Bis[4,5-dimethyl-2-(2-pyrid-yl)-1H-imidazole-κN,N](1H-imidazole-κN)copper(II) bis-(perchlorate).

In the title complex, [Cu(C(3)H(4)N(2))(C(10)H(11)N(3))(2)](ClO(4))(2), the Cu(II) cation has a distorted trigonal-bipyramidal geometry defined by a CuN(2)N'(2)N'' donor set. The imidazole ligand is disordered over two orientations of equal occupancy. Two of the perchlorate ion sites are located on a twofold rotation axis, and one of is disordered over two sites of equal occupancy. In the crystal structure there is a two-dimensional infinite network of hydrogen-bonded mol-ecules parallel to the ab plane.

Related literature

For related literature, see: Holm et al. (1996 ▶); Huang et al. (2004 ▶); Huang et al. (2005 ▶); Kapinos et al. (1998 ▶); Matthews et al. (1998 ▶); Tan et al. (1997 ▶).

Experimental

Crystal data

[Cu(C3H4N2)(C10H11N3)2](ClO4)2

M = 676.96

Tetragonal,

a = 14.6374 (5) Å

c = 27.3945 (14) Å

V = 5869.4 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.99 mm−1

T = 293 (2) K

0.32 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.74, T max = 0.79

32170 measured reflections

5775 independent reflections

5315 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.117

S = 1.08

5775 reflections

410 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.64 e Å−3

Absolute structure: Flack (1983 ▶), 2433 Friedel pairs

Flack parameter: 0.013 (17)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017273/kj2084sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017273/kj2084Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C3H4N2)(C10H11N3)2](ClO4)2	Z = 8
Mr = 676.96	F000 = 2776
Tetragonal, P41212	Dx = 1.532 Mg m−3
Hall symbol: P 4abw 2nw	Mo Kα radiation λ = 0.71073 Å
a = 14.6374 (5) Å	Cell parameters from 8320 reflections
b = 14.6374 (5) Å	θ = 2.5–23.8º
c = 27.3945 (14) Å	µ = 0.99 mm−1
α = 90º	T = 293 (2) K
β = 90º	Bipyramid, green
γ = 90º	0.32 × 0.26 × 0.24 mm
V = 5869.4 (4) Å3

Bruker SMART APEX CCD area-detector diffractometer	5775 independent reflections
Radiation source: sealed tube	5315 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.048
T = 273(2) K	θmax = 26.0º
φ and ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −18→14
Tmin = 0.74, Tmax = 0.79	k = −18→18
32170 measured reflections	l = −33→27

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048	w = 1/[σ2(Fo2) + (0.049P)2 + 5.1204P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.117	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.54 e Å−3
5775 reflections	Δρmin = −0.63 e Å−3
410 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2433 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.013 (17)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.49074 (3)	0.81891 (3)	0.002420 (17)	0.04289 (13)
C1	0.5381 (3)	0.7035 (3)	−0.09104 (15)	0.0491 (10)
H1A	0.5698	0.7544	−0.1023	0.059*
C2	0.5351 (3)	0.6266 (3)	−0.12011 (16)	0.0560 (11)
H2A	0.5649	0.6258	−0.1501	0.067*
C3	0.4875 (3)	0.5508 (3)	−0.10421 (17)	0.0590 (12)
H3B	0.4848	0.4985	−0.1234	0.071*
C4	0.4438 (3)	0.5534 (3)	−0.05947 (17)	0.0547 (10)
H4A	0.4104	0.5037	−0.0482	0.066*
C5	0.4516 (3)	0.6338 (3)	−0.03163 (14)	0.0406 (8)
C6	0.4098 (3)	0.6474 (3)	0.01525 (14)	0.0434 (9)
C7	0.3344 (3)	0.6321 (3)	0.08455 (16)	0.0555 (11)
C8	0.3702 (3)	0.7184 (3)	0.08219 (16)	0.0531 (11)
C9	0.2772 (4)	0.5869 (4)	0.1227 (2)	0.0822 (17)
H9A	0.2638	0.5254	0.1128	0.123*
H9B	0.2213	0.6202	0.1267	0.123*
H9C	0.3099	0.5859	0.1531	0.123*
C10	0.3611 (5)	0.7958 (5)	0.1173 (2)	0.0863 (19)
H10A	0.3258	0.7764	0.1450	0.129*
H10B	0.3309	0.8460	0.1016	0.129*
H10C	0.4206	0.8147	0.1280	0.129*
C11	0.6139 (3)	0.7685 (3)	0.09316 (16)	0.0532 (11)
H11A	0.5641	0.7359	0.1051	0.064*
C12	0.6937 (3)	0.7703 (3)	0.12029 (17)	0.0557 (11)
H12A	0.6976	0.7394	0.1499	0.067*
C13	0.7668 (3)	0.8185 (3)	0.10272 (17)	0.0579 (12)
H13A	0.8209	0.8210	0.1205	0.070*
C14	0.7602 (3)	0.8632 (3)	0.05894 (17)	0.0551 (11)
H14A	0.8098	0.8950	0.0462	0.066*
C15	0.6777 (3)	0.8597 (2)	0.03390 (15)	0.0412 (8)
C16	0.6608 (2)	0.9028 (2)	−0.01296 (14)	0.0383 (8)
C17	0.6694 (3)	0.9807 (3)	−0.08144 (15)	0.0502 (9)
C18	0.5849 (3)	0.9440 (3)	−0.07755 (15)	0.0479 (10)
C19	0.7111 (4)	1.0404 (4)	−0.1201 (2)	0.0766 (16)
H19A	0.6671	1.0515	−0.1454	0.115*
H19B	0.7636	1.0104	−0.1338	0.115*
H19C	0.7294	1.0975	−0.1059	0.115*
C20	0.5027 (4)	0.9551 (4)	−0.1099 (2)	0.0757 (16)
H20A	0.5189	0.9907	−0.1380	0.114*
H20B	0.4550	0.9856	−0.0921	0.114*
H20C	0.4815	0.8961	−0.1201	0.114*
C21	0.4109 (4)	1.0078 (3)	0.0069 (2)	0.0658 (13)	0.50
H21A	0.4679	1.0357	0.0090	0.079*	0.50
C22	0.2631 (3)	0.9850 (4)	0.0016 (2)	0.075 (5)	0.50
H22A	0.2004	0.9950	−0.0001	0.090*	0.50
N8	0.3313 (4)	1.0509 (4)	0.00487 (19)	0.069 (3)	0.50
H8A	0.3233	1.1091	0.0055	0.083*	0.50
C23	0.3044 (3)	0.9069 (5)	0.0015 (2)	0.0707 (14)	0.50
H23A	0.2751	0.8507	−0.0010	0.085*	0.50
N7	0.3958 (2)	0.9177 (2)	0.00537 (13)	0.0492 (8)	0.50
C23'	0.4109 (4)	1.0078 (3)	0.0069 (2)	0.0658 (13)	0.50
H21B	0.4679	1.0357	0.0090	0.079*	0.50
N8'	0.2631 (3)	0.9850 (4)	0.0016 (2)	0.075 (3)	0.50
H8'A	0.2051	0.9942	0.0000	0.090*	0.50
N7'	0.3958 (2)	0.9177 (2)	0.00537 (13)	0.0492 (8)	0.50
C21'	0.3044 (3)	0.9069 (5)	0.0015 (2)	0.0707 (14)	0.50
H23B	0.2751	0.8507	−0.0010	0.085*	0.50
C22'	0.3313 (4)	1.0509 (4)	0.00487 (19)	0.069 (3)	0.50
H22B	0.3226	1.1138	0.0055	0.083*	0.50
N1	0.4977 (2)	0.7080 (2)	−0.04776 (12)	0.0412 (7)
N2	0.4179 (2)	0.7263 (2)	0.03865 (12)	0.0463 (8)
N3	0.3601 (2)	0.5891 (2)	0.04254 (14)	0.0514 (9)
H3A	0.3468	0.5338	0.0347	0.062*
N4	0.6058 (2)	0.8120 (2)	0.05027 (12)	0.0420 (7)
N5	0.5794 (2)	0.8946 (2)	−0.03395 (12)	0.0419 (7)
N6	0.7161 (2)	0.9535 (2)	−0.04085 (13)	0.0481 (8)
H6	0.7720	0.9668	−0.0343	0.058*
Cl1	0.32257 (8)	0.32257 (8)	0.0000	0.0702 (5)
O11	0.2532 (6)	0.2691 (6)	−0.0184 (2)	0.081 (3)	0.50
O12	0.2849 (7)	0.4105 (5)	0.0068 (4)	0.084 (2)	0.50
O13	0.3603 (6)	0.2882 (6)	0.0403 (3)	0.089 (3)	0.50
O14	0.3877 (6)	0.3325 (6)	−0.0371 (3)	0.080 (2)	0.50
Cl2	0.99578 (7)	0.99578 (7)	0.0000	0.0583 (4)
O21	0.9987 (3)	0.9145 (2)	0.02515 (14)	0.0775 (11)
O22	1.0050 (3)	1.0666 (3)	0.03420 (14)	0.0815 (12)
Cl3	0.66607 (8)	0.15608 (7)	0.02360 (4)	0.0550 (3)
O31	0.7316 (3)	0.1668 (3)	−0.01093 (13)	0.0798 (12)
O32	0.6524 (3)	0.2387 (3)	0.04837 (15)	0.0804 (12)
O33	0.6871 (3)	0.0867 (3)	0.05352 (15)	0.0864 (13)
O34	0.5931 (3)	0.1353 (3)	−0.00339 (17)	0.0867 (12)

	U11	U22	U33	U12	U13	U23
Cu1	0.0378 (2)	0.0426 (3)	0.0483 (2)	−0.00376 (19)	0.0047 (2)	0.0029 (2)
C1	0.043 (2)	0.059 (3)	0.046 (2)	−0.0063 (19)	0.0089 (18)	0.0013 (19)
C2	0.050 (3)	0.074 (3)	0.044 (2)	0.003 (2)	0.0059 (19)	−0.011 (2)
C3	0.069 (3)	0.054 (3)	0.054 (3)	0.003 (2)	−0.006 (2)	−0.015 (2)
C4	0.056 (3)	0.045 (2)	0.063 (3)	−0.0016 (19)	0.001 (2)	−0.010 (2)
C5	0.0354 (19)	0.046 (2)	0.041 (2)	−0.0006 (16)	−0.0021 (16)	−0.0004 (17)
C6	0.041 (2)	0.046 (2)	0.043 (2)	−0.0021 (17)	0.0036 (17)	0.0039 (17)
C7	0.049 (2)	0.063 (3)	0.055 (2)	−0.003 (2)	0.005 (2)	0.011 (2)
C8	0.048 (2)	0.066 (3)	0.046 (2)	−0.006 (2)	0.0104 (19)	0.002 (2)
C9	0.084 (4)	0.086 (4)	0.077 (4)	−0.002 (3)	0.033 (3)	0.025 (3)
C10	0.099 (5)	0.092 (4)	0.068 (3)	−0.016 (4)	0.025 (3)	−0.022 (3)
C11	0.059 (3)	0.047 (2)	0.054 (3)	−0.007 (2)	−0.007 (2)	0.014 (2)
C12	0.061 (3)	0.049 (2)	0.057 (3)	−0.001 (2)	−0.015 (2)	0.006 (2)
C13	0.061 (3)	0.054 (3)	0.059 (3)	0.007 (2)	−0.023 (2)	−0.004 (2)
C14	0.043 (2)	0.057 (3)	0.066 (3)	−0.0044 (19)	−0.005 (2)	−0.006 (2)
C15	0.040 (2)	0.0344 (18)	0.049 (2)	−0.0007 (16)	−0.0077 (17)	−0.0044 (16)
C16	0.0306 (18)	0.0389 (19)	0.045 (2)	−0.0029 (15)	0.0010 (15)	0.0024 (16)
C17	0.055 (2)	0.046 (2)	0.050 (2)	0.0019 (19)	0.0063 (19)	0.0026 (18)
C18	0.047 (2)	0.049 (2)	0.048 (2)	0.0022 (18)	0.0001 (18)	0.0077 (18)
C19	0.065 (3)	0.079 (4)	0.086 (4)	−0.009 (3)	0.021 (3)	0.025 (3)
C20	0.072 (3)	0.095 (4)	0.060 (3)	0.003 (3)	−0.010 (3)	0.025 (3)
C21	0.083 (4)	0.044 (2)	0.071 (3)	−0.003 (2)	0.005 (3)	0.005 (2)
C22	0.055 (9)	0.089 (11)	0.081 (8)	0.02 (11)	0.01 (11)	0.02 (13)
N8	0.070 (7)	0.068 (7)	0.070 (6)	0.02 (10)	0.01 (9)	0.02 (9)
C23	0.046 (3)	0.095 (4)	0.071 (3)	−0.006 (3)	0.008 (3)	−0.011 (3)
N7	0.0397 (18)	0.0479 (19)	0.060 (2)	0.0012 (14)	−0.0002 (17)	−0.0015 (17)
C23'	0.083 (4)	0.044 (2)	0.071 (3)	−0.003 (2)	0.005 (3)	0.005 (2)
N8'	0.055 (6)	0.089 (6)	0.081 (3)	0.02 (10)	0.01 (9)	0.02 (11)
N7'	0.0397 (18)	0.0479 (19)	0.060 (2)	0.0012 (14)	−0.0002 (17)	−0.0015 (17)
C21'	0.046 (3)	0.095 (4)	0.071 (3)	−0.006 (3)	0.008 (3)	−0.011 (3)
C22'	0.070 (6)	0.068 (6)	0.070 (3)	0.02 (11)	0.01 (11)	0.02 (10)
N1	0.0327 (16)	0.0462 (18)	0.0449 (17)	−0.0019 (14)	0.0006 (14)	−0.0035 (14)
N2	0.0441 (19)	0.051 (2)	0.0436 (17)	−0.0092 (15)	0.0047 (15)	−0.0012 (16)
N3	0.050 (2)	0.0419 (18)	0.062 (2)	−0.0091 (15)	0.0039 (17)	0.0088 (17)
N4	0.0422 (17)	0.0372 (17)	0.0465 (18)	−0.0048 (14)	−0.0034 (14)	0.0044 (14)
N5	0.0346 (16)	0.0450 (18)	0.0460 (17)	−0.0004 (13)	0.0029 (14)	0.0051 (14)
N6	0.0363 (17)	0.049 (2)	0.059 (2)	−0.0059 (14)	−0.0003 (16)	0.0036 (16)
Cl1	0.0593 (6)	0.0593 (6)	0.0920 (13)	−0.0108 (8)	−0.0109 (8)	0.0109 (8)
O11	0.078 (6)	0.075 (5)	0.090 (6)	−0.035 (4)	0.034 (5)	−0.009 (5)
O12	0.102 (6)	0.052 (4)	0.098 (6)	−0.019 (4)	0.015 (6)	−0.027 (5)
O13	0.099 (6)	0.096 (6)	0.072 (5)	−0.050 (5)	−0.016 (5)	0.027 (4)
O14	0.095 (6)	0.074 (5)	0.072 (5)	−0.019 (5)	0.031 (5)	−0.014 (4)
Cl2	0.0531 (5)	0.0531 (5)	0.0686 (9)	−0.0092 (6)	0.0084 (6)	−0.0084 (6)
O21	0.094 (3)	0.0521 (19)	0.087 (2)	−0.0083 (19)	−0.043 (2)	0.0116 (18)
O22	0.093 (3)	0.074 (2)	0.078 (2)	−0.033 (2)	0.039 (2)	−0.0269 (19)
Cl3	0.0676 (7)	0.0422 (5)	0.0552 (6)	−0.0112 (5)	−0.0081 (5)	−0.0014 (4)
O31	0.072 (2)	0.097 (3)	0.070 (2)	−0.031 (2)	0.0292 (18)	−0.037 (2)
O32	0.078 (2)	0.064 (2)	0.099 (3)	0.0249 (19)	−0.039 (2)	−0.028 (2)
O33	0.085 (3)	0.083 (3)	0.092 (3)	0.039 (2)	−0.035 (2)	0.013 (2)
O34	0.095 (3)	0.065 (2)	0.101 (3)	−0.016 (2)	−0.024 (2)	−0.024 (2)

Cu1—N5	1.977 (3)	C18—N5	1.398 (5)
Cu1—N2	1.990 (3)	C18—C20	1.503 (7)
Cu1—N7	2.007 (3)	C19—H19A	0.9600
Cu1—N1	2.129 (3)	C19—H19B	0.9600
Cu1—N4	2.137 (3)	C19—H19C	0.9600
C1—N1	1.327 (5)	C20—H20A	0.9600
C1—C2	1.380 (6)	C20—H20B	0.9600
C1—H1A	0.9300	C20—H20C	0.9600
C2—C3	1.380 (7)	C21—N8	1.326 (7)
C2—H2A	0.9300	C21—N7	1.338 (6)
C3—C4	1.383 (7)	C21—H21A	0.9300
C3—H3B	0.9300	C22—C23	1.293 (8)
C4—C5	1.407 (6)	C22—N8	1.392 (8)
C4—H4A	0.9300	C22—H22A	0.9300
C5—N1	1.352 (5)	N8—H8A	0.8600
C5—C6	1.437 (5)	C23—N7	1.352 (6)
C6—N2	1.326 (5)	C23—H23A	0.9300
C6—N3	1.347 (5)	N3—H3A	0.8600
C7—N3	1.364 (6)	N6—H6	0.8600
C7—C8	1.369 (6)	Cl1—O13	1.334 (8)
C7—C9	1.493 (6)	Cl1—O13i	1.334 (8)
C8—N2	1.386 (5)	Cl1—O11i	1.378 (7)
C8—C10	1.492 (7)	Cl1—O11	1.378 (7)
C9—H9A	0.9600	Cl1—O14i	1.401 (8)
C9—H9B	0.9600	Cl1—O14	1.401 (8)
C9—H9C	0.9600	Cl1—O12	1.413 (8)
C10—H10A	0.9600	Cl1—O12i	1.413 (8)
C10—H10B	0.9600	O11—O11i	1.060 (15)
C10—H10C	0.9600	O11—O13i	1.551 (10)
C11—N4	1.342 (5)	O12—O14i	1.135 (11)
C11—C12	1.385 (6)	O12—O13i	1.486 (11)
C11—H11A	0.9300	O13—O12i	1.486 (11)
C12—C13	1.369 (7)	O13—O14i	1.515 (13)
C12—H12A	0.9300	O13—O11i	1.551 (10)
C13—C14	1.369 (6)	O14—O12i	1.135 (11)
C13—H13A	0.9300	O14—O13i	1.515 (13)
C14—C15	1.391 (6)	Cl2—O21i	1.375 (3)
C14—H14A	0.9300	Cl2—O21	1.375 (3)
C15—N4	1.340 (5)	Cl2—O22	1.403 (3)
C15—C16	1.452 (5)	Cl2—O22i	1.403 (3)
C16—N5	1.327 (5)	Cl3—O34	1.334 (4)
C16—N6	1.338 (5)	Cl3—O33	1.341 (4)
C17—C18	1.353 (6)	Cl3—O31	1.356 (3)
C17—N6	1.365 (5)	Cl3—O32	1.402 (4)
C17—C19	1.504 (6)
N5—Cu1—N2	170.20 (15)	C23—C22—N8	106.1 (4)
N5—Cu1—N7	94.06 (14)	C23—C22—H22A	127.0
N2—Cu1—N7	95.74 (15)	N8—C22—H22A	127.0
N5—Cu1—N1	94.06 (13)	C21—N8—C22	107.7 (5)
N2—Cu1—N1	80.10 (13)	C21—N8—H8A	126.2
N7—Cu1—N1	127.46 (14)	C22—N8—H8A	126.2
N5—Cu1—N4	79.52 (13)	C22—C23—N7	111.1 (5)
N2—Cu1—N4	94.82 (13)	C22—C23—H23A	124.4
N7—Cu1—N4	123.73 (14)	N7—C23—H23A	124.4
N1—Cu1—N4	108.79 (13)	C21—N7—C23	106.3 (4)
N1—C1—C2	122.9 (4)	C21—N7—Cu1	126.7 (3)
N1—C1—H1A	118.6	C23—N7—Cu1	126.7 (4)
C2—C1—H1A	118.6	C1—N1—C5	118.3 (3)
C1—C2—C3	119.3 (4)	C1—N1—Cu1	129.5 (3)
C1—C2—H2A	120.4	C5—N1—Cu1	112.2 (2)
C3—C2—H2A	120.4	C6—N2—C8	107.4 (3)
C2—C3—C4	119.4 (4)	C6—N2—Cu1	113.6 (3)
C2—C3—H3B	120.3	C8—N2—Cu1	139.0 (3)
C4—C3—H3B	120.3	C6—N3—C7	109.0 (4)
C3—C4—C5	117.8 (4)	C6—N3—H3A	125.5
C3—C4—H4A	121.1	C7—N3—H3A	125.5
C5—C4—H4A	121.1	C15—N4—C11	118.1 (4)
N1—C5—C4	122.4 (4)	C15—N4—Cu1	112.9 (3)
N1—C5—C6	113.2 (3)	C11—N4—Cu1	129.0 (3)
C4—C5—C6	124.4 (4)	C16—N5—C18	105.8 (3)
N2—C6—N3	109.3 (4)	C16—N5—Cu1	114.9 (3)
N2—C6—C5	120.9 (4)	C18—N5—Cu1	139.2 (3)
N3—C6—C5	129.7 (4)	C16—N6—C17	108.8 (3)
N3—C7—C8	106.2 (4)	C16—N6—H6	125.6
N3—C7—C9	122.7 (4)	C17—N6—H6	125.6
C8—C7—C9	131.0 (5)	O13—Cl1—O13i	177.0 (6)
C7—C8—N2	108.1 (4)	O13—Cl1—O11i	69.8 (5)
C7—C8—C10	129.4 (4)	O13i—Cl1—O11i	113.2 (5)
N2—C8—C10	122.5 (4)	O13—Cl1—O11	113.2 (5)
C7—C9—H9A	109.5	O13i—Cl1—O11	69.8 (5)
C7—C9—H9B	109.5	O11i—Cl1—O11	45.3 (6)
H9A—C9—H9B	109.5	O13—Cl1—O14i	67.2 (6)
C7—C9—H9C	109.5	O13i—Cl1—O14i	111.0 (6)
H9A—C9—H9C	109.5	O11i—Cl1—O14i	107.1 (5)
H9B—C9—H9C	109.5	O11—Cl1—O14i	136.7 (5)
C8—C10—H10A	109.5	O13—Cl1—O14	111.0 (6)
C8—C10—H10B	109.5	O13i—Cl1—O14	67.2 (6)
H10A—C10—H10B	109.5	O11i—Cl1—O14	136.7 (5)
C8—C10—H10C	109.5	O11—Cl1—O14	107.1 (5)
H10A—C10—H10C	109.5	O14i—Cl1—O14	112.7 (7)
H10B—C10—H10C	109.5	O13—Cl1—O12	113.4 (6)
N4—C11—C12	122.3 (4)	O13i—Cl1—O12	65.4 (6)
N4—C11—H11A	118.8	O11i—Cl1—O12	113.7 (6)
C12—C11—H11A	118.8	O11—Cl1—O12	106.2 (6)
C13—C12—C11	118.7 (4)	O14i—Cl1—O12	47.6 (5)
C13—C12—H12A	120.6	O14—Cl1—O12	105.5 (5)
C11—C12—H12A	120.6	O13—Cl1—O12i	65.4 (6)
C12—C13—C14	119.9 (4)	O13i—Cl1—O12i	113.4 (6)
C12—C13—H13A	120.0	O11i—Cl1—O12i	106.2 (6)
C14—C13—H13A	120.0	O11—Cl1—O12i	113.7 (6)
C13—C14—C15	118.4 (4)	O14i—Cl1—O12i	105.5 (5)
C13—C14—H14A	120.8	O14—Cl1—O12i	47.6 (5)
C15—C14—H14A	120.8	O12—Cl1—O12i	136.7 (7)
N4—C15—C14	122.4 (4)	O11i—O11—Cl1	67.4 (3)
N4—C15—C16	112.9 (3)	O11i—O11—O13i	119.0 (5)
C14—C15—C16	124.6 (4)	Cl1—O11—O13i	53.8 (4)
N5—C16—N6	110.2 (3)	O14i—O12—Cl1	65.7 (6)
N5—C16—C15	119.8 (3)	O14i—O12—O13i	118.1 (9)
N6—C16—C15	130.0 (4)	Cl1—O12—O13i	54.7 (4)
C18—C17—N6	106.2 (4)	Cl1—O13—O12i	59.8 (5)
C18—C17—C19	131.2 (4)	Cl1—O13—O14i	58.5 (5)
N6—C17—C19	122.6 (4)	O12i—O13—O14i	96.5 (6)
C17—C18—N5	108.9 (4)	Cl1—O13—O11i	56.4 (4)
C17—C18—C20	130.0 (4)	O12i—O13—O11i	94.5 (6)
N5—C18—C20	120.9 (4)	O14i—O13—O11i	93.6 (7)
C17—C19—H19A	109.5	O12i—O14—Cl1	66.7 (6)
C17—C19—H19B	109.5	O12i—O14—O13i	119.4 (8)
H19A—C19—H19B	109.5	Cl1—O14—O13i	54.3 (4)
C17—C19—H19C	109.5	O21i—Cl2—O21	107.7 (3)
H19A—C19—H19C	109.5	O21i—Cl2—O22	113.3 (3)
H19B—C19—H19C	109.5	O21—Cl2—O22	107.5 (2)
C18—C20—H20A	109.5	O21i—Cl2—O22i	107.5 (2)
C18—C20—H20B	109.5	O21—Cl2—O22i	113.3 (3)
H20A—C20—H20B	109.5	O22—Cl2—O22i	107.7 (3)
C18—C20—H20C	109.5	O34—Cl3—O33	110.5 (3)
H20A—C20—H20C	109.5	O34—Cl3—O31	101.9 (3)
H20B—C20—H20C	109.5	O33—Cl3—O31	110.6 (3)
N8—C21—N7	108.8 (5)	O34—Cl3—O32	110.5 (2)
N8—C21—H21A	125.6	O33—Cl3—O32	113.0 (3)
N7—C21—H21A	125.6	O31—Cl3—O32	109.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O12	0.86	2.16	3.001 (8)	166
N3—H3A···O14i	0.86	2.15	2.980 (10)	162
N6—H6···O21i	0.86	2.15	3.009 (5)	175

Cu1—N5	1.977 (3)
Cu1—N2	1.990 (3)
Cu1—N7	2.007 (3)
Cu1—N1	2.129 (3)
Cu1—N4	2.137 (3)

N5—Cu1—N2	170.20 (15)
N5—Cu1—N7	94.06 (14)
N2—Cu1—N7	95.74 (15)
N5—Cu1—N1	94.06 (13)
N2—Cu1—N1	80.10 (13)
N7—Cu1—N1	127.46 (14)
N5—Cu1—N4	79.52 (13)
N2—Cu1—N4	94.82 (13)
N7—Cu1—N4	123.73 (14)
N1—Cu1—N4	108.79 (13)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O12	0.86	2.16	3.001 (8)	166
N3—H3A⋯O14i	0.86	2.15	2.980 (10)	162
N6—H6⋯O21i	0.86	2.15	3.009 (5)	175

Symmetry code: (i) .