research communications
R,R)-1,2-(binaphthylphosphonito)ethane]dichloridoiron(II) dichloromethane disolvate
of bis[(aDepartment of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada
*Correspondence e-mail: alan.lough@utoronto.ca
In the title compound (systematic name: bis{1,2-bis[12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3(8),4,6,9,16,18(23),19,21-decaen-13-yl]ethane}dichloridoiron(II) dichloromethane disolvate), [FeCl2(C42H28O4P2)2]·2CH2Cl2, the FeII ion lies on a crystallographic twofold rotation axis and is coordinated by four P atoms from two (R,R)-1,2-bis(binaphthylphosphonito)ethane (BPE) ligands and two Cl ligands in a distorted cis-FeCl2P4 octahedral coordination geometry. In the crystal, weak C—H⋯O and C—H⋯π interactions link the molecules into layers lying parallel to (001). A weak intramolecular C—H⋯O hydrogen bond is also observed. The contains one CH2Cl2 solvent molecule, which is disordered over two sets of site with refined occupancies in the ratio 0.700 (6):0.300 (6).
Keywords: crystal structure; BINAP; BINOL; asymmetric catalysis.
CCDC reference: 2023248
1. Chemical context
The ligand (R,R)- or (S,S)-1,2-bis(binaphthylphosphonito)ethane (C42H28O4P2; BPE) prepared from either (R)- or (S)-1,1′-bi(2-naphthol) (C20H14O2; BINOL) has been used extensively in asymmetric catalysis, as has the related ligand (R) or (S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (C44H32P2; BINAP). For example, the BINAP ligand has been coordinated to ruthenium and used for the asymmetric hydrogenation of (Doucet et al., 1998), among many other examples. The BINAP ligand has also been coordinated to iron (Vogler, 2016) to make the complex [FeCl2(BINAP)2]. The BPE ligand and similar bidentate and monodentate phosphonite ligands have been coordinated to rhodium and iridium and used for asymmetric alkene and quinoline hydrogenation reactions, respectively (Claver et al., 2000; Norman et al., 2008; Reetz & Li, 2006), and to ruthenium for asymmetric transfer hydrogenation (Guo et al., 2005a,b).
As an extension of these studies, we now describe the synthesis and 2(BPE)2, which crystallized as a dichloromethane solvate.
of the iron(II) complex FeCl2. Structural commentary
The molecular structure of the title compound is shown in Fig. 1. The FeII ion lies on a crystallographic twofold rotation axis and is coordinated by four P atoms from two BPE ligands and two Cl ligands in a distorted cis-FeCl2P4 octahedral coordination geometry. The largest distortion from ideal coordination geometry is the P2—Fe—P2i angle of 108.49 (7)° (see Table 1 for symmetry codes). The distortion is based on steric grounds involving the bulky binaphthylphosphonito ligands. The Fe—P distances are the same within experimental error. The P atoms are bonded to two O atoms, one C atom and coordinated to the FeII ion in distorted tetrahedral geometries. The dihedral angles between the naphthalene rings in the BPE ligands (C1–C10/C11–20 and C21–C30/C31–C40) are the same, with values of 54.5 (2)°. A weak intramolecular C—H⋯O hydrogen bond is observed (Table 2). The contains one CH2Cl2 solvent molecule, which is disordered over two sets of sites with refined occupancies in the ratio 0.700 (6):0.300 (6).
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3. Supramolecular features
In the crystal, weak C—H⋯O hydrogen bonds link molecules into sheets parallel to (001) (Table 2 and Fig. 2). Within these layers weak C—H⋯π interactions also occur, and the centroid–centroid distance Cg2⋯Cg2(y, −1 + x, 1 − z) of 4.171 (5) Å (where Cg2 is the centroid of the C4–C9 benzene ring) may be a very weak π-stacking interaction.
4. Database survey
A search of the Cambridge Structural Database (CSD, Version 5.41, November, 2019; Groom et al., 2016) showed surprisingly that the title complex is the first iron(II) dichloride with bidentate phosphorus donors with P—O-bonded substituents. There are 36 structures of related iron diphosphine complexes FeCl2(P2)2 (P2 = a diphosphine) with P—C bonds reported. The majority, 33 complexes, crystallize with the chloride ions trans to each other, while there are three examples where the chloride ions are cis, as in the title complex. The complex trans-FeCl2(1,2-bis(diphenylphosphino)ethylene)2, for example, crystallizes with the chloride ions trans (Cecconi et al., 1981). An example with cis chloride ions is the complex cis-FeCl2(1,2-diphospholanoethane)2 (Field et al., 1998). In the trans complexes, the Fe—Cl distances range from 2.21 to 2.38 Å with 22 structures having a distance of 2.34–2.37 Å. This compares with the distances of 2.3422 (11) and 2.3423 (11) Å in the title complex.
5. Synthesis and crystallization
The ligand was synthesized according to a literature procedure using (R)-BINOL (Steinmetz et al., 1999). The iron complex was synthesized as follows: in a nitrogen-filled glovebox, FeCl2·1.5THF (6.0 mg, 0.030 mmol, 1 equivalent) was combined with (R,R)-BPE (50 mg, 0.08 mmol, 3 equivalents) in 10 ml THF and stirred in a 20 ml dram vial for 24 h. The THF was vacuumed off to yield a brown powder: 31P{1H} NMR (202 MHz, C6D6): 257.72 ppm, singlet.
To purify, the powder was dissolved in a minimum of DCM, precipitated out with addition of diethyl ether, and filtered over a glass frit. The precipitate collected on the frit was re-dissolved in DCM, and re-purified by the same procedure twice more. To obtain crystals, a concentrated DCM solution of the purified complex was left in a closed 20 ml dram vial in a nitrogen-filled glovebox for approximately one week at least, depending on the exact concentration. The crystals were orange coloured. Attempts to convert this complex into a hydride complex were unsuccessful.
6. Refinement
Crystal data, data collection and structure . H atoms were included in calculated positions with C—H = 0.95 and 0.99 Å for aromatic and methylene C atoms, respectively, and were included in a riding-model approximation with Uiso(H) = 1.2Ueq(C).
details are summarized in Table 3
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The major component of the disordered CH2Cl2 solvent molecule was refined without restraints while the minor component was restrained to have similar geometry and anisotropic displacement parameters to the major component using the SAME and SADI instructions in SHELXL (Sheldrick, 2015b).
Supporting information
CCDC reference: 2023248
https://doi.org/10.1107/S2056989020011160/hb7939sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020011160/hb7939Isup2.hkl
Data collection: APEX3 (Bruker, 2018); cell
APEX3 (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[FeCl2(C42H28O4P2)2]·2CH2Cl2 | Dx = 1.423 Mg m−3 |
Mr = 1613.77 | Cu Kα radiation, λ = 1.54178 Å |
Tetragonal, P43212 | Cell parameters from 6128 reflections |
a = 11.9850 (3) Å | θ = 3.4–67.3° |
c = 52.4508 (14) Å | µ = 4.84 mm−1 |
V = 7534.0 (4) Å3 | T = 150 K |
Z = 4 | Shard, orange |
F(000) = 3312 | 0.09 × 0.04 × 0.02 mm |
Bruker Kappa APEX DUO CCD diffractometer | 6096 reflections with I > 2σ(I) |
Radiation source: Bruker ImuS with multi-layer optics | Rint = 0.109 |
φ and ω scans | θmax = 67.8°, θmin = 3.4° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −14→14 |
Tmin = 0.649, Tmax = 0.740 | k = −14→14 |
97444 measured reflections | l = −62→60 |
6829 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0538P)2 + 2.6304P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.110 | (Δ/σ)max = 0.002 |
S = 1.04 | Δρmax = 0.39 e Å−3 |
6829 reflections | Δρmin = −0.65 e Å−3 |
502 parameters | Absolute structure: Flack x determined using 2237 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
51 restraints | Absolute structure parameter: 0.004 (4) |
Primary atom site location: structure-invariant direct methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Fe1 | 0.48561 (5) | 0.48561 (5) | 0.500000 | 0.0307 (2) | |
Cl1 | 0.56836 (9) | 0.60053 (9) | 0.53078 (2) | 0.0399 (2) | |
P1 | 0.61181 (9) | 0.35440 (9) | 0.50461 (2) | 0.0337 (2) | |
P2 | 0.43146 (9) | 0.39087 (9) | 0.46724 (2) | 0.0323 (2) | |
O1 | 0.7416 (2) | 0.3808 (3) | 0.49888 (5) | 0.0372 (6) | |
O2 | 0.6217 (2) | 0.2921 (2) | 0.53178 (5) | 0.0353 (6) | |
O3 | 0.4019 (2) | 0.4596 (2) | 0.44174 (5) | 0.0339 (6) | |
O4 | 0.3269 (2) | 0.3037 (2) | 0.46814 (5) | 0.0344 (6) | |
C1 | 0.7004 (4) | 0.2060 (4) | 0.53373 (7) | 0.0361 (9) | |
C2 | 0.6581 (4) | 0.0978 (4) | 0.53413 (8) | 0.0418 (10) | |
H2A | 0.579905 | 0.085380 | 0.533196 | 0.050* | |
C3 | 0.7300 (4) | 0.0097 (4) | 0.53589 (10) | 0.0496 (11) | |
H3A | 0.701999 | −0.064416 | 0.536442 | 0.060* | |
C4 | 0.8463 (4) | 0.0293 (4) | 0.53688 (11) | 0.0537 (12) | |
C5 | 0.9218 (6) | −0.0627 (6) | 0.53717 (18) | 0.089 (2) | |
H5A | 0.893658 | −0.136769 | 0.536834 | 0.107* | |
C6 | 1.0334 (6) | −0.0449 (6) | 0.5379 (2) | 0.113 (3) | |
H6A | 1.083186 | −0.106547 | 0.538366 | 0.136* | |
C7 | 1.0754 (5) | 0.0636 (6) | 0.53811 (19) | 0.092 (3) | |
H7A | 1.153776 | 0.074929 | 0.539014 | 0.111* | |
C8 | 1.0064 (4) | 0.1537 (5) | 0.53701 (12) | 0.0591 (14) | |
H8A | 1.037188 | 0.226617 | 0.536235 | 0.071* | |
C9 | 0.8892 (4) | 0.1397 (4) | 0.53701 (9) | 0.0456 (11) | |
C10 | 0.8124 (4) | 0.2319 (4) | 0.53615 (8) | 0.0373 (9) | |
C11 | 0.8094 (3) | 0.4228 (4) | 0.51800 (8) | 0.0379 (9) | |
C12 | 0.8427 (4) | 0.5346 (4) | 0.51600 (9) | 0.0465 (11) | |
H12A | 0.813430 | 0.580538 | 0.502853 | 0.056* | |
C13 | 0.9167 (4) | 0.5764 (4) | 0.53291 (10) | 0.0492 (11) | |
H13A | 0.942837 | 0.650745 | 0.530978 | 0.059* | |
C14 | 0.9554 (4) | 0.5108 (4) | 0.55342 (9) | 0.0474 (11) | |
C15 | 1.0300 (4) | 0.5549 (5) | 0.57174 (10) | 0.0575 (14) | |
H15A | 1.055261 | 0.629720 | 0.570101 | 0.069* | |
C16 | 1.0661 (4) | 0.4915 (6) | 0.59175 (10) | 0.0643 (16) | |
H16A | 1.117585 | 0.521650 | 0.603679 | 0.077* | |
C17 | 1.0269 (4) | 0.3816 (6) | 0.59468 (9) | 0.0601 (15) | |
H17A | 1.050230 | 0.338638 | 0.608946 | 0.072* | |
C18 | 0.9563 (4) | 0.3363 (5) | 0.57739 (9) | 0.0508 (12) | |
H18A | 0.930467 | 0.262106 | 0.579789 | 0.061* | |
C19 | 0.9200 (4) | 0.3976 (4) | 0.55571 (8) | 0.0426 (10) | |
C20 | 0.8477 (4) | 0.3513 (4) | 0.53680 (8) | 0.0371 (9) | |
C21 | 0.3784 (3) | 0.3994 (3) | 0.41950 (7) | 0.0335 (8) | |
C22 | 0.4624 (4) | 0.3994 (4) | 0.40081 (7) | 0.0362 (9) | |
H22A | 0.531106 | 0.436819 | 0.403744 | 0.043* | |
C23 | 0.4439 (4) | 0.3446 (4) | 0.37837 (7) | 0.0389 (10) | |
H23A | 0.499050 | 0.346153 | 0.365362 | 0.047* | |
C24 | 0.3424 (4) | 0.2853 (4) | 0.37431 (7) | 0.0363 (9) | |
C25 | 0.3247 (4) | 0.2241 (4) | 0.35164 (8) | 0.0417 (10) | |
H25A | 0.380036 | 0.224733 | 0.338670 | 0.050* | |
C26 | 0.2295 (5) | 0.1645 (4) | 0.34819 (8) | 0.0500 (12) | |
H26A | 0.217885 | 0.125179 | 0.332686 | 0.060* | |
C27 | 0.1484 (4) | 0.1608 (4) | 0.36740 (9) | 0.0481 (11) | |
H27A | 0.083146 | 0.116987 | 0.365020 | 0.058* | |
C28 | 0.1619 (4) | 0.2196 (4) | 0.38956 (8) | 0.0427 (10) | |
H28A | 0.106033 | 0.216276 | 0.402372 | 0.051* | |
C29 | 0.2589 (4) | 0.2855 (4) | 0.39357 (7) | 0.0355 (9) | |
C30 | 0.2764 (4) | 0.3487 (4) | 0.41655 (7) | 0.0333 (9) | |
C31 | 0.2185 (4) | 0.3375 (4) | 0.46197 (7) | 0.0339 (9) | |
C32 | 0.1400 (4) | 0.3397 (4) | 0.48183 (7) | 0.0373 (9) | |
H32A | 0.162733 | 0.324610 | 0.498837 | 0.045* | |
C33 | 0.0315 (4) | 0.3634 (4) | 0.47672 (8) | 0.0393 (9) | |
H33A | −0.022239 | 0.360296 | 0.490023 | 0.047* | |
C34 | −0.0025 (4) | 0.3928 (4) | 0.45168 (8) | 0.0388 (9) | |
C35 | −0.1140 (4) | 0.4256 (4) | 0.44645 (9) | 0.0450 (11) | |
H35A | −0.167964 | 0.422774 | 0.459712 | 0.054* | |
C36 | −0.1453 (4) | 0.4611 (5) | 0.42290 (9) | 0.0551 (13) | |
H36A | −0.220192 | 0.482903 | 0.419637 | 0.066* | |
C37 | −0.0645 (4) | 0.4647 (5) | 0.40342 (9) | 0.0516 (12) | |
H37A | −0.085610 | 0.489889 | 0.386940 | 0.062* | |
C38 | 0.0438 (4) | 0.4330 (4) | 0.40761 (8) | 0.0427 (10) | |
H38A | 0.096525 | 0.437562 | 0.394122 | 0.051* | |
C39 | 0.0780 (4) | 0.3936 (4) | 0.43172 (8) | 0.0361 (9) | |
C40 | 0.1903 (3) | 0.3591 (3) | 0.43689 (7) | 0.0323 (8) | |
C41 | 0.5918 (4) | 0.2427 (4) | 0.48152 (8) | 0.0401 (10) | |
H41A | 0.664247 | 0.207405 | 0.477382 | 0.048* | |
H41B | 0.541652 | 0.184854 | 0.488634 | 0.048* | |
C42 | 0.5401 (4) | 0.2936 (4) | 0.45746 (7) | 0.0373 (9) | |
H42A | 0.507843 | 0.234114 | 0.446639 | 0.045* | |
H42B | 0.597990 | 0.333187 | 0.447484 | 0.045* | |
Cl2 | −0.2595 (4) | 0.2896 (5) | 0.33679 (12) | 0.169 (2) | 0.700 (6) |
Cl3 | −0.1596 (4) | 0.1350 (3) | 0.36972 (10) | 0.1311 (17) | 0.700 (6) |
C1S | −0.1387 (12) | 0.2258 (12) | 0.3414 (3) | 0.097 (4) | 0.700 (6) |
H1SA | −0.078690 | 0.280818 | 0.344595 | 0.116* | 0.700 (6) |
H1SB | −0.118299 | 0.180567 | 0.326295 | 0.116* | 0.700 (6) |
Cl4 | −0.1512 (15) | 0.0882 (16) | 0.4023 (3) | 0.218 (7) | 0.300 (6) |
Cl5 | −0.1366 (19) | 0.188 (2) | 0.3518 (3) | 0.222 (7) | 0.300 (6) |
C2S | −0.182 (3) | 0.200 (2) | 0.3855 (4) | 0.125 (7) | 0.300 (6) |
H2SB | −0.144838 | 0.265583 | 0.393264 | 0.150* | 0.300 (6) |
H2SA | −0.263197 | 0.212535 | 0.386018 | 0.150* | 0.300 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0364 (3) | 0.0364 (3) | 0.0193 (4) | 0.0046 (3) | −0.0013 (2) | 0.0013 (2) |
Cl1 | 0.0458 (5) | 0.0441 (5) | 0.0298 (5) | 0.0011 (4) | −0.0063 (4) | −0.0011 (4) |
P1 | 0.0381 (5) | 0.0413 (5) | 0.0218 (5) | 0.0066 (4) | −0.0013 (4) | 0.0015 (4) |
P2 | 0.0380 (5) | 0.0394 (5) | 0.0197 (4) | 0.0048 (4) | −0.0016 (4) | 0.0007 (4) |
O1 | 0.0394 (15) | 0.0482 (16) | 0.0240 (12) | 0.0076 (12) | 0.0029 (12) | 0.0035 (13) |
O2 | 0.0358 (15) | 0.0446 (16) | 0.0255 (13) | 0.0077 (13) | 0.0001 (11) | 0.0056 (12) |
O3 | 0.0424 (15) | 0.0400 (15) | 0.0192 (12) | 0.0026 (12) | −0.0036 (11) | 0.0007 (10) |
O4 | 0.0382 (15) | 0.0406 (15) | 0.0244 (12) | 0.0027 (12) | −0.0025 (11) | 0.0038 (11) |
C1 | 0.037 (2) | 0.046 (2) | 0.0252 (18) | 0.0081 (19) | 0.0008 (16) | 0.0047 (17) |
C2 | 0.042 (2) | 0.049 (3) | 0.034 (2) | 0.000 (2) | −0.0020 (19) | 0.0056 (19) |
C3 | 0.052 (3) | 0.042 (3) | 0.054 (3) | 0.003 (2) | 0.002 (2) | 0.013 (2) |
C4 | 0.048 (3) | 0.047 (3) | 0.066 (3) | 0.014 (2) | 0.010 (2) | 0.015 (2) |
C5 | 0.064 (4) | 0.050 (3) | 0.153 (7) | 0.020 (3) | 0.022 (4) | 0.029 (4) |
C6 | 0.053 (4) | 0.065 (4) | 0.221 (10) | 0.025 (3) | 0.039 (5) | 0.048 (5) |
C7 | 0.042 (3) | 0.066 (4) | 0.169 (8) | 0.016 (3) | 0.021 (4) | 0.039 (4) |
C8 | 0.039 (3) | 0.057 (3) | 0.081 (4) | 0.005 (2) | 0.010 (2) | 0.020 (3) |
C9 | 0.038 (2) | 0.052 (3) | 0.047 (2) | 0.006 (2) | 0.0070 (19) | 0.015 (2) |
C10 | 0.038 (2) | 0.045 (2) | 0.0290 (19) | 0.0054 (18) | 0.0019 (16) | 0.0065 (17) |
C11 | 0.033 (2) | 0.049 (3) | 0.031 (2) | 0.0058 (19) | 0.0021 (17) | 0.0019 (18) |
C12 | 0.046 (2) | 0.046 (3) | 0.047 (3) | 0.007 (2) | 0.004 (2) | 0.008 (2) |
C13 | 0.045 (3) | 0.045 (3) | 0.058 (3) | 0.003 (2) | 0.001 (2) | −0.006 (2) |
C14 | 0.040 (2) | 0.055 (3) | 0.047 (3) | 0.005 (2) | 0.004 (2) | −0.006 (2) |
C15 | 0.043 (3) | 0.073 (4) | 0.057 (3) | 0.000 (3) | −0.001 (2) | −0.022 (3) |
C16 | 0.040 (2) | 0.109 (5) | 0.044 (3) | 0.003 (3) | −0.005 (2) | −0.018 (3) |
C17 | 0.039 (3) | 0.104 (5) | 0.037 (2) | 0.012 (3) | −0.002 (2) | 0.001 (3) |
C18 | 0.040 (2) | 0.078 (4) | 0.034 (2) | 0.005 (2) | −0.0028 (19) | 0.005 (2) |
C19 | 0.033 (2) | 0.060 (3) | 0.036 (2) | 0.003 (2) | 0.0031 (17) | −0.001 (2) |
C20 | 0.033 (2) | 0.048 (2) | 0.030 (2) | 0.0043 (19) | 0.0025 (16) | 0.0026 (18) |
C21 | 0.042 (2) | 0.038 (2) | 0.0201 (17) | 0.0032 (17) | −0.0021 (15) | −0.0026 (15) |
C22 | 0.039 (2) | 0.044 (2) | 0.0254 (18) | −0.0003 (18) | −0.0006 (16) | 0.0036 (16) |
C23 | 0.046 (2) | 0.050 (2) | 0.0207 (18) | 0.006 (2) | 0.0026 (16) | 0.0035 (17) |
C24 | 0.046 (2) | 0.041 (2) | 0.0213 (18) | 0.0038 (19) | 0.0014 (16) | 0.0027 (16) |
C25 | 0.057 (3) | 0.045 (2) | 0.0236 (19) | 0.002 (2) | 0.0025 (18) | −0.0011 (17) |
C26 | 0.073 (3) | 0.051 (3) | 0.026 (2) | −0.001 (2) | −0.007 (2) | −0.0067 (19) |
C27 | 0.056 (3) | 0.051 (3) | 0.037 (2) | −0.010 (2) | −0.009 (2) | −0.003 (2) |
C28 | 0.046 (2) | 0.053 (3) | 0.029 (2) | −0.003 (2) | 0.0014 (18) | −0.0013 (18) |
C29 | 0.043 (2) | 0.040 (2) | 0.0235 (18) | 0.0018 (18) | −0.0021 (16) | 0.0001 (16) |
C30 | 0.041 (2) | 0.037 (2) | 0.0221 (17) | 0.0039 (18) | −0.0010 (16) | 0.0013 (16) |
C31 | 0.038 (2) | 0.037 (2) | 0.0266 (19) | 0.0005 (17) | −0.0017 (16) | 0.0000 (16) |
C32 | 0.042 (2) | 0.046 (2) | 0.0237 (18) | 0.0016 (19) | −0.0004 (16) | 0.0028 (17) |
C33 | 0.043 (2) | 0.046 (2) | 0.029 (2) | 0.002 (2) | 0.0062 (17) | 0.0038 (17) |
C34 | 0.041 (2) | 0.043 (2) | 0.033 (2) | 0.0012 (19) | 0.0018 (18) | 0.0005 (17) |
C35 | 0.037 (2) | 0.058 (3) | 0.040 (2) | 0.004 (2) | 0.0042 (19) | 0.004 (2) |
C36 | 0.041 (2) | 0.080 (4) | 0.044 (3) | 0.012 (3) | 0.000 (2) | 0.013 (3) |
C37 | 0.045 (2) | 0.076 (4) | 0.033 (2) | 0.008 (3) | −0.0032 (19) | 0.014 (2) |
C38 | 0.043 (2) | 0.058 (3) | 0.028 (2) | 0.003 (2) | −0.0006 (17) | 0.0039 (19) |
C39 | 0.041 (2) | 0.041 (2) | 0.0261 (19) | −0.0013 (19) | 0.0011 (16) | −0.0008 (17) |
C40 | 0.036 (2) | 0.035 (2) | 0.0253 (18) | 0.0004 (17) | −0.0027 (16) | −0.0011 (15) |
C41 | 0.049 (3) | 0.042 (2) | 0.029 (2) | 0.009 (2) | 0.0003 (18) | 0.0005 (17) |
C42 | 0.043 (2) | 0.045 (2) | 0.0238 (18) | 0.0063 (19) | −0.0004 (16) | −0.0047 (17) |
Cl2 | 0.100 (3) | 0.182 (5) | 0.225 (5) | 0.005 (3) | −0.006 (3) | 0.093 (4) |
Cl3 | 0.100 (2) | 0.102 (3) | 0.191 (5) | −0.0034 (19) | −0.034 (3) | 0.026 (3) |
C1S | 0.098 (7) | 0.088 (7) | 0.105 (8) | −0.010 (6) | −0.023 (6) | 0.051 (6) |
Cl4 | 0.190 (11) | 0.248 (14) | 0.216 (13) | −0.008 (12) | 0.029 (11) | 0.023 (11) |
Cl5 | 0.201 (12) | 0.225 (14) | 0.241 (15) | 0.000 (12) | −0.008 (13) | −0.052 (12) |
C2S | 0.135 (14) | 0.110 (14) | 0.130 (14) | −0.003 (13) | 0.025 (13) | −0.071 (12) |
Fe1—P2 | 2.1594 (11) | C19—C20 | 1.429 (6) |
Fe1—P2i | 2.1595 (11) | C21—C30 | 1.375 (6) |
Fe1—P1i | 2.1952 (10) | C21—C22 | 1.405 (6) |
Fe1—P1 | 2.1952 (10) | C22—C23 | 1.366 (6) |
Fe1—Cl1i | 2.3422 (11) | C22—H22A | 0.9500 |
Fe1—Cl1 | 2.3423 (11) | C23—C24 | 1.426 (7) |
P1—O2 | 1.613 (3) | C23—H23A | 0.9500 |
P1—O1 | 1.616 (3) | C24—C25 | 1.413 (6) |
P1—C41 | 1.821 (4) | C24—C29 | 1.422 (6) |
P2—O3 | 1.611 (3) | C25—C26 | 1.359 (7) |
P2—O4 | 1.632 (3) | C25—H25A | 0.9500 |
P2—C42 | 1.821 (4) | C26—C27 | 1.401 (8) |
O1—C11 | 1.386 (5) | C26—H26A | 0.9500 |
O2—C1 | 1.401 (5) | C27—C28 | 1.369 (6) |
O3—C21 | 1.400 (5) | C27—H27A | 0.9500 |
O4—C31 | 1.398 (5) | C28—C29 | 1.420 (6) |
C1—C10 | 1.384 (6) | C28—H28A | 0.9500 |
C1—C2 | 1.393 (7) | C29—C30 | 1.439 (6) |
C2—C3 | 1.366 (7) | C30—C40 | 1.489 (6) |
C2—H2A | 0.9500 | C31—C40 | 1.383 (6) |
C3—C4 | 1.415 (7) | C31—C32 | 1.404 (6) |
C3—H3A | 0.9500 | C32—C33 | 1.358 (7) |
C4—C9 | 1.419 (8) | C32—H32A | 0.9500 |
C4—C5 | 1.426 (8) | C33—C34 | 1.419 (6) |
C5—C6 | 1.355 (10) | C33—H33A | 0.9500 |
C5—H5A | 0.9500 | C34—C35 | 1.420 (7) |
C6—C7 | 1.395 (11) | C34—C39 | 1.423 (6) |
C6—H6A | 0.9500 | C35—C36 | 1.359 (7) |
C7—C8 | 1.361 (8) | C35—H35A | 0.9500 |
C7—H7A | 0.9500 | C36—C37 | 1.409 (7) |
C8—C9 | 1.415 (7) | C36—H36A | 0.9500 |
C8—H8A | 0.9500 | C37—C38 | 1.370 (7) |
C9—C10 | 1.439 (6) | C37—H37A | 0.9500 |
C10—C20 | 1.493 (7) | C38—C39 | 1.411 (6) |
C11—C20 | 1.385 (6) | C38—H38A | 0.9500 |
C11—C12 | 1.401 (7) | C39—C40 | 1.434 (6) |
C12—C13 | 1.350 (7) | C41—C42 | 1.532 (6) |
C12—H12A | 0.9500 | C41—H41A | 0.9900 |
C13—C14 | 1.411 (7) | C41—H41B | 0.9900 |
C13—H13A | 0.9500 | C42—H42A | 0.9900 |
C14—C15 | 1.415 (7) | C42—H42B | 0.9900 |
C14—C19 | 1.426 (8) | Cl2—C1S | 1.656 (15) |
C15—C16 | 1.366 (9) | Cl3—C1S | 1.859 (11) |
C15—H15A | 0.9500 | C1S—H1SA | 0.9900 |
C16—C17 | 1.408 (10) | C1S—H1SB | 0.9900 |
C16—H16A | 0.9500 | Cl4—C2S | 1.644 (18) |
C17—C18 | 1.354 (8) | Cl5—C2S | 1.852 (15) |
C17—H17A | 0.9500 | C2S—H2SB | 0.9900 |
C18—C19 | 1.422 (7) | C2S—H2SA | 0.9900 |
C18—H18A | 0.9500 | ||
P2—Fe1—P2i | 108.49 (7) | C11—C20—C19 | 117.0 (4) |
P2—Fe1—P1i | 93.40 (4) | C11—C20—C10 | 118.9 (4) |
P2i—Fe1—P1i | 85.30 (4) | C19—C20—C10 | 124.0 (4) |
P2—Fe1—P1 | 85.30 (4) | C30—C21—O3 | 120.0 (3) |
P2i—Fe1—P1 | 93.40 (4) | C30—C21—C22 | 124.0 (4) |
P1i—Fe1—P1 | 177.78 (7) | O3—C21—C22 | 115.9 (4) |
P2—Fe1—Cl1i | 81.43 (4) | C23—C22—C21 | 119.0 (4) |
P2i—Fe1—Cl1i | 170.01 (5) | C23—C22—H22A | 120.5 |
P1i—Fe1—Cl1i | 93.07 (4) | C21—C22—H22A | 120.5 |
P1—Fe1—Cl1i | 88.52 (4) | C22—C23—C24 | 120.5 (4) |
P2—Fe1—Cl1 | 170.02 (5) | C22—C23—H23A | 119.8 |
P2i—Fe1—Cl1 | 81.43 (4) | C24—C23—H23A | 119.8 |
P1i—Fe1—Cl1 | 88.51 (4) | C25—C24—C29 | 119.6 (4) |
P1—Fe1—Cl1 | 93.07 (4) | C25—C24—C23 | 120.8 (4) |
Cl1i—Fe1—Cl1 | 88.69 (6) | C29—C24—C23 | 119.6 (4) |
O2—P1—O1 | 100.60 (15) | C26—C25—C24 | 120.7 (4) |
O2—P1—C41 | 104.87 (18) | C26—C25—H25A | 119.6 |
O1—P1—C41 | 98.46 (19) | C24—C25—H25A | 119.6 |
O2—P1—Fe1 | 118.67 (11) | C25—C26—C27 | 120.2 (4) |
O1—P1—Fe1 | 120.18 (12) | C25—C26—H26A | 119.9 |
C41—P1—Fe1 | 111.26 (15) | C27—C26—H26A | 119.9 |
O3—P2—O4 | 100.52 (14) | C28—C27—C26 | 120.8 (4) |
O3—P2—C42 | 104.53 (17) | C28—C27—H27A | 119.6 |
O4—P2—C42 | 98.48 (18) | C26—C27—H27A | 119.6 |
O3—P2—Fe1 | 117.25 (11) | C27—C28—C29 | 120.6 (4) |
O4—P2—Fe1 | 122.98 (11) | C27—C28—H28A | 119.7 |
C42—P2—Fe1 | 110.23 (14) | C29—C28—H28A | 119.7 |
C11—O1—P1 | 120.1 (2) | C28—C29—C24 | 118.0 (4) |
C1—O2—P1 | 117.1 (2) | C28—C29—C30 | 122.4 (4) |
C21—O3—P2 | 118.2 (2) | C24—C29—C30 | 119.6 (4) |
C31—O4—P2 | 121.4 (3) | C21—C30—C29 | 117.2 (4) |
C10—C1—C2 | 124.1 (4) | C21—C30—C40 | 119.9 (4) |
C10—C1—O2 | 119.6 (4) | C29—C30—C40 | 122.9 (4) |
C2—C1—O2 | 116.2 (4) | C40—C31—O4 | 120.1 (4) |
C3—C2—C1 | 119.4 (4) | C40—C31—C32 | 122.6 (4) |
C3—C2—H2A | 120.3 | O4—C31—C32 | 117.2 (3) |
C1—C2—H2A | 120.3 | C33—C32—C31 | 120.0 (4) |
C2—C3—C4 | 119.7 (5) | C33—C32—H32A | 120.0 |
C2—C3—H3A | 120.1 | C31—C32—H32A | 120.0 |
C4—C3—H3A | 120.1 | C32—C33—C34 | 120.6 (4) |
C3—C4—C9 | 120.8 (4) | C32—C33—H33A | 119.7 |
C3—C4—C5 | 119.8 (5) | C34—C33—H33A | 119.7 |
C9—C4—C5 | 119.4 (5) | C33—C34—C35 | 121.1 (4) |
C6—C5—C4 | 120.3 (7) | C33—C34—C39 | 119.2 (4) |
C6—C5—H5A | 119.8 | C35—C34—C39 | 119.6 (4) |
C4—C5—H5A | 119.8 | C36—C35—C34 | 121.5 (4) |
C5—C6—C7 | 120.2 (6) | C36—C35—H35A | 119.3 |
C5—C6—H6A | 119.9 | C34—C35—H35A | 119.3 |
C7—C6—H6A | 119.9 | C35—C36—C37 | 118.6 (5) |
C8—C7—C6 | 121.3 (6) | C35—C36—H36A | 120.7 |
C8—C7—H7A | 119.3 | C37—C36—H36A | 120.7 |
C6—C7—H7A | 119.3 | C38—C37—C36 | 121.8 (4) |
C7—C8—C9 | 120.6 (5) | C38—C37—H37A | 119.1 |
C7—C8—H8A | 119.7 | C36—C37—H37A | 119.1 |
C9—C8—H8A | 119.7 | C37—C38—C39 | 120.8 (4) |
C8—C9—C4 | 118.0 (4) | C37—C38—H38A | 119.6 |
C8—C9—C10 | 122.9 (5) | C39—C38—H38A | 119.6 |
C4—C9—C10 | 119.0 (4) | C38—C39—C34 | 117.7 (4) |
C1—C10—C9 | 116.8 (4) | C38—C39—C40 | 122.6 (4) |
C1—C10—C20 | 119.4 (4) | C34—C39—C40 | 119.7 (4) |
C9—C10—C20 | 123.7 (4) | C31—C40—C39 | 117.6 (4) |
C20—C11—O1 | 119.0 (4) | C31—C40—C30 | 119.8 (4) |
C20—C11—C12 | 123.4 (4) | C39—C40—C30 | 122.6 (3) |
O1—C11—C12 | 117.4 (4) | C42—C41—P1 | 107.9 (3) |
C13—C12—C11 | 119.5 (5) | C42—C41—H41A | 110.1 |
C13—C12—H12A | 120.2 | P1—C41—H41A | 110.1 |
C11—C12—H12A | 120.2 | C42—C41—H41B | 110.1 |
C12—C13—C14 | 120.6 (5) | P1—C41—H41B | 110.1 |
C12—C13—H13A | 119.7 | H41A—C41—H41B | 108.4 |
C14—C13—H13A | 119.7 | C41—C42—P2 | 108.2 (3) |
C13—C14—C15 | 121.1 (5) | C41—C42—H42A | 110.1 |
C13—C14—C19 | 119.7 (4) | P2—C42—H42A | 110.1 |
C15—C14—C19 | 119.1 (5) | C41—C42—H42B | 110.1 |
C16—C15—C14 | 120.9 (6) | P2—C42—H42B | 110.1 |
C16—C15—H15A | 119.5 | H42A—C42—H42B | 108.4 |
C14—C15—H15A | 119.5 | Cl2—C1S—Cl3 | 105.6 (8) |
C15—C16—C17 | 119.9 (5) | Cl2—C1S—H1SA | 110.6 |
C15—C16—H16A | 120.0 | Cl3—C1S—H1SA | 110.6 |
C17—C16—H16A | 120.0 | Cl2—C1S—H1SB | 110.6 |
C18—C17—C16 | 120.7 (5) | Cl3—C1S—H1SB | 110.6 |
C18—C17—H17A | 119.7 | H1SA—C1S—H1SB | 108.7 |
C16—C17—H17A | 119.7 | Cl4—C2S—Cl5 | 112.5 (14) |
C17—C18—C19 | 121.3 (6) | Cl4—C2S—H2SB | 109.1 |
C17—C18—H18A | 119.3 | Cl5—C2S—H2SB | 109.1 |
C19—C18—H18A | 119.3 | Cl4—C2S—H2SA | 109.1 |
C18—C19—C14 | 117.9 (5) | Cl5—C2S—H2SA | 109.1 |
C18—C19—C20 | 122.7 (5) | H2SB—C2S—H2SA | 107.8 |
C14—C19—C20 | 119.4 (4) | ||
O2—P1—O1—C11 | −44.5 (3) | C1—C10—C20—C19 | 130.0 (4) |
C41—P1—O1—C11 | −151.5 (3) | C9—C10—C20—C19 | −52.3 (6) |
Fe1—P1—O1—C11 | 87.8 (3) | P2—O3—C21—C30 | 76.9 (4) |
O1—P1—O2—C1 | −49.0 (3) | P2—O3—C21—C22 | −105.7 (4) |
C41—P1—O2—C1 | 52.8 (3) | C30—C21—C22—C23 | −1.0 (7) |
Fe1—P1—O2—C1 | 177.7 (3) | O3—C21—C22—C23 | −178.3 (4) |
O4—P2—O3—C21 | −50.9 (3) | C21—C22—C23—C24 | −2.1 (6) |
C42—P2—O3—C21 | 50.8 (3) | C22—C23—C24—C25 | −177.0 (4) |
Fe1—P2—O3—C21 | 173.2 (2) | C22—C23—C24—C29 | 1.5 (6) |
O3—P2—O4—C31 | −40.3 (3) | C29—C24—C25—C26 | −0.8 (7) |
C42—P2—O4—C31 | −146.9 (3) | C23—C24—C25—C26 | 177.7 (4) |
Fe1—P2—O4—C31 | 92.2 (3) | C24—C25—C26—C27 | −1.5 (8) |
P1—O2—C1—C10 | 76.8 (4) | C25—C26—C27—C28 | 2.0 (8) |
P1—O2—C1—C2 | −105.8 (4) | C26—C27—C28—C29 | −0.1 (8) |
C10—C1—C2—C3 | −3.0 (7) | C27—C28—C29—C24 | −2.1 (7) |
O2—C1—C2—C3 | 179.7 (4) | C27—C28—C29—C30 | 179.9 (4) |
C1—C2—C3—C4 | −1.0 (7) | C25—C24—C29—C28 | 2.6 (6) |
C2—C3—C4—C9 | 2.3 (8) | C23—C24—C29—C28 | −176.0 (4) |
C2—C3—C4—C5 | −176.3 (6) | C25—C24—C29—C30 | −179.3 (4) |
C3—C4—C5—C6 | 179.5 (8) | C23—C24—C29—C30 | 2.1 (6) |
C9—C4—C5—C6 | 0.9 (12) | O3—C21—C30—C29 | −178.2 (4) |
C4—C5—C6—C7 | −0.8 (16) | C22—C21—C30—C29 | 4.6 (6) |
C5—C6—C7—C8 | −1.3 (16) | O3—C21—C30—C40 | 0.7 (6) |
C6—C7—C8—C9 | 3.4 (13) | C22—C21—C30—C40 | −176.4 (4) |
C7—C8—C9—C4 | −3.2 (9) | C28—C29—C30—C21 | 173.0 (4) |
C7—C8—C9—C10 | 179.3 (6) | C24—C29—C30—C21 | −5.0 (6) |
C3—C4—C9—C8 | −177.6 (5) | C28—C29—C30—C40 | −5.9 (7) |
C5—C4—C9—C8 | 1.0 (8) | C24—C29—C30—C40 | 176.1 (4) |
C3—C4—C9—C10 | 0.0 (7) | P2—O4—C31—C40 | 72.6 (5) |
C5—C4—C9—C10 | 178.7 (6) | P2—O4—C31—C32 | −112.1 (4) |
C2—C1—C10—C9 | 5.3 (6) | C40—C31—C32—C33 | 0.2 (7) |
O2—C1—C10—C9 | −177.5 (4) | O4—C31—C32—C33 | −174.9 (4) |
C2—C1—C10—C20 | −176.8 (4) | C31—C32—C33—C34 | −3.9 (7) |
O2—C1—C10—C20 | 0.4 (6) | C32—C33—C34—C35 | −175.4 (5) |
C8—C9—C10—C1 | 173.8 (5) | C32—C33—C34—C39 | 2.1 (7) |
C4—C9—C10—C1 | −3.6 (6) | C33—C34—C35—C36 | 175.5 (5) |
C8—C9—C10—C20 | −4.0 (7) | C39—C34—C35—C36 | −1.9 (8) |
C4—C9—C10—C20 | 178.5 (4) | C34—C35—C36—C37 | 0.1 (9) |
P1—O1—C11—C20 | 76.4 (4) | C35—C36—C37—C38 | 0.4 (9) |
P1—O1—C11—C12 | −108.5 (4) | C36—C37—C38—C39 | 1.0 (9) |
C20—C11—C12—C13 | 0.7 (7) | C37—C38—C39—C34 | −2.8 (7) |
O1—C11—C12—C13 | −174.1 (4) | C37—C38—C39—C40 | 179.8 (5) |
C11—C12—C13—C14 | −3.9 (7) | C33—C34—C39—C38 | −174.3 (4) |
C12—C13—C14—C15 | −177.8 (5) | C35—C34—C39—C38 | 3.2 (7) |
C12—C13—C14—C19 | 2.7 (7) | C33—C34—C39—C40 | 3.3 (7) |
C13—C14—C15—C16 | 179.1 (5) | C35—C34—C39—C40 | −179.2 (4) |
C19—C14—C15—C16 | −1.4 (7) | O4—C31—C40—C39 | −179.9 (4) |
C14—C15—C16—C17 | −1.6 (8) | C32—C31—C40—C39 | 5.1 (6) |
C15—C16—C17—C18 | 2.1 (8) | O4—C31—C40—C30 | −1.4 (6) |
C16—C17—C18—C19 | 0.4 (8) | C32—C31—C40—C30 | −176.4 (4) |
C17—C18—C19—C14 | −3.3 (7) | C38—C39—C40—C31 | 170.8 (4) |
C17—C18—C19—C20 | 178.4 (5) | C34—C39—C40—C31 | −6.7 (6) |
C13—C14—C19—C18 | −176.7 (4) | C38—C39—C40—C30 | −7.8 (7) |
C15—C14—C19—C18 | 3.8 (6) | C34—C39—C40—C30 | 174.8 (4) |
C13—C14—C19—C20 | 1.6 (7) | C21—C30—C40—C31 | −49.4 (6) |
C15—C14—C19—C20 | −177.9 (4) | C29—C30—C40—C31 | 129.5 (4) |
O1—C11—C20—C19 | 178.3 (4) | C21—C30—C40—C39 | 129.1 (4) |
C12—C11—C20—C19 | 3.5 (6) | C29—C30—C40—C39 | −51.9 (6) |
O1—C11—C20—C10 | −1.3 (6) | O2—P1—C41—C42 | 159.7 (3) |
C12—C11—C20—C10 | −176.1 (4) | O1—P1—C41—C42 | −96.9 (3) |
C18—C19—C20—C11 | 173.7 (4) | Fe1—P1—C41—C42 | 30.2 (3) |
C14—C19—C20—C11 | −4.5 (6) | P1—C41—C42—P2 | −43.1 (4) |
C18—C19—C20—C10 | −6.7 (7) | O3—P2—C42—C41 | 167.6 (3) |
C14—C19—C20—C10 | 175.1 (4) | O4—P2—C42—C41 | −89.1 (3) |
C1—C10—C20—C11 | −50.5 (6) | Fe1—P2—C42—C41 | 40.8 (3) |
C9—C10—C20—C11 | 127.3 (4) |
Symmetry code: (i) y, x, −z+1. |
Cg2 and Cg3 are the centroids of the C24–C29 and C31–C40 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C32—H32A···O4i | 0.95 | 2.42 | 3.280 (5) | 150 |
C35—H35A···O1ii | 0.95 | 2.38 | 3.293 (5) | 162 |
C7—H7A···Cg2iii | 0.95 | 2.57 | 3.516 (6) | 178 |
C17—H17A···Cg3iii | 0.95 | 2.59 | 3.396 (6) | 143 |
Symmetry codes: (i) y, x, −z+1; (ii) x−1, y, z; (iii) y+1, x, −z+1. |
Funding information
RHM thanks NSERC Canada for a Discovery Grant.
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