Synthesis, crystal structure and Hirshfeld surface analysis of di-μ₂-iodido-bis­[(2,2′-bi­quinoline-κ² N,N′)copper(I)]

In the layer structure of di-μ₂-iodido-bis­[(2,2′-bi­quinoline-κ² N,N′)copper(I)], π–π inter­actions provide conectivity within and between the layers.

Abstract

The mol­ecular and crystal structures of the title compound, [Cu₂I₂(C₁₈H₁₂N₂)₂], were examined by single-crystal X-ray diffraction and Hirshfeld surface analysis. The Cu atom is coordinated in a distorted tetra­hedral geometry by two N atoms from the 2,2′-bi­quinoline ligands and the two μ₂-bridging iodide ligands. The mol­ecules are in contact via π–π-stacking inter­actions. Hirshfeld surface analysis showed that the most important contributions to the inter­molecular inter­actions are H⋯H (39.7%), H⋯I/I⋯H (17.8%), C⋯H/H⋯C (17.5%), C⋯C (16.5%), N⋯C/C⋯N (3.9%) and N⋯H/H⋯N (3.5%).

1. Chemical context

Metal complexes with N-heterocyclic ligands find wide applications in various fields such as catalysis and medicine, among others (Delgado-Rebollo et al., 2019 ▸; Novikov et al., 2021 ▸; Fong, 2016 ▸; Artemjev et al., 2022 ▸). Copper(I) bypiridine complexes are of inter­est because of their structural peculiarities, cuprophilic inter­actions, and important photochemical properties. Therefore, bypyridine-type systems are often the ligands of choice to explore new metal complexes with potentially useful properties (Ferraro et al., 2022 ▸; Starosta et al., 2012 ▸; Vatsadze et al., 2010 ▸). 2,2′-Bi­quinoline is an important and widely employed di­imine ligand. The geometry of the resulting metal derivatives depends on the ligand and counter-ion, the metal:ligand ratio and the solvent and synthetic conditions. Here we report the preparation and structural characterization of a copper iodide complex with 2,2′-bi­quinoline. We used Hirshfeld surface analysis to estimate the contribution of non-covalent inter­actions to the crystal structure.

2. Structural commentary

The title compound crystallizes in the centrosymmetric space group P with one crystallographically independent mol­ecule in the unit cell. The mol­ecular structure is illustrated in Fig. 1 ▸. The Cu atom is coordinated in a distorted tetra­hedral geometry (Table 1 ▸) by two nitro­gen atoms from the 2,2′-bi­quinoline ligands and the two μ₂-bridged iodide ligands. The Cu1—I1 and Cu1ⁱ—I1 distances [symmetry code: (i) −x + 1, −y, −z + 1] are 2.5734 (2) and 2.6487 (2) Å, which are close to the distances in similar compounds (Sun et al., 2013 ▸; Starosta et al., 2012 ▸) with a substituted quinoline ligand. The Cu—N distances of 2.0930 (13) and 2.0900 (14) Å are almost equal within standard uncertainty.

Figure 1.

Mol­ecular structure of the title compound, including atom and ring labelling. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (i) −x + 1, −y, −z + 1.]

Table 1. Selected geometric parameters (Å, °).

I1—Cu1	2.5734 (2)	Cu1—N2	2.0900 (14)
I1—Cu1i	2.6487 (2)	Cu1—N1	2.0930 (13)
Cu1—I1—Cu1i	68.829 (8)	N2—Cu1—I1i	110.91 (4)
N2—Cu1—N1	79.28 (5)	N1—Cu1—I1i	106.99 (4)
N2—Cu1—I1	122.14 (4)	I1—Cu1—I1i	111.171 (8)
N1—Cu1—I1	122.34 (4)

Symmetry code: (i) .

The quinoline fragments in the bi­quinoline ligand adopt, as expected, a planar geometry. The maximum and minimum deviations of the atoms from these planes are between −0.018 (2) and 0.026 (2) Å. The angle between the quinolines described by rings 1/2 (as defined in Fig. 1 ▸) is 5.08 (9)° and between 3/4 is 0.59 (8)°. Then, the quinoline formed by rings 1 and 2 (ring 5) makes an angle of 7.56 (5)° with the quinoline described by rings 3/4 (ring 6).

3. Supra­molecular features

The crystal packing is shown in Fig. 2 ▸, viewed down the c axis. Mol­ecules both within the layers and between them are connected by π–π-stacking inter­actions between six-membered rings of the quinoline rings. The π–π-stacking inter­action parameters are presented in Table 2 ▸. Ring 4, defined by N2/C18/C10–C13 in Fig. 1 ▸, participates in the shortest inter­actions. The contact with another ring 4, related by the symmetry operation −x, −y + 1, −z + 1, is perhaps the most efficient, based on the distance, the angle between the planes, and the shift between ring centroids.

Figure 2.

View along the c axis of the crystal packing of the title compound, showing the stacking of layers formed by the Cu complex.

Table 2. π–π-stacking inter­action parameters (Å, °).

Ring 1	Ring No.	Ring 2	Ring No.	Angle	Centroid–centroid distance	Shift distance between ring centroids
C1–C6	1	C1–C6(−x + 1, −y, −z + 2)	1	0.000	3.874	1.459
C13–C18	3	N1/C1/C6–C9(−x + 1, −y + 1, −z + 1)	2	4.772	3.711	1.480
		N2/C18/C10–C13(−x, −y + 1, −z + 1)	4	0.590	3.665	1.602
N1/C1/C6–C9	2	N2/C18/C10–C13(−x + 1, −y + 1, −z + 1)	4	5.301	3.564	1.139
		C13–C18(−x + 1, −y + 1, −z + 1)	3	4.772	3.711	1.283
N2/C18/C10–C13	4	N2/C18/C10–C13(−x, −y + 1, −z + 1)	4	0.000	3.652	1.555
		C13–C18(−x, −y + 1, −z + 1)	3	0.590	3.665	1.579
		N1/C1/C6–C9(−x + 1, −y + 1, −z + 1)	2	5.301	3.564	1.068

4. Database survey

A search in the Cambridge Structural Database (CSD, Version 5.43, update of 2022; Groom et al., 2016 ▸) showed only a few hits for bis­[(μ₂-halogen)-2,2′-bi­quinoline-di-copper(I)]. We only found data for compounds with substituted quinoline rings in position-4 with carboxyl­ate fragments. All compounds crystallize in the triclinic space group P . In IRIVIP (Vatsadze et al., 2010 ▸), n-hexyl carboxyl­ate groups are attached to the quinoline rings at position 4. In YIJFAA, YIJFEE, and YIJFII (Sun et al., 2013 ▸), ethyl carboxyl­ate fragments are attached, and in PAYKIL (Starosta et al., 2012 ▸), there are methyl carboxyl­ate fragments. In IRIVIP and YIJFAA, instead of the iodine atom, as in the title structure, there are chlorine atoms; in YIJFEE, there are bromine atoms. In other structures, the copper atoms are bonded through iodine atoms.

5. Hirshfeld surface analysis

Crystal Explorer21 was used to calculate the Hirshfeld surfaces and two-dimensional fingerprint plots (Spackman et al., 2021 ▸). The donor–acceptor groups are visualized using a standard (high) surface resolution and d _norm surfaces are mapped over a fixed colour scale from −0.0579 (red) to 1.3919 (blue) a.u., as illustrated in Fig. 3 ▸(a). Red spots on the surface correspond to C⋯C and I⋯H inter­actions. The presence of π-stacking inter­actions is confirmed by the characteristic red and blue triangles on the shape-index surface [Fig. 3 ▸(b)]. Fingerprint plots of the most important non-covalent inter­actions for the title compound are shown in Fig. 4 ▸. The largest contribution to the crystal packing is made by contacts of the H⋯H type (39.7%). Then contacts of the H⋯I/I⋯H and C⋯H/H⋯C types make approximately equal contributions (17.8 and 17.5%, respectively). C⋯C inter­actions responsible for π-stacking contribute 16.5%. Contacts that contribute less than 1% are not shown in Fig. 4 ▸.

Figure 3.

Hirshfeld surface mapped over (a) d _norm and (b) shape-index to visualize the inter­actions in the title compound.

Figure 4.

Two-dimensional fingerprint plots for the title compound divided into H⋯H (39.7%), H⋯I/I⋯H (17.8%), C⋯H/H⋯C (17.5%), C⋯C (16.5%), N⋯C/C⋯N (3.9%) and N⋯H/H⋯N (3.5%) inter­actions.

6. Synthesis and crystallization

The title compound was prepared by refluxing CuI with one equivalent of 2,2′-bi­quinoline in ethanol for 24 h. The compound precipitates as a purple solid in 87% yield. Found (%): C, 48.39; H, 2.71; N, 6.27. forC₃₆H₂₄Cu₂I₂N₄. Calculated (%): C, 48.61; H, 2.64; N, 6.19.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. C-bound H atoms were placed at calculated positions (C—H = 0.95 Å) and refined using a riding model with [U _iso(H) = 1.2U _eq(C)].

Table 3. Experimental details.

Crystal data
Chemical formula	[Cu2I2(C18H12N2)2]
M r	893.49
Crystal system, space group	Triclinic, P
Temperature (K)	100
a, b, c (Å)	8.2032 (2), 9.4084 (3), 10.8312 (3)
α, β, γ (°)	70.9328 (8), 76.1237 (9), 74.2486 (9)
V (Å3)	749.84 (4)
Z	1
Radiation type	Mo Kα
μ (mm−1)	3.51
Crystal size (mm)	0.12 × 0.10 × 0.06
Data collection
Diffractometer	Bruker D8 QUEST PHOTON-III CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 ▸)
T min, T max	0.656, 0.798
No. of measured, independent and observed [I > 2σ(I)] reflections	22231, 5464, 4875
R int	0.030
(sin θ/λ)max (Å−1)	0.759
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.021, 0.050, 1.07
No. of reflections	5464
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρmax, Δρmin (e Å−3)	0.93, −1.00

Computer programs: APEX3 (Bruker, 2018 ▸), SAINT (Bruker, 2013 ▸), SHELXT (Sheldrick, 2015a ▸), SHELXL (Sheldrick, 2015b ▸) and SHELXTL (Sheldrick, 2008 ▸).

Supplementary Material

CCDC reference: 2237760

Additional supporting information: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Crystal data

[Cu2I2(C18H12N2)2]	Z = 1
Mr = 893.49	F(000) = 432
Triclinic, P1	Dx = 1.979 Mg m−3
a = 8.2032 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4084 (3) Å	Cell parameters from 9951 reflections
c = 10.8312 (3) Å	θ = 2.3–32.6°
α = 70.9328 (8)°	µ = 3.51 mm−1
β = 76.1237 (9)°	T = 100 K
γ = 74.2486 (9)°	Plate, red
V = 749.84 (4) Å3	0.12 × 0.10 × 0.06 mm

Data collection

Bruker D8 QUEST PHOTON-III CCD diffractometer	4875 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.030
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 32.6°, θmin = 2.3°
Tmin = 0.656, Tmax = 0.798	h = −12→12
22231 measured reflections	k = −14→14
5464 independent reflections	l = −16→16

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021	H-atom parameters constrained
wR(F2) = 0.050	w = 1/[σ2(Fo2) + (0.0241P)2 + 0.2045P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
5464 reflections	Δρmax = 0.93 e Å−3
200 parameters	Δρmin = −1.00 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: difference Fourier map	Extinction coefficient: 0.00061 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.72676 (2)	0.05497 (2)	0.36228 (2)	0.01463 (4)
Cu1	0.47151 (3)	0.14895 (2)	0.52815 (2)	0.01482 (5)
N1	0.50362 (17)	0.22489 (16)	0.68043 (14)	0.0137 (2)
N2	0.32363 (17)	0.37275 (15)	0.48351 (13)	0.0126 (2)
C1	0.5986 (2)	0.14322 (19)	0.77875 (16)	0.0149 (3)
C2	0.7206 (2)	0.0086 (2)	0.76410 (18)	0.0188 (3)
H2	0.7335	−0.0253	0.6881	0.023*
C3	0.8205 (2)	−0.0730 (2)	0.86007 (19)	0.0225 (3)
H3	0.9050	−0.1616	0.8486	0.027*
C4	0.7991 (3)	−0.0268 (2)	0.97589 (19)	0.0235 (4)
H4	0.8658	−0.0869	1.0430	0.028*
C5	0.6831 (2)	0.1034 (2)	0.99178 (18)	0.0221 (3)
H5	0.6688	0.1333	1.0701	0.027*
C6	0.5837 (2)	0.1942 (2)	0.89164 (16)	0.0168 (3)
C7	0.4734 (2)	0.3365 (2)	0.89624 (17)	0.0204 (3)
H7	0.4603	0.3741	0.9702	0.024*
C8	0.3849 (2)	0.4209 (2)	0.79434 (17)	0.0186 (3)
H8	0.3134	0.5187	0.7954	0.022*
C9	0.4017 (2)	0.35984 (18)	0.68682 (16)	0.0134 (3)
C10	0.30656 (19)	0.44564 (18)	0.57445 (16)	0.0130 (3)
C11	0.2064 (2)	0.59515 (18)	0.56565 (17)	0.0151 (3)
H11	0.1989	0.6436	0.6318	0.018*
C12	0.1199 (2)	0.67017 (18)	0.46130 (17)	0.0161 (3)
H12	0.0505	0.7703	0.4552	0.019*
C13	0.1348 (2)	0.59756 (18)	0.36296 (16)	0.0135 (3)
C14	0.0488 (2)	0.6683 (2)	0.25249 (17)	0.0171 (3)
H14	−0.0225	0.7681	0.2431	0.021*
C15	0.0680 (2)	0.5933 (2)	0.15911 (17)	0.0183 (3)
H15	0.0103	0.6413	0.0850	0.022*
C16	0.1738 (2)	0.4440 (2)	0.17292 (17)	0.0181 (3)
H16	0.1868	0.3931	0.1074	0.022*
C17	0.2579 (2)	0.37192 (19)	0.27946 (17)	0.0162 (3)
H17	0.3279	0.2717	0.2876	0.019*
C18	0.23990 (19)	0.44731 (18)	0.37738 (16)	0.0129 (3)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
I1	0.01422 (5)	0.01364 (5)	0.01633 (6)	−0.00129 (3)	−0.00081 (3)	−0.00714 (4)
Cu1	0.01437 (9)	0.01477 (9)	0.01559 (10)	0.00062 (7)	−0.00375 (7)	−0.00671 (7)
N1	0.0120 (6)	0.0154 (6)	0.0140 (6)	−0.0033 (5)	−0.0023 (5)	−0.0041 (5)
N2	0.0117 (5)	0.0134 (6)	0.0131 (6)	−0.0013 (5)	−0.0023 (4)	−0.0049 (5)
C1	0.0130 (7)	0.0179 (7)	0.0145 (7)	−0.0057 (6)	−0.0020 (5)	−0.0035 (6)
C2	0.0187 (8)	0.0184 (7)	0.0188 (8)	−0.0028 (6)	−0.0069 (6)	−0.0028 (6)
C3	0.0211 (8)	0.0196 (8)	0.0249 (9)	−0.0041 (7)	−0.0097 (7)	0.0003 (7)
C4	0.0250 (9)	0.0243 (9)	0.0207 (8)	−0.0102 (7)	−0.0117 (7)	0.0042 (7)
C5	0.0252 (9)	0.0282 (9)	0.0150 (7)	−0.0111 (7)	−0.0076 (6)	−0.0013 (7)
C6	0.0149 (7)	0.0234 (8)	0.0133 (7)	−0.0081 (6)	−0.0018 (5)	−0.0036 (6)
C7	0.0183 (8)	0.0309 (9)	0.0160 (8)	−0.0060 (7)	−0.0015 (6)	−0.0121 (7)
C8	0.0170 (7)	0.0244 (8)	0.0175 (8)	−0.0024 (6)	−0.0030 (6)	−0.0113 (7)
C9	0.0113 (6)	0.0162 (7)	0.0138 (7)	−0.0027 (5)	−0.0015 (5)	−0.0059 (6)
C10	0.0103 (6)	0.0148 (6)	0.0145 (7)	−0.0032 (5)	−0.0009 (5)	−0.0053 (5)
C11	0.0147 (7)	0.0140 (6)	0.0186 (7)	−0.0033 (5)	−0.0016 (5)	−0.0077 (6)
C12	0.0152 (7)	0.0118 (6)	0.0206 (8)	−0.0023 (5)	−0.0009 (6)	−0.0055 (6)
C13	0.0116 (6)	0.0118 (6)	0.0159 (7)	−0.0019 (5)	−0.0022 (5)	−0.0026 (5)
C14	0.0137 (7)	0.0162 (7)	0.0181 (8)	−0.0016 (6)	−0.0033 (6)	−0.0012 (6)
C15	0.0175 (7)	0.0188 (7)	0.0166 (7)	−0.0013 (6)	−0.0058 (6)	−0.0023 (6)
C16	0.0175 (7)	0.0212 (8)	0.0164 (7)	−0.0011 (6)	−0.0043 (6)	−0.0077 (6)
C17	0.0152 (7)	0.0162 (7)	0.0180 (7)	−0.0006 (6)	−0.0036 (6)	−0.0072 (6)
C18	0.0104 (6)	0.0135 (6)	0.0145 (7)	−0.0021 (5)	−0.0016 (5)	−0.0041 (5)

Geometric parameters (Å, º)

I1—Cu1	2.5734 (2)	C7—C8	1.369 (3)
I1—Cu1i	2.6487 (2)	C7—H7	0.9500
Cu1—N2	2.0900 (14)	C8—C9	1.422 (2)
Cu1—N1	2.0930 (13)	C8—H8	0.9500
Cu1—I1i	2.6487 (2)	C9—C10	1.488 (2)
Cu1—Cu1i	2.9520 (4)	C10—C11	1.409 (2)
N1—C9	1.330 (2)	C11—C12	1.367 (2)
N1—C1	1.367 (2)	C11—H11	0.9500
N2—C10	1.3354 (19)	C12—C13	1.409 (2)
N2—C18	1.369 (2)	C12—H12	0.9500
C1—C2	1.414 (2)	C13—C14	1.415 (2)
C1—C6	1.421 (2)	C13—C18	1.423 (2)
C2—C3	1.374 (2)	C14—C15	1.369 (2)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.415 (3)	C15—C16	1.418 (2)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.365 (3)	C16—C17	1.372 (2)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.418 (2)	C17—C18	1.418 (2)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.406 (3)
Cu1—I1—Cu1i	68.829 (8)	C8—C7—H7	119.9
N2—Cu1—N1	79.28 (5)	C6—C7—H7	119.9
N2—Cu1—I1	122.14 (4)	C7—C8—C9	118.99 (16)
N1—Cu1—I1	122.34 (4)	C7—C8—H8	120.5
N2—Cu1—I1i	110.91 (4)	C9—C8—H8	120.5
N1—Cu1—I1i	106.99 (4)	N1—C9—C8	122.17 (15)
I1—Cu1—I1i	111.171 (8)	N1—C9—C10	116.58 (13)
N2—Cu1—Cu1i	141.62 (4)	C8—C9—C10	121.24 (15)
N1—Cu1—Cu1i	136.76 (4)	N2—C10—C11	122.82 (15)
I1—Cu1—Cu1i	56.791 (7)	N2—C10—C9	115.92 (14)
I1i—Cu1—Cu1i	54.380 (7)	C11—C10—C9	121.26 (14)
C9—N1—C1	119.18 (14)	C12—C11—C10	119.63 (14)
C9—N1—Cu1	113.35 (11)	C12—C11—H11	120.2
C1—N1—Cu1	126.92 (11)	C10—C11—H11	120.2
C10—N2—C18	118.23 (14)	C11—C12—C13	119.38 (15)
C10—N2—Cu1	113.89 (11)	C11—C12—H12	120.3
C18—N2—Cu1	127.82 (10)	C13—C12—H12	120.3
N1—C1—C2	118.85 (15)	C12—C13—C14	122.40 (15)
N1—C1—C6	121.75 (15)	C12—C13—C18	117.93 (15)
C2—C1—C6	119.33 (16)	C14—C13—C18	119.67 (14)
C3—C2—C1	119.82 (17)	C15—C14—C13	120.22 (16)
C3—C2—H2	120.1	C15—C14—H14	119.9
C1—C2—H2	120.1	C13—C14—H14	119.9
C2—C3—C4	120.78 (18)	C14—C15—C16	120.11 (16)
C2—C3—H3	119.6	C14—C15—H15	119.9
C4—C3—H3	119.6	C16—C15—H15	119.9
C5—C4—C3	120.43 (17)	C17—C16—C15	121.04 (15)
C5—C4—H4	119.8	C17—C16—H16	119.5
C3—C4—H4	119.8	C15—C16—H16	119.5
C4—C5—C6	120.13 (17)	C16—C17—C18	119.85 (15)
C4—C5—H5	119.9	C16—C17—H17	120.1
C6—C5—H5	119.9	C18—C17—H17	120.1
C7—C6—C5	122.99 (16)	N2—C18—C17	118.90 (14)
C7—C6—C1	117.63 (16)	N2—C18—C13	122.00 (14)
C5—C6—C1	119.34 (17)	C17—C18—C13	119.10 (15)
C8—C7—C6	120.15 (15)
C9—N1—C1—C2	−173.05 (15)	C18—N2—C10—C9	−179.42 (13)
Cu1—N1—C1—C2	16.1 (2)	Cu1—N2—C10—C9	3.07 (17)
C9—N1—C1—C6	3.8 (2)	N1—C9—C10—N2	4.8 (2)
Cu1—N1—C1—C6	−166.98 (11)	C8—C9—C10—N2	−175.83 (14)
N1—C1—C2—C3	178.35 (16)	N1—C9—C10—C11	−174.64 (14)
C6—C1—C2—C3	1.4 (3)	C8—C9—C10—C11	4.7 (2)
C1—C2—C3—C4	2.0 (3)	N2—C10—C11—C12	0.9 (2)
C2—C3—C4—C5	−2.6 (3)	C9—C10—C11—C12	−179.63 (15)
C3—C4—C5—C6	−0.4 (3)	C10—C11—C12—C13	−1.0 (2)
C4—C5—C6—C7	−174.13 (17)	C11—C12—C13—C14	179.90 (16)
C4—C5—C6—C1	3.8 (3)	C11—C12—C13—C18	0.2 (2)
N1—C1—C6—C7	−3.1 (2)	C12—C13—C14—C15	179.67 (15)
C2—C1—C6—C7	173.76 (16)	C18—C13—C14—C15	−0.7 (2)
N1—C1—C6—C5	178.82 (15)	C13—C14—C15—C16	0.2 (3)
C2—C1—C6—C5	−4.3 (2)	C14—C15—C16—C17	0.3 (3)
C5—C6—C7—C8	177.99 (17)	C15—C16—C17—C18	−0.3 (3)
C1—C6—C7—C8	0.0 (2)	C10—N2—C18—C17	179.51 (14)
C6—C7—C8—C9	2.2 (3)	Cu1—N2—C18—C17	−3.4 (2)
C1—N1—C9—C8	−1.5 (2)	C10—N2—C18—C13	−0.9 (2)
Cu1—N1—C9—C8	170.55 (12)	Cu1—N2—C18—C13	176.23 (11)
C1—N1—C9—C10	177.85 (13)	C16—C17—C18—N2	179.42 (15)
Cu1—N1—C9—C10	−10.14 (17)	C16—C17—C18—C13	−0.2 (2)
C7—C8—C9—N1	−1.6 (3)	C12—C13—C18—N2	0.7 (2)
C7—C8—C9—C10	179.14 (15)	C14—C13—C18—N2	−178.92 (15)
C18—N2—C10—C11	0.1 (2)	C12—C13—C18—C17	−179.65 (15)
Cu1—N2—C10—C11	−177.45 (12)	C14—C13—C18—C17	0.7 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Funding Statement

Funding for this research was provided by: Ministry of Science and Higher Education of the Russian Federation (subject No. 122011300061-3). This work was supported by the RUDN University Strategic Academic Leadership Program: Russian Foundation for Basic Research (grant No. 21-53-54001).