Triaqua-bis{μ-N-[N-(4-meth-oxy-2-oxidobenzyl-idene)glyc-yl]glycinato(3-)}cadmium(II)dicopper(II) dihydrate.

In the title compound, [CdCu(2)(C(12)H(11)N(2)O(5))(2)(H(2)O)(3)]·2H(2)O, the Cu(II) atoms are in a square plane of N(2)O(2) atoms contributed by the tetra-dentate Schiff base trianion. The Cu(II) atoms are coordinated by one phenolate O atom, one imine N atom, one amido N atom and one carboxyl-ate O atom. The Cd(II) atom is connected via the carboxyl-ate groups, forming a heterotrinuclear Cu(II)-Cd(II)-Cu(II) system. The Cd(II) atom is seven-coordinate in a penta-gonal-bipyramidal geometry with four O atoms from two carboxyl-ate groups and three aqua ligands. The heterotrinuclear mol-ecules are linked to the uncoordinated water mol-ecules by O-H⋯O hydrogen bonds into a three-dimensional framework.

Related literature

For the magnetic properties of heteronuclear Schiff-base complexes, see: Liu et al. (2004 ▶); Zou et al. (2003 ▶); Wu et al. (2007 ▶); Costes et al. (2006 ▶). For their optical properties; see: Akine et al. (2008 ▶). For the synthesis, see: Miyasaka et al. (1996 ▶).

Experimental

Crystal data

[Cdn class="Chemical">Cu2(C12H11N2O5)2(H2O)3]·2H2O

M = 856.02

Triclinic,

a = 9.813 (2) Å

b = 12.547 (3) Å

c = 12.598 (3) Å

α = 94.175 (4)°

β = 103.168 (3)°

γ = 90.148 (4)°

V = 1506.0 (6) Å3

Z = 2

Mo Kα radiation

μ = 2.18 mm−1

T = 296 K

0.30 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.529, T max = 0.619

7383 measured reflections

5169 independent reflections

4763 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 1.05

5169 reflections

417 parameters

H-atom parameters constrained

Δρmax = 1.00 e Å−3

Δρmin = −1.13 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAIn class="Chemical">NT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039440/ng2653sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039440/ng2653Isup2.hkl

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

[CdCu2(C12H11N2O5)2(H2O)3]·2H2O	Z = 2
Mr = 856.02	F(000) = 860
Triclinic, P1	Dx = 1.888 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.813 (2) Å	Cell parameters from 6310 reflections
b = 12.547 (3) Å	θ = 2.4–27.8°
c = 12.598 (3) Å	µ = 2.18 mm−1
α = 94.175 (4)°	T = 296 K
β = 103.168 (3)°	Block, violet
γ = 90.148 (4)°	0.30 × 0.25 × 0.22 mm
V = 1506.0 (6) Å3

Bruker SMART APEX CCD diffractometer	5169 independent reflections
Radiation source: fine-focus sealed tube	4763 reflections with I > 2σ(I)
graphite	Rint = 0.072
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→11
Tmin = 0.529, Tmax = 0.619	k = −11→14
7383 measured reflections	l = −14→12

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0755P)2 + 0.7984P] where P = (Fo2 + 2Fc2)/3
5169 reflections	(Δ/σ)max = 0.001
417 parameters	Δρmax = 1.00 e Å−3
0 restraints	Δρmin = −1.13 e Å−3

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
Cu1	0.54611 (4)	0.14993 (3)	0.11223 (4)	0.03071 (14)
Cu2	−0.10904 (4)	0.15156 (3)	0.32980 (3)	0.02996 (14)
Cd1	0.20503 (2)	0.285718 (19)	0.19598 (2)	0.03119 (12)
C1	0.5331 (4)	−0.0578 (3)	0.1873 (3)	0.0314 (7)
C2	0.4838 (4)	−0.1279 (3)	0.2518 (3)	0.0352 (8)
H2	0.4140	−0.1058	0.2870	0.042*
C3	0.5367 (4)	−0.2297 (3)	0.2644 (3)	0.0368 (8)
C4	0.6384 (4)	−0.2668 (3)	0.2106 (3)	0.0399 (9)
H4	0.6698	−0.3365	0.2156	0.048*
C5	0.6902 (4)	−0.1979 (3)	0.1506 (3)	0.0379 (8)
H5	0.7602	−0.2216	0.1162	0.046*
C6	0.6440 (4)	−0.0933 (3)	0.1375 (3)	0.0318 (7)
C12	0.5260 (5)	−0.3950 (3)	0.3460 (4)	0.0538 (11)
H12A	0.5008	−0.4342	0.2758	0.081*
H12B	0.4796	−0.4266	0.3957	0.081*
H12C	0.6255	−0.3972	0.3736	0.081*
C7	0.7203 (4)	−0.0258 (3)	0.0834 (3)	0.0340 (8)
H7	0.7910	−0.0567	0.0540	0.041*
C8	0.7864 (4)	0.1400 (3)	0.0230 (3)	0.0363 (8)
H8A	0.7799	0.1131	−0.0522	0.044*
H8B	0.8833	0.1364	0.0624	0.044*
C9	0.7392 (4)	0.2552 (3)	0.0264 (3)	0.0309 (7)
C10	0.5513 (4)	0.3681 (3)	0.0622 (3)	0.0351 (8)
H10A	0.5175	0.3910	−0.0109	0.042*
H10B	0.6151	0.4227	0.1048	0.042*
C11	0.4297 (4)	0.3510 (3)	0.1151 (3)	0.0319 (8)
C13	−0.0359 (4)	−0.0660 (3)	0.3442 (3)	0.0305 (7)
C18	−0.1321 (4)	−0.0824 (3)	0.4113 (3)	0.0335 (8)
C17	−0.1393 (4)	−0.1828 (3)	0.4521 (3)	0.0386 (8)
H17	−0.1992	−0.1922	0.4984	0.046*
C16	−0.0620 (4)	−0.2677 (3)	0.4267 (3)	0.0410 (9)
H16	−0.0676	−0.3332	0.4559	0.049*
C15	0.0253 (4)	−0.2527 (3)	0.3556 (3)	0.0371 (8)
C14	0.0404 (4)	−0.1550 (3)	0.3168 (3)	0.0344 (8)
H18	0.1021	−0.1472	0.2717	0.041*
C24	0.1580 (5)	−0.3390 (3)	0.2383 (4)	0.0483 (10)
H24A	0.0958	−0.3078	0.1789	0.072*
H24B	0.1793	−0.4104	0.2152	0.072*
H24C	0.2429	−0.2968	0.2601	0.072*
C19	−0.2290 (4)	−0.0041 (3)	0.4348 (3)	0.0347 (8)
H19	−0.2887	−0.0233	0.4782	0.042*
C20	−0.3461 (4)	0.1646 (3)	0.4241 (3)	0.0378 (8)
H20A	−0.3450	0.1684	0.5015	0.045*
H20B	−0.4383	0.1395	0.3838	0.045*
C21	−0.3162 (4)	0.2750 (3)	0.3911 (3)	0.0321 (7)
C22	−0.1562 (4)	0.3748 (3)	0.3139 (3)	0.0363 (8)
H22A	−0.1300	0.4271	0.3759	0.044*
H22B	−0.2278	0.4051	0.2586	0.044*
C23	−0.0309 (4)	0.3470 (3)	0.2686 (3)	0.0281 (7)
N1	0.6983 (3)	0.0738 (2)	0.0726 (2)	0.0318 (6)
N2	0.6222 (3)	0.2672 (2)	0.0577 (3)	0.0342 (7)
N3	−0.2407 (3)	0.0901 (2)	0.4011 (2)	0.0339 (7)
N4	−0.2090 (3)	0.2785 (2)	0.3474 (3)	0.0342 (7)
O1	0.4761 (3)	0.03723 (19)	0.1772 (2)	0.0352 (6)
O2	0.8121 (3)	0.3263 (2)	0.0003 (2)	0.0445 (7)
O3	0.4089 (3)	0.2550 (2)	0.1407 (2)	0.0348 (6)
O4	0.3531 (3)	0.4239 (2)	0.1324 (2)	0.0419 (6)
O5	0.4843 (3)	−0.2862 (2)	0.3354 (2)	0.0467 (7)
O6	−0.0138 (3)	0.02539 (18)	0.3055 (2)	0.0348 (6)
O7	−0.3929 (3)	0.3516 (2)	0.4086 (2)	0.0435 (7)
O8	0.0039 (3)	0.24752 (19)	0.2634 (2)	0.0327 (5)
O9	0.0383 (3)	0.41583 (19)	0.2384 (2)	0.0352 (6)
O10	0.0928 (3)	−0.3418 (2)	0.3282 (2)	0.0483 (7)
O11	0.3254 (3)	0.3184 (2)	0.3709 (2)	0.0412 (6)
H11C	0.4125	0.3135	0.3739	0.062*
H11D	0.3080	0.3810	0.3942	0.062*
O12	0.0844 (3)	0.2909 (2)	0.0208 (2)	0.0377 (6)
H12D	0.0086	0.2548	0.0113	0.057*
H12E	0.0657	0.3553	0.0074	0.057*
O13	0.2045 (3)	0.0988 (2)	0.1947 (3)	0.0557 (8)
H13A	0.1389	0.0784	0.2229	0.084*
H13C	0.2825	0.0788	0.2318	0.084*
O14	0.2161 (3)	0.4906 (2)	0.4629 (2)	0.0426 (6)
H14A	0.2556	0.5506	0.4612	0.064*
H14B	0.1309	0.4922	0.4286	0.064*
O15	0.1553 (3)	0.4549 (2)	0.9108 (3)	0.0534 (8)
H15B	0.2321	0.4841	0.9461	0.080*
H15C	0.0889	0.4979	0.9122	0.080*

	U11	U22	U33	U12	U13	U23
Cu1	0.0256 (2)	0.0291 (2)	0.0397 (3)	0.00437 (17)	0.01238 (18)	0.00152 (17)
Cu2	0.0280 (2)	0.0263 (2)	0.0380 (3)	0.00544 (17)	0.01270 (18)	0.00209 (17)
Cd1	0.02616 (17)	0.03008 (17)	0.03877 (18)	0.00474 (11)	0.01123 (11)	−0.00016 (11)
C1	0.0277 (17)	0.0302 (17)	0.0338 (18)	0.0049 (14)	0.0037 (14)	−0.0031 (14)
C2	0.0284 (18)	0.0325 (18)	0.044 (2)	0.0067 (14)	0.0072 (15)	0.0018 (15)
C3	0.0324 (19)	0.0315 (18)	0.042 (2)	0.0008 (15)	−0.0007 (16)	0.0022 (15)
C4	0.043 (2)	0.0287 (18)	0.041 (2)	0.0074 (16)	−0.0050 (17)	−0.0007 (15)
C5	0.0335 (19)	0.0363 (19)	0.040 (2)	0.0089 (15)	0.0029 (16)	−0.0068 (15)
C6	0.0276 (17)	0.0320 (18)	0.0331 (18)	0.0035 (14)	0.0032 (14)	−0.0040 (14)
C12	0.064 (3)	0.036 (2)	0.059 (3)	0.004 (2)	0.006 (2)	0.0156 (19)
C7	0.0263 (17)	0.039 (2)	0.0357 (19)	0.0067 (14)	0.0072 (14)	−0.0068 (15)
C8	0.0267 (18)	0.044 (2)	0.041 (2)	0.0026 (15)	0.0142 (15)	−0.0037 (16)
C9	0.0232 (17)	0.041 (2)	0.0287 (17)	0.0014 (14)	0.0068 (13)	0.0010 (14)
C10	0.0295 (18)	0.0327 (18)	0.044 (2)	0.0005 (15)	0.0091 (15)	0.0044 (15)
C11	0.0260 (18)	0.0343 (19)	0.0328 (18)	−0.0010 (15)	0.0021 (14)	−0.0006 (14)
C13	0.0312 (18)	0.0292 (17)	0.0288 (17)	0.0023 (14)	0.0021 (14)	0.0033 (13)
C18	0.0325 (19)	0.0351 (19)	0.0301 (18)	−0.0005 (15)	0.0020 (14)	0.0003 (14)
C17	0.042 (2)	0.036 (2)	0.0361 (19)	−0.0030 (16)	0.0065 (16)	0.0047 (15)
C16	0.047 (2)	0.0324 (19)	0.040 (2)	−0.0014 (16)	−0.0001 (17)	0.0103 (15)
C15	0.041 (2)	0.0307 (18)	0.0338 (19)	0.0055 (15)	−0.0017 (16)	−0.0005 (14)
C14	0.0355 (19)	0.0317 (18)	0.0347 (18)	0.0034 (15)	0.0049 (15)	0.0027 (14)
C24	0.047 (2)	0.034 (2)	0.065 (3)	0.0058 (17)	0.017 (2)	−0.0012 (18)
C19	0.0321 (19)	0.038 (2)	0.0352 (19)	−0.0047 (15)	0.0110 (15)	0.0008 (15)
C20	0.0291 (19)	0.040 (2)	0.046 (2)	0.0027 (15)	0.0148 (16)	0.0004 (16)
C21	0.0223 (17)	0.0376 (19)	0.0341 (18)	0.0021 (14)	0.0051 (14)	−0.0071 (14)
C22	0.0350 (19)	0.0316 (18)	0.043 (2)	0.0064 (15)	0.0115 (16)	0.0000 (15)
C23	0.0285 (17)	0.0270 (17)	0.0263 (16)	0.0073 (14)	0.0022 (13)	−0.0016 (13)
N1	0.0251 (15)	0.0350 (16)	0.0362 (16)	0.0046 (12)	0.0101 (12)	−0.0006 (12)
N2	0.0273 (15)	0.0343 (16)	0.0435 (17)	0.0026 (12)	0.0125 (13)	0.0047 (13)
N3	0.0316 (16)	0.0325 (16)	0.0398 (16)	0.0005 (12)	0.0136 (13)	−0.0008 (12)
N4	0.0304 (16)	0.0314 (15)	0.0434 (17)	0.0078 (12)	0.0140 (13)	0.0022 (12)
O1	0.0319 (13)	0.0284 (13)	0.0490 (15)	0.0075 (10)	0.0160 (11)	0.0050 (11)
O2	0.0309 (14)	0.0480 (16)	0.0585 (17)	−0.0004 (12)	0.0160 (13)	0.0110 (13)
O3	0.0306 (13)	0.0312 (13)	0.0480 (15)	0.0059 (10)	0.0198 (11)	0.0047 (11)
O4	0.0326 (14)	0.0335 (14)	0.0608 (18)	0.0093 (11)	0.0144 (12)	0.0000 (12)
O5	0.0508 (17)	0.0351 (14)	0.0559 (17)	0.0065 (12)	0.0130 (14)	0.0120 (12)
O6	0.0366 (14)	0.0241 (12)	0.0479 (15)	0.0053 (10)	0.0172 (11)	0.0054 (10)
O7	0.0290 (14)	0.0411 (15)	0.0608 (17)	0.0061 (11)	0.0156 (12)	−0.0093 (13)
O8	0.0304 (13)	0.0287 (12)	0.0420 (14)	0.0065 (10)	0.0141 (11)	0.0045 (10)
O9	0.0332 (14)	0.0265 (12)	0.0469 (15)	0.0008 (10)	0.0112 (11)	0.0030 (10)
O10	0.0637 (19)	0.0301 (14)	0.0515 (17)	0.0137 (13)	0.0121 (14)	0.0079 (12)
O11	0.0296 (13)	0.0465 (15)	0.0452 (15)	0.0062 (11)	0.0071 (11)	−0.0082 (12)
O12	0.0313 (13)	0.0406 (14)	0.0419 (14)	0.0023 (11)	0.0088 (11)	0.0053 (11)
O13	0.0466 (17)	0.0364 (15)	0.093 (2)	0.0109 (13)	0.0331 (17)	0.0098 (15)
O14	0.0462 (16)	0.0375 (14)	0.0413 (15)	0.0083 (12)	0.0054 (12)	−0.0002 (11)
O15	0.0424 (17)	0.0470 (17)	0.070 (2)	0.0006 (13)	0.0068 (15)	0.0164 (15)

Cu1—O1	1.887 (3)	C11—O4	1.224 (5)
Cu1—N2	1.889 (3)	C11—O3	1.296 (4)
Cu1—N1	1.916 (3)	C13—O6	1.315 (4)
Cu1—O3	1.960 (2)	C13—C14	1.411 (5)
Cu2—O6	1.882 (2)	C13—C18	1.427 (5)
Cu2—N4	1.898 (3)	C18—C17	1.402 (5)
Cu2—N3	1.922 (3)	C18—C19	1.431 (5)
Cu2—O8	1.985 (2)	C17—C16	1.370 (6)
Cd1—O11	2.258 (3)	C17—H17	0.9300
Cd1—O12	2.260 (3)	C16—C15	1.395 (6)
Cd1—O3	2.288 (2)	C16—H16	0.9300
Cd1—O13	2.345 (3)	C15—O10	1.364 (5)
Cd1—O8	2.380 (2)	C15—C14	1.372 (5)
Cd1—O9	2.432 (3)	C14—H18	0.9300
Cd1—O4	2.545 (3)	C24—O10	1.425 (5)
C1—O1	1.320 (4)	C24—H24A	0.9600
C1—C2	1.396 (5)	C24—H24B	0.9600
C1—C6	1.431 (5)	C24—H24C	0.9600
C2—C3	1.387 (5)	C19—N3	1.282 (5)
C2—H2	0.9300	C19—H19	0.9300
C3—O5	1.366 (5)	C20—N3	1.459 (5)
C3—C4	1.391 (6)	C20—C21	1.522 (5)
C4—C5	1.359 (6)	C20—H20A	0.9700
C4—H4	0.9300	C20—H20B	0.9700
C5—C6	1.399 (5)	C21—O7	1.260 (4)
C5—H5	0.9300	C21—N4	1.296 (5)
C6—C7	1.434 (5)	C22—N4	1.440 (5)
C12—O5	1.433 (5)	C22—C23	1.501 (5)
C12—H12A	0.9600	C22—H22A	0.9700
C12—H12B	0.9600	C22—H22B	0.9700
C12—H12C	0.9600	C23—O9	1.230 (4)
C7—N1	1.281 (5)	C23—O8	1.296 (4)
C7—H7	0.9300	O11—H11C	0.8502
C8—N1	1.464 (5)	O11—H11D	0.8500
C8—C9	1.520 (5)	O12—H12D	0.8499
C8—H8A	0.9700	O12—H12E	0.8500
C8—H8B	0.9700	O13—H13A	0.8499
C9—O2	1.249 (5)	O13—H13C	0.8500
C9—N2	1.302 (5)	O14—H14A	0.8500
C10—N2	1.450 (5)	O14—H14B	0.8500
C10—C11	1.515 (5)	O15—H15B	0.8500
C10—H10A	0.9700	O15—H15C	0.8499
C10—H10B	0.9700
O1—Cu1—N2	175.76 (13)	O6—C13—C18	125.0 (3)
O1—Cu1—N1	96.85 (12)	C14—C13—C18	117.3 (3)
N2—Cu1—N1	84.08 (13)	C17—C18—C13	118.9 (3)
O1—Cu1—O3	95.95 (11)	C17—C18—C19	117.1 (3)
N2—Cu1—O3	83.07 (12)	C13—C18—C19	123.9 (3)
N1—Cu1—O3	167.14 (12)	C16—C17—C18	122.9 (4)
O6—Cu2—N4	177.36 (13)	C16—C17—H17	118.6
O6—Cu2—N3	97.34 (12)	C18—C17—H17	118.6
N4—Cu2—N3	83.47 (13)	C17—C16—C15	117.7 (3)
O6—Cu2—O8	96.54 (11)	C17—C16—H16	121.1
N4—Cu2—O8	82.68 (12)	C15—C16—H16	121.1
N3—Cu2—O8	166.11 (12)	O10—C15—C14	123.4 (4)
O11—Cd1—O12	167.94 (10)	O10—C15—C16	114.9 (3)
O11—Cd1—O3	90.74 (10)	C14—C15—C16	121.7 (4)
O12—Cd1—O3	91.08 (9)	C15—C14—C13	121.3 (4)
O11—Cd1—O13	96.65 (11)	C15—C14—H18	119.4
O12—Cd1—O13	95.42 (11)	C13—C14—H18	119.4
O3—Cd1—O13	81.39 (10)	O10—C24—H24A	109.5
O11—Cd1—O8	88.27 (9)	O10—C24—H24B	109.5
O12—Cd1—O8	94.42 (9)	H24A—C24—H24B	109.5
O3—Cd1—O8	158.18 (9)	O10—C24—H24C	109.5
O13—Cd1—O8	77.08 (10)	H24A—C24—H24C	109.5
O11—Cd1—O9	86.73 (9)	H24B—C24—H24C	109.5
O12—Cd1—O9	85.32 (9)	N3—C19—C18	125.7 (3)
O3—Cd1—O9	147.44 (9)	N3—C19—H19	117.2
O13—Cd1—O9	131.15 (10)	C18—C19—H19	117.2
O8—Cd1—O9	54.25 (8)	N3—C20—C21	109.8 (3)
O11—Cd1—O4	91.13 (10)	N3—C20—H20A	109.7
O12—Cd1—O4	80.39 (9)	C21—C20—H20A	109.7
O3—Cd1—O4	53.67 (9)	N3—C20—H20B	109.7
O13—Cd1—O4	134.52 (10)	C21—C20—H20B	109.7
O8—Cd1—O4	148.13 (8)	H20A—C20—H20B	108.2
O9—Cd1—O4	93.90 (8)	O7—C21—N4	127.0 (4)
O1—C1—C2	118.2 (3)	O7—C21—C20	119.4 (3)
O1—C1—C6	124.2 (3)	N4—C21—C20	113.6 (3)
C2—C1—C6	117.6 (3)	N4—C22—C23	108.3 (3)
C3—C2—C1	121.4 (4)	N4—C22—H22A	110.0
C3—C2—H2	119.3	C23—C22—H22A	110.0
C1—C2—H2	119.3	N4—C22—H22B	110.0
O5—C3—C2	114.5 (4)	C23—C22—H22B	110.0
O5—C3—C4	124.5 (3)	H22A—C22—H22B	108.4
C2—C3—C4	121.0 (4)	O9—C23—O8	120.6 (3)
C5—C4—C3	117.9 (4)	O9—C23—C22	121.7 (3)
C5—C4—H4	121.1	O8—C23—C22	117.7 (3)
C3—C4—H4	121.1	C7—N1—C8	122.0 (3)
C4—C5—C6	123.6 (4)	C7—N1—Cu1	124.7 (3)
C4—C5—H5	118.2	C8—N1—Cu1	113.2 (2)
C6—C5—H5	118.2	C9—N2—C10	124.0 (3)
C5—C6—C1	118.3 (3)	C9—N2—Cu1	118.8 (3)
C5—C6—C7	117.1 (3)	C10—N2—Cu1	117.0 (2)
C1—C6—C7	124.3 (3)	C19—N3—C20	122.9 (3)
O5—C12—H12A	109.5	C19—N3—Cu2	123.0 (3)
O5—C12—H12B	109.5	C20—N3—Cu2	113.8 (2)
H12A—C12—H12B	109.5	C21—N4—C22	124.0 (3)
O5—C12—H12C	109.5	C21—N4—Cu2	119.2 (3)
H12A—C12—H12C	109.5	C22—N4—Cu2	116.8 (2)
H12B—C12—H12C	109.5	C1—O1—Cu1	124.3 (2)
N1—C7—C6	124.8 (3)	C11—O3—Cu1	115.3 (2)
N1—C7—H7	117.6	C11—O3—Cd1	97.6 (2)
C6—C7—H7	117.6	Cu1—O3—Cd1	146.97 (13)
N1—C8—C9	110.0 (3)	C11—O4—Cd1	87.5 (2)
N1—C8—H8A	109.7	C3—O5—C12	117.5 (3)
C9—C8—H8A	109.7	C13—O6—Cu2	123.8 (2)
N1—C8—H8B	109.7	C23—O8—Cu2	114.2 (2)
C9—C8—H8B	109.7	C23—O8—Cd1	92.9 (2)
H8A—C8—H8B	108.2	Cu2—O8—Cd1	151.75 (12)
O2—C9—N2	127.3 (4)	C23—O9—Cd1	92.2 (2)
O2—C9—C8	119.4 (3)	C15—O10—C24	117.8 (3)
N2—C9—C8	113.2 (3)	Cd1—O11—H11C	109.4
N2—C10—C11	107.5 (3)	Cd1—O11—H11D	109.4
N2—C10—H10A	110.2	H11C—O11—H11D	109.5
C11—C10—H10A	110.2	Cd1—O12—H12D	109.3
N2—C10—H10B	110.2	Cd1—O12—H12E	109.4
C11—C10—H10B	110.2	H12D—O12—H12E	109.5
H10A—C10—H10B	108.5	Cd1—O13—H13A	109.1
O4—C11—O3	121.0 (3)	Cd1—O13—H13C	109.4
O4—C11—C10	121.9 (3)	H13A—O13—H13C	109.5
O3—C11—C10	117.1 (3)	H14A—O14—H14B	109.5
O6—C13—C14	117.7 (3)	H15B—O15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11D···O14	0.85	1.91	2.715 (4)	158
O13—H13A···O6	0.85	2.14	2.987 (4)	175
O13—H13C···O1	0.85	2.21	2.829 (4)	129
O14—H14B···O9	0.85	2.48	3.045 (4)	125
O11—H11C···O7i	0.85	1.91	2.722 (4)	159
O12—H12D···O2ii	0.85	2.11	2.667 (4)	123
O12—H12E···O15iii	0.85	2.13	2.737 (4)	129
O14—H14A···O7iv	0.85	2.17	2.791 (4)	130
O15—H15B···O4v	0.85	2.55	3.067 (4)	121
O15—H15C···O9iv	0.85	2.36	2.934 (4)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H11D⋯O14	0.85	1.91	2.715 (4)	158
O13—H13A⋯O6	0.85	2.14	2.987 (4)	175
O13—H13C⋯O1	0.85	2.21	2.829 (4)	129
O14—H14B⋯O9	0.85	2.48	3.045 (4)	125
O11—H11C⋯O7i	0.85	1.91	2.722 (4)	159
O12—H12D⋯O2ii	0.85	2.11	2.667 (4)	123
O12—H12E⋯O15iii	0.85	2.13	2.737 (4)	129
O14—H14A⋯O7iv	0.85	2.17	2.791 (4)	130
O15—H15B⋯O4v	0.85	2.55	3.067 (4)	121
O15—H15C⋯O9iv	0.85	2.36	2.934 (4)	126

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