Crystal structure of bis­[(R,R)-1,2-(bi­naph­thyl­phospho­nito)ethane]­dichlorido­iron(II) di­chloro­methane disolvate

Rennie, B.E.; Lough, A.J.; Morris, R.H.

doi:10.1107/S2056989020011160

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Volume 76| Part 9| September 2020| Pages 1525-1527

https://doi.org/10.1107/S2056989020011160

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Crystal structure of bis[(R,R)-1,2-(binaphthylphosphonito)ethane]dichloridoiron(II) dichloromethane disolvate

Benjamin E. Rennie,^a Alan J. Lough ^a ^* and Robert H. Morris ^a

^aDepartment of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada
^*Correspondence e-mail: alan.lough@utoronto.ca

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 3 August 2020; accepted 14 August 2020; online 28 August 2020)

In the title compound (systematic name: bis{1,2-bis[12,14-dioxa-13-phosphapentacyclo[13.8.0.0^2,11.0^3,8.0^18,23]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 Fe^II 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 asymmetric unit 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 ketones (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 crystal structure of the iron(II) complex FeCl₂(BPE)₂, which crystallized as a dichloromethane solvate.

2. Structural commentary

The molecular structure of the title compound is shown in Fig. 1. The Fe^II 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 Fe^II 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 asymmetric unit 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).

Table 1
Selected geometric parameters (Å, °)

Fe1—P2	2.1594 (11)	Fe1—P1	2.1952 (10)
Fe1—P2ⁱ	2.1595 (11)	Fe1—Cl1ⁱ	2.3422 (11)
Fe1—P1ⁱ	2.1952 (10)	Fe1—Cl1	2.3423 (11)

P2—Fe1—P2ⁱ	108.49 (7)	P1—Fe1—Cl1ⁱ	88.52 (4)
P2—Fe1—P1ⁱ	93.40 (4)	P2—Fe1—Cl1	170.02 (5)
P2—Fe1—P1	85.30 (4)	P1—Fe1—Cl1	93.07 (4)
P1ⁱ—Fe1—P1	177.78 (7)	Cl1ⁱ—Fe1—Cl1	88.69 (6)
P2—Fe1—Cl1ⁱ	81.43 (4)
Symmetry code: (i) y, x, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

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.

Figure 1
The molecular structure of the title compound with 30% probability ellipsoids. Unlabeled atoms are related by the symmetry operator (y, x, −z + 1) and for the sake of clarity the disordered solvent molecule is not shown.

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.

Figure 2
Part of the crystal structure of the title compound showing the formation of [100] chains linked by weak C—H⋯O hydrogen bonds shown as blue lines. The disordered dichloromethane solvent molecules are not shown.

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 crystal structure 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 refinement details are summarized in Table 3. 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 U_iso(H) = 1.2U_eq(C).

Table 3
Experimental details

Crystal data
Chemical formula	[FeCl₂(C₄₂H₂₈O₄P₂)₂]·2CH₂Cl₂
M_r	1613.77
Crystal system, space group	Tetragonal, P4₃2₁2
Temperature (K)	150
a, c (Å)	11.9850 (3), 52.4508 (14)
V (Å³)	7534.0 (4)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	4.84
Crystal size (mm)	0.09 × 0.04 × 0.02

Data collection
Diffractometer	Bruker Kappa APEX DUO CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.649, 0.740
No. of measured, independent and observed [I > 2σ(I)] reflections	97444, 6829, 6096
R_int	0.109
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.110, 1.04
No. of reflections	6829
No. of parameters	502
No. of restraints	51
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.65
Absolute structure	Flack x determined using 2237 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.004 (4)
Computer programs: APEX3 and SAINT (Bruker, 2018 ), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b), PLATON (Spek, 2020 ) and SHELXTL (Sheldrick, 2008 ).

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

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989020011160/hb7939sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020011160/hb7939Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2018); cell refinement: 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).

Bis{1,2-bis[12,14-dioxa-13-phosphapentacyclo[13.8.0.0^2,11.0^3,8.0^18,23]tricosa-1(15),2(11),3(8),4,6,9,16,18(23),19,21-decaen-13-yl]ethane}dichloridoiron(II) dichloromethane disolvate top

Crystal data top

[FeCl₂(C₄₂H₂₈O₄P₂)₂]·2CH₂Cl₂	D_x = 1.423 Mg m⁻³
M_r = 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

Data collection top

Bruker Kappa APEX DUO CCD diffractometer	6096 reflections with I > 2σ(I)
Radiation source: Bruker ImuS with multi-layer optics	R_int = 0.109
φ and ω scans	θ_max = 67.8°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −14→14
T_min = 0.649, T_max = 0.740	k = −14→14
97444 measured reflections	l = −62→60
6829 independent reflections

Refinement top

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(F_o²) + (0.0538P)² + 2.6304P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.110	(Δ/σ)_max = 0.002
S = 1.04	Δρ_max = 0.39 e Å⁻³
6829 reflections	Δρ_min = −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

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	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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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