catena-Poly[[(8-amino­quinoline)­cobalt(II)]-di-μ-azido]

Setifi, F.; Setifi, Z.; Geiger, D.K.; Al-Douh, M.H.; Addala, A.

doi:10.1107/S2414314624008496

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 9| September 2024| x240849

https://doi.org/10.1107/S2414314624008496

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access

catena-Poly[[(8-aminoquinoline)cobalt(II)]-di-μ-azido]

Fatima Setifi,^a ^* Zouaoui Setifi,^b,^a David K. Geiger,^c ^* Mohammed Hadi Al-Douh ^d and Abderezak Addala ^a

^aLaboratoire de Chimie, Ingénierie Moléculaire et Nanostructures (LCIMN), Université Ferhat Abbas Sétif 1, Sétif 19000, Algeria, ^bDépartement de Technologie, Faculté de Technologie, Université 20 Août 1955-Skikda, BP 26, Route d'El-Hadaiek, Skikda 21000, Algeria, ^cDepartment of Chemistry, SUNY-College at Geneseo, Geneseo, NY 14454, USA, and ^dChemistry Department, Faculty of Science, Hadhramout University, Mukalla, Hadhramout, Yemen
^*Correspondence e-mail: fatima.setifi@univ-setif.dz, geiger@geneseo.edu

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 19 August 2024; accepted 27 August 2024; online 6 September 2024)

The title coordination polymer, [Co(N₃)₂(C₉H₈N₂)]_n, was synthesized solvothermally. The Co^II atom exhibits a distorted octahedral [CoN₆] coordination geometry with a bidentate 8-aminoquinoline ligand and four azide ligands. Bridging azide ligands result in chains extending along [100]. N—H⋯N hydrogen bonds join the chains to give an extended structure with sheets parallel to (002).

Keywords: crystal structure; cobalt(II); 8-aminoquinoline (8-aquin); azide anion.

CCDC reference: 2380120

Structure description

Pseudohalide and polynitrile compounds derived from transition-metal ions are of great interest from the perspective of their magnetic properties, rich molecular architectures and for their topologies (Atmani et al., 2008 ; Benmansour et al., 2008 , 2010 , 2012 ; Addala et al., 2015 ; Setifi et al., 2018 , 2019 ; Dmitrienko et al., 2020 ; Yuste et al., 2009 ; Merabet et al., 2022 ).

One of the pseudohalide ligands that has received much attention in the last decade is the azide [N₃⁻] ion, partly due to its ability to produce a wide variety of coordination compounds with different nuclearities ranging from simple mononuclear to polynuclear species. Different bonding modes are observed with the azide ion, which result in the formation of one-, two- and three-dimensional polymeric assemblies (Escuer et al., 2006 ).

As a part of our continuing study of the structural and magnetic properties of transition-metal complexes containing both azide and polypyridyl units (Setifi, Ghazzali et al., 2016 ; Setifi, Knaust et al., 2016 ; Setifi, Moon et al., 2016 ; Benamara et al., 2021 ; Merabet et al., 2023 ; Setifi, Setifi et al., 2022 , 2023 ), we report herein the crystal and molecular structure of a one-dimensional coordination polymer, (I), based on 8-aminoquinoline (8-aquin) as co-ligand and the azide anion as ligand with two different coordination modes.

The asymmetric unit of (I) is composed of a Co^II ion, a bidentate 8-aquin ligand and two azide ligands. The distorted octahedral coordination sphere is completed by two additional azide ligands. One of the azide anions binds to two Co centers in a 1,3 bidentate mode, whereas the other one connects two Co centers in a 1,1 bidentate mode. The resulting coordination geometry and supramolecular association is shown in Fig. 1. Pertinent Co—N bond lengths are exhibited in Table 1.

Table 1
Selected bond lengths (Å)

Co1—N1	2.1020 (13)	Co1—N8	2.1684 (13)
Co1—N7	2.1100 (12)	Co1—N6ⁱ	2.1685 (15)
Co1—N4	2.1222 (17)	Co1—N1ⁱⁱ	2.2047 (12)
Symmetry codes: (i) ; (ii) .

Figure 1
Representation of (the title compound showing the atom-labeling scheme. Non-H atom anisotropic displacement parameters are represented at the 50% probability level. Symmetry codes: (a) −x, −y + 1, −z + 1; (b) −x + 1, −y + 1, −z + 1.

The bridging ligands result in polymeric chains extending parallel to [100], as shown in Fig. 2. The chains are composed of Co^II ions joined by alternating bis μ-(1,1-N₃) units and bis μ-(1,3-N₃) units with corresponding Co⋯Co separations of 3.2817 (5) and 5.2427 (7) Å, respectively. The angle between the (N₃)₂ mean plane of the double end-to-end azide bridges and the plane defined by the Co^II and the bonded N_azide atom is 20.20 (14)°, corresponding to a flattened chair configuration for the eight-membered ring. For a flat bridge, an angle of 0° would be observed. This angle compares to values of 8.2 (2) and 25.6 (1)° for the structurally similarly bridged polymorphic Fe^II complexes with a 5,5′-dimethyl-2,2′-bipyridine ligand (Setifi, Bernès et al., 2022 ). In the 8-acquin complexes of Mn^II and Co^II, the comparable angles are 20.3 (6)° and 25.5 (4)°, respectively (Benamara et al., 2021).

Figure 2
Partial packing diagram showing the polymeric chain parallel to [100]. H atoms are not shown. Symmetry codes: (a) −x, −y + 1, −z + 1; (b) −x + 1, −y + 1, −z + 1.

N—H⋯N hydrogen-bonding interactions are observed in the extended structure (Table 2, Fig. 3). Within individual chains, R₂²(8) hydrogen-bonded rings are observed (Fig. 4). The polymeric chains are joined by hydrogen-bonding bridges involving the 8-amino substituent on the quinoline ligands and the terminal nitrogen atom of the μ-(1,1-azide) ligands of adjacent chains, resulting in sheets parallel to (002) containing N—H⋯N hydrogen-bond-derived R₂²(12) interchain rings, as seen in Figs. 3 and 5.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8A⋯N3ⁱⁱⁱ	0.84 (3)	2.46 (3)	3.218 (2)	151 (2)
N8—H8B⋯N4ⁱⁱ	0.88 (3)	2.73 (3)	3.502 (3)	148 (2)
Symmetry codes: (ii) ; (iii) .

Figure 3
Partial packing diagram showing sheets parallel to (002) formed by N—H⋯N bonds. Only H atoms involved in the interactions are represented. Symmetry codes: (a) −x, −y + 1, −z + 1; (b) −x + 1, −y + 1, −z + 1; (c) x, y + 1, z; (d) x + 1, y + 1, z; (e). −x, −y, −z + 1.

Figure 4
View of the intrachain R₂²(8) N—H⋯N motif. Only H atoms involved in the hydrogen bonds are shown. Symmetry code: (a) −x, −y + 1, −z + 1.

Figure 5
View of the interchain R₂²(12) N—H⋯N motif. Only H atoms involved in hydrogen bonding are shown. Symmetry code: (a) −x, −y, −z + 1.

Synthesis and crystallization

The title compound was prepared solvothermally under autogenous pressure from a mixture of cobalt(II) sulfate heptahydrate (28 mg, 0.1 mmol), 8-aminoquinoline (14 mg, 0.1 mmol) and sodium azide (13 mg, 0.2 mmol) in a mixture of water and ethanol (3:1 v/v, 20 ml). This mixture was sealed in a Teflon-lined autoclave and held at 393 K for 2 days, and then cooled to ambient temperature at a rate of 10 K h⁻¹ to give the product (yield 38%).

Refinement

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

Table 3
Experimental details

Crystal data
Chemical formula	[Co(N₃)₂(C₉H₈N₂)]
M_r	287.16
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	301
a, b, c (Å)	7.3526 (10), 8.3354 (13), 10.4053 (17)
α, β, γ (°)	97.221 (6), 102.413 (6), 111.334 (5)
V (Å³)	565.36 (15)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.51
Crystal size (mm)	0.35 × 0.30 × 0.22

Data collection
Diffractometer	Xcalibur CCD Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2014 $[Agilent (2014). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ )
T_min, T_max	0.769, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	29909, 4356, 3882
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.773

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.088, 1.06
No. of reflections	4356
No. of parameters	171
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.33
Computer programs: CrysAlis CCD and CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ), SHELXS97 (Sheldrick, 2008 ), SHELXL2014/7 (Sheldrick, 2015 ), ShelXle (Hübschle et al., 2011 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2380120

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314624008496/bt4154sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624008496/bt4154Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314624008496/bt4154Isup3.mol

checkCIF report

Computing details top

catena-Poly[[(8-aminoquinoline)cobalt(II)]-di-µ-azido-κ⁴N¹:N³-[(8-aminoquinoline)cobalt(II)]-di-µ-azido-κ⁴N¹:N¹] top

Crystal data top

[Co(N₃)₂(C₉H₈N₂)]	Z = 2
M_r = 287.16	F(000) = 290
Triclinic, P1	D_x = 1.687 Mg m⁻³
a = 7.3526 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3354 (13) Å	Cell parameters from 4847 reflections
c = 10.4053 (17) Å	θ = 4.2–32.3°
α = 97.221 (6)°	µ = 1.51 mm⁻¹
β = 102.413 (6)°	T = 301 K
γ = 111.334 (5)°	Block, purple
V = 565.36 (15) Å³	0.35 × 0.30 × 0.22 mm

Data collection top

Xcalibur CCD, Sapphire3 diffractometer	4356 independent reflections
Radiation source: fine-focus sealed tube	3882 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 33.3°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −11→11
T_min = 0.769, T_max = 1.000	k = −12→12
29909 measured reflections	l = −16→16

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0409P)² + 0.1945P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
4356 reflections	Δρ_max = 0.72 e Å⁻³
171 parameters	Δρ_min = −0.33 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. H atoms bonded to C were refined using a riding model, H atoms bonded to N were freely refined.

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

	x	y	z	U_iso*/U_eq
Co1	0.19673 (3)	0.48517 (2)	0.59913 (2)	0.03117 (6)
N1	0.0070 (2)	0.37549 (18)	0.40029 (12)	0.0377 (3)
N2	−0.0569 (3)	0.21922 (19)	0.35544 (13)	0.0432 (3)
N3	−0.1176 (4)	0.0705 (2)	0.3110 (2)	0.0744 (6)
N4	0.4085 (3)	0.7020 (2)	0.5489 (2)	0.0668 (6)
N5	0.5181 (2)	0.68214 (18)	0.48714 (14)	0.0386 (3)
N6	0.6244 (3)	0.6686 (2)	0.42249 (18)	0.0515 (4)
N7	0.30637 (18)	0.58191 (15)	0.81040 (12)	0.0309 (2)
N8	0.0067 (2)	0.26670 (17)	0.66848 (13)	0.0351 (2)
H8A	0.023 (4)	0.175 (3)	0.642 (2)	0.057 (7)*
H8B	−0.122 (4)	0.246 (4)	0.635 (3)	0.069 (8)*
C1	0.2139 (2)	0.47062 (17)	0.88451 (13)	0.0291 (2)
C2	0.0569 (2)	0.30410 (18)	0.81392 (14)	0.0313 (2)
C3	−0.0357 (3)	0.1882 (2)	0.88582 (19)	0.0423 (3)
H3	−0.1379	0.0784	0.8402	0.051*
C4	0.0224 (3)	0.2336 (3)	1.0283 (2)	0.0528 (5)
H4	−0.0415	0.153	1.0754	0.063*
C5	0.1714 (3)	0.3946 (3)	1.09811 (17)	0.0485 (4)
H5	0.2072	0.4232	1.192	0.058*
C6	0.2705 (2)	0.5171 (2)	1.02765 (14)	0.0380 (3)
C7	0.4267 (3)	0.6859 (3)	1.09254 (17)	0.0472 (4)
H7	0.4694	0.7209	1.1863	0.057*
C8	0.5135 (3)	0.7961 (2)	1.01716 (19)	0.0477 (4)
H8	0.6143	0.9081	1.0587	0.057*
C9	0.4499 (2)	0.7397 (2)	0.87556 (17)	0.0399 (3)
H9	0.5114	0.8166	0.8252	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.03912 (11)	0.03282 (10)	0.02878 (9)	0.01827 (8)	0.01518 (7)	0.01036 (7)
N1	0.0545 (7)	0.0401 (6)	0.0290 (5)	0.0302 (6)	0.0127 (5)	0.0079 (4)
N2	0.0667 (9)	0.0457 (7)	0.0283 (5)	0.0350 (7)	0.0140 (6)	0.0078 (5)
N3	0.1122 (18)	0.0450 (9)	0.0614 (11)	0.0375 (10)	0.0127 (11)	−0.0016 (8)
N4	0.0864 (13)	0.0440 (8)	0.0944 (14)	0.0265 (8)	0.0690 (12)	0.0229 (9)
N5	0.0422 (6)	0.0372 (6)	0.0418 (6)	0.0172 (5)	0.0174 (5)	0.0138 (5)
N6	0.0596 (9)	0.0660 (10)	0.0586 (9)	0.0427 (8)	0.0341 (8)	0.0322 (8)
N7	0.0330 (5)	0.0299 (5)	0.0327 (5)	0.0154 (4)	0.0094 (4)	0.0088 (4)
N8	0.0384 (6)	0.0306 (5)	0.0355 (6)	0.0125 (5)	0.0118 (5)	0.0065 (4)
C1	0.0347 (6)	0.0331 (6)	0.0295 (5)	0.0216 (5)	0.0125 (4)	0.0111 (4)
C2	0.0363 (6)	0.0321 (6)	0.0358 (6)	0.0195 (5)	0.0169 (5)	0.0137 (5)
C3	0.0457 (8)	0.0407 (7)	0.0561 (9)	0.0227 (6)	0.0275 (7)	0.0249 (7)
C4	0.0661 (11)	0.0702 (12)	0.0570 (10)	0.0443 (10)	0.0402 (9)	0.0426 (10)
C5	0.0646 (10)	0.0722 (12)	0.0359 (7)	0.0475 (10)	0.0247 (7)	0.0257 (8)
C6	0.0479 (8)	0.0513 (8)	0.0298 (6)	0.0352 (7)	0.0123 (5)	0.0115 (6)
C7	0.0541 (9)	0.0592 (10)	0.0331 (7)	0.0383 (8)	0.0005 (6)	−0.0009 (6)
C8	0.0439 (8)	0.0418 (8)	0.0489 (9)	0.0220 (7)	−0.0035 (7)	−0.0050 (7)
C9	0.0375 (7)	0.0325 (6)	0.0465 (8)	0.0138 (5)	0.0073 (6)	0.0065 (6)

Geometric parameters (Å, º) top

Co1—N1	2.1020 (13)	N8—H8B	0.88 (3)
Co1—N7	2.1100 (12)	C1—C2	1.418 (2)
Co1—N4	2.1222 (17)	C1—C6	1.4186 (19)
Co1—N8	2.1684 (13)	C2—C3	1.371 (2)
Co1—N6ⁱ	2.1685 (15)	C3—C4	1.411 (3)
Co1—N1ⁱⁱ	2.2047 (12)	C3—H3	0.93
N1—N2	1.2012 (19)	C4—C5	1.368 (3)
N1—Co1ⁱⁱ	2.2046 (12)	C4—H4	0.93
N2—N3	1.147 (2)	C5—C6	1.410 (3)
N4—N5	1.176 (2)	C5—H5	0.93
N5—N6	1.161 (2)	C6—C7	1.417 (3)
N6—Co1ⁱ	2.1685 (15)	C7—C8	1.355 (3)
N7—C9	1.3273 (19)	C7—H7	0.93
N7—C1	1.3653 (18)	C8—C9	1.407 (2)
N8—C2	1.4427 (19)	C8—H8	0.93
N8—H8A	0.84 (3)	C9—H9	0.93

N1—Co1—N7	163.50 (5)	Co1—N8—H8B	110.0 (18)
N1—Co1—N4	94.66 (8)	H8A—N8—H8B	108 (2)
N7—Co1—N4	96.60 (7)	N7—C1—C2	117.90 (12)
N1—Co1—N8	90.80 (5)	N7—C1—C6	122.02 (13)
N7—Co1—N8	78.65 (5)	C2—C1—C6	120.08 (13)
N4—Co1—N8	173.93 (8)	C3—C2—C1	119.16 (14)
N1—Co1—N6ⁱ	93.17 (6)	C3—C2—N8	123.91 (14)
N7—Co1—N6ⁱ	98.59 (6)	C1—C2—N8	116.92 (12)
N4—Co1—N6ⁱ	91.25 (7)	C2—C3—C4	120.74 (17)
N8—Co1—N6ⁱ	85.77 (6)	C2—C3—H3	119.6
N1—Co1—N1ⁱⁱ	80.75 (5)	C4—C3—H3	119.6
N7—Co1—N1ⁱⁱ	87.21 (4)	C5—C4—C3	120.97 (16)
N4—Co1—N1ⁱⁱ	90.05 (7)	C5—C4—H4	119.5
N8—Co1—N1ⁱⁱ	93.47 (5)	C3—C4—H4	119.5
N6ⁱ—Co1—N1ⁱⁱ	173.87 (6)	C4—C5—C6	119.92 (15)
N2—N1—Co1	119.76 (10)	C4—C5—H5	120.0
N2—N1—Co1ⁱⁱ	122.01 (12)	C6—C5—H5	120.0
Co1—N1—Co1ⁱⁱ	99.25 (5)	C5—C6—C7	123.32 (15)
N3—N2—N1	179.1 (2)	C5—C6—C1	119.12 (16)
N5—N4—Co1	121.28 (13)	C7—C6—C1	117.56 (15)
N6—N5—N4	176.53 (18)	C8—C7—C6	119.57 (15)
N5—N6—Co1ⁱ	137.61 (13)	C8—C7—H7	120.2
C9—N7—C1	118.25 (13)	C6—C7—H7	120.2
C9—N7—Co1	126.30 (11)	C7—C8—C9	119.45 (16)
C1—N7—Co1	115.42 (9)	C7—C8—H8	120.3
C2—N8—Co1	111.12 (9)	C9—C8—H8	120.3
C2—N8—H8A	108.7 (17)	N7—C9—C8	123.12 (16)
Co1—N8—H8A	109.8 (17)	N7—C9—H9	118.4
C2—N8—H8B	109.3 (18)	C8—C9—H9	118.4

C9—N7—C1—C2	178.36 (12)	C3—C4—C5—C6	−0.6 (3)
Co1—N7—C1—C2	0.21 (14)	C4—C5—C6—C7	−179.72 (15)
C9—N7—C1—C6	−1.73 (19)	C4—C5—C6—C1	−0.1 (2)
Co1—N7—C1—C6	−179.88 (9)	N7—C1—C6—C5	−178.82 (12)
N7—C1—C2—C3	178.61 (12)	C2—C1—C6—C5	1.10 (19)
C6—C1—C2—C3	−1.30 (19)	N7—C1—C6—C7	0.79 (19)
N7—C1—C2—N8	−0.50 (17)	C2—C1—C6—C7	−179.29 (12)
C6—C1—C2—N8	179.58 (12)	C5—C6—C7—C8	−179.68 (15)
Co1—N8—C2—C3	−178.54 (11)	C1—C6—C7—C8	0.7 (2)
Co1—N8—C2—C1	0.52 (15)	C6—C7—C8—C9	−1.3 (2)
C1—C2—C3—C4	0.6 (2)	C1—N7—C9—C8	1.2 (2)
N8—C2—C3—C4	179.60 (14)	Co1—N7—C9—C8	179.11 (11)
C2—C3—C4—C5	0.4 (3)	C7—C8—C9—N7	0.3 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8A···N3ⁱⁱⁱ	0.84 (3)	2.46 (3)	3.218 (2)	151 (2)
N8—H8B···N4ⁱⁱ	0.88 (3)	2.73 (3)	3.502 (3)	148 (2)

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

Acknowledgements

The Service Commun de Diffraction X of the Université de Brest is thanked 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); PRFU project (grant No. B00L01UN190120230003).

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