Bis{2-[2-(isopropyl-ammonio)ethyl-imino-meth-yl]-5-methoxy-phenolato}copper(II) bis-(perchlorate).

In the title compound, [Cu(C(13)H(20)N(2)O(2))(2)](ClO(4))(2), the Cu(II) atom in the complex dication is chelated by two phenolate O atoms and two imine N atoms from two zwitterionic 2-[2-(isopropyl-ammonio)ethyl-imino-meth-yl]-5-methoxy-phenolate ligands, forming a distorted square-planar geometry. One of the perchlorate anions is disordered over two sites with occupancies of 0.611 (15) and 0.389 (15). Intra-molecular N-H⋯O hydrogen bonds are observed in the complex dication. In the crystal structure, the perchlorate anions are linked to complex dications by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For general background to CuII complexes, see: Collinson & Fenton (1996 ▶); Hossain et al. (1996 ▶); Tarafder et al. (2002 ▶); Musie et al. (2003 ▶); García-Raso et al. (2003 ▶); Reddy et al. (2000 ▶); Ray et al. (2003 ▶); Arnold et al. (2003 ▶); Raptopoulou et al. (1998 ▶). For related structures, see: Wang et al. (2009a ▶,b ▶, 2010 ▶); Wang (2009 ▶). For bond lengths and angles in related CuII complexes, see: Hebbachi & Benali-Cherif (2005 ▶); Butcher et al. (2003 ▶); Elmali et al. (2000 ▶); Warda et al. (1997 ▶).

Experimental

Crystal data

[Cu(C13H20N2O2)2](ClO4)2

M = 735.06

Orthorhombic,

a = 17.4415 (13) Å

b = 14.009 (1) Å

c = 26.350 (2) Å

V = 6438.2 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.91 mm−1

T = 298 K

0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.839, T max = 0.861

36964 measured reflections

7004 independent reflections

3260 reflections with I > 2σ(I)

R int = 0.117

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.182

S = 1.01

7004 reflections

449 parameters

94 restraints

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017472/ci5083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017472/ci5083Isup2.hkl

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

[Cu(C13H20N2O2)2](ClO4)2	F(000) = 3064
Mr = 735.06	Dx = 1.517 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2387 reflections
a = 17.4415 (13) Å	θ = 2.4–24.5°
b = 14.009 (1) Å	µ = 0.91 mm−1
c = 26.350 (2) Å	T = 298 K
V = 6438.2 (8) Å3	Block, blue
Z = 8	0.20 × 0.18 × 0.17 mm

Bruker SMART CCD area-detector diffractometer	7004 independent reflections
Radiation source: fine-focus sealed tube	3260 reflections with I > 2σ(I)
graphite	Rint = 0.117
ω scan	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→20
Tmin = 0.839, Tmax = 0.861	k = −17→17
36964 measured reflections	l = −29→33

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0802P)2 + 0.2786P] where P = (Fo2 + 2Fc2)/3
7004 reflections	(Δ/σ)max = 0.001
449 parameters	Δρmax = 0.67 e Å−3
94 restraints	Δρmin = −0.38 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.20772 (3)	0.30739 (5)	0.29436 (2)	0.0430 (2)
Cl1	0.35617 (10)	0.50449 (12)	0.29759 (6)	0.0669 (5)
N1	0.2829 (2)	0.2199 (3)	0.32521 (16)	0.0443 (11)
N2	0.3178 (3)	0.3382 (3)	0.41567 (18)	0.0574 (13)
H2A	0.3298	0.3618	0.3849	0.069*
H2B	0.2676	0.3497	0.4207	0.069*
N3	0.1097 (2)	0.3435 (3)	0.26267 (15)	0.0417 (10)
N4	0.1766 (2)	0.4031 (3)	0.15898 (16)	0.0528 (12)
H4A	0.1910	0.3676	0.1321	0.063*
H4B	0.2056	0.3851	0.1856	0.063*
O1	0.2543 (2)	0.2985 (3)	0.22831 (13)	0.0514 (10)
O2	0.4443 (2)	0.2600 (3)	0.10520 (15)	0.0643 (11)
O3	0.17867 (19)	0.3576 (2)	0.35993 (12)	0.0444 (9)
O4	0.0587 (2)	0.5763 (3)	0.47332 (14)	0.0559 (10)
O5	0.3648 (3)	0.5847 (5)	0.3286 (3)	0.147 (2)
O6	0.3925 (4)	0.4248 (5)	0.3208 (3)	0.159 (3)
O7	0.3923 (3)	0.5183 (5)	0.2529 (2)	0.148 (2)
O8	0.2780 (3)	0.4867 (4)	0.2923 (3)	0.135 (2)
Cl2'	0.17958 (9)	0.25224 (11)	0.03722 (6)	0.0601 (4)	0.389 (15)
O9'	0.1570 (12)	0.2204 (11)	0.0869 (4)	0.129 (7)	0.389 (15)
O10'	0.2039 (11)	0.1768 (11)	0.0069 (7)	0.122 (8)	0.389 (15)
O11'	0.1144 (9)	0.3020 (11)	0.0192 (8)	0.141 (8)	0.389 (15)
O12'	0.2391 (10)	0.3202 (14)	0.0434 (8)	0.132 (10)	0.389 (15)
Cl2	0.17958 (9)	0.25224 (11)	0.03722 (6)	0.0601 (4)	0.611 (15)
O9	0.1079 (6)	0.2451 (11)	0.0606 (6)	0.164 (6)	0.611 (15)
O10	0.2095 (8)	0.1581 (7)	0.0317 (6)	0.145 (6)	0.611 (15)
O11	0.1749 (9)	0.2871 (9)	−0.0129 (3)	0.157 (6)	0.611 (15)
O12	0.2292 (6)	0.3064 (10)	0.0667 (5)	0.133 (6)	0.611 (15)
C1	0.3633 (3)	0.2031 (3)	0.2500 (2)	0.0433 (13)
C2	0.3208 (3)	0.2609 (4)	0.21648 (19)	0.0419 (12)
C3	0.3518 (3)	0.2759 (4)	0.1675 (2)	0.0496 (14)
H3	0.3243	0.3121	0.1441	0.060*
C4	0.4217 (3)	0.2383 (4)	0.1535 (2)	0.0466 (13)
C5	0.4627 (3)	0.1818 (4)	0.1865 (2)	0.0510 (14)
H5	0.5096	0.1557	0.1769	0.061*
C6	0.4335 (3)	0.1650 (4)	0.2330 (2)	0.0510 (15)
H6	0.4611	0.1262	0.2550	0.061*
C7	0.3393 (3)	0.1828 (4)	0.3006 (2)	0.0447 (13)
H7	0.3678	0.1372	0.3180	0.054*
C8	0.2723 (3)	0.1865 (4)	0.3781 (2)	0.0536 (15)
H8A	0.2791	0.1178	0.3793	0.064*
H8B	0.2205	0.2008	0.3890	0.064*
C9	0.3286 (4)	0.2335 (4)	0.4139 (2)	0.0597 (16)
H9A	0.3220	0.2073	0.4477	0.072*
H9B	0.3805	0.2194	0.4029	0.072*
C10	0.3603 (4)	0.3919 (5)	0.4532 (3)	0.084 (2)
H10	0.3401	0.3683	0.4856	0.101*
C11	0.4435 (4)	0.3724 (7)	0.4567 (4)	0.151 (4)
H11A	0.4674	0.3862	0.4247	0.182*
H11B	0.4515	0.3065	0.4651	0.182*
H11C	0.4657	0.4120	0.4826	0.182*
C12	0.3397 (4)	0.4960 (4)	0.4536 (3)	0.085 (2)
H12A	0.3656	0.5271	0.4812	0.102*
H12B	0.2853	0.5028	0.4578	0.102*
H12C	0.3551	0.5247	0.4222	0.102*
C13	0.5160 (3)	0.2259 (5)	0.0871 (3)	0.0691 (18)
H13A	0.5554	0.2416	0.1111	0.083*
H13B	0.5274	0.2552	0.0551	0.083*
H13C	0.5136	0.1579	0.0830	0.083*
C14	0.0646 (3)	0.4398 (4)	0.33394 (18)	0.0391 (12)
C15	0.1234 (3)	0.4187 (4)	0.36975 (19)	0.0397 (12)
C16	0.1200 (3)	0.4628 (4)	0.41700 (19)	0.0416 (13)
H16	0.1566	0.4472	0.4413	0.050*
C17	0.0644 (3)	0.5287 (4)	0.4289 (2)	0.0457 (13)
C18	0.0072 (3)	0.5516 (4)	0.3937 (2)	0.0482 (14)
H18	−0.0299	0.5971	0.4012	0.058*
C19	0.0073 (3)	0.5055 (4)	0.3478 (2)	0.0472 (14)
H19	−0.0321	0.5181	0.3250	0.057*
C20	0.0594 (3)	0.3960 (4)	0.28523 (19)	0.0438 (13)
H20	0.0140	0.4065	0.2675	0.053*
C21	0.0873 (3)	0.3067 (4)	0.2121 (2)	0.0573 (16)
H21A	0.0345	0.2853	0.2134	0.069*
H21B	0.1191	0.2520	0.2039	0.069*
C22	0.0957 (3)	0.3814 (5)	0.1706 (2)	0.0640 (18)
H22A	0.0706	0.3586	0.1401	0.077*
H22B	0.0701	0.4395	0.1812	0.077*
C23	0.1938 (4)	0.5072 (4)	0.1473 (2)	0.0620 (17)
H23	0.1742	0.5462	0.1753	0.074*
C24	0.2780 (4)	0.5209 (5)	0.1442 (3)	0.093 (2)
H24A	0.3018	0.4941	0.1738	0.112*
H24B	0.2894	0.5878	0.1424	0.112*
H24C	0.2973	0.4895	0.1144	0.112*
C25	0.1517 (4)	0.5364 (5)	0.0988 (2)	0.082 (2)
H25A	0.1738	0.5037	0.0703	0.098*
H25B	0.1564	0.6041	0.0940	0.098*
H25C	0.0985	0.5198	0.1017	0.098*
C26	0.1108 (4)	0.5532 (4)	0.5135 (2)	0.0648 (17)
H26A	0.1047	0.4873	0.5226	0.078*
H26B	0.1001	0.5927	0.5424	0.078*
H26C	0.1624	0.5640	0.5023	0.078*

	U11	U22	U33	U12	U13	U23
Cu1	0.0412 (4)	0.0492 (4)	0.0387 (4)	0.0057 (3)	−0.0002 (3)	0.0029 (3)
Cl1	0.0691 (11)	0.0669 (11)	0.0649 (11)	−0.0151 (9)	0.0239 (9)	−0.0104 (9)
N1	0.053 (3)	0.037 (2)	0.043 (3)	0.003 (2)	−0.005 (2)	0.005 (2)
N2	0.051 (3)	0.063 (3)	0.058 (3)	0.015 (2)	−0.012 (2)	−0.012 (2)
N3	0.039 (2)	0.049 (3)	0.037 (3)	−0.001 (2)	0.000 (2)	0.001 (2)
N4	0.051 (3)	0.074 (4)	0.034 (3)	0.017 (3)	−0.001 (2)	0.006 (2)
O1	0.046 (2)	0.064 (3)	0.044 (2)	0.019 (2)	0.0036 (18)	0.0074 (18)
O2	0.057 (3)	0.074 (3)	0.061 (3)	0.010 (2)	0.015 (2)	0.002 (2)
O3	0.041 (2)	0.051 (2)	0.041 (2)	0.0093 (18)	−0.0017 (16)	0.0019 (17)
O4	0.062 (3)	0.059 (3)	0.046 (2)	0.002 (2)	0.005 (2)	−0.0064 (19)
O5	0.115 (4)	0.140 (5)	0.186 (6)	−0.023 (4)	0.009 (4)	−0.075 (5)
O6	0.172 (6)	0.147 (5)	0.159 (6)	0.045 (5)	0.010 (5)	0.046 (5)
O7	0.124 (4)	0.236 (6)	0.083 (4)	0.000 (4)	0.044 (3)	0.022 (4)
O8	0.081 (4)	0.112 (4)	0.211 (6)	−0.031 (3)	0.039 (4)	−0.051 (4)
Cl2'	0.0687 (10)	0.0550 (10)	0.0566 (10)	−0.0030 (9)	−0.0040 (8)	0.0000 (8)
O9'	0.144 (11)	0.142 (10)	0.100 (9)	0.017 (8)	0.020 (8)	0.043 (8)
O10'	0.141 (11)	0.119 (11)	0.105 (10)	0.003 (8)	0.013 (8)	−0.047 (8)
O11'	0.116 (11)	0.145 (11)	0.161 (12)	0.028 (8)	−0.040 (9)	0.030 (8)
O12'	0.128 (12)	0.126 (12)	0.142 (13)	−0.047 (8)	0.004 (9)	−0.015 (9)
Cl2	0.0687 (10)	0.0550 (10)	0.0566 (10)	−0.0030 (9)	−0.0040 (8)	0.0000 (8)
O9	0.108 (8)	0.204 (10)	0.179 (10)	−0.006 (7)	0.050 (7)	−0.008 (8)
O10	0.188 (9)	0.102 (7)	0.144 (9)	0.044 (6)	−0.028 (8)	−0.011 (6)
O11	0.179 (10)	0.187 (10)	0.105 (8)	−0.003 (7)	−0.018 (7)	0.049 (6)
O12	0.082 (7)	0.208 (14)	0.109 (10)	−0.044 (7)	−0.002 (7)	−0.089 (9)
C1	0.043 (3)	0.039 (3)	0.047 (3)	0.005 (3)	−0.006 (3)	−0.003 (3)
C2	0.038 (3)	0.043 (3)	0.045 (3)	0.005 (3)	−0.003 (2)	−0.003 (2)
C3	0.046 (3)	0.057 (4)	0.046 (3)	0.014 (3)	−0.002 (3)	−0.002 (3)
C4	0.046 (3)	0.050 (3)	0.044 (3)	−0.007 (3)	0.005 (3)	−0.006 (3)
C5	0.039 (3)	0.050 (4)	0.064 (4)	0.007 (3)	0.002 (3)	−0.008 (3)
C6	0.045 (3)	0.052 (4)	0.056 (4)	0.013 (3)	−0.010 (3)	−0.004 (3)
C7	0.057 (3)	0.035 (3)	0.042 (3)	0.004 (3)	−0.011 (3)	0.000 (2)
C8	0.072 (4)	0.040 (3)	0.049 (3)	0.008 (3)	−0.001 (3)	0.011 (3)
C9	0.073 (4)	0.062 (4)	0.045 (3)	0.013 (3)	−0.009 (3)	0.007 (3)
C10	0.084 (5)	0.103 (6)	0.065 (5)	−0.010 (5)	−0.020 (4)	−0.003 (4)
C11	0.112 (6)	0.167 (8)	0.175 (8)	0.016 (6)	−0.071 (6)	−0.036 (6)
C12	0.094 (5)	0.077 (5)	0.084 (5)	−0.018 (4)	0.006 (4)	−0.024 (4)
C13	0.050 (4)	0.077 (5)	0.080 (5)	−0.003 (3)	0.021 (3)	−0.015 (4)
C14	0.038 (3)	0.046 (3)	0.033 (3)	0.002 (3)	0.007 (2)	0.004 (2)
C15	0.043 (3)	0.038 (3)	0.038 (3)	−0.003 (2)	0.006 (2)	0.009 (2)
C16	0.041 (3)	0.050 (3)	0.034 (3)	−0.004 (3)	−0.002 (2)	0.007 (2)
C17	0.053 (3)	0.042 (3)	0.042 (3)	−0.005 (3)	0.012 (3)	0.003 (3)
C18	0.043 (3)	0.044 (3)	0.058 (4)	0.008 (3)	0.008 (3)	0.001 (3)
C19	0.036 (3)	0.054 (4)	0.052 (4)	0.003 (3)	0.006 (3)	0.011 (3)
C20	0.032 (3)	0.059 (4)	0.041 (3)	−0.004 (3)	−0.002 (2)	0.013 (3)
C21	0.044 (3)	0.081 (4)	0.047 (4)	−0.006 (3)	−0.009 (3)	−0.006 (3)
C22	0.053 (4)	0.105 (5)	0.034 (3)	0.016 (4)	−0.010 (3)	0.002 (3)
C23	0.078 (5)	0.059 (4)	0.049 (4)	0.017 (4)	−0.003 (3)	−0.002 (3)
C24	0.095 (6)	0.078 (5)	0.107 (6)	−0.004 (4)	−0.007 (5)	0.019 (4)
C25	0.110 (6)	0.079 (5)	0.056 (4)	0.033 (4)	−0.004 (4)	0.012 (4)
C26	0.081 (5)	0.068 (4)	0.045 (4)	0.004 (4)	0.003 (3)	−0.008 (3)

Cu1—O1	1.925 (3)	C8—H8B	0.97
Cu1—O3	1.933 (3)	C9—H9A	0.97
Cu1—N3	1.969 (4)	C9—H9B	0.97
Cu1—N1	1.970 (4)	C10—C11	1.479 (7)
Cl1—O7	1.349 (5)	C10—C12	1.502 (6)
Cl1—O8	1.393 (5)	C10—H10	0.98
Cl1—O5	1.398 (6)	C11—H11A	0.96
Cl1—O6	1.422 (6)	C11—H11B	0.96
N1—C7	1.287 (6)	C11—H11C	0.96
N1—C8	1.481 (6)	C12—H12A	0.96
N2—C10	1.447 (7)	C12—H12B	0.96
N2—C9	1.480 (7)	C12—H12C	0.96
N2—H2A	0.90	C13—H13A	0.96
N2—H2B	0.90	C13—H13B	0.96
N3—C20	1.290 (6)	C13—H13C	0.96
N3—C21	1.480 (6)	C14—C19	1.407 (7)
N4—C22	1.476 (7)	C14—C15	1.424 (7)
N4—C23	1.520 (7)	C14—C20	1.426 (7)
N4—H4A	0.90	C15—C16	1.391 (7)
N4—H4B	0.90	C16—C17	1.375 (7)
O1—C2	1.312 (6)	C16—H16	0.93
O2—C4	1.366 (6)	C17—C18	1.400 (7)
O2—C13	1.421 (6)	C18—C19	1.370 (7)
O3—C15	1.315 (6)	C18—H18	0.93
O4—C17	1.351 (6)	C19—H19	0.93
O4—C26	1.431 (6)	C20—H20	0.93
Cl2'—O10'	1.391 (8)	C21—C22	1.521 (8)
Cl2'—O11'	1.416 (8)	C21—H21A	0.97
Cl2'—O12'	1.418 (9)	C21—H21B	0.97
Cl2'—O9'	1.437 (8)	C22—H22A	0.97
C1—C2	1.409 (7)	C22—H22B	0.97
C1—C6	1.410 (7)	C23—C24	1.484 (8)
C1—C7	1.427 (7)	C23—C25	1.529 (8)
C2—C3	1.416 (7)	C23—H23	0.98
C3—C4	1.379 (7)	C24—H24A	0.96
C3—H3	0.93	C24—H24B	0.96
C4—C5	1.376 (7)	C24—H24C	0.96
C5—C6	1.348 (7)	C25—H25A	0.96
C5—H5	0.93	C25—H25B	0.96
C6—H6	0.93	C25—H25C	0.96
C7—H7	0.93	C26—H26A	0.96
C8—C9	1.513 (8)	C26—H26B	0.96
C8—H8A	0.97	C26—H26C	0.96
O1—Cu1—O3	160.46 (15)	C11—C10—H10	103.6
O1—Cu1—N3	89.97 (16)	C12—C10—H10	103.6
O3—Cu1—N3	93.31 (16)	C10—C11—H11A	109.5
O1—Cu1—N1	92.98 (16)	C10—C11—H11B	109.5
O3—Cu1—N1	91.84 (16)	H11A—C11—H11B	109.5
N3—Cu1—N1	155.90 (17)	C10—C11—H11C	109.5
O7—Cl1—O8	113.3 (4)	H11A—C11—H11C	109.5
O7—Cl1—O5	110.2 (5)	H11B—C11—H11C	109.5
O8—Cl1—O5	107.9 (4)	C10—C12—H12A	109.5
O7—Cl1—O6	106.2 (4)	C10—C12—H12B	109.5
O8—Cl1—O6	109.8 (4)	H12A—C12—H12B	109.5
O5—Cl1—O6	109.4 (5)	C10—C12—H12C	109.5
C7—N1—C8	116.1 (4)	H12A—C12—H12C	109.5
C7—N1—Cu1	123.5 (4)	H12B—C12—H12C	109.5
C8—N1—Cu1	120.1 (3)	O2—C13—H13A	109.5
C10—N2—C9	118.1 (5)	O2—C13—H13B	109.5
C10—N2—H2A	107.8	H13A—C13—H13B	109.5
C9—N2—H2A	107.8	O2—C13—H13C	109.5
C10—N2—H2B	107.8	H13A—C13—H13C	109.5
C9—N2—H2B	107.8	H13B—C13—H13C	109.5
H2A—N2—H2B	107.1	C19—C14—C15	118.4 (5)
C20—N3—C21	115.7 (4)	C19—C14—C20	118.0 (5)
C20—N3—Cu1	122.8 (3)	C15—C14—C20	123.6 (5)
C21—N3—Cu1	121.4 (3)	O3—C15—C16	119.7 (5)
C22—N4—C23	115.3 (5)	O3—C15—C14	122.2 (5)
C22—N4—H4A	108.4	C16—C15—C14	118.1 (5)
C23—N4—H4A	108.4	C17—C16—C15	122.1 (5)
C22—N4—H4B	108.4	C17—C16—H16	118.9
C23—N4—H4B	108.4	C15—C16—H16	118.9
H4A—N4—H4B	107.5	O4—C17—C16	125.5 (5)
C2—O1—Cu1	127.9 (3)	O4—C17—C18	114.1 (5)
C4—O2—C13	119.4 (5)	C16—C17—C18	120.4 (5)
C15—O3—Cu1	127.2 (3)	C19—C18—C17	118.4 (5)
C17—O4—C26	118.8 (4)	C19—C18—H18	120.8
O10'—Cl2'—O11'	115.3 (10)	C17—C18—H18	120.8
O10'—Cl2'—O12'	110.6 (10)	C18—C19—C14	122.5 (5)
O11'—Cl2'—O12'	107.2 (11)	C18—C19—H19	118.7
O10'—Cl2'—O9'	111.7 (10)	C14—C19—H19	118.7
O11'—Cl2'—O9'	103.8 (9)	N3—C20—C14	128.1 (5)
O12'—Cl2'—O9'	107.7 (10)	N3—C20—H20	116.0
C2—C1—C6	118.4 (5)	C14—C20—H20	116.0
C2—C1—C7	123.2 (5)	N3—C21—C22	112.4 (5)
C6—C1—C7	118.5 (5)	N3—C21—H21A	109.1
O1—C2—C1	123.1 (5)	C22—C21—H21A	109.1
O1—C2—C3	119.7 (5)	N3—C21—H21B	109.1
C1—C2—C3	117.2 (5)	C22—C21—H21B	109.1
C4—C3—C2	121.6 (5)	H21A—C21—H21B	107.8
C4—C3—H3	119.2	N4—C22—C21	112.6 (4)
C2—C3—H3	119.2	N4—C22—H22A	109.1
O2—C4—C5	124.5 (5)	C21—C22—H22A	109.1
O2—C4—C3	114.7 (5)	N4—C22—H22B	109.1
C5—C4—C3	120.7 (5)	C21—C22—H22B	109.1
C6—C5—C4	118.6 (5)	H22A—C22—H22B	107.8
C6—C5—H5	120.7	C24—C23—N4	109.2 (5)
C4—C5—H5	120.7	C24—C23—C25	113.2 (6)
C5—C6—C1	123.5 (5)	N4—C23—C25	109.3 (5)
C5—C6—H6	118.3	C24—C23—H23	108.3
C1—C6—H6	118.3	N4—C23—H23	108.3
N1—C7—C1	127.8 (5)	C25—C23—H23	108.3
N1—C7—H7	116.1	C23—C24—H24A	109.5
C1—C7—H7	116.1	C23—C24—H24B	109.5
N1—C8—C9	111.6 (5)	H24A—C24—H24B	109.5
N1—C8—H8A	109.3	C23—C24—H24C	109.5
C9—C8—H8A	109.3	H24A—C24—H24C	109.5
N1—C8—H8B	109.3	H24B—C24—H24C	109.5
C9—C8—H8B	109.3	C23—C25—H25A	109.5
H8A—C8—H8B	108.0	C23—C25—H25B	109.5
N2—C9—C8	111.6 (4)	H25A—C25—H25B	109.5
N2—C9—H9A	109.3	C23—C25—H25C	109.5
C8—C9—H9A	109.3	H25A—C25—H25C	109.5
N2—C9—H9B	109.3	H25B—C25—H25C	109.5
C8—C9—H9B	109.3	O4—C26—H26A	109.5
H9A—C9—H9B	108.0	O4—C26—H26B	109.5
N2—C10—C11	116.8 (6)	H26A—C26—H26B	109.5
N2—C10—C12	112.8 (5)	O4—C26—H26C	109.5
C11—C10—C12	114.4 (7)	H26A—C26—H26C	109.5
N2—C10—H10	103.6	H26B—C26—H26C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O1	0.90	1.86	2.705 (5)	156
N4—H4A···O12	0.90	2.04	2.930 (13)	171
N2—H2B···O3	0.90	2.23	2.849 (5)	125
N2—H2A···O6	0.90	2.20	3.070 (9)	163

Table 1

Selected bond lengths (Å)

Cu1—O1	1.925 (3)
Cu1—O3	1.933 (3)
Cu1—N3	1.969 (4)
Cu1—N1	1.970 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯O1	0.90	1.86	2.705 (5)	156
N4—H4A⋯O12	0.90	2.04	2.930 (13)	171
N2—H2B⋯O3	0.90	2.23	2.849 (5)	125
N2—H2A⋯O6	0.90	2.20	3.070 (9)	163