Synthesis and crystal structure of bis­[trans-di­aqua­(1,4,8,11-tetra­aza­cyclo­tetra­decane-κ4N1,N4,N8,N11)nickel(II)] trans-(1,4,8,11-tetra­aza­cyclo­tetra­decane-κ4N1,N4,N8,N11)bis­[4,4′,4′′-(1,3,5-tri­methyl­benzene-2,4,6-tri­yl)tris­(hydrogen phenyl­phospho­nato-κO)]nickel(II) deca­hydrate

Tsymbal, L.V.; Ardeleanu, R.; Shova, S.; Lampeka, Y.D.

doi:10.1107/S2056989022006624

research communications

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 78| Part 7| July 2022| Pages 750-754

https://doi.org/10.1107/S2056989022006624

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Synthesis and crystal structure of bis[trans-diaqua(1,4,8,11-tetraazacyclotetradecane-κ⁴N¹,N⁴,N⁸,N¹¹)nickel(II)] trans-(1,4,8,11-tetraazacyclotetradecane-κ⁴N¹,N⁴,N⁸,N¹¹)bis[4,4′,4′′-(1,3,5-trimethylbenzene-2,4,6-triyl)tris(hydrogen phenylphosphonato-κO)]nickel(II) decahydrate

Liudmyla V. Tsymbal,^a Rodinel Ardeleanu,^b Sergiu Shova ^b and Yaroslaw D. Lampeka ^a ^*

^aL. V. Pisarzhevskii Institute of Physical Chemistry of the National Academy of, Sciences of Ukraine, Prospekt Nauki, 31, Kiev 03028, Ukraine, and ^b"Petru Poni" Institute of Macromolecular Chemistry, Department of, Inorganic, Polymers, Aleea Grigore Ghica Voda 41A, RO-700487 Iasi, Romania
^*Correspondence e-mail: lampeka@adamant.net

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 13 June 2022; accepted 26 June 2022; online 30 June 2022)

The components of the title compound, [Ni(C₁₀H₂₄N₄)(H₂O)₂]₂[Ni(C₁₀H₂₄N₄)(C₂₇H₂₄O₉P₃)₂]·10H₂O are two centrosymmetric [Ni(C₁₀H₂₄N₄)(H₂O)₂]²⁺ dications, a centrosymmetric [Ni(C₁₀H₂₄N₄)(C₂₇H₂₄O₉P₃)₂]⁴⁻ tetra-anion and five crystallographically unique water molecules of crystallization. All of the nickel ions are coordinated by the four secondary N atoms of the macrocyclic cyclam ligands, which adopt the most energetically stable trans-III conformation, and the mutually trans O atoms of either water molecules in the cations or the phosphonate groups in the anion in a tetragonally distorted NiN₄O₂ octahedral coordination geometry. Strong O—H⋯O hydrogen bonds between the protonated and the non-protonated phosphonate O atoms of neighboring anions result in the formation of layers oriented parallel to the bc plane, which are linked into a three-dimensional network by virtue of numerous N—H⋯O and O—H⋯O hydrogen bonds arising from the sec-NH groups of the macrocycles, phosphonate O atoms and coordinated and non-coordinated water molecules.

Keywords: crystal structure; cyclam; nickel; triphosphonic acid.

CCDC reference: 2178456

1. Chemical context

First-row transition-metal complexes of 14-membered cyclam-like tetraaza macrocyles (cyclam = 1,4,8,11-tetraazacyclotetradecane; C₁₀H₂₄N₄; L) are characterized by high thermodynamic stability and kinetic inertness (Yatsimirskii & Lampeka, 1985 ) and are popular metal-containing building units for the construction of MOFs (Lampeka & Tsymbal, 2004 ; Suh & Moon, 2007 ; Suh et al., 2012 ; Stackhouse & Ma, 2018 ). These crystalline coordination polymers, in which oligocarboxylates are the most common bridging ligands (Rao et al., 2004 ), possess permanent porosity and demonstrate many promising applications in different areas (MacGillivray & Lukehart, 2014 ; Kaskel, 2016 ).

The rigid trigonal aromatic linker 1,3,5-benzenetricarboxylate, C₉H₃O₆^3–, is widely used for the assembly of MOFs based on azamacrocyclic cations (Lampeka & Tsymbal, 2004). Its tris-monodentate coordination in the trans-axial coordination positions of the metal ions leads predominantly to the formation of two-dimensional coordination polymers with hexagonal nets of 6³ topology (Alexandrov et al., 2017 ). Usually, the modification of this bridge through the substitution of the carboxylic groups by para-carboxybenzyl fragments (the ligand H₃BTB, 4,4′,4′′-benzene-1,3,5-triyltribenzoic acid) does not affect the coordination properties of the carboxylate groups or the topological characteristics of polymeric nets but results in the enlargement of the hexagonal structural unit of the coordination polymers allowing interpenetration of the subnets (Lampeka et al., 2012 ; Gong et al., 2016 ). Compared to carboxylates, linkers with other coordinating functions, in particular oligophosphonates, have been studied to a much lesser extent (Gagnon et al., 2012 ; Firmino et al., 2018 ; Yücesan et al., 2018 ), though one can expect that the substitution of a mono-anionic carboxylic group by a di-anionic phosphonate group with distinct acidity, number of donor atoms and spatial directivity of coordination bonds will strongly influence the composition and topology of the coordination nets. However, except for a very recent publication (Tsymbal et al., 2022 ), no papers dealing with structural characterization of the complexes formed by metal azamacrocyclic cations and phosphonate ligands have been published to date.

We report here the synthesis and crystal structure of the product of the reaction of [Ni(L)](ClO₄)₂ with 4,4′,4′′-(1,3,5-trimethylbenzene-2,4,6-triyl)triphosphonic acid, H₆Me₃BTP) – the structural analogue of H₃BTB, namely, bis[trans-diaqua-(1,4,8,11-tetraazacyclotetradecane-κ⁴N¹,N⁴,N⁸,N¹¹)-nickel(II)] trans-{bis-[4,4′,4′′-(1,3,5-trimethylbenzene-2,4,6-triyl)tris(hydrogen phenylphosphonato-κO)-(1,4,8,11-tetraazacyclotetradecane-κ⁴N¹,N⁴,N⁸,N¹¹)-nickel(II)]} decahydrate, [Ni(L)(H₂O)₂]₂[Ni(L)(H₃Me₃BTP)₂]·10H₂O, I.

2. Structural commentary

The molecular structure of I is shown in Fig. 1. It represents a non-polymeric compound in which atom Ni1 is coordinated by two monodentate H₃Me₃BTP^3– ligands via their phosphonate O atoms, resulting in the formation of an [Ni(L)(H₃Me₃BTP)₂]^4– complex anion, which is charge-balanced by two structurally non-equivalent [Ni(L)(H₂O)₂]²⁺ divalent cations formed by atoms Ni2 and Ni3. The coordination geometries of all the nickel ions in I have much in common: the Ni²⁺ ions (all with site symmetry $[\overline{1}]$ ) are coordinated by the four secondary N atoms of the macrocyclic ligands L, which adopt the most energetically stable trans-III (R,R,S,S) conformation (Bosnich et al., 1965a ; Barefield et al., 1986 ) with the five-membered (N—Ni—N bite angles ≃ 85°) and six-membered (N—Ni—N bite angles ≃ 95°) chelate rings in gauche and chair conformations, respectively (Table 1). The coordination polyhedra of the metal ions can be described as tetragonally elongated trans-NiN₄O₂ octahedra with the Ni—N bond lengths [average value 2.068 (3) Å] slightly shorter than the Ni—O bonds which, in turn, do not display any dependence on the nature of the donor oxygen atoms. The location of the metal ions on crystallographic inversion centers enforces strict planarity of the Ni(N₄) coordination moieties and the axial Ni—O bonds are nearly orthogonal to the NiN₄ planes (deviations of the angles N—Ni—O from 90° do not exceed 2°).

Table 1
Selected geometric parameters (Å, °)

Ni1—N1	2.067 (4)	Ni2—O1W	2.105 (4)
Ni1—N2	2.064 (4)	Ni3—N5	2.070 (4)
Ni1—O1	2.134 (3)	Ni3—N6	2.056 (5)
Ni2—N3	2.072 (4)	Ni3—O2W	2.136 (3)
Ni2—N4	2.076 (4)

N1—Ni1—N2ⁱ	85.31 (16)	N3—Ni2—N4	95.34 (16)
N1—Ni1—N2	94.69 (16)	N5—Ni3—N6ⁱⁱⁱ	85.2 (2)
N3—Ni2—N4ⁱⁱ	84.66 (16)	N5—Ni3—N6	94.8 (2)
Symmetry codes: (i) ; (ii) ; (iii) .

Figure 1
The extended asymmetric unit in I showing the coordination environment of the Ni atoms and the atom-labeling scheme (displacement ellipsoids are drawn at the 30% probability level). C-bound H atoms and uncoordinated water molecules are omitted for clarity. Symmetry codes: (i) −x + 2, −y + 1, −z + 2; (ii) −x + 2, −y + 2, −z + 1; (iii) −x + 1, −y + 3, −z + 1.

The pendant benzene rings of the H₃Me₃BTP^3– tri-anion in I are substantially tilted relative to the central aromatic core [average angle between the mean planes = 76 (5)°] and this feature is caused by repulsive interactions between the hydrogen atoms of the pendant rings and those of the methyl substituents of the central ring. The P—OH bond lengths [average value 1.57 (3) Å] are larger than the other P—O bonds [average value 1.501 (5) Å], thus indicating the partially delocalized character of the phosphonate groups.

3. Supramolecular features

In the crystal of I, the [Ni1(L)(H₃Me₃BTP)₂]^4– anions, [Ni2/Ni3(L)(H₂O)₂]²⁺ cations and water molecules of crystallization are linked by numerous hydrogen bonds with participation of the phosphonate groups, the secondary amino groups of the macrocycles and both the coordinated and crystalline water molecules (Table 2). A distinct lamellar structure is inherent for this compound. In particular, strong hydrogen-bonding interactions between the protonated fragments of the P1 and P3 phosphonate groups of one molecule as the donors with the non-protonated O4 and O5 atoms of the P2 group of another molecule as the acceptors [P1—O3—H3C⋯O5(x, y − 1, z), P3—O9—H9C⋯O49(x, y − 1, z + 1)], together with a weak N1—H1⋯O6 (x, y − 1, z) hydrogen bond between the secondary amino group of the macrocyclic cation [Ni1(L)] and protonated P2—O6 phosphonate fragment result in the formation of anionic layers oriented parallel to the bc plane. The distance between the parallel mean planes of the staggered by 60° trimethylbenzene rings of neighboring H₃Me₃BTP^3– anions is 5.248 (3) Å, thus allowing us to exclude the possibility of aromatic π–π stacking interactions between them. Additionally, the negative charge of the layers are partially compensated by the incorporation within the layers of the [Ni2(L)(H₂O)₂]²⁺ cations via hydrogen bonding between the coordinated water molecules and the phosphonate O7 atom [O1W—H1WB⋯O7(x, y, z − 1)] (Fig. 2).

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6^iv	1.00	2.32	3.196 (5)	146
N2—H2⋯O6W	1.00	2.18	3.039 (6)	143
N3—H3⋯O7^v	1.00	2.13	3.102 (6)	162
N4—H4⋯O4W	1.00	2.06	3.056 (6)	173
N5—H5⋯O9^vi	1.00	2.07	3.003 (6)	155
N6—H6⋯O7Wⁱⁱ	1.00	1.98	2.956 (6)	166
O3—H3C⋯O5^iv	0.84	1.84	2.654 (5)	162
O6—H6C⋯O3W^vii	0.84	1.75	2.550 (5)	159
O9—H9C⋯O4^viii	0.84	1.74	2.517 (5)	154
O1W—H1WB⋯O7^v	0.87	1.81	2.679 (5)	173
O1W—H1WA⋯O4W	0.87	2.45	3.256 (6)	155
O2W—H2WB⋯O4	0.86	1.90	2.729 (5)	164
O2W—H2WA⋯O7W^ix	0.86	1.81	2.675 (6)	174
O3W—H3WB⋯O2	0.87	1.81	2.676 (4)	177
O3W—H3WA⋯O7^v	0.85	1.84	2.689 (5)	174
O4W—H4WB⋯O3	0.87	2.26	3.115 (6)	167
O4W—H4WA⋯O8^v	0.87	1.93	2.796 (6)	172
O5W—H5WB⋯O5^x	0.87	1.98	2.813 (5)	159
O5W—H5WA⋯O8^xi	0.87	1.87	2.725 (5)	168
O6W—H6WB⋯O2	0.87	2.02	2.799 (6)	149
O6W—H6WA⋯O5W	0.87	2.00	2.842 (5)	164
O7W—H7WB⋯O3W	0.85	2.02	2.731 (5)	140
O7W—H7WA⋯O5W	0.86	1.83	2.688 (5)	173
Symmetry codes: (ii) ; (iv) ; (v) ; (vi) ; (vii) x, y+1, z; (viii) ; (ix) ; (x) ; (xi) .

Figure 2
The hydrogen-bonded (dashed lines) layers in I viewed down the a axis. C-bound H atoms and macrocyclic cations formed by Ni3 have been omitted; C and N atoms of the macrocyclic cations formed by Ni2 are shown in green.

The second macrocyclic aqua cation [Ni3(L)(H₂O)₂]²⁺, due to hydrogen bonding of the coordinated water molecule with the phosphonate O4 atom (O2W—H2WB⋯O4), serves as the bridge between the layers, arranging them into a three-dimensional network (Fig. 3), which is further stabilized by numerous O—H⋯O hydrogen bonds involving the water molecules of crystallization, O3W–O7W (Table 2).

Figure 3
The structure of I viewed down the b axis. C-bound H atoms have been omitted; C and N atoms of the macrocyclic cation formed by Ni2 and Ni3 are shown in green and violet, respectively. Water molecules of crystallization are not shown; hydrogen bonds are depicted as dashed lines.

4. Database survey

A search of the Cambridge Structural Database (CSD, version 5.43, last update March 2022; Groom et al., 2016 ) gave no hits related to H₆Me₃BTP or its complexes with metal ions, so the present work is the first structural characterization of a complex of this ligand. At the same time, several works dealing with the structures of the non-methylated analogue of the phosphonate under consideration, namely, 4,4′,4′′-benzene-1,3,5-triyl-triphosphonic acid (H₆BTP), have been published. They include a methanol solvate of the free acid (CSD refcode AKEPEO; Vilela et al., 2021 ) and its pyridinium salt (YOLGEM; Beckmann et al., 2008 ), molecular complexes with solvated Co^II and Ni^II ions (OQIZAR and OQIZEV; Pili et al., 2016 ) and coordination polymers formed by Sr^II (SOTZOR; Vaidhyanathan et al., 2009 ), Zn^II (ISELAV02; Hermer et al., 2016 ), Y^III (AKEPOY; Vilela et al., 2021), Zr^IV (COCLIR; Taddei et al., 2014 ) and V^IV/V (COQNAY; Ouellette et al., 2009 ). Interestingly, as in I, in all the metal complexes except COCLIR and ISELAV02, the ligand acts as a H₃BTP^3– tri-anion with three monodeprotonated phosphonate groups. On the other hand, because of the absence of methyl substituents, the molecules of the anions H_nBTP^(6–n)– as a whole are flatter than H₃Me₃BTP^3– in I with a maximal tilting angle of pendant versus central benzene rings of ca 49° observed in ISELAV02. In addition, in the majority of complexes formed by H_nBTP^(6–n)– ligands (except AKEPOY and ISELAV02), aromatic π–π stacking interactions of different strengths are observed with centroid-to-centroid distances between the central aromatic rings ranging from 3.4 to 3.9 Å.

The Cambridge Structural Database contains also 18 hits describing the structure of the [Ni(L)(H₂O)₂]²⁺ complex cation in salts of different inorganic and organic anions as well as the charge-compensating part in anionic coordination polymers. In general, the structure of this cation in I is similar to other compounds, both from the point of view of the conformation of the macrocycle and the bond distances and angles characterizing the coordination polyhedron of the metal.

5. Synthesis and crystallization

All chemicals and solvents used in this work were purchased from Sigma–Aldrich and used without further purification. The acid H₆Me₃BTP was synthesized according to a procedure described previously for the preparation of H₆BTP (Vaidhyanathan et al., 2009), starting from 1,3,5-trimethyl-2,4,6-tris(4′-bromophenyl)benzene instead of 1,3,5-tris(4′-bromophenyl)benzene. The complex [Ni(L)](ClO₄)₂ was prepared from ethanol solutions as described in the literature (Bosnich et al., 1965b ).

The title compound [Ni(L)(H₂O)₂]₂[Ni(L)(H₃Me₃BTP)₂]·10H₂O, I, was prepared as follows. A solution of [Ni(L)](ClO₄)₂ (46 mg, 0.1 mmol) in 5 ml of water was added to 5 ml of an aqueous solution of H₆Me₃BTP (18 mg, 0.03 mmol) containing 2 ml of pyridine. The pink precipitate, which formed in a week, was filtered off, washed with small amounts of water, methanol and diethyl ether, and dried in air. Yield: 7 mg (10% based on acid). Analysis calculated for C₈₄H₁₄₈N₁₂Ni₃O₃₂P₆: C 45.85, H 6.78, N 7.64%. Found: C 45.73, H 6.87, N 7.51%. Single crystals of I suitable for X-ray diffraction analysis were selected from the sample resulting from the synthesis.

Caution! Perchlorate salts of metal complexes are potentially explosive and should be handled with care.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. H atoms in I were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.95 Å (ring H atoms), 0.98 Å (methyl H atoms), 0.99 Å (methylene H atoms), N—H distances of 1.00 Å, O—H distances of 0.84 Å (protonated phosphonate groups) and 0.87 Å (water molecules) with U_iso(H) values of 1.2U_eq or 1.5U_eq times those of the corresponding parent atoms.

Table 3
Experimental details

Crystal data
Chemical formula	[Ni(C₁₀H₂₄N₄)(H₂O)₂]₂[Ni(C₁₀H₂₄N₄)(C₂₇H₂₄O₉P₃)₂]·10H₂O
M_r	2200.09
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	160
a, b, c (Å)	9.8779 (5), 17.2467 (11), 17.6707 (11)
α, β, γ (°)	61.409 (6), 77.515 (5), 77.713 (5)
V (Å³)	2559.7 (3)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	0.72
Crystal size (mm)	0.40 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku Xcalibur Eos
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2020 $[Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.701, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	23737, 9657, 6598
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.161, 1.02
No. of reflections	9657
No. of parameters	629
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.46
Computer programs: CrysAlis PRO (Rigaku OD, 2020 $[Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), Mercury (Macrae et al., 2020 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2178456

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989022006624/hb8026sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989022006624/hb8026Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2020); cell refinement: CrysAlis PRO (Rigaku OD, 2020); data reduction: CrysAlis PRO (Rigaku OD, 2020); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

\ Bis[trans-diaqua(1,4,8,11-tetraazacyclotetradecane-κ⁴N¹,\ N⁴,N⁸,N¹¹)nickel(II)] trans-(1,4,8,11-tetraazacyclotetradecane-κ⁴N¹,N⁴,\ N⁸,N¹¹)bis[4,4',4''-(1,3,5-trimethylbenzene-2,4,6-triyl)\ tris(hydrogen phenylphosphonato-κO)]nickel(II) decahydrate top

Crystal data top

[Ni(C₁₀H₂₄N₄)(H₂O)₂]₂[Ni(C₁₀H₂₄N₄)(C₂₇H₂₄O₉P₃)₂]·10H₂O	Z = 1
M_r = 2200.09	F(000) = 1166
Triclinic, P1	D_x = 1.427 Mg m⁻³
a = 9.8779 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 17.2467 (11) Å	Cell parameters from 5403 reflections
c = 17.6707 (11) Å	θ = 2.1–26.3°
α = 61.409 (6)°	µ = 0.72 mm⁻¹
β = 77.515 (5)°	T = 160 K
γ = 77.713 (5)°	Prism, clear light colourless
V = 2559.7 (3) Å³	0.40 × 0.10 × 0.10 mm

Data collection top

Rigaku Xcalibur Eos diffractometer	9657 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	6598 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
Detector resolution: 16.1593 pixels mm^-1	θ_max = 25.7°, θ_min = 2.1°
ω scans	h = −11→12
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	k = −21→20
T_min = 0.701, T_max = 1.000	l = −21→21
23737 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.067	H-atom parameters constrained
wR(F²) = 0.161	w = 1/[σ²(F_o²) + (0.0527P)² + 4.2781P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
9657 reflections	Δρ_max = 0.67 e Å⁻³
629 parameters	Δρ_min = −0.46 e Å⁻³
1 restraint

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
Ni1	1.000000	0.500000	1.000000	0.0228 (2)
P2	0.77348 (14)	1.51832 (8)	0.73137 (8)	0.0273 (3)
P1	0.86291 (13)	0.70402 (8)	0.82874 (8)	0.0243 (3)
P3	0.75955 (15)	0.78200 (9)	1.49060 (8)	0.0332 (3)
O5	0.6838 (4)	1.5710 (2)	0.7750 (2)	0.0380 (9)
C29	0.7561 (5)	1.4015 (3)	0.7965 (3)	0.0241 (10)
O4	0.7456 (4)	1.5452 (2)	0.6413 (2)	0.0333 (8)
O3W	1.0380 (3)	0.6623 (2)	0.6411 (2)	0.0311 (8)
H3WA	0.998703	0.703601	0.598132	0.047*
H3WB	1.016063	0.687031	0.675752	0.047*
O4W	0.6258 (4)	0.8895 (3)	0.6511 (3)	0.0607 (12)
H4WA	0.622702	0.869018	0.615193	0.091*
H4WB	0.655562	0.843018	0.696393	0.091*
C22	0.7292 (4)	0.9758 (3)	0.9717 (3)	0.0193 (10)
C38	0.7501 (5)	0.8505 (3)	1.3753 (3)	0.0274 (11)
C26	0.7310 (5)	1.2190 (3)	0.9041 (3)	0.0230 (10)
N1	0.9914 (4)	0.4354 (3)	0.9286 (2)	0.0275 (9)
H1	0.956271	0.481640	0.873064	0.033*
O3	0.7242 (4)	0.7049 (2)	0.7985 (2)	0.0387 (9)
H3C	0.724711	0.656089	0.798510	0.058*
C34	0.7272 (4)	0.9926 (3)	1.1008 (3)	0.0211 (10)
N2	1.1919 (4)	0.5419 (3)	0.9365 (3)	0.0330 (10)
H2	1.173656	0.596679	0.881233	0.040*
C3	1.2935 (5)	0.4794 (4)	0.9119 (4)	0.0421 (14)
H3A	1.320107	0.425875	0.965248	0.051*
H3B	1.378830	0.507709	0.878884	0.051*
O2	0.9773 (4)	0.7334 (2)	0.7517 (2)	0.0349 (8)
O9	0.7490 (5)	0.6880 (2)	1.5017 (2)	0.0490 (11)
H9C	0.757613	0.649777	1.553173	0.074*
C35	0.7357 (5)	0.9486 (3)	1.1963 (3)	0.0245 (10)
C41	0.7258 (5)	0.9377 (3)	1.0620 (3)	0.0229 (10)
C23	0.7243 (5)	1.0683 (3)	0.9212 (3)	0.0229 (10)
C30	0.6330 (5)	1.3737 (3)	0.8509 (3)	0.0335 (12)
H30	0.555907	1.416974	0.852158	0.040*
C25	0.7243 (5)	1.1221 (3)	0.9602 (3)	0.0216 (10)
C5	0.8806 (6)	0.3769 (4)	0.9791 (3)	0.0381 (13)
H5A	0.916444	0.324112	1.029994	0.046*
H5B	0.851180	0.356262	0.942372	0.046*
C33	0.7319 (5)	1.1422 (3)	1.0923 (3)	0.0280 (11)
H33A	0.769682	1.105369	1.147602	0.042*
H33B	0.637231	1.170079	1.102996	0.042*
H33C	0.791865	1.188533	1.053584	0.042*
C39	0.6285 (5)	0.9036 (3)	1.3453 (3)	0.0321 (12)
H39	0.549541	0.906986	1.385777	0.039*
C42	0.7241 (6)	0.8387 (3)	1.1158 (3)	0.0333 (12)
H42A	0.818887	0.807974	1.111379	0.050*
H42B	0.661713	0.818665	1.094399	0.050*
H42C	0.690678	0.825159	1.176739	0.050*
O7	0.9019 (4)	0.7838 (2)	1.5071 (2)	0.0399 (9)
C36	0.8576 (5)	0.8993 (3)	1.2269 (3)	0.0283 (11)
H36	0.938419	0.898840	1.186477	0.034*
C19	0.7533 (4)	0.9154 (3)	0.9299 (3)	0.0194 (10)
C21	0.6772 (5)	0.8176 (3)	0.8889 (3)	0.0282 (11)
H21	0.603252	0.793241	0.884480	0.034*
O8	0.6378 (4)	0.8126 (3)	1.5414 (2)	0.0476 (10)
C20	0.6477 (5)	0.8787 (3)	0.9222 (3)	0.0287 (11)
H20	0.553187	0.895677	0.940187	0.034*
C2	1.2358 (6)	0.4512 (4)	0.8569 (3)	0.0407 (14)
H2A	1.196217	0.505379	0.808660	0.049*
H2B	1.314402	0.421415	0.830904	0.049*
C37	0.8665 (5)	0.8500 (3)	1.3151 (3)	0.0306 (12)
H37	0.952338	0.815768	1.334400	0.037*
C32	0.7271 (4)	1.0848 (3)	1.0504 (3)	0.0211 (10)
C24	0.7140 (6)	1.1079 (3)	0.8254 (3)	0.0314 (12)
H24A	0.660985	1.072081	0.815897	0.047*
H24B	0.808141	1.108441	0.793050	0.047*
H24C	0.666278	1.168989	0.805139	0.047*
Ni2	1.000000	1.000000	0.500000	0.0233 (2)
O1W	0.9604 (4)	0.8687 (2)	0.5872 (2)	0.0452 (10)
H1WA	0.881040	0.872384	0.618973	0.068*
H1WB	0.944450	0.844264	0.557414	0.068*
N3	0.9605 (4)	0.9803 (3)	0.4004 (2)	0.0297 (10)
H3	0.924717	0.921388	0.427638	0.036*
C10	1.0986 (5)	0.9720 (4)	0.3496 (3)	0.0380 (13)
H10A	1.128892	1.031639	0.311897	0.046*
H10B	1.091906	0.945314	0.312116	0.046*
N4	0.7940 (5)	1.0447 (3)	0.5321 (3)	0.0377 (11)
H4	0.744740	0.990779	0.568716	0.045*
C9	0.7973 (6)	1.0856 (4)	0.5889 (3)	0.0408 (14)
H9A	0.703665	1.090138	0.621780	0.049*
H9B	0.824723	1.146279	0.553175	0.049*
C7	0.7183 (6)	1.0577 (4)	0.4022 (3)	0.0418 (14)
H7A	0.689758	0.997677	0.440380	0.050*
H7B	0.646435	1.092349	0.362786	0.050*
C6	0.8543 (5)	1.0479 (3)	0.3477 (3)	0.0350 (12)
H6A	0.837243	1.030970	0.304733	0.042*
H6B	0.891090	1.106025	0.315290	0.042*
C8	0.7168 (6)	1.1019 (4)	0.4586 (4)	0.0434 (14)
H8A	0.758644	1.158069	0.423021	0.052*
H8B	0.618830	1.116899	0.480465	0.052*
Ni3	0.500000	1.500000	0.500000	0.0280 (2)
O2W	0.5104 (4)	1.5055 (2)	0.6168 (2)	0.0374 (9)
H2WA	0.451405	1.548647	0.620771	0.056*
H2WB	0.589347	1.520291	0.613928	0.056*
N5	0.3476 (5)	1.4161 (3)	0.5683 (3)	0.0436 (12)
H5	0.333782	1.392139	0.529340	0.052*
O7W	1.3235 (4)	0.6425 (3)	0.6174 (3)	0.0660 (14)
H7WA	1.366682	0.665639	0.637536	0.099*
H7WB	1.244232	0.671069	0.624896	0.099*
N6	0.6644 (5)	1.3992 (3)	0.5280 (3)	0.0464 (12)
H6	0.671366	1.374659	0.486100	0.056*
C14	0.7918 (6)	1.4389 (5)	0.5068 (4)	0.0558 (18)
H14A	0.873557	1.397569	0.499126	0.067*
H14B	0.802863	1.450247	0.554899	0.067*
O6W	1.2369 (4)	0.7283 (3)	0.7946 (2)	0.0541 (11)
H6WA	1.317921	0.726218	0.763661	0.081*
H6WB	1.177461	0.729258	0.764271	0.081*
O5W	1.4763 (3)	0.7022 (2)	0.6828 (2)	0.0395 (9)
H5WA	1.538341	0.732237	0.641517	0.059*
H5WB	1.524801	0.660758	0.722817	0.059*
O1	0.9002 (4)	0.6178 (2)	0.9039 (2)	0.0326 (8)
O6	0.9335 (4)	1.5164 (2)	0.7321 (2)	0.0402 (9)
H6C	0.960853	1.564111	0.692096	0.060*
C17	0.9212 (5)	0.8304 (3)	0.8664 (3)	0.0229 (10)
H17	1.015334	0.815323	0.846193	0.027*
C16	0.8155 (5)	0.7918 (3)	0.8618 (3)	0.0216 (10)
C18	0.8904 (5)	0.8913 (3)	0.9005 (3)	0.0238 (10)
H18	0.964113	0.916614	0.903815	0.029*
C40	0.6201 (5)	0.9525 (3)	1.2561 (3)	0.0302 (12)
H40	0.535465	0.988328	1.236326	0.036*
C1	1.1247 (6)	0.3895 (3)	0.9048 (3)	0.0375 (13)
H1A	1.108999	0.364727	0.867554	0.045*
H1B	1.157958	0.339182	0.958205	0.045*
C28	0.8659 (5)	1.3371 (3)	0.7957 (3)	0.0323 (12)
H28	0.950712	1.353974	0.758385	0.039*
C31	0.6206 (5)	1.2844 (3)	0.9032 (3)	0.0319 (12)
H31	0.534822	1.267424	0.939145	0.038*
C13	0.6486 (8)	1.3227 (4)	0.6163 (4)	0.0614 (19)
H13A	0.651043	1.342483	0.660143	0.074*
H13B	0.728211	1.275571	0.620745	0.074*
C15	0.2154 (6)	1.4748 (5)	0.5758 (4)	0.0502 (16)
H15A	0.212231	1.487228	0.625394	0.060*
H15B	0.133940	1.444182	0.586810	0.060*
C11	0.3777 (8)	1.3401 (5)	0.6484 (4)	0.0606 (19)
H11A	0.300674	1.302890	0.671624	0.073*
H11B	0.383358	1.360212	0.691424	0.073*
C27	0.8528 (5)	1.2485 (3)	0.8489 (3)	0.0315 (12)
H27	0.930342	1.205552	0.847868	0.038*
C12	0.5140 (8)	1.2849 (4)	0.6361 (4)	0.065 (2)
H12A	0.519087	1.227524	0.689642	0.078*
H12B	0.509541	1.271311	0.588269	0.078*
C4	1.2423 (5)	0.5705 (4)	0.9910 (3)	0.0360 (13)
H4A	1.318132	0.607996	0.956861	0.043*
H4B	1.279137	0.517994	1.041693	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0278 (5)	0.0183 (4)	0.0225 (4)	0.0031 (4)	−0.0059 (3)	−0.0108 (4)
P2	0.0380 (8)	0.0178 (6)	0.0273 (7)	−0.0020 (6)	−0.0117 (6)	−0.0089 (5)
P1	0.0314 (7)	0.0195 (6)	0.0258 (6)	0.0026 (6)	−0.0079 (5)	−0.0139 (5)
P3	0.0495 (9)	0.0290 (7)	0.0222 (7)	−0.0109 (7)	−0.0112 (6)	−0.0074 (6)
O5	0.056 (2)	0.0220 (18)	0.042 (2)	0.0005 (18)	−0.0129 (18)	−0.0184 (17)
C29	0.031 (3)	0.023 (2)	0.019 (2)	0.000 (2)	−0.0063 (19)	−0.010 (2)
O4	0.051 (2)	0.0229 (18)	0.0265 (18)	−0.0077 (17)	−0.0132 (16)	−0.0072 (15)
O3W	0.0317 (19)	0.0298 (19)	0.0354 (19)	0.0021 (16)	−0.0082 (15)	−0.0185 (16)
O4W	0.064 (3)	0.059 (3)	0.060 (3)	−0.013 (2)	−0.008 (2)	−0.026 (2)
C22	0.017 (2)	0.022 (2)	0.020 (2)	−0.002 (2)	0.0003 (18)	−0.012 (2)
C38	0.040 (3)	0.022 (2)	0.025 (3)	−0.007 (2)	−0.011 (2)	−0.010 (2)
C26	0.030 (3)	0.019 (2)	0.022 (2)	−0.002 (2)	−0.005 (2)	−0.011 (2)
N1	0.036 (2)	0.021 (2)	0.026 (2)	0.0064 (19)	−0.0090 (18)	−0.0131 (18)
O3	0.049 (2)	0.027 (2)	0.054 (2)	0.0082 (18)	−0.0240 (18)	−0.0272 (19)
C34	0.019 (2)	0.025 (2)	0.021 (2)	0.006 (2)	−0.0042 (18)	−0.014 (2)
N2	0.039 (3)	0.031 (2)	0.030 (2)	−0.003 (2)	−0.0034 (19)	−0.016 (2)
C3	0.033 (3)	0.052 (4)	0.046 (3)	−0.004 (3)	0.006 (2)	−0.032 (3)
O2	0.047 (2)	0.031 (2)	0.0312 (19)	−0.0057 (17)	0.0045 (16)	−0.0216 (17)
O9	0.090 (3)	0.034 (2)	0.028 (2)	−0.021 (2)	−0.022 (2)	−0.0065 (17)
C35	0.028 (3)	0.023 (2)	0.024 (2)	−0.004 (2)	−0.004 (2)	−0.012 (2)
C41	0.023 (2)	0.019 (2)	0.027 (2)	0.000 (2)	−0.0026 (19)	−0.012 (2)
C23	0.026 (3)	0.022 (2)	0.019 (2)	0.004 (2)	−0.0033 (19)	−0.010 (2)
C30	0.028 (3)	0.022 (3)	0.046 (3)	0.003 (2)	−0.006 (2)	−0.014 (2)
C25	0.021 (2)	0.018 (2)	0.025 (2)	0.001 (2)	−0.0017 (19)	−0.010 (2)
C5	0.053 (4)	0.030 (3)	0.034 (3)	−0.007 (3)	−0.010 (3)	−0.014 (2)
C33	0.035 (3)	0.022 (2)	0.031 (3)	0.000 (2)	−0.008 (2)	−0.016 (2)
C39	0.033 (3)	0.040 (3)	0.023 (3)	−0.007 (3)	−0.003 (2)	−0.013 (2)
C42	0.052 (3)	0.021 (3)	0.027 (3)	−0.004 (2)	−0.009 (2)	−0.010 (2)
O7	0.053 (2)	0.038 (2)	0.0282 (19)	−0.0107 (19)	−0.0119 (17)	−0.0096 (17)
C36	0.038 (3)	0.025 (3)	0.024 (3)	0.001 (2)	−0.006 (2)	−0.014 (2)
C19	0.023 (2)	0.018 (2)	0.015 (2)	0.001 (2)	−0.0015 (18)	−0.0077 (19)
C21	0.026 (3)	0.032 (3)	0.036 (3)	−0.002 (2)	−0.006 (2)	−0.023 (2)
O8	0.054 (2)	0.053 (3)	0.0258 (19)	−0.001 (2)	−0.0044 (17)	−0.0116 (19)
C20	0.023 (3)	0.033 (3)	0.036 (3)	0.004 (2)	−0.001 (2)	−0.024 (2)
C2	0.036 (3)	0.048 (4)	0.041 (3)	0.010 (3)	−0.005 (2)	−0.029 (3)
C37	0.038 (3)	0.025 (3)	0.030 (3)	0.007 (2)	−0.015 (2)	−0.013 (2)
C32	0.020 (2)	0.023 (2)	0.022 (2)	0.004 (2)	−0.0025 (18)	−0.013 (2)
C24	0.050 (3)	0.021 (2)	0.025 (3)	−0.003 (2)	−0.007 (2)	−0.012 (2)
Ni2	0.0292 (5)	0.0196 (4)	0.0220 (4)	0.0031 (4)	−0.0055 (4)	−0.0117 (4)
O1W	0.073 (3)	0.036 (2)	0.033 (2)	−0.014 (2)	−0.0077 (19)	−0.0169 (18)
N3	0.042 (3)	0.027 (2)	0.023 (2)	−0.007 (2)	−0.0027 (18)	−0.0130 (18)
C10	0.049 (3)	0.044 (3)	0.031 (3)	−0.007 (3)	−0.005 (2)	−0.024 (3)
N4	0.046 (3)	0.031 (2)	0.040 (3)	−0.002 (2)	−0.009 (2)	−0.019 (2)
C9	0.041 (3)	0.047 (3)	0.037 (3)	−0.002 (3)	0.001 (2)	−0.025 (3)
C7	0.046 (3)	0.041 (3)	0.037 (3)	0.001 (3)	−0.014 (3)	−0.016 (3)
C6	0.050 (3)	0.029 (3)	0.031 (3)	0.001 (3)	−0.015 (2)	−0.016 (2)
C8	0.047 (4)	0.039 (3)	0.043 (3)	0.002 (3)	−0.009 (3)	−0.020 (3)
Ni3	0.0357 (5)	0.0258 (5)	0.0275 (5)	−0.0032 (4)	−0.0080 (4)	−0.0148 (4)
O2W	0.046 (2)	0.043 (2)	0.034 (2)	−0.0071 (19)	−0.0093 (17)	−0.0240 (18)
N5	0.058 (3)	0.045 (3)	0.039 (3)	−0.017 (3)	−0.008 (2)	−0.023 (2)
O7W	0.037 (2)	0.102 (4)	0.104 (4)	0.006 (2)	−0.008 (2)	−0.089 (3)
N6	0.050 (3)	0.050 (3)	0.056 (3)	0.008 (3)	−0.023 (2)	−0.037 (3)
C14	0.042 (4)	0.071 (5)	0.079 (5)	0.013 (3)	−0.014 (3)	−0.059 (4)
O6W	0.052 (3)	0.059 (3)	0.042 (2)	0.004 (2)	−0.0005 (19)	−0.023 (2)
O5W	0.035 (2)	0.041 (2)	0.041 (2)	−0.0007 (18)	−0.0030 (16)	−0.0199 (18)
O1	0.045 (2)	0.0221 (18)	0.0296 (19)	0.0041 (16)	−0.0121 (16)	−0.0115 (15)
O6	0.042 (2)	0.026 (2)	0.044 (2)	−0.0058 (18)	−0.0156 (17)	−0.0044 (17)
C17	0.023 (2)	0.022 (2)	0.021 (2)	0.000 (2)	0.0004 (19)	−0.010 (2)
C16	0.028 (3)	0.020 (2)	0.019 (2)	0.000 (2)	−0.0066 (19)	−0.010 (2)
C18	0.025 (3)	0.022 (2)	0.028 (3)	−0.004 (2)	−0.005 (2)	−0.014 (2)
C40	0.025 (3)	0.034 (3)	0.031 (3)	0.001 (2)	−0.007 (2)	−0.015 (2)
C1	0.048 (3)	0.030 (3)	0.043 (3)	0.010 (3)	−0.016 (3)	−0.025 (3)
C28	0.036 (3)	0.027 (3)	0.032 (3)	−0.007 (2)	0.009 (2)	−0.017 (2)
C31	0.021 (3)	0.024 (3)	0.041 (3)	0.000 (2)	0.004 (2)	−0.011 (2)
C13	0.090 (5)	0.038 (4)	0.060 (4)	0.013 (4)	−0.044 (4)	−0.020 (3)
C15	0.041 (4)	0.070 (5)	0.058 (4)	−0.014 (3)	0.006 (3)	−0.046 (4)
C11	0.087 (5)	0.057 (4)	0.042 (4)	−0.035 (4)	−0.005 (3)	−0.017 (3)
C27	0.035 (3)	0.023 (3)	0.031 (3)	0.000 (2)	0.006 (2)	−0.013 (2)
C12	0.106 (6)	0.034 (4)	0.048 (4)	−0.015 (4)	−0.034 (4)	−0.002 (3)
C4	0.039 (3)	0.035 (3)	0.034 (3)	−0.003 (3)	−0.011 (2)	−0.014 (3)

Geometric parameters (Å, º) top

Ni1—N1ⁱ	2.067 (4)	C24—H24A	0.9800
Ni1—N1	2.067 (4)	C24—H24B	0.9800
Ni1—N2	2.064 (4)	C24—H24C	0.9800
Ni1—N2ⁱ	2.064 (4)	Ni2—N3ⁱⁱ	2.072 (4)
Ni1—O1ⁱ	2.134 (3)	Ni2—N3	2.072 (4)
Ni1—O1	2.134 (3)	Ni2—N4	2.076 (4)
P2—O5	1.495 (4)	Ni2—N4ⁱⁱ	2.076 (4)
P2—C29	1.804 (5)	Ni2—O1Wⁱⁱ	2.105 (4)
P2—O4	1.502 (3)	Ni2—O1W	2.105 (4)
P2—O6	1.576 (4)	O1W—H1WA	0.8701
P1—O3	1.570 (4)	O1W—H1WB	0.8691
P1—O2	1.518 (3)	N3—H3	1.0000
P1—O1	1.483 (3)	N3—C10	1.481 (6)
P1—C16	1.811 (5)	N3—C6	1.479 (6)
P3—C38	1.813 (5)	C10—H10A	0.9900
P3—O9	1.562 (4)	C10—H10B	0.9900
P3—O7	1.506 (4)	C10—C9ⁱⁱ	1.496 (7)
P3—O8	1.499 (4)	N4—H4	1.0000
C29—C30	1.391 (7)	N4—C9	1.486 (6)
C29—C28	1.381 (7)	N4—C8	1.457 (7)
O3W—H3WA	0.8523	C9—H9A	0.9900
O3W—H3WB	0.8700	C9—H9B	0.9900
O4W—H4WA	0.8687	C7—H7A	0.9900
O4W—H4WB	0.8702	C7—H7B	0.9900
C22—C41	1.400 (6)	C7—C6	1.504 (7)
C22—C23	1.402 (6)	C7—C8	1.513 (7)
C22—C19	1.497 (6)	C6—H6A	0.9900
C38—C39	1.380 (7)	C6—H6B	0.9900
C38—C37	1.390 (7)	C8—H8A	0.9900
C26—C25	1.488 (6)	C8—H8B	0.9900
C26—C31	1.388 (6)	Ni3—N5	2.070 (4)
C26—C27	1.392 (6)	Ni3—N5ⁱⁱⁱ	2.070 (5)
N1—H1	1.0000	Ni3—N6	2.056 (5)
N1—C5	1.482 (6)	Ni3—N6ⁱⁱⁱ	2.056 (5)
N1—C1	1.474 (6)	Ni3—O2Wⁱⁱⁱ	2.137 (3)
O3—H3C	0.8400	Ni3—O2W	2.136 (3)
C34—C35	1.497 (6)	O2W—H2WA	0.8638
C34—C41	1.414 (6)	O2W—H2WB	0.8553
C34—C32	1.401 (6)	N5—H5	1.0000
N2—H2	1.0000	N5—C15	1.497 (7)
N2—C3	1.469 (6)	N5—C11	1.431 (8)
N2—C4	1.477 (6)	O7W—H7WA	0.8613
C3—H3A	0.9900	O7W—H7WB	0.8521
C3—H3B	0.9900	N6—H6	1.0000
C3—C2	1.521 (7)	N6—C14	1.452 (7)
O9—H9C	0.8400	N6—C13	1.487 (8)
C35—C36	1.368 (7)	C14—H14A	0.9900
C35—C40	1.392 (6)	C14—H14B	0.9900
C41—C42	1.507 (6)	C14—C15ⁱⁱⁱ	1.507 (9)
C23—C25	1.396 (6)	O6W—H6WA	0.8706
C23—C24	1.510 (6)	O6W—H6WB	0.8688
C30—H30	0.9500	O5W—H5WA	0.8696
C30—C31	1.382 (7)	O5W—H5WB	0.8704
C25—C32	1.409 (6)	O6—H6C	0.8400
C5—H5A	0.9900	C17—H17	0.9500
C5—H5B	0.9900	C17—C16	1.387 (6)
C5—C4ⁱ	1.513 (7)	C17—C18	1.396 (6)
C33—H33A	0.9800	C18—H18	0.9500
C33—H33B	0.9800	C40—H40	0.9500
C33—H33C	0.9800	C1—H1A	0.9900
C33—C32	1.506 (6)	C1—H1B	0.9900
C39—H39	0.9500	C28—H28	0.9500
C39—C40	1.399 (6)	C28—C27	1.375 (7)
C42—H42A	0.9800	C31—H31	0.9500
C42—H42B	0.9800	C13—H13A	0.9900
C42—H42C	0.9800	C13—H13B	0.9900
C36—H36	0.9500	C13—C12	1.506 (9)
C36—C37	1.385 (6)	C15—H15A	0.9900
C19—C20	1.391 (6)	C15—H15B	0.9900
C19—C18	1.393 (6)	C11—H11A	0.9900
C21—H21	0.9500	C11—H11B	0.9900
C21—C20	1.389 (6)	C11—C12	1.514 (10)
C21—C16	1.398 (6)	C27—H27	0.9500
C20—H20	0.9500	C12—H12A	0.9900
C2—H2A	0.9900	C12—H12B	0.9900
C2—H2B	0.9900	C4—H4A	0.9900
C2—C1	1.513 (7)	C4—H4B	0.9900
C37—H37	0.9500

N1—Ni1—N1ⁱ	180.0	N4—Ni2—O1W	89.10 (17)
N1—Ni1—O1ⁱ	91.79 (14)	N4ⁱⁱ—Ni2—O1W	90.90 (17)
N1ⁱ—Ni1—O1ⁱ	88.21 (14)	N4ⁱⁱ—Ni2—O1Wⁱⁱ	89.10 (17)
N1ⁱ—Ni1—O1	91.79 (14)	N4—Ni2—N4ⁱⁱ	180.00 (13)
N1—Ni1—O1	88.21 (14)	Ni2—O1W—H1WA	106.8
N1—Ni1—N2ⁱ	85.31 (16)	Ni2—O1W—H1WB	108.1
N1ⁱ—Ni1—N2	85.31 (16)	H1WA—O1W—H1WB	104.5
N1ⁱ—Ni1—N2ⁱ	94.69 (16)	Ni2—N3—H3	107.3
N1—Ni1—N2	94.69 (16)	C10—N3—Ni2	105.7 (3)
N2ⁱ—Ni1—N2	180.0	C10—N3—H3	107.3
N2ⁱ—Ni1—O1	90.47 (15)	C6—N3—Ni2	114.6 (3)
N2—Ni1—O1	89.53 (15)	C6—N3—H3	107.3
N2ⁱ—Ni1—O1ⁱ	89.53 (15)	C6—N3—C10	114.3 (4)
N2—Ni1—O1ⁱ	90.47 (15)	N3—C10—H10A	109.9
O1ⁱ—Ni1—O1	180.0	N3—C10—H10B	109.9
O5—P2—C29	110.3 (2)	N3—C10—C9ⁱⁱ	109.1 (4)
O5—P2—O4	115.4 (2)	H10A—C10—H10B	108.3
O5—P2—O6	111.3 (2)	C9ⁱⁱ—C10—H10A	109.9
O4—P2—C29	108.0 (2)	C9ⁱⁱ—C10—H10B	109.9
O4—P2—O6	110.5 (2)	Ni2—N4—H4	106.9
O6—P2—C29	100.2 (2)	C9—N4—Ni2	106.4 (3)
O3—P1—C16	102.1 (2)	C9—N4—H4	106.9
O2—P1—O3	110.2 (2)	C8—N4—Ni2	115.2 (3)
O2—P1—C16	107.1 (2)	C8—N4—H4	106.9
O1—P1—O3	111.4 (2)	C8—N4—C9	114.0 (4)
O1—P1—O2	115.2 (2)	C10ⁱⁱ—C9—H9A	110.1
O1—P1—C16	110.06 (19)	C10ⁱⁱ—C9—H9B	110.1
O9—P3—C38	101.5 (2)	N4—C9—C10ⁱⁱ	108.1 (4)
O7—P3—C38	107.6 (2)	N4—C9—H9A	110.1
O7—P3—O9	109.8 (2)	N4—C9—H9B	110.1
O8—P3—C38	109.4 (2)	H9A—C9—H9B	108.4
O8—P3—O9	111.8 (2)	H7A—C7—H7B	107.3
O8—P3—O7	115.7 (2)	C6—C7—H7A	108.1
C30—C29—P2	120.9 (4)	C6—C7—H7B	108.1
C28—C29—P2	121.0 (4)	C6—C7—C8	116.9 (5)
C28—C29—C30	118.0 (4)	C8—C7—H7A	108.1
H3WA—O3W—H3WB	98.3	C8—C7—H7B	108.1
H4WA—O4W—H4WB	104.4	N3—C6—C7	112.6 (4)
C41—C22—C23	120.1 (4)	N3—C6—H6A	109.1
C41—C22—C19	118.6 (4)	N3—C6—H6B	109.1
C23—C22—C19	120.9 (4)	C7—C6—H6A	109.1
C39—C38—P3	121.3 (4)	C7—C6—H6B	109.1
C39—C38—C37	118.6 (4)	H6A—C6—H6B	107.8
C37—C38—P3	120.1 (4)	N4—C8—C7	111.9 (5)
C31—C26—C25	123.6 (4)	N4—C8—H8A	109.2
C31—C26—C27	116.3 (4)	N4—C8—H8B	109.2
C27—C26—C25	120.1 (4)	C7—C8—H8A	109.2
Ni1—N1—H1	106.9	C7—C8—H8B	109.2
C5—N1—Ni1	104.8 (3)	H8A—C8—H8B	107.9
C5—N1—H1	106.9	O2W—Ni3—O2Wⁱⁱⁱ	180.0
C1—N1—Ni1	116.4 (3)	N5ⁱⁱⁱ—Ni3—O2W	91.54 (15)
C1—N1—H1	106.9	N5—Ni3—O2W	88.46 (15)
C1—N1—C5	114.2 (4)	N5ⁱⁱⁱ—Ni3—O2Wⁱⁱⁱ	88.46 (15)
P1—O3—H3C	109.5	N5—Ni3—O2Wⁱⁱⁱ	91.54 (15)
C41—C34—C35	117.8 (4)	N5—Ni3—N5ⁱⁱⁱ	180.0
C32—C34—C35	121.4 (4)	N6—Ni3—O2W	89.19 (16)
C32—C34—C41	120.8 (4)	N6ⁱⁱⁱ—Ni3—O2W	90.81 (16)
Ni1—N2—H2	106.6	N6ⁱⁱⁱ—Ni3—O2Wⁱⁱⁱ	89.19 (16)
C3—N2—Ni1	116.1 (3)	N6—Ni3—O2Wⁱⁱⁱ	90.81 (16)
C3—N2—H2	106.6	N5—Ni3—N6ⁱⁱⁱ	85.2 (2)
C3—N2—C4	114.4 (4)	N5—Ni3—N6	94.8 (2)
C4—N2—Ni1	106.0 (3)	N5ⁱⁱⁱ—Ni3—N6	85.2 (2)
C4—N2—H2	106.6	N5ⁱⁱⁱ—Ni3—N6ⁱⁱⁱ	94.8 (2)
N2—C3—H3A	109.1	N6ⁱⁱⁱ—Ni3—N6	180.0
N2—C3—H3B	109.1	Ni3—O2W—H2WA	110.2
N2—C3—C2	112.3 (4)	Ni3—O2W—H2WB	109.7
H3A—C3—H3B	107.9	H2WA—O2W—H2WB	103.1
C2—C3—H3A	109.1	Ni3—N5—H5	106.1
C2—C3—H3B	109.1	C15—N5—Ni3	105.8 (4)
P3—O9—H9C	109.5	C15—N5—H5	106.1
C36—C35—C34	119.7 (4)	C11—N5—Ni3	117.4 (4)
C36—C35—C40	118.5 (4)	C11—N5—H5	106.1
C40—C35—C34	121.7 (4)	C11—N5—C15	114.5 (5)
C22—C41—C34	119.4 (4)	H7WA—O7W—H7WB	94.0
C22—C41—C42	119.5 (4)	Ni3—N6—H6	106.1
C34—C41—C42	121.1 (4)	C14—N6—Ni3	107.9 (4)
C22—C23—C24	118.7 (4)	C14—N6—H6	106.1
C25—C23—C22	120.0 (4)	C14—N6—C13	114.0 (5)
C25—C23—C24	121.2 (4)	C13—N6—Ni3	115.9 (4)
C29—C30—H30	119.4	C13—N6—H6	106.1
C31—C30—C29	121.2 (5)	N6—C14—H14A	109.8
C31—C30—H30	119.4	N6—C14—H14B	109.8
C23—C25—C26	118.9 (4)	N6—C14—C15ⁱⁱⁱ	109.4 (5)
C23—C25—C32	120.8 (4)	H14A—C14—H14B	108.2
C32—C25—C26	120.2 (4)	C15ⁱⁱⁱ—C14—H14A	109.8
N1—C5—H5A	110.0	C15ⁱⁱⁱ—C14—H14B	109.8
N1—C5—H5B	110.0	H6WA—O6W—H6WB	104.5
N1—C5—C4ⁱ	108.4 (4)	H5WA—O5W—H5WB	104.5
H5A—C5—H5B	108.4	P1—O1—Ni1	167.3 (2)
C4ⁱ—C5—H5A	110.0	P2—O6—H6C	109.5
C4ⁱ—C5—H5B	110.0	C16—C17—H17	119.7
H33A—C33—H33B	109.5	C16—C17—C18	120.5 (4)
H33A—C33—H33C	109.5	C18—C17—H17	119.7
H33B—C33—H33C	109.5	C21—C16—P1	122.4 (4)
C32—C33—H33A	109.5	C17—C16—P1	118.7 (3)
C32—C33—H33B	109.5	C17—C16—C21	118.7 (4)
C32—C33—H33C	109.5	C19—C18—C17	121.1 (4)
C38—C39—H39	119.6	C19—C18—H18	119.5
C38—C39—C40	120.8 (5)	C17—C18—H18	119.5
C40—C39—H39	119.6	C35—C40—C39	120.0 (5)
C41—C42—H42A	109.5	C35—C40—H40	120.0
C41—C42—H42B	109.5	C39—C40—H40	120.0
C41—C42—H42C	109.5	N1—C1—C2	112.0 (4)
H42A—C42—H42B	109.5	N1—C1—H1A	109.2
H42A—C42—H42C	109.5	N1—C1—H1B	109.2
H42B—C42—H42C	109.5	C2—C1—H1A	109.2
C35—C36—H36	119.1	C2—C1—H1B	109.2
C35—C36—C37	121.8 (5)	H1A—C1—H1B	107.9
C37—C36—H36	119.1	C29—C28—H28	120.0
C20—C19—C22	124.0 (4)	C27—C28—C29	120.1 (5)
C20—C19—C18	117.9 (4)	C27—C28—H28	120.0
C18—C19—C22	118.0 (4)	C26—C31—H31	119.3
C20—C21—H21	119.9	C30—C31—C26	121.4 (4)
C20—C21—C16	120.2 (4)	C30—C31—H31	119.3
C16—C21—H21	119.9	N6—C13—H13A	109.2
C19—C20—H20	119.3	N6—C13—H13B	109.2
C21—C20—C19	121.5 (4)	N6—C13—C12	112.1 (5)
C21—C20—H20	119.3	H13A—C13—H13B	107.9
C3—C2—H2A	108.4	C12—C13—H13A	109.2
C3—C2—H2B	108.4	C12—C13—H13B	109.2
H2A—C2—H2B	107.5	N5—C15—C14ⁱⁱⁱ	110.1 (5)
C1—C2—C3	115.4 (4)	N5—C15—H15A	109.6
C1—C2—H2A	108.4	N5—C15—H15B	109.6
C1—C2—H2B	108.4	C14ⁱⁱⁱ—C15—H15A	109.6
C38—C37—H37	120.0	C14ⁱⁱⁱ—C15—H15B	109.6
C36—C37—C38	120.1 (5)	H15A—C15—H15B	108.2
C36—C37—H37	120.0	N5—C11—H11A	109.3
C34—C32—C25	118.8 (4)	N5—C11—H11B	109.3
C34—C32—C33	120.2 (4)	N5—C11—C12	111.5 (5)
C25—C32—C33	121.0 (4)	H11A—C11—H11B	108.0
C23—C24—H24A	109.5	C12—C11—H11A	109.3
C23—C24—H24B	109.5	C12—C11—H11B	109.3
C23—C24—H24C	109.5	C26—C27—H27	118.5
H24A—C24—H24B	109.5	C28—C27—C26	123.0 (5)
H24A—C24—H24C	109.5	C28—C27—H27	118.5
H24B—C24—H24C	109.5	C13—C12—C11	118.5 (6)
O1Wⁱⁱ—Ni2—O1W	180.0	C13—C12—H12A	107.7
N3—Ni2—O1W	88.65 (15)	C13—C12—H12B	107.7
N3ⁱⁱ—Ni2—O1Wⁱⁱ	88.65 (15)	C11—C12—H12A	107.7
N3—Ni2—O1Wⁱⁱ	91.35 (15)	C11—C12—H12B	107.7
N3ⁱⁱ—Ni2—O1W	91.35 (15)	H12A—C12—H12B	107.1
N3—Ni2—N3ⁱⁱ	180.0	N2—C4—C5ⁱ	107.4 (4)
N3—Ni2—N4ⁱⁱ	84.66 (16)	N2—C4—H4A	110.2
N3ⁱⁱ—Ni2—N4ⁱⁱ	95.34 (16)	N2—C4—H4B	110.2
N3ⁱⁱ—Ni2—N4	84.66 (16)	C5ⁱ—C4—H4A	110.2
N3—Ni2—N4	95.34 (16)	C5ⁱ—C4—H4B	110.2
N4—Ni2—O1Wⁱⁱ	90.90 (17)	H4A—C4—H4B	108.5

Ni1—N1—C5—C4ⁱ	44.0 (4)	O7—P3—C38—C37	38.0 (5)
Ni1—N1—C1—C2	−55.0 (5)	C36—C35—C40—C39	−2.7 (7)
Ni1—N2—C3—C2	55.3 (5)	C19—C22—C41—C34	169.3 (4)
Ni1—N2—C4—C5ⁱ	−42.6 (4)	C19—C22—C41—C42	−9.3 (6)
P2—C29—C30—C31	−177.8 (4)	C19—C22—C23—C25	−169.7 (4)
P2—C29—C28—C27	177.0 (4)	C19—C22—C23—C24	12.3 (6)
P3—C38—C39—C40	−176.5 (4)	O8—P3—C38—C39	−15.9 (5)
P3—C38—C37—C36	177.2 (4)	O8—P3—C38—C37	164.4 (4)
O5—P2—C29—C30	29.0 (5)	C20—C19—C18—C17	−1.5 (7)
O5—P2—C29—C28	−149.2 (4)	C20—C21—C16—P1	173.3 (4)
C29—C30—C31—C26	0.7 (8)	C20—C21—C16—C17	−2.0 (7)
C29—C28—C27—C26	1.1 (8)	C37—C38—C39—C40	3.2 (7)
O4—P2—C29—C30	−98.0 (4)	C32—C34—C35—C36	−105.9 (5)
O4—P2—C29—C28	83.8 (4)	C32—C34—C35—C40	77.4 (6)
C22—C23—C25—C26	175.0 (4)	C32—C34—C41—C22	2.2 (7)
C22—C23—C25—C32	−1.0 (7)	C32—C34—C41—C42	−179.2 (4)
C22—C19—C20—C21	−174.9 (4)	C24—C23—C25—C26	−7.1 (7)
C22—C19—C18—C17	175.5 (4)	C24—C23—C25—C32	176.9 (4)
C38—C39—C40—C35	−0.6 (8)	Ni2—N3—C10—C9ⁱⁱ	43.0 (5)
C26—C25—C32—C34	−177.1 (4)	Ni2—N3—C6—C7	−54.7 (5)
C26—C25—C32—C33	2.1 (7)	Ni2—N4—C9—C10ⁱⁱ	−41.1 (5)
O3—P1—O1—Ni1	149.1 (9)	Ni2—N4—C8—C7	55.8 (5)
O3—P1—C16—C21	25.1 (4)	C10—N3—C6—C7	−176.9 (4)
O3—P1—C16—C17	−159.6 (3)	C9—N4—C8—C7	179.2 (5)
C34—C35—C36—C37	−173.4 (4)	C6—N3—C10—C9ⁱⁱ	170.0 (4)
C34—C35—C40—C39	174.0 (4)	C6—C7—C8—N4	−71.7 (6)
N2—C3—C2—C1	−71.6 (6)	C8—N4—C9—C10ⁱⁱ	−169.2 (4)
C3—N2—C4—C5ⁱ	−171.9 (4)	C8—C7—C6—N3	71.3 (6)
C3—C2—C1—N1	71.1 (6)	Ni3—N5—C15—C14ⁱⁱⁱ	37.7 (5)
O2—P1—O1—Ni1	22.6 (10)	Ni3—N5—C11—C12	−53.9 (6)
O2—P1—C16—C21	141.0 (4)	Ni3—N6—C14—C15ⁱⁱⁱ	−39.2 (5)
O2—P1—C16—C17	−43.8 (4)	Ni3—N6—C13—C12	52.9 (6)
O9—P3—C38—C39	102.4 (4)	N5—C11—C12—C13	69.6 (7)
O9—P3—C38—C37	−77.3 (4)	N6—C13—C12—C11	−69.2 (7)
C35—C34—C41—C22	−175.0 (4)	C14—N6—C13—C12	178.9 (5)
C35—C34—C41—C42	3.6 (7)	O1—P1—C16—C21	−93.2 (4)
C35—C34—C32—C25	177.6 (4)	O1—P1—C16—C17	82.0 (4)
C35—C34—C32—C33	−1.6 (7)	O6—P2—C29—C30	146.4 (4)
C35—C36—C37—C38	−0.8 (8)	O6—P2—C29—C28	−31.8 (4)
C41—C22—C23—C25	3.8 (7)	C16—P1—O1—Ni1	−98.5 (10)
C41—C22—C23—C24	−174.2 (4)	C16—C21—C20—C19	−0.2 (7)
C41—C22—C19—C20	85.7 (6)	C16—C17—C18—C19	−0.7 (7)
C41—C22—C19—C18	−91.1 (5)	C18—C19—C20—C21	1.9 (7)
C41—C34—C35—C36	71.2 (6)	C18—C17—C16—P1	−173.0 (3)
C41—C34—C35—C40	−105.5 (5)	C18—C17—C16—C21	2.4 (7)
C41—C34—C32—C25	0.6 (7)	C40—C35—C36—C37	3.4 (7)
C41—C34—C32—C33	−178.6 (4)	C1—N1—C5—C4ⁱ	172.6 (4)
C23—C22—C41—C34	−4.4 (7)	C28—C29—C30—C31	0.4 (8)
C23—C22—C41—C42	177.0 (4)	C31—C26—C25—C23	110.8 (5)
C23—C22—C19—C20	−100.7 (5)	C31—C26—C25—C32	−73.2 (6)
C23—C22—C19—C18	82.5 (5)	C31—C26—C27—C28	0.1 (7)
C23—C25—C32—C34	−1.2 (7)	C13—N6—C14—C15ⁱⁱⁱ	−169.4 (5)
C23—C25—C32—C33	178.0 (4)	C15—N5—C11—C12	−179.0 (5)
C30—C29—C28—C27	−1.3 (7)	C11—N5—C15—C14ⁱⁱⁱ	168.7 (5)
C25—C26—C31—C30	178.9 (5)	C27—C26—C25—C23	−69.4 (6)
C25—C26—C27—C28	−179.7 (5)	C27—C26—C25—C32	106.6 (5)
C5—N1—C1—C2	−177.5 (4)	C27—C26—C31—C30	−0.9 (7)
C39—C38—C37—C36	−2.5 (7)	C4—N2—C3—C2	179.3 (5)
O7—P3—C38—C39	−142.3 (4)

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y+2, −z+1; (iii) −x+1, −y+3, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6^iv	1.00	2.32	3.196 (5)	146
N2—H2···O6W	1.00	2.18	3.039 (6)	143
N3—H3···07^v	1.00	2.13	3.102 (6)	162
N4—H4···O4W	1.00	2.06	3.056 (6)	173
N5—H5···O9^vi	1.00	2.07	3.003 (6)	155
N6—H6···O7Wⁱⁱ	1.00	1.98	2.956 (6)	166
O3—H3C···O5^iv	0.84	1.84	2.654 (5)	162
O6—H6C···O3W^vii	0.84	1.75	2.550 (5)	159
O9—H9C···O4^viii	0.84	1.74	2.517 (5)	154
O1W—H1WB···O7^v	0.87	1.81	2.679 (5)	173
O1W—H1WA···O4W	0.87	2.45	3.256 (6)	155
O2W—H2WB···O4	0.86	1.90	2.729 (5)	164
O2W—H2WA···O7W^ix	0.86	1.81	2.675 (6)	174
O3W—H3WB···O2	0.87	1.81	2.676 (4)	177
O3W—H3WA···O7^v	0.85	1.84	2.689 (5)	174
O4W—H4WB···O3	0.87	2.26	3.115 (6)	167
O4W—H4WA···O8^v	0.87	1.93	2.796 (6)	172
O5W—H5WB···O5^x	0.87	1.98	2.813 (5)	159
O5W—H5WA···O8^xi	0.87	1.87	2.725 (5)	168
O6W—H6WB···O2	0.87	2.02	2.799 (6)	149
O6W—H6WA···O5W	0.87	2.00	2.842 (5)	164
O7W—H7WB···O3W	0.85	2.02	2.731 (5)	140
O7W—H7WA···O5W	0.86	1.83	2.688 (5)	173

Symmetry codes: (ii) −x+2, −y+2, −z+1; (iv) x, y−1, z; (v) x, y, z−1; (vi) −x+1, −y+2, −z+2; (vii) x, y+1, z; (viii) x, y−1, z+1; (ix) x−1, y+1, z; (x) x+1, y−1, z; (xi) x+1, y, z−1.

Selected geometric parameters (Å, °). top

Ni1—N1	2.067 (4)	Ni2—N3	2.072 (4)	Ni3—N5	2.070 (4)
Ni1—N2	2.064 (4)	Ni2—N4	2.076 (4)	Ni3—N6	2.056 (4)
Ni1—O1	2.134 (3)	Ni2—O1W	2.105 (4)	Ni3—O2W	2.136 (3)

N1—Ni1—N2i	85.31 (16)	N3—Ni2—N4ii	84.66 (16)	N5—Ni3—N6iii	85.2 (2)
N1—Ni1—N2	94.69 (16)	N3—Ni2—N4	95.34 (16)	N5—Ni3—N6	94.8 (2)

Symmetry codes: (i) –x+2, –y+1, –z+2; (ii) –x+2, –y+2, –z+1; (iii) –x+1, –y+3, –z+1.

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