Poly[[(μ3-adamantane-1,3-di­acetato)[μ-N-(pyridin-3-yl)isonicotinamide]­nickel(II)] monohydrate], a layered coordination polymer with triangular (3,6) topology

Travis, J.Z.; LaDuca, R.L.

doi:10.1107/S2414314623008696

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 8| Part 10| October 2023| x230869

https://doi.org/10.1107/S2414314623008696

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Poly[[(μ₃-adamantane-1,3-diacetato)[μ-N-(pyridin-3-yl)isonicotinamide]nickel(II)] monohydrate], a layered coordination polymer with triangular (3,6) topology

Jamelah Z. Travis ^a and Robert L. LaDuca ^b ^*

^aDepartment of Chemistry, Hope College, Holland, MI 49423, USA, and ^bE-194 Holmes Hall, Michigan State University, Lyman Briggs College, 919 E. Shaw Lane, East Lansing, MI 48825, USA
^*Correspondence e-mail: laduca@msu.edu

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 24 August 2023; accepted 4 October 2023; online 5 October 2023)

The title compound, {[Ni(C₁₄H₁₈O₄)(C₁₁H₉N₃O)]·H₂O}_n, contains octahedrally coordinated Ni^II ions ligated by 1,3-adamantanediacetato (ada) ligands and N-(pyridin-3-yl)isonicotinamide (3-pina) ligands, to form coordination polymer layers with a triangular (3,6) grid topology based on [Ni₂(OCO)₂] dimeric units. The diperiodic layer motifs stack in an ABAB pattern mediated by C—H⋯O supramolecular interactions between ada ligands and water molecules of crystallization to form the full triperiodic crystal structure of the title compound.

Keywords: crystal structure; polymer; topology; nickel; isonicotinamide.

CCDC reference: 2299081

Structure description

The title complex was obtained during attempts to prepare divalent nickel coordination polymers featuring 1,3-adamantanediacetate (ada) ligands and the hydrogen-bonding-capable dipyridylamide ligand N-(pyridin-3-yl)isonicotinamide (3-pina). We have reported nickel ada coordination polymers featuring N,N′-(ethane-1,2-diyl)diisonicotinamide (edin) and N,N′-(propane-1,3-diyl)diisonicotinamide (pdin) (Travis et al., 2018 ). [Ni(ada)(edin)]_n manifests an intriguing self-penetrated layer structure with a 3,5-connected binodal (4²6)(4²6⁷8) topology. {[Ni₅(ada)₅(pdin)₅(H₂O)₅]·8H₂O}_n shows a looped layer structure with a 3-connected (4)(4.8⁵) topology. Additionally, our group reported a cadmium adamantanedicarboxylate (adc) coordination polymer containing 3-pina coligands (LaRose & LaDuca, 2017 ). The triperiodic phase {[Cd₂(adc)₂(3-pina)₂]·H₂O}_n exhibited a non-interpenetrated network with 6⁵8 cds topology.

The asymmetric unit of the title compound contains a nickel atom, a fully deprotonated ada ligand, an N-(pyridin-3-yl)isonicotinamide (3-pina) ligand, and one water molecule of crystallization (Fig. 1). The Ni atoms possess an octahedral {N₂O₄} coordination environment with the nominal axial positions taken up by pyridyl N atom belonging to the isonicotinamide side of a 3-pina ligand, and a pyridyl N atom belonging to the 3-pyridyl side of another 3-pina ligand. The nominal equatorial plane contains a chelating carboxylate group from an ada ligand, and cis-oriented O atom donors belonging to two different ada ligands. Bond lengths and angles within the coordination environment are listed in Table 1.

Table 1
Selected geometric parameters (Å, °)

Ni1—O1	2.023 (2)	Ni1—O4ⁱⁱ	2.132 (2)
Ni1—O2ⁱ	2.038 (2)	Ni1—N1	2.089 (3)
Ni1—O3ⁱⁱ	2.131 (2)	Ni1—N3ⁱⁱⁱ	2.099 (3)

O1—Ni1—O2ⁱ	112.60 (10)	O2ⁱ—Ni1—N3ⁱⁱⁱ	89.11 (10)
O1—Ni1—O3ⁱⁱ	152.96 (9)	O3ⁱⁱ—Ni1—O4ⁱⁱ	61.82 (9)
O1—Ni1—O4ⁱⁱ	91.42 (9)	N1—Ni1—O3ⁱⁱ	89.29 (10)
O1—Ni1—N1	86.69 (10)	N1—Ni1—O4ⁱⁱ	89.94 (10)
O1—Ni1—N3ⁱⁱⁱ	94.55 (10)	N1—Ni1—N3ⁱⁱⁱ	176.07 (11)
O2ⁱ—Ni1—O3ⁱⁱ	93.85 (10)	N3ⁱⁱⁱ—Ni1—O3ⁱⁱ	91.27 (10)
O2ⁱ—Ni1—O4ⁱⁱ	155.53 (9)	N3ⁱⁱⁱ—Ni1—O4ⁱⁱ	93.75 (10)
O2ⁱ—Ni1—N1	86.97 (11)
Symmetry codes: (i) ; (ii) ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Figure 1
Nickel coordination environment in the title compound with full ligand set. Displacement ellipsoids are drawn at the 50% probability level. Color code: Ni, green; O, red; N, light blue; C, black. H-atom positions are shown as gray sticks. Symmetry codes are as listed in Table 1

The bridging/chelating ada ligands connect to three Ni atoms, and form [Ni(ada)]_n monoperiodic coordination polymer chains arranged along the b-axis direction (Fig. 2). The chain motifs contain embedded syn–syn bridged [Ni₂(OCO)₂] dimeric units with an Ni⋯Ni through-space distance of 4.277 (1) Å. Adjacent and parallel chain motifs are pillared by 3-pina ligands into diperiodic coordination polymer layers of stoichiometry [Ni(ada)(3-pina)]_n (Fig. 3); these are oriented parallel to the ab crystal planes. The topology of the title compound can be inferred by considering the [Ni₂(OCO)₂] dimeric units as 6-connected nodes, with two connections provided by the full span of the ada ligands. Each [Ni₂(OCO)₂] dimeric unit node also connects to four others via 3-pina ligands. The resultant 6-connected layered topology is that of a (3,6) triangular net (Fig. 4).

Figure 2
[Ni(ada)]_n coordination polymer chain motif in the title compound, featuring [Ni₂(OCO)₂] dimeric units.

Figure 3
[Ni(ada)(3-pina)]_n coordination polymer layer motif in the title compound.

Figure 4
Schematic perspective of the 6-connected (3,6) triangular layer topology in the title compound. Centroids of the [Ni₂(OCO)₂] dimeric units are shown as gold spheres. Connections mediated by the ada ligands and 3-pina ligands are drawn as red rods and blue rods, respectively.

Parallel [Ni(ada)(3-pina)]_n layer motifs stack in an ABAB pattern along the c-axis axis, via classical and non-classical hydrogen-bonding pathways (Fig. 5). The water molecules of crystallization are anchored to the layer motifs via O—H⋯O hydrogen bonding donation to ada carboxylate O atoms. The water molecules of crystallization engage in interlamellar C—H⋯O interactions with 3-pina pyridyl C atoms [C⋯O distance = 3.187 (1) Å]. Metrical parameters for the hydrogen bonding in the title compound are given in Table 2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O4	0.87	1.98	2.809 (5)	159
N2—H2⋯O5^iv	0.88	2.00	2.874 (4)	173
C1—H1⋯O2ⁱ	0.95	2.49	2.957 (4)	111
C5—H5⋯O1	0.95	2.48	2.928 (4)	109
C7—H7⋯O2^v	0.95	2.68	3.027 (4)	102
C9—H9⋯O5	0.95	2.41	2.922 (4)	114
Symmetry codes: (i) ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (v) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Figure 5
ABAB stacking of coordination polymer layers in the title compound.

Synthesis and crystallization

Ni(NO₃)₂·6H₂O (108 mg, 0.37 mmol), 1,3-adamantanediacetic acid (adaH₂, 93 mg, 0.37 mmol), N-(pyridin-3-yl)isonicotinamide (3-pina, 74 mg, 0.37 mmol), and 0.75 ml of a 1.0 M NaOH solution were placed into 10 ml distilled H₂O in a Teflon-lined acid digestion bomb. The bomb was sealed and heated in an oven at 393 K for 48 h, and then cooled slowly to 273 K. Green crystals of the title complex were obtained in 43% yield.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3.

Table 3
Experimental details

Crystal data
Chemical formula	[Ni(C₁₄H₁₈O₄)(C₁₁H₉N₃O)]·H₂O
M_r	526.22
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	173
a, b, c (Å)	21.789 (3), 9.5494 (12), 22.200 (3)
V (Å³)	4619.2 (10)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.89
Crystal size (mm)	0.30 × 0.08 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.606, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	71364, 4216, 3175
R_int	0.112
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.134, 1.05
No. of reflections	4216
No. of parameters	319
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.45
Computer programs: COSMO (Bruker, 2009 ), SAINT (Bruker, 2014 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), CrystalMaker X (Palmer, 2020 ), and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2299081

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314623008696/bh4079sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314623008696/bh4079Isup2.hkl

checkCIF report

Computing details top

Data collection: COSMO (Bruker, 2009); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: CrystalMaker X (Palmer, 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Poly[[(µ₃-adamantane-1,3-diacetato)[µ-N-(pyridin-3-yl)isonicotinamide]nickel(II)] monohydrate], top

Crystal data top

[Ni(C₁₄H₁₈O₄)(C₁₁H₉N₃O)]·H₂O	D_x = 1.513 Mg m⁻³
M_r = 526.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9950 reflections
a = 21.789 (3) Å	θ = 2.5–25.2°
b = 9.5494 (12) Å	µ = 0.89 mm⁻¹
c = 22.200 (3) Å	T = 173 K
V = 4619.2 (10) Å³	Needle, green
Z = 8	0.30 × 0.08 × 0.05 mm
F(000) = 2208

Data collection top

Bruker APEXII CCD diffractometer	4216 independent reflections
Radiation source: sealed tube	3175 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.112
Detector resolution: 836.6 pixels mm^-1	θ_max = 25.3°, θ_min = 1.8°
φ and ω scans	h = −26→26
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −11→11
T_min = 0.606, T_max = 0.745	l = −26→26
71364 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: mixed
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0727P)² + 4.9019P] where P = (F_o² + 2F_c²)/3
4216 reflections	(Δ/σ)_max = 0.001
319 parameters	Δρ_max = 0.76 e Å⁻³
1 restraint	Δρ_min = −0.44 e Å⁻³

Special details top

Refinement. All H atoms attached to C and N atoms were placed in calculated positions and refined with a riding model. The H atoms in the water molecule of crystallization could not be found in a difference map, so they were placed in calculated positions.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.48258 (2)	0.33446 (4)	0.56257 (2)	0.01734 (16)
O1	0.42593 (10)	0.5016 (2)	0.55617 (11)	0.0231 (5)
O1W	0.3792 (3)	1.3710 (4)	0.74898 (18)	0.0821 (13)
H1WA	0.390684	1.346055	0.713002	0.123*
H1WB	0.360617	1.450646	0.743741	0.123*
O2	0.46532 (11)	0.6932 (2)	0.51276 (11)	0.0234 (6)
O3	0.51363 (11)	1.1459 (2)	0.60389 (11)	0.0220 (5)
O4	0.44420 (11)	1.2773 (2)	0.64741 (11)	0.0221 (6)
O5	0.27987 (11)	−0.1308 (2)	0.41445 (13)	0.0302 (6)
N1	0.41408 (12)	0.2205 (3)	0.51861 (13)	0.0201 (6)
N2	0.22128 (13)	0.0684 (3)	0.41194 (13)	0.0217 (7)
H2	0.224054	0.160150	0.414096	0.026*
N3	0.05497 (12)	0.0519 (3)	0.39871 (12)	0.0178 (6)
C1	0.42734 (15)	0.1183 (3)	0.47886 (16)	0.0203 (8)
H1	0.469232	0.096548	0.471564	0.024*
C2	0.38285 (16)	0.0435 (3)	0.44816 (15)	0.0202 (8)
H2A	0.394093	−0.029367	0.421168	0.024*
C3	0.32140 (15)	0.0766 (3)	0.45745 (15)	0.0182 (7)
C4	0.30765 (15)	0.1819 (4)	0.49923 (16)	0.0220 (8)
H4	0.266192	0.206588	0.507133	0.026*
C5	0.35474 (16)	0.2495 (4)	0.52878 (16)	0.0231 (8)
H5	0.344752	0.319468	0.557552	0.028*
C6	0.27282 (15)	−0.0048 (4)	0.42567 (15)	0.0196 (8)
C7	0.11246 (16)	0.0945 (3)	0.40809 (15)	0.0191 (7)
H7	0.118697	0.184913	0.424881	0.023*
C8	0.16377 (15)	0.0138 (3)	0.39462 (15)	0.0181 (7)
C9	0.15514 (16)	−0.1157 (4)	0.36646 (16)	0.0205 (8)
H9	0.189018	−0.172723	0.355280	0.025*
C10	0.09520 (16)	−0.1579 (3)	0.35549 (16)	0.0209 (8)
H10	0.087462	−0.244906	0.336192	0.025*
C11	0.04719 (16)	−0.0741 (3)	0.37246 (15)	0.0208 (8)
H11	0.006559	−0.106242	0.365398	0.025*
C12	0.42397 (15)	0.6283 (3)	0.54030 (15)	0.0178 (7)
C13	0.36516 (16)	0.7067 (4)	0.55572 (16)	0.0212 (8)
H13A	0.330417	0.640170	0.553238	0.025*
H13B	0.358407	0.779695	0.524739	0.025*
C14	0.36697 (17)	0.6684 (3)	0.66913 (16)	0.0229 (8)
H14A	0.406004	0.615760	0.666328	0.027*
H14B	0.332713	0.601025	0.665009	0.027*
C15	0.36373 (16)	0.7771 (4)	0.61809 (16)	0.0206 (8)
C16	0.30221 (16)	0.8574 (4)	0.62426 (17)	0.0243 (8)
H16A	0.298905	0.927903	0.591727	0.029*
H16B	0.267546	0.791093	0.620060	0.029*
C17	0.29848 (17)	0.9305 (4)	0.68564 (17)	0.0282 (9)
H17	0.258643	0.982035	0.688746	0.034*
C18	0.30197 (18)	0.8208 (4)	0.73539 (18)	0.0314 (9)
H18A	0.267426	0.754089	0.731347	0.038*
H18B	0.298775	0.866780	0.775231	0.038*
C19	0.36298 (17)	0.7421 (4)	0.73080 (16)	0.0261 (8)
H19	0.365533	0.670741	0.763675	0.031*
C20	0.41681 (15)	0.8826 (3)	0.62541 (15)	0.0174 (7)
H20A	0.456463	0.832699	0.621716	0.021*
H20B	0.414628	0.953113	0.592798	0.021*
C21	0.41646 (17)	0.8455 (4)	0.73669 (16)	0.0242 (8)
H21A	0.455797	0.793969	0.734058	0.029*
H21B	0.414621	0.891740	0.776565	0.029*
C22	0.41396 (16)	0.9572 (4)	0.68684 (15)	0.0208 (8)
C23	0.35179 (17)	1.0350 (4)	0.69142 (18)	0.0254 (8)
H23A	0.349127	1.083998	0.730630	0.030*
H23B	0.348930	1.105950	0.659028	0.030*
C24	0.46870 (17)	1.0572 (4)	0.69556 (16)	0.0231 (8)
H24A	0.463732	1.106082	0.734587	0.028*
H24B	0.506748	1.000850	0.697935	0.028*
C25	0.47650 (16)	1.1662 (3)	0.64650 (16)	0.0199 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0174 (2)	0.0116 (2)	0.0231 (3)	−0.00055 (17)	0.00082 (18)	−0.00025 (18)
O1	0.0210 (13)	0.0152 (12)	0.0332 (14)	0.0007 (10)	0.0007 (11)	0.0018 (11)
O1W	0.140 (4)	0.049 (2)	0.057 (2)	0.026 (3)	0.017 (3)	0.0070 (19)
O2	0.0243 (13)	0.0187 (12)	0.0271 (14)	−0.0046 (10)	0.0064 (11)	−0.0022 (11)
O3	0.0235 (13)	0.0164 (12)	0.0261 (14)	0.0008 (10)	0.0024 (11)	0.0002 (10)
O4	0.0238 (13)	0.0135 (12)	0.0291 (14)	0.0024 (10)	0.0039 (11)	−0.0009 (10)
O5	0.0239 (14)	0.0104 (12)	0.0563 (18)	−0.0011 (10)	−0.0040 (13)	−0.0058 (12)
N1	0.0178 (15)	0.0145 (14)	0.0280 (16)	−0.0001 (12)	0.0012 (13)	0.0004 (12)
N2	0.0205 (16)	0.0085 (14)	0.0361 (18)	−0.0013 (12)	−0.0021 (13)	−0.0017 (12)
N3	0.0186 (15)	0.0148 (14)	0.0201 (15)	−0.0001 (12)	0.0000 (12)	0.0011 (12)
C1	0.0148 (17)	0.0146 (17)	0.031 (2)	0.0020 (13)	−0.0006 (15)	0.0006 (15)
C2	0.0246 (19)	0.0109 (16)	0.0250 (19)	0.0027 (14)	0.0017 (15)	−0.0002 (14)
C3	0.0205 (18)	0.0105 (16)	0.0236 (18)	−0.0014 (14)	−0.0028 (14)	0.0020 (14)
C4	0.0149 (17)	0.0196 (18)	0.031 (2)	0.0015 (14)	0.0023 (15)	0.0004 (15)
C5	0.0248 (19)	0.0170 (18)	0.027 (2)	−0.0007 (15)	0.0038 (15)	−0.0035 (15)
C6	0.0210 (19)	0.0127 (17)	0.0253 (19)	0.0002 (14)	0.0011 (14)	0.0015 (14)
C7	0.0246 (19)	0.0117 (16)	0.0209 (18)	0.0006 (14)	0.0006 (14)	0.0019 (14)
C8	0.0192 (17)	0.0154 (17)	0.0196 (18)	−0.0009 (14)	−0.0009 (14)	−0.0004 (14)
C9	0.0220 (18)	0.0148 (16)	0.0249 (19)	0.0023 (15)	−0.0003 (15)	−0.0021 (15)
C10	0.0257 (19)	0.0133 (17)	0.0236 (19)	−0.0017 (15)	−0.0016 (15)	−0.0019 (14)
C11	0.0206 (18)	0.0182 (18)	0.0235 (18)	−0.0031 (15)	−0.0023 (15)	0.0007 (15)
C12	0.0208 (18)	0.0147 (17)	0.0180 (17)	−0.0019 (14)	−0.0035 (14)	−0.0029 (14)
C13	0.0214 (18)	0.0156 (17)	0.026 (2)	0.0009 (14)	−0.0009 (15)	0.0024 (14)
C14	0.0238 (18)	0.0146 (17)	0.030 (2)	−0.0032 (15)	0.0024 (15)	0.0024 (15)
C15	0.0210 (18)	0.0170 (17)	0.0237 (19)	0.0008 (14)	0.0028 (15)	−0.0037 (15)
C16	0.0171 (18)	0.0238 (19)	0.032 (2)	0.0011 (15)	0.0015 (15)	−0.0018 (16)
C17	0.023 (2)	0.0242 (19)	0.038 (2)	0.0028 (16)	0.0068 (17)	−0.0097 (17)
C18	0.034 (2)	0.031 (2)	0.029 (2)	−0.0110 (18)	0.0106 (18)	−0.0060 (17)
C19	0.035 (2)	0.0202 (19)	0.0235 (19)	−0.0047 (17)	0.0051 (17)	0.0025 (16)
C20	0.0204 (18)	0.0137 (16)	0.0182 (17)	0.0000 (14)	0.0007 (14)	0.0025 (14)
C21	0.033 (2)	0.0191 (18)	0.0208 (19)	−0.0024 (16)	−0.0016 (16)	0.0014 (15)
C22	0.0247 (19)	0.0171 (17)	0.0208 (18)	−0.0039 (15)	−0.0013 (15)	−0.0006 (14)
C23	0.029 (2)	0.0176 (18)	0.030 (2)	0.0024 (16)	0.0016 (16)	−0.0030 (15)
C24	0.030 (2)	0.0171 (17)	0.0223 (19)	−0.0020 (15)	−0.0021 (15)	0.0006 (15)
C25	0.0247 (19)	0.0124 (17)	0.0225 (18)	−0.0054 (15)	−0.0038 (15)	0.0010 (14)

Geometric parameters (Å, º) top

Ni1—O1	2.023 (2)	C11—H11	0.9500
Ni1—O2ⁱ	2.038 (2)	C12—C13	1.523 (5)
Ni1—O3ⁱⁱ	2.131 (2)	C13—H13A	0.9900
Ni1—O4ⁱⁱ	2.132 (2)	C13—H13B	0.9900
Ni1—N1	2.089 (3)	C13—C15	1.539 (5)
Ni1—N3ⁱⁱⁱ	2.099 (3)	C14—H14A	0.9900
O1—C12	1.261 (4)	C14—H14B	0.9900
O1W—H1WA	0.8700	C14—C15	1.538 (5)
O1W—H1WB	0.8701	C14—C19	1.542 (5)
O2—C12	1.253 (4)	C15—C16	1.551 (5)
O3—C25	1.260 (4)	C15—C20	1.542 (5)
O4—C25	1.273 (4)	C16—H16A	0.9900
O5—C6	1.238 (4)	C16—H16B	0.9900
N1—C1	1.347 (4)	C16—C17	1.533 (5)
N1—C5	1.342 (4)	C17—H17	1.0000
N2—H2	0.8800	C17—C18	1.525 (5)
N2—C6	1.357 (4)	C17—C23	1.536 (5)
N2—C8	1.411 (4)	C18—H18A	0.9900
N3—C7	1.334 (4)	C18—H18B	0.9900
N3—C11	1.347 (4)	C18—C19	1.530 (5)
C1—H1	0.9500	C19—H19	1.0000
C1—C2	1.384 (5)	C19—C21	1.533 (5)
C2—H2A	0.9500	C20—H20A	0.9900
C2—C3	1.391 (5)	C20—H20B	0.9900
C3—C4	1.400 (5)	C20—C22	1.540 (5)
C3—C6	1.491 (5)	C21—H21A	0.9900
C4—H4	0.9500	C21—H21B	0.9900
C4—C5	1.378 (5)	C21—C22	1.538 (5)
C5—H5	0.9500	C22—C23	1.548 (5)
C7—H7	0.9500	C22—C24	1.541 (5)
C7—C8	1.390 (5)	C23—H23A	0.9900
C8—C9	1.399 (5)	C23—H23B	0.9900
C9—H9	0.9500	C24—H24A	0.9900
C9—C10	1.388 (5)	C24—H24B	0.9900
C10—H10	0.9500	C24—C25	1.516 (5)
C10—C11	1.370 (5)

O1—Ni1—O2ⁱ	112.60 (10)	C15—C14—H14A	109.6
O1—Ni1—O3ⁱⁱ	152.96 (9)	C15—C14—H14B	109.6
O1—Ni1—O4ⁱⁱ	91.42 (9)	C15—C14—C19	110.1 (3)
O1—Ni1—N1	86.69 (10)	C19—C14—H14A	109.6
O1—Ni1—N3ⁱⁱⁱ	94.55 (10)	C19—C14—H14B	109.6
O2ⁱ—Ni1—O3ⁱⁱ	93.85 (10)	C13—C15—C16	108.2 (3)
O2ⁱ—Ni1—O4ⁱⁱ	155.53 (9)	C13—C15—C20	111.4 (3)
O2ⁱ—Ni1—N1	86.97 (11)	C14—C15—C13	111.6 (3)
O2ⁱ—Ni1—N3ⁱⁱⁱ	89.11 (10)	C14—C15—C16	108.0 (3)
O3ⁱⁱ—Ni1—O4ⁱⁱ	61.82 (9)	C14—C15—C20	109.2 (3)
N1—Ni1—O3ⁱⁱ	89.29 (10)	C20—C15—C16	108.4 (3)
N1—Ni1—O4ⁱⁱ	89.94 (10)	C15—C16—H16A	109.6
N1—Ni1—N3ⁱⁱⁱ	176.07 (11)	C15—C16—H16B	109.6
N3ⁱⁱⁱ—Ni1—O3ⁱⁱ	91.27 (10)	H16A—C16—H16B	108.1
N3ⁱⁱⁱ—Ni1—O4ⁱⁱ	93.75 (10)	C17—C16—C15	110.5 (3)
C12—O1—Ni1	142.9 (2)	C17—C16—H16A	109.6
H1WA—O1W—H1WB	104.5	C17—C16—H16B	109.6
C12—O2—Ni1ⁱ	137.5 (2)	C16—C17—H17	109.3
C25—O3—Ni1^iv	89.42 (19)	C16—C17—C23	109.3 (3)
C25—O4—Ni1^iv	89.0 (2)	C18—C17—C16	109.1 (3)
C1—N1—Ni1	122.0 (2)	C18—C17—H17	109.3
C5—N1—Ni1	120.2 (2)	C18—C17—C23	110.4 (3)
C5—N1—C1	117.8 (3)	C23—C17—H17	109.3
C6—N2—H2	116.3	C17—C18—H18A	109.8
C6—N2—C8	127.3 (3)	C17—C18—H18B	109.8
C8—N2—H2	116.3	C17—C18—C19	109.4 (3)
C7—N3—Ni1^v	118.9 (2)	H18A—C18—H18B	108.2
C7—N3—C11	117.3 (3)	C19—C18—H18A	109.8
C11—N3—Ni1^v	123.0 (2)	C19—C18—H18B	109.8
N1—C1—H1	118.4	C14—C19—H19	109.5
N1—C1—C2	123.1 (3)	C18—C19—C14	109.4 (3)
C2—C1—H1	118.4	C18—C19—H19	109.5
C1—C2—H2A	120.5	C18—C19—C21	109.8 (3)
C1—C2—C3	118.9 (3)	C21—C19—C14	109.1 (3)
C3—C2—H2A	120.5	C21—C19—H19	109.5
C2—C3—C4	117.9 (3)	C15—C20—H20A	109.3
C2—C3—C6	119.6 (3)	C15—C20—H20B	109.3
C4—C3—C6	122.4 (3)	H20A—C20—H20B	108.0
C3—C4—H4	120.3	C22—C20—C15	111.4 (3)
C5—C4—C3	119.5 (3)	C22—C20—H20A	109.3
C5—C4—H4	120.3	C22—C20—H20B	109.3
N1—C5—C4	122.7 (3)	C19—C21—H21A	109.4
N1—C5—H5	118.6	C19—C21—H21B	109.4
C4—C5—H5	118.6	C19—C21—C22	111.0 (3)
O5—C6—N2	123.9 (3)	H21A—C21—H21B	108.0
O5—C6—C3	120.9 (3)	C22—C21—H21A	109.4
N2—C6—C3	115.2 (3)	C22—C21—H21B	109.4
N3—C7—H7	118.2	C20—C22—C23	108.4 (3)
N3—C7—C8	123.5 (3)	C20—C22—C24	111.5 (3)
C8—C7—H7	118.2	C21—C22—C20	108.4 (3)
C7—C8—N2	116.8 (3)	C21—C22—C23	108.5 (3)
C7—C8—C9	118.6 (3)	C21—C22—C24	108.2 (3)
C9—C8—N2	124.6 (3)	C24—C22—C23	111.8 (3)
C8—C9—H9	121.3	C17—C23—C22	110.1 (3)
C10—C9—C8	117.5 (3)	C17—C23—H23A	109.6
C10—C9—H9	121.3	C17—C23—H23B	109.6
C9—C10—H10	120.0	C22—C23—H23A	109.6
C11—C10—C9	120.1 (3)	C22—C23—H23B	109.6
C11—C10—H10	120.0	H23A—C23—H23B	108.1
N3—C11—C10	123.0 (3)	C22—C24—H24A	108.5
N3—C11—H11	118.5	C22—C24—H24B	108.5
C10—C11—H11	118.5	H24A—C24—H24B	107.5
O1—C12—C13	115.9 (3)	C25—C24—C22	115.0 (3)
O2—C12—O1	125.9 (3)	C25—C24—H24A	108.5
O2—C12—C13	118.1 (3)	C25—C24—H24B	108.5
C12—C13—H13A	108.4	O3—C25—Ni1^iv	59.84 (17)
C12—C13—H13B	108.4	O3—C25—O4	119.7 (3)
C12—C13—C15	115.7 (3)	O3—C25—C24	120.4 (3)
H13A—C13—H13B	107.4	O4—C25—Ni1^iv	59.89 (17)
C15—C13—H13A	108.4	O4—C25—C24	119.9 (3)
C15—C13—H13B	108.4	C24—C25—Ni1^iv	175.6 (2)
H14A—C14—H14B	108.2

Ni1—O1—C12—O2	9.4 (6)	C12—C13—C15—C14	−64.2 (4)
Ni1—O1—C12—C13	−171.6 (3)	C12—C13—C15—C16	177.1 (3)
Ni1ⁱ—O2—C12—O1	50.8 (5)	C12—C13—C15—C20	58.0 (4)
Ni1ⁱ—O2—C12—C13	−128.2 (3)	C13—C15—C16—C17	−179.6 (3)
Ni1^iv—O3—C25—O4	−3.3 (3)	C13—C15—C20—C22	177.8 (3)
Ni1^iv—O3—C25—C24	174.9 (3)	C14—C15—C16—C17	59.5 (4)
Ni1^iv—O4—C25—O3	3.3 (3)	C14—C15—C20—C22	−58.6 (4)
Ni1^iv—O4—C25—C24	−174.9 (3)	C14—C19—C21—C22	60.2 (4)
Ni1—N1—C1—C2	−178.5 (3)	C15—C14—C19—C18	60.5 (4)
Ni1—N1—C5—C4	177.2 (3)	C15—C14—C19—C21	−59.6 (4)
Ni1^v—N3—C7—C8	167.3 (3)	C15—C16—C17—C18	−60.6 (4)
Ni1^v—N3—C11—C10	−169.7 (3)	C15—C16—C17—C23	60.1 (4)
O1—C12—C13—C15	88.5 (4)	C15—C20—C22—C21	58.2 (4)
O2—C12—C13—C15	−92.4 (4)	C15—C20—C22—C23	−59.3 (4)
N1—C1—C2—C3	1.5 (5)	C15—C20—C22—C24	177.2 (3)
N2—C8—C9—C10	176.3 (3)	C16—C15—C20—C22	58.8 (4)
N3—C7—C8—N2	−174.6 (3)	C16—C17—C18—C19	60.6 (4)
N3—C7—C8—C9	3.9 (5)	C16—C17—C23—C22	−60.5 (4)
C1—N1—C5—C4	−1.8 (5)	C17—C18—C19—C14	−60.5 (4)
C1—C2—C3—C4	−2.0 (5)	C17—C18—C19—C21	59.1 (4)
C1—C2—C3—C6	−178.8 (3)	C18—C17—C23—C22	59.6 (4)
C2—C3—C4—C5	0.8 (5)	C18—C19—C21—C22	−59.6 (4)
C2—C3—C6—O5	33.1 (5)	C19—C14—C15—C13	−177.9 (3)
C2—C3—C6—N2	−148.4 (3)	C19—C14—C15—C16	−59.1 (4)
C3—C4—C5—N1	1.2 (5)	C19—C14—C15—C20	58.6 (4)
C4—C3—C6—O5	−143.5 (4)	C19—C21—C22—C20	−59.0 (4)
C4—C3—C6—N2	35.0 (5)	C19—C21—C22—C23	58.4 (4)
C5—N1—C1—C2	0.4 (5)	C19—C21—C22—C24	179.9 (3)
C6—N2—C8—C7	152.4 (3)	C20—C15—C16—C17	−58.7 (4)
C6—N2—C8—C9	−26.1 (5)	C20—C22—C23—C17	59.5 (4)
C6—C3—C4—C5	177.5 (3)	C20—C22—C24—C25	55.4 (4)
C7—N3—C11—C10	0.0 (5)	C21—C22—C23—C17	−58.0 (4)
C7—C8—C9—C10	−2.1 (5)	C21—C22—C24—C25	174.5 (3)
C8—N2—C6—O5	13.6 (6)	C22—C24—C25—O3	−96.9 (4)
C8—N2—C6—C3	−164.8 (3)	C22—C24—C25—O4	81.2 (4)
C8—C9—C10—C11	−0.4 (5)	C23—C17—C18—C19	−59.5 (4)
C9—C10—C11—N3	1.6 (5)	C23—C22—C24—C25	−66.1 (4)
C11—N3—C7—C8	−2.8 (5)	C24—C22—C23—C17	−177.2 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O4	0.87	1.98	2.809 (5)	159
N2—H2···O5^vi	0.88	2.00	2.874 (4)	173
C1—H1···O2ⁱ	0.95	2.49	2.957 (4)	111
C5—H5···O1	0.95	2.48	2.928 (4)	109
C7—H7···O2^vii	0.95	2.68	3.027 (4)	102
C9—H9···O5	0.95	2.41	2.922 (4)	114

Symmetry codes: (i) −x+1, −y+1, −z+1; (vi) −x+1/2, y+1/2, z; (vii) −x+1/2, y−1/2, z.

Funding information

Funding for this work was provided by the Lyman Briggs College of Science at Michigan State University.

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