research communications
Cyclopentadienone triisocyanide iron complexes: general synthesis and crystal structures of tris(2,6-dimethylphenyl isocyanide)(η4-tetraphenylcyclopentadienone)iron and tris(naphthalen-2-yl isocyanide)(η4-tetraphenylcyclopentadienone)iron acetone hemisolvate
aDepartment of Chemistry and Applied Biosciences, Laboratory of Organic Chemistry, ETH Zurich, Zurich 8093, Switzerland
*Correspondence e-mail: peter.chen@org.chem.ethz.ch
Irradiation of a toluene solution containing cyclopentadienone tricarbonyl iron complexes and η4-tetraphenylcyclopenatedienone)iron, [Fe(C9H9N)3(C29H20O)], and tris(naphthalen-2-yl isocyanide)(η4-tetraphenylcyclopenatedienone)iron acetone hemisolvate, [Fe(C11H7N)3(C29H20O)]2·C3H6O, could be characterized crystallographically. The air-stable compounds were purified by column chromatography and were characterized by 1H NMR, 13C NMR, elemental analysis and HRMS. NMR and XRD data indicate generally more electron-rich Fe0 centers compared to the corresponding tricarbonyl compounds.
with blue LEDs afforded the formation and isolation of 12 triisocyanide complexes, two of which, namely tris(2,6-dimethylphenyl isocyanide)(Keywords: crystal structure; isocyanide; cyclopentadienone iron complex; LEDs.
1. Chemical context
While cyclopentadienone tricarbonyl iron complexes are well known species and have been established as pre-catalysts for hydrogenation and transfer hydrogenation reactions among other types and reactions (Quintard & Rodriguez, 2014; Pignataro & Gennari, 2020), the corresponding triisocyanide complexes have thus far not been described in the literature. Considering the electronic similarity between CO and CNR (R = alkyl or aryl) ligands (Pruchnik & Duraj, 1990), the incorporation of isocyanide ligands into the cyclopentadienone iron complex framework could open up new handles to tune the electronic and steric properties of the compounds by variation of the R group on the isocyanide ligands.
Inspired by the procedure described for obtaining cyclopentadienone triacetonitrile complexes by irradiation of the corresponding tricarbonyl complexes with light in acetonitrile solution (Knölker et al., 1999), it was found that irradiating a toluene solution (ca 0.1 M total concentration) of a cyclopentadienone tricarbonyl complex [1 equiv., cyclopentadienone = tetraphenylcyclopentadienone (TPCPD) or 1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one (BTTHI)] and a slight excess of an isocyanide RNC [4 equiv., R = CH2Ts (Ts = toluenesulfonyl), tBu, Bu, 2,6-DMP (DMP = dimethylphenyl), 2-Naphth (Naphth = Naphthyl), CH2Ph] with blue LEDs under a nitrogen atmosphere overnight afforded the corresponding triisocyanide complexes in moderate to good yields (20–85%) (Fig. 1). For two of the twelve isolated compounds, namely Fe(CN-2,6-DMP)3-TPCPD and Fe(CN-2-Naphth)3-TPCPD, single crystals suitable for XRD could be obtained. Their structures are reported herein.
The isolated complexes were inactive in hydrogenation and transfer hydrogenation reactions of acetophenone in iPrOH (1 mol% catalyst loading, 363 K, 10 bar H2). Addition of Me3NO, as is routinely done for activating the corresponding tricarbonyl complexes, did not lead to turnover either. It is assumed that neither Me3NO nor elevated temperatures are able to cleave one of the Fe—CNR bonds to free up a coordination site needed for catalysis. While potential applications of these complexes in catalysis were unsuccessful, our studies nevertheless prompted us to seek systematic relationships between the ligand properties and either the structural or the functional properties of the complexes.
2. Structural commentary
Comparisons to tricarbonyl(η4-tetraphenylcyclopentadienone)iron [Fe(CO)3-TPCPD] will be based on the reported structure (Gupta et al., 2000; CCDC deposition number 142285).
Fe(CN-2,6-DMP)3-TPCPD (Fig. 2) crystallizes in the Pca21 and features one complex molecule per with no co-crystallized solvent molecules. The average Fe—CNR bond distance is 1.84 (1) Å. The average C—Fe—C angle is 94 (3)°. Fe(CN-2-Naphth)3-TPCPD (Figs. 3 and 4) crystallizes in the P21 and features two complex molecules and a co-crystallized acetone molecule in the The average Fe—CNR distance is 1.831 (6) Å. The average C—Fe—C angle is 96 (2)°. In one of the complex molecules, there is disorder in two of the three naphthyl groups with site-occupancy factors of 0.911 (3) and 0.089 (3). Fe(CN-2,6-DMP)3-TPCPD shows a C=O double bond length of 1.243 (5) Å, while the two complexes in the of Fe(CN-2-Naphth)3-TPCPD show lengths of 1.247 (4) and 1.243 (4) Å. These values are marginally longer than the C=O double bond in Fe(CO)3-TPCPD, in which the C=O double bond length is 1.22 (1) Å. Both compounds feature the iron atom in the formal 0 The cyclopentadienone ligand is coordinated in an η4 fashion.
In Fe(CN-2,6-DMP)3-TPCPD, the average distance between Fe and the diene carbon atoms (C5, C6, C7, C8) is 2.11 (3) Å and the Fe distance to the ketonic carbon atom (C4) is 2.361 (4) Å. In Fe(CN-2-Naphth)3-TPCPD, the average distance between Fe and the diene carbon atoms (C5, C6, C7, C8) is 2.10 (3) Å and the distances from Fe to the ketonic carbon atom (C4) are 2.367 (3) and 2.373 (3) Å. Compared to values in Fe(CO)3-TPCPD [2.14 (2) Å and 2.40 (1) Å, respectively], the values measured in the isocyanide complexes are marginally smaller, i.e. the Fe–diene bond is shorter.
The envelope angles, defined as the angle between the plane spanned by C5, C6, C7 and C8 with the plane spanned by C4, C5, C8 and O1, are 14.1689 (3)° for Fe(CN-2,6-DMP)3-TPCPD and 15.6550 (2)° and 12.8805 (2)° in Fe(CN-2-Naphth)3-TPCPD. They are lower than the envelope angle for Fe(CO)3-TPCPD, which is reported to be 16°. The isocyanide complexes show a flatter cyclopentadienone ligand, which, together with the elongated C=O double bonds, could indicate more `cyclopentadienyl character', reflecting the high electron density on iron and its presumed propensity to redistribute its electrons into the ligands.
The C—N—C angles in the isocyanide ligands in Fe(CN-2,6-DMP)3-TPCPD are 178.6 (4), 163.5 (4) and 159.5 (4)°. In Fe(CN-2-Naphth)3-TPCPD, the angles are 170.5 (3), 168.6 (3) and 168.5 (3)° for the complex without disorder and 175.8 (3), 162.6 (3) and 157.9 (12)° in the complex with disorder. The bending away from 180° indicates significant back-bonding from the Fe0 center into the π*CN orbitals of the ligands. For Fe(CN-2,6-DMP)3-TPCPD, the isocyanide ligand showing an almost linear C—N—C angle of 178.6 (4)°, is located parallel to the C=O double bond of the cyclopentadienone ligand. This could indicate that, in this position in the Fe(CNR)3 fragment, only a little back-bonding takes place, and that the Fe0 atom prefers to distribute its electron density into the two isocyanide ligands facing away from the C=O double bond. In Fe(CN-2-Naphth)3-TPCPD, the spread of the angles is generally lower. It can furthermore be observed that the C—N—C bends are angled towards the cyclopentadienone ligand in the same molecule. As the features two interlocked Fe(CN-2-Naphth)3-TPCPD molecules (the C—N—C bends face away from the other complex molecule in the pairs), it is proposed that the lower spread and lack of trend as to which position in the Fe(CNR) fragment experiences how much back-bonding is due to crystal-packing forces. This is not observed in Fe(CN-2,6-DMP)3-TPCPD, since there is no obvious intermolecular interaction in this case.
13C NMR analysis revealed similar experimental evidence for the higher electron density on iron. Table 1 shows the 13C NMR chemical shifts for the ring carbon atoms C4, C5, C6, C7 and C8 in the complexes Fe(CX)3-TPCPD (X = O, NR). The corresponding values for complexes with the BTTHI ligand are shifted ca 5 ppm downfield for C4 and C6/C7 and ca 10 ppm upfield for C5/C8 and follow the same overall trend as the complexes with TPCPD. It can be observed that the signals are all shifted upfield, i.e. to lower chemical shifts, compared to the parent tricarbonyl complex. This observation can be explained by considering that are weaker π-acceptors and stronger σ-donors compared to CO. They thus render the iron center more electron rich and therefore lead to more electron density and thus shielding in the cyclopentadienone ligand. Complexes with isocyanide ligands bearing electron-withdrawing or aromatic substituents (CH2Ts, 2-Naphth, 2,6-DMP) show more deshielded signals compared to isocyanide ligands with electron-donating substituents (CH2Ph, Bu, tBu).
Furthermore, 13C NMR analysis showed that the CNR signals are generally more shielded by 2–5 ppm for complexes bearing the TPCPD ligand compared to the BTTHI ligand, indicative of stronger dFe to π*CN back-bonding with BTTHI, since more back-donation generally leads to higher chemical shifts (Pruchnik & Duraj, 1990). TPCPD can thus be said to be a stronger acceptor than BTTHI, rendering the Fe center less electron rich.
3. Supramolecular features
In the crystal of Fe(CN-2-Naphth)3-TPCPD, the complexes form pairs with the Fe(CNR)3 fragments facing each other. The complexes are rotated by approximately 180° relative to each other. The naphthyl groups form an interlocked structure. No obvious intermolecular interactions are observed in Fe(CN-2,6-DMP)3-TPCPD.
4. Database survey
In a search of the Cambridge Structural Database (WebCSD, accessed May 2023, Groom et al., 2016), three structures featuring an iron triisocyanide moiety with the iron center in the 0 were found in which the iron is bound to a diene (Fig. 5). Bassett and co-workers reported the complex tris(tert-butylisocyanide)(η4-N1,N4-di-tert-butyl-2,3-diphenylbuta-1,3-diene-1,4-diimine)iron, which could be accessed by either treating Fe2(CNtBu)9 or Fe(CNtBu)5 with diphenylacetylene (Bassett et al., 1978, CCDC deposition number 1107207; Bassett et al., 1980, CCDC deposition number 1107208). Sunada and co-workers reported the structure of tris(η4-adamantyl isocyanide)(1,3,5,7-cyclotetraene)iron (Sunada et al., 2015, CCDC deposition number 1416957). The compound was prepared by treating di(1,3,5,7-cyclotetraene)iron with three equivalents of adamantyl isocyanide. The analogous structure with tBuNC instead of adamantyl isocyanide was also reported (Bassett et al., 1981), but not crystallographically characterized. Brennessel and Ellis reported the structure of Fe(η4-anthracene)(CN-2,6-DMP)3 (Brennessel & Ellis, 2022, CCDC deposition number 2127596). The structure features the most similar coordination environment around iron compared to Fe(CN-2,6-DMP)3-TPCPD and Fe(CN-2-Naphth)3-TPCPD found in the database. The average C—Fe—C angle is 95 (5)°, which is very similar to the values observed in Fe(CN-2,6-DMP)3-TPCPD and Fe(CN-2-Naphth)3-TPCPD [94 (3)° and 96 (2)°, respectively]. The reported envelope angle between the iron coordinating η4-diene unit and the exo-naphthalene portion is 30.76 (16)° for Fe(η4-anthracene)(CN-2,6-DMP)3, which is significantly higher than the angle observed with the carbonyl units in the cyclopentadienone complexes. This could be due to more aromatic character in the cyclopentadienone ligand made possible by the ketone unit. Both tris(η4-adamantylisocyanide)(1,3,5,7-cyclotetraene)iron and Fe(η4-anthracene)(CN-2,6-DMP)3 show a similar back-bonding situation to Fe(CN-2,6-DMP)3-TPCPD, namely that the isocyanide ligands on the side of the 2,3 positions of the diene (C6 and C7) show more acute C—N—C angles than the ligand on the side of the 1,4 positions (C5 and C8) [177.6 (3), 174.1 (3) and 166.5 (3)° and 170.8 (2), 162.0 (2 and 138.9 (2° for Fe(η4-anthracene)(CN-2,6-DMP)3 and tris(η4-adamantylisocyanide)(1,3,5,7-cyclotetraene)iron, respectively]. Since in these crystals no obvious intermolecular interactions can be observed, as in the case for Fe(CN-2,6-DMP)3-TPCPD, the differences in angles depending on the position could be rationalized by electronic effects.
5. Synthesis and crystallization
The general procedure for the synthesis of the triisocyanide complexes is as follows: Under an atmosphere of N2, the iron tricarbonyl complex (1 equiv.) and the isocyanide (4 equiv.) were dissolved in toluene (ca 0.1 M total concentration). Drying or degassing of the solvent was not found to be necessary. The solution was irradiated with blue LEDs (RND Components RND 135-00259, 4.8 W, 470 nm) at room temperature overnight. The next day, the solution was directly loaded onto a silica and purified by using the appropriate as indicated below. The relevant, yellow-colored fractions were combined and concentrated under reduced pressure. For complexes bearing the TPCPD ligands with electron-rich (CNCH2Ph, CNtBu, CNBu), it was necessary to perform rotary evaporation at 298 K instead of 313 K because of the thermal instability of these compounds, as evidenced by the observation of the dark-purple color of the TPCPD ligand during thin layer (TLC) analysis. The complexes were isolated as yellow to orange solids and were characterized by 1H NMR, 13C NMR, elemental analysis and HRMS. Single crystals of the compounds Fe(CN-2,6-DMP)3-TPCPD and Fe(CN-2-Naphth)3-TPCPD were obtained by suspending the solids in acetone to obtain a filtering off the solids and storing the at 253 K in a freezer.
The decomposition upon heating, presumably due to the loss of the cyclopentadienone ligand, appears to depend on how electron rich the complex is as a whole, as indicated by 13C NMR, with more electron density on the cyclopentadienone ligand leading to thermal instability. Combining the observations made above, it can be said that more thermally stable complexes can be expected by combining strongly π-accepting isocyanide ligands with weakly electron-accepting cyclopentadienone ligands, reminiscent of a push–pull interaction between the cyclopentadienone ligand and the isocyanide ligands mitigated by the iron center.
Fe(CO)3-BTTHI and tetraphenylcyclopentadienone were prepared according to literature methods (Moulin et al., 2013; Liang, 2019).
Tricarbonyl(η4-tetraphenylcyclopentadienone)iron: A dried and argon-flushed 100 ml two-necked round-bottom flask equipped with a stir bar and a reflux condenser was charged with 2.0 g tetraphenylcyclopentadienone (5.2 mmol, 1 equiv.), 1.88 g Fe2(CO)9 (5.2 mmol, 1 equiv.) and 50 ml dry toluene. The mixture was heated to reflux overnight. The next day, the mixture was allowed to cool to room temperature. The mixture was passed through a pad of silica and eluted first with toluene to remove Fe(CO)5 and unreacted tetraphenylcyclopentadienone. The was changed to EtOAc and the orange band was collected. The orange solution was concentrated under reduced pressure. The product was obtained as a yellow–orange solid after drying in vacuo (2.0 g, 74%). 1H NMR (δ, 400 MHz, CDCl3): 7.64–7.54 (m, 4H), 7.32–7-23 (m, 8H), 7.23–7.14 (m, 8H). 13C NMR (δ, 100 MHz, CDCl3): 208.7, 170.0, 132.0, 131.0, 130.4, 130.1, 128.9, 128.21, 128.18, 128.0, 104.2, 82.7. Analysis calculated for C32H20FeO4 (%): C, 73.30; H, 3.84. Found: C, 73.51; H, 3.97.
Fe(CNCH2Ts)3-BTTHI: Yield: 54%. TLC (SiO2, EtOAc): rf = 0.2. 1H NMR (δ, 400 MHz, CDCl3): 7.88 (d, J = 8.2 Hz, 6H), 7.44 (d, J = 8.2 Hz, 6H), 4.84 (s, 6H), 2.46 (s, 9H), 2.24 (s, br, 4H), 1.62 (s, br, 4H), 0.00 (s, 18H). 13C NMR (δ, 100 MHz, CDCl3): 188.0, 178.3, 146.5, 133.5, 130.6, 129.2, 105.5, 66.7, 64.4, 25.1, 23.0, 21.9, 0.29. HRMS (m/z): [M + H]+ calculated for C42H54FeN3O7S3Si2: 920.2006. Found: 920.1993. Analysis calculated for C42H53FeN3O7S3Si2 (%): C, 54.83; H, 5.81; N, 4.57. Found: C, 53.56; H, 5.69; N, 4.62.
Fe(CNtBu)3-BTTHI: Yield: 30%. TLC (SiO2, EtOAc): rf = 0.15. 1H NMR (δ, 400 MHz, CDCl3): 2.39–2.22 (m, 4H), 1.63 (s, br, 4H), 1.43 (s, 27H), 0.21 (s, 18H). 13C NMR (δ, 100 MHz, CDCl3): 175.0, 100.7, 62.2, 56.1, 31.6, 25.5, 23.4, 1.2 (CO not observed). HRMS (m/z): [M + H]+ calculated for C30H54FeN3OSi2: 584.3149. Found: 584.3165. Analysis calculated for C30H53FeN3OSi2 (%): C, 61.72; H, 9.15; N, 7.20. Found: C, 58.65; H, 8.85; N, 6.31.
Fe(CNBu)3-BTTHI: Yield: 45%. TLC (SiO2, EtOAc): rf = 0.2. 1H NMR (δ, 300 MHz, CDCl3): 3.59 (t, J = 6.6 Hz, 6H), 2.40–2.23 (m, 4H), 1.72–1.58 [m, 10H, overlapping signals from CNBu CH2 (1×) and BTTHI CH2 (2×)], 1.57–1.38 (m, 6H), 0.95 (t, J = 7.3 Hz, 9H), 0.18 (s, 18H). 13C NMR (δ, 100 MHz, CDCl3): 174.4, 101.0, 61.6, 44.5, 32.3, 24.6, 23.4, 19.8, 13.5, 0.8. (CO not observed). HRMS (m/z): [M + H]+ calculated for C30H54FeN3OSi2: 584.3149. Found: 584.3136. Analysis calculated for C30H53FeN3OSi2 (%): C, 61.72; H, 9.15; N, 7.20. Found: C, 60.90; H, 8.99; N 6.77.
Fe(CN-2,6-DMP)3-BTTHI: Yield: 60%. TLC (SiO2, 4:1 hexane/EtOAc): rf = 0.2. 1H NMR (δ, 500 MHz, CDCl3): 7.04 (s, br, 9H), 2.71–2.63 (m, 2H), 2.50–2.46 (m, 2H), 2.44 (s, 18H), 1.93–1.84 (m, 2H), 1.84–1.74 (m, 2H), 0.23 (s, 18H). 13C NMR (δ, 125 MHz, CDCl3): 134.6, 129.9, 128.0, 126.7, 104.3, 65.7, 25.7, 23.4, 19.3, 0.9 (CNR and CO not observed). HRMS (m/z): [M + H]+ calculated for C42H54FeN3OSi2: 728.3149. Found: 728.3169. Analysis calculated for C42H54FeN3OSi2 (%): C, 69.30; H, 7.34; N, 5.77. Found: C, 68.61; H, 7.50; N, 5.65.
Fe(CN-2-Naphth)3-BTTHI: Yield: 48%. TLC (SiO2, 2:1 hexane/EtOAc): rf = 0.3. 1H NMR (δ, 400 MHz, CDCl3): 7.90–7.76 (m, 12H), 7.59–7.45 (m, 9H), 2.79–2.65 (m, 2H), 2.59–2.49 (m, 2H), 1.96–1.79 (m, 4H), 0.29 (s, 18H). 13C NMR (δ, 100 MHz, CDCl3): 182.8, 178.2, 133.4, 132.0, 129.7, 128.0, 127.9, 127.8, 127.3, 126.7, 124.6, 124.0, 104.8, 66.6, 25.7, 23.5, 1.0. HRMS (m/z): [M + H]+ calculated for C48H48FeN3OSi2: 794.2680. Found: 794.2669. Analysis calculated for C48H47FeN3OSi2 (%): C, 72.62; H, 5.97; N, 5.29. Found: C, 72.45; H, 6.17; N, 5.14.
Fe(CNCH2Ph)3-BTTHI: Yield: 72%. TLC (SiO2, EtOAc): rf = 0.25. 1H NMR (δ, 400 MHz, CDCl3): 7.40–7.27 (m, 15H), 4.85 (s, 6H), 2.31–2.23 (m, 4H), 1.61–1.52 (m, 4H), 0.17 (s, 18H). 13C NMR (δ, 100 MHz, CDCl3): 134.6, 129.0, 128.2, 127.0, 102.3, 63.9, 48.8, 25.3, 23.2, 0.8 (CNR and CO not observed). HRMS (m/z): [M + H]+ calculated for C39H48FeN3OSi2: 686.2680. Found: 686.2669. Analysis calculated for C39H47FeN3OSi2 (%): C, 68.20; H, 7.04; N, 6.12. Found: C, 67.42; H, 7.08; N, 6.16.
Fe(CNCH2Ts)3-TPCPD: Yield: 50%. TLC (SiO2, EtOAc): rf = 0.35. 1H NMR (δ, 400 MHz, CDCl3): 7.78 (d, J = 8.0 Hz, 6H), 7.45–7.38 (m, 4H), 7.32 (d, J = 8.0 Hz, 4H), 7.13–7.02 (m, 8H), 7.02–6.92 (m, 8H), 4.75 (s, 6H), 2.43 (s, 9H). 13C NMR (δ, 100 MHz, CDCl3): 184.8, 146.4, 134.4, 133.6, 133.3, 132.4, 130.9, 130.6, 129.1, 127.5, 127.45, 127.2, 126.1, 99.1, 79.5, 64.5, 21.9. (CO not observed). HRMS (m/z): [M + H]+ calculated for C56H48FeN3O7S3: 1026.1998. Found: 1026.1989. Analysis calculated for C56H47FeN3O7S3 (%): C, 65.55; H, 4.62; N, 4.10. Found: C, 64.41; H, 4.76; N, 4.05.
Fe(CNtBu)3-TPCPD: Yield: 20%. TLC (SiO2, EtOAc): rf = 0.2. 1H NMR (δ, 400 MHz, CDCl3): 7.63–7.56 (m, 4H), 7.21–7.16 (m, 4H), 7.13–6.97 (m, 12H), 1.28 (s, 27H). 13C NMR (δ, 100 MHz, CDCl3): 170.0, 161.8, 136.7, 135.5, 132.8, 131.0, 126.9, 126.7, 126.2, 124.8, 95.6, 75.0, 56.7, 31.1. HRMS (m/z): [M + H]+ calculated for C44H48FeN3O: 690.3141. Found: 690.3134. Analysis calculated for C44H47FeN3O (%): C, 76.62; H, 6.87; N, 6.09. Found: C, 74.18; H, 6.81; N, 5.80.
Fe(CNBu)3-TPCPD: Yield: 84%. TLC (SiO2, EtOAc): rf = 0.2. 1H NMR (δ, 400 MHz, CDCl3): 7.65–7.58 (m, 4H), 7.21–7.15 (m, 4H), 7.12–7.00 (m, 12H), 3.50 (t, J = 6.6 Hz, 6H), 1.52–1.43 (m, 6H), 1.34–1.20 (m, 6H), 0.84 (t, J = 7.4 Hz, 9H). 13C NMR (δ, 100 MHz, CDCl3): 171.7, 163.3, 136.8, 135.5, 132.7, 130.6, 127.0, 126.9, 126.3, 124.8, 96.1, 74.8, 44.8, 32.0, 19.7, 13.5. HRMS (m/z): [M + H]+ calculated for C44H48FeN3O: 690.3141. Found: 690.3126. Analysis calculated for C44H47FeN3O (%): C, 76.62; H, 6.87; N, 6.09. Found: C, 75.85; H, 7.07; N, 6.00.
Fe(CN-2,6-DMP)3-TPCPD: Yield: 85%. TLC (SiO2, 2:1 hexane/EtOAc): rf: 0.25. 1H NMR (δ, 500 MHz, CDCl3): 7.79–7.74 (m, 4H), 7.34–7.28 (m, 4H), 7.12–7.04 (m, 8H), 7.04–7.00 (7H), 7.00–6.95 (m, 6H), 2.19 (s, 18H). 13C NMR (δ, 125 MHz, CDCl3): 181.9, 165.9, 135.8, 134.9, 134.6, 132.8, 130.9, 129.7, 127.8, 127.3, 127.2, 127.1, 126.8, 125.5, 98.8, 77.4, 18.9. HRMS (m/z): [M + H]+ calculated for C56H48FeN3O: 834.3141. Found: 834.3137. Analysis calculated for C56H47FeN3O (%): C, 80.66; H, 5.68; N, 5.04. Found: C, 79.94; H, 5.87; N, 4.96.
Fe(CN-2-Naphth)3-TPCPD: Yield: 79%. TLC (SiO2, 1:1 hexane/EtOAc): rf = 0.2. 1H NMR (δ, 500 MHz, CDCl3): 7.87–7.83 (m, 4H), 7.83–7.79 (m, 3H), 7.75 (d, J = 8.8 Hz, 3H), 7.73–7.70 (m, 3H), 7.55–7.48 (m, 9H), 7.44–7.39 (m, 4H), 7.22–7.13 (m, 11H), 7.12–7.07 (m, 4H). 13C NMR (δ, 125 MHz, CDCl3): 180.2, 165.3, 135.6, 134.5, 133.2, 132.8, 132.1, 131.1, 129.4, 127.9, 127.7, 127.6, 127.49, 127.46, 127.2, 127.0, 126.8, 125.8, 124.6, 123.8, 98.8, 78.5. HRMS (m/z): [M + H]+ calculated for C62H42FeN3O: 900.2672. Found: 900.2649. Analysis calculated for C62H41FeN3O (%): C, 82.75; H, 4.59; N, 4.67. Found: C, 79.73; H, 4.82; N, 4.36.
Fe(CNCH2Ph)3-TPCPD: Yield: 48%. TLC (SiO2, EtOAc): rf = 0.2. 1H NMR (δ, 300 MHz, CDCl3): 7.65–7.57 (m, 4H), 7.25–7.11 (m, 12H), 7.11–6.98 (m, 15H), 6.99–6.88 (m, 4H), 4.72 (s, 6H). 13C NMR (δ, 100 MHz, CDCl3): 173.6, 163.6, 136.2, 134.9, 133.9, 132.7, 130.9, 128.9, 128.0, 127.1, 127.03, 126.96, 126.4, 125.2, 96.6, 76.0, 48.9. HRMS (m/z): [M + H]+ calculated for C53H42FeN3O: 792.2672. Found: 792.2672. Analysis calculated for C53H41FeN3O (%): C, 80.40; H, 5.22; N, 5.31. Found: C, 77.91; H, 5.26; N, 5.12.
6. Refinement
Crystal data, data collection and structure . H atoms were positioned geometrically (C—H = 0.95–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(H). The crystal for Fe(CN-2-Naphth)3-TPCPD was twinned. Two domains, with approximate refined mass fractions of 3:1 and rotated by approximately 179°, were found and integrated simultaneously. The best model in terms of residual densities and their location, R values and weighting scheme was obtained using de-twinned HKLF4 data.
details are summarized in Table 2
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Supporting information
https://doi.org/10.1107/S205698902300498X/mw2197sup1.cif
contains datablocks I, twin. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902300498X/mw2197Isup2.hkl
Structure factors: contains datablock twin. DOI: https://doi.org/10.1107/S205698902300498X/mw2197twinsup3.hkl
Data collection: CrysAlis PRO 1.171.41.119a (Rigaku OD, 2021) for (I); CrysAlis PRO 1.171.42.79a (Rigaku OD, 2022) for twin. Cell
CrysAlis PRO 1.171.41.119a (Rigaku OD, 2021) for (I); CrysAlis PRO 1.171.42.79a (Rigaku OD, 2022) for twin. Data reduction: CrysAlis PRO 1.171.41.119a (Rigaku OD, 2021) for (I); CrysAlis PRO 1.171.42.79a (Rigaku OD, 2022) for twin. For both structures, program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: Mercury (Macrae et al., 2020).[Fe(C9H9N)3(C29H20O)] | Dx = 1.293 Mg m−3 |
Mr = 833.81 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, Pca21 | Cell parameters from 11706 reflections |
a = 16.7473 (3) Å | θ = 3.6–79.3° |
b = 12.1998 (2) Å | µ = 3.16 mm−1 |
c = 20.9668 (4) Å | T = 100 K |
V = 4283.81 (13) Å3 | Needle, clear yellow |
Z = 4 | 0.14 × 0.03 × 0.02 mm |
F(000) = 1752 |
XtaLAB Synergy, Dualflex, Pilatus 300K diffractometer | 7440 independent reflections |
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source | 6449 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.081 |
Detector resolution: 5.8140 pixels mm-1 | θmax = 80.1°, θmin = 3.6° |
ω scans | h = −21→20 |
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2021) | k = −15→15 |
Tmin = 0.697, Tmax = 1.000 | l = −26→21 |
33622 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.063P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.109 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.36 e Å−3 |
7440 reflections | Δρmin = −0.40 e Å−3 |
556 parameters | Absolute structure: Flack x determined using 1989 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: −0.008 (4) |
Primary atom site location: dual |
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. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.44212 (3) | 0.29727 (4) | 0.49025 (3) | 0.01969 (13) | |
O1 | 0.34098 (16) | 0.1785 (2) | 0.37047 (13) | 0.0247 (6) | |
N1 | 0.5466 (2) | 0.2208 (3) | 0.38217 (18) | 0.0258 (7) | |
N2 | 0.5401 (2) | 0.2204 (3) | 0.60128 (19) | 0.0278 (7) | |
N3 | 0.51844 (17) | 0.5183 (2) | 0.48677 (19) | 0.0255 (6) | |
C1 | 0.5072 (2) | 0.2484 (3) | 0.4249 (2) | 0.0259 (9) | |
C2 | 0.5031 (2) | 0.2504 (3) | 0.55733 (19) | 0.0241 (8) | |
C3 | 0.4886 (2) | 0.4325 (3) | 0.4898 (2) | 0.0240 (7) | |
C4 | 0.3418 (2) | 0.2250 (3) | 0.4232 (2) | 0.0219 (8) | |
C5 | 0.35340 (18) | 0.1724 (2) | 0.4859 (2) | 0.0210 (6) | |
C6 | 0.3355 (2) | 0.2502 (3) | 0.53539 (19) | 0.0199 (7) | |
C7 | 0.3282 (2) | 0.3565 (3) | 0.50543 (18) | 0.0208 (7) | |
C8 | 0.3381 (2) | 0.3442 (3) | 0.43788 (18) | 0.0211 (7) | |
C9 | 0.3600 (2) | 0.0516 (2) | 0.4933 (2) | 0.0233 (7) | |
C10 | 0.4154 (2) | −0.0087 (3) | 0.4587 (2) | 0.0270 (8) | |
H10 | 0.451113 | 0.028206 | 0.430856 | 0.032* | |
C11 | 0.4194 (3) | −0.1221 (3) | 0.4642 (2) | 0.0337 (9) | |
H11 | 0.457570 | −0.161958 | 0.439927 | 0.040* | |
C12 | 0.3681 (3) | −0.1774 (3) | 0.5049 (2) | 0.0356 (10) | |
H12 | 0.371492 | −0.254748 | 0.509268 | 0.043* | |
C13 | 0.3116 (3) | −0.1186 (3) | 0.5392 (2) | 0.0334 (9) | |
H13 | 0.275669 | −0.155950 | 0.566711 | 0.040* | |
C14 | 0.3076 (3) | −0.0055 (3) | 0.5335 (2) | 0.0297 (8) | |
H14 | 0.268673 | 0.033951 | 0.557136 | 0.036* | |
C15 | 0.3175 (2) | 0.2258 (3) | 0.6031 (2) | 0.0224 (7) | |
C16 | 0.3635 (2) | 0.1555 (3) | 0.64050 (19) | 0.0250 (8) | |
H16 | 0.410074 | 0.122967 | 0.622858 | 0.030* | |
C17 | 0.3424 (2) | 0.1321 (3) | 0.7032 (2) | 0.0289 (8) | |
H17 | 0.375556 | 0.086079 | 0.728307 | 0.035* | |
C18 | 0.2733 (2) | 0.1755 (3) | 0.7291 (2) | 0.0286 (8) | |
H18 | 0.258942 | 0.159492 | 0.771960 | 0.034* | |
C19 | 0.2253 (2) | 0.2427 (3) | 0.6918 (2) | 0.0284 (8) | |
H19 | 0.176829 | 0.270689 | 0.708802 | 0.034* | |
C20 | 0.2475 (2) | 0.2692 (3) | 0.62986 (19) | 0.0241 (8) | |
H20 | 0.214970 | 0.317101 | 0.605363 | 0.029* | |
C21 | 0.3020 (2) | 0.4560 (3) | 0.54132 (19) | 0.0229 (7) | |
C22 | 0.3432 (2) | 0.4931 (3) | 0.59502 (19) | 0.0263 (8) | |
H22 | 0.392299 | 0.459712 | 0.606579 | 0.032* | |
C23 | 0.3130 (3) | 0.5785 (3) | 0.6317 (2) | 0.0296 (8) | |
H23 | 0.341359 | 0.602888 | 0.668332 | 0.036* | |
C24 | 0.2411 (3) | 0.6282 (3) | 0.6147 (2) | 0.0323 (9) | |
H24 | 0.219540 | 0.685330 | 0.640286 | 0.039* | |
C25 | 0.2011 (2) | 0.5939 (3) | 0.5604 (2) | 0.0314 (9) | |
H25 | 0.153037 | 0.629211 | 0.547934 | 0.038* | |
C26 | 0.2311 (2) | 0.5081 (3) | 0.5241 (2) | 0.0269 (8) | |
H26 | 0.203041 | 0.484711 | 0.487102 | 0.032* | |
C27 | 0.3286 (2) | 0.4318 (3) | 0.38982 (19) | 0.0241 (8) | |
C28 | 0.3420 (2) | 0.5434 (3) | 0.4046 (2) | 0.0281 (8) | |
H28 | 0.363307 | 0.562470 | 0.445112 | 0.034* | |
C29 | 0.3246 (3) | 0.6253 (3) | 0.3611 (2) | 0.0308 (9) | |
H29 | 0.332359 | 0.699903 | 0.372456 | 0.037* | |
C30 | 0.2959 (3) | 0.5993 (3) | 0.3011 (2) | 0.0381 (10) | |
H30 | 0.283663 | 0.655662 | 0.271401 | 0.046* | |
C31 | 0.2851 (3) | 0.4899 (3) | 0.2846 (2) | 0.0352 (9) | |
H31 | 0.266627 | 0.471371 | 0.243156 | 0.042* | |
C32 | 0.3011 (2) | 0.4076 (3) | 0.3285 (2) | 0.0272 (8) | |
H32 | 0.293296 | 0.333263 | 0.316540 | 0.033* | |
C33 | 0.5933 (2) | 0.1901 (3) | 0.33020 (19) | 0.0245 (8) | |
C34 | 0.5665 (2) | 0.2148 (3) | 0.2688 (2) | 0.0278 (9) | |
C35 | 0.4882 (3) | 0.2716 (4) | 0.2592 (2) | 0.0394 (10) | |
H35A | 0.446900 | 0.234730 | 0.284361 | 0.059* | |
H35B | 0.473743 | 0.269284 | 0.213920 | 0.059* | |
H35C | 0.492766 | 0.348139 | 0.272994 | 0.059* | |
C36 | 0.6154 (3) | 0.1832 (3) | 0.2180 (2) | 0.0363 (10) | |
H36 | 0.598949 | 0.197116 | 0.175438 | 0.044* | |
C37 | 0.6878 (3) | 0.1316 (3) | 0.2294 (2) | 0.0406 (11) | |
H37 | 0.721016 | 0.112063 | 0.194436 | 0.049* | |
C38 | 0.7122 (3) | 0.1085 (3) | 0.2905 (2) | 0.0370 (10) | |
H38 | 0.761845 | 0.072581 | 0.297136 | 0.044* | |
C39 | 0.6658 (2) | 0.1366 (3) | 0.3426 (2) | 0.0298 (9) | |
C40 | 0.6909 (3) | 0.1127 (4) | 0.4099 (3) | 0.0440 (11) | |
H40A | 0.697759 | 0.181828 | 0.433163 | 0.066* | |
H40B | 0.741584 | 0.072510 | 0.409616 | 0.066* | |
H40C | 0.649900 | 0.068351 | 0.430990 | 0.066* | |
C41 | 0.5568 (2) | 0.1777 (3) | 0.6620 (2) | 0.0263 (8) | |
C42 | 0.5805 (2) | 0.0682 (3) | 0.6658 (2) | 0.0293 (8) | |
C43 | 0.5935 (3) | 0.0009 (3) | 0.6074 (3) | 0.0432 (11) | |
H43A | 0.541778 | −0.021491 | 0.589824 | 0.065* | |
H43B | 0.624754 | −0.064352 | 0.618305 | 0.065* | |
H43C | 0.622491 | 0.044347 | 0.575618 | 0.065* | |
C44 | 0.5888 (3) | 0.0228 (4) | 0.7264 (3) | 0.0397 (11) | |
H44 | 0.604670 | −0.051553 | 0.730785 | 0.048* | |
C45 | 0.5742 (3) | 0.0855 (5) | 0.7802 (3) | 0.0460 (12) | |
H45 | 0.579116 | 0.053327 | 0.821313 | 0.055* | |
C46 | 0.5524 (3) | 0.1944 (4) | 0.7748 (3) | 0.0452 (12) | |
H46 | 0.543125 | 0.236364 | 0.812217 | 0.054* | |
C47 | 0.5439 (3) | 0.2434 (4) | 0.7156 (2) | 0.0352 (10) | |
C48 | 0.5181 (4) | 0.3609 (4) | 0.7074 (3) | 0.0601 (16) | |
H48A | 0.549030 | 0.394599 | 0.672876 | 0.090* | |
H48B | 0.527450 | 0.401122 | 0.747135 | 0.090* | |
H48C | 0.461175 | 0.363298 | 0.696745 | 0.090* | |
C49 | 0.5590 (2) | 0.6118 (3) | 0.46513 (19) | 0.0251 (8) | |
C50 | 0.5748 (2) | 0.6956 (3) | 0.5084 (2) | 0.0272 (8) | |
C51 | 0.5468 (3) | 0.6862 (3) | 0.5761 (2) | 0.0335 (9) | |
H51A | 0.488492 | 0.679505 | 0.576812 | 0.050* | |
H51B | 0.562872 | 0.751732 | 0.599833 | 0.050* | |
H51C | 0.570728 | 0.621185 | 0.595776 | 0.050* | |
C52 | 0.6185 (2) | 0.7852 (3) | 0.4862 (3) | 0.0323 (8) | |
H52 | 0.632142 | 0.842696 | 0.514717 | 0.039* | |
C53 | 0.6423 (2) | 0.7911 (3) | 0.4229 (2) | 0.0330 (9) | |
H53 | 0.670757 | 0.853558 | 0.408235 | 0.040* | |
C54 | 0.6251 (2) | 0.7071 (3) | 0.3812 (2) | 0.0331 (9) | |
H54 | 0.641741 | 0.712719 | 0.338044 | 0.040* | |
C55 | 0.5837 (2) | 0.6142 (3) | 0.4012 (2) | 0.0309 (9) | |
C56 | 0.5695 (3) | 0.5184 (4) | 0.3583 (2) | 0.0438 (11) | |
H56A | 0.596322 | 0.453630 | 0.375809 | 0.066* | |
H56B | 0.590747 | 0.534355 | 0.315812 | 0.066* | |
H56C | 0.511980 | 0.504244 | 0.355315 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0222 (2) | 0.0168 (2) | 0.0200 (3) | −0.00091 (18) | 0.0003 (3) | 0.0004 (2) |
O1 | 0.0310 (14) | 0.0216 (11) | 0.0215 (15) | 0.0005 (10) | −0.0023 (11) | −0.0012 (10) |
N1 | 0.0261 (17) | 0.0258 (15) | 0.026 (2) | −0.0001 (12) | 0.0045 (14) | −0.0020 (13) |
N2 | 0.0252 (16) | 0.0279 (15) | 0.030 (2) | −0.0020 (13) | −0.0012 (15) | 0.0070 (15) |
N3 | 0.0288 (14) | 0.0203 (12) | 0.0273 (16) | −0.0042 (10) | −0.0006 (15) | 0.0011 (14) |
C1 | 0.0249 (19) | 0.0188 (15) | 0.034 (3) | −0.0028 (14) | −0.0081 (18) | 0.0025 (15) |
C2 | 0.0270 (19) | 0.0181 (15) | 0.027 (2) | −0.0033 (13) | −0.0001 (17) | −0.0010 (14) |
C3 | 0.0262 (16) | 0.0259 (15) | 0.0197 (18) | 0.0019 (12) | −0.0009 (17) | 0.0007 (16) |
C4 | 0.0197 (17) | 0.0207 (15) | 0.025 (2) | −0.0003 (13) | −0.0009 (15) | −0.0027 (14) |
C5 | 0.0188 (14) | 0.0172 (13) | 0.0270 (19) | −0.0026 (10) | 0.0010 (17) | −0.0038 (16) |
C6 | 0.0177 (16) | 0.0190 (14) | 0.023 (2) | −0.0017 (12) | 0.0010 (14) | 0.0010 (14) |
C7 | 0.0219 (16) | 0.0192 (14) | 0.021 (2) | 0.0002 (12) | −0.0009 (13) | −0.0009 (13) |
C8 | 0.0195 (17) | 0.0179 (15) | 0.026 (2) | 0.0014 (12) | −0.0052 (14) | 0.0002 (14) |
C9 | 0.0290 (16) | 0.0202 (14) | 0.0206 (19) | −0.0010 (12) | −0.0047 (17) | −0.0004 (16) |
C10 | 0.0296 (19) | 0.0218 (16) | 0.030 (2) | −0.0014 (14) | −0.0023 (16) | −0.0044 (15) |
C11 | 0.041 (2) | 0.0235 (17) | 0.037 (2) | 0.0063 (15) | −0.0090 (18) | −0.0079 (16) |
C12 | 0.053 (3) | 0.0182 (15) | 0.035 (3) | 0.0018 (16) | −0.0157 (19) | 0.0020 (15) |
C13 | 0.053 (3) | 0.0231 (16) | 0.024 (2) | −0.0080 (17) | −0.0036 (19) | 0.0026 (16) |
C14 | 0.039 (2) | 0.0248 (17) | 0.026 (2) | −0.0059 (15) | 0.0000 (17) | −0.0030 (15) |
C15 | 0.0235 (17) | 0.0185 (14) | 0.025 (2) | −0.0040 (12) | −0.0021 (16) | −0.0019 (14) |
C16 | 0.0270 (18) | 0.0222 (15) | 0.026 (2) | −0.0022 (13) | 0.0007 (15) | 0.0008 (14) |
C17 | 0.035 (2) | 0.0249 (16) | 0.027 (2) | −0.0061 (15) | −0.0033 (16) | 0.0035 (15) |
C18 | 0.038 (2) | 0.0278 (17) | 0.020 (2) | −0.0089 (15) | 0.0047 (17) | −0.0019 (15) |
C19 | 0.0304 (19) | 0.0258 (17) | 0.029 (2) | −0.0030 (15) | 0.0060 (16) | −0.0047 (15) |
C20 | 0.0244 (18) | 0.0217 (15) | 0.026 (2) | −0.0017 (13) | 0.0018 (15) | 0.0004 (14) |
C21 | 0.0255 (18) | 0.0170 (14) | 0.026 (2) | −0.0030 (13) | 0.0003 (15) | 0.0006 (14) |
C22 | 0.032 (2) | 0.0230 (16) | 0.024 (2) | −0.0008 (14) | 0.0003 (16) | 0.0015 (14) |
C23 | 0.044 (2) | 0.0198 (15) | 0.025 (2) | −0.0057 (15) | 0.0055 (17) | −0.0016 (15) |
C24 | 0.046 (2) | 0.0188 (15) | 0.032 (2) | −0.0007 (15) | 0.0160 (19) | −0.0039 (15) |
C25 | 0.031 (2) | 0.0255 (17) | 0.038 (3) | 0.0020 (15) | 0.0082 (18) | 0.0041 (16) |
C26 | 0.0271 (18) | 0.0208 (15) | 0.033 (2) | 0.0017 (14) | 0.0005 (16) | 0.0017 (15) |
C27 | 0.0231 (18) | 0.0234 (16) | 0.026 (2) | −0.0006 (13) | 0.0033 (15) | −0.0002 (14) |
C28 | 0.034 (2) | 0.0219 (16) | 0.028 (2) | 0.0001 (15) | 0.0001 (17) | 0.0010 (15) |
C29 | 0.045 (2) | 0.0189 (15) | 0.029 (2) | 0.0008 (15) | −0.0017 (18) | 0.0030 (15) |
C30 | 0.057 (3) | 0.0260 (18) | 0.032 (3) | 0.0050 (18) | −0.005 (2) | 0.0089 (16) |
C31 | 0.052 (3) | 0.0304 (18) | 0.023 (2) | 0.0019 (18) | −0.005 (2) | 0.0032 (17) |
C32 | 0.034 (2) | 0.0227 (16) | 0.025 (2) | 0.0029 (14) | −0.0006 (16) | −0.0026 (15) |
C33 | 0.0279 (19) | 0.0210 (15) | 0.025 (2) | −0.0031 (13) | 0.0051 (16) | −0.0022 (14) |
C34 | 0.036 (2) | 0.0228 (16) | 0.025 (2) | −0.0030 (15) | −0.0001 (17) | −0.0035 (14) |
C35 | 0.043 (3) | 0.039 (2) | 0.036 (3) | 0.0051 (19) | −0.007 (2) | 0.0013 (18) |
C36 | 0.052 (3) | 0.0286 (19) | 0.028 (2) | −0.0115 (18) | 0.006 (2) | −0.0041 (17) |
C37 | 0.048 (3) | 0.031 (2) | 0.043 (3) | −0.0051 (18) | 0.022 (2) | −0.0098 (19) |
C38 | 0.031 (2) | 0.0283 (18) | 0.051 (3) | −0.0012 (16) | 0.009 (2) | −0.0083 (18) |
C39 | 0.0281 (19) | 0.0234 (16) | 0.038 (3) | 0.0002 (14) | 0.0027 (17) | −0.0037 (16) |
C40 | 0.043 (3) | 0.043 (2) | 0.045 (3) | 0.008 (2) | −0.010 (2) | −0.002 (2) |
C41 | 0.0236 (19) | 0.0289 (17) | 0.026 (2) | −0.0015 (14) | −0.0038 (16) | 0.0023 (16) |
C42 | 0.0234 (18) | 0.0296 (18) | 0.035 (2) | 0.0001 (14) | −0.0050 (17) | 0.0051 (17) |
C43 | 0.050 (3) | 0.032 (2) | 0.048 (3) | 0.0078 (18) | −0.003 (2) | −0.006 (2) |
C44 | 0.033 (2) | 0.037 (2) | 0.049 (3) | −0.0057 (17) | −0.009 (2) | 0.016 (2) |
C45 | 0.034 (2) | 0.075 (3) | 0.029 (3) | −0.009 (2) | −0.0069 (19) | 0.014 (3) |
C46 | 0.038 (2) | 0.069 (3) | 0.029 (3) | 0.003 (2) | −0.005 (2) | −0.012 (2) |
C47 | 0.032 (2) | 0.042 (2) | 0.032 (3) | 0.0019 (18) | −0.0067 (19) | −0.008 (2) |
C48 | 0.068 (4) | 0.050 (3) | 0.062 (4) | 0.021 (3) | −0.024 (3) | −0.026 (3) |
C49 | 0.0253 (17) | 0.0208 (16) | 0.029 (2) | −0.0012 (13) | −0.0029 (15) | 0.0063 (14) |
C50 | 0.0263 (18) | 0.0222 (16) | 0.033 (2) | 0.0015 (13) | −0.0022 (15) | 0.0013 (15) |
C51 | 0.035 (2) | 0.0312 (19) | 0.034 (3) | −0.0050 (16) | 0.0024 (18) | −0.0064 (17) |
C52 | 0.0310 (18) | 0.0212 (14) | 0.045 (2) | −0.0027 (12) | 0.002 (2) | −0.0024 (18) |
C53 | 0.0257 (19) | 0.0243 (17) | 0.049 (3) | −0.0022 (15) | 0.0031 (18) | 0.0094 (17) |
C54 | 0.031 (2) | 0.0333 (19) | 0.034 (3) | −0.0034 (15) | 0.0037 (17) | 0.0109 (18) |
C55 | 0.033 (2) | 0.0288 (18) | 0.031 (2) | −0.0020 (15) | −0.0021 (17) | 0.0040 (16) |
C56 | 0.057 (3) | 0.045 (2) | 0.029 (3) | −0.012 (2) | 0.004 (2) | −0.002 (2) |
Fe1—C1 | 1.850 (4) | C28—C29 | 1.385 (5) |
Fe1—C2 | 1.830 (4) | C29—H29 | 0.9500 |
Fe1—C3 | 1.825 (3) | C29—C30 | 1.383 (6) |
Fe1—C4 | 2.361 (4) | C30—H30 | 0.9500 |
Fe1—C5 | 2.130 (3) | C30—C31 | 1.390 (6) |
Fe1—C6 | 2.101 (4) | C31—H31 | 0.9500 |
Fe1—C7 | 2.065 (3) | C31—C32 | 1.387 (6) |
Fe1—C8 | 2.137 (3) | C32—H32 | 0.9500 |
O1—C4 | 1.243 (5) | C33—C34 | 1.397 (6) |
N1—C1 | 1.162 (6) | C33—C39 | 1.403 (5) |
N1—C33 | 1.392 (5) | C34—C35 | 1.496 (6) |
N2—C2 | 1.169 (5) | C34—C36 | 1.397 (6) |
N2—C41 | 1.403 (6) | C35—H35A | 0.9800 |
N3—C3 | 1.162 (4) | C35—H35B | 0.9800 |
N3—C49 | 1.403 (4) | C35—H35C | 0.9800 |
C4—C5 | 1.475 (6) | C36—H36 | 0.9500 |
C4—C8 | 1.487 (4) | C36—C37 | 1.386 (7) |
C5—C6 | 1.438 (5) | C37—H37 | 0.9500 |
C5—C9 | 1.487 (4) | C37—C38 | 1.375 (7) |
C6—C7 | 1.447 (5) | C38—H38 | 0.9500 |
C6—C15 | 1.482 (6) | C38—C39 | 1.384 (6) |
C7—C8 | 1.434 (6) | C39—C40 | 1.501 (7) |
C7—C21 | 1.494 (5) | C40—H40A | 0.9800 |
C8—C27 | 1.478 (5) | C40—H40B | 0.9800 |
C9—C10 | 1.388 (5) | C40—H40C | 0.9800 |
C9—C14 | 1.402 (5) | C41—C42 | 1.397 (5) |
C10—H10 | 0.9500 | C41—C47 | 1.398 (6) |
C10—C11 | 1.390 (5) | C42—C43 | 1.490 (6) |
C11—H11 | 0.9500 | C42—C44 | 1.392 (6) |
C11—C12 | 1.387 (6) | C43—H43A | 0.9800 |
C12—H12 | 0.9500 | C43—H43B | 0.9800 |
C12—C13 | 1.387 (6) | C43—H43C | 0.9800 |
C13—H13 | 0.9500 | C44—H44 | 0.9500 |
C13—C14 | 1.387 (5) | C44—C45 | 1.386 (8) |
C14—H14 | 0.9500 | C45—H45 | 0.9500 |
C15—C16 | 1.393 (5) | C45—C46 | 1.383 (8) |
C15—C20 | 1.404 (5) | C46—H46 | 0.9500 |
C16—H16 | 0.9500 | C46—C47 | 1.383 (7) |
C16—C17 | 1.390 (6) | C47—C48 | 1.507 (7) |
C17—H17 | 0.9500 | C48—H48A | 0.9800 |
C17—C18 | 1.383 (6) | C48—H48B | 0.9800 |
C18—H18 | 0.9500 | C48—H48C | 0.9800 |
C18—C19 | 1.390 (6) | C49—C50 | 1.391 (5) |
C19—H19 | 0.9500 | C49—C55 | 1.404 (6) |
C19—C20 | 1.389 (6) | C50—C51 | 1.498 (6) |
C20—H20 | 0.9500 | C50—C52 | 1.396 (5) |
C21—C22 | 1.396 (5) | C51—H51A | 0.9800 |
C21—C26 | 1.394 (5) | C51—H51B | 0.9800 |
C22—H22 | 0.9500 | C51—H51C | 0.9800 |
C22—C23 | 1.390 (5) | C52—H52 | 0.9500 |
C23—H23 | 0.9500 | C52—C53 | 1.387 (7) |
C23—C24 | 1.396 (6) | C53—H53 | 0.9500 |
C24—H24 | 0.9500 | C53—C54 | 1.377 (6) |
C24—C25 | 1.386 (6) | C54—H54 | 0.9500 |
C25—H25 | 0.9500 | C54—C55 | 1.393 (5) |
C25—C26 | 1.388 (5) | C55—C56 | 1.493 (6) |
C26—H26 | 0.9500 | C56—H56A | 0.9800 |
C27—C28 | 1.414 (5) | C56—H56B | 0.9800 |
C27—C32 | 1.398 (6) | C56—H56C | 0.9800 |
C28—H28 | 0.9500 | ||
C1—Fe1—C4 | 81.84 (15) | C24—C25—C26 | 120.3 (4) |
C1—Fe1—C5 | 98.56 (15) | C26—C25—H25 | 119.9 |
C1—Fe1—C6 | 138.28 (15) | C21—C26—H26 | 119.7 |
C1—Fe1—C7 | 140.51 (16) | C25—C26—C21 | 120.6 (4) |
C1—Fe1—C8 | 100.74 (16) | C25—C26—H26 | 119.7 |
C2—Fe1—C1 | 98.02 (16) | C28—C27—C8 | 122.0 (3) |
C2—Fe1—C4 | 137.55 (14) | C32—C27—C8 | 120.7 (3) |
C2—Fe1—C5 | 101.46 (16) | C32—C27—C28 | 117.2 (3) |
C2—Fe1—C6 | 92.42 (16) | C27—C28—H28 | 119.5 |
C2—Fe1—C7 | 120.43 (17) | C29—C28—C27 | 121.1 (4) |
C2—Fe1—C8 | 158.98 (16) | C29—C28—H28 | 119.5 |
C3—Fe1—C1 | 92.11 (17) | C28—C29—H29 | 119.8 |
C3—Fe1—C2 | 92.78 (17) | C30—C29—C28 | 120.5 (4) |
C3—Fe1—C4 | 129.67 (15) | C30—C29—H29 | 119.8 |
C3—Fe1—C5 | 160.77 (14) | C29—C30—H30 | 120.3 |
C3—Fe1—C6 | 127.73 (15) | C29—C30—C31 | 119.4 (4) |
C3—Fe1—C7 | 94.48 (14) | C31—C30—H30 | 120.3 |
C3—Fe1—C8 | 95.90 (14) | C30—C31—H31 | 119.8 |
C5—Fe1—C4 | 37.91 (15) | C32—C31—C30 | 120.3 (4) |
C5—Fe1—C8 | 66.48 (13) | C32—C31—H31 | 119.8 |
C6—Fe1—C4 | 63.99 (14) | C27—C32—H32 | 119.3 |
C6—Fe1—C5 | 39.73 (14) | C31—C32—C27 | 121.4 (3) |
C6—Fe1—C8 | 67.18 (14) | C31—C32—H32 | 119.3 |
C7—Fe1—C4 | 64.22 (13) | N1—C33—C34 | 118.9 (4) |
C7—Fe1—C5 | 67.20 (12) | N1—C33—C39 | 117.8 (4) |
C7—Fe1—C6 | 40.63 (13) | C34—C33—C39 | 123.3 (4) |
C7—Fe1—C8 | 39.85 (15) | C33—C34—C35 | 120.4 (4) |
C8—Fe1—C4 | 38.22 (12) | C33—C34—C36 | 117.0 (4) |
C1—N1—C33 | 178.6 (4) | C36—C34—C35 | 122.6 (4) |
C2—N2—C41 | 159.5 (4) | C34—C35—H35A | 109.5 |
C3—N3—C49 | 163.5 (4) | C34—C35—H35B | 109.5 |
N1—C1—Fe1 | 177.1 (4) | C34—C35—H35C | 109.5 |
N2—C2—Fe1 | 178.1 (4) | H35A—C35—H35B | 109.5 |
N3—C3—Fe1 | 177.1 (4) | H35A—C35—H35C | 109.5 |
O1—C4—Fe1 | 135.1 (3) | H35B—C35—H35C | 109.5 |
O1—C4—C5 | 126.5 (3) | C34—C36—H36 | 119.7 |
O1—C4—C8 | 129.0 (3) | C37—C36—C34 | 120.5 (4) |
C5—C4—Fe1 | 62.53 (18) | C37—C36—H36 | 119.7 |
C5—C4—C8 | 104.3 (3) | C36—C37—H37 | 119.6 |
C8—C4—Fe1 | 62.74 (18) | C38—C37—C36 | 120.8 (4) |
C4—C5—Fe1 | 79.56 (19) | C38—C37—H37 | 119.6 |
C4—C5—C9 | 122.3 (3) | C37—C38—H38 | 119.4 |
C6—C5—Fe1 | 69.06 (18) | C37—C38—C39 | 121.2 (4) |
C6—C5—C4 | 109.2 (3) | C39—C38—H38 | 119.4 |
C6—C5—C9 | 126.5 (4) | C33—C39—C40 | 120.5 (4) |
C9—C5—Fe1 | 130.8 (2) | C38—C39—C33 | 117.0 (4) |
C5—C6—Fe1 | 71.21 (19) | C38—C39—C40 | 122.4 (4) |
C5—C6—C7 | 107.2 (3) | C39—C40—H40A | 109.5 |
C5—C6—C15 | 127.0 (3) | C39—C40—H40B | 109.5 |
C7—C6—Fe1 | 68.35 (19) | C39—C40—H40C | 109.5 |
C7—C6—C15 | 125.4 (3) | H40A—C40—H40B | 109.5 |
C15—C6—Fe1 | 131.2 (3) | H40A—C40—H40C | 109.5 |
C6—C7—Fe1 | 71.02 (19) | H40B—C40—H40C | 109.5 |
C6—C7—C21 | 122.3 (3) | C42—C41—N2 | 117.6 (4) |
C8—C7—Fe1 | 72.8 (2) | C42—C41—C47 | 123.1 (4) |
C8—C7—C6 | 109.0 (3) | C47—C41—N2 | 119.1 (4) |
C8—C7—C21 | 128.1 (3) | C41—C42—C43 | 121.4 (4) |
C21—C7—Fe1 | 129.3 (2) | C44—C42—C41 | 117.5 (4) |
C4—C8—Fe1 | 79.0 (2) | C44—C42—C43 | 121.1 (4) |
C7—C8—Fe1 | 67.4 (2) | C42—C43—H43A | 109.5 |
C7—C8—C4 | 108.1 (3) | C42—C43—H43B | 109.5 |
C7—C8—C27 | 125.8 (3) | C42—C43—H43C | 109.5 |
C27—C8—Fe1 | 129.2 (3) | H43A—C43—H43B | 109.5 |
C27—C8—C4 | 124.8 (3) | H43A—C43—H43C | 109.5 |
C10—C9—C5 | 121.4 (3) | H43B—C43—H43C | 109.5 |
C10—C9—C14 | 118.0 (3) | C42—C44—H44 | 119.8 |
C14—C9—C5 | 120.6 (3) | C45—C44—C42 | 120.4 (4) |
C9—C10—H10 | 119.4 | C45—C44—H44 | 119.8 |
C9—C10—C11 | 121.1 (4) | C44—C45—H45 | 119.7 |
C11—C10—H10 | 119.4 | C46—C45—C44 | 120.6 (5) |
C10—C11—H11 | 119.9 | C46—C45—H45 | 119.7 |
C12—C11—C10 | 120.3 (4) | C45—C46—H46 | 119.4 |
C12—C11—H11 | 119.9 | C45—C46—C47 | 121.1 (5) |
C11—C12—H12 | 120.3 | C47—C46—H46 | 119.4 |
C11—C12—C13 | 119.4 (3) | C41—C47—C48 | 119.8 (4) |
C13—C12—H12 | 120.3 | C46—C47—C41 | 117.3 (4) |
C12—C13—H13 | 119.9 | C46—C47—C48 | 122.9 (5) |
C14—C13—C12 | 120.2 (4) | C47—C48—H48A | 109.5 |
C14—C13—H13 | 119.9 | C47—C48—H48B | 109.5 |
C9—C14—H14 | 119.5 | C47—C48—H48C | 109.5 |
C13—C14—C9 | 121.1 (4) | H48A—C48—H48B | 109.5 |
C13—C14—H14 | 119.5 | H48A—C48—H48C | 109.5 |
C16—C15—C6 | 123.4 (3) | H48B—C48—H48C | 109.5 |
C16—C15—C20 | 118.0 (4) | N3—C49—C55 | 117.9 (3) |
C20—C15—C6 | 118.4 (3) | C50—C49—N3 | 118.5 (4) |
C15—C16—H16 | 119.4 | C50—C49—C55 | 123.5 (3) |
C17—C16—C15 | 121.1 (4) | C49—C50—C51 | 120.1 (3) |
C17—C16—H16 | 119.4 | C49—C50—C52 | 117.2 (4) |
C16—C17—H17 | 119.8 | C52—C50—C51 | 122.7 (4) |
C18—C17—C16 | 120.4 (4) | C50—C51—H51A | 109.5 |
C18—C17—H17 | 119.8 | C50—C51—H51B | 109.5 |
C17—C18—H18 | 120.4 | C50—C51—H51C | 109.5 |
C17—C18—C19 | 119.2 (4) | H51A—C51—H51B | 109.5 |
C19—C18—H18 | 120.4 | H51A—C51—H51C | 109.5 |
C18—C19—H19 | 119.7 | H51B—C51—H51C | 109.5 |
C20—C19—C18 | 120.6 (4) | C50—C52—H52 | 119.6 |
C20—C19—H19 | 119.7 | C53—C52—C50 | 120.7 (4) |
C15—C20—H20 | 119.7 | C53—C52—H52 | 119.6 |
C19—C20—C15 | 120.6 (4) | C52—C53—H53 | 119.7 |
C19—C20—H20 | 119.7 | C54—C53—C52 | 120.5 (4) |
C22—C21—C7 | 121.6 (3) | C54—C53—H53 | 119.7 |
C26—C21—C7 | 119.3 (3) | C53—C54—H54 | 119.4 |
C26—C21—C22 | 118.8 (3) | C53—C54—C55 | 121.3 (4) |
C21—C22—H22 | 119.6 | C55—C54—H54 | 119.4 |
C23—C22—C21 | 120.7 (4) | C49—C55—C56 | 120.8 (4) |
C23—C22—H22 | 119.6 | C54—C55—C49 | 116.7 (4) |
C22—C23—H23 | 120.1 | C54—C55—C56 | 122.4 (4) |
C22—C23—C24 | 119.8 (4) | C55—C56—H56A | 109.5 |
C24—C23—H23 | 120.1 | C55—C56—H56B | 109.5 |
C23—C24—H24 | 120.2 | C55—C56—H56C | 109.5 |
C25—C24—C23 | 119.7 (4) | H56A—C56—H56B | 109.5 |
C25—C24—H24 | 120.2 | H56A—C56—H56C | 109.5 |
C24—C25—H25 | 119.9 | H56B—C56—H56C | 109.5 |
Fe1—C4—C5—C6 | 63.3 (2) | C7—C21—C26—C25 | 173.5 (3) |
Fe1—C4—C5—C9 | −132.0 (3) | C8—C4—C5—Fe1 | −48.3 (2) |
Fe1—C4—C8—C7 | −61.6 (2) | C8—C4—C5—C6 | 15.0 (3) |
Fe1—C4—C8—C27 | 130.5 (4) | C8—C4—C5—C9 | 179.7 (3) |
Fe1—C5—C6—C7 | 59.1 (2) | C8—C7—C21—C22 | −132.2 (4) |
Fe1—C5—C6—C15 | −128.0 (4) | C8—C7—C21—C26 | 53.1 (5) |
Fe1—C5—C9—C10 | −51.3 (6) | C8—C27—C28—C29 | −173.0 (4) |
Fe1—C5—C9—C14 | 131.7 (4) | C8—C27—C32—C31 | 174.1 (4) |
Fe1—C6—C7—C8 | 63.3 (2) | C9—C5—C6—Fe1 | 125.9 (3) |
Fe1—C6—C7—C21 | −125.1 (3) | C9—C5—C6—C7 | −175.0 (3) |
Fe1—C6—C15—C16 | −49.1 (5) | C9—C5—C6—C15 | −2.1 (6) |
Fe1—C6—C15—C20 | 135.7 (3) | C9—C10—C11—C12 | −0.4 (6) |
Fe1—C7—C8—C4 | 69.3 (2) | C10—C9—C14—C13 | 0.9 (6) |
Fe1—C7—C8—C27 | −122.9 (4) | C10—C11—C12—C13 | 1.2 (6) |
Fe1—C7—C21—C22 | −33.2 (5) | C11—C12—C13—C14 | −1.0 (6) |
Fe1—C7—C21—C26 | 152.1 (3) | C12—C13—C14—C9 | −0.1 (6) |
Fe1—C8—C27—C28 | −61.0 (5) | C14—C9—C10—C11 | −0.7 (6) |
Fe1—C8—C27—C32 | 122.9 (4) | C15—C6—C7—Fe1 | 126.0 (3) |
O1—C4—C5—Fe1 | 127.5 (4) | C15—C6—C7—C8 | −170.7 (3) |
O1—C4—C5—C6 | −169.2 (4) | C15—C6—C7—C21 | 0.9 (5) |
O1—C4—C5—C9 | −4.5 (5) | C15—C16—C17—C18 | 2.3 (5) |
O1—C4—C8—Fe1 | −127.4 (4) | C16—C15—C20—C19 | 0.2 (5) |
O1—C4—C8—C7 | 171.0 (4) | C16—C17—C18—C19 | 0.0 (5) |
O1—C4—C8—C27 | 3.0 (6) | C17—C18—C19—C20 | −2.2 (6) |
N1—C33—C34—C35 | −1.1 (5) | C18—C19—C20—C15 | 2.1 (5) |
N1—C33—C34—C36 | 179.6 (3) | C20—C15—C16—C17 | −2.3 (5) |
N1—C33—C39—C38 | −178.8 (3) | C21—C7—C8—Fe1 | 126.9 (4) |
N1—C33—C39—C40 | 0.6 (5) | C21—C7—C8—C4 | −163.8 (3) |
N2—C41—C42—C43 | 4.5 (6) | C21—C7—C8—C27 | 3.9 (6) |
N2—C41—C42—C44 | −173.3 (4) | C21—C22—C23—C24 | −0.3 (6) |
N2—C41—C47—C46 | 172.8 (4) | C22—C21—C26—C25 | −1.3 (5) |
N2—C41—C47—C48 | −4.5 (6) | C22—C23—C24—C25 | −1.6 (6) |
N3—C49—C50—C51 | −1.5 (5) | C23—C24—C25—C26 | 2.1 (6) |
N3—C49—C50—C52 | 177.1 (3) | C24—C25—C26—C21 | −0.6 (6) |
N3—C49—C55—C54 | −178.9 (4) | C26—C21—C22—C23 | 1.8 (6) |
N3—C49—C55—C56 | −2.1 (6) | C27—C28—C29—C30 | −2.1 (6) |
C2—N2—C41—C42 | 101.2 (11) | C28—C27—C32—C31 | −2.1 (6) |
C2—N2—C41—C47 | −74.3 (12) | C28—C29—C30—C31 | −0.4 (7) |
C3—N3—C49—C50 | −175.2 (11) | C29—C30—C31—C32 | 1.5 (7) |
C3—N3—C49—C55 | 2.9 (14) | C30—C31—C32—C27 | −0.2 (7) |
C4—C5—C6—Fe1 | −70.2 (2) | C32—C27—C28—C29 | 3.3 (6) |
C4—C5—C6—C7 | −11.1 (4) | C33—C34—C36—C37 | −1.3 (5) |
C4—C5—C6—C15 | 161.8 (3) | C34—C33—C39—C38 | 0.5 (5) |
C4—C5—C9—C10 | 53.9 (5) | C34—C33—C39—C40 | 179.9 (4) |
C4—C5—C9—C14 | −123.1 (4) | C34—C36—C37—C38 | 1.4 (6) |
C4—C8—C27—C28 | −166.6 (3) | C35—C34—C36—C37 | 179.4 (4) |
C4—C8—C27—C32 | 17.3 (6) | C36—C37—C38—C39 | −0.5 (6) |
C5—C4—C8—Fe1 | 48.2 (2) | C37—C38—C39—C33 | −0.4 (5) |
C5—C4—C8—C7 | −13.4 (4) | C37—C38—C39—C40 | −179.8 (4) |
C5—C4—C8—C27 | 178.7 (3) | C39—C33—C34—C35 | 179.7 (4) |
C5—C6—C7—Fe1 | −60.9 (2) | C39—C33—C34—C36 | 0.3 (5) |
C5—C6—C7—C8 | 2.4 (4) | C41—C42—C44—C45 | −0.2 (6) |
C5—C6—C7—C21 | 173.9 (3) | C42—C41—C47—C46 | −2.5 (6) |
C5—C6—C15—C16 | 48.0 (5) | C42—C41—C47—C48 | −179.8 (4) |
C5—C6—C15—C20 | −127.2 (4) | C42—C44—C45—C46 | −1.1 (7) |
C5—C9—C10—C11 | −177.7 (4) | C43—C42—C44—C45 | −178.0 (4) |
C5—C9—C14—C13 | 178.0 (4) | C44—C45—C46—C47 | 0.7 (7) |
C6—C5—C9—C10 | −144.1 (4) | C45—C46—C47—C41 | 1.1 (7) |
C6—C5—C9—C14 | 38.8 (5) | C45—C46—C47—C48 | 178.3 (5) |
C6—C7—C8—Fe1 | −62.2 (2) | C47—C41—C42—C43 | 179.8 (4) |
C6—C7—C8—C4 | 7.1 (4) | C47—C41—C42—C44 | 2.1 (6) |
C6—C7—C8—C27 | 174.9 (3) | C49—C50—C52—C53 | 2.3 (5) |
C6—C7—C21—C22 | 58.0 (5) | C50—C49—C55—C54 | −0.9 (6) |
C6—C7—C21—C26 | −116.8 (4) | C50—C49—C55—C56 | 176.0 (4) |
C6—C15—C16—C17 | −177.6 (3) | C50—C52—C53—C54 | −1.8 (6) |
C6—C15—C20—C19 | 175.7 (3) | C51—C50—C52—C53 | −179.2 (4) |
C7—C6—C15—C16 | −140.3 (4) | C52—C53—C54—C55 | −0.2 (6) |
C7—C6—C15—C20 | 44.5 (5) | C53—C54—C55—C49 | 1.4 (6) |
C7—C8—C27—C28 | 27.6 (6) | C53—C54—C55—C56 | −175.3 (4) |
C7—C8—C27—C32 | −148.5 (4) | C55—C49—C50—C51 | −179.6 (4) |
C7—C21—C22—C23 | −173.0 (3) | C55—C49—C50—C52 | −1.0 (5) |
[Fe(C11H7N)3(C29H20O)]2·C3H6O | F(000) = 1936 |
Mr = 1857.73 | Dx = 1.326 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
a = 15.2471 (1) Å | Cell parameters from 61660 reflections |
b = 19.8604 (1) Å | θ = 2.9–78.4° |
c = 15.5785 (1) Å | µ = 2.98 mm−1 |
β = 99.378 (1)° | T = 100 K |
V = 4654.33 (5) Å3 | Needle, clear colourless |
Z = 2 | 0.18 × 0.07 × 0.05 mm |
XtaLAB Synergy, Dualflex, Pilatus 300K diffractometer | 18788 independent reflections |
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source | 17761 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.050 |
Detector resolution: 5.8140 pixels mm-1 | θmax = 78.8°, θmin = 2.9° |
ω scans | h = −19→19 |
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2021) | k = −23→24 |
Tmin = 0.779, Tmax = 1.000 | l = −19→19 |
89473 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0732P)2 + 0.229P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.100 | (Δ/σ)max = 0.001 |
S = 1.07 | Δρmax = 0.28 e Å−3 |
18788 reflections | Δρmin = −0.37 e Å−3 |
1390 parameters | Absolute structure: Classical Flack (1983) method preferred over Parsons because s.u. lower |
1606 restraints | Absolute structure parameter: −0.004 (2) |
Primary atom site location: dual |
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. Twinned specimen. De-twinned HKLF4 gave best results. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Fe1A | 0.57957 (3) | 0.45750 (2) | 0.58041 (3) | 0.01517 (10) | |
O1A | 0.51344 (13) | 0.30215 (10) | 0.51440 (13) | 0.0201 (4) | |
N1A | 0.67302 (16) | 0.34102 (13) | 0.67723 (16) | 0.0224 (5) | |
N2A | 0.54485 (17) | 0.53463 (13) | 0.73647 (17) | 0.0243 (5) | |
N3A | 0.73794 (16) | 0.53525 (14) | 0.54475 (17) | 0.0235 (5) | |
C1A | 0.63882 (18) | 0.38791 (15) | 0.64210 (18) | 0.0182 (5) | |
C2A | 0.56081 (18) | 0.50575 (14) | 0.67578 (18) | 0.0188 (5) | |
C3A | 0.67717 (19) | 0.50556 (14) | 0.56222 (18) | 0.0191 (5) | |
C4A | 0.50553 (18) | 0.36441 (15) | 0.50618 (18) | 0.0194 (6) | |
C5A | 0.55382 (17) | 0.41021 (14) | 0.45526 (17) | 0.0172 (5) | |
C6A | 0.51530 (17) | 0.47630 (14) | 0.45515 (17) | 0.0170 (5) | |
C7A | 0.45269 (17) | 0.47642 (14) | 0.51526 (17) | 0.0172 (5) | |
C8A | 0.45225 (17) | 0.40968 (14) | 0.55248 (17) | 0.0172 (5) | |
C9A | 0.70183 (19) | 0.27731 (15) | 0.70810 (18) | 0.0199 (5) | |
C10A | 0.6534 (2) | 0.22088 (17) | 0.6712 (2) | 0.0241 (6) | |
H10A | 0.604652 | 0.226301 | 0.625213 | 0.029* | |
C11A | 0.6779 (2) | 0.15860 (16) | 0.7027 (2) | 0.0248 (6) | |
H11A | 0.646115 | 0.120231 | 0.677981 | 0.030* | |
C12A | 0.75027 (19) | 0.14989 (15) | 0.77214 (19) | 0.0217 (6) | |
C13A | 0.7735 (2) | 0.08573 (17) | 0.8091 (2) | 0.0304 (7) | |
H13A | 0.740520 | 0.047119 | 0.786928 | 0.036* | |
C14A | 0.8428 (2) | 0.07900 (18) | 0.8762 (2) | 0.0339 (7) | |
H14A | 0.856863 | 0.035855 | 0.900958 | 0.041* | |
C15A | 0.8936 (2) | 0.13552 (18) | 0.9090 (2) | 0.0282 (7) | |
H15A | 0.942079 | 0.130263 | 0.955290 | 0.034* | |
C16A | 0.87303 (19) | 0.19785 (16) | 0.8741 (2) | 0.0234 (6) | |
H16A | 0.908102 | 0.235582 | 0.895785 | 0.028* | |
C17A | 0.79993 (18) | 0.20695 (15) | 0.80594 (19) | 0.0190 (5) | |
C18A | 0.77404 (18) | 0.27145 (15) | 0.77292 (18) | 0.0195 (5) | |
H18A | 0.806232 | 0.310309 | 0.795322 | 0.023* | |
C19A | 0.51160 (19) | 0.56466 (15) | 0.80555 (19) | 0.0209 (6) | |
C20A | 0.56227 (19) | 0.56089 (16) | 0.8899 (2) | 0.0231 (6) | |
H20A | 0.619182 | 0.540154 | 0.898781 | 0.028* | |
C21A | 0.5283 (2) | 0.58748 (16) | 0.9583 (2) | 0.0247 (6) | |
H21A | 0.562294 | 0.585714 | 1.015100 | 0.030* | |
C22A | 0.4429 (2) | 0.61767 (15) | 0.9458 (2) | 0.0236 (6) | |
C23A | 0.4047 (2) | 0.64311 (18) | 1.0168 (2) | 0.0328 (7) | |
H23A | 0.437245 | 0.640741 | 1.074214 | 0.039* | |
C24A | 0.3217 (3) | 0.6709 (2) | 1.0030 (3) | 0.0431 (9) | |
H24A | 0.296726 | 0.687512 | 1.050820 | 0.052* | |
C25A | 0.2729 (3) | 0.6750 (2) | 0.9187 (3) | 0.0473 (10) | |
H25A | 0.215342 | 0.694618 | 0.910039 | 0.057* | |
C26A | 0.3074 (2) | 0.6511 (2) | 0.8482 (3) | 0.0369 (8) | |
H26A | 0.273691 | 0.654116 | 0.791436 | 0.044* | |
C27A | 0.3935 (2) | 0.62181 (16) | 0.8609 (2) | 0.0243 (6) | |
C28A | 0.43005 (19) | 0.59519 (16) | 0.7902 (2) | 0.0237 (6) | |
H28A | 0.398284 | 0.598495 | 0.732556 | 0.028* | |
C29A | 0.80196 (19) | 0.56989 (16) | 0.50659 (19) | 0.0217 (6) | |
C30A | 0.8045 (2) | 0.64098 (17) | 0.5122 (2) | 0.0258 (6) | |
H30A | 0.765661 | 0.664522 | 0.543548 | 0.031* | |
C31A | 0.8643 (2) | 0.67528 (17) | 0.4715 (2) | 0.0291 (7) | |
H31A | 0.866065 | 0.723057 | 0.474331 | 0.035* | |
C32A | 0.9232 (2) | 0.64074 (18) | 0.4254 (2) | 0.0272 (7) | |
C33A | 0.9860 (2) | 0.6753 (2) | 0.3829 (2) | 0.0396 (9) | |
H33A | 0.990077 | 0.722974 | 0.386526 | 0.048* | |
C34A | 1.0404 (2) | 0.6406 (3) | 0.3372 (3) | 0.0486 (11) | |
H34A | 1.081593 | 0.664290 | 0.308811 | 0.058* | |
C35A | 1.0356 (2) | 0.5696 (3) | 0.3317 (3) | 0.0463 (10) | |
H35A | 1.073381 | 0.545934 | 0.299303 | 0.056* | |
C36A | 0.9775 (2) | 0.5352 (2) | 0.3725 (2) | 0.0351 (8) | |
H36A | 0.975569 | 0.487424 | 0.368836 | 0.042* | |
C37A | 0.91958 (19) | 0.56911 (18) | 0.42043 (19) | 0.0246 (6) | |
C38A | 0.85803 (19) | 0.53476 (16) | 0.4627 (2) | 0.0233 (6) | |
H38A | 0.855382 | 0.486981 | 0.460808 | 0.028* | |
C39A | 0.61525 (18) | 0.38679 (15) | 0.39642 (18) | 0.0193 (5) | |
C40A | 0.67738 (18) | 0.42953 (15) | 0.36753 (19) | 0.0207 (6) | |
H40A | 0.683802 | 0.474357 | 0.388900 | 0.025* | |
C41A | 0.7300 (2) | 0.40735 (17) | 0.3079 (2) | 0.0259 (6) | |
H41A | 0.771436 | 0.437220 | 0.288756 | 0.031* | |
C42A | 0.7221 (2) | 0.34175 (18) | 0.2764 (2) | 0.0285 (7) | |
H42A | 0.757937 | 0.326560 | 0.235712 | 0.034* | |
C43A | 0.6613 (2) | 0.29889 (17) | 0.3051 (2) | 0.0284 (7) | |
H43A | 0.655601 | 0.253943 | 0.284034 | 0.034* | |
C44A | 0.6086 (2) | 0.32084 (16) | 0.3642 (2) | 0.0235 (6) | |
H44A | 0.567307 | 0.290659 | 0.383178 | 0.028* | |
C45A | 0.52444 (18) | 0.53034 (15) | 0.39123 (19) | 0.0198 (5) | |
C46A | 0.55581 (19) | 0.59498 (16) | 0.4140 (2) | 0.0230 (6) | |
H46A | 0.574176 | 0.605952 | 0.473555 | 0.028* | |
C47A | 0.5606 (2) | 0.64365 (17) | 0.3505 (2) | 0.0287 (7) | |
H47A | 0.581106 | 0.687717 | 0.366764 | 0.034* | |
C48A | 0.5352 (2) | 0.62750 (18) | 0.2634 (2) | 0.0307 (7) | |
H48A | 0.538339 | 0.660522 | 0.219918 | 0.037* | |
C49A | 0.5052 (2) | 0.56322 (18) | 0.2398 (2) | 0.0279 (6) | |
H49A | 0.488549 | 0.552140 | 0.180053 | 0.033* | |
C50A | 0.49930 (19) | 0.51486 (16) | 0.30310 (19) | 0.0224 (6) | |
H50A | 0.478080 | 0.471039 | 0.286393 | 0.027* | |
C51A | 0.38688 (18) | 0.53063 (15) | 0.52111 (18) | 0.0182 (5) | |
C52A | 0.29681 (19) | 0.51478 (16) | 0.49939 (19) | 0.0217 (6) | |
H52A | 0.279400 | 0.469455 | 0.486776 | 0.026* | |
C53A | 0.2320 (2) | 0.56482 (18) | 0.4960 (2) | 0.0272 (6) | |
H53A | 0.170942 | 0.553425 | 0.480824 | 0.033* | |
C54A | 0.2565 (2) | 0.63095 (18) | 0.5147 (2) | 0.0303 (7) | |
H54A | 0.212541 | 0.665145 | 0.511339 | 0.036* | |
C55A | 0.3452 (2) | 0.64695 (16) | 0.5382 (2) | 0.0280 (7) | |
H55A | 0.362133 | 0.692280 | 0.551516 | 0.034* | |
C56A | 0.4103 (2) | 0.59708 (15) | 0.54263 (19) | 0.0224 (6) | |
H56A | 0.471029 | 0.608517 | 0.560455 | 0.027* | |
C57A | 0.39119 (18) | 0.38613 (15) | 0.61099 (18) | 0.0190 (5) | |
C58A | 0.35409 (19) | 0.32133 (15) | 0.5997 (2) | 0.0221 (6) | |
H58A | 0.370876 | 0.292262 | 0.556750 | 0.026* | |
C59A | 0.2930 (2) | 0.29936 (17) | 0.6509 (2) | 0.0277 (7) | |
H59A | 0.268651 | 0.255334 | 0.642781 | 0.033* | |
C60A | 0.2672 (2) | 0.34098 (18) | 0.7136 (2) | 0.0287 (7) | |
H60A | 0.225122 | 0.325909 | 0.748065 | 0.034* | |
C61A | 0.3038 (2) | 0.40517 (18) | 0.7255 (2) | 0.0265 (6) | |
H61A | 0.286521 | 0.434007 | 0.768500 | 0.032* | |
C62A | 0.36511 (19) | 0.42737 (16) | 0.67538 (19) | 0.0216 (6) | |
H62A | 0.389856 | 0.471177 | 0.684733 | 0.026* | |
Fe1B | 0.83999 (3) | 0.48533 (2) | 0.86648 (3) | 0.01583 (10) | |
O1B | 0.92081 (13) | 0.63902 (11) | 0.92958 (13) | 0.0213 (4) | |
N1B | 0.74010 (16) | 0.60604 (13) | 0.78767 (17) | 0.0225 (5) | |
N2B | 0.68892 (17) | 0.39653 (13) | 0.89964 (18) | 0.0250 (5) | |
N3B | 0.85773 (17) | 0.43202 (14) | 0.69046 (16) | 0.0239 (5) | |
C1B | 0.77407 (17) | 0.55748 (15) | 0.81883 (18) | 0.0188 (5) | |
C2B | 0.74839 (19) | 0.43019 (15) | 0.88633 (18) | 0.0196 (5) | |
C3B | 0.84823 (17) | 0.45049 (15) | 0.75983 (18) | 0.0198 (5) | |
C4B | 0.92462 (18) | 0.57659 (15) | 0.93463 (18) | 0.0194 (6) | |
C5B | 0.96763 (17) | 0.52974 (15) | 0.88028 (18) | 0.0184 (5) | |
C6B | 0.97052 (17) | 0.46366 (15) | 0.91895 (17) | 0.0186 (5) | |
C7B | 0.91703 (17) | 0.46555 (15) | 0.98714 (17) | 0.0178 (5) | |
C8B | 0.88065 (18) | 0.53202 (15) | 0.99053 (18) | 0.0188 (5) | |
C9B | 0.72516 (19) | 0.67210 (15) | 0.75815 (19) | 0.0209 (6) | |
C10B | 0.65394 (19) | 0.68525 (16) | 0.6900 (2) | 0.0240 (6) | |
H10B | 0.616139 | 0.649723 | 0.665635 | 0.029* | |
C11B | 0.6399 (2) | 0.74952 (17) | 0.6594 (2) | 0.0243 (6) | |
H11B | 0.592032 | 0.758444 | 0.613650 | 0.029* | |
C12B | 0.6961 (2) | 0.80323 (16) | 0.6950 (2) | 0.0235 (6) | |
C13B | 0.6836 (2) | 0.87017 (17) | 0.6651 (2) | 0.0282 (7) | |
H13B | 0.634660 | 0.880663 | 0.621153 | 0.034* | |
C14B | 0.7408 (2) | 0.92001 (17) | 0.6984 (2) | 0.0314 (7) | |
H14B | 0.731748 | 0.964686 | 0.676944 | 0.038* | |
C15B | 0.8133 (2) | 0.90552 (18) | 0.7645 (2) | 0.0306 (7) | |
H15B | 0.853157 | 0.940443 | 0.786874 | 0.037* | |
C16B | 0.8265 (2) | 0.84174 (17) | 0.7966 (2) | 0.0266 (6) | |
H16B | 0.875198 | 0.832655 | 0.841453 | 0.032* | |
C17B | 0.76811 (19) | 0.78889 (15) | 0.76337 (19) | 0.0213 (6) | |
C18B | 0.78143 (19) | 0.72194 (16) | 0.7949 (2) | 0.0218 (6) | |
H18B | 0.828619 | 0.711806 | 0.840886 | 0.026* | |
C19B | 0.6131 (2) | 0.35925 (18) | 0.9116 (3) | 0.0221 (7) | 0.911 (3) |
C20B | 0.5515 (2) | 0.33995 (18) | 0.8379 (2) | 0.0248 (7) | 0.911 (3) |
H20B | 0.560941 | 0.352261 | 0.781151 | 0.030* | 0.911 (3) |
C21B | 0.4783 (2) | 0.30340 (18) | 0.8490 (2) | 0.0271 (7) | 0.911 (3) |
H21B | 0.437479 | 0.289478 | 0.799411 | 0.032* | 0.911 (3) |
C22B | 0.4622 (2) | 0.28597 (17) | 0.9331 (2) | 0.0254 (7) | 0.911 (3) |
C23B | 0.3855 (2) | 0.2489 (2) | 0.9462 (3) | 0.0303 (8) | 0.911 (3) |
H23B | 0.344887 | 0.233554 | 0.897237 | 0.036* | 0.911 (3) |
C24B | 0.3695 (3) | 0.2350 (2) | 1.0284 (3) | 0.0342 (9) | 0.911 (3) |
H24B | 0.317937 | 0.210406 | 1.036257 | 0.041* | 0.911 (3) |
C25B | 0.4295 (3) | 0.2573 (2) | 1.1013 (3) | 0.0362 (9) | 0.911 (3) |
H25B | 0.417843 | 0.248078 | 1.158200 | 0.043* | 0.911 (3) |
C26B | 0.5045 (3) | 0.2923 (2) | 1.0910 (2) | 0.0332 (8) | 0.911 (3) |
H26B | 0.544671 | 0.306553 | 1.140757 | 0.040* | 0.911 (3) |
C27B | 0.5228 (3) | 0.3072 (2) | 1.0069 (3) | 0.0248 (8) | 0.911 (3) |
C28B | 0.5998 (2) | 0.34384 (18) | 0.9947 (2) | 0.0243 (7) | 0.911 (3) |
H28B | 0.641734 | 0.357599 | 1.043476 | 0.029* | 0.911 (3) |
C29B | 0.8895 (2) | 0.40251 (19) | 0.6196 (2) | 0.0216 (8) | 0.911 (3) |
C30B | 0.8312 (2) | 0.36323 (18) | 0.5594 (2) | 0.0230 (7) | 0.911 (3) |
H30B | 0.770749 | 0.357988 | 0.565929 | 0.028* | 0.911 (3) |
C31B | 0.8630 (2) | 0.33285 (18) | 0.4917 (2) | 0.0239 (7) | 0.911 (3) |
H31B | 0.824236 | 0.306230 | 0.451373 | 0.029* | 0.911 (3) |
C32B | 0.9529 (2) | 0.34066 (18) | 0.4811 (2) | 0.0223 (7) | 0.911 (3) |
C33B | 0.9873 (2) | 0.30916 (19) | 0.4119 (2) | 0.0277 (7) | 0.911 (3) |
H33B | 0.949890 | 0.281407 | 0.371841 | 0.033* | 0.911 (3) |
C34B | 1.0743 (3) | 0.3186 (2) | 0.4026 (2) | 0.0329 (8) | 0.911 (3) |
H34B | 1.096570 | 0.297663 | 0.355705 | 0.039* | 0.911 (3) |
C35B | 1.1307 (2) | 0.3589 (2) | 0.4614 (2) | 0.0338 (8) | 0.911 (3) |
H35B | 1.190824 | 0.364882 | 0.454062 | 0.041* | 0.911 (3) |
C36B | 1.1002 (2) | 0.3898 (2) | 0.5292 (2) | 0.0309 (8) | 0.911 (3) |
H36B | 1.139090 | 0.416943 | 0.568682 | 0.037* | 0.911 (3) |
C37B | 1.0105 (2) | 0.3813 (2) | 0.5407 (2) | 0.0224 (7) | 0.911 (3) |
C38B | 0.9766 (2) | 0.4121 (2) | 0.6107 (2) | 0.0244 (7) | 0.911 (3) |
H38B | 1.014153 | 0.439353 | 0.651268 | 0.029* | 0.911 (3) |
C39B | 1.01292 (18) | 0.55284 (15) | 0.80852 (19) | 0.0207 (6) | |
C40B | 1.0962 (2) | 0.52835 (18) | 0.7958 (2) | 0.0321 (7) | |
H40B | 1.126573 | 0.496574 | 0.835617 | 0.039* | |
C41B | 1.1349 (2) | 0.5500 (2) | 0.7259 (3) | 0.0418 (9) | |
H41B | 1.190619 | 0.532068 | 0.717528 | 0.050* | |
C42B | 1.0928 (2) | 0.5974 (2) | 0.6683 (3) | 0.0396 (9) | |
H42B | 1.119921 | 0.612392 | 0.620926 | 0.048* | |
C43B | 1.0111 (2) | 0.6230 (2) | 0.6800 (2) | 0.0363 (8) | |
H43B | 0.981738 | 0.655371 | 0.640591 | 0.044* | |
C44B | 0.9721 (2) | 0.60103 (18) | 0.7498 (2) | 0.0286 (7) | |
H44B | 0.916392 | 0.619253 | 0.757747 | 0.034* | |
C45B | 1.03063 (18) | 0.40615 (15) | 0.90813 (18) | 0.0188 (5) | |
C46B | 1.01554 (19) | 0.35929 (16) | 0.8411 (2) | 0.0235 (6) | |
H46B | 0.966305 | 0.364944 | 0.795786 | 0.028* | |
C47B | 1.0717 (2) | 0.30408 (17) | 0.8396 (2) | 0.0266 (6) | |
H47B | 1.060388 | 0.272563 | 0.793226 | 0.032* | |
C48B | 1.1436 (2) | 0.29478 (16) | 0.9048 (2) | 0.0259 (6) | |
H48B | 1.181247 | 0.256750 | 0.903943 | 0.031* | |
C49B | 1.1602 (2) | 0.34130 (18) | 0.9711 (2) | 0.0306 (7) | |
H49B | 1.210247 | 0.335789 | 1.015613 | 0.037* | |
C50B | 1.1042 (2) | 0.39609 (17) | 0.9733 (2) | 0.0278 (7) | |
H50B | 1.116039 | 0.427377 | 1.019838 | 0.033* | |
C51B | 0.91505 (18) | 0.41028 (15) | 1.05049 (18) | 0.0191 (5) | |
C52B | 0.9313 (2) | 0.42455 (16) | 1.13966 (19) | 0.0236 (6) | |
H52B | 0.936576 | 0.469965 | 1.158958 | 0.028* | |
C53B | 0.9397 (2) | 0.37234 (17) | 1.2002 (2) | 0.0274 (7) | |
H53B | 0.948924 | 0.382393 | 1.260626 | 0.033* | |
C54B | 0.9346 (2) | 0.30613 (17) | 1.1730 (2) | 0.0272 (6) | |
H54B | 0.942342 | 0.270743 | 1.214536 | 0.033* | |
C55B | 0.9182 (2) | 0.29127 (16) | 1.0844 (2) | 0.0253 (6) | |
H55B | 0.914824 | 0.245770 | 1.065358 | 0.030* | |
C56B | 0.9069 (2) | 0.34332 (16) | 1.02437 (19) | 0.0231 (6) | |
H56B | 0.893207 | 0.333024 | 0.964118 | 0.028* | |
C57B | 0.82839 (19) | 0.55533 (15) | 1.05734 (18) | 0.0203 (6) | |
C58B | 0.8589 (2) | 0.60964 (16) | 1.1105 (2) | 0.0254 (6) | |
H58B | 0.908401 | 0.635041 | 1.098741 | 0.031* | |
C59B | 0.8177 (2) | 0.62699 (17) | 1.1804 (2) | 0.0292 (7) | |
H59B | 0.840065 | 0.663567 | 1.216815 | 0.035* | |
C60B | 0.7441 (2) | 0.59151 (17) | 1.1979 (2) | 0.0276 (6) | |
H60B | 0.716516 | 0.603317 | 1.246236 | 0.033* | |
C61B | 0.7112 (2) | 0.53847 (18) | 1.1437 (2) | 0.0271 (6) | |
H61B | 0.660111 | 0.514472 | 1.154100 | 0.033* | |
C62B | 0.75330 (19) | 0.52061 (16) | 1.0743 (2) | 0.0229 (6) | |
H62B | 0.730631 | 0.484204 | 1.037704 | 0.028* | |
O1 | 0.49104 (17) | 0.46261 (14) | 0.07107 (18) | 0.0412 (6) | |
C1 | 0.4135 (2) | 0.45163 (19) | 0.0431 (2) | 0.0345 (7) | |
C2 | 0.3474 (3) | 0.4399 (3) | 0.1032 (3) | 0.0576 (13) | |
H2A | 0.338023 | 0.391409 | 0.109046 | 0.086* | |
H2B | 0.290947 | 0.461557 | 0.079428 | 0.086* | |
H2C | 0.370223 | 0.459071 | 0.160499 | 0.086* | |
C3 | 0.3779 (3) | 0.4484 (2) | −0.0521 (2) | 0.0429 (9) | |
H3A | 0.339416 | 0.487317 | −0.068767 | 0.064* | |
H3B | 0.343598 | 0.406839 | −0.064905 | 0.064* | |
H3C | 0.427457 | 0.448860 | −0.085079 | 0.064* | |
C29C | 0.9079 (18) | 0.4224 (17) | 0.6256 (19) | 0.026 (6) | 0.089 (3) |
C38C | 0.866 (2) | 0.3738 (16) | 0.5692 (19) | 0.0230 (7) | 0.089 (3) |
H38C | 0.806871 | 0.359483 | 0.571348 | 0.028* | 0.089 (3) |
C37C | 0.9160 (17) | 0.3467 (11) | 0.5082 (14) | 0.020 (5) | 0.089 (3) |
C36C | 0.8793 (19) | 0.2968 (13) | 0.4492 (17) | 0.021 (5) | 0.089 (3) |
H36C | 0.820539 | 0.281090 | 0.449957 | 0.025* | 0.089 (3) |
C35C | 0.9295 (18) | 0.2701 (15) | 0.3890 (18) | 0.0277 (7) | 0.089 (3) |
H35C | 0.904696 | 0.237224 | 0.347822 | 0.033* | 0.089 (3) |
C34C | 1.0173 (19) | 0.2930 (17) | 0.391 (2) | 0.0277 (7) | 0.089 (3) |
H34C | 1.051866 | 0.271978 | 0.353096 | 0.033* | 0.089 (3) |
C33C | 1.0567 (19) | 0.3446 (16) | 0.4447 (17) | 0.026 (5) | 0.089 (3) |
H33C | 1.113704 | 0.362489 | 0.440700 | 0.031* | 0.089 (3) |
C32C | 1.0038 (18) | 0.3678 (16) | 0.5059 (19) | 0.021 (6) | 0.089 (3) |
C31C | 1.042 (2) | 0.4187 (15) | 0.5635 (18) | 0.023 (5) | 0.089 (3) |
H31C | 1.099956 | 0.435503 | 0.559880 | 0.028* | 0.089 (3) |
C30C | 0.9947 (17) | 0.4440 (17) | 0.6259 (18) | 0.022 (6) | 0.089 (3) |
H30C | 1.021361 | 0.475551 | 0.668029 | 0.027* | 0.089 (3) |
C19C | 0.6385 (18) | 0.3566 (15) | 0.9468 (16) | 0.022 (5) | 0.089 (3) |
C27C | 0.5010 (14) | 0.3005 (11) | 0.9272 (17) | 0.035 (6) | 0.089 (3) |
C25C | 0.3569 (18) | 0.2418 (15) | 0.906 (2) | 0.037 (6) | 0.089 (3) |
H25C | 0.306747 | 0.224472 | 0.867854 | 0.044* | 0.089 (3) |
C20C | 0.6507 (16) | 0.3508 (15) | 1.0366 (16) | 0.0243 (7) | 0.089 (3) |
H20C | 0.701562 | 0.368029 | 1.073340 | 0.029* | 0.089 (3) |
C24C | 0.366 (2) | 0.2352 (17) | 0.995 (2) | 0.0342 (9) | 0.089 (3) |
H24C | 0.320658 | 0.212152 | 1.018728 | 0.041* | 0.089 (3) |
C21C | 0.5822 (15) | 0.3176 (15) | 1.0686 (18) | 0.027 (5) | 0.089 (3) |
H21C | 0.587951 | 0.312112 | 1.129876 | 0.032* | 0.089 (3) |
C26C | 0.4252 (16) | 0.2752 (14) | 0.8738 (17) | 0.0254 (7) | 0.089 (3) |
H26C | 0.420284 | 0.281098 | 0.812709 | 0.030* | 0.089 (3) |
C22C | 0.5054 (17) | 0.2917 (18) | 1.0172 (18) | 0.028 (7) | 0.089 (3) |
C28C | 0.5660 (19) | 0.3333 (16) | 0.8884 (18) | 0.025 (6) | 0.089 (3) |
H28C | 0.561018 | 0.339066 | 0.827228 | 0.030* | 0.089 (3) |
C23C | 0.4378 (17) | 0.2604 (17) | 1.0536 (19) | 0.034 (6) | 0.089 (3) |
H23C | 0.440667 | 0.256530 | 1.114759 | 0.040* | 0.089 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1A | 0.01549 (19) | 0.0134 (2) | 0.01623 (19) | −0.00060 (16) | 0.00133 (14) | 0.00003 (16) |
O1A | 0.0235 (10) | 0.0133 (10) | 0.0222 (10) | −0.0006 (8) | 0.0002 (8) | −0.0005 (8) |
N1A | 0.0236 (12) | 0.0205 (13) | 0.0219 (12) | −0.0004 (10) | −0.0004 (9) | 0.0023 (10) |
N2A | 0.0257 (12) | 0.0216 (13) | 0.0264 (13) | −0.0041 (10) | 0.0068 (10) | −0.0062 (10) |
N3A | 0.0202 (12) | 0.0248 (13) | 0.0250 (12) | −0.0038 (10) | 0.0026 (10) | 0.0022 (10) |
C1A | 0.0190 (12) | 0.0185 (14) | 0.0168 (12) | −0.0016 (10) | 0.0016 (10) | −0.0001 (10) |
C2A | 0.0164 (12) | 0.0166 (13) | 0.0223 (14) | −0.0021 (10) | 0.0003 (10) | 0.0002 (10) |
C3A | 0.0221 (13) | 0.0143 (13) | 0.0200 (13) | 0.0004 (10) | 0.0008 (10) | −0.0008 (10) |
C4A | 0.0190 (13) | 0.0210 (15) | 0.0173 (13) | −0.0013 (11) | −0.0004 (10) | 0.0004 (10) |
C5A | 0.0171 (12) | 0.0166 (14) | 0.0167 (12) | −0.0010 (10) | −0.0007 (10) | −0.0007 (10) |
C6A | 0.0145 (11) | 0.0189 (14) | 0.0159 (12) | −0.0017 (10) | −0.0022 (9) | −0.0005 (10) |
C7A | 0.0161 (12) | 0.0164 (14) | 0.0175 (12) | −0.0012 (10) | −0.0016 (9) | −0.0015 (10) |
C8A | 0.0164 (12) | 0.0160 (13) | 0.0175 (12) | −0.0026 (10) | −0.0023 (10) | −0.0014 (10) |
C9A | 0.0220 (13) | 0.0186 (14) | 0.0194 (13) | 0.0019 (11) | 0.0045 (10) | 0.0031 (11) |
C10A | 0.0215 (14) | 0.0264 (16) | 0.0226 (14) | −0.0013 (12) | −0.0015 (11) | −0.0009 (12) |
C11A | 0.0252 (14) | 0.0194 (15) | 0.0288 (16) | −0.0034 (11) | 0.0016 (12) | −0.0035 (12) |
C12A | 0.0239 (14) | 0.0200 (15) | 0.0221 (14) | 0.0010 (11) | 0.0065 (11) | 0.0003 (11) |
C13A | 0.0380 (18) | 0.0167 (15) | 0.0353 (17) | 0.0011 (13) | 0.0021 (14) | −0.0014 (13) |
C14A | 0.0407 (19) | 0.0238 (17) | 0.0363 (18) | 0.0106 (14) | 0.0040 (15) | 0.0079 (14) |
C15A | 0.0254 (14) | 0.0333 (18) | 0.0245 (15) | 0.0109 (13) | −0.0008 (12) | 0.0024 (13) |
C16A | 0.0211 (13) | 0.0254 (16) | 0.0230 (14) | 0.0028 (11) | 0.0016 (11) | −0.0015 (11) |
C17A | 0.0181 (13) | 0.0199 (15) | 0.0198 (13) | 0.0027 (10) | 0.0054 (10) | −0.0009 (11) |
C18A | 0.0196 (13) | 0.0182 (14) | 0.0204 (13) | −0.0014 (11) | 0.0021 (10) | −0.0009 (11) |
C19A | 0.0222 (13) | 0.0191 (14) | 0.0226 (14) | −0.0042 (11) | 0.0069 (11) | −0.0038 (11) |
C20A | 0.0195 (13) | 0.0214 (15) | 0.0277 (15) | 0.0021 (11) | 0.0017 (11) | −0.0021 (12) |
C21A | 0.0281 (15) | 0.0227 (15) | 0.0226 (14) | 0.0005 (12) | 0.0020 (11) | 0.0000 (11) |
C22A | 0.0297 (15) | 0.0167 (14) | 0.0259 (15) | 0.0011 (11) | 0.0091 (12) | 0.0024 (11) |
C23A | 0.047 (2) | 0.0261 (17) | 0.0285 (16) | 0.0037 (14) | 0.0164 (15) | 0.0036 (13) |
C24A | 0.053 (2) | 0.037 (2) | 0.048 (2) | 0.0112 (17) | 0.0338 (19) | 0.0068 (17) |
C25A | 0.0354 (19) | 0.052 (3) | 0.061 (3) | 0.0202 (17) | 0.0257 (18) | 0.016 (2) |
C26A | 0.0270 (16) | 0.045 (2) | 0.0407 (19) | 0.0096 (15) | 0.0107 (14) | 0.0114 (16) |
C27A | 0.0230 (14) | 0.0229 (15) | 0.0278 (15) | 0.0012 (11) | 0.0069 (11) | 0.0064 (12) |
C28A | 0.0219 (13) | 0.0266 (16) | 0.0219 (14) | −0.0024 (11) | 0.0014 (11) | 0.0026 (12) |
C29A | 0.0178 (13) | 0.0239 (16) | 0.0233 (14) | −0.0059 (11) | 0.0025 (11) | 0.0029 (11) |
C30A | 0.0261 (14) | 0.0229 (16) | 0.0279 (15) | 0.0000 (12) | 0.0026 (12) | −0.0013 (12) |
C31A | 0.0330 (16) | 0.0208 (16) | 0.0306 (16) | −0.0076 (12) | −0.0033 (13) | 0.0019 (12) |
C32A | 0.0242 (14) | 0.0340 (18) | 0.0218 (14) | −0.0094 (12) | −0.0014 (11) | 0.0064 (12) |
C33A | 0.0339 (18) | 0.048 (2) | 0.0344 (18) | −0.0175 (16) | −0.0028 (14) | 0.0141 (16) |
C34A | 0.0286 (18) | 0.086 (4) | 0.0316 (19) | −0.0132 (19) | 0.0073 (15) | 0.018 (2) |
C35A | 0.0292 (18) | 0.078 (3) | 0.0332 (19) | 0.0036 (18) | 0.0103 (15) | 0.0026 (19) |
C36A | 0.0261 (16) | 0.049 (2) | 0.0303 (17) | 0.0019 (15) | 0.0051 (13) | −0.0031 (16) |
C37A | 0.0180 (13) | 0.0327 (18) | 0.0216 (14) | −0.0028 (11) | −0.0012 (11) | 0.0023 (12) |
C38A | 0.0217 (13) | 0.0205 (15) | 0.0262 (15) | −0.0013 (11) | −0.0005 (11) | 0.0019 (12) |
C39A | 0.0192 (13) | 0.0227 (15) | 0.0150 (12) | 0.0030 (11) | −0.0004 (10) | 0.0020 (11) |
C40A | 0.0219 (13) | 0.0191 (14) | 0.0206 (13) | 0.0019 (11) | 0.0019 (11) | 0.0004 (11) |
C41A | 0.0235 (14) | 0.0311 (17) | 0.0236 (14) | 0.0031 (12) | 0.0050 (11) | 0.0033 (12) |
C42A | 0.0283 (16) | 0.0359 (19) | 0.0223 (14) | 0.0063 (13) | 0.0066 (12) | −0.0029 (13) |
C43A | 0.0344 (16) | 0.0239 (16) | 0.0269 (15) | 0.0057 (13) | 0.0053 (13) | −0.0054 (12) |
C44A | 0.0244 (14) | 0.0218 (15) | 0.0238 (14) | 0.0015 (11) | 0.0027 (11) | −0.0014 (11) |
C45A | 0.0172 (12) | 0.0194 (14) | 0.0230 (14) | 0.0017 (10) | 0.0041 (10) | 0.0025 (11) |
C46A | 0.0193 (13) | 0.0215 (15) | 0.0281 (15) | −0.0007 (11) | 0.0036 (11) | 0.0027 (12) |
C47A | 0.0262 (15) | 0.0192 (15) | 0.0399 (18) | −0.0007 (12) | 0.0036 (13) | 0.0074 (13) |
C48A | 0.0285 (15) | 0.0285 (18) | 0.0359 (17) | 0.0013 (13) | 0.0079 (13) | 0.0161 (14) |
C49A | 0.0283 (15) | 0.0314 (17) | 0.0239 (15) | 0.0063 (13) | 0.0041 (12) | 0.0043 (13) |
C50A | 0.0227 (13) | 0.0214 (15) | 0.0231 (14) | 0.0024 (11) | 0.0035 (11) | 0.0011 (11) |
C51A | 0.0205 (13) | 0.0174 (14) | 0.0167 (12) | 0.0010 (10) | 0.0034 (10) | 0.0003 (10) |
C52A | 0.0224 (13) | 0.0206 (14) | 0.0215 (14) | −0.0003 (11) | 0.0022 (11) | −0.0017 (11) |
C53A | 0.0204 (14) | 0.0339 (18) | 0.0276 (15) | 0.0047 (12) | 0.0044 (11) | 0.0029 (13) |
C54A | 0.0312 (16) | 0.0301 (18) | 0.0317 (17) | 0.0142 (13) | 0.0111 (13) | 0.0066 (14) |
C55A | 0.0386 (17) | 0.0159 (15) | 0.0301 (16) | 0.0035 (12) | 0.0076 (13) | 0.0007 (12) |
C56A | 0.0241 (14) | 0.0185 (15) | 0.0247 (14) | −0.0017 (11) | 0.0037 (11) | −0.0018 (11) |
C57A | 0.0159 (12) | 0.0200 (14) | 0.0197 (13) | 0.0007 (10) | −0.0008 (10) | 0.0024 (11) |
C58A | 0.0205 (13) | 0.0203 (15) | 0.0251 (14) | −0.0030 (11) | 0.0027 (11) | 0.0006 (11) |
C59A | 0.0246 (14) | 0.0250 (16) | 0.0326 (16) | −0.0049 (12) | 0.0019 (12) | 0.0076 (13) |
C60A | 0.0228 (15) | 0.0354 (19) | 0.0285 (16) | −0.0013 (13) | 0.0059 (12) | 0.0103 (14) |
C61A | 0.0232 (14) | 0.0335 (18) | 0.0231 (14) | 0.0034 (12) | 0.0043 (12) | 0.0024 (13) |
C62A | 0.0205 (13) | 0.0221 (15) | 0.0217 (14) | −0.0009 (11) | 0.0016 (11) | 0.0014 (11) |
Fe1B | 0.01538 (19) | 0.0150 (2) | 0.0168 (2) | 0.00048 (16) | 0.00164 (15) | 0.00101 (16) |
O1B | 0.0217 (10) | 0.0164 (11) | 0.0242 (10) | −0.0007 (7) | −0.0012 (8) | 0.0019 (8) |
N1B | 0.0182 (11) | 0.0223 (13) | 0.0266 (13) | 0.0014 (9) | 0.0024 (9) | 0.0048 (10) |
N2B | 0.0259 (12) | 0.0201 (13) | 0.0303 (13) | −0.0019 (10) | 0.0082 (10) | −0.0017 (10) |
N3B | 0.0242 (12) | 0.0288 (14) | 0.0182 (12) | 0.0023 (10) | 0.0017 (9) | −0.0013 (10) |
C1B | 0.0148 (12) | 0.0186 (14) | 0.0226 (14) | −0.0012 (10) | 0.0015 (10) | −0.0015 (11) |
C2B | 0.0217 (13) | 0.0168 (14) | 0.0199 (13) | 0.0024 (10) | 0.0019 (10) | 0.0011 (10) |
C3B | 0.0158 (12) | 0.0190 (14) | 0.0231 (13) | 0.0006 (10) | −0.0009 (10) | 0.0022 (11) |
C4B | 0.0163 (12) | 0.0216 (16) | 0.0190 (13) | 0.0002 (10) | −0.0009 (10) | 0.0020 (11) |
C5B | 0.0146 (12) | 0.0179 (14) | 0.0215 (13) | −0.0003 (10) | −0.0006 (10) | 0.0004 (11) |
C6B | 0.0163 (12) | 0.0190 (14) | 0.0193 (12) | 0.0007 (10) | −0.0007 (10) | 0.0001 (11) |
C7B | 0.0168 (12) | 0.0186 (15) | 0.0167 (12) | 0.0006 (10) | −0.0014 (9) | −0.0001 (10) |
C8B | 0.0190 (12) | 0.0178 (14) | 0.0188 (13) | −0.0010 (10) | 0.0009 (10) | −0.0012 (11) |
C9B | 0.0195 (13) | 0.0205 (15) | 0.0225 (14) | 0.0037 (11) | 0.0033 (11) | 0.0034 (11) |
C10B | 0.0199 (14) | 0.0262 (16) | 0.0249 (15) | 0.0003 (11) | 0.0006 (11) | 0.0019 (12) |
C11B | 0.0210 (14) | 0.0271 (16) | 0.0234 (14) | 0.0038 (12) | −0.0002 (11) | 0.0049 (12) |
C12B | 0.0255 (14) | 0.0239 (16) | 0.0215 (14) | 0.0054 (12) | 0.0050 (11) | 0.0027 (11) |
C13B | 0.0344 (16) | 0.0255 (17) | 0.0234 (15) | 0.0079 (13) | 0.0010 (12) | 0.0053 (12) |
C14B | 0.0471 (19) | 0.0192 (16) | 0.0274 (16) | 0.0036 (13) | 0.0050 (14) | 0.0048 (12) |
C15B | 0.0394 (17) | 0.0239 (16) | 0.0280 (16) | −0.0026 (13) | 0.0038 (13) | −0.0017 (13) |
C16B | 0.0282 (15) | 0.0261 (17) | 0.0248 (15) | 0.0015 (12) | 0.0018 (12) | 0.0017 (12) |
C17B | 0.0217 (13) | 0.0210 (15) | 0.0215 (14) | 0.0036 (11) | 0.0045 (11) | 0.0025 (11) |
C18B | 0.0187 (13) | 0.0248 (16) | 0.0215 (14) | 0.0038 (11) | 0.0017 (11) | 0.0026 (11) |
C19B | 0.0196 (16) | 0.0173 (17) | 0.0304 (19) | −0.0010 (13) | 0.0069 (14) | 0.0008 (15) |
C20B | 0.0245 (16) | 0.0259 (18) | 0.0241 (17) | −0.0002 (13) | 0.0043 (13) | 0.0024 (14) |
C21B | 0.0210 (15) | 0.0283 (18) | 0.0307 (17) | −0.0009 (13) | 0.0007 (13) | −0.0017 (14) |
C22B | 0.0205 (16) | 0.0205 (17) | 0.0347 (17) | 0.0026 (13) | 0.0031 (13) | 0.0039 (14) |
C23B | 0.0197 (16) | 0.0295 (19) | 0.041 (2) | 0.0018 (14) | 0.0039 (15) | 0.0076 (17) |
C24B | 0.0253 (16) | 0.0265 (18) | 0.053 (2) | 0.0005 (13) | 0.0127 (17) | 0.0136 (19) |
C25B | 0.037 (2) | 0.035 (2) | 0.041 (2) | 0.0037 (16) | 0.0168 (17) | 0.0135 (18) |
C26B | 0.0345 (18) | 0.035 (2) | 0.0312 (19) | 0.0017 (15) | 0.0074 (15) | 0.0055 (16) |
C27B | 0.0223 (17) | 0.022 (2) | 0.0308 (18) | 0.0012 (14) | 0.0062 (14) | 0.0021 (14) |
C28B | 0.0225 (15) | 0.0247 (17) | 0.0246 (16) | −0.0008 (13) | 0.0009 (12) | −0.0007 (13) |
C29B | 0.0244 (17) | 0.0226 (19) | 0.0180 (16) | 0.0042 (14) | 0.0042 (13) | 0.0024 (14) |
C30B | 0.0213 (16) | 0.0259 (17) | 0.0216 (15) | 0.0003 (13) | 0.0033 (13) | −0.0005 (12) |
C31B | 0.0239 (17) | 0.0272 (18) | 0.0195 (15) | 0.0008 (13) | −0.0002 (13) | −0.0005 (13) |
C32B | 0.0237 (16) | 0.0239 (17) | 0.0186 (15) | 0.0044 (13) | 0.0013 (13) | 0.0051 (13) |
C33B | 0.0341 (18) | 0.0293 (19) | 0.0204 (16) | 0.0072 (14) | 0.0064 (13) | 0.0031 (13) |
C34B | 0.0369 (19) | 0.040 (2) | 0.0251 (18) | 0.0136 (16) | 0.0144 (15) | 0.0086 (15) |
C35B | 0.0250 (17) | 0.043 (2) | 0.0357 (19) | 0.0058 (15) | 0.0117 (14) | 0.0155 (16) |
C36B | 0.0253 (17) | 0.037 (2) | 0.0305 (18) | −0.0027 (14) | 0.0041 (14) | 0.0079 (15) |
C37B | 0.0196 (15) | 0.024 (2) | 0.0234 (19) | 0.0030 (13) | 0.0026 (14) | 0.0056 (15) |
C38B | 0.0239 (16) | 0.027 (2) | 0.0215 (16) | −0.0025 (14) | 0.0002 (13) | −0.0002 (14) |
C39B | 0.0180 (13) | 0.0201 (15) | 0.0240 (14) | −0.0018 (10) | 0.0030 (11) | 0.0013 (11) |
C40B | 0.0225 (15) | 0.0282 (17) | 0.047 (2) | 0.0053 (13) | 0.0099 (14) | 0.0117 (15) |
C41B | 0.0297 (17) | 0.041 (2) | 0.061 (3) | 0.0050 (15) | 0.0252 (17) | 0.0108 (18) |
C42B | 0.0408 (19) | 0.041 (2) | 0.042 (2) | −0.0020 (16) | 0.0232 (16) | 0.0099 (16) |
C43B | 0.0313 (17) | 0.047 (2) | 0.0320 (17) | 0.0013 (15) | 0.0077 (14) | 0.0160 (16) |
C44B | 0.0239 (14) | 0.0328 (18) | 0.0301 (16) | 0.0023 (13) | 0.0072 (12) | 0.0105 (13) |
C45B | 0.0180 (12) | 0.0180 (14) | 0.0208 (13) | 0.0011 (10) | 0.0042 (10) | 0.0042 (11) |
C46B | 0.0198 (13) | 0.0242 (15) | 0.0255 (15) | 0.0027 (11) | 0.0007 (11) | −0.0017 (12) |
C47B | 0.0260 (15) | 0.0248 (16) | 0.0288 (16) | 0.0035 (12) | 0.0041 (12) | −0.0046 (12) |
C48B | 0.0242 (14) | 0.0226 (16) | 0.0318 (16) | 0.0057 (11) | 0.0067 (12) | 0.0027 (12) |
C49B | 0.0240 (15) | 0.0319 (18) | 0.0320 (16) | 0.0087 (13) | −0.0070 (13) | −0.0027 (14) |
C50B | 0.0273 (15) | 0.0246 (16) | 0.0283 (15) | 0.0062 (12) | −0.0046 (12) | −0.0068 (12) |
C51B | 0.0168 (12) | 0.0213 (14) | 0.0188 (13) | 0.0016 (10) | 0.0016 (10) | 0.0028 (11) |
C52B | 0.0274 (14) | 0.0196 (15) | 0.0226 (14) | 0.0047 (11) | 0.0008 (11) | −0.0005 (11) |
C53B | 0.0327 (16) | 0.0298 (17) | 0.0193 (14) | 0.0044 (13) | 0.0028 (12) | 0.0033 (12) |
C54B | 0.0317 (16) | 0.0254 (17) | 0.0259 (15) | 0.0020 (12) | 0.0085 (12) | 0.0086 (12) |
C55B | 0.0290 (15) | 0.0189 (15) | 0.0288 (15) | −0.0029 (11) | 0.0073 (12) | 0.0007 (12) |
C56B | 0.0259 (14) | 0.0223 (15) | 0.0217 (14) | −0.0038 (11) | 0.0056 (11) | −0.0003 (12) |
C57B | 0.0207 (13) | 0.0196 (14) | 0.0200 (13) | 0.0046 (11) | 0.0018 (10) | 0.0035 (11) |
C58B | 0.0262 (14) | 0.0205 (15) | 0.0304 (15) | −0.0006 (11) | 0.0072 (12) | −0.0019 (12) |
C59B | 0.0343 (16) | 0.0242 (17) | 0.0297 (16) | −0.0008 (13) | 0.0073 (13) | −0.0076 (13) |
C60B | 0.0278 (15) | 0.0309 (17) | 0.0256 (15) | 0.0062 (13) | 0.0083 (12) | −0.0007 (13) |
C61B | 0.0229 (14) | 0.0313 (17) | 0.0281 (15) | 0.0011 (12) | 0.0067 (12) | 0.0030 (13) |
C62B | 0.0218 (13) | 0.0236 (16) | 0.0226 (14) | 0.0005 (11) | 0.0014 (11) | −0.0010 (11) |
O1 | 0.0399 (14) | 0.0360 (14) | 0.0473 (14) | −0.0044 (11) | 0.0060 (11) | −0.0055 (12) |
C1 | 0.0410 (19) | 0.0263 (18) | 0.0365 (18) | −0.0007 (14) | 0.0075 (14) | −0.0054 (14) |
C2 | 0.048 (2) | 0.088 (4) | 0.038 (2) | −0.016 (2) | 0.0090 (18) | −0.012 (2) |
C3 | 0.053 (2) | 0.038 (2) | 0.0365 (19) | −0.0081 (17) | 0.0046 (16) | −0.0040 (16) |
C29C | 0.024 (10) | 0.029 (15) | 0.024 (11) | −0.001 (9) | 0.004 (8) | −0.002 (9) |
C38C | 0.0213 (16) | 0.0259 (17) | 0.0216 (15) | 0.0003 (13) | 0.0033 (13) | −0.0005 (12) |
C37C | 0.021 (10) | 0.020 (11) | 0.019 (10) | 0.003 (8) | 0.000 (8) | 0.003 (8) |
C36C | 0.031 (11) | 0.010 (11) | 0.021 (10) | 0.008 (8) | 0.004 (8) | 0.001 (8) |
C35C | 0.0341 (18) | 0.0293 (19) | 0.0204 (16) | 0.0072 (14) | 0.0064 (13) | 0.0031 (13) |
C34C | 0.0341 (18) | 0.0293 (19) | 0.0204 (16) | 0.0072 (14) | 0.0064 (13) | 0.0031 (13) |
C33C | 0.031 (11) | 0.034 (12) | 0.011 (10) | 0.012 (8) | 0.002 (8) | 0.003 (8) |
C32C | 0.025 (10) | 0.025 (12) | 0.013 (12) | 0.001 (9) | 0.003 (9) | 0.001 (9) |
C31C | 0.030 (12) | 0.019 (13) | 0.022 (11) | −0.001 (10) | 0.008 (9) | 0.000 (9) |
C30C | 0.021 (10) | 0.026 (15) | 0.021 (12) | 0.004 (9) | 0.005 (9) | 0.000 (10) |
C19C | 0.025 (11) | 0.014 (12) | 0.026 (8) | 0.001 (10) | 0.004 (7) | −0.006 (9) |
C27C | 0.030 (11) | 0.033 (14) | 0.043 (10) | −0.007 (10) | 0.008 (8) | −0.004 (10) |
C25C | 0.025 (12) | 0.032 (16) | 0.055 (9) | 0.000 (11) | 0.013 (10) | 0.014 (12) |
C20C | 0.0225 (15) | 0.0247 (17) | 0.0246 (16) | −0.0008 (13) | 0.0009 (12) | −0.0007 (13) |
C24C | 0.0253 (16) | 0.0265 (18) | 0.053 (2) | 0.0005 (13) | 0.0127 (17) | 0.0136 (19) |
C21C | 0.017 (9) | 0.017 (13) | 0.047 (11) | −0.001 (8) | 0.005 (8) | 0.000 (11) |
C26C | 0.0205 (16) | 0.0205 (17) | 0.0347 (17) | 0.0026 (13) | 0.0031 (13) | 0.0039 (14) |
C22C | 0.012 (10) | 0.029 (16) | 0.045 (10) | 0.001 (9) | 0.007 (8) | 0.002 (11) |
C28C | 0.025 (10) | 0.024 (13) | 0.025 (11) | −0.006 (9) | 0.002 (9) | −0.011 (11) |
C23C | 0.018 (10) | 0.034 (14) | 0.052 (12) | 0.005 (9) | 0.014 (8) | 0.016 (12) |
Fe1A—C1A | 1.835 (3) | C7B—C51B | 1.480 (4) |
Fe1A—C2A | 1.829 (3) | C8B—C57B | 1.484 (4) |
Fe1A—C3A | 1.828 (3) | C9B—C10B | 1.414 (4) |
Fe1A—C4A | 2.367 (3) | C9B—C18B | 1.373 (4) |
Fe1A—C5A | 2.142 (3) | C10B—H10B | 0.9500 |
Fe1A—C6A | 2.070 (3) | C10B—C11B | 1.367 (5) |
Fe1A—C7A | 2.067 (3) | C11B—H11B | 0.9500 |
Fe1A—C8A | 2.141 (3) | C11B—C12B | 1.423 (5) |
O1A—C4A | 1.247 (4) | C12B—C13B | 1.411 (4) |
N1A—C1A | 1.160 (4) | C12B—C17B | 1.428 (4) |
N1A—C9A | 1.399 (4) | C13B—H13B | 0.9500 |
N2A—C2A | 1.165 (4) | C13B—C14B | 1.364 (5) |
N2A—C19A | 1.396 (4) | C14B—H14B | 0.9500 |
N3A—C3A | 1.167 (4) | C14B—C15B | 1.413 (5) |
N3A—C29A | 1.403 (4) | C15B—H15B | 0.9500 |
C4A—C5A | 1.480 (4) | C15B—C16B | 1.364 (5) |
C4A—C8A | 1.476 (4) | C16B—H16B | 0.9500 |
C5A—C6A | 1.438 (4) | C16B—C17B | 1.419 (5) |
C5A—C39A | 1.488 (4) | C17B—C18B | 1.421 (4) |
C6A—C7A | 1.442 (4) | C18B—H18B | 0.9500 |
C6A—C45A | 1.486 (4) | C19B—C20B | 1.413 (5) |
C7A—C8A | 1.447 (4) | C19B—C28B | 1.377 (5) |
C7A—C51A | 1.484 (4) | C20B—H20B | 0.9500 |
C8A—C57A | 1.481 (4) | C20B—C21B | 1.367 (5) |
C9A—C10A | 1.412 (4) | C21B—H21B | 0.9500 |
C9A—C18A | 1.372 (4) | C21B—C22B | 1.416 (5) |
C10A—H10A | 0.9500 | C22B—C23B | 1.424 (5) |
C10A—C11A | 1.361 (5) | C22B—C27B | 1.417 (5) |
C11A—H11A | 0.9500 | C23B—H23B | 0.9500 |
C11A—C12A | 1.425 (4) | C23B—C24B | 1.371 (6) |
C12A—C13A | 1.419 (4) | C24B—H24B | 0.9500 |
C12A—C17A | 1.416 (4) | C24B—C25B | 1.409 (6) |
C13A—H13A | 0.9500 | C25B—H25B | 0.9500 |
C13A—C14A | 1.366 (5) | C25B—C26B | 1.369 (5) |
C14A—H14A | 0.9500 | C26B—H26B | 0.9500 |
C14A—C15A | 1.412 (5) | C26B—C27B | 1.415 (5) |
C15A—H15A | 0.9500 | C27B—C28B | 1.419 (5) |
C15A—C16A | 1.368 (5) | C28B—H28B | 0.9500 |
C16A—H16A | 0.9500 | C29B—C30B | 1.416 (5) |
C16A—C17A | 1.420 (4) | C29B—C38B | 1.370 (5) |
C17A—C18A | 1.413 (4) | C30B—H30B | 0.9500 |
C18A—H18A | 0.9500 | C30B—C31B | 1.370 (5) |
C19A—C20A | 1.413 (4) | C31B—H31B | 0.9500 |
C19A—C28A | 1.369 (4) | C31B—C32B | 1.416 (5) |
C20A—H20A | 0.9500 | C32B—C33B | 1.419 (5) |
C20A—C21A | 1.366 (4) | C32B—C37B | 1.420 (5) |
C21A—H21A | 0.9500 | C33B—H33B | 0.9500 |
C21A—C22A | 1.417 (4) | C33B—C34B | 1.370 (5) |
C22A—C23A | 1.425 (4) | C34B—H34B | 0.9500 |
C22A—C27A | 1.414 (4) | C34B—C35B | 1.401 (6) |
C23A—H23A | 0.9500 | C35B—H35B | 0.9500 |
C23A—C24A | 1.366 (5) | C35B—C36B | 1.367 (5) |
C24A—H24A | 0.9500 | C36B—H36B | 0.9500 |
C24A—C25A | 1.402 (7) | C36B—C37B | 1.418 (5) |
C25A—H25A | 0.9500 | C37B—C38B | 1.419 (5) |
C25A—C26A | 1.375 (5) | C38B—H38B | 0.9500 |
C26A—H26A | 0.9500 | C39B—C40B | 1.404 (4) |
C26A—C27A | 1.420 (4) | C39B—C44B | 1.398 (4) |
C27A—C28A | 1.416 (4) | C40B—H40B | 0.9500 |
C28A—H28A | 0.9500 | C40B—C41B | 1.388 (5) |
C29A—C30A | 1.415 (5) | C41B—H41B | 0.9500 |
C29A—C38A | 1.369 (4) | C41B—C42B | 1.385 (6) |
C30A—H30A | 0.9500 | C42B—H42B | 0.9500 |
C30A—C31A | 1.372 (5) | C42B—C43B | 1.385 (5) |
C31A—H31A | 0.9500 | C43B—H43B | 0.9500 |
C31A—C32A | 1.416 (5) | C43B—C44B | 1.391 (4) |
C32A—C33A | 1.425 (4) | C44B—H44B | 0.9500 |
C32A—C37A | 1.425 (5) | C45B—C46B | 1.389 (4) |
C33A—H33A | 0.9500 | C45B—C50B | 1.399 (4) |
C33A—C34A | 1.365 (6) | C46B—H46B | 0.9500 |
C34A—H34A | 0.9500 | C46B—C47B | 1.394 (4) |
C34A—C35A | 1.413 (7) | C47B—H47B | 0.9500 |
C35A—H35A | 0.9500 | C47B—C48B | 1.380 (5) |
C35A—C36A | 1.358 (5) | C48B—H48B | 0.9500 |
C36A—H36A | 0.9500 | C48B—C49B | 1.379 (5) |
C36A—C37A | 1.416 (5) | C49B—H49B | 0.9500 |
C37A—C38A | 1.408 (4) | C49B—C50B | 1.387 (4) |
C38A—H38A | 0.9500 | C50B—H50B | 0.9500 |
C39A—C40A | 1.400 (4) | C51B—C52B | 1.400 (4) |
C39A—C44A | 1.400 (4) | C51B—C56B | 1.390 (4) |
C40A—H40A | 0.9500 | C52B—H52B | 0.9500 |
C40A—C41A | 1.393 (4) | C52B—C53B | 1.394 (4) |
C41A—H41A | 0.9500 | C53B—H53B | 0.9500 |
C41A—C42A | 1.391 (5) | C53B—C54B | 1.380 (5) |
C42A—H42A | 0.9500 | C54B—H54B | 0.9500 |
C42A—C43A | 1.386 (5) | C54B—C55B | 1.392 (5) |
C43A—H43A | 0.9500 | C55B—H55B | 0.9500 |
C43A—C44A | 1.388 (4) | C55B—C56B | 1.386 (4) |
C44A—H44A | 0.9500 | C56B—H56B | 0.9500 |
C45A—C46A | 1.395 (4) | C57B—C58B | 1.393 (4) |
C45A—C50A | 1.398 (4) | C57B—C62B | 1.398 (4) |
C46A—H46A | 0.9500 | C58B—H58B | 0.9500 |
C46A—C47A | 1.394 (4) | C58B—C59B | 1.387 (4) |
C47A—H47A | 0.9500 | C59B—H59B | 0.9500 |
C47A—C48A | 1.386 (5) | C59B—C60B | 1.389 (5) |
C48A—H48A | 0.9500 | C60B—H60B | 0.9500 |
C48A—C49A | 1.385 (5) | C60B—C61B | 1.391 (5) |
C49A—H49A | 0.9500 | C61B—H61B | 0.9500 |
C49A—C50A | 1.390 (4) | C61B—C62B | 1.390 (4) |
C50A—H50A | 0.9500 | C62B—H62B | 0.9500 |
C51A—C52A | 1.396 (4) | O1—C1 | 1.211 (4) |
C51A—C56A | 1.394 (4) | C1—C2 | 1.502 (5) |
C52A—H52A | 0.9500 | C1—C3 | 1.495 (5) |
C52A—C53A | 1.396 (4) | C2—H2A | 0.9800 |
C53A—H53A | 0.9500 | C2—H2B | 0.9800 |
C53A—C54A | 1.384 (5) | C2—H2C | 0.9800 |
C54A—H54A | 0.9500 | C3—H3A | 0.9800 |
C54A—C55A | 1.379 (5) | C3—H3B | 0.9800 |
C55A—H55A | 0.9500 | C3—H3C | 0.9800 |
C55A—C56A | 1.396 (4) | C29C—C38C | 1.39 (2) |
C56A—H56A | 0.9500 | C29C—C30C | 1.391 (19) |
C57A—C58A | 1.405 (4) | C38C—H38C | 0.9500 |
C57A—C62A | 1.402 (4) | C38C—C37C | 1.419 (19) |
C58A—H58A | 0.9500 | C37C—C36C | 1.403 (19) |
C58A—C59A | 1.392 (4) | C37C—C32C | 1.410 (19) |
C59A—H59A | 0.9500 | C36C—H36C | 0.9500 |
C59A—C60A | 1.384 (5) | C36C—C35C | 1.408 (19) |
C60A—H60A | 0.9500 | C35C—H35C | 0.9500 |
C60A—C61A | 1.392 (5) | C35C—C34C | 1.409 (19) |
C61A—H61A | 0.9500 | C34C—H34C | 0.9500 |
C61A—C62A | 1.385 (4) | C34C—C33C | 1.39 (2) |
C62A—H62A | 0.9500 | C33C—H33C | 0.9500 |
Fe1B—C1B | 1.836 (3) | C33C—C32C | 1.423 (19) |
Fe1B—C2B | 1.840 (3) | C32C—C31C | 1.414 (19) |
Fe1B—C3B | 1.823 (3) | C31C—H31C | 0.9500 |
Fe1B—C4B | 2.373 (3) | C31C—C30C | 1.398 (19) |
Fe1B—C5B | 2.116 (3) | C30C—H30C | 0.9500 |
Fe1B—C6B | 2.070 (3) | C19C—C20C | 1.385 (19) |
Fe1B—C7B | 2.085 (3) | C19C—C28C | 1.392 (19) |
Fe1B—C8B | 2.142 (3) | C27C—C26C | 1.402 (18) |
O1B—C4B | 1.243 (4) | C27C—C22C | 1.404 (19) |
N1B—C1B | 1.163 (4) | C27C—C28C | 1.403 (19) |
N1B—C9B | 1.397 (4) | C25C—H25C | 0.9500 |
N2B—C2B | 1.172 (4) | C25C—C24C | 1.39 (2) |
N2B—C19B | 1.410 (4) | C25C—C26C | 1.391 (19) |
N2B—C19C | 1.39 (2) | C20C—H20C | 0.9500 |
N3B—C3B | 1.172 (4) | C20C—C21C | 1.394 (19) |
N3B—C29B | 1.404 (4) | C24C—H24C | 0.9500 |
N3B—C29C | 1.38 (2) | C24C—C23C | 1.39 (2) |
C4B—C5B | 1.481 (4) | C21C—H21C | 0.9500 |
C4B—C8B | 1.477 (4) | C21C—C22C | 1.404 (19) |
C5B—C6B | 1.442 (4) | C26C—H26C | 0.9500 |
C5B—C39B | 1.479 (4) | C22C—C23C | 1.400 (18) |
C6B—C7B | 1.441 (4) | C28C—H28C | 0.9500 |
C6B—C45B | 1.491 (4) | C23C—H23C | 0.9500 |
C7B—C8B | 1.436 (4) | ||
C1A—Fe1A—C4A | 79.78 (11) | C5B—C4B—Fe1B | 61.55 (15) |
C1A—Fe1A—C5A | 98.52 (12) | C8B—C4B—Fe1B | 62.62 (15) |
C1A—Fe1A—C6A | 138.31 (12) | C8B—C4B—C5B | 104.3 (2) |
C1A—Fe1A—C7A | 137.35 (12) | C4B—C5B—Fe1B | 80.46 (16) |
C1A—Fe1A—C8A | 97.18 (12) | C6B—C5B—Fe1B | 68.15 (15) |
C2A—Fe1A—C1A | 95.62 (13) | C6B—C5B—C4B | 108.6 (2) |
C2A—Fe1A—C4A | 132.89 (11) | C6B—C5B—C39B | 127.7 (3) |
C2A—Fe1A—C5A | 159.93 (11) | C39B—C5B—Fe1B | 126.0 (2) |
C2A—Fe1A—C6A | 123.96 (12) | C39B—C5B—C4B | 122.8 (3) |
C2A—Fe1A—C7A | 92.63 (12) | C5B—C6B—Fe1B | 71.57 (15) |
C2A—Fe1A—C8A | 98.10 (11) | C5B—C6B—C45B | 128.9 (2) |
C3A—Fe1A—C1A | 97.51 (12) | C7B—C6B—Fe1B | 70.28 (14) |
C3A—Fe1A—C2A | 95.24 (12) | C7B—C6B—C5B | 107.6 (2) |
C3A—Fe1A—C4A | 131.86 (11) | C7B—C6B—C45B | 122.4 (2) |
C3A—Fe1A—C5A | 96.94 (12) | C45B—C6B—Fe1B | 133.1 (2) |
C3A—Fe1A—C6A | 91.83 (12) | C6B—C7B—Fe1B | 69.13 (14) |
C3A—Fe1A—C7A | 123.31 (12) | C6B—C7B—C51B | 123.2 (3) |
C3A—Fe1A—C8A | 159.05 (12) | C8B—C7B—Fe1B | 72.29 (15) |
C5A—Fe1A—C4A | 37.90 (10) | C8B—C7B—C6B | 108.6 (2) |
C6A—Fe1A—C4A | 64.25 (10) | C8B—C7B—C51B | 127.4 (2) |
C6A—Fe1A—C5A | 39.87 (11) | C51B—C7B—Fe1B | 132.2 (2) |
C6A—Fe1A—C8A | 67.30 (10) | C4B—C8B—Fe1B | 79.63 (17) |
C7A—Fe1A—C4A | 64.44 (10) | C4B—C8B—C57B | 125.0 (3) |
C7A—Fe1A—C5A | 67.34 (10) | C7B—C8B—Fe1B | 68.01 (15) |
C7A—Fe1A—C6A | 40.80 (10) | C7B—C8B—C4B | 108.3 (2) |
C7A—Fe1A—C8A | 40.18 (11) | C7B—C8B—C57B | 124.6 (3) |
C8A—Fe1A—C4A | 37.80 (10) | C57B—C8B—Fe1B | 131.2 (2) |
C8A—Fe1A—C5A | 66.10 (10) | N1B—C9B—C10B | 119.0 (3) |
C1A—N1A—C9A | 168.6 (3) | C18B—C9B—N1B | 118.8 (3) |
C2A—N2A—C19A | 170.5 (3) | C18B—C9B—C10B | 122.1 (3) |
C3A—N3A—C29A | 168.5 (3) | C9B—C10B—H10B | 120.3 |
N1A—C1A—Fe1A | 175.5 (3) | C11B—C10B—C9B | 119.4 (3) |
N2A—C2A—Fe1A | 176.5 (3) | C11B—C10B—H10B | 120.3 |
N3A—C3A—Fe1A | 175.5 (3) | C10B—C11B—H11B | 119.5 |
O1A—C4A—Fe1A | 133.9 (2) | C10B—C11B—C12B | 120.9 (3) |
O1A—C4A—C5A | 128.0 (3) | C12B—C11B—H11B | 119.5 |
O1A—C4A—C8A | 127.3 (3) | C11B—C12B—C17B | 118.8 (3) |
C5A—C4A—Fe1A | 62.77 (15) | C13B—C12B—C11B | 122.5 (3) |
C8A—C4A—Fe1A | 62.76 (14) | C13B—C12B—C17B | 118.7 (3) |
C8A—C4A—C5A | 104.4 (2) | C12B—C13B—H13B | 119.5 |
C4A—C5A—Fe1A | 79.34 (16) | C14B—C13B—C12B | 121.0 (3) |
C4A—C5A—C39A | 123.8 (3) | C14B—C13B—H13B | 119.5 |
C6A—C5A—Fe1A | 67.36 (15) | C13B—C14B—H14B | 119.8 |
C6A—C5A—C4A | 108.8 (2) | C13B—C14B—C15B | 120.3 (3) |
C6A—C5A—C39A | 125.6 (2) | C15B—C14B—H14B | 119.8 |
C39A—C5A—Fe1A | 131.10 (19) | C14B—C15B—H15B | 119.8 |
C5A—C6A—Fe1A | 72.76 (15) | C16B—C15B—C14B | 120.5 (3) |
C5A—C6A—C7A | 108.3 (2) | C16B—C15B—H15B | 119.8 |
C5A—C6A—C45A | 125.3 (2) | C15B—C16B—H16B | 119.8 |
C7A—C6A—Fe1A | 69.51 (15) | C15B—C16B—C17B | 120.4 (3) |
C7A—C6A—C45A | 125.3 (2) | C17B—C16B—H16B | 119.8 |
C45A—C6A—Fe1A | 132.87 (19) | C16B—C17B—C12B | 119.0 (3) |
C6A—C7A—Fe1A | 69.69 (14) | C16B—C17B—C18B | 121.3 (3) |
C6A—C7A—C8A | 107.8 (2) | C18B—C17B—C12B | 119.6 (3) |
C6A—C7A—C51A | 124.5 (2) | C9B—C18B—C17B | 119.1 (3) |
C8A—C7A—Fe1A | 72.65 (15) | C9B—C18B—H18B | 120.5 |
C8A—C7A—C51A | 126.3 (2) | C17B—C18B—H18B | 120.5 |
C51A—C7A—Fe1A | 133.59 (19) | N2B—C19B—C20B | 119.0 (3) |
C4A—C8A—Fe1A | 79.43 (16) | C28B—C19B—N2B | 119.4 (3) |
C4A—C8A—C57A | 124.0 (3) | C28B—C19B—C20B | 121.6 (3) |
C7A—C8A—Fe1A | 67.17 (15) | C19B—C20B—H20B | 120.3 |
C7A—C8A—C4A | 108.9 (2) | C21B—C20B—C19B | 119.3 (3) |
C7A—C8A—C57A | 125.5 (2) | C21B—C20B—H20B | 120.3 |
C57A—C8A—Fe1A | 130.93 (19) | C20B—C21B—H21B | 119.5 |
N1A—C9A—C10A | 117.6 (3) | C20B—C21B—C22B | 121.0 (3) |
C18A—C9A—N1A | 119.9 (3) | C22B—C21B—H21B | 119.5 |
C18A—C9A—C10A | 122.4 (3) | C21B—C22B—C23B | 121.9 (3) |
C9A—C10A—H10A | 120.7 | C21B—C22B—C27B | 119.3 (3) |
C11A—C10A—C9A | 118.7 (3) | C27B—C22B—C23B | 118.8 (3) |
C11A—C10A—H10A | 120.7 | C22B—C23B—H23B | 119.6 |
C10A—C11A—H11A | 119.4 | C24B—C23B—C22B | 120.8 (4) |
C10A—C11A—C12A | 121.2 (3) | C24B—C23B—H23B | 119.6 |
C12A—C11A—H11A | 119.4 | C23B—C24B—H24B | 120.0 |
C13A—C12A—C11A | 121.9 (3) | C23B—C24B—C25B | 119.9 (4) |
C17A—C12A—C11A | 119.1 (3) | C25B—C24B—H24B | 120.0 |
C17A—C12A—C13A | 119.0 (3) | C24B—C25B—H25B | 119.7 |
C12A—C13A—H13A | 119.7 | C26B—C25B—C24B | 120.7 (4) |
C14A—C13A—C12A | 120.6 (3) | C26B—C25B—H25B | 119.7 |
C14A—C13A—H13A | 119.7 | C25B—C26B—H26B | 119.7 |
C13A—C14A—H14A | 119.7 | C25B—C26B—C27B | 120.7 (4) |
C13A—C14A—C15A | 120.7 (3) | C27B—C26B—H26B | 119.7 |
C15A—C14A—H14A | 119.7 | C22B—C27B—C28B | 119.3 (3) |
C14A—C15A—H15A | 120.1 | C26B—C27B—C22B | 119.1 (3) |
C16A—C15A—C14A | 119.9 (3) | C26B—C27B—C28B | 121.6 (3) |
C16A—C15A—H15A | 120.1 | C19B—C28B—C27B | 119.4 (3) |
C15A—C16A—H16A | 119.5 | C19B—C28B—H28B | 120.3 |
C15A—C16A—C17A | 120.9 (3) | C27B—C28B—H28B | 120.3 |
C17A—C16A—H16A | 119.5 | N3B—C29B—C30B | 119.4 (3) |
C12A—C17A—C16A | 118.9 (3) | C38B—C29B—N3B | 119.0 (3) |
C18A—C17A—C12A | 119.3 (3) | C38B—C29B—C30B | 121.6 (3) |
C18A—C17A—C16A | 121.8 (3) | C29B—C30B—H30B | 120.3 |
C9A—C18A—C17A | 119.2 (3) | C31B—C30B—C29B | 119.3 (3) |
C9A—C18A—H18A | 120.4 | C31B—C30B—H30B | 120.3 |
C17A—C18A—H18A | 120.4 | C30B—C31B—H31B | 119.6 |
N2A—C19A—C20A | 118.8 (3) | C30B—C31B—C32B | 120.8 (3) |
C28A—C19A—N2A | 119.2 (3) | C32B—C31B—H31B | 119.6 |
C28A—C19A—C20A | 122.0 (3) | C31B—C32B—C33B | 121.6 (3) |
C19A—C20A—H20A | 120.5 | C31B—C32B—C37B | 119.5 (3) |
C21A—C20A—C19A | 119.1 (3) | C33B—C32B—C37B | 118.8 (3) |
C21A—C20A—H20A | 120.5 | C32B—C33B—H33B | 119.9 |
C20A—C21A—H21A | 119.6 | C34B—C33B—C32B | 120.2 (4) |
C20A—C21A—C22A | 120.8 (3) | C34B—C33B—H33B | 119.9 |
C22A—C21A—H21A | 119.6 | C33B—C34B—H34B | 119.7 |
C21A—C22A—C23A | 121.7 (3) | C33B—C34B—C35B | 120.7 (3) |
C27A—C22A—C21A | 119.4 (3) | C35B—C34B—H34B | 119.7 |
C27A—C22A—C23A | 118.9 (3) | C34B—C35B—H35B | 119.6 |
C22A—C23A—H23A | 119.8 | C36B—C35B—C34B | 120.8 (3) |
C24A—C23A—C22A | 120.4 (3) | C36B—C35B—H35B | 119.6 |
C24A—C23A—H23A | 119.8 | C35B—C36B—H36B | 120.0 |
C23A—C24A—H24A | 119.7 | C35B—C36B—C37B | 120.1 (4) |
C23A—C24A—C25A | 120.5 (3) | C37B—C36B—H36B | 120.0 |
C25A—C24A—H24A | 119.7 | C36B—C37B—C32B | 119.4 (3) |
C24A—C25A—H25A | 119.5 | C36B—C37B—C38B | 121.7 (4) |
C26A—C25A—C24A | 120.9 (3) | C38B—C37B—C32B | 118.9 (3) |
C26A—C25A—H25A | 119.5 | C29B—C38B—C37B | 119.8 (3) |
C25A—C26A—H26A | 120.2 | C29B—C38B—H38B | 120.1 |
C25A—C26A—C27A | 119.7 (4) | C37B—C38B—H38B | 120.1 |
C27A—C26A—H26A | 120.2 | C40B—C39B—C5B | 122.9 (3) |
C22A—C27A—C26A | 119.6 (3) | C44B—C39B—C5B | 119.6 (3) |
C22A—C27A—C28A | 119.3 (3) | C44B—C39B—C40B | 117.5 (3) |
C28A—C27A—C26A | 121.1 (3) | C39B—C40B—H40B | 119.6 |
C19A—C28A—C27A | 119.4 (3) | C41B—C40B—C39B | 120.8 (3) |
C19A—C28A—H28A | 120.3 | C41B—C40B—H40B | 119.6 |
C27A—C28A—H28A | 120.3 | C40B—C41B—H41B | 119.7 |
N3A—C29A—C30A | 118.5 (3) | C42B—C41B—C40B | 120.6 (3) |
C38A—C29A—N3A | 119.7 (3) | C42B—C41B—H41B | 119.7 |
C38A—C29A—C30A | 121.7 (3) | C41B—C42B—H42B | 120.2 |
C29A—C30A—H30A | 120.6 | C41B—C42B—C43B | 119.7 (3) |
C31A—C30A—C29A | 118.7 (3) | C43B—C42B—H42B | 120.2 |
C31A—C30A—H30A | 120.6 | C42B—C43B—H43B | 120.1 |
C30A—C31A—H31A | 119.4 | C42B—C43B—C44B | 119.8 (3) |
C30A—C31A—C32A | 121.2 (3) | C44B—C43B—H43B | 120.1 |
C32A—C31A—H31A | 119.4 | C39B—C44B—H44B | 119.2 |
C31A—C32A—C33A | 122.2 (3) | C43B—C44B—C39B | 121.6 (3) |
C31A—C32A—C37A | 119.3 (3) | C43B—C44B—H44B | 119.2 |
C37A—C32A—C33A | 118.6 (3) | C46B—C45B—C6B | 124.6 (3) |
C32A—C33A—H33A | 119.7 | C46B—C45B—C50B | 117.7 (3) |
C34A—C33A—C32A | 120.7 (4) | C50B—C45B—C6B | 117.5 (3) |
C34A—C33A—H33A | 119.7 | C45B—C46B—H46B | 119.6 |
C33A—C34A—H34A | 119.8 | C45B—C46B—C47B | 120.9 (3) |
C33A—C34A—C35A | 120.4 (3) | C47B—C46B—H46B | 119.6 |
C35A—C34A—H34A | 119.8 | C46B—C47B—H47B | 119.7 |
C34A—C35A—H35A | 119.8 | C48B—C47B—C46B | 120.6 (3) |
C36A—C35A—C34A | 120.4 (4) | C48B—C47B—H47B | 119.7 |
C36A—C35A—H35A | 119.8 | C47B—C48B—H48B | 120.4 |
C35A—C36A—H36A | 119.4 | C49B—C48B—C47B | 119.3 (3) |
C35A—C36A—C37A | 121.2 (4) | C49B—C48B—H48B | 120.4 |
C37A—C36A—H36A | 119.4 | C48B—C49B—H49B | 119.8 |
C36A—C37A—C32A | 118.8 (3) | C48B—C49B—C50B | 120.4 (3) |
C38A—C37A—C32A | 118.8 (3) | C50B—C49B—H49B | 119.8 |
C38A—C37A—C36A | 122.4 (3) | C45B—C50B—H50B | 119.4 |
C29A—C38A—C37A | 120.3 (3) | C49B—C50B—C45B | 121.2 (3) |
C29A—C38A—H38A | 119.8 | C49B—C50B—H50B | 119.4 |
C37A—C38A—H38A | 119.8 | C52B—C51B—C7B | 119.5 (3) |
C40A—C39A—C5A | 122.4 (3) | C56B—C51B—C7B | 121.7 (3) |
C40A—C39A—C44A | 117.8 (3) | C56B—C51B—C52B | 118.5 (3) |
C44A—C39A—C5A | 119.8 (3) | C51B—C52B—H52B | 119.9 |
C39A—C40A—H40A | 119.5 | C53B—C52B—C51B | 120.2 (3) |
C41A—C40A—C39A | 121.0 (3) | C53B—C52B—H52B | 119.9 |
C41A—C40A—H40A | 119.5 | C52B—C53B—H53B | 119.8 |
C40A—C41A—H41A | 119.8 | C54B—C53B—C52B | 120.4 (3) |
C42A—C41A—C40A | 120.4 (3) | C54B—C53B—H53B | 119.8 |
C42A—C41A—H41A | 119.8 | C53B—C54B—H54B | 120.0 |
C41A—C42A—H42A | 120.5 | C53B—C54B—C55B | 119.9 (3) |
C43A—C42A—C41A | 119.0 (3) | C55B—C54B—H54B | 120.0 |
C43A—C42A—H42A | 120.5 | C54B—C55B—H55B | 120.2 |
C42A—C43A—H43A | 119.6 | C56B—C55B—C54B | 119.5 (3) |
C42A—C43A—C44A | 120.8 (3) | C56B—C55B—H55B | 120.2 |
C44A—C43A—H43A | 119.6 | C51B—C56B—H56B | 119.3 |
C39A—C44A—H44A | 119.5 | C55B—C56B—C51B | 121.4 (3) |
C43A—C44A—C39A | 121.0 (3) | C55B—C56B—H56B | 119.3 |
C43A—C44A—H44A | 119.5 | C58B—C57B—C8B | 119.5 (3) |
C46A—C45A—C6A | 124.1 (3) | C58B—C57B—C62B | 118.3 (3) |
C46A—C45A—C50A | 118.6 (3) | C62B—C57B—C8B | 121.9 (3) |
C50A—C45A—C6A | 117.3 (3) | C57B—C58B—H58B | 119.7 |
C45A—C46A—H46A | 119.6 | C59B—C58B—C57B | 120.6 (3) |
C47A—C46A—C45A | 120.9 (3) | C59B—C58B—H58B | 119.7 |
C47A—C46A—H46A | 119.6 | C58B—C59B—H59B | 119.6 |
C46A—C47A—H47A | 120.1 | C58B—C59B—C60B | 120.8 (3) |
C48A—C47A—C46A | 119.7 (3) | C60B—C59B—H59B | 119.6 |
C48A—C47A—H47A | 120.1 | C59B—C60B—H60B | 120.4 |
C47A—C48A—H48A | 120.0 | C59B—C60B—C61B | 119.2 (3) |
C49A—C48A—C47A | 120.0 (3) | C61B—C60B—H60B | 120.4 |
C49A—C48A—H48A | 120.0 | C60B—C61B—H61B | 120.0 |
C48A—C49A—H49A | 119.8 | C62B—C61B—C60B | 119.9 (3) |
C48A—C49A—C50A | 120.3 (3) | C62B—C61B—H61B | 120.0 |
C50A—C49A—H49A | 119.8 | C57B—C62B—H62B | 119.4 |
C45A—C50A—H50A | 119.8 | C61B—C62B—C57B | 121.1 (3) |
C49A—C50A—C45A | 120.4 (3) | C61B—C62B—H62B | 119.4 |
C49A—C50A—H50A | 119.8 | O1—C1—C2 | 121.2 (3) |
C52A—C51A—C7A | 118.0 (3) | O1—C1—C3 | 122.7 (3) |
C56A—C51A—C7A | 123.5 (2) | C3—C1—C2 | 116.1 (3) |
C56A—C51A—C52A | 118.4 (3) | C1—C2—H2A | 109.5 |
C51A—C52A—H52A | 119.6 | C1—C2—H2B | 109.5 |
C51A—C52A—C53A | 120.7 (3) | C1—C2—H2C | 109.5 |
C53A—C52A—H52A | 119.6 | H2A—C2—H2B | 109.5 |
C52A—C53A—H53A | 119.9 | H2A—C2—H2C | 109.5 |
C54A—C53A—C52A | 120.2 (3) | H2B—C2—H2C | 109.5 |
C54A—C53A—H53A | 119.9 | C1—C3—H3A | 109.5 |
C53A—C54A—H54A | 120.2 | C1—C3—H3B | 109.5 |
C55A—C54A—C53A | 119.6 (3) | C1—C3—H3C | 109.5 |
C55A—C54A—H54A | 120.2 | H3A—C3—H3B | 109.5 |
C54A—C55A—H55A | 119.7 | H3A—C3—H3C | 109.5 |
C54A—C55A—C56A | 120.5 (3) | H3B—C3—H3C | 109.5 |
C56A—C55A—H55A | 119.7 | N3B—C29C—C38C | 108 (2) |
C51A—C56A—C55A | 120.5 (3) | N3B—C29C—C30C | 127 (2) |
C51A—C56A—H56A | 119.7 | C38C—C29C—C30C | 124 (2) |
C55A—C56A—H56A | 119.7 | C29C—C38C—H38C | 121.8 |
C58A—C57A—C8A | 119.5 (3) | C29C—C38C—C37C | 116 (3) |
C62A—C57A—C8A | 122.4 (3) | C37C—C38C—H38C | 121.8 |
C62A—C57A—C58A | 118.0 (3) | C36C—C37C—C38C | 120 (2) |
C57A—C58A—H58A | 119.7 | C36C—C37C—C32C | 118 (2) |
C59A—C58A—C57A | 120.6 (3) | C32C—C37C—C38C | 121 (2) |
C59A—C58A—H58A | 119.7 | C37C—C36C—H36C | 120.0 |
C58A—C59A—H59A | 119.7 | C37C—C36C—C35C | 120 (3) |
C60A—C59A—C58A | 120.7 (3) | C35C—C36C—H36C | 120.0 |
C60A—C59A—H59A | 119.7 | C36C—C35C—H35C | 120.6 |
C59A—C60A—H60A | 120.4 | C36C—C35C—C34C | 119 (2) |
C59A—C60A—C61A | 119.2 (3) | C34C—C35C—H35C | 120.6 |
C61A—C60A—H60A | 120.4 | C35C—C34C—H34C | 117.8 |
C60A—C61A—H61A | 119.7 | C33C—C34C—C35C | 124 (3) |
C62A—C61A—C60A | 120.6 (3) | C33C—C34C—H34C | 117.8 |
C62A—C61A—H61A | 119.7 | C34C—C33C—H33C | 123.1 |
C57A—C62A—H62A | 119.5 | C34C—C33C—C32C | 114 (3) |
C61A—C62A—C57A | 120.9 (3) | C32C—C33C—H33C | 123.1 |
C61A—C62A—H62A | 119.5 | C37C—C32C—C33C | 124 (2) |
C1B—Fe1B—C2B | 98.74 (12) | C37C—C32C—C31C | 120 (2) |
C1B—Fe1B—C4B | 78.86 (11) | C31C—C32C—C33C | 116 (2) |
C1B—Fe1B—C5B | 98.60 (12) | C32C—C31C—H31C | 120.4 |
C1B—Fe1B—C6B | 138.56 (12) | C30C—C31C—C32C | 119 (2) |
C1B—Fe1B—C7B | 134.61 (12) | C30C—C31C—H31C | 120.4 |
C1B—Fe1B—C8B | 94.92 (12) | C29C—C30C—C31C | 119 (2) |
C2B—Fe1B—C4B | 138.73 (11) | C29C—C30C—H30C | 120.3 |
C2B—Fe1B—C5B | 160.37 (12) | C31C—C30C—H30C | 120.3 |
C2B—Fe1B—C6B | 121.14 (12) | C20C—C19C—N2B | 126 (2) |
C2B—Fe1B—C7B | 93.89 (12) | C20C—C19C—C28C | 126 (2) |
C2B—Fe1B—C8B | 102.83 (12) | C28C—C19C—N2B | 107.0 (19) |
C3B—Fe1B—C1B | 92.42 (13) | C26C—C27C—C22C | 117 (2) |
C3B—Fe1B—C2B | 95.40 (13) | C26C—C27C—C28C | 119 (2) |
C3B—Fe1B—C4B | 125.77 (11) | C28C—C27C—C22C | 124 (2) |
C3B—Fe1B—C5B | 92.98 (12) | C24C—C25C—H25C | 121.8 |
C3B—Fe1B—C6B | 94.38 (12) | C24C—C25C—C26C | 116 (3) |
C3B—Fe1B—C7B | 129.62 (12) | C26C—C25C—H25C | 121.8 |
C3B—Fe1B—C8B | 159.03 (11) | C19C—C20C—H20C | 122.7 |
C5B—Fe1B—C4B | 37.99 (10) | C19C—C20C—C21C | 115 (2) |
C5B—Fe1B—C8B | 66.52 (11) | C21C—C20C—H20C | 122.7 |
C6B—Fe1B—C4B | 64.17 (11) | C25C—C24C—H24C | 118.0 |
C6B—Fe1B—C5B | 40.28 (11) | C25C—C24C—C23C | 124 (3) |
C6B—Fe1B—C7B | 40.59 (10) | C23C—C24C—H24C | 118.0 |
C6B—Fe1B—C8B | 67.38 (11) | C20C—C21C—H21C | 117.5 |
C7B—Fe1B—C4B | 63.59 (10) | C20C—C21C—C22C | 125 (2) |
C7B—Fe1B—C5B | 67.24 (11) | C22C—C21C—H21C | 117.5 |
C7B—Fe1B—C8B | 39.70 (11) | C27C—C26C—H26C | 118.2 |
C8B—Fe1B—C4B | 37.75 (10) | C25C—C26C—C27C | 124 (3) |
C1B—N1B—C9B | 162.6 (3) | C25C—C26C—H26C | 118.2 |
C2B—N2B—C19B | 175.8 (3) | C21C—C22C—C27C | 115 (2) |
C2B—N2B—C19C | 157.9 (12) | C23C—C22C—C27C | 123 (3) |
C3B—N3B—C29B | 165.0 (3) | C23C—C22C—C21C | 122 (2) |
C3B—N3B—C29C | 152.5 (14) | C19C—C28C—C27C | 114 (2) |
N1B—C1B—Fe1B | 173.4 (2) | C19C—C28C—H28C | 122.8 |
N2B—C2B—Fe1B | 178.2 (3) | C27C—C28C—H28C | 122.8 |
N3B—C3B—Fe1B | 175.0 (3) | C24C—C23C—C22C | 117 (3) |
O1B—C4B—Fe1B | 135.8 (2) | C24C—C23C—H23C | 121.7 |
O1B—C4B—C5B | 127.7 (3) | C22C—C23C—H23C | 121.7 |
O1B—C4B—C8B | 127.9 (3) | ||
Fe1A—C4A—C5A—C6A | −61.44 (18) | O1B—C4B—C8B—C7B | −169.1 (3) |
Fe1A—C4A—C5A—C39A | 132.8 (3) | O1B—C4B—C8B—C57B | −5.2 (5) |
Fe1A—C4A—C8A—C7A | 61.26 (17) | N1B—C9B—C10B—C11B | −178.6 (3) |
Fe1A—C4A—C8A—C57A | −132.7 (3) | N1B—C9B—C18B—C17B | 178.2 (3) |
Fe1A—C5A—C6A—C7A | −60.74 (17) | N2B—C19B—C20B—C21B | 179.5 (3) |
Fe1A—C5A—C6A—C45A | 130.8 (3) | N2B—C19B—C28B—C27B | 179.0 (3) |
Fe1A—C5A—C39A—C40A | −55.7 (4) | N2B—C19C—C20C—C21C | 169 (3) |
Fe1A—C5A—C39A—C44A | 127.9 (3) | N2B—C19C—C28C—C27C | −170.8 (19) |
Fe1A—C6A—C7A—C8A | −63.09 (18) | N3B—C29B—C30B—C31B | −178.1 (3) |
Fe1A—C6A—C7A—C51A | 129.6 (3) | N3B—C29B—C38B—C37B | 178.4 (3) |
Fe1A—C6A—C45A—C46A | −26.3 (4) | N3B—C29C—C38C—C37C | −167 (2) |
Fe1A—C6A—C45A—C50A | 154.1 (2) | N3B—C29C—C30C—C31C | 167 (3) |
Fe1A—C7A—C8A—C4A | −69.26 (19) | C1B—N1B—C9B—C10B | 156.2 (9) |
Fe1A—C7A—C8A—C57A | 124.9 (3) | C1B—N1B—C9B—C18B | −22.3 (11) |
Fe1A—C7A—C51A—C52A | −151.0 (2) | C2B—N2B—C19C—C20C | 14 (6) |
Fe1A—C7A—C51A—C56A | 32.5 (4) | C2B—N2B—C19C—C28C | −176 (2) |
Fe1A—C8A—C57A—C58A | −132.2 (3) | C3B—N3B—C29B—C30B | 131.6 (11) |
Fe1A—C8A—C57A—C62A | 50.9 (4) | C3B—N3B—C29B—C38B | −48.0 (14) |
O1A—C4A—C5A—Fe1A | −126.0 (3) | C3B—N3B—C29C—C38C | 161 (2) |
O1A—C4A—C5A—C6A | 172.5 (3) | C3B—N3B—C29C—C30C | −5 (6) |
O1A—C4A—C5A—C39A | 6.8 (5) | C4B—C5B—C6B—Fe1B | 71.13 (19) |
O1A—C4A—C8A—Fe1A | 126.1 (3) | C4B—C5B—C6B—C7B | 9.7 (3) |
O1A—C4A—C8A—C7A | −172.7 (3) | C4B—C5B—C6B—C45B | −157.8 (3) |
O1A—C4A—C8A—C57A | −6.6 (5) | C4B—C5B—C39B—C40B | 135.0 (3) |
N1A—C9A—C10A—C11A | −177.3 (3) | C4B—C5B—C39B—C44B | −45.2 (4) |
N1A—C9A—C18A—C17A | 177.3 (2) | C4B—C8B—C57B—C58B | −41.2 (4) |
N2A—C19A—C20A—C21A | −177.0 (3) | C4B—C8B—C57B—C62B | 144.8 (3) |
N2A—C19A—C28A—C27A | 175.9 (3) | C5B—C4B—C8B—Fe1B | −46.74 (18) |
N3A—C29A—C30A—C31A | −177.0 (3) | C5B—C4B—C8B—C7B | 15.8 (3) |
N3A—C29A—C38A—C37A | 176.8 (3) | C5B—C4B—C8B—C57B | 179.7 (3) |
C1A—N1A—C9A—C10A | −3.5 (16) | C5B—C6B—C7B—Fe1B | 62.24 (18) |
C1A—N1A—C9A—C18A | 177.4 (13) | C5B—C6B—C7B—C8B | 0.4 (3) |
C3A—N3A—C29A—C30A | 102.3 (15) | C5B—C6B—C7B—C51B | −170.2 (2) |
C3A—N3A—C29A—C38A | −75.6 (16) | C5B—C6B—C45B—C46B | −85.4 (4) |
C4A—C5A—C6A—Fe1A | 69.26 (19) | C5B—C6B—C45B—C50B | 99.1 (4) |
C4A—C5A—C6A—C7A | 8.5 (3) | C5B—C39B—C40B—C41B | 177.9 (3) |
C4A—C5A—C6A—C45A | −160.0 (2) | C5B—C39B—C44B—C43B | −178.3 (3) |
C4A—C5A—C39A—C40A | −162.5 (3) | C6B—C5B—C39B—C40B | −33.2 (5) |
C4A—C5A—C39A—C44A | 21.1 (4) | C6B—C5B—C39B—C44B | 146.6 (3) |
C4A—C8A—C57A—C58A | −25.2 (4) | C6B—C7B—C8B—Fe1B | 59.85 (18) |
C4A—C8A—C57A—C62A | 157.9 (3) | C6B—C7B—C8B—C4B | −10.4 (3) |
C5A—C4A—C8A—Fe1A | −48.41 (18) | C6B—C7B—C8B—C57B | −174.4 (3) |
C5A—C4A—C8A—C7A | 12.9 (3) | C6B—C7B—C51B—C52B | 126.9 (3) |
C5A—C4A—C8A—C57A | 178.9 (2) | C6B—C7B—C51B—C56B | −46.1 (4) |
C5A—C6A—C7A—Fe1A | 62.81 (18) | C6B—C45B—C46B—C47B | −175.1 (3) |
C5A—C6A—C7A—C8A | −0.3 (3) | C6B—C45B—C50B—C49B | 175.8 (3) |
C5A—C6A—C7A—C51A | −167.6 (2) | C7B—C6B—C45B—C46B | 108.7 (3) |
C5A—C6A—C45A—C46A | −125.5 (3) | C7B—C6B—C45B—C50B | −66.8 (4) |
C5A—C6A—C45A—C50A | 54.9 (4) | C7B—C8B—C57B—C58B | 120.2 (3) |
C5A—C39A—C40A—C41A | −175.7 (3) | C7B—C8B—C57B—C62B | −53.8 (4) |
C5A—C39A—C44A—C43A | 176.0 (3) | C7B—C51B—C52B—C53B | −172.7 (3) |
C6A—C5A—C39A—C40A | 34.1 (4) | C7B—C51B—C56B—C55B | 170.3 (3) |
C6A—C5A—C39A—C44A | −142.3 (3) | C8B—C4B—C5B—Fe1B | 47.35 (19) |
C6A—C7A—C8A—Fe1A | 61.18 (17) | C8B—C4B—C5B—C6B | −15.6 (3) |
C6A—C7A—C8A—C4A | −8.1 (3) | C8B—C4B—C5B—C39B | 174.2 (2) |
C6A—C7A—C8A—C57A | −173.9 (2) | C8B—C7B—C51B—C52B | −41.9 (4) |
C6A—C7A—C51A—C52A | 114.8 (3) | C8B—C7B—C51B—C56B | 145.1 (3) |
C6A—C7A—C51A—C56A | −61.7 (4) | C8B—C57B—C58B—C59B | −171.8 (3) |
C6A—C45A—C46A—C47A | −178.4 (3) | C8B—C57B—C62B—C61B | 172.4 (3) |
C6A—C45A—C50A—C49A | 179.3 (3) | C9B—C10B—C11B—C12B | 0.1 (4) |
C7A—C6A—C45A—C46A | 67.9 (4) | C10B—C9B—C18B—C17B | −0.3 (4) |
C7A—C6A—C45A—C50A | −111.7 (3) | C10B—C11B—C12B—C13B | −180.0 (3) |
C7A—C8A—C57A—C58A | 138.5 (3) | C10B—C11B—C12B—C17B | 0.4 (4) |
C7A—C8A—C57A—C62A | −38.4 (4) | C11B—C12B—C13B—C14B | −177.4 (3) |
C7A—C51A—C52A—C53A | −174.2 (3) | C11B—C12B—C17B—C16B | 177.3 (3) |
C7A—C51A—C56A—C55A | 173.3 (3) | C11B—C12B—C17B—C18B | −0.8 (4) |
C8A—C4A—C5A—Fe1A | 48.41 (18) | C12B—C13B—C14B—C15B | −0.8 (5) |
C8A—C4A—C5A—C6A | −13.0 (3) | C12B—C17B—C18B—C9B | 0.8 (4) |
C8A—C4A—C5A—C39A | −178.8 (2) | C13B—C12B—C17B—C16B | −2.3 (4) |
C8A—C7A—C51A—C52A | −50.1 (4) | C13B—C12B—C17B—C18B | 179.5 (3) |
C8A—C7A—C51A—C56A | 133.4 (3) | C13B—C14B—C15B—C16B | −0.7 (5) |
C8A—C57A—C58A—C59A | −176.7 (3) | C14B—C15B—C16B—C17B | 0.6 (5) |
C8A—C57A—C62A—C61A | 176.1 (3) | C15B—C16B—C17B—C12B | 0.9 (5) |
C9A—C10A—C11A—C12A | 0.6 (5) | C15B—C16B—C17B—C18B | 179.1 (3) |
C10A—C9A—C18A—C17A | −1.7 (4) | C16B—C17B—C18B—C9B | −177.3 (3) |
C10A—C11A—C12A—C13A | 176.4 (3) | C17B—C12B—C13B—C14B | 2.3 (5) |
C10A—C11A—C12A—C17A | −2.9 (4) | C18B—C9B—C10B—C11B | −0.2 (4) |
C11A—C12A—C13A—C14A | −179.4 (3) | C19B—C20B—C21B—C22B | 1.5 (5) |
C11A—C12A—C17A—C16A | −178.9 (3) | C20B—C19B—C28B—C27B | 0.5 (5) |
C11A—C12A—C17A—C18A | 3.0 (4) | C20B—C21B—C22B—C23B | 178.9 (3) |
C12A—C13A—C14A—C15A | −1.1 (5) | C20B—C21B—C22B—C27B | 0.4 (5) |
C12A—C17A—C18A—C9A | −0.7 (4) | C21B—C22B—C23B—C24B | −177.3 (4) |
C13A—C12A—C17A—C16A | 1.8 (4) | C21B—C22B—C27B—C26B | 177.3 (4) |
C13A—C12A—C17A—C18A | −176.4 (3) | C21B—C22B—C27B—C28B | −1.9 (5) |
C13A—C14A—C15A—C16A | 0.7 (5) | C22B—C23B—C24B—C25B | −0.3 (6) |
C14A—C15A—C16A—C17A | 1.1 (5) | C22B—C27B—C28B—C19B | 1.4 (6) |
C15A—C16A—C17A—C12A | −2.3 (4) | C23B—C22B—C27B—C26B | −1.3 (6) |
C15A—C16A—C17A—C18A | 175.8 (3) | C23B—C22B—C27B—C28B | 179.6 (3) |
C16A—C17A—C18A—C9A | −178.8 (3) | C23B—C24B—C25B—C26B | −0.7 (6) |
C17A—C12A—C13A—C14A | −0.1 (5) | C24B—C25B—C26B—C27B | 0.7 (6) |
C18A—C9A—C10A—C11A | 1.8 (4) | C25B—C26B—C27B—C22B | 0.3 (6) |
C19A—C20A—C21A—C22A | 0.9 (5) | C25B—C26B—C27B—C28B | 179.5 (4) |
C20A—C19A—C28A—C27A | −2.3 (5) | C26B—C27B—C28B—C19B | −177.7 (4) |
C20A—C21A—C22A—C23A | 177.3 (3) | C27B—C22B—C23B—C24B | 1.2 (5) |
C20A—C21A—C22A—C27A | −1.7 (5) | C28B—C19B—C20B—C21B | −2.0 (5) |
C21A—C22A—C23A—C24A | −178.8 (3) | C29B—C30B—C31B—C32B | −0.4 (5) |
C21A—C22A—C27A—C26A | 179.0 (3) | C30B—C29B—C38B—C37B | −1.1 (5) |
C21A—C22A—C27A—C28A | 0.5 (4) | C30B—C31B—C32B—C33B | 179.5 (3) |
C22A—C23A—C24A—C25A | −0.3 (6) | C30B—C31B—C32B—C37B | −1.0 (5) |
C22A—C27A—C28A—C19A | 1.5 (4) | C31B—C32B—C33B—C34B | 178.9 (3) |
C23A—C22A—C27A—C26A | 0.0 (5) | C31B—C32B—C37B—C36B | −179.1 (3) |
C23A—C22A—C27A—C28A | −178.5 (3) | C31B—C32B—C37B—C38B | 1.3 (5) |
C23A—C24A—C25A—C26A | 0.2 (7) | C32B—C33B—C34B—C35B | 0.5 (6) |
C24A—C25A—C26A—C27A | −0.1 (6) | C32B—C37B—C38B—C29B | −0.3 (5) |
C25A—C26A—C27A—C22A | −0.1 (5) | C33B—C32B—C37B—C36B | 0.4 (5) |
C25A—C26A—C27A—C28A | 178.4 (4) | C33B—C32B—C37B—C38B | −179.1 (3) |
C26A—C27A—C28A—C19A | −177.1 (3) | C33B—C34B—C35B—C36B | −0.2 (6) |
C27A—C22A—C23A—C24A | 0.1 (5) | C34B—C35B—C36B—C37B | −0.1 (6) |
C28A—C19A—C20A—C21A | 1.1 (5) | C35B—C36B—C37B—C32B | −0.1 (5) |
C29A—C30A—C31A—C32A | −0.7 (5) | C35B—C36B—C37B—C38B | 179.5 (3) |
C30A—C29A—C38A—C37A | −1.0 (5) | C36B—C37B—C38B—C29B | −179.8 (3) |
C30A—C31A—C32A—C33A | −179.8 (3) | C37B—C32B—C33B—C34B | −0.7 (5) |
C30A—C31A—C32A—C37A | 0.8 (5) | C38B—C29B—C30B—C31B | 1.5 (5) |
C31A—C32A—C33A—C34A | −178.3 (3) | C39B—C5B—C6B—Fe1B | −119.3 (3) |
C31A—C32A—C37A—C36A | 178.6 (3) | C39B—C5B—C6B—C7B | 179.3 (3) |
C31A—C32A—C37A—C38A | −0.9 (4) | C39B—C5B—C6B—C45B | 11.7 (5) |
C32A—C33A—C34A—C35A | −0.5 (6) | C39B—C40B—C41B—C42B | 1.5 (6) |
C32A—C37A—C38A—C29A | 1.0 (4) | C40B—C39B—C44B—C43B | 1.5 (5) |
C33A—C32A—C37A—C36A | −0.9 (5) | C40B—C41B—C42B—C43B | −0.7 (7) |
C33A—C32A—C37A—C38A | 179.6 (3) | C41B—C42B—C43B—C44B | 0.3 (6) |
C33A—C34A—C35A—C36A | −0.5 (6) | C42B—C43B—C44B—C39B | −0.8 (6) |
C34A—C35A—C36A—C37A | 0.8 (6) | C44B—C39B—C40B—C41B | −1.9 (5) |
C35A—C36A—C37A—C32A | −0.1 (5) | C45B—C6B—C7B—Fe1B | −129.3 (3) |
C35A—C36A—C37A—C38A | 179.4 (3) | C45B—C6B—C7B—C8B | 168.9 (2) |
C36A—C37A—C38A—C29A | −178.5 (3) | C45B—C6B—C7B—C51B | −1.7 (4) |
C37A—C32A—C33A—C34A | 1.2 (5) | C45B—C46B—C47B—C48B | 0.1 (5) |
C38A—C29A—C30A—C31A | 0.8 (5) | C46B—C45B—C50B—C49B | 0.0 (5) |
C39A—C5A—C6A—Fe1A | −125.3 (3) | C46B—C47B—C48B—C49B | −0.9 (5) |
C39A—C5A—C6A—C7A | 174.0 (2) | C47B—C48B—C49B—C50B | 1.3 (5) |
C39A—C5A—C6A—C45A | 5.5 (4) | C48B—C49B—C50B—C45B | −0.9 (5) |
C39A—C40A—C41A—C42A | −0.5 (5) | C50B—C45B—C46B—C47B | 0.4 (4) |
C40A—C39A—C44A—C43A | −0.6 (4) | C51B—C7B—C8B—Fe1B | −130.0 (3) |
C40A—C41A—C42A—C43A | 0.0 (5) | C51B—C7B—C8B—C4B | 159.7 (3) |
C41A—C42A—C43A—C44A | 0.2 (5) | C51B—C7B—C8B—C57B | −4.3 (4) |
C42A—C43A—C44A—C39A | 0.1 (5) | C51B—C52B—C53B—C54B | 1.9 (5) |
C44A—C39A—C40A—C41A | 0.8 (4) | C52B—C51B—C56B—C55B | −2.8 (4) |
C45A—C6A—C7A—Fe1A | −128.7 (3) | C52B—C53B—C54B—C55B | −2.1 (5) |
C45A—C6A—C7A—C8A | 168.2 (2) | C53B—C54B—C55B—C56B | −0.1 (5) |
C45A—C6A—C7A—C51A | 0.9 (4) | C54B—C55B—C56B—C51B | 2.6 (5) |
C45A—C46A—C47A—C48A | −1.0 (5) | C56B—C51B—C52B—C53B | 0.6 (4) |
C46A—C45A—C50A—C49A | −0.3 (4) | C57B—C58B—C59B—C60B | −1.3 (5) |
C46A—C47A—C48A—C49A | 0.0 (5) | C58B—C57B—C62B—C61B | −1.7 (4) |
C47A—C48A—C49A—C50A | 0.8 (5) | C58B—C59B—C60B—C61B | −0.7 (5) |
C48A—C49A—C50A—C45A | −0.7 (5) | C59B—C60B—C61B—C62B | 1.5 (5) |
C50A—C45A—C46A—C47A | 1.2 (4) | C60B—C61B—C62B—C57B | −0.3 (5) |
C51A—C7A—C8A—Fe1A | −131.8 (3) | C62B—C57B—C58B—C59B | 2.5 (5) |
C51A—C7A—C8A—C4A | 158.9 (3) | C29C—C38C—C37C—C36C | 179 (2) |
C51A—C7A—C8A—C57A | −6.9 (4) | C29C—C38C—C37C—C32C | 1 (2) |
C51A—C52A—C53A—C54A | −0.3 (5) | C38C—C29C—C30C—C31C | 4 (4) |
C52A—C51A—C56A—C55A | −3.2 (4) | C38C—C37C—C36C—C35C | −180 (2) |
C52A—C53A—C54A—C55A | −1.2 (5) | C38C—C37C—C32C—C33C | −178 (3) |
C53A—C54A—C55A—C56A | 0.5 (5) | C38C—C37C—C32C—C31C | −2 (4) |
C54A—C55A—C56A—C51A | 1.7 (5) | C37C—C36C—C35C—C34C | 2 (4) |
C56A—C51A—C52A—C53A | 2.5 (4) | C37C—C32C—C31C—C30C | 4 (5) |
C57A—C58A—C59A—C60A | 0.3 (5) | C36C—C37C—C32C—C33C | 3 (5) |
C58A—C57A—C62A—C61A | −0.8 (4) | C36C—C37C—C32C—C31C | 179 (3) |
C58A—C59A—C60A—C61A | −0.5 (5) | C36C—C35C—C34C—C33C | −5 (5) |
C59A—C60A—C61A—C62A | 0.1 (5) | C35C—C34C—C33C—C32C | 7 (5) |
C60A—C61A—C62A—C57A | 0.6 (5) | C34C—C33C—C32C—C37C | −6 (5) |
C62A—C57A—C58A—C59A | 0.4 (4) | C34C—C33C—C32C—C31C | 178 (3) |
Fe1B—C4B—C5B—C6B | −62.95 (18) | C33C—C32C—C31C—C30C | −180 (3) |
Fe1B—C4B—C5B—C39B | 126.9 (3) | C32C—C37C—C36C—C35C | −1 (4) |
Fe1B—C4B—C8B—C7B | 62.52 (18) | C32C—C31C—C30C—C29C | −5 (5) |
Fe1B—C4B—C8B—C57B | −133.5 (3) | C30C—C29C—C38C—C37C | −1 (3) |
Fe1B—C5B—C6B—C7B | −61.40 (18) | C19C—C20C—C21C—C22C | −1 (4) |
Fe1B—C5B—C6B—C45B | 131.1 (3) | C27C—C22C—C23C—C24C | 3 (5) |
Fe1B—C5B—C39B—C40B | −122.1 (3) | C25C—C24C—C23C—C22C | −3 (4) |
Fe1B—C5B—C39B—C44B | 57.8 (4) | C20C—C19C—C28C—C27C | −1 (4) |
Fe1B—C6B—C7B—C8B | −61.83 (18) | C20C—C21C—C22C—C27C | 1 (4) |
Fe1B—C6B—C7B—C51B | 127.5 (3) | C20C—C21C—C22C—C23C | −178 (3) |
Fe1B—C6B—C45B—C46B | 16.0 (4) | C24C—C25C—C26C—C27C | 1 (3) |
Fe1B—C6B—C45B—C50B | −159.4 (2) | C21C—C22C—C23C—C24C | −178 (3) |
Fe1B—C7B—C8B—C4B | −70.24 (19) | C26C—C27C—C22C—C21C | 180 (2) |
Fe1B—C7B—C8B—C57B | 125.7 (3) | C26C—C27C—C22C—C23C | −1 (4) |
Fe1B—C7B—C51B—C52B | −142.0 (2) | C26C—C27C—C28C—C19C | 180 (2) |
Fe1B—C7B—C51B—C56B | 44.9 (4) | C26C—C25C—C24C—C23C | 1 (2) |
Fe1B—C8B—C57B—C58B | −149.9 (2) | C22C—C27C—C26C—C25C | −1 (4) |
Fe1B—C8B—C57B—C62B | 36.1 (4) | C22C—C27C—C28C—C19C | 1 (4) |
O1B—C4B—C5B—Fe1B | −127.7 (3) | C28C—C19C—C20C—C21C | 0 (4) |
O1B—C4B—C5B—C6B | 169.3 (3) | C28C—C27C—C26C—C25C | 180 (2) |
O1B—C4B—C5B—C39B | −0.8 (5) | C28C—C27C—C22C—C21C | −1 (4) |
O1B—C4B—C8B—Fe1B | 128.3 (3) | C28C—C27C—C22C—C23C | 178 (3) |
X | C4 | C5/C8 | C6/C7 |
O | 170.0 / 181.4 | 82.7 / 71.9 | 104.2 / 111.1 |
NCH2Ts | n/a / 178.3 | 79.5 / 66.7 | 99.1 / 105.5 |
N-2-Naphth | 165.3 / 178.2 | 78.5 / 66.6 | 98.8 / 104.8 |
N-2,6-DMP | 165.9 / n/a | 77.4 / 65.7 | 98.8 / 104.3 |
NCH2Ph | 163.6 / n/a | 76.0 / 63.9 | 96.6 / 102.3 |
NBu | 163.3 / n/a | 74.8 / 61.6 | 96.1 / 101.0 |
NtBu | 161.8 / 175.0 | 75.1 / 62.2 | 95.6 / 100.7 |
All spectra recorded in CDCl3. Spectra were referenced to the solvent signal at 77.16 ppm (Fulmer et al., 2010). 13C NMR data for Fe(CO)3-BTTHI were obtained from the literature (Moulin et al., 2013). |
Acknowledgements
X-ray services were provided by SMoCC – The Small Molecule Crystallography Center of ETH Zurich. The authors thank Nils Trapp and Michael Solar for the measurements and determination of the crystal structures shown in this work.
Funding information
Funding for this research was provided by: NCCR Catalysis (grant No. 180544); ETH Zürich.
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