Di-μ-hydroxido-bis­{[bis­(6-methyl-2-pyridylmeth­yl)(2-phenyl­ethyl)amine-κ³N′,N′′,N′′′]copper(II)} bis(perchlorate)

The title compund, [Cu₂(OH)₂(C₂₂H₂₅N₃)₂](ClO₄)₂, is a copper(II) dimer, with two [CuL]²⁺ units [L is bis­(6-methyl-2-pyridylmethyl)­(2-phenyl­ethyl)amine] bridged by hydroxide groups to define the {[CuL](μ-OH)₂[CuL]}²⁺ cation. Charge balance is provided by perchlorate counter-anions. The cation has a crystallographic inversion centre halfway between the Cu^II ions, which are separated by 3.0161 (8) Å. The central core of the cation is an almost regular Cu₂O₂ parallelogram of sides 1.931 (2) and 1.935 (2) Å, with a Cu—O—Cu angle of 102.55 (11)°. The coordination geometry around each Cu^II centre can be best described as a square-based pyramid, with three N atoms from L ligands and two hydr­oxide O atoms completing the coordination environment. Each cationic unit is hydrogen bonded to two perchlorate anions by means of hydroxide–perchlorate O—H...O inter­actions.

S1. Comment

The finding that the reaction of molecular oxygen with aromatic organic substrates can be catalyzed by Cu^I complexes has produced an increasing interest in the study of its properties (Spodine & Manzur, 1992; Mizuno et al., 2006). It has also attracted interest for modelling oxygen-carrying (van Holde et al., 2001) and oxygenating or oxidoreductase proteins (Solomon et al., 2001; Brazeau et al., 2004). Normally, bis(hydroxo)-bridged dicopper(II) complexes are the final products of the reaction between cuprous complexes and dioxygen (Mirica et al., 2004; Rojas et al., 2004). In this context, one of the most interesting family of ligands is the bis(pyridine-2-ylalkyl)amines (Mirica et al., 2004; Shearer et al., 2005), since their steric and electronic properties can be varied over a wide range (Hayashi et al., 2000).

The structure of the title compound, (I), consists of a molecular cation with the charge counterbalanced by two perchlorate anions. The molecular dication corresponds to a dimer exhibiting two [CuL]²⁺ units which are connected by two hydroxyl ligands, acting in a µ₂-fashion. The ligand L is connected to each Cu^II centre in a tridentate fashion through its N donor atoms. The coordination geometry around each Cu^II centre is best described as a square-based pyramid (τ < 0.01; Addison et al., 1984), with two pyridyl N atoms (N1 and N3) and two hydroxyl O atoms [O1 and O1ⁱ; symmetry code: (i) 1 - x, 1 - y, 1 - z] in a cis configuration occupying the basal positions, leaving the amine atom N2 at the remaining apical one. The dication is then constructed around a central Cu₂O₂ parallelogram of sides 1.931 (2) (Cu—O1) and 1.935 (2) Å (Cu—O1ⁱ) with a Cu—O—Cu angle of 102.55 (11)°. The existence of a (crystallographic) inversion centre is a consequence of the anti configuration of both apical sites with respect to the central Cu₂O₂ plane. This coordination mode for 6-methylpyridyl tridentate amine complexes has been previously described in related cupric compounds as an amine-e/e mode (Rojas et al., 2004; Manzur et al., 2007). The measured Cu···Cu distance is 3.0161 (8) Å, which lies in the longest segment of the values described for this coordination mode in some closely related complexes (Rojas et al., 2004; Manzur et al., 2007).

Interestingly, the centroid of the C12–C17 phenyl group on the phenylethyl arm of the L ligand coordinated to one of the Cu^II centres points directly to the methyl group [C7ⁱⁱ; symmetry code: (ii) 2 - x,2 - y,1 - z] of its neigbouring L ligand in the dimer. The centroid-to-carbon distance, Cg1···C7ⁱⁱ, is 3.671 (1) Å, while the three H···Cg1 distances amount to 3.47 (1) Å.

As described for [L'(CH₃CN)Cu(µ-OH)₂Cu(CH₃CN)L'](ClO₄)₂, where L' is bis{dibenzyl[6-methyl-2-(pyridylmethyl)amine]} (Rojas et al., 2005), the perchlorate anions and hydroxyl groups of (I) interact via hydrogen bonding (Fig. 2 and Table 2). These interactions cause the deviation of the O—H vector by 63.9° from the Cu₂O₂ plane, with each of the two H atoms on opposite sides of the plane. It has been pointed out that the deviation of these H atoms from the Cu₂O₂ plane plays an important role in determining the magnetic coupling exchange in binuclear copper(II) complexes (Ruiz et al., 1997).

Although a packing view of the structure of (I) suggests some additional Cl—O···H interactions, the disorder observed for three of the perchlorate O atoms precludes their accurate characterization.

Related literature

For related literature, see: Addison et al. (1984); Brazeau et al. (2004); Hayashi et al. (2000); Holde et al. (2001); Manzur et al. (2007); Mirica et al. (2004); Mizuno et al. (2006); Rojas et al. (2004, 2005); Ruiz et al. (1997); Shearer et al. (2005); Solomon et al. (2001); Spodine & Manzur (1992).

S2. Experimental

The ligand, L, bis(6-methyl-2-pyridylmethyl)(2-phenylethyl)amine, was synthesized by the reaction of two equivalents [Please give actual amounts] of (2-bromomethyl)(6-methyl)pyridine with 2-phenylethyl-amine in refluxing acetonitrile (Volume?) for 24 h in the presence of sodium carbonate. The title copper(II) dimer was obtained by the treatment of a dichloromethane solution of the copper(I) complex [prepared in situ from Cu(CH₃CN)₄ClO₄ and the ligand] with molecular oxygen at room temperature. After standing overnight, crystals of (I) suitable for X-ray diffraction studies were separated.

Caution: Perchlorate complexes are potentially explosive, and should be handled very carefully. The small quantities used in our studies were not found to present a hazard.

S3. Refinement

H atoms bound to C atoms were included in calculated positions, with C—H = 0.93–0.97 Å, and allowed to ride with U_iso(H) = 1.2 or 1.5 times U_eq(C). The hydroxy atom H1 was located in a difference Fourier map and its isotropic displacement parameter was subsequently refined, but its coordinates were kept fixed. During the last stages of refinement, some disorder was observed for the perchlorate O atoms not involved in hydrogen bonding (O3, O4 and O5). This was modelled using two positions, A and B, for each O atom. The partial occupancies were first refined and then held constant at the convergence values of 0.55 and 0.45, respectively. The Cl—O distance for the disordered atoms was restrained to be 1.42 (1) Å.

Computing details

Data collection: SMART-NT (Bruker, 2001); cell refinement: SAINT-NT (Bruker, 1999); data reduction: SAINT-NT; program(s) used to solve structure: SHELXTL-NT (Bruker, 1999); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

Figures

Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 20% probability level. H atoms of the organic ligand and the minor component of the disordered counterion have been omitted for clarity. Hydrogen bonds are shown as single dashed lines, and π–π contacts as double-dashed lines. [Symmetry code: (i) 1 - x, 1 - y, 1 - z.] Fig. 2. Please provide Figure 2 and caption.

Di-µ-hydroxo-bis{[bis(6-methyl-2-pyridylmethyl)(2-phenylethyl)amine- κ³N',N'',N''']copper(II)} bis(perchlorate)

Crystal data

[Cu2(OH)2(C22H25N3)2](ClO4)2	F(000) = 1060
Mr = 1022.92	Dx = 1.524 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2100 reflections
a = 9.9239 (11) Å	θ = 2.8–19.5°
b = 16.5696 (19) Å	µ = 1.14 mm^−1
c = 13.9248 (16) Å	T = 298 K
β = 103.229 (2)°	Block, blue
V = 2229.0 (4) Å^3	0.41 × 0.17 × 0.13 mm
Z = 2

Data collection

Siemens SMART CCD area-detector diffractometer	3964 independent reflections
Radiation source: fine-focus sealed tube	2909 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ϕ and ω scans	θmax = 25.2°, θmin = 1.9°
Absorption correction: part of the refinement model (ΔF) (SADABS in SAINT-NT; Bruker, 1999)	h = −11→11
Tmin = 0.652, Tmax = 0.866	k = −19→19
13767 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0811P)^2] where P = (Fo^2 + 2Fc^2)/3
3964 reflections	(Δ/σ)max < 0.001
319 parameters	Δρmax = 0.57 e Å^−3
6 restraints	Δρmin = −0.31 e Å^−3

Special details

Experimental. Each frame was mesured during 10 s, using 0.3 /% between frames.

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.

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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.39102 (4)	0.53606 (3)	0.41763 (3)	0.03802 (18)
O1	0.4145 (2)	0.49178 (16)	0.54868 (17)	0.0440 (6)
H1	0.3788	0.5043	0.5990	0.054 (12)*
N1	0.1913 (3)	0.5678 (2)	0.4137 (2)	0.0461 (7)
C1	0.1483 (4)	0.4308 (3)	0.3506 (3)	0.0602 (11)
H1A	0.1615	0.3951	0.4073	0.072*
H1B	0.0787	0.4068	0.2980	0.072*
C2	0.0963 (4)	0.5114 (3)	0.3776 (3)	0.0543 (10)
C3	−0.0417 (4)	0.5234 (3)	0.3715 (4)	0.0739 (14)
H3	−0.1056	0.4835	0.3455	0.089*
C4	−0.0847 (5)	0.5946 (4)	0.4039 (4)	0.0788 (15)
H4	−0.1784	0.6038	0.3993	0.095*
C5	0.0106 (5)	0.6520 (3)	0.4431 (3)	0.0696 (13)
H5	−0.0175	0.7005	0.4660	0.084*
C6	0.1501 (4)	0.6374 (3)	0.4484 (3)	0.0545 (10)
C7	0.2570 (5)	0.6974 (3)	0.4934 (4)	0.0745 (14)
H7A	0.3387	0.6698	0.5282	0.112*
H7B	0.2222	0.7308	0.5386	0.112*
H7C	0.2793	0.7304	0.4426	0.112*
N2	0.2776 (3)	0.43728 (19)	0.3191 (2)	0.0454 (7)
C10	0.3633 (4)	0.3646 (2)	0.3419 (3)	0.0506 (10)
H10A	0.3885	0.3586	0.4130	0.061*
H10B	0.4482	0.3737	0.3201	0.061*
C11	0.3015 (5)	0.2847 (2)	0.2978 (4)	0.0718 (13)
H11A	0.2089	0.2785	0.3084	0.086*
H11B	0.2956	0.2843	0.2273	0.086*
C12	0.3919 (5)	0.2159 (2)	0.3461 (3)	0.0601 (11)
C13	0.3714 (5)	0.1804 (3)	0.4311 (4)	0.0728 (13)
H13	0.2979	0.1975	0.4572	0.087*
C14	0.4560 (6)	0.1210 (3)	0.4778 (4)	0.0835 (16)
H14	0.4405	0.0985	0.5355	0.100*
C15	0.5634 (6)	0.0942 (3)	0.4404 (5)	0.0856 (16)
H15	0.6208	0.0532	0.4721	0.103*
C16	0.5859 (5)	0.1279 (3)	0.3563 (4)	0.0802 (15)
H16	0.6585	0.1094	0.3301	0.096*
C17	0.5019 (5)	0.1893 (3)	0.3097 (4)	0.0722 (13)
H17	0.5197	0.2129	0.2533	0.087*
N3	0.4102 (3)	0.57877 (18)	0.2840 (2)	0.0422 (7)
C20	0.2592 (5)	0.4663 (3)	0.2188 (3)	0.0606 (12)
H20A	0.1659	0.4873	0.1970	0.073*
H20B	0.2683	0.4211	0.1765	0.073*
C21	0.3596 (4)	0.5307 (2)	0.2060 (3)	0.0470 (9)
C22	0.3941 (5)	0.5427 (3)	0.1169 (3)	0.0594 (11)
H22	0.3586	0.5088	0.0640	0.071*
C23	0.4802 (5)	0.6044 (3)	0.1063 (3)	0.0721 (13)
H23	0.5049	0.6125	0.0465	0.087*
C24	0.5302 (5)	0.6544 (3)	0.1847 (3)	0.0647 (12)
H24	0.5882	0.6972	0.1782	0.078*
C25	0.4941 (4)	0.6411 (2)	0.2738 (3)	0.0480 (9)
C26	0.5456 (4)	0.6942 (2)	0.3600 (3)	0.0602 (11)
H26A	0.4772	0.7345	0.3632	0.090*
H26B	0.6296	0.7201	0.3534	0.090*
H26C	0.5633	0.6626	0.4193	0.090*
Cl1	0.31371 (15)	0.61419 (8)	0.80233 (9)	0.0761 (4)
O2	0.3428 (4)	0.5652 (3)	0.7274 (3)	0.1062 (13)
O3A	0.1872 (11)	0.6523 (8)	0.754 (2)	0.148 (9)	0.45
O4A	0.4110 (16)	0.6693 (10)	0.8592 (17)	0.178 (10)	0.45
O5A	0.2839 (15)	0.5531 (7)	0.8670 (11)	0.087 (4)	0.45
O3B	0.2421 (15)	0.6843 (6)	0.7572 (17)	0.151 (6)	0.55
O4B	0.4497 (4)	0.6397 (7)	0.8511 (10)	0.085 (3)	0.55
O5B	0.2323 (17)	0.5784 (9)	0.8635 (14)	0.153 (6)	0.55

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0357 (3)	0.0445 (3)	0.0324 (3)	0.00033 (18)	0.00476 (18)	0.00206 (19)
O1	0.0406 (14)	0.0597 (16)	0.0319 (13)	0.0031 (12)	0.0089 (11)	0.0049 (12)
N1	0.0386 (17)	0.058 (2)	0.0410 (17)	0.0073 (15)	0.0072 (14)	0.0060 (16)
C1	0.050 (2)	0.063 (3)	0.067 (3)	−0.011 (2)	0.010 (2)	−0.007 (2)
C2	0.039 (2)	0.071 (3)	0.051 (2)	0.000 (2)	0.0059 (18)	0.003 (2)
C3	0.038 (2)	0.102 (4)	0.079 (3)	−0.004 (2)	0.008 (2)	0.006 (3)
C4	0.046 (3)	0.112 (5)	0.081 (4)	0.025 (3)	0.019 (2)	0.012 (3)
C5	0.063 (3)	0.083 (3)	0.069 (3)	0.029 (3)	0.027 (2)	0.010 (3)
C6	0.058 (3)	0.061 (3)	0.045 (2)	0.013 (2)	0.0132 (19)	0.008 (2)
C7	0.081 (3)	0.064 (3)	0.083 (3)	0.007 (3)	0.026 (3)	−0.015 (3)
N2	0.0439 (18)	0.0499 (18)	0.0427 (18)	−0.0026 (14)	0.0106 (14)	0.0025 (15)
C10	0.051 (2)	0.050 (2)	0.048 (2)	−0.0098 (18)	0.0056 (18)	−0.0073 (18)
C11	0.076 (3)	0.056 (3)	0.071 (3)	−0.006 (2)	−0.008 (3)	−0.012 (2)
C12	0.070 (3)	0.042 (2)	0.064 (3)	−0.014 (2)	0.004 (2)	−0.010 (2)
C13	0.079 (3)	0.062 (3)	0.085 (4)	−0.013 (3)	0.033 (3)	−0.011 (3)
C14	0.118 (5)	0.053 (3)	0.078 (4)	−0.014 (3)	0.018 (3)	0.005 (3)
C15	0.097 (4)	0.054 (3)	0.095 (4)	0.003 (3)	−0.002 (3)	0.001 (3)
C16	0.077 (3)	0.069 (3)	0.094 (4)	0.007 (3)	0.019 (3)	−0.019 (3)
C17	0.089 (4)	0.068 (3)	0.063 (3)	−0.015 (3)	0.024 (3)	−0.014 (3)
N3	0.0420 (17)	0.0481 (18)	0.0359 (16)	0.0041 (14)	0.0079 (13)	0.0076 (14)
C20	0.067 (3)	0.068 (3)	0.039 (2)	−0.004 (2)	−0.005 (2)	−0.003 (2)
C21	0.047 (2)	0.056 (2)	0.036 (2)	0.0077 (18)	0.0037 (17)	0.0036 (18)
C22	0.065 (3)	0.069 (3)	0.043 (2)	0.008 (2)	0.009 (2)	0.001 (2)
C23	0.082 (3)	0.093 (4)	0.048 (3)	0.007 (3)	0.029 (2)	0.006 (3)
C24	0.069 (3)	0.068 (3)	0.061 (3)	0.003 (2)	0.023 (2)	0.017 (2)
C25	0.048 (2)	0.054 (2)	0.042 (2)	0.0084 (19)	0.0091 (18)	0.0095 (18)
C26	0.065 (3)	0.056 (3)	0.059 (3)	−0.009 (2)	0.013 (2)	0.005 (2)
Cl1	0.0963 (10)	0.0748 (8)	0.0647 (8)	0.0014 (7)	0.0335 (7)	−0.0055 (7)
O2	0.080 (3)	0.160 (4)	0.082 (3)	−0.003 (2)	0.027 (2)	−0.051 (3)
O3A	0.148 (13)	0.070 (8)	0.209 (18)	0.026 (9)	0.004 (13)	−0.033 (11)
O4A	0.35 (2)	0.080 (12)	0.093 (10)	−0.074 (12)	0.024 (14)	−0.025 (9)
O5A	0.095 (8)	0.101 (8)	0.084 (7)	−0.015 (6)	0.057 (6)	0.010 (6)
O3B	0.149 (10)	0.099 (10)	0.208 (16)	0.054 (8)	0.050 (11)	0.024 (12)
O4B	0.124 (6)	0.065 (7)	0.064 (5)	−0.039 (5)	0.018 (4)	−0.031 (5)
O5B	0.176 (15)	0.183 (13)	0.138 (11)	−0.004 (9)	0.118 (11)	−0.020 (9)

Geometric parameters (Å, º)

Cu1—O1	1.931 (2)	C12—C13	1.378 (6)
Cu1—O1^i	1.935 (2)	C13—C14	1.359 (7)
Cu1—N3	2.040 (3)	C13—H13	0.9300
Cu1—N1	2.039 (3)	C14—C15	1.363 (7)
Cu1—N2	2.263 (3)	C14—H14	0.9300
Cu1—Cu1^i	3.0161 (8)	C15—C16	1.361 (7)
O1—Cu1^i	1.935 (2)	C15—H15	0.9300
O1—H1	0.88	C16—C17	1.380 (7)
N1—C2	1.340 (5)	C16—H16	0.9300
N1—C6	1.349 (5)	C17—H17	0.9300
C1—N2	1.453 (5)	N3—C21	1.348 (5)
C1—C2	1.510 (6)	N3—C25	1.354 (5)
C1—H1A	0.9700	C20—C21	1.498 (6)
C1—H1B	0.9700	C20—H20A	0.9700
C2—C3	1.368 (6)	C20—H20B	0.9700
C3—C4	1.365 (7)	C21—C22	1.374 (6)
C3—H3	0.9300	C22—C23	1.362 (6)
C4—C5	1.365 (7)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.370 (6)
C5—C6	1.390 (6)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.385 (5)
C6—C7	1.484 (6)	C24—H24	0.9300
C7—H7A	0.9600	C25—C26	1.483 (5)
C7—H7B	0.9600	C26—H26A	0.9600
C7—H7C	0.9600	C26—H26B	0.9600
N2—C20	1.449 (5)	C26—H26C	0.9600
N2—C10	1.467 (5)	Cl1—O2	1.403 (4)
C10—C11	1.528 (5)	Cl1—O5B	1.4293 (11)
C10—H10A	0.9700	Cl1—O3B	1.4295 (10)
C10—H10B	0.9700	Cl1—O4A	1.4295 (11)
C11—C12	1.510 (6)	Cl1—O4B	1.4294 (11)
C11—H11A	0.9700	Cl1—O5A	1.4294 (10)
C11—H11B	0.9700	Cl1—O3A	1.4297 (11)
C12—C17	1.377 (6)
O1—Cu1—O1^i	77.45 (11)	C17—C12—C13	117.7 (5)
O1—Cu1—N3	167.88 (11)	C17—C12—C11	121.2 (5)
O1^i—Cu1—N3	90.44 (11)	C13—C12—C11	121.1 (5)
O1—Cu1—N1	91.69 (11)	C14—C13—C12	121.6 (5)
O1^i—Cu1—N1	167.82 (11)	C14—C13—H13	119.2
N3—Cu1—N1	100.31 (12)	C12—C13—H13	119.2
O1—Cu1—N2	103.52 (11)	C13—C14—C15	120.3 (5)
O1^i—Cu1—N2	107.74 (11)	C13—C14—H14	119.9
N3—Cu1—N2	80.51 (12)	C15—C14—H14	119.9
N1—Cu1—N2	79.92 (12)	C16—C15—C14	119.5 (5)
Cu1—O1—Cu1^i	102.55 (11)	C16—C15—H15	120.3
Cu1—O1—H1	133	C14—C15—H15	120.3
Cu1^i—O1—H1	115.10 (19)	C15—C16—C17	120.4 (5)
C2—N1—C6	119.0 (3)	C15—C16—H16	119.8
C2—N1—Cu1	115.2 (3)	C17—C16—H16	119.8
C6—N1—Cu1	125.7 (3)	C12—C17—C16	120.5 (5)
N2—C1—C2	112.7 (3)	C12—C17—H17	119.8
N2—C1—H1A	109.1	C16—C17—H17	119.8
C2—C1—H1A	109.1	C21—N3—C25	119.3 (3)
N2—C1—H1B	109.1	C21—N3—Cu1	115.8 (2)
C2—C1—H1B	109.1	C25—N3—Cu1	123.3 (2)
H1A—C1—H1B	107.8	N2—C20—C21	114.2 (3)
N1—C2—C3	122.1 (4)	N2—C20—H20A	108.7
N1—C2—C1	117.4 (3)	C21—C20—H20A	108.7
C3—C2—C1	120.4 (4)	N2—C20—H20B	108.7
C4—C3—C2	119.3 (5)	C21—C20—H20B	108.7
C4—C3—H3	120.4	H20A—C20—H20B	107.6
C2—C3—H3	120.4	N3—C21—C22	121.2 (4)
C5—C4—C3	119.6 (4)	N3—C21—C20	117.4 (3)
C5—C4—H4	120.2	C22—C21—C20	121.3 (4)
C3—C4—H4	120.2	C23—C22—C21	119.9 (4)
C4—C5—C6	119.3 (5)	C23—C22—H22	120.0
C4—C5—H5	120.3	C21—C22—H22	120.0
C6—C5—H5	120.3	C22—C23—C24	119.3 (4)
N1—C6—C5	120.6 (4)	C22—C23—H23	120.4
N1—C6—C7	118.5 (4)	C24—C23—H23	120.4
C5—C6—C7	120.8 (4)	C23—C24—C25	119.7 (4)
C6—C7—H7A	109.5	C23—C24—H24	120.1
C6—C7—H7B	109.5	C25—C24—H24	120.1
H7A—C7—H7B	109.5	N3—C25—C24	120.5 (4)
C6—C7—H7C	109.5	N3—C25—C26	118.3 (3)
H7A—C7—H7C	109.5	C24—C25—C26	121.2 (4)
H7B—C7—H7C	109.5	C25—C26—H26A	109.5
C20—N2—C1	113.0 (3)	C25—C26—H26B	109.5
C20—N2—C10	114.8 (3)	H26A—C26—H26B	109.5
C1—N2—C10	112.5 (3)	C25—C26—H26C	109.5
C20—N2—Cu1	106.3 (2)	H26A—C26—H26C	109.5
C1—N2—Cu1	102.8 (2)	H26B—C26—H26C	109.5
C10—N2—Cu1	106.2 (2)	O2—Cl1—O5B	116.3 (8)
N2—C10—C11	117.7 (3)	O2—Cl1—O3B	108.0 (10)
N2—C10—H10A	107.9	O5B—Cl1—O3B	107.9 (10)
C11—C10—H10A	107.9	O2—Cl1—O4A	123.6 (10)
N2—C10—H10B	107.9	O2—Cl1—O4B	101.1 (5)
C11—C10—H10B	107.9	O5B—Cl1—O4B	116.1 (11)
H10A—C10—H10B	107.2	O3B—Cl1—O4B	106.8 (8)
C12—C11—C10	109.4 (4)	O2—Cl1—O5A	99.6 (7)
C12—C11—H11A	109.8	O4A—Cl1—O5A	108.3 (13)
C10—C11—H11A	109.8	O2—Cl1—O3A	102.3 (12)
C12—C11—H11B	109.8	O4A—Cl1—O3A	112.8 (11)
C10—C11—H11B	109.8	O5A—Cl1—O3A	108.9 (12)
H11A—C11—H11B	108.2

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.88	2.15	2.999 (4)	161