Poly[[(μ3-adamantane-1,3-di­carboxyl­ato)aqua­[μ-N-(pyridin-3-yl)isonicotinamide]­nickel(II)] monohydrate], a layered coordination polymer with (4,4) topology

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

doi:10.1107/S2414314623007587

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 8| Part 9| September 2023| x230758

https://doi.org/10.1107/S2414314623007587

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Poly[[(μ₃-adamantane-1,3-dicarboxylato)aqua[μ-N-(pyridin-3-yl)isonicotinamide]nickel(II)] monohydrate], a layered coordination polymer with (4,4) topology

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

^aDepartment of Chemistry, Hope College, Holland, MI 49423, USA, and ^bE-35 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 L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 23 August 2023; accepted 30 August 2023; online 8 September 2023)

The title compound, {[Ni(C₁₂H₁₄O₄)(C₁₁H₉N₃O)(H₂O)]·H₂O}_n, contains octahedrally coordinated Ni^II ions ligated by adamantane-1,3-dicarboxylate (adc) and N-(pyridin-3-yl)isonicotinamide (3-pina) ligands forming coordination polymer layers with a (4,4) grid topology. These diperiodic layer motifs aggregate in an AAA pattern mediated by supramolecular C—H⋯O interactions to form the full triperiodic crystal structure of the title compound.

Keywords: crystal structure; coordination polymer; adamantane-1,3-dicarboxylate; N-(pyridin-3-yl)isonicotinamide; nickel(II).

CCDC reference: 2291890

Structure description

The title complex was obtained during attempts to prepare divalent nickel coordination polymers featuring adamantane-1,3-dicarboxylate (adc) ligands and hydrogen-bonding-capable dipyridylamide ligands. We have reported nickel adc coordination polymers featuring 4,4′-dipyridylamine (dpa) (Travis et al., 2018 ). {[Ni(adc)(dpa)]·6.5H₂O}_n manifests a stacked arrangement of (4,4) rectangular-grid diperiodic coordination polymer motifs, while the crystal structure of the partially protonated compound {[Ni₂(adc)(adcH)₂(dpa)₂]·H₂O}_n displays an uncommon 10³ topology triperiodic srs network.

The asymmetric unit of the title compound, {[Ni(adc)(3-pina)(H₂O)]·H₂O}_n, contains two Ni^II atoms on crystallographic inversion centers (Ni1 and Ni2), a complete adc ligand, an N-(pyridin-3-yl)isonicotinamide (3-pina) ligand, one water molecule bound to Ni1, and one water molecule of crystallization (Fig. 1). Operation of the crystallographic inversion centers generates two distinct coordination environments. The Ni1 atoms possess an octahedral {N₂O₄} coordination environment with trans aqua ligands, trans O-atom donors from two adc ligands, and trans 3-pyridyl N-donor atoms from two 3-pina ligands. The Ni2 atoms also display an octahedral {N₂O₄} coordination environment, but there are no bound water molecules. Instead, 4-pyridyl N-donor atoms belonging to the isonicotinamide termini of two 3-pina ligands adopt the nominal trans-axial positions. The nominal equatorial plane at the Ni2 atoms are taken up by chelating carboxylate groups belonging to two adc ligands. The bond lengths and angles within the coordination environment are listed in Table 1.

Table 1
Selected geometric parameters (Å, °)

Ni1—O1ⁱ	2.0216 (19)	Ni2—O3	2.0766 (18)
Ni1—O1	2.0216 (19)	Ni2—O3ⁱⁱ	2.0766 (18)
Ni1—O6ⁱ	2.079 (2)	Ni2—O4	2.1113 (18)
Ni1—O6	2.079 (2)	Ni2—O4ⁱⁱ	2.1113 (18)
Ni1—N1	2.138 (2)	Ni2—N2ⁱⁱⁱ	2.058 (2)
Ni1—N1ⁱ	2.138 (2)	Ni2—N2^iv	2.058 (2)

O1ⁱ—Ni1—O1	180.0	O3ⁱⁱ—Ni2—O3	180.0
O1—Ni1—O6ⁱ	90.58 (8)	O3—Ni2—O4ⁱⁱ	116.95 (7)
O1—Ni1—O6	89.42 (8)	O3—Ni2—O4	63.05 (7)
O1ⁱ—Ni1—O6ⁱ	89.42 (8)	O3ⁱⁱ—Ni2—O4	116.95 (7)
O1ⁱ—Ni1—O6	90.58 (8)	O3ⁱⁱ—Ni2—O4ⁱⁱ	63.05 (7)
O1—Ni1—N1	90.06 (8)	O4—Ni2—O4ⁱⁱ	180.0
O1—Ni1—N1ⁱ	89.94 (8)	N2ⁱⁱⁱ—Ni2—O3ⁱⁱ	92.34 (8)
O1ⁱ—Ni1—N1ⁱ	90.06 (8)	N2ⁱⁱⁱ—Ni2—O3	87.67 (8)
O1ⁱ—Ni1—N1	89.94 (8)	N2^iv—Ni2—O3	92.33 (8)
O6ⁱ—Ni1—O6	180.0	N2^iv—Ni2—O3ⁱⁱ	87.66 (8)
O6—Ni1—N1	93.49 (9)	N2^iv—Ni2—O4	94.86 (8)
O6ⁱ—Ni1—N1	86.51 (9)	N2ⁱⁱⁱ—Ni2—O4	85.14 (8)
O6ⁱ—Ni1—N1ⁱ	93.49 (9)	N2ⁱⁱⁱ—Ni2—O4ⁱⁱ	94.86 (8)
O6—Ni1—N1ⁱ	86.51 (9)	N2^iv—Ni2—O4ⁱⁱ	85.14 (8)
N1—Ni1—N1ⁱ	180.0	N2ⁱⁱⁱ—Ni2—N2^iv	180.0
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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

The adc ligands adopt a chelating/monodentate binding mode, producing [Ni₂(H₂O)₂(adc)₂]_n monoperiodic chain motifs with an Ni1⋯Ni2 through-ligand distance of 9.694 (1) Å (Fig. 2). These are arranged parallel to the [1 $[\overline{1}]$ $[\overline{1}]$ ] direction. In turn, the chain motifs are linked into diperiodic [Ni₂(H₂O)₂(adc)₂(3-pina)₂]_n coordination polymer layer motifs with (4,4) grid topology (Fig. 3); these are oriented parallel to the (101) crystal planes. The bound water molecules (O6) engage in hydrogen bonding to adc carboxylate O atoms (O2 and O3) (Table 2). Water molecules of crystallization are held to the layer motifs by N—H⋯O hydrogen-bonding interactions involving the 3-pina amide groups (Table 2). Nonclassical C—H⋯O hydrogen-bonding interactions [C22⋯O5 distance = 3.110 (1) Å] promote aggregation of the [Ni₂(H₂O)₂(adc)₂(3-pina)₂]_n layers into the triperiodic full crystal structure of the title compound. The layers stack in an AAA pattern along both the a and the c crystal directions (Fig. 4).

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O3^v	0.87 (1)	2.04 (2)	2.886 (3)	163 (3)
O6—H6B⋯O2ⁱ	0.85 (2)	1.86 (2)	2.684 (3)	163 (3)
N3—H3⋯O1W	0.88	1.94	2.769 (3)	157
O1W—H1WA⋯O4^vi	0.84 (2)	2.00 (2)	2.831 (3)	169 (4)
O1W—H1WB⋯O2ⁱⁱⁱ	0.84 (2)	2.10 (2)	2.921 (3)	165 (4)
Symmetry codes: (i) ; (iii) ; (v) ; (vi) .

Figure 2
The [Ni₂(H₂O)₂(adc)₂]_n coordination polymer chain motif in the title compound.

Figure 3
The [Ni₂(H₂O)₂(adc)₂(3-pina)₂]_n coordination polymer layer motif in the title compound.

Figure 4
The AAA stacking of coordination polymer layers in the title compound.

Synthesis and crystallization

Ni(NO₃)₂·6H₂O (108 mg, 0.37 mmol), adamantane-1,3-dicarboxylic acid (adcH₂) (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 in 10 ml of distilled water 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 71% yield.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. H atoms attached to O atoms were located in a difference Fourier map and refined freely with U_iso(H) values fixed at 1.5U_eq(O).

Table 3
Experimental details

Crystal data
Chemical formula	[Ni(C₁₂H₁₄O₄)(C₁₁H₉N₃O)(H₂O)]·H₂O
M_r	516.18
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	173
a, b, c (Å)	10.718 (4), 10.933 (3), 11.586 (3)
α, β, γ (°)	113.462 (4), 109.626 (4), 96.053 (4)
V (Å³)	1127.2 (6)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.91
Crystal size (mm)	0.35 × 0.31 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD
No. of measured, independent and observed [I > 2σ(I)] reflections	12251, 4169, 3363
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.115, 1.07
No. of reflections	4169
No. of parameters	339
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.39
Computer programs: COSMO (Bruker, 2009 ), APEX2 (Bruker, 2013 ), SAINT (Bruker, 2013), olex2.solve (Bourhis et al., 2015 ), SHELXTL (Sheldrick, 2015 ), CrystalMakerX (Palmer, 2020 ), and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2291890

Crystal structure: contains datablocks I, 1R. DOI: https://doi.org/10.1107/S2414314623007587/vm4062sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314623007587/vm4062Isup2.hkl

checkCIF report

Computing details top

Data collection: COSMO (Bruker, 2009); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXTL (Sheldrick, 2015); molecular graphics: CrystalMakerX (Palmer, 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

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

Crystal data top

[Ni(C₁₂H₁₄O₄)(C₁₁H₉N₃O)(H₂O)]·H₂O	Z = 2
M_r = 516.18	F(000) = 540
Triclinic, P1	D_x = 1.521 Mg m⁻³
a = 10.718 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.933 (3) Å	Cell parameters from 6384 reflections
c = 11.586 (3) Å	θ = 2.2–25.4°
α = 113.462 (4)°	µ = 0.91 mm⁻¹
β = 109.626 (4)°	T = 173 K
γ = 96.053 (4)°	Block, green
V = 1127.2 (6) Å³	0.35 × 0.31 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	3363 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 25.5°, θ_min = 2.1°
Detector resolution: 836.6 pixels mm^-1	h = −12→12
φ and ω scans	k = −13→13
12251 measured reflections	l = −14→13
4169 independent reflections

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.062P)² + 0.5423P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
4169 reflections	Δρ_max = 0.82 e Å⁻³
339 parameters	Δρ_min = −0.38 e Å⁻³
7 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Ni1	1.000000	0.000000	0.000000	0.01704 (15)
Ni2	0.500000	0.500000	0.500000	0.01567 (15)
O1	0.8747 (2)	0.02292 (19)	0.0998 (2)	0.0207 (4)
O2	0.9879 (2)	0.2140 (2)	0.3019 (2)	0.0278 (5)
O3	0.44548 (19)	0.28855 (18)	0.3693 (2)	0.0194 (4)
O4	0.64885 (19)	0.39367 (18)	0.54244 (19)	0.0185 (4)
O5	1.2822 (2)	0.3913 (2)	−0.0396 (2)	0.0257 (5)
O6	0.8399 (2)	−0.1579 (2)	−0.1770 (2)	0.0323 (5)
H6A	0.7521 (16)	−0.180 (3)	−0.228 (3)	0.049*
H6B	0.880 (3)	−0.185 (4)	−0.231 (3)	0.049*
N1	0.9443 (2)	0.1585 (2)	−0.0536 (2)	0.0196 (5)
N2	1.4116 (2)	0.4695 (2)	−0.3776 (2)	0.0188 (5)
N3	1.0701 (2)	0.3768 (2)	−0.1866 (2)	0.0205 (5)
H3	1.027254	0.396693	−0.253463	0.043 (11)*
C1	0.8886 (3)	0.1069 (3)	0.2187 (3)	0.0186 (6)
C2	0.7255 (3)	0.1976 (3)	0.3250 (3)	0.0173 (6)
H2A	0.684592	0.228008	0.254351	0.021*
H2B	0.804113	0.275068	0.404075	0.013 (7)*
C3	0.7765 (3)	0.0702 (3)	0.2634 (3)	0.0180 (6)
C4	0.6536 (3)	−0.0489 (3)	0.1424 (3)	0.0214 (6)
H4A	0.611146	−0.021060	0.069887	0.026*
H4B	0.685396	−0.130982	0.101700	0.012 (7)*
C5	0.8406 (3)	0.0254 (3)	0.3757 (3)	0.0231 (7)
H5A	0.874709	−0.055787	0.337929	0.028*
H5B	0.919763	0.102021	0.455123	0.017 (7)*
C6	0.5469 (3)	−0.0859 (3)	0.1919 (3)	0.0253 (7)
H6	0.467734	−0.164142	0.111628	0.021 (8)*
C7	0.4942 (3)	0.0395 (3)	0.2508 (3)	0.0218 (6)
H7A	0.423551	0.015057	0.281145	0.026*
H7B	0.451510	0.067798	0.178771	0.011 (7)*
C8	0.6825 (3)	0.1151 (3)	0.4850 (3)	0.0238 (7)
H8A	0.761453	0.192252	0.564112	0.029*
H8B	0.614538	0.092712	0.519184	0.033 (9)*
C9	0.7322 (3)	−0.0122 (3)	0.4243 (3)	0.0274 (7)
H9	0.774107	−0.041601	0.496624	0.030 (9)*
C10	0.6096 (4)	−0.1307 (3)	0.3019 (4)	0.0316 (8)
H10A	0.640577	−0.213959	0.263009	0.038*
H10B	0.539579	−0.154594	0.333230	0.027 (8)*
C11	0.6161 (3)	0.1596 (3)	0.3742 (3)	0.0175 (6)
C12	0.5672 (3)	0.2864 (3)	0.4325 (3)	0.0170 (6)
C14	0.8279 (3)	0.1933 (3)	−0.0554 (3)	0.0240 (7)
H14	0.770731	0.149260	−0.027780	0.030 (9)*
C15	1.0241 (3)	0.2222 (3)	−0.0922 (3)	0.0204 (6)
H15	1.108039	0.199666	−0.089106	0.039 (10)*
C16	0.7881 (3)	0.2911 (3)	−0.0962 (3)	0.0239 (7)
H16	0.705149	0.313949	−0.095664	0.028 (8)*
C17	0.9894 (3)	0.3197 (3)	−0.1365 (3)	0.0188 (6)
C18	0.8696 (3)	0.3553 (3)	−0.1376 (3)	0.0220 (6)
H18	0.843662	0.422547	−0.166249	0.022 (8)*
C19	1.2793 (3)	0.3958 (3)	−0.4378 (3)	0.0204 (6)
H19	1.233694	0.352711	−0.535775	0.002 (6)*
C20	1.2063 (3)	0.3793 (3)	−0.3659 (3)	0.0204 (6)
H20	1.112088	0.327124	−0.413126	0.016 (7)*
C21	1.2716 (3)	0.4397 (3)	−0.2230 (3)	0.0173 (6)
C22	1.4077 (3)	0.5186 (3)	−0.1589 (3)	0.0193 (6)
H22	1.455078	0.562638	−0.061051	0.015 (7)*
C23	1.4739 (3)	0.5327 (3)	−0.2388 (3)	0.0211 (6)
H23	1.566465	0.588835	−0.194019	0.034 (9)*
C24	1.2087 (3)	0.4033 (3)	−0.1390 (3)	0.0193 (6)
O1W	0.9387 (2)	0.5047 (2)	−0.3366 (3)	0.0396 (6)
H1WA	0.8521 (19)	0.483 (4)	−0.370 (4)	0.059*
H1WB	0.969 (4)	0.590 (2)	−0.312 (4)	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0171 (3)	0.0182 (3)	0.0183 (3)	0.0030 (2)	0.0112 (2)	0.0079 (2)
Ni2	0.0158 (3)	0.0161 (3)	0.0184 (3)	0.0053 (2)	0.0106 (2)	0.0079 (2)
O1	0.0223 (11)	0.0220 (10)	0.0215 (11)	0.0055 (8)	0.0152 (9)	0.0086 (9)
O2	0.0206 (11)	0.0250 (11)	0.0283 (12)	−0.0013 (9)	0.0137 (10)	0.0024 (9)
O3	0.0157 (11)	0.0188 (9)	0.0242 (11)	0.0059 (8)	0.0093 (9)	0.0094 (9)
O4	0.0179 (11)	0.0182 (9)	0.0207 (11)	0.0059 (8)	0.0093 (9)	0.0088 (9)
O5	0.0213 (11)	0.0356 (12)	0.0254 (11)	0.0057 (9)	0.0089 (10)	0.0201 (10)
O6	0.0156 (11)	0.0406 (13)	0.0269 (13)	0.0016 (10)	0.0110 (10)	0.0024 (10)
N1	0.0183 (13)	0.0221 (12)	0.0204 (13)	0.0038 (10)	0.0103 (11)	0.0103 (10)
N2	0.0178 (13)	0.0207 (12)	0.0214 (13)	0.0054 (10)	0.0103 (11)	0.0111 (10)
N3	0.0198 (13)	0.0272 (12)	0.0234 (13)	0.0070 (10)	0.0108 (11)	0.0183 (11)
C1	0.0200 (16)	0.0212 (14)	0.0218 (15)	0.0103 (12)	0.0125 (13)	0.0125 (13)
C2	0.0170 (15)	0.0172 (13)	0.0210 (15)	0.0037 (11)	0.0122 (13)	0.0086 (12)
C3	0.0189 (15)	0.0208 (13)	0.0200 (15)	0.0066 (12)	0.0139 (13)	0.0095 (12)
C4	0.0186 (15)	0.0212 (14)	0.0249 (16)	0.0066 (12)	0.0135 (13)	0.0072 (13)
C5	0.0232 (17)	0.0285 (15)	0.0283 (17)	0.0144 (13)	0.0153 (14)	0.0176 (14)
C6	0.0229 (17)	0.0165 (14)	0.0337 (18)	0.0006 (12)	0.0186 (15)	0.0047 (13)
C7	0.0180 (15)	0.0176 (13)	0.0326 (17)	0.0039 (12)	0.0171 (14)	0.0092 (13)
C8	0.0305 (18)	0.0300 (15)	0.0277 (17)	0.0146 (14)	0.0215 (15)	0.0197 (14)
C9	0.0336 (19)	0.0363 (17)	0.0376 (19)	0.0212 (15)	0.0267 (16)	0.0280 (16)
C10	0.042 (2)	0.0187 (14)	0.052 (2)	0.0130 (14)	0.0340 (18)	0.0201 (15)
C11	0.0170 (15)	0.0180 (13)	0.0211 (15)	0.0065 (11)	0.0124 (13)	0.0084 (12)
C12	0.0187 (16)	0.0182 (13)	0.0186 (15)	0.0047 (12)	0.0121 (13)	0.0092 (12)
C14	0.0224 (16)	0.0247 (15)	0.0284 (17)	0.0039 (13)	0.0149 (14)	0.0124 (13)
C15	0.0186 (15)	0.0215 (14)	0.0227 (15)	0.0047 (12)	0.0107 (13)	0.0102 (12)
C16	0.0178 (16)	0.0277 (15)	0.0296 (17)	0.0075 (12)	0.0140 (14)	0.0127 (14)
C17	0.0182 (15)	0.0199 (13)	0.0198 (15)	0.0029 (11)	0.0106 (13)	0.0090 (12)
C18	0.0223 (16)	0.0222 (14)	0.0240 (16)	0.0052 (12)	0.0120 (13)	0.0114 (13)
C19	0.0223 (16)	0.0219 (14)	0.0161 (15)	0.0045 (12)	0.0078 (13)	0.0085 (12)
C20	0.0141 (15)	0.0241 (14)	0.0233 (16)	0.0028 (12)	0.0080 (13)	0.0114 (13)
C21	0.0195 (15)	0.0170 (13)	0.0223 (15)	0.0084 (11)	0.0130 (13)	0.0112 (12)
C22	0.0180 (15)	0.0226 (14)	0.0181 (15)	0.0039 (12)	0.0069 (13)	0.0109 (12)
C23	0.0179 (16)	0.0234 (14)	0.0234 (16)	0.0032 (12)	0.0096 (13)	0.0118 (13)
C24	0.0199 (16)	0.0190 (13)	0.0206 (15)	0.0055 (12)	0.0098 (13)	0.0092 (12)
O1W	0.0216 (12)	0.0367 (13)	0.0624 (18)	0.0055 (11)	0.0071 (13)	0.0337 (14)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	2.0216 (19)	C5—H5B	0.9900
Ni1—O1	2.0216 (19)	C5—C9	1.536 (4)
Ni1—O6ⁱ	2.079 (2)	C6—H6	1.0000
Ni1—O6	2.079 (2)	C6—C7	1.531 (4)
Ni1—N1	2.138 (2)	C6—C10	1.519 (4)
Ni1—N1ⁱ	2.138 (2)	C7—H7A	0.9900
Ni2—O3	2.0766 (18)	C7—H7B	0.9900
Ni2—O3ⁱⁱ	2.0766 (18)	C7—C11	1.537 (4)
Ni2—O4	2.1113 (18)	C8—H8A	0.9900
Ni2—O4ⁱⁱ	2.1113 (18)	C8—H8B	0.9900
Ni2—N2ⁱⁱⁱ	2.058 (2)	C8—C9	1.531 (4)
Ni2—N2^iv	2.058 (2)	C8—C11	1.533 (4)
O1—C1	1.260 (3)	C9—H9	1.0000
O2—C1	1.258 (3)	C9—C10	1.530 (5)
O3—C12	1.272 (3)	C10—H10A	0.9900
O4—C12	1.269 (3)	C10—H10B	0.9900
O5—C24	1.224 (3)	C11—C12	1.515 (3)
O6—H6A	0.871 (14)	C14—H14	0.9500
O6—H6B	0.849 (18)	C14—C16	1.382 (4)
N1—C14	1.337 (4)	C15—H15	0.9500
N1—C15	1.340 (4)	C15—C17	1.389 (4)
N2—C19	1.339 (4)	C16—H16	0.9500
N2—C23	1.344 (4)	C16—C18	1.382 (4)
N3—H3	0.8800	C17—C18	1.378 (4)
N3—C17	1.410 (3)	C18—H18	0.9500
N3—C24	1.351 (4)	C19—H19	0.9500
C1—C3	1.534 (4)	C19—C20	1.366 (4)
C2—H2A	0.9900	C20—H20	0.9500
C2—H2B	0.9900	C20—C21	1.386 (4)
C2—C3	1.542 (4)	C21—C22	1.385 (4)
C2—C11	1.551 (4)	C21—C24	1.500 (4)
C3—C4	1.530 (4)	C22—H22	0.9500
C3—C5	1.544 (4)	C22—C23	1.384 (4)
C4—H4A	0.9900	C23—H23	0.9500
C4—H4B	0.9900	O1W—H1WA	0.840 (18)
C4—C6	1.526 (4)	O1W—H1WB	0.842 (18)
C5—H5A	0.9900

O1ⁱ—Ni1—O1	180.0	C7—C6—H6	109.0
O1—Ni1—O6ⁱ	90.58 (8)	C10—C6—C4	110.4 (2)
O1—Ni1—O6	89.42 (8)	C10—C6—H6	109.0
O1ⁱ—Ni1—O6ⁱ	89.42 (8)	C10—C6—C7	109.6 (3)
O1ⁱ—Ni1—O6	90.58 (8)	C6—C7—H7A	109.9
O1—Ni1—N1	90.06 (8)	C6—C7—H7B	109.9
O1—Ni1—N1ⁱ	89.94 (8)	C6—C7—C11	108.9 (2)
O1ⁱ—Ni1—N1ⁱ	90.06 (8)	H7A—C7—H7B	108.3
O1ⁱ—Ni1—N1	89.94 (8)	C11—C7—H7A	109.9
O6ⁱ—Ni1—O6	180.0	C11—C7—H7B	109.9
O6—Ni1—N1	93.49 (9)	H8A—C8—H8B	108.2
O6ⁱ—Ni1—N1	86.51 (9)	C9—C8—H8A	109.7
O6ⁱ—Ni1—N1ⁱ	93.49 (9)	C9—C8—H8B	109.7
O6—Ni1—N1ⁱ	86.51 (9)	C9—C8—C11	109.9 (2)
N1—Ni1—N1ⁱ	180.0	C11—C8—H8A	109.7
O3ⁱⁱ—Ni2—O3	180.0	C11—C8—H8B	109.7
O3—Ni2—O4ⁱⁱ	116.95 (7)	C5—C9—H9	109.5
O3—Ni2—O4	63.05 (7)	C8—C9—C5	109.1 (2)
O3ⁱⁱ—Ni2—O4	116.95 (7)	C8—C9—H9	109.5
O3ⁱⁱ—Ni2—O4ⁱⁱ	63.05 (7)	C10—C9—C5	109.9 (3)
O4—Ni2—O4ⁱⁱ	180.0	C10—C9—C8	109.3 (3)
N2ⁱⁱⁱ—Ni2—O3ⁱⁱ	92.34 (8)	C10—C9—H9	109.5
N2ⁱⁱⁱ—Ni2—O3	87.67 (8)	C6—C10—C9	109.3 (2)
N2^iv—Ni2—O3	92.33 (8)	C6—C10—H10A	109.8
N2^iv—Ni2—O3ⁱⁱ	87.66 (8)	C6—C10—H10B	109.8
N2^iv—Ni2—O4	94.86 (8)	C9—C10—H10A	109.8
N2ⁱⁱⁱ—Ni2—O4	85.14 (8)	C9—C10—H10B	109.8
N2ⁱⁱⁱ—Ni2—O4ⁱⁱ	94.86 (8)	H10A—C10—H10B	108.3
N2^iv—Ni2—O4ⁱⁱ	85.14 (8)	C7—C11—C2	109.4 (2)
N2ⁱⁱⁱ—Ni2—N2^iv	180.0	C8—C11—C2	108.7 (2)
C1—O1—Ni1	133.44 (18)	C8—C11—C7	109.7 (2)
C12—O3—Ni2	89.28 (15)	C12—C11—C2	108.2 (2)
C12—O4—Ni2	87.83 (15)	C12—C11—C7	110.0 (2)
Ni1—O6—H6A	143 (2)	C12—C11—C8	110.8 (2)
Ni1—O6—H6B	101 (2)	O3—C12—Ni2	59.03 (13)
H6A—O6—H6B	107 (3)	O3—C12—C11	120.5 (2)
C14—N1—Ni1	121.94 (19)	O4—C12—Ni2	60.60 (13)
C14—N1—C15	118.1 (2)	O4—C12—O3	119.1 (2)
C15—N1—Ni1	119.93 (18)	O4—C12—C11	120.4 (2)
C19—N2—Ni2^v	118.35 (19)	C11—C12—Ni2	170.38 (19)
C19—N2—C23	117.7 (2)	N1—C14—H14	118.9
C23—N2—Ni2^v	123.49 (19)	N1—C14—C16	122.2 (3)
C17—N3—H3	117.7	C16—C14—H14	118.9
C24—N3—H3	117.7	N1—C15—H15	118.6
C24—N3—C17	124.6 (2)	N1—C15—C17	122.8 (3)
O1—C1—C3	116.0 (2)	C17—C15—H15	118.6
O2—C1—O1	124.8 (3)	C14—C16—H16	120.2
O2—C1—C3	119.1 (2)	C18—C16—C14	119.6 (3)
H2A—C2—H2B	108.2	C18—C16—H16	120.2
C3—C2—H2A	109.7	C15—C17—N3	121.4 (2)
C3—C2—H2B	109.7	C18—C17—N3	119.7 (2)
C3—C2—C11	109.7 (2)	C18—C17—C15	118.8 (3)
C11—C2—H2A	109.7	C16—C18—H18	120.8
C11—C2—H2B	109.7	C17—C18—C16	118.5 (3)
C1—C3—C2	110.6 (2)	C17—C18—H18	120.8
C1—C3—C5	107.9 (2)	N2—C19—H19	118.2
C2—C3—C5	108.7 (2)	N2—C19—C20	123.5 (3)
C4—C3—C1	111.7 (2)	C20—C19—H19	118.2
C4—C3—C2	109.0 (2)	C19—C20—H20	120.5
C4—C3—C5	108.9 (2)	C19—C20—C21	119.0 (3)
C3—C4—H4A	109.6	C21—C20—H20	120.5
C3—C4—H4B	109.6	C20—C21—C24	122.1 (2)
H4A—C4—H4B	108.1	C22—C21—C20	118.1 (3)
C6—C4—C3	110.1 (2)	C22—C21—C24	119.0 (2)
C6—C4—H4A	109.6	C21—C22—H22	120.3
C6—C4—H4B	109.6	C23—C22—C21	119.4 (3)
C3—C5—H5A	109.7	C23—C22—H22	120.3
C3—C5—H5B	109.7	N2—C23—C22	122.1 (3)
H5A—C5—H5B	108.2	N2—C23—H23	118.9
C9—C5—C3	109.9 (2)	C22—C23—H23	118.9
C9—C5—H5A	109.7	O5—C24—N3	124.6 (3)
C9—C5—H5B	109.7	O5—C24—C21	119.4 (3)
C4—C6—H6	109.0	N3—C24—C21	115.8 (2)
C4—C6—C7	109.8 (2)	H1WA—O1W—H1WB	109 (3)

Ni1—O1—C1—O2	9.4 (4)	C5—C9—C10—C6	−59.2 (3)
Ni1—O1—C1—C3	−168.59 (17)	C6—C7—C11—C2	59.9 (3)
Ni1—N1—C14—C16	−176.9 (2)	C6—C7—C11—C8	−59.2 (3)
Ni1—N1—C15—C17	175.9 (2)	C6—C7—C11—C12	178.7 (2)
Ni2—O3—C12—O4	8.7 (2)	C7—C6—C10—C9	−61.6 (3)
Ni2—O3—C12—C11	−168.8 (2)	C7—C11—C12—O3	−8.7 (3)
Ni2—O4—C12—O3	−8.5 (2)	C7—C11—C12—O4	173.8 (2)
Ni2—O4—C12—C11	169.0 (2)	C8—C9—C10—C6	60.4 (3)
Ni2^v—N2—C19—C20	−173.9 (2)	C8—C11—C12—O3	−130.2 (3)
Ni2^v—N2—C23—C22	174.8 (2)	C8—C11—C12—O4	52.3 (3)
O1—C1—C3—C2	−132.5 (2)	C9—C8—C11—C2	−60.7 (3)
O1—C1—C3—C4	−10.9 (3)	C9—C8—C11—C7	58.8 (3)
O1—C1—C3—C5	108.7 (3)	C9—C8—C11—C12	−179.5 (2)
O2—C1—C3—C2	49.3 (3)	C10—C6—C7—C11	60.8 (3)
O2—C1—C3—C4	170.9 (2)	C11—C2—C3—C1	−178.0 (2)
O2—C1—C3—C5	−69.5 (3)	C11—C2—C3—C4	58.8 (3)
N1—C14—C16—C18	0.4 (4)	C11—C2—C3—C5	−59.7 (3)
N1—C15—C17—N3	−175.0 (2)	C11—C8—C9—C5	61.0 (3)
N1—C15—C17—C18	1.7 (4)	C11—C8—C9—C10	−59.2 (3)
N2—C19—C20—C21	−0.9 (4)	C14—N1—C15—C17	−1.5 (4)
N3—C17—C18—C16	175.9 (3)	C14—C16—C18—C17	−0.2 (4)
C1—C3—C4—C6	177.9 (2)	C15—N1—C14—C16	0.4 (4)
C1—C3—C5—C9	179.9 (2)	C15—C17—C18—C16	−0.8 (4)
C2—C3—C4—C6	−59.6 (3)	C17—N3—C24—O5	−6.1 (4)
C2—C3—C5—C9	59.9 (3)	C17—N3—C24—C21	169.4 (2)
C2—C11—C12—O3	110.7 (3)	C19—N2—C23—C22	2.8 (4)
C2—C11—C12—O4	−66.8 (3)	C19—C20—C21—C22	2.2 (4)
C3—C2—C11—C7	−59.5 (3)	C19—C20—C21—C24	−167.4 (2)
C3—C2—C11—C8	60.3 (3)	C20—C21—C22—C23	−1.0 (4)
C3—C2—C11—C12	−179.3 (2)	C20—C21—C24—O5	140.1 (3)
C3—C4—C6—C7	61.0 (3)	C20—C21—C24—N3	−35.7 (4)
C3—C4—C6—C10	−60.0 (3)	C21—C22—C23—N2	−1.6 (4)
C3—C5—C9—C8	−60.5 (3)	C22—C21—C24—O5	−29.4 (4)
C3—C5—C9—C10	59.4 (3)	C22—C21—C24—N3	154.9 (2)
C4—C3—C5—C9	−58.8 (3)	C23—N2—C19—C20	−1.6 (4)
C4—C6—C7—C11	−60.8 (3)	C24—N3—C17—C15	−34.5 (4)
C4—C6—C10—C9	59.5 (3)	C24—N3—C17—C18	148.9 (3)
C5—C3—C4—C6	58.9 (3)	C24—C21—C22—C23	168.9 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O3^vi	0.87 (1)	2.04 (2)	2.886 (3)	163 (3)
O6—H6B···O2ⁱ	0.85 (2)	1.86 (2)	2.684 (3)	163 (3)
N3—H3···O1W	0.88	1.94	2.769 (3)	157
O1W—H1WA···O4^vii	0.84 (2)	2.00 (2)	2.831 (3)	169 (4)
O1W—H1WB···O2ⁱⁱⁱ	0.84 (2)	2.10 (2)	2.921 (3)	165 (4)

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

Funding information

Funding for this research was provided by: Lyman Briggs College, Michigan State University.

References

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