Bis[N′-(2-methyl­propyl­idene)-4-(prop-2-en-1-yloxy)benzohydrazidato-κ2N′,O]nickel(II)

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

doi:10.1107/S2414314625009885

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 10| Part 11| November 2025| x250988

https://doi.org/10.1107/S2414314625009885

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Bis[N′-(2-methylpropylidene)-4-(prop-2-en-1-yloxy)benzohydrazidato-κ²N′,O]nickel(II)

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

^aDepartment of Pharmacy, Pabna University of Science and Technology, Pabna-6600, Bangladesh, ^bDepartment of Chemistry, Rajshahi University, Rajshahi-6205, Bangladesh, ^cDivision of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 1-1 Tsushima-naka, 3-Chome, Okayama, 700-8530, Japan, ^dCenter for Environmental Conservation and Research Safety, University of Toyama, 3190 Gofuku, Toyama, 930-8555, Japan, and ^eDepartment of Chemical and Pharmaceutical Science, University of Trieste, Italy
^*Correspondence e-mail: [email protected]

Edited by M. Weil, Vienna University of Technology, Austria (Received 14 October 2025; accepted 6 November 2025; online 11 November 2025)

In the mononuclear title complex, [Ni(C₁₄H₁₇N₂O₂)₂], the nickel(II) atom exhibits a slightly distorted square-planar coordination environment with the metal located on a crystallographic center of symmetry that induces a trans configuration of the N,O chelating ligands. In the crystal, weak C—H⋯O and C—H⋯π interactions consolidate the packing.

Keywords: crystal structure; nickel(II) complex; aroylhydrazone ligand.

CCDC reference: 2335124

Structure description

Hydrazone ligands have attracted special attention for their chelating capabilities. The corresponding nickel(II) complexes are of considerable interest since they exhibit a broad spectrum of structure-dependent physiological and pharmacological activities (Al-Qadsy et al., 2021 ; Neethu et al., 2021 ; Krishnamoorthy et al., 2012 ; Yang et al., 2020 ).

The title nickel(II) complex crystallizes in the monoclinic space group P2₁/c with the metal located on an inversion center, so that the asymmetric unit comprises a half molecule (Fig. 1). The Ni^II atom exhibits a slightly distorted square-planar coordination environment with the chelating ligands in a trans configuration imposed by symmetry. The coordinating enolizable O atom and the azomethine N atom of the deprotonated ligand form a five-membered nearly planar chelate ring (r.m.s. deviation from planarity = 0.0084 Å). The Ni—N1 and Ni—O1 bond lengths of 1.8671 (13) and 1.8382 (11) Å and the chelate angle of 83.64 (5)° are in agreement with those of previously reported complexes (Al-Qadsy et al., 2021; Khan et al., 2023 , 2025 ; Krishnamoorthy et al., 2012; Neethu et al., 2021; Yang et al., 2020), irrespective of the substituents present in the ligand. The C5—O1 bond length of 1.3080 (18) Å lies in between a C—O single and a C=O double bond. The bond lengths N1—C4 of 1.285 (2) Å and N2—C5 of 1.308 (2) Å are indicative of a conjugated system within the —CH=N—N=C—O fragment, even after the deprotonation of its enolized carbonyl O atom. The benzylidene entity (C5–C11) is practically co-planar with the N₂O₂ coordination plane [dihedral angle of 3.09 (5)°] and also to the allyloxy fragment [7.73 (14)°]. An intramolecular hydrogen bond between a methine group (C4—H4) and the chelating O atom (Table 1) stabilizes the molecular conformation.

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the benzyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1ⁱ	0.95	2.47	2.9822 (19)	114
C12—H12A⋯O1ⁱⁱ	0.99	2.58	3.451 (2)	148
C12—H12B⋯Cg3ⁱⁱⁱ	0.99	2.64	3.4762 (17)	143
Symmetry codes: (i) ; (ii) ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title complex with displacement ellipsoids drawn at the 50% probability level. Atoms marked with a prime character and all non-labelled atoms are generated by inversion symmetry. [Symmetry code: −x + 1, −y + 1, −z.]

The packing of the complex molecules is consolidated by a weak intermolecular hydrogen bond between a methylene group (C12—H12A) and the ligating O atom of a neighbouring complex. C—H⋯π interactions between the second H atom of this methylene group and the centroid (Cg3) of the benzyl ring are also observed (Table 1), while no apparent π–π interactions are present. In the crystal packing (Fig. 2) the shortest separation of Ni^II atoms is 8.5593 (2) Å.

Figure 2
Crystal packing of the title complex with H atoms removed for clarity.

Synthesis and crystallization

Isobutyraldehyde (0.216 g, 3.0 mmol) in 10 ml of ethanol was added to a 30 ml ethanolic solution of 4-(allyloxy)benzoylhydrazine (0.576 g, 3.0 mmol), followed by refluxing for one h. To this mixture Ni(CH₃COO)₂·4H₂O (0.373 g, 1.5 mmol, in 30 ml) was introduced, and refluxing was prolonged for additional three h. The yellow precipitate formed was then filtered off while hot. Finally, the product was dried and stored in a vacuum desiccator containing anhydrous CaCl₂. Single crystals of the nickel(II) complex, suitable for X-ray diffraction, were obtained through gradual evaporation from a mixture of chloroform and toluene (3:1, v/v) over a period of 3 weeks. Yellow crystals, yield: 0.604 g (73%); melting point: 485–487 K. IR data (KBr disc, cm⁻¹): 1606 ν(C=N), 1587 ν(C=C), 997 ν(N—N), 596 ν(M—N), 465 ν(M—O). ¹H NMR (CDCl₃, 400 MHz), δ: 7.82 (d, 2×2H, C-6, 8, J = 8.8 Hz), 6.85 (d, 2×2H, C-5, 9, J = 8.8 Hz), 6.50 (d, 2×1H, C-11, CH=N, J = 8.0 Hz), 6.4–6.0 (m, 2×1H, C-2, H_c), 5.41 (d, 2×1H, C-1, H_a, J = 17.6 Hz), 5.29 (d, 2×1H, C-1, H_b, J = 10.4 Hz), 4.56 (d, 2×2H, C-3, OCH₂, J = 5.6 Hz,), 3.72–3.63 (m, 2×1H, C-12), 1.16 (d, 2×6H, C-13,14, J = 8.4 Hz). HRMS (FAB) calculated for C₂₈H₃₄N₄NiO₄, [M+H]⁺: 549.20086, found [M+H]⁺: 549.20062.

Refinement

Crystal data, data collection, and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Ni(C₁₄H₁₇N₂O₂)₂]
M_r	549.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	12.5241 (3), 13.4196 (4), 8.5593 (2)
β (°)	109.274 (8)
V (Å³)	1357.91 (9)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.75
Crystal size (mm)	0.22 × 0.11 × 0.07

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Rigaku, 1995 )
T_min, T_max	0.722, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	12824, 3106, 2678
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.081, 1.04
No. of reflections	3106
No. of parameters	171
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.22
Computer programs: RAPID-AUTO (Rigaku, 2019 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 1999 ) and WinGX (Farrugia, 2012 ).

Structural data

CCDC reference: 2335124

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314625009885/wm4238sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625009885/wm4238Isup2.hkl

checkCIF report

Computing details top

Bis[N'-(2-methylpropylidene)-4-(prop-2-en-1-yloxy)benzohydrazidato-κ²N',O]nickel(II) top

Crystal data top

[Ni(C₁₄H₁₇N₂O₂)₂]	F(000) = 580
M_r = 549.30	D_x = 1.343 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71075 Å
a = 12.5241 (3) Å	Cell parameters from 10492 reflections
b = 13.4196 (4) Å	θ = 2.3–27.5°
c = 8.5593 (2) Å	µ = 0.75 mm⁻¹
β = 109.274 (8)°	T = 173 K
V = 1357.91 (9) Å³	Prism, yellow
Z = 2	0.22 × 0.11 × 0.07 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2678 reflections with I > 2σ(I)
ω scans	R_int = 0.031
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	θ_max = 27.5°, θ_min = 2.3°
T_min = 0.722, T_max = 0.949	h = −16→16
12824 measured reflections	k = −17→17
3106 independent reflections	l = −11→11

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0388P)² + 0.5845P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3106 reflections	Δρ_max = 0.43 e Å⁻³
171 parameters	Δρ_min = −0.21 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
Ni1	0.500000	0.500000	0.000000	0.02365 (9)
O1	0.40545 (9)	0.48867 (8)	0.12389 (13)	0.0272 (2)
O2	0.18732 (9)	0.38385 (9)	0.66963 (13)	0.0302 (3)
N1	0.59615 (11)	0.42033 (10)	0.16621 (15)	0.0251 (3)
N2	0.55099 (11)	0.39157 (10)	0.28959 (16)	0.0265 (3)
C1	0.89710 (15)	0.35433 (15)	0.3488 (3)	0.0423 (4)
H1A	0.913977	0.331595	0.250634	0.051*
H1B	0.945166	0.318522	0.446480	0.051*
H1C	0.911834	0.426013	0.363773	0.051*
C2	0.74500 (17)	0.22294 (14)	0.3009 (2)	0.0411 (4)
H2A	0.798169	0.184695	0.390729	0.049*
H2B	0.750983	0.201381	0.194659	0.049*
H2C	0.667728	0.211635	0.300996	0.049*
C3	0.77329 (14)	0.33389 (12)	0.3261 (2)	0.0290 (3)
H3	0.758739	0.355730	0.428933	0.035*
C4	0.69787 (14)	0.39313 (12)	0.18425 (19)	0.0274 (3)
H4	0.727860	0.412281	0.100237	0.033*
C5	0.45128 (13)	0.43305 (11)	0.25439 (18)	0.0245 (3)
C6	0.38466 (13)	0.41678 (11)	0.36654 (18)	0.0239 (3)
C7	0.42822 (13)	0.36377 (12)	0.51408 (19)	0.0264 (3)
H7	0.502209	0.336480	0.543159	0.032*
C8	0.36562 (13)	0.35007 (12)	0.61932 (19)	0.0268 (3)
H8	0.396352	0.313752	0.719449	0.032*
C9	0.25697 (13)	0.39030 (11)	0.57628 (18)	0.0247 (3)
C10	0.21195 (14)	0.44225 (12)	0.42783 (19)	0.0278 (3)
H10	0.137429	0.468481	0.397653	0.033*
C11	0.27520 (13)	0.45567 (12)	0.32482 (19)	0.0264 (3)
H11	0.244144	0.491699	0.224447	0.032*
C12	0.22916 (14)	0.33458 (12)	0.82672 (19)	0.0289 (3)
H12A	0.301977	0.364646	0.894171	0.035*
H12B	0.242193	0.263153	0.810353	0.035*
C13	0.14474 (17)	0.34507 (15)	0.9136 (2)	0.0416 (4)
H13	0.160758	0.310432	1.015534	0.050*
C14	0.05119 (18)	0.39645 (17)	0.8655 (3)	0.0511 (5)
H14A	0.030867	0.432590	0.764502	0.061*
H14B	0.003345	0.397763	0.931571	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02442 (15)	0.02543 (15)	0.02219 (15)	0.00068 (11)	0.00916 (10)	0.00268 (11)
O1	0.0265 (5)	0.0313 (6)	0.0251 (5)	0.0021 (5)	0.0102 (4)	0.0048 (4)
O2	0.0293 (6)	0.0368 (6)	0.0278 (6)	0.0051 (5)	0.0139 (5)	0.0085 (5)
N1	0.0277 (6)	0.0259 (6)	0.0237 (6)	0.0000 (5)	0.0111 (5)	0.0009 (5)
N2	0.0291 (7)	0.0281 (7)	0.0253 (6)	0.0002 (5)	0.0130 (5)	0.0033 (5)
C1	0.0313 (9)	0.0417 (10)	0.0533 (11)	0.0065 (8)	0.0132 (8)	0.0076 (9)
C2	0.0491 (11)	0.0308 (9)	0.0409 (10)	0.0014 (8)	0.0114 (8)	0.0049 (8)
C3	0.0296 (8)	0.0293 (8)	0.0288 (8)	0.0042 (7)	0.0107 (6)	0.0013 (6)
C4	0.0301 (8)	0.0282 (8)	0.0263 (7)	0.0005 (6)	0.0127 (6)	0.0008 (6)
C5	0.0275 (7)	0.0226 (7)	0.0234 (7)	−0.0035 (6)	0.0086 (6)	−0.0016 (6)
C6	0.0251 (7)	0.0233 (7)	0.0240 (7)	−0.0029 (6)	0.0091 (6)	−0.0001 (6)
C7	0.0232 (7)	0.0290 (8)	0.0268 (7)	0.0017 (6)	0.0079 (6)	0.0013 (6)
C8	0.0286 (8)	0.0271 (8)	0.0243 (7)	0.0016 (6)	0.0083 (6)	0.0044 (6)
C9	0.0271 (8)	0.0229 (7)	0.0260 (7)	−0.0015 (6)	0.0114 (6)	−0.0002 (6)
C10	0.0265 (8)	0.0281 (8)	0.0292 (8)	0.0047 (6)	0.0099 (6)	0.0042 (6)
C11	0.0299 (8)	0.0242 (7)	0.0251 (7)	0.0020 (6)	0.0088 (6)	0.0042 (6)
C12	0.0347 (9)	0.0279 (8)	0.0251 (7)	0.0009 (7)	0.0111 (6)	0.0040 (6)
C13	0.0523 (11)	0.0428 (10)	0.0383 (10)	0.0070 (9)	0.0265 (9)	0.0117 (8)
C14	0.0483 (12)	0.0591 (13)	0.0584 (13)	0.0099 (10)	0.0345 (10)	0.0159 (10)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	1.8382 (11)	C4—H4	0.9500
Ni1—O1	1.8382 (11)	C5—C6	1.481 (2)
Ni1—N1ⁱ	1.8671 (13)	C6—C7	1.394 (2)
Ni1—N1	1.8671 (13)	C6—C11	1.399 (2)
O1—C5	1.3080 (18)	C7—C8	1.388 (2)
O2—C9	1.3663 (18)	C7—H7	0.9500
O2—C12	1.4334 (18)	C8—C9	1.396 (2)
N1—C4	1.285 (2)	C8—H8	0.9500
N1—N2	1.4065 (17)	C9—C10	1.395 (2)
N2—C5	1.308 (2)	C10—C11	1.378 (2)
C1—C3	1.523 (2)	C10—H10	0.9500
C1—H1A	0.9800	C11—H11	0.9500
C1—H1B	0.9800	C12—C13	1.486 (2)
C1—H1C	0.9800	C12—H12A	0.9900
C2—C3	1.529 (2)	C12—H12B	0.9900
C2—H2A	0.9800	C13—C14	1.304 (3)
C2—H2B	0.9800	C13—H13	0.9500
C2—H2C	0.9800	C14—H14A	0.9500
C3—C4	1.497 (2)	C14—H14B	0.9500
C3—H3	1.0000

O1ⁱ—Ni1—O1	180.0	O1—C5—N2	123.77 (14)
O1ⁱ—Ni1—N1ⁱ	83.64 (5)	O1—C5—C6	117.08 (13)
O1—Ni1—N1ⁱ	96.36 (5)	N2—C5—C6	119.15 (13)
O1ⁱ—Ni1—N1	96.36 (5)	C7—C6—C11	118.63 (14)
O1—Ni1—N1	83.64 (5)	C7—C6—C5	121.78 (14)
N1ⁱ—Ni1—N1	180.0	C11—C6—C5	119.59 (14)
C5—O1—Ni1	110.80 (10)	C8—C7—C6	121.30 (14)
C9—O2—C12	118.13 (12)	C8—C7—H7	119.4
C4—N1—N2	117.41 (13)	C6—C7—H7	119.4
C4—N1—Ni1	128.23 (11)	C7—C8—C9	119.21 (14)
N2—N1—Ni1	114.28 (10)	C7—C8—H8	120.4
C5—N2—N1	107.47 (12)	C9—C8—H8	120.4
C3—C1—H1A	109.5	O2—C9—C10	114.85 (13)
C3—C1—H1B	109.5	O2—C9—C8	125.18 (13)
H1A—C1—H1B	109.5	C10—C9—C8	119.97 (14)
C3—C1—H1C	109.5	C11—C10—C9	120.22 (14)
H1A—C1—H1C	109.5	C11—C10—H10	119.9
H1B—C1—H1C	109.5	C9—C10—H10	119.9
C3—C2—H2A	109.5	C10—C11—C6	120.66 (14)
C3—C2—H2B	109.5	C10—C11—H11	119.7
H2A—C2—H2B	109.5	C6—C11—H11	119.7
C3—C2—H2C	109.5	O2—C12—C13	108.98 (13)
H2A—C2—H2C	109.5	O2—C12—H12A	109.9
H2B—C2—H2C	109.5	C13—C12—H12A	109.9
C4—C3—C1	110.55 (14)	O2—C12—H12B	109.9
C4—C3—C2	110.35 (14)	C13—C12—H12B	109.9
C1—C3—C2	111.84 (15)	H12A—C12—H12B	108.3
C4—C3—H3	108.0	C14—C13—C12	127.31 (17)
C1—C3—H3	108.0	C14—C13—H13	116.3
C2—C3—H3	108.0	C12—C13—H13	116.3
N1—C4—C3	125.70 (14)	C13—C14—H14A	120.0
N1—C4—H4	117.1	C13—C14—H14B	120.0
C3—C4—H4	117.1	H14A—C14—H14B	120.0

N1ⁱ—Ni1—O1—C5	179.15 (10)	N2—C5—C6—C7	4.2 (2)
N1—Ni1—O1—C5	−0.84 (10)	O1—C5—C6—C11	3.6 (2)
O1ⁱ—Ni1—N1—C4	4.90 (15)	N2—C5—C6—C11	−176.09 (14)
O1—Ni1—N1—C4	−175.10 (15)	C11—C6—C7—C8	−0.6 (2)
O1ⁱ—Ni1—N1—N2	−178.37 (10)	C5—C6—C7—C8	179.14 (14)
O1—Ni1—N1—N2	1.63 (10)	C6—C7—C8—C9	0.0 (2)
C4—N1—N2—C5	175.12 (14)	C12—O2—C9—C10	−177.85 (14)
Ni1—N1—N2—C5	−1.98 (15)	C12—O2—C9—C8	1.9 (2)
N2—N1—C4—C3	−0.5 (2)	C7—C8—C9—O2	−178.80 (14)
Ni1—N1—C4—C3	176.19 (12)	C7—C8—C9—C10	0.9 (2)
C1—C3—C4—N1	−154.63 (17)	O2—C9—C10—C11	178.54 (14)
C2—C3—C4—N1	81.1 (2)	C8—C9—C10—C11	−1.2 (2)
Ni1—O1—C5—N2	−0.14 (19)	C9—C10—C11—C6	0.6 (2)
Ni1—O1—C5—C6	−179.85 (10)	C7—C6—C11—C10	0.3 (2)
N1—N2—C5—O1	1.4 (2)	C5—C6—C11—C10	−179.43 (14)
N1—N2—C5—C6	−178.90 (12)	C9—O2—C12—C13	174.40 (14)
O1—C5—C6—C7	−176.10 (14)	O2—C12—C13—C14	−5.0 (3)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the benzyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.95	2.47	2.9822 (19)	114
C12—H12A···O1ⁱⁱ	0.99	2.58	3.451 (2)	148
C12—H12B···Cg3ⁱⁱⁱ	0.99	2.64	3.4762 (17)	143

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

Acknowledgements

MBHH, and SSK are grateful to the Department of Chemistry, Rajshahi University, Rajshahi-6205, Bangladesh for providing 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.

References

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