[μ-rel-(3R,6S)-10,22-Dichloro-3,6-dimethyl-3,6,14,18-tetra­azatricyclo­[18.3.1.18,12]penta­cosa-1(24),8,10,12(25),13,18,20,22-octane-24,25-diolato-κ4N3,N6,O24,O25:κ4N14,N18,O24,O25]dicopper(II) perchlorate

Liu, H.; Li, Y.-Z.; Hu, D.; Pan, Z.-Q.; Hu, X.-L.

doi:10.1107/S1600536806035859

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[μ-rel-(3R,6S)-10,22-Dichloro-3,6-dimethyl-3,6,14,18-tetraazatricyclo[18.3.1.1^8,12]pentacosa-1(24),8,10,12(25),13,18,20,22-octane-24,25-diolato-κ⁴N³,N⁶,O²⁴,O²⁵:κ⁴N¹⁴,N¹⁸,O²⁴,O²⁵]dicopper(II) perchlorate

H. Liu, Y.-Z. Li, D. Hu, Z.-Q. Pan and X.-L. Hu

The title complex, [Cu₂(C₂₃H₂₆Cl₂N₄O₂)](ClO₄)₂, has been synthesized by condensation between N,N′-dimethyl-N,N′-bis(3-formyl-5-chlorosalicylidene)ethylenediamine and 1,3-propanediamine in the presence of copper(II). The complex is a phenol-based macrocyclic dinuclear complex, with the two Cu^II ions in N(amine)₂O₂ and N(imine)₂O₂ sites, and a Cu

Cu separation of 3.0138 (14) Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035859/hg2075sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035859/hg2075Isup2.hkl Contains datablock I

CCDC reference: 624712

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.011 Å
R factor = 0.061
wR factor = 0.126
Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         11

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               5798
           Count of symmetry unique reflns         3092
           Completeness (_total/calc)            187.52%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2706
           Fraction of Friedel pairs measured     0.875
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of N1     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of N2     = .          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

[µ-rel-(3R,6S)-10,22-Dichloro-3,6-dimethyl-3,6,14,18- tetraazatricyclo[18.3.1.1^8,12]pentacosa-1(24),8,10,12(25),13,18,20,22- octane-24,25-diolato- κ⁴N³,N⁶,O²⁴,O²⁵:κ⁴N¹⁴,N¹⁸,O²⁴,O²⁵]dicopper(II) perchlorate top

Crystal data top

[Cu₂(C₂₃H₂₆Cl₂N₄O₂)](ClO₄)₂	F(000) = 796
M_r = 787.36	D_x = 1.762 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2271 reflections
a = 8.7105 (16) Å	θ = 2.3–19.9°
b = 9.5778 (18) Å	µ = 1.85 mm⁻¹
c = 18.104 (3) Å	T = 298 K
β = 100.761 (18)°	Needle, dark green
V = 1483.8 (5) Å³	0.32 × 0.26 × 0.24 mm
Z = 2

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5798 independent reflections
Radiation source: sealed tube	4438 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
φ and ω scans	θ_max = 26.0°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
T_min = 0.57, T_max = 0.64	k = −11→11
15477 measured reflections	l = −22→22

Refinement top

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)] = 0.061	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.05P)² + 1.88P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
5798 reflections	Δρ_max = 0.37 e Å⁻³
390 parameters	Δρ_min = −0.67 e Å⁻³
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (2)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2472 (9)	0.7053 (9)	0.6394 (4)	0.0398 (17)
C2	0.2562 (8)	0.6453 (8)	0.5704 (4)	0.0433 (19)
C3	0.1295 (9)	0.6533 (8)	0.5112 (5)	0.0440 (19)
H3	0.1355	0.6132	0.4650	0.053*
C4	−0.0063 (8)	0.7213 (9)	0.5210 (4)	0.0415 (17)
C5	−0.0153 (11)	0.7813 (10)	0.5899 (4)	0.055 (2)
H5	−0.1062	0.8268	0.5965	0.066*
C6	0.1114 (9)	0.7732 (8)	0.6492 (4)	0.0447 (19)
C7	0.0856 (8)	0.8166 (9)	0.7239 (4)	0.0425 (16)
H7A	−0.0156	0.8619	0.7180	0.051*
H7B	0.0814	0.7336	0.7542	0.051*
C8	0.1637 (9)	0.9629 (10)	0.8358 (4)	0.0471 (19)
H8A	0.0583	0.9356	0.8396	0.057*
H8B	0.1663	1.0641	0.8339	0.057*
C9	0.2733 (9)	0.9153 (9)	0.9060 (4)	0.048 (2)
H9A	0.2814	0.9870	0.9444	0.058*
H9B	0.2329	0.8312	0.9253	0.058*
C10	0.5196 (8)	0.7931 (8)	0.9381 (4)	0.0456 (19)
H10A	0.4654	0.7042	0.9345	0.055*
H10B	0.5246	0.8280	0.9888	0.055*
C11	0.6974 (9)	0.6902 (9)	0.8630 (5)	0.0470 (19)
C12	0.6827 (9)	0.7688 (9)	0.9259 (4)	0.048 (2)
C13	0.8029 (9)	0.7700 (9)	0.9883 (5)	0.049 (2)
H13	0.7931	0.8226	1.0304	0.059*
C14	0.9377 (8)	0.6925 (8)	0.9879 (4)	0.0410 (17)
C15	0.9523 (8)	0.6139 (8)	0.9251 (4)	0.0429 (18)
H15	1.0425	0.5621	0.9248	0.051*
C16	0.8322 (8)	0.6128 (8)	0.8626 (4)	0.0417 (17)
C17	0.8539 (9)	0.5206 (8)	0.8005 (4)	0.0413 (17)
H17	0.9475	0.4713	0.8076	0.050*
C18	0.8198 (9)	0.3991 (9)	0.6872 (4)	0.0449 (18)
H18A	0.7764	0.3077	0.6937	0.054*
H18B	0.9324	0.3923	0.7021	0.054*
C19	0.7805 (9)	0.4381 (10)	0.6048 (4)	0.050 (2)
H19A	0.8073	0.5351	0.5985	0.060*
H19B	0.8412	0.3811	0.5765	0.060*
C20	0.6082 (8)	0.4162 (8)	0.5748 (4)	0.0445 (18)
H20A	0.5889	0.4229	0.5204	0.053*
H20B	0.5790	0.3231	0.5880	0.053*
C21	0.3835 (8)	0.5497 (7)	0.5598 (4)	0.0364 (16)
H21	0.3703	0.5046	0.5135	0.044*
C22	0.2086 (10)	1.0351 (8)	0.7190 (4)	0.049 (2)
H22A	0.1965	1.0112	0.6667	0.074*
H22B	0.3085	1.0784	0.7353	0.074*
H22C	0.1273	1.0986	0.7260	0.074*
C23	0.5420 (9)	1.0083 (9)	0.8948 (5)	0.052 (2)
H23A	0.5337	1.0612	0.9389	0.078*
H23B	0.5162	1.0668	0.8512	0.078*
H23C	0.6469	0.9744	0.8988	0.078*
Cl1	−0.1592 (2)	0.7410 (2)	0.44426 (10)	0.0467 (5)
Cl2	1.0895 (2)	0.7020 (2)	1.06212 (11)	0.0495 (5)
Cl3	0.3256 (2)	0.42379 (19)	0.82301 (10)	0.0408 (4)
Cl4	0.6355 (2)	0.9702 (2)	0.67227 (11)	0.0434 (5)
Cu1	0.40054 (11)	0.80931 (9)	0.78585 (6)	0.0478 (3)
Cu2	0.55938 (10)	0.59222 (9)	0.70586 (5)	0.0411 (2)
N1	0.1985 (7)	0.9071 (8)	0.7634 (4)	0.0456 (16)
N2	0.4311 (7)	0.8870 (7)	0.8877 (4)	0.0430 (15)
N3	0.7610 (7)	0.4990 (6)	0.7380 (4)	0.0427 (15)
N4	0.5081 (7)	0.5211 (7)	0.6054 (4)	0.0473 (17)
O1	0.3721 (6)	0.7059 (6)	0.6947 (3)	0.0438 (12)
O2	0.5789 (6)	0.6926 (6)	0.8033 (3)	0.0442 (12)
O3	0.3856 (6)	0.4132 (6)	0.7563 (3)	0.0488 (14)
O4	0.4523 (6)	0.4115 (6)	0.8863 (3)	0.0507 (14)
O5	0.2127 (5)	0.3225 (6)	0.8336 (3)	0.0468 (13)
O6	0.2675 (6)	0.5596 (5)	0.8279 (3)	0.0423 (12)
O7	0.5757 (6)	0.9821 (6)	0.7381 (3)	0.0449 (13)
O8	0.6706 (6)	0.8244 (6)	0.6563 (3)	0.0487 (13)
O9	0.7588 (6)	1.0608 (6)	0.6716 (3)	0.0455 (13)
O10	0.5169 (6)	1.0258 (6)	0.6192 (3)	0.0473 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.046 (4)	0.044 (4)	0.035 (4)	0.002 (3)	0.023 (3)	0.000 (3)
C2	0.038 (4)	0.041 (4)	0.047 (5)	0.015 (3)	−0.003 (3)	−0.013 (3)
C3	0.044 (4)	0.044 (4)	0.046 (5)	0.016 (3)	0.014 (4)	−0.017 (3)
C4	0.035 (4)	0.061 (5)	0.028 (4)	0.009 (3)	0.005 (3)	−0.001 (3)
C5	0.069 (5)	0.060 (6)	0.035 (4)	−0.003 (4)	0.007 (4)	−0.010 (4)
C6	0.047 (4)	0.049 (5)	0.041 (4)	0.011 (3)	0.014 (3)	−0.014 (3)
C7	0.040 (4)	0.044 (4)	0.046 (4)	−0.002 (4)	0.016 (3)	−0.015 (4)
C8	0.043 (4)	0.052 (5)	0.046 (5)	0.015 (4)	0.004 (3)	−0.002 (4)
C9	0.058 (5)	0.045 (5)	0.044 (4)	0.023 (4)	0.017 (4)	−0.012 (4)
C10	0.048 (4)	0.040 (4)	0.044 (4)	0.023 (4)	−0.004 (3)	0.001 (3)
C11	0.039 (4)	0.052 (5)	0.049 (5)	0.006 (4)	0.005 (3)	−0.009 (4)
C12	0.037 (4)	0.063 (6)	0.040 (4)	0.022 (4)	−0.002 (3)	−0.012 (4)
C13	0.043 (4)	0.050 (5)	0.043 (4)	−0.003 (3)	−0.019 (3)	0.008 (3)
C14	0.045 (4)	0.041 (4)	0.037 (4)	0.011 (3)	0.010 (3)	0.001 (3)
C15	0.042 (4)	0.037 (4)	0.050 (5)	0.006 (3)	0.007 (3)	−0.011 (3)
C16	0.033 (3)	0.041 (4)	0.054 (5)	0.012 (3)	0.018 (3)	−0.008 (4)
C17	0.048 (4)	0.039 (4)	0.040 (4)	0.001 (3)	0.016 (3)	−0.003 (3)
C18	0.041 (4)	0.044 (5)	0.052 (5)	0.016 (3)	0.014 (3)	−0.003 (4)
C19	0.051 (5)	0.058 (6)	0.045 (5)	0.001 (4)	0.019 (4)	−0.018 (4)
C20	0.049 (4)	0.044 (4)	0.039 (4)	0.018 (4)	0.004 (3)	−0.004 (3)
C21	0.046 (4)	0.026 (4)	0.035 (4)	0.011 (3)	0.003 (3)	−0.006 (3)
C22	0.058 (5)	0.055 (5)	0.037 (4)	0.021 (4)	0.011 (4)	0.011 (3)
C23	0.048 (4)	0.065 (6)	0.047 (5)	−0.005 (4)	0.017 (4)	−0.021 (4)
Cl1	0.0451 (10)	0.0469 (10)	0.0411 (10)	0.0149 (8)	−0.0106 (8)	−0.0169 (8)
Cl2	0.0478 (10)	0.0468 (11)	0.0481 (11)	0.0046 (9)	−0.0062 (8)	−0.0056 (9)
Cl3	0.0392 (9)	0.0386 (10)	0.0466 (10)	0.0079 (7)	0.0132 (8)	0.0027 (8)
Cl4	0.0438 (10)	0.0452 (11)	0.0413 (11)	−0.0066 (8)	0.0078 (8)	0.0175 (8)
Cu1	0.0444 (5)	0.0405 (6)	0.0545 (6)	0.0108 (4)	−0.0011 (4)	−0.0105 (4)
Cu2	0.0383 (5)	0.0448 (5)	0.0378 (5)	0.0071 (4)	0.0011 (4)	−0.0025 (4)
N1	0.045 (3)	0.055 (4)	0.039 (4)	0.005 (3)	0.014 (3)	0.006 (3)
N2	0.040 (3)	0.042 (4)	0.049 (4)	0.014 (3)	0.012 (3)	−0.003 (3)
N3	0.042 (3)	0.038 (4)	0.051 (4)	0.006 (3)	0.015 (3)	−0.013 (3)
N4	0.046 (4)	0.052 (4)	0.047 (4)	0.022 (3)	0.016 (3)	−0.014 (3)
O1	0.042 (3)	0.049 (3)	0.045 (3)	0.002 (2)	0.021 (2)	−0.011 (3)
O2	0.038 (3)	0.048 (3)	0.048 (3)	0.015 (2)	0.011 (2)	−0.002 (3)
O3	0.054 (3)	0.050 (3)	0.047 (3)	0.012 (3)	0.020 (3)	−0.008 (3)
O4	0.052 (3)	0.039 (3)	0.057 (3)	−0.008 (2)	−0.001 (3)	0.015 (3)
O5	0.044 (3)	0.046 (3)	0.055 (3)	−0.001 (3)	0.021 (2)	0.008 (3)
O6	0.054 (3)	0.027 (3)	0.051 (3)	0.011 (2)	0.025 (2)	−0.011 (2)
O7	0.042 (3)	0.044 (3)	0.045 (3)	0.011 (2)	−0.001 (2)	−0.011 (3)
O8	0.043 (3)	0.053 (3)	0.052 (3)	−0.009 (3)	0.017 (2)	−0.002 (3)
O9	0.050 (3)	0.045 (3)	0.047 (3)	−0.005 (2)	0.024 (2)	0.006 (2)
O10	0.047 (3)	0.056 (3)	0.037 (3)	0.006 (2)	0.003 (2)	0.010 (2)

Geometric parameters (Å, º) top

C1—O1	1.334 (9)	C17—H17	0.9300
C1—C2	1.390 (10)	C18—N3	1.482 (9)
C1—C6	1.390 (10)	C18—C19	1.515 (11)
C2—C3	1.390 (11)	C18—H18A	0.9700
C2—C21	1.478 (9)	C18—H18B	0.9700
C3—C4	1.390 (10)	C19—C20	1.512 (11)
C3—H3	0.9300	C19—H19A	0.9700
C4—C5	1.390 (10)	C19—H19B	0.9700
C4—Cl1	1.745 (7)	C20—N4	1.502 (9)
C5—C6	1.390 (11)	C20—H20A	0.9700
C5—H5	0.9300	C20—H20B	0.9700
C6—C7	1.473 (9)	C21—N4	1.265 (9)
C7—N1	1.403 (9)	C21—H21	0.9300
C7—H7A	0.9700	C22—N1	1.478 (10)
C7—H7B	0.9700	C22—H22A	0.9600
C8—N1	1.496 (10)	C22—H22B	0.9600
C8—C9	1.511 (10)	C22—H22C	0.9600
C8—H8A	0.9700	C23—N2	1.501 (10)
C8—H8B	0.9700	C23—H23A	0.9600
C9—N2	1.498 (9)	C23—H23B	0.9600
C9—H9A	0.9700	C23—H23C	0.9600
C9—H9B	0.9700	Cl3—O6	1.405 (5)
C10—N2	1.405 (9)	Cl3—O3	1.406 (5)
C10—C12	1.497 (10)	Cl3—O5	1.419 (5)
C10—H10A	0.9700	Cl3—O4	1.440 (6)
C10—H10B	0.9700	Cl4—O10	1.380 (5)
C11—O2	1.349 (9)	Cl4—O9	1.383 (5)
C11—C12	1.390 (11)	Cl4—O7	1.391 (6)
C11—C16	1.390 (10)	Cl4—O8	1.470 (6)
C12—C13	1.390 (10)	Cu1—O2	1.892 (5)
C13—C14	1.390 (11)	Cu1—O1	1.900 (5)
C13—H13	0.9300	Cu1—N2	1.960 (6)
C14—C15	1.390 (10)	Cu1—N1	1.968 (6)
C14—Cl2	1.702 (7)	Cu2—N4	1.915 (6)
C15—C16	1.390 (10)	Cu2—O1	1.941 (5)
C15—H15	0.9300	Cu2—N3	1.960 (6)
C16—C17	1.469 (10)	Cu2—O2	1.988 (5)
C17—N3	1.279 (10)

O1—C1—C2	120.1 (6)	C20—C19—H19B	109.6
O1—C1—C6	119.7 (6)	C18—C19—H19B	109.6
C2—C1—C6	120.0 (7)	H19A—C19—H19B	108.1
C3—C2—C1	120.0 (7)	N4—C20—C19	112.4 (6)
C3—C2—C21	116.2 (7)	N4—C20—H20A	109.1
C1—C2—C21	122.9 (7)	C19—C20—H20A	109.1
C4—C3—C2	120.0 (7)	N4—C20—H20B	109.1
C4—C3—H3	120.0	C19—C20—H20B	109.1
C2—C3—H3	120.0	H20A—C20—H20B	107.9
C5—C4—C3	120.0 (7)	N4—C21—C2	128.4 (7)
C5—C4—Cl1	120.5 (6)	N4—C21—H21	115.8
C3—C4—Cl1	119.4 (5)	C2—C21—H21	115.8
C4—C5—C6	120.0 (8)	N1—C22—H22A	109.5
C4—C5—H5	120.0	N1—C22—H22B	109.5
C6—C5—H5	120.0	H22A—C22—H22B	109.5
C5—C6—C1	120.0 (7)	N1—C22—H22C	109.5
C5—C6—C7	117.2 (7)	H22A—C22—H22C	109.5
C1—C6—C7	121.9 (7)	H22B—C22—H22C	109.5
N1—C7—C6	115.5 (6)	N2—C23—H23A	109.5
N1—C7—H7A	108.4	N2—C23—H23B	109.5
C6—C7—H7A	108.4	H23A—C23—H23B	109.5
N1—C7—H7B	108.4	N2—C23—H23C	109.5
C6—C7—H7B	108.4	H23A—C23—H23C	109.5
H7A—C7—H7B	107.5	H23B—C23—H23C	109.5
N1—C8—C9	115.4 (6)	O6—Cl3—O3	108.5 (3)
N1—C8—H8A	108.4	O6—Cl3—O5	111.0 (3)
C9—C8—H8A	108.4	O3—Cl3—O5	116.4 (4)
N1—C8—H8B	108.4	O6—Cl3—O4	104.9 (3)
C9—C8—H8B	108.4	O3—Cl3—O4	109.0 (3)
H8A—C8—H8B	107.5	O5—Cl3—O4	106.5 (3)
N2—C9—C8	109.2 (6)	O10—Cl4—O9	103.5 (3)
N2—C9—H9A	109.8	O10—Cl4—O7	102.3 (3)
C8—C9—H9A	109.8	O9—Cl4—O7	111.8 (3)
N2—C9—H9B	109.8	O10—Cl4—O8	112.7 (3)
C8—C9—H9B	109.8	O9—Cl4—O8	113.9 (3)
H9A—C9—H9B	108.3	O7—Cl4—O8	111.8 (3)
N2—C10—C12	115.1 (7)	O2—Cu1—O1	78.9 (2)
N2—C10—H10A	108.5	O2—Cu1—N2	96.0 (2)
C12—C10—H10A	108.5	O1—Cu1—N2	170.9 (3)
N2—C10—H10B	108.5	O2—Cu1—N1	172.1 (3)
C12—C10—H10B	108.5	O1—Cu1—N1	95.9 (3)
H10A—C10—H10B	107.5	N2—Cu1—N1	88.4 (3)
O2—C11—C12	118.3 (7)	N4—Cu2—O1	93.3 (2)
O2—C11—C16	121.7 (7)	N4—Cu2—N3	99.0 (3)
C12—C11—C16	120.0 (7)	O1—Cu2—N3	167.5 (2)
C11—C12—C13	120.0 (7)	N4—Cu2—O2	168.7 (2)
C11—C12—C10	116.1 (7)	O1—Cu2—O2	75.6 (2)
C13—C12—C10	118.0 (7)	N3—Cu2—O2	91.9 (2)
C14—C13—C12	120.0 (8)	C7—N1—C22	110.0 (6)
C14—C13—H13	120.0	C7—N1—C8	115.4 (6)
C12—C13—H13	120.0	C22—N1—C8	102.9 (6)
C15—C14—C13	120.0 (7)	C7—N1—Cu1	109.0 (5)
C15—C14—Cl2	119.9 (6)	C22—N1—Cu1	111.4 (5)
C13—C14—Cl2	120.0 (6)	C8—N1—Cu1	108.0 (5)
C16—C15—C14	120.0 (7)	C10—N2—C9	112.8 (6)
C16—C15—H15	120.0	C10—N2—C23	100.0 (6)
C14—C15—H15	120.0	C9—N2—C23	116.3 (6)
C15—C16—C11	120.0 (7)	C10—N2—Cu1	109.3 (5)
C15—C16—C17	116.3 (6)	C9—N2—Cu1	108.0 (5)
C11—C16—C17	123.6 (7)	C23—N2—Cu1	110.3 (5)
N3—C17—C16	128.6 (7)	C17—N3—C18	114.8 (6)
N3—C17—H17	115.7	C17—N3—Cu2	124.9 (5)
C16—C17—H17	115.7	C18—N3—Cu2	120.3 (5)
N3—C18—C19	114.3 (6)	C21—N4—C20	113.0 (6)
N3—C18—H18A	108.7	C21—N4—Cu2	124.3 (5)
C19—C18—H18A	108.7	C20—N4—Cu2	122.6 (5)
N3—C18—H18B	108.7	C1—O1—Cu1	127.6 (5)
C19—C18—H18B	108.7	C1—O1—Cu2	128.8 (5)
H18A—C18—H18B	107.6	Cu1—O1—Cu2	103.4 (2)
C20—C19—C18	110.2 (7)	C11—O2—Cu1	128.7 (5)
C20—C19—H19A	109.6	C11—O2—Cu2	129.0 (5)
C18—C19—H19A	109.6	Cu1—O2—Cu2	101.9 (2)

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