Di-μ2-chlorido-bis­{chlorido­[2,4,6-tris­(pyridin-2-yl)-1,3,5-triazine-κ3N2,N1,N6]nickel(II)}

Ha, K.

doi:10.1107/S2414314621000936

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 6| Part 1| January 2021| x210093

https://doi.org/10.1107/S2414314621000936

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Di-μ₂-chlorido-bis{chlorido[2,4,6-tris(pyridin-2-yl)-1,3,5-triazine-κ³N²,N¹,N⁶]nickel(II)}

Kwang Ha ^a ^*

^aChonnam National University, School of Chemical Engineering, Research Institute of Catalysis, Gwangju, Republic of Korea
^*Correspondence e-mail: hakwang@chonnam.ac.kr

Edited by W. Imhof, University Koblenz-Landau, Germany (Received 21 January 2021; accepted 26 January 2021; online 29 January 2021)

In the title compound, [Ni₂Cl₄(C₁₈H₁₂N₆)₂], the Ni^II ions are hexa-coordinated in a distorted octahedral coordination environment defined by three N atoms of the tridentate 2,4,6-tri-2-pyridyl-1,3,5-triazine ligand and three Cl⁻ anions in a meridional geometry. The two Ni^II ions are bridged by two Cl anionic ligands, thereby forming a dinuclear complex. A crystallographic centre of inversion is located at the centroid of the Ni₂Cl₂ ring.

Keywords: crystal structure; nickel(II) complex; 2,4,6-tri-2-pyridyl-1,3,5-triazine; dinuclear complex.

CCDC reference: 2058987

Structure description

With reference to the title compound, [Ni₂Cl₄(tptz)₂] (tptz = 2,4,6-tri-2-pyridyl-1,3,5-triazine), the crystal structures of related chlorido Ni^II complexes [NiCl₂(tptz)(CH₃OH)] (Hadadzadeh et al., 2012 ), [NiCl(H-tptz)(H₂O)₂]Cl₂·2H₂O (Zibaseresht & Hartshorn, 2005 ) and [NiCl₂(py)(tptz)] (py = pyridine) (Ha, 2019 ) have been determined previously.

In the complex, the two Ni^II cations are bridged by two chlorido ligands to form a dinuclear complex. A crystallographic centre of inversion is located at the centroid of the Ni₂Cl₂ ring. The asymmetric unit therefore contains one half of the complex (Fig. 1). Each Ni^II atom is hexa-coordinated in a considerably distorted octahedral coordination environment defined by three N atoms of the tridentate tptz ligand, two bridging Cl⁻ ligands and one terminal Cl⁻ anion. The main contributions to the distortion are the tight N—Ni—N chelating angles [N1—Ni1—N4 = 76.96 (6)° and N1—Ni1—N6 = 77.52 (6)°] and the chlorido bridges, which result in a non-linear trans arrangement of the N4—Ni1—N6 and N1—Ni1—Cl axes [N4—Ni1—N6 = 154.46 (6)° and N1—Ni1—Cl1 = 169.87 (5)°]. On the other hand the Cl2—Ni1—Cl1ⁱ axis (symmetry code: (i) −x, −y + 1, −z) is almost linear [Cl2—Ni1—Cl1ⁱ = 176.25 (2)°]. The Ni—N(pyridyl) bonds [Ni1—N4/N6 = 2.130 (2) and 2.129 (2) Å] are slightly longer than the Ni—N(triazine) bond [Ni1—N1 = 1.970 (2) Å]. The three Ni—Cl bond lengths are somewhat different [Ni1—Cl1ⁱ = 2.5812 (5), Ni1—Cl1 = 2.3326 (5) and Ni1—Cl2 = 2.3538 (5) Å]. The two pyridyl rings that coordinat to the Ni^II atom are located approximately parallel to the respective triazine ring, making dihedral angles of 4.51 (6) and 4.95 (6)°, respectively. The dihedral angle between the non-coordinating pyridyl substituent and the triazine ring is 7.56 (6)°.

Figure 1
Molecular structure of the title compound showing the atom labelling and displacement ellipsoids drawn at the 50% probability level for non-H atoms. Symmetry code: (i) −x, −y + 1, −z.

The complex displays numerous intermolecular π–π interactions between adjacent six-membered rings. For Cg1 (the centroid of ring N5/C8–C12) and Cg2ⁱⁱ [the centroid of ring N6/C14–C18; symmetry code: (ii) x, −y + $[{3\over 2}]$ , z − $[{1\over 2}]$ ], the centroid–centroid distance is 4.138 (1) Å and the dihedral angle between the ring planes is 5.44 (10)°. In addition, the complex reveals intermolecular C—H⋯Cl hydrogen bonds with distances of 2.773 (3)–3.605 (2) Å between the donor and acceptor atoms, to stabilize the crystal structure (Table 1, Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cl2ⁱ	0.94	2.76	3.605 (2)	150
C15—H15⋯Cl2ⁱⁱ	0.94	2.57	3.471 (2)	162
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
Crystal structure of the title compound showing π–π interactions as well as weak C–H⋯Cl hydrogen bonds.

Synthesis and crystallization

To a solution of NiCl₂·6 H₂O (0.2670 g, 1.123 mmol) in ethanol (30 ml) was added 2,4,6-tri-2-pyridyl-1,3,5-triazine (0.2814 g, 0.901 mmol). The solution was stirred for 12 h at room temperature. The formed precipitate was separated by filtration, washed with ethanol and acetone, and dried at 323 K, to give a pale-green powder (0.3363 g, 84%). Brown crystals suitable for X-ray analysis were obtained by slow evaporation from a dimethyl sulfoxide (DMSO) solution at 363 K.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The remaining maximum (0.33 e Å⁻³) and minimum (−0.20 e Å⁻³) electron density in the difference Fourier map are located 0.73 and 1.28 Å, respectively, from atoms C2 and C9.

Table 2
Experimental details

Crystal data
Chemical formula	[Ni₂Cl₄(C₁₈H₁₂N₆)₂]
M_r	883.89
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	223
a, b, c (Å)	13.0130 (4), 12.8275 (4), 11.0153 (3)
β (°)	106.5083 (11)
V (Å³)	1762.93 (9)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.42
Crystal size (mm)	0.25 × 0.15 × 0.13

Data collection
Diffractometer	PHOTON 100 CMOS detector
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.660, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	48040, 3487, 2828
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.067, 1.06
No. of reflections	3487
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.20
Computer programs: APEX2 and SAINT (Bruker, 2016), SHELXT2014/7 (Sheldrick, 2015a ), SHELXL2014/7 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Structural data

CCDC reference: 2058987

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314621000936/im4011sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621000936/im4011Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014/7 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015b).

Di-µ₂-chlorido-bis{chlorido[2,4,6-tris(pyridin-2-yl)-1,3,5-triazine-κ³N²,N¹,N⁶]nickel(II)} top

Crystal data top

[Ni₂Cl₄(C₁₈H₁₂N₆)₂]	F(000) = 896
M_r = 883.89	D_x = 1.665 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.0130 (4) Å	Cell parameters from 9969 reflections
b = 12.8275 (4) Å	θ = 2.3–28.2°
c = 11.0153 (3) Å	µ = 1.42 mm⁻¹
β = 106.5083 (11)°	T = 223 K
V = 1762.93 (9) Å³	Block, brown
Z = 2	0.25 × 0.15 × 0.13 mm

Data collection top

PHOTON 100 CMOS detector diffractometer	2828 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.059
φ and ω scans	θ_max = 26.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −16→16
T_min = 0.660, T_max = 0.745	k = −15→15
48040 measured reflections	l = −13→13
3487 independent 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0314P)² + 0.698P] where P = (F_o² + 2F_c²)/3
3487 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

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. Hydrogen atoms on C atoms were positioned geometrically and allowed to ride on their respective parent atoms: C—H = 0.94 Å and U_iso(H) = 1.2 U_eq(C).

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

	x	y	z	U_iso*/U_eq
Ni1	0.14246 (2)	0.51866 (2)	0.04761 (2)	0.02427 (9)
Cl1	0.01562 (4)	0.48538 (4)	−0.14563 (4)	0.02986 (13)
Cl2	0.29409 (4)	0.52462 (4)	−0.02845 (5)	0.03079 (13)
N1	0.22767 (13)	0.54763 (12)	0.22294 (15)	0.0248 (4)
N2	0.32398 (14)	0.48592 (13)	0.42305 (15)	0.0287 (4)
N3	0.29552 (13)	0.66875 (13)	0.38378 (15)	0.0276 (4)
N4	0.18958 (13)	0.36721 (12)	0.12204 (15)	0.0267 (4)
N5	0.42794 (15)	0.52970 (14)	0.66906 (16)	0.0374 (4)
N6	0.13351 (12)	0.68398 (12)	0.05789 (14)	0.0247 (4)
C1	0.26891 (15)	0.47112 (15)	0.30292 (18)	0.0246 (4)
C2	0.24779 (16)	0.36589 (15)	0.24522 (18)	0.0256 (4)
C3	0.28603 (17)	0.27542 (16)	0.3092 (2)	0.0339 (5)
H3	0.3234	0.2769	0.3958	0.041*
C4	0.26843 (19)	0.18244 (17)	0.2435 (2)	0.0409 (6)
H4	0.2930	0.1192	0.2848	0.049*
C5	0.21447 (19)	0.18388 (17)	0.1169 (2)	0.0413 (6)
H5	0.2045	0.1219	0.0696	0.050*
C6	0.17494 (17)	0.27710 (15)	0.0595 (2)	0.0324 (5)
H6	0.1364	0.2769	−0.0268	0.039*
C7	0.33706 (15)	0.58634 (16)	0.45819 (18)	0.0278 (4)
C8	0.39884 (16)	0.61154 (17)	0.59008 (19)	0.0302 (5)
C9	0.42105 (16)	0.71422 (18)	0.6268 (2)	0.0338 (5)
H9	0.3990	0.7689	0.5684	0.041*
C10	0.47666 (17)	0.73425 (19)	0.7519 (2)	0.0394 (6)
H10	0.4937	0.8030	0.7802	0.047*
C11	0.50621 (18)	0.6520 (2)	0.8335 (2)	0.0426 (6)
H11	0.5435	0.6635	0.9190	0.051*
C12	0.48059 (18)	0.5520 (2)	0.7888 (2)	0.0438 (6)
H12	0.5015	0.4964	0.8462	0.053*
C13	0.23995 (15)	0.64467 (15)	0.26684 (18)	0.0237 (4)
C14	0.18376 (15)	0.72372 (15)	0.17355 (18)	0.0238 (4)
C15	0.18125 (16)	0.82788 (15)	0.2024 (2)	0.0301 (5)
H15	0.2164	0.8528	0.2839	0.036*
C16	0.12571 (17)	0.89494 (16)	0.1083 (2)	0.0350 (5)
H16	0.1212	0.9663	0.1255	0.042*
C17	0.07695 (17)	0.85609 (16)	−0.0108 (2)	0.0336 (5)
H17	0.0406	0.9009	−0.0766	0.040*
C18	0.08231 (15)	0.75012 (16)	−0.03215 (19)	0.0287 (5)
H18	0.0485	0.7239	−0.1134	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.03109 (15)	0.01883 (14)	0.02120 (14)	0.00130 (10)	0.00470 (11)	0.00041 (10)
Cl1	0.0330 (3)	0.0344 (3)	0.0216 (2)	−0.0031 (2)	0.0068 (2)	−0.0029 (2)
Cl2	0.0314 (3)	0.0313 (3)	0.0298 (3)	0.0037 (2)	0.0088 (2)	0.0046 (2)
N1	0.0300 (9)	0.0208 (8)	0.0235 (8)	0.0015 (7)	0.0073 (7)	0.0012 (7)
N2	0.0311 (9)	0.0288 (9)	0.0254 (9)	0.0020 (7)	0.0066 (7)	0.0031 (7)
N3	0.0288 (9)	0.0281 (9)	0.0239 (9)	−0.0008 (7)	0.0044 (7)	−0.0001 (7)
N4	0.0331 (9)	0.0217 (9)	0.0280 (9)	−0.0003 (7)	0.0130 (7)	−0.0009 (7)
N5	0.0392 (11)	0.0432 (11)	0.0257 (9)	−0.0010 (9)	0.0028 (8)	0.0043 (8)
N6	0.0283 (9)	0.0215 (9)	0.0246 (9)	0.0013 (7)	0.0079 (7)	0.0015 (7)
C1	0.0256 (10)	0.0243 (10)	0.0249 (10)	0.0028 (8)	0.0088 (8)	0.0034 (8)
C2	0.0301 (11)	0.0237 (10)	0.0260 (10)	0.0024 (8)	0.0129 (8)	0.0027 (8)
C3	0.0400 (12)	0.0304 (12)	0.0350 (12)	0.0078 (9)	0.0165 (10)	0.0107 (10)
C4	0.0541 (15)	0.0222 (11)	0.0527 (15)	0.0098 (10)	0.0253 (12)	0.0115 (10)
C5	0.0569 (15)	0.0214 (11)	0.0533 (15)	−0.0005 (10)	0.0280 (12)	−0.0030 (10)
C6	0.0440 (13)	0.0241 (11)	0.0332 (12)	−0.0018 (9)	0.0177 (10)	−0.0026 (9)
C7	0.0258 (11)	0.0324 (11)	0.0257 (10)	0.0007 (9)	0.0081 (8)	0.0014 (9)
C8	0.0259 (11)	0.0396 (13)	0.0252 (10)	0.0003 (9)	0.0073 (9)	0.0018 (9)
C9	0.0294 (11)	0.0392 (13)	0.0307 (11)	0.0010 (9)	0.0051 (9)	0.0000 (10)
C10	0.0309 (12)	0.0491 (15)	0.0368 (13)	−0.0024 (11)	0.0075 (10)	−0.0112 (11)
C11	0.0362 (13)	0.0603 (16)	0.0269 (12)	−0.0022 (12)	0.0019 (10)	−0.0053 (11)
C12	0.0429 (14)	0.0539 (15)	0.0289 (12)	−0.0010 (12)	0.0012 (10)	0.0068 (11)
C13	0.0239 (10)	0.0241 (10)	0.0242 (10)	0.0001 (8)	0.0083 (8)	0.0012 (8)
C14	0.0252 (10)	0.0213 (10)	0.0262 (10)	−0.0006 (8)	0.0092 (8)	−0.0001 (8)
C15	0.0347 (12)	0.0236 (11)	0.0322 (11)	−0.0021 (9)	0.0095 (9)	−0.0030 (9)
C16	0.0401 (13)	0.0187 (11)	0.0492 (14)	0.0022 (9)	0.0174 (11)	0.0017 (10)
C17	0.0349 (12)	0.0252 (11)	0.0414 (13)	0.0069 (9)	0.0119 (10)	0.0106 (10)
C18	0.0298 (11)	0.0291 (11)	0.0277 (11)	0.0039 (9)	0.0090 (9)	0.0058 (8)

Geometric parameters (Å, º) top

Ni1—N1	1.9700 (16)	C4—C5	1.372 (3)
Ni1—N6	2.1286 (16)	C4—H4	0.9400
Ni1—N4	2.1300 (16)	C5—C6	1.382 (3)
Ni1—Cl1	2.3326 (5)	C5—H5	0.9400
Ni1—Cl2	2.3538 (5)	C6—H6	0.9400
Ni1—Cl1ⁱ	2.5812 (5)	C7—C8	1.482 (3)
Cl1—Ni1ⁱ	2.5811 (5)	C8—C9	1.384 (3)
N1—C1	1.326 (2)	C9—C10	1.387 (3)
N1—C13	1.329 (2)	C9—H9	0.9400
N2—C1	1.327 (3)	C10—C11	1.368 (3)
N2—C7	1.342 (3)	C10—H10	0.9400
N3—C13	1.322 (2)	C11—C12	1.381 (3)
N3—C7	1.353 (3)	C11—H11	0.9400
N4—C6	1.331 (3)	C12—H12	0.9400
N4—C2	1.353 (2)	C13—C14	1.481 (3)
N5—C12	1.333 (3)	C14—C15	1.376 (3)
N5—C8	1.347 (3)	C15—C16	1.382 (3)
N6—C18	1.331 (2)	C15—H15	0.9400
N6—C14	1.355 (2)	C16—C17	1.379 (3)
C1—C2	1.484 (3)	C16—H16	0.9400
C2—C3	1.375 (3)	C17—C18	1.385 (3)
C3—C4	1.380 (3)	C17—H17	0.9400
C3—H3	0.9400	C18—H18	0.9400

N1—Ni1—N6	77.52 (6)	C4—C5—H5	120.2
N1—Ni1—N4	76.96 (6)	C6—C5—H5	120.2
N6—Ni1—N4	154.46 (6)	N4—C6—C5	122.3 (2)
N1—Ni1—Cl1	169.87 (5)	N4—C6—H6	118.8
N6—Ni1—Cl1	101.28 (4)	C5—C6—H6	118.8
N4—Ni1—Cl1	103.65 (5)	N2—C7—N3	125.40 (18)
N1—Ni1—Cl2	92.73 (5)	N2—C7—C8	118.76 (18)
N6—Ni1—Cl2	92.90 (4)	N3—C7—C8	115.81 (18)
N4—Ni1—Cl2	89.31 (5)	N5—C8—C9	123.76 (19)
Cl1—Ni1—Cl2	97.384 (19)	N5—C8—C7	115.95 (18)
N1—Ni1—Cl1ⁱ	83.52 (5)	C9—C8—C7	120.27 (19)
N6—Ni1—Cl1ⁱ	86.30 (4)	C8—C9—C10	118.3 (2)
N4—Ni1—Cl1ⁱ	89.84 (5)	C8—C9—H9	120.9
Cl1—Ni1—Cl1ⁱ	86.370 (18)	C10—C9—H9	120.9
Cl2—Ni1—Cl1ⁱ	176.246 (19)	C11—C10—C9	118.7 (2)
Ni1—Cl1—Ni1ⁱ	93.631 (18)	C11—C10—H10	120.7
C1—N1—C13	117.87 (17)	C9—C10—H10	120.7
C1—N1—Ni1	121.36 (13)	C10—C11—C12	119.2 (2)
C13—N1—Ni1	120.64 (13)	C10—C11—H11	120.4
C1—N2—C7	114.41 (17)	C12—C11—H11	120.4
C13—N3—C7	114.93 (17)	N5—C12—C11	123.8 (2)
C6—N4—C2	117.72 (17)	N5—C12—H12	118.1
C6—N4—Ni1	127.55 (14)	C11—C12—H12	118.1
C2—N4—Ni1	114.53 (12)	N3—C13—N1	123.33 (18)
C12—N5—C8	116.3 (2)	N3—C13—C14	122.80 (17)
C18—N6—C14	117.79 (17)	N1—C13—C14	113.86 (16)
C18—N6—Ni1	128.22 (13)	N6—C14—C15	123.07 (18)
C14—N6—Ni1	113.93 (12)	N6—C14—C13	113.96 (16)
N1—C1—N2	123.94 (18)	C15—C14—C13	122.96 (18)
N1—C1—C2	113.45 (17)	C14—C15—C16	118.22 (19)
N2—C1—C2	122.61 (17)	C14—C15—H15	120.9
N4—C2—C3	122.83 (19)	C16—C15—H15	120.9
N4—C2—C1	113.64 (16)	C17—C16—C15	119.33 (19)
C3—C2—C1	123.51 (18)	C17—C16—H16	120.3
C2—C3—C4	118.6 (2)	C15—C16—H16	120.3
C2—C3—H3	120.7	C16—C17—C18	119.0 (2)
C4—C3—H3	120.7	C16—C17—H17	120.5
C5—C4—C3	118.8 (2)	C18—C17—H17	120.5
C5—C4—H4	120.6	N6—C18—C17	122.54 (19)
C3—C4—H4	120.6	N6—C18—H18	118.7
C4—C5—C6	119.6 (2)	C17—C18—H18	118.7

C13—N1—C1—N2	−1.8 (3)	N2—C7—C8—C9	174.92 (19)
Ni1—N1—C1—N2	−177.77 (14)	N3—C7—C8—C9	−6.9 (3)
C13—N1—C1—C2	178.24 (16)	N5—C8—C9—C10	0.2 (3)
Ni1—N1—C1—C2	2.3 (2)	C7—C8—C9—C10	178.34 (18)
C7—N2—C1—N1	−1.2 (3)	C8—C9—C10—C11	−0.6 (3)
C7—N2—C1—C2	178.72 (17)	C9—C10—C11—C12	0.5 (3)
C6—N4—C2—C3	−4.1 (3)	C8—N5—C12—C11	−0.4 (3)
Ni1—N4—C2—C3	−179.45 (15)	C10—C11—C12—N5	0.0 (4)
C6—N4—C2—C1	174.13 (17)	C7—N3—C13—N1	−1.9 (3)
Ni1—N4—C2—C1	−1.2 (2)	C7—N3—C13—C14	176.77 (17)
N1—C1—C2—N4	−0.6 (2)	C1—N1—C13—N3	3.5 (3)
N2—C1—C2—N4	179.51 (17)	Ni1—N1—C13—N3	179.50 (14)
N1—C1—C2—C3	177.70 (18)	C1—N1—C13—C14	−175.29 (16)
N2—C1—C2—C3	−2.2 (3)	Ni1—N1—C13—C14	0.7 (2)
N4—C2—C3—C4	3.0 (3)	C18—N6—C14—C15	2.1 (3)
C1—C2—C3—C4	−175.10 (19)	Ni1—N6—C14—C15	−175.50 (15)
C2—C3—C4—C5	0.6 (3)	C18—N6—C14—C13	−179.03 (16)
C3—C4—C5—C6	−2.9 (3)	Ni1—N6—C14—C13	3.4 (2)
C2—N4—C6—C5	1.7 (3)	N3—C13—C14—N6	178.41 (17)
Ni1—N4—C6—C5	176.33 (16)	N1—C13—C14—N6	−2.8 (2)
C4—C5—C6—N4	1.8 (3)	N3—C13—C14—C15	−2.7 (3)
C1—N2—C7—N3	3.0 (3)	N1—C13—C14—C15	176.14 (18)
C1—N2—C7—C8	−179.11 (17)	N6—C14—C15—C16	−0.7 (3)
C13—N3—C7—N2	−1.5 (3)	C13—C14—C15—C16	−179.52 (18)
C13—N3—C7—C8	−179.46 (17)	C14—C15—C16—C17	−1.3 (3)
C12—N5—C8—C9	0.3 (3)	C15—C16—C17—C18	1.8 (3)
C12—N5—C8—C7	−177.95 (19)	C14—N6—C18—C17	−1.4 (3)
N2—C7—C8—N5	−6.8 (3)	Ni1—N6—C18—C17	175.71 (15)
N3—C7—C8—N5	171.38 (17)	C16—C17—C18—N6	−0.5 (3)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cl2ⁱⁱ	0.94	2.76	3.605 (2)	150
C15—H15···Cl2ⁱⁱⁱ	0.94	2.57	3.471 (2)	162

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

Acknowledgements

The author thanks the KBSI, Seoul Center, for the X-ray data collection.

Funding information

This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (grant No. 2018R1D1A1B07050550).

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