[mu]-Chloro-bis{[benzylbis(2-pyridyl­methyl)­amine-[kappa]³N]­chloro­copper(II)} perchlorate hemi­hydrate

In the title dinuclear Cu^II compound, [Cu₂Cl₃(C₁₉H₁₉N₃)₃]ClO₄·0.5H₂O, the coordination geometry around the Cu atoms is square pyramidal, with the bridging Cl atom at the apical positions. The Cu-Cl-Cu angle is 136.9 (1)° and the Cu...Cu distance is 4.961 (1) Å.

S1. Comment

The abbreviation for the tridentate benzyl(2-pyridylmethyl)amine ligand in the title compound, (I), is bzpy, and that of its 2-hydroxy derivative is phpyH. In the crystals of [Cu(phpyH)Cl]ClO₄^.CH₃OH, which is a model compound for galactose oxidase, a rather long Cu^II–phenolic oxygen distance of 2.570 (4) Å was observed (Ito et al., 1998).

S2. Experimental

Preparation of the bzpy ligand and its chlorocopper(II) complex was carried out by an analagous method to that described previously by Ito et al. (1998). Crystals of the title compound, [Cu₂(bzpy)₂Cl₃]ClO₄^.0.5H₂O, were grown from an MeOH/CH₃CN solution.

S3. Refinement

The water O atom lies on an inversion centre the water H atoms were not introduced. Positional parameters of all the other H atoms were calculated geometrically and fixed with U(H) = 1.2U_eq(parent atom).

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

(I)

Crystal data

[Cu2Cl3(C19H19N3)2]ClO4·0.5H2O	Z = 2
Mr = 920.67	Dx = 1.524 Mg m^−3
Triclinic, P1	Mo Kα radiation, λ = 0.71073 Å
a = 13.799 (2) Å	Cell parameters from 25 reflections
b = 14.488 (2) Å	θ = 10–15°
c = 12.608 (2) Å	µ = 1.38 mm^−1
α = 99.33 (1)°	T = 300 K
β = 111.86 (1)°	Sphere, blue
γ = 113.14 (1)°	0.3 mm (radius)
V = 2005.9 (6) Å^3

Data collection

Rigaku AFC-5S diffractometer	Rint = 0.012
θ–2θ scans	θmax = 27.5°
Absorption correction: for a sphere (International Tables for Crystallography, 1992, Vol.C)	h = 0→18
Tmin = 0.545, Tmax = 0.552	k = −19→19
9581 measured reflections	l = −16→16
9196 independent reflections	3 standard reflections every 100 reflections
6985 reflections with I > 2σ(I)	intensity decay: 4.3%

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.1(Fo^2 + 2Fc^2)/3)^2]
wR(F^2) = 0.141	(Δ/σ)max = 0.004
S = 1.02	Δρmax = 0.42 e Å^−3
9196 reflections	Δρmin = −0.35 e Å^−3
493 parameters

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Cu1	0.33950 (3)	0.22173 (3)	0.19568 (3)	0.03784 (9)
Cu2	0.36224 (3)	0.15547 (3)	−0.19073 (3)	0.03861 (10)
Cl1	0.30204 (7)	0.09911 (7)	0.28385 (8)	0.0572 (2)
Cl2	0.38586 (8)	0.31866 (6)	−0.18914 (8)	0.0545 (2)
Cl3	0.33147 (7)	0.11426 (6)	−0.00579 (7)	0.0461 (2)
Cl4	−0.00835 (7)	−0.34483 (7)	−0.66328 (9)	0.0564 (2)
O1	0.0894 (3)	−0.2478 (4)	−0.6377 (6)	0.151 (2)
O2	−0.1165 (3)	−0.3620 (5)	−0.7477 (6)	0.174 (2)
O3	0.0050 (6)	−0.4296 (5)	−0.6863 (8)	0.232 (3)
O4	−0.0073 (7)	−0.3427 (7)	−0.5558 (6)	0.238 (3)
O5	1.0000	0.5000	1.0000	0.294 (9)
N1	0.1713 (2)	0.1952 (2)	0.1056 (2)	0.0432 (6)
N2	0.3791 (2)	0.3591 (2)	0.1548 (2)	0.0425 (6)
N3	0.5185 (2)	0.2893 (2)	0.2789 (2)	0.0435 (6)
N4	0.1840 (2)	0.0717 (2)	−0.2892 (2)	0.0447 (7)
N5	0.3470 (2)	0.0091 (2)	−0.2641 (2)	0.0405 (6)
N6	0.5349 (2)	0.1999 (2)	−0.0959 (2)	0.0418 (6)
C1	0.0740 (3)	0.1250 (3)	0.1076 (3)	0.0492 (8)
C2	−0.0397 (3)	0.1069 (3)	0.0328 (4)	0.061 (1)
C3	−0.0525 (3)	0.1607 (4)	−0.0466 (4)	0.068 (1)
C4	0.0475 (3)	0.2352 (3)	−0.0460 (3)	0.060 (1)
C5	0.1593 (3)	0.2522 (3)	0.0322 (3)	0.0453 (8)
C6	0.2723 (3)	0.3304 (3)	0.0380 (3)	0.0515 (9)
C7	0.4886 (3)	0.3861 (2)	0.1427 (3)	0.0485 (8)
C8	0.5710 (3)	0.3653 (2)	0.2391 (3)	0.0473 (8)
C9	0.6951 (3)	0.4179 (3)	0.2839 (4)	0.0614 (10)
C10	0.7640 (3)	0.3887 (3)	0.3688 (4)	0.068 (1)
C11	0.7090 (3)	0.3103 (3)	0.4076 (4)	0.063 (1)
C12	0.5866 (3)	0.2628 (3)	0.3619 (3)	0.0517 (8)
C13	0.4077 (3)	0.4517 (3)	0.2569 (3)	0.0551 (9)
C14	0.3224 (3)	0.4257 (3)	0.3090 (3)	0.0571 (9)
C15	0.2274 (4)	0.4454 (3)	0.2690 (5)	0.080 (1)
C16	0.1518 (5)	0.4256 (5)	0.3187 (8)	0.118 (2)
C17	0.1711 (8)	0.3875 (5)	0.4107 (10)	0.148 (3)
C18	0.2664 (7)	0.3667 (4)	0.4563 (5)	0.115 (2)
C19	0.3438 (5)	0.3873 (3)	0.4033 (4)	0.079 (1)
C20	0.1090 (3)	0.1121 (3)	−0.3071 (3)	0.0554 (10)
C21	−0.0133 (3)	0.0466 (4)	−0.3542 (4)	0.067 (1)
C22	−0.0590 (3)	−0.0613 (4)	−0.3859 (4)	0.070 (1)
C23	0.0169 (3)	−0.1038 (3)	−0.3707 (4)	0.063 (1)
C24	0.1390 (3)	−0.0346 (3)	−0.3199 (3)	0.0465 (8)
C25	0.2283 (3)	−0.0746 (2)	−0.2866 (3)	0.0484 (8)
C26	0.4488 (3)	0.0061 (2)	−0.1697 (3)	0.0465 (8)
C27	0.5568 (3)	0.1173 (2)	−0.0968 (3)	0.0420 (7)
C28	0.6713 (3)	0.1330 (3)	−0.0296 (3)	0.0568 (10)
C29	0.7645 (3)	0.2362 (4)	0.0424 (4)	0.066 (1)
C30	0.7424 (3)	0.3216 (3)	0.0430 (4)	0.065 (1)
C31	0.6269 (3)	0.3007 (3)	−0.0280 (3)	0.0537 (9)
C32	0.3493 (3)	−0.0033 (3)	−0.3841 (3)	0.0481 (8)
C33	0.4604 (3)	0.0853 (3)	−0.3734 (3)	0.0437 (8)
C34	0.5607 (3)	0.0744 (3)	−0.3503 (3)	0.056 (1)
C35	0.6644 (4)	0.1589 (4)	−0.3326 (4)	0.071 (1)
C36	0.6678 (4)	0.2544 (4)	−0.3398 (4)	0.075 (1)
C37	0.5671 (4)	0.2639 (3)	−0.3671 (4)	0.070 (1)
C38	0.4641 (3)	0.1792 (3)	−0.3836 (3)	0.0545 (10)
H1	0.0834	0.0863	0.1623	0.0591*
H2	−0.1083	0.0575	0.0365	0.0735*
H3	−0.1310	0.1465	−0.1024	0.0818*
H4	0.0396	0.2750	−0.0995	0.0725*
H5	0.2688	0.3944	0.0326	0.0618*
H6	0.2797	0.2988	−0.0295	0.0618*
H7	0.4672	0.3422	0.0632	0.0582*
H8	0.5279	0.4606	0.1526	0.0582*
H9	0.7322	0.4733	0.2566	0.0737*
H10	0.8494	0.4231	0.3999	0.0817*
H11	0.7553	0.2889	0.4658	0.0758*
H12	0.5484	0.2089	0.3903	0.0620*
H13	0.4868	0.4768	0.3220	0.0661*
H14	0.4068	0.5080	0.2262	0.0661*
H15	0.2139	0.4738	0.2045	0.0959*
H16	0.0854	0.4387	0.2882	0.1411*
H17	0.1183	0.3743	0.4457	0.1771*
H18	0.2792	0.3393	0.5217	0.1379*
H19	0.4105	0.3744	0.4330	0.0954*
H20	0.1413	0.1884	−0.2866	0.0665*
H21	−0.0651	0.0772	−0.3642	0.0805*
H22	−0.1437	−0.1080	−0.4188	0.0844*
H23	−0.0147	−0.1802	−0.3950	0.0752*
H24	0.1992	−0.1385	−0.3527	0.0581*
H25	0.2373	−0.0909	−0.2138	0.0581*
H26	0.4243	−0.0230	−0.1151	0.0559*
H27	0.4702	−0.0390	−0.2095	0.0559*
H28	0.6852	0.0729	−0.0332	0.0682*
H29	0.8440	0.2489	0.0917	0.0791*
H30	0.8065	0.3942	0.0919	0.0782*
H31	0.6119	0.3599	−0.0288	0.0644*
H32	0.3454	−0.0708	−0.4132	0.0577*
H33	0.2804	−0.0032	−0.4420	0.0577*
H34	0.5580	0.0078	−0.3465	0.0672*
H35	0.7344	0.1517	−0.3153	0.0855*
H36	0.7406	0.3139	−0.3255	0.0895*
H37	0.5683	0.3292	−0.3747	0.0844*
H38	0.3936	0.1860	−0.4026	0.0654*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0334 (2)	0.0351 (2)	0.0394 (2)	0.0130 (1)	0.0167 (1)	0.0124 (1)
Cu2	0.0392 (2)	0.0314 (2)	0.0411 (2)	0.0154 (1)	0.0188 (2)	0.0099 (1)
Cl1	0.0473 (4)	0.0572 (5)	0.0615 (5)	0.0196 (4)	0.0225 (4)	0.0336 (4)
Cl2	0.0686 (5)	0.0395 (4)	0.0678 (5)	0.0287 (4)	0.0397 (4)	0.0250 (4)
Cl3	0.0553 (4)	0.0404 (4)	0.0435 (4)	0.0198 (3)	0.0296 (3)	0.0125 (3)
Cl4	0.0454 (4)	0.0578 (5)	0.0701 (5)	0.0246 (4)	0.0299 (4)	0.0293 (4)
O1	0.064 (2)	0.130 (4)	0.246 (6)	0.026 (2)	0.067 (3)	0.110 (4)
O2	0.055 (2)	0.165 (5)	0.273 (7)	0.045 (3)	0.032 (3)	0.148 (5)
O3	0.137 (5)	0.123 (4)	0.321 (10)	0.090 (4)	0.014 (5)	−0.023 (5)
O4	0.196 (7)	0.266 (9)	0.145 (5)	0.002 (6)	0.118 (5)	0.035 (5)
O5	0.30 (2)	0.25 (2)	0.36 (2)	0.10 (1)	0.22 (2)	0.12 (1)
N1	0.041 (1)	0.041 (1)	0.043 (1)	0.020 (1)	0.020 (1)	0.009 (1)
N2	0.048 (1)	0.037 (1)	0.044 (1)	0.019 (1)	0.026 (1)	0.014 (1)
N3	0.037 (1)	0.040 (1)	0.041 (1)	0.013 (1)	0.016 (1)	0.006 (1)
N4	0.044 (1)	0.045 (1)	0.039 (1)	0.020 (1)	0.018 (1)	0.012 (1)
N5	0.043 (1)	0.036 (1)	0.040 (1)	0.016 (1)	0.022 (1)	0.0098 (10)
N6	0.043 (1)	0.040 (1)	0.039 (1)	0.015 (1)	0.023 (1)	0.0101 (10)
C1	0.041 (2)	0.044 (2)	0.056 (2)	0.017 (1)	0.024 (1)	0.012 (1)
C2	0.040 (2)	0.055 (2)	0.075 (2)	0.018 (2)	0.026 (2)	0.011 (2)
C3	0.047 (2)	0.080 (3)	0.061 (2)	0.034 (2)	0.016 (2)	0.008 (2)
C4	0.062 (2)	0.075 (2)	0.052 (2)	0.043 (2)	0.024 (2)	0.024 (2)
C5	0.051 (2)	0.049 (2)	0.041 (2)	0.029 (1)	0.023 (1)	0.013 (1)
C6	0.061 (2)	0.054 (2)	0.051 (2)	0.032 (2)	0.031 (2)	0.025 (1)
C7	0.052 (2)	0.039 (2)	0.054 (2)	0.015 (1)	0.033 (1)	0.015 (1)
C8	0.045 (2)	0.038 (1)	0.048 (2)	0.011 (1)	0.027 (1)	0.004 (1)
C9	0.047 (2)	0.052 (2)	0.065 (2)	0.008 (2)	0.031 (2)	0.006 (2)
C10	0.036 (2)	0.071 (2)	0.067 (2)	0.014 (2)	0.019 (2)	0.001 (2)
C11	0.046 (2)	0.069 (2)	0.057 (2)	0.026 (2)	0.015 (2)	0.009 (2)
C12	0.043 (2)	0.051 (2)	0.047 (2)	0.019 (1)	0.016 (1)	0.011 (1)
C13	0.064 (2)	0.035 (2)	0.063 (2)	0.018 (1)	0.037 (2)	0.009 (1)
C14	0.064 (2)	0.036 (2)	0.062 (2)	0.016 (1)	0.038 (2)	0.001 (1)
C15	0.072 (3)	0.056 (2)	0.107 (3)	0.029 (2)	0.051 (3)	0.006 (2)
C16	0.091 (4)	0.073 (3)	0.179 (7)	0.024 (3)	0.093 (5)	−0.004 (4)
C17	0.146 (6)	0.057 (3)	0.211 (9)	−0.008 (3)	0.150 (7)	−0.026 (4)
C18	0.160 (6)	0.053 (3)	0.090 (4)	0.000 (3)	0.090 (4)	−0.002 (2)
C19	0.106 (3)	0.049 (2)	0.062 (2)	0.014 (2)	0.051 (2)	0.006 (2)
C20	0.053 (2)	0.065 (2)	0.047 (2)	0.034 (2)	0.019 (1)	0.017 (2)
C21	0.053 (2)	0.089 (3)	0.058 (2)	0.040 (2)	0.023 (2)	0.021 (2)
C22	0.041 (2)	0.082 (3)	0.068 (2)	0.020 (2)	0.022 (2)	0.020 (2)
C23	0.049 (2)	0.056 (2)	0.066 (2)	0.014 (2)	0.027 (2)	0.017 (2)
C24	0.044 (2)	0.046 (2)	0.039 (1)	0.015 (1)	0.020 (1)	0.011 (1)
C25	0.046 (2)	0.034 (1)	0.057 (2)	0.013 (1)	0.026 (1)	0.012 (1)
C26	0.049 (2)	0.041 (2)	0.050 (2)	0.022 (1)	0.023 (1)	0.018 (1)
C27	0.044 (1)	0.047 (2)	0.036 (1)	0.021 (1)	0.022 (1)	0.015 (1)
C28	0.052 (2)	0.067 (2)	0.056 (2)	0.031 (2)	0.028 (2)	0.023 (2)
C29	0.044 (2)	0.081 (3)	0.056 (2)	0.026 (2)	0.018 (2)	0.013 (2)
C30	0.046 (2)	0.061 (2)	0.058 (2)	0.008 (2)	0.024 (2)	0.002 (2)
C31	0.048 (2)	0.044 (2)	0.057 (2)	0.013 (1)	0.029 (2)	0.008 (1)
C32	0.050 (2)	0.049 (2)	0.038 (1)	0.021 (1)	0.022 (1)	0.007 (1)
C33	0.046 (2)	0.050 (2)	0.033 (1)	0.021 (1)	0.022 (1)	0.010 (1)
C34	0.064 (2)	0.068 (2)	0.053 (2)	0.038 (2)	0.037 (2)	0.026 (2)
C35	0.056 (2)	0.111 (4)	0.054 (2)	0.041 (2)	0.034 (2)	0.032 (2)
C36	0.068 (2)	0.073 (3)	0.063 (2)	0.012 (2)	0.039 (2)	0.020 (2)
C37	0.095 (3)	0.057 (2)	0.070 (2)	0.032 (2)	0.054 (2)	0.029 (2)
C38	0.069 (2)	0.062 (2)	0.049 (2)	0.037 (2)	0.037 (2)	0.023 (2)

Geometric parameters (Å, º)

Cu1—Cl1	2.238 (1)	C13—C14	1.506 (5)
Cu1—Cl3	2.695 (1)	C13—H13	0.960
Cu1—N1	2.004 (3)	C13—H14	0.960
Cu1—N2	2.053 (3)	C14—C15	1.379 (6)
Cu1—N3	1.999 (3)	C14—C19	1.376 (6)
Cu2—Cl2	2.252 (1)	C15—C16	1.369 (8)
Cu2—Cl3	2.639 (1)	C15—H15	0.960
Cu2—N4	1.988 (3)	C16—C17	1.35 (1)
Cu2—N5	2.066 (2)	C16—H16	0.960
Cu2—N6	1.985 (3)	C17—C18	1.40 (1)
Cl4—O1	1.393 (4)	C17—H17	0.960
Cl4—O2	1.364 (4)	C18—C19	1.422 (7)
Cl4—O3	1.315 (5)	C18—H18	0.960
Cl4—O4	1.345 (6)	C19—H19	0.960
N1—C1	1.342 (4)	C20—C21	1.384 (5)
N1—C5	1.344 (4)	C20—H20	0.960
N2—C6	1.488 (4)	C21—C22	1.355 (7)
N2—C7	1.480 (4)	C21—H21	0.960
N2—C13	1.502 (4)	C22—C23	1.381 (6)
N3—C8	1.347 (4)	C22—H22	0.960
N3—C12	1.344 (4)	C23—C24	1.385 (5)
N4—C20	1.345 (4)	C23—H23	0.960
N4—C24	1.335 (4)	C24—C25	1.511 (5)
N5—C25	1.489 (4)	C25—H24	0.960
N5—C26	1.486 (4)	C25—H25	0.960
N5—C32	1.508 (4)	C26—C27	1.508 (4)
N6—C27	1.344 (4)	C26—H26	0.960
N6—C31	1.343 (4)	C26—H27	0.960
C1—C2	1.384 (5)	C27—C28	1.388 (4)
C1—H1	0.960	C28—C29	1.376 (6)
C2—C3	1.367 (6)	C28—H28	0.960
C2—H2	0.960	C29—C30	1.385 (6)
C3—C4	1.374 (6)	C29—H29	0.960
C3—H3	0.960	C30—C31	1.380 (5)
C4—C5	1.380 (5)	C30—H30	0.960
C4—H4	0.960	C31—H31	0.960
C5—C6	1.490 (5)	C32—C33	1.504 (4)
C6—H5	0.960	C32—H32	0.960
C6—H6	0.960	C32—H33	0.960
C7—C8	1.490 (5)	C33—C34	1.382 (5)
C7—H7	0.960	C33—C38	1.370 (5)
C7—H8	0.960	C34—C35	1.377 (6)
C8—C9	1.395 (5)	C34—H34	0.960
C9—C10	1.391 (6)	C35—C36	1.384 (7)
C9—H9	0.960	C35—H35	0.960
C10—C11	1.374 (6)	C36—C37	1.371 (7)
C10—H10	0.960	C36—H36	0.960
C11—C12	1.376 (5)	C37—C38	1.377 (6)
C11—H11	0.960	C37—H37	0.960
C12—H12	0.960	C38—H38	0.960
Cu1···Cl3	2.6946 (8)	C1···C2^v	3.293 (5)
Cu2···Cl3	2.6389 (8)	C1···C1^v	3.394 (6)
O1···C35^i	3.317 (6)	C3···C29^vi	3.566 (6)
O1···C21^ii	3.468 (7)	C10···C17^vii	3.463 (7)
O1···C36^i	3.503 (7)	C11···C36^viii	3.598 (6)
O2···C9^iii	3.428 (6)	C12···C37^viii	3.523 (5)
O2···C20^ii	3.527 (7)	C12···C36^viii	3.540 (6)
O3···C16^iv	3.434 (8)	C20···C22^ii	3.562 (6)
O4···C17^v	3.346 (8)	C34···C34^i	3.394 (7)
O4···C10^iii	3.594 (9)
Cl1—Cu1—Cl3	102.3 (1)	C11—C12—H12	118.9
Cl1—Cu1—N1	97.6 (1)	N2—C13—C14	115.1 (3)
Cl1—Cu1—N2	165.1 (1)	N2—C13—H13	108.1
Cl1—Cu1—N3	98.0 (1)	N2—C13—H14	108.1
Cl3—Cu1—N1	94.1 (1)	C14—C13—H13	108.1
Cl3—Cu1—N2	92.5 (1)	C14—C13—H14	108.1
Cl3—Cu1—N3	88.5 (1)	H13—C13—H14	109.5
N1—Cu1—N2	82.0 (1)	C13—C14—C15	121.4 (4)
N1—Cu1—N3	163.3 (1)	C13—C14—C19	119.1 (4)
N2—Cu1—N3	81.4 (1)	C15—C14—C19	119.4 (4)
Cl2—Cu2—Cl3	111.8 (1)	C14—C15—C16	121.9 (6)
Cl2—Cu2—N4	97.8 (1)	C14—C15—H15	119.1
Cl2—Cu2—N5	153.4 (1)	C16—C15—H15	119.1
Cl2—Cu2—N6	97.7 (1)	C15—C16—C17	119.5 (7)
Cl3—Cu2—N4	85.9 (1)	C15—C16—H16	120.3
Cl3—Cu2—N5	94.8 (1)	C17—C16—H16	120.2
Cl3—Cu2—N6	89.4 (1)	C16—C17—C18	121.6 (5)
N4—Cu2—N5	82.5 (1)	C16—C17—H17	119
N4—Cu2—N6	164.5 (1)	C18—C17—H17	119
N5—Cu2—N6	83.2 (1)	C17—C18—C19	118.2 (6)
Cu1—Cl3—Cu2	136.9 (1)	C17—C18—H18	120.9
O1—Cl4—O2	114.2 (3)	C19—C18—H18	120.9
O1—Cl4—O3	114.8 (4)	C14—C19—C18	119.4 (6)
O1—Cl4—O4	106.1 (4)	C14—C19—H19	120.3
O2—Cl4—O3	112.1 (4)	C18—C19—H19	120.3
O2—Cl4—O4	110.2 (5)	N4—C20—C21	121.8 (4)
O3—Cl4—O4	97.9 (6)	N4—C20—H20	119.1
Cu1—N1—C1	127.0 (2)	C21—C20—H20	119.1
Cu1—N1—C5	113.4 (2)	C20—C21—C22	119.0 (4)
C1—N1—C5	119.5 (3)	C20—C21—H21	120.5
Cu1—N2—C6	105.6 (2)	C22—C21—H21	120.5
Cu1—N2—C7	105.6 (2)	C21—C22—C23	119.7 (3)
Cu1—N2—C13	111.6 (2)	C21—C22—H22	120.2
C6—N2—C7	113.1 (2)	C23—C22—H22	120.2
C6—N2—C13	112.8 (3)	C22—C23—C24	119.1 (4)
C7—N2—C13	107.9 (2)	C22—C23—H23	120.5
Cu1—N3—C8	113.3 (2)	C24—C23—H23	120.5
Cu1—N3—C12	127.2 (2)	N4—C24—C23	121.3 (3)
C8—N3—C12	119.5 (3)	N4—C24—C25	116.9 (3)
Cu2—N4—C20	126.1 (2)	C23—C24—C25	121.6 (3)
Cu2—N4—C24	113.7 (2)	N5—C25—C24	110.3 (2)
C20—N4—C24	119.2 (3)	N5—C25—H24	109.3
Cu2—N5—C25	106.0 (2)	N5—C25—H25	109.3
Cu2—N5—C26	105.9 (2)	C24—C25—H24	109.3
Cu2—N5—C32	111.2 (2)	C24—C25—H25	109.3
C25—N5—C26	112.3 (2)	H24—C25—H25	109.5
C25—N5—C32	109.0 (2)	N5—C26—C27	111.1 (2)
C26—N5—C32	112.2 (2)	N5—C26—H26	109.1
Cu2—N6—C27	114.1 (2)	N5—C26—H27	109.1
Cu2—N6—C31	127.0 (2)	C27—C26—H26	109.1
C27—N6—C31	118.8 (3)	C27—C26—H27	109.1
N1—C1—C2	121.6 (3)	H26—C26—H27	109.5
N1—C1—H1	119.2	N6—C27—C26	116.2 (3)
C2—C1—H1	119.2	N6—C27—C28	122.0 (3)
C1—C2—C3	118.7 (3)	C26—C27—C28	121.7 (3)
C1—C2—H2	120.6	C27—C28—C29	118.8 (3)
C3—C2—H2	120.6	C27—C28—H28	120.6
C2—C3—C4	119.7 (3)	C29—C28—H28	120.6
C2—C3—H3	120.1	C28—C29—C30	119.4 (3)
C4—C3—H3	120.1	C28—C29—H29	120.3
C3—C4—C5	119.4 (4)	C30—C29—H29	120.3
C3—C4—H4	120.3	C29—C30—C31	118.9 (3)
C5—C4—H4	120.3	C29—C30—H30	120.5
N1—C5—C4	120.9 (3)	C31—C30—H30	120.5
N1—C5—C6	116.0 (3)	N6—C31—C30	122.1 (3)
C4—C5—C6	123.0 (3)	N6—C31—H31	119.0
N2—C6—C5	111.0 (3)	C30—C31—H31	119.0
N2—C6—H5	109.1	N5—C32—C33	113.1 (2)
N2—C6—H6	109.1	N5—C32—H32	108.6
C5—C6—H5	109.1	N5—C32—H33	108.6
C5—C6—H6	109.1	C33—C32—H32	108.6
H5—C6—H6	109.5	C33—C32—H33	108.6
N2—C7—C8	108.9 (2)	H32—C32—H33	109.5
N2—C7—H7	109.6	C32—C33—C34	120.8 (3)
N2—C7—H8	109.6	C32—C33—C38	119.9 (3)
C8—C7—H7	109.6	C34—C33—C38	119.3 (3)
C8—C7—H8	109.6	C33—C34—C35	120.1 (4)
H7—C7—H8	109.5	C33—C34—H34	120.0
N3—C8—C7	116.1 (3)	C35—C34—H34	120.0
N3—C8—C9	121.0 (3)	C34—C35—C36	119.9 (4)
C7—C8—C9	122.9 (3)	C34—C35—H35	120.0
C8—C9—C10	118.8 (3)	C36—C35—H35	120.0
C8—C9—H9	120.6	C35—C36—C37	120.0 (4)
C10—C9—H9	120.6	C35—C36—H36	120.0
C9—C10—C11	119.5 (3)	C37—C36—H36	120.0
C9—C10—H10	120.2	C36—C37—C38	119.5 (4)
C11—C10—H10	120.2	C36—C37—H37	120.2
C10—C11—C12	119.0 (4)	C38—C37—H37	120.2
C10—C11—H11	120.5	C33—C38—C37	121.1 (4)
C12—C11—H11	120.5	C33—C38—H38	119.5
N3—C12—C11	122.2 (3)	C37—C38—H38	119.5
N3—C12—H12	118.9

Symmetry codes: (i) −x+1, −y, −z−1; (ii) −x, −y, −z−1; (iii) x−1, y−1, z−1; (iv) x, y−1, z−1; (v) −x, −y, −z; (vi) x−1, y, z; (vii) −x+1, −y+1, −z+1; (viii) x, y, z+1.