(Acetonitrile)[bis-(2-pyridylmeth-yl)amine]bis-(perchlorato)copper(II).

In the title compound, [Cu(ClO(4))(2)(C(12)H(13)N(3))(C(2)H(3)N)], the Cu(II) atom is six-coordinate in a Jahn-Teller distorted octahedral geometry, with coordination by the tridentate chelating ligand, an acetonitrile mol-ecule, and two axial perchlorate anions. The tridentate ligand bis-(2-pyridylmeth-yl)amine chelates meridionally and equatorially while an acetonitrile mol-ecule is coordinated at the fourth equatorial site. The two perchlorate anions are disordered with site occupancy factors of 0.72/0.28. The amine H is involved in intra-molecular hydrogen bonding to the perchlorate O atoms and there are extensive but weak inter-molecular C-H⋯O inter-actions.

Related literature

For related literature, see: Belle et al. (2002 ▶); Gultneh et al. (1999 ▶); Humphreys et al. (2002 ▶); Palaniandavar et al. (1995 ▶).

Experimental

Crystal data

[Cu(ClO4)2(C12H13N3)(C2H3N)]

M = 502.75

Monoclinic,

a = 8.3046 (16) Å

b = 31.453 (4) Å

c = 8.4978 (11) Å

β = 118.646 (10)°

V = 1948.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.45 mm−1

T = 293 (2) K

0.45 × 0.21 × 0.07 mm

Data collection

Bruker P4S diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.757, T max = 0.964 (expected range = 0.709–0.904)

4638 measured reflections

4347 independent reflections

2718 reflections with I > 2σ(I)

R int = 0.030

3 standard reflections every 97 reflections intensity decay: <2%

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.193

S = 1.04

4347 reflections

320 parameters

92 restraints

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.46 e Å−3

Data collection: XSCANS (Bruker, 1997 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2000 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067001/bq2058sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067001/bq2058Isup2.hkl

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

[Cu(ClO4)2(C12H13N3)(C2H3N)]	F000 = 1020
Mr = 502.75	Dx = 1.714 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 54 reflections
a = 8.3046 (16) Å	θ = 2.6–13.1º
b = 31.453 (4) Å	µ = 1.45 mm−1
c = 8.4978 (11) Å	T = 293 (2) K
β = 118.646 (10)º	Plate, blue
V = 1948.0 (5) Å3	0.45 × 0.21 × 0.07 mm
Z = 4

Bruker P4S diffractometer	Rint = 0.030
Radiation source: fine-focus sealed tube	θmax = 27.5º
Monochromator: graphite	θmin = 2.6º
T = 293(2) K	h = 0→9
2θ/ω scans	k = −40→0
Absorption correction: empirical (using intensity measurements) via psi scans(North et al., 1968)	l = −11→9
Tmin = 0.757, Tmax = 0.964	3 standard reflections
4638 measured reflections	every 97 reflections
4347 independent reflections	intensity decay: <2%
2718 reflections with I > 2σ(I)

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)] = 0.064	H-atom parameters constrained
wR(F2) = 0.193	w = 1/[σ2(Fo2) + (0.0863P)2 + 3.5739P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
4347 reflections	Δρmax = 0.49 e Å−3
320 parameters	Δρmin = −0.46 e Å−3
92 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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)
Cu	0.85396 (9)	0.12165 (2)	−0.01007 (9)	0.0455 (2)
Cl1	0.5466 (2)	0.19134 (7)	−0.4772 (2)	0.0704 (5)
Cl2	1.07924 (18)	0.04196 (5)	0.29953 (18)	0.0480 (4)
O11	0.6293 (8)	0.1760 (2)	−0.2975 (7)	0.104 (2)
O12	0.5827 (15)	0.1680 (3)	−0.5954 (12)	0.107 (4)	0.708 (9)
O13	0.3563 (10)	0.1998 (4)	−0.5489 (12)	0.106 (3)	0.708 (9)
O14	0.6252 (16)	0.2343 (3)	−0.4642 (15)	0.128 (4)	0.708 (9)
O12A	0.412 (3)	0.1546 (6)	−0.561 (3)	0.123 (7)	0.292 (9)
O13A	0.673 (3)	0.1865 (9)	−0.538 (3)	0.121 (8)	0.292 (9)
O14A	0.449 (3)	0.2264 (6)	−0.510 (3)	0.134 (8)	0.292 (9)
O21	1.2524 (7)	0.0234 (2)	0.4056 (8)	0.105 (2)
O22	1.0940 (12)	0.0848 (3)	0.2525 (18)	0.073 (3)	0.73 (3)
O23	0.9968 (17)	0.0176 (3)	0.1363 (12)	0.091 (4)	0.73 (3)
O24	0.9656 (18)	0.0399 (5)	0.378 (2)	0.114 (5)	0.73 (3)
O22A	1.083 (3)	0.0726 (9)	0.180 (4)	0.061 (5)	0.27 (3)
O23A	0.945 (3)	0.0114 (7)	0.200 (4)	0.103 (11)	0.27 (3)
O24A	1.031 (4)	0.0626 (11)	0.422 (3)	0.120 (13)	0.27 (3)
N	0.8033 (7)	0.07655 (17)	−0.1923 (6)	0.0535 (12)
H0A	0.8722	0.0536	−0.1326	0.064*
N1	0.8876 (7)	0.16941 (18)	0.1547 (7)	0.0578 (13)
N1A	0.6448 (6)	0.09486 (15)	0.0037 (6)	0.0437 (10)
N1B	1.0370 (7)	0.14026 (16)	−0.0821 (7)	0.0505 (12)
C1	0.9117 (9)	0.1962 (2)	0.2536 (9)	0.0592 (16)
C2	0.9472 (12)	0.2296 (3)	0.3847 (12)	0.085 (2)
H21	0.9179	0.2194	0.4746	0.127*
H22	0.8726	0.2539	0.3259	0.127*
H23	1.0744	0.2375	0.4402	0.127*
C1A	0.5988 (8)	0.1008 (2)	0.1336 (7)	0.0501 (14)
H1AA	0.6635	0.1206	0.2237	0.060*
C2A	0.4574 (8)	0.0783 (2)	0.1363 (8)	0.0568 (16)
H2AA	0.4302	0.0820	0.2296	0.068*
C3A	0.3585 (8)	0.0508 (2)	0.0004 (9)	0.0579 (16)
H3AA	0.2603	0.0361	−0.0017	0.069*
C4A	0.4043 (8)	0.04453 (19)	−0.1353 (9)	0.0544 (15)
H4AA	0.3383	0.0256	−0.2285	0.065*
C5A	0.5498 (7)	0.06705 (18)	−0.1285 (7)	0.0440 (12)
C6A	0.6090 (8)	0.0636 (2)	−0.2696 (8)	0.0608 (17)
H6AA	0.5946	0.0345	−0.3126	0.073*
H6AB	0.5331	0.0818	−0.3704	0.073*
C1B	1.1723 (8)	0.1693 (2)	0.0060 (9)	0.0613 (17)
H1BA	1.1857	0.1809	0.1123	0.074*
C2B	1.2893 (10)	0.1821 (3)	−0.0557 (13)	0.081 (2)
H2BA	1.3817	0.2018	0.0070	0.097*
C3B	1.2643 (11)	0.1644 (3)	−0.2174 (13)	0.090 (3)
H3BA	1.3384	0.1731	−0.2658	0.108*
C4B	1.1319 (11)	0.1345 (3)	−0.3037 (11)	0.075 (2)
H4BA	1.1176	0.1220	−0.4087	0.090*
C5B	1.0171 (9)	0.1229 (2)	−0.2317 (9)	0.0580 (16)
C6B	0.8664 (10)	0.0902 (2)	−0.3200 (8)	0.0624 (17)
H6BA	0.7647	0.1024	−0.4259	0.075*
H6BB	0.9120	0.0659	−0.3569	0.075*

	U11	U22	U33	U12	U13	U23
Cu	0.0421 (4)	0.0597 (5)	0.0456 (4)	−0.0037 (3)	0.0299 (3)	−0.0057 (3)
Cl1	0.0599 (10)	0.0979 (14)	0.0629 (10)	0.0036 (9)	0.0371 (9)	−0.0078 (9)
Cl2	0.0430 (7)	0.0613 (9)	0.0422 (7)	−0.0001 (6)	0.0225 (6)	−0.0009 (6)
O11	0.086 (4)	0.151 (6)	0.072 (4)	0.032 (4)	0.036 (3)	0.023 (4)
O12	0.120 (8)	0.114 (8)	0.098 (6)	0.021 (6)	0.061 (6)	−0.035 (5)
O13	0.070 (5)	0.147 (9)	0.101 (6)	0.021 (5)	0.041 (5)	0.001 (6)
O14	0.146 (9)	0.093 (7)	0.154 (9)	−0.027 (6)	0.079 (8)	−0.022 (6)
O12A	0.110 (12)	0.124 (13)	0.105 (11)	−0.020 (11)	0.026 (10)	−0.011 (11)
O13A	0.122 (16)	0.131 (18)	0.163 (16)	0.012 (13)	0.110 (13)	0.011 (14)
O14A	0.122 (13)	0.092 (12)	0.166 (13)	0.027 (12)	0.050 (13)	0.006 (12)
O21	0.066 (3)	0.113 (5)	0.103 (5)	0.021 (3)	0.014 (3)	0.016 (4)
O22	0.070 (4)	0.064 (5)	0.072 (6)	−0.010 (4)	0.023 (4)	−0.004 (4)
O23	0.099 (7)	0.075 (6)	0.057 (5)	−0.009 (5)	0.003 (5)	−0.010 (4)
O24	0.127 (9)	0.137 (11)	0.137 (10)	0.022 (8)	0.111 (9)	0.025 (8)
O22A	0.065 (7)	0.066 (9)	0.065 (9)	0.014 (7)	0.041 (8)	0.020 (7)
O23A	0.101 (19)	0.106 (19)	0.08 (2)	−0.064 (15)	0.026 (15)	−0.010 (14)
O24A	0.22 (4)	0.11 (2)	0.076 (16)	−0.01 (2)	0.11 (2)	−0.034 (16)
N	0.057 (3)	0.071 (3)	0.045 (3)	0.001 (2)	0.035 (2)	−0.003 (2)
N1	0.056 (3)	0.065 (3)	0.065 (3)	−0.009 (3)	0.039 (3)	−0.014 (3)
N1A	0.040 (2)	0.049 (3)	0.050 (3)	0.000 (2)	0.028 (2)	0.000 (2)
N1B	0.049 (3)	0.061 (3)	0.054 (3)	0.013 (2)	0.035 (2)	0.014 (2)
C1	0.049 (3)	0.074 (5)	0.060 (4)	−0.004 (3)	0.030 (3)	−0.005 (3)
C2	0.094 (6)	0.067 (5)	0.100 (6)	−0.017 (4)	0.053 (5)	−0.029 (4)
C1A	0.042 (3)	0.074 (4)	0.042 (3)	−0.002 (3)	0.026 (3)	−0.006 (3)
C2A	0.043 (3)	0.084 (5)	0.054 (4)	0.001 (3)	0.032 (3)	0.007 (3)
C3A	0.039 (3)	0.072 (4)	0.066 (4)	0.001 (3)	0.028 (3)	0.015 (3)
C4A	0.038 (3)	0.049 (3)	0.066 (4)	−0.002 (3)	0.017 (3)	−0.002 (3)
C5A	0.036 (3)	0.048 (3)	0.048 (3)	0.008 (2)	0.020 (2)	−0.002 (2)
C6A	0.049 (3)	0.084 (5)	0.048 (3)	−0.004 (3)	0.023 (3)	−0.016 (3)
C1B	0.047 (3)	0.063 (4)	0.074 (4)	−0.006 (3)	0.030 (3)	0.008 (3)
C2B	0.055 (4)	0.085 (5)	0.118 (7)	0.010 (4)	0.054 (5)	0.030 (5)
C3B	0.076 (5)	0.103 (7)	0.125 (8)	0.024 (5)	0.075 (6)	0.053 (6)
C4B	0.080 (5)	0.093 (6)	0.083 (5)	0.033 (4)	0.064 (4)	0.034 (4)
C5B	0.055 (4)	0.075 (4)	0.061 (4)	0.019 (3)	0.040 (3)	0.023 (3)
C6B	0.074 (4)	0.080 (5)	0.051 (3)	0.014 (4)	0.045 (3)	0.003 (3)

Cu—N1	1.980 (5)	N1B—C1B	1.360 (8)
Cu—N1B	1.980 (5)	C1—C2	1.455 (10)
Cu—N1A	1.984 (4)	C2—H21	0.9600
Cu—N	1.991 (5)	C2—H22	0.9600
Cu—O22A	2.379 (17)	C2—H23	0.9600
Cu—O22	2.455 (9)	C1A—C2A	1.380 (8)
Cu—O11	2.828 (5)	C1A—H1AA	0.9300
Cl1—O14A	1.317 (13)	C2A—C3A	1.360 (9)
Cl1—O12	1.387 (7)	C2A—H2AA	0.9300
Cl1—O13A	1.389 (13)	C3A—C4A	1.390 (9)
Cl1—O13	1.420 (7)	C3A—H3AA	0.9300
Cl1—O11	1.425 (5)	C4A—C5A	1.377 (8)
Cl1—O14	1.483 (8)	C4A—H4AA	0.9300
Cl1—O12A	1.524 (14)	C5A—C6A	1.503 (8)
Cl2—O24	1.394 (7)	C6A—H6AA	0.9700
Cl2—O21	1.406 (5)	C6A—H6AB	0.9700
Cl2—O23A	1.407 (13)	C1B—C2B	1.367 (9)
Cl2—O22A	1.412 (12)	C1B—H1BA	0.9300
Cl2—O22	1.428 (7)	C2B—C3B	1.403 (12)
Cl2—O24A	1.435 (12)	C2B—H2BA	0.9300
Cl2—O23	1.438 (7)	C3B—C4B	1.364 (12)
N—C6A	1.477 (8)	C3B—H3BA	0.9300
N—C6B	1.478 (7)	C4B—C5B	1.405 (8)
N—H0A	0.9100	C4B—H4BA	0.9300
N1—C1	1.137 (8)	C5B—C6B	1.512 (10)
N1A—C5A	1.341 (7)	C6B—H6BA	0.9700
N1A—C1A	1.344 (6)	C6B—H6BB	0.9700
N1B—C5B	1.320 (8)
N1—Cu—N1B	97.2 (2)	C1A—N1A—Cu	126.2 (4)
N1—Cu—N1A	96.40 (19)	C5B—N1B—C1B	119.8 (5)
N1B—Cu—N1A	165.3 (2)	C5B—N1B—Cu	114.5 (4)
N1—Cu—N	175.1 (2)	C1B—N1B—Cu	125.6 (4)
N1B—Cu—N	83.0 (2)	N1—C1—C2	178.1 (8)
N1A—Cu—N	83.01 (19)	C1—C2—H21	109.5
N1—Cu—O22A	102.5 (9)	C1—C2—H22	109.5
N1B—Cu—O22A	85.3 (4)	H21—C2—H22	109.5
N1A—Cu—O22A	97.0 (5)	C1—C2—H23	109.5
N—Cu—O22A	82.4 (9)	H21—C2—H23	109.5
N1—Cu—O22	86.4 (4)	H22—C2—H23	109.5
N1B—Cu—O22	90.6 (3)	N1A—C1A—C2A	121.4 (6)
N1A—Cu—O22	95.6 (3)	N1A—C1A—H1AA	119.3
N—Cu—O22	98.5 (4)	C2A—C1A—H1AA	119.3
O22A—Cu—O22	16.4 (6)	C3A—C2A—C1A	119.0 (6)
N1—Cu—O11	87.9 (2)	C3A—C2A—H2AA	120.5
N1B—Cu—O11	80.84 (18)	C1A—C2A—H2AA	120.5
N1A—Cu—O11	94.23 (19)	C2A—C3A—C4A	120.0 (6)
N—Cu—O11	87.3 (2)	C2A—C3A—H3AA	120.0
O12—Cl1—O13	111.7 (6)	C4A—C3A—H3AA	120.0
O14A—Cl1—O11	116.3 (11)	C5A—C4A—C3A	118.4 (6)
O12—Cl1—O11	115.9 (5)	C5A—C4A—H4AA	120.8
O13A—Cl1—O11	107.6 (10)	C3A—C4A—H4AA	120.8
O13—Cl1—O11	112.9 (5)	N1A—C5A—C4A	121.5 (5)
O12—Cl1—O14	107.2 (6)	N1A—C5A—C6A	115.4 (5)
O13—Cl1—O14	102.8 (6)	C4A—C5A—C6A	123.1 (5)
O11—Cl1—O14	105.1 (5)	N—C6A—C5A	109.3 (5)
O14A—Cl1—O12A	107.3 (12)	N—C6A—H6AA	109.8
O13A—Cl1—O12A	104.8 (12)	C5A—C6A—H6AA	109.8
O24—Cl2—O21	113.2 (6)	N—C6A—H6AB	109.8
O21—Cl2—O23A	112.0 (11)	C5A—C6A—H6AB	109.8
O21—Cl2—O22A	112.0 (9)	H6AA—C6A—H6AB	108.3
O23A—Cl2—O22A	108.6 (10)	N1B—C1B—C2B	122.6 (7)
O24—Cl2—O22	110.2 (6)	N1B—C1B—H1BA	118.7
O21—Cl2—O22	111.8 (4)	C2B—C1B—H1BA	118.7
O21—Cl2—O24A	106.0 (10)	C1B—C2B—C3B	117.4 (8)
O23A—Cl2—O24A	109.1 (12)	C1B—C2B—H2BA	121.3
O22A—Cl2—O24A	108.9 (11)	C3B—C2B—H2BA	121.3
O24—Cl2—O23	108.6 (6)	C4B—C3B—C2B	120.2 (7)
O21—Cl2—O23	105.4 (5)	C4B—C3B—H3BA	119.9
O22—Cl2—O23	107.3 (5)	C2B—C3B—H3BA	119.9
Cl1—O11—Cu	155.4 (4)	C3B—C4B—C5B	119.1 (8)
Cl2—O22—Cu	124.0 (5)	C3B—C4B—H4BA	120.5
Cl2—O22A—Cu	130.1 (12)	C5B—C4B—H4BA	120.5
C6A—N—C6B	116.7 (5)	N1B—C5B—C4B	120.9 (7)
C6A—N—Cu	108.7 (4)	N1B—C5B—C6B	116.8 (5)
C6B—N—Cu	110.3 (4)	C4B—C5B—C6B	122.2 (7)
C6A—N—H0A	106.9	N—C6B—C5B	109.5 (5)
C6B—N—H0A	106.9	N—C6B—H6BA	109.8
Cu—N—H0A	106.9	C5B—C6B—H6BA	109.8
C1—N1—Cu	177.8 (6)	N—C6B—H6BB	109.8
C5A—N1A—C1A	119.6 (5)	C5B—C6B—H6BB	109.8
C5A—N1A—Cu	114.1 (3)	H6BA—C6B—H6BB	108.2
O14A—Cl1—O11—Cu	−174.7 (16)	O22—Cu—N1A—C5A	−109.8 (5)
O12—Cl1—O11—Cu	3.7 (12)	O11—Cu—N1A—C5A	74.8 (4)
O13A—Cl1—O11—Cu	−35.7 (16)	N1—Cu—N1A—C1A	−19.9 (5)
O13—Cl1—O11—Cu	134.3 (10)	N1B—Cu—N1A—C1A	−177.9 (7)
O14—Cl1—O11—Cu	−114.4 (10)	N—Cu—N1A—C1A	165.0 (5)
O12A—Cl1—O11—Cu	72.2 (14)	O22A—Cu—N1A—C1A	83.6 (10)
N1—Cu—O11—Cl1	152.0 (10)	O22—Cu—N1A—C1A	67.1 (6)
N1B—Cu—O11—Cl1	54.3 (10)	O11—Cu—N1A—C1A	−108.2 (5)
N1A—Cu—O11—Cl1	−111.8 (10)	N1—Cu—N1B—C5B	−161.1 (4)
N—Cu—O11—Cl1	−29.0 (10)	N1A—Cu—N1B—C5B	−3.1 (10)
O22A—Cu—O11—Cl1	22 (3)	N—Cu—N1B—C5B	14.0 (4)
O22—Cu—O11—Cl1	93 (2)	O22A—Cu—N1B—C5B	96.9 (10)
O24—Cl2—O22—Cu	−76.8 (8)	O22—Cu—N1B—C5B	112.5 (5)
O21—Cl2—O22—Cu	156.4 (6)	O11—Cu—N1B—C5B	−74.4 (4)
O23A—Cl2—O22—Cu	9.1 (16)	N1—Cu—N1B—C1B	17.1 (5)
O22A—Cl2—O22—Cu	60 (2)	N1A—Cu—N1B—C1B	175.0 (7)
O24A—Cl2—O22—Cu	−99.3 (11)	N—Cu—N1B—C1B	−167.9 (5)
O23—Cl2—O22—Cu	41.3 (8)	O22A—Cu—N1B—C1B	−85.0 (10)
N1—Cu—O22—Cl2	132.1 (10)	O22—Cu—N1B—C1B	−69.4 (6)
N1B—Cu—O22—Cl2	−130.7 (10)	O11—Cu—N1B—C1B	103.7 (5)
N1A—Cu—O22—Cl2	36.0 (10)	C5A—N1A—C1A—C2A	1.2 (9)
N—Cu—O22—Cl2	−47.7 (10)	Cu—N1A—C1A—C2A	−175.6 (4)
O22A—Cu—O22—Cl2	−59.7 (17)	N1A—C1A—C2A—C3A	−2.6 (10)
O11—Cu—O22—Cl2	−169.2 (11)	C1A—C2A—C3A—C4A	2.1 (10)
O24—Cl2—O22A—Cu	−21 (3)	C2A—C3A—C4A—C5A	−0.5 (9)
O21—Cl2—O22A—Cu	−171.5 (18)	C1A—N1A—C5A—C4A	0.5 (8)
O23A—Cl2—O22A—Cu	64 (2)	Cu—N1A—C5A—C4A	177.7 (4)
O22—Cl2—O22A—Cu	−76 (3)	C1A—N1A—C5A—C6A	178.4 (5)
O24A—Cl2—O22A—Cu	−55 (2)	Cu—N1A—C5A—C6A	−4.4 (6)
O23—Cl2—O22A—Cu	86 (2)	C3A—C4A—C5A—N1A	−0.9 (9)
N1—Cu—O22A—Cl2	83 (3)	C3A—C4A—C5A—C6A	−178.6 (6)
N1B—Cu—O22A—Cl2	180 (3)	C6B—N—C6A—C5A	−158.4 (5)
N1A—Cu—O22A—Cl2	−15 (3)	Cu—N—C6A—C5A	−32.9 (6)
N—Cu—O22A—Cl2	−97 (3)	N1A—C5A—C6A—N	25.0 (8)
O22—Cu—O22A—Cl2	71 (2)	C4A—C5A—C6A—N	−157.1 (6)
O11—Cu—O22A—Cl2	−148.2 (9)	C5B—N1B—C1B—C2B	1.1 (10)
N1B—Cu—N—C6A	−150.7 (4)	Cu—N1B—C1B—C2B	−177.0 (5)
N1A—Cu—N—C6A	25.0 (4)	N1B—C1B—C2B—C3B	0.6 (11)
O22A—Cu—N—C6A	123.1 (6)	C1B—C2B—C3B—C4B	−2.2 (11)
O22—Cu—N—C6A	119.7 (5)	C2B—C3B—C4B—C5B	2.2 (11)
O11—Cu—N—C6A	−69.6 (4)	C1B—N1B—C5B—C4B	−1.1 (9)
N1B—Cu—N—C6B	−21.5 (4)	Cu—N1B—C5B—C4B	177.1 (5)
N1A—Cu—N—C6B	154.2 (4)	C1B—N1B—C5B—C6B	178.8 (6)
O22A—Cu—N—C6B	−107.7 (6)	Cu—N1B—C5B—C6B	−3.0 (7)
O22—Cu—N—C6B	−111.1 (5)	C3B—C4B—C5B—N1B	−0.5 (10)
O11—Cu—N—C6B	59.6 (4)	C3B—C4B—C5B—C6B	179.6 (7)
N1—Cu—N1A—C5A	163.1 (4)	C6A—N—C6B—C5B	149.5 (6)
N1B—Cu—N1A—C5A	5.1 (10)	Cu—N—C6B—C5B	24.8 (6)
N—Cu—N1A—C5A	−12.0 (4)	N1B—C5B—C6B—N	−14.8 (8)
O22A—Cu—N1A—C5A	−93.4 (9)	C4B—C5B—C6B—N	165.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O22A	0.91	2.45	2.89 (3)	110
N—H0A···O23	0.91	2.30	3.084 (12)	144
N—H0A···O23i	0.91	2.50	3.317 (10)	150
C2—H21···O13Aii	0.96	2.23	2.98 (2)	133
C2—H22···O14iii	0.96	2.36	3.103 (14)	134
C1A—H1AA···O12ii	0.93	2.46	3.176 (9)	134
C3A—H3AA···O23iv	0.93	2.53	3.376 (15)	152
C3A—H3AA···O23Aiv	0.93	2.29	2.993 (14)	133
C6A—H6AA···O21i	0.97	2.56	3.381 (9)	143
C2B—H2BA···O14Av	0.93	2.35	3.112 (16)	140
C3B—H3BA···O11vi	0.93	2.56	3.429 (10)	156
C4B—H4BA···O24Avii	0.93	2.25	3.06 (3)	145
C6B—H6BA···O12	0.97	2.56	3.425 (13)	149
C6B—H6BB···O24Avii	0.97	2.51	3.211 (16)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯O22A	0.91	2.45	2.89 (3)	110
N—H0A⋯O23	0.91	2.30	3.084 (12)	144
N—H0A⋯O23i	0.91	2.50	3.317 (10)	150
C2—H21⋯O13Aii	0.96	2.23	2.98 (2)	133
C2—H22⋯O14iii	0.96	2.36	3.103 (14)	134
C1A—H1AA⋯O12ii	0.93	2.46	3.176 (9)	134
C3A—H3AA⋯O23iv	0.93	2.53	3.376 (15)	152
C3A—H3AA⋯O23Aiv	0.93	2.29	2.993 (14)	133
C6A—H6AA⋯O21i	0.97	2.56	3.381 (9)	143
C2B—H2BA⋯O14Av	0.93	2.35	3.112 (16)	140
C3B—H3BA⋯O11vi	0.93	2.56	3.429 (10)	156
C4B—H4BA⋯O24Avii	0.93	2.25	3.06 (3)	145
C6B—H6BA⋯O12	0.97	2.56	3.425 (13)	149
C6B—H6BB⋯O24Avii	0.97	2.51	3.211 (16)	129

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .