C10D—C9D112.1 (6)F1C—C12C—C11C108.4 (6)
C9D—C11D—H11C108.9F1C—C12C—H12C108.5
C9D—C11D—H11D108.9F1C—C12C—C13C106.3 (6)
H11C—C11D—H11D107.7C11C—C12C—H12C108.5
C12D—C11D—C9D113.4 (7)C11C—C12C—C13C116.5 (6)
C12D—C11D—H11C108.9C13C—C12C—H12C108.5
C12D—C11D—H11D108.9O1C—C13C—C12C105.0 (6)
F1D—C12D—C11D107.5 (6)O1C—C13C—C14C107.1 (6)
F1D—C12D—H12D108.8O1C—C13C—C18C98.6 (6)
F1D—C12D—C13D106.1 (7)C12C—C13C—C14C113.1 (6)
C11D—C12D—H12D108.8C12C—C13C—C18C113.5 (6)
C11D—C12D—C13D116.5 (6)C18C—C13C—C14C117.4 (6)
C13D—C12D—H12D108.8C13C—C14C—C8C110.6 (6)
O1D—C13D—C12D102.6 (6)C13C—C14C—C15C108.2 (6)
O1D—C13D—C14D107.5 (6)C15C—C14C—C8C110.7 (6)
O1D—C13D—C18D98.4 (6)C27C—C14C—C8C111.7 (6)
C12D—C13D—C14D116.1 (6)C27C—C14C—C13C108.9 (6)
C12D—C13D—C18D113.4 (6)C27C—C14C—C15C106.6 (6)
C18D—C13D—C14D116.0 (6)C14C—C15C—H15G108.6
C13D—C14D—C8D110.6 (6)C14C—C15C—H15H108.6
C15D—C14D—C8D110.6 (6)H15G—C15C—H15H107.6
C15D—C14D—C13D108.7 (6)C16C—C15C—C14C114.5 (6)
C15D—C14D—C27D107.5 (7)C16C—C15C—H15G108.6
C27D—C14D—C8D110.4 (6)C16C—C15C—H15H108.6
C27D—C14D—C13D109.0 (6)C15C—C16C—H16G109.2
C14D—C15D—H15C108.5C15C—C16C—H16H109.2
C14D—C15D—H15D108.5C15C—C16C—C17C111.9 (6)
H15C—C15D—H15D107.5H16G—C16C—H16H107.9
C16D—C15D—C14D115.2 (6)C17C—C16C—H16G109.2
C16D—C15D—H15C108.5C17C—C16C—H16H109.2
C16D—C15D—H15D108.5C18C—C17C—C16C108.8 (6)
C15D—C16D—H16C109.0C22C—C17C—C16C112.3 (7)
C15D—C16D—H16D109.0C22C—C17C—C18C112.4 (7)
C15D—C16D—C17D113.1 (6)C22C—C17C—C28C115.4 (6)
H16C—C16D—H16D107.8C28C—C17C—C16C108.2 (7)
C17D—C16D—H16C109.0C28C—C17C—C18C98.9 (6)
C17D—C16D—H16D109.0C13C—C18C—H18C104.6
C18D—C17D—C16D110.2 (6)C17C—C18C—C13C99.6 (6)
C22D—C17D—C16D115.1 (6)C17C—C18C—H18C104.6
C22D—C17D—C18D110.8 (6)C17C—C18C—C19C113.3 (6)
C22D—C17D—C28D115.4 (7)C19C—C18C—C13C128.0 (6)
C28D—C17D—C16D105.0 (6)C19C—C18C—H18C104.6
C28D—C17D—C18D99.0 (6)C18C—C19C—H19G109.7
C13D—C18D—H18D105.9C18C—C19C—H19H109.7
C17D—C18D—C13D100.4 (6)C18C—C19C—C20C110.0 (6)
C17D—C18D—H18D105.9H19G—C19C—H19H108.2
C17D—C18D—C19D111.5 (6)C20C—C19C—H19G109.7
C19D—C18D—C13D125.9 (7)C20C—C19C—H19H109.7
C19D—C18D—H18D105.9C19C—C20C—C29C111.3 (6)
C18D—C19D—H19C109.7C21C—C20C—C19C110.2 (6)
C18D—C19D—H19D109.7C21C—C20C—C29C108.3 (6)
C18D—C19D—C20D110.0 (6)C30C—C20C—C19C109.2 (6)
H19C—C19D—H19D108.2C30C—C20C—C21C109.7 (7)
C20D—C19D—H19C109.7C30C—C20C—C29C108.1 (7)
C20D—C19D—H19D109.7C20C—C21C—H21G108.7
C21D—C20D—C19D110.8 (6)C20C—C21C—H21H108.7
C29D—C20D—C19D111.4 (7)H21G—C21C—H21H107.6
C29D—C20D—C21D111.4 (7)C22C—C21C—C20C114.3 (7)
C29D—C20D—C30D107.5 (7)C22C—C21C—H21G108.7
C30D—C20D—C19D107.5 (7)C22C—C21C—H21H108.7
C30D—C20D—C21D108.1 (7)C17C—C22C—C21C110.7 (6)
C20D—C21D—H21C108.7C17C—C22C—H22G109.5
C20D—C21D—H21D108.7C17C—C22C—H22H109.5
C20D—C21D—C22D114.3 (7)C21C—C22C—H22G109.5
H21C—C21D—H21D107.6C21C—C22C—H22H109.5
C22D—C21D—H21C108.7H22G—C22C—H22H108.1
C22D—C21D—H21D108.7C4C—C23C—H23J109.5
C17D—C22D—C21D110.0 (7)C4C—C23C—H23K109.5
C17D—C22D—H22C109.7C4C—C23C—H23L109.5
C17D—C22D—H22D109.7H23J—C23C—H23K109.5
C21D—C22D—H22C109.7H23J—C23C—H23L109.5
C21D—C22D—H22D109.7H23K—C23C—H23L109.5
H22C—C22D—H22D108.2C4C—C24C—H24J109.5
C4D—C23D—H23D109.5C4C—C24C—H24K109.5
C4D—C23D—H23E109.5C4C—C24C—H24L109.5
C4D—C23D—H23F109.5H24J—C24C—H24K109.5
H23D—C23D—H23E109.5H24J—C24C—H24L109.5
H23D—C23D—H23F109.5H24K—C24C—H24L109.5
H23E—C23D—H23F109.5C10C—C25C—H25J109.5
C4D—C24D—H24D109.5C10C—C25C—H25K109.5
C4D—C24D—H24E109.5C10C—C25C—H25L109.5
C4D—C24D—H24F109.5H25J—C25C—H25K109.5
H24D—C24D—H24E109.5H25J—C25C—H25L109.5
H24D—C24D—H24F109.5H25K—C25C—H25L109.5
H24E—C24D—H24F109.5C8C—C26C—H26J109.5
C10D—C25D—H25D109.5C8C—C26C—H26K109.5
C10D—C25D—H25E109.5C8C—C26C—H26L109.5
C10D—C25D—H25F109.5H26J—C26C—H26K109.5
H25D—C25D—H25E109.5H26J—C26C—H26L109.5
H25D—C25D—H25F109.5H26K—C26C—H26L109.5
H25E—C25D—H25F109.5C14C—C27C—H27J109.5
C8D—C26D—H26D109.5C14C—C27C—H27K109.5
C8D—C26D—H26E109.5C14C—C27C—H27L109.5
C8D—C26D—H26F109.5H27J—C27C—H27K109.5
H26D—C26D—H26E109.5H27J—C27C—H27L109.5
H26D—C26D—H26F109.5H27K—C27C—H27L109.5
H26E—C26D—H26F109.5O1C—C28C—C17C108.9 (6)
C14D—C27D—H27D109.5O2C—C28C—O1C121.8 (8)
C14D—C27D—H27E109.5O2C—C28C—C17C129.3 (8)
C14D—C27D—H27F109.5C20C—C29C—H29J109.5
H27D—C27D—H27E109.5C20C—C29C—H29K109.5
H27D—C27D—H27F109.5C20C—C29C—H29L109.5
H27E—C27D—H27F109.5H29J—C29C—H29K109.5
O1D—C28D—C17D109.2 (6)H29J—C29C—H29L109.5
O2D—C28D—O1D121.6 (7)H29K—C29C—H29L109.5
O2D—C28D—C17D129.2 (7)C20C—C30C—H30J109.5
C20D—C29D—H29D109.5C20C—C30C—H30K109.5
C20D—C29D—H29E109.5C20C—C30C—H30L109.5
C20D—C29D—H29F109.5H30J—C30C—H30K109.5
H29D—C29D—H29E109.5H30J—C30C—H30L109.5
H29D—C29D—H29F109.5H30K—C30C—H30L109.5
F1A—C12A—C13A—O1A162.2 (6)F1B—C12B—C13B—O1B164.5 (6)
F1A—C12A—C13A—C14A−81.1 (8)F1B—C12B—C13B—C14B−78.7 (8)
F1A—C12A—C13A—C18A56.5 (8)F1B—C12B—C13B—C18B58.7 (8)
O1A—C13A—C14A—C8A67.9 (7)O1B—C13B—C14B—C8B66.1 (7)
O1A—C13A—C14A—C15A−54.4 (7)O1B—C13B—C14B—C15B−55.9 (7)
O1A—C13A—C14A—C27A−170.8 (5)O1B—C13B—C14B—C27B−171.2 (6)
O1A—C13A—C18A—C17A47.2 (6)O1B—C13B—C18B—C17B47.7 (6)
O1A—C13A—C18A—C19A174.2 (7)O1B—C13B—C18B—C19B175.3 (7)
O3A—C3A—C4A—C5A−179.9 (6)O3B—C3B—C4B—C5B−177.0 (6)
O3A—C3A—C4A—C23A62.4 (8)O3B—C3B—C4B—C23B66.4 (8)
O3A—C3A—C4A—C24A−52.7 (9)O3B—C3B—C4B—C24B−50.5 (8)
C1A—C2A—C3A—O3A−175.0 (6)C1B—C2B—C3B—O3B178.5 (6)
C1A—C2A—C3A—C4A57.8 (9)C1B—C2B—C3B—C4B54.3 (9)
C2A—C1A—C10A—C5A51.6 (8)C2B—C1B—C10B—C5B53.6 (8)
C2A—C1A—C10A—C9A167.6 (6)C2B—C1B—C10B—C9B169.2 (6)
C2A—C1A—C10A—C25A−71.6 (8)C2B—C1B—C10B—C25B−69.7 (8)
C2A—C3A—C4A—C5A−52.3 (8)C2B—C3B—C4B—C5B−51.5 (8)
C2A—C3A—C4A—C23A−170.0 (7)C2B—C3B—C4B—C23B−168.1 (7)
C2A—C3A—C4A—C24A74.9 (9)C2B—C3B—C4B—C24B75.0 (8)
C3A—C4A—C5A—C6A−175.7 (7)C3B—C4B—C5B—C6B−175.8 (6)
C3A—C4A—C5A—C10A52.2 (9)C3B—C4B—C5B—C10B53.9 (8)
C4A—C5A—C6A—C7A162.3 (7)C4B—C5B—C6B—C7B165.3 (6)
C4A—C5A—C10A—C1A−51.6 (9)C4B—C5B—C10B—C1B−53.6 (7)
C4A—C5A—C10A—C9A−168.4 (6)C4B—C5B—C10B—C9B−170.3 (6)
C4A—C5A—C10A—C25A67.0 (8)C4B—C5B—C10B—C25B64.8 (8)
C5A—C6A—C7A—C8A54.2 (9)C5B—C6B—C7B—C8B56.5 (8)
C6A—C5A—C10A—C1A174.9 (6)C6B—C5B—C10B—C1B174.5 (6)
C6A—C5A—C10A—C9A58.1 (8)C6B—C5B—C10B—C9B57.8 (7)
C6A—C5A—C10A—C25A−66.5 (8)C6B—C5B—C10B—C25B−67.0 (8)
C6A—C7A—C8A—C9A−43.3 (9)C6B—C7B—C8B—C9B−47.4 (8)
C6A—C7A—C8A—C14A−162.3 (7)C6B—C7B—C8B—C14B−165.5 (6)
C6A—C7A—C8A—C26A75.7 (8)C6B—C7B—C8B—C26B72.3 (8)
C7A—C8A—C9A—C10A43.1 (9)C7B—C8B—C9B—C10B46.8 (8)
C7A—C8A—C9A—C11A177.2 (7)C7B—C8B—C9B—C11B178.6 (6)
C7A—C8A—C14A—C13A179.5 (6)C7B—C8B—C14B—C13B179.8 (6)
C7A—C8A—C14A—C15A−59.8 (8)C7B—C8B—C14B—C15B−60.2 (8)
C7A—C8A—C14A—C27A60.0 (8)C7B—C8B—C14B—C27B58.7 (7)
C8A—C9A—C10A—C1A−166.7 (6)C8B—C9B—C10B—C1B−167.0 (6)
C8A—C9A—C10A—C5A−50.7 (8)C8B—C9B—C10B—C5B−52.0 (8)
C8A—C9A—C10A—C25A75.4 (8)C8B—C9B—C10B—C25B74.7 (8)
C8A—C9A—C11A—C12A54.8 (8)C8B—C9B—C11B—C12B54.1 (9)
C8A—C14A—C15A—C16A−162.0 (7)C8B—C14B—C15B—C16B−161.7 (6)
C9A—C8A—C14A—C13A58.3 (7)C9B—C8B—C14B—C13B59.8 (7)
C9A—C8A—C14A—C15A179.0 (6)C9B—C8B—C14B—C15B179.9 (6)
C9A—C8A—C14A—C27A−61.1 (7)C9B—C8B—C14B—C27B−61.3 (7)
C9A—C11A—C12A—F1A76.5 (7)C9B—C11B—C12B—F1B76.2 (8)
C9A—C11A—C12A—C13A−41.2 (9)C9B—C11B—C12B—C13B−43.1 (10)
C10A—C1A—C2A—C3A−57.9 (9)C10B—C1B—C2B—C3B−56.4 (8)
C10A—C5A—C6A—C7A−62.0 (9)C10B—C5B—C6B—C7B−61.8 (8)
C10A—C9A—C11A—C12A−169.7 (6)C10B—C9B—C11B—C12B−173.0 (7)
C11A—C9A—C10A—C1A61.3 (8)C11B—C9B—C10B—C1B63.0 (8)
C11A—C9A—C10A—C5A177.3 (6)C11B—C9B—C10B—C5B178.0 (6)
C11A—C9A—C10A—C25A−56.6 (8)C11B—C9B—C10B—C25B−55.3 (8)
C11A—C12A—C13A—O1A−79.9 (8)C11B—C12B—C13B—O1B−76.2 (8)
C11A—C12A—C13A—C14A36.8 (9)C11B—C12B—C13B—C14B40.7 (10)
C11A—C12A—C13A—C18A174.4 (6)C11B—C12B—C13B—C18B178.0 (7)
C12A—C13A—C14A—C8A−46.2 (8)C12B—C13B—C14B—C8B−49.4 (8)
C12A—C13A—C14A—C15A−168.5 (6)C12B—C13B—C14B—C15B−171.4 (6)
C12A—C13A—C14A—C27A75.1 (8)C12B—C13B—C14B—C27B73.2 (8)
C12A—C13A—C18A—C17A155.5 (6)C12B—C13B—C18B—C17B157.6 (6)
C12A—C13A—C18A—C19A−77.5 (9)C12B—C13B—C18B—C19B−74.8 (9)
C13A—O1A—C28A—O2A−176.9 (8)C13B—O1B—C28B—O2B−175.1 (8)
C13A—O1A—C28A—C17A4.7 (8)C13B—O1B—C28B—C17B4.2 (9)
C13A—C14A—C15A—C16A−39.8 (9)C13B—C14B—C15B—C16B−39.8 (8)
C13A—C18A—C19A—C20A−179.4 (6)C13B—C18B—C19B—C20B−179.1 (7)
C14A—C8A—C9A—C10A163.8 (6)C14B—C8B—C9B—C10B166.6 (6)
C14A—C8A—C9A—C11A−62.1 (8)C14B—C8B—C9B—C11B−61.7 (7)
C14A—C13A—C18A—C17A−67.5 (8)C14B—C13B—C18B—C17B−67.1 (8)
C14A—C13A—C18A—C19A59.5 (9)C14B—C13B—C18B—C19B60.5 (10)
C14A—C15A—C16A—C17A44.7 (9)C14B—C15B—C16B—C17B47.3 (9)
C15A—C16A—C17A—C18A−60.8 (9)C15B—C16B—C17B—C18B−63.5 (8)
C15A—C16A—C17A—C22A172.8 (6)C15B—C16B—C17B—C22B170.6 (6)
C15A—C16A—C17A—C28A45.6 (8)C15B—C16B—C17B—C28B41.6 (9)
C16A—C17A—C18A—C13A66.2 (8)C16B—C17B—C18B—C13B66.8 (7)
C16A—C17A—C18A—C19A−70.3 (8)C16B—C17B—C18B—C19B−70.7 (8)
C16A—C17A—C22A—C21A71.0 (8)C16B—C17B—C22B—C21B72.2 (9)
C16A—C17A—C28A—O1A−88.5 (7)C16B—C17B—C28B—O1B−86.3 (8)
C16A—C17A—C28A—O2A93.2 (11)C16B—C17B—C28B—O2B92.9 (11)
C17A—C18A—C19A—C20A−57.3 (8)C17B—C18B—C19B—C20B−56.6 (8)
C18A—C13A—C14A—C8A177.5 (6)C18B—C13B—C14B—C8B175.9 (6)
C18A—C13A—C14A—C15A55.2 (8)C18B—C13B—C14B—C15B53.9 (8)
C18A—C13A—C14A—C27A−61.2 (8)C18B—C13B—C14B—C27B−61.4 (8)
C18A—C17A—C22A—C21A−55.1 (9)C18B—C17B—C22B—C21B−51.8 (9)
C18A—C17A—C28A—O1A25.9 (8)C18B—C17B—C28B—O1B26.5 (8)
C18A—C17A—C28A—O2A−152.4 (10)C18B—C17B—C28B—O2B−154.3 (10)
C18A—C19A—C20A—C21A54.2 (9)C18B—C19B—C20B—C21B54.9 (8)
C18A—C19A—C20A—C29A−68.7 (9)C18B—C19B—C20B—C29B−66.2 (8)
C18A—C19A—C20A—C30A172.2 (7)C18B—C19B—C20B—C30B173.9 (7)
C19A—C20A—C21A—C22A−54.1 (10)C19B—C20B—C21B—C22B−53.7 (9)
C20A—C21A—C22A—C17A54.4 (9)C20B—C21B—C22B—C17B52.1 (9)
C22A—C17A—C18A—C13A−165.5 (6)C22B—C17B—C18B—C13B−166.9 (6)
C22A—C17A—C18A—C19A58.1 (9)C22B—C17B—C18B—C19B55.6 (8)
C22A—C17A—C28A—O1A144.5 (6)C22B—C17B—C28B—O1B146.3 (7)
C22A—C17A—C28A—O2A−33.8 (13)C22B—C17B—C28B—O2B−34.5 (13)
C23A—C4A—C5A—C6A−60.2 (9)C23B—C4B—C5B—C6B−59.8 (8)
C23A—C4A—C5A—C10A167.7 (7)C23B—C4B—C5B—C10B169.9 (6)
C24A—C4A—C5A—C6A60.1 (9)C24B—C4B—C5B—C6B59.2 (8)
C24A—C4A—C5A—C10A−72.0 (9)C24B—C4B—C5B—C10B−71.1 (8)
C26A—C8A—C9A—C10A−72.9 (8)C26B—C8B—C9B—C10B−69.7 (8)
C26A—C8A—C9A—C11A61.2 (8)C26B—C8B—C9B—C11B62.1 (8)
C26A—C8A—C14A—C13A−63.2 (7)C26B—C8B—C14B—C13B−62.6 (8)
C26A—C8A—C14A—C15A57.5 (8)C26B—C8B—C14B—C15B57.5 (8)
C26A—C8A—C14A—C27A177.4 (6)C26B—C8B—C14B—C27B176.3 (6)
C27A—C14A—C15A—C16A76.4 (8)C27B—C14B—C15B—C16B76.8 (8)
C28A—O1A—C13A—C12A−149.1 (6)C28B—O1B—C13B—C12B−148.7 (7)
C28A—O1A—C13A—C14A88.9 (7)C28B—O1B—C13B—C14B90.1 (7)
C28A—O1A—C13A—C18A−32.4 (7)C28B—O1B—C13B—C18B−32.9 (7)
C28A—C17A—C18A—C13A−44.2 (7)C28B—C17B—C18B—C13B−44.7 (7)
C28A—C17A—C18A—C19A179.4 (6)C28B—C17B—C18B—C19B177.8 (6)
C28A—C17A—C22A—C21A−166.9 (7)C28B—C17B—C22B—C21B−163.3 (7)
C29A—C20A—C21A—C22A69.3 (9)C29B—C20B—C21B—C22B69.3 (8)
C30A—C20A—C21A—C22A−171.8 (7)C30B—C20B—C21B—C22B−172.1 (7)
F1D—C12D—C13D—O1D161.7 (5)F1C—C12C—C13C—O1C163.8 (6)
F1D—C12D—C13D—C14D−81.3 (8)F1C—C12C—C13C—C14C−79.7 (8)
F1D—C12D—C13D—C18D56.7 (8)F1C—C12C—C13C—C18C57.3 (8)
O1D—C13D—C14D—C8D68.0 (7)O1C—C13C—C14C—C8C65.3 (7)
O1D—C13D—C14D—C15D−53.6 (8)O1C—C13C—C14C—C15C−56.1 (8)
O1D—C13D—C14D—C27D−170.5 (6)O1C—C13C—C14C—C27C−171.6 (6)
O1D—C13D—C18D—C17D46.1 (6)O1C—C13C—C18C—C17C47.3 (6)
O1D—C13D—C18D—C19D172.4 (6)O1C—C13C—C18C—C19C177.2 (7)
O3D—C3D—C4D—C5D179.0 (6)O3C—C3C—C4C—C5C−175.9 (6)
O3D—C3D—C4D—C23D62.1 (8)O3C—C3C—C4C—C23C66.0 (8)
O3D—C3D—C4D—C24D−53.6 (9)O3C—C3C—C4C—C24C−51.1 (8)
C1D—C2D—C3D—O3D−174.5 (6)C1C—C2C—C3C—O3C178.4 (6)
C1D—C2D—C3D—C4D57.0 (9)C1C—C2C—C3C—C4C55.4 (9)
C2D—C1D—C10D—C5D51.5 (8)C2C—C1C—C10C—C5C54.2 (8)
C2D—C1D—C10D—C9D166.9 (6)C2C—C1C—C10C—C9C168.4 (6)
C2D—C1D—C10D—C25D−72.6 (8)C2C—C1C—C10C—C25C−69.5 (7)
C2D—C3D—C4D—C5D−52.6 (8)C2C—C3C—C4C—C5C−51.9 (8)
C2D—C3D—C4D—C23D−169.6 (7)C2C—C3C—C4C—C23C−170.0 (7)
C2D—C3D—C4D—C24D74.8 (9)C2C—C3C—C4C—C24C72.9 (8)
C3D—C4D—C5D—C6D−176.3 (7)C3C—C4C—C5C—C6C−175.3 (6)
C3D—C4D—C5D—C10D52.4 (8)C3C—C4C—C5C—C10C53.2 (8)
C4D—C5D—C6D—C7D162.2 (6)C4C—C5C—C6C—C7C164.7 (6)
C4D—C5D—C10D—C1D−52.0 (9)C4C—C5C—C10C—C1C−53.4 (8)
C4D—C5D—C10D—C9D−168.0 (6)C4C—C5C—C10C—C9C−169.3 (6)
C4D—C5D—C10D—C25D66.7 (9)C4C—C5C—C10C—C25C65.6 (8)
C5D—C6D—C7D—C8D54.4 (9)C5C—C6C—C7C—C8C55.9 (8)
C6D—C5D—C10D—C1D174.8 (6)C6C—C5C—C10C—C1C173.8 (6)
C6D—C5D—C10D—C9D58.8 (8)C6C—C5C—C10C—C9C57.8 (7)
C6D—C5D—C10D—C25D−66.5 (9)C6C—C5C—C10C—C25C−67.3 (8)
C6D—C7D—C8D—C9D−42.7 (9)C6C—C7C—C8C—C9C−47.6 (8)
C6D—C7D—C8D—C14D−161.2 (6)C6C—C7C—C8C—C14C−164.4 (6)
C6D—C7D—C8D—C26D76.6 (8)C6C—C7C—C8C—C26C73.1 (8)
C7D—C8D—C9D—C10D42.9 (9)C7C—C8C—C9C—C10C48.5 (8)
C7D—C8D—C9D—C11D176.6 (6)C7C—C8C—C9C—C11C178.6 (6)
C7D—C8D—C14D—C13D179.3 (6)C7C—C8C—C14C—C13C−179.9 (6)
C7D—C8D—C14D—C15D−60.3 (8)C7C—C8C—C14C—C15C−59.9 (7)
C7D—C8D—C14D—C27D58.6 (8)C7C—C8C—C14C—C27C58.7 (7)
C8D—C9D—C10D—C1D−166.7 (6)C8C—C9C—C10C—C1C−167.4 (6)
C8D—C9D—C10D—C5D−50.7 (8)C8C—C9C—C10C—C5C−53.0 (7)
C8D—C9D—C10D—C25D76.3 (8)C8C—C9C—C10C—C25C73.6 (7)
C8D—C9D—C11D—C12D55.9 (8)C8C—C9C—C11C—C12C55.8 (8)
C8D—C14D—C15D—C16D−160.9 (7)C8C—C14C—C15C—C16C−162.0 (6)
C9D—C8D—C14D—C13D58.1 (8)C9C—C8C—C14C—C13C61.2 (7)
C9D—C8D—C14D—C15D178.5 (6)C9C—C8C—C14C—C15C−178.9 (5)
C9D—C8D—C14D—C27D−62.6 (7)C9C—C8C—C14C—C27C−60.3 (7)
C9D—C11D—C12D—F1D76.8 (7)C9C—C11C—C12C—F1C75.4 (8)
C9D—C11D—C12D—C13D−42.0 (10)C9C—C11C—C12C—C13C−44.3 (9)
C10D—C1D—C2D—C3D−56.5 (9)C10C—C1C—C2C—C3C−57.5 (8)
C10D—C5D—C6D—C7D−63.2 (9)C10C—C5C—C6C—C7C−61.4 (8)
C10D—C9D—C11D—C12D−168.7 (6)C10C—C9C—C11C—C12C−172.8 (6)
C11D—C9D—C10D—C1D61.4 (8)C11C—C9C—C10C—C1C64.8 (7)
C11D—C9D—C10D—C5D177.3 (6)C11C—C9C—C10C—C5C179.2 (6)
C11D—C9D—C10D—C25D−55.6 (8)C11C—C9C—C10C—C25C−54.1 (8)
C11D—C12D—C13D—O1D−78.7 (8)C11C—C12C—C13C—O1C−75.3 (7)
C11D—C12D—C13D—C14D38.3 (10)C11C—C12C—C13C—C14C41.1 (9)
C11D—C12D—C13D—C18D176.3 (7)C11C—C12C—C13C—C18C178.2 (6)
C12D—C13D—C14D—C8D−46.2 (9)C12C—C13C—C14C—C8C−49.9 (8)
C12D—C13D—C14D—C15D−167.8 (7)C12C—C13C—C14C—C15C−171.3 (6)
C12D—C13D—C14D—C27D75.3 (8)C12C—C13C—C14C—C27C73.2 (8)
C12D—C13D—C18D—C17D153.7 (6)C12C—C13C—C18C—C17C157.8 (6)
C12D—C13D—C18D—C19D−79.9 (9)C12C—C13C—C18C—C19C−72.3 (9)
C13D—O1D—C28D—O2D−174.1 (7)C13C—O1C—C28C—O2C−174.4 (8)
C13D—O1D—C28D—C17D4.8 (8)C13C—O1C—C28C—C17C3.8 (8)
C13D—C14D—C15D—C16D−39.4 (9)C13C—C14C—C15C—C16C−40.6 (9)
C13D—C18D—C19D—C20D−179.0 (6)C13C—C18C—C19C—C20C−179.6 (7)
C14D—C8D—C9D—C10D163.2 (6)C14C—C8C—C9C—C10C167.2 (5)
C14D—C8D—C9D—C11D−63.1 (8)C14C—C8C—C9C—C11C−62.8 (7)
C14D—C13D—C18D—C17D−68.2 (8)C14C—C13C—C18C—C17C−67.1 (7)
C14D—C13D—C18D—C19D58.1 (9)C14C—C13C—C18C—C19C62.8 (10)
C14D—C15D—C16D—C17D43.4 (10)C14C—C15C—C16C—C17C48.1 (9)
C15D—C16D—C17D—C18D−59.1 (9)C15C—C16C—C17C—C18C−64.6 (8)
C15D—C16D—C17D—C22D174.7 (6)C15C—C16C—C17C—C22C170.4 (6)
C15D—C16D—C17D—C28D46.7 (8)C15C—C16C—C17C—C28C41.8 (9)
C16D—C17D—C18D—C13D66.5 (7)C16C—C17C—C18C—C13C67.8 (7)
C16D—C17D—C18D—C19D−68.9 (8)C16C—C17C—C18C—C19C−71.0 (8)
C16D—C17D—C22D—C21D70.1 (8)C16C—C17C—C22C—C21C72.0 (9)
C16D—C17D—C28D—O1D−88.9 (7)C16C—C17C—C28C—O1C−86.4 (8)
C16D—C17D—C28D—O2D89.9 (10)C16C—C17C—C28C—O2C91.6 (11)
C17D—C18D—C19D—C20D−57.4 (8)C17C—C18C—C19C—C20C−55.2 (8)
C18D—C13D—C14D—C8D176.9 (6)C18C—C13C—C14C—C8C174.9 (6)
C18D—C13D—C14D—C15D55.3 (8)C18C—C13C—C14C—C15C53.5 (8)
C18D—C13D—C14D—C27D−61.6 (8)C18C—C13C—C14C—C27C−62.1 (8)
C18D—C17D—C22D—C21D−55.7 (8)C18C—C17C—C22C—C21C−51.1 (9)
C18D—C17D—C28D—O1D25.0 (7)C18C—C17C—C28C—O1C26.8 (8)
C18D—C17D—C28D—O2D−156.2 (8)C18C—C17C—C28C—O2C−155.2 (9)
C18D—C19D—C20D—C21D52.9 (8)C18C—C19C—C20C—C21C54.3 (8)
C18D—C19D—C20D—C29D−71.7 (8)C18C—C19C—C20C—C29C−65.9 (8)
C18D—C19D—C20D—C30D170.8 (7)C18C—C19C—C20C—C30C174.8 (6)
C19D—C20D—C21D—C22D−52.3 (9)C19C—C20C—C21C—C22C−55.2 (8)
C20D—C21D—C22D—C17D53.5 (9)C20C—C21C—C22C—C17C53.1 (9)
C22D—C17D—C18D—C13D−165.0 (6)C22C—C17C—C18C—C13C−167.2 (6)
C22D—C17D—C18D—C19D59.6 (8)C22C—C17C—C18C—C19C54.0 (8)
C22D—C17D—C28D—O1D143.3 (6)C22C—C17C—C28C—O1C146.8 (7)
C22D—C17D—C28D—O2D−37.9 (12)C22C—C17C—C28C—O2C−35.2 (13)
C23D—C4D—C5D—C6D−61.0 (9)C23C—C4C—C5C—C6C−58.0 (8)
C23D—C4D—C5D—C10D167.7 (7)C23C—C4C—C5C—C10C170.5 (6)
C24D—C4D—C5D—C6D58.5 (9)C24C—C4C—C5C—C6C61.1 (8)
C24D—C4D—C5D—C10D−72.8 (9)C24C—C4C—C5C—C10C−70.5 (8)
C26D—C8D—C9D—C10D−74.0 (8)C26C—C8C—C9C—C10C−68.5 (7)
C26D—C8D—C9D—C11D59.7 (8)C26C—C8C—C9C—C11C61.5 (8)
C26D—C8D—C14D—C13D−62.9 (8)C26C—C8C—C14C—C13C−62.0 (8)
C26D—C8D—C14D—C15D57.5 (8)C26C—C8C—C14C—C15C57.9 (8)
C26D—C8D—C14D—C27D176.4 (6)C26C—C8C—C14C—C27C176.5 (6)
C27D—C14D—C15D—C16D78.5 (8)C27C—C14C—C15C—C16C76.4 (8)
C28D—O1D—C13D—C12D−148.4 (6)C28C—O1C—C13C—C12C−149.5 (7)
C28D—O1D—C13D—C14D88.7 (7)C28C—O1C—C13C—C14C90.0 (7)
C28D—O1D—C13D—C18D−32.1 (7)C28C—O1C—C13C—C18C−32.2 (7)
C28D—C17D—C18D—C13D−43.3 (7)C28C—C17C—C18C—C13C−44.9 (6)
C28D—C17D—C18D—C19D−178.7 (6)C28C—C17C—C18C—C19C176.3 (6)
C28D—C17D—C22D—C21D−167.2 (7)C28C—C17C—C22C—C21C−163.4 (7)
C29D—C20D—C21D—C22D72.3 (9)C29C—C20C—C21C—C22C66.8 (8)
C30D—C20D—C21D—C22D−169.9 (7)C30C—C20C—C21C—C22C−175.4 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O13—H13···O3A0.821.932.720 (8)161
O14—H14···O3Di0.821.942.714 (9)157
O3A—H3A···O3Cii0.822.032.819 (8)163
O3D—H3D···O3Biii0.822.012.816 (8)166
O3B—H3B···O14iv0.822.012.715 (8)144
O3C—H3C···O13ii0.822.072.708 (9)135
Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, y+1/2, −z+1; (iii) −x, y+1/2, −z; (iv) −x+1, y−1/2, −z.
12-α-Fluoro-3β-hydroxytaraxer-28,14β-olide methanol hemisolvate (2) top
Crystal data top
2C30H47FO3·CH4ODx = 1.199 Mg m−3
Mr = 981.39Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, C2221Cell parameters from 8721 reflections
a = 6.6077 (2) Åθ = 4.5–70.2°
b = 13.8730 (4) ŵ = 0.64 mm−1
c = 59.326 (2) ÅT = 240 K
V = 5438.3 (3) Å3Block, clear light colourless
Z = 40.34 × 0.2 × 0.1 mm
F(000) = 2152
Data collection top
XtaLAB AFC11 (RINC): Kappa single
diffractometer		5184 independent reflections
Radiation source: Rotating-anode X-ray tube (dual wavelength), Rigaku (Cu) X-ray DW Source4937 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.059
Detector resolution: 10.0000 pixels mm-1θmax = 70.8°, θmin = 1.5°
ω scansh = −7→8
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2020)		k = −16→16
Tmin = 0.907, Tmax = 1.000l = −72→72
24920 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.073 w = 1/[σ2(Fo2) + (0.0838P)2 + 12.3803P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.203(Δ/σ)max < 0.001
S = 1.09Δρmax = 0.27 e Å−3
5184 reflectionsΔρmin = −0.28 e Å−3
328 parametersAbsolute structure: Refined as an inversion twin
0 restraintsAbsolute structure parameter: 0.5 (5)
Primary atom site location: structure-invariant direct methods
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
F10.2840 (7)0.0871 (2)0.60866 (5)0.0576 (10)
O10.0832 (6)0.3645 (3)0.59306 (6)0.0436 (8)
O2−0.0826 (7)0.3722 (4)0.56100 (7)0.0658 (13)
O30.6529 (8)0.3849 (3)0.73386 (7)0.0665 (13)
H3A0.5557850.4118290.7397520.100*0.5
H3B0.7735050.3805090.7374720.100*0.5
C10.4758 (9)0.2447 (4)0.68283 (9)0.0437 (12)
H1A0.4129550.1808990.6817260.052*
H1B0.6048460.2424510.6747150.052*
C20.5162 (11)0.2679 (4)0.70767 (9)0.0525 (14)
H2A0.3883980.2657050.7160370.063*
H2B0.6064850.2188550.7140210.063*
C30.6117 (9)0.3666 (4)0.71045 (9)0.0472 (13)
H30.7434710.3652170.7025090.057*
C40.4848 (9)0.4487 (4)0.69983 (9)0.0441 (12)
C50.4351 (8)0.4211 (3)0.67510 (8)0.0379 (11)
H50.5681050.4169610.6674750.045*
C60.3173 (11)0.4984 (4)0.66195 (9)0.0508 (14)
H6A0.1762140.4992080.6670360.061*
H6B0.3760970.5619180.6649670.061*
C70.3242 (10)0.4781 (4)0.63663 (9)0.0469 (13)
H7A0.4648190.4828640.6314830.056*
H7B0.2460820.5278040.6287670.056*
C80.2402 (8)0.3780 (3)0.63000 (8)0.0373 (11)
C90.3416 (8)0.3015 (3)0.64534 (8)0.0355 (10)
H90.493 (10)0.315 (4)0.6416 (9)0.043*
C100.3357 (8)0.3201 (3)0.67148 (8)0.0358 (10)
C110.2845 (9)0.1979 (4)0.63895 (9)0.0431 (12)
H11A0.3948750.1547610.6434210.052*
H11B0.1637790.1790760.6474910.052*
C120.2426 (9)0.1840 (4)0.61396 (8)0.0419 (12)
H120.0967720.1958860.6112980.050*
C130.3628 (7)0.2502 (4)0.59854 (8)0.0368 (10)
C140.2859 (7)0.3553 (4)0.60376 (8)0.0356 (10)
C150.4196 (9)0.4272 (3)0.59122 (9)0.0411 (11)
H15A0.5552150.4277290.5979020.049*
H15B0.3624010.4921090.5925960.049*
C160.4338 (9)0.3991 (4)0.56613 (9)0.0429 (12)
H16A0.5684120.3726340.5629800.051*
H16B0.4150980.4565350.5567560.051*
C170.2702 (8)0.3231 (4)0.56014 (9)0.0407 (11)
C180.3136 (8)0.2272 (3)0.57298 (8)0.0373 (10)
H180.1865240.1894740.5728170.045*
C190.4753 (9)0.1659 (4)0.56080 (9)0.0444 (12)
H19A0.6070200.1974580.5625580.053*
H19B0.4833750.1029410.5682240.053*
C200.4361 (10)0.1499 (4)0.53556 (9)0.0504 (14)
C210.4139 (10)0.2492 (4)0.52433 (9)0.0509 (13)
H21A0.5420270.2842950.5256760.061*
H21B0.3855690.2403180.5082490.061*
C220.2463 (10)0.3086 (5)0.53479 (9)0.0500 (13)
H22A0.1164990.2768300.5318850.060*
H22B0.2428060.3718810.5274450.060*
C230.6245 (14)0.5380 (5)0.69954 (11)0.071 (2)
H23A0.7312040.5285460.6885280.106*
H23B0.6838080.5469270.7143450.106*
H23C0.5461240.5946120.6955470.106*
C240.3007 (12)0.4738 (5)0.71449 (10)0.0593 (17)
H24A0.2090240.5145910.7060020.089*
H24B0.3454520.5077310.7278970.089*
H24C0.2314650.4150520.7188410.089*
C250.1217 (8)0.3094 (5)0.68184 (9)0.0474 (13)
H25A0.1333050.2881530.6973620.071*
H25B0.0451360.2622550.6732830.071*
H25C0.0525510.3710390.6813520.071*
C260.0101 (9)0.3819 (5)0.63399 (10)0.0543 (15)
H26A−0.0478270.3185910.6314110.081*
H26B−0.0504520.4278690.6236780.081*
H26C−0.0164720.4016760.6493890.081*
C270.5939 (8)0.2380 (4)0.60303 (9)0.0411 (11)
H27A0.6695690.2781130.5926180.062*
H27B0.6316460.1710740.6008960.062*
H27C0.6243310.2572900.6183820.062*
C280.0753 (8)0.3567 (4)0.57053 (9)0.0431 (12)
C290.2449 (13)0.0879 (5)0.53177 (11)0.0668 (19)
H29A0.2645190.0247980.5384760.100*
H29B0.2208220.0808230.5157260.100*
H29C0.1293510.1190890.5387260.100*
C300.6189 (14)0.0987 (6)0.52549 (12)0.077 (2)
H30A0.7386130.1382080.5275680.115*
H30B0.5966670.0881490.5095150.115*
H30C0.6379470.0371830.5329610.115*
O40.0000000.3097 (5)0.7500000.091 (2)
H40.1170000.3294340.7498900.136*0.5
C310.0000000.2096 (7)0.7500000.071 (3)
H31A0.0370800.1865690.7353100.085*0.5
H31B−0.1327400.1865690.7537700.085*0.5
H31C0.0956600.1865690.7609200.085*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.087 (3)0.0345 (15)0.0507 (18)−0.0143 (17)−0.0015 (17)0.0007 (13)
O10.0282 (17)0.055 (2)0.0472 (19)0.0035 (16)−0.0022 (15)0.0099 (16)
O20.039 (2)0.106 (4)0.053 (2)0.011 (2)−0.0054 (19)0.012 (2)
O30.083 (3)0.071 (3)0.046 (2)0.005 (3)−0.013 (2)−0.009 (2)
C10.053 (3)0.034 (2)0.045 (3)0.004 (2)0.000 (2)0.003 (2)
C20.065 (4)0.050 (3)0.043 (3)0.015 (3)−0.005 (3)0.005 (2)
C30.041 (3)0.061 (3)0.040 (3)0.002 (3)0.000 (2)−0.005 (2)
C40.049 (3)0.043 (3)0.041 (3)−0.002 (2)0.005 (2)−0.002 (2)
C50.041 (3)0.032 (2)0.041 (3)0.000 (2)0.007 (2)0.0018 (19)
C60.076 (4)0.032 (2)0.045 (3)0.001 (3)0.003 (3)0.004 (2)
C70.068 (4)0.028 (2)0.045 (3)0.004 (2)0.000 (3)0.005 (2)
C80.033 (3)0.037 (2)0.042 (3)0.004 (2)−0.002 (2)0.006 (2)
C90.035 (3)0.029 (2)0.042 (2)−0.0049 (19)0.002 (2)0.0055 (19)
C100.038 (3)0.028 (2)0.042 (2)−0.0011 (19)0.000 (2)0.0054 (18)
C110.049 (3)0.035 (2)0.046 (3)−0.004 (2)0.002 (2)0.005 (2)
C120.048 (3)0.035 (2)0.043 (3)−0.012 (2)0.000 (2)0.005 (2)
C130.034 (3)0.036 (2)0.040 (3)−0.003 (2)−0.0015 (19)0.0046 (19)
C140.029 (2)0.037 (2)0.041 (2)−0.002 (2)−0.0042 (19)0.006 (2)
C150.040 (3)0.033 (2)0.050 (3)−0.005 (2)0.001 (2)0.008 (2)
C160.043 (3)0.043 (3)0.043 (3)−0.005 (2)0.003 (2)0.012 (2)
C170.035 (3)0.044 (3)0.044 (3)0.002 (2)−0.002 (2)0.007 (2)
C180.033 (2)0.038 (2)0.041 (3)0.002 (2)0.000 (2)0.005 (2)
C190.046 (3)0.044 (3)0.043 (3)0.011 (2)−0.002 (2)0.006 (2)
C200.062 (4)0.048 (3)0.042 (3)0.009 (3)0.000 (3)0.003 (2)
C210.062 (4)0.052 (3)0.039 (3)0.002 (3)0.004 (3)0.004 (2)
C220.048 (3)0.057 (3)0.046 (3)0.009 (3)−0.001 (3)0.007 (2)
C230.099 (6)0.058 (4)0.056 (4)−0.027 (4)−0.001 (4)−0.009 (3)
C240.081 (5)0.053 (3)0.044 (3)0.019 (3)0.008 (3)−0.004 (3)
C250.037 (3)0.060 (3)0.045 (3)−0.005 (3)0.005 (2)0.006 (2)
C260.043 (3)0.074 (4)0.045 (3)0.013 (3)0.005 (2)0.005 (3)
C270.031 (2)0.050 (3)0.043 (3)0.003 (2)−0.004 (2)0.004 (2)
C280.032 (3)0.053 (3)0.045 (3)0.007 (2)−0.006 (2)0.009 (2)
C290.082 (5)0.064 (4)0.054 (4)−0.013 (4)−0.007 (3)−0.003 (3)
C300.110 (7)0.069 (4)0.051 (4)0.035 (4)0.013 (4)0.003 (3)
O40.110 (7)0.057 (4)0.106 (6)0.000−0.019 (5)0.000
C310.069 (6)0.058 (5)0.084 (7)0.000−0.001 (5)0.000
Geometric parameters (Å, º) top
F1—C121.408 (6)C16—H16A0.9800
O1—C141.487 (6)C16—H16B0.9800
O1—C281.342 (6)C16—C171.551 (8)
O2—C281.206 (7)C17—C181.559 (7)
O3—H3A0.8206C17—C221.526 (7)
O3—H3B0.8272C17—C281.502 (7)
O3—C31.438 (6)C18—H180.9900
C1—H1A0.9800C18—C191.545 (7)
C1—H1B0.9800C19—H19A0.9800
C1—C21.531 (7)C19—H19B0.9800
C1—C101.550 (7)C19—C201.535 (7)
C2—H2A0.9800C20—C211.537 (8)
C2—H2B0.9800C20—C291.545 (10)
C2—C31.517 (8)C20—C301.523 (10)
C3—H30.9900C21—H21A0.9800
C3—C41.548 (8)C21—H21B0.9800
C4—C51.552 (7)C21—C221.514 (8)
C4—C231.545 (9)C22—H22A0.9800
C4—C241.536 (9)C22—H22B0.9800
C5—H50.9900C23—H23A0.9700
C5—C61.537 (7)C23—H23B0.9700
C5—C101.562 (6)C23—H23C0.9700
C6—H6A0.9800C24—H24A0.9700
C6—H6B0.9800C24—H24B0.9700
C6—C71.529 (8)C24—H24C0.9700
C7—H7A0.9800C25—H25A0.9700
C7—H7B0.9800C25—H25B0.9700
C7—C81.546 (7)C25—H25C0.9700
C8—C91.550 (6)C26—H26A0.9700
C8—C141.616 (7)C26—H26B0.9700
C8—C261.540 (8)C26—H26C0.9700
C9—H91.04 (6)C27—H27A0.9700
C9—C101.573 (7)C27—H27B0.9700
C9—C111.533 (7)C27—H27C0.9700
C10—C251.549 (7)C29—H29A0.9700
C11—H11A0.9800C29—H29B0.9700
C11—H11B0.9800C29—H29C0.9700
C11—C121.520 (7)C30—H30A0.9700
C12—H120.9900C30—H30B0.9700
C12—C131.521 (7)C30—H30C0.9700
C13—C141.574 (7)O4—H4i0.8199
C13—C181.583 (7)O4—H40.8200
C13—C271.560 (7)O4—C311.389 (12)
C14—C151.527 (7)C31—H31A0.9601
C15—H15A0.9800C31—H31B0.9600
C15—H15B0.9800C31—H31C0.9600
C15—C161.541 (7)
C28—O1—C14117.0 (4)C15—C16—C17110.5 (4)
C3—O3—H3A110.1H16A—C16—H16B108.1
C3—O3—H3B114.8C17—C16—H16A109.5
H1A—C1—H1B107.9C17—C16—H16B109.5
C2—C1—H1A109.1C16—C17—C18109.8 (4)
C2—C1—H1B109.1C22—C17—C16112.8 (4)
C2—C1—C10112.4 (4)C22—C17—C18112.9 (4)
C10—C1—H1A109.1C28—C17—C16107.0 (4)
C10—C1—H1B109.1C28—C17—C18102.9 (4)
C1—C2—H2A109.3C28—C17—C22110.9 (4)
C1—C2—H2B109.3C13—C18—H18106.9
H2A—C2—H2B108.0C17—C18—C13109.5 (4)
C3—C2—C1111.5 (5)C17—C18—H18106.9
C3—C2—H2A109.3C19—C18—C13114.7 (4)
C3—C2—H2B109.3C19—C18—C17111.6 (4)
O3—C3—C2110.1 (5)C19—C18—H18106.9
O3—C3—H3107.3C18—C19—H19A108.6
O3—C3—C4111.4 (4)C18—C19—H19B108.6
C2—C3—H3107.3H19A—C19—H19B107.5
C2—C3—C4113.2 (5)C20—C19—C18114.8 (4)
C4—C3—H3107.3C20—C19—H19A108.6
C3—C4—C5108.6 (4)C20—C19—H19B108.6
C23—C4—C3105.7 (5)C19—C20—C21108.0 (5)
C23—C4—C5108.3 (4)C19—C20—C29111.1 (5)
C24—C4—C3111.5 (5)C21—C20—C29111.0 (5)
C24—C4—C5115.1 (5)C30—C20—C19108.5 (5)
C24—C4—C23107.3 (5)C30—C20—C21108.9 (5)
C4—C5—H5105.0C30—C20—C29109.4 (6)
C4—C5—C10116.1 (4)C20—C21—H21A109.1
C6—C5—C4114.6 (4)C20—C21—H21B109.1
C6—C5—H5105.0H21A—C21—H21B107.9
C6—C5—C10110.0 (4)C22—C21—C20112.4 (5)
C10—C5—H5105.0C22—C21—H21A109.1
C5—C6—H6A109.5C22—C21—H21B109.1
C5—C6—H6B109.5C17—C22—H22A108.8
H6A—C6—H6B108.1C17—C22—H22B108.8
C7—C6—C5110.8 (4)C21—C22—C17113.6 (5)
C7—C6—H6A109.5C21—C22—H22A108.8
C7—C6—H6B109.5C21—C22—H22B108.8
C6—C7—H7A108.8H22A—C22—H22B107.7
C6—C7—H7B108.8C4—C23—H23A109.5
C6—C7—C8113.9 (4)C4—C23—H23B109.5
H7A—C7—H7B107.7C4—C23—H23C109.5
C8—C7—H7A108.8H23A—C23—H23B109.5
C8—C7—H7B108.8H23A—C23—H23C109.5
C7—C8—C9108.1 (4)H23B—C23—H23C109.5
C7—C8—C14110.7 (4)C4—C24—H24A109.5
C9—C8—C14110.6 (4)C4—C24—H24B109.5
C26—C8—C7106.5 (5)C4—C24—H24C109.5
C26—C8—C9111.1 (4)H24A—C24—H24B109.5
C26—C8—C14109.8 (4)H24A—C24—H24C109.5
C8—C9—H9100 (3)H24B—C24—H24C109.5
C8—C9—C10117.1 (4)C10—C25—H25A109.5
C10—C9—H9102 (3)C10—C25—H25B109.5
C11—C9—C8113.0 (4)C10—C25—H25C109.5
C11—C9—H9110 (3)H25A—C25—H25B109.5
C11—C9—C10113.1 (4)H25A—C25—H25C109.5
C1—C10—C5107.1 (4)H25B—C25—H25C109.5
C1—C10—C9107.6 (4)C8—C26—H26A109.5
C5—C10—C9105.8 (4)C8—C26—H26B109.5
C25—C10—C1107.9 (4)C8—C26—H26C109.5
C25—C10—C5114.6 (4)H26A—C26—H26B109.5
C25—C10—C9113.4 (4)H26A—C26—H26C109.5
C9—C11—H11A108.8H26B—C26—H26C109.5
C9—C11—H11B108.8C13—C27—H27A109.5
H11A—C11—H11B107.7C13—C27—H27B109.5
C12—C11—C9113.8 (4)C13—C27—H27C109.5
C12—C11—H11A108.8H27A—C27—H27B109.5
C12—C11—H11B108.8H27A—C27—H27C109.5
F1—C12—C11107.7 (4)H27B—C27—H27C109.5
F1—C12—H12108.2O1—C28—C17113.6 (4)
F1—C12—C13109.9 (4)O2—C28—O1119.1 (5)
C11—C12—H12108.2O2—C28—C17127.2 (5)
C13—C12—C11114.5 (4)C20—C29—H29A109.5
C13—C12—H12108.2C20—C29—H29B109.5
C12—C13—C14105.8 (4)C20—C29—H29C109.5
C12—C13—C18110.3 (4)H29A—C29—H29B109.5
C12—C13—C27110.1 (4)H29A—C29—H29C109.5
C14—C13—C18108.0 (4)H29B—C29—H29C109.5
C27—C13—C14112.5 (4)C20—C30—H30A109.5
C27—C13—C18110.0 (4)C20—C30—H30B109.5
O1—C14—C8103.1 (4)C20—C30—H30C109.5
O1—C14—C13106.6 (4)H30A—C30—H30B109.5
O1—C14—C15104.9 (4)H30A—C30—H30C109.5
C13—C14—C8115.5 (4)H30B—C30—H30C109.5
C15—C14—C8116.8 (4)H4—O4—H4i141.1
C15—C14—C13108.8 (4)C31—O4—H4i109.459 (11)
C14—C15—H15A109.7C31—O4—H4109.5
C14—C15—H15B109.7O4—C31—H31A109.5
C14—C15—C16109.9 (4)O4—C31—H31B109.5
H15A—C15—H15B108.2O4—C31—H31C109.5
C16—C15—H15A109.7H31A—C31—H31B109.5
C16—C15—H15B109.7H31A—C31—H31C109.5
C15—C16—H16A109.5H31B—C31—H31C109.5
C15—C16—H16B109.5
F1—C12—C13—C14173.2 (4)C12—C13—C18—C19−101.2 (5)
F1—C12—C13—C1856.6 (5)C13—C14—C15—C1651.5 (5)
F1—C12—C13—C27−65.0 (6)C13—C18—C19—C20−175.6 (5)
O1—C14—C15—C16−62.3 (5)C14—O1—C28—O2−173.5 (5)
O3—C3—C4—C5−176.6 (5)C14—O1—C28—C179.8 (6)
O3—C3—C4—C2367.5 (6)C14—C8—C9—C10172.4 (4)
O3—C3—C4—C24−48.8 (7)C14—C8—C9—C11−53.6 (5)
C1—C2—C3—O3−178.4 (5)C14—C13—C18—C1717.3 (5)
C1—C2—C3—C456.1 (6)C14—C13—C18—C19143.7 (4)
C2—C1—C10—C555.1 (6)C14—C15—C16—C1713.8 (6)
C2—C1—C10—C9168.5 (5)C15—C16—C17—C18−65.6 (5)
C2—C1—C10—C25−68.7 (6)C15—C16—C17—C22167.5 (4)
C2—C3—C4—C5−51.8 (6)C15—C16—C17—C2845.3 (5)
C2—C3—C4—C23−167.7 (5)C16—C17—C18—C1346.3 (6)
C2—C3—C4—C2476.0 (6)C16—C17—C18—C19−81.8 (5)
C3—C4—C5—C6−177.3 (5)C16—C17—C22—C2176.2 (6)
C3—C4—C5—C1052.7 (6)C16—C17—C28—O1−60.8 (6)
C4—C5—C6—C7164.8 (5)C16—C17—C28—O2122.8 (6)
C4—C5—C10—C1−54.3 (6)C17—C18—C19—C20−50.4 (6)
C4—C5—C10—C9−168.9 (4)C18—C13—C14—O143.2 (5)
C4—C5—C10—C2565.3 (6)C18—C13—C14—C8157.0 (4)
C5—C6—C7—C857.5 (7)C18—C13—C14—C15−69.5 (5)
C6—C5—C10—C1173.5 (4)C18—C17—C22—C21−48.9 (7)
C6—C5—C10—C958.9 (5)C18—C17—C28—O154.9 (6)
C6—C5—C10—C25−66.8 (5)C18—C17—C28—O2−121.5 (7)
C6—C7—C8—C9−49.6 (6)C18—C19—C20—C2155.7 (7)
C6—C7—C8—C14−170.8 (5)C18—C19—C20—C29−66.2 (6)
C6—C7—C8—C2669.9 (6)C18—C19—C20—C30173.5 (5)
C7—C8—C9—C1051.1 (6)C19—C20—C21—C22−57.5 (7)
C7—C8—C9—C11−174.9 (5)C20—C21—C22—C1756.2 (7)
C7—C8—C14—O1−107.5 (4)C22—C17—C18—C13173.1 (4)
C7—C8—C14—C13136.6 (4)C22—C17—C18—C1945.0 (6)
C7—C8—C14—C156.8 (6)C22—C17—C28—O1175.8 (5)
C8—C9—C10—C1−170.5 (4)C22—C17—C28—O2−0.6 (9)
C8—C9—C10—C5−56.2 (5)C23—C4—C5—C6−63.0 (7)
C8—C9—C10—C2570.2 (5)C23—C4—C5—C10167.0 (5)
C8—C9—C11—C1230.9 (7)C24—C4—C5—C657.0 (6)
C8—C14—C15—C16−175.6 (4)C24—C4—C5—C10−73.0 (6)
C9—C8—C14—O1132.7 (4)C26—C8—C9—C10−65.4 (6)
C9—C8—C14—C1316.9 (6)C26—C8—C9—C1168.6 (6)
C9—C8—C14—C15−112.9 (5)C26—C8—C14—O19.7 (5)
C9—C11—C12—F1153.5 (4)C26—C8—C14—C13−106.1 (5)
C9—C11—C12—C1330.9 (7)C26—C8—C14—C15124.1 (5)
C10—C1—C2—C3−58.2 (7)C27—C13—C14—O1164.8 (4)
C10—C5—C6—C7−62.2 (6)C27—C13—C14—C8−81.3 (5)
C10—C9—C11—C12166.9 (4)C27—C13—C14—C1552.2 (5)
C11—C9—C10—C155.5 (6)C27—C13—C18—C17−105.9 (5)
C11—C9—C10—C5169.8 (4)C27—C13—C18—C1920.5 (6)
C11—C9—C10—C25−63.8 (6)C28—O1—C14—C8174.9 (4)
C11—C12—C13—C14−65.5 (5)C28—O1—C14—C13−63.0 (5)
C11—C12—C13—C18178.0 (4)C28—O1—C14—C1552.3 (5)
C11—C12—C13—C2756.3 (6)C28—C17—C18—C13−67.4 (5)
C12—C13—C14—O1−74.9 (4)C28—C17—C18—C19164.6 (4)
C12—C13—C14—C838.9 (5)C28—C17—C22—C21−163.7 (5)
C12—C13—C14—C15172.4 (4)C29—C20—C21—C2264.5 (6)
C12—C13—C18—C17132.5 (5)C30—C20—C21—C22−175.0 (6)
Symmetry code: (i) −x, y, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O3ii0.822.122.784 (10)138
O3—H3B···O4iii0.831.942.695 (6)152
O4—H4···O3ii0.821.962.695 (6)149
Symmetry codes: (ii) −x+1, y, −z+3/2; (iii) x+1, y, z.
 

Acknowledgements

The authors thank the staff in the Department of Chemistry XRD Facility in the Faculty of Science and Engineering at the University of Manchester for their assistance in data collection and analysis.

Funding information

Funding for this research was provided by: Biotechnology and Biological Sciences Research Council (studentship No. 2110646 to Megan A Eadsforth; grant No. BB/S00047X/1 to R. T. O'Keefe, R. A. Bryce, R. C. Whitehead).

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ISSN: 2056-9890
Volume 80| Part 8| August 2024| Pages 857-862
https://doi.org/10.1107/S2056989024006480
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