Di-μ-adipato-κ4O1,O1′:O6,O6′-bis­[(2,2′-di­pyridyl­amine-κ2N,N′)zinc(II)] trihydrate

Setifi, F.; Setifi, Z.; Pham Chien, T.; Al-Douh, M.H.; Addala, A.

doi:10.1107/S2414314624009064

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 9| September 2024| x240906

https://doi.org/10.1107/S2414314624009064

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Di-μ-adipato-κ⁴O¹,O^1′:O⁶,O^6′-bis[(2,2′-dipyridylamine-κ²N,N′)zinc(II)] trihydrate

Fatima Setifi,^a ^* Zouaoui Setifi,^b,^a Thang Pham Chien,^c ^* Mohammad Hadi Al-Douh ^d and Abderezak Addala ^a

^aLaboratoire de Chimie, Ingénierie Moléculaire et Nanostructures (LCIMN), Université Ferhat Abbas Sétif 1, Sétif 19000, Algeria, ^bDépartment de Technologie, Faculté de Technologie, Université 20 Août 1955-Skikda, BP 26, Route d'El-Hadaiek, Skikda 21000, Algeria, ^cDepartment of Inorganic Chemistry, Faculty of Chemistry, VNU University of Science, Vietnam National University, Hanoi, 19 Le Thanh Tong, Hanoi, Vietnam, and ^dChemistry Department, Faculty of Science, Hadhramout University, Mukalla, Hadhramout, Yemen
^*Correspondence e-mail: fatima.setifi@univ-setif.dz, phamchienthang@hus.edu.vn

Edited by M. Weil, Vienna University of Technology, Austria (Received 28 August 2024; accepted 16 September 2024; online 20 September 2024)

The title compound, [Zn₂(C₆H₈O₄)₂(C₁₀H₉N₃)₂]·3H₂O or {Zn₂[(C₅H₄N)₂NH]₂[μ-(CH₂)₄(COO)₂]₂}·3H₂O, was separated from the solvothermal reaction of zinc(II) sulfate heptahydrate, 2,2′-dipyridylamine and sodium adipate. The dinuclear metal complex has a centrosymmetric structure, with the Zn^II atom adopting a highly distorted octahedral coordination sphere composed of four oxygen atoms from bridging adipato ligands and two pyridine nitrogen atoms. In the crystal, the title compound aggregates into a tri-periodic supramolecular structure through intermolecular hydrogen-bonding networks of the form O—H⋯O and N—H⋯O.

Keywords: crystal structure; zinc(II) complexes; 2,2′-dipyridylamine; adipate dianion; octahedral coordination.

CCDC reference: 2384469

Structure description

Polynitrile and bis-carboxylate compounds derived from transition-metal ions are of great interest with respect to their magnetic and luminescence properties, diverse molecular structures and for their topologies (Addala et al. 2019 ; Benmansour et al., 2010 ; Klongdee et al., 2023 ).

As a part of our continuing studies of the structural, magnetic and luminescence properties of coordination complexes containing polynitrile and/or bis-carboxylate and polypyridyl units (Setifi et al., 2006 , 2016 ; Lehchili et al., 2017 ), we report here the molecular and crystal structure of the dinuclear compound, [Zn₂(adp)₂(dpa)₂]·3H₂O, based on the adipate dianion (adp) as ligand and the 2,2′-dipyridylamine (dpa) as co-ligand.

The asymmetric unit of the title compound consists of half of the metal complex molecule and two water molecules (one of which exhibits half-occupancy). The molecule is completed by inversion symmetry. The Zn^II atom is octahedrally coordinated by two (O,O′) donor sets of carboxylato groups from two different adp ligands and one (N,N)-chelating dpa co-ligand (Fig. 1). Except the Zn—O4 contact with a significantly long bond of 2.567 (2) Å, the lengths of other Zn—O bonds are in the range of 2.0073 (19)–2.2146 (17) Å, while Zn1—N1 and Zn1—N3 bond lengths are 2.0473 (16) and 2.0470 (16) Å, respectively. As a result of the long Zn—O4 bond, the highly distorted octahedral coordination environment of Zn^II ion is best described as [5 + 1]. This bonding situation of the present dinuclear Zn^II compound closely resembles Ni^II and Cu^II counterparts previously reported (Setifi et al., 2014 ).

Figure 1
The molecular structure of the title compound showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: ($) −x + 1, −y + 1, −z + 1.]

In the crystal, complex molecules aggregate into a tri-periodic supramolecular hydrogen-bonding network. The NH groups of dpa form hydrogen bonds with the O5 water molecules, which in turn provide hydrogen bonds to carboxylate oxygen atoms (O1 and O4) of adp (Table 1, Fig. 2a). In addition, the half-occupied O6 water molecule is also involved in weaker hydrogen bonds with adp through O2 and O4 atoms (Table 1, Fig. 2b).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O1	0.85	1.89	2.728 (3)	167
O5—H5B⋯O4ⁱ	0.85	2.10	2.877 (3)	151
O6—H6A⋯O4	0.85	2.26	3.107 (5)	173
O6—H6B⋯O2ⁱⁱ	0.85	2.58	3.275 (5)	140
N2—H2⋯O5ⁱⁱⁱ	0.86	1.97	2.824 (2)	177
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) ; (iii) .

Figure 2
Partial packing diagram showing the hydrogen-bonding interactions involving (a) O5 water molecules (shown in projection down the a axis) and (b) O6 water molecules (shown in projection down the b axis). Hydrogen atoms bonded to carbon atoms were omitted for clarity. [Symmetry codes: (i) x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z − $[{1\over 2}]$ ; (iii) −x + 1, −y, −z + 1; (iv) −x + $[{1\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (v) x − $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z + $[{1\over 2}]$ ; (vi) x − $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z − $[{1\over 2}]$ ; (vii) −x + $[{1\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{3\over 2}]$ ; (viii) x, y + 1, z; (ix) −x + $[{1\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{3\over 2}]$ ; (x) x + $[{1\over 2}]$ , −y + $[{3\over 2}]$ , z − $[{1\over 2}]$ ; (xi) x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z + $[{1\over 2}]$ ; (xii) −x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (xiii) −x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{3\over 2}]$ ].

Synthesis and crystallization

The title compound was prepared solvothermally under autogenous pressure from a mixture of zinc(II) sulfate heptahydrate (29 mg, 0.1 mmol), 2,2′-dipyridylamine (24 mg, 0.2 mmol) and sodium adipate (0.2 mol l⁻¹) in a mixture of water and ethanol (4:1 v/v, 25 ml). This mixture was sealed in a Teflon-lined autoclave and held at 393 K for 2 d, and then cooled to ambient temperature at a rate of 10 K h⁻¹ to give the product in form of colorless needles (yield 36%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The O6 atom and associated H atoms of the second water molecule were refined with an occupancy of 0.5. Hydrogen atoms of the water molecules were included in calculated positions and were refined in a riding model, with O—H distances of 0.85 Å and U_iso(H) = 1.5U_eq(O).

Table 2
Experimental details

Crystal data
Chemical formula	[Zn₂(C₆H₈O₄)₂(C₁₀H₉N₃)₂]·3H₂O
M_r	815.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	302
a, b, c (Å)	8.2105 (3), 14.4478 (6), 15.2042 (8)
β (°)	101.694 (2)
V (Å³)	1766.14 (14)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.43
Crystal size (mm)	0.18 × 0.11 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur with Sapphire CCD
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ )
T_min, T_max	0.492, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	20158, 6416, 4033
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.762

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.102, 1.02
No. of reflections	6416
No. of parameters	241
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.86
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ), CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), OLEX2 1.5 (Dolomanov et al., 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2384469

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314624009064/wm4220sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624009064/wm4220Isup2.hkl

checkCIF report

Computing details top

Di-µ-adipato-κ⁴O¹,O^1':O⁶,O^6'-bis{[N-(pyridin-2-yl-κN)pyridin-2-amine-κN¹]zinc(II)} trihydrate top

Crystal data top

[Zn₂(C₆H₈O₄)₂(C₁₀H₉N₃)₂]·3H₂O	F(000) = 844
M_r = 815.44	D_x = 1.533 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.2105 (3) Å	Cell parameters from 1439 reflections
b = 14.4478 (6) Å	θ = 2.3–26.3°
c = 15.2042 (8) Å	µ = 1.43 mm⁻¹
β = 101.694 (2)°	T = 302 K
V = 1766.14 (14) Å³	Needle, colourless
Z = 2	0.18 × 0.11 × 0.06 mm

Data collection top

Oxford Diffraction Xcalibur with Sapphire CCD diffractometer	4033 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray source	R_int = 0.038
ω scans	θ_max = 32.8°, θ_min = 3.6°
Absorption correction: multi-scan (Crysalis Red; Oxford Diffraction, 2009)	h = −10→12
T_min = 0.492, T_max = 1.000	k = −22→21
20158 measured reflections	l = −23→21
6416 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0328P)² + 0.9459P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
6416 reflections	Δρ_max = 0.48 e Å⁻³
241 parameters	Δρ_min = −0.86 e Å⁻³
0 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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)
Zn1	0.52923 (3)	0.23563 (2)	0.59713 (2)	0.03924 (9)
O4	0.3690 (3)	0.31102 (13)	0.70690 (14)	0.0791 (7)
O2	0.7724 (3)	0.30383 (15)	0.60833 (13)	0.0752 (6)
O1	0.6465 (2)	0.25296 (11)	0.47921 (12)	0.0498 (4)
O5	0.6289 (3)	0.16459 (13)	0.31903 (14)	0.0725 (6)
H5A	0.639294	0.199470	0.364850	0.109*
H5B	0.722914	0.167391	0.303780	0.109*
O6	0.0902 (5)	0.1631 (3)	0.6599 (3)	0.0730 (11)	0.5
H6A	0.171671	0.199984	0.675684	0.109*	0.5
H6B	0.008471	0.190701	0.674841	0.109*	0.5
N1	0.3655 (2)	0.13927 (11)	0.53175 (11)	0.0347 (4)
N2	0.4477 (2)	0.01757 (11)	0.63553 (12)	0.0375 (4)
H2	0.420818	−0.037731	0.647937	0.045*
N3	0.6264 (2)	0.14173 (11)	0.69451 (11)	0.0352 (4)
O3	0.4049 (3)	0.35591 (12)	0.57654 (16)	0.0757 (6)
C1	0.3528 (2)	0.05144 (13)	0.55665 (13)	0.0320 (4)
C2	0.2422 (3)	−0.01017 (15)	0.50387 (15)	0.0423 (5)
H2A	0.235752	−0.071351	0.521863	0.051*
C3	0.1439 (3)	0.02034 (18)	0.42585 (16)	0.0488 (6)
H3	0.069354	−0.019799	0.390602	0.059*
C4	0.1559 (3)	0.11133 (18)	0.39960 (16)	0.0503 (6)
H4	0.090285	0.133564	0.346685	0.060*
C5	0.2670 (3)	0.16751 (16)	0.45378 (16)	0.0462 (5)
H5	0.275555	0.228659	0.436171	0.055*
C6	0.5767 (2)	0.05380 (13)	0.69865 (13)	0.0315 (4)
C7	0.6539 (3)	−0.00637 (14)	0.76730 (14)	0.0369 (4)
H7	0.618034	−0.067305	0.768749	0.044*
C8	0.7820 (3)	0.02557 (16)	0.83172 (15)	0.0434 (5)
H8	0.834264	−0.013415	0.877486	0.052*
C9	0.8335 (3)	0.11660 (16)	0.82839 (16)	0.0485 (5)
H9	0.919951	0.139854	0.871929	0.058*
C10	0.7542 (3)	0.17143 (15)	0.75964 (16)	0.0456 (5)
H10	0.789670	0.232347	0.757327	0.055*
C16	0.3524 (3)	0.36974 (15)	0.64708 (19)	0.0480 (6)
C15	0.2705 (3)	0.46125 (15)	0.65891 (17)	0.0473 (5)
H15A	0.341863	0.494613	0.707215	0.057*
H15B	0.167041	0.448608	0.678170	0.057*
C14	0.2323 (3)	0.52446 (14)	0.57801 (15)	0.0403 (5)
H14A	0.161271	0.492051	0.528875	0.048*
H14B	0.335121	0.539790	0.559240	0.048*
C13	0.8531 (3)	0.38678 (15)	0.40257 (19)	0.0519 (6)
H13A	0.949705	0.402554	0.377984	0.062*
H13B	0.777494	0.351921	0.357227	0.062*
C12	0.9082 (3)	0.32560 (18)	0.4846 (2)	0.0611 (7)
H12A	0.965667	0.272054	0.467267	0.073*
H12B	0.986835	0.359756	0.529059	0.073*
C11	0.7690 (3)	0.29305 (14)	0.52654 (16)	0.0420 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.04188 (14)	0.02539 (11)	0.04678 (16)	−0.00240 (9)	0.00029 (10)	0.00485 (10)
O4	0.1090 (17)	0.0462 (11)	0.0712 (14)	0.0344 (11)	−0.0072 (12)	0.0039 (9)
O2	0.1084 (17)	0.0698 (13)	0.0417 (11)	−0.0076 (12)	0.0020 (10)	0.0048 (9)
O1	0.0475 (8)	0.0476 (9)	0.0585 (11)	−0.0147 (7)	0.0204 (8)	−0.0152 (7)
O5	0.1197 (18)	0.0454 (10)	0.0540 (12)	−0.0324 (11)	0.0216 (11)	−0.0117 (8)
O6	0.068 (3)	0.060 (2)	0.095 (3)	−0.0104 (19)	0.027 (2)	−0.015 (2)
N1	0.0350 (8)	0.0316 (8)	0.0364 (9)	−0.0025 (6)	0.0044 (7)	0.0024 (7)
N2	0.0445 (9)	0.0270 (8)	0.0396 (10)	−0.0074 (7)	0.0050 (7)	0.0037 (7)
N3	0.0383 (8)	0.0266 (7)	0.0388 (9)	0.0020 (6)	0.0028 (7)	−0.0011 (6)
O3	0.0923 (14)	0.0387 (9)	0.1157 (18)	−0.0024 (9)	0.0674 (14)	−0.0157 (10)
C1	0.0309 (9)	0.0323 (9)	0.0342 (10)	−0.0020 (7)	0.0100 (7)	−0.0012 (7)
C2	0.0439 (11)	0.0360 (10)	0.0468 (13)	−0.0097 (8)	0.0090 (9)	−0.0051 (9)
C3	0.0393 (11)	0.0579 (14)	0.0463 (14)	−0.0089 (10)	0.0022 (9)	−0.0121 (11)
C4	0.0464 (12)	0.0623 (15)	0.0379 (13)	0.0038 (11)	−0.0015 (10)	0.0010 (11)
C5	0.0489 (12)	0.0428 (12)	0.0432 (13)	−0.0014 (9)	0.0011 (10)	0.0067 (9)
C6	0.0338 (9)	0.0289 (9)	0.0336 (10)	0.0031 (7)	0.0112 (7)	−0.0011 (7)
C7	0.0436 (11)	0.0317 (9)	0.0374 (11)	0.0049 (8)	0.0128 (8)	0.0034 (8)
C8	0.0459 (12)	0.0439 (12)	0.0389 (12)	0.0116 (9)	0.0052 (9)	0.0050 (9)
C9	0.0479 (12)	0.0467 (13)	0.0443 (13)	0.0032 (10)	−0.0063 (10)	−0.0024 (10)
C10	0.0490 (12)	0.0327 (10)	0.0486 (13)	−0.0028 (9)	−0.0059 (10)	−0.0032 (9)
C16	0.0352 (10)	0.0348 (11)	0.0721 (17)	−0.0011 (8)	0.0067 (10)	−0.0129 (11)
C15	0.0572 (13)	0.0351 (11)	0.0547 (14)	0.0089 (9)	0.0237 (11)	0.0008 (10)
C14	0.0405 (10)	0.0337 (10)	0.0482 (13)	−0.0049 (8)	0.0126 (9)	−0.0022 (9)
C13	0.0521 (13)	0.0379 (11)	0.0749 (18)	0.0038 (10)	0.0342 (12)	0.0127 (11)
C12	0.0382 (12)	0.0476 (13)	0.097 (2)	−0.0029 (10)	0.0115 (12)	0.0249 (13)
C11	0.0505 (12)	0.0241 (8)	0.0501 (14)	0.0025 (8)	0.0071 (10)	0.0064 (8)

Geometric parameters (Å, º) top

Zn1—O4	2.567 (2)	C3—C4	1.383 (4)
Zn1—O2	2.202 (2)	C4—H4	0.9300
Zn1—O1	2.2146 (17)	C4—C5	1.366 (3)
Zn1—N1	2.0473 (16)	C5—H5	0.9300
Zn1—N3	2.0470 (16)	C6—C7	1.407 (3)
Zn1—O3	2.0073 (19)	C7—H7	0.9300
Zn1—C11	2.563 (2)	C7—C8	1.364 (3)
O4—C16	1.231 (3)	C8—H8	0.9300
O2—C11	1.248 (3)	C8—C9	1.385 (3)
O1—C11	1.253 (3)	C9—H9	0.9300
O5—H5A	0.8500	C9—C10	1.367 (3)
O5—H5B	0.8504	C10—H10	0.9300
O6—H6A	0.8508	C16—C15	1.511 (3)
O6—H6B	0.8500	C15—H15A	0.9700
N1—C1	1.334 (2)	C15—H15B	0.9700
N1—C5	1.355 (3)	C15—C14	1.513 (3)
N2—H2	0.8600	C14—H14A	0.9700
N2—C1	1.381 (2)	C14—H14B	0.9700
N2—C6	1.380 (2)	C14—C13ⁱ	1.519 (3)
N3—C6	1.340 (2)	C13—H13A	0.9700
N3—C10	1.358 (3)	C13—H13B	0.9700
O3—C16	1.250 (3)	C13—C12	1.520 (3)
C1—C2	1.402 (3)	C12—H12A	0.9700
C2—H2A	0.9300	C12—H12B	0.9700
C2—C3	1.365 (3)	C12—C11	1.493 (3)
C3—H3	0.9300

O2—Zn1—O4	109.63 (8)	C4—C5—H5	118.1
O2—Zn1—O1	58.38 (7)	N2—C6—C7	116.65 (17)
O2—Zn1—C11	29.12 (7)	N3—C6—N2	121.67 (17)
O1—Zn1—O4	147.40 (6)	N3—C6—C7	121.68 (18)
O1—Zn1—C11	29.26 (6)	C6—C7—H7	120.3
N1—Zn1—O4	103.40 (7)	C8—C7—C6	119.32 (19)
N1—Zn1—O2	146.89 (8)	C8—C7—H7	120.3
N1—Zn1—O1	91.96 (6)	C7—C8—H8	120.3
N1—Zn1—C11	120.07 (7)	C7—C8—C9	119.4 (2)
N3—Zn1—O4	89.24 (6)	C9—C8—H8	120.3
N3—Zn1—O2	91.51 (7)	C8—C9—H9	120.8
N3—Zn1—O1	119.40 (7)	C10—C9—C8	118.5 (2)
N3—Zn1—N1	91.24 (6)	C10—C9—H9	120.8
N3—Zn1—C11	107.32 (7)	N3—C10—C9	123.5 (2)
O3—Zn1—O4	54.76 (7)	N3—C10—H10	118.2
O3—Zn1—O2	92.81 (8)	C9—C10—H10	118.2
O3—Zn1—O1	93.82 (7)	O4—C16—O3	121.2 (2)
O3—Zn1—N1	104.48 (8)	O4—C16—C15	120.0 (2)
O3—Zn1—N3	142.92 (8)	O3—C16—C15	118.8 (2)
O3—Zn1—C11	93.66 (7)	C16—C15—H15A	108.0
C11—Zn1—O4	132.29 (7)	C16—C15—H15B	108.0
C16—O4—Zn1	78.85 (16)	C16—C15—C14	117.1 (2)
C11—O2—Zn1	91.72 (15)	H15A—C15—H15B	107.3
C11—O1—Zn1	90.99 (15)	C14—C15—H15A	108.0
H5A—O5—H5B	104.5	C14—C15—H15B	108.0
H6A—O6—H6B	104.4	C15—C14—H14A	109.1
C1—N1—Zn1	126.18 (13)	C15—C14—H14B	109.1
C1—N1—C5	117.85 (18)	C15—C14—C13ⁱ	112.29 (19)
C5—N1—Zn1	115.89 (14)	H14A—C14—H14B	107.9
C1—N2—H2	113.3	C13ⁱ—C14—H14A	109.1
C6—N2—H2	113.3	C13ⁱ—C14—H14B	109.1
C6—N2—C1	133.48 (16)	C14ⁱ—C13—H13A	108.8
C6—N3—Zn1	125.79 (13)	C14ⁱ—C13—H13B	108.8
C6—N3—C10	117.58 (17)	C14ⁱ—C13—C12	113.8 (2)
C10—N3—Zn1	116.62 (13)	H13A—C13—H13B	107.7
C16—O3—Zn1	104.91 (17)	C12—C13—H13A	108.8
N1—C1—N2	121.38 (17)	C12—C13—H13B	108.8
N1—C1—C2	121.34 (18)	C13—C12—H12A	108.7
N2—C1—C2	117.28 (18)	C13—C12—H12B	108.7
C1—C2—H2A	120.2	H12A—C12—H12B	107.6
C3—C2—C1	119.5 (2)	C11—C12—C13	114.03 (19)
C3—C2—H2A	120.2	C11—C12—H12A	108.7
C2—C3—H3	120.2	C11—C12—H12B	108.7
C2—C3—C4	119.6 (2)	O2—C11—Zn1	59.17 (14)
C4—C3—H3	120.2	O2—C11—O1	118.9 (2)
C3—C4—H4	121.0	O2—C11—C12	121.4 (2)
C5—C4—C3	118.0 (2)	O1—C11—Zn1	59.75 (12)
C5—C4—H4	121.0	O1—C11—C12	119.6 (2)
N1—C5—C4	123.8 (2)	C12—C11—Zn1	179.3 (2)
N1—C5—H5	118.1

Zn1—O4—C16—O3	4.8 (2)	C1—N1—C5—C4	0.0 (3)
Zn1—O4—C16—C15	−174.0 (2)	C1—N2—C6—N3	5.6 (3)
Zn1—O2—C11—O1	−0.5 (2)	C1—N2—C6—C7	−174.1 (2)
Zn1—O2—C11—C12	−179.62 (18)	C1—C2—C3—C4	0.6 (3)
Zn1—O1—C11—O2	0.5 (2)	C2—C3—C4—C5	−0.1 (4)
Zn1—O1—C11—C12	179.63 (18)	C3—C4—C5—N1	−0.2 (4)
Zn1—N1—C1—N2	3.8 (3)	C5—N1—C1—N2	−179.40 (19)
Zn1—N1—C1—C2	−176.34 (15)	C5—N1—C1—C2	0.4 (3)
Zn1—N1—C5—C4	177.1 (2)	C6—N2—C1—N1	−7.0 (3)
Zn1—N3—C6—N2	−1.2 (3)	C6—N2—C1—C2	173.1 (2)
Zn1—N3—C6—C7	178.48 (14)	C6—N3—C10—C9	−0.1 (3)
Zn1—N3—C10—C9	−179.1 (2)	C6—C7—C8—C9	0.0 (3)
Zn1—O3—C16—O4	−6.3 (3)	C7—C8—C9—C10	−0.5 (4)
Zn1—O3—C16—C15	172.52 (17)	C8—C9—C10—N3	0.5 (4)
O4—C16—C15—C14	−171.6 (2)	C10—N3—C6—N2	179.91 (19)
N1—C1—C2—C3	−0.7 (3)	C10—N3—C6—C7	−0.4 (3)
N2—C1—C2—C3	179.1 (2)	C16—C15—C14—C13ⁱ	178.8 (2)
N2—C6—C7—C8	−179.88 (19)	C14ⁱ—C13—C12—C11	61.0 (3)
N3—C6—C7—C8	0.4 (3)	C13—C12—C11—O2	−127.6 (3)
O3—C16—C15—C14	9.6 (3)	C13—C12—C11—O1	53.3 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1	0.85	1.89	2.728 (3)	167
O5—H5B···O4ⁱⁱ	0.85	2.10	2.877 (3)	151
O6—H6A···O4	0.85	2.26	3.107 (5)	173
O6—H6B···O2ⁱⁱⁱ	0.85	2.58	3.275 (5)	140
N2—H2···O5^iv	0.86	1.97	2.824 (2)	177

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

Acknowledgements

La plateforme technique DRX de l'institut Lavoisier de Versailles is thanked for its support for the single-crystal X-ray crystallographic data collection and analysis.

Funding information

Funding for this research was provided by: the Algerian MESRS (Ministère de l'Enseignement Supérieur et de la Recherche Scientifique), the Algerian DGRSDT (Direction Générale de la Recherche Scientifique et du Développement Technologique) and the PRFU project (grant No. B00L01UN190120230003).

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