[(6-Methyl-2-pyridylmeth-yl)(2-pyridylmeth-yl)amine][(2-pyridylmeth-yl)amine]copper(II) bis-(perchlorate).

The title compound, [Cu(C(6)H(8)N(2))(C(13)H(15)N(3))](ClO(4))(2), is a mixed ligand complex with the Cu(II) atom coordinated by (6-methyl-2-pyridylmeth-yl)(2-pyridylmeth-yl)amine, acting as a tridentate ligand, and 2-(2-amino-meth-yl)pyridine, as a bidentate ligand, leading to an N(5) square-pyramidal geometry. The amine H atoms are involved in hydrogen bonding to the perchlorate O atoms and there are extensive but weak inter-molecular C-H⋯O inter-actions in the crystal structure. The perchlorate ions are each disordered over two positions, with site occupancies of 0.601 (8):0.399 (8) and 0.659 (11):0.341 (11).

Related literature

For related literature, see: Cho et al. (2006 ▶); Gultneh et al. (2003 ▶); Hetterscheid et al. (2004 ▶); Mizuno et al. (2003 ▶); Ohtsu et al. (2001 ▶); Oki et al. (1990 ▶); Addison et al. (1984 ▶).

Experimental

Crystal data

[Cu(C6H8N2)(C13H15N3)](ClO4)2

M = 583.86

Monoclinic,

a = 9.3178 (10) Å

b = 13.9691 (19) Å

c = 19.223 (3) Å

β = 99.931 (11)°

V = 2464.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.16 mm−1

T = 293 (2) K

0.45 × 0.22 × 0.17 mm

Data collection

Bruker P4S diffractometer

Absorption correction: ψ-scan (North et al., 1968 ▶) T min = 0.444, T max = 0.505 (expected range = 0.722–0.821)

5832 measured reflections

5494 independent reflections

3410 reflections with I > 2σ(I)

R int = 0.023

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

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.145

S = 1.02

5494 reflections

394 parameters

118 restraints

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.25 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062952/tk2224sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062952/tk2224Isup2.hkl

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

[Cu(C6H8N2)(C13H15N3)](ClO4)2	F000 = 1196
Mr = 583.86	Dx = 1.574 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 40 reflections
a = 9.3178 (10) Å	θ = 5.1–12.5º
b = 13.9691 (19) Å	µ = 1.16 mm−1
c = 19.223 (3) Å	T = 293 (2) K
β = 99.931 (11)º	Needle, dark blue
V = 2464.6 (6) Å3	0.45 × 0.22 × 0.17 mm
Z = 4

Bruker P4S diffractometer	Rint = 0.023
Radiation source: fine-focus sealed tube	θmax = 27.5º
Monochromator: graphite	θmin = 2.6º
T = 293(2) K	h = 0→10
ω scans	k = 0→18
Absorption correction: empirical (using intensity measurements)ψ-scan (North et al., 1968)	l = −24→24
Tmin = 0.444, Tmax = 0.505	3 standard reflections
5832 measured reflections	every 97 reflections
5494 independent reflections	intensity decay: <2%
3410 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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.145	w = 1/[σ2(Fo2) + (0.0609P)2 + 0.9236P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
5494 reflections	Δρmax = 0.40 e Å−3
394 parameters	Δρmin = −0.25 e Å−3
118 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	0.82061 (5)	0.75715 (3)	0.13019 (2)	0.05120 (17)
Cl1	0.31446 (13)	0.67766 (9)	0.06898 (6)	0.0720 (3)
Cl2	0.79982 (12)	0.81545 (7)	−0.12730 (6)	0.0641 (3)
O11	0.3166 (9)	0.7331 (9)	0.1286 (5)	0.152 (4)	0.601 (8)
O12	0.1675 (7)	0.6764 (9)	0.0381 (6)	0.153 (4)	0.601 (8)
O13	0.3873 (12)	0.7307 (8)	0.0218 (5)	0.159 (4)	0.601 (8)
O14	0.3776 (16)	0.5943 (7)	0.0733 (8)	0.209 (5)	0.601 (8)
O11A	0.256 (2)	0.7538 (10)	0.0342 (10)	0.183 (6)	0.399 (8)
O12A	0.4019 (17)	0.6278 (13)	0.0278 (9)	0.175 (5)	0.399 (8)
O13A	0.2181 (16)	0.6067 (10)	0.0823 (9)	0.155 (5)	0.399 (8)
O14A	0.4133 (19)	0.6940 (15)	0.1287 (7)	0.194 (7)	0.399 (8)
O21	0.9137 (13)	0.7800 (12)	−0.0783 (7)	0.115 (4)	0.659 (11)
O22	0.7988 (12)	0.9139 (5)	−0.1336 (7)	0.135 (4)	0.659 (11)
O23	0.7929 (11)	0.7683 (7)	−0.1931 (3)	0.111 (3)	0.659 (11)
O24	0.6647 (8)	0.7921 (7)	−0.1036 (5)	0.124 (3)	0.659 (11)
O21A	0.941 (2)	0.780 (2)	−0.0915 (13)	0.114 (7)	0.341 (11)
O22A	0.735 (2)	0.8536 (14)	−0.0741 (7)	0.130 (5)	0.341 (11)
O23A	0.840 (3)	0.8895 (13)	−0.1687 (11)	0.152 (8)	0.341 (11)
O24A	0.728 (2)	0.7459 (10)	−0.1643 (11)	0.128 (6)	0.341 (11)
N1	0.9081 (4)	0.6274 (2)	0.14801 (18)	0.0582 (8)
N2	0.7204 (4)	0.6948 (3)	0.04142 (19)	0.0711 (10)
H2B	0.6256	0.6870	0.0439	0.085*
H2C	0.7261	0.7336	0.0046	0.085*
N	1.0124 (4)	0.8442 (3)	0.1207 (2)	0.0676 (10)
H0A	1.0778	0.8088	0.1015	0.081*
N1A	0.7231 (4)	0.8851 (2)	0.10460 (16)	0.0528 (8)
C1	0.9991 (6)	0.5995 (4)	0.2061 (3)	0.0838 (15)
H1A	1.0200	0.6419	0.2438	0.101*
C2	1.0625 (6)	0.5108 (4)	0.2119 (3)	0.0928 (17)
H2A	1.1239	0.4928	0.2532	0.111*
C3	1.0343 (6)	0.4493 (4)	0.1563 (3)	0.0893 (16)
H3A	1.0773	0.3890	0.1591	0.107*
C4	0.9423 (5)	0.4767 (3)	0.0963 (3)	0.0747 (13)
H4A	0.9213	0.4352	0.0581	0.090*
C5	0.8813 (5)	0.5668 (3)	0.0934 (2)	0.0586 (10)
C6	0.7826 (7)	0.6032 (4)	0.0292 (3)	0.0898 (16)
H6A	0.8371	0.6090	−0.0093	0.108*
H6B	0.7048	0.5574	0.0151	0.108*
C1A	0.5863 (5)	0.9080 (3)	0.1121 (2)	0.0678 (12)
H1AA	0.5272	0.8609	0.1264	0.081*
C2A	0.5311 (6)	0.9987 (4)	0.0992 (3)	0.0824 (15)
H2AA	0.4362	1.0128	0.1048	0.099*
C3A	0.6177 (7)	1.0677 (4)	0.0780 (3)	0.0912 (17)
H3AA	0.5820	1.1294	0.0688	0.109*
C4A	0.7575 (6)	1.0460 (3)	0.0703 (2)	0.0750 (13)
H4AA	0.8179	1.0927	0.0565	0.090*
C5A	0.8077 (5)	0.9526 (3)	0.0835 (2)	0.0591 (10)
C6A	0.9570 (5)	0.9222 (3)	0.0733 (2)	0.0691 (12)
H6AA	0.9535	0.9019	0.0248	0.083*
H6AB	1.0228	0.9764	0.0819	0.083*
N1B	0.8682 (4)	0.8030 (2)	0.23229 (17)	0.0591 (9)
C1B	0.7839 (6)	0.7840 (4)	0.2815 (3)	0.0811 (16)
C11B	0.6648 (6)	0.7120 (5)	0.2627 (3)	0.105 (2)
H11A	0.7063	0.6510	0.2546	0.158*
H11B	0.6007	0.7322	0.2207	0.158*
H11C	0.6108	0.7066	0.3008	0.158*
C2B	0.8124 (8)	0.8284 (6)	0.3461 (3)	0.120 (3)
H2BA	0.7582	0.8131	0.3808	0.145*
C3B	0.9221 (11)	0.8958 (7)	0.3591 (4)	0.146 (4)
H3BA	0.9395	0.9281	0.4020	0.175*
C4B	1.0036 (8)	0.9143 (4)	0.3092 (4)	0.116 (3)
H4BA	1.0768	0.9602	0.3174	0.139*
C5B	0.9783 (6)	0.8648 (3)	0.2458 (3)	0.0728 (14)
C6B	1.0765 (6)	0.8746 (4)	0.1921 (3)	0.0904 (17)
H6BA	1.1056	0.9411	0.1904	0.108*
H6BB	1.1638	0.8372	0.2076	0.108*

	U11	U22	U33	U12	U13	U23
Cu	0.0506 (3)	0.0457 (3)	0.0560 (3)	0.0023 (2)	0.0057 (2)	−0.0030 (2)
Cl1	0.0659 (7)	0.0798 (8)	0.0700 (7)	−0.0029 (6)	0.0109 (6)	−0.0066 (6)
Cl2	0.0725 (7)	0.0507 (6)	0.0661 (6)	0.0027 (5)	0.0036 (5)	−0.0019 (5)
O11	0.095 (6)	0.257 (12)	0.103 (6)	0.002 (7)	0.011 (5)	−0.087 (7)
O12	0.062 (4)	0.198 (10)	0.191 (9)	−0.012 (5)	−0.003 (5)	−0.065 (8)
O13	0.164 (8)	0.168 (8)	0.166 (7)	−0.005 (7)	0.083 (7)	0.047 (7)
O14	0.248 (11)	0.127 (7)	0.258 (12)	0.083 (8)	0.063 (10)	0.051 (8)
O11A	0.175 (12)	0.153 (11)	0.226 (12)	0.070 (9)	0.045 (11)	0.080 (9)
O12A	0.165 (9)	0.185 (12)	0.205 (12)	0.053 (10)	0.115 (9)	0.029 (11)
O13A	0.127 (10)	0.128 (10)	0.227 (12)	−0.046 (8)	0.076 (9)	0.015 (9)
O14A	0.164 (13)	0.270 (17)	0.116 (10)	−0.105 (13)	−0.059 (10)	0.006 (11)
O21	0.113 (7)	0.134 (7)	0.084 (5)	0.029 (6)	−0.019 (5)	0.004 (5)
O22	0.132 (7)	0.053 (4)	0.210 (11)	−0.012 (4)	0.000 (7)	0.003 (5)
O23	0.129 (7)	0.125 (7)	0.073 (4)	0.017 (5)	0.001 (4)	−0.024 (4)
O24	0.098 (5)	0.107 (6)	0.175 (8)	−0.004 (4)	0.052 (5)	0.021 (5)
O21A	0.072 (9)	0.133 (12)	0.122 (14)	0.042 (9)	−0.021 (9)	−0.038 (11)
O22A	0.128 (11)	0.127 (11)	0.140 (10)	0.051 (9)	0.042 (8)	−0.022 (9)
O23A	0.200 (16)	0.091 (12)	0.168 (16)	−0.026 (11)	0.037 (12)	0.051 (11)
O24A	0.111 (11)	0.092 (8)	0.167 (13)	−0.025 (8)	−0.019 (9)	−0.045 (9)
N1	0.058 (2)	0.0481 (19)	0.067 (2)	0.0039 (16)	0.0069 (17)	−0.0052 (16)
N2	0.075 (2)	0.071 (2)	0.063 (2)	0.005 (2)	−0.0003 (19)	−0.0083 (19)
N	0.051 (2)	0.057 (2)	0.097 (3)	0.0004 (17)	0.020 (2)	−0.001 (2)
N1A	0.051 (2)	0.0505 (18)	0.0553 (19)	0.0033 (16)	0.0048 (15)	−0.0013 (15)
C1	0.084 (4)	0.069 (3)	0.088 (3)	0.026 (3)	−0.015 (3)	−0.013 (3)
C2	0.092 (4)	0.077 (4)	0.100 (4)	0.029 (3)	−0.009 (3)	0.001 (3)
C3	0.082 (4)	0.053 (3)	0.136 (5)	0.014 (3)	0.027 (4)	0.001 (3)
C4	0.072 (3)	0.055 (3)	0.099 (4)	0.000 (2)	0.023 (3)	−0.019 (3)
C5	0.054 (2)	0.051 (2)	0.072 (3)	−0.0076 (19)	0.016 (2)	−0.010 (2)
C6	0.115 (4)	0.071 (3)	0.077 (3)	0.012 (3)	0.001 (3)	−0.020 (3)
C1A	0.061 (3)	0.070 (3)	0.069 (3)	0.014 (2)	0.002 (2)	−0.001 (2)
C2A	0.076 (3)	0.086 (4)	0.080 (3)	0.032 (3)	−0.001 (3)	−0.004 (3)
C3A	0.120 (5)	0.061 (3)	0.085 (4)	0.029 (3)	−0.004 (3)	−0.001 (3)
C4A	0.100 (4)	0.054 (3)	0.066 (3)	0.002 (3)	0.000 (3)	0.005 (2)
C5A	0.074 (3)	0.053 (2)	0.047 (2)	0.001 (2)	−0.001 (2)	−0.0026 (18)
C6A	0.069 (3)	0.068 (3)	0.073 (3)	−0.013 (2)	0.017 (2)	0.001 (2)
N1B	0.065 (2)	0.054 (2)	0.056 (2)	0.0133 (18)	0.0019 (17)	−0.0060 (16)
C1B	0.082 (4)	0.100 (4)	0.060 (3)	0.047 (3)	0.008 (3)	0.001 (3)
C11B	0.087 (4)	0.142 (6)	0.095 (4)	0.010 (4)	0.037 (3)	0.025 (4)
C2B	0.125 (6)	0.174 (8)	0.061 (4)	0.084 (6)	0.012 (4)	−0.008 (4)
C3B	0.157 (8)	0.168 (8)	0.093 (5)	0.090 (7)	−0.029 (5)	−0.067 (6)
C4B	0.114 (5)	0.085 (4)	0.125 (5)	0.029 (4)	−0.048 (4)	−0.044 (4)
C5B	0.077 (3)	0.054 (3)	0.076 (3)	0.020 (2)	−0.021 (3)	−0.010 (2)
C6B	0.066 (3)	0.079 (4)	0.113 (4)	−0.016 (3)	−0.019 (3)	0.022 (3)

Cu—N1	1.993 (3)	C3—C4	1.367 (7)
Cu—N2	1.998 (3)	C3—H3A	0.9300
Cu—N1A	2.027 (3)	C4—C5	1.378 (6)
Cu—N1B	2.039 (3)	C4—H4A	0.9300
Cu—N	2.195 (3)	C5—C6	1.496 (7)
Cl1—O14	1.301 (9)	C6—H6A	0.9700
Cl1—O11A	1.321 (10)	C6—H6B	0.9700
Cl1—O14A	1.362 (10)	C1A—C2A	1.374 (6)
Cl1—O11	1.381 (7)	C1A—H1AA	0.9300
Cl1—O13A	1.391 (9)	C2A—C3A	1.364 (8)
Cl1—O12	1.396 (7)	C2A—H2AA	0.9300
Cl1—O12A	1.414 (11)	C3A—C4A	1.370 (7)
Cl1—O13	1.430 (7)	C3A—H3AA	0.9300
Cl2—O24A	1.315 (11)	C4A—C5A	1.394 (6)
Cl2—O22A	1.380 (10)	C4A—H4AA	0.9300
Cl2—O22	1.381 (7)	C5A—C6A	1.499 (6)
Cl2—O21	1.383 (8)	C6A—H6AA	0.9700
Cl2—O23A	1.396 (12)	C6A—H6AB	0.9700
Cl2—O23	1.417 (6)	N1B—C5B	1.332 (6)
Cl2—O24	1.448 (6)	N1B—C1B	1.356 (6)
Cl2—O21A	1.461 (13)	C1B—C2B	1.371 (8)
N1—C5	1.337 (5)	C1B—C11B	1.495 (8)
N1—C1	1.337 (6)	C11B—H11A	0.9600
N2—C6	1.440 (6)	C11B—H11B	0.9600
N2—H2B	0.9000	C11B—H11C	0.9600
N2—H2C	0.9000	C2B—C3B	1.380 (11)
N—C6A	1.456 (6)	C2B—H2BA	0.9300
N—C6B	1.462 (6)	C3B—C4B	1.347 (11)
N—H0A	0.9100	C3B—H3BA	0.9300
N1A—C5A	1.336 (5)	C4B—C5B	1.386 (7)
N1A—C1A	1.346 (5)	C4B—H4BA	0.9300
C1—C2	1.369 (7)	C5B—C6B	1.499 (7)
C1—H1A	0.9300	C6B—H6BA	0.9700
C2—C3	1.361 (7)	C6B—H6BB	0.9700
C2—H2A	0.9300
N1—Cu—N2	82.37 (15)	C3—C4—C5	118.9 (5)
N1—Cu—N1A	175.43 (13)	C3—C4—H4A	120.5
N2—Cu—N1A	93.06 (14)	C5—C4—H4A	120.5
N1—Cu—N1B	96.05 (14)	N1—C5—C4	121.8 (4)
N2—Cu—N1B	161.97 (16)	N1—C5—C6	116.0 (4)
N1A—Cu—N1B	88.33 (13)	C4—C5—C6	122.3 (4)
N1—Cu—N	101.74 (14)	N2—C6—C5	112.0 (4)
N2—Cu—N	115.93 (16)	N2—C6—H6A	109.2
N1A—Cu—N	80.11 (13)	C5—C6—H6A	109.2
N1B—Cu—N	82.03 (15)	N2—C6—H6B	109.2
O11A—Cl1—O14A	116.7 (11)	C5—C6—H6B	109.2
O14—Cl1—O11	120.5 (8)	H6A—C6—H6B	107.9
O11A—Cl1—O13A	116.5 (10)	N1A—C1A—C2A	122.2 (5)
O14A—Cl1—O13A	109.2 (9)	N1A—C1A—H1AA	118.9
O14—Cl1—O12	114.6 (8)	C2A—C1A—H1AA	118.9
O11—Cl1—O12	103.5 (5)	C3A—C2A—C1A	118.9 (5)
O11A—Cl1—O12A	109.8 (10)	C3A—C2A—H2AA	120.6
O14A—Cl1—O12A	100.6 (10)	C1A—C2A—H2AA	120.6
O13A—Cl1—O12A	101.9 (9)	C2A—C3A—C4A	119.9 (5)
O12—Cl1—O12A	111.9 (9)	C2A—C3A—H3AA	120.1
O14—Cl1—O13	104.2 (7)	C4A—C3A—H3AA	120.1
O11—Cl1—O13	107.2 (7)	C3A—C4A—C5A	118.9 (5)
O12—Cl1—O13	105.9 (7)	C3A—C4A—H4AA	120.6
O24A—Cl2—O22A	116.2 (10)	C5A—C4A—H4AA	120.6
O24A—Cl2—O21	111.1 (12)	N1A—C5A—C4A	121.2 (4)
O22—Cl2—O21	114.2 (7)	N1A—C5A—C6A	116.7 (4)
O24A—Cl2—O23A	113.6 (11)	C4A—C5A—C6A	122.0 (4)
O22A—Cl2—O23A	109.3 (9)	N—C6A—C5A	111.5 (4)
O22—Cl2—O23	112.7 (6)	N—C6A—H6AA	109.3
O21—Cl2—O23	110.6 (7)	C5A—C6A—H6AA	109.3
O22—Cl2—O24	105.0 (5)	N—C6A—H6AB	109.3
O21—Cl2—O24	108.2 (7)	C5A—C6A—H6AB	109.3
O23—Cl2—O24	105.5 (5)	H6AA—C6A—H6AB	108.0
O24A—Cl2—O21A	109.3 (12)	C5B—N1B—C1B	120.6 (4)
O22A—Cl2—O21A	104.7 (11)	C5B—N1B—Cu	115.1 (3)
O23A—Cl2—O21A	102.4 (12)	C1B—N1B—Cu	123.7 (3)
C5—N1—C1	118.4 (4)	N1B—C1B—C2B	119.9 (6)
C5—N1—Cu	115.2 (3)	N1B—C1B—C11B	117.3 (4)
C1—N1—Cu	126.1 (3)	C2B—C1B—C11B	122.8 (6)
C6—N2—Cu	112.6 (3)	C1B—C11B—H11A	109.5
C6—N2—H2B	109.1	C1B—C11B—H11B	109.5
Cu—N2—H2B	109.1	H11A—C11B—H11B	109.5
C6—N2—H2C	109.1	C1B—C11B—H11C	109.5
Cu—N2—H2C	109.1	H11A—C11B—H11C	109.5
H2B—N2—H2C	107.8	H11B—C11B—H11C	109.5
C6A—N—C6B	114.4 (4)	C1B—C2B—C3B	119.6 (7)
C6A—N—Cu	105.1 (3)	C1B—C2B—H2BA	120.2
C6B—N—Cu	106.8 (3)	C3B—C2B—H2BA	120.2
C6A—N—H0A	110.1	C4B—C3B—C2B	119.5 (7)
C6B—N—H0A	110.1	C4B—C3B—H3BA	120.3
Cu—N—H0A	110.1	C2B—C3B—H3BA	120.3
C5A—N1A—C1A	118.9 (4)	C3B—C4B—C5B	119.9 (7)
C5A—N1A—Cu	115.6 (3)	C3B—C4B—H4BA	120.0
C1A—N1A—Cu	125.3 (3)	C5B—C4B—H4BA	120.0
N1—C1—C2	122.3 (5)	N1B—C5B—C4B	120.2 (6)
N1—C1—H1A	118.9	N1B—C5B—C6B	117.8 (4)
C2—C1—H1A	118.9	C4B—C5B—C6B	121.9 (6)
C3—C2—C1	119.0 (5)	N—C6B—C5B	114.9 (4)
C3—C2—H2A	120.5	N—C6B—H6BA	108.5
C1—C2—H2A	120.5	C5B—C6B—H6BA	108.5
C2—C3—C4	119.6 (5)	N—C6B—H6BB	108.5
C2—C3—H3A	120.2	C5B—C6B—H6BB	108.5
C4—C3—H3A	120.2	H6BA—C6B—H6BB	107.5
N2—Cu—N1—C5	9.1 (3)	C5A—N1A—C1A—C2A	−0.4 (6)
N1A—Cu—N1—C5	7.6 (19)	Cu—N1A—C1A—C2A	174.5 (3)
N1B—Cu—N1—C5	171.0 (3)	N1A—C1A—C2A—C3A	0.1 (7)
N—Cu—N1—C5	−105.9 (3)	C1A—C2A—C3A—C4A	−0.4 (8)
N2—Cu—N1—C1	−177.1 (4)	C2A—C3A—C4A—C5A	0.9 (7)
N1A—Cu—N1—C1	−179 (36)	C1A—N1A—C5A—C4A	1.0 (6)
N1B—Cu—N1—C1	−15.1 (4)	Cu—N1A—C5A—C4A	−174.4 (3)
N—Cu—N1—C1	67.9 (4)	C1A—N1A—C5A—C6A	−177.6 (4)
N1—Cu—N2—C6	−12.6 (4)	Cu—N1A—C5A—C6A	7.0 (4)
N1A—Cu—N2—C6	167.3 (4)	C3A—C4A—C5A—N1A	−1.2 (7)
N1B—Cu—N2—C6	−98.7 (6)	C3A—C4A—C5A—C6A	177.3 (4)
N—Cu—N2—C6	86.8 (4)	C6B—N—C6A—C5A	−81.9 (5)
N1—Cu—N—C6A	150.8 (3)	Cu—N—C6A—C5A	34.9 (4)
N2—Cu—N—C6A	63.7 (3)	N1A—C5A—C6A—N	−30.2 (5)
N1A—Cu—N—C6A	−24.9 (3)	C4A—C5A—C6A—N	151.2 (4)
N1B—Cu—N—C6A	−114.6 (3)	N1—Cu—N1B—C5B	105.0 (3)
N1—Cu—N—C6B	−87.2 (3)	N2—Cu—N1B—C5B	−171.0 (4)
N2—Cu—N—C6B	−174.4 (3)	N1A—Cu—N1B—C5B	−76.3 (3)
N1A—Cu—N—C6B	97.0 (3)	N—Cu—N1B—C5B	4.0 (3)
N1B—Cu—N—C6B	7.3 (3)	N1—Cu—N1B—C1B	−84.0 (4)
N1—Cu—N1A—C5A	−103.9 (17)	N2—Cu—N1B—C1B	0.0 (7)
N2—Cu—N1A—C5A	−105.4 (3)	N1A—Cu—N1B—C1B	94.7 (3)
N1B—Cu—N1A—C5A	92.6 (3)	N—Cu—N1B—C1B	174.9 (4)
N—Cu—N1A—C5A	10.4 (3)	C5B—N1B—C1B—C2B	−0.4 (7)
N1—Cu—N1A—C1A	81.0 (18)	Cu—N1B—C1B—C2B	−170.9 (4)
N2—Cu—N1A—C1A	79.6 (3)	C5B—N1B—C1B—C11B	−178.6 (4)
N1B—Cu—N1A—C1A	−82.4 (3)	Cu—N1B—C1B—C11B	10.9 (6)
N—Cu—N1A—C1A	−164.6 (3)	N1B—C1B—C2B—C3B	3.4 (9)
C5—N1—C1—C2	−1.5 (8)	C11B—C1B—C2B—C3B	−178.5 (6)
Cu—N1—C1—C2	−175.2 (4)	C1B—C2B—C3B—C4B	−2.7 (11)
N1—C1—C2—C3	1.2 (9)	C2B—C3B—C4B—C5B	−0.9 (11)
C1—C2—C3—C4	−0.8 (9)	C1B—N1B—C5B—C4B	−3.2 (6)
C2—C3—C4—C5	0.6 (8)	Cu—N1B—C5B—C4B	168.1 (4)
C1—N1—C5—C4	1.4 (6)	C1B—N1B—C5B—C6B	173.7 (4)
Cu—N1—C5—C4	175.7 (3)	Cu—N1B—C5B—C6B	−15.0 (5)
C1—N1—C5—C6	−178.1 (5)	C3B—C4B—C5B—N1B	3.9 (8)
Cu—N1—C5—C6	−3.7 (5)	C3B—C4B—C5B—C6B	−172.9 (6)
C3—C4—C5—N1	−0.9 (7)	C6A—N—C6B—C5B	99.2 (5)
C3—C4—C5—C6	178.5 (5)	Cu—N—C6B—C5B	−16.7 (5)
Cu—N2—C6—C5	13.8 (6)	N1B—C5B—C6B—N	22.1 (6)
N1—C5—C6—N2	−6.8 (7)	C4B—C5B—C6B—N	−161.0 (4)
C4—C5—C6—N2	173.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O12A	0.90	2.21	3.080 (17)	161
N2—H2B···O13	0.90	2.27	3.103 (12)	154
N2—H2C···O24	0.90	2.22	3.064 (9)	157
N2—H2C···O22A	0.90	2.27	3.158 (19)	169
N2—H2C···O21	0.90	2.64	3.374 (17)	139
N—H0A···O12i	0.91	2.44	3.301 (10)	158
N—H0A···O11Ai	0.91	2.40	3.291 (19)	165
C3—H3A···O23ii	0.93	2.54	3.456 (10)	169
C4—H4A···O12iii	0.93	2.45	3.374 (10)	172
C1A—H1AA···O14A	0.93	2.57	3.438 (18)	156
C2A—H2AA···O22iv	0.93	2.56	3.475 (13)	167
C2A—H2AA···O22Aiv	0.93	2.46	3.199 (14)	136
C6A—H6AB···O22v	0.97	2.35	3.294 (10)	164
C11B—H11B···O14A	0.96	2.32	3.180 (12)	148
C6B—H6BA···O22v	0.97	2.53	3.433 (10)	154
C6B—H6BA···O23Av	0.97	2.47	3.433 (17)	172
C6B—H6BB···O23vi	0.97	2.54	3.375 (10)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O12A	0.90	2.21	3.080 (17)	161
N2—H2B⋯O13	0.90	2.27	3.103 (12)	154
N2—H2C⋯O24	0.90	2.22	3.064 (9)	157
N2—H2C⋯O22A	0.90	2.27	3.158 (19)	169
N2—H2C⋯O21	0.90	2.64	3.374 (17)	139
N—H0A⋯O12i	0.91	2.44	3.301 (10)	158
N—H0A⋯O11Ai	0.91	2.40	3.291 (19)	165
C3—H3A⋯O23ii	0.93	2.54	3.456 (10)	169
C4—H4A⋯O12iii	0.93	2.45	3.374 (10)	172
C1A—H1AA⋯O14A	0.93	2.57	3.438 (18)	156
C2A—H2AA⋯O22iv	0.93	2.56	3.475 (13)	167
C2A—H2AA⋯O22Aiv	0.93	2.46	3.199 (14)	136
C6A—H6AB⋯O22v	0.97	2.35	3.294 (10)	164
C11B—H11B⋯O14A	0.96	2.32	3.180 (12)	148
C6B—H6BA⋯O22v	0.97	2.53	3.433 (10)	154
C6B—H6BA⋯O23Av	0.97	2.47	3.433 (17)	172
C6B—H6BB⋯O23vi	0.97	2.54	3.375 (10)	144

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