Aqua­(azido)(μ-azido)bis­{2-[(2-dimethyl­amino­ethyl­imino)meth­yl]-6-methoxy­phenolato}dicopper(II) monohydrate

The asymmetric unit of the title compound, [Cu₂(C₁₂H₁₇N₂O₂)₂(N₃)(μ-N₃)(H₂O)]·H₂O, consists of a dinuclear complex mol­ecule and a solvent water mol­ecule. One Cu atom is six-coordinated by the phenol O atom and by one imine and one amine N atoms from one Schiff base ligand, the phenol and ether O atoms of the second Schiff base, together with a terminal N atom of the bridging azide ligand, in an octa­hedral geometry. The coordination environment of the second Cu atom contains a phenol O and imine and amine N atoms from one Schiff base ligand, two further N atoms, one from the bridging and the other from a terminal azide ligand, and a coordinated water mol­ecule, also in an octa­hedral geometry. The crystal structure involves O—H...N and O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.066
• wR factor = 0.177
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.16 Ratio
PLAT220_ALERT_2_B Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       4.11 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.33 Ratio
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C22
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N4
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N6
PLAT420_ALERT_2_B D-H Without Acceptor       O5W    -   H5WB   ...          ?
PLAT420_ALERT_2_B D-H Without Acceptor       O6W    -   H6WB   ...          ?

Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            deep
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           28.31
           From the CIF: _diffrn_reflns_theta_full          28.31
           From the CIF: _reflns_number_total               6982
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         7364
           Completeness (_total/calc)             94.81%
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.94
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4     -   C22     ..       5.76 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N8     -   N9      ..       5.16 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N9
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5WB   ..  N10     ..       2.69 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.944
            Tmax scaled      0.567 Tmin scaled      0.522
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.21
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu2         (2)       2.24
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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S1. Comment

Polynuclear complexes play an important role in the development of coordination chemistry (Eshel et al., 2000; Jiang et al., 2005; Escuer et al., 2000; El-Behairy et al., 1997; Manhas et al., 2005). Some of the complexes have been found to have pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). A prime strategy for designing these molecular materials is to use suitable bridging ligands (Salem, 2005; Dohlakiya & Patel, 2005; Dey et al., 2004). The azide ligand displays a number of coordination modes and has become one of the most extensively studied building blocks in the field. We recently reported the structure of an azide-bridged polynuclear copper(II) complex (Diao, 2007) and we report herein the crystal structure of the related title complex (I), Fig 1.

The complex is an azide-bridged dinuclear copper(II) complex. One Cu atom is six-coordinated by the phenolic O atom, one imine, and one amine N atoms from one Schiff base ligand, the phenolic and ether O atoms of the second Schiff base, together with a terminal N atom of the bridging azide ligand, in an octahedral geometry. The coordination sphere of the second Cu atom contains a phenolic O, imine and amine N atoms from one Schiff base ligand, two N atoms one from the bridging and the other from a terminal azide ligand, and a coordinated water molecule, also in an octahedral geometry.

Related literature

For background on the chemistry of polynuclear complexes, see: Eshel et al. (2000); Jiang et al. (2005); Escuer et al. (2000); El-Behairy et al. (1997); Manhas et al. (2005). For their biological activity, see: Brückner et al. (2000); Harrop et al. (2003); Ren et al. (2002). For polynuclear complexes involving bridging ligands, see: Salem (2005); Dohlakiya & Patel (2005); Dey et al. (2004). For a related structure, see: Diao (2007).

S2. Experimental

2-Hydroxy-3-methoxybenzaldehyde (0.2 mmol, 30.5 mg), N,N-dimethylethane-1,2-diamine (0.2 mmol, 17.5 mg), NaN₃ (0.2 mmol, 13.0 mg), and Cu(CH₃COO)₂.H₂O (0.2 mmol, 40.0 mg) were dissolved in an 95% ethanol solution (30 ml). The mixture was stirred at room temperature for 30 min to give a deep blue solution. After keeping the solution in air for a few days, deep blue crystals were formed.

S3. Refinement

The crystals were very weakly diffracting and few high angle reflections were obtained. This explains the low measured fraction of data in this determination. Water H atoms were located from a difference Fourier map and refined isotropically. All other H atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, U_iso = 1.2U_eq (C) for aromatic, 0.97 Å, U_iso = 1.2U_eq (C) for CH₂ and 0.96 Å, U_iso = 1.5U_eq (C) for CH₃ atoms.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures

Fig. 1. The structure of the complex with displacement parameters drawn at the 30% probability level. Hydrogen atoms have been omitted for clarity.

Aqua(azido)(µ-azido)bis{2-[(2-dimethylaminoethylimino)methyl]- 6-methoxyphenolato}dicopper(II) monohydrate

Crystal data

[Cu2(C12H17N2O2)2(N3)2(H2O)]·H2O	F(000) = 1432
Mr = 689.72	Dx = 1.548 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2127 reflections
a = 16.232 (3) Å	θ = 2.4–25.3°
b = 13.540 (2) Å	µ = 1.49 mm^−1
c = 13.997 (3) Å	T = 293 K
β = 105.821 (2)°	Block, deep blue
V = 2959.7 (9) Å^3	0.45 × 0.40 × 0.38 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	6982 independent reflections
Radiation source: fine-focus sealed tube	4183 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.083
ω scans	θmax = 28.3°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −20→20
Tmin = 0.553, Tmax = 0.601	k = −17→18
25203 measured reflections	l = −18→18

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.178	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.082P)^2] where P = (Fo^2 + 2Fc^2)/3
6982 reflections	(Δ/σ)max < 0.001
397 parameters	Δρmax = 0.85 e Å^−3
6 restraints	Δρmin = −0.53 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	0.22488 (4)	0.59328 (4)	0.30915 (4)	0.03150 (18)
Cu2	0.28782 (4)	0.41861 (4)	0.46588 (4)	0.03647 (19)
O1	0.3838 (2)	0.7739 (2)	0.5713 (2)	0.0438 (9)
O2	0.2983 (2)	0.6832 (2)	0.4120 (2)	0.0352 (8)
O3	0.1096 (2)	0.6710 (2)	0.3377 (2)	0.0392 (8)
O4	0.19356 (19)	0.5165 (2)	0.4158 (2)	0.0304 (7)
O5W	0.3560 (2)	0.5452 (2)	0.5539 (3)	0.0452 (9)
O6W	0.1580 (5)	0.9882 (5)	0.3801 (7)	0.138 (3)
N1	0.2379 (2)	0.6839 (3)	0.2025 (3)	0.0325 (9)
N2	0.1402 (2)	0.5160 (3)	0.1842 (3)	0.0353 (9)
N3	0.2400 (3)	0.3880 (3)	0.5808 (3)	0.0411 (10)
N4	0.3881 (3)	0.3180 (3)	0.5377 (3)	0.0473 (11)
N5	0.2209 (4)	0.3096 (4)	0.3707 (3)	0.0614 (14)
N6	0.1723 (3)	0.2499 (4)	0.3811 (4)	0.0616 (14)
N7	0.1258 (4)	0.1903 (5)	0.3929 (7)	0.134 (3)
N8	0.3252 (3)	0.4832 (3)	0.3445 (3)	0.0370 (9)
N9	0.3824 (3)	0.4609 (3)	0.3142 (3)	0.0497 (11)
N10	0.4393 (4)	0.4366 (5)	0.2847 (5)	0.094 (2)
C1	0.3224 (3)	0.7735 (3)	0.3996 (3)	0.0292 (10)
C2	0.3684 (3)	0.8273 (3)	0.4848 (4)	0.0358 (11)
C3	0.3930 (3)	0.9227 (4)	0.4769 (4)	0.0477 (13)
H3	0.4214	0.9571	0.5338	0.057*
C4	0.3763 (4)	0.9686 (4)	0.3858 (5)	0.0549 (15)
H4	0.3930	1.0338	0.3816	0.066*
C5	0.3355 (4)	0.9186 (3)	0.3019 (4)	0.0473 (13)
H5	0.3256	0.9496	0.2406	0.057*
C6	0.3079 (3)	0.8201 (3)	0.3068 (4)	0.0345 (11)
C7	0.4359 (4)	0.8197 (5)	0.6593 (4)	0.0646 (18)
H7A	0.4902	0.8373	0.6493	0.097*
H7B	0.4446	0.7744	0.7139	0.097*
H7C	0.4078	0.8780	0.6736	0.097*
C8	0.2659 (3)	0.7731 (3)	0.2133 (3)	0.0351 (11)
H8	0.2585	0.8108	0.1560	0.042*
C9	0.1970 (3)	0.6477 (4)	0.1016 (3)	0.0418 (12)
H9A	0.2359	0.6047	0.0793	0.050*
H9B	0.1819	0.7027	0.0558	0.050*
C10	0.1179 (3)	0.5917 (4)	0.1052 (4)	0.0413 (12)
H10A	0.0760	0.6370	0.1184	0.050*
H10B	0.0929	0.5603	0.0416	0.050*
C11	0.1836 (4)	0.4311 (4)	0.1517 (4)	0.0564 (16)
H11A	0.1454	0.4007	0.0947	0.085*
H11B	0.1999	0.3838	0.2046	0.085*
H11C	0.2338	0.4540	0.1347	0.085*
C12	0.0606 (4)	0.4801 (4)	0.2041 (4)	0.0552 (15)
H12A	0.0330	0.5336	0.2282	0.083*
H12B	0.0740	0.4287	0.2531	0.083*
H12C	0.0229	0.4546	0.1439	0.083*
C13	0.1423 (3)	0.5545 (3)	0.4650 (3)	0.0301 (10)
C14	0.0934 (3)	0.6376 (3)	0.4233 (3)	0.0341 (11)
C15	0.0346 (3)	0.6781 (4)	0.4664 (4)	0.0455 (13)
H15	0.0013	0.7313	0.4363	0.055*
C16	0.0250 (3)	0.6399 (5)	0.5546 (4)	0.0545 (16)
H16	−0.0147	0.6676	0.5837	0.065*
C17	0.0733 (3)	0.5619 (5)	0.5986 (4)	0.0510 (14)
H17	0.0671	0.5379	0.6584	0.061*
C18	0.1334 (3)	0.5161 (4)	0.5550 (4)	0.0404 (12)
C19	0.0756 (4)	0.7652 (4)	0.2999 (5)	0.0628 (17)
H19A	0.0143	0.7616	0.2785	0.094*
H19B	0.0970	0.7830	0.2447	0.094*
H19C	0.0928	0.8140	0.3512	0.094*
C20	0.1824 (3)	0.4335 (4)	0.6068 (4)	0.0444 (13)
H20	0.1701	0.4122	0.6645	0.053*
C21	0.2859 (4)	0.3068 (5)	0.6420 (5)	0.0649 (18)
H21A	0.2825	0.3137	0.7098	0.078*
H21B	0.2604	0.2440	0.6163	0.078*
C22	0.3736 (5)	0.3103 (6)	0.6392 (6)	0.089 (2)
H22A	0.4022	0.2512	0.6711	0.107*
H22B	0.4009	0.3664	0.6783	0.107*
C23	0.4751 (4)	0.3570 (5)	0.5539 (6)	0.087 (2)
H23A	0.5143	0.3174	0.6027	0.130*
H23B	0.4769	0.4239	0.5770	0.130*
H23C	0.4909	0.3551	0.4927	0.130*
C24	0.3826 (6)	0.2214 (5)	0.4905 (7)	0.121 (4)
H24A	0.3864	0.2290	0.4237	0.182*
H24B	0.3289	0.1911	0.4896	0.182*
H24C	0.4287	0.1805	0.5271	0.182*
H5WA	0.339 (5)	0.595 (4)	0.516 (5)	0.146*
H5WB	0.398 (4)	0.564 (5)	0.603 (4)	0.146*
H6WB	0.193 (5)	0.960 (5)	0.351 (7)	0.146*
H6WA	0.163 (6)	1.0516 (10)	0.377 (8)	0.146*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0369 (3)	0.0282 (3)	0.0286 (3)	−0.0004 (2)	0.0074 (2)	0.0004 (2)
Cu2	0.0433 (4)	0.0298 (3)	0.0350 (3)	0.0013 (3)	0.0084 (3)	0.0036 (2)
O1	0.047 (2)	0.045 (2)	0.0332 (19)	−0.0109 (16)	0.0007 (16)	−0.0076 (16)
O2	0.0448 (19)	0.0294 (17)	0.0280 (17)	−0.0084 (14)	0.0039 (15)	0.0026 (14)
O3	0.0408 (19)	0.0353 (18)	0.042 (2)	0.0120 (15)	0.0128 (16)	0.0020 (15)
O4	0.0332 (17)	0.0309 (17)	0.0282 (17)	0.0033 (13)	0.0104 (14)	0.0050 (13)
O5W	0.054 (2)	0.037 (2)	0.038 (2)	−0.0076 (17)	0.0005 (17)	0.0050 (16)
O6W	0.136 (6)	0.104 (5)	0.193 (8)	−0.007 (5)	0.078 (5)	−0.027 (6)
N1	0.035 (2)	0.031 (2)	0.029 (2)	0.0001 (17)	0.0049 (17)	0.0046 (16)
N2	0.044 (2)	0.033 (2)	0.026 (2)	−0.0020 (18)	0.0043 (18)	−0.0004 (17)
N3	0.054 (3)	0.036 (2)	0.033 (2)	−0.004 (2)	0.011 (2)	0.0099 (18)
N4	0.053 (3)	0.038 (2)	0.045 (3)	0.009 (2)	0.005 (2)	0.010 (2)
N5	0.088 (4)	0.041 (3)	0.044 (3)	−0.011 (3)	0.000 (3)	−0.003 (2)
N6	0.046 (3)	0.037 (3)	0.088 (4)	0.005 (2)	−0.004 (3)	0.001 (3)
N7	0.075 (5)	0.067 (5)	0.252 (10)	−0.018 (4)	0.034 (6)	0.017 (6)
N8	0.038 (2)	0.037 (2)	0.040 (2)	0.0066 (18)	0.017 (2)	0.0013 (18)
N9	0.059 (3)	0.040 (3)	0.055 (3)	0.005 (2)	0.023 (3)	0.003 (2)
N10	0.103 (5)	0.099 (5)	0.103 (5)	0.030 (4)	0.067 (4)	0.012 (4)
C1	0.026 (2)	0.025 (2)	0.036 (3)	0.0001 (18)	0.008 (2)	−0.0030 (19)
C2	0.039 (3)	0.032 (3)	0.037 (3)	0.000 (2)	0.011 (2)	−0.001 (2)
C3	0.049 (3)	0.038 (3)	0.053 (3)	−0.013 (2)	0.008 (3)	−0.014 (3)
C4	0.068 (4)	0.031 (3)	0.068 (4)	−0.016 (3)	0.022 (3)	−0.005 (3)
C5	0.064 (4)	0.032 (3)	0.051 (3)	−0.005 (2)	0.024 (3)	0.007 (2)
C6	0.036 (3)	0.026 (2)	0.041 (3)	−0.002 (2)	0.011 (2)	0.002 (2)
C7	0.057 (4)	0.087 (5)	0.041 (3)	−0.030 (3)	−0.003 (3)	−0.006 (3)
C8	0.038 (3)	0.036 (3)	0.034 (3)	0.002 (2)	0.014 (2)	0.006 (2)
C9	0.058 (3)	0.039 (3)	0.028 (3)	−0.006 (2)	0.011 (2)	0.003 (2)
C10	0.044 (3)	0.048 (3)	0.029 (2)	0.000 (2)	0.003 (2)	−0.002 (2)
C11	0.083 (5)	0.040 (3)	0.039 (3)	0.004 (3)	0.005 (3)	−0.008 (2)
C12	0.052 (3)	0.058 (4)	0.050 (3)	−0.024 (3)	0.006 (3)	−0.003 (3)
C13	0.024 (2)	0.036 (3)	0.029 (2)	−0.0091 (19)	0.0049 (19)	−0.009 (2)
C14	0.030 (2)	0.038 (3)	0.033 (3)	−0.005 (2)	0.005 (2)	−0.010 (2)
C15	0.032 (3)	0.050 (3)	0.056 (4)	−0.002 (2)	0.014 (3)	−0.016 (3)
C16	0.043 (3)	0.070 (4)	0.057 (4)	−0.006 (3)	0.024 (3)	−0.025 (3)
C17	0.044 (3)	0.075 (4)	0.038 (3)	−0.015 (3)	0.018 (3)	−0.015 (3)
C18	0.036 (3)	0.050 (3)	0.039 (3)	−0.015 (2)	0.016 (2)	−0.011 (2)
C19	0.073 (4)	0.049 (4)	0.065 (4)	0.027 (3)	0.016 (3)	0.015 (3)
C20	0.047 (3)	0.056 (3)	0.031 (3)	−0.018 (3)	0.012 (2)	0.004 (2)
C21	0.080 (5)	0.062 (4)	0.057 (4)	0.004 (3)	0.025 (4)	0.028 (3)
C22	0.087 (6)	0.089 (6)	0.086 (6)	0.028 (4)	0.013 (4)	0.050 (4)
C23	0.047 (4)	0.071 (5)	0.139 (7)	0.019 (3)	0.018 (4)	0.016 (5)
C24	0.122 (7)	0.062 (5)	0.142 (8)	0.048 (5)	−0.027 (6)	−0.029 (5)

Geometric parameters (Å, º)

Cu1—N1	1.987 (4)	C5—C6	1.414 (6)
Cu1—O4	1.995 (3)	C5—H5	0.9300
Cu1—O2	2.010 (3)	C6—C8	1.448 (6)
Cu1—N8	2.163 (4)	C7—H7A	0.9600
Cu1—N2	2.176 (4)	C7—H7B	0.9600
Cu1—O3	2.275 (3)	C7—H7C	0.9600
Cu2—O4	2.001 (3)	C8—H8	0.9300
Cu2—N3	2.010 (4)	C9—C10	1.503 (7)
Cu2—N5	2.085 (5)	C9—H9A	0.9700
Cu2—N8	2.140 (4)	C9—H9B	0.9700
Cu2—N4	2.150 (4)	C10—H10A	0.9700
Cu2—O5W	2.222 (3)	C10—H10B	0.9700
O1—C2	1.373 (6)	C11—H11A	0.9600
O1—C7	1.431 (6)	C11—H11B	0.9600
O2—C1	1.310 (5)	C11—H11C	0.9600
O3—C14	1.372 (6)	C12—H12A	0.9600
O3—C19	1.432 (6)	C12—H12B	0.9600
O4—C13	1.319 (5)	C12—H12C	0.9600
O5W—H5WA	0.86 (6)	C13—C18	1.407 (6)
O5W—H5WB	0.86 (6)	C13—C14	1.409 (7)
O6W—H6WB	0.87 (8)	C14—C15	1.373 (6)
O6W—H6WA	0.866 (10)	C15—C16	1.387 (7)
N1—C8	1.285 (6)	C15—H15	0.9300
N1—C9	1.472 (6)	C16—C17	1.358 (8)
N2—C12	1.476 (6)	C16—H16	0.9300
N2—C10	1.478 (6)	C17—C18	1.425 (7)
N2—C11	1.483 (6)	C17—H17	0.9300
N3—C20	1.253 (7)	C18—C20	1.448 (7)
N3—C21	1.467 (7)	C19—H19A	0.9600
N4—C24	1.456 (8)	C19—H19B	0.9600
N4—C23	1.466 (7)	C19—H19C	0.9600
N4—C22	1.506 (8)	C20—H20	0.9300
N5—N6	1.166 (7)	C21—C22	1.437 (9)
N6—N7	1.146 (7)	C21—H21A	0.9700
N8—N9	1.161 (6)	C21—H21B	0.9700
N9—N10	1.157 (7)	C22—H22A	0.9700
C1—C6	1.405 (6)	C22—H22B	0.9700
C1—C2	1.422 (6)	C23—H23A	0.9600
C2—C3	1.366 (6)	C23—H23B	0.9600
C3—C4	1.377 (8)	C23—H23C	0.9600
C3—H3	0.9300	C24—H24A	0.9600
C4—C5	1.360 (7)	C24—H24B	0.9600
C4—H4	0.9300	C24—H24C	0.9600
N1—Cu1—O4	169.90 (14)	O1—C7—H7A	109.5
N1—Cu1—O2	90.00 (14)	O1—C7—H7B	109.5
O4—Cu1—O2	90.10 (12)	H7A—C7—H7B	109.5
N1—Cu1—N8	111.68 (15)	O1—C7—H7C	109.5
O4—Cu1—N8	78.43 (14)	H7A—C7—H7C	109.5
O2—Cu1—N8	89.51 (14)	H7B—C7—H7C	109.5
N1—Cu1—N2	82.33 (15)	N1—C8—C6	125.7 (4)
O4—Cu1—N2	96.73 (13)	N1—C8—H8	117.1
O2—Cu1—N2	171.31 (13)	C6—C8—H8	117.1
N8—Cu1—N2	97.11 (15)	N1—C9—C10	107.5 (4)
N1—Cu1—O3	96.18 (14)	N1—C9—H9A	110.2
O4—Cu1—O3	73.73 (12)	C10—C9—H9A	110.2
O2—Cu1—O3	87.11 (13)	N1—C9—H9B	110.2
N8—Cu1—O3	151.94 (14)	C10—C9—H9B	110.2
N2—Cu1—O3	89.64 (14)	H9A—C9—H9B	108.5
O4—Cu2—N3	89.51 (15)	N2—C10—C9	109.8 (4)
O4—Cu2—N5	91.72 (17)	N2—C10—H10A	109.7
N3—Cu2—N5	96.77 (19)	C9—C10—H10A	109.7
O4—Cu2—N8	78.84 (13)	N2—C10—H10B	109.7
N3—Cu2—N8	166.90 (16)	C9—C10—H10B	109.7
N5—Cu2—N8	89.60 (18)	H10A—C10—H10B	108.2
O4—Cu2—N4	172.95 (15)	N2—C11—H11A	109.5
N3—Cu2—N4	84.47 (17)	N2—C11—H11B	109.5
N5—Cu2—N4	92.64 (19)	H11A—C11—H11B	109.5
N8—Cu2—N4	106.72 (16)	N2—C11—H11C	109.5
O4—Cu2—O5W	84.30 (13)	H11A—C11—H11C	109.5
N3—Cu2—O5W	87.57 (15)	H11B—C11—H11C	109.5
N5—Cu2—O5W	174.10 (16)	N2—C12—H12A	109.5
N8—Cu2—O5W	85.36 (14)	N2—C12—H12B	109.5
N4—Cu2—O5W	91.76 (15)	H12A—C12—H12B	109.5
C2—O1—C7	117.0 (4)	N2—C12—H12C	109.5
C1—O2—Cu1	127.7 (3)	H12A—C12—H12C	109.5
C14—O3—C19	118.0 (4)	H12B—C12—H12C	109.5
C14—O3—Cu1	111.4 (3)	O4—C13—C18	123.9 (4)
C19—O3—Cu1	126.8 (3)	O4—C13—C14	117.4 (4)
C13—O4—Cu1	120.9 (3)	C18—C13—C14	118.8 (4)
C13—O4—Cu2	127.3 (3)	O3—C14—C15	125.0 (5)
Cu1—O4—Cu2	106.29 (14)	O3—C14—C13	113.8 (4)
Cu2—O5W—H5WA	104 (5)	C15—C14—C13	121.2 (5)
Cu2—O5W—H5WB	146 (5)	C14—C15—C16	120.1 (5)
H5WA—O5W—H5WB	109 (8)	C14—C15—H15	119.9
H6WB—O6W—H6WA	109 (8)	C16—C15—H15	119.9
C8—N1—C9	118.6 (4)	C17—C16—C15	120.2 (5)
C8—N1—Cu1	126.8 (3)	C17—C16—H16	119.9
C9—N1—Cu1	113.8 (3)	C15—C16—H16	119.9
C12—N2—C10	108.8 (4)	C16—C17—C18	121.5 (5)
C12—N2—C11	108.5 (4)	C16—C17—H17	119.3
C10—N2—C11	110.4 (4)	C18—C17—H17	119.3
C12—N2—Cu1	113.6 (3)	C13—C18—C17	118.2 (5)
C10—N2—Cu1	103.8 (3)	C13—C18—C20	123.8 (5)
C11—N2—Cu1	111.7 (3)	C17—C18—C20	118.0 (5)
C20—N3—C21	119.9 (5)	O3—C19—H19A	109.5
C20—N3—Cu2	127.8 (4)	O3—C19—H19B	109.5
C21—N3—Cu2	112.1 (4)	H19A—C19—H19B	109.5
C24—N4—C23	109.3 (6)	O3—C19—H19C	109.5
C24—N4—C22	111.1 (6)	H19A—C19—H19C	109.5
C23—N4—C22	105.6 (5)	H19B—C19—H19C	109.5
C24—N4—Cu2	114.3 (4)	N3—C20—C18	125.9 (5)
C23—N4—Cu2	114.7 (4)	N3—C20—H20	117.1
C22—N4—Cu2	101.1 (3)	C18—C20—H20	117.1
N6—N5—Cu2	131.6 (5)	C22—C21—N3	108.0 (5)
N7—N6—N5	178.5 (7)	C22—C21—H21A	110.1
N9—N8—Cu2	127.7 (4)	N3—C21—H21A	110.1
N9—N8—Cu1	136.3 (4)	C22—C21—H21B	110.1
Cu2—N8—Cu1	96.01 (16)	N3—C21—H21B	110.1
N10—N9—N8	178.5 (6)	H21A—C21—H21B	108.4
O2—C1—C6	124.1 (4)	C21—C22—N4	116.0 (6)
O2—C1—C2	118.3 (4)	C21—C22—H22A	108.3
C6—C1—C2	117.6 (4)	N4—C22—H22A	108.3
C3—C2—O1	125.6 (4)	C21—C22—H22B	108.3
C3—C2—C1	121.0 (5)	N4—C22—H22B	108.3
O1—C2—C1	113.4 (4)	H22A—C22—H22B	107.4
C2—C3—C4	120.9 (5)	N4—C23—H23A	109.5
C2—C3—H3	119.5	N4—C23—H23B	109.5
C4—C3—H3	119.5	H23A—C23—H23B	109.5
C5—C4—C3	120.0 (5)	N4—C23—H23C	109.5
C5—C4—H4	120.0	H23A—C23—H23C	109.5
C3—C4—H4	120.0	H23B—C23—H23C	109.5
C4—C5—C6	120.9 (5)	N4—C24—H24A	109.5
C4—C5—H5	119.5	N4—C24—H24B	109.5
C6—C5—H5	119.5	H24A—C24—H24B	109.5
C1—C6—C5	119.5 (4)	N4—C24—H24C	109.5
C1—C6—C8	123.9 (4)	H24A—C24—H24C	109.5
C5—C6—C8	116.6 (4)	H24B—C24—H24C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5W—H5WB···N10^i	0.86 (6)	2.69 (4)	3.481 (8)	155 (8)
O5W—H5WA···O1	0.86 (6)	2.59 (6)	3.129 (5)	122 (6)
O5W—H5WA···O2	0.86 (6)	1.86 (6)	2.702 (4)	167 (8)

Symmetry code: (i) −x+1, −y+1, −z+1.