Crystal structure of [2-({2-[(2-azanidyl­benzyl­idene)amino]­benzyl­idene}amino)-4-chloro­phenol­ato]nickel(II)

Kobayashi, F.; Koga, A.; Ohtani, R.; Hayami, S.; Nakamura, M.

doi:10.1107/S2056989017004613

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Volume 73| Part 4| April 2017| Pages 637-639

https://doi.org/10.1107/S2056989017004613

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Crystal structure of [2-({2-[(2-azanidylbenzylidene)amino]benzylidene}amino)-4-chlorophenolato]nickel(II)

Fumiya Kobayashi,^a Atsushi Koga,^a Ryo Ohtani,^a Shinya Hayami ^a and Masaaki Nakamura ^a ^*

^aDepartment of Chemistry, Graduate School of Science and Technology, Kumamoto University, 2-39-1 Kurokami, Kumamoto 860-8555, Japan
^*Correspondence e-mail: nakamura@sci.kumamoto-u.ac.jp

Edited by H. Ishida, Okayama University, Japan (Received 2 February 2017; accepted 23 March 2017; online 31 March 2017)

The title complex, [Ni(C₂₀H₁₄ClN₃O)], with an asymmetrically chloride-appended Schiff base ligand has been synthesized and structurally characterized at 100 K. In the compound, the central nickel(II) ion has a square-planar coordination geometry with N₃O donors of the π-conjugated tetradentate Schiff base ligand. In the crystal, the complexes are connected into an inversion dimer via an Ni⋯Ni interaction [3.1753 (5) Å] and a pair of π–π interactions [centroid–centroid distance = 3.8416 (16) Å]. The dimers are linked via a C—H⋯Cl hydrogen bond, forming a chain along the c-axis direction. The dimer chains interact with each other through π–π interactions [centroid–centroid distance = 3.8736 (16) Å], forming a layer expanding parallel to the ac plane.

Keywords: crystal structure; nickel(II) complex; 2-aminobenzaldehyde; asymmetric structure; supramolecular structure.

CCDC reference: 1539785

1. Chemical context

Metal complexes with a tetradentate Schiff base ligand as represented by H₂(salen) [N,N′-ethylenebis(salicylideneimine)] and its derivatives have played extremely important roles in the field of coordination chemistry. Up to now, a large number of salen derivatives have been prepared and used for complexation in the expectation of a wide range of features such as catalytic ability, magnetic, dielectric and luminescence properties and so on (Bermejo et al., 1996 ). In these cases, symmetric tetradentate ligands mainly produce N₂O₂ or N₄ type coordination environments. In this research, we have designed asymmetric structures, both in the coordination environment and in the molecular configuration, for the construction of the supramolecular structure through intermolecular hydrogen bonds, and synthesized the title nickel(II) complex using an asymmetrically chloride-appended tetradentate Schiff base ligand.

The structure of the title compound, which features a widely spread π-conjugated ring system, is also useful for supramolecular assemblies through π–π interactions. The mononuclear copper(II) complex with a similar N₃O type asymmetrical ligand was reported by Ghorai & Mukherjee (2014 ).

2. Structural commentary

The nickel(II) atom is in a square-planar coordination with an asymmetrical coordination environment formed by the N₃O donor set including one phenolate O atom, two imine N atoms and one amino N atom of the tetradentate Schiff base ligand (Fig. 1). The Ni—O1, Ni—N1, Ni—N2, and Ni—N3 bond lengths are 1.8617 (18), 1.878 (2), 1.896 (2) and 1.831 (2) Å, respectively. The complex molecule is approximately planar; the coordination plane (N1–N3/O1/Ni1) makes dihedral angles of 4.15 (12), 10.22 (12) and 13.42 (12)°, respectively, with the C1–C6, C8–C13 and C15–C20 benzene rings.

Figure 1
The molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level.

3. Supramolecular features

In the crystal, pairs of complex molecules related by an inversion centre are dimerized by an Ni⋯Ni interaction [3.1753 (5) Å] and a pair of π–π interactions between the C1–C6 and C15–C20 benzene rings [centroid–centroid distance = 3.8415 (16) Å]. Such dimerization caused by an Ni⋯Ni interaction has also been observed in symmetric Ni(salen) compounds (Aullón et al., 1996 ; Siegler & Lutz, 2009 ). The dimeric molecules of the title compound are linked by C—H⋯Cl hydrogen bonds (Table 1), producing a chain of dimers along the c axis (Fig. 2). The dimers further interact with each other through π–π interactions between the C1–C6 and C8–C13 benzene rings [centroid–centroid distance = 3.8738 (17) Å], forming a column along the a axis (Fig. 3). Together, these C—H⋯Cl and π–π interactions result in a layer parallel to the ac plane. The layers are further linked by a short C—H⋯C contact (Table 1), giving a three-dimensional network (Fig. 4).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cl1ⁱ	0.95	2.76	3.540 (3)	140
C10—H10⋯C20ⁱⁱ	0.95	2.80	3.626 (4)	146
Symmetry codes: (i) x, y, z-1; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
Packing diagrams of the title compound, showing (a) a chain structure running along the c axis formed by C—H⋯Cl hydrogen bonds (red dashed lines) and (b) the chains viewed along the a axis.

Figure 3
A packing diagram of the title compound, showing the column structure along the a axis formed by Ni⋯Ni interactions (green solid lines) and π–π interactions (red dashed lines).

Figure 4
Packing diagrams of the title compound assembled by (a) C—H⋯Cl hydrogen bonds and C—H⋯C short contacts, and (b) π–π interactions and short contacts.

4. Synthesis and crystallization

The tetradentate Schiff base ligand was prepared by the reaction of 2-aminobenzaldehyde (Smith & Opie, 1948 ) (0.228 g, 2.0 mmol) and 2-amino-4-chlorophenol (0.144 g, 1.0 mmol) in methanol (50 ml) under stirring for 1 h. The resulting solution including the ligand was used for complexation with the Ni^II ion. A methanol solution (50 ml) of Ni(CH₃COO)₂·4H₂O (0.249 g, 1.0 mmol) was added to the solution and stirred for 1 h. The resulting solution was allowed to stand for a few days, during which time dark-purple block-shaped crystals precipitated. They were collected by suction filtration and dried in air to give single crystals of the title compound suitable for X-ray diffraction.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The position of the N-bound H atom was refined with N—H = 0.86 (1) Å and U_iso(H) = 1.5U_eq(N). Other H atoms were treated as riding with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	[Ni(C₂₀H₁₄ClN₃O)]
M_r	406.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.5510 (4), 17.8689 (9), 12.6834 (6)
β (°)	109.9504 (14)
V (Å³)	1608.64 (14)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.39
Crystal size (mm)	0.46 × 0.27 × 0.25

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995 )
T_min, T_max	0.476, 0.712
No. of measured, independent and observed [F² > 2.0σ(F²)] reflections	15243, 3638, 3177
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.103, 1.04
No. of reflections	3638
No. of parameters	238
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.35, −0.37
Computer programs: RAPID-AUTO (Rigaku, 1995 ), SHELXS2013 (Sheldrick, 2008 ), SHELXL2016 (Sheldrick, 2015 ) and CrystalStructure (Rigaku, 2014 ).

Supporting information

CCDC reference: 1539785

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989017004613/is5472sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017004613/is5472Isup2.hkl

checkCIF report

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1995); cell refinement: RAPID-AUTO (Rigaku, 1995); data reduction: RAPID-AUTO (Rigaku, 1995); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: CrystalStructure (Rigaku, 2014); software used to prepare material for publication: CrystalStructure (Rigaku, 2014).

[2-({2-[(2-Azanidylbenzylidene)amino]benzylidene}amino)-4-chlorophenolato]nickel(II) top

Crystal data top

[Ni(C₂₀H₁₄ClN₃O)]	F(000) = 832.00
M_r = 406.50	D_x = 1.678 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71075 Å
a = 7.5510 (4) Å	Cell parameters from 13442 reflections
b = 17.8689 (9) Å	θ = 3.0–27.4°
c = 12.6834 (6) Å	µ = 1.39 mm⁻¹
β = 109.9504 (14)°	T = 100 K
V = 1608.64 (14) Å³	Block, purple
Z = 4	0.46 × 0.27 × 0.25 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3177 reflections with F² > 2.0σ(F²)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.039
ω scans	θ_max = 27.4°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→8
T_min = 0.476, T_max = 0.712	k = −23→23
15243 measured reflections	l = −16→16
3638 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0527P)² + 1.948P] where P = (F_o² + 2F_c²)/3
3638 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 1.35 e Å⁻³
1 restraint	Δρ_min = −0.37 e Å⁻³
Primary atom site location: structure-invariant direct methods

Special details top

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

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
Ni1	0.29838 (4)	0.53846 (2)	0.46051 (3)	0.01597 (11)
Cl1	0.22371 (10)	0.39200 (4)	0.93185 (6)	0.03146 (17)
O1	0.3645 (3)	0.58686 (10)	0.59854 (15)	0.0230 (4)
N1	0.2079 (3)	0.46083 (11)	0.52811 (18)	0.0195 (4)
N2	0.2225 (3)	0.49436 (12)	0.31594 (18)	0.0193 (4)
N3	0.3976 (3)	0.62220 (12)	0.41867 (19)	0.0221 (4)
C1	0.3301 (4)	0.54570 (14)	0.6762 (2)	0.0205 (5)
C2	0.3738 (4)	0.56917 (15)	0.7885 (2)	0.0229 (5)
C3	0.3380 (4)	0.52243 (15)	0.8656 (2)	0.0237 (5)
C4	0.2594 (4)	0.45198 (15)	0.8321 (2)	0.0236 (5)
C5	0.2109 (4)	0.42792 (15)	0.7223 (2)	0.0224 (5)
C6	0.2447 (4)	0.47561 (15)	0.6445 (2)	0.0207 (5)
C7	0.1169 (4)	0.40146 (14)	0.4813 (2)	0.0210 (5)
C8	0.0936 (3)	0.37840 (14)	0.3689 (2)	0.0197 (5)
C9	0.0092 (4)	0.30739 (15)	0.3366 (2)	0.0235 (5)
C10	−0.0089 (4)	0.27609 (15)	0.2338 (2)	0.0259 (6)
C11	0.0649 (4)	0.31435 (15)	0.1634 (2)	0.0251 (5)
C12	0.1469 (4)	0.38395 (15)	0.1918 (2)	0.0230 (5)
C13	0.1542 (3)	0.41975 (13)	0.2923 (2)	0.0187 (5)
C14	0.2147 (4)	0.53457 (14)	0.2259 (2)	0.0199 (5)
C15	0.2954 (4)	0.60452 (14)	0.2207 (2)	0.0214 (5)
C16	0.2781 (4)	0.63380 (15)	0.1133 (2)	0.0247 (5)
C17	0.3660 (4)	0.69883 (15)	0.1023 (2)	0.0262 (5)
C18	0.4758 (4)	0.73809 (15)	0.2007 (2)	0.0267 (6)
C19	0.4922 (4)	0.71300 (14)	0.3054 (2)	0.0253 (6)
C20	0.3979 (3)	0.64586 (14)	0.3194 (2)	0.0210 (5)
H1	0.452 (4)	0.6459 (17)	0.478 (2)	0.0315*
H2	0.42785	0.61711	0.81103	0.0275*
H3	0.36681	0.5382	0.94116	0.0285*
H5	0.15584	0.38005	0.70055	0.0268*
H7	0.06228	0.37131	0.52382	0.0253*
H9	−0.03614	0.28057	0.38682	0.0282*
H10	−0.07053	0.22937	0.21193	0.0310*
H11	0.05913	0.2923	0.09418	0.0301*
H12	0.19936	0.40819	0.14264	0.0276*
H14	0.14485	0.51283	0.15561	0.0239*
H16	0.2041	0.60767	0.04782	0.0296*
H17	0.35399	0.71755	0.03007	0.0314*
H18	0.53905	0.7827	0.19338	0.0321*
H19	0.56662	0.74021	0.36959	0.0304*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01684 (17)	0.01610 (17)	0.01561 (17)	0.00035 (11)	0.00636 (13)	0.00011 (12)
Cl1	0.0320 (4)	0.0439 (4)	0.0214 (3)	−0.0047 (3)	0.0130 (3)	0.0036 (3)
O1	0.0285 (10)	0.0222 (9)	0.0181 (9)	0.0016 (8)	0.0076 (8)	−0.0014 (7)
N1	0.0167 (10)	0.0209 (11)	0.0216 (11)	0.0035 (8)	0.0072 (9)	0.0015 (8)
N2	0.0177 (10)	0.0202 (10)	0.0215 (10)	0.0012 (8)	0.0088 (9)	0.0001 (8)
N3	0.0210 (11)	0.0203 (11)	0.0238 (11)	0.0001 (9)	0.0062 (9)	−0.0002 (9)
C1	0.0183 (12)	0.0243 (13)	0.0183 (12)	0.0059 (10)	0.0054 (10)	0.0001 (10)
C2	0.0230 (12)	0.0228 (12)	0.0200 (12)	0.0049 (10)	0.0036 (10)	−0.0025 (10)
C3	0.0204 (12)	0.0315 (14)	0.0190 (12)	0.0063 (11)	0.0064 (10)	−0.0022 (11)
C4	0.0198 (12)	0.0304 (14)	0.0222 (13)	0.0036 (10)	0.0092 (10)	0.0040 (11)
C5	0.0180 (12)	0.0254 (13)	0.0241 (13)	0.0006 (10)	0.0078 (10)	−0.0024 (11)
C6	0.0171 (11)	0.0261 (13)	0.0196 (12)	0.0047 (10)	0.0070 (10)	−0.0001 (10)
C7	0.0188 (12)	0.0246 (13)	0.0211 (12)	0.0017 (10)	0.0085 (10)	0.0024 (10)
C8	0.0160 (11)	0.0228 (12)	0.0197 (12)	0.0032 (9)	0.0055 (10)	0.0023 (10)
C9	0.0195 (12)	0.0238 (13)	0.0276 (13)	−0.0001 (10)	0.0085 (11)	0.0055 (11)
C10	0.0218 (13)	0.0217 (12)	0.0310 (14)	−0.0024 (10)	0.0049 (11)	−0.0047 (11)
C11	0.0241 (13)	0.0267 (13)	0.0221 (13)	0.0019 (11)	0.0048 (11)	−0.0039 (11)
C12	0.0252 (13)	0.0232 (13)	0.0206 (12)	0.0038 (10)	0.0077 (11)	0.0003 (10)
C13	0.0167 (11)	0.0183 (12)	0.0209 (12)	0.0025 (9)	0.0062 (10)	0.0012 (10)
C14	0.0189 (12)	0.0216 (12)	0.0203 (12)	0.0019 (10)	0.0080 (10)	−0.0009 (10)
C15	0.0207 (12)	0.0182 (12)	0.0279 (13)	0.0029 (10)	0.0115 (11)	0.0015 (10)
C16	0.0242 (13)	0.0246 (13)	0.0274 (14)	0.0022 (11)	0.0116 (11)	−0.0010 (11)
C17	0.0302 (14)	0.0236 (13)	0.0291 (14)	0.0032 (11)	0.0158 (12)	0.0052 (11)
C18	0.0273 (13)	0.0204 (12)	0.0364 (15)	0.0002 (11)	0.0160 (12)	0.0038 (11)
C19	0.0216 (12)	0.0211 (13)	0.0330 (15)	−0.0002 (10)	0.0087 (11)	0.0007 (11)
C20	0.0165 (11)	0.0193 (12)	0.0285 (13)	0.0055 (9)	0.0094 (10)	0.0044 (10)

Geometric parameters (Å, º) top

Ni1—N3	1.831 (2)	C8—C13	1.416 (3)
Ni1—O1	1.8617 (18)	C8—C9	1.416 (4)
Ni1—N1	1.878 (2)	C9—C10	1.382 (4)
Ni1—N2	1.896 (2)	C9—H9	0.9500
Cl1—C4	1.748 (3)	C10—C11	1.383 (4)
O1—C1	1.324 (3)	C10—H10	0.9500
N1—C7	1.293 (3)	C11—C12	1.381 (4)
N1—C6	1.430 (3)	C11—H11	0.9500
N2—C14	1.333 (3)	C12—C13	1.410 (3)
N2—C13	1.424 (3)	C12—H12	0.9500
N3—C20	1.329 (3)	C14—C15	1.402 (3)
N3—H1	0.836 (18)	C14—H14	0.9500
C1—C6	1.403 (4)	C15—C16	1.424 (4)
C1—C2	1.412 (3)	C15—C20	1.432 (4)
C2—C3	1.381 (4)	C16—C17	1.369 (4)
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.395 (4)	C17—C18	1.425 (4)
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.382 (4)	C18—C19	1.367 (4)
C5—C6	1.392 (4)	C18—H18	0.9500
C5—H5	0.9500	C19—C20	1.436 (4)
C7—C8	1.436 (3)	C19—H19	0.9500
C7—H7	0.9500

N3—Ni1—O1	83.57 (9)	C13—C8—C7	125.0 (2)
N3—Ni1—N1	169.92 (10)	C9—C8—C7	115.8 (2)
O1—Ni1—N1	86.35 (9)	C10—C9—C8	121.7 (2)
N3—Ni1—N2	94.46 (10)	C10—C9—H9	119.1
O1—Ni1—N2	176.53 (9)	C8—C9—H9	119.1
N1—Ni1—N2	95.61 (9)	C9—C10—C11	118.5 (2)
C1—O1—Ni1	112.57 (16)	C9—C10—H10	120.8
C7—N1—C6	120.7 (2)	C11—C10—H10	120.8
C7—N1—Ni1	128.02 (18)	C12—C11—C10	121.4 (3)
C6—N1—Ni1	111.23 (16)	C12—C11—H11	119.3
C14—N2—C13	114.6 (2)	C10—C11—H11	119.3
C14—N2—Ni1	121.00 (18)	C11—C12—C13	121.3 (2)
C13—N2—Ni1	124.14 (16)	C11—C12—H12	119.3
C20—N3—Ni1	131.89 (19)	C13—C12—H12	119.3
C20—N3—H1	122 (2)	C12—C13—C8	117.5 (2)
Ni1—N3—H1	106 (2)	C12—C13—N2	121.0 (2)
O1—C1—C6	118.0 (2)	C8—C13—N2	121.5 (2)
O1—C1—C2	123.2 (2)	N2—C14—C15	128.9 (2)
C6—C1—C2	118.7 (2)	N2—C14—H14	115.6
C3—C2—C1	120.0 (3)	C15—C14—H14	115.6
C3—C2—H2	120.0	C14—C15—C16	118.3 (2)
C1—C2—H2	120.0	C14—C15—C20	122.2 (2)
C2—C3—C4	119.7 (2)	C16—C15—C20	119.5 (2)
C2—C3—H3	120.1	C17—C16—C15	121.3 (3)
C4—C3—H3	120.1	C17—C16—H16	119.3
C5—C4—C3	121.8 (2)	C15—C16—H16	119.3
C5—C4—Cl1	119.0 (2)	C16—C17—C18	119.1 (3)
C3—C4—Cl1	119.2 (2)	C16—C17—H17	120.5
C4—C5—C6	118.3 (2)	C18—C17—H17	120.5
C4—C5—H5	120.8	C19—C18—C17	121.5 (2)
C6—C5—H5	120.8	C19—C18—H18	119.3
C5—C6—C1	121.4 (2)	C17—C18—H18	119.3
C5—C6—N1	126.9 (2)	C18—C19—C20	120.6 (3)
C1—C6—N1	111.7 (2)	C18—C19—H19	119.7
N1—C7—C8	123.8 (2)	C20—C19—H19	119.7
N1—C7—H7	118.1	N3—C20—C15	119.2 (2)
C8—C7—H7	118.1	N3—C20—C19	122.9 (2)
C13—C8—C9	119.2 (2)	C15—C20—C19	117.8 (2)

N3—Ni1—O1—C1	−176.59 (18)	Ni1—N1—C7—C8	10.2 (4)
N1—Ni1—O1—C1	3.42 (17)	N1—C7—C8—C13	−4.8 (4)
N3—Ni1—N1—C7	173.9 (5)	N1—C7—C8—C9	172.8 (2)
O1—Ni1—N1—C7	174.0 (2)	C13—C8—C9—C10	2.6 (4)
N2—Ni1—N1—C7	−3.1 (2)	C7—C8—C9—C10	−175.2 (2)
N3—Ni1—N1—C6	−3.6 (6)	C8—C9—C10—C11	2.7 (4)
O1—Ni1—N1—C6	−3.50 (16)	C9—C10—C11—C12	−3.2 (4)
N2—Ni1—N1—C6	179.37 (16)	C10—C11—C12—C13	−1.7 (4)
N3—Ni1—N2—C14	−15.0 (2)	C11—C12—C13—C8	6.9 (4)
N1—Ni1—N2—C14	164.51 (19)	C11—C12—C13—N2	−173.9 (2)
N3—Ni1—N2—C13	170.91 (19)	C9—C8—C13—C12	−7.2 (3)
N1—Ni1—N2—C13	−9.6 (2)	C7—C8—C13—C12	170.3 (2)
O1—Ni1—N3—C20	−171.4 (2)	C9—C8—C13—N2	173.6 (2)
N1—Ni1—N3—C20	−171.3 (4)	C7—C8—C13—N2	−8.9 (4)
N2—Ni1—N3—C20	5.7 (2)	C14—N2—C13—C12	22.3 (3)
Ni1—O1—C1—C6	−2.6 (3)	Ni1—N2—C13—C12	−163.25 (19)
Ni1—O1—C1—C2	177.86 (19)	C14—N2—C13—C8	−158.5 (2)
O1—C1—C2—C3	−178.4 (2)	Ni1—N2—C13—C8	15.9 (3)
C6—C1—C2—C3	2.1 (4)	C13—N2—C14—C15	−169.2 (2)
C1—C2—C3—C4	0.3 (4)	Ni1—N2—C14—C15	16.1 (4)
C2—C3—C4—C5	−1.8 (4)	N2—C14—C15—C16	175.5 (2)
C2—C3—C4—Cl1	177.5 (2)	N2—C14—C15—C20	−2.7 (4)
C3—C4—C5—C6	0.9 (4)	C14—C15—C16—C17	−174.8 (2)
Cl1—C4—C5—C6	−178.37 (19)	C20—C15—C16—C17	3.5 (4)
C4—C5—C6—C1	1.5 (4)	C15—C16—C17—C18	−0.4 (4)
C4—C5—C6—N1	178.9 (2)	C16—C17—C18—C19	−1.3 (4)
O1—C1—C6—C5	177.4 (2)	C17—C18—C19—C20	−0.2 (4)
C2—C1—C6—C5	−3.0 (4)	Ni1—N3—C20—C15	4.8 (4)
O1—C1—C6—N1	−0.2 (3)	Ni1—N3—C20—C19	−177.35 (19)
C2—C1—C6—N1	179.3 (2)	C14—C15—C20—N3	−8.6 (4)
C7—N1—C6—C5	7.7 (4)	C16—C15—C20—N3	173.2 (2)
Ni1—N1—C6—C5	−174.6 (2)	C14—C15—C20—C19	173.4 (2)
C7—N1—C6—C1	−174.8 (2)	C16—C15—C20—C19	−4.8 (3)
Ni1—N1—C6—C1	2.9 (3)	C18—C19—C20—N3	−174.7 (2)
C6—N1—C7—C8	−172.5 (2)	C18—C19—C20—C15	3.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cl1ⁱ	0.95	2.76	3.540 (3)	140
C10—H10···C20ⁱⁱ	0.95	2.80	3.626 (4)	146

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

Funding information

Funding for this research was provided by: JSPS Grant-in-Aid for Young Scientists (B) (award No. JP15K17833); JSPS Grant-in-Aid for Scientific Research on Innovative Areas (Dynamical Ordering and Integrated Functions) (award No. JP16H00777); KAKENHI Grant-in-Aid for Scientific Research (B) (award No. JP26288026); Cooperative Research Program of the Network Joint Research Centre for Materials and Devices.

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