Crystal structure and luminescence spectrum of a one-dimensional nickel(II) coordination polymer incorporating 1,4-bis­[(2-methyl­imidazol-1-yl)meth­yl]benzene and adamantane-1,3-di­carboxyl­ate co-ligands

Zhang, Y.; Qin, H.; Wu, B.

doi:10.1107/S2056989023006059

research communications

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ISSN: 2056-9890

Volume 79| Part 8| August 2023| Pages 722-725

https://doi.org/10.1107/S2056989023006059

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Crystal structure and luminescence spectrum of a one-dimensional nickel(II) coordination polymer incorporating 1,4-bis[(2-methylimidazol-1-yl)methyl]benzene and adamantane-1,3-dicarboxylate co-ligands

Yong Zhang,^a ^* Hongni Qin ^a and Bing Wu ^b

^aSuzhou Industrial Park Institute of Services Outsourcing, Suzhou 215123, Jiangsu, People's Republic of China, and ^bCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China
^*Correspondence e-mail: zhangyong@siso.edu.cn

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 17 October 2022; accepted 10 July 2023; online 14 July 2023)

An Ni^II coordination polymer, namely, poly[(μ₂-adamantane-1,3-dicarboxylato-κ⁴O¹,O^1′:O³,O^3′)[μ₂-1,4-bis(2-methyl-imidazol-1-ylmethyl)benzene-κ²N³:N^3′]nickel(II)], [Ni(C₁₂H₁₄O₄)(C₁₆H₁₈N₄)]_n or [Ni(adc)(bmib)]_n, (I) [adc = adamantane-1,3-dicarboxylate, C₁₂H₁₄O₄^2– and bmib = 1,4-bis(2-methyl-imidazol-1-ylmethyl)benzene, C₁₆H₁₈N₄] was synthesized and characterized. It exhibits a one-dimensional extended structure built up from alternating [Ni₂(bmib)₂] 26-membered rings and [Ni₂(adc)₂] 16-membered rings. The nickel atom lies on a crystallographic twofold axis and both ligands are completed by mirror symmetry. The solid-state luminescence spectra of (I) and the bmib ligand show strong emissions at 442 and 410 nm, respectively.

Keywords: crystal structure; nickel; coordination polymer.

CCDC reference: 2280450

1. Chemical context

Coordination polymers have been widely studied because of their diverse and interesting structures (Bao et al., 2019 ; Zhang & Lin 2014 ; Wang et al., 2020 ; Parmar et al., 2021 ) and potential applications in sorption (Fan et al., 2021 ), luminescent materials (Zhou et al., 2021 ), magnetism (Yang et al., 2021a ), catalytic splitting of water (Li et al., 2019 ), catalytic degrading of pollutants (Jiang et al., 2018 ) and battery materials (Yang et al., 2021b ; Bao et al., 2019). In the construction of coordination polymers, N-donor (imidazole or triazole ligands) and O-donor (polycarboxylate ligands) co-ligand systems lead to various interesting networks (Yang et al., 2014 ; Sun et al., 2013 ; Zhang et al., 2021a ,b ). 1,4-Bis(2-methyl-imidazol-1-ylmethyl)benzene (C₁₆H₁₈N₄; bmib) is a semi-flexible bidentate N-donor ligand and is widely used in the construction of different coordination polymers (Yang et al., 2014; Sun et al., 2013). Four Ni-bmib coordination polymers are documented: [Ni(bcpb)(bmib)_0.5]_n (H₂bcpb = 3,5-bis(4-carboxyphenyl)pyridine) has a (3,4)-connected three-dimensional amd network, with the point symbol of (6^2.8)(6^3.8^.10²) (Fan et al., 2014a ). {[Ni(tptc)_0.5(bmib)]·0.25H₂O}_n (H₄tptc = terphenyl-2,5,2′,5′-tetracarboxylic acid) shows a (4,4)-coordinated three-dimensional network with a point symbol of (4^.6^4.8²)₂(4^2.8⁴) (Fan et al., 2014b ). [Ni(bmib)(bpda)] (H₂bpda = biphenyl-3,4′-dicarboxylic acid) exhibits a threefold interpenetrated (6^5.8) network (Sun et al., 2013). {[Ni₂(glu)₂(bmib)₂(H₂O)₂]·H₂O}_n (glu = glutarate) exhibits a 4-connected three-dimensional framework with point symbol 6⁶, but is not a typical dia network (Zhao et al., 2020 ). The adamantane-1,3-dicarboxylate dianion (C₁₂H₁₄O₄^2–; adc) is a good O-donor bridging ligand for constructing coordination polymers (Zhao et al., 2017 ). In this work, the title Ni^II coordination polymer [Ni(adc)(bmib)]_n, (I), was synthesized and its crystal structure was determined.

2. Structural commentary

The structural motif of the title coordination polymer (I) is a one-dimensional chain. The Ni^II atom in (I) lies on a crystallographic twofold axis and adopts a distorted cis-NiN₂O₄ octahedral coordination geometry arising from four oxygen atoms from two carboxylate groups in two adc ligands [Ni1—O1 = 2.179 (3) Å; Ni1—O2 = 2.096 (3) Å] and two nitrogen atoms of two bmib ligands [Ni1—N2 = 2.050 (3) Å] (Table 1, Fig. 1). Atoms O1 and O1ⁱ lie opposite to each other with the bond angle O1—Ni1—O1ⁱ [symmetry code: (i) 1 – x, y, –z] = 142.26 (15)°. These Ni—O and Ni—N bond lengths are typical and show no deviations from those in other distorted octahedral Ni^II coordination polymers (Fan et al., 2014a,b). The other bond angles are in the range 61.20 (11)–156.75 (13)° (Fan et al., 2014a,b). The dihedral angle between the imidazole and benzene rings of the bmib molecule is 78.8 (2)° and that between the imidazole rings is 67.1 (2)°. The bmib ligand exhibits a gauche conformation and the torsion angle N1—C4—C1—C3 is −117.9 (5)°. In the extended structure, two bmib ligands bridge two Ni^II atoms and construct a [Ni₂(bmib)₂] 26-membered ring with an Ni⋯Ni distance of 12.100 (2) Å. Two carboxylate groups of one adc ligand exhibit an O,O-chelating mode such that two adc ligands link two Ni^II atoms and construct an [Ni₂(adc)₂] 16-membered ring with Ni⋯Ni = 8.0978 (16) Å. The Ni^II atoms are alternately connected by the bridging bmib and adc moieties, resulting in a chain containing alternative [Ni₂(bmib)₂] and [Ni₂(adc)₂] loops propagating along the b-axis direction (Fig. 2).

Table 1
Selected geometric parameters (Å, °)

Ni1—O1	2.179 (3)	Ni1—N2	2.050 (3)
Ni1—O2	2.096 (3)

O1—Ni1—O1ⁱ	142.26 (15)	N2—Ni1—O1	95.55 (12)
O2—Ni1—O1	61.20 (11)	N2—Ni1—O2ⁱ	91.42 (13)
O2—Ni1—O1ⁱ	91.22 (12)	N2—Ni1—O2	156.75 (13)
O2—Ni1—O2ⁱ	89.19 (18)	N2—Ni1—N2ⁱ	97.01 (19)
N2—Ni1—O1ⁱ	109.38 (12)
Symmetry code: (i) .

Figure 1
A view of the title compound with displacement ellipsoids drawn at the 50% probability level. Symmetry codes: (i) −x + 1, y, −z; (ii) x, −y + 1, z; (iii) x, −y, z.

Figure 2
The one-dimensional supramolecular structure of (I)

3. Supramolecular features

Each [Ni(bmib)(adc)]_n chain is surrounded by six further chains (Fig. 3). There are no C—H⋯O hydrogen bond interactions or aromatic π–π stacking interactions between the rings, thus the three-dimensional supramolecular architecture of (I) must therefore be established by van der Waals interactions.

Figure 3
The stacking of [010] chains in the crystal structure of (I)

. The bonds of one chain are shown in blue and the bonds of six adjacent chains are shown in purple.

4. Luminescence properties

The solid-state luminescence spectra of (I) and the bmib ligand were measured at room temperature (Fig. 4). Compound (I) and bmib exhibit strong emissions at 442 nm and 410 nm, respectively, upon excitation at 340 nm. The emissions can be attributed to an intraligand charge-transfer transition (Yang et al., 2014).

Figure 4
Solid-state luminescence spectra of (I)

and the bmib ligand at room temperature.

5. Database survey

The bmib ligand is widely used in coordination chemistry but for Ni–bmib compounds, a search of the Cambridge Structural Database (CSD, version 5.42, update of September 2021; Groom et al., 2016) revealed only the four coordination polymers noted in the Chemical context section.

6. Synthesis and crystallization

A mixture of bmib (0.22 mmol), Ni(NO₃)₂^.6H₂O (0.28 mmol), H₂adc (0.22 mmol), NaOH (0.38 mmol) and H₂O (14.0 ml) was added to a 20.0 ml Teflon-lined stainless steel autoclave, which was then sealed and heated to 393 K for 5 d. Green crystals of (I) were obtained when the mixture was cooled to room temperature.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The hydrogen atoms (CH, CH₂, CH₃ groups) were placed geometrically (C—H = 0.93–0.98 Å) and refined using a riding model with U_iso(H) = 1.2U_eq(C) for CH and CH₂ or 1.5U_eq(C) for CH₃ groups.

Table 2
Experimental details

Crystal data
Chemical formula	[Ni(C₁₂H₁₄O₄)(C₁₆H₁₈N₄)]
M_r	547.28
Crystal system, space group	Monoclinic, C2/m
Temperature (K)	293
a, b, c (Å)	14.489 (3), 20.198 (4), 10.741 (2)
β (°)	127.46 (3)
V (Å³)	2495.2 (12)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.82
Crystal size (mm)	0.60 × 0.20 × 0.10

Data collection
Diffractometer	Rigaku Mercury CCD
Absorption correction	Multi-scan (Jacobson, 1998 )
T_min, T_max	0.639, 0.922
No. of measured, independent and observed [I > 2σ(I)] reflections	12149, 2343, 1975
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.148, 1.15
No. of reflections	2343
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.42
Computer programs: CrysAlis PRO (Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), OLEX2.solve (Bourhis et al., 2015 ), SHELXL (Sheldrick, 2015 ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 2280450

Crystal structure: contains datablock . DOI: https://doi.org/10.1107/S2056989023006059/hb8041sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023006059/hb8041Isup3.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

Poly[(µ₂-adamantane-1,3-dicarboxylato-κ⁴O¹,O^1':O³,O^3')[µ₂-1,4-bis(2-methyl-imidazol-1-ylmethyl)benzene-κ²N³:N^3']nickel(II)] top

Crystal data top

[Ni(C₁₂H₁₄O₄)(C₁₆H₁₈N₄)]	F(000) = 1152
M_r = 547.28	D_x = 1.457 Mg m⁻³
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
a = 14.489 (3) Å	Cell parameters from 4170 reflections
b = 20.198 (4) Å	θ = 3.1–25.3°
c = 10.741 (2) Å	µ = 0.82 mm⁻¹
β = 127.46 (3)°	T = 293 K
V = 2495.2 (12) Å³	Block, green
Z = 4	0.60 × 0.20 × 0.10 mm

Data collection top

Rigaku Mercury CCD diffractometer	2343 independent reflections
Graphite monochromator	1975 reflections with I > 2σ(I)
Detector resolution: 7.31 pixels mm^-1	R_int = 0.060
ω scans	θ_max = 25.4°, θ_min = 3.1°
Absorption correction: multi-scan (Jacobson, 1998)	h = −17→17
T_min = 0.639, T_max = 0.922	k = −20→24
12149 measured reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.065	H-atom parameters constrained
wR(F²) = 0.148	w = 1/[σ²(F_o²) + (0.058P)² + 5.3646P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
2343 reflections	Δρ_max = 0.39 e Å⁻³
174 parameters	Δρ_min = −0.42 e Å⁻³
0 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	Occ. (<1)
Ni1	0.500000	0.20046 (3)	0.000000	0.0398 (3)
O1	0.3442 (2)	0.16556 (13)	−0.0328 (3)	0.0482 (7)
O2	0.5165 (3)	0.12656 (14)	0.1494 (4)	0.0516 (8)
N1	0.3458 (3)	0.32448 (17)	−0.3947 (4)	0.0485 (9)
N2	0.4156 (3)	0.26772 (16)	−0.1800 (4)	0.0443 (8)
C1	0.3348 (4)	0.4311 (2)	−0.5188 (5)	0.0451 (10)
C2	0.4275 (5)	0.4655 (3)	−0.4023 (7)	0.107 (3)
H2	0.492752	0.442846	−0.320417	0.129*
C3	0.2413 (4)	0.4653 (2)	−0.6326 (6)	0.0684 (15)
H3	0.175274	0.442626	−0.712964	0.082*
C4	0.3337 (5)	0.3562 (2)	−0.5266 (5)	0.0570 (12)
H4A	0.261252	0.341958	−0.623726	0.068*
H4B	0.396716	0.341706	−0.528253	0.068*
C5	0.4370 (4)	0.28896 (19)	−0.2772 (5)	0.0435 (10)
C6	0.3077 (4)	0.2912 (2)	−0.2387 (6)	0.0532 (12)
H6	0.270297	0.284149	−0.193745	0.064*
C7	0.2632 (4)	0.3262 (2)	−0.3714 (6)	0.0593 (13)
H7	0.191169	0.347080	−0.433802	0.071*
C8	0.5450 (4)	0.2746 (3)	−0.2605 (6)	0.0625 (13)
H8A	0.540177	0.295302	−0.344794	0.094*
H8B	0.611035	0.291763	−0.162159	0.094*
H8C	0.553297	0.227662	−0.263841	0.094*
C9	0.3562 (3)	0.06300 (18)	0.0957 (4)	0.0350 (9)
C10	0.2234 (3)	0.06224 (19)	−0.0132 (5)	0.0437 (10)
H10A	0.194962	0.063122	−0.121488	0.052*
H10B	0.194416	0.101283	0.005507	0.052*
C11	0.4003 (4)	0.06176 (19)	0.2666 (5)	0.0449 (10)
H11A	0.374414	0.101241	0.288638	0.054*
H11B	0.484678	0.061300	0.336412	0.054*
C12	0.4004 (5)	0.000000	0.0664 (6)	0.0355 (12)
H12A	0.484704	0.000000	0.135236	0.043*
H12B	0.374053	0.000001	−0.041030	0.043*
C13	0.1788 (5)	0.000000	0.0159 (7)	0.0460 (15)
H13	0.093556	−0.000001	−0.054721	0.055*
C14	0.2219 (6)	0.000000	0.1860 (8)	0.0551 (17)
H14A	0.193036	0.038915	0.205261	0.066*	0.5
H14B	0.193036	−0.038915	0.205261	0.066*	0.5
C15	0.3539 (6)	0.000000	0.2952 (7)	0.0476 (15)
H15	0.381400	0.000000	0.404170	0.057*
C16	0.4075 (4)	0.12241 (18)	0.0692 (5)	0.0409 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0486 (5)	0.0269 (4)	0.0458 (5)	0.000	0.0297 (4)	0.000
O1	0.0517 (17)	0.0344 (15)	0.0601 (19)	0.0081 (13)	0.0348 (16)	0.0121 (14)
O2	0.0451 (18)	0.0369 (16)	0.0623 (19)	−0.0034 (13)	0.0273 (15)	0.0097 (14)
N1	0.067 (2)	0.0355 (19)	0.044 (2)	0.0131 (17)	0.035 (2)	0.0066 (16)
N2	0.056 (2)	0.0316 (18)	0.052 (2)	0.0027 (16)	0.0361 (19)	0.0022 (16)
C1	0.057 (3)	0.037 (2)	0.037 (2)	0.0043 (19)	0.026 (2)	0.0010 (18)
C2	0.075 (4)	0.056 (3)	0.075 (4)	0.015 (3)	−0.014 (3)	0.006 (3)
C3	0.051 (3)	0.039 (2)	0.063 (3)	−0.004 (2)	0.008 (2)	−0.004 (2)
C4	0.089 (4)	0.039 (2)	0.044 (3)	0.008 (2)	0.040 (3)	0.003 (2)
C5	0.059 (3)	0.030 (2)	0.048 (2)	0.0016 (19)	0.036 (2)	0.0002 (18)
C6	0.064 (3)	0.045 (3)	0.067 (3)	0.013 (2)	0.049 (3)	0.008 (2)
C7	0.062 (3)	0.050 (3)	0.069 (3)	0.020 (2)	0.041 (3)	0.011 (2)
C8	0.066 (3)	0.061 (3)	0.073 (3)	0.010 (2)	0.049 (3)	0.018 (3)
C9	0.040 (2)	0.0280 (19)	0.038 (2)	0.0037 (16)	0.0242 (18)	0.0045 (16)
C10	0.044 (2)	0.035 (2)	0.047 (2)	0.0057 (18)	0.026 (2)	0.0032 (18)
C11	0.057 (3)	0.034 (2)	0.046 (2)	0.0007 (19)	0.033 (2)	−0.0039 (18)
C12	0.043 (3)	0.027 (3)	0.037 (3)	0.000	0.025 (3)	0.000
C13	0.032 (3)	0.046 (3)	0.056 (4)	0.000	0.024 (3)	0.000
C14	0.073 (5)	0.044 (3)	0.078 (5)	0.000	0.061 (4)	0.000
C15	0.063 (4)	0.048 (3)	0.040 (3)	0.000	0.036 (3)	0.000
C16	0.050 (3)	0.028 (2)	0.050 (2)	0.0044 (18)	0.033 (2)	0.0029 (19)

Geometric parameters (Å, º) top

Ni1—O1	2.179 (3)	C6—C7	1.352 (6)
Ni1—O1ⁱ	2.179 (3)	C7—H7	0.9300
Ni1—O2ⁱ	2.096 (3)	C8—H8A	0.9600
Ni1—O2	2.096 (3)	C8—H8B	0.9600
Ni1—N2ⁱ	2.050 (3)	C8—H8C	0.9600
Ni1—N2	2.050 (3)	C9—C10	1.528 (5)
O1—C16	1.257 (5)	C9—C11	1.534 (5)
O2—C16	1.260 (5)	C9—C12	1.540 (5)
N1—C4	1.465 (5)	C9—C16	1.526 (5)
N1—C5	1.351 (5)	C10—H10A	0.9700
N1—C7	1.364 (6)	C10—H10B	0.9700
N2—C5	1.328 (5)	C10—C13	1.530 (5)
N2—C6	1.367 (5)	C11—H11A	0.9700
C1—C2	1.345 (7)	C11—H11B	0.9700
C1—C3	1.339 (6)	C11—C15	1.535 (5)
C1—C4	1.513 (6)	C12—H12A	0.9700
C2—C2ⁱⁱ	1.395 (11)	C12—H12B	0.9700
C2—H2	0.9300	C13—H13	0.9800
C3—C3ⁱⁱ	1.403 (9)	C13—C14	1.529 (9)
C3—H3	0.9300	C14—H14A	0.9700
C4—H4A	0.9700	C14—H14B	0.9700
C4—H4B	0.9700	C14—C15	1.518 (9)
C5—C8	1.491 (6)	C15—H15	0.9800
C6—H6	0.9300

O1—Ni1—O1ⁱ	142.26 (15)	H8B—C8—H8C	109.5
O2—Ni1—O1	61.20 (11)	C10—C9—C11	109.2 (3)
O2—Ni1—O1ⁱ	91.22 (12)	C10—C9—C12	108.8 (3)
O2ⁱ—Ni1—O1	91.22 (12)	C11—C9—C12	108.0 (3)
O2ⁱ—Ni1—O1ⁱ	61.20 (11)	C16—C9—C10	113.3 (3)
O2—Ni1—O2ⁱ	89.19 (18)	C16—C9—C11	109.9 (3)
N2—Ni1—O1ⁱ	109.38 (12)	C16—C9—C12	107.6 (3)
N2—Ni1—O1	95.55 (12)	C9—C10—H10A	109.6
N2ⁱ—Ni1—O1	109.38 (12)	C9—C10—H10B	109.6
N2ⁱ—Ni1—O1ⁱ	95.55 (12)	C9—C10—C13	110.1 (4)
N2—Ni1—O2ⁱ	91.42 (13)	H10A—C10—H10B	108.1
N2—Ni1—O2	156.75 (13)	C13—C10—H10A	109.6
N2ⁱ—Ni1—O2ⁱ	156.75 (13)	C13—C10—H10B	109.6
N2ⁱ—Ni1—O2	91.42 (13)	C9—C11—H11A	109.7
N2—Ni1—N2ⁱ	97.01 (19)	C9—C11—H11B	109.7
C5—N1—C4	127.6 (4)	C9—C11—C15	109.8 (4)
C5—N1—C7	108.1 (4)	H11A—C11—H11B	108.2
C7—N1—C4	124.3 (4)	C15—C11—H11A	109.7
C5—N2—Ni1	131.7 (3)	C15—C11—H11B	109.7
C5—N2—C6	105.9 (4)	C9—C12—C9ⁱⁱⁱ	111.4 (4)
C6—N2—Ni1	121.6 (3)	C9ⁱⁱⁱ—C12—H12A	109.3
C2—C1—C4	122.6 (4)	C9—C12—H12A	109.3
C3—C1—C2	117.8 (4)	C9ⁱⁱⁱ—C12—H12B	109.3
C3—C1—C4	119.6 (4)	C9—C12—H12B	109.3
C1—C2—C2ⁱⁱ	121.1 (3)	H12A—C12—H12B	108.0
C1—C2—H2	119.4	C10—C13—C10ⁱⁱⁱ	110.5 (5)
C2ⁱⁱ—C2—H2	119.4	C10—C13—H13	109.4
C1—C3—C3ⁱⁱ	121.1 (3)	C10ⁱⁱⁱ—C13—H13	109.4
C1—C3—H3	119.5	C14—C13—C10	109.1 (3)
C3ⁱⁱ—C3—H3	119.5	C14—C13—C10ⁱⁱⁱ	109.1 (3)
N1—C4—C1	113.1 (4)	C14—C13—H13	109.4
N1—C4—H4A	109.0	C13—C14—H14A	109.8
N1—C4—H4B	109.0	C13—C14—H14B	109.8
C1—C4—H4A	109.0	H14A—C14—H14B	108.3
C1—C4—H4B	109.0	C15—C14—C13	109.3 (5)
H4A—C4—H4B	107.8	C15—C14—H14A	109.8
N1—C5—C8	125.0 (4)	C15—C14—H14B	109.8
N2—C5—N1	110.1 (4)	C11—C15—C11ⁱⁱⁱ	108.7 (5)
N2—C5—C8	124.9 (4)	C11ⁱⁱⁱ—C15—H15	109.2
N2—C6—H6	124.9	C11—C15—H15	109.2
C7—C6—N2	110.2 (4)	C14—C15—C11	110.2 (3)
C7—C6—H6	124.9	C14—C15—C11ⁱⁱⁱ	110.2 (3)
N1—C7—H7	127.1	C14—C15—H15	109.2
C6—C7—N1	105.7 (4)	O1—C16—Ni1	62.3 (2)
C6—C7—H7	127.1	O1—C16—O2	119.8 (4)
C5—C8—H8A	109.5	O1—C16—C9	121.8 (4)
C5—C8—H8B	109.5	O2—C16—Ni1	58.5 (2)
C5—C8—H8C	109.5	O2—C16—C9	118.4 (3)
H8A—C8—H8B	109.5	C9—C16—Ni1	167.7 (3)
H8A—C8—H8C	109.5

Ni1—O1—C16—O2	11.1 (4)	C9—C10—C13—C14	60.6 (5)
Ni1—O1—C16—C9	−166.6 (3)	C9—C11—C15—C11ⁱⁱⁱ	61.8 (6)
Ni1—O2—C16—O1	−11.6 (4)	C9—C11—C15—C14	−59.1 (5)
Ni1—O2—C16—C9	166.2 (3)	C10—C9—C11—C15	58.2 (4)
Ni1—N2—C5—N1	168.9 (3)	C10—C9—C12—C9ⁱⁱⁱ	−58.9 (5)
Ni1—N2—C5—C8	−10.1 (6)	C10—C9—C16—Ni1	−105.9 (14)
Ni1—N2—C6—C7	−170.2 (3)	C10—C9—C16—O1	0.1 (5)
N2—C6—C7—N1	−0.3 (5)	C10—C9—C16—O2	−177.6 (4)
C2—C1—C3—C3ⁱⁱ	1.7 (7)	C10—C13—C14—C15	−60.4 (3)
C2—C1—C4—N1	63.2 (7)	C10ⁱⁱⁱ—C13—C14—C15	60.4 (3)
C3—C1—C2—C2ⁱⁱ	−1.8 (7)	C11—C9—C10—C13	−59.4 (4)
C3—C1—C4—N1	−117.9 (5)	C11—C9—C12—C9ⁱⁱⁱ	59.6 (5)
C4—N1—C5—N2	−179.6 (4)	C11—C9—C16—Ni1	131.7 (13)
C4—N1—C5—C8	−0.6 (7)	C11—C9—C16—O1	−122.4 (4)
C4—N1—C7—C6	179.8 (4)	C11—C9—C16—O2	59.9 (5)
C4—C1—C2—C2ⁱⁱ	177.1 (3)	C12—C9—C10—C13	58.2 (5)
C4—C1—C3—C3ⁱⁱ	−177.2 (3)	C12—C9—C11—C15	−60.0 (5)
C5—N1—C4—C1	−111.5 (5)	C12—C9—C16—Ni1	14.4 (15)
C5—N1—C7—C6	0.0 (5)	C12—C9—C16—O1	120.3 (4)
C5—N2—C6—C7	0.4 (5)	C12—C9—C16—O2	−57.4 (5)
C6—N2—C5—N1	−0.4 (5)	C13—C14—C15—C11	60.0 (3)
C6—N2—C5—C8	−179.4 (4)	C13—C14—C15—C11ⁱⁱⁱ	−60.0 (3)
C7—N1—C4—C1	68.7 (6)	C16—C9—C10—C13	177.8 (4)
C7—N1—C5—N2	0.2 (5)	C16—C9—C11—C15	−177.0 (4)
C7—N1—C5—C8	179.2 (4)	C16—C9—C12—C9ⁱⁱⁱ	178.1 (3)
C9—C10—C13—C10ⁱⁱⁱ	−59.4 (6)

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

Funding information

The authors thank Suzhou Industrial Park Institute of Services Outsourcing for financial support.

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