Crystal structure of bis-{μ-1-[(E)-(3-meth-oxy-phen-yl)diazen-yl]naphthalen-2-olato-κ(3) N (2),O:O}bis-({1-[(E)-(3-meth-oxy-phen-yl)diazen-yl]naphthalen-2-olato-κ(2) N (2),O}copper(II)).

The title dinuclear Cu(II) complex, [Cu2(C17H13N2O2)4], is located on an inversion centre. The Cu(II) atoms are each five-coordinated in a distorted square-pyramidal geometry by two N atoms and two O atoms from two bidentate ligands and one bridging O atom from another ligand. In the dinuclear complex, the Cu⋯Cu separation is 3.366 (3) Å. In the crystal, complex mol-ecules are linked via weak C-H⋯O hydrogen bonds, forming a layer parallel to (-101).

Related literature

For general background to azo compounds and their use in dyes, pigments and advanced materials, see: Lee et al. (2004 ▸). For background to metal–azo complexes, see: Carella et al. (2007 ▸); Kulikovska et al. (2007 ▸); Patnaik et al. (2007 ▸); Leng et al. (2001 ▸). For related structures of azo compounds, see: Chetioui et al. (2013a ▸,b ▸).

Experimental

Crystal data

[Cu2(C17H13N2O2)4]

M = 1236.26

Monoclinic,

a = 16.260 (5) Å

b = 7.707 (5) Å

c = 22.325 (5) Å

β = 104.268 (5)°

V = 2711 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.86 mm−1

T = 173 K

0.45 × 0.10 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▸) T min = 0.855, T max = 0.966

25289 measured reflections

6516 independent reflections

4941 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.091

S = 1.02

6516 reflections

388 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2006 ▸); cell refinement: SAINT (Bruker, 2006 ▸); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015020824/is5425sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015020824/is5425Isup2.hkl

Click here for additional data file.

x y z . DOI: 10.1107/S2056989015020824/is5425fig1.tif

The mol­ecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms. [Symmetry code: (i) −x + 1, −y, −z + 2.]

Click here for additional data file.

. DOI: 10.1107/S2056989015020824/is5425fig2.tif

Asymmetric unit of the title compound.

Click here for additional data file.

a . DOI: 10.1107/S2056989015020824/is5425fig3.tif

A packing diagram of the title compound viewed along the a axis.

CCDC reference: 1434923

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Cu2(C17H13N2O2)4]	F(000) = 1276
Mr = 1236.26	Dx = 1.514 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2052 reflections
a = 16.260 (5) Å	θ = 3.1–28.6°
b = 7.707 (5) Å	µ = 0.86 mm−1
c = 22.325 (5) Å	T = 173 K
β = 104.268 (5)°	Plate, red
V = 2711 (2) Å3	0.45 × 0.10 × 0.04 mm
Z = 2

Bruker APEXII CCD diffractometer	6516 independent reflections
Radiation source: fine-focus sealed tube	4941 reflections with I > 2σ(I)
Triumph monochromator	Rint = 0.041
φ and ω scans	θmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −21→21
Tmin = 0.855, Tmax = 0.966	k = −4→10
25289 measured reflections	l = −28→29

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0392P)2 + 1.8473P] where P = (Fo2 + 2Fc2)/3
6516 reflections	(Δ/σ)max = 0.001
388 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.33 e Å−3
0 constraints

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cu	0.43895 (2)	0.16467 (3)	0.96464 (2)	0.0168 (1)
O1	0.03530 (9)	0.1354 (2)	0.96483 (8)	0.0327 (5)
O2	0.51647 (8)	0.14161 (18)	1.04496 (7)	0.0179 (4)
O3	0.83178 (9)	0.3080 (2)	0.93754 (8)	0.0298 (5)
O4	0.35788 (9)	0.21050 (19)	0.88861 (7)	0.0197 (4)
N1	0.34448 (10)	0.1210 (2)	1.00735 (8)	0.0168 (5)
N2	0.34504 (10)	0.1706 (2)	1.06202 (8)	0.0184 (5)
N3	0.52791 (10)	0.2345 (2)	0.91924 (8)	0.0164 (5)
N4	0.52351 (11)	0.1912 (2)	0.86321 (8)	0.0177 (5)
C1	0.26175 (13)	0.0628 (3)	0.97394 (10)	0.0180 (6)
C2	0.18925 (13)	0.1284 (3)	0.98921 (10)	0.0198 (6)
C3	0.11017 (13)	0.0752 (3)	0.95503 (11)	0.0255 (7)
C4	0.10379 (15)	−0.0434 (3)	0.90725 (11)	0.0312 (8)
C5	0.17587 (16)	−0.1075 (3)	0.89314 (11)	0.0298 (7)
C6	0.25590 (14)	−0.0540 (3)	0.92616 (10)	0.0224 (7)
C7	0.41663 (13)	0.2373 (3)	1.10110 (10)	0.0181 (6)
C8	0.49944 (13)	0.2220 (3)	1.09202 (10)	0.0169 (6)
C9	0.56755 (14)	0.2969 (3)	1.13794 (10)	0.0219 (6)
C10	0.55333 (14)	0.3848 (3)	1.18703 (11)	0.0246 (7)
C11	0.47097 (14)	0.4023 (3)	1.19736 (10)	0.0227 (6)
C12	0.40167 (14)	0.3241 (3)	1.15493 (10)	0.0216 (6)
C13	0.32039 (15)	0.3378 (3)	1.16662 (11)	0.0301 (7)
C14	0.30890 (17)	0.4270 (4)	1.21729 (12)	0.0378 (9)
C15	0.37733 (18)	0.5083 (4)	1.25783 (12)	0.0382 (9)
C16	0.45651 (17)	0.4960 (3)	1.24817 (11)	0.0326 (8)
C17	0.03923 (16)	0.2459 (4)	1.01626 (13)	0.0375 (9)
C18	0.60985 (13)	0.3057 (3)	0.94875 (10)	0.0169 (6)
C19	0.68012 (13)	0.2692 (3)	0.92585 (10)	0.0191 (6)
C20	0.75860 (13)	0.3374 (3)	0.95597 (10)	0.0209 (6)
C21	0.76648 (14)	0.4400 (3)	1.00807 (11)	0.0223 (6)
C22	0.69622 (13)	0.4775 (3)	1.02969 (10)	0.0218 (6)
C23	0.61679 (13)	0.4110 (3)	1.00022 (10)	0.0185 (6)
C24	0.44976 (13)	0.1318 (2)	0.82480 (10)	0.0168 (6)
C25	0.36914 (12)	0.1495 (3)	0.83733 (10)	0.0174 (6)
C26	0.29605 (14)	0.1012 (3)	0.78953 (10)	0.0235 (7)
C27	0.30412 (14)	0.0283 (3)	0.73592 (10)	0.0245 (7)
C28	0.38469 (14)	0.0045 (3)	0.72267 (10)	0.0215 (6)
C29	0.45840 (13)	0.0612 (3)	0.76664 (10)	0.0187 (6)
C30	0.53741 (14)	0.0439 (3)	0.75208 (11)	0.0269 (7)
C31	0.54277 (16)	−0.0265 (3)	0.69672 (12)	0.0343 (8)
C32	0.47031 (16)	−0.0870 (3)	0.65411 (12)	0.0339 (8)
C33	0.39286 (16)	−0.0727 (3)	0.66692 (11)	0.0294 (7)
C34	0.82769 (15)	0.1918 (3)	0.88753 (12)	0.0325 (8)
H2	0.30450	−0.09610	0.91630	0.0270*
H3	0.17100	−0.18740	0.86120	0.0360*
H4	0.05060	−0.07980	0.88470	0.0370*
H6	0.19410	0.20630	1.02170	0.0240*
H9	0.62290	0.28490	1.13400	0.0260*
H10	0.59910	0.43550	1.21490	0.0300*
H13	0.27410	0.28580	1.13970	0.0360*
H14	0.25510	0.43340	1.22460	0.0450*
H15	0.36870	0.57080	1.29140	0.0460*
H16	0.50180	0.55010	1.27540	0.0390*
H17A	−0.01720	0.27850	1.01780	0.0560*
H17B	0.06640	0.18600	1.05360	0.0560*
H17C	0.07120	0.34810	1.01220	0.0560*
H19	0.67470	0.20030	0.89090	0.0230*
H21	0.81930	0.48350	1.02840	0.0270*
H22	0.70180	0.54800	1.06430	0.0260*
H23	0.56930	0.43680	1.01480	0.0220*
H26	0.24210	0.12030	0.79540	0.0280*
H27	0.25560	−0.00710	0.70690	0.0290*
H30	0.58650	0.08050	0.78030	0.0320*
H31	0.59530	−0.03410	0.68740	0.0410*
H32	0.47500	−0.13690	0.61720	0.0410*
H33	0.34490	−0.11420	0.63870	0.0350*
H34A	0.88270	0.18260	0.87920	0.0490*
H34B	0.80980	0.07960	0.89810	0.0490*
H34C	0.78780	0.23480	0.85150	0.0490*

	U11	U22	U33	U12	U13	U23
Cu	0.0133 (1)	0.0211 (1)	0.0158 (1)	−0.0002 (1)	0.0031 (1)	−0.0003 (1)
O1	0.0145 (7)	0.0488 (11)	0.0344 (10)	−0.0003 (7)	0.0051 (7)	0.0115 (8)
O2	0.0150 (7)	0.0213 (7)	0.0169 (8)	0.0020 (6)	0.0028 (6)	−0.0012 (6)
O3	0.0157 (7)	0.0429 (10)	0.0325 (10)	−0.0056 (7)	0.0090 (7)	−0.0074 (8)
O4	0.0156 (7)	0.0272 (8)	0.0155 (8)	0.0031 (6)	0.0026 (6)	−0.0003 (6)
N1	0.0142 (8)	0.0169 (8)	0.0185 (9)	0.0008 (6)	0.0025 (7)	0.0013 (7)
N2	0.0163 (8)	0.0208 (8)	0.0178 (9)	0.0007 (7)	0.0038 (7)	0.0028 (8)
N3	0.0134 (8)	0.0183 (8)	0.0168 (9)	−0.0015 (7)	0.0026 (7)	−0.0004 (7)
N4	0.0174 (8)	0.0179 (8)	0.0168 (9)	−0.0006 (7)	0.0026 (7)	−0.0006 (7)
C1	0.0170 (10)	0.0188 (10)	0.0172 (11)	−0.0033 (8)	0.0023 (8)	0.0042 (8)
C2	0.0176 (10)	0.0217 (11)	0.0204 (11)	−0.0010 (8)	0.0051 (8)	0.0049 (8)
C3	0.0163 (10)	0.0344 (13)	0.0246 (12)	−0.0020 (9)	0.0030 (9)	0.0127 (10)
C4	0.0235 (12)	0.0421 (14)	0.0236 (13)	−0.0137 (10)	−0.0024 (10)	0.0079 (11)
C5	0.0353 (13)	0.0297 (12)	0.0221 (13)	−0.0104 (10)	0.0028 (10)	−0.0024 (10)
C6	0.0235 (11)	0.0231 (11)	0.0206 (12)	−0.0024 (9)	0.0053 (9)	0.0016 (9)
C7	0.0173 (10)	0.0184 (10)	0.0178 (11)	0.0014 (8)	0.0028 (8)	0.0015 (8)
C8	0.0189 (10)	0.0164 (9)	0.0150 (10)	0.0002 (8)	0.0033 (8)	0.0033 (8)
C9	0.0186 (10)	0.0252 (11)	0.0200 (12)	−0.0002 (8)	0.0014 (8)	0.0003 (9)
C10	0.0244 (11)	0.0270 (11)	0.0192 (12)	−0.0046 (9)	−0.0007 (9)	−0.0018 (9)
C11	0.0301 (12)	0.0215 (10)	0.0166 (11)	0.0021 (9)	0.0057 (9)	0.0018 (9)
C12	0.0248 (11)	0.0221 (10)	0.0178 (11)	0.0050 (9)	0.0053 (8)	0.0044 (9)
C13	0.0279 (12)	0.0411 (13)	0.0218 (12)	0.0042 (11)	0.0073 (9)	0.0011 (11)
C14	0.0353 (14)	0.0505 (16)	0.0321 (15)	0.0114 (12)	0.0169 (12)	0.0013 (13)
C15	0.0564 (17)	0.0413 (15)	0.0209 (13)	0.0058 (13)	0.0173 (12)	−0.0045 (11)
C16	0.0444 (15)	0.0321 (13)	0.0208 (13)	−0.0015 (11)	0.0069 (11)	−0.0040 (10)
C17	0.0221 (12)	0.0458 (15)	0.0481 (17)	0.0037 (11)	0.0155 (11)	0.0111 (14)
C18	0.0152 (9)	0.0163 (10)	0.0183 (11)	−0.0017 (7)	0.0022 (8)	0.0019 (8)
C19	0.0180 (10)	0.0204 (10)	0.0186 (11)	−0.0027 (8)	0.0042 (8)	−0.0009 (8)
C20	0.0154 (9)	0.0231 (10)	0.0247 (12)	−0.0011 (9)	0.0057 (8)	0.0040 (9)
C21	0.0182 (10)	0.0207 (10)	0.0249 (12)	−0.0056 (8)	−0.0004 (9)	0.0017 (9)
C22	0.0256 (11)	0.0165 (10)	0.0219 (12)	−0.0016 (8)	0.0033 (9)	−0.0024 (9)
C23	0.0171 (10)	0.0174 (9)	0.0201 (11)	0.0008 (8)	0.0031 (8)	0.0009 (8)
C24	0.0168 (9)	0.0158 (10)	0.0166 (10)	0.0001 (7)	0.0019 (8)	0.0004 (8)
C25	0.0169 (9)	0.0162 (9)	0.0177 (11)	0.0016 (8)	0.0018 (8)	0.0039 (8)
C26	0.0161 (10)	0.0305 (12)	0.0219 (12)	0.0017 (9)	0.0007 (9)	0.0022 (10)
C27	0.0191 (10)	0.0291 (12)	0.0209 (12)	−0.0008 (9)	−0.0037 (9)	0.0015 (9)
C28	0.0253 (11)	0.0206 (10)	0.0162 (11)	0.0013 (9)	0.0008 (9)	0.0024 (8)
C29	0.0209 (10)	0.0177 (10)	0.0170 (11)	0.0014 (8)	0.0035 (8)	0.0015 (8)
C30	0.0231 (11)	0.0330 (12)	0.0243 (13)	−0.0026 (10)	0.0054 (9)	−0.0060 (10)
C31	0.0297 (13)	0.0430 (15)	0.0323 (14)	0.0017 (11)	0.0119 (11)	−0.0098 (12)
C32	0.0402 (14)	0.0423 (14)	0.0193 (13)	0.0058 (12)	0.0073 (11)	−0.0092 (11)
C33	0.0326 (13)	0.0314 (13)	0.0197 (12)	0.0021 (10)	−0.0022 (10)	−0.0031 (10)
C34	0.0233 (12)	0.0455 (15)	0.0313 (14)	0.0008 (10)	0.0119 (10)	−0.0005 (11)

Cu—O2	1.929 (2)	C22—C23	1.395 (3)
Cu—O4	1.908 (2)	C24—C25	1.413 (3)
Cu—N1	2.026 (2)	C24—C29	1.446 (3)
Cu—N3	2.033 (2)	C25—C26	1.437 (3)
Cu—O2i	2.494 (2)	C26—C27	1.358 (3)
O1—C3	1.370 (3)	C27—C28	1.424 (3)
O1—C17	1.418 (3)	C28—C29	1.418 (3)
O2—C8	1.307 (3)	C28—C33	1.415 (3)
O3—C20	1.370 (3)	C29—C30	1.407 (3)
O3—C34	1.420 (3)	C30—C31	1.372 (4)
O4—C25	1.292 (3)	C31—C32	1.399 (4)
N1—N2	1.277 (3)	C32—C33	1.363 (4)
N1—C1	1.440 (3)	C2—H6	0.9300
N2—C7	1.371 (3)	C4—H4	0.9300
N3—N4	1.280 (3)	C5—H3	0.9300
N3—C18	1.441 (3)	C6—H2	0.9300
N4—C24	1.370 (3)	C9—H9	0.9300
C1—C2	1.400 (3)	C10—H10	0.9300
C1—C6	1.381 (3)	C13—H13	0.9300
C2—C3	1.386 (3)	C14—H14	0.9300
C3—C4	1.389 (3)	C15—H15	0.9300
C4—C5	1.378 (4)	C16—H16	0.9300
C5—C6	1.391 (4)	C17—H17A	0.9600
C7—C8	1.415 (3)	C17—H17B	0.9600
C7—C12	1.447 (3)	C17—H17C	0.9600
C8—C9	1.432 (3)	C19—H19	0.9300
C9—C10	1.356 (3)	C21—H21	0.9300
C10—C11	1.420 (3)	C22—H22	0.9300
C11—C12	1.416 (3)	C23—H23	0.9300
C11—C16	1.412 (3)	C26—H26	0.9300
C12—C13	1.413 (4)	C27—H27	0.9300
C13—C14	1.375 (4)	C30—H30	0.9300
C14—C15	1.398 (4)	C31—H31	0.9300
C15—C16	1.360 (4)	C32—H32	0.9300
C18—C19	1.391 (3)	C33—H33	0.9300
C18—C23	1.388 (3)	C34—H34A	0.9600
C19—C20	1.391 (3)	C34—H34B	0.9600
C20—C21	1.386 (3)	C34—H34C	0.9600
C21—C22	1.376 (3)
O2—Cu—O4	173.62 (6)	O4—C25—C26	118.72 (19)
O2—Cu—N1	86.83 (7)	C24—C25—C26	117.77 (19)
O2—Cu—N3	96.06 (7)	C25—C26—C27	121.3 (2)
O2—Cu—O2i	81.69 (5)	C26—C27—C28	122.0 (2)
O4—Cu—N1	90.67 (7)	C27—C28—C29	118.7 (2)
O4—Cu—N3	85.87 (7)	C27—C28—C33	121.8 (2)
O2i—Cu—O4	104.51 (6)	C29—C28—C33	119.5 (2)
N1—Cu—N3	173.71 (6)	C24—C29—C28	119.0 (2)
O2i—Cu—N1	98.82 (6)	C24—C29—C30	122.6 (2)
O2i—Cu—N3	87.14 (6)	C28—C29—C30	118.4 (2)
C3—O1—C17	117.92 (19)	C29—C30—C31	120.7 (2)
Cu—O2—C8	118.96 (13)	C30—C31—C32	121.0 (2)
Cu—O2—Cui	98.31 (6)	C31—C32—C33	119.8 (2)
Cui—O2—C8	129.90 (13)	C28—C33—C32	120.7 (2)
C20—O3—C34	117.68 (18)	C1—C2—H6	121.00
Cu—O4—C25	120.22 (14)	C3—C2—H6	121.00
Cu—N1—N2	124.93 (13)	C3—C4—H4	120.00
Cu—N1—C1	121.87 (14)	C5—C4—H4	120.00
N2—N1—C1	111.97 (17)	C4—C5—H3	120.00
N1—N2—C7	121.70 (17)	C6—C5—H3	120.00
Cu—N3—N4	122.90 (13)	C1—C6—H2	121.00
Cu—N3—C18	124.34 (14)	C5—C6—H2	121.00
N4—N3—C18	111.64 (17)	C8—C9—H9	119.00
N3—N4—C24	121.91 (18)	C10—C9—H9	119.00
N1—C1—C2	119.78 (19)	C9—C10—H10	119.00
N1—C1—C6	118.75 (19)	C11—C10—H10	119.00
C2—C1—C6	121.5 (2)	C12—C13—H13	120.00
C1—C2—C3	118.8 (2)	C14—C13—H13	120.00
O1—C3—C2	123.5 (2)	C13—C14—H14	120.00
O1—C3—C4	116.4 (2)	C15—C14—H14	120.00
C2—C3—C4	120.1 (2)	C14—C15—H15	120.00
C3—C4—C5	120.3 (2)	C16—C15—H15	120.00
C4—C5—C6	120.7 (2)	C11—C16—H16	119.00
C1—C6—C5	118.7 (2)	C15—C16—H16	120.00
N2—C7—C8	124.5 (2)	O1—C17—H17A	109.00
N2—C7—C12	114.30 (19)	O1—C17—H17B	109.00
C8—C7—C12	121.2 (2)	O1—C17—H17C	109.00
O2—C8—C7	123.5 (2)	H17A—C17—H17B	110.00
O2—C8—C9	119.14 (19)	H17A—C17—H17C	109.00
C7—C8—C9	117.3 (2)	H17B—C17—H17C	109.00
C8—C9—C10	121.6 (2)	C18—C19—H19	120.00
C9—C10—C11	122.3 (2)	C20—C19—H19	120.00
C10—C11—C12	118.5 (2)	C20—C21—H21	120.00
C10—C11—C16	122.0 (2)	C22—C21—H21	120.00
C12—C11—C16	119.5 (2)	C21—C22—H22	120.00
C7—C12—C11	118.9 (2)	C23—C22—H22	120.00
C7—C12—C13	123.0 (2)	C18—C23—H23	121.00
C11—C12—C13	118.1 (2)	C22—C23—H23	121.00
C12—C13—C14	120.8 (2)	C25—C26—H26	119.00
C13—C14—C15	120.6 (3)	C27—C26—H26	119.00
C14—C15—C16	120.0 (3)	C26—C27—H27	119.00
C11—C16—C15	121.0 (2)	C28—C27—H27	119.00
N3—C18—C19	120.37 (19)	C29—C30—H30	120.00
N3—C18—C23	118.57 (19)	C31—C30—H30	120.00
C19—C18—C23	121.1 (2)	C30—C31—H31	120.00
C18—C19—C20	119.0 (2)	C32—C31—H31	120.00
O3—C20—C19	123.6 (2)	C31—C32—H32	120.00
O3—C20—C21	116.0 (2)	C33—C32—H32	120.00
C19—C20—C21	120.4 (2)	C28—C33—H33	120.00
C20—C21—C22	120.1 (2)	C32—C33—H33	120.00
C21—C22—C23	120.7 (2)	O3—C34—H34A	109.00
C18—C23—C22	118.8 (2)	O3—C34—H34B	109.00
N4—C24—C25	123.76 (19)	O3—C34—H34C	109.00
N4—C24—C29	115.09 (19)	H34A—C34—H34B	110.00
C25—C24—C29	120.95 (19)	H34A—C34—H34C	109.00
O4—C25—C24	123.49 (19)	H34B—C34—H34C	110.00
N1—Cu—O2—C8	−45.86 (15)	C2—C3—C4—C5	−0.7 (4)
N1—Cu—O2—Cui	99.40 (6)	C3—C4—C5—C6	−0.4 (4)
N3—Cu—O2—C8	128.53 (15)	C4—C5—C6—C1	0.9 (3)
N3—Cu—O2—Cui	−86.20 (6)	N2—C7—C8—O2	−0.1 (4)
O2i—Cu—O2—C8	−145.26 (15)	N2—C7—C8—C9	−179.0 (2)
O2i—Cu—O2—Cui	0.00 (5)	C12—C7—C8—O2	178.4 (2)
N1—Cu—O4—C25	−137.83 (16)	C12—C7—C8—C9	−0.5 (3)
N3—Cu—O4—C25	47.43 (16)	N2—C7—C12—C11	−178.1 (2)
O2i—Cu—O4—C25	−38.53 (16)	N2—C7—C12—C13	0.5 (3)
O2—Cu—N1—N2	34.04 (15)	C8—C7—C12—C11	3.2 (3)
O2—Cu—N1—C1	−159.66 (15)	C8—C7—C12—C13	−178.1 (2)
O4—Cu—N1—N2	−140.09 (15)	O2—C8—C9—C10	178.6 (2)
O4—Cu—N1—C1	26.21 (15)	C7—C8—C9—C10	−2.4 (3)
O2i—Cu—N1—N2	115.12 (15)	C8—C9—C10—C11	2.6 (4)
O2i—Cu—N1—C1	−78.58 (15)	C9—C10—C11—C12	0.4 (3)
O2—Cu—N3—N4	146.18 (15)	C9—C10—C11—C16	−179.2 (2)
O2—Cu—N3—C18	−20.73 (16)	C10—C11—C12—C7	−3.2 (3)
O4—Cu—N3—N4	−39.93 (15)	C10—C11—C12—C13	178.1 (2)
O4—Cu—N3—C18	153.17 (16)	C16—C11—C12—C7	176.4 (2)
O2i—Cu—N3—N4	64.85 (15)	C16—C11—C12—C13	−2.3 (3)
O2i—Cu—N3—C18	−102.06 (16)	C10—C11—C16—C15	−178.7 (2)
O2—Cu—O2i—Cui	0.00 (6)	C12—C11—C16—C15	1.8 (4)
O2—Cu—O2i—C8i	−139.47 (17)	C7—C12—C13—C14	−177.6 (2)
O4—Cu—O2i—Cui	−178.46 (6)	C11—C12—C13—C14	1.0 (4)
O4—Cu—O2i—C8i	42.07 (17)	C12—C13—C14—C15	1.0 (4)
N1—Cu—O2i—Cui	−85.46 (7)	C13—C14—C15—C16	−1.6 (4)
N1—Cu—O2i—C8i	135.08 (17)	C14—C15—C16—C11	0.2 (4)
N3—Cu—O2i—Cui	96.56 (7)	N3—C18—C19—C20	−178.9 (2)
N3—Cu—O2i—C8i	−42.91 (17)	C23—C18—C19—C20	1.1 (3)
C17—O1—C3—C2	−5.9 (3)	N3—C18—C23—C22	178.8 (2)
C17—O1—C3—C4	175.1 (2)	C19—C18—C23—C22	−1.3 (3)
Cu—O2—C8—C7	38.8 (3)	C18—C19—C20—O3	179.4 (2)
Cu—O2—C8—C9	−142.38 (17)	C18—C19—C20—C21	0.1 (3)
Cui—O2—C8—C7	−93.9 (2)	O3—C20—C21—C22	179.5 (2)
Cui—O2—C8—C9	84.9 (2)	C19—C20—C21—C22	−1.1 (3)
C34—O3—C20—C19	−4.5 (3)	C20—C21—C22—C23	1.0 (3)
C34—O3—C20—C21	174.8 (2)	C21—C22—C23—C18	0.2 (3)
Cu—O4—C25—C24	−35.0 (3)	N4—C24—C25—O4	−6.0 (3)
Cu—O4—C25—C26	146.85 (17)	N4—C24—C25—C26	172.24 (19)
Cu—N1—N2—C7	−10.0 (3)	C29—C24—C25—O4	179.5 (2)
C1—N1—N2—C7	−177.49 (18)	C29—C24—C25—C26	−2.3 (3)
Cu—N1—C1—C2	−141.16 (17)	N4—C24—C29—C28	−176.91 (19)
Cu—N1—C1—C6	37.2 (3)	N4—C24—C29—C30	4.1 (3)
N2—N1—C1—C2	26.8 (3)	C25—C24—C29—C28	−1.9 (3)
N2—N1—C1—C6	−154.92 (19)	C25—C24—C29—C30	179.0 (2)
N1—N2—C7—C8	−15.3 (3)	O4—C25—C26—C27	−176.6 (2)
N1—N2—C7—C12	166.09 (18)	C24—C25—C26—C27	5.1 (3)
Cu—N3—N4—C24	16.2 (2)	C25—C26—C27—C28	−3.5 (4)
C18—N3—N4—C24	−175.38 (17)	C26—C27—C28—C29	−0.9 (3)
Cu—N3—C18—C19	146.59 (17)	C26—C27—C28—C33	179.5 (2)
Cu—N3—C18—C23	−33.5 (3)	C27—C28—C29—C24	3.6 (3)
N4—N3—C18—C19	−21.6 (3)	C27—C28—C29—C30	−177.4 (2)
N4—N3—C18—C23	158.35 (19)	C33—C28—C29—C24	−176.9 (2)
N3—N4—C24—C25	15.1 (3)	C33—C28—C29—C30	2.2 (3)
N3—N4—C24—C29	−170.09 (17)	C27—C28—C33—C32	177.1 (2)
N1—C1—C2—C3	177.8 (2)	C29—C28—C33—C32	−2.5 (3)
C6—C1—C2—C3	−0.5 (3)	C24—C29—C30—C31	178.9 (2)
N1—C1—C6—C5	−178.8 (2)	C28—C29—C30—C31	−0.1 (3)
C2—C1—C6—C5	−0.5 (3)	C29—C30—C31—C32	−1.7 (4)
C1—C2—C3—O1	−177.9 (2)	C30—C31—C32—C33	1.5 (4)
C1—C2—C3—C4	1.1 (3)	C31—C32—C33—C28	0.7 (4)
O1—C3—C4—C5	178.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O4ii	0.93	2.45	3.267 (3)	146
C32—H32···O1iii	0.93	2.51	3.394 (4)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22⋯O4i	0.93	2.45	3.267 (3)	146
C32—H32⋯O1ii	0.93	2.51	3.394 (4)	158

Symmetry codes: (i) ; (ii) .