A new Schiff base–copper(II) complex: [N-(2-hydroxy­ethyl)-N′-(2-oxidobenzyl­idene)ethyl­ene­di­amine-1κ⁴O,N,N′,O′][μ-N-(2-oxidobenzyl­idene)-N′-(2-oxidoeth­yl)ethyl­enediamine-1κO:2κ⁴O,N,N′,O′]­dicopper(II) perchlorate methanol solvate

The synthesis and characterization of the title Cu^II complex, [Cu₂(C₁₁H₁₄N₂O₂)(C₁₁H₁₅N₂O₂)]ClO₄·CH₄O, is described. The reaction of salicylaldehyde and N-(2-hydroxy­ethyl)ethyl­enediamine with [Cu(ClO₄)₂]·6H₂O produced the binuclear Cu^II complex in which the adjacent Cu^II atoms are connected by a μ-O bridge. One of the Cu^II atoms is in an elongated square-pyramidal geometry and the other has a distorted square-planar geometry.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in solvent or counterion
• R factor = 0.045
• wR factor = 0.125
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.568     0.762
            Tmin(prime) and Tmax expected:      0.659     0.762
            RR(prime) =      0.862
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.85
PLAT221_ALERT_4_C Large Solvent/Anion  O     Ueq(max)/Ueq(min) ...       3.51 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      23.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H4A    ...          ?

   0 ALERT level A = In general: serious problem
   0 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

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

[N-(2-hydroxyethyl)-N'-(2-oxidobenzylidene)ethylenediamine- 1κ⁴O,N,N',O'][µ-N-(2-oxidobenzylidene)-N'-(2-oxidoethyl)ethylenediamine- 1κO:2κ⁴O,N,N',O']dicopper(II) perchlorate methanol solvate

Crystal data

[Cu2(C11H14N2O2)(C11H15N2O2)]ClO4·CH4O	F(000) = 1384
Mr = 672.06	Dx = 1.621 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1002 reflections
a = 12.479 (3) Å	θ = 3.1–25.8°
b = 15.731 (4) Å	µ = 1.70 mm^−1
c = 14.274 (4) Å	T = 294 K
β = 100.590 (4)°	Block, blue
V = 2754.5 (13) Å^3	0.24 × 0.20 × 0.16 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	5622 independent reflections
Radiation source: fine-focus sealed tube	3994 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.568, Tmax = 0.762	k = −19→19
15671 measured reflections	l = −17→15

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0651P)^2 + 0.0776P] where P = (Fo^2 + 2Fc^2)/3
5622 reflections	(Δ/σ)max = 0.003
410 parameters	Δρmax = 0.79 e Å^−3
48 restraints	Δρmin = −0.43 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	Occ. (<1)
Cu1	1.07496 (4)	0.22159 (3)	0.27019 (3)	0.03698 (15)
Cu2	0.87922 (4)	0.32670 (3)	0.31201 (3)	0.03805 (16)
O1	0.9230 (2)	0.20327 (19)	0.2210 (2)	0.0475 (7)
O2	1.1016 (2)	0.3462 (2)	0.18224 (19)	0.0476 (7)
H2B	1.0367	0.3746	0.1902	0.057*
O3	0.9139 (2)	0.40634 (18)	0.22139 (19)	0.0440 (7)
O4	1.0291 (2)	0.29745 (17)	0.36490 (17)	0.0379 (6)
N1	1.1200 (3)	0.1243 (2)	0.2046 (2)	0.0409 (8)
N2	1.2361 (3)	0.2388 (2)	0.3165 (2)	0.0449 (8)
H2A	1.2524	0.2601	0.3782	0.054*
N3	0.7240 (3)	0.3349 (2)	0.2679 (2)	0.0426 (8)
N4	0.8396 (3)	0.2661 (2)	0.4232 (2)	0.0469 (9)
H4A	0.8318	0.3028	0.4746	0.056*
C1	0.8792 (3)	0.1428 (3)	0.1620 (3)	0.0393 (9)
C2	0.7662 (4)	0.1440 (3)	0.1266 (3)	0.0488 (11)
H2	0.7244	0.1880	0.1444	0.059*
C3	0.7161 (4)	0.0819 (3)	0.0666 (3)	0.0542 (12)
H3	0.6413	0.0846	0.0443	0.065*
C4	0.7756 (4)	0.0151 (3)	0.0387 (3)	0.0602 (13)
H4	0.7413	−0.0269	−0.0019	0.072*
C5	0.8853 (4)	0.0121 (3)	0.0716 (3)	0.0534 (12)
H5	0.9252	−0.0330	0.0537	0.064*
C6	0.9401 (3)	0.0759 (2)	0.1323 (3)	0.0380 (9)
C7	1.0570 (4)	0.0700 (3)	0.1564 (3)	0.0419 (10)
H7	1.0894	0.0223	0.1350	0.050*
C8	1.2395 (4)	0.1138 (3)	0.2160 (3)	0.0535 (12)
H8A	1.2657	0.1399	0.1629	0.064*
H8B	1.2582	0.0539	0.2178	0.064*
C9	1.2911 (4)	0.1563 (3)	0.3085 (3)	0.0569 (12)
H9A	1.2836	0.1201	0.3620	0.068*
H9B	1.3681	0.1654	0.3095	0.068*
C10	1.2789 (4)	0.3079 (3)	0.2608 (3)	0.0573 (12)
H10A	1.3470	0.3295	0.2968	0.069*
H10B	1.2932	0.2850	0.2012	0.069*
C11	1.1982 (4)	0.3787 (3)	0.2407 (3)	0.0525 (11)
H11A	1.1815	0.4006	0.2999	0.063*
H11B	1.2281	0.4247	0.2082	0.063*
C12	0.8454 (4)	0.4375 (3)	0.1476 (3)	0.0416 (10)
C13	0.8884 (4)	0.4912 (3)	0.0848 (3)	0.0521 (11)
H13	0.9624	0.5040	0.0966	0.063*
C14	0.8214 (5)	0.5252 (3)	0.0054 (3)	0.0630 (14)
H14	0.8508	0.5610	−0.0350	0.076*
C15	0.7120 (5)	0.5066 (3)	−0.0144 (3)	0.0685 (15)
H15	0.6683	0.5284	−0.0689	0.082*
C16	0.6671 (4)	0.4558 (3)	0.0466 (3)	0.0596 (13)
H16	0.5927	0.4445	0.0334	0.072*
C17	0.7318 (4)	0.4205 (3)	0.1287 (3)	0.0428 (10)
C18	0.6773 (4)	0.3715 (3)	0.1909 (3)	0.0453 (10)
H18	0.6021	0.3658	0.1738	0.054*
C19	0.6594 (4)	0.2907 (3)	0.3293 (3)	0.0568 (13)
H19A	0.5974	0.2625	0.2909	0.068*
H19B	0.6326	0.3310	0.3711	0.068*
C20	0.7335 (4)	0.2264 (3)	0.3872 (3)	0.0602 (13)
H20A	0.7013	0.2067	0.4401	0.072*
H20B	0.7431	0.1778	0.3477	0.072*
C21	0.9328 (4)	0.2115 (3)	0.4622 (3)	0.0563 (12)
H21A	0.9310	0.1597	0.4250	0.068*
H21B	0.9303	0.1962	0.5276	0.068*
C22	1.0345 (4)	0.2609 (3)	0.4577 (3)	0.0472 (11)
H22A	1.0434	0.3056	0.5052	0.057*
H22B	1.0973	0.2235	0.4718	0.057*
Cl1	0.43492 (10)	0.22710 (9)	0.04127 (9)	0.0650 (4)
O5	0.4856 (4)	0.2075 (3)	0.1354 (3)	0.1128 (16)
O6	0.3248 (7)	0.1999 (9)	0.0176 (8)	0.059 (4)	0.352 (4)
O7	0.4242 (14)	0.3244 (4)	0.0538 (11)	0.135 (7)	0.352 (4)
O8	0.4937 (11)	0.2162 (13)	−0.0304 (7)	0.117 (7)	0.352 (4)
O6A	0.3235 (5)	0.2463 (8)	0.0287 (6)	0.070 (4)	0.524 (14)
O7A	0.4934 (10)	0.2822 (9)	−0.0073 (8)	0.128 (6)	0.524 (14)
O8A	0.4408 (11)	0.1408 (6)	−0.0068 (8)	0.151 (6)	0.524 (14)
O6B	0.359 (2)	0.2963 (15)	0.0433 (13)	0.049 (9)	0.124 (14)
O7B	0.5137 (13)	0.2527 (16)	−0.0146 (11)	0.042 (10)	0.124 (14)
O8B	0.376 (2)	0.1541 (12)	−0.0021 (12)	0.060 (11)	0.124 (14)
O9	0.4584 (7)	0.0032 (6)	0.1707 (7)	0.220 (4)
H9	0.4521	0.0395	0.1260	0.264*
C23	0.5387 (8)	0.0205 (9)	0.2425 (7)	0.196 (7)
H23A	0.5513	0.0807	0.2456	0.295*
H23B	0.6038	−0.0081	0.2328	0.295*
H23C	0.5194	0.0013	0.3010	0.295*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0358 (3)	0.0442 (3)	0.0318 (3)	0.0010 (2)	0.0083 (2)	−0.0024 (2)
Cu2	0.0414 (3)	0.0421 (3)	0.0328 (3)	0.0016 (2)	0.0126 (2)	0.0052 (2)
O1	0.0391 (16)	0.0512 (18)	0.0524 (18)	−0.0001 (14)	0.0088 (14)	−0.0159 (14)
O2	0.0427 (17)	0.0612 (19)	0.0389 (16)	−0.0016 (14)	0.0072 (13)	0.0063 (13)
O3	0.0450 (17)	0.0457 (17)	0.0426 (16)	0.0011 (13)	0.0114 (13)	0.0107 (13)
O4	0.0453 (16)	0.0437 (15)	0.0255 (13)	0.0004 (13)	0.0090 (12)	−0.0002 (11)
N1	0.041 (2)	0.047 (2)	0.0364 (19)	0.0082 (16)	0.0110 (15)	0.0004 (15)
N2	0.042 (2)	0.059 (2)	0.0332 (18)	−0.0006 (17)	0.0058 (15)	0.0023 (16)
N3	0.043 (2)	0.049 (2)	0.0393 (19)	0.0018 (16)	0.0167 (16)	0.0020 (16)
N4	0.053 (2)	0.056 (2)	0.0359 (19)	0.0004 (18)	0.0182 (17)	0.0044 (16)
C1	0.046 (2)	0.041 (2)	0.031 (2)	−0.0058 (19)	0.0104 (18)	−0.0008 (17)
C2	0.045 (3)	0.055 (3)	0.046 (2)	0.000 (2)	0.009 (2)	−0.004 (2)
C3	0.051 (3)	0.067 (3)	0.044 (2)	−0.012 (2)	0.007 (2)	−0.003 (2)
C4	0.072 (4)	0.060 (3)	0.049 (3)	−0.021 (3)	0.011 (3)	−0.013 (2)
C5	0.072 (3)	0.042 (3)	0.048 (3)	−0.003 (2)	0.017 (2)	−0.006 (2)
C6	0.048 (3)	0.036 (2)	0.030 (2)	−0.0019 (18)	0.0106 (18)	0.0016 (16)
C7	0.058 (3)	0.036 (2)	0.034 (2)	0.008 (2)	0.016 (2)	0.0009 (17)
C8	0.044 (3)	0.063 (3)	0.056 (3)	0.008 (2)	0.016 (2)	−0.001 (2)
C9	0.041 (3)	0.077 (3)	0.051 (3)	0.014 (2)	0.006 (2)	0.009 (2)
C10	0.040 (3)	0.078 (3)	0.054 (3)	−0.010 (2)	0.010 (2)	0.006 (2)
C11	0.055 (3)	0.055 (3)	0.048 (3)	−0.012 (2)	0.011 (2)	0.003 (2)
C12	0.053 (3)	0.037 (2)	0.036 (2)	0.0087 (19)	0.012 (2)	0.0017 (17)
C13	0.064 (3)	0.047 (3)	0.049 (3)	0.007 (2)	0.021 (2)	0.012 (2)
C14	0.088 (4)	0.059 (3)	0.047 (3)	0.010 (3)	0.023 (3)	0.017 (2)
C15	0.090 (4)	0.071 (4)	0.042 (3)	0.014 (3)	0.006 (3)	0.017 (2)
C16	0.062 (3)	0.064 (3)	0.050 (3)	0.013 (3)	0.003 (2)	0.002 (2)
C17	0.054 (3)	0.039 (2)	0.035 (2)	0.0092 (19)	0.0100 (19)	−0.0011 (17)
C18	0.044 (3)	0.049 (3)	0.044 (2)	0.004 (2)	0.010 (2)	−0.006 (2)
C19	0.048 (3)	0.073 (3)	0.053 (3)	−0.007 (2)	0.020 (2)	0.006 (2)
C20	0.060 (3)	0.067 (3)	0.057 (3)	−0.013 (3)	0.022 (2)	0.015 (2)
C21	0.064 (3)	0.064 (3)	0.043 (3)	0.006 (2)	0.016 (2)	0.022 (2)
C22	0.058 (3)	0.057 (3)	0.027 (2)	0.004 (2)	0.0108 (19)	0.0024 (18)
Cl1	0.0441 (7)	0.0989 (11)	0.0511 (7)	0.0022 (7)	0.0067 (5)	0.0107 (7)
O5	0.089 (3)	0.169 (5)	0.068 (3)	0.000 (3)	−0.017 (2)	0.019 (3)
O6	0.060 (8)	0.066 (9)	0.051 (6)	−0.020 (7)	0.009 (5)	−0.009 (7)
O7	0.102 (12)	0.055 (8)	0.23 (2)	0.007 (8)	−0.013 (13)	−0.008 (10)
O8	0.109 (13)	0.16 (2)	0.105 (12)	−0.017 (14)	0.070 (10)	−0.025 (12)
O6A	0.048 (5)	0.100 (11)	0.059 (5)	0.013 (5)	0.003 (4)	0.008 (6)
O7A	0.101 (9)	0.146 (14)	0.157 (11)	0.004 (9)	0.072 (8)	0.042 (9)
O8A	0.088 (10)	0.150 (11)	0.205 (13)	0.012 (8)	0.002 (8)	−0.096 (10)
O6B	0.051 (13)	0.049 (13)	0.056 (12)	0.011 (9)	0.033 (9)	0.013 (9)
O7B	0.055 (13)	0.030 (12)	0.053 (12)	0.013 (9)	0.037 (9)	−0.011 (8)
O8B	0.060 (14)	0.059 (14)	0.062 (13)	−0.012 (9)	0.016 (9)	−0.019 (9)
O9	0.191 (9)	0.214 (8)	0.260 (10)	−0.042 (7)	0.053 (7)	0.062 (8)
C23	0.085 (6)	0.320 (18)	0.175 (11)	0.017 (9)	0.000 (7)	0.117 (11)

Geometric parameters (Å, º)

Cu1—O1	1.920 (3)	C10—H10A	0.97
Cu1—N1	1.931 (3)	C10—H10B	0.97
Cu1—O4	1.966 (3)	C11—H11A	0.97
Cu1—N2	2.017 (4)	C11—H11B	0.97
Cu1—O2	2.384 (3)	C12—C13	1.408 (6)
Cu2—O3	1.907 (3)	C12—C17	1.419 (6)
Cu2—N3	1.928 (4)	C13—C14	1.385 (6)
Cu2—O4	1.939 (3)	C13—H13	0.93
Cu2—N4	1.991 (3)	C14—C15	1.374 (7)
O1—C1	1.320 (5)	C14—H14	0.93
O2—C11	1.429 (5)	C15—C16	1.373 (7)
O2—H2B	0.95	C15—H15	0.93
O3—C12	1.322 (5)	C16—C17	1.409 (6)
O4—C22	1.434 (4)	C16—H16	0.93
N1—C7	1.274 (5)	C17—C18	1.438 (6)
N1—C8	1.479 (5)	C18—H18	0.93
N2—C9	1.483 (6)	C19—C20	1.510 (7)
N2—C10	1.502 (6)	C19—H19A	0.97
N2—H2A	0.93	C19—H19B	0.97
N3—C18	1.282 (5)	C20—H20A	0.97
N3—C19	1.471 (5)	C20—H20B	0.97
N4—C20	1.468 (6)	C21—C22	1.500 (6)
N4—C21	1.470 (6)	C21—H21A	0.97
N4—H4A	0.95	C21—H21B	0.97
C1—C2	1.409 (6)	C22—H22A	0.97
C1—C6	1.409 (6)	C22—H22B	0.97
C2—C3	1.372 (6)	Cl1—O8	1.375 (7)
C2—H2	0.93	Cl1—O7A	1.396 (6)
C3—C4	1.386 (7)	Cl1—O6A	1.402 (6)
C3—H3	0.93	Cl1—O5	1.411 (3)
C4—C5	1.364 (7)	Cl1—O6	1.420 (7)
C4—H4	0.93	Cl1—O7B	1.433 (8)
C5—C6	1.416 (6)	Cl1—O8B	1.442 (8)
C5—H5	0.93	Cl1—O6B	1.451 (9)
C6—C7	1.438 (6)	Cl1—O8A	1.529 (6)
C7—H7	0.93	Cl1—O7	1.549 (7)
C8—C9	1.514 (6)	O9—C23	1.323 (8)
C8—H8A	0.97	O9—H9	0.85
C8—H8B	0.97	C23—H23A	0.96
C9—H9A	0.97	C23—H23B	0.96
C9—H9B	0.97	C23—H23C	0.96
C10—C11	1.493 (7)
O1—Cu1—N1	93.42 (13)	N2—C10—H10B	109.6
O1—Cu1—O4	87.13 (11)	H10A—C10—H10B	108.1
N1—Cu1—O4	164.18 (12)	O2—C11—C10	108.2 (4)
O1—Cu1—N2	177.47 (13)	O2—C11—H11A	110.1
N1—Cu1—N2	84.46 (15)	C10—C11—H11A	110.1
O4—Cu1—N2	95.29 (13)	O2—C11—H11B	110.1
O1—Cu1—O2	98.92 (12)	C10—C11—H11B	110.1
N1—Cu1—O2	108.38 (12)	H11A—C11—H11B	108.4
O4—Cu1—O2	87.10 (11)	O3—C12—C13	117.6 (4)
N2—Cu1—O2	80.49 (12)	O3—C12—C17	124.0 (4)
O3—Cu2—N3	94.26 (13)	C13—C12—C17	118.4 (4)
O3—Cu2—O4	95.56 (11)	C14—C13—C12	120.6 (5)
N3—Cu2—O4	169.18 (13)	C14—C13—H13	119.7
O3—Cu2—N4	167.53 (14)	C12—C13—H13	119.7
N3—Cu2—N4	84.87 (14)	C15—C14—C13	120.9 (5)
O4—Cu2—N4	86.50 (13)	C15—C14—H14	119.5
C1—O1—Cu1	127.4 (3)	C13—C14—H14	119.5
C11—O2—Cu1	99.8 (2)	C16—C15—C14	119.9 (5)
C11—O2—H2B	114.1	C16—C15—H15	120.0
Cu1—O2—H2B	96.8	C14—C15—H15	120.0
C12—O3—Cu2	126.1 (3)	C15—C16—C17	121.2 (5)
C22—O4—Cu2	109.5 (2)	C15—C16—H16	119.4
C22—O4—Cu1	114.9 (2)	C17—C16—H16	119.4
Cu2—O4—Cu1	104.96 (12)	C16—C17—C12	119.0 (4)
C7—N1—C8	119.6 (4)	C16—C17—C18	117.5 (4)
C7—N1—Cu1	126.0 (3)	C12—C17—C18	123.5 (4)
C8—N1—Cu1	114.4 (3)	N3—C18—C17	125.3 (4)
C9—N2—C10	112.3 (3)	N3—C18—H18	117.3
C9—N2—Cu1	107.8 (3)	C17—C18—H18	117.3
C10—N2—Cu1	110.7 (3)	N3—C19—C20	107.1 (4)
C9—N2—H2A	111.4	N3—C19—H19A	110.3
C10—N2—H2A	101.7	C20—C19—H19A	110.3
Cu1—N2—H2A	112.9	N3—C19—H19B	110.3
C18—N3—C19	120.7 (4)	C20—C19—H19B	110.3
C18—N3—Cu2	125.5 (3)	H19A—C19—H19B	108.5
C19—N3—Cu2	113.7 (3)	N4—C20—C19	109.2 (4)
C20—N4—C21	118.9 (4)	N4—C20—H20A	109.8
C20—N4—Cu2	105.3 (3)	C19—C20—H20A	109.8
C21—N4—Cu2	106.6 (3)	N4—C20—H20B	109.8
C20—N4—H4A	108.3	C19—C20—H20B	109.8
C21—N4—H4A	104.4	H20A—C20—H20B	108.3
Cu2—N4—H4A	113.5	N4—C21—C22	107.4 (4)
O1—C1—C2	119.3 (4)	N4—C21—H21A	110.2
O1—C1—C6	123.2 (4)	C22—C21—H21A	110.2
C2—C1—C6	117.5 (4)	N4—C21—H21B	110.2
C3—C2—C1	121.8 (4)	C22—C21—H21B	110.2
C3—C2—H2	119.1	H21A—C21—H21B	108.5
C1—C2—H2	119.1	O4—C22—C21	110.5 (3)
C2—C3—C4	120.8 (5)	O4—C22—H22A	109.5
C2—C3—H3	119.6	C21—C22—H22A	109.5
C4—C3—H3	119.6	O4—C22—H22B	109.5
C5—C4—C3	118.9 (4)	C21—C22—H22B	109.5
C5—C4—H4	120.5	H22A—C22—H22B	108.1
C3—C4—H4	120.5	O7A—Cl1—O6A	113.5 (5)
C4—C5—C6	121.8 (4)	O8—Cl1—O5	118.4 (6)
C4—C5—H5	119.1	O7A—Cl1—O5	115.2 (5)
C6—C5—H5	119.1	O6A—Cl1—O5	115.5 (4)
C1—C6—C5	119.1 (4)	O8—Cl1—O6	114.3 (6)
C1—C6—C7	123.7 (4)	O5—Cl1—O6	113.9 (5)
C5—C6—C7	117.1 (4)	O5—Cl1—O7B	111.0 (7)
N1—C7—C6	125.7 (4)	O5—Cl1—O8B	109.8 (7)
N1—C7—H7	117.1	O7B—Cl1—O8B	109.5 (8)
C6—C7—H7	117.1	O5—Cl1—O6B	109.0 (7)
N1—C8—C9	107.8 (3)	O7B—Cl1—O6B	108.7 (7)
N1—C8—H8A	110.1	O8B—Cl1—O6B	108.7 (8)
C9—C8—H8A	110.1	O7A—Cl1—O8A	104.8 (6)
N1—C8—H8B	110.1	O6A—Cl1—O8A	105.2 (5)
C9—C8—H8B	110.1	O5—Cl1—O8A	100.5 (5)
H8A—C8—H8B	108.5	O8—Cl1—O7	106.1 (6)
N2—C9—C8	109.0 (4)	O5—Cl1—O7	98.0 (5)
N2—C9—H9A	109.9	O6—Cl1—O7	103.0 (6)
C8—C9—H9A	109.9	C23—O9—H9	113.3
N2—C9—H9B	109.9	O9—C23—H23A	109.5
C8—C9—H9B	109.9	O9—C23—H23B	109.5
H9A—C9—H9B	108.3	H23A—C23—H23B	109.5
C11—C10—N2	110.4 (4)	O9—C23—H23C	109.5
C11—C10—H10A	109.6	H23A—C23—H23C	109.5
N2—C10—H10A	109.6	H23B—C23—H23C	109.5
C11—C10—H10B	109.6
N1—Cu1—O1—C1	−1.1 (3)	O1—C1—C2—C3	−178.8 (4)
O4—Cu1—O1—C1	−165.2 (3)	C6—C1—C2—C3	1.0 (6)
O2—Cu1—O1—C1	108.1 (3)	C1—C2—C3—C4	0.1 (7)
O1—Cu1—O2—C11	159.5 (2)	C2—C3—C4—C5	−0.2 (7)
N1—Cu1—O2—C11	−103.8 (3)	C3—C4—C5—C6	−0.9 (7)
O4—Cu1—O2—C11	72.9 (3)	O1—C1—C6—C5	177.7 (4)
N2—Cu1—O2—C11	−23.0 (3)	C2—C1—C6—C5	−2.1 (6)
N3—Cu2—O3—C12	−10.4 (3)	O1—C1—C6—C7	−5.3 (6)
O4—Cu2—O3—C12	165.1 (3)	C2—C1—C6—C7	174.9 (4)
N4—Cu2—O3—C12	−95.9 (7)	C4—C5—C6—C1	2.1 (6)
O3—Cu2—O4—C22	159.6 (2)	C4—C5—C6—C7	−175.1 (4)
N3—Cu2—O4—C22	−45.2 (7)	C8—N1—C7—C6	−174.1 (4)
N4—Cu2—O4—C22	−8.0 (3)	Cu1—N1—C7—C6	7.7 (6)
O3—Cu2—O4—Cu1	−76.53 (14)	C1—C6—C7—N1	−2.0 (6)
N3—Cu2—O4—Cu1	78.7 (6)	C5—C6—C7—N1	175.1 (4)
N4—Cu2—O4—Cu1	115.81 (15)	C7—N1—C8—C9	−153.0 (4)
O1—Cu1—O4—C22	101.1 (3)	Cu1—N1—C8—C9	25.4 (4)
N1—Cu1—O4—C22	8.7 (6)	C10—N2—C9—C8	−81.5 (5)
N2—Cu1—O4—C22	−79.6 (3)	Cu1—N2—C9—C8	40.7 (4)
O2—Cu1—O4—C22	−159.8 (3)	N1—C8—C9—N2	−42.9 (5)
O1—Cu1—O4—Cu2	−19.18 (14)	C9—N2—C10—C11	159.3 (4)
N1—Cu1—O4—Cu2	−111.6 (5)	Cu1—N2—C10—C11	38.8 (4)
N2—Cu1—O4—Cu2	160.07 (14)	Cu1—O2—C11—C10	49.1 (3)
O2—Cu1—O4—Cu2	79.91 (12)	N2—C10—C11—O2	−63.1 (5)
O1—Cu1—N1—C7	−5.6 (4)	Cu2—O3—C12—C13	−175.6 (3)
O4—Cu1—N1—C7	85.9 (6)	Cu2—O3—C12—C17	4.9 (6)
N2—Cu1—N1—C7	175.8 (4)	O3—C12—C13—C14	179.2 (4)
O2—Cu1—N1—C7	−106.2 (3)	C17—C12—C13—C14	−1.2 (6)
O1—Cu1—N1—C8	176.1 (3)	C12—C13—C14—C15	−0.7 (7)
O4—Cu1—N1—C8	−92.4 (5)	C13—C14—C15—C16	2.0 (8)
N2—Cu1—N1—C8	−2.5 (3)	C14—C15—C16—C17	−1.3 (8)
O2—Cu1—N1—C8	75.6 (3)	C15—C16—C17—C12	−0.6 (7)
N1—Cu1—N2—C9	−21.5 (3)	C15—C16—C17—C18	177.1 (4)
O4—Cu1—N2—C9	142.6 (3)	O3—C12—C17—C16	−178.6 (4)
O2—Cu1—N2—C9	−131.2 (3)	C13—C12—C17—C16	1.9 (6)
N1—Cu1—N2—C10	101.7 (3)	O3—C12—C17—C18	3.9 (6)
O4—Cu1—N2—C10	−94.2 (3)	C13—C12—C17—C18	−175.7 (4)
O2—Cu1—N2—C10	−8.1 (3)	C19—N3—C18—C17	176.1 (4)
O3—Cu2—N3—C18	11.4 (4)	Cu2—N3—C18—C17	−6.9 (6)
O4—Cu2—N3—C18	−143.9 (5)	C16—C17—C18—N3	179.7 (4)
N4—Cu2—N3—C18	178.9 (4)	C12—C17—C18—N3	−2.7 (7)
O3—Cu2—N3—C19	−171.4 (3)	C18—N3—C19—C20	156.8 (4)
O4—Cu2—N3—C19	33.4 (8)	Cu2—N3—C19—C20	−20.5 (5)
N4—Cu2—N3—C19	−3.9 (3)	C21—N4—C20—C19	−165.9 (4)
O3—Cu2—N4—C20	114.4 (6)	Cu2—N4—C20—C19	−46.5 (4)
N3—Cu2—N4—C20	27.8 (3)	N3—C19—C20—N4	44.2 (5)
O4—Cu2—N4—C20	−145.6 (3)	C20—N4—C21—C22	158.4 (4)
O3—Cu2—N4—C21	−118.4 (6)	Cu2—N4—C21—C22	39.7 (4)
N3—Cu2—N4—C21	155.1 (3)	Cu2—O4—C22—C21	33.0 (4)
O4—Cu2—N4—C21	−18.4 (3)	Cu1—O4—C22—C21	−84.8 (4)
Cu1—O1—C1—C2	−174.2 (3)	N4—C21—C22—O4	−48.9 (5)
Cu1—O1—C1—C6	6.0 (6)