Crystal structure of bis­[4-(all­yloxy)-N′-(but-2-en-1-yl­idene)benzohydrazidato]nickel(II)

Khan, S.S.; Howlader, M.B.H.; Sheikh, M.C.; Miyatake, R.; Zangrando, E.

doi:10.1107/S2056989023002918

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ISSN: 2056-9890

Volume 79| Part 5| May 2023| Pages 465-468

https://doi.org/10.1107/S2056989023002918

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Crystal structure of bis[4-(allyloxy)-N′-(but-2-en-1-ylidene)benzohydrazidato]nickel(II)

Sultana Shakila Khan,^a Md. Belayet Hossain Howlader,^a ^* Md. Chanmiya Sheikh,^b Ryuta Miyatake ^c and Ennio Zangrando ^d

^aDepartment of Chemistry, Rajshahi University, Rajshahi-6205, Bangladesh, ^bDepartment of Applied Science, Faculty of Science, Okayama University of Science, Japan, ^cCenter for Environmental Conservation and Research Safety, University of Toyama, 3190 Gofuku, Toyama, 930-8555, Japan, and ^dDepartment of Chemical and Pharmaceutical Sciences, University of Trieste, Italy
^*Correspondence e-mail: mbhhowlader@yahoo.com

Edited by S. Parkin, University of Kentucky, USA (Received 24 February 2023; accepted 27 March 2023; online 14 April 2023)

In the title complex, [Ni(C₁₄H₁₅N₂O₂)₂], the nickel(II) atom exhibits a square-planar coordination geometry, being coordinated by two negatively charged N,O chelating ligands in a trans configuration, with the metal located on a crystallographic center of symmetry. The X-ray structural characterization showed the complex to be disordered over two orientations with refined occupancies of 0.898 (2) and 0.102 (2). The whole molecule is close to planar, the five- and six-membered rings subtending a dihedral angle of 7.5 (2)°. The crystal packing is supported by C—H⋯π and C—H⋯O interactions that form a di-periodic layered network.

Keywords: crystal structure; nickel complex; allyloxy; benzohydrazide.

CCDC reference: 2232075

1. Chemical context

Hydrazones are a specific class of Schiff-base compounds that are distinguished by the presence of a –CO—NH—N= pharmacophore group, and exhibit a wide range of biological activity (Khan et al., 2003 ; Joshi et al., 2008 ; Terzioglu & Gürsoy, 2003 ). Hydrazone molecules display a number of features, such as their degree of flexibility, a conjugated π-system and an NH unit that readily participates in hydrogen bonding and may be easily deprotonated. In addition, hydrazone molecules behave as bidentate ligands through their carbonyl oxygen and azomethine nitrogen atoms, and are widely used in coordination chemistry for their ability to form complexes with metal ions in variable oxidation states (Abou-Melha, 2021 ; Abser et al., 2013 ; Saygıdeğer Demir et al., 2021 ; Gond et al., 2022 ; Velásquez et al., 2020 ). In this respect, the formation of metal complexes plays an important role in enhancing the biological activity of hydrazones (Sathyadevi et al., 2012 ). In addition, providing the molecule with additional donor sites in this type of ligand can modulate the nuclearity of complexes (Vrdoljak et al., 2023 ). As part of our studies in this area, this paper describes the crystal structure of a bis[benzohydrazidato]nickel(II) complex.

2. Structural commentary

The nickel(II) cation of the title complex, [Ni(C₁₄H₁₅N₂O₂)₂], is located on a crystallographic inversion centre and exhibits a square-planar coordination geometry, with a trans configuration of the N,O-chelating ligands, as imposed by the crystal symmetry. An ellipsoid plot of the complex is shown Fig. 1. The structural characterization revealed that the complex is disordered over two orientations (Fig. 2) with refined occupancies of 0.898 (2) and 0.102 (2). As a result of the low percentage of the second component, the discussion is limited to the species at higher occupancy (Fig. 1). The Ni—O and Ni—N bond lengths are 1.8432 (16) and 1.8596 (18) Å, respectively, and the O1—Ni—N1 chelating angle is 84.13 (7)°. The C2—C3 and C13—C14 bond lengths are 1.319 (4) and 1.258 (5) Å, respectively, which confirm their double bond character (Allen et al., 1987 ). Intramolecular C4—H4⋯O1 and C11a—H11a⋯O1a interactions (Table 1), where the C⋯O distances are 2.975 (3) and 2.801 (3) Å, respectively, reinforce the crystal structure.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C6–C11 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1ⁱ	0.95	2.46	2.975 (3)	114
C8—H8⋯O2ⁱⁱ	0.95	2.55	3.466 (5)	161
C11a—H11a⋯O1a	0.95	2.48	2.801 (3)	100
C12—H12b⋯Cg1ⁱⁱⁱ	0.95	2.88	3.781 (4)	152
Symmetry codes: (i) ; (ii) ; (iii) .

Figure 1
An ellipsoid plot (probability at 50%) of the Ni^II complex with atom labels for the crystallographically independent part.

Figure 2
The two disordered species in the crystal with occupancies of ca 0.90/0.10.

The X-ray diffraction analysis revealed that non-hydrogen atoms of the ligand are nearly coplanar; the maximum deviations being 0.308 (3) and 0.313 (5) Å for the allyl carbon atoms C13 and C14, respectively, on either side of the molecular mean plane. The five- and six-membered rings form a dihedral angle of 7.5 (2)°. This conformation, which is rather common for this type of molecule (Al-Qadsy et al., 2021 ; Al Banna et al., 2022 ; Krishnamoorthy et al., 2012 ), allows for electron delocalization throughout the molecule.

3. Supramolecular features

Despite the presence of phenyl rings in the ligands, there is no evidence of π–π stacking. The crystal packing is, however, supported by unconventional hydrogen bonds of type C—H⋯O, e.g. C8—H8⋯O2(−x + 1, −y + 1, −z + 1) that connect complexes to form ribbons in the [111] direction (Fig. 3, Table 1). In addition, C—H⋯π interactions are realized by centrosymmetrically related complexes (H⋯phenyl centroid distance = 2.88 Å, Table 1) and give rise to a polymeric chain in the crystallographic [011] direction (Fig. 4). These interactions form a di-periodic architecture, as depicted in Fig. 5.

Figure 3
Mono-periodic chain formed by unconventional C—H⋯O hydrogen bonds (dotted lines) parallel to the [111] direction.

Figure 4
Detail of the crystal packing showing C—H⋯π interactions, forming a mono-periodic chain in the [011] direction.

Figure 5
The di-periodic network built by C—H⋯O (blue dotted lines) and C—H⋯π (orange dotted lines) interactions. Only H atoms involved in the interactions are shown.

4. Synthesis and crystallization

To a solution of 4-(allyloxy)benzohydrazide (0.514 g, 2.6 mmol in 20 mL of ethanol), crotonaldehyde (0.187 g, 2.6 mmol) was added and the mixture was refluxed for an hour. Then a solution of nickel(II) acetate tetrahydrate (0.335 g, 1.3 mmol in 10 mL of ethanol) was added and refluxing was continued for an additional two hours. The resulting orange precipitate was filtered off and washed with hot ethanol. The product was recrystallized from a mixture of chloroform and toluene (1:1, v/v), and orange crystals, suitable for X-ray diffraction, were formed. Yield: 0.44 g, 60%, melting point: 511–513 K.

FT–IR (KBr), (cm⁻¹): 1636 for ν(C=N—N=C) moiety. Absence of ν(N—H) and ν(C=O) bands. ¹H NMR (CDCl₃, 400 MHz), δ: 7.85 (d, 2×2H, J = 8.8 Hz, C-2, 6), 6.85 (d, 2×2H, J = 9.2 Hz, C-3, 5), 6.92 (d, 2×1H, J = 10 Hz, –CH=N,) , 6.41 (m, 2×1H, –CH=CH—CH₃), 4.56 (dt, 2×1H, J = 5.2 Hz, =CH—CH₃), 1.99 (dd, 2×3H, J = 6.8 Hz, 2.8 Hz, –CH₃), 4.56 (d, 2×2H, J = 6.8 Hz, –OCH₂), 5.42 (dq, 2×H_a, J = 17.2 Hz, 3.2 Hz, =CH₂), 5.30 (dq, 2×H_b, J = 10.8 Hz, 3.2 Hz, =CH₂) , 6.05 (m, 2×H_c, –CH=CH₂). HRMS (FAB) calculated for C₂₈H₃₀N₄O₄Ni, [M + H]⁺: 545.1692, found: 545.1693.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The structure is disordered, having a second component with a low occupancy of about 10%. The whole component at lower occupancy was refined with DELU and RIGU restraints, with bond lengths restrained to those at higher occupancy by use of the instruction SAME (Sheldrick, 2015b ). The hydrogen atoms were included at idealized positions, using a riding model with fixed isotropic displacement parameters [C—H = 0.95–0.99 Å; U_iso(H) = 1.2 or 1.5 U_eq(C)].

Table 2
Experimental details

Crystal data
Chemical formula	[Ni(C₁₄H₁₅N₂O₂)₂]
M_r	545.27
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	173
a, b, c (Å)	8.0978 (8), 9.2021 (9), 9.3316 (10)
α, β, γ (°)	84.027 (6), 88.091 (6), 84.170 (6)
V (Å³)	687.83 (12)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	0.74
Crystal size (mm)	0.29 × 0.19 × 0.11

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995 )
T_min, T_max	0.739, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	6566, 3120, 2678
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.098, 1.03
No. of reflections	3120
No. of parameters	333
No. of restraints	196
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.20
Computer programs: RAPID-AUTO (Rigaku, 2018 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b), DIAMOND (Brandenburg, 1999 ) and WinGX publication routines (Farrugia, 2012 ).

Supporting information

CCDC reference: 2232075

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989023002918/pk2680sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023002918/pk2680Isup2.hkl

checkCIF report

Computing details top

Cell refinement: RAPID-AUTO (Rigaku, 2018); data reduction: RAPID-AUTO (Rigaku, 2018); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/2 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).

Bis[4-(allyloxy)-N'-(but-2-en-1-ylidene)benzohydrazidato]nickel(II) top

Crystal data top

[Ni(C₁₄H₁₅N₂O₂)₂]	Z = 1
M_r = 545.27	F(000) = 286
Triclinic, P1	D_x = 1.316 Mg m⁻³
a = 8.0978 (8) Å	Mo Kα radiation, λ = 0.71075 Å
b = 9.2021 (9) Å	Cell parameters from 8347 reflections
c = 9.3316 (10) Å	θ = 2.0–27.4°
α = 84.027 (6)°	µ = 0.74 mm⁻¹
β = 88.091 (6)°	T = 173 K
γ = 84.170 (6)°	Prism, colorless
V = 687.83 (12) Å³	0.29 × 0.19 × 0.11 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2678 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.027
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
T_min = 0.739, T_max = 0.988	k = −11→10
6566 measured reflections	l = −12→12
3120 independent reflections

Refinement top

Refinement on F²	196 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0653P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3120 reflections	Δρ_max = 0.64 e Å⁻³
333 parameters	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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ni1	0.000000	0.000000	0.000000	0.05459 (14)
O1	0.0243 (2)	0.07363 (16)	0.17356 (18)	0.0578 (4)	0.898 (2)
O2	0.2723 (5)	0.4718 (5)	0.6267 (4)	0.0674 (10)	0.898 (2)
N1	0.2013 (2)	0.07530 (17)	−0.04863 (19)	0.0579 (4)	0.898 (2)
N2	0.2596 (2)	0.15342 (17)	0.05752 (18)	0.0576 (4)	0.898 (2)
C1	0.6805 (6)	0.1843 (6)	−0.3689 (5)	0.0823 (13)	0.898 (2)
H1A	0.716800	0.236081	−0.290787	0.123*	0.898 (2)
H1B	0.663757	0.253188	−0.455829	0.123*	0.898 (2)
H1C	0.765440	0.104813	−0.388854	0.123*	0.898 (2)
C2	0.5204 (4)	0.1213 (3)	−0.3251 (3)	0.0697 (7)	0.898 (2)
H2	0.469034	0.073371	−0.394546	0.084*	0.898 (2)
C3	0.4453 (3)	0.1270 (2)	−0.1979 (2)	0.0630 (5)	0.898 (2)
H3	0.496134	0.171140	−0.125341	0.076*	0.898 (2)
C4	0.2889 (4)	0.0685 (4)	−0.1661 (4)	0.0568 (9)	0.898 (2)
H4	0.245553	0.019621	−0.239171	0.068*	0.898 (2)
C5	0.1563 (3)	0.1451 (2)	0.1675 (2)	0.0552 (5)	0.898 (2)
C6	0.1878 (3)	0.2237 (2)	0.2942 (2)	0.0541 (5)	0.898 (2)
C7	0.3212 (3)	0.3097 (2)	0.2903 (2)	0.0596 (5)	0.898 (2)
H7	0.395956	0.312765	0.209668	0.072*	0.898 (2)
C8	0.3441 (4)	0.3901 (3)	0.4036 (3)	0.0620 (6)	0.898 (2)
H8	0.434157	0.449102	0.399809	0.074*	0.898 (2)
C9	0.2377 (6)	0.3857 (6)	0.5226 (4)	0.0582 (9)	0.898 (2)
C10	0.1064 (4)	0.2975 (3)	0.5305 (3)	0.0568 (6)	0.898 (2)
H10	0.034480	0.291804	0.613008	0.068*	0.898 (2)
C11	0.0832 (3)	0.2176 (2)	0.4142 (3)	0.0570 (6)	0.898 (2)
H11	−0.006304	0.158031	0.417885	0.068*	0.898 (2)
C12	0.1649 (5)	0.4721 (5)	0.7530 (4)	0.0683 (10)	0.898 (2)
H12A	0.175044	0.374580	0.809471	0.082*	0.898 (2)
H12B	0.047605	0.497658	0.725636	0.082*	0.898 (2)
C13	0.2227 (4)	0.5876 (3)	0.8394 (3)	0.0822 (7)	0.898 (2)
H13	0.250302	0.677449	0.789198	0.099*	0.898 (2)
C14	0.2360 (9)	0.5703 (6)	0.9742 (5)	0.159 (3)	0.898 (2)
H14A	0.209241	0.481443	1.026860	0.190*	0.898 (2)
H14B	0.272886	0.646034	1.023245	0.190*	0.898 (2)
O1'	0.1078 (17)	0.0981 (16)	0.1178 (14)	0.061 (3)	0.102 (2)
O2'	0.262 (3)	0.459 (4)	0.634 (3)	0.052 (6)	0.102 (2)
N1'	−0.1507 (14)	−0.0071 (12)	0.1524 (15)	0.054 (3)	0.102 (2)
N2'	−0.1064 (15)	0.0573 (14)	0.2739 (15)	0.055 (3)	0.102 (2)
C1'	−0.664 (4)	−0.157 (3)	0.394 (3)	0.055 (5)	0.102 (2)
H1'1	−0.755231	−0.211867	0.369214	0.082*	0.102 (2)
H1'2	−0.605399	−0.210640	0.476523	0.082*	0.102 (2)
H1'3	−0.708624	−0.059756	0.418061	0.082*	0.102 (2)
C2'	−0.545 (2)	−0.142 (3)	0.267 (3)	0.066 (5)	0.102 (2)
H2'	−0.564913	−0.182154	0.179826	0.079*	0.102 (2)
C3'	−0.4083 (19)	−0.0693 (19)	0.278 (2)	0.064 (4)	0.102 (2)
H3'	−0.380715	−0.041637	0.368440	0.077*	0.102 (2)
C4'	−0.305 (2)	−0.034 (3)	0.152 (3)	0.048 (5)	0.102 (2)
H4'	−0.355132	−0.029991	0.061133	0.057*	0.102 (2)
C5'	0.0340 (17)	0.1135 (17)	0.2405 (17)	0.054 (3)	0.102 (2)
C6'	0.115 (3)	0.199 (2)	0.345 (2)	0.057 (5)	0.102 (2)
C7'	0.248 (2)	0.2777 (18)	0.3065 (17)	0.045 (3)	0.102 (2)
H7'	0.303354	0.273720	0.215557	0.054*	0.102 (2)
C8'	0.295 (3)	0.363 (3)	0.408 (2)	0.057 (5)	0.102 (2)
H8'	0.390159	0.415000	0.389954	0.069*	0.102 (2)
C9'	0.205 (5)	0.374 (5)	0.538 (3)	0.047 (5)	0.102 (2)
C10'	0.067 (3)	0.299 (3)	0.578 (3)	0.058 (6)	0.102 (2)
H10'	0.005157	0.306756	0.665513	0.070*	0.102 (2)
C11'	0.031 (2)	0.211 (2)	0.475 (2)	0.057 (5)	0.102 (2)
H11'	−0.059768	0.152927	0.495134	0.069*	0.102 (2)
C12'	0.181 (3)	0.489 (3)	0.766 (2)	0.043 (4)	0.102 (2)
H12C	0.123609	0.403449	0.807081	0.052*	0.102 (2)
H12D	0.096411	0.574476	0.749571	0.052*	0.102 (2)
C13'	0.310 (3)	0.522 (2)	0.872 (2)	0.067 (5)	0.102 (2)
H13'	0.419193	0.474347	0.874300	0.080*	0.102 (2)
C14'	0.260 (4)	0.618 (4)	0.956 (4)	0.090 (11)	0.102 (2)
H14C	0.149387	0.663448	0.950229	0.108*	0.102 (2)
H14D	0.333053	0.643923	1.024081	0.108*	0.102 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0642 (2)	0.04564 (18)	0.0584 (2)	−0.01815 (13)	−0.01564 (14)	−0.00945 (13)
O1	0.0649 (9)	0.0544 (8)	0.0601 (9)	−0.0232 (7)	−0.0120 (8)	−0.0138 (7)
O2	0.082 (2)	0.0662 (17)	0.0625 (12)	−0.0312 (13)	−0.0128 (11)	−0.0200 (11)
N1	0.0698 (10)	0.0464 (8)	0.0617 (10)	−0.0166 (7)	−0.0183 (8)	−0.0099 (7)
N2	0.0645 (9)	0.0519 (8)	0.0613 (10)	−0.0190 (7)	−0.0158 (8)	−0.0114 (7)
C1	0.078 (2)	0.075 (3)	0.095 (3)	−0.0150 (15)	0.004 (2)	−0.0096 (17)
C2	0.0775 (16)	0.0562 (13)	0.0769 (17)	−0.0096 (11)	−0.0073 (14)	−0.0095 (12)
C3	0.0672 (13)	0.0575 (11)	0.0676 (14)	−0.0134 (10)	−0.0136 (11)	−0.0111 (10)
C4	0.0702 (15)	0.041 (2)	0.0612 (15)	−0.0112 (14)	−0.0175 (12)	−0.0067 (13)
C5	0.0619 (11)	0.0455 (9)	0.0613 (12)	−0.0135 (8)	−0.0175 (10)	−0.0067 (8)
C6	0.0590 (13)	0.0477 (11)	0.0592 (12)	−0.0166 (10)	−0.0154 (9)	−0.0073 (9)
C7	0.0623 (13)	0.0613 (12)	0.0605 (12)	−0.0236 (10)	−0.0126 (10)	−0.0106 (9)
C8	0.0648 (16)	0.0640 (15)	0.0636 (13)	−0.0295 (11)	−0.0125 (11)	−0.0111 (10)
C9	0.065 (3)	0.0514 (15)	0.0631 (17)	−0.0172 (17)	−0.0226 (13)	−0.0110 (14)
C10	0.0567 (15)	0.0579 (12)	0.0596 (15)	−0.0159 (11)	−0.0068 (11)	−0.0125 (12)
C11	0.0588 (15)	0.0527 (11)	0.0640 (17)	−0.0199 (11)	−0.0138 (13)	−0.0089 (13)
C12	0.084 (2)	0.061 (2)	0.0657 (17)	−0.0187 (15)	−0.0127 (14)	−0.0189 (14)
C13	0.109 (2)	0.0719 (15)	0.0724 (16)	−0.0207 (15)	−0.0135 (14)	−0.0226 (13)
C14	0.294 (7)	0.114 (4)	0.083 (2)	−0.071 (4)	−0.069 (3)	−0.011 (2)
O1'	0.053 (6)	0.068 (8)	0.066 (6)	−0.017 (6)	−0.012 (5)	−0.012 (5)
O2'	0.033 (8)	0.057 (11)	0.070 (8)	−0.009 (7)	−0.009 (6)	−0.013 (7)
N1'	0.045 (5)	0.034 (5)	0.084 (7)	0.002 (4)	−0.020 (5)	−0.014 (5)
N2'	0.054 (5)	0.044 (6)	0.070 (7)	−0.012 (5)	−0.010 (4)	−0.010 (5)
C1'	0.053 (8)	0.030 (9)	0.083 (11)	−0.007 (7)	−0.029 (7)	−0.006 (8)
C2'	0.062 (8)	0.055 (10)	0.084 (12)	−0.010 (7)	−0.020 (8)	−0.010 (9)
C3'	0.055 (6)	0.051 (8)	0.089 (9)	−0.009 (6)	−0.022 (6)	−0.003 (7)
C4'	0.046 (6)	0.017 (10)	0.077 (9)	0.005 (5)	−0.034 (5)	0.007 (6)
C5'	0.054 (6)	0.042 (7)	0.068 (7)	−0.014 (5)	−0.016 (5)	−0.007 (5)
C6'	0.055 (8)	0.056 (9)	0.064 (8)	−0.028 (7)	0.000 (6)	−0.011 (7)
C7'	0.037 (7)	0.038 (7)	0.062 (7)	−0.018 (6)	−0.001 (5)	−0.006 (6)
C8'	0.050 (9)	0.056 (10)	0.070 (8)	−0.029 (7)	0.005 (6)	−0.011 (7)
C9'	0.034 (8)	0.048 (11)	0.060 (8)	−0.007 (7)	−0.005 (5)	−0.006 (7)
C10'	0.044 (9)	0.070 (11)	0.069 (9)	−0.033 (8)	0.007 (7)	−0.024 (8)
C11'	0.052 (9)	0.059 (9)	0.067 (8)	−0.022 (7)	0.000 (6)	−0.013 (7)
C12'	0.047 (8)	0.022 (8)	0.058 (8)	−0.001 (6)	−0.009 (6)	0.007 (6)
C13'	0.071 (10)	0.053 (9)	0.077 (9)	0.003 (7)	−0.027 (8)	−0.014 (8)
C14'	0.071 (12)	0.084 (19)	0.12 (2)	0.011 (13)	−0.038 (12)	−0.051 (18)

Geometric parameters (Å, º) top

Ni1—O1'ⁱ	1.793 (13)	C13—C14	1.258 (5)
Ni1—O1'	1.793 (13)	C13—H13	0.9500
Ni1—O1	1.8432 (16)	C14—H14A	0.9500
Ni1—O1ⁱ	1.8432 (16)	C14—H14B	0.9500
Ni1—N1'ⁱ	1.843 (14)	O1'—C5'	1.287 (15)
Ni1—N1'	1.843 (14)	O2'—C9'	1.363 (16)
Ni1—N1	1.8596 (18)	O2'—C12'	1.423 (17)
Ni1—N1ⁱ	1.8596 (18)	N1'—C4'	1.301 (17)
O1—C5	1.308 (2)	N1'—N2'	1.406 (14)
O2—C9	1.369 (3)	N2'—C5'	1.311 (14)
O2—C12	1.442 (4)	C1'—C2'	1.509 (18)
N1—C4	1.289 (4)	C1'—H1'1	0.9800
N1—N2	1.4034 (19)	C1'—H1'2	0.9800
N2—C5	1.304 (3)	C1'—H1'3	0.9800
C1—C2	1.501 (4)	C2'—C3'	1.360 (16)
C1—H1A	0.9800	C2'—H2'	0.9500
C1—H1B	0.9800	C3'—C4'	1.441 (19)
C1—H1C	0.9800	C3'—H3'	0.9500
C2—C3	1.319 (4)	C4'—H4'	0.9500
C2—H2	0.9500	C5'—C6'	1.519 (15)
C3—C4	1.436 (4)	C6'—C7'	1.368 (16)
C3—H3	0.9500	C6'—C11'	1.386 (17)
C4—H4	0.9500	C7'—C8'	1.381 (16)
C5—C6	1.490 (3)	C7'—H7'	0.9500
C6—C11	1.381 (4)	C8'—C9'	1.401 (17)
C6—C7	1.400 (3)	C8'—H8'	0.9500
C7—C8	1.379 (3)	C9'—C10'	1.397 (17)
C7—H7	0.9500	C10'—C11'	1.374 (16)
C8—C9	1.383 (4)	C10'—H10'	0.9500
C8—H8	0.9500	C11'—H11'	0.9500
C9—C10	1.397 (3)	C12'—C13'	1.534 (18)
C10—C11	1.401 (3)	C12'—H12C	0.9900
C10—H10	0.9500	C12'—H12D	0.9900
C11—H11	0.9500	C13'—C14'	1.263 (18)
C12—C13	1.518 (3)	C13'—H13'	0.9500
C12—H12A	0.9900	C14'—H14C	0.9500
C12—H12B	0.9900	C14'—H14D	0.9500

O1'ⁱ—Ni1—O1'	180.0	H12A—C12—H12B	108.8
O1—Ni1—O1ⁱ	180.00 (4)	C14—C13—C12	123.3 (4)
O1'ⁱ—Ni1—N1'ⁱ	82.3 (5)	C14—C13—H13	118.4
O1'—Ni1—N1'ⁱ	97.7 (5)	C12—C13—H13	118.4
O1—Ni1—N1'ⁱ	125.4 (3)	C13—C14—H14A	120.0
O1ⁱ—Ni1—N1'ⁱ	54.6 (3)	C13—C14—H14B	120.0
O1'ⁱ—Ni1—N1'	97.7 (5)	H14A—C14—H14B	120.0
O1'—Ni1—N1'	82.3 (5)	C5'—O1'—Ni1	114.5 (12)
N1'ⁱ—Ni1—N1'	180.0	C9'—O2'—C12'	125 (2)
O1—Ni1—N1	84.13 (7)	C4'—N1'—N2'	114.5 (17)
O1ⁱ—Ni1—N1	95.87 (7)	C4'—N1'—Ni1	128.3 (15)
O1—Ni1—N1ⁱ	95.87 (7)	N2'—N1'—Ni1	115.4 (8)
O1ⁱ—Ni1—N1ⁱ	84.13 (7)	C5'—N2'—N1'	106.7 (12)
N1—Ni1—N1ⁱ	180.0	C2'—C1'—H1'1	109.5
C5—O1—Ni1	109.78 (15)	C2'—C1'—H1'2	109.5
C9—O2—C12	117.6 (3)	H1'1—C1'—H1'2	109.5
C4—N1—N2	117.3 (2)	C2'—C1'—H1'3	109.5
C4—N1—Ni1	128.85 (17)	H1'1—C1'—H1'3	109.5
N2—N1—Ni1	113.84 (14)	H1'2—C1'—H1'3	109.5
C5—N2—N1	107.80 (16)	C3'—C2'—C1'	119 (2)
C2—C1—H1A	109.5	C3'—C2'—H2'	120.4
C2—C1—H1B	109.5	C1'—C2'—H2'	120.4
H1A—C1—H1B	109.5	C2'—C3'—C4'	120.4 (18)
C2—C1—H1C	109.5	C2'—C3'—H3'	119.8
H1A—C1—H1C	109.5	C4'—C3'—H3'	119.8
H1B—C1—H1C	109.5	N1'—C4'—C3'	126 (2)
C3—C2—C1	125.3 (3)	N1'—C4'—H4'	116.9
C3—C2—H2	117.4	C3'—C4'—H4'	116.9
C1—C2—H2	117.4	O1'—C5'—N2'	121.1 (14)
C2—C3—C4	121.9 (2)	O1'—C5'—C6'	117.6 (13)
C2—C3—H3	119.1	N2'—C5'—C6'	121.3 (13)
C4—C3—H3	119.1	C7'—C6'—C11'	121.5 (13)
N1—C4—C3	126.8 (3)	C7'—C6'—C5'	123.1 (15)
N1—C4—H4	116.6	C11'—C6'—C5'	114.7 (15)
C3—C4—H4	116.6	C6'—C7'—C8'	115.9 (13)
N2—C5—O1	124.2 (2)	C6'—C7'—H7'	122.1
N2—C5—C6	118.43 (19)	C8'—C7'—H7'	122.1
O1—C5—C6	117.4 (2)	C7'—C8'—C9'	121.2 (15)
C11—C6—C7	119.07 (18)	C7'—C8'—H8'	119.4
C11—C6—C5	120.9 (2)	C9'—C8'—H8'	119.4
C7—C6—C5	120.0 (2)	O2'—C9'—C10'	118.7 (18)
C8—C7—C6	120.0 (2)	O2'—C9'—C8'	117.2 (18)
C8—C7—H7	120.0	C10'—C9'—C8'	124.0 (16)
C6—C7—H7	120.0	C11'—C10'—C9'	112.0 (16)
C7—C8—C9	120.8 (2)	C11'—C10'—H10'	124.0
C7—C8—H8	119.6	C9'—C10'—H10'	124.0
C9—C8—H8	119.6	C10'—C11'—C6'	125.4 (15)
O2—C9—C8	115.2 (3)	C10'—C11'—H11'	117.3
O2—C9—C10	124.7 (3)	C6'—C11'—H11'	117.3
C8—C9—C10	120.2 (2)	O2'—C12'—C13'	109.1 (19)
C9—C10—C11	118.5 (2)	O2'—C12'—H12C	109.9
C9—C10—H10	120.7	C13'—C12'—H12C	109.9
C11—C10—H10	120.7	O2'—C12'—H12D	109.9
C6—C11—C10	121.4 (2)	C13'—C12'—H12D	109.9
C6—C11—H11	119.3	H12C—C12'—H12D	108.3
C10—C11—H11	119.3	C14'—C13'—C12'	115.3 (19)
O2—C12—C13	105.3 (3)	C14'—C13'—H13'	122.3
O2—C12—H12A	110.7	C12'—C13'—H13'	122.3
C13—C12—H12A	110.7	C13'—C14'—H14C	120.0
O2—C12—H12B	110.7	C13'—C14'—H14D	120.0
C13—C12—H12B	110.7	H14C—C14'—H14D	120.0

N1—Ni1—O1—C5	4.34 (13)	N1'ⁱ—Ni1—O1'—C5'	−179.7 (12)
N1ⁱ—Ni1—O1—C5	−175.66 (13)	N1'—Ni1—O1'—C5'	0.3 (12)
O1—Ni1—N1—C4	177.9 (3)	O1'ⁱ—Ni1—N1'—C4'	−18 (2)
O1ⁱ—Ni1—N1—C4	−2.1 (3)	O1'—Ni1—N1'—C4'	162 (2)
O1—Ni1—N1—N2	−4.24 (12)	O1'ⁱ—Ni1—N1'—N2'	178.1 (9)
O1ⁱ—Ni1—N1—N2	175.76 (12)	O1'—Ni1—N1'—N2'	−1.9 (9)
C4—N1—N2—C5	−178.9 (2)	C4'—N1'—N2'—C5'	−163.0 (18)
Ni1—N1—N2—C5	3.05 (18)	Ni1—N1'—N2'—C5'	3.0 (14)
C1—C2—C3—C4	177.7 (4)	C1'—C2'—C3'—C4'	−171 (2)
N2—N1—C4—C3	3.1 (5)	N2'—N1'—C4'—C3'	−30 (4)
Ni1—N1—C4—C3	−179.1 (2)	Ni1—N1'—C4'—C3'	165.8 (19)
C2—C3—C4—N1	−176.1 (3)	C2'—C3'—C4'—N1'	−158 (3)
N1—N2—C5—O1	0.8 (3)	Ni1—O1'—C5'—N2'	2 (2)
N1—N2—C5—C6	−178.15 (15)	Ni1—O1'—C5'—C6'	−178.4 (14)
Ni1—O1—C5—N2	−4.2 (2)	N1'—N2'—C5'—O1'	−3 (2)
Ni1—O1—C5—C6	174.79 (13)	N1'—N2'—C5'—C6'	177.0 (16)
N2—C5—C6—C11	−179.42 (19)	O1'—C5'—C6'—C7'	10 (3)
O1—C5—C6—C11	1.6 (3)	N2'—C5'—C6'—C7'	−169.9 (19)
N2—C5—C6—C7	3.0 (3)	O1'—C5'—C6'—C11'	−179 (2)
O1—C5—C6—C7	−175.96 (18)	N2'—C5'—C6'—C11'	1 (3)
C11—C6—C7—C8	−1.8 (3)	C11'—C6'—C7'—C8'	3 (4)
C5—C6—C7—C8	175.8 (2)	C5'—C6'—C7'—C8'	173 (2)
C6—C7—C8—C9	0.7 (5)	C6'—C7'—C8'—C9'	−4 (4)
C12—O2—C9—C8	179.7 (5)	C12'—O2'—C9'—C10'	−8 (7)
C12—O2—C9—C10	−0.5 (9)	C12'—O2'—C9'—C8'	176 (4)
C7—C8—C9—O2	−179.1 (4)	C7'—C8'—C9'—O2'	179 (4)
C7—C8—C9—C10	1.0 (7)	C7'—C8'—C9'—C10'	2 (7)
O2—C9—C10—C11	178.5 (5)	O2'—C9'—C10'—C11'	−176 (4)
C8—C9—C10—C11	−1.7 (7)	C8'—C9'—C10'—C11'	0 (6)
C7—C6—C11—C10	1.1 (3)	C9'—C10'—C11'—C6'	−2 (5)
C5—C6—C11—C10	−176.5 (2)	C7'—C6'—C11'—C10'	0 (5)
C9—C10—C11—C6	0.6 (5)	C5'—C6'—C11'—C10'	−171 (2)
C9—O2—C12—C13	−174.3 (5)	C9'—O2'—C12'—C13'	154 (4)
O2—C12—C13—C14	−138.1 (6)	O2'—C12'—C13'—C14'	145 (3)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C6–C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.95	2.46	2.975 (3)	114
C8—H8···O2ⁱⁱ	0.95	2.55	3.466 (5)	161
C11a—H11a···O1a	0.95	2.48	2.801 (3)	100
C12—H12b···Cg1ⁱⁱⁱ	0.95	2.88	3.781 (4)	152

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

Acknowledgements

MBHH and SSK are grateful to the Department of Chemistry, Rajshahi University for the provision of laboratory facilities. MCS and RM acknowledge the Center for Environmental Conservation and Research Safety, University of Toyama, for providing facilities for single-crystal X-ray analyses.

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