Crystal structure of (aceto-nitrile-κN)iodido-(2-(naphthalen-1-yl)-6-{1-[(2,4,6-tri-methyl-phen-yl)imino]ethyl}-pyridine-κ2N,N')copper(I).

In the mononuclear title complex, [CuI(C2H3N)(C26H24N2)], the CuI ion has a distorted tetra-hedral coordination environment, defined by two N atoms of the chelating 2-(naphthalen-1-yl)-6-[(2,4,6-tri-methyl-phen-yl)imino]-pyridine ligand, one N atom of an aceto-nitrile ligand and one iodide ligand. Within the complex, there are weak intra-molecular C-H⋯N hydrogen bonds, while weak inter-molecular C-H⋯I inter-actions between complex mol-ecules, help to facilitate a three-dimensional network.

Chemical context

Coordination complexes of copper(I) halides bearing a variety of co-ligands have been of inter­est in coordination chemistry (Karahan et al., 2015 ▸; Dennehy et al., 2011 ▸; Oshio et al., 1996 ▸; Seward et al., 2003 ▸) due, in some measure, to their preparative accessibility, structural variability, magnetic properties (Oshio et al., 1996 ▸) and their relevance to biological or medicinal applications (Corey et al., 1987 ▸; Dias et al., 2006 ▸). The role of copper(I) is evident in several biologically important reactions, such as a di­oxy­gen carrier and models for several enzymes (Krupanidhi et al., 2008 ▸). Elsewhere, these compounds have been reported to be luminescent (Aslanidis et al., 2010 ▸; Gallego et al., 2012 ▸) and exhibit corrosion inhibit­ing properties (Tian et al., 2004 ▸). The structures of metal complexes bearing naphthyl-substituted N,N-pyridine-alkyl­amides were reported by Armitage et al. (2015 ▸) and related structures were presented by Wattanakanjana et al. (2014 ▸). Cotton et al. (1999 ▸) highlighted details of the affinity of nitrile ligands for CuI ions. Within this context, we report herein the crystal structure of the title complex, [CuI(C2H3N)(C26H24N2)].

Structural commentary

The mol­ecular structure of the title complex is shown in Fig. 1 ▸. The CuI ion is coordinated by atoms N1 and N2 of the 2-(naphthalen-1-yl)-6-[(2,4,6-tri­methyl­phen­yl)imino]­pyridine ligand, by atom N3 of an aceto­nitrile ligand and by an iodide anion (I1), leading to a distorted tetra­hedral coordination environment. The two N atoms of the bidentate ligand chelate to CuI with similar Cu—N bond lengths [Cu1—N1 = 2.091 (4), Cu1—N2 = 2.085 (4) Å]. A comparable N,N′-binding has been observed in related structures with bis­[2-(2-pyrid­yl)eth­yl]amine ligands (Osako et al., 2001 ▸). At 1.960 (5) Å, the Cu1—N3 distance is significantly shorter than the Cu—Npyridine and Cu—Nimine distances. The Cu1—I distance amounts to 2.5479 (9) Å. The N2—Cu1—N1 bite angle of the chelating ligand is 78.86 (18)°, while the N3—Cu—I angle between the monodentate aceto­nitrile and iodide ligands is closer to tetra­hedral, 112.74 (15)°. The naphthyl ring system is inclined by 58.20 (17)° to the central N=C(CH3)—pyridine moiety, whereas the tri­methyl­phenyl ring is almost perpendicular to the latter, at 84.8 (3)°. Within the complex, an intra­molecular C—H⋯N hydrogen-bonding inter­action is present, stabil­izing the mol­ecular conformation (Table 1 ▸, Fig. 1 ▸).

Figure 1

The mol­ecular structure of the title complex, with displacement ellipsoids drawn at the 50% probability level. The C—H⋯N hydrogen bond is shown as a dashed line.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26B⋯N1	0.98	2.52	2.891 (8)	102

Supra­molecular features

In the crystal, weak C—H⋯I contacts involving a phenyl H atom [C16—H16B⋯Ii, 3.958 (6) Å, 152°; symmetry code: (i) x, y − 1, z] and a H atom of the aceto­nitrile methyl group [[C28—H28B⋯Ii, 4.010 (6) Å, 109°] link the complex mol­ecules, forming a three-dimensional network (Fig. 2 ▸).

Figure 2

Part of the crystal structure, showing inter­molecular C—H⋯I inter­actions (dashed lines).

Synthesis and crystallization

All synthetic manipulations were performed under a nitro­gen atmosphere, using standard Schlenk techniques. Solvents were distilled under nitro­gen from appropriate drying agents and degassed prior to use (Armarego et al., 1996 ▸). The 2-(naphthalen-1-yl)-6-[(2,4,6-tri­methyl­phen­yl)imino]­pyridine ligand (L mes) was synthesized according to a modified literature procedure (Armitage et al., 2015 ▸).

A solution of 0.0262 g of CuI (0.137 mmol) in 5 ml of aceto­nitrile was mixed with a solution of 0.05 g of L mes (0.134 mmol) in 5 ml of aceto­nitrile. The mixture was stirred at room temperature for 24 h before evaporating the volatiles. The residue was extracted with n-hexane (5 × 3 ml). The extracts were combined and the solvent removed under reduced pressure to give a red solid which was recrystallized from aceto­nitrile solution. Yield: 54%. M.p. >253 K (decomp). 1H NMR (400 MHz, CD2Cl2): δ 1.88 [s, 6H, ortho- (CH3)2], 1.97 (s, 3H, N≡CCH3), 2.16 (s, 3H, N=CCH3), 2.20 [s, 3H, para-(CH3)2], 6.84 (s, 2H, Mes-H), 7.39 (s, 1H, Nap-H), 7.45 (t, J 7.8, 2H, Nap-H/Py–H), 7.51 (s, 1H, Py–H), 7.73 (s, 1H, Py-H), 7.81 (s, 2H, Nap-H), 7.87 (d, J 3.7, 2H, Nap-H), 8.04 (s, 1H, Nap-H). IR νmax (solid)/cm−1 1620 (C=Nimine), 1555 (C=Npy). ESI MS: m/z 428 [M–I–MeCN]+.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. Hydrogen atoms were positioned geometrically, with C—H = 0.95 Å and with U iso(H) = 1.2U eq(C) for H atoms on Csp 2 and 0.98 Å with U iso(H) = 1.5U eq(C) for H atoms on Csp 3.

Table 2

Experimental details

Crystal data
Chemical formula	[CuI(C2H3N)(C26H24N2)]
M r	595.97
Crystal system, space group	Monoclinic, P21/c
Temperature (K)	150
a, b, c (Å)	14.689 (3), 8.0775 (15), 21.861 (4)
β (°)	103.942 (3)
V (Å3)	2517.4 (8)
Z	4
Radiation type	Mo Kα
μ (mm−1)	2.11
Crystal size (mm)	0.25 × 0.07 × 0.03
Data collection
Diffractometer	Bruker APEX 2000 CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001 ▸)
T min, T max	0.679, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	19143, 4936, 2757
R int	0.125
(sin θ/λ)max (Å−1)	0.617
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.051, 0.085, 0.77
No. of reflections	4936
No. of parameters	303
H-atom treatment	H-atom parameters constrained
Δρmax, Δρmin (e Å−3)	1.13, −0.81

Computer programs: SMART and SAINT (Bruker, 2001 ▸), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989016018685/wm5341sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016018685/wm5341Isup2.hkl

CCDC reference: 1518571

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

[CuI(C2H3N)(C26H24N2)]	F(000) = 1192
Mr = 595.97	Dx = 1.572 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 639 reflections
a = 14.689 (3) Å	θ = 2.9–23.2°
b = 8.0775 (15) Å	µ = 2.11 mm−1
c = 21.861 (4) Å	T = 150 K
β = 103.942 (3)°	Needle, orange
V = 2517.4 (8) Å3	0.25 × 0.07 × 0.03 mm
Z = 4

Bruker APEX 2000 CCD area detector diffractometer	4936 independent reflections
Radiation source: fine-focus sealed tube	2757 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.125
phi and ω scans	θmax = 26.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −18→17
Tmin = 0.679, Tmax = 0.862	k = −9→9
19143 measured reflections	l = −26→26

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 0.77	w = 1/[σ2(Fo2) + (0.0178P)2] where P = (Fo2 + 2Fc2)/3
4936 reflections	(Δ/σ)max = 0.002
303 parameters	Δρmax = 1.13 e Å−3
0 restraints	Δρmin = −0.81 e Å−3

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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cu1	0.27041 (5)	0.46133 (9)	0.24724 (3)	0.0280 (2)
I1	0.27321 (3)	0.69329 (5)	0.16873 (2)	0.03325 (13)
N1	0.2948 (3)	0.5389 (6)	0.3410 (2)	0.0241 (12)
N2	0.1440 (3)	0.3972 (5)	0.2685 (2)	0.0196 (11)
N3	0.3532 (3)	0.2768 (6)	0.2390 (2)	0.0307 (13)
C1	0.3799 (4)	0.6189 (7)	0.3735 (3)	0.0241 (14)
C2	0.3847 (4)	0.7897 (8)	0.3723 (3)	0.0277 (15)
C3	0.4709 (4)	0.8651 (7)	0.3999 (3)	0.0309 (16)
H3	0.4755	0.9824	0.3996	0.037*
C4	0.5483 (4)	0.7737 (8)	0.4270 (3)	0.0322 (16)
C5	0.5416 (4)	0.6047 (8)	0.4277 (3)	0.0335 (16)
H5	0.5956	0.5412	0.4463	0.040*
C6	0.4569 (4)	0.5231 (7)	0.4015 (3)	0.0293 (15)
C7	0.2277 (4)	0.5153 (7)	0.3683 (3)	0.0245 (14)
C8	0.2289 (4)	0.5595 (7)	0.4358 (2)	0.0293 (15)
H8A	0.2892	0.6104	0.4560	0.044*
H8B	0.2200	0.4590	0.4588	0.044*
H8C	0.1781	0.6378	0.4363	0.044*
C9	0.1407 (4)	0.4362 (7)	0.3290 (3)	0.0237 (14)
C10	0.0617 (4)	0.4098 (7)	0.3511 (3)	0.0246 (14)
H10	0.0612	0.4389	0.3931	0.030*
C11	−0.0174 (4)	0.3404 (7)	0.3115 (3)	0.0260 (15)
H11	−0.0723	0.3197	0.3260	0.031*
C12	−0.0143 (4)	0.3028 (7)	0.2511 (3)	0.0249 (14)
H12	−0.0679	0.2569	0.2230	0.030*
C13	0.0668 (4)	0.3312 (7)	0.2308 (3)	0.0224 (14)
C14	0.0726 (4)	0.2803 (7)	0.1655 (3)	0.0193 (13)
C15	0.1401 (4)	0.1717 (7)	0.1593 (3)	0.0281 (15)
H15	0.1865	0.1391	0.1956	0.034*
C16	0.1429 (4)	0.1057 (7)	0.0993 (3)	0.0282 (15)
H16	0.1905	0.0295	0.0955	0.034*
C17	0.0766 (4)	0.1533 (7)	0.0478 (3)	0.0303 (16)
H17	0.0781	0.1087	0.0079	0.036*
C18	0.0056 (4)	0.2669 (7)	0.0517 (3)	0.0244 (15)
C19	0.0043 (4)	0.3361 (7)	0.1116 (3)	0.0224 (14)
C20	−0.0648 (4)	0.4581 (7)	0.1131 (3)	0.0266 (15)
H20	−0.0671	0.5070	0.1522	0.032*
C21	−0.1273 (4)	0.5060 (7)	0.0600 (3)	0.0305 (16)
H21	−0.1712	0.5906	0.0626	0.037*
C22	−0.1293 (4)	0.4334 (8)	0.0006 (3)	0.0337 (16)
H22	−0.1754	0.4644	−0.0361	0.040*
C23	−0.0625 (4)	0.3175 (7)	−0.0021 (3)	0.0294 (15)
H23	−0.0620	0.2693	−0.0417	0.035*
C24	0.3003 (4)	0.8937 (7)	0.3427 (3)	0.0347 (17)
H24A	0.2747	0.8572	0.2992	0.052*
H24B	0.3189	1.0102	0.3428	0.052*
H24C	0.2524	0.8811	0.3668	0.052*
C25	0.6418 (4)	0.8592 (8)	0.4547 (3)	0.051 (2)
H25A	0.6356	0.9314	0.4895	0.076*
H25B	0.6598	0.9255	0.4220	0.076*
H25C	0.6901	0.7755	0.4704	0.076*
C26	0.4524 (4)	0.3376 (7)	0.4039 (3)	0.0379 (17)
H26A	0.5139	0.2910	0.4037	0.057*
H26B	0.4055	0.2970	0.3672	0.057*
H26C	0.4347	0.3036	0.4426	0.057*
C27	0.4029 (4)	0.1710 (8)	0.2387 (3)	0.0284 (15)
C28	0.4682 (4)	0.0349 (7)	0.2396 (3)	0.0367 (17)
H28A	0.5068	0.0200	0.2825	0.055*
H28B	0.5088	0.0601	0.2112	0.055*
H28C	0.4330	−0.0670	0.2257	0.055*

	U11	U22	U33	U12	U13	U23
Cu1	0.0280 (4)	0.0304 (5)	0.0269 (4)	−0.0010 (4)	0.0089 (4)	−0.0029 (4)
I1	0.0350 (2)	0.0339 (3)	0.0303 (2)	0.0026 (2)	0.00674 (18)	0.0044 (2)
N1	0.024 (3)	0.027 (3)	0.021 (3)	−0.003 (2)	0.002 (2)	−0.003 (2)
N2	0.018 (3)	0.021 (3)	0.018 (3)	0.001 (2)	0.000 (2)	0.003 (2)
N3	0.025 (3)	0.033 (3)	0.037 (3)	0.004 (3)	0.012 (3)	−0.002 (3)
C1	0.022 (4)	0.032 (4)	0.017 (3)	−0.005 (3)	0.002 (3)	−0.002 (3)
C2	0.038 (4)	0.029 (4)	0.017 (3)	−0.007 (3)	0.009 (3)	−0.006 (3)
C3	0.040 (4)	0.025 (4)	0.028 (4)	−0.013 (3)	0.008 (3)	−0.006 (3)
C4	0.024 (4)	0.042 (5)	0.028 (4)	−0.008 (3)	0.001 (3)	0.007 (3)
C5	0.033 (4)	0.033 (4)	0.028 (4)	−0.004 (3)	−0.004 (3)	−0.001 (3)
C6	0.036 (4)	0.028 (4)	0.022 (4)	−0.009 (3)	0.003 (3)	0.002 (3)
C7	0.029 (4)	0.018 (3)	0.025 (4)	−0.003 (3)	0.005 (3)	−0.003 (3)
C8	0.018 (3)	0.039 (4)	0.030 (4)	−0.008 (3)	0.005 (3)	0.002 (3)
C9	0.027 (4)	0.015 (3)	0.027 (4)	−0.001 (3)	0.003 (3)	0.007 (3)
C10	0.029 (4)	0.024 (4)	0.024 (4)	0.004 (3)	0.012 (3)	0.002 (3)
C11	0.021 (3)	0.024 (4)	0.037 (4)	−0.001 (3)	0.016 (3)	0.002 (3)
C12	0.018 (3)	0.028 (4)	0.029 (4)	−0.001 (3)	0.006 (3)	0.001 (3)
C13	0.021 (3)	0.014 (3)	0.030 (4)	0.002 (3)	0.002 (3)	−0.002 (3)
C14	0.014 (3)	0.021 (3)	0.023 (3)	−0.005 (3)	0.004 (3)	0.003 (3)
C15	0.022 (3)	0.027 (4)	0.033 (4)	0.000 (3)	0.001 (3)	0.003 (3)
C16	0.026 (4)	0.029 (4)	0.034 (4)	0.005 (3)	0.014 (3)	0.000 (3)
C17	0.034 (4)	0.028 (4)	0.031 (4)	−0.006 (3)	0.011 (3)	−0.005 (3)
C18	0.021 (3)	0.025 (4)	0.026 (4)	−0.006 (3)	0.002 (3)	0.003 (3)
C19	0.024 (3)	0.018 (4)	0.025 (3)	−0.004 (3)	0.006 (3)	−0.001 (3)
C20	0.027 (4)	0.024 (4)	0.026 (4)	−0.007 (3)	0.003 (3)	−0.002 (3)
C21	0.023 (4)	0.029 (4)	0.038 (4)	0.007 (3)	0.004 (3)	0.004 (3)
C22	0.031 (4)	0.036 (4)	0.029 (4)	−0.001 (3)	−0.001 (3)	0.008 (3)
C23	0.034 (4)	0.034 (4)	0.020 (3)	−0.008 (3)	0.007 (3)	−0.001 (3)
C24	0.038 (4)	0.032 (4)	0.037 (4)	−0.004 (3)	0.014 (3)	−0.008 (3)
C25	0.041 (4)	0.047 (5)	0.054 (5)	−0.024 (4)	−0.008 (4)	0.001 (4)
C26	0.042 (4)	0.032 (4)	0.034 (4)	0.001 (3)	−0.002 (3)	0.007 (3)
C27	0.024 (4)	0.040 (4)	0.022 (3)	−0.006 (3)	0.006 (3)	0.000 (3)
C28	0.035 (4)	0.031 (4)	0.046 (4)	0.006 (3)	0.014 (3)	0.000 (3)

Cu1—N3	1.960 (5)	C13—C14	1.507 (7)
Cu1—N2	2.085 (4)	C14—C15	1.355 (7)
Cu1—N1	2.091 (4)	C14—C19	1.426 (7)
Cu1—I1	2.5479 (9)	C15—C16	1.427 (7)
N1—C7	1.282 (7)	C15—H15	0.9500
N1—C1	1.434 (6)	C16—C17	1.354 (7)
N2—C13	1.342 (6)	C16—H16	0.9500
N2—C9	1.372 (6)	C17—C18	1.408 (7)
N3—C27	1.125 (7)	C17—H17	0.9500
C1—C2	1.382 (7)	C18—C23	1.409 (7)
C1—C6	1.386 (7)	C18—C19	1.427 (7)
C2—C3	1.403 (7)	C19—C20	1.420 (7)
C2—C24	1.508 (7)	C20—C21	1.351 (7)
C3—C4	1.366 (8)	C20—H20	0.9500
C3—H3	0.9500	C21—C22	1.420 (8)
C4—C5	1.369 (8)	C21—H21	0.9500
C4—C25	1.527 (7)	C22—C23	1.368 (7)
C5—C6	1.402 (7)	C22—H22	0.9500
C5—H5	0.9500	C23—H23	0.9500
C6—C26	1.501 (7)	C24—H24A	0.9800
C7—C9	1.500 (7)	C24—H24B	0.9800
C7—C8	1.515 (7)	C24—H24C	0.9800
C8—H8A	0.9800	C25—H25A	0.9800
C8—H8B	0.9800	C25—H25B	0.9800
C8—H8C	0.9800	C25—H25C	0.9800
C9—C10	1.377 (7)	C26—H26A	0.9800
C10—C11	1.389 (7)	C26—H26B	0.9800
C10—H10	0.9500	C26—H26C	0.9800
C11—C12	1.364 (7)	C27—C28	1.456 (8)
C11—H11	0.9500	C28—H28A	0.9800
C12—C13	1.387 (7)	C28—H28B	0.9800
C12—H12	0.9500	C28—H28C	0.9800
N3—Cu1—N2	115.94 (19)	C15—C14—C19	120.5 (5)
N3—Cu1—N1	110.75 (19)	C15—C14—C13	118.8 (5)
N2—Cu1—N1	78.86 (18)	C19—C14—C13	120.5 (5)
N3—Cu1—I1	112.74 (15)	C14—C15—C16	121.2 (5)
N2—Cu1—I1	119.51 (12)	C14—C15—H15	119.4
N1—Cu1—I1	114.43 (13)	C16—C15—H15	119.4
C7—N1—C1	120.8 (5)	C17—C16—C15	118.9 (6)
C7—N1—Cu1	116.2 (4)	C17—C16—H16	120.5
C1—N1—Cu1	122.9 (4)	C15—C16—H16	120.5
C13—N2—C9	117.5 (5)	C16—C17—C18	122.0 (6)
C13—N2—Cu1	128.9 (4)	C16—C17—H17	119.0
C9—N2—Cu1	113.5 (4)	C18—C17—H17	119.0
C27—N3—Cu1	175.3 (5)	C17—C18—C23	121.7 (6)
C2—C1—C6	121.7 (6)	C17—C18—C19	119.0 (5)
C2—C1—N1	118.9 (5)	C23—C18—C19	119.2 (5)
C6—C1—N1	119.2 (5)	C20—C19—C14	124.3 (5)
C1—C2—C3	118.0 (6)	C20—C19—C18	117.5 (5)
C1—C2—C24	121.6 (5)	C14—C19—C18	118.2 (5)
C3—C2—C24	120.4 (6)	C21—C20—C19	121.4 (6)
C4—C3—C2	121.5 (6)	C21—C20—H20	119.3
C4—C3—H3	119.2	C19—C20—H20	119.3
C2—C3—H3	119.2	C20—C21—C22	121.8 (6)
C3—C4—C5	119.3 (6)	C20—C21—H21	119.1
C3—C4—C25	120.2 (6)	C22—C21—H21	119.1
C5—C4—C25	120.5 (6)	C23—C22—C21	117.8 (6)
C4—C5—C6	121.6 (6)	C23—C22—H22	121.1
C4—C5—H5	119.2	C21—C22—H22	121.1
C6—C5—H5	119.2	C22—C23—C18	122.3 (6)
C1—C6—C5	117.9 (6)	C22—C23—H23	118.8
C1—C6—C26	122.3 (6)	C18—C23—H23	118.8
C5—C6—C26	119.8 (6)	C2—C24—H24A	109.5
N1—C7—C9	116.2 (5)	C2—C24—H24B	109.5
N1—C7—C8	126.0 (5)	H24A—C24—H24B	109.5
C9—C7—C8	117.8 (5)	C2—C24—H24C	109.5
C7—C8—H8A	109.5	H24A—C24—H24C	109.5
C7—C8—H8B	109.5	H24B—C24—H24C	109.5
H8A—C8—H8B	109.5	C4—C25—H25A	109.5
C7—C8—H8C	109.5	C4—C25—H25B	109.5
H8A—C8—H8C	109.5	H25A—C25—H25B	109.5
H8B—C8—H8C	109.5	C4—C25—H25C	109.5
N2—C9—C10	122.0 (5)	H25A—C25—H25C	109.5
N2—C9—C7	115.2 (5)	H25B—C25—H25C	109.5
C10—C9—C7	122.7 (5)	C6—C26—H26A	109.5
C9—C10—C11	119.6 (5)	C6—C26—H26B	109.5
C9—C10—H10	120.2	H26A—C26—H26B	109.5
C11—C10—H10	120.2	C6—C26—H26C	109.5
C12—C11—C10	118.3 (5)	H26A—C26—H26C	109.5
C12—C11—H11	120.8	H26B—C26—H26C	109.5
C10—C11—H11	120.8	N3—C27—C28	178.7 (7)
C11—C12—C13	120.2 (5)	C27—C28—H28A	109.5
C11—C12—H12	119.9	C27—C28—H28B	109.5
C13—C12—H12	119.9	H28A—C28—H28B	109.5
N2—C13—C12	122.2 (5)	C27—C28—H28C	109.5
N2—C13—C14	117.2 (5)	H28A—C28—H28C	109.5
C12—C13—C14	120.5 (5)	H28B—C28—H28C	109.5
N3—Cu1—N1—C7	−113.7 (4)	N1—C7—C9—N2	0.5 (7)
N2—Cu1—N1—C7	0.1 (4)	C8—C7—C9—N2	−179.3 (5)
I1—Cu1—N1—C7	117.6 (4)	N1—C7—C9—C10	−177.1 (5)
N3—Cu1—N1—C1	68.3 (5)	C8—C7—C9—C10	3.0 (8)
N2—Cu1—N1—C1	−178.0 (5)	N2—C9—C10—C11	0.6 (8)
I1—Cu1—N1—C1	−60.5 (4)	C7—C9—C10—C11	178.1 (5)
N3—Cu1—N2—C13	−74.9 (5)	C9—C10—C11—C12	−1.0 (8)
N1—Cu1—N2—C13	177.3 (5)	C10—C11—C12—C13	1.0 (9)
I1—Cu1—N2—C13	65.3 (5)	C9—N2—C13—C12	0.2 (8)
N3—Cu1—N2—C9	108.0 (4)	Cu1—N2—C13—C12	−176.7 (4)
N1—Cu1—N2—C9	0.2 (4)	C9—N2—C13—C14	−176.8 (5)
I1—Cu1—N2—C9	−111.7 (3)	Cu1—N2—C13—C14	6.3 (7)
C7—N1—C1—C2	−86.8 (7)	C11—C12—C13—N2	−0.7 (9)
Cu1—N1—C1—C2	91.2 (6)	C11—C12—C13—C14	176.2 (5)
C7—N1—C1—C6	97.6 (7)	N2—C13—C14—C15	56.3 (7)
Cu1—N1—C1—C6	−84.4 (6)	C12—C13—C14—C15	−120.8 (6)
C6—C1—C2—C3	0.7 (9)	N2—C13—C14—C19	−128.1 (5)
N1—C1—C2—C3	−174.8 (5)	C12—C13—C14—C19	54.8 (8)
C6—C1—C2—C24	−179.1 (5)	C19—C14—C15—C16	−2.4 (8)
N1—C1—C2—C24	5.4 (8)	C13—C14—C15—C16	173.3 (5)
C1—C2—C3—C4	0.2 (9)	C14—C15—C16—C17	0.1 (9)
C24—C2—C3—C4	180.0 (5)	C15—C16—C17—C18	0.5 (9)
C2—C3—C4—C5	−0.3 (9)	C16—C17—C18—C23	179.2 (6)
C2—C3—C4—C25	178.0 (5)	C16—C17—C18—C19	1.1 (8)
C3—C4—C5—C6	−0.5 (10)	C15—C14—C19—C20	−175.4 (5)
C25—C4—C5—C6	−178.8 (5)	C13—C14—C19—C20	9.0 (8)
C2—C1—C6—C5	−1.4 (9)	C15—C14—C19—C18	3.9 (8)
N1—C1—C6—C5	174.1 (5)	C13—C14—C19—C18	−171.7 (5)
C2—C1—C6—C26	179.1 (5)	C17—C18—C19—C20	176.1 (5)
N1—C1—C6—C26	−5.4 (9)	C23—C18—C19—C20	−2.1 (8)
C4—C5—C6—C1	1.3 (9)	C17—C18—C19—C14	−3.2 (8)
C4—C5—C6—C26	−179.2 (6)	C23—C18—C19—C14	178.6 (5)
C1—N1—C7—C9	177.8 (5)	C14—C19—C20—C21	179.7 (5)
Cu1—N1—C7—C9	−0.3 (7)	C18—C19—C20—C21	0.5 (8)
C1—N1—C7—C8	−2.4 (9)	C19—C20—C21—C22	2.1 (9)
Cu1—N1—C7—C8	179.5 (4)	C20—C21—C22—C23	−3.0 (9)
C13—N2—C9—C10	−0.2 (8)	C21—C22—C23—C18	1.3 (9)
Cu1—N2—C9—C10	177.2 (4)	C17—C18—C23—C22	−176.9 (5)
C13—N2—C9—C7	−177.8 (5)	C19—C18—C23—C22	1.2 (9)
Cu1—N2—C9—C7	−0.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26B···N1	0.98	2.52	2.891 (8)	102