An adduct of (1,10-phenanthroline)­diperchloratobis­(pyridine-4-carbox­aldehyde oxime-κN¹)copper(II) and pyridine-4-carbox­aldehyde oxime

In the structure of [Cu(ClO₄)₂(PA)₂(μ-phen)]·PA [PA = pyridine-4-carbox­aldehyde oxime or 4-pyridine­aldoxime (C₆H₆N₂O) and phen = 1,10-phenanthroline (C₁₂H₈N₂)], the coordination geometry around the Cu^II atom may be described as a distorted octahedron. Four N atoms, two from a phen ligand and two from PA ligands, occupy the equatorial positions, while two O atoms from two perchlorate groups occupy the axial positions. The PA mol­ecules which are not involved in the Cu^II coordination link the complexes through O—H...N and O—H...O hydrogen bonds, forming layers parallel to the ac plane.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.069
• wR factor = 0.122
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....        Cl1

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   N8     -   C30      =       7.62 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         O1
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....        Cl2
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT430_ALERT_2_C Short Inter D...A Contact  O4     ..  O4       =       2.86 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              Cl O4

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

S1. Comment

It is well known that the design of complexes of the copper ion with various organic ligands is an interesting field (Richards & Durrant, 2002; Melnik et al., 2000) because of their diversity in coordination chemistry and model applications in biomolecules. As a strong bidentate ligand and a chromophoric group, 1,10-phenanthroline (phen) is involved in many copper complexes (Liu et al., 2002; Chen et al., 2003; Wang et al., 2002; Devi & Zubieta, 2003; Clarke et al., 2003; Guo et al., 2002). 4-Pyridinealdoxime (PA) can be considered as a linear bridging ligand and few complexes of transition metals with PA have been reported (Allan & Paton, 1993). We report here, the structure of a coordination aggregate, (I), constructed by Cu(ClO₄)₂, phen and PA, in which the PA functions as a terminal ligand.

The asymmetric unit of (I) contains a discrete [Cu(PA)₂(µ-phen)(ClO₄)₂] complex and a PA molecule. A displacement ellipsoid plot of the complex is shown in Fig. 1. The coordination environment of the central Cu^II atom can be described as a distorted octahadron with two N atoms (N1 and N2) from a phen ligand and two N atoms (N3 and N5) from PA ligands occupying the equatorial positions, and two O atoms (O1 and O6) from two perchlorate groups occupying the axial positions. The Cu^II atom is displaced from the equatorial plane by 0.095 (3) Å, in the direction of O1. The average Cu—N distance of 2.005 (11) Å is comparable to that [2.020 (3) Å] found in [Cu(phen)₂py(ClO₄)]⁺ (py = pyridine; Niu et al., 2001). The length of the two axial Cu—O coordination bonds are not equal. The Cu1—O6 bond length [2.960 (5) Å] is considerably longer than Cu1—O1 bond length [2.357 (4) Å]. The shorter Cu—O length is slightly longer than that found between Cu^II and the O atom of a water molecule (2.274 Å; Liu et al., 2002). The longer Cu—O distance suggests a very weak bonding. However, it is still shorter than that found in [Cu(phen)₂py(ClO₄)]⁺ (Niu et al., 2001). The fact that atoms O1 and O6 have smaller displacement parameters compared to those of the other O atoms of perchlorate groups confirms the interactions between Cu^II and perchlorate groups.

The phen ligand is planar and it makes a dihedral angle of 4.0 (2)° with the equatorial plane. The coordinated PA molecules play a role of terminal ligand instead of the expected linear bridging ligand. However, the PA molecules which are not involved in the Cu^II coordination connect the complexes through hydrogen bondings. As can be seen from Fig. 2, the O—H···N and O—H···O hydrogen bonds (Table 2) between the complexes and uncoordinted PA molecules, as well as O—H···O hydrogen bonds between coordinated PA molecules and perchlorate groups, result in the formation of thick layers parallel to the ac plane.

S2. Experimental

To a methanol solution (20 ml) of Cu(ClO₄)₂·6H₂O (0.5 mmol) and phen (0.5 mmol), 4-pyridinealdoxime (1.0 mmol) was added. The mixture was stirred for 2 h in air before being left at room temperature for 30 min. The resulting dark-blue solution was filtered and allowed to evaporate at room temperature. After 2 d, blue crystals of the complex suitable for X-ray analysis were obtained. They were collected by suction filtration and air-dried. All chemicals were purchased commercially and used without further purification.

S3. Refinement

H atoms were placed in geometrical positions and allowed for using a riding model [C—H = 0.93 Å, O—H = 0.82 Å and U_iso(H) = 1.2U_eq(parent C) and 1.5U_eq(parent N)].

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The structure of (I), showing 35% probability displacement ellipsoids and the atomic-numbering scheme. The coordination bonds are shown as open lines and dashed line indicates a longer coordination bond.
	Fig. 2. A view of the molecular packing down the a axis.

(1,10-phenanthroline)diperchloratobis(pyridine-4-carboxaldehyde oxime-κN¹)copper(II)–pyridine-4-carboxaldehyde oxime (1/1)

Crystal data

[Cu(ClO4)2(C6H6N2O)2(C12H8N2)]·C6H6N2O	Z = 2
Mr = 809.03	F(000) = 826
Triclinic, P1	Dx = 1.570 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2981 (7) Å	Cell parameters from 3143 reflections
b = 13.525 (2) Å	θ = 2.3–20.4°
c = 16.5280 (13) Å	µ = 0.87 mm^−1
α = 104.16 (2)°	T = 293 K
β = 90.05 (2)°	Plate, blue
γ = 107.34 (2)°	0.3 × 0.1 × 0.08 mm
V = 1711.3 (4) Å^3

Data collection

Bruker SMART APEX CCD diffractometer	5970 independent reflections
Radiation source: fine-focus sealed tube	3289 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 15X15microns pixels mm^-1	θmax = 25.0°, θmin = 2.3°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 1999)	k = −15→16
Tmin = 0.726, Tmax = 0.933	l = −19→19
7700 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.001P)^2 + 0.5P] where P = (Fo^2 + 2Fc^2)/3
5970 reflections	(Δ/σ)max < 0.001
469 parameters	Δρmax = 0.48 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.09414 (9)	0.26802 (5)	0.16579 (4)	0.0465 (2)
Cl1	0.3914 (2)	0.17811 (11)	0.04745 (9)	0.0556 (4)
Cl2	−0.1104 (2)	0.50287 (13)	0.30679 (10)	0.0591 (4)
O1	0.2588 (5)	0.1597 (3)	0.1023 (2)	0.0719 (12)
O2	0.3431 (6)	0.2234 (3)	−0.0134 (2)	0.0885 (14)
O3	0.5380 (6)	0.2547 (4)	0.0957 (3)	0.1069 (17)
O4	0.4224 (6)	0.0828 (3)	0.0081 (3)	0.1054 (17)
O5	−0.2428 (6)	0.5396 (4)	0.2866 (3)	0.0916 (14)
O6	−0.0907 (7)	0.4202 (4)	0.2409 (3)	0.1094 (18)
O7	0.0371 (7)	0.5866 (4)	0.3219 (5)	0.167 (3)
O8	−0.1382 (8)	0.4670 (5)	0.3779 (3)	0.138 (2)
O9	−0.6744 (5)	−0.1994 (3)	0.2955 (2)	0.0736 (12)
H9B	−0.7545	−0.1869	0.3203	0.110*
O10	0.6307 (6)	0.4008 (4)	0.6276 (2)	0.0974 (15)
H10B	0.7284	0.4009	0.6354	0.146*
O11	0.5907 (9)	0.1546 (4)	0.4727 (3)	0.134 (2)
H11A	0.6094	0.2196	0.4828	0.201*
N1	−0.0218 (6)	0.2489 (3)	0.0534 (2)	0.0450 (11)
N2	0.2399 (5)	0.4030 (3)	0.1425 (2)	0.0395 (10)
N3	−0.0832 (6)	0.1422 (4)	0.1854 (3)	0.0520 (12)
N4	−0.5769 (7)	−0.1088 (4)	0.2756 (3)	0.0619 (14)
N5	0.2095 (6)	0.2973 (3)	0.2811 (3)	0.0502 (12)
N6	0.5813 (7)	0.3645 (4)	0.5427 (3)	0.0684 (15)
N7	1.0796 (8)	−0.1207 (5)	0.3561 (3)	0.0804 (17)
N8	0.7362 (10)	0.1303 (6)	0.4518 (3)	0.110 (2)
C1	−0.1479 (7)	0.1669 (4)	0.0085 (3)	0.0557 (16)
H1A	−0.1993	0.1101	0.0316	0.067*
C2	−0.2049 (8)	0.1635 (5)	−0.0716 (4)	0.0686 (18)
H2A	−0.2933	0.1053	−0.1014	0.082*
C3	−0.1312 (9)	0.2449 (5)	−0.1055 (4)	0.0681 (18)
H3A	−0.1691	0.2433	−0.1589	0.082*
C4	0.0031 (7)	0.3328 (5)	−0.0606 (3)	0.0517 (15)
C5	0.0897 (9)	0.4232 (6)	−0.0894 (4)	0.0679 (18)
H5A	0.0557	0.4272	−0.1418	0.081*
C6	0.2189 (8)	0.5034 (5)	−0.0440 (4)	0.0631 (18)
H6A	0.2724	0.5613	−0.0655	0.076*
C7	0.2752 (8)	0.5011 (5)	0.0365 (4)	0.0516 (15)
C8	0.4124 (8)	0.5794 (5)	0.0871 (4)	0.0628 (17)
H8A	0.4717	0.6392	0.0692	0.075*
C9	0.4589 (8)	0.5679 (4)	0.1623 (4)	0.0648 (17)
H9A	0.5496	0.6196	0.1964	0.078*
C10	0.3700 (8)	0.4789 (4)	0.1872 (3)	0.0561 (16)
H10A	0.4035	0.4717	0.2386	0.067*
C11	0.1921 (7)	0.4140 (4)	0.0674 (3)	0.0381 (13)
C12	0.0546 (7)	0.3301 (4)	0.0190 (3)	0.0421 (13)
C13	−0.0586 (8)	0.0470 (5)	0.1752 (3)	0.0560 (16)
H13A	0.0444	0.0394	0.1575	0.067*
C14	−0.1785 (9)	−0.0401 (4)	0.1896 (3)	0.0581 (16)
H14A	−0.1575	−0.1055	0.1806	0.070*
C15	−0.3278 (8)	−0.0302 (5)	0.2171 (3)	0.0483 (15)
C16	−0.3574 (8)	0.0662 (5)	0.2269 (3)	0.0635 (17)
H16A	−0.4597	0.0750	0.2448	0.076*
C17	−0.2325 (8)	0.1497 (5)	0.2097 (3)	0.0593 (16)
H17A	−0.2537	0.2147	0.2154	0.071*
C18	−0.4503 (8)	−0.1211 (5)	0.2371 (3)	0.0577 (17)
H18A	−0.4353	−0.1885	0.2215	0.069*
C19	0.1289 (7)	0.3255 (4)	0.3488 (3)	0.0516 (15)
H19A	0.0191	0.3278	0.3410	0.062*
C20	0.2002 (8)	0.3516 (4)	0.4297 (3)	0.0532 (15)
H20A	0.1398	0.3715	0.4749	0.064*
C21	0.3612 (8)	0.3475 (4)	0.4425 (3)	0.0443 (14)
C22	0.4432 (8)	0.3179 (4)	0.3727 (4)	0.0617 (16)
H22A	0.5522	0.3137	0.3787	0.074*
C23	0.3638 (8)	0.2945 (4)	0.2941 (3)	0.0586 (16)
H23A	0.4226	0.2756	0.2479	0.070*
C24	0.4397 (8)	0.3784 (4)	0.5283 (3)	0.0578 (16)
H24A	0.3856	0.4083	0.5725	0.069*
C25	1.1135 (10)	−0.0145 (7)	0.3731 (4)	0.084 (2)
H25A	1.2225	0.0257	0.3661	0.101*
C26	1.0002 (12)	0.0399 (5)	0.3999 (4)	0.082 (2)
H26A	1.0320	0.1142	0.4111	0.098*
C27	0.8359 (10)	−0.0193 (5)	0.4099 (3)	0.0652 (18)
C28	0.7996 (9)	−0.1284 (5)	0.3925 (4)	0.0698 (19)
H28A	0.6916	−0.1710	0.3985	0.084*
C29	0.9241 (11)	−0.1747 (6)	0.3662 (4)	0.077 (2)
H29A	0.8962	−0.2489	0.3550	0.092*
C30	0.7029 (11)	0.0268 (6)	0.4362 (4)	0.089 (2)
H30A	0.5953	−0.0165	0.4419	0.106*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0473 (5)	0.0518 (4)	0.0409 (4)	0.0090 (3)	−0.0018 (3)	0.0206 (3)
Cl1	0.0565 (11)	0.0523 (10)	0.0617 (10)	0.0215 (8)	0.0161 (9)	0.0154 (8)
Cl2	0.0558 (11)	0.0681 (11)	0.0616 (10)	0.0278 (9)	0.0058 (8)	0.0207 (8)
O1	0.062 (3)	0.081 (3)	0.089 (3)	0.033 (2)	0.037 (2)	0.038 (2)
O2	0.114 (4)	0.098 (3)	0.074 (3)	0.045 (3)	0.021 (3)	0.045 (3)
O3	0.070 (3)	0.109 (4)	0.111 (4)	−0.008 (3)	−0.006 (3)	0.016 (3)
O4	0.112 (4)	0.061 (3)	0.152 (4)	0.044 (3)	0.056 (4)	0.022 (3)
O5	0.075 (3)	0.113 (4)	0.110 (4)	0.058 (3)	−0.006 (3)	0.034 (3)
O6	0.173 (6)	0.105 (4)	0.074 (3)	0.091 (4)	0.002 (3)	0.008 (3)
O7	0.063 (4)	0.105 (4)	0.322 (9)	0.004 (4)	−0.040 (5)	0.061 (5)
O8	0.174 (6)	0.228 (6)	0.092 (4)	0.136 (5)	0.064 (4)	0.096 (4)
O9	0.067 (3)	0.075 (3)	0.072 (3)	0.000 (2)	0.001 (2)	0.033 (2)
O10	0.106 (4)	0.133 (4)	0.055 (3)	0.060 (3)	−0.029 (3)	0.000 (3)
O11	0.191 (7)	0.129 (5)	0.105 (4)	0.097 (5)	0.011 (4)	0.013 (3)
N1	0.047 (3)	0.048 (3)	0.044 (3)	0.017 (2)	0.004 (2)	0.016 (2)
N2	0.043 (3)	0.041 (3)	0.034 (2)	0.015 (2)	0.001 (2)	0.007 (2)
N3	0.056 (4)	0.053 (3)	0.051 (3)	0.013 (3)	0.002 (3)	0.024 (2)
N4	0.052 (4)	0.067 (4)	0.057 (3)	−0.006 (3)	−0.006 (3)	0.029 (3)
N5	0.052 (3)	0.056 (3)	0.046 (3)	0.019 (3)	0.001 (3)	0.017 (2)
N6	0.081 (4)	0.078 (4)	0.043 (3)	0.034 (3)	−0.017 (3)	−0.002 (3)
N7	0.086 (5)	0.073 (4)	0.082 (4)	0.009 (4)	0.012 (3)	0.037 (3)
N8	0.164 (8)	0.140 (6)	0.057 (4)	0.101 (6)	0.000 (4)	0.015 (4)
C1	0.050 (4)	0.057 (4)	0.054 (4)	0.005 (3)	−0.005 (3)	0.017 (3)
C2	0.056 (4)	0.082 (5)	0.055 (4)	0.005 (4)	−0.014 (3)	0.015 (4)
C3	0.072 (5)	0.093 (5)	0.044 (4)	0.031 (4)	−0.008 (4)	0.020 (4)
C4	0.046 (4)	0.078 (4)	0.040 (3)	0.026 (4)	0.008 (3)	0.024 (3)
C5	0.072 (5)	0.097 (5)	0.057 (4)	0.039 (4)	0.014 (4)	0.044 (4)
C6	0.060 (5)	0.076 (5)	0.079 (5)	0.029 (4)	0.023 (4)	0.055 (4)
C7	0.053 (4)	0.052 (4)	0.064 (4)	0.026 (3)	0.016 (3)	0.029 (3)
C8	0.065 (5)	0.052 (4)	0.085 (5)	0.022 (4)	0.026 (4)	0.036 (4)
C9	0.068 (5)	0.041 (4)	0.076 (5)	0.006 (3)	0.002 (4)	0.012 (3)
C10	0.063 (4)	0.046 (4)	0.052 (4)	0.009 (3)	0.001 (3)	0.009 (3)
C11	0.040 (3)	0.039 (3)	0.043 (3)	0.022 (3)	0.007 (3)	0.013 (3)
C12	0.044 (4)	0.051 (3)	0.041 (3)	0.023 (3)	0.003 (3)	0.018 (3)
C13	0.059 (4)	0.056 (4)	0.057 (4)	0.021 (4)	0.011 (3)	0.019 (3)
C14	0.076 (5)	0.044 (4)	0.056 (4)	0.016 (4)	0.005 (3)	0.019 (3)
C15	0.045 (4)	0.052 (4)	0.041 (3)	0.005 (3)	0.002 (3)	0.013 (3)
C16	0.064 (5)	0.056 (4)	0.070 (4)	0.016 (4)	0.013 (3)	0.018 (3)
C17	0.059 (5)	0.055 (4)	0.072 (4)	0.021 (4)	0.002 (4)	0.026 (3)
C18	0.057 (4)	0.053 (4)	0.055 (4)	0.001 (4)	−0.004 (3)	0.017 (3)
C19	0.047 (4)	0.063 (4)	0.055 (4)	0.023 (3)	−0.003 (3)	0.024 (3)
C20	0.055 (4)	0.065 (4)	0.045 (4)	0.026 (3)	0.004 (3)	0.017 (3)
C21	0.057 (4)	0.041 (3)	0.040 (3)	0.016 (3)	0.005 (3)	0.019 (3)
C22	0.052 (4)	0.083 (4)	0.057 (4)	0.026 (3)	−0.010 (3)	0.023 (3)
C23	0.051 (4)	0.089 (5)	0.044 (4)	0.031 (4)	0.007 (3)	0.021 (3)
C24	0.067 (5)	0.064 (4)	0.042 (4)	0.022 (4)	−0.001 (3)	0.009 (3)
C25	0.089 (7)	0.093 (6)	0.068 (5)	0.008 (5)	0.004 (4)	0.040 (4)
C26	0.104 (7)	0.052 (5)	0.075 (5)	−0.001 (5)	−0.020 (5)	0.021 (4)
C27	0.095 (6)	0.057 (5)	0.044 (4)	0.029 (5)	−0.007 (4)	0.007 (3)
C28	0.080 (5)	0.056 (5)	0.072 (4)	0.016 (4)	0.007 (4)	0.019 (3)
C29	0.092 (6)	0.062 (5)	0.078 (5)	0.020 (5)	0.012 (4)	0.026 (4)
C30	0.143 (8)	0.070 (5)	0.058 (4)	0.050 (5)	−0.003 (4)	0.006 (4)

Geometric parameters (Å, º)

Cu1—N3	1.986 (5)	C5—H5A	0.93
Cu1—N2	1.993 (4)	C6—C7	1.421 (7)
Cu1—N1	2.014 (4)	C6—H6A	0.93
Cu1—N5	2.026 (4)	C7—C11	1.390 (6)
Cu1—O1	2.357 (4)	C7—C8	1.401 (8)
Cu1—O6	2.960 (5)	C8—C9	1.360 (7)
Cl1—O4	1.392 (4)	C8—H8A	0.93
Cl1—O2	1.413 (4)	C9—C10	1.369 (7)
Cl1—O3	1.426 (4)	C9—H9A	0.93
Cl1—O1	1.430 (4)	C10—H10A	0.93
Cl2—O7	1.371 (5)	C11—C12	1.419 (7)
Cl2—O8	1.372 (4)	C13—C14	1.368 (7)
Cl2—O5	1.404 (4)	C13—H13A	0.93
Cl2—O6	1.406 (4)	C14—C15	1.352 (7)
O9—N4	1.367 (5)	C14—H14A	0.93
O9—H9B	0.82	C15—C16	1.368 (7)
O10—N6	1.386 (5)	C15—C18	1.452 (7)
O10—H10B	0.82	C16—C17	1.375 (7)
O11—N8	1.366 (8)	C16—H16A	0.93
O11—H11A	0.82	C17—H17A	0.93
N1—C1	1.333 (6)	C18—H18A	0.93
N1—C12	1.350 (6)	C19—C20	1.381 (6)
N2—C10	1.317 (6)	C19—H19A	0.93
N2—C11	1.358 (5)	C20—C21	1.372 (7)
N3—C17	1.327 (7)	C20—H20A	0.93
N3—C13	1.335 (6)	C21—C22	1.376 (7)
N4—C18	1.262 (7)	C21—C24	1.467 (7)
N5—C23	1.312 (6)	C22—C23	1.376 (7)
N5—C19	1.338 (6)	C22—H22A	0.93
N6—C24	1.275 (7)	C23—H23A	0.93
N7—C29	1.314 (8)	C24—H24A	0.93
N7—C25	1.336 (8)	C25—C26	1.370 (9)
N8—C30	1.301 (8)	C25—H25A	0.93
C1—C2	1.392 (7)	C26—C27	1.393 (9)
C1—H1A	0.93	C26—H26A	0.93
C2—C3	1.342 (7)	C27—C28	1.371 (7)
C2—H2A	0.93	C27—C30	1.440 (9)
C3—C4	1.408 (7)	C28—C29	1.379 (8)
C3—H3A	0.93	C28—H28A	0.93
C4—C12	1.396 (6)	C29—H29A	0.93
C4—C5	1.414 (7)	C30—H30A	0.93
C5—C6	1.340 (8)
N3—Cu1—N2	170.4 (2)	C9—C8—C7	120.0 (5)
N3—Cu1—N1	91.45 (18)	C9—C8—H8A	120.0
N2—Cu1—N1	82.81 (18)	C7—C8—H8A	120.0
N3—Cu1—N5	90.61 (17)	C8—C9—C10	118.9 (6)
N2—Cu1—N5	94.71 (17)	C8—C9—H9A	120.5
N1—Cu1—N5	176.18 (18)	C10—C9—H9A	120.5
N3—Cu1—O1	91.59 (18)	N2—C10—C9	123.7 (5)
N2—Cu1—O1	96.12 (15)	N2—C10—H10A	118.1
N1—Cu1—O1	90.40 (15)	C9—C10—H10A	118.1
N5—Cu1—O1	92.76 (17)	N2—C11—C7	122.7 (5)
N3—Cu1—O6	93.53 (19)	N2—C11—C12	117.0 (5)
N2—Cu1—O6	78.72 (15)	C7—C11—C12	120.2 (5)
N1—Cu1—O6	88.83 (14)	N1—C12—C4	122.4 (5)
N5—Cu1—O6	87.83 (16)	N1—C12—C11	117.0 (4)
O1—Cu1—O6	174.84 (14)	C4—C12—C11	120.6 (5)
O4—Cl1—O2	109.6 (3)	N3—C13—C14	122.8 (6)
O4—Cl1—O3	111.8 (3)	N3—C13—H13A	118.6
O2—Cl1—O3	107.8 (3)	C14—C13—H13A	118.6
O4—Cl1—O1	110.9 (3)	C15—C14—C13	119.5 (6)
O2—Cl1—O1	108.8 (3)	C15—C14—H14A	120.2
O3—Cl1—O1	107.8 (3)	C13—C14—H14A	120.2
O7—Cl2—O8	108.0 (4)	C14—C15—C16	118.9 (6)
O7—Cl2—O5	108.6 (3)	C14—C15—C18	119.2 (6)
O8—Cl2—O5	110.9 (3)	C16—C15—C18	121.9 (6)
O7—Cl2—O6	108.6 (4)	C15—C16—C17	118.4 (6)
O8—Cl2—O6	109.3 (3)	C15—C16—H16A	120.8
O5—Cl2—O6	111.5 (3)	C17—C16—H16A	120.8
Cl1—O1—Cu1	131.0 (2)	N3—C17—C16	123.4 (6)
Cl2—O6—Cu1	150.7 (3)	N3—C17—H17A	118.3
N4—O9—H9B	109.5	C16—C17—H17A	118.3
N6—O10—H10B	109.5	N4—C18—C15	120.1 (6)
N8—O11—H11A	109.5	N4—C18—H18A	120.0
C1—N1—C12	118.7 (5)	C15—C18—H18A	120.0
C1—N1—Cu1	129.8 (4)	N5—C19—C20	123.4 (5)
C12—N1—Cu1	111.3 (3)	N5—C19—H19A	118.3
C10—N2—C11	117.8 (5)	C20—C19—H19A	118.3
C10—N2—Cu1	130.5 (4)	C21—C20—C19	119.1 (5)
C11—N2—Cu1	111.7 (3)	C21—C20—H20A	120.4
C17—N3—C13	116.9 (5)	C19—C20—H20A	120.4
C17—N3—Cu1	121.0 (4)	C20—C21—C22	117.2 (5)
C13—N3—Cu1	122.1 (4)	C20—C21—C24	119.4 (5)
C18—N4—O9	113.6 (5)	C22—C21—C24	123.3 (6)
C23—N5—C19	116.9 (5)	C21—C22—C23	120.0 (6)
C23—N5—Cu1	123.8 (4)	C21—C22—H22A	120.0
C19—N5—Cu1	119.3 (4)	C23—C22—H22A	120.0
C24—N6—O10	110.2 (5)	N5—C23—C22	123.3 (5)
C29—N7—C25	115.6 (7)	N5—C23—H23A	118.3
C30—N8—O11	108.1 (8)	C22—C23—H23A	118.3
N1—C1—C2	122.2 (5)	N6—C24—C21	120.7 (5)
N1—C1—H1A	118.9	N6—C24—H24A	119.7
C2—C1—H1A	118.9	C21—C24—H24A	119.7
C3—C2—C1	119.4 (6)	N7—C25—C26	125.1 (7)
C3—C2—H2A	120.3	N7—C25—H25A	117.5
C1—C2—H2A	120.3	C26—C25—H25A	117.5
C2—C3—C4	120.4 (5)	C25—C26—C27	118.1 (7)
C2—C3—H3A	119.8	C25—C26—H26A	120.9
C4—C3—H3A	119.8	C27—C26—H26A	120.9
C12—C4—C3	117.0 (5)	C28—C27—C26	117.3 (7)
C12—C4—C5	117.4 (5)	C28—C27—C30	118.5 (8)
C3—C4—C5	125.6 (6)	C26—C27—C30	124.2 (7)
C6—C5—C4	122.6 (6)	C27—C28—C29	119.6 (7)
C6—C5—H5A	118.7	C27—C28—H28A	120.2
C4—C5—H5A	118.7	C29—C28—H28A	120.2
C5—C6—C7	120.8 (6)	N7—C29—C28	124.2 (6)
C5—C6—H6A	119.6	N7—C29—H29A	117.9
C7—C6—H6A	119.6	C28—C29—H29A	117.9
C11—C7—C8	116.8 (5)	N8—C30—C27	118.7 (8)
C11—C7—C6	118.4 (6)	N8—C30—H30A	120.7
C8—C7—C6	124.7 (6)	C27—C30—H30A	120.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9B···N7^i	0.82	1.88	2.660 (7)	160
O10—H10B···O7^ii	0.82	2.01	2.823 (7)	169
O11—H11A···N6	0.82	2.05	2.816 (7)	156

Symmetry codes: (i) x−2, y, z; (ii) −x+1, −y+1, −z+1.