1. Chemical context
This compound was prepared as part of a Course-based Undergraduate Research Experience (CURE) (Stone et al., 2020
; Huang et al., 2019
). The foundation of this CURE was to further examine addition reactions to tricarbonyl(tropone)iron(0) (I) and tricarbonyl(η5-ketocycloheptadienyl)iron(0) tetrafluoroborate (II) (Fig. 1
). The research focus of one author lies in the synthesis of unique and diverse azapolycyclic skeletons from common synthetic building blocks such as compound I due to the biological importance of such scaffolds. Although seven-membered carbocyclic rings are found in a number of biologically active natural products (Shoemaker & Griffith, 2021
), their synthesis tends to present a greater challenge compared to similar five- or six-membered rings because of the increased enthalpic and entropic barriers associated with their formation (Phelan et al., 2020
; Huang et al., 2018
). The addition of a number of different nucleophiles to compound II has previously been reported, including amines (Phelan et al., 2020
), azide, and cyanide (Eisenstadt, 1975
). This raised the question as to whether or not triphenylphosphine would be sufficiently nucleophilic to react with compound II. Previously, the reaction of several phosphines (PEt3, PnPr3, PnBu3 or PMe2Ph) with tricarbonyl(η5-cycloheptadienyl)iron(II) tetrafluoroborate in methylene chloride resulted in the formation of the corresponding tricarbonyl[η4-(5-exo-phosphine)cycloheptadiene]iron(0) tetrafluoroborate (Brown et al., 1982
). Similar to that system, the reaction of compound II and triphenylphosphine resulted in the formation of tricarbonyl[η4-6-exo-(triphenylphosphino)cyclohepta-2,4-dien-1-one]iron(0) tetrafluoroborate (III) (Fig. 1
). Ultimately, this and similar phosphonium salts could be a precursor for Wittig olefinations that would provide efficient access to tropone rings with diverse substituents.
| Figure 1 Tricarbonyl(tropone)iron(0) (I), tricarbonyl(η5-ketocycloheptadienyl)iron(II) tetrafluoroborate (II), and tricarbonyl[η4-6-exo-(triphenylphosphino)cyclohepta-2,4-dien-1-one]iron(0) tetrafluoroborate (III) and the procedure outlining the synthesis of III from I and II. |
3. Supramolecular features
Solid-state stability between the molecules of III within the asymmetric unit is afforded by an array of C—H⋯O and C—H⋯F hydrogen bonds (Table 1
) as determined through PLATON analysis (Spek, 2020
). The two independent tricarbonyl[η4-6-exo-(triphenylphosphino)cyclohepta-2,4-dien-1-one]iron(0) cations from the asymmetric unit lie parallel to the (100) plane and are stabilized by intermolecular C—H⋯O hydrogen bonds. The addition of C—H⋯F hydrogen bonding involving the [BF4]− anions increases the dimensionality of the solid-state structure into both diperiodic sheets and extended 3D networks, which also contain C—H⋯π and Y—X⋯π (Y = B,C; X = F, O) interactions (Table 2
) according to PLATON (Spek, 2020
) (Figs. 3
and 4
). The resulting 3D network was also found to contain solvent-accessible voids of ∼101 Å3 within which the interstitial CH2Cl2 was located (Fig. 5
).
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | C32—H32⋯F5 | 1.00 | 2.37 | 3.198 (3) | 140 | C43—H43⋯F6i | 0.95 | 2.33 | 3.240 (3) | 160 | C44—H44⋯O8ii | 0.95 | 2.56 | 3.467 (3) | 159 | C46—H46⋯F7iii | 0.95 | 2.40 | 3.151 (3) | 136 | C49—H49⋯O7iv | 0.95 | 2.60 | 3.339 (3) | 135 | C50—H50⋯F6iv | 0.95 | 2.53 | 3.471 (3) | 169 | C52—H52⋯O1 | 0.95 | 2.37 | 3.286 (3) | 161 | C53—H53⋯F4iii | 0.95 | 2.66 | 3.500 (3) | 148 | C56—H56⋯F6iv | 0.95 | 2.48 | 3.362 (3) | 155 | C2—H2⋯F3v | 1.00 | 2.50 | 3.493 (3) | 170 | C4—H4⋯F4iii | 1.00 | 2.42 | 3.393 (3) | 165 | C7—H7⋯O5 | 1.00 | 2.34 | 3.192 (3) | 143 | C13—H13⋯F1v | 0.95 | 2.41 | 3.232 (3) | 144 | C19—H19⋯O2vi | 0.95 | 2.51 | 3.393 (3) | 154 | C28—H28⋯O5 | 0.95 | 2.41 | 3.319 (4) | 161 | C57A—H57A⋯F4 | 0.99 | 2.47 | 3.276 (4) | 139 | Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . | |
Cation 1 | Cation 2 | Torsion angle | Value | Torsion angle | Value | Ring 1 | | | | P1—C11—C16—C15 | 175.9 (2) | P2—C39—C40—C41 | −176.5 (2) | C11—C16—C15—C14 | −0.7 (4) | C39—C40—C41—C42 | 1.0 (4) | C16—C15—C14—C13 | −0.7 (4) | C40—C41—C42—C43 | 1.2 (4) | C15—C14—C13—C12 | 1.2 (4) | C41—C42—C43—C44 | −2.2 (4) | C14—C13—C12—C11 | −0.2 (4) | C42—C43—C44—C39 | 0.9 (4) | C13—C12—C11—P1 | −175.4 (2) | C43—C44—C39—P2 | 175.6 (2) | | | | | Ring 2 | | | | P1—C17—C18—C19 | −175.5 (2) | P2—C45—C50—C49 | 178.8 (2) | C17—C18—C19—C20 | −0.1 (4) | C45—C50—C49—C48 | 0.8 (4) | C18—C19—C20—C21 | 0.4 (4) | C50—C49—C48—C47 | −0.1 (4) | C19—C20—C21—C22 | −0.2 (5) | C49—C48—C47—C46 | −1.5 (4) | C20—C21—C22—C17 | −1.2 (4) | C48—C47—C46—C45 | 2.3 (4) | C21—C22—C17—P1 | 176.0 (2) | C47—C46—C45—P2 | 179.7 (2) | | | | | Ring 3 | | | | P1—C23—C28—C27 | −170.3 (2) | P2—C51—C52—C53 | 176.9 (2) | C23—C28—C27—C26 | −1.1 (4) | C51—C52—C53—C54 | 0.1 (4) | C28—C27—C26—C25 | 1.1 (4) | C52—C53—C54—C55 | −0.5 (4) | C27—C26—C25—C24 | 0.1 (5) | C53—C54—C55—C56 | −0.1 (5) | C26—C25—C24—C23 | −1.3 (5) | C54—C55—C56—C51 | 1.2 (5) | C25—C24—C23—P1 | 171.4 (2) | C55—C56—C51—P2 | −177.7 (2) | | |
| Figure 3 View of the C—H⋯O and C—H⋯F hydrogen bonds from the (101) plane of III. When coupled with the C—H⋯π and Y—X⋯π (Y = B, C; X = F, O) interactions, this repeat unit extends into a three-dimensional network. Anisotropic displacement ellipsoids have been set to the 50% probability level. |
| Figure 4 Projection of the C—H⋯π and Y—X⋯π (Y = B, C; X = F, O) interactions in the ac plane of III. Their combination with the hydrogen bonds yields a three-dimensional extended network in the solid state. Anisotropic displacement ellipsoids have been set to the 50% probability level (Cg = ring centroids). |
| Figure 5 View into the (120) plane showing the interstitial CH2Cl2 solvent molecules lying within the solvent-accessible voids of III. These voids are generated from the packing supported by the C—H⋯O and C—H⋯F hydrogen bonds and C—H⋯π and Y—X⋯π (Y = B, C; X = F, O) interactions. The anisotropic displacement ellipsoids for CH2Cl2 have been set to the 50% probability level. |
The Z′ > 1 nature of the structural model for III suggests the presence of structural differences between molecules within the asymmetric unit. Barring differences in the thermal parameters for the various atoms within the independent components, overlaying the tricarbonyl[η4-6-exo-(triphenylphosphino)cyclohepta-2,4-dien-1-one]iron(0) cations and [BF4]− anions showed that the anions had better alignment while differences in the some of the constituent torsion angles within phenyl rings from the tricarbonyl[η4-6-exo-(triphenylphosphino)cyclohepta-2,4-dien-1-one]iron(0) cations were more pronounced visually (Fig. 6
). Table 3
summarizes the torsion angles from the phenyl rings of the tricarbonyl[η4-6-exo-(triphenylphosphino)cyclohepta-2,4-dien-1-one]iron(0) cations.
X—Y⋯Cg | Y⋯Cg | X⋯Cg | X—H⋯Cg | C54—H54⋯Cg2i | 2.99 | 3.929 (3) | 171 | B1—F1⋯Cg1ii | 3.429 (2) | 4.790 (3) | 165.56 (17) | B2—F6⋯Cg3iii | 3.653 (2) | 4.913 (3) | 150.99 (17) | C9—O3⋯Cg2iv | 3.393 (2) | 3.858 (3) | 105.37 (19) | C38—08⋯Cg4v | 3.467 (2) | 3.925 (3) | 105.10 (18) | Symmetry codes: (i) −1 + x, 1 + y, z; (ii) x, 1 + y, z; (iii) 1 + x, −1 + y, z; (iv) 2 − x, 1 − y, 1 − z; (v) 1 − x, 1 − y, 2 − z. | |
| Figure 6 Molecular overlay of between both cations constituting the symmetric unit of III demonstrating that the greatest disparity between them exists within the torsion angles of the the phenyl rings. The first tricarbonyl[η4-6-exo-(triphenylphosphino)cyclohepta-2,4-dien-1-one]iron(0) tetrafluorrborate is in black while the second is in yellow. Anisotropic displacement ellipsoids have been set to the 50% probability level. |
4. Database survey
The structure of this report is not found in the Cambridge Structural Database (CSD version 5.43; Groom et al., 2016
). To date, the structures of six tricarbonyl(η4-tropone derivative)iron(0) compounds have been reported. In addition to the structure of compound I (Dodge, 1964
), three of the remaining reports have one additional substituent in the 6-position, H (Sotokawa et al., 1987
), t-Bu (Coquerel et al., 2002
) and morpholi-4-yl (Huang et al., 2018
). From the various reports, comparison of their structural features suggested that the presence of the formally cationic phosphorous had minimal impact on the bond lengths.
5. Synthesis and crystallization
All chemicals were purchased from commercial vendors and used as is. Compounds I and II were prepared according to literature procedures (Huang et al., 2019
). NMR spectra were obtained in d3-acetonitrile using a Bruker Avance III HD 400 FT-NMR spectrometer. The synthesis was performed using standard Schlenk conditions as outlined in Fig. 1
, but all subsequent manipulations of the product were conducted in air. Compound II (0.0054 g, 0.016 mmol) and triphenylphosphine (0.0043 g, 0.016 mmol) were added to a 50 mL round-bottom flask along with a stir bar. Methylene chloride (12 mL) was added, and the reaction mixture was stirred at room temperature for 30 minutes. A color change from pastel yellow to a darker yellow was observed. The solution was reduced in vacuo to approximately 5 mL and the resulting solution was layered with diethyl ether (7 mL) before being placed in the freezer for 48 h. The sample formed a pastel yellow solid and was filtered via cannula. The solid was dried in vacuo to give the desired product (0.0085 g, 88% yield). Crystals were grown by slow vapor diffusion of diethyl ether at room temperature into a solution of the compound in methylene chloride. 1H NMR (400 MHz, CD3CN): δ 7.87 (m, 9H, Hmeta, Hpara), 7.75 (m, 6H, Hortho), 5.80 (t, J = 6.2 Hz, 1H, H4), 5.20 (t, J = 7.0 Hz, 1H, H1), 4.86 (td, J = 12.7, 4.7 Hz, 1H, H7), 3.21 (dd, J = 13.0, 7.5 Hz, 1H, H3), 3.16 (d, J = 6.6 Hz, 1H, H2), 2.18 (m, 1H, H6A/B), 1.99 (q, J = 12.2 Hz, 1H, H6A/B); 31P{1H} NMR (162 MHz, CD3CN): δ 23.3 (s); 13C{1H} NMR (100 MHz, CD3CN): δ 207.9 (s, No DEPT, C8–10), 202.6 (d, J = 15.4 Hz, No DEPT, C5), 135.9 (d, J = 3.2 Hz, DEPT +, Cpara), 134.8 (d, J = 9.5 Hz, DEPT +, Cmeta), 131.1 (d, J = 12.7 Hz, DEPT +, Cortho), 117.2 (d, J = 81.6 Hz, No DEPT, Cipso), 94.6 (s, DEPT +, C4), 89.8 (s, DEPT +, C1), 56.7 (s, DEPT +, C2), 49.5 (d, J = 7.4 Hz, DEPT +, C3), 41.2 (d, J = 31.8 Hz, DEPT +, C7), 37.2 (s, DEPT –, C6). Peaks were assigned using COSY, HMBC and HSQC NMR spectra. Protons of the tropone ring are labeled by the number of the carbon atom to which they are bonded. IR (cm−1, CH3CN): 2059 (m, Fe—C≡O), 2014 (m, Fe—C≡O), 1966 (vs, Fe—C≡O), 1710 (m, C=O), 1609 (m, C=C).
6. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 4
. All non-hydrogen atoms were refined anisotropically. H atoms bound to carbon were positioned geometrically and constrained to ride on their parent atoms. Uiso(H) values were set to a multiple of Ueq(C) with 1.2 times all CH and CH2 groups.
Crystal data | Chemical formula | [Fe(C28H22O4)(CO)3]BF4·0.5CH2Cl2 | Mr | 638.57 | Crystal system, space group | Triclinic, P![[\overline{1}]](teximages/vu2002fi1.svg) | Temperature (K) | 100 | a, b, c (Å) | 9.9343 (2), 10.9767 (3), 26.4168 (6) | α, β, γ (°) | 86.993 (2), 82.468 (2), 77.300 (2) | V (Å3) | 2785.09 (12) | Z | 4 | Radiation type | Mo Kα | μ (mm−1) | 0.76 | Crystal size (mm) | 0.3 × 0.14 × 0.08 | | Data collection | Diffractometer | Rigaku Oxford Diffraction XtaLAB Mini II | Absorption correction | Analytical (CrysAlis PRO; Rigaku OD, 2023 ) | Tmin, Tmax | 0.841, 0.969 | No. of measured, independent and observed [I > 2σ(I)] reflections | 59046, 9882, 7785 | Rint | 0.054 | (sin θ/λ)max (Å−1) | 0.597 | | Refinement | R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.103, 1.03 | No. of reflections | 9882 | No. of parameters | 730 | No. of restraints | 9 | H-atom treatment | H-atom parameters constrained | Δρmax, Δρmin (e Å−3) | 0.54, −0.43 | Computer programs: CrysAlis PRO (Rigaku OD, 2023 ), SHELXT (Sheldrick, 2015a ), SHELXL2016/6 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ). | |
Supporting information
Tricarbonyl[
η4-6-
exo-(triphenylphosphino)cyclohepta-2,4-dien-1-one]\ iron(0) tetrafluoroborate dichloromethane hemisolvate
top Crystal data top [Fe(C28H22O4)(CO)3]BF4·0.5CH2Cl2 | Z = 4 |
Mr = 638.57 | F(000) = 1300 |
Triclinic, P1 | Dx = 1.523 Mg m−3 |
a = 9.9343 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.9767 (3) Å | Cell parameters from 14608 reflections |
c = 26.4168 (6) Å | θ = 2.3–25.9° |
α = 86.993 (2)° | µ = 0.76 mm−1 |
β = 82.468 (2)° | T = 100 K |
γ = 77.300 (2)° | Block, yellow |
V = 2785.09 (12) Å3 | 0.3 × 0.14 × 0.08 mm |
Data collection top Rigaku Oxford Diffraction XtaLAB Mini II diffractometer | 9882 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Rigaku (Mo) X-ray Source | 7785 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 25.1°, θmin = 2.0° |
ω scans | h = −11→11 |
Absorption correction: analytical (CrysAlisPro; Rigaku OD, 2023) | k = −13→13 |
Tmin = 0.841, Tmax = 0.969 | l = −31→31 |
59046 measured reflections | |
Refinement top Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0554P)2 + 0.9998P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
9882 reflections | Δρmax = 0.54 e Å−3 |
730 parameters | Δρmin = −0.43 e Å−3 |
9 restraints | |
Special details top Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P2 | 0.49890 (7) | 0.80234 (6) | 0.85505 (2) | 0.01236 (16) | |
Fe2 | 0.76338 (4) | 0.40071 (4) | 0.89551 (2) | 0.01306 (11) | |
O5 | 0.8797 (2) | 0.49399 (18) | 0.75394 (7) | 0.0214 (5) | |
O6 | 0.6413 (2) | 0.28814 (19) | 0.81779 (7) | 0.0266 (5) | |
O7 | 0.9804 (2) | 0.18494 (18) | 0.92305 (7) | 0.0231 (5) | |
O8 | 0.5743 (2) | 0.3482 (2) | 0.98587 (7) | 0.0285 (5) | |
C29 | 0.6417 (3) | 0.5823 (2) | 0.89315 (10) | 0.0145 (6) | |
H29 | 0.556816 | 0.593076 | 0.918838 | 0.017* | |
C30 | 0.7655 (3) | 0.5796 (2) | 0.91661 (10) | 0.0149 (6) | |
H30 | 0.756979 | 0.598566 | 0.953652 | 0.018* | |
C31 | 0.8961 (3) | 0.5230 (2) | 0.89111 (10) | 0.0159 (6) | |
H31 | 0.977935 | 0.502297 | 0.910803 | 0.019* | |
C32 | 0.9086 (3) | 0.4713 (3) | 0.84151 (10) | 0.0160 (6) | |
H32 | 0.997745 | 0.409752 | 0.832129 | 0.019* | |
C33 | 0.8442 (3) | 0.5353 (3) | 0.79735 (10) | 0.0155 (6) | |
C34 | 0.7409 (3) | 0.6599 (2) | 0.80507 (10) | 0.0165 (6) | |
H34A | 0.713284 | 0.694001 | 0.771616 | 0.020* | |
H34B | 0.786063 | 0.719880 | 0.819411 | 0.020* | |
C35 | 0.6098 (3) | 0.6455 (2) | 0.84144 (9) | 0.0136 (6) | |
H35 | 0.556541 | 0.595660 | 0.824317 | 0.016* | |
C36 | 0.6867 (3) | 0.3314 (3) | 0.84864 (10) | 0.0175 (6) | |
C37 | 0.8977 (3) | 0.2693 (3) | 0.91181 (10) | 0.0173 (6) | |
C38 | 0.6482 (3) | 0.3682 (3) | 0.95096 (10) | 0.0173 (6) | |
C39 | 0.5932 (3) | 0.8834 (2) | 0.89063 (9) | 0.0122 (6) | |
C40 | 0.6901 (3) | 0.9485 (2) | 0.86506 (10) | 0.0166 (6) | |
H40 | 0.702505 | 0.953906 | 0.828798 | 0.020* | |
C41 | 0.7676 (3) | 1.0048 (3) | 0.89304 (10) | 0.0192 (6) | |
H41 | 0.832112 | 1.049971 | 0.875878 | 0.023* | |
C42 | 0.7511 (3) | 0.9952 (3) | 0.94643 (11) | 0.0200 (7) | |
H42 | 0.803154 | 1.035219 | 0.965383 | 0.024* | |
C43 | 0.6592 (3) | 0.9277 (3) | 0.97171 (10) | 0.0157 (6) | |
H43 | 0.650592 | 0.919132 | 1.007893 | 0.019* | |
C44 | 0.5792 (3) | 0.8722 (2) | 0.94406 (10) | 0.0139 (6) | |
H44 | 0.515241 | 0.826836 | 0.961476 | 0.017* | |
C45 | 0.3386 (3) | 0.7855 (2) | 0.89292 (10) | 0.0134 (6) | |
C46 | 0.3015 (3) | 0.6696 (3) | 0.90128 (10) | 0.0169 (6) | |
H46 | 0.361384 | 0.596876 | 0.886685 | 0.020* | |
C47 | 0.1768 (3) | 0.6603 (3) | 0.93104 (11) | 0.0205 (7) | |
H47 | 0.153518 | 0.581082 | 0.937688 | 0.025* | |
C48 | 0.0867 (3) | 0.7676 (3) | 0.95092 (11) | 0.0201 (7) | |
H48 | 0.000884 | 0.761797 | 0.970466 | 0.024* | |
C49 | 0.1227 (3) | 0.8837 (3) | 0.94208 (10) | 0.0183 (6) | |
H49 | 0.060856 | 0.956466 | 0.955709 | 0.022* | |
C50 | 0.2479 (3) | 0.8940 (3) | 0.91362 (10) | 0.0160 (6) | |
H50 | 0.272247 | 0.973078 | 0.908149 | 0.019* | |
C51 | 0.4586 (3) | 0.8938 (2) | 0.79783 (9) | 0.0142 (6) | |
C52 | 0.4425 (3) | 0.8367 (3) | 0.75349 (10) | 0.0169 (6) | |
H52 | 0.456999 | 0.748360 | 0.752392 | 0.020* | |
C53 | 0.4047 (3) | 0.9112 (3) | 0.71075 (10) | 0.0218 (7) | |
H53 | 0.393439 | 0.873265 | 0.680526 | 0.026* | |
C54 | 0.3839 (3) | 1.0399 (3) | 0.71241 (11) | 0.0262 (7) | |
H54 | 0.359061 | 1.089691 | 0.683175 | 0.031* | |
C55 | 0.3990 (3) | 1.0971 (3) | 0.75671 (11) | 0.0268 (7) | |
H55 | 0.384692 | 1.185501 | 0.757477 | 0.032* | |
C56 | 0.4353 (3) | 1.0245 (3) | 0.79987 (10) | 0.0199 (7) | |
H56 | 0.444019 | 1.063075 | 0.830287 | 0.024* | |
P1 | 0.94285 (7) | 0.20756 (6) | 0.64553 (2) | 0.01226 (16) | |
O1 | 0.5518 (2) | 0.53885 (18) | 0.72809 (7) | 0.0245 (5) | |
Fe1 | 0.70408 (4) | 0.60845 (4) | 0.59115 (2) | 0.01357 (11) | |
C1 | 0.8213 (3) | 0.4256 (2) | 0.60006 (9) | 0.0126 (6) | |
H1 | 0.913470 | 0.411913 | 0.578387 | 0.015* | |
C2 | 0.7095 (3) | 0.4278 (2) | 0.57052 (10) | 0.0160 (6) | |
H2 | 0.731133 | 0.405510 | 0.533685 | 0.019* | |
O2 | 0.4934 (2) | 0.81613 (18) | 0.55330 (8) | 0.0254 (5) | |
C3 | 0.5726 (3) | 0.4871 (3) | 0.58972 (11) | 0.0185 (6) | |
H3 | 0.499787 | 0.506083 | 0.565967 | 0.022* | |
O3 | 0.9219 (2) | 0.6536 (2) | 0.50941 (8) | 0.0273 (5) | |
C4 | 0.5435 (3) | 0.5435 (3) | 0.63893 (10) | 0.0174 (6) | |
H4 | 0.453410 | 0.606242 | 0.643897 | 0.021* | |
O4 | 0.7946 (2) | 0.73153 (19) | 0.67411 (8) | 0.0272 (5) | |
C5 | 0.5929 (3) | 0.4868 (3) | 0.68714 (10) | 0.0174 (6) | |
C6 | 0.6918 (3) | 0.3593 (3) | 0.68483 (10) | 0.0171 (6) | |
H6A | 0.649606 | 0.299488 | 0.668921 | 0.021* | |
H6B | 0.707112 | 0.328216 | 0.719929 | 0.021* | |
C7 | 0.8327 (3) | 0.3667 (2) | 0.65366 (9) | 0.0130 (6) | |
H7 | 0.880827 | 0.416729 | 0.672986 | 0.016* | |
C8 | 0.5753 (3) | 0.7365 (3) | 0.56836 (10) | 0.0173 (6) | |
C9 | 0.8363 (3) | 0.6373 (3) | 0.54088 (11) | 0.0186 (6) | |
C10 | 0.7618 (3) | 0.6834 (3) | 0.64182 (11) | 0.0181 (6) | |
C11 | 0.8592 (3) | 0.1224 (2) | 0.60744 (10) | 0.0125 (6) | |
C12 | 0.8886 (3) | 0.1261 (2) | 0.55398 (10) | 0.0133 (6) | |
H12 | 0.957399 | 0.168329 | 0.538081 | 0.016* | |
C13 | 0.8167 (3) | 0.0676 (2) | 0.52443 (10) | 0.0159 (6) | |
H13 | 0.836029 | 0.070149 | 0.488247 | 0.019* | |
C14 | 0.7169 (3) | 0.0058 (3) | 0.54771 (10) | 0.0186 (6) | |
H14 | 0.669280 | −0.035317 | 0.527338 | 0.022* | |
C15 | 0.6853 (3) | 0.0030 (3) | 0.60082 (10) | 0.0177 (6) | |
H15 | 0.615918 | −0.039006 | 0.616404 | 0.021* | |
C16 | 0.7559 (3) | 0.0620 (2) | 0.63085 (10) | 0.0150 (6) | |
H16 | 0.734259 | 0.061266 | 0.666957 | 0.018* | |
C17 | 1.1110 (3) | 0.2205 (2) | 0.61364 (9) | 0.0139 (6) | |
C18 | 1.2036 (3) | 0.1120 (3) | 0.59409 (9) | 0.0155 (6) | |
H18 | 1.175348 | 0.034497 | 0.595495 | 0.019* | |
C19 | 1.3374 (3) | 0.1205 (3) | 0.57264 (10) | 0.0189 (7) | |
H19 | 1.400826 | 0.047994 | 0.559412 | 0.023* | |
C20 | 1.3790 (3) | 0.2337 (3) | 0.57043 (11) | 0.0221 (7) | |
H20 | 1.470133 | 0.238330 | 0.555546 | 0.026* | |
C21 | 1.2875 (3) | 0.3400 (3) | 0.58992 (11) | 0.0236 (7) | |
H21 | 1.316252 | 0.417319 | 0.588198 | 0.028* | |
C22 | 1.1544 (3) | 0.3338 (3) | 0.61191 (10) | 0.0188 (6) | |
H22 | 1.092670 | 0.406478 | 0.625785 | 0.023* | |
C23 | 0.9730 (3) | 0.1234 (3) | 0.70496 (10) | 0.0157 (6) | |
C24 | 0.9921 (3) | −0.0070 (3) | 0.70735 (11) | 0.0226 (7) | |
H24 | 0.976679 | −0.050371 | 0.679188 | 0.027* | |
C25 | 1.0334 (3) | −0.0724 (3) | 0.75100 (12) | 0.0298 (8) | |
H25 | 1.044555 | −0.160654 | 0.753021 | 0.036* | |
C26 | 1.0588 (3) | −0.0089 (3) | 0.79202 (11) | 0.0272 (8) | |
H26 | 1.087283 | −0.054269 | 0.821806 | 0.033* | |
C27 | 1.0425 (3) | 0.1197 (3) | 0.78950 (10) | 0.0253 (7) | |
H27 | 1.061477 | 0.162045 | 0.817316 | 0.030* | |
C28 | 0.9983 (3) | 0.1875 (3) | 0.74612 (10) | 0.0194 (6) | |
H28 | 0.985532 | 0.275874 | 0.744555 | 0.023* | |
B1 | 1.1632 (3) | 0.7161 (3) | 0.59857 (12) | 0.0190 (7) | |
F1 | 1.06555 (19) | 0.81871 (17) | 0.58349 (7) | 0.0392 (5) | |
F2 | 1.09598 (19) | 0.62678 (16) | 0.62366 (7) | 0.0344 (5) | |
F3 | 1.25338 (19) | 0.66298 (17) | 0.55619 (6) | 0.0332 (5) | |
F4 | 1.24188 (19) | 0.75704 (18) | 0.63210 (7) | 0.0371 (5) | |
B2 | 1.2845 (4) | 0.2994 (3) | 0.90769 (14) | 0.0241 (8) | |
F5 | 1.2026 (2) | 0.3128 (2) | 0.86803 (8) | 0.0563 (6) | |
F6 | 1.3542 (2) | 0.17533 (15) | 0.91095 (6) | 0.0358 (5) | |
F7 | 1.38046 (19) | 0.37573 (18) | 0.89795 (8) | 0.0454 (5) | |
F8 | 1.1993 (2) | 0.33346 (18) | 0.95371 (7) | 0.0453 (5) | |
Cl1A | 1.25733 (10) | 0.41520 (8) | 0.72180 (3) | 0.0411 (2) | |
Cl2A | 1.18892 (9) | 0.61367 (8) | 0.79693 (3) | 0.0331 (2) | |
C57A | 1.1926 (4) | 0.5766 (3) | 0.73249 (11) | 0.0316 (7) | |
H57A | 1.251916 | 0.624921 | 0.710549 | 0.038* | |
H57B | 1.097398 | 0.601362 | 0.722659 | 0.038* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P2 | 0.0146 (4) | 0.0111 (4) | 0.0105 (3) | −0.0010 (3) | −0.0010 (3) | −0.0018 (3) |
Fe2 | 0.0128 (2) | 0.0127 (2) | 0.0132 (2) | −0.00214 (16) | −0.00068 (16) | −0.00078 (15) |
O5 | 0.0223 (11) | 0.0224 (12) | 0.0170 (10) | −0.0010 (9) | 0.0020 (9) | −0.0053 (8) |
O6 | 0.0321 (13) | 0.0305 (13) | 0.0221 (11) | −0.0144 (10) | −0.0070 (10) | −0.0037 (10) |
O7 | 0.0209 (11) | 0.0180 (12) | 0.0293 (11) | −0.0023 (10) | −0.0039 (9) | 0.0023 (9) |
O8 | 0.0297 (13) | 0.0345 (14) | 0.0203 (11) | −0.0111 (11) | 0.0054 (10) | 0.0043 (10) |
C29 | 0.0149 (15) | 0.0135 (15) | 0.0123 (13) | −0.0005 (12) | 0.0044 (11) | −0.0014 (11) |
C30 | 0.0204 (15) | 0.0107 (14) | 0.0149 (13) | −0.0050 (12) | −0.0041 (12) | −0.0002 (11) |
C31 | 0.0180 (15) | 0.0121 (15) | 0.0194 (14) | −0.0062 (12) | −0.0051 (12) | 0.0019 (11) |
C32 | 0.0106 (14) | 0.0142 (15) | 0.0230 (15) | −0.0035 (12) | 0.0009 (12) | −0.0011 (12) |
C33 | 0.0137 (14) | 0.0141 (15) | 0.0185 (14) | −0.0059 (12) | 0.0034 (12) | −0.0006 (11) |
C34 | 0.0195 (15) | 0.0147 (15) | 0.0128 (13) | −0.0009 (12) | 0.0029 (11) | −0.0003 (11) |
C35 | 0.0151 (14) | 0.0111 (14) | 0.0127 (13) | 0.0011 (11) | −0.0014 (11) | −0.0019 (11) |
C36 | 0.0163 (15) | 0.0162 (16) | 0.0181 (15) | −0.0027 (12) | 0.0015 (12) | 0.0036 (12) |
C37 | 0.0190 (16) | 0.0166 (16) | 0.0171 (14) | −0.0066 (13) | 0.0003 (12) | −0.0024 (12) |
C38 | 0.0187 (16) | 0.0125 (15) | 0.0204 (15) | −0.0002 (12) | −0.0075 (13) | 0.0006 (12) |
C39 | 0.0112 (14) | 0.0103 (14) | 0.0140 (13) | 0.0010 (11) | −0.0025 (11) | −0.0017 (10) |
C40 | 0.0203 (15) | 0.0146 (15) | 0.0132 (13) | −0.0024 (12) | 0.0013 (12) | −0.0007 (11) |
C41 | 0.0157 (15) | 0.0205 (16) | 0.0219 (15) | −0.0079 (13) | 0.0039 (12) | −0.0027 (12) |
C42 | 0.0164 (15) | 0.0222 (17) | 0.0215 (15) | −0.0020 (13) | −0.0035 (12) | −0.0089 (12) |
C43 | 0.0154 (15) | 0.0174 (16) | 0.0122 (13) | 0.0011 (12) | −0.0009 (11) | −0.0029 (11) |
C44 | 0.0146 (14) | 0.0104 (14) | 0.0149 (13) | −0.0006 (11) | 0.0022 (11) | −0.0018 (11) |
C45 | 0.0139 (14) | 0.0151 (15) | 0.0121 (13) | −0.0029 (12) | −0.0055 (11) | −0.0006 (11) |
C46 | 0.0157 (15) | 0.0161 (16) | 0.0189 (14) | −0.0025 (12) | −0.0023 (12) | −0.0042 (12) |
C47 | 0.0202 (16) | 0.0203 (17) | 0.0241 (15) | −0.0091 (13) | −0.0076 (13) | 0.0030 (12) |
C48 | 0.0120 (15) | 0.0276 (18) | 0.0216 (15) | −0.0054 (13) | −0.0027 (12) | −0.0015 (13) |
C49 | 0.0144 (15) | 0.0215 (17) | 0.0170 (14) | 0.0016 (12) | −0.0022 (12) | −0.0040 (12) |
C50 | 0.0192 (15) | 0.0127 (15) | 0.0164 (14) | −0.0019 (12) | −0.0055 (12) | −0.0021 (11) |
C51 | 0.0151 (14) | 0.0132 (15) | 0.0126 (13) | −0.0005 (12) | −0.0003 (11) | −0.0002 (11) |
C52 | 0.0161 (15) | 0.0173 (16) | 0.0174 (14) | −0.0041 (12) | 0.0000 (12) | −0.0042 (12) |
C53 | 0.0190 (16) | 0.0320 (19) | 0.0136 (14) | −0.0036 (14) | −0.0025 (12) | −0.0015 (13) |
C54 | 0.0269 (18) | 0.033 (2) | 0.0160 (15) | −0.0023 (15) | −0.0049 (13) | 0.0083 (13) |
C55 | 0.0343 (19) | 0.0172 (17) | 0.0269 (17) | −0.0002 (14) | −0.0066 (14) | 0.0023 (13) |
C56 | 0.0286 (17) | 0.0125 (15) | 0.0175 (14) | −0.0005 (13) | −0.0050 (13) | −0.0004 (12) |
P1 | 0.0142 (4) | 0.0106 (4) | 0.0114 (3) | −0.0015 (3) | −0.0006 (3) | −0.0023 (3) |
O1 | 0.0242 (12) | 0.0230 (12) | 0.0231 (11) | −0.0030 (9) | 0.0086 (9) | −0.0082 (9) |
Fe1 | 0.0123 (2) | 0.0118 (2) | 0.0157 (2) | −0.00230 (16) | 0.00080 (16) | −0.00029 (16) |
C1 | 0.0148 (14) | 0.0106 (14) | 0.0109 (12) | −0.0016 (11) | 0.0028 (11) | −0.0023 (10) |
C2 | 0.0225 (16) | 0.0093 (14) | 0.0171 (14) | −0.0055 (12) | −0.0020 (12) | −0.0013 (11) |
O2 | 0.0208 (12) | 0.0184 (12) | 0.0360 (12) | −0.0016 (10) | −0.0063 (10) | 0.0042 (10) |
C3 | 0.0164 (15) | 0.0165 (16) | 0.0246 (15) | −0.0080 (12) | −0.0049 (12) | 0.0059 (12) |
O3 | 0.0255 (12) | 0.0338 (14) | 0.0228 (11) | −0.0115 (10) | 0.0045 (10) | 0.0023 (9) |
C4 | 0.0087 (14) | 0.0159 (16) | 0.0258 (15) | −0.0025 (12) | 0.0033 (12) | 0.0025 (12) |
O4 | 0.0359 (13) | 0.0264 (13) | 0.0219 (11) | −0.0117 (10) | −0.0031 (10) | −0.0035 (10) |
C5 | 0.0112 (14) | 0.0169 (16) | 0.0230 (15) | −0.0059 (12) | 0.0066 (12) | 0.0000 (12) |
C6 | 0.0187 (15) | 0.0176 (16) | 0.0130 (13) | −0.0031 (12) | 0.0047 (12) | −0.0009 (11) |
C7 | 0.0158 (14) | 0.0106 (14) | 0.0122 (13) | −0.0021 (11) | 0.0004 (11) | −0.0031 (11) |
C8 | 0.0152 (15) | 0.0172 (16) | 0.0205 (15) | −0.0087 (13) | 0.0038 (12) | −0.0022 (12) |
C9 | 0.0209 (16) | 0.0161 (16) | 0.0191 (15) | −0.0027 (13) | −0.0057 (13) | −0.0001 (12) |
C10 | 0.0178 (15) | 0.0135 (15) | 0.0193 (15) | −0.0012 (12) | 0.0058 (12) | 0.0038 (12) |
C11 | 0.0132 (14) | 0.0097 (14) | 0.0139 (13) | −0.0005 (11) | −0.0018 (11) | −0.0017 (11) |
C12 | 0.0123 (14) | 0.0115 (15) | 0.0148 (13) | −0.0017 (11) | 0.0019 (11) | −0.0012 (11) |
C13 | 0.0170 (15) | 0.0168 (15) | 0.0124 (13) | 0.0002 (12) | −0.0016 (11) | −0.0026 (11) |
C14 | 0.0190 (16) | 0.0179 (16) | 0.0205 (14) | −0.0052 (13) | −0.0044 (12) | −0.0058 (12) |
C15 | 0.0163 (15) | 0.0154 (15) | 0.0209 (14) | −0.0053 (12) | 0.0025 (12) | −0.0011 (12) |
C16 | 0.0185 (15) | 0.0134 (15) | 0.0126 (13) | −0.0026 (12) | −0.0010 (11) | −0.0014 (11) |
C17 | 0.0146 (14) | 0.0155 (15) | 0.0111 (13) | −0.0011 (12) | −0.0026 (11) | −0.0019 (11) |
C18 | 0.0174 (15) | 0.0162 (15) | 0.0139 (13) | −0.0036 (12) | −0.0045 (11) | −0.0028 (11) |
C19 | 0.0129 (15) | 0.0249 (17) | 0.0161 (14) | 0.0047 (13) | −0.0049 (12) | −0.0039 (12) |
C20 | 0.0118 (15) | 0.0287 (18) | 0.0256 (16) | −0.0050 (13) | −0.0007 (12) | −0.0007 (13) |
C21 | 0.0170 (16) | 0.0215 (17) | 0.0341 (17) | −0.0074 (13) | −0.0035 (13) | −0.0022 (14) |
C22 | 0.0169 (15) | 0.0156 (16) | 0.0242 (15) | −0.0025 (12) | −0.0038 (12) | −0.0055 (12) |
C23 | 0.0139 (14) | 0.0177 (15) | 0.0126 (13) | 0.0000 (12) | 0.0023 (11) | 0.0015 (11) |
C24 | 0.0269 (17) | 0.0185 (17) | 0.0221 (15) | −0.0032 (13) | −0.0052 (13) | −0.0004 (12) |
C25 | 0.0345 (19) | 0.0215 (18) | 0.0311 (18) | −0.0018 (15) | −0.0054 (15) | 0.0066 (14) |
C26 | 0.0226 (17) | 0.038 (2) | 0.0151 (15) | 0.0037 (15) | −0.0015 (13) | 0.0095 (14) |
C27 | 0.0242 (17) | 0.034 (2) | 0.0129 (14) | 0.0034 (14) | 0.0005 (12) | −0.0068 (13) |
C28 | 0.0185 (16) | 0.0220 (17) | 0.0156 (14) | −0.0003 (13) | −0.0004 (12) | −0.0040 (12) |
B1 | 0.0183 (18) | 0.0163 (18) | 0.0203 (17) | 0.0000 (14) | −0.0015 (14) | −0.0007 (14) |
F1 | 0.0316 (11) | 0.0366 (12) | 0.0390 (11) | 0.0082 (9) | 0.0001 (9) | 0.0159 (9) |
F2 | 0.0425 (12) | 0.0244 (10) | 0.0363 (10) | −0.0137 (9) | 0.0039 (9) | 0.0046 (8) |
F3 | 0.0360 (11) | 0.0324 (11) | 0.0274 (10) | −0.0036 (9) | 0.0068 (8) | −0.0092 (8) |
F4 | 0.0352 (11) | 0.0458 (13) | 0.0344 (10) | −0.0141 (9) | −0.0067 (9) | −0.0093 (9) |
B2 | 0.0226 (19) | 0.0179 (19) | 0.0313 (19) | −0.0027 (15) | −0.0054 (16) | 0.0039 (15) |
F5 | 0.0337 (12) | 0.0883 (18) | 0.0516 (13) | −0.0204 (12) | −0.0224 (10) | 0.0308 (12) |
F6 | 0.0588 (13) | 0.0175 (10) | 0.0240 (9) | 0.0039 (9) | −0.0005 (9) | 0.0003 (7) |
F7 | 0.0285 (11) | 0.0290 (12) | 0.0799 (16) | −0.0121 (9) | 0.0014 (10) | −0.0064 (11) |
F8 | 0.0466 (13) | 0.0345 (12) | 0.0496 (12) | −0.0045 (10) | 0.0119 (10) | −0.0154 (10) |
Cl1A | 0.0475 (6) | 0.0249 (5) | 0.0523 (5) | −0.0028 (4) | −0.0173 (4) | −0.0064 (4) |
Cl2A | 0.0452 (5) | 0.0323 (5) | 0.0239 (4) | −0.0120 (4) | −0.0065 (4) | 0.0026 (3) |
C57A | 0.041 (2) | 0.0278 (15) | 0.0252 (14) | −0.0055 (15) | −0.0040 (14) | 0.0010 (13) |
Geometric parameters (Å, º) top P2—C35 | 1.853 (3) | Fe1—C2 | 2.071 (3) |
P2—C39 | 1.799 (3) | Fe1—C3 | 2.065 (3) |
P2—C45 | 1.807 (3) | Fe1—C4 | 2.127 (3) |
P2—C51 | 1.810 (3) | Fe1—C8 | 1.816 (3) |
Fe2—C29 | 2.094 (3) | Fe1—C9 | 1.809 (3) |
Fe2—C30 | 2.074 (3) | Fe1—C10 | 1.822 (3) |
Fe2—C31 | 2.068 (3) | C1—H1 | 1.0000 |
Fe2—C32 | 2.134 (3) | C1—C2 | 1.434 (4) |
Fe2—C36 | 1.815 (3) | C1—C7 | 1.533 (3) |
Fe2—C37 | 1.812 (3) | C2—H2 | 1.0000 |
Fe2—C38 | 1.808 (3) | C2—C3 | 1.412 (4) |
O5—C33 | 1.234 (3) | O2—C8 | 1.149 (3) |
O6—C36 | 1.150 (3) | C3—H3 | 1.0000 |
O7—C37 | 1.149 (3) | C3—C4 | 1.436 (4) |
O8—C38 | 1.145 (3) | O3—C9 | 1.145 (3) |
C29—H29 | 1.0000 | C4—H4 | 1.0000 |
C29—C30 | 1.442 (4) | C4—C5 | 1.482 (4) |
C29—C35 | 1.538 (3) | O4—C10 | 1.144 (3) |
C30—H30 | 1.0000 | C5—C6 | 1.522 (4) |
C30—C31 | 1.408 (4) | C6—H6A | 0.9900 |
C31—H31 | 1.0000 | C6—H6B | 0.9900 |
C31—C32 | 1.435 (4) | C6—C7 | 1.544 (4) |
C32—H32 | 1.0000 | C7—H7 | 1.0000 |
C32—C33 | 1.475 (4) | C11—C12 | 1.404 (3) |
C33—C34 | 1.524 (4) | C11—C16 | 1.402 (4) |
C34—H34A | 0.9900 | C12—H12 | 0.9500 |
C34—H34B | 0.9900 | C12—C13 | 1.390 (4) |
C34—C35 | 1.546 (4) | C13—H13 | 0.9500 |
C35—H35 | 1.0000 | C13—C14 | 1.384 (4) |
C39—C40 | 1.405 (4) | C14—H14 | 0.9500 |
C39—C44 | 1.401 (3) | C14—C15 | 1.397 (4) |
C40—H40 | 0.9500 | C15—H15 | 0.9500 |
C40—C41 | 1.388 (4) | C15—C16 | 1.393 (4) |
C41—H41 | 0.9500 | C16—H16 | 0.9500 |
C41—C42 | 1.399 (4) | C17—C18 | 1.411 (4) |
C42—H42 | 0.9500 | C17—C22 | 1.400 (4) |
C42—C43 | 1.383 (4) | C18—H18 | 0.9500 |
C43—H43 | 0.9500 | C18—C19 | 1.396 (4) |
C43—C44 | 1.396 (4) | C19—H19 | 0.9500 |
C44—H44 | 0.9500 | C19—C20 | 1.389 (4) |
C45—C46 | 1.399 (4) | C20—H20 | 0.9500 |
C45—C50 | 1.413 (4) | C20—C21 | 1.388 (4) |
C46—H46 | 0.9500 | C21—H21 | 0.9500 |
C46—C47 | 1.399 (4) | C21—C22 | 1.388 (4) |
C47—H47 | 0.9500 | C22—H22 | 0.9500 |
C47—C48 | 1.393 (4) | C23—C24 | 1.402 (4) |
C48—H48 | 0.9500 | C23—C28 | 1.403 (4) |
C48—C49 | 1.398 (4) | C24—H24 | 0.9500 |
C49—H49 | 0.9500 | C24—C25 | 1.386 (4) |
C49—C50 | 1.390 (4) | C25—H25 | 0.9500 |
C50—H50 | 0.9500 | C25—C26 | 1.397 (4) |
C51—C52 | 1.400 (4) | C26—H26 | 0.9500 |
C51—C56 | 1.405 (4) | C26—C27 | 1.384 (4) |
C52—H52 | 0.9500 | C27—H27 | 0.9500 |
C52—C53 | 1.401 (4) | C27—C28 | 1.400 (4) |
C53—H53 | 0.9500 | C28—H28 | 0.9500 |
C53—C54 | 1.384 (4) | B1—F1 | 1.394 (4) |
C54—H54 | 0.9500 | B1—F2 | 1.396 (4) |
C54—C55 | 1.397 (4) | B1—F3 | 1.404 (3) |
C55—H55 | 0.9500 | B1—F4 | 1.406 (4) |
C55—C56 | 1.397 (4) | B2—F5 | 1.392 (4) |
C56—H56 | 0.9500 | B2—F6 | 1.389 (4) |
P1—C7 | 1.853 (3) | B2—F7 | 1.393 (4) |
P1—C11 | 1.799 (3) | B2—F8 | 1.405 (4) |
P1—C17 | 1.801 (3) | Cl1A—C57A | 1.771 (3) |
P1—C23 | 1.805 (3) | Cl2A—C57A | 1.765 (3) |
O1—C5 | 1.229 (3) | C57A—H57A | 0.9900 |
Fe1—C1 | 2.106 (3) | C57A—H57B | 0.9900 |
| | | |
C39—P2—C35 | 107.22 (12) | C3—Fe1—C1 | 72.32 (11) |
C39—P2—C45 | 109.80 (12) | C3—Fe1—C2 | 39.93 (11) |
C39—P2—C51 | 108.45 (12) | C3—Fe1—C4 | 40.04 (10) |
C45—P2—C35 | 109.27 (12) | C8—Fe1—C1 | 159.35 (11) |
C45—P2—C51 | 109.02 (12) | C8—Fe1—C2 | 119.34 (12) |
C51—P2—C35 | 113.05 (12) | C8—Fe1—C3 | 90.88 (12) |
C29—Fe2—C32 | 85.14 (10) | C8—Fe1—C4 | 89.74 (11) |
C30—Fe2—C29 | 40.48 (10) | C8—Fe1—C10 | 101.08 (12) |
C30—Fe2—C32 | 72.09 (10) | C9—Fe1—C1 | 89.05 (11) |
C31—Fe2—C29 | 72.52 (11) | C9—Fe1—C2 | 95.78 (12) |
C31—Fe2—C30 | 39.75 (10) | C9—Fe1—C3 | 127.05 (12) |
C31—Fe2—C32 | 39.90 (10) | C9—Fe1—C4 | 167.04 (12) |
C36—Fe2—C29 | 98.70 (11) | C9—Fe1—C8 | 91.88 (12) |
C36—Fe2—C30 | 136.74 (11) | C9—Fe1—C10 | 96.79 (12) |
C36—Fe2—C31 | 134.13 (11) | C10—Fe1—C1 | 99.29 (11) |
C36—Fe2—C32 | 95.62 (11) | C10—Fe1—C2 | 137.07 (11) |
C37—Fe2—C29 | 160.40 (12) | C10—Fe1—C3 | 134.26 (11) |
C37—Fe2—C30 | 120.23 (12) | C10—Fe1—C4 | 95.51 (11) |
C37—Fe2—C31 | 92.41 (12) | Fe1—C1—H1 | 112.0 |
C37—Fe2—C32 | 91.19 (11) | C2—C1—Fe1 | 68.62 (15) |
C37—Fe2—C36 | 100.82 (12) | C2—C1—H1 | 112.0 |
C38—Fe2—C29 | 88.42 (11) | C2—C1—C7 | 125.5 (2) |
C38—Fe2—C30 | 95.26 (11) | C7—C1—Fe1 | 119.90 (17) |
C38—Fe2—C31 | 126.49 (11) | C7—C1—H1 | 112.0 |
C38—Fe2—C32 | 166.34 (12) | Fe1—C2—H2 | 119.4 |
C38—Fe2—C36 | 97.26 (12) | C1—C2—Fe1 | 71.24 (15) |
C38—Fe2—C37 | 90.87 (12) | C1—C2—H2 | 119.4 |
Fe2—C29—H29 | 111.9 | C3—C2—Fe1 | 69.78 (15) |
C30—C29—Fe2 | 69.04 (15) | C3—C2—C1 | 119.7 (2) |
C30—C29—H29 | 111.9 | C3—C2—H2 | 119.4 |
C30—C29—C35 | 125.5 (2) | Fe1—C3—H3 | 118.9 |
C35—C29—Fe2 | 119.85 (17) | C2—C3—Fe1 | 70.29 (15) |
C35—C29—H29 | 111.9 | C2—C3—H3 | 118.9 |
Fe2—C30—H30 | 119.5 | C2—C3—C4 | 120.8 (2) |
C29—C30—Fe2 | 70.48 (15) | C4—C3—Fe1 | 72.34 (16) |
C29—C30—H30 | 119.5 | C4—C3—H3 | 118.9 |
C31—C30—Fe2 | 69.88 (15) | Fe1—C4—H4 | 114.0 |
C31—C30—C29 | 119.4 (2) | C3—C4—Fe1 | 67.62 (15) |
C31—C30—H30 | 119.5 | C3—C4—H4 | 114.0 |
Fe2—C31—H31 | 118.8 | C3—C4—C5 | 126.6 (2) |
C30—C31—Fe2 | 70.37 (16) | C5—C4—Fe1 | 111.10 (18) |
C30—C31—H31 | 118.8 | C5—C4—H4 | 114.0 |
C30—C31—C32 | 121.2 (2) | O1—C5—C4 | 121.2 (3) |
C32—C31—Fe2 | 72.50 (15) | O1—C5—C6 | 120.7 (3) |
C32—C31—H31 | 118.8 | C4—C5—C6 | 118.0 (2) |
Fe2—C32—H32 | 114.1 | C5—C6—H6A | 109.4 |
C31—C32—Fe2 | 67.59 (15) | C5—C6—H6B | 109.4 |
C31—C32—H32 | 114.1 | C5—C6—C7 | 111.0 (2) |
C31—C32—C33 | 125.5 (2) | H6A—C6—H6B | 108.0 |
C33—C32—Fe2 | 112.39 (18) | C7—C6—H6A | 109.4 |
C33—C32—H32 | 114.1 | C7—C6—H6B | 109.4 |
O5—C33—C32 | 121.1 (2) | P1—C7—H7 | 108.6 |
O5—C33—C34 | 119.6 (2) | C1—C7—P1 | 106.93 (17) |
C32—C33—C34 | 119.1 (2) | C1—C7—C6 | 114.4 (2) |
C33—C34—H34A | 109.3 | C1—C7—H7 | 108.6 |
C33—C34—H34B | 109.3 | C6—C7—P1 | 109.73 (18) |
C33—C34—C35 | 111.5 (2) | C6—C7—H7 | 108.6 |
H34A—C34—H34B | 108.0 | O2—C8—Fe1 | 178.8 (3) |
C35—C34—H34A | 109.3 | O3—C9—Fe1 | 178.6 (3) |
C35—C34—H34B | 109.3 | O4—C10—Fe1 | 178.2 (3) |
P2—C35—H35 | 108.9 | C12—C11—P1 | 119.8 (2) |
C29—C35—P2 | 107.10 (17) | C16—C11—P1 | 119.85 (19) |
C29—C35—C34 | 113.7 (2) | C16—C11—C12 | 120.1 (2) |
C29—C35—H35 | 108.9 | C11—C12—H12 | 120.1 |
C34—C35—P2 | 109.12 (18) | C13—C12—C11 | 119.8 (2) |
C34—C35—H35 | 108.9 | C13—C12—H12 | 120.1 |
O6—C36—Fe2 | 177.8 (2) | C12—C13—H13 | 120.0 |
O7—C37—Fe2 | 178.2 (3) | C14—C13—C12 | 120.0 (2) |
O8—C38—Fe2 | 179.3 (3) | C14—C13—H13 | 120.0 |
C40—C39—P2 | 120.3 (2) | C13—C14—H14 | 119.6 |
C44—C39—P2 | 119.8 (2) | C13—C14—C15 | 120.8 (3) |
C44—C39—C40 | 119.7 (2) | C15—C14—H14 | 119.6 |
C39—C40—H40 | 120.2 | C14—C15—H15 | 120.1 |
C41—C40—C39 | 119.7 (2) | C16—C15—C14 | 119.8 (3) |
C41—C40—H40 | 120.2 | C16—C15—H15 | 120.1 |
C40—C41—H41 | 119.9 | C11—C16—H16 | 120.2 |
C40—C41—C42 | 120.3 (3) | C15—C16—C11 | 119.6 (2) |
C42—C41—H41 | 119.9 | C15—C16—H16 | 120.2 |
C41—C42—H42 | 119.9 | C18—C17—P1 | 118.9 (2) |
C43—C42—C41 | 120.3 (3) | C22—C17—P1 | 120.9 (2) |
C43—C42—H42 | 119.9 | C22—C17—C18 | 120.0 (2) |
C42—C43—H43 | 120.0 | C17—C18—H18 | 120.6 |
C42—C43—C44 | 120.0 (2) | C19—C18—C17 | 118.8 (3) |
C44—C43—H43 | 120.0 | C19—C18—H18 | 120.6 |
C39—C44—H44 | 120.0 | C18—C19—H19 | 119.6 |
C43—C44—C39 | 120.1 (3) | C20—C19—C18 | 120.7 (3) |
C43—C44—H44 | 120.0 | C20—C19—H19 | 119.6 |
C46—C45—P2 | 122.0 (2) | C19—C20—H20 | 119.9 |
C46—C45—C50 | 119.8 (3) | C21—C20—C19 | 120.2 (3) |
C50—C45—P2 | 118.2 (2) | C21—C20—H20 | 119.9 |
C45—C46—H46 | 119.9 | C20—C21—H21 | 119.9 |
C47—C46—C45 | 120.3 (3) | C22—C21—C20 | 120.3 (3) |
C47—C46—H46 | 119.9 | C22—C21—H21 | 119.9 |
C46—C47—H47 | 120.1 | C17—C22—H22 | 120.0 |
C48—C47—C46 | 119.8 (3) | C21—C22—C17 | 120.0 (3) |
C48—C47—H47 | 120.1 | C21—C22—H22 | 120.0 |
C47—C48—H48 | 120.0 | C24—C23—P1 | 120.0 (2) |
C47—C48—C49 | 119.9 (3) | C24—C23—C28 | 120.2 (3) |
C49—C48—H48 | 120.0 | C28—C23—P1 | 119.0 (2) |
C48—C49—H49 | 119.6 | C23—C24—H24 | 120.2 |
C50—C49—C48 | 120.9 (3) | C25—C24—C23 | 119.7 (3) |
C50—C49—H49 | 119.6 | C25—C24—H24 | 120.2 |
C45—C50—H50 | 120.4 | C24—C25—H25 | 119.9 |
C49—C50—C45 | 119.2 (3) | C24—C25—C26 | 120.2 (3) |
C49—C50—H50 | 120.4 | C26—C25—H25 | 119.9 |
C52—C51—P2 | 121.0 (2) | C25—C26—H26 | 119.8 |
C52—C51—C56 | 120.5 (2) | C27—C26—C25 | 120.4 (3) |
C56—C51—P2 | 118.3 (2) | C27—C26—H26 | 119.8 |
C51—C52—H52 | 120.3 | C26—C27—H27 | 119.9 |
C51—C52—C53 | 119.3 (3) | C26—C27—C28 | 120.2 (3) |
C53—C52—H52 | 120.3 | C28—C27—H27 | 119.9 |
C52—C53—H53 | 119.9 | C23—C28—H28 | 120.4 |
C54—C53—C52 | 120.2 (3) | C27—C28—C23 | 119.3 (3) |
C54—C53—H53 | 119.9 | C27—C28—H28 | 120.4 |
C53—C54—H54 | 119.7 | F1—B1—F2 | 110.1 (3) |
C53—C54—C55 | 120.6 (3) | F1—B1—F3 | 110.7 (2) |
C55—C54—H54 | 119.7 | F1—B1—F4 | 108.4 (3) |
C54—C55—H55 | 120.0 | F2—B1—F3 | 109.8 (2) |
C56—C55—C54 | 120.1 (3) | F2—B1—F4 | 109.3 (2) |
C56—C55—H55 | 120.0 | F3—B1—F4 | 108.6 (2) |
C51—C56—H56 | 120.4 | F5—B2—F7 | 109.7 (3) |
C55—C56—C51 | 119.3 (3) | F5—B2—F8 | 109.4 (3) |
C55—C56—H56 | 120.4 | F6—B2—F5 | 108.6 (3) |
C11—P1—C7 | 107.74 (12) | F6—B2—F7 | 109.7 (3) |
C11—P1—C17 | 110.56 (12) | F6—B2—F8 | 109.9 (3) |
C11—P1—C23 | 109.76 (13) | F7—B2—F8 | 109.5 (3) |
C17—P1—C7 | 108.54 (12) | Cl1A—C57A—H57A | 109.2 |
C17—P1—C23 | 106.44 (12) | Cl1A—C57A—H57B | 109.2 |
C23—P1—C7 | 113.81 (12) | Cl2A—C57A—Cl1A | 112.05 (17) |
C1—Fe1—C4 | 84.95 (10) | Cl2A—C57A—H57A | 109.2 |
C2—Fe1—C1 | 40.14 (10) | Cl2A—C57A—H57B | 109.2 |
C2—Fe1—C4 | 72.30 (11) | H57A—C57A—H57B | 107.9 |
| | | |
P2—C39—C40—C41 | −176.5 (2) | P1—C11—C12—C13 | −175.4 (2) |
P2—C39—C44—C43 | 175.57 (19) | P1—C11—C16—C15 | 175.9 (2) |
P2—C45—C46—C47 | 179.7 (2) | P1—C17—C18—C19 | −175.46 (19) |
P2—C45—C50—C49 | 178.8 (2) | P1—C17—C22—C21 | 176.0 (2) |
P2—C51—C52—C53 | 176.9 (2) | P1—C23—C24—C25 | 171.4 (2) |
P2—C51—C56—C55 | −177.7 (2) | P1—C23—C28—C27 | −170.3 (2) |
Fe2—C29—C30—C31 | 51.8 (2) | O1—C5—C6—C7 | −116.4 (3) |
Fe2—C29—C35—P2 | 179.24 (13) | Fe1—C1—C2—C3 | −52.1 (2) |
Fe2—C29—C35—C34 | −60.1 (3) | Fe1—C1—C7—P1 | 179.98 (13) |
Fe2—C30—C31—C32 | 53.9 (2) | Fe1—C1—C7—C6 | 58.3 (3) |
Fe2—C31—C32—C33 | 102.3 (3) | Fe1—C2—C3—C4 | −53.9 (2) |
Fe2—C32—C33—O5 | −115.5 (2) | Fe1—C3—C4—C5 | −100.3 (3) |
Fe2—C32—C33—C34 | 69.6 (3) | Fe1—C4—C5—O1 | 109.3 (3) |
O5—C33—C34—C35 | 121.2 (3) | Fe1—C4—C5—C6 | −73.2 (3) |
C29—C30—C31—Fe2 | −52.0 (2) | C1—C2—C3—Fe1 | 52.8 (2) |
C29—C30—C31—C32 | 1.9 (4) | C1—C2—C3—C4 | −1.1 (4) |
C30—C29—C35—P2 | −96.3 (3) | C2—C1—C7—P1 | 96.1 (3) |
C30—C29—C35—C34 | 24.3 (4) | C2—C1—C7—C6 | −25.6 (4) |
C30—C31—C32—Fe2 | −53.0 (2) | C2—C3—C4—Fe1 | 53.0 (2) |
C30—C31—C32—C33 | 49.3 (4) | C2—C3—C4—C5 | −47.4 (4) |
C31—C32—C33—O5 | 166.8 (3) | C3—C4—C5—O1 | −173.5 (3) |
C31—C32—C33—C34 | −8.1 (4) | C3—C4—C5—C6 | 4.0 (4) |
C32—C33—C34—C35 | −63.8 (3) | C4—C5—C6—C7 | 66.0 (3) |
C33—C34—C35—P2 | 173.40 (18) | C5—C6—C7—P1 | −173.67 (18) |
C33—C34—C35—C29 | 53.9 (3) | C5—C6—C7—C1 | −53.5 (3) |
C35—P2—C39—C40 | 85.3 (2) | C7—P1—C11—C12 | 89.3 (2) |
C35—P2—C39—C44 | −88.9 (2) | C7—P1—C11—C16 | −85.0 (2) |
C35—P2—C45—C46 | −10.1 (3) | C7—P1—C17—C18 | −167.5 (2) |
C35—P2—C45—C50 | 171.1 (2) | C7—P1—C17—C22 | 17.9 (3) |
C35—P2—C51—C52 | 33.2 (3) | C7—P1—C23—C24 | 149.2 (2) |
C35—P2—C51—C56 | −150.7 (2) | C7—P1—C23—C28 | −40.5 (3) |
C35—C29—C30—Fe2 | −112.4 (2) | C7—C1—C2—Fe1 | 112.2 (2) |
C35—C29—C30—C31 | −60.7 (4) | C7—C1—C2—C3 | 60.1 (4) |
C39—P2—C35—C29 | 57.4 (2) | C11—P1—C7—C1 | −59.7 (2) |
C39—P2—C35—C34 | −66.1 (2) | C11—P1—C7—C6 | 64.9 (2) |
C39—P2—C45—C46 | −127.4 (2) | C11—P1—C17—C18 | −49.5 (2) |
C39—P2—C45—C50 | 53.8 (2) | C11—P1—C17—C22 | 135.9 (2) |
C39—P2—C51—C52 | 151.9 (2) | C11—P1—C23—C24 | 28.4 (3) |
C39—P2—C51—C56 | −32.0 (3) | C11—P1—C23—C28 | −161.3 (2) |
C39—C40—C41—C42 | 1.0 (4) | C11—C12—C13—C14 | −0.2 (4) |
C40—C39—C44—C43 | 1.3 (4) | C12—C11—C16—C15 | 1.6 (4) |
C40—C41—C42—C43 | 1.2 (4) | C12—C13—C14—C15 | 1.2 (4) |
C41—C42—C43—C44 | −2.1 (4) | C13—C14—C15—C16 | −0.7 (4) |
C42—C43—C44—C39 | 0.9 (4) | C14—C15—C16—C11 | −0.7 (4) |
C44—C39—C40—C41 | −2.2 (4) | C16—C11—C12—C13 | −1.2 (4) |
C45—P2—C35—C29 | −61.5 (2) | C17—P1—C7—C1 | 60.1 (2) |
C45—P2—C35—C34 | 174.99 (17) | C17—P1—C7—C6 | −175.37 (18) |
C45—P2—C39—C40 | −156.1 (2) | C17—P1—C11—C12 | −29.1 (2) |
C45—P2—C39—C44 | 29.7 (2) | C17—P1—C11—C16 | 156.6 (2) |
C45—P2—C51—C52 | −88.5 (2) | C17—P1—C23—C24 | −91.3 (2) |
C45—P2—C51—C56 | 87.5 (2) | C17—P1—C23—C28 | 79.0 (2) |
C45—C46—C47—C48 | 2.3 (4) | C17—C18—C19—C20 | −0.1 (4) |
C46—C45—C50—C49 | 0.0 (4) | C18—C17—C22—C21 | 1.4 (4) |
C46—C47—C48—C49 | −1.5 (4) | C18—C19—C20—C21 | 0.4 (4) |
C47—C48—C49—C50 | −0.1 (4) | C19—C20—C21—C22 | 0.3 (4) |
C48—C49—C50—C45 | 0.8 (4) | C20—C21—C22—C17 | −1.2 (4) |
C50—C45—C46—C47 | −1.5 (4) | C22—C17—C18—C19 | −0.8 (4) |
C51—P2—C35—C29 | 176.90 (17) | C23—P1—C7—C1 | 178.39 (18) |
C51—P2—C35—C34 | 53.4 (2) | C23—P1—C7—C6 | −57.1 (2) |
C51—P2—C39—C40 | −37.1 (2) | C23—P1—C11—C12 | −146.3 (2) |
C51—P2—C39—C44 | 148.7 (2) | C23—P1—C11—C16 | 39.5 (2) |
C51—P2—C45—C46 | 113.9 (2) | C23—P1—C17—C18 | 69.6 (2) |
C51—P2—C45—C50 | −64.9 (2) | C23—P1—C17—C22 | −105.0 (2) |
C51—C52—C53—C54 | 0.1 (4) | C23—C24—C25—C26 | −1.3 (5) |
C52—C51—C56—C55 | −1.6 (4) | C24—C23—C28—C27 | 0.0 (4) |
C52—C53—C54—C55 | −0.5 (4) | C24—C25—C26—C27 | 0.1 (5) |
C53—C54—C55—C56 | −0.1 (5) | C25—C26—C27—C28 | 1.1 (4) |
C54—C55—C56—C51 | 1.2 (5) | C26—C27—C28—C23 | −1.1 (4) |
C56—C51—C52—C53 | 1.0 (4) | C28—C23—C24—C25 | 1.2 (4) |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
C32—H32···F5 | 1.00 | 2.37 | 3.198 (3) | 140 |
C43—H43···F6i | 0.95 | 2.33 | 3.240 (3) | 160 |
C44—H44···O8ii | 0.95 | 2.56 | 3.467 (3) | 159 |
C46—H46···F7iii | 0.95 | 2.40 | 3.151 (3) | 136 |
C49—H49···O7iv | 0.95 | 2.60 | 3.339 (3) | 135 |
C50—H50···F6iv | 0.95 | 2.53 | 3.471 (3) | 169 |
C52—H52···O1 | 0.95 | 2.37 | 3.286 (3) | 161 |
C53—H53···F4iii | 0.95 | 2.66 | 3.500 (3) | 148 |
C56—H56···F6iv | 0.95 | 2.48 | 3.362 (3) | 155 |
C2—H2···F3v | 1.00 | 2.50 | 3.493 (3) | 170 |
C4—H4···F4iii | 1.00 | 2.42 | 3.393 (3) | 165 |
C7—H7···O5 | 1.00 | 2.34 | 3.192 (3) | 143 |
C13—H13···F1v | 0.95 | 2.41 | 3.232 (3) | 144 |
C19—H19···O2vi | 0.95 | 2.51 | 3.393 (3) | 154 |
C28—H28···O5 | 0.95 | 2.41 | 3.319 (4) | 161 |
C57A—H57A···F4 | 0.99 | 2.47 | 3.276 (4) | 139 |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+1, −z+2; (iii) x−1, y, z; (iv) x−1, y+1, z; (v) −x+2, −y+1, −z+1; (vi) x+1, y−1, z. |
Phenyl ring torsion angles (°) topCation 1 | | Cation 2 | |
Torsion angle | Value | Torsion angle | Value |
Ring 1 | | | |
P1—C11—C16—C15 | 175.9 (2) | P2—C39—C40—C41 | -176.5 (2) |
C11—C16—C15—C14 | -0.7 (4) | C39—C40—C41—C42 | 1.0 (4) |
C16—C15—C14—C13 | -0.7 (4) | C40—C41—C42—C43 | 1.2 (4) |
C15—C14—C13—C12 | 1.2 (4) | C41—C42—C43—C44 | -2.2 (4) |
C14—C13—C12—C11 | -0.2 (4) | C42—C43—C44—C39 | 0.9 (4) |
C13—C12—C11—P1 | -175.4 (2) | C43—C44—C39—P2 | 175.6 (2) |
| | | |
Ring 2 | | | |
P1—C17—C18—C19 | -175.5 (2) | P2—C45—C50—C49 | 178.8 (2) |
C17—C18—C19—C20 | -0.1 (4) | C45—C50—C49—C48 | 0.8 (4) |
C18—C19—C20—C21 | 0.4 (4) | C50—C49—C48—C47 | -0.1 (4) |
C19—C20—C21—C22 | -0.2 (5) | C49—C48—C47—C46 | -1.5 (4) |
C20—C21—C22—C17 | -1.2 (4) | C48—C47—C46—C45 | 2.3 (4) |
C21—C22—C17—P1 | 176.0 (2) | C47—C46—C45—P2 | 179.7 (2) |
| | | |
Ring 3 | | | |
P1—C23—C28—C27 | -170.3 (2) | P2—C51—C52—C53 | 176.9 (2) |
C23—C28—C27—C26 | -1.1 (4) | C51—C52—C53—C54 | 0.1 (4) |
C28—C27—C26—C25 | 1.1 (4) | C52—C53—C54—C55 | -0.5 (4) |
C27—C26—C25—C24 | 0.1 (5) | C53—C54—C55—C56 | -0.1 (5) |
C26—C25—C24—C23 | -1.3 (5) | C54—C55—C56—C51 | 1.2 (5) |
C25—C24—C23—P1 | 171.4 (2) | C55—C56—C51—P2 | -177.7 (2) |
X—Y···π interactions (Å,°) topCg1–Cg5 are the centroids of the C11–C16, C17–C22, C39–C44 and C45–C50 rings, respectively. |
X—Y···Cg | Y···Cg | X···Cg | X—H···Cg |
C54—H54···Cg2i | 2.99 | 3.929 (3) | 171 |
B1—F1···Cg1ii | 3.429 (2) | 4.790 (3) | 165.56 (17) |
B2—F6···Cg3iii | 3.653 (2) | 4.913 (3) | 150.99 (17) |
C9—O3···Cg2iv | 3.393 (2) | 3.858 (3) | 105.37 (19) |
C38—08···Cg4v | 3.467 (2) | 3.925 (3) | 105.10 (18) |
Symmetry codes: (i) -1 + x, 1 + y, z; (ii) x, 1 + y, z; (iii) 1 + x, -1 + y, z; (iv) 2 - x, 1 - y, 1 - z; (v) 1 - x, 1 - y, 2 - z. |
Funding information
The authors gratefully acknowledge the McCutchen Foundation for partial support of the X-ray diffractometer.
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