Dichloro[N,N-dimethyl-1-(1-methyl-1H-tetrazol-5-yl-κN⁴)methanamine-κN]copper(II)

The title compound, [CuCl₂(C₅H₁₁N₅)], is the first structurally characterized molecular chelate complex involving an α-­amino­alkyl­tetrazole. There are two complex mol­ecules in the asymmetric unit. The ligand mol­ecules are bidentate. Both Cu atoms reveal rather distorted square-planar coordinations. The complex mol­ecules are linked together by van der Waals interactions only.

S1. Comment

5-(α-Aminoalkyl)-1R-tetrazoles represent an interesting class of ligands which have various coordination abilities because of the presence of five N atoms. Moreover, the coordination chemistry of these ligands is of considerable interest, due to the fact that they are isosteric with peptide units (Lodyga-Chruscinska et al., 1999). However, no structures of transition metal complexes with α-aminoalkyltetrazole ligands have been described to date. In this paper, we report the molecular and crystal structures of the copper(II) chloride complex with N,N-dimethyl-1-(1-methyl-1H-tetrazol-5-yl)methanamine, (I). \sch

There are two complex molecules in the asymmetric unit of (I), and these are denoted A and B; molecule A is illustrated in Fig. 1. The N,N-dimethyl-1-(1-methyl-1H-tetrazol-5-yl)methanamine ligands are bidentate. Both Cu atoms reveal rather distorted square-planar coordination, with the coordination environment of the Cu atom being formed by atom N4 of the tetrazole ring, atom N5 of the N,N-dimethylmethanamine and the two Cl atoms (Table 1). The mean deviations from the least-squares plane for the four atoms coordinated to the Cu atoms are 0.2435 (15) Å for molecule A and 0.2113 (16) Å for molecule B. The Cu atoms are 0.0511 (13) and 0.0475 (13) Å distant from the corresponding least-squares plane in molecules A and B, respectively.

The tetrazole rings of molecules A and B have very similar geometries, close to those previously observed for 1,5-substituted tetrazole rings (Cambridge Structural Database, Version 5.23, September 2002; Allen & Kennard, 1993). The rings are essentially planar, with mean deviations from the least-squares plane for the tetrazole ring atoms of 0.004 (2) and 0.005 (2) Å for molecules A and B, respectively.

The chelate rings formed by atoms Cu, N4, C5, C6 and N5 are not planar. The Cu, N4, C5 and C6 atoms lie in the plane, with mean deviations from the least-squares plane of 0.016 (2) Å for molecule A and 0.009 (2) Å for molecule B. The dihedral angles between these planes and the C6/N5/Cu planes are 31.13 (14) and 31.91 (15)° for molecules A and B, respectively.

There are no hydrogen bonds in the structure of (I); the complex molecules are linked together only by van der Waals interactions (Fig. 2).

S2. Experimental

The N,N-dimethyl-1-(1-methyl-1H-tetrazol-5-yl)methanamine ligand was synthesized by aminomethylation of 1-methyltetrazole with dimethylamine hydrochloride and formaldehyde, according to the technique described by Karavai & Gaponik (1991). Green crystals of the title complex were obtained by slow evaporation in air of an equimolar solution of copper(II) chloride and N,N-dimethyl-1-(1-methyl-1H-tetrazol-5-yl)methanamine in a mixture of ethanol and butanol (v/v 3:1) [yield 91%, m.p. 548 K (decomposition)].

S3. Refinement

H atoms were included in their idealized positions, with C—H distances of 0.96 Å, and were refined using a riding model, with U_iso(H) = 1.5U_eq(C) for the methyl groups and 1.2U_eq(C) for the methylene group.

Computing details

Data collection: R3m Software (Nicolet, 1980); cell refinement: R3m Software; data reduction: R3m Software; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP 3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. A view of the structure of molecule A of (I), showing the atom-numbering scheme; for molecule B, the suffix A is replaced by the suffix B. Displacement ellipsoids are plotted at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The crystal packing of (I) viewed along the b axis.

Dichloro[N,N-dimethyl-1-(1-methyl-1H-tetrazol-5-yl-κN⁴)methanamine- κN]copper(II)

Crystal data

[CuCl2(C5N5H11)]	F(000) = 1112
Mr = 275.63	Dx = 1.773 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 18.043 (3) Å	θ = 16.9–21.9°
b = 7.1948 (13) Å	µ = 2.60 mm^−1
c = 18.048 (3) Å	T = 293 K
β = 118.205 (13)°	Prism, green
V = 2064.7 (6) Å^3	0.60 × 0.35 × 0.10 mm
Z = 8

Data collection

Nicolet R3m four-circle diffractometer	4431 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 30.1°, θmin = 1.3°
ω/2θ scans	h = 0→25
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.305, Tmax = 0.781	l = −25→22
6427 measured reflections	3 standard reflections every 100 reflections
6052 independent reflections	intensity decay: none

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.19	w = 1/[σ^2(Fo^2) + (0.032P)^2 + 4.2852P] where P = (Fo^2 + 2Fc^2)/3
6052 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.45 e Å^−3

Special details

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
N1A	0.25795 (19)	0.2669 (4)	0.61968 (17)	0.0333 (6)
N2A	0.1808 (2)	0.2038 (5)	0.6031 (2)	0.0436 (8)
N3A	0.1816 (2)	0.1817 (5)	0.6746 (2)	0.0435 (8)
N4A	0.25869 (19)	0.2278 (5)	0.73724 (18)	0.0361 (7)
C5A	0.3052 (2)	0.2795 (5)	0.7024 (2)	0.0291 (6)
C6A	0.3927 (2)	0.3412 (6)	0.7556 (2)	0.0341 (7)
H6A1	0.3961	0.4757	0.7550	0.041*
H6A2	0.4293	0.2895	0.7351	0.041*
N5A	0.41822 (17)	0.2736 (4)	0.84254 (17)	0.0303 (6)
C7A	0.4497 (3)	0.0799 (6)	0.8514 (3)	0.0473 (10)
H7A1	0.4055	0.0010	0.8124	0.071*
H7A2	0.4675	0.0373	0.9077	0.071*
H7A3	0.4964	0.0762	0.8397	0.071*
C8A	0.4870 (2)	0.3933 (7)	0.9030 (2)	0.0434 (9)
H8A1	0.4672	0.5189	0.8979	0.065*
H8A2	0.5335	0.3889	0.8912	0.065*
H8A3	0.5047	0.3496	0.9592	0.065*
C9A	0.2770 (3)	0.3076 (7)	0.5514 (2)	0.0519 (11)
H9A1	0.2283	0.2829	0.4985	0.078*
H9A2	0.3228	0.2306	0.5568	0.078*
H9A3	0.2925	0.4360	0.5538	0.078*
Cl1A	0.18621 (6)	0.29754 (17)	0.85725 (7)	0.0475 (2)
Cl2A	0.38137 (7)	0.2010 (2)	0.99607 (6)	0.0556 (3)
Cu1A	0.31100 (3)	0.25693 (6)	0.86078 (2)	0.03054 (11)
N1B	0.87934 (17)	0.2382 (4)	0.74284 (18)	0.0324 (6)
N2B	0.8954 (2)	0.1794 (5)	0.8202 (2)	0.0407 (7)
N3B	0.8238 (2)	0.1599 (5)	0.81909 (19)	0.0418 (7)
N4B	0.76154 (18)	0.2065 (5)	0.74183 (18)	0.0352 (7)
C5B	0.7967 (2)	0.2520 (5)	0.6954 (2)	0.0294 (6)
C6B	0.7438 (2)	0.3153 (6)	0.6077 (2)	0.0336 (7)
H6B1	0.7641	0.2634	0.5710	0.040*
H6B2	0.7447	0.4497	0.6045	0.040*
N5B	0.65677 (18)	0.2484 (4)	0.58234 (17)	0.0310 (6)
C7B	0.6484 (3)	0.0533 (6)	0.5528 (3)	0.0466 (9)
H7B1	0.6879	−0.0235	0.5976	0.070*
H7B2	0.6597	0.0470	0.5060	0.070*
H7B3	0.5923	0.0102	0.5358	0.070*
C8B	0.5961 (3)	0.3651 (7)	0.5128 (2)	0.0450 (9)
H8B1	0.6008	0.4915	0.5315	0.067*
H8B2	0.5400	0.3209	0.4954	0.067*
H8B3	0.6079	0.3586	0.4663	0.067*
C9B	0.9485 (3)	0.2739 (8)	0.7243 (3)	0.0557 (12)
H9B1	1.0010	0.2501	0.7735	0.084*
H9B2	0.9466	0.4012	0.7076	0.084*
H9B3	0.9433	0.1938	0.6795	0.084*
Cl1B	0.64304 (6)	0.27437 (17)	0.81533 (6)	0.0488 (3)
Cl2B	0.50249 (6)	0.1940 (2)	0.62028 (7)	0.0616 (3)
Cu1B	0.63848 (2)	0.23736 (6)	0.68995 (2)	0.03061 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0353 (14)	0.0362 (16)	0.0248 (12)	−0.0006 (12)	0.0113 (11)	−0.0022 (12)
N2A	0.0427 (18)	0.048 (2)	0.0322 (15)	−0.0058 (15)	0.0111 (14)	−0.0015 (14)
N3A	0.0336 (16)	0.054 (2)	0.0366 (16)	−0.0094 (15)	0.0117 (13)	0.0023 (15)
N4A	0.0294 (14)	0.0473 (19)	0.0301 (14)	−0.0088 (13)	0.0128 (12)	0.0008 (13)
C5A	0.0311 (15)	0.0315 (17)	0.0255 (14)	0.0005 (13)	0.0139 (12)	−0.0003 (12)
C6A	0.0313 (16)	0.045 (2)	0.0298 (16)	−0.0025 (15)	0.0175 (14)	−0.0018 (15)
N5A	0.0258 (12)	0.0390 (16)	0.0256 (12)	0.0009 (11)	0.0117 (10)	−0.0030 (11)
C7A	0.047 (2)	0.046 (2)	0.050 (2)	0.0159 (19)	0.0236 (19)	0.0021 (19)
C8A	0.0322 (17)	0.060 (3)	0.0362 (18)	−0.0077 (17)	0.0143 (15)	−0.0123 (18)
C9A	0.062 (3)	0.069 (3)	0.0314 (18)	0.008 (2)	0.0270 (19)	0.0028 (19)
Cl1A	0.0368 (4)	0.0655 (7)	0.0474 (5)	0.0025 (4)	0.0259 (4)	0.0020 (5)
Cl2A	0.0472 (5)	0.0879 (9)	0.0290 (4)	0.0035 (5)	0.0158 (4)	0.0115 (5)
Cu1A	0.0288 (2)	0.0380 (2)	0.02599 (19)	−0.00010 (17)	0.01385 (16)	0.00172 (17)
N1B	0.0258 (13)	0.0381 (16)	0.0323 (14)	0.0000 (12)	0.0130 (11)	0.0010 (12)
N2B	0.0324 (15)	0.0484 (19)	0.0357 (16)	0.0002 (14)	0.0113 (13)	0.0052 (14)
N3B	0.0344 (15)	0.055 (2)	0.0310 (15)	0.0001 (15)	0.0113 (13)	0.0091 (14)
N4B	0.0283 (14)	0.0506 (19)	0.0267 (13)	0.0023 (13)	0.0131 (11)	0.0076 (12)
C5B	0.0291 (15)	0.0314 (16)	0.0294 (14)	0.0009 (13)	0.0152 (12)	0.0014 (13)
C6B	0.0311 (16)	0.0429 (19)	0.0297 (15)	0.0013 (15)	0.0168 (13)	0.0040 (14)
N5B	0.0276 (13)	0.0388 (15)	0.0252 (12)	0.0025 (12)	0.0113 (11)	−0.0014 (12)
C7B	0.054 (2)	0.043 (2)	0.046 (2)	−0.0038 (19)	0.027 (2)	−0.0116 (18)
C8B	0.040 (2)	0.060 (3)	0.0297 (17)	0.0078 (19)	0.0125 (15)	0.0055 (17)
C9B	0.0334 (19)	0.082 (4)	0.060 (3)	0.000 (2)	0.0288 (19)	0.007 (2)
Cl1B	0.0456 (5)	0.0728 (7)	0.0356 (4)	0.0006 (5)	0.0256 (4)	−0.0003 (5)
Cl2B	0.0298 (4)	0.1044 (10)	0.0483 (6)	−0.0137 (5)	0.0166 (4)	−0.0128 (6)
Cu1B	0.02625 (19)	0.0388 (2)	0.0282 (2)	−0.00182 (17)	0.01401 (16)	−0.00178 (17)

Geometric parameters (Å, º)

N1A—C5A	1.327 (4)	N1B—C5B	1.326 (4)
N1A—N2A	1.356 (5)	N1B—N2B	1.354 (4)
N1A—C9A	1.458 (5)	N1B—C9B	1.459 (5)
N2A—N3A	1.295 (5)	N2B—N3B	1.289 (4)
N3A—N4A	1.355 (4)	N3B—N4B	1.356 (4)
N4A—C5A	1.318 (4)	N4B—C5B	1.311 (4)
N4A—Cu1A	1.979 (3)	N4B—Cu1B	1.973 (3)
C5A—C6A	1.475 (5)	C5B—C6B	1.481 (5)
C6A—N5A	1.493 (4)	C6B—N5B	1.492 (4)
C6A—H6A1	0.9700	C6B—H6B1	0.9700
C6A—H6A2	0.9700	C6B—H6B2	0.9700
N5A—C8A	1.480 (5)	N5B—C8B	1.477 (5)
N5A—C7A	1.484 (5)	N5B—C7B	1.483 (5)
N5A—Cu1A	2.114 (3)	N5B—Cu1B	2.120 (3)
C7A—H7A1	0.9600	C7B—H7B1	0.9600
C7A—H7A2	0.9600	C7B—H7B2	0.9600
C7A—H7A3	0.9600	C7B—H7B3	0.9600
C8A—H8A1	0.9600	C8B—H8B1	0.9600
C8A—H8A2	0.9600	C8B—H8B2	0.9600
C8A—H8A3	0.9600	C8B—H8B3	0.9600
C9A—H9A1	0.9600	C9B—H9B1	0.9600
C9A—H9A2	0.9600	C9B—H9B2	0.9600
C9A—H9A3	0.9600	C9B—H9B3	0.9600
Cl1A—Cu1A	2.2413 (11)	Cl1B—Cu1B	2.2411 (11)
Cl2A—Cu1A	2.1922 (11)	Cl2B—Cu1B	2.1869 (11)
C5A—N1A—N2A	108.6 (3)	C5B—N1B—N2B	108.5 (3)
C5A—N1A—C9A	130.9 (3)	C5B—N1B—C9B	131.3 (3)
N2A—N1A—C9A	120.5 (3)	N2B—N1B—C9B	120.2 (3)
N3A—N2A—N1A	107.1 (3)	N3B—N2B—N1B	107.1 (3)
N2A—N3A—N4A	108.9 (3)	N2B—N3B—N4B	109.1 (3)
C5A—N4A—N3A	107.8 (3)	C5B—N4B—N3B	107.7 (3)
C5A—N4A—Cu1A	115.8 (2)	C5B—N4B—Cu1B	116.4 (2)
N3A—N4A—Cu1A	136.1 (2)	N3B—N4B—Cu1B	135.7 (2)
N4A—C5A—N1A	107.6 (3)	N4B—C5B—N1B	107.7 (3)
N4A—C5A—C6A	120.1 (3)	N4B—C5B—C6B	119.8 (3)
N1A—C5A—C6A	132.3 (3)	N1B—C5B—C6B	132.4 (3)
C5A—C6A—N5A	106.8 (3)	C5B—C6B—N5B	106.4 (3)
C5A—C6A—H6A1	110.4	C5B—C6B—H6B1	110.4
N5A—C6A—H6A1	110.4	N5B—C6B—H6B1	110.4
C5A—C6A—H6A2	110.4	C5B—C6B—H6B2	110.4
N5A—C6A—H6A2	110.4	N5B—C6B—H6B2	110.4
H6A1—C6A—H6A2	108.6	H6B1—C6B—H6B2	108.6
C8A—N5A—C7A	108.8 (3)	C8B—N5B—C7B	108.9 (3)
C8A—N5A—C6A	108.7 (3)	C8B—N5B—C6B	109.1 (3)
C7A—N5A—C6A	109.3 (3)	C7B—N5B—C6B	109.2 (3)
C8A—N5A—Cu1A	115.3 (2)	C8B—N5B—Cu1B	115.2 (2)
C7A—N5A—Cu1A	105.2 (2)	C7B—N5B—Cu1B	105.1 (2)
C6A—N5A—Cu1A	109.4 (2)	C6B—N5B—Cu1B	109.1 (2)
N5A—C7A—H7A1	109.5	N5B—C7B—H7B1	109.5
N5A—C7A—H7A2	109.5	N5B—C7B—H7B2	109.5
H7A1—C7A—H7A2	109.5	H7B1—C7B—H7B2	109.5
N5A—C7A—H7A3	109.5	N5B—C7B—H7B3	109.5
H7A1—C7A—H7A3	109.5	H7B1—C7B—H7B3	109.5
H7A2—C7A—H7A3	109.5	H7B2—C7B—H7B3	109.5
N5A—C8A—H8A1	109.5	N5B—C8B—H8B1	109.5
N5A—C8A—H8A2	109.5	N5B—C8B—H8B2	109.5
H8A1—C8A—H8A2	109.5	H8B1—C8B—H8B2	109.5
N5A—C8A—H8A3	109.5	N5B—C8B—H8B3	109.5
H8A1—C8A—H8A3	109.5	H8B1—C8B—H8B3	109.5
H8A2—C8A—H8A3	109.5	H8B2—C8B—H8B3	109.5
N1A—C9A—H9A1	109.5	N1B—C9B—H9B1	109.5
N1A—C9A—H9A2	109.5	N1B—C9B—H9B2	109.5
H9A1—C9A—H9A2	109.5	H9B1—C9B—H9B2	109.5
N1A—C9A—H9A3	109.5	N1B—C9B—H9B3	109.5
H9A1—C9A—H9A3	109.5	H9B1—C9B—H9B3	109.5
H9A2—C9A—H9A3	109.5	H9B2—C9B—H9B3	109.5
N4A—Cu1A—N5A	79.33 (11)	N4B—Cu1B—N5B	79.12 (11)
N4A—Cu1A—Cl2A	162.22 (11)	N4B—Cu1B—Cl2B	164.19 (11)
N5A—Cu1A—Cl2A	95.33 (8)	N5B—Cu1B—Cl2B	95.55 (8)
N4A—Cu1A—Cl1A	92.52 (9)	N4B—Cu1B—Cl1B	92.19 (9)
N5A—Cu1A—Cl1A	165.78 (9)	N5B—Cu1B—Cl1B	166.76 (9)
Cl2A—Cu1A—Cl1A	95.79 (4)	Cl2B—Cu1B—Cl1B	95.35 (5)
C5A—N1A—N2A—N3A	1.0 (4)	C5B—N1B—N2B—N3B	−0.5 (4)
C9A—N1A—N2A—N3A	−179.4 (4)	C9B—N1B—N2B—N3B	179.8 (4)
N1A—N2A—N3A—N4A	−0.7 (5)	N1B—N2B—N3B—N4B	−0.3 (5)
N2A—N3A—N4A—C5A	0.2 (5)	N2B—N3B—N4B—C5B	1.0 (5)
N2A—N3A—N4A—Cu1A	173.3 (3)	N2B—N3B—N4B—Cu1B	−173.5 (3)
N3A—N4A—C5A—N1A	0.4 (4)	N3B—N4B—C5B—N1B	−1.2 (4)
Cu1A—N4A—C5A—N1A	−174.3 (2)	Cu1B—N4B—C5B—N1B	174.5 (2)
N3A—N4A—C5A—C6A	178.9 (3)	N3B—N4B—C5B—C6B	−178.1 (3)
Cu1A—N4A—C5A—C6A	4.2 (4)	Cu1B—N4B—C5B—C6B	−2.4 (5)
N2A—N1A—C5A—N4A	−0.8 (4)	N2B—N1B—C5B—N4B	1.1 (4)
C9A—N1A—C5A—N4A	179.6 (4)	C9B—N1B—C5B—N4B	−179.2 (4)
N2A—N1A—C5A—C6A	−179.1 (4)	N2B—N1B—C5B—C6B	177.4 (4)
C9A—N1A—C5A—C6A	1.3 (7)	C9B—N1B—C5B—C6B	−2.9 (7)
N4A—C5A—C6A—N5A	17.8 (5)	N4B—C5B—C6B—N5B	−19.9 (5)
N1A—C5A—C6A—N5A	−164.1 (4)	N1B—C5B—C6B—N5B	164.2 (4)
C5A—C6A—N5A—C8A	−155.9 (3)	C5B—C6B—N5B—C8B	157.1 (3)
C5A—C6A—N5A—C7A	85.5 (3)	C5B—C6B—N5B—C7B	−84.0 (3)
C5A—C6A—N5A—Cu1A	−29.2 (3)	C5B—C6B—N5B—Cu1B	30.4 (3)
C5A—N4A—Cu1A—N5A	−17.0 (3)	C5B—N4B—Cu1B—N5B	16.3 (3)
N3A—N4A—Cu1A—N5A	170.3 (4)	N3B—N4B—Cu1B—N5B	−169.6 (4)
C5A—N4A—Cu1A—Cl2A	−90.9 (4)	C5B—N4B—Cu1B—Cl2B	87.8 (4)
N3A—N4A—Cu1A—Cl2A	96.5 (5)	N3B—N4B—Cu1B—Cl2B	−98.1 (5)
C5A—N4A—Cu1A—Cl1A	151.2 (3)	C5B—N4B—Cu1B—Cl1B	−153.6 (3)
N3A—N4A—Cu1A—Cl1A	−21.4 (4)	N3B—N4B—Cu1B—Cl1B	20.5 (4)
C8A—N5A—Cu1A—N4A	148.6 (3)	C8B—N5B—Cu1B—N4B	−149.3 (3)
C7A—N5A—Cu1A—N4A	−91.5 (2)	C7B—N5B—Cu1B—N4B	90.8 (3)
C6A—N5A—Cu1A—N4A	25.8 (2)	C6B—N5B—Cu1B—N4B	−26.2 (2)
C8A—N5A—Cu1A—Cl2A	−48.5 (3)	C8B—N5B—Cu1B—Cl2B	45.7 (3)
C7A—N5A—Cu1A—Cl2A	71.4 (2)	C7B—N5B—Cu1B—Cl2B	−74.2 (2)
C6A—N5A—Cu1A—Cl2A	−171.3 (2)	C6B—N5B—Cu1B—Cl2B	168.8 (2)
C8A—N5A—Cu1A—Cl1A	92.8 (4)	C8B—N5B—Cu1B—Cl1B	−99.6 (4)
C7A—N5A—Cu1A—Cl1A	−147.3 (3)	C7B—N5B—Cu1B—Cl1B	140.5 (4)
C6A—N5A—Cu1A—Cl1A	−30.0 (5)	C6B—N5B—Cu1B—Cl1B	23.5 (5)