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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 79| Part 7| July 2023| Pages 626-632
https://doi.org/10.1107/S205698902300498X

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

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André Bütikofera and Peter Chena*

aDepartment of Chemistry and Applied Biosciences, Laboratory of Organic Chemistry, ETH Zurich, Zurich 8093, Switzerland
*Correspondence e-mail: peter.chen@org.chem.ethz.ch

Edited by J. T. Mague, Tulane University, USA (Received 15 May 2023; accepted 6 June 2023; online 13 June 2023)

Irradiation of a toluene solution containing cyclo­penta­dienone tricarbonyl iron complexes and isocyanides with blue LEDs afforded the formation and isolation of 12 triisocyanide complexes, two of which, namely tris­(2,6-di­methyl­phenyl isocyanide)(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.

CCDC references: 2248733; 2260413

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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[Quintard, A. & Rodriguez, J. (2014). Angew. Chem. Int. Ed. 53, 4044-4055.]; Pignataro & Gennari, 2020[Pignataro, L. & Gennari, C. (2020). Eur. J. Org. Chem. 2020, 3192-3205.]), 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[Pruchnik, F. P. & Duraj, S. A. (1990). Organometallic Chemistry of the Transition Elements, edited by F. P. Pruchnik and S. A. Duraj, pp. 617-645. New York: Springer US.]), 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[Knölker, H.-J., Goesmann, H. & Klauss, R. (1999). Angew. Chem. Int. Ed. 38, 702-705.]), 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[link]). 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.

[Scheme 1]
[Figure 1]
Figure 1
Synthetic route to access cyclo­penta­dienone triisocyanide complexes starting from the corresponding tricarbonyl complexes by irradiation with blue LEDs.

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[Gupta, H. K., Rampersad, N., Stradiotto, M. & McGlinchey, M. J. (2000). Organometallics, 19, 184-191.]; CCDC deposition number 142285).

Fe(CN-2,6-DMP)3-TPCPD (Fig. 2[link]) crystallizes in the Pca21 space group and features one complex mol­ecule per asymmetric unit 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[link] and 4[link]) crystallizes in the P21 space group and features two complex mol­ecules and a co-crystallized acetone mol­ecule in the asymmetric unit. 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 crystal structure 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 oxidation state. The cyclo­penta­dienone ligand is coordinated in an η4 fashion.

[Figure 2]
Figure 2
Crystal structure of Fe(CN-2,6-DMP)3-TPCPD. Displacement ellipsoids are shown at the 50% probability level. Hydrogen atoms are not shown for clarity.
[Figure 3]
Figure 3
Crystal structure of Fe(CN-2-Naphth)3-TPCPD. Displacement ellipsoids are shown at the 50% probability level. The second complex in the asymmetric unit, hydrogen atoms and the co-crystallized acetone mol­ecule are not shown for clarity.
[Figure 4]
Figure 4
The two independent Fe(CN-2-Naphth)3-TPCPD mol­ecules in the asymmetric unit viewed along the Fe–Fe axis. In the crystal, the mol­ecules appear in pairs that are rotated by 180° with respect to each other and show an inter­locked arrangement of the naphthyl groups.

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 asymmetric unit 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[link] 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 isocyanides 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).

Table 1
13C NMR chemical shifts (in p.p.m.) for the cyclo­penta­dienone ring carbon atoms (C4, C5, C6, C7, C8) (TPCPD / BTTHI)

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 p.p.m. (Fulmer et al., 2010[Fulmer, G. R., Miller, A. J. M., Sherden, N. H., Gottlieb, H. E., Nudelman, A., Stoltz, B. M., Bercaw, J. E. & Goldberg, K. I. (2010). Organometallics, 29, 2176-2179.]). 13C NMR data for Fe(CO)3-BTTHI were obtained from the literature (Moulin et al., 2013[Moulin, S., Dentel, H., Pagnoux-Ozherelyeva, A., Gaillard, S., Poater, A., Cavallo, L., Lohier, J.-F. & Renaud, J. L. (2013). Chem. Eur. J. 19, 17881-17890.]).

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[Pruchnik, F. P. & Duraj, S. A. (1990). Organometallic Chemistry of the Transition Elements, edited by F. P. Pruchnik and S. A. Duraj, pp. 617-645. New York: Springer US.]). 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[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]), three structures featuring an iron triisocyanide moiety with the iron center in the 0 oxidation state were found in which the iron is bound to a diene (Fig. 5[link]). 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[Bassett, J.-M., Green, M., Howard, J. A. K. & Stone, F. G. A. (1978). J. Chem. Soc. Chem. Commun. pp. 1000-1001.], CCDC deposition number 1107207; Bassett et al., 1980[Bassett, J.-M., Green, M., Howard, J. A. K. & Stone, F. G. A. (1980). J. Chem. Soc. Dalton Trans. pp. 1779-1788.], 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[Sunada, Y., Noda, D., Soejima, H., Tsutsumi, H. & Nagashima, H. (2015). Organometallics, 34, 2896-2906.], 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[Bassett, J.-M., Barker, G. K., Green, M., Howard, J. A. K., Stone, F. G. A. & Wolsey, W. C. (1981). J. Chem. Soc. Dalton Trans. pp. 219-227.]), but not crystallographically characterized. Brennessel and Ellis reported the structure of Fe(η4-anthracene)(CN-2,6-DMP)3 (Brennessel & Ellis, 2022[Brennessel, W. W. & Ellis, J. E. (2022). Acta Cryst. E78, 60-65.], 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.

[Figure 5]
Figure 5
Crystallographically characterized Fe0 triisocyanide diene complexes reported in the CSD.

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 packed column and purified by column chromatography using the appropriate eluent as indicated below. The relevant, yellow-colored fractions were combined and concentrated under reduced pressure. For complexes bearing the TPCPD ligands with electron-rich isocyanides (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 chromatography (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 saturated solution, filtering off the solids and storing the saturated solution 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[Moulin, S., Dentel, H., Pagnoux-Ozherelyeva, A., Gaillard, S., Poater, A., Cavallo, L., Lohier, J.-F. & Renaud, J. L. (2013). Chem. Eur. J. 19, 17881-17890.]; Liang, 2019[Liang, Y. (2019). Spectrochim. Acta A Mol. Biomol. Spectrosc. 216, 395-403.]).

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 eluent 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 refinement details are summarized in Table 2[link]. 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.

Table 2
Experimental details

  Fe(CN-2,6-DMP)3-TPCPD Fe(CN-2-Naphth)3-TPCPD
Crystal data
Chemical formula [Fe(C9H9N)3(C29H20O)] [Fe(C11H7N)3(C29H20O)]2·C3H6O
Mr 833.81 1857.73
Crystal system, space group Orthorhombic, Pca21 Monoclinic, P21
Temperature (K) 100 100
a, b, c (Å) 16.7473 (3), 12.1998 (2), 20.9668 (4) 15.2471 (1), 19.8604 (1), 15.5785 (1)
α, β, γ (°) 90, 90, 90 90, 99.378 (1), 90
V (Å3) 4283.81 (13) 4654.33 (5)
Z 4 2
Radiation type Cu Kα Cu Kα
μ (mm−1) 3.16 2.98
Crystal size (mm) 0.14 × 0.03 × 0.02 0.18 × 0.07 × 0.05
 
Data collection
Diffractometer XtaLAB Synergy, Dualflex, Pilatus 300K XtaLAB Synergy, Dualflex, Pilatus 300K
Absorption correction Gaussian (CrysAlis PRO; Rigaku OD, 2021[Rigaku OD (2021). CrysAlis PRO version 1.171.41.119a. Rigaku Oxford Diffraction Ltd, Yarnton, England.]) Gaussian (CrysAlis PRO; Rigaku OD, 2021[Rigaku OD (2021). CrysAlis PRO version 1.171.41.119a. Rigaku Oxford Diffraction Ltd, Yarnton, England.])
Tmin, Tmax 0.697, 1.000 0.779, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 33622, 7440, 6449 89473, 18788, 17761
Rint 0.081 0.050
(sin θ/λ)max (Å−1) 0.639 0.636
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.109, 1.05 0.036, 0.100, 1.07
No. of reflections 7440 18788
No. of parameters 556 1390
No. of restraints 1 1606
H-atom treatment H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.36, −0.40 0.28, −0.37
Absolute structure Flack x determined using 1989 quotients [(I+)-(I−)]/[(I+)+(I−)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.]) Classical Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]) method preferred over Parsons because s.u. lower
Absolute structure parameter −0.008 (4) −0.004 (2)
Computer programs: CrysAlis PRO (Rigaku OD, 2021[Rigaku OD (2021). CrysAlis PRO version 1.171.41.119a. Rigaku Oxford Diffraction Ltd, Yarnton, England.], 2022[Rigaku OD (2022). CrysAlis PRO version 1.171.42.79a. Rigaku Oxford Diffraction Ltd, Yarnton, England.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018/3 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and Mercury (Macrae et al., 2020[Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226-235.]).

Supporting information

CCDC references: 2248733; 2260413

Crystal structure: contains datablocks I, twin. DOI: https://doi.org/10.1107/S205698902300498X/mw2197sup1.cif

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

checkCIF report


Computing details top

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 refinement: 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).

Tris(2,6-dimethylphenyl isocyanide)(η4-tetraphenylcyclopentadienone)iron (I) top
Crystal data top
[Fe(C9H9N)3(C29H20O)]Dx = 1.293 Mg m−3
Mr = 833.81Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pca21Cell parameters from 11706 reflections
a = 16.7473 (3) Åθ = 3.6–79.3°
b = 12.1998 (2) ŵ = 3.16 mm−1
c = 20.9668 (4) ÅT = 100 K
V = 4283.81 (13) Å3Needle, clear yellow
Z = 40.14 × 0.03 × 0.02 mm
F(000) = 1752
Data collection top
XtaLAB Synergy, Dualflex, Pilatus 300K
diffractometer		7440 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source6449 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.081
Detector resolution: 5.8140 pixels mm-1θmax = 80.1°, θmin = 3.6°
ω scansh = −21→20
Absorption correction: gaussian
(CrysAlisPro; Rigaku OD, 2021)		k = −15→15
Tmin = 0.697, Tmax = 1.000l = −26→21
33622 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.05Δρmax = 0.36 e Å−3
7440 reflectionsΔρmin = −0.40 e Å−3
556 parametersAbsolute structure: Flack x determined using 1989 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: −0.008 (4)
Primary atom site location: dual
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.44212 (3)0.29727 (4)0.49025 (3)0.01969 (13)
O10.34098 (16)0.1785 (2)0.37047 (13)0.0247 (6)
N10.5466 (2)0.2208 (3)0.38217 (18)0.0258 (7)
N20.5401 (2)0.2204 (3)0.60128 (19)0.0278 (7)
N30.51844 (17)0.5183 (2)0.48677 (19)0.0255 (6)
C10.5072 (2)0.2484 (3)0.4249 (2)0.0259 (9)
C20.5031 (2)0.2504 (3)0.55733 (19)0.0241 (8)
C30.4886 (2)0.4325 (3)0.4898 (2)0.0240 (7)
C40.3418 (2)0.2250 (3)0.4232 (2)0.0219 (8)
C50.35340 (18)0.1724 (2)0.4859 (2)0.0210 (6)
C60.3355 (2)0.2502 (3)0.53539 (19)0.0199 (7)
C70.3282 (2)0.3565 (3)0.50543 (18)0.0208 (7)
C80.3381 (2)0.3442 (3)0.43788 (18)0.0211 (7)
C90.3600 (2)0.0516 (2)0.4933 (2)0.0233 (7)
C100.4154 (2)−0.0087 (3)0.4587 (2)0.0270 (8)
H100.4511130.0282060.4308560.032*
C110.4194 (3)−0.1221 (3)0.4642 (2)0.0337 (9)
H110.457570−0.1619580.4399270.040*
C120.3681 (3)−0.1774 (3)0.5049 (2)0.0356 (10)
H120.371492−0.2547480.5092680.043*
C130.3116 (3)−0.1186 (3)0.5392 (2)0.0334 (9)
H130.275669−0.1559500.5667110.040*
C140.3076 (3)−0.0055 (3)0.5335 (2)0.0297 (8)
H140.2686730.0339510.5571360.036*
C150.3175 (2)0.2258 (3)0.6031 (2)0.0224 (7)
C160.3635 (2)0.1555 (3)0.64050 (19)0.0250 (8)
H160.4100740.1229670.6228580.030*
C170.3424 (2)0.1321 (3)0.7032 (2)0.0289 (8)
H170.3755560.0860790.7283070.035*
C180.2733 (2)0.1755 (3)0.7291 (2)0.0286 (8)
H180.2589420.1594920.7719600.034*
C190.2253 (2)0.2427 (3)0.6918 (2)0.0284 (8)
H190.1768290.2706890.7088020.034*
C200.2475 (2)0.2692 (3)0.62986 (19)0.0241 (8)
H200.2149700.3171010.6053630.029*
C210.3020 (2)0.4560 (3)0.54132 (19)0.0229 (7)
C220.3432 (2)0.4931 (3)0.59502 (19)0.0263 (8)
H220.3922990.4597120.6065790.032*
C230.3130 (3)0.5785 (3)0.6317 (2)0.0296 (8)
H230.3413590.6028880.6683320.036*
C240.2411 (3)0.6282 (3)0.6147 (2)0.0323 (9)
H240.2195400.6853300.6402860.039*
C250.2011 (2)0.5939 (3)0.5604 (2)0.0314 (9)
H250.1530370.6292110.5479340.038*
C260.2311 (2)0.5081 (3)0.5241 (2)0.0269 (8)
H260.2030410.4847110.4871020.032*
C270.3286 (2)0.4318 (3)0.38982 (19)0.0241 (8)
C280.3420 (2)0.5434 (3)0.4046 (2)0.0281 (8)
H280.3633070.5624700.4451120.034*
C290.3246 (3)0.6253 (3)0.3611 (2)0.0308 (9)
H290.3323590.6999030.3724560.037*
C300.2959 (3)0.5993 (3)0.3011 (2)0.0381 (10)
H300.2836630.6556620.2714010.046*
C310.2851 (3)0.4899 (3)0.2846 (2)0.0352 (9)
H310.2666270.4713710.2431560.042*
C320.3011 (2)0.4076 (3)0.3285 (2)0.0272 (8)
H320.2932960.3332630.3165400.033*
C330.5933 (2)0.1901 (3)0.33020 (19)0.0245 (8)
C340.5665 (2)0.2148 (3)0.2688 (2)0.0278 (9)
C350.4882 (3)0.2716 (4)0.2592 (2)0.0394 (10)
H35A0.4469000.2347300.2843610.059*
H35B0.4737430.2692840.2139200.059*
H35C0.4927660.3481390.2729940.059*
C360.6154 (3)0.1832 (3)0.2180 (2)0.0363 (10)
H360.5989490.1971160.1754380.044*
C370.6878 (3)0.1316 (3)0.2294 (2)0.0406 (11)
H370.7210160.1120630.1944360.049*
C380.7122 (3)0.1085 (3)0.2905 (2)0.0370 (10)
H380.7618450.0725810.2971360.044*
C390.6658 (2)0.1366 (3)0.3426 (2)0.0298 (9)
C400.6909 (3)0.1127 (4)0.4099 (3)0.0440 (11)
H40A0.6977590.1818280.4331630.066*
H40B0.7415840.0725100.4096160.066*
H40C0.6499000.0683510.4309900.066*
C410.5568 (2)0.1777 (3)0.6620 (2)0.0263 (8)
C420.5805 (2)0.0682 (3)0.6658 (2)0.0293 (8)
C430.5935 (3)0.0009 (3)0.6074 (3)0.0432 (11)
H43A0.541778−0.0214910.5898240.065*
H43B0.624754−0.0643520.6183050.065*
H43C0.6224910.0443470.5756180.065*
C440.5888 (3)0.0228 (4)0.7264 (3)0.0397 (11)
H440.604670−0.0515530.7307850.048*
C450.5742 (3)0.0855 (5)0.7802 (3)0.0460 (12)
H450.5791160.0533270.8213130.055*
C460.5524 (3)0.1944 (4)0.7748 (3)0.0452 (12)
H460.5431250.2363640.8122170.054*
C470.5439 (3)0.2434 (4)0.7156 (2)0.0352 (10)
C480.5181 (4)0.3609 (4)0.7074 (3)0.0601 (16)
H48A0.5490300.3945990.6728760.090*
H48B0.5274500.4011220.7471350.090*
H48C0.4611750.3632980.6967450.090*
C490.5590 (2)0.6118 (3)0.46513 (19)0.0251 (8)
C500.5748 (2)0.6956 (3)0.5084 (2)0.0272 (8)
C510.5468 (3)0.6862 (3)0.5761 (2)0.0335 (9)
H51A0.4884920.6795050.5768120.050*
H51B0.5628720.7517320.5998330.050*
H51C0.5707280.6211850.5957760.050*
C520.6185 (2)0.7852 (3)0.4862 (3)0.0323 (8)
H520.6321420.8426960.5147170.039*
C530.6423 (2)0.7911 (3)0.4229 (2)0.0330 (9)
H530.6707570.8535580.4082350.040*
C540.6251 (2)0.7071 (3)0.3812 (2)0.0331 (9)
H540.6417410.7127190.3380440.040*
C550.5837 (2)0.6142 (3)0.4012 (2)0.0309 (9)
C560.5695 (3)0.5184 (4)0.3583 (2)0.0438 (11)
H56A0.5963220.4536300.3758090.066*
H56B0.5907470.5343550.3158120.066*
H56C0.5119800.5042440.3553150.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0222 (2)0.0168 (2)0.0200 (3)−0.00091 (18)0.0003 (3)0.0004 (2)
O10.0310 (14)0.0216 (11)0.0215 (15)0.0005 (10)−0.0023 (11)−0.0012 (10)
N10.0261 (17)0.0258 (15)0.026 (2)−0.0001 (12)0.0045 (14)−0.0020 (13)
N20.0252 (16)0.0279 (15)0.030 (2)−0.0020 (13)−0.0012 (15)0.0070 (15)
N30.0288 (14)0.0203 (12)0.0273 (16)−0.0042 (10)−0.0006 (15)0.0011 (14)
C10.0249 (19)0.0188 (15)0.034 (3)−0.0028 (14)−0.0081 (18)0.0025 (15)
C20.0270 (19)0.0181 (15)0.027 (2)−0.0033 (13)−0.0001 (17)−0.0010 (14)
C30.0262 (16)0.0259 (15)0.0197 (18)0.0019 (12)−0.0009 (17)0.0007 (16)
C40.0197 (17)0.0207 (15)0.025 (2)−0.0003 (13)−0.0009 (15)−0.0027 (14)
C50.0188 (14)0.0172 (13)0.0270 (19)−0.0026 (10)0.0010 (17)−0.0038 (16)
C60.0177 (16)0.0190 (14)0.023 (2)−0.0017 (12)0.0010 (14)0.0010 (14)
C70.0219 (16)0.0192 (14)0.021 (2)0.0002 (12)−0.0009 (13)−0.0009 (13)
C80.0195 (17)0.0179 (15)0.026 (2)0.0014 (12)−0.0052 (14)0.0002 (14)
C90.0290 (16)0.0202 (14)0.0206 (19)−0.0010 (12)−0.0047 (17)−0.0004 (16)
C100.0296 (19)0.0218 (16)0.030 (2)−0.0014 (14)−0.0023 (16)−0.0044 (15)
C110.041 (2)0.0235 (17)0.037 (2)0.0063 (15)−0.0090 (18)−0.0079 (16)
C120.053 (3)0.0182 (15)0.035 (3)0.0018 (16)−0.0157 (19)0.0020 (15)
C130.053 (3)0.0231 (16)0.024 (2)−0.0080 (17)−0.0036 (19)0.0026 (16)
C140.039 (2)0.0248 (17)0.026 (2)−0.0059 (15)0.0000 (17)−0.0030 (15)
C150.0235 (17)0.0185 (14)0.025 (2)−0.0040 (12)−0.0021 (16)−0.0019 (14)
C160.0270 (18)0.0222 (15)0.026 (2)−0.0022 (13)0.0007 (15)0.0008 (14)
C170.035 (2)0.0249 (16)0.027 (2)−0.0061 (15)−0.0033 (16)0.0035 (15)
C180.038 (2)0.0278 (17)0.020 (2)−0.0089 (15)0.0047 (17)−0.0019 (15)
C190.0304 (19)0.0258 (17)0.029 (2)−0.0030 (15)0.0060 (16)−0.0047 (15)
C200.0244 (18)0.0217 (15)0.026 (2)−0.0017 (13)0.0018 (15)0.0004 (14)
C210.0255 (18)0.0170 (14)0.026 (2)−0.0030 (13)0.0003 (15)0.0006 (14)
C220.032 (2)0.0230 (16)0.024 (2)−0.0008 (14)0.0003 (16)0.0015 (14)
C230.044 (2)0.0198 (15)0.025 (2)−0.0057 (15)0.0055 (17)−0.0016 (15)
C240.046 (2)0.0188 (15)0.032 (2)−0.0007 (15)0.0160 (19)−0.0039 (15)
C250.031 (2)0.0255 (17)0.038 (3)0.0020 (15)0.0082 (18)0.0041 (16)
C260.0271 (18)0.0208 (15)0.033 (2)0.0017 (14)0.0005 (16)0.0017 (15)
C270.0231 (18)0.0234 (16)0.026 (2)−0.0006 (13)0.0033 (15)−0.0002 (14)
C280.034 (2)0.0219 (16)0.028 (2)0.0001 (15)0.0001 (17)0.0010 (15)
C290.045 (2)0.0189 (15)0.029 (2)0.0008 (15)−0.0017 (18)0.0030 (15)
C300.057 (3)0.0260 (18)0.032 (3)0.0050 (18)−0.005 (2)0.0089 (16)
C310.052 (3)0.0304 (18)0.023 (2)0.0019 (18)−0.005 (2)0.0032 (17)
C320.034 (2)0.0227 (16)0.025 (2)0.0029 (14)−0.0006 (16)−0.0026 (15)
C330.0279 (19)0.0210 (15)0.025 (2)−0.0031 (13)0.0051 (16)−0.0022 (14)
C340.036 (2)0.0228 (16)0.025 (2)−0.0030 (15)−0.0001 (17)−0.0035 (14)
C350.043 (3)0.039 (2)0.036 (3)0.0051 (19)−0.007 (2)0.0013 (18)
C360.052 (3)0.0286 (19)0.028 (2)−0.0115 (18)0.006 (2)−0.0041 (17)
C370.048 (3)0.031 (2)0.043 (3)−0.0051 (18)0.022 (2)−0.0098 (19)
C380.031 (2)0.0283 (18)0.051 (3)−0.0012 (16)0.009 (2)−0.0083 (18)
C390.0281 (19)0.0234 (16)0.038 (3)0.0002 (14)0.0027 (17)−0.0037 (16)
C400.043 (3)0.043 (2)0.045 (3)0.008 (2)−0.010 (2)−0.002 (2)
C410.0236 (19)0.0289 (17)0.026 (2)−0.0015 (14)−0.0038 (16)0.0023 (16)
C420.0234 (18)0.0296 (18)0.035 (2)0.0001 (14)−0.0050 (17)0.0051 (17)
C430.050 (3)0.032 (2)0.048 (3)0.0078 (18)−0.003 (2)−0.006 (2)
C440.033 (2)0.037 (2)0.049 (3)−0.0057 (17)−0.009 (2)0.016 (2)
C450.034 (2)0.075 (3)0.029 (3)−0.009 (2)−0.0069 (19)0.014 (3)
C460.038 (2)0.069 (3)0.029 (3)0.003 (2)−0.005 (2)−0.012 (2)
C470.032 (2)0.042 (2)0.032 (3)0.0019 (18)−0.0067 (19)−0.008 (2)
C480.068 (4)0.050 (3)0.062 (4)0.021 (3)−0.024 (3)−0.026 (3)
C490.0253 (17)0.0208 (16)0.029 (2)−0.0012 (13)−0.0029 (15)0.0063 (14)
C500.0263 (18)0.0222 (16)0.033 (2)0.0015 (13)−0.0022 (15)0.0013 (15)
C510.035 (2)0.0312 (19)0.034 (3)−0.0050 (16)0.0024 (18)−0.0064 (17)
C520.0310 (18)0.0212 (14)0.045 (2)−0.0027 (12)0.002 (2)−0.0024 (18)
C530.0257 (19)0.0243 (17)0.049 (3)−0.0022 (15)0.0031 (18)0.0094 (17)
C540.031 (2)0.0333 (19)0.034 (3)−0.0034 (15)0.0037 (17)0.0109 (18)
C550.033 (2)0.0288 (18)0.031 (2)−0.0020 (15)−0.0021 (17)0.0040 (16)
C560.057 (3)0.045 (2)0.029 (3)−0.012 (2)0.004 (2)−0.002 (2)
Geometric parameters (Å, º) top
Fe1—C11.850 (4)C28—C291.385 (5)
Fe1—C21.830 (4)C29—H290.9500
Fe1—C31.825 (3)C29—C301.383 (6)
Fe1—C42.361 (4)C30—H300.9500
Fe1—C52.130 (3)C30—C311.390 (6)
Fe1—C62.101 (4)C31—H310.9500
Fe1—C72.065 (3)C31—C321.387 (6)
Fe1—C82.137 (3)C32—H320.9500
O1—C41.243 (5)C33—C341.397 (6)
N1—C11.162 (6)C33—C391.403 (5)
N1—C331.392 (5)C34—C351.496 (6)
N2—C21.169 (5)C34—C361.397 (6)
N2—C411.403 (6)C35—H35A0.9800
N3—C31.162 (4)C35—H35B0.9800
N3—C491.403 (4)C35—H35C0.9800
C4—C51.475 (6)C36—H360.9500
C4—C81.487 (4)C36—C371.386 (7)
C5—C61.438 (5)C37—H370.9500
C5—C91.487 (4)C37—C381.375 (7)
C6—C71.447 (5)C38—H380.9500
C6—C151.482 (6)C38—C391.384 (6)
C7—C81.434 (6)C39—C401.501 (7)
C7—C211.494 (5)C40—H40A0.9800
C8—C271.478 (5)C40—H40B0.9800
C9—C101.388 (5)C40—H40C0.9800
C9—C141.402 (5)C41—C421.397 (5)
C10—H100.9500C41—C471.398 (6)
C10—C111.390 (5)C42—C431.490 (6)
C11—H110.9500C42—C441.392 (6)
C11—C121.387 (6)C43—H43A0.9800
C12—H120.9500C43—H43B0.9800
C12—C131.387 (6)C43—H43C0.9800
C13—H130.9500C44—H440.9500
C13—C141.387 (5)C44—C451.386 (8)
C14—H140.9500C45—H450.9500
C15—C161.393 (5)C45—C461.383 (8)
C15—C201.404 (5)C46—H460.9500
C16—H160.9500C46—C471.383 (7)
C16—C171.390 (6)C47—C481.507 (7)
C17—H170.9500C48—H48A0.9800
C17—C181.383 (6)C48—H48B0.9800
C18—H180.9500C48—H48C0.9800
C18—C191.390 (6)C49—C501.391 (5)
C19—H190.9500C49—C551.404 (6)
C19—C201.389 (6)C50—C511.498 (6)
C20—H200.9500C50—C521.396 (5)
C21—C221.396 (5)C51—H51A0.9800
C21—C261.394 (5)C51—H51B0.9800
C22—H220.9500C51—H51C0.9800
C22—C231.390 (5)C52—H520.9500
C23—H230.9500C52—C531.387 (7)
C23—C241.396 (6)C53—H530.9500
C24—H240.9500C53—C541.377 (6)
C24—C251.386 (6)C54—H540.9500
C25—H250.9500C54—C551.393 (5)
C25—C261.388 (5)C55—C561.493 (6)
C26—H260.9500C56—H56A0.9800
C27—C281.414 (5)C56—H56B0.9800
C27—C321.398 (6)C56—H56C0.9800
C28—H280.9500
C1—Fe1—C481.84 (15)C24—C25—C26120.3 (4)
C1—Fe1—C598.56 (15)C26—C25—H25119.9
C1—Fe1—C6138.28 (15)C21—C26—H26119.7
C1—Fe1—C7140.51 (16)C25—C26—C21120.6 (4)
C1—Fe1—C8100.74 (16)C25—C26—H26119.7
C2—Fe1—C198.02 (16)C28—C27—C8122.0 (3)
C2—Fe1—C4137.55 (14)C32—C27—C8120.7 (3)
C2—Fe1—C5101.46 (16)C32—C27—C28117.2 (3)
C2—Fe1—C692.42 (16)C27—C28—H28119.5
C2—Fe1—C7120.43 (17)C29—C28—C27121.1 (4)
C2—Fe1—C8158.98 (16)C29—C28—H28119.5
C3—Fe1—C192.11 (17)C28—C29—H29119.8
C3—Fe1—C292.78 (17)C30—C29—C28120.5 (4)
C3—Fe1—C4129.67 (15)C30—C29—H29119.8
C3—Fe1—C5160.77 (14)C29—C30—H30120.3
C3—Fe1—C6127.73 (15)C29—C30—C31119.4 (4)
C3—Fe1—C794.48 (14)C31—C30—H30120.3
C3—Fe1—C895.90 (14)C30—C31—H31119.8
C5—Fe1—C437.91 (15)C32—C31—C30120.3 (4)
C5—Fe1—C866.48 (13)C32—C31—H31119.8
C6—Fe1—C463.99 (14)C27—C32—H32119.3
C6—Fe1—C539.73 (14)C31—C32—C27121.4 (3)
C6—Fe1—C867.18 (14)C31—C32—H32119.3
C7—Fe1—C464.22 (13)N1—C33—C34118.9 (4)
C7—Fe1—C567.20 (12)N1—C33—C39117.8 (4)
C7—Fe1—C640.63 (13)C34—C33—C39123.3 (4)
C7—Fe1—C839.85 (15)C33—C34—C35120.4 (4)
C8—Fe1—C438.22 (12)C33—C34—C36117.0 (4)
C1—N1—C33178.6 (4)C36—C34—C35122.6 (4)
C2—N2—C41159.5 (4)C34—C35—H35A109.5
C3—N3—C49163.5 (4)C34—C35—H35B109.5
N1—C1—Fe1177.1 (4)C34—C35—H35C109.5
N2—C2—Fe1178.1 (4)H35A—C35—H35B109.5
N3—C3—Fe1177.1 (4)H35A—C35—H35C109.5
O1—C4—Fe1135.1 (3)H35B—C35—H35C109.5
O1—C4—C5126.5 (3)C34—C36—H36119.7
O1—C4—C8129.0 (3)C37—C36—C34120.5 (4)
C5—C4—Fe162.53 (18)C37—C36—H36119.7
C5—C4—C8104.3 (3)C36—C37—H37119.6
C8—C4—Fe162.74 (18)C38—C37—C36120.8 (4)
C4—C5—Fe179.56 (19)C38—C37—H37119.6
C4—C5—C9122.3 (3)C37—C38—H38119.4
C6—C5—Fe169.06 (18)C37—C38—C39121.2 (4)
C6—C5—C4109.2 (3)C39—C38—H38119.4
C6—C5—C9126.5 (4)C33—C39—C40120.5 (4)
C9—C5—Fe1130.8 (2)C38—C39—C33117.0 (4)
C5—C6—Fe171.21 (19)C38—C39—C40122.4 (4)
C5—C6—C7107.2 (3)C39—C40—H40A109.5
C5—C6—C15127.0 (3)C39—C40—H40B109.5
C7—C6—Fe168.35 (19)C39—C40—H40C109.5
C7—C6—C15125.4 (3)H40A—C40—H40B109.5
C15—C6—Fe1131.2 (3)H40A—C40—H40C109.5
C6—C7—Fe171.02 (19)H40B—C40—H40C109.5
C6—C7—C21122.3 (3)C42—C41—N2117.6 (4)
C8—C7—Fe172.8 (2)C42—C41—C47123.1 (4)
C8—C7—C6109.0 (3)C47—C41—N2119.1 (4)
C8—C7—C21128.1 (3)C41—C42—C43121.4 (4)
C21—C7—Fe1129.3 (2)C44—C42—C41117.5 (4)
C4—C8—Fe179.0 (2)C44—C42—C43121.1 (4)
C7—C8—Fe167.4 (2)C42—C43—H43A109.5
C7—C8—C4108.1 (3)C42—C43—H43B109.5
C7—C8—C27125.8 (3)C42—C43—H43C109.5
C27—C8—Fe1129.2 (3)H43A—C43—H43B109.5
C27—C8—C4124.8 (3)H43A—C43—H43C109.5
C10—C9—C5121.4 (3)H43B—C43—H43C109.5
C10—C9—C14118.0 (3)C42—C44—H44119.8
C14—C9—C5120.6 (3)C45—C44—C42120.4 (4)
C9—C10—H10119.4C45—C44—H44119.8
C9—C10—C11121.1 (4)C44—C45—H45119.7
C11—C10—H10119.4C46—C45—C44120.6 (5)
C10—C11—H11119.9C46—C45—H45119.7
C12—C11—C10120.3 (4)C45—C46—H46119.4
C12—C11—H11119.9C45—C46—C47121.1 (5)
C11—C12—H12120.3C47—C46—H46119.4
C11—C12—C13119.4 (3)C41—C47—C48119.8 (4)
C13—C12—H12120.3C46—C47—C41117.3 (4)
C12—C13—H13119.9C46—C47—C48122.9 (5)
C14—C13—C12120.2 (4)C47—C48—H48A109.5
C14—C13—H13119.9C47—C48—H48B109.5
C9—C14—H14119.5C47—C48—H48C109.5
C13—C14—C9121.1 (4)H48A—C48—H48B109.5
C13—C14—H14119.5H48A—C48—H48C109.5
C16—C15—C6123.4 (3)H48B—C48—H48C109.5
C16—C15—C20118.0 (4)N3—C49—C55117.9 (3)
C20—C15—C6118.4 (3)C50—C49—N3118.5 (4)
C15—C16—H16119.4C50—C49—C55123.5 (3)
C17—C16—C15121.1 (4)C49—C50—C51120.1 (3)
C17—C16—H16119.4C49—C50—C52117.2 (4)
C16—C17—H17119.8C52—C50—C51122.7 (4)
C18—C17—C16120.4 (4)C50—C51—H51A109.5
C18—C17—H17119.8C50—C51—H51B109.5
C17—C18—H18120.4C50—C51—H51C109.5
C17—C18—C19119.2 (4)H51A—C51—H51B109.5
C19—C18—H18120.4H51A—C51—H51C109.5
C18—C19—H19119.7H51B—C51—H51C109.5
C20—C19—C18120.6 (4)C50—C52—H52119.6
C20—C19—H19119.7C53—C52—C50120.7 (4)
C15—C20—H20119.7C53—C52—H52119.6
C19—C20—C15120.6 (4)C52—C53—H53119.7
C19—C20—H20119.7C54—C53—C52120.5 (4)
C22—C21—C7121.6 (3)C54—C53—H53119.7
C26—C21—C7119.3 (3)C53—C54—H54119.4
C26—C21—C22118.8 (3)C53—C54—C55121.3 (4)
C21—C22—H22119.6C55—C54—H54119.4
C23—C22—C21120.7 (4)C49—C55—C56120.8 (4)
C23—C22—H22119.6C54—C55—C49116.7 (4)
C22—C23—H23120.1C54—C55—C56122.4 (4)
C22—C23—C24119.8 (4)C55—C56—H56A109.5
C24—C23—H23120.1C55—C56—H56B109.5
C23—C24—H24120.2C55—C56—H56C109.5
C25—C24—C23119.7 (4)H56A—C56—H56B109.5
C25—C24—H24120.2H56A—C56—H56C109.5
C24—C25—H25119.9H56B—C56—H56C109.5
Fe1—C4—C5—C663.3 (2)C7—C21—C26—C25173.5 (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—C615.0 (3)
Fe1—C4—C8—C27130.5 (4)C8—C4—C5—C9179.7 (3)
Fe1—C5—C6—C759.1 (2)C8—C7—C21—C22−132.2 (4)
Fe1—C5—C6—C15−128.0 (4)C8—C7—C21—C2653.1 (5)
Fe1—C5—C9—C10−51.3 (6)C8—C27—C28—C29−173.0 (4)
Fe1—C5—C9—C14131.7 (4)C8—C27—C32—C31174.1 (4)
Fe1—C6—C7—C863.3 (2)C9—C5—C6—Fe1125.9 (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—C20135.7 (3)C9—C10—C11—C12−0.4 (6)
Fe1—C7—C8—C469.3 (2)C10—C9—C14—C130.9 (6)
Fe1—C7—C8—C27−122.9 (4)C10—C11—C12—C131.2 (6)
Fe1—C7—C21—C22−33.2 (5)C11—C12—C13—C14−1.0 (6)
Fe1—C7—C21—C26152.1 (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—C32122.9 (4)C15—C6—C7—Fe1126.0 (3)
O1—C4—C5—Fe1127.5 (4)C15—C6—C7—C8−170.7 (3)
O1—C4—C5—C6−169.2 (4)C15—C6—C7—C210.9 (5)
O1—C4—C5—C9−4.5 (5)C15—C16—C17—C182.3 (5)
O1—C4—C8—Fe1−127.4 (4)C16—C15—C20—C190.2 (5)
O1—C4—C8—C7171.0 (4)C16—C17—C18—C190.0 (5)
O1—C4—C8—C273.0 (6)C17—C18—C19—C20−2.2 (6)
N1—C33—C34—C35−1.1 (5)C18—C19—C20—C152.1 (5)
N1—C33—C34—C36179.6 (3)C20—C15—C16—C17−2.3 (5)
N1—C33—C39—C38−178.8 (3)C21—C7—C8—Fe1126.9 (4)
N1—C33—C39—C400.6 (5)C21—C7—C8—C4−163.8 (3)
N2—C41—C42—C434.5 (6)C21—C7—C8—C273.9 (6)
N2—C41—C42—C44−173.3 (4)C21—C22—C23—C24−0.3 (6)
N2—C41—C47—C46172.8 (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—C262.1 (6)
N3—C49—C50—C52177.1 (3)C24—C25—C26—C21−0.6 (6)
N3—C49—C55—C54−178.9 (4)C26—C21—C22—C231.8 (6)
N3—C49—C55—C56−2.1 (6)C27—C28—C29—C30−2.1 (6)
C2—N2—C41—C42101.2 (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—C321.5 (7)
C3—N3—C49—C552.9 (14)C30—C31—C32—C27−0.2 (7)
C4—C5—C6—Fe1−70.2 (2)C32—C27—C28—C293.3 (6)
C4—C5—C6—C7−11.1 (4)C33—C34—C36—C37−1.3 (5)
C4—C5—C6—C15161.8 (3)C34—C33—C39—C380.5 (5)
C4—C5—C9—C1053.9 (5)C34—C33—C39—C40179.9 (4)
C4—C5—C9—C14−123.1 (4)C34—C36—C37—C381.4 (6)
C4—C8—C27—C28−166.6 (3)C35—C34—C36—C37179.4 (4)
C4—C8—C27—C3217.3 (6)C36—C37—C38—C39−0.5 (6)
C5—C4—C8—Fe148.2 (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—C27178.7 (3)C39—C33—C34—C35179.7 (4)
C5—C6—C7—Fe1−60.9 (2)C39—C33—C34—C360.3 (5)
C5—C6—C7—C82.4 (4)C41—C42—C44—C45−0.2 (6)
C5—C6—C7—C21173.9 (3)C42—C41—C47—C46−2.5 (6)
C5—C6—C15—C1648.0 (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—C13178.0 (4)C44—C45—C46—C470.7 (7)
C6—C5—C9—C10−144.1 (4)C45—C46—C47—C411.1 (7)
C6—C5—C9—C1438.8 (5)C45—C46—C47—C48178.3 (5)
C6—C7—C8—Fe1−62.2 (2)C47—C41—C42—C43179.8 (4)
C6—C7—C8—C47.1 (4)C47—C41—C42—C442.1 (6)
C6—C7—C8—C27174.9 (3)C49—C50—C52—C532.3 (5)
C6—C7—C21—C2258.0 (5)C50—C49—C55—C54−0.9 (6)
C6—C7—C21—C26−116.8 (4)C50—C49—C55—C56176.0 (4)
C6—C15—C16—C17−177.6 (3)C50—C52—C53—C54−1.8 (6)
C6—C15—C20—C19175.7 (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—C2044.5 (5)C53—C54—C55—C491.4 (6)
C7—C8—C27—C2827.6 (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)
Tris(naphthalen-2-yl isocyanide)(η4-tetraphenylcyclopentadienone)iron acetone hemisolvate (twin) top
Crystal data top
[Fe(C11H7N)3(C29H20O)]2·C3H6OF(000) = 1936
Mr = 1857.73Dx = 1.326 Mg m−3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
a = 15.2471 (1) ÅCell parameters from 61660 reflections
b = 19.8604 (1) Åθ = 2.9–78.4°
c = 15.5785 (1) ŵ = 2.98 mm−1
β = 99.378 (1)°T = 100 K
V = 4654.33 (5) Å3Needle, clear colourless
Z = 20.18 × 0.07 × 0.05 mm
Data collection top
XtaLAB Synergy, Dualflex, Pilatus 300K
diffractometer		18788 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source17761 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.050
Detector resolution: 5.8140 pixels mm-1θmax = 78.8°, θmin = 2.9°
ω scansh = −19→19
Absorption correction: gaussian
(CrysAlisPro; Rigaku OD, 2021)		k = −23→24
Tmin = 0.779, Tmax = 1.000l = −19→19
89473 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.07Δρmax = 0.28 e Å−3
18788 reflectionsΔρmin = −0.37 e Å−3
1390 parametersAbsolute structure: Classical Flack (1983) method preferred over Parsons because s.u. lower
1606 restraintsAbsolute structure parameter: −0.004 (2)
Primary atom site location: dual
Special details top

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

Refinement. Twinned specimen. De-twinned HKLF4 gave best results.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Fe1A0.57957 (3)0.45750 (2)0.58041 (3)0.01517 (10)
O1A0.51344 (13)0.30215 (10)0.51440 (13)0.0201 (4)
N1A0.67302 (16)0.34102 (13)0.67723 (16)0.0224 (5)
N2A0.54485 (17)0.53463 (13)0.73647 (17)0.0243 (5)
N3A0.73794 (16)0.53525 (14)0.54475 (17)0.0235 (5)
C1A0.63882 (18)0.38791 (15)0.64210 (18)0.0182 (5)
C2A0.56081 (18)0.50575 (14)0.67578 (18)0.0188 (5)
C3A0.67717 (19)0.50556 (14)0.56222 (18)0.0191 (5)
C4A0.50553 (18)0.36441 (15)0.50618 (18)0.0194 (6)
C5A0.55382 (17)0.41021 (14)0.45526 (17)0.0172 (5)
C6A0.51530 (17)0.47630 (14)0.45515 (17)0.0170 (5)
C7A0.45269 (17)0.47642 (14)0.51526 (17)0.0172 (5)
C8A0.45225 (17)0.40968 (14)0.55248 (17)0.0172 (5)
C9A0.70183 (19)0.27731 (15)0.70810 (18)0.0199 (5)
C10A0.6534 (2)0.22088 (17)0.6712 (2)0.0241 (6)
H10A0.6046520.2263010.6252130.029*
C11A0.6779 (2)0.15860 (16)0.7027 (2)0.0248 (6)
H11A0.6461150.1202310.6779810.030*
C12A0.75027 (19)0.14989 (15)0.77214 (19)0.0217 (6)
C13A0.7735 (2)0.08573 (17)0.8091 (2)0.0304 (7)
H13A0.7405200.0471190.7869280.036*
C14A0.8428 (2)0.07900 (18)0.8762 (2)0.0339 (7)
H14A0.8568630.0358550.9009580.041*
C15A0.8936 (2)0.13552 (18)0.9090 (2)0.0282 (7)
H15A0.9420790.1302630.9552900.034*
C16A0.87303 (19)0.19785 (16)0.8741 (2)0.0234 (6)
H16A0.9081020.2355820.8957850.028*
C17A0.79993 (18)0.20695 (15)0.80594 (19)0.0190 (5)
C18A0.77404 (18)0.27145 (15)0.77292 (18)0.0195 (5)
H18A0.8062320.3103090.7953220.023*
C19A0.51160 (19)0.56466 (15)0.80555 (19)0.0209 (6)
C20A0.56227 (19)0.56089 (16)0.8899 (2)0.0231 (6)
H20A0.6191820.5401540.8987810.028*
C21A0.5283 (2)0.58748 (16)0.9583 (2)0.0247 (6)
H21A0.5622940.5857141.0151000.030*
C22A0.4429 (2)0.61767 (15)0.9458 (2)0.0236 (6)
C23A0.4047 (2)0.64311 (18)1.0168 (2)0.0328 (7)
H23A0.4372450.6407411.0742140.039*
C24A0.3217 (3)0.6709 (2)1.0030 (3)0.0431 (9)
H24A0.2967260.6875121.0508200.052*
C25A0.2729 (3)0.6750 (2)0.9187 (3)0.0473 (10)
H25A0.2153420.6946180.9100390.057*
C26A0.3074 (2)0.6511 (2)0.8482 (3)0.0369 (8)
H26A0.2736910.6541160.7914360.044*
C27A0.3935 (2)0.62181 (16)0.8609 (2)0.0243 (6)
C28A0.43005 (19)0.59519 (16)0.7902 (2)0.0237 (6)
H28A0.3982840.5984950.7325560.028*
C29A0.80196 (19)0.56989 (16)0.50659 (19)0.0217 (6)
C30A0.8045 (2)0.64098 (17)0.5122 (2)0.0258 (6)
H30A0.7656610.6645220.5435480.031*
C31A0.8643 (2)0.67528 (17)0.4715 (2)0.0291 (7)
H31A0.8660650.7230570.4743310.035*
C32A0.9232 (2)0.64074 (18)0.4254 (2)0.0272 (7)
C33A0.9860 (2)0.6753 (2)0.3829 (2)0.0396 (9)
H33A0.9900770.7229740.3865260.048*
C34A1.0404 (2)0.6406 (3)0.3372 (3)0.0486 (11)
H34A1.0815930.6642900.3088110.058*
C35A1.0356 (2)0.5696 (3)0.3317 (3)0.0463 (10)
H35A1.0733810.5459340.2993030.056*
C36A0.9775 (2)0.5352 (2)0.3725 (2)0.0351 (8)
H36A0.9755690.4874240.3688360.042*
C37A0.91958 (19)0.56911 (18)0.42043 (19)0.0246 (6)
C38A0.85803 (19)0.53476 (16)0.4627 (2)0.0233 (6)
H38A0.8553820.4869810.4608080.028*
C39A0.61525 (18)0.38679 (15)0.39642 (18)0.0193 (5)
C40A0.67738 (18)0.42953 (15)0.36753 (19)0.0207 (6)
H40A0.6838020.4743570.3889000.025*
C41A0.7300 (2)0.40735 (17)0.3079 (2)0.0259 (6)
H41A0.7714360.4372200.2887560.031*
C42A0.7221 (2)0.34175 (18)0.2764 (2)0.0285 (7)
H42A0.7579370.3265600.2357120.034*
C43A0.6613 (2)0.29889 (17)0.3051 (2)0.0284 (7)
H43A0.6556010.2539430.2840340.034*
C44A0.6086 (2)0.32084 (16)0.3642 (2)0.0235 (6)
H44A0.5673070.2906590.3831780.028*
C45A0.52444 (18)0.53034 (15)0.39123 (19)0.0198 (5)
C46A0.55581 (19)0.59498 (16)0.4140 (2)0.0230 (6)
H46A0.5741760.6059520.4735550.028*
C47A0.5606 (2)0.64365 (17)0.3505 (2)0.0287 (7)
H47A0.5811060.6877170.3667640.034*
C48A0.5352 (2)0.62750 (18)0.2634 (2)0.0307 (7)
H48A0.5383390.6605220.2199180.037*
C49A0.5052 (2)0.56322 (18)0.2398 (2)0.0279 (6)
H49A0.4885490.5521400.1800530.033*
C50A0.49930 (19)0.51486 (16)0.30310 (19)0.0224 (6)
H50A0.4780800.4710390.2863930.027*
C51A0.38688 (18)0.53063 (15)0.52111 (18)0.0182 (5)
C52A0.29681 (19)0.51478 (16)0.49939 (19)0.0217 (6)
H52A0.2794000.4694550.4867760.026*
C53A0.2320 (2)0.56482 (18)0.4960 (2)0.0272 (6)
H53A0.1709420.5534250.4808240.033*
C54A0.2565 (2)0.63095 (18)0.5147 (2)0.0303 (7)
H54A0.2125410.6651450.5113390.036*
C55A0.3452 (2)0.64695 (16)0.5382 (2)0.0280 (7)
H55A0.3621330.6922800.5515160.034*
C56A0.4103 (2)0.59708 (15)0.54263 (19)0.0224 (6)
H56A0.4710290.6085170.5604550.027*
C57A0.39119 (18)0.38613 (15)0.61099 (18)0.0190 (5)
C58A0.35409 (19)0.32133 (15)0.5997 (2)0.0221 (6)
H58A0.3708760.2922620.5567500.026*
C59A0.2930 (2)0.29936 (17)0.6509 (2)0.0277 (7)
H59A0.2686510.2553340.6427810.033*
C60A0.2672 (2)0.34098 (18)0.7136 (2)0.0287 (7)
H60A0.2251220.3259090.7480650.034*
C61A0.3038 (2)0.40517 (18)0.7255 (2)0.0265 (6)
H61A0.2865210.4340070.7685000.032*
C62A0.36511 (19)0.42737 (16)0.67538 (19)0.0216 (6)
H62A0.3898560.4711770.6847330.026*
Fe1B0.83999 (3)0.48533 (2)0.86648 (3)0.01583 (10)
O1B0.92081 (13)0.63902 (11)0.92958 (13)0.0213 (4)
N1B0.74010 (16)0.60604 (13)0.78767 (17)0.0225 (5)
N2B0.68892 (17)0.39653 (13)0.89964 (18)0.0250 (5)
N3B0.85773 (17)0.43202 (14)0.69046 (16)0.0239 (5)
C1B0.77407 (17)0.55748 (15)0.81883 (18)0.0188 (5)
C2B0.74839 (19)0.43019 (15)0.88633 (18)0.0196 (5)
C3B0.84823 (17)0.45049 (15)0.75983 (18)0.0198 (5)
C4B0.92462 (18)0.57659 (15)0.93463 (18)0.0194 (6)
C5B0.96763 (17)0.52974 (15)0.88028 (18)0.0184 (5)
C6B0.97052 (17)0.46366 (15)0.91895 (17)0.0186 (5)
C7B0.91703 (17)0.46555 (15)0.98714 (17)0.0178 (5)
C8B0.88065 (18)0.53202 (15)0.99053 (18)0.0188 (5)
C9B0.72516 (19)0.67210 (15)0.75815 (19)0.0209 (6)
C10B0.65394 (19)0.68525 (16)0.6900 (2)0.0240 (6)
H10B0.6161390.6497230.6656350.029*
C11B0.6399 (2)0.74952 (17)0.6594 (2)0.0243 (6)
H11B0.5920320.7584440.6136500.029*
C12B0.6961 (2)0.80323 (16)0.6950 (2)0.0235 (6)
C13B0.6836 (2)0.87017 (17)0.6651 (2)0.0282 (7)
H13B0.6346600.8806630.6211530.034*
C14B0.7408 (2)0.92001 (17)0.6984 (2)0.0314 (7)
H14B0.7317480.9646860.6769440.038*
C15B0.8133 (2)0.90552 (18)0.7645 (2)0.0306 (7)
H15B0.8531570.9404430.7868740.037*
C16B0.8265 (2)0.84174 (17)0.7966 (2)0.0266 (6)
H16B0.8751980.8326550.8414530.032*
C17B0.76811 (19)0.78889 (15)0.76337 (19)0.0213 (6)
C18B0.78143 (19)0.72194 (16)0.7949 (2)0.0218 (6)
H18B0.8286190.7118060.8408860.026*
C19B0.6131 (2)0.35925 (18)0.9116 (3)0.0221 (7)0.911 (3)
C20B0.5515 (2)0.33995 (18)0.8379 (2)0.0248 (7)0.911 (3)
H20B0.5609410.3522610.7811510.030*0.911 (3)
C21B0.4783 (2)0.30340 (18)0.8490 (2)0.0271 (7)0.911 (3)
H21B0.4374790.2894780.7994110.032*0.911 (3)
C22B0.4622 (2)0.28597 (17)0.9331 (2)0.0254 (7)0.911 (3)
C23B0.3855 (2)0.2489 (2)0.9462 (3)0.0303 (8)0.911 (3)
H23B0.3448870.2335540.8972370.036*0.911 (3)
C24B0.3695 (3)0.2350 (2)1.0284 (3)0.0342 (9)0.911 (3)
H24B0.3179370.2104061.0362570.041*0.911 (3)
C25B0.4295 (3)0.2573 (2)1.1013 (3)0.0362 (9)0.911 (3)
H25B0.4178430.2480781.1582000.043*0.911 (3)
C26B0.5045 (3)0.2923 (2)1.0910 (2)0.0332 (8)0.911 (3)
H26B0.5446710.3065531.1407570.040*0.911 (3)
C27B0.5228 (3)0.3072 (2)1.0069 (3)0.0248 (8)0.911 (3)
C28B0.5998 (2)0.34384 (18)0.9947 (2)0.0243 (7)0.911 (3)
H28B0.6417340.3575991.0434760.029*0.911 (3)
C29B0.8895 (2)0.40251 (19)0.6196 (2)0.0216 (8)0.911 (3)
C30B0.8312 (2)0.36323 (18)0.5594 (2)0.0230 (7)0.911 (3)
H30B0.7707490.3579880.5659290.028*0.911 (3)
C31B0.8630 (2)0.33285 (18)0.4917 (2)0.0239 (7)0.911 (3)
H31B0.8242360.3062300.4513730.029*0.911 (3)
C32B0.9529 (2)0.34066 (18)0.4811 (2)0.0223 (7)0.911 (3)
C33B0.9873 (2)0.30916 (19)0.4119 (2)0.0277 (7)0.911 (3)
H33B0.9498900.2814070.3718410.033*0.911 (3)
C34B1.0743 (3)0.3186 (2)0.4026 (2)0.0329 (8)0.911 (3)
H34B1.0965700.2976630.3557050.039*0.911 (3)
C35B1.1307 (2)0.3589 (2)0.4614 (2)0.0338 (8)0.911 (3)
H35B1.1908240.3648820.4540620.041*0.911 (3)
C36B1.1002 (2)0.3898 (2)0.5292 (2)0.0309 (8)0.911 (3)
H36B1.1390900.4169430.5686820.037*0.911 (3)
C37B1.0105 (2)0.3813 (2)0.5407 (2)0.0224 (7)0.911 (3)
C38B0.9766 (2)0.4121 (2)0.6107 (2)0.0244 (7)0.911 (3)
H38B1.0141530.4393530.6512680.029*0.911 (3)
C39B1.01292 (18)0.55284 (15)0.80852 (19)0.0207 (6)
C40B1.0962 (2)0.52835 (18)0.7958 (2)0.0321 (7)
H40B1.1265730.4965740.8356170.039*
C41B1.1349 (2)0.5500 (2)0.7259 (3)0.0418 (9)
H41B1.1906190.5320680.7175280.050*
C42B1.0928 (2)0.5974 (2)0.6683 (3)0.0396 (9)
H42B1.1199210.6123920.6209260.048*
C43B1.0111 (2)0.6230 (2)0.6800 (2)0.0363 (8)
H43B0.9817380.6553710.6405910.044*
C44B0.9721 (2)0.60103 (18)0.7498 (2)0.0286 (7)
H44B0.9163920.6192530.7577470.034*
C45B1.03063 (18)0.40615 (15)0.90813 (18)0.0188 (5)
C46B1.01554 (19)0.35929 (16)0.8411 (2)0.0235 (6)
H46B0.9663050.3649440.7957860.028*
C47B1.0717 (2)0.30408 (17)0.8396 (2)0.0266 (6)
H47B1.0603880.2725630.7932260.032*
C48B1.1436 (2)0.29478 (16)0.9048 (2)0.0259 (6)
H48B1.1812470.2567500.9039430.031*
C49B1.1602 (2)0.34130 (18)0.9711 (2)0.0306 (7)
H49B1.2102470.3357891.0156130.037*
C50B1.1042 (2)0.39609 (17)0.9733 (2)0.0278 (7)
H50B1.1160390.4273771.0198380.033*
C51B0.91505 (18)0.41028 (15)1.05049 (18)0.0191 (5)
C52B0.9313 (2)0.42455 (16)1.13966 (19)0.0236 (6)
H52B0.9365760.4699651.1589580.028*
C53B0.9397 (2)0.37234 (17)1.2002 (2)0.0274 (7)
H53B0.9489240.3823931.2606260.033*
C54B0.9346 (2)0.30613 (17)1.1730 (2)0.0272 (6)
H54B0.9423420.2707431.2145360.033*
C55B0.9182 (2)0.29127 (16)1.0844 (2)0.0253 (6)
H55B0.9148240.2457701.0653580.030*
C56B0.9069 (2)0.34332 (16)1.02437 (19)0.0231 (6)
H56B0.8932070.3330240.9641180.028*
C57B0.82839 (19)0.55533 (15)1.05734 (18)0.0203 (6)
C58B0.8589 (2)0.60964 (16)1.1105 (2)0.0254 (6)
H58B0.9084010.6350411.0987410.031*
C59B0.8177 (2)0.62699 (17)1.1804 (2)0.0292 (7)
H59B0.8400650.6635671.2168150.035*
C60B0.7441 (2)0.59151 (17)1.1979 (2)0.0276 (6)
H60B0.7165160.6033171.2462360.033*
C61B0.7112 (2)0.53847 (18)1.1437 (2)0.0271 (6)
H61B0.6601110.5144721.1541000.033*
C62B0.75330 (19)0.52061 (16)1.0743 (2)0.0229 (6)
H62B0.7306310.4842041.0377040.028*
O10.49104 (17)0.46261 (14)0.07107 (18)0.0412 (6)
C10.4135 (2)0.45163 (19)0.0431 (2)0.0345 (7)
C20.3474 (3)0.4399 (3)0.1032 (3)0.0576 (13)
H2A0.3380230.3914090.1090460.086*
H2B0.2909470.4615570.0794280.086*
H2C0.3702230.4590710.1604990.086*
C30.3779 (3)0.4484 (2)−0.0521 (2)0.0429 (9)
H3A0.3394160.487317−0.0687670.064*
H3B0.3435980.406839−0.0649050.064*
H3C0.4274570.448860−0.0850790.064*
C29C0.9079 (18)0.4224 (17)0.6256 (19)0.026 (6)0.089 (3)
C38C0.866 (2)0.3738 (16)0.5692 (19)0.0230 (7)0.089 (3)
H38C0.8068710.3594830.5713480.028*0.089 (3)
C37C0.9160 (17)0.3467 (11)0.5082 (14)0.020 (5)0.089 (3)
C36C0.8793 (19)0.2968 (13)0.4492 (17)0.021 (5)0.089 (3)
H36C0.8205390.2810900.4499570.025*0.089 (3)
C35C0.9295 (18)0.2701 (15)0.3890 (18)0.0277 (7)0.089 (3)
H35C0.9046960.2372240.3478220.033*0.089 (3)
C34C1.0173 (19)0.2930 (17)0.391 (2)0.0277 (7)0.089 (3)
H34C1.0518660.2719780.3530960.033*0.089 (3)
C33C1.0567 (19)0.3446 (16)0.4447 (17)0.026 (5)0.089 (3)
H33C1.1137040.3624890.4407000.031*0.089 (3)
C32C1.0038 (18)0.3678 (16)0.5059 (19)0.021 (6)0.089 (3)
C31C1.042 (2)0.4187 (15)0.5635 (18)0.023 (5)0.089 (3)
H31C1.0999560.4355030.5598800.028*0.089 (3)
C30C0.9947 (17)0.4440 (17)0.6259 (18)0.022 (6)0.089 (3)
H30C1.0213610.4755510.6680290.027*0.089 (3)
C19C0.6385 (18)0.3566 (15)0.9468 (16)0.022 (5)0.089 (3)
C27C0.5010 (14)0.3005 (11)0.9272 (17)0.035 (6)0.089 (3)
C25C0.3569 (18)0.2418 (15)0.906 (2)0.037 (6)0.089 (3)
H25C0.3067470.2244720.8678540.044*0.089 (3)
C20C0.6507 (16)0.3508 (15)1.0366 (16)0.0243 (7)0.089 (3)
H20C0.7015620.3680291.0733400.029*0.089 (3)
C24C0.366 (2)0.2352 (17)0.995 (2)0.0342 (9)0.089 (3)
H24C0.3206580.2121521.0187280.041*0.089 (3)
C21C0.5822 (15)0.3176 (15)1.0686 (18)0.027 (5)0.089 (3)
H21C0.5879510.3121121.1298760.032*0.089 (3)
C26C0.4252 (16)0.2752 (14)0.8738 (17)0.0254 (7)0.089 (3)
H26C0.4202840.2810980.8127090.030*0.089 (3)
C22C0.5054 (17)0.2917 (18)1.0172 (18)0.028 (7)0.089 (3)
C28C0.5660 (19)0.3333 (16)0.8884 (18)0.025 (6)0.089 (3)
H28C0.5610180.3390660.8272280.030*0.089 (3)
C23C0.4378 (17)0.2604 (17)1.0536 (19)0.034 (6)0.089 (3)
H23C0.4406670.2565301.1147590.040*0.089 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe1A0.01549 (19)0.0134 (2)0.01623 (19)−0.00060 (16)0.00133 (14)0.00003 (16)
O1A0.0235 (10)0.0133 (10)0.0222 (10)−0.0006 (8)0.0002 (8)−0.0005 (8)
N1A0.0236 (12)0.0205 (13)0.0219 (12)−0.0004 (10)−0.0004 (9)0.0023 (10)
N2A0.0257 (12)0.0216 (13)0.0264 (13)−0.0041 (10)0.0068 (10)−0.0062 (10)
N3A0.0202 (12)0.0248 (13)0.0250 (12)−0.0038 (10)0.0026 (10)0.0022 (10)
C1A0.0190 (12)0.0185 (14)0.0168 (12)−0.0016 (10)0.0016 (10)−0.0001 (10)
C2A0.0164 (12)0.0166 (13)0.0223 (14)−0.0021 (10)0.0003 (10)0.0002 (10)
C3A0.0221 (13)0.0143 (13)0.0200 (13)0.0004 (10)0.0008 (10)−0.0008 (10)
C4A0.0190 (13)0.0210 (15)0.0173 (13)−0.0013 (11)−0.0004 (10)0.0004 (10)
C5A0.0171 (12)0.0166 (14)0.0167 (12)−0.0010 (10)−0.0007 (10)−0.0007 (10)
C6A0.0145 (11)0.0189 (14)0.0159 (12)−0.0017 (10)−0.0022 (9)−0.0005 (10)
C7A0.0161 (12)0.0164 (14)0.0175 (12)−0.0012 (10)−0.0016 (9)−0.0015 (10)
C8A0.0164 (12)0.0160 (13)0.0175 (12)−0.0026 (10)−0.0023 (10)−0.0014 (10)
C9A0.0220 (13)0.0186 (14)0.0194 (13)0.0019 (11)0.0045 (10)0.0031 (11)
C10A0.0215 (14)0.0264 (16)0.0226 (14)−0.0013 (12)−0.0015 (11)−0.0009 (12)
C11A0.0252 (14)0.0194 (15)0.0288 (16)−0.0034 (11)0.0016 (12)−0.0035 (12)
C12A0.0239 (14)0.0200 (15)0.0221 (14)0.0010 (11)0.0065 (11)0.0003 (11)
C13A0.0380 (18)0.0167 (15)0.0353 (17)0.0011 (13)0.0021 (14)−0.0014 (13)
C14A0.0407 (19)0.0238 (17)0.0363 (18)0.0106 (14)0.0040 (15)0.0079 (14)
C15A0.0254 (14)0.0333 (18)0.0245 (15)0.0109 (13)−0.0008 (12)0.0024 (13)
C16A0.0211 (13)0.0254 (16)0.0230 (14)0.0028 (11)0.0016 (11)−0.0015 (11)
C17A0.0181 (13)0.0199 (15)0.0198 (13)0.0027 (10)0.0054 (10)−0.0009 (11)
C18A0.0196 (13)0.0182 (14)0.0204 (13)−0.0014 (11)0.0021 (10)−0.0009 (11)
C19A0.0222 (13)0.0191 (14)0.0226 (14)−0.0042 (11)0.0069 (11)−0.0038 (11)
C20A0.0195 (13)0.0214 (15)0.0277 (15)0.0021 (11)0.0017 (11)−0.0021 (12)
C21A0.0281 (15)0.0227 (15)0.0226 (14)0.0005 (12)0.0020 (11)0.0000 (11)
C22A0.0297 (15)0.0167 (14)0.0259 (15)0.0011 (11)0.0091 (12)0.0024 (11)
C23A0.047 (2)0.0261 (17)0.0285 (16)0.0037 (14)0.0164 (15)0.0036 (13)
C24A0.053 (2)0.037 (2)0.048 (2)0.0112 (17)0.0338 (19)0.0068 (17)
C25A0.0354 (19)0.052 (3)0.061 (3)0.0202 (17)0.0257 (18)0.016 (2)
C26A0.0270 (16)0.045 (2)0.0407 (19)0.0096 (15)0.0107 (14)0.0114 (16)
C27A0.0230 (14)0.0229 (15)0.0278 (15)0.0012 (11)0.0069 (11)0.0064 (12)
C28A0.0219 (13)0.0266 (16)0.0219 (14)−0.0024 (11)0.0014 (11)0.0026 (12)
C29A0.0178 (13)0.0239 (16)0.0233 (14)−0.0059 (11)0.0025 (11)0.0029 (11)
C30A0.0261 (14)0.0229 (16)0.0279 (15)0.0000 (12)0.0026 (12)−0.0013 (12)
C31A0.0330 (16)0.0208 (16)0.0306 (16)−0.0076 (12)−0.0033 (13)0.0019 (12)
C32A0.0242 (14)0.0340 (18)0.0218 (14)−0.0094 (12)−0.0014 (11)0.0064 (12)
C33A0.0339 (18)0.048 (2)0.0344 (18)−0.0175 (16)−0.0028 (14)0.0141 (16)
C34A0.0286 (18)0.086 (4)0.0316 (19)−0.0132 (19)0.0073 (15)0.018 (2)
C35A0.0292 (18)0.078 (3)0.0332 (19)0.0036 (18)0.0103 (15)0.0026 (19)
C36A0.0261 (16)0.049 (2)0.0303 (17)0.0019 (15)0.0051 (13)−0.0031 (16)
C37A0.0180 (13)0.0327 (18)0.0216 (14)−0.0028 (11)−0.0012 (11)0.0023 (12)
C38A0.0217 (13)0.0205 (15)0.0262 (15)−0.0013 (11)−0.0005 (11)0.0019 (12)
C39A0.0192 (13)0.0227 (15)0.0150 (12)0.0030 (11)−0.0004 (10)0.0020 (11)
C40A0.0219 (13)0.0191 (14)0.0206 (13)0.0019 (11)0.0019 (11)0.0004 (11)
C41A0.0235 (14)0.0311 (17)0.0236 (14)0.0031 (12)0.0050 (11)0.0033 (12)
C42A0.0283 (16)0.0359 (19)0.0223 (14)0.0063 (13)0.0066 (12)−0.0029 (13)
C43A0.0344 (16)0.0239 (16)0.0269 (15)0.0057 (13)0.0053 (13)−0.0054 (12)
C44A0.0244 (14)0.0218 (15)0.0238 (14)0.0015 (11)0.0027 (11)−0.0014 (11)
C45A0.0172 (12)0.0194 (14)0.0230 (14)0.0017 (10)0.0041 (10)0.0025 (11)
C46A0.0193 (13)0.0215 (15)0.0281 (15)−0.0007 (11)0.0036 (11)0.0027 (12)
C47A0.0262 (15)0.0192 (15)0.0399 (18)−0.0007 (12)0.0036 (13)0.0074 (13)
C48A0.0285 (15)0.0285 (18)0.0359 (17)0.0013 (13)0.0079 (13)0.0161 (14)
C49A0.0283 (15)0.0314 (17)0.0239 (15)0.0063 (13)0.0041 (12)0.0043 (13)
C50A0.0227 (13)0.0214 (15)0.0231 (14)0.0024 (11)0.0035 (11)0.0011 (11)
C51A0.0205 (13)0.0174 (14)0.0167 (12)0.0010 (10)0.0034 (10)0.0003 (10)
C52A0.0224 (13)0.0206 (14)0.0215 (14)−0.0003 (11)0.0022 (11)−0.0017 (11)
C53A0.0204 (14)0.0339 (18)0.0276 (15)0.0047 (12)0.0044 (11)0.0029 (13)
C54A0.0312 (16)0.0301 (18)0.0317 (17)0.0142 (13)0.0111 (13)0.0066 (14)
C55A0.0386 (17)0.0159 (15)0.0301 (16)0.0035 (12)0.0076 (13)0.0007 (12)
C56A0.0241 (14)0.0185 (15)0.0247 (14)−0.0017 (11)0.0037 (11)−0.0018 (11)
C57A0.0159 (12)0.0200 (14)0.0197 (13)0.0007 (10)−0.0008 (10)0.0024 (11)
C58A0.0205 (13)0.0203 (15)0.0251 (14)−0.0030 (11)0.0027 (11)0.0006 (11)
C59A0.0246 (14)0.0250 (16)0.0326 (16)−0.0049 (12)0.0019 (12)0.0076 (13)
C60A0.0228 (15)0.0354 (19)0.0285 (16)−0.0013 (13)0.0059 (12)0.0103 (14)
C61A0.0232 (14)0.0335 (18)0.0231 (14)0.0034 (12)0.0043 (12)0.0024 (13)
C62A0.0205 (13)0.0221 (15)0.0217 (14)−0.0009 (11)0.0016 (11)0.0014 (11)
Fe1B0.01538 (19)0.0150 (2)0.0168 (2)0.00048 (16)0.00164 (15)0.00101 (16)
O1B0.0217 (10)0.0164 (11)0.0242 (10)−0.0007 (7)−0.0012 (8)0.0019 (8)
N1B0.0182 (11)0.0223 (13)0.0266 (13)0.0014 (9)0.0024 (9)0.0048 (10)
N2B0.0259 (12)0.0201 (13)0.0303 (13)−0.0019 (10)0.0082 (10)−0.0017 (10)
N3B0.0242 (12)0.0288 (14)0.0182 (12)0.0023 (10)0.0017 (9)−0.0013 (10)
C1B0.0148 (12)0.0186 (14)0.0226 (14)−0.0012 (10)0.0015 (10)−0.0015 (11)
C2B0.0217 (13)0.0168 (14)0.0199 (13)0.0024 (10)0.0019 (10)0.0011 (10)
C3B0.0158 (12)0.0190 (14)0.0231 (13)0.0006 (10)−0.0009 (10)0.0022 (11)
C4B0.0163 (12)0.0216 (16)0.0190 (13)0.0002 (10)−0.0009 (10)0.0020 (11)
C5B0.0146 (12)0.0179 (14)0.0215 (13)−0.0003 (10)−0.0006 (10)0.0004 (11)
C6B0.0163 (12)0.0190 (14)0.0193 (12)0.0007 (10)−0.0007 (10)0.0001 (11)
C7B0.0168 (12)0.0186 (15)0.0167 (12)0.0006 (10)−0.0014 (9)−0.0001 (10)
C8B0.0190 (12)0.0178 (14)0.0188 (13)−0.0010 (10)0.0009 (10)−0.0012 (11)
C9B0.0195 (13)0.0205 (15)0.0225 (14)0.0037 (11)0.0033 (11)0.0034 (11)
C10B0.0199 (14)0.0262 (16)0.0249 (15)0.0003 (11)0.0006 (11)0.0019 (12)
C11B0.0210 (14)0.0271 (16)0.0234 (14)0.0038 (12)−0.0002 (11)0.0049 (12)
C12B0.0255 (14)0.0239 (16)0.0215 (14)0.0054 (12)0.0050 (11)0.0027 (11)
C13B0.0344 (16)0.0255 (17)0.0234 (15)0.0079 (13)0.0010 (12)0.0053 (12)
C14B0.0471 (19)0.0192 (16)0.0274 (16)0.0036 (13)0.0050 (14)0.0048 (12)
C15B0.0394 (17)0.0239 (16)0.0280 (16)−0.0026 (13)0.0038 (13)−0.0017 (13)
C16B0.0282 (15)0.0261 (17)0.0248 (15)0.0015 (12)0.0018 (12)0.0017 (12)
C17B0.0217 (13)0.0210 (15)0.0215 (14)0.0036 (11)0.0045 (11)0.0025 (11)
C18B0.0187 (13)0.0248 (16)0.0215 (14)0.0038 (11)0.0017 (11)0.0026 (11)
C19B0.0196 (16)0.0173 (17)0.0304 (19)−0.0010 (13)0.0069 (14)0.0008 (15)
C20B0.0245 (16)0.0259 (18)0.0241 (17)−0.0002 (13)0.0043 (13)0.0024 (14)
C21B0.0210 (15)0.0283 (18)0.0307 (17)−0.0009 (13)0.0007 (13)−0.0017 (14)
C22B0.0205 (16)0.0205 (17)0.0347 (17)0.0026 (13)0.0031 (13)0.0039 (14)
C23B0.0197 (16)0.0295 (19)0.041 (2)0.0018 (14)0.0039 (15)0.0076 (17)
C24B0.0253 (16)0.0265 (18)0.053 (2)0.0005 (13)0.0127 (17)0.0136 (19)
C25B0.037 (2)0.035 (2)0.041 (2)0.0037 (16)0.0168 (17)0.0135 (18)
C26B0.0345 (18)0.035 (2)0.0312 (19)0.0017 (15)0.0074 (15)0.0055 (16)
C27B0.0223 (17)0.022 (2)0.0308 (18)0.0012 (14)0.0062 (14)0.0021 (14)
C28B0.0225 (15)0.0247 (17)0.0246 (16)−0.0008 (13)0.0009 (12)−0.0007 (13)
C29B0.0244 (17)0.0226 (19)0.0180 (16)0.0042 (14)0.0042 (13)0.0024 (14)
C30B0.0213 (16)0.0259 (17)0.0216 (15)0.0003 (13)0.0033 (13)−0.0005 (12)
C31B0.0239 (17)0.0272 (18)0.0195 (15)0.0008 (13)−0.0002 (13)−0.0005 (13)
C32B0.0237 (16)0.0239 (17)0.0186 (15)0.0044 (13)0.0013 (13)0.0051 (13)
C33B0.0341 (18)0.0293 (19)0.0204 (16)0.0072 (14)0.0064 (13)0.0031 (13)
C34B0.0369 (19)0.040 (2)0.0251 (18)0.0136 (16)0.0144 (15)0.0086 (15)
C35B0.0250 (17)0.043 (2)0.0357 (19)0.0058 (15)0.0117 (14)0.0155 (16)
C36B0.0253 (17)0.037 (2)0.0305 (18)−0.0027 (14)0.0041 (14)0.0079 (15)
C37B0.0196 (15)0.024 (2)0.0234 (19)0.0030 (13)0.0026 (14)0.0056 (15)
C38B0.0239 (16)0.027 (2)0.0215 (16)−0.0025 (14)0.0002 (13)−0.0002 (14)
C39B0.0180 (13)0.0201 (15)0.0240 (14)−0.0018 (10)0.0030 (11)0.0013 (11)
C40B0.0225 (15)0.0282 (17)0.047 (2)0.0053 (13)0.0099 (14)0.0117 (15)
C41B0.0297 (17)0.041 (2)0.061 (3)0.0050 (15)0.0252 (17)0.0108 (18)
C42B0.0408 (19)0.041 (2)0.042 (2)−0.0020 (16)0.0232 (16)0.0099 (16)
C43B0.0313 (17)0.047 (2)0.0320 (17)0.0013 (15)0.0077 (14)0.0160 (16)
C44B0.0239 (14)0.0328 (18)0.0301 (16)0.0023 (13)0.0072 (12)0.0105 (13)
C45B0.0180 (12)0.0180 (14)0.0208 (13)0.0011 (10)0.0042 (10)0.0042 (11)
C46B0.0198 (13)0.0242 (15)0.0255 (15)0.0027 (11)0.0007 (11)−0.0017 (12)
C47B0.0260 (15)0.0248 (16)0.0288 (16)0.0035 (12)0.0041 (12)−0.0046 (12)
C48B0.0242 (14)0.0226 (16)0.0318 (16)0.0057 (11)0.0067 (12)0.0027 (12)
C49B0.0240 (15)0.0319 (18)0.0320 (16)0.0087 (13)−0.0070 (13)−0.0027 (14)
C50B0.0273 (15)0.0246 (16)0.0283 (15)0.0062 (12)−0.0046 (12)−0.0068 (12)
C51B0.0168 (12)0.0213 (14)0.0188 (13)0.0016 (10)0.0016 (10)0.0028 (11)
C52B0.0274 (14)0.0196 (15)0.0226 (14)0.0047 (11)0.0008 (11)−0.0005 (11)
C53B0.0327 (16)0.0298 (17)0.0193 (14)0.0044 (13)0.0028 (12)0.0033 (12)
C54B0.0317 (16)0.0254 (17)0.0259 (15)0.0020 (12)0.0085 (12)0.0086 (12)
C55B0.0290 (15)0.0189 (15)0.0288 (15)−0.0029 (11)0.0073 (12)0.0007 (12)
C56B0.0259 (14)0.0223 (15)0.0217 (14)−0.0038 (11)0.0056 (11)−0.0003 (12)
C57B0.0207 (13)0.0196 (14)0.0200 (13)0.0046 (11)0.0018 (10)0.0035 (11)
C58B0.0262 (14)0.0205 (15)0.0304 (15)−0.0006 (11)0.0072 (12)−0.0019 (12)
C59B0.0343 (16)0.0242 (17)0.0297 (16)−0.0008 (13)0.0073 (13)−0.0076 (13)
C60B0.0278 (15)0.0309 (17)0.0256 (15)0.0062 (13)0.0083 (12)−0.0007 (13)
C61B0.0229 (14)0.0313 (17)0.0281 (15)0.0011 (12)0.0067 (12)0.0030 (13)
C62B0.0218 (13)0.0236 (16)0.0226 (14)0.0005 (11)0.0014 (11)−0.0010 (11)
O10.0399 (14)0.0360 (14)0.0473 (14)−0.0044 (11)0.0060 (11)−0.0055 (12)
C10.0410 (19)0.0263 (18)0.0365 (18)−0.0007 (14)0.0075 (14)−0.0054 (14)
C20.048 (2)0.088 (4)0.038 (2)−0.016 (2)0.0090 (18)−0.012 (2)
C30.053 (2)0.038 (2)0.0365 (19)−0.0081 (17)0.0046 (16)−0.0040 (16)
C29C0.024 (10)0.029 (15)0.024 (11)−0.001 (9)0.004 (8)−0.002 (9)
C38C0.0213 (16)0.0259 (17)0.0216 (15)0.0003 (13)0.0033 (13)−0.0005 (12)
C37C0.021 (10)0.020 (11)0.019 (10)0.003 (8)0.000 (8)0.003 (8)
C36C0.031 (11)0.010 (11)0.021 (10)0.008 (8)0.004 (8)0.001 (8)
C35C0.0341 (18)0.0293 (19)0.0204 (16)0.0072 (14)0.0064 (13)0.0031 (13)
C34C0.0341 (18)0.0293 (19)0.0204 (16)0.0072 (14)0.0064 (13)0.0031 (13)
C33C0.031 (11)0.034 (12)0.011 (10)0.012 (8)0.002 (8)0.003 (8)
C32C0.025 (10)0.025 (12)0.013 (12)0.001 (9)0.003 (9)0.001 (9)
C31C0.030 (12)0.019 (13)0.022 (11)−0.001 (10)0.008 (9)0.000 (9)
C30C0.021 (10)0.026 (15)0.021 (12)0.004 (9)0.005 (9)0.000 (10)
C19C0.025 (11)0.014 (12)0.026 (8)0.001 (10)0.004 (7)−0.006 (9)
C27C0.030 (11)0.033 (14)0.043 (10)−0.007 (10)0.008 (8)−0.004 (10)
C25C0.025 (12)0.032 (16)0.055 (9)0.000 (11)0.013 (10)0.014 (12)
C20C0.0225 (15)0.0247 (17)0.0246 (16)−0.0008 (13)0.0009 (12)−0.0007 (13)
C24C0.0253 (16)0.0265 (18)0.053 (2)0.0005 (13)0.0127 (17)0.0136 (19)
C21C0.017 (9)0.017 (13)0.047 (11)−0.001 (8)0.005 (8)0.000 (11)
C26C0.0205 (16)0.0205 (17)0.0347 (17)0.0026 (13)0.0031 (13)0.0039 (14)
C22C0.012 (10)0.029 (16)0.045 (10)0.001 (9)0.007 (8)0.002 (11)
C28C0.025 (10)0.024 (13)0.025 (11)−0.006 (9)0.002 (9)−0.011 (11)
C23C0.018 (10)0.034 (14)0.052 (12)0.005 (9)0.014 (8)0.016 (12)
Geometric parameters (Å, º) top
Fe1A—C1A1.835 (3)C7B—C51B1.480 (4)
Fe1A—C2A1.829 (3)C8B—C57B1.484 (4)
Fe1A—C3A1.828 (3)C9B—C10B1.414 (4)
Fe1A—C4A2.367 (3)C9B—C18B1.373 (4)
Fe1A—C5A2.142 (3)C10B—H10B0.9500
Fe1A—C6A2.070 (3)C10B—C11B1.367 (5)
Fe1A—C7A2.067 (3)C11B—H11B0.9500
Fe1A—C8A2.141 (3)C11B—C12B1.423 (5)
O1A—C4A1.247 (4)C12B—C13B1.411 (4)
N1A—C1A1.160 (4)C12B—C17B1.428 (4)
N1A—C9A1.399 (4)C13B—H13B0.9500
N2A—C2A1.165 (4)C13B—C14B1.364 (5)
N2A—C19A1.396 (4)C14B—H14B0.9500
N3A—C3A1.167 (4)C14B—C15B1.413 (5)
N3A—C29A1.403 (4)C15B—H15B0.9500
C4A—C5A1.480 (4)C15B—C16B1.364 (5)
C4A—C8A1.476 (4)C16B—H16B0.9500
C5A—C6A1.438 (4)C16B—C17B1.419 (5)
C5A—C39A1.488 (4)C17B—C18B1.421 (4)
C6A—C7A1.442 (4)C18B—H18B0.9500
C6A—C45A1.486 (4)C19B—C20B1.413 (5)
C7A—C8A1.447 (4)C19B—C28B1.377 (5)
C7A—C51A1.484 (4)C20B—H20B0.9500
C8A—C57A1.481 (4)C20B—C21B1.367 (5)
C9A—C10A1.412 (4)C21B—H21B0.9500
C9A—C18A1.372 (4)C21B—C22B1.416 (5)
C10A—H10A0.9500C22B—C23B1.424 (5)
C10A—C11A1.361 (5)C22B—C27B1.417 (5)
C11A—H11A0.9500C23B—H23B0.9500
C11A—C12A1.425 (4)C23B—C24B1.371 (6)
C12A—C13A1.419 (4)C24B—H24B0.9500
C12A—C17A1.416 (4)C24B—C25B1.409 (6)
C13A—H13A0.9500C25B—H25B0.9500
C13A—C14A1.366 (5)C25B—C26B1.369 (5)
C14A—H14A0.9500C26B—H26B0.9500
C14A—C15A1.412 (5)C26B—C27B1.415 (5)
C15A—H15A0.9500C27B—C28B1.419 (5)
C15A—C16A1.368 (5)C28B—H28B0.9500
C16A—H16A0.9500C29B—C30B1.416 (5)
C16A—C17A1.420 (4)C29B—C38B1.370 (5)
C17A—C18A1.413 (4)C30B—H30B0.9500
C18A—H18A0.9500C30B—C31B1.370 (5)
C19A—C20A1.413 (4)C31B—H31B0.9500
C19A—C28A1.369 (4)C31B—C32B1.416 (5)
C20A—H20A0.9500C32B—C33B1.419 (5)
C20A—C21A1.366 (4)C32B—C37B1.420 (5)
C21A—H21A0.9500C33B—H33B0.9500
C21A—C22A1.417 (4)C33B—C34B1.370 (5)
C22A—C23A1.425 (4)C34B—H34B0.9500
C22A—C27A1.414 (4)C34B—C35B1.401 (6)
C23A—H23A0.9500C35B—H35B0.9500
C23A—C24A1.366 (5)C35B—C36B1.367 (5)
C24A—H24A0.9500C36B—H36B0.9500
C24A—C25A1.402 (7)C36B—C37B1.418 (5)
C25A—H25A0.9500C37B—C38B1.419 (5)
C25A—C26A1.375 (5)C38B—H38B0.9500
C26A—H26A0.9500C39B—C40B1.404 (4)
C26A—C27A1.420 (4)C39B—C44B1.398 (4)
C27A—C28A1.416 (4)C40B—H40B0.9500
C28A—H28A0.9500C40B—C41B1.388 (5)
C29A—C30A1.415 (5)C41B—H41B0.9500
C29A—C38A1.369 (4)C41B—C42B1.385 (6)
C30A—H30A0.9500C42B—H42B0.9500
C30A—C31A1.372 (5)C42B—C43B1.385 (5)
C31A—H31A0.9500C43B—H43B0.9500
C31A—C32A1.416 (5)C43B—C44B1.391 (4)
C32A—C33A1.425 (4)C44B—H44B0.9500
C32A—C37A1.425 (5)C45B—C46B1.389 (4)
C33A—H33A0.9500C45B—C50B1.399 (4)
C33A—C34A1.365 (6)C46B—H46B0.9500
C34A—H34A0.9500C46B—C47B1.394 (4)
C34A—C35A1.413 (7)C47B—H47B0.9500
C35A—H35A0.9500C47B—C48B1.380 (5)
C35A—C36A1.358 (5)C48B—H48B0.9500
C36A—H36A0.9500C48B—C49B1.379 (5)
C36A—C37A1.416 (5)C49B—H49B0.9500
C37A—C38A1.408 (4)C49B—C50B1.387 (4)
C38A—H38A0.9500C50B—H50B0.9500
C39A—C40A1.400 (4)C51B—C52B1.400 (4)
C39A—C44A1.400 (4)C51B—C56B1.390 (4)
C40A—H40A0.9500C52B—H52B0.9500
C40A—C41A1.393 (4)C52B—C53B1.394 (4)
C41A—H41A0.9500C53B—H53B0.9500
C41A—C42A1.391 (5)C53B—C54B1.380 (5)
C42A—H42A0.9500C54B—H54B0.9500
C42A—C43A1.386 (5)C54B—C55B1.392 (5)
C43A—H43A0.9500C55B—H55B0.9500
C43A—C44A1.388 (4)C55B—C56B1.386 (4)
C44A—H44A0.9500C56B—H56B0.9500
C45A—C46A1.395 (4)C57B—C58B1.393 (4)
C45A—C50A1.398 (4)C57B—C62B1.398 (4)
C46A—H46A0.9500C58B—H58B0.9500
C46A—C47A1.394 (4)C58B—C59B1.387 (4)
C47A—H47A0.9500C59B—H59B0.9500
C47A—C48A1.386 (5)C59B—C60B1.389 (5)
C48A—H48A0.9500C60B—H60B0.9500
C48A—C49A1.385 (5)C60B—C61B1.391 (5)
C49A—H49A0.9500C61B—H61B0.9500
C49A—C50A1.390 (4)C61B—C62B1.390 (4)
C50A—H50A0.9500C62B—H62B0.9500
C51A—C52A1.396 (4)O1—C11.211 (4)
C51A—C56A1.394 (4)C1—C21.502 (5)
C52A—H52A0.9500C1—C31.495 (5)
C52A—C53A1.396 (4)C2—H2A0.9800
C53A—H53A0.9500C2—H2B0.9800
C53A—C54A1.384 (5)C2—H2C0.9800
C54A—H54A0.9500C3—H3A0.9800
C54A—C55A1.379 (5)C3—H3B0.9800
C55A—H55A0.9500C3—H3C0.9800
C55A—C56A1.396 (4)C29C—C38C1.39 (2)
C56A—H56A0.9500C29C—C30C1.391 (19)
C57A—C58A1.405 (4)C38C—H38C0.9500
C57A—C62A1.402 (4)C38C—C37C1.419 (19)
C58A—H58A0.9500C37C—C36C1.403 (19)
C58A—C59A1.392 (4)C37C—C32C1.410 (19)
C59A—H59A0.9500C36C—H36C0.9500
C59A—C60A1.384 (5)C36C—C35C1.408 (19)
C60A—H60A0.9500C35C—H35C0.9500
C60A—C61A1.392 (5)C35C—C34C1.409 (19)
C61A—H61A0.9500C34C—H34C0.9500
C61A—C62A1.385 (4)C34C—C33C1.39 (2)
C62A—H62A0.9500C33C—H33C0.9500
Fe1B—C1B1.836 (3)C33C—C32C1.423 (19)
Fe1B—C2B1.840 (3)C32C—C31C1.414 (19)
Fe1B—C3B1.823 (3)C31C—H31C0.9500
Fe1B—C4B2.373 (3)C31C—C30C1.398 (19)
Fe1B—C5B2.116 (3)C30C—H30C0.9500
Fe1B—C6B2.070 (3)C19C—C20C1.385 (19)
Fe1B—C7B2.085 (3)C19C—C28C1.392 (19)
Fe1B—C8B2.142 (3)C27C—C26C1.402 (18)
O1B—C4B1.243 (4)C27C—C22C1.404 (19)
N1B—C1B1.163 (4)C27C—C28C1.403 (19)
N1B—C9B1.397 (4)C25C—H25C0.9500
N2B—C2B1.172 (4)C25C—C24C1.39 (2)
N2B—C19B1.410 (4)C25C—C26C1.391 (19)
N2B—C19C1.39 (2)C20C—H20C0.9500
N3B—C3B1.172 (4)C20C—C21C1.394 (19)
N3B—C29B1.404 (4)C24C—H24C0.9500
N3B—C29C1.38 (2)C24C—C23C1.39 (2)
C4B—C5B1.481 (4)C21C—H21C0.9500
C4B—C8B1.477 (4)C21C—C22C1.404 (19)
C5B—C6B1.442 (4)C26C—H26C0.9500
C5B—C39B1.479 (4)C22C—C23C1.400 (18)
C6B—C7B1.441 (4)C28C—H28C0.9500
C6B—C45B1.491 (4)C23C—H23C0.9500
C7B—C8B1.436 (4)
C1A—Fe1A—C4A79.78 (11)C5B—C4B—Fe1B61.55 (15)
C1A—Fe1A—C5A98.52 (12)C8B—C4B—Fe1B62.62 (15)
C1A—Fe1A—C6A138.31 (12)C8B—C4B—C5B104.3 (2)
C1A—Fe1A—C7A137.35 (12)C4B—C5B—Fe1B80.46 (16)
C1A—Fe1A—C8A97.18 (12)C6B—C5B—Fe1B68.15 (15)
C2A—Fe1A—C1A95.62 (13)C6B—C5B—C4B108.6 (2)
C2A—Fe1A—C4A132.89 (11)C6B—C5B—C39B127.7 (3)
C2A—Fe1A—C5A159.93 (11)C39B—C5B—Fe1B126.0 (2)
C2A—Fe1A—C6A123.96 (12)C39B—C5B—C4B122.8 (3)
C2A—Fe1A—C7A92.63 (12)C5B—C6B—Fe1B71.57 (15)
C2A—Fe1A—C8A98.10 (11)C5B—C6B—C45B128.9 (2)
C3A—Fe1A—C1A97.51 (12)C7B—C6B—Fe1B70.28 (14)
C3A—Fe1A—C2A95.24 (12)C7B—C6B—C5B107.6 (2)
C3A—Fe1A—C4A131.86 (11)C7B—C6B—C45B122.4 (2)
C3A—Fe1A—C5A96.94 (12)C45B—C6B—Fe1B133.1 (2)
C3A—Fe1A—C6A91.83 (12)C6B—C7B—Fe1B69.13 (14)
C3A—Fe1A—C7A123.31 (12)C6B—C7B—C51B123.2 (3)
C3A—Fe1A—C8A159.05 (12)C8B—C7B—Fe1B72.29 (15)
C5A—Fe1A—C4A37.90 (10)C8B—C7B—C6B108.6 (2)
C6A—Fe1A—C4A64.25 (10)C8B—C7B—C51B127.4 (2)
C6A—Fe1A—C5A39.87 (11)C51B—C7B—Fe1B132.2 (2)
C6A—Fe1A—C8A67.30 (10)C4B—C8B—Fe1B79.63 (17)
C7A—Fe1A—C4A64.44 (10)C4B—C8B—C57B125.0 (3)
C7A—Fe1A—C5A67.34 (10)C7B—C8B—Fe1B68.01 (15)
C7A—Fe1A—C6A40.80 (10)C7B—C8B—C4B108.3 (2)
C7A—Fe1A—C8A40.18 (11)C7B—C8B—C57B124.6 (3)
C8A—Fe1A—C4A37.80 (10)C57B—C8B—Fe1B131.2 (2)
C8A—Fe1A—C5A66.10 (10)N1B—C9B—C10B119.0 (3)
C1A—N1A—C9A168.6 (3)C18B—C9B—N1B118.8 (3)
C2A—N2A—C19A170.5 (3)C18B—C9B—C10B122.1 (3)
C3A—N3A—C29A168.5 (3)C9B—C10B—H10B120.3
N1A—C1A—Fe1A175.5 (3)C11B—C10B—C9B119.4 (3)
N2A—C2A—Fe1A176.5 (3)C11B—C10B—H10B120.3
N3A—C3A—Fe1A175.5 (3)C10B—C11B—H11B119.5
O1A—C4A—Fe1A133.9 (2)C10B—C11B—C12B120.9 (3)
O1A—C4A—C5A128.0 (3)C12B—C11B—H11B119.5
O1A—C4A—C8A127.3 (3)C11B—C12B—C17B118.8 (3)
C5A—C4A—Fe1A62.77 (15)C13B—C12B—C11B122.5 (3)
C8A—C4A—Fe1A62.76 (14)C13B—C12B—C17B118.7 (3)
C8A—C4A—C5A104.4 (2)C12B—C13B—H13B119.5
C4A—C5A—Fe1A79.34 (16)C14B—C13B—C12B121.0 (3)
C4A—C5A—C39A123.8 (3)C14B—C13B—H13B119.5
C6A—C5A—Fe1A67.36 (15)C13B—C14B—H14B119.8
C6A—C5A—C4A108.8 (2)C13B—C14B—C15B120.3 (3)
C6A—C5A—C39A125.6 (2)C15B—C14B—H14B119.8
C39A—C5A—Fe1A131.10 (19)C14B—C15B—H15B119.8
C5A—C6A—Fe1A72.76 (15)C16B—C15B—C14B120.5 (3)
C5A—C6A—C7A108.3 (2)C16B—C15B—H15B119.8
C5A—C6A—C45A125.3 (2)C15B—C16B—H16B119.8
C7A—C6A—Fe1A69.51 (15)C15B—C16B—C17B120.4 (3)
C7A—C6A—C45A125.3 (2)C17B—C16B—H16B119.8
C45A—C6A—Fe1A132.87 (19)C16B—C17B—C12B119.0 (3)
C6A—C7A—Fe1A69.69 (14)C16B—C17B—C18B121.3 (3)
C6A—C7A—C8A107.8 (2)C18B—C17B—C12B119.6 (3)
C6A—C7A—C51A124.5 (2)C9B—C18B—C17B119.1 (3)
C8A—C7A—Fe1A72.65 (15)C9B—C18B—H18B120.5
C8A—C7A—C51A126.3 (2)C17B—C18B—H18B120.5
C51A—C7A—Fe1A133.59 (19)N2B—C19B—C20B119.0 (3)
C4A—C8A—Fe1A79.43 (16)C28B—C19B—N2B119.4 (3)
C4A—C8A—C57A124.0 (3)C28B—C19B—C20B121.6 (3)
C7A—C8A—Fe1A67.17 (15)C19B—C20B—H20B120.3
C7A—C8A—C4A108.9 (2)C21B—C20B—C19B119.3 (3)
C7A—C8A—C57A125.5 (2)C21B—C20B—H20B120.3
C57A—C8A—Fe1A130.93 (19)C20B—C21B—H21B119.5
N1A—C9A—C10A117.6 (3)C20B—C21B—C22B121.0 (3)
C18A—C9A—N1A119.9 (3)C22B—C21B—H21B119.5
C18A—C9A—C10A122.4 (3)C21B—C22B—C23B121.9 (3)
C9A—C10A—H10A120.7C21B—C22B—C27B119.3 (3)
C11A—C10A—C9A118.7 (3)C27B—C22B—C23B118.8 (3)
C11A—C10A—H10A120.7C22B—C23B—H23B119.6
C10A—C11A—H11A119.4C24B—C23B—C22B120.8 (4)
C10A—C11A—C12A121.2 (3)C24B—C23B—H23B119.6
C12A—C11A—H11A119.4C23B—C24B—H24B120.0
C13A—C12A—C11A121.9 (3)C23B—C24B—C25B119.9 (4)
C17A—C12A—C11A119.1 (3)C25B—C24B—H24B120.0
C17A—C12A—C13A119.0 (3)C24B—C25B—H25B119.7
C12A—C13A—H13A119.7C26B—C25B—C24B120.7 (4)
C14A—C13A—C12A120.6 (3)C26B—C25B—H25B119.7
C14A—C13A—H13A119.7C25B—C26B—H26B119.7
C13A—C14A—H14A119.7C25B—C26B—C27B120.7 (4)
C13A—C14A—C15A120.7 (3)C27B—C26B—H26B119.7
C15A—C14A—H14A119.7C22B—C27B—C28B119.3 (3)
C14A—C15A—H15A120.1C26B—C27B—C22B119.1 (3)
C16A—C15A—C14A119.9 (3)C26B—C27B—C28B121.6 (3)
C16A—C15A—H15A120.1C19B—C28B—C27B119.4 (3)
C15A—C16A—H16A119.5C19B—C28B—H28B120.3
C15A—C16A—C17A120.9 (3)C27B—C28B—H28B120.3
C17A—C16A—H16A119.5N3B—C29B—C30B119.4 (3)
C12A—C17A—C16A118.9 (3)C38B—C29B—N3B119.0 (3)
C18A—C17A—C12A119.3 (3)C38B—C29B—C30B121.6 (3)
C18A—C17A—C16A121.8 (3)C29B—C30B—H30B120.3
C9A—C18A—C17A119.2 (3)C31B—C30B—C29B119.3 (3)
C9A—C18A—H18A120.4C31B—C30B—H30B120.3
C17A—C18A—H18A120.4C30B—C31B—H31B119.6
N2A—C19A—C20A118.8 (3)C30B—C31B—C32B120.8 (3)
C28A—C19A—N2A119.2 (3)C32B—C31B—H31B119.6
C28A—C19A—C20A122.0 (3)C31B—C32B—C33B121.6 (3)
C19A—C20A—H20A120.5C31B—C32B—C37B119.5 (3)
C21A—C20A—C19A119.1 (3)C33B—C32B—C37B118.8 (3)
C21A—C20A—H20A120.5C32B—C33B—H33B119.9
C20A—C21A—H21A119.6C34B—C33B—C32B120.2 (4)
C20A—C21A—C22A120.8 (3)C34B—C33B—H33B119.9
C22A—C21A—H21A119.6C33B—C34B—H34B119.7
C21A—C22A—C23A121.7 (3)C33B—C34B—C35B120.7 (3)
C27A—C22A—C21A119.4 (3)C35B—C34B—H34B119.7
C27A—C22A—C23A118.9 (3)C34B—C35B—H35B119.6
C22A—C23A—H23A119.8C36B—C35B—C34B120.8 (3)
C24A—C23A—C22A120.4 (3)C36B—C35B—H35B119.6
C24A—C23A—H23A119.8C35B—C36B—H36B120.0
C23A—C24A—H24A119.7C35B—C36B—C37B120.1 (4)
C23A—C24A—C25A120.5 (3)C37B—C36B—H36B120.0
C25A—C24A—H24A119.7C36B—C37B—C32B119.4 (3)
C24A—C25A—H25A119.5C36B—C37B—C38B121.7 (4)
C26A—C25A—C24A120.9 (3)C38B—C37B—C32B118.9 (3)
C26A—C25A—H25A119.5C29B—C38B—C37B119.8 (3)
C25A—C26A—H26A120.2C29B—C38B—H38B120.1
C25A—C26A—C27A119.7 (4)C37B—C38B—H38B120.1
C27A—C26A—H26A120.2C40B—C39B—C5B122.9 (3)
C22A—C27A—C26A119.6 (3)C44B—C39B—C5B119.6 (3)
C22A—C27A—C28A119.3 (3)C44B—C39B—C40B117.5 (3)
C28A—C27A—C26A121.1 (3)C39B—C40B—H40B119.6
C19A—C28A—C27A119.4 (3)C41B—C40B—C39B120.8 (3)
C19A—C28A—H28A120.3C41B—C40B—H40B119.6
C27A—C28A—H28A120.3C40B—C41B—H41B119.7
N3A—C29A—C30A118.5 (3)C42B—C41B—C40B120.6 (3)
C38A—C29A—N3A119.7 (3)C42B—C41B—H41B119.7
C38A—C29A—C30A121.7 (3)C41B—C42B—H42B120.2
C29A—C30A—H30A120.6C41B—C42B—C43B119.7 (3)
C31A—C30A—C29A118.7 (3)C43B—C42B—H42B120.2
C31A—C30A—H30A120.6C42B—C43B—H43B120.1
C30A—C31A—H31A119.4C42B—C43B—C44B119.8 (3)
C30A—C31A—C32A121.2 (3)C44B—C43B—H43B120.1
C32A—C31A—H31A119.4C39B—C44B—H44B119.2
C31A—C32A—C33A122.2 (3)C43B—C44B—C39B121.6 (3)
C31A—C32A—C37A119.3 (3)C43B—C44B—H44B119.2
C37A—C32A—C33A118.6 (3)C46B—C45B—C6B124.6 (3)
C32A—C33A—H33A119.7C46B—C45B—C50B117.7 (3)
C34A—C33A—C32A120.7 (4)C50B—C45B—C6B117.5 (3)
C34A—C33A—H33A119.7C45B—C46B—H46B119.6
C33A—C34A—H34A119.8C45B—C46B—C47B120.9 (3)
C33A—C34A—C35A120.4 (3)C47B—C46B—H46B119.6
C35A—C34A—H34A119.8C46B—C47B—H47B119.7
C34A—C35A—H35A119.8C48B—C47B—C46B120.6 (3)
C36A—C35A—C34A120.4 (4)C48B—C47B—H47B119.7
C36A—C35A—H35A119.8C47B—C48B—H48B120.4
C35A—C36A—H36A119.4C49B—C48B—C47B119.3 (3)
C35A—C36A—C37A121.2 (4)C49B—C48B—H48B120.4
C37A—C36A—H36A119.4C48B—C49B—H49B119.8
C36A—C37A—C32A118.8 (3)C48B—C49B—C50B120.4 (3)
C38A—C37A—C32A118.8 (3)C50B—C49B—H49B119.8
C38A—C37A—C36A122.4 (3)C45B—C50B—H50B119.4
C29A—C38A—C37A120.3 (3)C49B—C50B—C45B121.2 (3)
C29A—C38A—H38A119.8C49B—C50B—H50B119.4
C37A—C38A—H38A119.8C52B—C51B—C7B119.5 (3)
C40A—C39A—C5A122.4 (3)C56B—C51B—C7B121.7 (3)
C40A—C39A—C44A117.8 (3)C56B—C51B—C52B118.5 (3)
C44A—C39A—C5A119.8 (3)C51B—C52B—H52B119.9
C39A—C40A—H40A119.5C53B—C52B—C51B120.2 (3)
C41A—C40A—C39A121.0 (3)C53B—C52B—H52B119.9
C41A—C40A—H40A119.5C52B—C53B—H53B119.8
C40A—C41A—H41A119.8C54B—C53B—C52B120.4 (3)
C42A—C41A—C40A120.4 (3)C54B—C53B—H53B119.8
C42A—C41A—H41A119.8C53B—C54B—H54B120.0
C41A—C42A—H42A120.5C53B—C54B—C55B119.9 (3)
C43A—C42A—C41A119.0 (3)C55B—C54B—H54B120.0
C43A—C42A—H42A120.5C54B—C55B—H55B120.2
C42A—C43A—H43A119.6C56B—C55B—C54B119.5 (3)
C42A—C43A—C44A120.8 (3)C56B—C55B—H55B120.2
C44A—C43A—H43A119.6C51B—C56B—H56B119.3
C39A—C44A—H44A119.5C55B—C56B—C51B121.4 (3)
C43A—C44A—C39A121.0 (3)C55B—C56B—H56B119.3
C43A—C44A—H44A119.5C58B—C57B—C8B119.5 (3)
C46A—C45A—C6A124.1 (3)C58B—C57B—C62B118.3 (3)
C46A—C45A—C50A118.6 (3)C62B—C57B—C8B121.9 (3)
C50A—C45A—C6A117.3 (3)C57B—C58B—H58B119.7
C45A—C46A—H46A119.6C59B—C58B—C57B120.6 (3)
C47A—C46A—C45A120.9 (3)C59B—C58B—H58B119.7
C47A—C46A—H46A119.6C58B—C59B—H59B119.6
C46A—C47A—H47A120.1C58B—C59B—C60B120.8 (3)
C48A—C47A—C46A119.7 (3)C60B—C59B—H59B119.6
C48A—C47A—H47A120.1C59B—C60B—H60B120.4
C47A—C48A—H48A120.0C59B—C60B—C61B119.2 (3)
C49A—C48A—C47A120.0 (3)C61B—C60B—H60B120.4
C49A—C48A—H48A120.0C60B—C61B—H61B120.0
C48A—C49A—H49A119.8C62B—C61B—C60B119.9 (3)
C48A—C49A—C50A120.3 (3)C62B—C61B—H61B120.0
C50A—C49A—H49A119.8C57B—C62B—H62B119.4
C45A—C50A—H50A119.8C61B—C62B—C57B121.1 (3)
C49A—C50A—C45A120.4 (3)C61B—C62B—H62B119.4
C49A—C50A—H50A119.8O1—C1—C2121.2 (3)
C52A—C51A—C7A118.0 (3)O1—C1—C3122.7 (3)
C56A—C51A—C7A123.5 (2)C3—C1—C2116.1 (3)
C56A—C51A—C52A118.4 (3)C1—C2—H2A109.5
C51A—C52A—H52A119.6C1—C2—H2B109.5
C51A—C52A—C53A120.7 (3)C1—C2—H2C109.5
C53A—C52A—H52A119.6H2A—C2—H2B109.5
C52A—C53A—H53A119.9H2A—C2—H2C109.5
C54A—C53A—C52A120.2 (3)H2B—C2—H2C109.5
C54A—C53A—H53A119.9C1—C3—H3A109.5
C53A—C54A—H54A120.2C1—C3—H3B109.5
C55A—C54A—C53A119.6 (3)C1—C3—H3C109.5
C55A—C54A—H54A120.2H3A—C3—H3B109.5
C54A—C55A—H55A119.7H3A—C3—H3C109.5
C54A—C55A—C56A120.5 (3)H3B—C3—H3C109.5
C56A—C55A—H55A119.7N3B—C29C—C38C108 (2)
C51A—C56A—C55A120.5 (3)N3B—C29C—C30C127 (2)
C51A—C56A—H56A119.7C38C—C29C—C30C124 (2)
C55A—C56A—H56A119.7C29C—C38C—H38C121.8
C58A—C57A—C8A119.5 (3)C29C—C38C—C37C116 (3)
C62A—C57A—C8A122.4 (3)C37C—C38C—H38C121.8
C62A—C57A—C58A118.0 (3)C36C—C37C—C38C120 (2)
C57A—C58A—H58A119.7C36C—C37C—C32C118 (2)
C59A—C58A—C57A120.6 (3)C32C—C37C—C38C121 (2)
C59A—C58A—H58A119.7C37C—C36C—H36C120.0
C58A—C59A—H59A119.7C37C—C36C—C35C120 (3)
C60A—C59A—C58A120.7 (3)C35C—C36C—H36C120.0
C60A—C59A—H59A119.7C36C—C35C—H35C120.6
C59A—C60A—H60A120.4C36C—C35C—C34C119 (2)
C59A—C60A—C61A119.2 (3)C34C—C35C—H35C120.6
C61A—C60A—H60A120.4C35C—C34C—H34C117.8
C60A—C61A—H61A119.7C33C—C34C—C35C124 (3)
C62A—C61A—C60A120.6 (3)C33C—C34C—H34C117.8
C62A—C61A—H61A119.7C34C—C33C—H33C123.1
C57A—C62A—H62A119.5C34C—C33C—C32C114 (3)
C61A—C62A—C57A120.9 (3)C32C—C33C—H33C123.1
C61A—C62A—H62A119.5C37C—C32C—C33C124 (2)
C1B—Fe1B—C2B98.74 (12)C37C—C32C—C31C120 (2)
C1B—Fe1B—C4B78.86 (11)C31C—C32C—C33C116 (2)
C1B—Fe1B—C5B98.60 (12)C32C—C31C—H31C120.4
C1B—Fe1B—C6B138.56 (12)C30C—C31C—C32C119 (2)
C1B—Fe1B—C7B134.61 (12)C30C—C31C—H31C120.4
C1B—Fe1B—C8B94.92 (12)C29C—C30C—C31C119 (2)
C2B—Fe1B—C4B138.73 (11)C29C—C30C—H30C120.3
C2B—Fe1B—C5B160.37 (12)C31C—C30C—H30C120.3
C2B—Fe1B—C6B121.14 (12)C20C—C19C—N2B126 (2)
C2B—Fe1B—C7B93.89 (12)C20C—C19C—C28C126 (2)
C2B—Fe1B—C8B102.83 (12)C28C—C19C—N2B107.0 (19)
C3B—Fe1B—C1B92.42 (13)C26C—C27C—C22C117 (2)
C3B—Fe1B—C2B95.40 (13)C26C—C27C—C28C119 (2)
C3B—Fe1B—C4B125.77 (11)C28C—C27C—C22C124 (2)
C3B—Fe1B—C5B92.98 (12)C24C—C25C—H25C121.8
C3B—Fe1B—C6B94.38 (12)C24C—C25C—C26C116 (3)
C3B—Fe1B—C7B129.62 (12)C26C—C25C—H25C121.8
C3B—Fe1B—C8B159.03 (11)C19C—C20C—H20C122.7
C5B—Fe1B—C4B37.99 (10)C19C—C20C—C21C115 (2)
C5B—Fe1B—C8B66.52 (11)C21C—C20C—H20C122.7
C6B—Fe1B—C4B64.17 (11)C25C—C24C—H24C118.0
C6B—Fe1B—C5B40.28 (11)C25C—C24C—C23C124 (3)
C6B—Fe1B—C7B40.59 (10)C23C—C24C—H24C118.0
C6B—Fe1B—C8B67.38 (11)C20C—C21C—H21C117.5
C7B—Fe1B—C4B63.59 (10)C20C—C21C—C22C125 (2)
C7B—Fe1B—C5B67.24 (11)C22C—C21C—H21C117.5
C7B—Fe1B—C8B39.70 (11)C27C—C26C—H26C118.2
C8B—Fe1B—C4B37.75 (10)C25C—C26C—C27C124 (3)
C1B—N1B—C9B162.6 (3)C25C—C26C—H26C118.2
C2B—N2B—C19B175.8 (3)C21C—C22C—C27C115 (2)
C2B—N2B—C19C157.9 (12)C23C—C22C—C27C123 (3)
C3B—N3B—C29B165.0 (3)C23C—C22C—C21C122 (2)
C3B—N3B—C29C152.5 (14)C19C—C28C—C27C114 (2)
N1B—C1B—Fe1B173.4 (2)C19C—C28C—H28C122.8
N2B—C2B—Fe1B178.2 (3)C27C—C28C—H28C122.8
N3B—C3B—Fe1B175.0 (3)C24C—C23C—C22C117 (3)
O1B—C4B—Fe1B135.8 (2)C24C—C23C—H23C121.7
O1B—C4B—C5B127.7 (3)C22C—C23C—H23C121.7
O1B—C4B—C8B127.9 (3)
Fe1A—C4A—C5A—C6A−61.44 (18)O1B—C4B—C8B—C7B−169.1 (3)
Fe1A—C4A—C5A—C39A132.8 (3)O1B—C4B—C8B—C57B−5.2 (5)
Fe1A—C4A—C8A—C7A61.26 (17)N1B—C9B—C10B—C11B−178.6 (3)
Fe1A—C4A—C8A—C57A−132.7 (3)N1B—C9B—C18B—C17B178.2 (3)
Fe1A—C5A—C6A—C7A−60.74 (17)N2B—C19B—C20B—C21B179.5 (3)
Fe1A—C5A—C6A—C45A130.8 (3)N2B—C19B—C28B—C27B179.0 (3)
Fe1A—C5A—C39A—C40A−55.7 (4)N2B—C19C—C20C—C21C169 (3)
Fe1A—C5A—C39A—C44A127.9 (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—C51A129.6 (3)N3B—C29B—C38B—C37B178.4 (3)
Fe1A—C6A—C45A—C46A−26.3 (4)N3B—C29C—C38C—C37C−167 (2)
Fe1A—C6A—C45A—C50A154.1 (2)N3B—C29C—C30C—C31C167 (3)
Fe1A—C7A—C8A—C4A−69.26 (19)C1B—N1B—C9B—C10B156.2 (9)
Fe1A—C7A—C8A—C57A124.9 (3)C1B—N1B—C9B—C18B−22.3 (11)
Fe1A—C7A—C51A—C52A−151.0 (2)C2B—N2B—C19C—C20C14 (6)
Fe1A—C7A—C51A—C56A32.5 (4)C2B—N2B—C19C—C28C−176 (2)
Fe1A—C8A—C57A—C58A−132.2 (3)C3B—N3B—C29B—C30B131.6 (11)
Fe1A—C8A—C57A—C62A50.9 (4)C3B—N3B—C29B—C38B−48.0 (14)
O1A—C4A—C5A—Fe1A−126.0 (3)C3B—N3B—C29C—C38C161 (2)
O1A—C4A—C5A—C6A172.5 (3)C3B—N3B—C29C—C30C−5 (6)
O1A—C4A—C5A—C39A6.8 (5)C4B—C5B—C6B—Fe1B71.13 (19)
O1A—C4A—C8A—Fe1A126.1 (3)C4B—C5B—C6B—C7B9.7 (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—C40B135.0 (3)
N1A—C9A—C10A—C11A−177.3 (3)C4B—C5B—C39B—C44B−45.2 (4)
N1A—C9A—C18A—C17A177.3 (2)C4B—C8B—C57B—C58B−41.2 (4)
N2A—C19A—C20A—C21A−177.0 (3)C4B—C8B—C57B—C62B144.8 (3)
N2A—C19A—C28A—C27A175.9 (3)C5B—C4B—C8B—Fe1B−46.74 (18)
N3A—C29A—C30A—C31A−177.0 (3)C5B—C4B—C8B—C7B15.8 (3)
N3A—C29A—C38A—C37A176.8 (3)C5B—C4B—C8B—C57B179.7 (3)
C1A—N1A—C9A—C10A−3.5 (16)C5B—C6B—C7B—Fe1B62.24 (18)
C1A—N1A—C9A—C18A177.4 (13)C5B—C6B—C7B—C8B0.4 (3)
C3A—N3A—C29A—C30A102.3 (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—Fe1A69.26 (19)C5B—C6B—C45B—C50B99.1 (4)
C4A—C5A—C6A—C7A8.5 (3)C5B—C39B—C40B—C41B177.9 (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—C44A21.1 (4)C6B—C5B—C39B—C44B146.6 (3)
C4A—C8A—C57A—C58A−25.2 (4)C6B—C7B—C8B—Fe1B59.85 (18)
C4A—C8A—C57A—C62A157.9 (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—C7A12.9 (3)C6B—C7B—C51B—C52B126.9 (3)
C5A—C4A—C8A—C57A178.9 (2)C6B—C7B—C51B—C56B−46.1 (4)
C5A—C6A—C7A—Fe1A62.81 (18)C6B—C45B—C46B—C47B−175.1 (3)
C5A—C6A—C7A—C8A−0.3 (3)C6B—C45B—C50B—C49B175.8 (3)
C5A—C6A—C7A—C51A−167.6 (2)C7B—C6B—C45B—C46B108.7 (3)
C5A—C6A—C45A—C46A−125.5 (3)C7B—C6B—C45B—C50B−66.8 (4)
C5A—C6A—C45A—C50A54.9 (4)C7B—C8B—C57B—C58B120.2 (3)
C5A—C39A—C40A—C41A−175.7 (3)C7B—C8B—C57B—C62B−53.8 (4)
C5A—C39A—C44A—C43A176.0 (3)C7B—C51B—C52B—C53B−172.7 (3)
C6A—C5A—C39A—C40A34.1 (4)C7B—C51B—C56B—C55B170.3 (3)
C6A—C5A—C39A—C44A−142.3 (3)C8B—C4B—C5B—Fe1B47.35 (19)
C6A—C7A—C8A—Fe1A61.18 (17)C8B—C4B—C5B—C6B−15.6 (3)
C6A—C7A—C8A—C4A−8.1 (3)C8B—C4B—C5B—C39B174.2 (2)
C6A—C7A—C8A—C57A−173.9 (2)C8B—C7B—C51B—C52B−41.9 (4)
C6A—C7A—C51A—C52A114.8 (3)C8B—C7B—C51B—C56B145.1 (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—C61B172.4 (3)
C6A—C45A—C50A—C49A179.3 (3)C9B—C10B—C11B—C12B0.1 (4)
C7A—C6A—C45A—C46A67.9 (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—C58A138.5 (3)C10B—C11B—C12B—C17B0.4 (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—C16B177.3 (3)
C7A—C51A—C56A—C55A173.3 (3)C11B—C12B—C17B—C18B−0.8 (4)
C8A—C4A—C5A—Fe1A48.41 (18)C12B—C13B—C14B—C15B−0.8 (5)
C8A—C4A—C5A—C6A−13.0 (3)C12B—C17B—C18B—C9B0.8 (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—C18B179.5 (3)
C8A—C7A—C51A—C56A133.4 (3)C13B—C14B—C15B—C16B−0.7 (5)
C8A—C57A—C58A—C59A−176.7 (3)C14B—C15B—C16B—C17B0.6 (5)
C8A—C57A—C62A—C61A176.1 (3)C15B—C16B—C17B—C12B0.9 (5)
C9A—C10A—C11A—C12A0.6 (5)C15B—C16B—C17B—C18B179.1 (3)
C10A—C9A—C18A—C17A−1.7 (4)C16B—C17B—C18B—C9B−177.3 (3)
C10A—C11A—C12A—C13A176.4 (3)C17B—C12B—C13B—C14B2.3 (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—C22B1.5 (5)
C11A—C12A—C17A—C16A−178.9 (3)C20B—C19B—C28B—C27B0.5 (5)
C11A—C12A—C17A—C18A3.0 (4)C20B—C21B—C22B—C23B178.9 (3)
C12A—C13A—C14A—C15A−1.1 (5)C20B—C21B—C22B—C27B0.4 (5)
C12A—C17A—C18A—C9A−0.7 (4)C21B—C22B—C23B—C24B−177.3 (4)
C13A—C12A—C17A—C16A1.8 (4)C21B—C22B—C27B—C26B177.3 (4)
C13A—C12A—C17A—C18A−176.4 (3)C21B—C22B—C27B—C28B−1.9 (5)
C13A—C14A—C15A—C16A0.7 (5)C22B—C23B—C24B—C25B−0.3 (6)
C14A—C15A—C16A—C17A1.1 (5)C22B—C27B—C28B—C19B1.4 (6)
C15A—C16A—C17A—C12A−2.3 (4)C23B—C22B—C27B—C26B−1.3 (6)
C15A—C16A—C17A—C18A175.8 (3)C23B—C22B—C27B—C28B179.6 (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—C27B0.7 (6)
C18A—C9A—C10A—C11A1.8 (4)C25B—C26B—C27B—C22B0.3 (6)
C19A—C20A—C21A—C22A0.9 (5)C25B—C26B—C27B—C28B179.5 (4)
C20A—C19A—C28A—C27A−2.3 (5)C26B—C27B—C28B—C19B−177.7 (4)
C20A—C21A—C22A—C23A177.3 (3)C27B—C22B—C23B—C24B1.2 (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—C26A179.0 (3)C30B—C29B—C38B—C37B−1.1 (5)
C21A—C22A—C27A—C28A0.5 (4)C30B—C31B—C32B—C33B179.5 (3)
C22A—C23A—C24A—C25A−0.3 (6)C30B—C31B—C32B—C37B−1.0 (5)
C22A—C27A—C28A—C19A1.5 (4)C31B—C32B—C33B—C34B178.9 (3)
C23A—C22A—C27A—C26A0.0 (5)C31B—C32B—C37B—C36B−179.1 (3)
C23A—C22A—C27A—C28A−178.5 (3)C31B—C32B—C37B—C38B1.3 (5)
C23A—C24A—C25A—C26A0.2 (7)C32B—C33B—C34B—C35B0.5 (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—C36B0.4 (5)
C25A—C26A—C27A—C28A178.4 (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—C24A0.1 (5)C34B—C35B—C36B—C37B−0.1 (6)
C28A—C19A—C20A—C21A1.1 (5)C35B—C36B—C37B—C32B−0.1 (5)
C29A—C30A—C31A—C32A−0.7 (5)C35B—C36B—C37B—C38B179.5 (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—C37A0.8 (5)C38B—C29B—C30B—C31B1.5 (5)
C31A—C32A—C33A—C34A−178.3 (3)C39B—C5B—C6B—Fe1B−119.3 (3)
C31A—C32A—C37A—C36A178.6 (3)C39B—C5B—C6B—C7B179.3 (3)
C31A—C32A—C37A—C38A−0.9 (4)C39B—C5B—C6B—C45B11.7 (5)
C32A—C33A—C34A—C35A−0.5 (6)C39B—C40B—C41B—C42B1.5 (6)
C32A—C37A—C38A—C29A1.0 (4)C40B—C39B—C44B—C43B1.5 (5)
C33A—C32A—C37A—C36A−0.9 (5)C40B—C41B—C42B—C43B−0.7 (7)
C33A—C32A—C37A—C38A179.6 (3)C41B—C42B—C43B—C44B0.3 (6)
C33A—C34A—C35A—C36A−0.5 (6)C42B—C43B—C44B—C39B−0.8 (6)
C34A—C35A—C36A—C37A0.8 (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—C38A179.4 (3)C45B—C6B—C7B—C8B168.9 (2)
C36A—C37A—C38A—C29A−178.5 (3)C45B—C6B—C7B—C51B−1.7 (4)
C37A—C32A—C33A—C34A1.2 (5)C45B—C46B—C47B—C48B0.1 (5)
C38A—C29A—C30A—C31A0.8 (5)C46B—C45B—C50B—C49B0.0 (5)
C39A—C5A—C6A—Fe1A−125.3 (3)C46B—C47B—C48B—C49B−0.9 (5)
C39A—C5A—C6A—C7A174.0 (2)C47B—C48B—C49B—C50B1.3 (5)
C39A—C5A—C6A—C45A5.5 (4)C48B—C49B—C50B—C45B−0.9 (5)
C39A—C40A—C41A—C42A−0.5 (5)C50B—C45B—C46B—C47B0.4 (4)
C40A—C39A—C44A—C43A−0.6 (4)C51B—C7B—C8B—Fe1B−130.0 (3)
C40A—C41A—C42A—C43A0.0 (5)C51B—C7B—C8B—C4B159.7 (3)
C41A—C42A—C43A—C44A0.2 (5)C51B—C7B—C8B—C57B−4.3 (4)
C42A—C43A—C44A—C39A0.1 (5)C51B—C52B—C53B—C54B1.9 (5)
C44A—C39A—C40A—C41A0.8 (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—C8A168.2 (2)C53B—C54B—C55B—C56B−0.1 (5)
C45A—C6A—C7A—C51A0.9 (4)C54B—C55B—C56B—C51B2.6 (5)
C45A—C46A—C47A—C48A−1.0 (5)C56B—C51B—C52B—C53B0.6 (4)
C46A—C45A—C50A—C49A−0.3 (4)C57B—C58B—C59B—C60B−1.3 (5)
C46A—C47A—C48A—C49A0.0 (5)C58B—C57B—C62B—C61B−1.7 (4)
C47A—C48A—C49A—C50A0.8 (5)C58B—C59B—C60B—C61B−0.7 (5)
C48A—C49A—C50A—C45A−0.7 (5)C59B—C60B—C61B—C62B1.5 (5)
C50A—C45A—C46A—C47A1.2 (4)C60B—C61B—C62B—C57B−0.3 (5)
C51A—C7A—C8A—Fe1A−131.8 (3)C62B—C57B—C58B—C59B2.5 (5)
C51A—C7A—C8A—C4A158.9 (3)C29C—C38C—C37C—C36C179 (2)
C51A—C7A—C8A—C57A−6.9 (4)C29C—C38C—C37C—C32C1 (2)
C51A—C52A—C53A—C54A−0.3 (5)C38C—C29C—C30C—C31C4 (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—C56A0.5 (5)C38C—C37C—C32C—C31C−2 (4)
C54A—C55A—C56A—C51A1.7 (5)C37C—C36C—C35C—C34C2 (4)
C56A—C51A—C52A—C53A2.5 (4)C37C—C32C—C31C—C30C4 (5)
C57A—C58A—C59A—C60A0.3 (5)C36C—C37C—C32C—C33C3 (5)
C58A—C57A—C62A—C61A−0.8 (4)C36C—C37C—C32C—C31C179 (3)
C58A—C59A—C60A—C61A−0.5 (5)C36C—C35C—C34C—C33C−5 (5)
C59A—C60A—C61A—C62A0.1 (5)C35C—C34C—C33C—C32C7 (5)
C60A—C61A—C62A—C57A0.6 (5)C34C—C33C—C32C—C37C−6 (5)
C62A—C57A—C58A—C59A0.4 (4)C34C—C33C—C32C—C31C178 (3)
Fe1B—C4B—C5B—C6B−62.95 (18)C33C—C32C—C31C—C30C−180 (3)
Fe1B—C4B—C5B—C39B126.9 (3)C32C—C37C—C36C—C35C−1 (4)
Fe1B—C4B—C8B—C7B62.52 (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—C45B131.1 (3)C27C—C22C—C23C—C24C3 (5)
Fe1B—C5B—C39B—C40B−122.1 (3)C25C—C24C—C23C—C22C−3 (4)
Fe1B—C5B—C39B—C44B57.8 (4)C20C—C19C—C28C—C27C−1 (4)
Fe1B—C6B—C7B—C8B−61.83 (18)C20C—C21C—C22C—C27C1 (4)
Fe1B—C6B—C7B—C51B127.5 (3)C20C—C21C—C22C—C23C−178 (3)
Fe1B—C6B—C45B—C46B16.0 (4)C24C—C25C—C26C—C27C1 (3)
Fe1B—C6B—C45B—C50B−159.4 (2)C21C—C22C—C23C—C24C−178 (3)
Fe1B—C7B—C8B—C4B−70.24 (19)C26C—C27C—C22C—C21C180 (2)
Fe1B—C7B—C8B—C57B125.7 (3)C26C—C27C—C22C—C23C−1 (4)
Fe1B—C7B—C51B—C52B−142.0 (2)C26C—C27C—C28C—C19C180 (2)
Fe1B—C7B—C51B—C56B44.9 (4)C26C—C25C—C24C—C23C1 (2)
Fe1B—C8B—C57B—C58B−149.9 (2)C22C—C27C—C26C—C25C−1 (4)
Fe1B—C8B—C57B—C62B36.1 (4)C22C—C27C—C28C—C19C1 (4)
O1B—C4B—C5B—Fe1B−127.7 (3)C28C—C19C—C20C—C21C0 (4)
O1B—C4B—C5B—C6B169.3 (3)C28C—C27C—C26C—C25C180 (2)
O1B—C4B—C5B—C39B−0.8 (5)C28C—C27C—C22C—C21C−1 (4)
O1B—C4B—C8B—Fe1B128.3 (3)C28C—C27C—C22C—C23C178 (3)
13C NMR chemical shifts (in ppm) for the cyclopentadienone ring carbon atoms (C4, C5, C6, C7, C8) (TPCPD/BTTHI) top
XC4C5/C8C6/C7
O170.0 / 181.482.7 / 71.9104.2 / 111.1
NCH2Tsn/a / 178.379.5 / 66.799.1 / 105.5
N-2-Naphth165.3 / 178.278.5 / 66.698.8 / 104.8
N-2,6-DMP165.9 / n/a77.4 / 65.798.8 / 104.3
NCH2Ph163.6 / n/a76.0 / 63.996.6 / 102.3
NBu163.3 / n/a74.8 / 61.696.1 / 101.0
NtBu161.8 / 175.075.1 / 62.295.6 / 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.

References

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Volume 79| Part 7| July 2023| Pages 626-632
https://doi.org/10.1107/S205698902300498X
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