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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 82| Part 3| March 2026| Pages 271-277
https://doi.org/10.1107/S2056989026001234

Crystal structures of an azo­benzene-bridged aza-18-crown-6 cryptand and a sodium complex thereof

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Christoph Schwaba and Elisabeth Kreidta*

aOtto-Hahn-Strasse 6A, 44227 Dortmund, Germany
*Correspondence e-mail: [email protected]

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 23 December 2025; accepted 5 February 2026; online 10 February 2026)

We report the single-crystal X-ray diffraction structures of the azo­benzene-bridged aza-18-crown-6 cryptand 7,16-[3,3′-(diazene-1,2-di­yl)bis­(1,3-phenyl­enecarbon­yl)]-1,4,10,13-tetra­oxa-7,16-di­aza­cyclo­octa­decane, C26H32N4O6, 1, and its sodium complex poly[[{μ-7,16-[3,3′-(diazene-1,2-di­yl)bis­(1,3-phenyl­enecarbon­yl)]-1,4,10,13-tetra­oxa-7,16-di­aza­cyclo­octa­deca­ne}bis­{tetra­kis­[3,5-bis­(tri­fluoro­meth­yl)phen­yl]borato}disodium] benzene disolvate], {[Na2(C32H12F24B)2(C26H32N4O6)]·2C6H6}n. The free ligand 1 crystallizes in space group P21/n and adopts an elongated strain-distorted crown conformation with a slightly twisted azo­benzene unit. In contrast, 2 [obtained with sodium tetra­kis-3,5-bis­(tri­fluoro­meth­yl)phenyl borate (NaBArF)] crystallizes in space group P1 and features multiple Na+ centers that assemble into a three-dimensional network in the solid state. Hirshfeld surface analysis was used to provide a complementary, qu­anti­tative description of the dominant inter­molecular contacts governing the crystal packing.

CCDC references: 2528906; 2528905

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1. Chemical context

The azo­benzene-functionalized crown ethers reported by Shinkai and co-workers in the early 1980s (Shinkai et al., 1980View full citation, 1982View full citation; Shinkai & Manabe, 1984View full citation) are considered prototypical examples of photoresponsive tools for mol­ecular recognition and transport (Hua & Flood, 2010View full citation; Hein et al., 2025View full citation). They have even been referred to as the first generation of mol­ecular machines (Kinbara & Aida, 2005View full citation). As described by Shinkai and co-workers, in 1 the reversible trans/cis photoisomerization of the azo­benzene moiety can be used to modulate the conformation and binding properties of the 18-crown-6 cavity, allowing control of its binding affinity and selectivity towards different alkali metal cations (Shinkai et al., 1980View full citation).

[Scheme 1]

Analogous ligands with azo­pyridines and thia­crown ethers had also been described. For these also solid-state structural data are available (Shinkai et al., 1984View full citation). Single-crystal X-ray diffraction studies are valuable for understanding the geometric preferences of the macrocycle, the orientation of the azo­benzene unit relative to the crown ether and, in case of the complexes, the coordination geometry of the cation. These structural insights are critical for understanding the cooperative effects between the azo­benzene moiety and the crown ether ring, and their ability to form complexes with metal cations. However, for the parent compound 1, no solid-state structural characterization had been reported until now. In the present study, we focused on the crystallization of the free ligand 1 and its sodium complex 2 to gain a more detailed structural understanding of the cation coordination environment in the solid state.

2. Structural commentary

Compound 1 crystallized overnight from a boiling hot toluene solution that was slowly cooled to room temperature, yielding yellow needle-shaped crystals in the centrosymmetric space group P21/n. The mol­ecular structure is illustrated in Fig. 1[link].

[Figure 1]
Figure 1
Mol­ecular structure of 1 showing the atom labelling and 50% probability ellipsoids.

Compound 1 consists of a crown ether framework (1,4,10,13-tetra­oxa-7,16-di­aza­cyclo­octa­deca­ne), whose N1 and N4 nitro­gen atoms connect via an amide bond to an azo­benzene unit, thereby forming a macrobicyclic cryptand. The amide bond lengths are 1.3629 (4) Å for the C1—N1 bond and 1.3650 (4) Å for the C14—N4 bond, which is in the normal range of amide bonds (Allen et al., 1987View full citation). The sp2-hybridized nitro­gen atoms exhibit a slight pyramidalization and therefore deviate from ideal trigonal planar geometry. For N3, the pyramidalization χn, as defined by Winkler & Dunitz (1971View full citation), is χn = 7.12°, and for N4 it is χn = 9.33°, indicating a slight deviation from ideal planarity. The corresponding bond-angle sums are 355.81° (N3) and 352.22° (N4), values that are consistent with those expected for sp2-hybridized nitro­gen atoms (Glover & Rosser, 2018View full citation). These slight deviations are likely a consequence of intra­molecular strain.

In compound 1, the aza­crown ether ring is significantly elongated because of the strain imposed by the azo­benzene unit. The mean distance between the opposing central carbon atoms (C24⋯C17 and C23⋯C18) is 3.6680 (6) Å, whereas the separation between the bridging nitro­gen atoms (N3 and N4) amounts to 7.5848 (5) Å. These values differ from those typically observed in unstrained aza-18-crown-6 derivates, where the distances between the opposing inward-facing donor atoms generally lie in the range of 5.4-6.0 Å (Simonov et al., 2003View full citation; Chekhlov & Martynov, 1999View full citation).

The Csp3—Csp3 bond lengths within the aza­crown ether unit range from 1.5100 (5) to 1.5248 (5) Å, which are slightly shorter than the typical C—C single bond length of 1.52 Å (Allen et al., 1987View full citation). The bond-angle sums around the tetra­hedral Csp3 atoms are in the range 435.81-442.90°, consistent with the values expected for sp3-hybridized carbon atoms (Allen et al.,1987View full citation). A gradual increase in the bond-angle sum is observed towards the bridging nitro­gen atoms, indicating a slight widening of the tetra­hedral environment in this part of the macrocycle, which may be attributed to intra­molecular strain within the aza­crown ether framework.

The Csp3—Osp3 bond lengths are in the range of 1.4194 (4)–1.4434 (5) Å, while the C—O—C bond angles are in the range 110.71 (3)–115.84 (3)°, both of which fall within the expected ranges for ether bonds (Allen et al., 1987View full citation).

The azo­benzene unit is non-planar, with the two phenyl rings twisted relative to each other. The torsion angle (C—N=N—C) is −171.60 (3)°, reflecting a moderate torsion about the N=N bond. This deviation from coplanarity is best explained by intra­molecular strain within the macrocyclic framework and by crystal-packing effects. Similar distortions are also observed in the crystal structures of non-bridged azo­benzene derivatives (Strüben et al., 2016View full citation).

The N2=N3 bond length is 1.2514 (4) Å, which falls within the expected range for an azo double bond of 1.23–1.26 Å (Allen et al., 1987View full citation). The C—N=N bond angles of 111.81 (3) and 115.60 (3)° are close to the typical values observed in azo­benzene derivatives (Allen et al., 1987View full citation; Strüben et al., 2016View full citation).

Having described the structural features of the free ligand, attention may now be directed to the corresponding sodium complex (2), which was obtained by heating compound 1 in the presence of sodium tetra­kis-3,5-bis­(tri­fluoro­meth­yl)phenyl borate (NaBArF). Crystals suitable for X-ray diffraction were grown over three days in an NMR tube containing benzene, with approximately one-quarter of the tube immersed in an oil bath at 353 K, yielding block-like crystals in the triclinic space group PMathematical equation.

As shown in Fig. 2[link], the crystal structure contains two sodium cations. One (Na2) is coordinated by four oxygen atoms from the bottom-side of the crown ether, while the second one is coordinated by the carbonyl oxygen atoms of the bridging amide functionality. Notably, the weakly coordinating BArF anions are also inter­acting with the sodium centers.

[Figure 2]
Figure 2
Mol­ecular structure of the sodium complex 2 showing the atom labelling and 50% probability ellipsoids.

Na1 is found in a distorted octa­hedral coordination geometry with a coordination number of six, being coordinated by four oxygen atoms (O3–O6) of the crown ether ring and two fluorine atoms (F6 and F45) from two different BArF anions. The Na—O bond lengths range from 2.313 (2) to 2.366 (2) Å, while the Na—F distances are 2.362 (2) Å for Na1—F6 and 2.896 (3) Å for Na1—F45. The values for the Na—O bond lengths are slightly shorter than those reported for unstrained aza­crown ether derivatives, which typically fall in the range of 2.4–2.6 Å (Özbey et al., 1998View full citation; Hu et al., 2004View full citation; Rodríguez-Rodríguez et al., 2014View full citation). The Na—F distances are in line with those reported in literature, which typically fall in the range of 2.3–2.9 Å (Evans et al., 2023View full citation; D'Amato et al., 2021View full citation; Pascu et al., 2005View full citation).

Na2 has a coordination number of eight, being coordinated axially by the carbonyl oxygen atoms O1 and O2 from two different ligand mol­ecules, and by six fluorine atoms (F1, F2, F27, F28, F41, F48) from four different BArF anions. The Na—O bond lengths are 2.275 (2) Å and 2.194 (2) Å, while the Na—F contacts range from 2.482 (2) Å to 2.979 (2) Å. The values of the Na—O bond lengths are slightly shorter than those reported in the literature (Zhang et al., 2011View full citation; Mahmoud et al., 2019View full citation; Li et al., 2015View full citation), whereas the Na—F distances are in good agreement with the literature (Evans et al., 2023View full citation; D'Amato et al., 2021View full citation; Pascu et al., 2005View full citation).

Apart from variations in some bond angles within the macrocycle, no significant changes in bond lengths or angles are observed in comparison to the free ligand. The only notable difference concerns the torsion angle within the azo­benzene unit (C—N=N—C), with changes from −171.60 (3)° in the free ligand to −177.7 (2)° in the sodium complex. This shift towards a more planar conformation is likely a consequence of crystal-packing effects or the slight structural reorganization of the crown-ether unit induced by the sodium coordination.

3. Supra­molecular features

The extended structure of compound 1 is shown in Fig. 3[link]. The crystal packing is driven by short H⋯O contacts (Table 1[link]), which link the mol­ecules into a chain propagating along the [100] direction. To further analyze the supra­molecular packing inter­actions, a Hirshfeld surface analysis was performed (Spackman & Jayatilaka, 2009View full citation). The Hirshfeld surface was mapped over dnorm in the range from −0.22 to 1.44 arbitrary units, generated by CrystalExplorer21 (Spackman et al., 2021View full citation) and is shown in Fig. 4[link]. The fingerprint plots are illustrated in Fig. 5[link] and were also generated by CrystalExplorer21. Particularly notable are the short H⋯O contacts, which are shown in red on the Hirshfeld surface. They have a significant influence on the crystal packing and account for 20.8% of the overall inter­molecular inter­actions in the crystal. The H⋯H contacts (56.1%) represent the biggest fraction but contribute less significantly to the overall crystal packing.

Table 1
Geometric parameters (Å, °) and chain directions for selected C—H⋯O contacts

  C21—H21A⋯O3 C26—H26B⋯O2 C9—H9⋯O6
D—H 1.012 (11) 1.005 (11) 1.008 (11)
H⋯A 2.498 (11) 2.395 (11) 2.405 (11)
D⋯A 3.5028 (5) 3.3917 (5) 3.3677 (4)
D—H⋯A 171.7 (8) 171.3 (9) 159.6 (9)
Direction of chain [100] [001] [100]
[Figure 3]
Figure 3
The crystal packing of compound 1.
[Figure 4]
Figure 4
Hirshfeld surface of compound 1 (left) and Hirshfeld surface of compound 1 with a neighbouring mol­ecule, illustrating the inter­molecular contacts (right); generated by CrystalExplorer21.
[Figure 5]
Figure 5
Two-dimensional fingerprint plots of compound 1 showing (a) all contributions in the crystal and those delineated into (b) H⋯H, (c) H⋯C/C⋯H and (d) H⋯O/O⋯H inter­actions.

For compound 2, the extended structure is shown in Fig. 6[link]. The packing is consolidated by Na⋯O inter­actions, involving the crown-ether and carbonyl oxygen atoms, and by Na⋯F contacts with the BArF anions. Together they generate a three-dimensional coordination-polymer framework. A Hirshfeld surface analysis (mapped over dnorm in the range from −0.73 to 2.03 arbitrary units) of the sodium complex 2 (Fig. 7[link]) reveals that the particularly short Na⋯O and Na⋯F contacts (shown in red on the surface) exert a strong influence on the overall crystal packing, although the fingerprint plots (Fig. 8[link]) show that these contacts represent only a small fraction of the inter­actions in the crystal (Na⋯O: 0.7%; Na⋯F: 1.3%). The largest fraction of inter­actions is represented by H⋯F contacts (42.2%), but these contribute only marginally to the overall crystal packing.

[Figure 6]
Figure 6
The crystal packing of the sodium complex 2.
[Figure 7]
Figure 7
Hirshfeld surface of the sodium complex 2 generated by CrystalExplorer21.
[Figure 8]
Figure 8
Two-dimensional fingerprint plots of the sodium complex 2 showing (a) all contributions in the crystal and those delineated into (b) H⋯H, (c) H⋯C/C⋯H, (d) H⋯F/F⋯H, (e) Na⋯F/F⋯Na and (f) Na⋯O/O⋯Na inter­actions.

4. Database survey

Several crystallographically characterized structures with motifs similar to compound 1 have been reported. The following examples were identified in the Cambridge Structural Database (WebCSD, September 2025; Groom et al., 2016View full citation): 1,10-(3,3′-dicarbonyl-1,1′-azo­benzene)-1,10-di­aza-4,7,14,17-tetra­thia­cyclo-octa­decane, C26N4O2S4 (CEMXAT; Ammon et al., 1984View full citation), 1,10-[6,6′-dicarbonyl-2,2′-azo­pyridine-C(6),C(6′)]-1,10-di­aza-4,7,14,17-tetra­thia­cyclo-octa­decane, C24N6O6 (CEMXEX; Ammon et al., 1984View full citation), 1,10-diazo­nia-18-crown-6 tartrate hexa­hydrate, C16H20N2O16 (HOCXIG; Chekhlov & Martynov, 1999View full citation), 1,4,10,13-tetra­oxa-7,16-di­aza­cyclo­octa­decane bis­[(1,2,5)oxa­diazolo[3,4-d]pyrimidine-5,7(4H,6H)-dione) clathrate dihydrate, C28H34N10O12 (BEGWAM; Simonov et al., 2003View full citation) and (E)-[diazene-1,2-diylbis(4,1-phenyl­ene)]bis­(di­methyl­silanol) C16H22N2O2Si2 (OXUKAV; Strüben et al., 2016View full citation).

In CEMXAT, the oxygen atoms of the crown ether ring are replaced by sulfur atoms. As expected, this substitution leads to a more flexible and less stretched macrocyclic framework compared to compound 1. The mean distance between the centered carbon atoms is wider [5.5920 (4) Å], the distance between the bridging nitro­gen atoms remains comparable [7.8380 (7) Å]. The torsion angle of the azo­benzene unit (C—N=N—C) is larger [175.7213 (3)°] than in 1, indicating a more planar conformation.

In CEMXEX, the azo­benzene unit is replaced by an azo­pyridine fragment. The macrocycle adopts a stretched conformation, comparable to that in 1. The mean distance between the central opposing carbon atoms is 3.8950 (5) Å, while the separation between the bridging nitro­gen atoms amounts to 7.0906 (7) Å. The torsion angle of the azo­pyridine unit (C—N=N—C) is 173.7839 (5)°, indicating conformation similar to that in 1.

In HOCXIG, the structure of a protonated unbridged aza­crown ether, the mean distance between the opposing oxygen atoms [5.720 (4) Å] and nitro­gen atoms [5.399 (3) Å] lie within a similar range, indicating an unstrained macrocyclic framework with a more regular, near-circular geometry compared to compound 1.

Finally, in BEGWAM, a neutral aza­crown ether, the macrocycle also displays an unstrained and near-circular conformation. The mean distances between the opposing oxygen atoms [5.8641 (3) Å] and the opposing nitro­gen atoms [5.4364 (3) Å] lie within a comparable range.

In addition, the CSD contains entries with similar coordination environments to that observed in compound 2, providing a useful basis for comparison: catena-[hexa­kis­[μ-pyridin-4-yl(2H-pyrrol-2-yl­idene)methano­lato]bis­(aceto­nitrile)­dimanganesedisodium aceto­nitrile solvate], C66H51Mn2N15Na2O6 (BUHSAA; Li et al., 2015View full citation), (2)-[μ2-2,6-bis­(n-hex­yl)pyrrolo­[3,4-f]iso­indole-1,3,5,7(2H,6H)-tetrone](μ2-2,5,8,11,14,16,19,22,25,28-deca­oxa-1,15(1,5)-dinaphthal­ena­cyclo-octa­cosa­phane)bis­{tetra­kis­[3,5-bis­(tri­fluoro­meth­yl)phen­yl]borate-F,F′}disodiumpseudorotaxane hepta­hydrate, C122H96B2F48N2Na2O14 (FOFGAJ; Pascu et al., 2005View full citation), (N,N′-bis­(but-3-en­yl)-1,10-di­aza-18-crown-6)sodium hexa­fluoro­phosphate, C20H38F6N2NaO4P (FOFGAJ; Hu et al., 2004View full citation), {2,2′-[(1,4,10,13-tetra­oxa-7,16-di­aza­cyclo­octa­decane-7,16-di­yl)bis­(methyl­ene)]bis-1H-benzimidazole}­sodium perchlorate, C28H38N6O8NaCl (FOFRO; Rodríguez-Rodríguez et al., 2014View full citation), bis­[μ-(3-{2-[1-amino-1,3-dioxobutan-2-yl­idene]hydraz­in­yl}-4-hy­droxy­benzene-1-sulfonato)]hexa­aqua­disodium, C20H32N6O18Na2S2 (FIZHUU; Mahmoud et al., 2019View full citation) and catena-[(μ-tetra­kis­[3,5-bis­(tri­fluoro­meth­yl)phen­yl]borato)bis­(aqua)­sodium], C32H16BF24NaO2 (RENPIK01; Evans et al., 2023View full citation).

In FOFGAJ, the sodium cation is located inside the cavity of the aza­crown ether and is additionally coordinated by two vinyl groups of the side arms attached to the nitro­gen atoms. The average Na—O bond length is 2.532 (2) Å, while the Na—N bond length is 2.893 (2) Å. The Na—O distance is therefore longer than that observed in 2. In FOFROJ, where the sodium is also located within an aza­crown ether cavity, similar values are observed.

In BUHSAA, the Na—O distances of 1.264 (2) and 2.325 (1) Å are slightly longer than in 2. The same applies for FIZHUU [2.299 (2) Å] and AQIYIJ [2.325 (3) Å].

The structures of FEKXAV and RENPIK01 contain inter­actions between a sodium cation and fluorine atoms of the CF3 groups of a BArF anion, similar to 2. In FEKXAV, the Na—F distance is 2.93934 (2) Å, while in RENPIK01 the Na—F distance ranges from 2.35 (2) to 2.48 (2) Å, values that are comparable with those observed in 2.

5. Synthesis and crystallization

The reaction schemes for the synthesis of compounds 1 and 2 are shown in Fig. 9[link].

[Figure 9]
Figure 9
Reaction scheme for the synthesis of the ligand 1 and its sodium complex 2.

Compound 1, C26H32N4O6.

A solution of 3,3′-(diazene-1,2-di­yl)dibenzoyl chloride (117 mg, 0.38 mmol) in MeCN (100 mL) and a solution of 1,4,10,13-tetra­oxa-7,16-di­aza­cyclo­octa­decane (3, 100 mg, 0.38 mmol) in MeCN (100 mL) were added dropwise and simultaneously to a stirred solution of NEt3 (0.38 mL, 279 mg, 2.76 mmol) in MeCN (150 mL), preheated to 353 K. The mixture was allowed to cool to room temperature during the addition. After completion of the addition the solution was stirred for 16 h at room temperature. The solvent was removed in vacuo and the crude product was dissolved in CHCl3 and washed with water (3 × 20 mL). After removal of the volatiles, the residue was purified by silica gel column chromatography (DCM/MeOH 25:1) to yield 1 as a yellow–orange solid (135 mg, 0.27 mmol, 72%). Crystals suitable for X-ray diffraction were obtained by recrystallization from boiling hot toluene solution, giving 1 as yellow needle-shaped crystals.

1H-NMR (600 MHz, CDCl3, δ/ppm J/Hz): 8.07 (2H, t, J = 1.85, Carom.), 7.92–7.93 (2H, m, Carom), 7.75–7.76 (2H, m, Carom), 7.60 (2H, t, J = 7.64), 3.15–4.25 (24H, m, CH2).

HRMS (ESI+) m/z calculated for C26H32N4O6: [M+Na]+ 519.2220, found 519.2216.

Compound 2, C102H68B2F48N4Na2O6.

34,37,313,316-Tetra­oxa-31,310,6,7-tetra­aza-3(1,10)-cyclo­octa­decana-1,5(1,3)-dibenzena­cyclo­hepta­phan-6-ene-2,4-dione (4 mg, 0.008 mmol) was dissolved in benzene (0.5 mL) in an NMR tube and NaBArF (14 mg, 0.016 mmol) was added. The mixture was heated at 353 K for 15 min, during which the solution became colorless and an orange solid precipitated. The tube was then filled to approximately five-sixth with benzene and placed to about one-quarter of its length in an oil bath kept at 353 K. Crystals of the sodium complex 2, suitable for X-ray diffraction, were obtained after three days as yellow block-like crystals in the upper part of the tube.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Hydrogen atoms were positioned geometrically and refined using a riding model with Uiso(H) set to 1.2Ueq of the carrier atom (1.5Ueq for methyl groups). Two CF3 groups are rotationally disordered about the C—CF3 bonds: at C34 (sets F51/F2/F4 and F1/F3/F10) with ratio 0.651 (4):0.349 (4), and at C41 (sets F11/F14/F9 and F12/F13/F10) with ratio 0.771 (6):0.229 (6). The disorder was modeled with PART instructions; distance-similarity restraints (SADI) and displacement-parameter restraints (RIGU, SIMU, ISOR) were applied to maintain reasonable geometry and ADPs for the disordered atoms.

Table 2
Experimental details

  1 2
Crystal data
Chemical formula C26H32N4O6 [Na2(C32H12F24B)2(C26H32N4O6)]·2C6H6
Mr 496.57 2425.20
Crystal system, space group Monoclinic, P21/n Triclinic, PMathematical equation
Temperature (K) 100 100
a, b, c (Å) 14.9099 (7), 7.7078 (3), 22.1751 (10) 13.5857 (6), 13.8054 (6), 27.8552 (11)
α, β, γ (°) 90, 108.751 (1), 90 84.152 (2), 78.185 (2), 89.238 (2)
V (Å3) 2413.16 (18) 5087.0 (4)
Z 4 2
Radiation type Ag Kα, λ = 0.56086 Å Cu Kα
μ (mm−1) 0.06 1.49
Crystal size (mm) 0.8 × 0.3 × 0.2 0.30 × 0.29 × 0.24
 
Data collection
Diffractometer Bruker APEXII CCD Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Krause et al., 2015View full citation) Multi-scan (SADABS; Krause et al., 2015View full citation)
Tmin, Tmax 0.408, 0.435 0.342, 0.471
No. of measured, independent and observed reflections 1669726, 27661, 24282 [I ≥ 2u(I)] 168897, 20857, 18230 [I > 2σ(I)]
Rint 0.065 0.044
(sin θ/λ)max (Å−1) 1.111 0.626
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.115, 1.04 0.071, 0.205, 1.08
No. of reflections 27661 20857
No. of parameters 453 1473
No. of restraints 0 244
H-atom treatment All H-atom parameters refined H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.66, −0.33 1.45, −0.76
Computer programs: APEX4 and SAINT (Bruker, 2016View full citation), OLEX2.solve and OLEX2.refine (Bourhis et al., 2015View full citation), SHELXT (Sheldrick, 2015aView full citation), SHELXL (Sheldrick, 2015bView full citation) and OLEX2 (Dolomanov et al., 2009View full citation).

Supporting information

CCDC references: 2528906; 2528905

Crystal structure: contains datablocks 1, 2. DOI: https://doi.org/10.1107/S2056989026001234/vm2322sup1.cif

Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989026001234/vm23221sup2.hkl

Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989026001234/vm23222sup3.hkl

checkCIF report


Computing details top

7,16-[3,3'-(Diazene-1,2-diyl)bis(1,3-phenylenecarbonyl)]-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane (1) top
Crystal data top
C26H32N4O6F(000) = 1056.322
Mr = 496.57Dx = 1.367 Mg m−3
Monoclinic, P21/nAg Kα radiation, λ = 0.56086 Å
a = 14.9099 (7) ÅCell parameters from 9994 reflections
b = 7.7078 (3) Åθ = 2.2–18.1°
c = 22.1751 (10) ŵ = 0.06 mm−1
β = 108.751 (1)°T = 100 K
V = 2413.16 (18) Å3Needle, yellow
Z = 40.8 × 0.3 × 0.2 mm
Data collection top
Bruker APEXII CCD
diffractometer		24282 reflections with I ≥ 2u(I)
Detector resolution: 7.9 pixels mm-1Rint = 0.065
φ and ω scansθmax = 38.5°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)		h = −33→33
Tmin = 0.408, Tmax = 0.435k = −17→17
1669726 measured reflectionsl = −49→49
27661 independent reflections
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullPrimary atom site location: iterative
R[F2 > 2σ(F2)] = 0.040All H-atom parameters refined
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0585P)2 + 0.3262P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
27661 reflectionsΔρmax = 0.66 e Å−3
453 parametersΔρmin = −0.33 e Å−3
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O30.55481 (2)0.46129 (4)0.219451 (13)0.01385 (4)
O60.514125 (19)0.20077 (4)0.342646 (14)0.01290 (4)
O40.771280 (19)0.39051 (4)0.347818 (12)0.01249 (4)
O50.71583 (2)−0.06721 (4)0.353696 (14)0.01520 (4)
O20.36419 (2)0.80557 (4)0.264270 (14)0.01417 (4)
O10.87734 (3)−0.00660 (4)0.539160 (15)0.01636 (5)
N40.39753 (2)0.51839 (4)0.282315 (13)0.00963 (3)
N20.66862 (2)0.61248 (4)0.492513 (14)0.01188 (4)
N10.88028 (2)0.12433 (4)0.448014 (13)0.01081 (4)
N30.61260 (2)0.66152 (4)0.520678 (14)0.01133 (4)
C120.40783 (2)0.71471 (4)0.371663 (15)0.00998 (4)
C80.52280 (2)0.71185 (4)0.476844 (15)0.01011 (4)
C20.86078 (2)0.29794 (4)0.536550 (15)0.01067 (4)
C140.38541 (2)0.68225 (4)0.301726 (15)0.00983 (4)
C110.34626 (2)0.81097 (5)0.394823 (17)0.01231 (4)
C150.38848 (2)0.50407 (5)0.214721 (15)0.01147 (4)
C90.46051 (2)0.80144 (5)0.500862 (16)0.01223 (4)
C60.75456 (2)0.53760 (4)0.531792 (15)0.01057 (4)
C70.78606 (2)0.40326 (5)0.501719 (15)0.01114 (4)
C100.37218 (2)0.85171 (5)0.459331 (18)0.01338 (5)
C260.36959 (2)0.36854 (4)0.313840 (16)0.01113 (4)
C10.87632 (2)0.12759 (5)0.508558 (15)0.01114 (4)
C30.90911 (2)0.33823 (5)0.600311 (16)0.01242 (4)
C130.49581 (2)0.66452 (4)0.412558 (15)0.01082 (4)
C190.85884 (3)0.31131 (5)0.351561 (17)0.01328 (5)
C50.80275 (2)0.58062 (5)0.595111 (16)0.01229 (4)
C200.91627 (2)0.27134 (5)0.420240 (16)0.01183 (4)
C40.88167 (3)0.48247 (5)0.628526 (16)0.01325 (5)
C180.71091 (2)0.39965 (5)0.283500 (16)0.01310 (5)
C160.47464 (2)0.57375 (5)0.199716 (16)0.01262 (4)
C230.65659 (3)0.03910 (5)0.377230 (18)0.01458 (5)
C170.62048 (2)0.49376 (5)0.281401 (16)0.01219 (4)
C240.56377 (3)0.06357 (5)0.324276 (18)0.01334 (5)
C210.88415 (2)−0.04816 (5)0.420429 (18)0.01286 (4)
C250.41595 (3)0.19833 (4)0.307544 (18)0.01305 (5)
C220.79114 (3)−0.14859 (5)0.40218 (2)0.01460 (5)
H26a0.3841 (7)0.3932 (12)0.3586 (5)0.018 (2)*
H17a0.5966 (7)0.4510 (12)0.3156 (5)0.018 (2)*
H20a0.9832 (7)0.2423 (13)0.4216 (4)0.0174 (19)*
H15a0.3814 (7)0.3807 (12)0.2031 (4)0.0159 (19)*
H130.5396 (7)0.5974 (13)0.3980 (5)0.021 (2)*
H50.7806 (7)0.6765 (13)0.6160 (5)0.022 (2)*
H24a0.5751 (8)0.0947 (14)0.2843 (5)0.025 (2)*
H70.7512 (7)0.3784 (13)0.4568 (5)0.021 (2)*
H16a0.4916 (7)0.6843 (13)0.2190 (5)0.018 (2)*
H15b0.3320 (7)0.5691 (13)0.1877 (5)0.019 (2)*
H110.2830 (7)0.8464 (14)0.3678 (5)0.025 (2)*
H21a0.9051 (7)−0.0336 (13)0.3816 (5)0.021 (2)*
H20b0.9205 (7)0.3730 (12)0.4479 (4)0.017 (2)*
H19a0.8471 (7)0.2078 (13)0.3249 (5)0.021 (2)*
H90.4790 (7)0.8261 (14)0.5479 (5)0.023 (2)*
H17b0.6319 (7)0.6175 (13)0.2876 (5)0.020 (2)*
H18a0.7431 (8)0.4558 (14)0.2590 (5)0.026 (2)*
H26b0.2991 (7)0.3530 (12)0.2951 (5)0.0164 (19)*
H19b0.8978 (7)0.3895 (13)0.3338 (5)0.021 (2)*
H16b0.4584 (7)0.5834 (13)0.1548 (5)0.020 (2)*
H40.9183 (7)0.5114 (14)0.6721 (5)0.022 (2)*
H23a0.6445 (8)−0.0198 (14)0.4144 (5)0.026 (2)*
H100.3293 (7)0.9177 (12)0.4755 (5)0.019 (2)*
H23b0.6863 (8)0.1538 (14)0.3909 (5)0.028 (3)*
H24b0.5271 (8)−0.0452 (15)0.3178 (5)0.028 (2)*
H21b0.9323 (7)−0.1188 (13)0.4526 (5)0.019 (2)*
H22a0.7717 (7)−0.1685 (14)0.4396 (5)0.025 (2)*
H25a0.3844 (7)0.1060 (13)0.3239 (5)0.020 (2)*
H18b0.6953 (7)0.2842 (14)0.2675 (5)0.024 (2)*
H30.9626 (7)0.2633 (14)0.6260 (5)0.023 (2)*
H22b0.8009 (8)−0.2615 (15)0.3827 (5)0.029 (3)*
H25b0.4077 (7)0.1686 (12)0.2626 (4)0.017 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.01159 (8)0.01825 (10)0.01036 (8)0.00223 (7)0.00163 (6)−0.00202 (7)
O60.01144 (8)0.01153 (8)0.01427 (9)0.00090 (6)0.00208 (7)−0.00249 (7)
O40.01149 (8)0.01642 (10)0.00939 (7)0.00372 (7)0.00311 (6)0.00088 (7)
O50.01271 (9)0.01924 (11)0.01301 (9)0.00376 (8)0.00327 (7)−0.00292 (8)
O20.01719 (10)0.01029 (8)0.01243 (9)0.00170 (7)0.00114 (7)0.00233 (7)
O10.02231 (12)0.01391 (10)0.01229 (9)0.00253 (9)0.00478 (8)0.00345 (7)
N40.01076 (8)0.00882 (8)0.00912 (8)−0.00035 (6)0.00292 (6)−0.00009 (6)
N20.01041 (8)0.01532 (10)0.00953 (8)0.00245 (7)0.00266 (6)−0.00006 (7)
N10.01111 (8)0.01178 (9)0.00971 (8)0.00118 (7)0.00357 (6)−0.00012 (7)
N30.01062 (8)0.01365 (9)0.00939 (8)0.00127 (7)0.00277 (6)−0.00112 (7)
C120.00969 (8)0.00974 (9)0.00990 (9)0.00075 (7)0.00231 (7)−0.00055 (7)
C80.00983 (8)0.01099 (9)0.00939 (9)0.00076 (7)0.00295 (7)−0.00092 (7)
C20.01023 (9)0.01293 (10)0.00819 (8)0.00101 (7)0.00202 (7)0.00000 (7)
C140.00937 (8)0.00929 (9)0.00971 (9)0.00038 (7)0.00148 (7)0.00022 (7)
C110.01027 (9)0.01296 (10)0.01344 (10)0.00226 (8)0.00344 (8)−0.00048 (8)
C150.01093 (9)0.01344 (10)0.00890 (9)−0.00083 (8)0.00159 (7)−0.00095 (8)
C90.01238 (10)0.01384 (11)0.01130 (10)0.00113 (8)0.00496 (8)−0.00172 (8)
C60.00988 (9)0.01269 (10)0.00867 (8)0.00081 (7)0.00230 (7)−0.00039 (7)
C70.01035 (9)0.01413 (11)0.00806 (8)0.00185 (8)0.00173 (7)−0.00072 (8)
C100.01194 (10)0.01511 (12)0.01411 (11)0.00242 (9)0.00563 (8)−0.00170 (9)
C260.01048 (9)0.00992 (9)0.01307 (10)−0.00087 (7)0.00388 (8)0.00067 (8)
C10.01086 (9)0.01265 (10)0.00912 (9)0.00178 (8)0.00210 (7)0.00076 (8)
C30.01186 (10)0.01500 (11)0.00877 (9)0.00089 (8)0.00103 (7)0.00038 (8)
C130.00998 (9)0.01231 (10)0.00956 (9)0.00182 (7)0.00230 (7)−0.00146 (7)
C190.01242 (10)0.01732 (12)0.01097 (10)0.00324 (9)0.00497 (8)0.00201 (9)
C50.01255 (10)0.01395 (11)0.00942 (9)−0.00016 (8)0.00219 (8)−0.00215 (8)
C200.01002 (9)0.01432 (11)0.01126 (10)0.00075 (8)0.00357 (7)0.00080 (8)
C40.01333 (10)0.01575 (12)0.00857 (9)−0.00039 (9)0.00058 (8)−0.00149 (8)
C180.01208 (10)0.01771 (12)0.00958 (9)0.00204 (9)0.00358 (8)0.00135 (9)
C160.01191 (10)0.01590 (12)0.00972 (9)0.00084 (8)0.00299 (8)0.00245 (8)
C230.01311 (11)0.01623 (12)0.01355 (11)0.00248 (9)0.00311 (9)−0.00316 (9)
C170.01145 (9)0.01481 (11)0.00978 (9)0.00106 (8)0.00266 (8)0.00021 (8)
C240.01191 (10)0.01279 (11)0.01468 (11)−0.00001 (8)0.00336 (8)−0.00290 (9)
C210.01191 (10)0.01310 (11)0.01366 (11)0.00267 (8)0.00421 (8)−0.00119 (9)
C250.01228 (10)0.00948 (9)0.01554 (11)−0.00091 (8)0.00190 (9)−0.00062 (8)
C220.01394 (11)0.01178 (11)0.01712 (13)0.00144 (9)0.00366 (9)−0.00079 (9)
Geometric parameters (Å, º) top
O3—C161.4266 (5)C7—H70.983 (10)
O3—C171.4296 (4)C10—H100.971 (10)
O6—C241.4234 (5)C26—C251.5100 (5)
O6—C251.4200 (4)C26—H26a0.964 (10)
O4—C191.4193 (4)C26—H26b1.006 (9)
O4—C181.4227 (4)C3—C41.3998 (5)
O5—C231.4213 (5)C3—H31.001 (10)
O5—C221.4262 (5)C13—H130.967 (10)
O2—C141.2347 (4)C19—C201.5196 (5)
O1—C11.2344 (5)C19—H19a0.975 (10)
N4—C141.3650 (4)C19—H19b1.001 (10)
N4—C151.4653 (4)C5—C41.3949 (5)
N4—C261.4777 (4)C5—H50.984 (10)
N2—N31.2514 (4)C20—H20a1.014 (9)
N2—C61.4199 (4)C20—H20b0.985 (9)
N1—C11.3629 (4)C4—H40.970 (10)
N1—C201.4709 (5)C18—C171.5185 (5)
N1—C211.4724 (5)C18—H18a0.938 (11)
N3—C81.4323 (4)C18—H18b0.959 (11)
C12—C141.4988 (4)C16—H16a0.950 (10)
C12—C111.4000 (5)C16—H16b0.949 (10)
C12—C131.3886 (4)C23—C241.5116 (5)
C8—C91.3932 (4)C23—H23a1.007 (11)
C8—C131.3995 (4)C23—H23b0.991 (11)
C2—C71.3941 (4)C17—H17a0.992 (10)
C2—C11.5019 (5)C17—H17b0.970 (10)
C2—C31.3999 (4)C24—H24a0.984 (11)
C11—C101.3924 (5)C24—H24b0.986 (11)
C11—H110.980 (11)C21—C221.5249 (5)
C15—C161.5245 (5)C21—H21a1.012 (10)
C15—H15a0.982 (9)C21—H21b0.995 (10)
C15—H15b0.998 (10)C25—H25a0.985 (10)
C9—C101.3975 (5)C25—H25b0.991 (9)
C9—H91.008 (10)C22—H22a0.975 (11)
C6—C71.3924 (5)C22—H22b1.003 (11)
C6—C51.3961 (4)
C17—O3—C16115.85 (3)H19b—C19—O4110.9 (6)
C25—O6—C24111.88 (3)H19b—C19—C20107.8 (6)
C18—O4—C19110.71 (3)H19b—C19—H19a105.5 (8)
C22—O5—C23114.10 (3)C4—C5—C6118.62 (3)
C15—N4—C14114.47 (3)H5—C5—C6120.6 (6)
C26—N4—C14119.21 (3)H5—C5—C4120.8 (6)
C26—N4—C15118.54 (3)C19—C20—N1114.33 (3)
C6—N2—N3115.60 (3)H20a—C20—N1107.8 (5)
C20—N1—C1122.38 (3)H20a—C20—C19107.9 (5)
C21—N1—C1116.47 (3)H20b—C20—N1108.1 (6)
C21—N1—C20116.96 (3)H20b—C20—C19111.5 (6)
C8—N3—N2111.81 (3)H20b—C20—H20a107.0 (8)
C11—C12—C14120.91 (3)C5—C4—C3120.74 (3)
C13—C12—C14118.61 (3)H4—C4—C3118.4 (6)
C13—C12—C11120.09 (3)H4—C4—C5120.8 (6)
C9—C8—N3117.87 (3)C17—C18—O4108.89 (3)
C13—C8—N3121.37 (3)H18a—C18—O4109.1 (7)
C13—C8—C9120.66 (3)H18a—C18—C17112.1 (7)
C1—C2—C7118.82 (3)H18b—C18—O4109.0 (6)
C3—C2—C7119.38 (3)H18b—C18—C17108.9 (6)
C3—C2—C1120.91 (3)H18b—C18—H18a108.8 (9)
N4—C14—O2122.10 (3)C15—C16—O3113.62 (3)
C12—C14—O2119.42 (3)H16a—C16—O3109.4 (6)
C12—C14—N4118.21 (3)H16a—C16—C15109.8 (6)
C10—C11—C12119.88 (3)H16b—C16—O3106.0 (6)
H11—C11—C12122.6 (6)H16b—C16—C15108.0 (6)
H11—C11—C10117.4 (6)H16b—C16—H16a110.0 (8)
C16—C15—N4112.94 (3)C24—C23—O5107.97 (3)
H15a—C15—N4107.9 (5)H23a—C23—O5109.7 (6)
H15a—C15—C16108.2 (6)H23a—C23—C24109.4 (6)
H15b—C15—N4111.0 (6)H23b—C23—O5111.0 (6)
H15b—C15—C16107.5 (6)H23b—C23—C24109.5 (6)
H15b—C15—H15a109.3 (8)H23b—C23—H23a109.3 (9)
C10—C9—C8119.23 (3)C18—C17—O3105.84 (3)
H9—C9—C8119.7 (6)H17a—C17—O3111.9 (5)
H9—C9—C10121.1 (6)H17a—C17—C18110.6 (6)
C7—C6—N2112.66 (3)H17b—C17—O3110.0 (6)
C5—C6—N2126.27 (3)H17b—C17—C18110.6 (6)
C5—C6—C7120.97 (3)H17b—C17—H17a108.0 (8)
C6—C7—C2120.01 (3)C23—C24—O6107.51 (3)
H7—C7—C2121.1 (6)H24a—C24—O6109.4 (6)
H7—C7—C6118.7 (6)H24a—C24—C23110.6 (6)
C9—C10—C11120.40 (3)H24b—C24—O6111.0 (7)
H10—C10—C11119.9 (6)H24b—C24—C23109.5 (7)
H10—C10—C9119.7 (6)H24b—C24—H24a108.9 (9)
C25—C26—N4115.36 (3)C22—C21—N1114.52 (3)
H26a—C26—N4109.2 (6)H21a—C21—N1108.5 (6)
H26a—C26—C25108.0 (6)H21a—C21—C22109.5 (6)
H26b—C26—N4108.3 (5)H21b—C21—N1108.2 (6)
H26b—C26—C25107.9 (5)H21b—C21—C22107.3 (6)
H26b—C26—H26a107.9 (8)H21b—C21—H21a108.7 (8)
N1—C1—O1121.96 (3)C26—C25—O6111.08 (3)
C2—C1—O1118.79 (3)H25a—C25—O6109.7 (6)
C2—C1—N1118.98 (3)H25a—C25—C26107.9 (6)
C4—C3—C2119.87 (3)H25b—C25—O6109.1 (5)
H3—C3—C2120.2 (6)H25b—C25—C26112.4 (6)
H3—C3—C4119.9 (6)H25b—C25—H25a106.5 (8)
C8—C13—C12119.64 (3)C21—C22—O5113.91 (3)
H13—C13—C12121.9 (6)H22a—C22—O5109.5 (6)
H13—C13—C8118.5 (6)H22a—C22—C21110.4 (6)
C20—C19—O4110.93 (3)H22b—C22—O5104.2 (6)
H19a—C19—O4109.5 (6)H22b—C22—C21108.0 (6)
H19a—C19—C20112.1 (6)H22b—C22—H22a110.7 (9)
O3—C16—C15—N475.11 (3)C8—C13—C12—C14172.35 (3)
O3—C17—C18—O4−166.08 (3)C8—C13—C12—C11−0.50 (4)
O6—C24—C23—O5−166.56 (3)C2—C7—C6—C56.63 (4)
O6—C25—C26—N468.96 (3)C2—C1—N1—C2030.84 (4)
O4—C19—C20—N173.35 (3)C2—C1—N1—C21−172.90 (3)
O5—C22—C21—N162.93 (3)C2—C3—C4—C54.13 (4)
O2—C14—N4—C153.22 (4)C14—N4—C15—C1675.33 (3)
O2—C14—N4—C26−145.64 (3)C14—N4—C26—C25−158.72 (3)
O2—C14—C12—C1151.03 (4)C14—C12—C11—C10−174.68 (3)
O2—C14—C12—C13−121.76 (3)C15—N4—C26—C2553.67 (3)
O1—C1—N1—C20−155.20 (3)C15—C16—O3—C17−92.93 (3)
O1—C1—N1—C211.05 (4)C6—C7—C2—C1163.55 (3)
O1—C1—C2—C7−123.76 (4)C6—C7—C2—C3−5.77 (4)
O1—C1—C2—C345.39 (4)C6—C5—C4—C3−3.32 (4)
N4—C14—C12—C11−134.73 (3)C7—C2—C3—C40.46 (4)
N4—C14—C12—C1352.47 (3)C7—C6—C5—C4−2.05 (4)
N2—N3—C8—C9−167.33 (3)C10—C11—C12—C13−1.99 (4)
N2—N3—C8—C1316.24 (4)C10—C9—C8—C13−3.28 (4)
N2—C6—C7—C2−169.91 (3)C26—N4—C15—C16−135.58 (3)
N2—C6—C5—C4173.99 (4)C26—C25—O6—C24−164.27 (3)
N1—C1—C2—C750.39 (4)C1—N1—C20—C19−138.24 (3)
N1—C1—C2—C3−140.47 (3)C1—N1—C21—C2273.02 (3)
N3—N2—C6—C7144.69 (3)C1—C2—C3—C4−168.62 (3)
N3—N2—C6—C5−31.63 (4)C19—O4—C18—C17−176.96 (3)
N3—C8—C9—C10−179.74 (3)C19—C20—N1—C2165.61 (3)
N3—C8—C13—C12179.50 (3)C20—N1—C21—C22−129.41 (3)
C12—C14—N4—C15−170.85 (3)C20—C19—O4—C18−169.69 (3)
C12—C14—N4—C2640.28 (3)C18—C17—O3—C16−163.18 (3)
C12—C11—C10—C91.87 (4)C23—O5—C22—C21−94.39 (3)
C12—C13—C8—C93.16 (4)C23—C24—O6—C25−161.06 (3)
C8—N3—N2—C6−171.60 (3)C24—C23—O5—C22−160.18 (3)
C8—C9—C10—C110.75 (4)
Poly[[{µ-7,16-[3,3'-(diazene-1,2-diyl)bis(1,3-phenylenecarbonyl)]-1,4,10,13-\ tetraoxa-7,16-diazacyclooctadecane}bis{tetrakis[3,5-bis(trifluoromethyl)\ phenyl]borato}disodium] benzene disolvate] (2) top
Crystal data top
[Na2(C32H12F24B)2(C26H32N4O6)]·2C6H6Z = 2
Mr = 2425.20F(000) = 2440
Triclinic, P1Dx = 1.583 Mg m−3
a = 13.5857 (6) ÅCu Kα radiation, λ = 1.54178 Å
b = 13.8054 (6) ÅCell parameters from 5022 reflections
c = 27.8552 (11) Åθ = 3.2–50.6°
α = 84.152 (2)°µ = 1.49 mm−1
β = 78.185 (2)°T = 100 K
γ = 89.238 (2)°Block, yellow
V = 5087.0 (4) Å30.30 × 0.28 × 0.24 mm
Data collection top
Bruker APEXII CCD
diffractometer		18230 reflections with I > 2σ(I)
φ and ω scansRint = 0.044
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)		θmax = 75.0°, θmin = 1.6°
Tmin = 0.342, Tmax = 0.471h = −17→16
168897 measured reflectionsk = −17→17
20857 independent reflectionsl = −34→34
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.071H-atom parameters constrained
wR(F2) = 0.205 w = 1/[σ2(Fo2) + (0.107P)2 + 6.5402P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
20857 reflectionsΔρmax = 1.45 e Å−3
1473 parametersΔρmin = −0.76 e Å−3
244 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Na10.79144 (8)0.56214 (8)0.69720 (4)0.0363 (2)
Na20.82395 (8)0.04313 (7)0.80949 (5)0.0404 (3)
F10.64788 (12)0.08277 (12)0.84767 (7)0.0397 (4)
F491.16929 (13)0.95580 (13)0.33335 (7)0.0436 (4)
F420.45824 (15)−0.16014 (13)0.69901 (7)0.0464 (4)
F20.67148 (13)0.12595 (14)0.77007 (7)0.0488 (4)
F320.11455 (15)−0.44091 (12)0.92366 (8)0.0496 (5)
F250.17784 (15)0.28699 (14)0.87623 (7)0.0492 (4)
F280.00420 (15)0.00748 (14)0.80757 (8)0.0514 (5)
F310.00300 (15)−0.43162 (14)0.87917 (7)0.0501 (5)
F27−0.06317 (15)−0.11943 (16)0.79216 (8)0.0582 (5)
F481.08307 (17)0.92317 (14)0.28133 (7)0.0553 (5)
F30.55899 (14)0.19707 (12)0.82154 (9)0.0540 (5)
O10.73355 (14)0.92050 (12)0.79017 (7)0.0319 (4)
O60.76352 (14)0.41487 (13)0.74800 (7)0.0338 (4)
F200.82181 (15)0.74482 (16)0.23338 (7)0.0537 (5)
F501.02660 (15)1.02375 (12)0.33210 (9)0.0579 (5)
F30−0.02954 (15)−0.38043 (15)0.95094 (7)0.0533 (5)
F260.32964 (16)0.28838 (14)0.88404 (9)0.0599 (6)
F230.37819 (14)0.73798 (19)0.40928 (7)0.0614 (6)
F180.77922 (18)0.89430 (14)0.23004 (7)0.0585 (5)
F170.48010 (16)1.08002 (16)0.42721 (8)0.0591 (5)
F350.53559 (15)−0.46707 (15)0.91413 (10)0.0635 (6)
F190.68738 (16)0.78969 (18)0.20878 (7)0.0589 (5)
F440.32652 (15)−0.07330 (18)0.70404 (7)0.0576 (5)
F461.04253 (16)0.55450 (16)0.45488 (8)0.0627 (6)
O50.63713 (14)0.57436 (13)0.74975 (7)0.0340 (4)
F330.39215 (19)−0.51580 (14)0.95178 (9)0.0675 (7)
F410.16972 (17)−0.02471 (18)1.08371 (7)0.0606 (5)
F400.02645 (14)−0.01428 (16)1.06328 (9)0.0634 (6)
F340.4135 (2)−0.45001 (15)0.87792 (8)0.0670 (7)
F290.08372 (15)−0.07806 (19)0.75250 (7)0.0615 (6)
F430.4703 (2)−0.01010 (15)0.67082 (7)0.0620 (6)
O40.84497 (15)0.71919 (14)0.70406 (8)0.0382 (4)
F240.2121 (3)0.33598 (13)0.94105 (8)0.0777 (8)
F150.52199 (18)1.18410 (17)0.47126 (8)0.0646 (6)
F471.17825 (15)0.62878 (16)0.42027 (11)0.0697 (7)
O30.94666 (16)0.54332 (15)0.72298 (8)0.0418 (5)
F370.47979 (18)−0.1502 (2)1.05499 (8)0.0709 (7)
O20.87808 (16)0.19102 (14)0.81237 (9)0.0422 (5)
F160.6039 (2)1.17583 (17)0.39756 (8)0.0681 (6)
F210.37267 (15)0.8021 (2)0.33648 (10)0.0790 (8)
F390.1001 (2)0.11241 (17)1.08176 (9)0.0800 (8)
F451.0975 (2)0.55171 (16)0.37743 (9)0.0705 (6)
F360.3411 (2)−0.2174 (3)1.08526 (8)0.0896 (10)
N30.66167 (16)0.78773 (15)0.76902 (8)0.0287 (4)
N20.77477 (17)0.55690 (16)0.89839 (8)0.0315 (4)
N10.77800 (17)0.50508 (16)0.93773 (8)0.0323 (5)
F510.6968 (3)0.3585 (2)0.49322 (13)0.0542 (7)0.651 (4)
N40.93762 (17)0.34103 (15)0.78021 (9)0.0324 (5)
F220.40159 (19)0.6514 (2)0.34986 (11)0.0832 (8)
C790.41705 (18)−0.34668 (18)0.94001 (9)0.0272 (5)
C810.4380 (2)−0.44388 (19)0.92118 (10)0.0308 (5)
C610.43523 (19)−0.04553 (18)0.75695 (9)0.0290 (5)
C680.14867 (17)−0.10063 (17)0.85063 (9)0.0255 (5)
H680.169181−0.0358500.8380880.031*
C20.68657 (18)0.79091 (18)0.85298 (10)0.0282 (5)
C531.02377 (19)0.85840 (18)0.36372 (9)0.0286 (5)
C590.37658 (17)−0.06285 (16)0.84663 (9)0.0242 (4)
C710.08055 (19)−0.28456 (18)0.88820 (9)0.0283 (5)
C750.35422 (17)−0.17995 (17)0.93006 (9)0.0239 (4)
C581.0760 (2)0.94004 (19)0.32896 (10)0.0318 (5)
C600.36990 (18)−0.08507 (17)0.79970 (9)0.0256 (5)
H600.318774−0.1289520.7966490.031*
C10.69211 (18)0.84015 (17)0.80227 (10)0.0282 (5)
C740.0253 (2)−0.0837 (2)0.79684 (11)0.0363 (6)
C830.25377 (17)−0.00701 (17)0.92802 (9)0.0262 (5)
C630.52154 (19)0.03838 (17)0.80627 (10)0.0300 (5)
C720.16071 (18)−0.24374 (17)0.90343 (9)0.0249 (5)
H720.190336−0.2800160.9275870.030*
C760.37507 (19)−0.16899 (19)0.97609 (9)0.0292 (5)
H760.363200−0.1077740.9889350.035*
C670.19896 (17)−0.15134 (17)0.88439 (9)0.0237 (4)
C541.0797 (2)0.7798 (2)0.37699 (10)0.0343 (5)
H541.1510020.7801830.3674000.041*
C40.73122 (19)0.65049 (18)0.90253 (10)0.0294 (5)
C640.45656 (18)−0.00113 (17)0.84866 (10)0.0275 (5)
H640.4664730.0139960.8798550.033*
C800.38002 (17)−0.27064 (17)0.91234 (9)0.0243 (4)
H800.371781−0.2803020.8801070.029*
C700.03493 (18)−0.2345 (2)0.85324 (10)0.0302 (5)
H70−0.018687−0.2629610.8422270.036*
C360.6486 (2)0.9616 (2)0.43628 (10)0.0347 (6)
H360.6130060.9463990.4119590.042*
C30.72610 (19)0.69805 (18)0.85692 (9)0.0287 (5)
H30.7499590.6667050.8279830.034*
C80.8276 (2)0.41532 (19)0.92672 (10)0.0326 (5)
C510.86629 (19)0.78246 (19)0.40981 (9)0.0299 (5)
C200.57063 (19)0.72539 (17)0.78492 (10)0.0284 (5)
H20A0.5108940.7677470.7866140.034*
H20B0.5699270.6948660.8187300.034*
C690.06970 (18)−0.14197 (19)0.83484 (9)0.0281 (5)
C520.92043 (19)0.86063 (18)0.37989 (9)0.0290 (5)
H520.8848260.9167270.3705070.035*
C430.68772 (19)0.78214 (18)0.38127 (9)0.0289 (5)
C840.2630 (2)0.08982 (18)0.90750 (10)0.0292 (5)
H840.2974840.1037610.8742520.035*
C850.2235 (2)0.16704 (19)0.93402 (10)0.0325 (5)
C350.7185 (2)0.8954 (2)0.45012 (10)0.0349 (6)
F60.7269 (3)0.6070 (4)0.62560 (10)0.1230 (15)
C890.20010 (19)−0.02175 (18)0.97705 (10)0.0311 (5)
H890.188559−0.0865550.9921760.037*
C60.6597 (2)0.7883 (2)0.94151 (11)0.0367 (6)
H60.6371770.8198840.9705110.044*
C860.1739 (2)0.1504 (2)0.98276 (11)0.0358 (6)
H860.1478090.2028501.0009730.043*
C650.5989 (2)0.1104 (2)0.81109 (12)0.0382 (6)
C450.6853 (2)0.78828 (18)0.29371 (9)0.0292 (5)
C440.73653 (19)0.79285 (18)0.33199 (9)0.0284 (5)
H440.8071840.8036480.3241360.034*
C780.4328 (2)−0.3348 (2)0.98695 (10)0.0329 (5)
H780.456530−0.3867921.0065050.040*
C50.6980 (2)0.6952 (2)0.94536 (10)0.0346 (6)
H50.7014510.6624180.9766470.042*
C261.0049 (2)0.42298 (18)0.78141 (11)0.0321 (5)
H26A1.0668040.4171590.7560430.039*
H26B1.0245330.4169200.8138980.039*
C620.51167 (19)0.01764 (18)0.75991 (10)0.0312 (5)
H620.5558720.0457840.7310590.037*
C570.9240 (2)0.7025 (2)0.42114 (11)0.0365 (6)
H570.8910730.6472880.4407240.044*
C770.4128 (2)−0.2447 (2)1.00401 (10)0.0344 (6)
C470.5323 (2)0.76036 (19)0.35215 (10)0.0325 (5)
C300.70528 (19)0.6976 (2)0.46927 (9)0.0314 (5)
C460.5828 (2)0.77201 (18)0.30334 (9)0.0303 (5)
H460.5478710.7688640.2772680.036*
C480.5834 (2)0.7654 (2)0.39029 (9)0.0323 (5)
H480.5467630.7572610.4233830.039*
C100.8990 (2)0.30204 (18)0.86919 (11)0.0334 (6)
C190.5598 (2)0.64553 (18)0.75285 (10)0.0314 (5)
H19A0.4942710.6123100.7659140.038*
H19B0.5587700.6757540.7191640.038*
C70.6535 (2)0.83700 (19)0.89552 (10)0.0329 (5)
H70.6270360.9009620.8933970.040*
C210.6949 (2)0.82243 (19)0.71667 (10)0.0337 (6)
H21A0.6733190.8907180.7111170.040*
H21B0.6618530.7827240.6967630.040*
C490.4219 (2)0.7403 (3)0.36258 (11)0.0449 (7)
C660.4225 (2)−0.0715 (2)0.70775 (10)0.0349 (6)
C90.8428 (2)0.38435 (18)0.87982 (10)0.0320 (5)
H90.8145190.4198650.8549620.038*
C110.9078 (2)0.27262 (18)0.81853 (12)0.0348 (6)
C370.6290 (2)1.0498 (2)0.45701 (11)0.0385 (6)
C160.8056 (2)0.3240 (2)0.73360 (13)0.0410 (7)
H16A0.7931540.3140450.7006460.049*
H16B0.7726900.2700520.7573550.049*
C180.6246 (2)0.50050 (19)0.79052 (11)0.0368 (6)
H18A0.5529070.4950190.8071660.044*
H18B0.6640060.5177170.8147120.044*
C730.0424 (2)−0.3839 (2)0.91049 (11)0.0378 (6)
C500.7429 (2)0.8037 (2)0.24191 (10)0.0359 (6)
C880.1148 (3)0.0337 (2)1.05892 (15)0.0536 (9)
C870.1632 (2)0.0548 (2)1.00431 (11)0.0369 (6)
C220.8074 (2)0.81712 (19)0.69938 (10)0.0345 (6)
H22A0.8256180.8442500.6644030.041*
H22B0.8403750.8579220.7188440.041*
C250.9619 (2)0.52419 (19)0.77284 (11)0.0359 (6)
H25A0.8969950.5295290.7962190.043*
H25B1.0086720.5735170.7791530.043*
C310.6931 (2)0.6057 (2)0.45463 (10)0.0376 (6)
H310.7034610.5983920.4204120.045*
C290.6877 (2)0.7033 (2)0.52002 (10)0.0376 (6)
H290.6930230.7646650.5319710.045*
C900.2362 (3)0.2692 (2)0.90921 (11)0.0418 (7)
C120.9377 (2)0.2480 (2)0.90618 (13)0.0420 (7)
H120.9756270.1909250.8992680.050*
C140.8653 (2)0.3616 (2)0.96365 (11)0.0394 (6)
H140.8537140.3817500.9959420.047*
F70.6254 (5)0.7164 (3)0.61997 (10)0.157 (2)
C820.4279 (3)−0.2290 (2)1.05449 (12)0.0476 (7)
C551.0282 (2)0.7002 (2)0.40485 (11)0.0377 (6)
C150.9177 (2)0.3234 (2)0.73211 (11)0.0377 (6)
H15A0.9457310.2596410.7230840.045*
H15B0.9511470.3744930.7066940.045*
C320.6664 (3)0.5241 (2)0.48841 (13)0.0472 (7)
C170.6603 (2)0.4053 (2)0.77174 (12)0.0402 (6)
H17A0.6521360.3533090.7995020.048*
H17B0.6199050.3874190.7481210.048*
F530.6487 (5)0.4236 (3)0.42838 (16)0.0829 (13)0.651 (4)
C280.6624 (2)0.6211 (3)0.55363 (11)0.0450 (7)
F380.4716 (4)−0.3013 (3)1.07532 (13)0.158 (2)
C130.9202 (3)0.2783 (2)0.95306 (13)0.0457 (7)
H130.9461680.2414950.9783270.055*
C561.0863 (2)0.6095 (2)0.41498 (12)0.0455 (7)
C230.9498 (2)0.7195 (2)0.70751 (14)0.0477 (7)
H23A0.9551180.7301430.7415050.057*
H23B0.9852970.7737880.6848860.057*
C400.7687 (3)0.9237 (3)0.48562 (14)0.0531 (8)
H400.8199030.8828380.4948850.064*
C240.9990 (2)0.6251 (3)0.69449 (13)0.0487 (7)
H24A1.0020850.6191560.6590990.058*
H24B1.0688560.6255050.6998310.058*
C330.6520 (2)0.5314 (3)0.53834 (12)0.0497 (8)
H330.6353880.4756550.5614960.060*
B20.2969 (2)−0.10015 (19)0.89780 (10)0.0235 (5)
F80.5764 (4)0.5769 (4)0.63442 (11)0.156 (2)
C420.5589 (3)1.1218 (2)0.43876 (12)0.0450 (7)
C380.6770 (3)1.0742 (3)0.49333 (15)0.0531 (8)
H380.6628211.1335560.5078040.064*
C340.6474 (4)0.4295 (3)0.47183 (17)0.0710 (10)
C270.6470 (3)0.6313 (4)0.60749 (12)0.0631 (11)
C390.7463 (3)1.0095 (3)0.50793 (18)0.0667 (11)
B10.7436 (2)0.7898 (2)0.42783 (10)0.0297 (6)
F40.5481 (3)0.3968 (3)0.49816 (19)0.0848 (12)0.651 (4)
F120.7703 (18)0.9965 (14)0.5882 (7)0.1334 (19)0.229 (6)
C950.3063 (3)−0.5185 (2)0.76995 (14)0.0929 (18)
H950.314583−0.5813850.7858350.111*
C940.3364 (3)−0.5005 (2)0.71906 (13)0.0891 (16)
H940.365336−0.5510790.7001650.107*
C930.3243 (2)−0.4084 (2)0.69582 (8)0.0754 (13)
H930.344936−0.3960910.6610390.090*
C920.2821 (2)−0.33433 (18)0.72347 (12)0.0698 (12)
H920.273783−0.2714060.7075830.084*
C910.2519 (2)−0.3523 (2)0.77436 (12)0.0774 (14)
H910.223029−0.3017090.7932530.093*
C960.2640 (2)−0.4444 (3)0.79760 (8)0.0839 (16)
H960.243429−0.4566980.8323800.101*
C980.9851 (4)0.6908 (3)0.55626 (16)0.112 (2)
H980.9459410.6431740.5462050.134*
C991.0817 (4)0.6686 (3)0.56317 (19)0.124 (3)
H991.1084590.6057390.5578400.149*
C1001.1391 (3)0.7383 (4)0.5779 (2)0.149 (4)
H1001.2050340.7230730.5825970.179*
C1011.0999 (4)0.8302 (3)0.58567 (19)0.127 (3)
H1011.1390920.8778420.5957190.152*
C1021.0033 (4)0.8524 (3)0.57876 (19)0.142 (3)
H1020.9765750.9152780.5840840.171*
C970.9460 (4)0.7827 (4)0.56405 (17)0.131 (3)
H970.8799980.7979460.5593270.158*
C410.8018 (5)1.0322 (4)0.5480 (3)0.1022 (18)
F110.7722 (6)0.9573 (4)0.5871 (2)0.1334 (19)0.771 (6)
F140.7752 (5)1.1196 (4)0.5645 (2)0.1277 (17)0.771 (6)
F50.6600 (7)0.3428 (6)0.4916 (4)0.0848 (12)0.349 (4)
F540.5776 (8)0.4334 (6)0.4431 (3)0.0829 (13)0.349 (4)
F520.7243 (6)0.4212 (4)0.4222 (2)0.0542 (7)0.349 (4)
F130.8040 (17)1.0874 (12)0.5621 (8)0.1277 (17)0.229 (6)
F100.8627 (12)0.9582 (11)0.5646 (8)0.1187 (17)0.229 (6)
F90.9024 (4)1.0369 (3)0.5308 (2)0.1187 (17)0.771 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Na10.0347 (5)0.0317 (5)0.0435 (6)−0.0021 (4)−0.0130 (5)0.0012 (4)
Na20.0292 (5)0.0224 (5)0.0718 (8)−0.0030 (4)−0.0142 (5)−0.0080 (5)
F10.0319 (8)0.0366 (8)0.0533 (10)−0.0072 (6)−0.0105 (7)−0.0128 (7)
F490.0354 (8)0.0477 (10)0.0474 (10)−0.0170 (7)−0.0151 (7)0.0118 (8)
F420.0630 (11)0.0385 (9)0.0442 (9)0.0117 (8)−0.0224 (8)−0.0134 (7)
F20.0393 (9)0.0456 (10)0.0560 (11)−0.0181 (8)0.0000 (8)0.0034 (8)
F320.0565 (11)0.0286 (8)0.0664 (12)−0.0124 (7)−0.0241 (9)0.0070 (8)
F250.0570 (11)0.0467 (10)0.0430 (10)0.0116 (8)−0.0132 (8)0.0049 (8)
F280.0608 (12)0.0443 (10)0.0578 (11)0.0163 (8)−0.0337 (9)−0.0043 (8)
F310.0609 (11)0.0441 (10)0.0496 (10)−0.0276 (9)−0.0193 (9)−0.0052 (8)
F270.0435 (10)0.0704 (13)0.0709 (13)−0.0032 (9)−0.0393 (10)0.0020 (10)
F480.0822 (14)0.0503 (11)0.0342 (9)−0.0325 (10)−0.0177 (9)0.0076 (8)
F30.0441 (10)0.0222 (8)0.0938 (15)−0.0051 (7)−0.0090 (10)−0.0066 (8)
O10.0323 (9)0.0206 (8)0.0440 (10)−0.0040 (7)−0.0105 (8)−0.0023 (7)
O60.0348 (9)0.0212 (8)0.0473 (11)−0.0018 (7)−0.0113 (8)−0.0053 (7)
F200.0568 (11)0.0655 (12)0.0335 (9)0.0280 (10)0.0002 (8)−0.0028 (8)
F500.0458 (10)0.0243 (8)0.0939 (16)−0.0043 (7)0.0027 (10)0.0065 (9)
F300.0537 (11)0.0582 (11)0.0422 (10)−0.0246 (9)0.0023 (8)0.0009 (8)
F260.0592 (12)0.0326 (9)0.0894 (16)−0.0138 (8)−0.0263 (11)0.0109 (9)
F230.0355 (9)0.1041 (18)0.0407 (10)−0.0165 (10)−0.0051 (8)0.0078 (10)
F180.0777 (14)0.0439 (10)0.0410 (10)−0.0065 (9)0.0110 (9)0.0109 (8)
F170.0549 (12)0.0632 (13)0.0646 (13)0.0194 (10)−0.0231 (10)−0.0129 (10)
F350.0373 (10)0.0493 (11)0.1088 (18)0.0093 (8)−0.0149 (10)−0.0328 (12)
F190.0567 (12)0.0943 (16)0.0271 (8)0.0073 (11)−0.0114 (8)−0.0084 (9)
F440.0459 (10)0.0940 (16)0.0408 (10)0.0187 (10)−0.0219 (8)−0.0197 (10)
F460.0581 (12)0.0528 (12)0.0641 (13)0.0078 (9)−0.0005 (10)0.0308 (10)
O50.0355 (10)0.0227 (8)0.0423 (10)−0.0020 (7)−0.0053 (8)−0.0005 (7)
F330.0890 (16)0.0311 (9)0.0663 (13)−0.0153 (10)0.0221 (12)−0.0041 (9)
F410.0619 (13)0.0806 (15)0.0368 (10)−0.0031 (11)−0.0048 (9)−0.0037 (9)
F400.0362 (10)0.0606 (12)0.0803 (15)−0.0075 (9)0.0040 (9)0.0232 (11)
F340.1185 (19)0.0427 (10)0.0566 (12)0.0306 (11)−0.0504 (13)−0.0224 (9)
F290.0507 (11)0.0998 (17)0.0314 (9)0.0251 (11)−0.0108 (8)0.0071 (10)
F430.1007 (17)0.0529 (11)0.0276 (9)−0.0200 (11)−0.0051 (9)0.0047 (8)
O40.0399 (10)0.0286 (9)0.0454 (11)−0.0092 (8)−0.0112 (9)0.0053 (8)
F240.167 (3)0.0241 (9)0.0442 (11)0.0094 (12)−0.0242 (13)−0.0093 (8)
F150.0775 (15)0.0651 (13)0.0573 (12)0.0339 (11)−0.0201 (11)−0.0264 (10)
F470.0399 (10)0.0562 (12)0.113 (2)0.0003 (9)−0.0306 (11)0.0239 (12)
O30.0413 (11)0.0367 (10)0.0479 (12)−0.0037 (8)−0.0162 (9)0.0086 (9)
F370.0725 (14)0.1047 (19)0.0419 (11)−0.0375 (13)−0.0179 (10)−0.0199 (11)
O20.0418 (11)0.0222 (9)0.0650 (14)−0.0025 (8)−0.0145 (10)−0.0081 (9)
F160.0863 (16)0.0577 (13)0.0524 (12)0.0106 (11)−0.0050 (11)0.0116 (10)
F210.0367 (10)0.113 (2)0.0779 (16)−0.0099 (11)−0.0192 (10)0.0515 (15)
F390.110 (2)0.0496 (12)0.0602 (14)−0.0120 (12)0.0351 (13)−0.0162 (10)
F450.0969 (18)0.0500 (12)0.0663 (14)0.0244 (12)−0.0222 (13)−0.0060 (10)
F360.0874 (17)0.147 (3)0.0331 (10)−0.0573 (18)0.0037 (11)−0.0282 (13)
N30.0328 (11)0.0223 (9)0.0321 (11)−0.0056 (8)−0.0111 (9)0.0015 (8)
N20.0362 (11)0.0294 (11)0.0293 (11)0.0003 (9)−0.0101 (9)0.0013 (8)
N10.0351 (11)0.0304 (11)0.0307 (11)−0.0056 (9)−0.0082 (9)0.0039 (9)
F510.078 (2)0.0340 (13)0.0499 (14)−0.0099 (13)−0.0139 (14)0.0019 (11)
N40.0350 (11)0.0227 (10)0.0424 (12)−0.0007 (8)−0.0133 (9)−0.0067 (9)
F220.0622 (14)0.0873 (18)0.101 (2)−0.0401 (13)−0.0126 (13)−0.0176 (15)
C790.0274 (11)0.0264 (11)0.0273 (12)−0.0002 (9)−0.0068 (9)0.0018 (9)
C810.0343 (13)0.0274 (12)0.0307 (12)0.0011 (10)−0.0092 (10)0.0030 (10)
C610.0321 (12)0.0252 (11)0.0292 (12)0.0027 (9)−0.0071 (10)0.0014 (9)
C680.0240 (11)0.0262 (11)0.0269 (11)0.0000 (9)−0.0075 (9)−0.0010 (9)
C20.0269 (11)0.0255 (11)0.0339 (13)−0.0040 (9)−0.0103 (10)−0.0030 (9)
C530.0321 (12)0.0267 (12)0.0282 (12)−0.0055 (9)−0.0091 (10)−0.0016 (9)
C590.0241 (11)0.0189 (10)0.0300 (12)0.0012 (8)−0.0088 (9)0.0016 (8)
C710.0269 (11)0.0291 (12)0.0296 (12)−0.0051 (9)−0.0054 (9)−0.0060 (10)
C750.0216 (10)0.0261 (11)0.0244 (11)−0.0032 (8)−0.0062 (8)−0.0007 (9)
C580.0339 (13)0.0261 (12)0.0367 (13)−0.0051 (10)−0.0108 (11)−0.0014 (10)
C600.0250 (11)0.0220 (10)0.0304 (12)−0.0002 (8)−0.0081 (9)−0.0005 (9)
C10.0274 (11)0.0215 (11)0.0366 (13)−0.0007 (9)−0.0093 (10)−0.0022 (9)
C740.0296 (13)0.0463 (15)0.0363 (14)0.0033 (11)−0.0142 (11)−0.0055 (12)
C830.0220 (11)0.0252 (11)0.0341 (12)−0.0016 (8)−0.0114 (9)−0.0042 (9)
C630.0274 (12)0.0217 (11)0.0408 (14)−0.0011 (9)−0.0085 (10)0.0011 (10)
C720.0252 (11)0.0266 (11)0.0237 (11)−0.0026 (9)−0.0073 (9)−0.0015 (9)
C760.0293 (12)0.0324 (12)0.0285 (12)0.0007 (10)−0.0103 (10)−0.0062 (10)
C670.0235 (11)0.0242 (11)0.0243 (11)−0.0008 (8)−0.0062 (9)−0.0039 (8)
C540.0274 (12)0.0360 (14)0.0387 (14)−0.0034 (10)−0.0073 (10)0.0018 (11)
C40.0296 (12)0.0285 (12)0.0314 (12)−0.0017 (9)−0.0091 (10)−0.0031 (10)
C640.0269 (11)0.0235 (11)0.0333 (12)−0.0010 (9)−0.0105 (10)−0.0004 (9)
C800.0248 (11)0.0257 (11)0.0231 (11)−0.0010 (9)−0.0072 (9)−0.0009 (9)
C700.0243 (11)0.0377 (13)0.0318 (12)−0.0025 (10)−0.0093 (9)−0.0103 (10)
C360.0357 (13)0.0401 (14)0.0267 (12)−0.0006 (11)−0.0035 (10)−0.0019 (10)
C30.0311 (12)0.0263 (11)0.0298 (12)−0.0007 (9)−0.0083 (10)−0.0039 (9)
C80.0326 (13)0.0275 (12)0.0370 (13)−0.0081 (10)−0.0096 (10)0.0064 (10)
C510.0315 (12)0.0315 (12)0.0272 (12)−0.0038 (10)−0.0075 (10)−0.0018 (9)
C200.0286 (12)0.0236 (11)0.0341 (12)−0.0027 (9)−0.0093 (10)−0.0016 (9)
C690.0240 (11)0.0352 (13)0.0270 (12)0.0038 (9)−0.0078 (9)−0.0072 (10)
C520.0327 (12)0.0271 (12)0.0285 (12)−0.0020 (9)−0.0096 (10)−0.0019 (9)
C430.0324 (12)0.0286 (12)0.0251 (12)−0.0015 (9)−0.0056 (9)0.0004 (9)
C840.0341 (13)0.0253 (11)0.0315 (12)0.0008 (9)−0.0138 (10)−0.0048 (9)
C850.0391 (14)0.0255 (12)0.0374 (14)0.0012 (10)−0.0170 (11)−0.0055 (10)
C350.0334 (13)0.0387 (14)0.0326 (13)−0.0010 (11)−0.0060 (11)−0.0041 (11)
F60.105 (2)0.231 (4)0.0418 (13)0.066 (3)−0.0362 (14)−0.0198 (19)
C890.0268 (12)0.0243 (11)0.0406 (14)−0.0025 (9)−0.0024 (10)−0.0045 (10)
C60.0387 (14)0.0393 (14)0.0340 (14)−0.0001 (11)−0.0078 (11)−0.0118 (11)
C860.0337 (13)0.0278 (12)0.0472 (16)0.0014 (10)−0.0070 (11)−0.0115 (11)
C650.0318 (13)0.0257 (12)0.0544 (17)−0.0046 (10)−0.0030 (12)−0.0025 (11)
C450.0387 (13)0.0233 (11)0.0250 (12)0.0023 (9)−0.0067 (10)0.0002 (9)
C440.0308 (12)0.0260 (11)0.0277 (12)−0.0014 (9)−0.0055 (10)0.0002 (9)
C780.0375 (14)0.0343 (13)0.0286 (12)0.0035 (10)−0.0132 (10)0.0020 (10)
C50.0373 (14)0.0388 (14)0.0295 (13)−0.0049 (11)−0.0112 (11)−0.0016 (10)
C260.0323 (13)0.0245 (12)0.0419 (14)−0.0039 (10)−0.0142 (11)−0.0004 (10)
C620.0305 (12)0.0231 (11)0.0369 (13)0.0002 (9)−0.0034 (10)0.0047 (10)
C570.0333 (13)0.0349 (14)0.0387 (14)−0.0059 (11)−0.0070 (11)0.0085 (11)
C770.0382 (14)0.0407 (14)0.0277 (13)0.0021 (11)−0.0147 (11)−0.0036 (11)
C470.0347 (13)0.0320 (13)0.0304 (13)−0.0057 (10)−0.0097 (10)0.0052 (10)
C300.0249 (11)0.0433 (14)0.0254 (12)−0.0009 (10)−0.0052 (9)0.0004 (10)
C460.0411 (14)0.0251 (11)0.0264 (12)−0.0020 (10)−0.0124 (10)0.0016 (9)
C480.0328 (13)0.0387 (14)0.0239 (11)−0.0041 (10)−0.0056 (10)0.0041 (10)
C100.0322 (13)0.0215 (11)0.0469 (15)−0.0058 (9)−0.0116 (11)0.0028 (10)
C190.0307 (12)0.0274 (12)0.0379 (13)−0.0039 (10)−0.0111 (10)−0.0036 (10)
C70.0318 (13)0.0294 (12)0.0401 (14)0.0004 (10)−0.0110 (11)−0.0078 (10)
C210.0425 (14)0.0270 (12)0.0333 (13)−0.0084 (10)−0.0148 (11)0.0040 (10)
C490.0385 (15)0.0590 (19)0.0363 (15)−0.0132 (13)−0.0134 (12)0.0125 (13)
C660.0378 (14)0.0346 (13)0.0312 (13)0.0033 (11)−0.0070 (11)0.0013 (10)
C90.0341 (13)0.0245 (11)0.0382 (14)−0.0046 (10)−0.0128 (11)0.0041 (10)
C110.0307 (13)0.0209 (11)0.0545 (17)−0.0011 (9)−0.0135 (12)−0.0015 (11)
C370.0383 (14)0.0396 (15)0.0356 (14)0.0023 (12)−0.0029 (11)−0.0044 (11)
C160.0446 (16)0.0270 (13)0.0586 (18)0.0024 (11)−0.0217 (14)−0.0153 (12)
C180.0423 (15)0.0268 (12)0.0397 (14)−0.0022 (11)−0.0065 (12)0.0004 (11)
C730.0375 (14)0.0378 (14)0.0394 (15)−0.0152 (11)−0.0110 (12)−0.0010 (11)
C500.0432 (15)0.0371 (14)0.0264 (12)0.0059 (11)−0.0068 (11)−0.0002 (10)
C880.0452 (17)0.0307 (14)0.072 (2)−0.0054 (13)0.0226 (16)−0.0109 (14)
C870.0320 (13)0.0311 (13)0.0453 (15)−0.0040 (10)−0.0003 (11)−0.0083 (11)
C220.0448 (15)0.0241 (12)0.0330 (13)−0.0095 (10)−0.0071 (11)0.0044 (10)
C250.0427 (15)0.0236 (12)0.0426 (15)−0.0032 (10)−0.0122 (12)−0.0020 (10)
C310.0424 (15)0.0412 (15)0.0301 (13)−0.0076 (12)−0.0126 (11)0.0032 (11)
C290.0356 (14)0.0502 (16)0.0267 (13)0.0074 (12)−0.0073 (10)−0.0017 (11)
C900.0601 (19)0.0273 (13)0.0413 (15)0.0047 (12)−0.0166 (14)−0.0072 (11)
C120.0409 (15)0.0247 (12)0.0615 (19)−0.0018 (11)−0.0184 (14)0.0078 (12)
C140.0454 (16)0.0355 (14)0.0376 (14)−0.0068 (12)−0.0154 (12)0.0101 (11)
F70.301 (6)0.137 (3)0.0295 (12)0.101 (4)−0.030 (2)−0.0163 (16)
C820.066 (2)0.0480 (17)0.0356 (15)0.0058 (15)−0.0245 (15)−0.0087 (13)
C550.0350 (14)0.0366 (14)0.0399 (15)−0.0013 (11)−0.0091 (11)0.0078 (11)
C150.0429 (15)0.0299 (13)0.0446 (15)0.0033 (11)−0.0144 (12)−0.0133 (11)
C320.0481 (17)0.0437 (17)0.0520 (18)−0.0107 (13)−0.0215 (14)0.0089 (14)
C170.0392 (15)0.0243 (12)0.0558 (18)−0.0051 (11)−0.0072 (13)−0.0027 (12)
F530.130 (4)0.0579 (18)0.070 (2)0.007 (3)−0.038 (3)−0.0160 (17)
C280.0383 (15)0.063 (2)0.0302 (14)0.0057 (14)−0.0070 (11)0.0091 (13)
F380.321 (6)0.110 (2)0.101 (2)0.120 (3)−0.157 (3)−0.061 (2)
C130.0509 (18)0.0372 (15)0.0500 (18)−0.0011 (13)−0.0207 (14)0.0115 (13)
C560.0415 (16)0.0458 (17)0.0455 (17)−0.0017 (13)−0.0081 (13)0.0115 (13)
C230.0387 (15)0.0366 (15)0.066 (2)−0.0116 (12)−0.0121 (14)0.0050 (14)
C400.0515 (19)0.0541 (19)0.065 (2)0.0148 (15)−0.0293 (17)−0.0251 (17)
C240.0390 (16)0.0509 (18)0.0539 (19)−0.0041 (13)−0.0101 (14)0.0081 (15)
C330.0399 (16)0.062 (2)0.0433 (17)−0.0098 (14)−0.0139 (13)0.0234 (15)
B20.0253 (12)0.0212 (11)0.0258 (12)−0.0022 (9)−0.0101 (10)−0.0002 (9)
F80.159 (4)0.245 (6)0.0458 (16)−0.094 (4)0.0219 (19)−0.001 (2)
C420.0503 (17)0.0460 (17)0.0369 (15)0.0096 (14)−0.0047 (13)−0.0064 (12)
C380.056 (2)0.0452 (18)0.066 (2)0.0073 (15)−0.0213 (17)−0.0229 (16)
C340.088 (3)0.0485 (19)0.087 (3)−0.0143 (18)−0.043 (2)−0.0001 (18)
C270.066 (2)0.088 (3)0.0286 (16)0.018 (2)−0.0040 (15)0.0117 (17)
C390.070 (2)0.063 (2)0.085 (3)0.0181 (19)−0.042 (2)−0.039 (2)
B10.0301 (14)0.0340 (14)0.0247 (13)−0.0012 (11)−0.0058 (10)−0.0018 (11)
F40.072 (2)0.0543 (19)0.130 (3)−0.0187 (16)−0.024 (2)−0.0120 (19)
F120.213 (4)0.114 (4)0.117 (3)0.029 (4)−0.118 (3)−0.050 (3)
C950.096 (4)0.069 (3)0.116 (5)−0.036 (3)−0.044 (3)0.033 (3)
C940.103 (4)0.066 (3)0.107 (4)0.003 (3)−0.024 (3)−0.046 (3)
C930.075 (3)0.105 (4)0.044 (2)−0.019 (3)−0.0058 (19)−0.010 (2)
C920.054 (2)0.054 (2)0.103 (4)−0.0120 (17)−0.023 (2)0.001 (2)
C910.045 (2)0.101 (4)0.089 (3)−0.009 (2)−0.001 (2)−0.048 (3)
C960.059 (3)0.138 (5)0.052 (2)−0.039 (3)−0.0033 (19)−0.007 (3)
C980.147 (6)0.111 (5)0.070 (3)0.021 (4)−0.007 (4)−0.006 (3)
C990.096 (5)0.096 (4)0.153 (7)−0.009 (4)0.046 (5)−0.032 (4)
C1000.077 (4)0.117 (6)0.225 (10)−0.012 (4)0.053 (5)−0.049 (6)
C1010.114 (5)0.119 (5)0.124 (6)−0.002 (4)0.043 (5)−0.040 (5)
C1020.186 (9)0.152 (7)0.102 (5)0.063 (7)−0.043 (6)−0.056 (5)
C970.195 (9)0.134 (6)0.077 (4)0.050 (6)−0.048 (5)−0.031 (4)
C410.133 (4)0.071 (3)0.137 (4)0.053 (3)−0.084 (4)−0.067 (3)
F110.213 (4)0.114 (4)0.117 (3)0.029 (4)−0.118 (3)−0.050 (3)
F140.180 (4)0.087 (3)0.169 (3)0.067 (3)−0.126 (3)−0.092 (3)
F50.072 (2)0.0543 (19)0.130 (3)−0.0187 (16)−0.024 (2)−0.0120 (19)
F540.130 (4)0.0579 (18)0.070 (2)0.007 (3)−0.038 (3)−0.0160 (17)
F520.078 (2)0.0340 (13)0.0499 (14)−0.0099 (13)−0.0139 (14)0.0019 (11)
F130.180 (4)0.087 (3)0.169 (3)0.067 (3)−0.126 (3)−0.092 (3)
F100.110 (3)0.092 (3)0.193 (5)0.008 (2)−0.112 (3)−0.036 (3)
F90.110 (3)0.092 (3)0.193 (5)0.008 (2)−0.112 (3)−0.036 (3)
Geometric parameters (Å, º) top
Na1—O62.344 (2)C43—C441.391 (4)
Na1—O52.313 (2)C43—C481.406 (4)
Na1—O42.334 (2)C43—B11.644 (4)
Na1—O32.366 (2)C84—H840.9500
Na1—F45i2.896 (3)C84—C851.398 (4)
Na1—F62.362 (3)C85—C861.384 (4)
Na2—F12.489 (2)C85—C901.502 (4)
Na2—F22.723 (2)C35—C401.398 (4)
Na2—F28ii2.482 (2)C35—B11.647 (4)
Na2—F27ii2.729 (3)F6—C271.314 (5)
Na2—F48i2.584 (2)C89—H890.9500
Na2—O1iii2.275 (2)C89—C871.393 (4)
Na2—F41iv2.979 (2)C6—H60.9500
Na2—O22.194 (2)C6—C51.383 (4)
F1—C651.348 (4)C6—C71.402 (4)
F49—C581.321 (3)C86—H860.9500
F42—C661.338 (3)C86—C871.389 (4)
F2—C651.348 (3)C45—C441.395 (4)
F32—C731.335 (4)C45—C461.380 (4)
F25—C901.335 (4)C45—C501.490 (4)
F28—C741.337 (4)C44—H440.9500
F31—C731.341 (3)C78—H780.9500
F27—C741.341 (3)C78—C771.379 (4)
F48—C581.354 (3)C5—H50.9500
F3—C651.342 (3)C26—H26A0.9900
O1—C11.234 (3)C26—H26B0.9900
O6—C161.432 (3)C26—C251.522 (4)
O6—C171.424 (4)C62—H620.9500
F20—C501.333 (3)C57—H570.9500
F50—C581.330 (3)C57—C551.397 (4)
F30—C731.336 (4)C77—C821.500 (4)
F26—C901.334 (4)C47—C461.386 (4)
F23—C491.312 (4)C47—C481.391 (4)
F18—C501.335 (4)C47—C491.492 (4)
F17—C421.333 (4)C30—C311.394 (4)
F35—C811.339 (3)C30—C291.395 (4)
F19—C501.336 (3)C30—B11.642 (4)
F44—C661.330 (3)C46—H460.9500
F46—C561.317 (4)C48—H480.9500
O5—C191.424 (3)C10—C91.384 (4)
O5—C181.431 (3)C10—C111.489 (4)
F33—C811.314 (3)C10—C121.396 (4)
F41—C881.329 (5)C19—H19A0.9900
F40—C881.356 (4)C19—H19B0.9900
F34—C811.325 (3)C7—H70.9500
F29—C741.320 (3)C21—H21A0.9900
F43—C661.327 (3)C21—H21B0.9900
O4—C221.442 (3)C21—C221.509 (4)
O4—C231.447 (4)C9—H90.9500
F24—C901.336 (3)C37—C421.492 (4)
F15—C421.331 (4)C37—C381.381 (5)
F47—C561.321 (4)C16—H16A0.9900
O3—C251.443 (4)C16—H16B0.9900
O3—C241.421 (4)C16—C151.515 (4)
F37—C821.307 (4)C18—H18A0.9900
O2—C111.241 (3)C18—H18B0.9900
F16—C421.341 (4)C18—C171.501 (4)
F21—C491.327 (4)C88—C871.529 (5)
F39—C881.307 (4)C22—H22A0.9900
F45—C561.362 (4)C22—H22B0.9900
F36—C821.326 (5)C25—H25A0.9900
N3—C11.362 (3)C25—H25B0.9900
N3—C201.481 (3)C31—H310.9500
N3—C211.467 (3)C31—C321.393 (4)
N2—N11.255 (3)C29—H290.9500
N2—C41.419 (3)C29—C281.394 (4)
N1—C81.433 (4)C12—H120.9500
F51—C341.339 (5)C12—C131.385 (5)
N4—C261.471 (3)C14—H140.9500
N4—C111.350 (4)C14—C131.386 (5)
N4—C151.464 (4)F7—C271.272 (6)
F22—C491.358 (4)C82—F381.301 (4)
C79—C811.493 (4)C55—C561.505 (4)
C79—C801.389 (3)C15—H15A0.9900
C79—C781.394 (4)C15—H15B0.9900
C61—C601.397 (3)C32—C331.378 (5)
C61—C621.385 (4)C32—C341.472 (5)
C61—C661.495 (4)C17—H17A0.9900
C68—H680.9500C17—H17B0.9900
C68—C671.399 (3)F53—C341.218 (6)
C68—C691.390 (3)C28—C331.369 (5)
C2—C11.492 (4)C28—C271.493 (5)
C2—C31.386 (4)C13—H130.9500
C2—C71.392 (4)C23—H23A0.9900
C53—C581.493 (3)C23—H23B0.9900
C53—C541.380 (4)C23—C241.500 (5)
C53—C521.385 (4)C40—H400.9500
C59—C601.394 (3)C40—C391.395 (5)
C59—C641.403 (3)C24—H24A0.9900
C59—B21.644 (4)C24—H24B0.9900
C71—C721.392 (3)C33—H330.9500
C71—C701.381 (4)F8—C271.287 (6)
C71—C731.500 (4)C38—H380.9500
C75—C761.392 (3)C38—C391.383 (5)
C75—C801.406 (3)C34—F41.451 (6)
C75—B21.640 (3)C34—F51.290 (9)
C60—H600.9500C34—F541.359 (8)
C74—C691.485 (4)C34—F521.566 (7)
C83—C841.396 (3)C39—C411.528 (6)
C83—C891.406 (4)F12—C411.174 (16)
C83—B21.644 (4)C95—H950.9500
C63—C641.388 (4)C95—C941.3900
C63—C651.491 (4)C95—C961.3900
C63—C621.384 (4)C94—H940.9500
C72—H720.9500C94—C931.3900
C72—C671.395 (3)C93—H930.9500
C76—H760.9500C93—C921.3900
C76—C771.394 (4)C92—H920.9500
C67—B21.641 (3)C92—C911.3900
C54—H540.9500C91—H910.9500
C54—C551.387 (4)C91—C961.3900
C4—C31.384 (4)C96—H960.9500
C4—C51.389 (4)C98—H980.9500
C64—H640.9500C98—C991.3900
C80—H800.9500C98—C971.3900
C70—H700.9500C99—H990.9500
C70—C691.379 (4)C99—C1001.3900
C36—H360.9500C100—H1000.9500
C36—C351.393 (4)C100—C1011.3900
C36—C371.399 (4)C101—H1010.9500
C3—H30.9500C101—C1021.3900
C8—C91.390 (4)C102—H1020.9500
C8—C141.386 (4)C102—C971.3900
C51—C521.410 (4)C97—H970.9500
C51—C571.393 (4)C41—F111.420 (10)
C51—B11.644 (4)C41—F141.352 (6)
C20—H20A0.9900C41—F130.895 (16)
C20—H20B0.9900C41—F101.407 (15)
C20—C191.515 (3)C41—F91.353 (9)
C52—H520.9500
O6—Na1—O379.01 (7)O5—C19—C20114.7 (2)
O6—Na1—F45i86.19 (8)O5—C19—H19A108.6
O6—Na1—F6126.92 (14)O5—C19—H19B108.6
O5—Na1—O673.07 (7)C20—C19—H19A108.6
O5—Na1—O495.05 (8)C20—C19—H19B108.6
O5—Na1—O3124.56 (9)H19A—C19—H19B107.6
O5—Na1—F45i143.01 (9)C2—C7—C6119.5 (2)
O5—Na1—F693.62 (10)C2—C7—H7120.2
O4—Na1—O6136.59 (9)C6—C7—H7120.2
O4—Na1—O374.14 (8)N3—C21—H21A109.1
O4—Na1—F45i120.38 (9)N3—C21—H21B109.1
O4—Na1—F694.72 (14)N3—C21—C22112.7 (2)
O3—Na1—F45i78.95 (8)H21A—C21—H21B107.8
F6—Na1—O3140.51 (12)C22—C21—H21A109.1
F6—Na1—F45i74.53 (10)C22—C21—H21B109.1
F1—Na2—F248.28 (6)F23—C49—F21108.6 (3)
F1—Na2—F27ii137.74 (7)F23—C49—F22104.3 (3)
F1—Na2—F48i128.91 (8)F23—C49—C47114.3 (2)
F1—Na2—F41iv78.10 (7)F21—C49—F22104.4 (3)
F2—Na2—F27ii133.04 (7)F21—C49—C47112.9 (2)
F2—Na2—F41iv124.83 (7)F22—C49—C47111.5 (3)
F28ii—Na2—F1156.07 (9)F42—C66—C61111.8 (2)
F28ii—Na2—F2152.66 (8)F44—C66—F42105.9 (2)
F28ii—Na2—F27ii47.46 (6)F44—C66—C61112.4 (2)
F28ii—Na2—F48i73.25 (8)F43—C66—F42106.5 (2)
F28ii—Na2—F41iv78.21 (7)F43—C66—F44107.2 (2)
F27ii—Na2—F41iv93.40 (7)F43—C66—C61112.6 (2)
F48i—Na2—F280.67 (7)C8—C9—H9119.9
F48i—Na2—F27ii75.86 (8)C10—C9—C8120.3 (2)
F48i—Na2—F41iv149.14 (8)C10—C9—H9119.9
O1iii—Na2—F177.07 (7)O2—C11—N4121.5 (3)
O1iii—Na2—F272.55 (7)O2—C11—C10120.3 (3)
O1iii—Na2—F28ii115.29 (8)N4—C11—C10117.7 (2)
O1iii—Na2—F27ii67.89 (7)C36—C37—C42120.6 (3)
O1iii—Na2—F48i91.04 (8)C38—C37—C36121.1 (3)
O1iii—Na2—F41iv111.92 (8)C38—C37—C42118.3 (3)
O2—Na2—F192.83 (8)O6—C16—H16A109.6
O2—Na2—F287.51 (8)O6—C16—H16B109.6
O2—Na2—F28ii80.80 (8)O6—C16—C15110.2 (2)
O2—Na2—F27ii127.44 (8)H16A—C16—H16B108.1
O2—Na2—F48i81.57 (8)C15—C16—H16A109.6
O2—Na2—O1iii159.66 (9)C15—C16—H16B109.6
O2—Na2—F41iv82.53 (9)O5—C18—H18A109.9
C65—F1—Na2108.00 (16)O5—C18—H18B109.9
C65—F2—Na296.66 (17)O5—C18—C17108.8 (2)
C74—F28—Na2v110.53 (16)H18A—C18—H18B108.3
C74—F27—Na2v98.11 (17)C17—C18—H18A109.9
C58—F48—Na2i148.09 (16)C17—C18—H18B109.9
C1—O1—Na2vi148.68 (18)F32—C73—F31106.2 (2)
C16—O6—Na1123.57 (19)F32—C73—F30106.5 (2)
C17—O6—Na1110.34 (16)F32—C73—C71112.6 (2)
C17—O6—C16112.0 (2)F31—C73—C71112.2 (2)
C19—O5—Na1133.32 (16)F30—C73—F31106.6 (2)
C19—O5—C18114.8 (2)F30—C73—C71112.3 (2)
C18—O5—Na1111.32 (16)F20—C50—F18106.2 (3)
C88—F41—Na2iv129.6 (2)F20—C50—F19106.7 (2)
C22—O4—Na1137.77 (17)F20—C50—C45112.6 (2)
C22—O4—C23110.9 (2)F18—C50—F19105.5 (2)
C23—O4—Na1110.73 (17)F18—C50—C45112.3 (2)
C25—O3—Na1127.28 (18)F19—C50—C45113.0 (2)
C24—O3—Na199.11 (17)F41—C88—F40105.4 (3)
C24—O3—C25116.1 (2)F41—C88—C87113.0 (3)
C11—O2—Na2174.3 (2)F40—C88—C87109.2 (3)
C56—F45—Na1i155.4 (2)F39—C88—F41106.0 (4)
C1—N3—C20119.3 (2)F39—C88—F40110.1 (3)
C1—N3—C21117.1 (2)F39—C88—C87112.8 (3)
C21—N3—C20119.5 (2)C89—C87—C88119.6 (3)
N1—N2—C4117.2 (2)C86—C87—C89120.5 (3)
N2—N1—C8109.7 (2)C86—C87—C88119.9 (3)
C11—N4—C26123.8 (2)O4—C22—C21112.8 (2)
C11—N4—C15118.1 (2)O4—C22—H22A109.0
C15—N4—C26117.1 (2)O4—C22—H22B109.0
C80—C79—C81121.3 (2)C21—C22—H22A109.0
C80—C79—C78120.5 (2)C21—C22—H22B109.0
C78—C79—C81118.2 (2)H22A—C22—H22B107.8
F35—C81—C79112.8 (2)O3—C25—C26111.0 (2)
F33—C81—F35104.6 (2)O3—C25—H25A109.4
F33—C81—F34107.4 (3)O3—C25—H25B109.4
F33—C81—C79113.0 (2)C26—C25—H25A109.4
F34—C81—F35104.7 (2)C26—C25—H25B109.4
F34—C81—C79113.6 (2)H25A—C25—H25B108.0
C60—C61—C66119.8 (2)C30—C31—H31118.8
C62—C61—C60120.4 (2)C32—C31—C30122.3 (3)
C62—C61—C66119.8 (2)C32—C31—H31118.8
C67—C68—H68118.9C30—C29—H29119.2
C69—C68—H68118.9C28—C29—C30121.6 (3)
C69—C68—C67122.1 (2)C28—C29—H29119.2
C3—C2—C1117.2 (2)F25—C90—F24105.8 (3)
C3—C2—C7119.2 (2)F25—C90—C85112.3 (2)
C7—C2—C1123.3 (2)F26—C90—F25105.1 (3)
C54—C53—C58118.7 (2)F26—C90—F24107.8 (3)
C54—C53—C52121.5 (2)F26—C90—C85112.9 (2)
C52—C53—C58119.7 (2)F24—C90—C85112.5 (3)
C60—C59—C64115.6 (2)C10—C12—H12120.3
C60—C59—B2125.0 (2)C13—C12—C10119.4 (3)
C64—C59—B2119.3 (2)C13—C12—H12120.3
C72—C71—C73119.5 (2)C8—C14—H14120.3
C70—C71—C72121.0 (2)C8—C14—C13119.4 (3)
C70—C71—C73119.5 (2)C13—C14—H14120.3
C76—C75—C80115.2 (2)F37—C82—F36104.9 (3)
C76—C75—B2125.6 (2)F37—C82—C77113.0 (3)
C80—C75—B2119.0 (2)F36—C82—C77111.6 (3)
F49—C58—F48105.2 (2)F38—C82—F37107.5 (3)
F49—C58—F50108.2 (2)F38—C82—F36105.4 (4)
F49—C58—C53114.1 (2)F38—C82—C77113.7 (3)
F48—C58—C53111.7 (2)C54—C55—C57120.8 (3)
F50—C58—F48103.5 (2)C54—C55—C56118.5 (3)
F50—C58—C53113.3 (2)C57—C55—C56120.7 (3)
C61—C60—H60118.6N4—C15—C16110.4 (2)
C59—C60—C61122.8 (2)N4—C15—H15A109.6
C59—C60—H60118.6N4—C15—H15B109.6
O1—C1—N3122.1 (2)C16—C15—H15A109.6
O1—C1—C2120.2 (2)C16—C15—H15B109.6
N3—C1—C2117.1 (2)H15A—C15—H15B108.1
F28—C74—F27103.9 (2)C31—C32—C34120.9 (3)
F28—C74—C69112.8 (2)C33—C32—C31120.6 (3)
F27—C74—C69112.9 (2)C33—C32—C34118.4 (3)
F29—C74—F28107.2 (3)O6—C17—C18109.0 (2)
F29—C74—F27106.2 (2)O6—C17—H17A109.9
F29—C74—C69113.2 (2)O6—C17—H17B109.9
C84—C83—C89115.3 (2)C18—C17—H17A109.9
C84—C83—B2124.1 (2)C18—C17—H17B109.9
C89—C83—B2120.6 (2)H17A—C17—H17B108.3
C64—C63—C65118.6 (2)C29—C28—C27119.2 (3)
C62—C63—C64121.6 (2)C33—C28—C29121.5 (3)
C62—C63—C65119.7 (2)C33—C28—C27119.3 (3)
C71—C72—H72118.9C12—C13—C14121.0 (3)
C71—C72—C67122.2 (2)C12—C13—H13119.5
C67—C72—H72118.9C14—C13—H13119.5
C75—C76—H76118.9F46—C56—F47107.1 (3)
C75—C76—C77122.3 (2)F46—C56—F45105.8 (3)
C77—C76—H76118.9F46—C56—C55113.1 (3)
C68—C67—B2118.9 (2)F47—C56—F45105.9 (3)
C72—C67—C68115.6 (2)F47—C56—C55112.5 (3)
C72—C67—B2125.5 (2)F45—C56—C55111.8 (3)
C53—C54—H54121.2O4—C23—H23A109.4
C53—C54—C55117.6 (2)O4—C23—H23B109.4
C55—C54—H54121.2O4—C23—C24111.1 (3)
C3—C4—N2111.8 (2)H23A—C23—H23B108.0
C3—C4—C5120.8 (2)C24—C23—H23A109.4
C5—C4—N2127.4 (2)C24—C23—H23B109.4
C59—C64—H64119.1C35—C40—H40118.7
C63—C64—C59121.7 (2)C39—C40—C35122.5 (3)
C63—C64—H64119.1C39—C40—H40118.7
C79—C80—C75122.7 (2)O3—C24—C23112.3 (3)
C79—C80—H80118.6O3—C24—H24A109.1
C75—C80—H80118.6O3—C24—H24B109.1
C71—C70—H70121.1C23—C24—H24A109.1
C69—C70—C71117.9 (2)C23—C24—H24B109.1
C69—C70—H70121.1H24A—C24—H24B107.9
C35—C36—H36118.9C32—C33—H33120.9
C35—C36—C37122.2 (3)C28—C33—C32118.1 (3)
C37—C36—H36118.9C28—C33—H33120.9
C2—C3—H3119.6C59—B2—C83110.41 (19)
C4—C3—C2120.8 (2)C75—B2—C59108.09 (19)
C4—C3—H3119.6C75—B2—C83112.81 (19)
C9—C8—N1121.7 (2)C75—B2—C67109.72 (19)
C14—C8—N1118.1 (3)C67—B2—C59109.55 (19)
C14—C8—C9120.1 (3)C67—B2—C83106.24 (19)
C52—C51—B1119.8 (2)F17—C42—F16105.5 (3)
C57—C51—C52115.2 (2)F17—C42—C37112.9 (3)
C57—C51—B1125.0 (2)F15—C42—F17106.5 (3)
N3—C20—H20A108.2F15—C42—F16106.4 (3)
N3—C20—H20B108.2F15—C42—C37113.1 (3)
N3—C20—C19116.4 (2)F16—C42—C37111.9 (3)
H20A—C20—H20B107.4C37—C38—H38121.1
C19—C20—H20A108.2C37—C38—C39117.8 (3)
C19—C20—H20B108.2C39—C38—H38121.1
C68—C69—C74117.7 (2)F51—C34—C32110.7 (3)
C70—C69—C68121.1 (2)F51—C34—F495.2 (4)
C70—C69—C74121.2 (2)C32—C34—F52106.7 (4)
C53—C52—C51122.2 (2)F53—C34—F51114.6 (5)
C53—C52—H52118.9F53—C34—C32119.7 (4)
C51—C52—H52118.9F53—C34—F4106.0 (5)
C44—C43—C48115.9 (2)F4—C34—C32107.3 (4)
C44—C43—B1124.4 (2)F5—C34—C32129.4 (6)
C48—C43—B1119.7 (2)F5—C34—F54113.0 (6)
C83—C84—H84118.8F5—C34—F5296.6 (6)
C83—C84—C85122.5 (2)F54—C34—C32113.5 (5)
C85—C84—H84118.8F54—C34—F5284.3 (5)
C84—C85—C90119.2 (3)F6—C27—C28112.6 (3)
C86—C85—C84120.8 (2)F7—C27—F6104.7 (5)
C86—C85—C90120.0 (2)F7—C27—C28115.7 (3)
C36—C35—C40115.5 (3)F7—C27—F8104.2 (4)
C36—C35—B1124.5 (2)F8—C27—F6104.2 (4)
C40—C35—B1120.0 (3)F8—C27—C28114.3 (4)
C27—F6—Na1146.5 (3)C40—C39—C41118.9 (4)
C83—C89—H89118.7C38—C39—C40120.7 (3)
C87—C89—C83122.7 (2)C38—C39—C41120.3 (3)
C87—C89—H89118.7C51—B1—C35107.8 (2)
C5—C6—H6119.5C43—B1—C51110.6 (2)
C5—C6—C7121.1 (3)C43—B1—C35109.9 (2)
C7—C6—H6119.5C30—B1—C51108.2 (2)
C85—C86—H86120.9C30—B1—C43108.1 (2)
C85—C86—C87118.2 (2)C30—B1—C35112.2 (2)
C87—C86—H86120.9C94—C95—H95120.0
F1—C65—F2105.2 (2)C94—C95—C96120.0
F1—C65—C63113.3 (2)C96—C95—H95120.0
F2—C65—C63112.9 (3)C95—C94—H94120.0
F3—C65—F1105.0 (2)C95—C94—C93120.0
F3—C65—F2107.5 (2)C93—C94—H94120.0
F3—C65—C63112.3 (2)C94—C93—H93120.0
C44—C45—C50118.7 (2)C92—C93—C94120.0
C46—C45—C44120.9 (2)C92—C93—H93120.0
C46—C45—C50120.3 (2)C93—C92—H92120.0
C43—C44—C45122.2 (2)C91—C92—C93120.0
C43—C44—H44118.9C91—C92—H92120.0
C45—C44—H44118.9C92—C91—H91120.0
C79—C78—H78121.2C92—C91—C96120.0
C77—C78—C79117.6 (2)C96—C91—H91120.0
C77—C78—H78121.2C95—C96—H96120.0
C4—C5—H5120.7C91—C96—C95120.0
C6—C5—C4118.7 (3)C91—C96—H96120.0
C6—C5—H5120.7C99—C98—H98120.0
N4—C26—H26A108.3C99—C98—C97120.0
N4—C26—H26B108.3C97—C98—H98120.0
N4—C26—C25115.8 (2)C98—C99—H99120.0
H26A—C26—H26B107.4C100—C99—C98120.0
C25—C26—H26A108.3C100—C99—H99120.0
C25—C26—H26B108.3C99—C100—H100120.0
C61—C62—H62121.1C99—C100—C101120.0
C63—C62—C61117.8 (2)C101—C100—H100120.0
C63—C62—H62121.1C100—C101—H101120.0
C51—C57—H57118.7C102—C101—C100120.0
C51—C57—C55122.6 (2)C102—C101—H101120.0
C55—C57—H57118.7C101—C102—H102120.0
C76—C77—C82119.1 (3)C101—C102—C97120.0
C78—C77—C76121.4 (2)C97—C102—H102120.0
C78—C77—C82119.4 (3)C98—C97—H97120.0
C46—C47—C48120.9 (2)C102—C97—C98120.0
C46—C47—C49118.1 (2)C102—C97—H97120.0
C48—C47—C49121.0 (2)F12—C41—C39117.2 (14)
C31—C30—C29115.8 (3)F12—C41—F1065.8 (11)
C31—C30—B1120.2 (2)F11—C41—C39105.2 (5)
C29—C30—B1123.9 (3)F14—C41—C39111.8 (4)
C45—C46—C47118.1 (2)F14—C41—F11109.4 (7)
C45—C46—H46120.9F14—C41—F9106.1 (6)
C47—C46—H46120.9F13—C41—C39129.8 (12)
C43—C48—H48119.1F13—C41—F1285.3 (14)
C47—C48—C43121.9 (2)F13—C41—F10113.4 (13)
C47—C48—H48119.1F10—C41—C39116.8 (7)
C9—C10—C11116.3 (2)F9—C41—C39111.3 (5)
C9—C10—C12119.8 (3)F9—C41—F11113.1 (5)
C12—C10—C11123.7 (3)
Na1—O6—C16—C1571.4 (3)C89—C83—B2—C75−46.6 (3)
Na1—O6—C17—C18−44.2 (3)C89—C83—B2—C6773.7 (3)
Na1—O5—C19—C20−89.8 (3)C86—C85—C90—F25−108.0 (3)
Na1—O5—C18—C17−43.9 (3)C86—C85—C90—F26133.4 (3)
Na1—O4—C22—C2134.6 (4)C86—C85—C90—F2411.2 (4)
Na1—O4—C23—C2412.6 (3)C65—C63—C64—C59174.5 (2)
Na1—O3—C25—C26112.5 (2)C65—C63—C62—C61−176.5 (2)
Na1—O3—C24—C2362.1 (3)C44—C43—C48—C47−0.3 (4)
Na1i—F45—C56—F46−108.8 (4)C44—C43—B1—C51−15.1 (3)
Na1i—F45—C56—F474.7 (6)C44—C43—B1—C35103.8 (3)
Na1i—F45—C56—C55127.6 (4)C44—C43—B1—C30−133.4 (3)
Na1—F6—C27—F771.2 (8)C44—C45—C46—C470.0 (4)
Na1—F6—C27—C28−162.3 (5)C44—C45—C50—F2053.8 (3)
Na1—F6—C27—F8−37.9 (9)C44—C45—C50—F18−66.0 (3)
Na2—F1—C65—F2−13.6 (2)C44—C45—C50—F19174.8 (2)
Na2—F1—C65—F3−126.82 (17)C78—C79—C81—F35−65.9 (3)
Na2—F1—C65—C63110.2 (2)C78—C79—C81—F3352.5 (3)
Na2—F2—C65—F111.8 (2)C78—C79—C81—F34175.1 (3)
Na2—F2—C65—F3123.3 (2)C78—C79—C80—C75−1.7 (4)
Na2—F2—C65—C63−112.2 (2)C78—C77—C82—F37131.1 (3)
Na2v—F28—C74—F27−0.9 (3)C78—C77—C82—F36−110.9 (3)
Na2v—F28—C74—F29111.25 (19)C78—C77—C82—F388.1 (5)
Na2v—F28—C74—C69−123.6 (2)C5—C4—C3—C2−0.8 (4)
Na2v—F27—C74—F280.8 (2)C5—C6—C7—C2−0.1 (4)
Na2v—F27—C74—F29−112.1 (2)C26—N4—C11—O2−157.6 (3)
Na2v—F27—C74—C69123.3 (2)C26—N4—C11—C1030.0 (4)
Na2i—F48—C58—F49−31.3 (4)C26—N4—C15—C16−124.3 (3)
Na2i—F48—C58—F5082.1 (4)C62—C61—C60—C590.9 (4)
Na2i—F48—C58—C53−155.6 (3)C62—C61—C66—F42102.7 (3)
Na2vi—O1—C1—N3−166.1 (2)C62—C61—C66—F44−138.4 (3)
Na2vi—O1—C1—C25.3 (5)C62—C61—C66—F43−17.1 (4)
Na2iv—F41—C88—F40−86.5 (3)C62—C63—C64—C59−1.0 (4)
Na2iv—F41—C88—F3930.3 (3)C62—C63—C65—F1−138.5 (3)
Na2iv—F41—C88—C87154.33 (19)C62—C63—C65—F2−19.0 (4)
F28—C74—C69—C68−48.5 (3)C62—C63—C65—F3102.7 (3)
F28—C74—C69—C70132.6 (3)C57—C51—C52—C53−1.1 (4)
F27—C74—C69—C68−165.9 (2)C57—C51—B1—C43−107.6 (3)
F27—C74—C69—C7015.2 (4)C57—C51—B1—C35132.3 (3)
O6—C16—C15—N457.6 (3)C57—C51—B1—C3010.7 (4)
O5—C18—C17—O659.6 (3)C57—C55—C56—F46−27.1 (4)
F41—C88—C87—C8948.2 (4)C57—C55—C56—F47−148.6 (3)
F41—C88—C87—C86−129.1 (3)C57—C55—C56—F4592.3 (4)
F40—C88—C87—C89−68.7 (4)C30—C31—C32—C33−0.8 (5)
F40—C88—C87—C86114.0 (3)C30—C31—C32—C34175.8 (3)
F29—C74—C69—C6873.4 (3)C30—C29—C28—C33−1.2 (5)
F29—C74—C69—C70−105.5 (3)C30—C29—C28—C27178.5 (3)
O4—C23—C24—O3−54.2 (4)C46—C45—C44—C43−0.5 (4)
F39—C88—C87—C89168.5 (3)C46—C45—C50—F20−127.6 (3)
F39—C88—C87—C86−8.8 (5)C46—C45—C50—F18112.6 (3)
N3—C20—C19—O562.3 (3)C46—C45—C50—F19−6.6 (4)
N3—C21—C22—O461.4 (3)C46—C47—C48—C43−0.1 (4)
N2—N1—C8—C9−15.6 (3)C46—C47—C49—F23−174.8 (3)
N2—N1—C8—C14161.0 (2)C46—C47—C49—F21−49.9 (4)
N2—C4—C3—C2−179.5 (2)C46—C47—C49—F2267.2 (3)
N2—C4—C5—C6178.5 (3)C48—C43—C44—C450.6 (4)
N1—N2—C4—C3−176.1 (2)C48—C43—B1—C51166.1 (2)
N1—N2—C4—C55.2 (4)C48—C43—B1—C35−75.0 (3)
N1—C8—C9—C10174.0 (2)C48—C43—B1—C3047.8 (3)
N1—C8—C14—C13−175.2 (3)C48—C47—C46—C450.3 (4)
N4—C26—C25—O3−67.3 (3)C48—C47—C49—F236.5 (4)
C79—C78—C77—C762.0 (4)C48—C47—C49—F21131.3 (3)
C79—C78—C77—C82179.5 (3)C48—C47—C49—F22−111.6 (3)
C81—C79—C80—C75176.4 (2)C10—C12—C13—C14−0.3 (5)
C81—C79—C78—C77−179.7 (2)C19—O5—C18—C17143.3 (2)
C68—C67—B2—C59−51.6 (3)C7—C2—C1—O149.4 (4)
C68—C67—B2—C75−170.1 (2)C7—C2—C1—N3−138.7 (3)
C68—C67—B2—C8367.7 (3)C7—C2—C3—C41.2 (4)
C53—C54—C55—C57−3.7 (4)C7—C6—C5—C40.5 (4)
C53—C54—C55—C56173.3 (3)C21—N3—C1—O110.0 (4)
C71—C72—C67—C682.7 (4)C21—N3—C1—C2−161.7 (2)
C71—C72—C67—B2−176.3 (2)C21—N3—C20—C1943.0 (3)
C71—C70—C69—C680.5 (4)C49—C47—C46—C45−178.5 (3)
C71—C70—C69—C74179.4 (2)C49—C47—C48—C43178.6 (3)
C75—C76—C77—C780.9 (4)C66—C61—C60—C59−179.0 (2)
C75—C76—C77—C82−176.6 (3)C66—C61—C62—C63−179.0 (2)
C58—C53—C54—C55−173.0 (3)C9—C8—C14—C131.5 (4)
C58—C53—C52—C51175.3 (2)C9—C10—C11—O2−121.0 (3)
C60—C61—C62—C631.0 (4)C9—C10—C11—N451.4 (3)
C60—C61—C66—F42−77.3 (3)C9—C10—C12—C13−0.8 (4)
C60—C61—C66—F4441.6 (3)C11—N4—C26—C25−120.2 (3)
C60—C61—C66—F43162.8 (2)C11—N4—C15—C1666.7 (3)
C60—C59—C64—C632.8 (3)C11—C10—C9—C8177.7 (2)
C60—C59—B2—C75110.0 (2)C11—C10—C12—C13−176.0 (3)
C60—C59—B2—C83−126.2 (2)C37—C36—C35—C40−0.8 (4)
C60—C59—B2—C67−9.5 (3)C37—C36—C35—B1179.0 (3)
C1—N3—C20—C19−160.5 (2)C37—C38—C39—C401.7 (7)
C1—N3—C21—C2265.0 (3)C37—C38—C39—C41−179.9 (5)
C1—C2—C3—C4174.8 (2)C16—O6—C17—C18174.0 (2)
C1—C2—C7—C6−174.0 (2)C18—O5—C19—C2081.0 (3)
C83—C84—C85—C860.9 (4)C73—C71—C72—C67−179.4 (2)
C83—C84—C85—C90−179.7 (2)C73—C71—C70—C69177.7 (2)
C83—C89—C87—C863.4 (4)C50—C45—C44—C43178.1 (2)
C83—C89—C87—C88−173.9 (3)C50—C45—C46—C47−178.5 (2)
C72—C71—C70—C69−1.6 (4)C22—O4—C23—C24−159.9 (3)
C72—C71—C73—F32−30.8 (4)C25—O3—C24—C23−77.5 (3)
C72—C71—C73—F31−150.5 (2)C31—C30—C29—C281.8 (4)
C72—C71—C73—F3089.4 (3)C31—C30—B1—C51−79.6 (3)
C72—C67—B2—C59127.4 (2)C31—C30—B1—C4340.2 (3)
C72—C67—B2—C758.9 (3)C31—C30—B1—C35161.5 (2)
C72—C67—B2—C83−113.3 (3)C31—C32—C33—C281.5 (5)
C76—C75—C80—C794.4 (3)C31—C32—C34—F51131.9 (4)
C76—C75—B2—C59116.1 (3)C31—C32—C34—F53−4.8 (7)
C76—C75—B2—C83−6.2 (3)C31—C32—C34—F4−125.4 (4)
C76—C75—B2—C67−124.5 (2)C31—C32—C34—F5150.4 (7)
C76—C77—C82—F37−51.3 (4)C31—C32—C34—F54−54.3 (7)
C76—C77—C82—F3666.7 (4)C31—C32—C34—F5236.7 (5)
C76—C77—C82—F38−174.3 (4)C29—C30—C31—C32−0.8 (4)
C67—C68—C69—C74−176.7 (2)C29—C30—B1—C5197.2 (3)
C67—C68—C69—C702.2 (4)C29—C30—B1—C43−143.0 (3)
C54—C53—C58—F49−33.0 (3)C29—C30—B1—C35−21.7 (4)
C54—C53—C58—F4886.1 (3)C29—C28—C33—C32−0.6 (5)
C54—C53—C58—F50−157.4 (3)C29—C28—C27—F6−97.9 (5)
C54—C53—C52—C51−1.4 (4)C29—C28—C27—F722.4 (6)
C54—C55—C56—F46155.9 (3)C29—C28—C27—F8143.4 (4)
C54—C55—C56—F4734.4 (4)C90—C85—C86—C87179.7 (3)
C54—C55—C56—F45−84.7 (4)C12—C10—C9—C82.2 (4)
C4—N2—N1—C8−177.7 (2)C12—C10—C11—O254.3 (4)
C64—C59—C60—C61−2.8 (3)C12—C10—C11—N4−133.2 (3)
C64—C59—B2—C75−72.3 (3)C14—C8—C9—C10−2.6 (4)
C64—C59—B2—C8351.6 (3)C15—N4—C26—C2571.5 (3)
C64—C59—B2—C67168.2 (2)C15—N4—C11—O210.6 (4)
C64—C63—C65—F145.8 (3)C15—N4—C11—C10−161.7 (2)
C64—C63—C65—F2165.3 (2)C17—O6—C16—C15−152.6 (3)
C64—C63—C65—F3−73.0 (3)C23—O4—C22—C21−155.9 (3)
C64—C63—C62—C61−1.0 (4)C40—C35—B1—C51−50.9 (4)
C80—C79—C81—F35116.0 (3)C40—C35—B1—C43−171.5 (3)
C80—C79—C81—F33−125.7 (3)C40—C35—B1—C3068.2 (4)
C80—C79—C81—F34−3.0 (4)C40—C39—C41—F12−83.4 (13)
C80—C79—C78—C77−1.6 (4)C40—C39—C41—F11−64.0 (7)
C80—C75—C76—C77−4.0 (4)C40—C39—C41—F14177.3 (6)
C80—C75—B2—C59−68.2 (3)C40—C39—C41—F13169 (2)
C80—C75—B2—C83169.5 (2)C40—C39—C41—F10−8.2 (14)
C80—C75—B2—C6751.2 (3)C40—C39—C41—F958.8 (7)
C70—C71—C72—C67−0.1 (4)C24—O3—C25—C26−121.0 (3)
C70—C71—C73—F32149.9 (2)C33—C32—C34—F51−51.4 (5)
C70—C71—C73—F3130.1 (4)C33—C32—C34—F53171.9 (5)
C70—C71—C73—F30−89.9 (3)C33—C32—C34—F451.3 (5)
C36—C35—C40—C393.7 (6)C33—C32—C34—F5−32.9 (9)
C36—C35—B1—C51129.4 (3)C33—C32—C34—F54122.4 (6)
C36—C35—B1—C438.8 (4)C33—C32—C34—F52−146.6 (4)
C36—C35—B1—C30−111.5 (3)C33—C28—C27—F681.7 (5)
C36—C37—C42—F1737.6 (4)C33—C28—C27—F7−158.0 (5)
C36—C37—C42—F15158.7 (3)C33—C28—C27—F8−37.0 (6)
C36—C37—C42—F16−81.2 (4)B2—C59—C60—C61175.0 (2)
C36—C37—C38—C391.1 (6)B2—C59—C64—C63−175.1 (2)
C3—C2—C1—O1−123.9 (3)B2—C75—C76—C77171.8 (2)
C3—C2—C1—N348.0 (3)B2—C75—C80—C79−171.7 (2)
C3—C2—C7—C6−0.8 (4)B2—C83—C84—C85178.6 (2)
C3—C4—C5—C6−0.1 (4)B2—C83—C89—C87179.2 (2)
C8—C14—C13—C12−0.1 (5)C42—C37—C38—C39−176.2 (4)
C51—C57—C55—C541.3 (5)C38—C37—C42—F17−145.0 (3)
C51—C57—C55—C56−175.6 (3)C38—C37—C42—F15−23.9 (4)
C20—N3—C1—O1−147.1 (2)C38—C37—C42—F1696.2 (4)
C20—N3—C1—C241.2 (3)C38—C39—C41—F1298.1 (13)
C20—N3—C21—C22−138.0 (2)C38—C39—C41—F11117.5 (5)
C69—C68—C67—C72−3.8 (4)C38—C39—C41—F14−1.2 (10)
C69—C68—C67—B2175.4 (2)C38—C39—C41—F13−10 (2)
C52—C53—C58—F49150.2 (2)C38—C39—C41—F10173.3 (11)
C52—C53—C58—F48−90.6 (3)C38—C39—C41—F9−119.6 (5)
C52—C53—C58—F5025.8 (3)C34—C32—C33—C28−175.2 (3)
C52—C53—C54—C553.7 (4)C27—C28—C33—C32179.8 (3)
C52—C51—C57—C551.1 (4)B1—C51—C52—C53179.9 (2)
C52—C51—B1—C4371.4 (3)B1—C51—C57—C55−179.9 (3)
C52—C51—B1—C35−48.8 (3)B1—C43—C44—C45−178.2 (2)
C52—C51—B1—C30−170.4 (2)B1—C43—C48—C47178.6 (2)
C84—C83—C89—C87−3.3 (4)B1—C35—C40—C39−176.1 (4)
C84—C83—B2—C5915.1 (3)B1—C30—C31—C32176.2 (3)
C84—C83—B2—C75136.2 (2)B1—C30—C29—C28−175.1 (3)
C84—C83—B2—C67−103.6 (3)C95—C94—C93—C920.0
C84—C85—C86—C87−0.9 (4)C94—C95—C96—C910.0
C84—C85—C90—F2572.6 (3)C94—C93—C92—C910.0
C84—C85—C90—F26−45.9 (4)C93—C92—C91—C960.0
C84—C85—C90—F24−168.1 (3)C92—C91—C96—C950.0
C85—C86—C87—C89−1.1 (4)C96—C95—C94—C930.0
C85—C86—C87—C88176.2 (3)C98—C99—C100—C1010.0
C35—C36—C37—C42175.7 (3)C99—C98—C97—C1020.0
C35—C36—C37—C38−1.6 (5)C99—C100—C101—C1020.0
C35—C40—C39—C38−4.2 (7)C100—C101—C102—C970.0
C35—C40—C39—C41177.3 (5)C101—C102—C97—C980.0
C89—C83—C84—C851.2 (4)C97—C98—C99—C1000.0
C89—C83—B2—C59−167.6 (2)
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z; (iii) x, y−1, z; (iv) −x+1, −y, −z+2; (v) x−1, y, z; (vi) x, y+1, z.
Geometric parameters (Å, °) and chain directions for selected C—H···O contacts top
C21—H21A···O3C26—H26B···O2C9—H9···O6
D—H1.012 (11)1.005 (11)1.008 (11)
H···A2.498 (11)2.395 (11)2.405 (11)
D···A3.5028 (5)3.3917 (5)3.3677 (4)
D—H···A171.7 (8)171.3 (9)159.6 (9)
Direction of chain[100][001][100]
 

Acknowledgements

We thank Professor Carsten Strohmann and Tobias Schrimpf for scientific as well as instrumental support.

Funding information

Financial support was generously granted by the ‘NRW Returning Scholars Program’ of the State of North Rhine-Westphalia.

References

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ISSN: 2056-9890
Volume 82| Part 3| March 2026| Pages 271-277
https://doi.org/10.1107/S2056989026001234
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