{N′-[(E)-1-(5-Chloro-2-oxidophen­yl)ethyl­idene]-4-meth­oxy­benzohydrazidato-κ3O,N′,O′}(1H-imidazole-κN3)nickel(II)

Chang, J.-G.

doi:10.1107/S2414314622002954

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 7| Part 3| March 2022| x220295

https://doi.org/10.1107/S2414314622002954

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{N′-[(E)-1-(5-Chloro-2-oxidophenyl)ethylidene]-4-methoxybenzohydrazidato-κ³O,N′,O′}(1H-imidazole-κN³)nickel(II)

Jian-Guo Chang ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: tsucjg@163.com

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 13 March 2022; accepted 16 March 2022; online 22 March 2022)

In the title complex, [Ni(C₁₆H₁₃ClN₂O₃)(C₃H₄N₂)], the Ni^II ion is coordinated by two O atoms and one N atom derived from the dianionic N′-[(1E)-1-(5-chloro-2-hydroxyphenyl)ethylidene]-4-methoxybenzohydrazide ligand and one N atom from the imidazole molecule. The N₂O₂ donor set defines an approximate square-planar geometry. The dihedral angles between the imidazole ring and the fused six-membered and methoxybenzene rings are 17.78 (14) and 13.23 (16)°, respectively; the dihedral angle between the C₆ rings is 6.63 (12)°. The most prominent feature of the molecular packing is the formation of 4₁-helical chains (along the c axis) mediated by imidazole-N—H⋯O(phenoxide) hydrogen bonding; these are linked by methyl-C—H⋯Cl interactions.

Keywords: crystal structure; acylhydrazone; hydrogen bonding; imidazole; nickel complex.

CCDC reference: 2159183

Structure description

Acylhydrazones, as a special kind of Schiff base, have been widely investigated because of their strong coordination ability (Singh et al., 1982 ; Salem, 1998 ; Yu et al., 2010 ) and flexible coordination modes involving the N and O donor atoms (Liu et al., 2005 ; Chang, 2011 ; Zheng et al., 2011 ). As has been widely reported in the literature, acylhydrazone complexes display various biological activities such as anti-microbial (Yang et al., 2020 ), anti-tubercular (Peng, 2011 ), anti-cancer (Morgan et al., 2003 ) and anti-oxidant (Chang et al., 2015 ). As an extension of work into the structural characterization of aroylhydrazone complexes, the title complex, [Ni(C₁₆H₁₃ClN₂O₃)(C₃H₄N₂)], has been synthesized and its crystal structure determined.

The Ni^II ion in the title compound is coordinated by two O atoms and one N atom from the dianionic N′-[(1E)-1-(5-chloro-2-hydroxyphenyl)ethylidene]-4-methoxybenzohydrazide ligand and one N atom from the imidazole molecule. In this complex, the Ni atom is located in a slightly distorted square-planar environment (Fig. 1 and Table 1). The Ni—O bond lengths are systematically shorter than the Ni—N bonds, and the maximum deviation from the ideal square-planar geometry in terms of angles is found for O1—Ni1—N2 = 82.18 (7)°. The two benzene rings, C1–C6 (A) and C10–C15 (B), and the imidazole ring (C) make dihedral angles of 6.63 (12)° (A/B), 17.78 (14)° (A/C) and 13.23 (16)° (B/C).

Table 1
Selected geometric parameters (Å, °)

Ni1—O1	1.8995 (15)	Ni1—N2	1.9344 (17)
Ni1—O2	1.8820 (15)	Ni1—N3	1.9664 (18)

O1—Ni1—N2	82.18 (7)	O2—Ni1—N2	94.33 (7)
O1—Ni1—N3	90.33 (7)	O2—Ni1—N3	93.16 (7)
O2—Ni1—O1	173.63 (7)	N2—Ni1—N3	172.50 (8)

Figure 1
The molecular structure, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

The molecular packing is consolidated by imidazole-N—H⋯O(phenoxide) hydrogen bonding (Table 2) along the c axis, which leads to a 4₁ helical chain. The chains are connected by C—H⋯Cl interactions (Table 2) into a three-dimensional architecture; a view of the unit-cell contents is given in Fig. 2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O2ⁱ	0.92 (4)	1.93 (4)	2.818 (3)	161 (3)
C8—H8A⋯Cl1ⁱⁱ	0.96	2.86	3.700 (3)	147
Symmetry codes: (i) $[-y+{\script{5\over 4}}, x+{\script{1\over 4}}, -z+{\script{5\over 4}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

Figure 2
A view in projection down the c axis of the unit-cell contents.

Synthesis and crystallization

The Schiff base ligand, N′-[(1E)-1-(5-chloro-2-hydroxyphenyl)ethylidene]-4-methoxybenzohydrazide (0.100 mmol, 0.0319 g), 1H-imidazole (0.100 mmol, 0.0068 g), Ni(NO₃)₂·6H₂O (0.100 mmol, 0.0292 g), methanol (10 ml) and distilled water (5 ml) were mixed in a 50 ml flask. The mixture was stirred at room temperature for 1 h, the pH was adjusted with saturated sodium carbonate solution to about 8 followed by filtration. Red rectangular block-shaped crystals were obtained after about one month by evaporating the filtrate in air (yield 31%).

Refinement

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

Table 3
Experimental details

Crystal data
Chemical formula	[Ni(C₁₆H₁₃ClN₂O₃)(C₃H₄N₂)]
M_r	443.52
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	295
a, c (Å)	30.879 (4), 8.0750 (16)
V (Å³)	7700 (3)
Z	16
Radiation type	Mo Kα
μ (mm⁻¹)	1.18
Crystal size (mm)	0.35 × 0.25 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2003 )
T_min, T_max	0.735, 0.860
No. of measured, independent and observed [I > 2σ(I)] reflections	23938, 4924, 3431
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.678

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.106, 1.00
No. of reflections	4924
No. of parameters	259
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.21
Computer programs: APEX2 and SAINT (Bruker, 2003), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2159183

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314622002954/tk4076sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314622002954/tk4076Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

{N'-[(E)-1-(5-Chloro-2-oxidophenyl)ethylidene]-4-methoxybenzohydrazidato-κ³O,N',O'}(1H-imidazole-κN³)nickel(II) top

Crystal data top

[Ni(C₁₆H₁₃ClN₂O₃)(C₃H₄N₂)]	D_x = 1.530 Mg m⁻³
M_r = 443.52	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 5154 reflections
a = 30.879 (4) Å	θ = 2.6–25.1°
c = 8.0750 (16) Å	µ = 1.18 mm⁻¹
V = 7700 (3) Å³	T = 295 K
Z = 16	Block, brown
F(000) = 3648	0.35 × 0.25 × 0.16 mm

Data collection top

Bruker APEXII CCD area detector diffractometer	3431 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
phi and ω scans	θ_max = 28.8°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −28→40
T_min = 0.735, T_max = 0.860	k = −41→39
23938 measured reflections	l = −10→10
4924 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0616P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
4924 reflections	Δρ_max = 0.79 e Å⁻³
259 parameters	Δρ_min = −0.20 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
Ni1	0.67356 (2)	0.70309 (2)	0.69948 (3)	0.03734 (10)
Cl1	0.68036 (2)	0.49257 (2)	1.08616 (9)	0.06233 (19)
O1	0.71130 (5)	0.74129 (5)	0.5847 (2)	0.0506 (4)
O2	0.63727 (4)	0.66083 (5)	0.7940 (2)	0.0468 (4)
O3	0.86943 (7)	0.82096 (6)	0.1939 (3)	0.0818 (6)
N1	0.75900 (5)	0.68423 (6)	0.6093 (2)	0.0444 (4)
N2	0.72374 (5)	0.66565 (5)	0.6917 (2)	0.0407 (4)
N3	0.62734 (6)	0.74687 (6)	0.6931 (2)	0.0469 (4)
N4	0.59505 (7)	0.80650 (7)	0.6168 (3)	0.0573 (5)
H4	0.5865 (10)	0.8318 (11)	0.566 (4)	0.100 (11)*
C1	0.69302 (6)	0.60618 (6)	0.8443 (3)	0.0395 (5)
C2	0.70039 (8)	0.56518 (7)	0.9178 (3)	0.0468 (5)
H2	0.728018	0.553255	0.912614	0.056*
C3	0.66852 (8)	0.54265 (7)	0.9955 (3)	0.0471 (5)
C4	0.62689 (8)	0.55887 (7)	1.0092 (3)	0.0494 (5)
H4A	0.605335	0.543496	1.064097	0.059*
C5	0.61852 (7)	0.59863 (7)	0.9385 (3)	0.0478 (5)
H5	0.590670	0.609875	0.946780	0.057*
C6	0.64995 (7)	0.62290 (7)	0.8548 (3)	0.0406 (5)
C7	0.72926 (7)	0.62824 (7)	0.7636 (3)	0.0418 (5)
C8	0.77365 (8)	0.60794 (9)	0.7632 (4)	0.0637 (7)
H8A	0.772858	0.581362	0.701572	0.095*
H8B	0.782430	0.602062	0.875021	0.095*
H8C	0.793945	0.627451	0.712772	0.095*
C9	0.74864 (7)	0.72329 (7)	0.5599 (3)	0.0430 (5)
C10	0.78074 (7)	0.74904 (7)	0.4658 (3)	0.0436 (5)
C11	0.82214 (7)	0.73375 (8)	0.4304 (3)	0.0512 (6)
H11	0.830661	0.706668	0.468830	0.061*
C12	0.85065 (8)	0.75850 (8)	0.3386 (3)	0.0585 (6)
H12	0.878025	0.747719	0.313970	0.070*
C13	0.83883 (8)	0.79913 (8)	0.2832 (3)	0.0544 (6)
C14	0.79796 (8)	0.81495 (8)	0.3173 (3)	0.0531 (6)
H14	0.789633	0.842107	0.279077	0.064*
C15	0.76968 (7)	0.79008 (7)	0.4085 (3)	0.0487 (5)
H15	0.742350	0.801047	0.432655	0.058*
C16	0.85944 (10)	0.86421 (8)	0.1450 (4)	0.0709 (8)
H16A	0.836204	0.863811	0.066026	0.106*
H16B	0.884538	0.877267	0.095671	0.106*
H16C	0.850860	0.880669	0.240361	0.106*
C17	0.58978 (7)	0.75137 (7)	0.7827 (3)	0.0517 (6)
H17	0.579704	0.732134	0.862486	0.062*
C18	0.56989 (8)	0.78836 (8)	0.7357 (4)	0.0587 (6)
H18	0.543965	0.799272	0.776902	0.070*
C19	0.62897 (8)	0.78101 (7)	0.5950 (3)	0.0527 (6)
H19	0.651171	0.786450	0.519968	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.03354 (15)	0.03200 (15)	0.04649 (18)	0.00236 (10)	−0.00014 (11)	−0.00031 (11)
Cl1	0.0762 (4)	0.0409 (3)	0.0699 (4)	0.0076 (3)	−0.0036 (3)	0.0093 (3)
O1	0.0434 (8)	0.0419 (8)	0.0666 (11)	0.0041 (7)	0.0079 (7)	0.0037 (7)
O2	0.0370 (8)	0.0403 (8)	0.0633 (10)	0.0022 (6)	−0.0021 (7)	0.0089 (7)
O3	0.0736 (13)	0.0594 (11)	0.1126 (18)	−0.0087 (10)	0.0426 (12)	0.0024 (11)
N1	0.0367 (9)	0.0453 (10)	0.0512 (11)	−0.0002 (8)	−0.0009 (8)	−0.0029 (8)
N2	0.0367 (9)	0.0404 (9)	0.0451 (10)	−0.0002 (7)	−0.0013 (7)	−0.0040 (8)
N3	0.0440 (10)	0.0410 (10)	0.0557 (12)	0.0050 (8)	0.0017 (8)	0.0010 (8)
N4	0.0515 (12)	0.0400 (11)	0.0804 (16)	0.0071 (9)	0.0033 (11)	0.0071 (10)
C1	0.0424 (11)	0.0376 (11)	0.0387 (11)	0.0045 (9)	−0.0046 (9)	−0.0029 (9)
C2	0.0489 (12)	0.0433 (12)	0.0484 (13)	0.0082 (10)	−0.0056 (10)	−0.0024 (10)
C3	0.0566 (13)	0.0373 (11)	0.0473 (12)	0.0045 (10)	−0.0057 (10)	−0.0007 (9)
C4	0.0540 (13)	0.0441 (12)	0.0502 (13)	−0.0020 (10)	−0.0010 (11)	0.0026 (10)
C5	0.0412 (12)	0.0456 (12)	0.0565 (15)	0.0023 (9)	−0.0021 (10)	0.0009 (10)
C6	0.0405 (11)	0.0393 (11)	0.0420 (12)	0.0018 (9)	−0.0058 (9)	−0.0013 (9)
C7	0.0400 (11)	0.0418 (11)	0.0435 (12)	0.0069 (9)	−0.0056 (9)	−0.0027 (9)
C8	0.0442 (13)	0.0688 (16)	0.0781 (19)	0.0146 (12)	0.0061 (12)	0.0174 (14)
C9	0.0408 (11)	0.0439 (12)	0.0445 (13)	−0.0017 (9)	−0.0017 (9)	−0.0078 (9)
C10	0.0429 (12)	0.0463 (12)	0.0417 (12)	−0.0041 (9)	−0.0024 (9)	−0.0076 (9)
C11	0.0454 (12)	0.0461 (13)	0.0620 (15)	−0.0011 (10)	0.0004 (11)	−0.0066 (11)
C12	0.0408 (12)	0.0607 (15)	0.0741 (18)	0.0006 (11)	0.0106 (12)	−0.0041 (13)
C13	0.0504 (13)	0.0525 (14)	0.0602 (16)	−0.0101 (10)	0.0098 (11)	−0.0101 (11)
C14	0.0566 (14)	0.0463 (13)	0.0566 (15)	−0.0028 (11)	0.0043 (11)	−0.0021 (11)
C15	0.0422 (12)	0.0495 (13)	0.0545 (14)	0.0021 (10)	0.0060 (10)	−0.0012 (10)
C16	0.0801 (19)	0.0578 (16)	0.0749 (19)	−0.0166 (14)	0.0204 (15)	−0.0005 (14)
C17	0.0507 (13)	0.0438 (12)	0.0604 (15)	0.0005 (10)	0.0077 (11)	0.0029 (11)
C18	0.0496 (14)	0.0459 (13)	0.0805 (18)	0.0100 (11)	0.0115 (13)	−0.0003 (12)
C19	0.0485 (13)	0.0432 (12)	0.0665 (16)	0.0074 (10)	0.0089 (11)	0.0090 (11)

Geometric parameters (Å, º) top

Ni1—O1	1.8995 (15)	C5—H5	0.9300
Ni1—O2	1.8820 (15)	C5—C6	1.400 (3)
Ni1—N2	1.9344 (17)	C7—C8	1.507 (3)
Ni1—N3	1.9664 (18)	C8—H8A	0.9600
Cl1—C3	1.750 (2)	C8—H8B	0.9600
O1—C9	1.296 (2)	C8—H8C	0.9600
O2—C6	1.329 (2)	C9—C10	1.481 (3)
O3—C13	1.367 (3)	C10—C11	1.392 (3)
O3—C16	1.426 (3)	C10—C15	1.392 (3)
N1—N2	1.399 (2)	C11—H11	0.9300
N1—C9	1.310 (3)	C11—C12	1.381 (3)
N2—C7	1.304 (3)	C12—H12	0.9300
N3—C17	1.374 (3)	C12—C13	1.381 (3)
N3—C19	1.320 (3)	C13—C14	1.381 (3)
N4—H4	0.92 (4)	C14—H14	0.9300
N4—C18	1.356 (3)	C14—C15	1.376 (3)
N4—C19	1.322 (3)	C15—H15	0.9300
C1—C2	1.417 (3)	C16—H16A	0.9600
C1—C6	1.429 (3)	C16—H16B	0.9600
C1—C7	1.463 (3)	C16—H16C	0.9600
C2—H2	0.9300	C17—H17	0.9300
C2—C3	1.359 (3)	C17—C18	1.351 (3)
C3—C4	1.384 (3)	C18—H18	0.9300
C4—H4A	0.9300	C19—H19	0.9300
C4—C5	1.378 (3)

O1—Ni1—N2	82.18 (7)	C7—C8—H8B	109.5
O1—Ni1—N3	90.33 (7)	C7—C8—H8C	109.5
O2—Ni1—O1	173.63 (7)	H8A—C8—H8B	109.5
O2—Ni1—N2	94.33 (7)	H8A—C8—H8C	109.5
O2—Ni1—N3	93.16 (7)	H8B—C8—H8C	109.5
N2—Ni1—N3	172.50 (8)	O1—C9—N1	124.4 (2)
C9—O1—Ni1	110.80 (13)	O1—C9—C10	116.41 (19)
C6—O2—Ni1	125.85 (13)	N1—C9—C10	119.18 (19)
C13—O3—C16	117.3 (2)	C11—C10—C9	122.5 (2)
C9—N1—N2	109.43 (17)	C15—C10—C9	119.69 (19)
N1—N2—Ni1	113.18 (12)	C15—C10—C11	117.8 (2)
C7—N2—Ni1	128.30 (15)	C10—C11—H11	119.7
C7—N2—N1	118.25 (17)	C12—C11—C10	120.5 (2)
C17—N3—Ni1	131.96 (16)	C12—C11—H11	119.7
C19—N3—Ni1	122.48 (16)	C11—C12—H12	119.7
C19—N3—C17	105.51 (18)	C13—C12—C11	120.5 (2)
C18—N4—H4	120 (2)	C13—C12—H12	119.7
C19—N4—H4	132 (2)	O3—C13—C12	115.9 (2)
C19—N4—C18	107.6 (2)	O3—C13—C14	124.3 (2)
C2—C1—C6	116.57 (19)	C14—C13—C12	119.9 (2)
C2—C1—C7	118.67 (18)	C13—C14—H14	120.4
C6—C1—C7	124.76 (18)	C15—C14—C13	119.3 (2)
C1—C2—H2	118.8	C15—C14—H14	120.4
C3—C2—C1	122.3 (2)	C10—C15—H15	119.0
C3—C2—H2	118.8	C14—C15—C10	122.0 (2)
C2—C3—Cl1	119.64 (17)	C14—C15—H15	119.0
C2—C3—C4	121.6 (2)	O3—C16—H16A	109.5
C4—C3—Cl1	118.72 (18)	O3—C16—H16B	109.5
C3—C4—H4A	121.2	O3—C16—H16C	109.5
C5—C4—C3	117.6 (2)	H16A—C16—H16B	109.5
C5—C4—H4A	121.2	H16A—C16—H16C	109.5
C4—C5—H5	118.4	H16B—C16—H16C	109.5
C4—C5—C6	123.1 (2)	N3—C17—H17	125.6
C6—C5—H5	118.4	C18—C17—N3	108.8 (2)
O2—C6—C1	124.79 (19)	C18—C17—H17	125.6
O2—C6—C5	116.47 (18)	N4—C18—H18	126.6
C5—C6—C1	118.72 (19)	C17—C18—N4	106.7 (2)
N2—C7—C1	120.71 (18)	C17—C18—H18	126.6
N2—C7—C8	119.1 (2)	N3—C19—N4	111.4 (2)
C1—C7—C8	120.19 (19)	N3—C19—H19	124.3
C7—C8—H8A	109.5	N4—C19—H19	124.3

Ni1—O1—C9—N1	−0.8 (3)	C2—C1—C7—C8	−1.5 (3)
Ni1—O1—C9—C10	177.82 (14)	C2—C3—C4—C5	1.0 (3)
Ni1—O2—C6—C1	−6.1 (3)	C3—C4—C5—C6	0.0 (3)
Ni1—O2—C6—C5	172.09 (15)	C4—C5—C6—O2	−179.5 (2)
Ni1—N2—C7—C1	9.6 (3)	C4—C5—C6—C1	−1.2 (3)
Ni1—N2—C7—C8	−170.21 (18)	C6—C1—C2—C3	−0.4 (3)
Ni1—N3—C17—C18	177.28 (18)	C6—C1—C7—N2	−1.1 (3)
Ni1—N3—C19—N4	−177.80 (17)	C6—C1—C7—C8	178.7 (2)
Cl1—C3—C4—C5	179.21 (18)	C7—C1—C2—C3	179.8 (2)
O1—C9—C10—C11	179.9 (2)	C7—C1—C6—O2	−0.7 (3)
O1—C9—C10—C15	−0.5 (3)	C7—C1—C6—C5	−178.9 (2)
O3—C13—C14—C15	179.9 (2)	C9—N1—N2—Ni1	0.9 (2)
N1—N2—C7—C1	−176.82 (18)	C9—N1—N2—C7	−173.69 (19)
N1—N2—C7—C8	3.4 (3)	C9—C10—C11—C12	178.4 (2)
N1—C9—C10—C11	−1.4 (3)	C9—C10—C15—C14	−178.5 (2)
N1—C9—C10—C15	178.2 (2)	C10—C11—C12—C13	1.2 (4)
N2—Ni1—O1—C9	0.95 (14)	C11—C10—C15—C14	1.1 (3)
N2—Ni1—O2—C6	10.33 (18)	C11—C12—C13—O3	179.8 (2)
N2—N1—C9—O1	0.0 (3)	C11—C12—C13—C14	−1.0 (4)
N2—N1—C9—C10	−178.63 (17)	C12—C13—C14—C15	0.9 (4)
N3—Ni1—O1—C9	−179.41 (15)	C13—C14—C15—C10	−1.0 (4)
N3—Ni1—O2—C6	−170.01 (17)	C15—C10—C11—C12	−1.2 (3)
N3—C17—C18—N4	0.3 (3)	C16—O3—C13—C12	−175.6 (3)
C1—C2—C3—Cl1	−178.99 (17)	C16—O3—C13—C14	5.3 (4)
C1—C2—C3—C4	−0.8 (4)	C17—N3—C19—N4	−0.1 (3)
C2—C1—C6—O2	179.5 (2)	C18—N4—C19—N3	0.3 (3)
C2—C1—C6—C5	1.3 (3)	C19—N3—C17—C18	−0.2 (3)
C2—C1—C7—N2	178.7 (2)	C19—N4—C18—C17	−0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O2ⁱ	0.92 (4)	1.93 (4)	2.818 (3)	161 (3)
C8—H8A···Cl1ⁱⁱ	0.96	2.86	3.700 (3)	147

Symmetry codes: (i) −y+5/4, x+1/4, −z+5/4; (ii) −x+3/2, −y+1, z−1/2.

Funding information

The author would like to thank Taishan University for support of this work.

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