μ-(2,6-Bis{[3-(di-methyl-amino)-prop-yl]imino-meth-yl}-4-methyl-phenolato)-μ-hydroxido-bis-[(thio-cyanato-κN)copper(II)].

In the title compound, [Cu2(C19H31N4O)(OH)(NCS)2], the mol-ecular structure of the dinuclear complex reveals two penta-coordinated Cu(II) ions, which are bridged by the phenolate O atom of the ligand and by an exogenous hydroxide ion. The bridging atoms occupy equatorial positions in the coordination sphere of the metal atoms and complete the equatorial coordination planes with two ligand N atoms, the apical positions being occupied by thio-cyanate N atoms. The crystal structure also features π-π stacking inter-actions involving the benzene rings with a centroid-centroid distance of 3.764 (4)Å. The crystal studied was a non-merohedral twin, with a refined BASF value of 0.203 (2).

Related literature

For related structures, see: Matsufuji et al. (2005 ▶); Amase et al. (2005 ▶); Erxleben & Hermann (2000 ▶); Higuchi et al. (1995 ▶); Koga et al. (1998 ▶); Knight et al. (2008 ▶). For applications and properties of binuclear copper (II) complexes, see: Adams et al. (2000 ▶); Al-Obaidi (2011 ▶); Anupama et al. (2012 ▶); Aytaç (2010 ▶); Hurley (2002 ▶); Saha & Koner (2004 ▶); Sreedaran et al. (2008 ▶).

Experimental

Crystal data

[Cu2(C19H31N4O)(OH)(NCS)2]

M = 591.73

Monoclinic,

a = 11.9706 (5) Å

b = 13.7518 (7) Å

c = 16.9887 (8) Å

β = 109.396 (2)°

V = 2637.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.80 mm−1

T = 298 K

0.35 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.572, T max = 0.715

15757 measured reflections

15757 independent reflections

12691 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 1.01

15757 reflections

303 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.53 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813024768/bx2448sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024768/bx2448Isup2.hkl

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

[Cu2(C19H31N4O)(OH)(NCS)2]	F(000) = 1224
Mr = 591.73	Dx = 1.490 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6965 reflections
a = 11.9706 (5) Å	θ = 2.5–28.5°
b = 13.7518 (7) Å	µ = 1.80 mm−1
c = 16.9887 (8) Å	T = 298 K
β = 109.396 (2)°	Rectangular, green
V = 2637.9 (2) Å3	0.35 × 0.25 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	15757 independent reflections
Radiation source: fine-focus sealed tube	12691 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
phi and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (TWINABS; Bruker, 2004)	h = −14→13
Tmin = 0.572, Tmax = 0.715	k = −16→16
15757 measured reflections	l = −19→20

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0461P)2 + 2.7323P] where P = (Fo2 + 2Fc2)/3
15757 reflections	(Δ/σ)max = 0.001
303 parameters	Δρmax = 0.73 e Å−3
2 restraints	Δρmin = −0.53 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
C1	0.14435 (16)	0.08416 (13)	0.14686 (11)	0.0324 (4)
C2	0.02153 (16)	0.09626 (14)	0.13278 (12)	0.0348 (5)
C3	−0.05365 (17)	0.12155 (15)	0.05291 (12)	0.0420 (5)
H3	−0.1340	0.1291	0.0446	0.050*
C4	−0.01470 (18)	0.13587 (14)	−0.01390 (13)	0.0455 (5)
C5	0.10368 (18)	0.12202 (15)	−0.00002 (13)	0.0434 (5)
H5	0.1318	0.1300	−0.0445	0.052*
C6	0.18437 (16)	0.09648 (14)	0.07788 (12)	0.0351 (5)
C7	0.17786 (18)	0.19821 (16)	0.46594 (14)	0.0439 (5)
C8	0.60543 (19)	0.19201 (15)	0.32423 (13)	0.0425 (5)
C9	0.30672 (19)	0.08411 (16)	0.08337 (14)	0.0445 (5)
H9	0.3224	0.0936	0.0338	0.053*
C10	−0.0999 (2)	0.16307 (17)	−0.09907 (13)	0.0642 (7)
H10A	−0.1784	0.1425	−0.1035	0.096*
H10B	−0.0762	0.1317	−0.1415	0.096*
H10C	−0.0990	0.2323	−0.1062	0.096*
C11	−0.03213 (17)	0.08429 (16)	0.19646 (14)	0.0430 (5)
H11	−0.1136	0.0941	0.1793	0.052*
C12	−0.06173 (19)	0.0563 (2)	0.32495 (15)	0.0586 (7)
H12A	−0.1417	0.0738	0.2910	0.070*
H12B	−0.0352	0.1028	0.3703	0.070*
C13	−0.0625 (2)	−0.0435 (2)	0.36024 (16)	0.0645 (7)
H13A	−0.0833	−0.0900	0.3147	0.077*
H13B	−0.1236	−0.0461	0.3860	0.077*
C14	0.0528 (2)	−0.0738 (2)	0.42343 (14)	0.0645 (7)
H14A	0.0759	−0.0250	0.4671	0.077*
H14B	0.0403	−0.1342	0.4488	0.077*
C15	0.1269 (3)	−0.16821 (18)	0.33008 (16)	0.0740 (8)
H15A	0.1060	−0.2252	0.3546	0.111*
H15B	0.1956	−0.1816	0.3146	0.111*
H15C	0.0622	−0.1502	0.2813	0.111*
C16	0.51179 (18)	0.05934 (19)	0.13281 (16)	0.0579 (7)
H16A	0.5629	0.1092	0.1667	0.070*
H16B	0.4998	0.0741	0.0747	0.070*
C17	0.5721 (2)	−0.0382 (2)	0.15419 (18)	0.0704 (8)
H17A	0.5198	−0.0876	0.1207	0.084*
H17B	0.6430	−0.0374	0.1385	0.084*
C18	0.60619 (18)	−0.0670 (2)	0.24424 (17)	0.0659 (8)
H18A	0.6542	−0.1254	0.2525	0.079*
H18B	0.6553	−0.0160	0.2778	0.079*
C19	0.5583 (2)	−0.1110 (2)	0.36522 (16)	0.0779 (8)
H19A	0.6109	−0.1653	0.3714	0.117*
H19B	0.4962	−0.1278	0.3869	0.117*
H19C	0.6016	−0.0563	0.3955	0.117*
C20	0.4338 (2)	−0.16796 (18)	0.23131 (18)	0.0767 (8)
H20A	0.4841	−0.2227	0.2327	0.115*
H20B	0.3930	−0.1498	0.1744	0.115*
H20C	0.3771	−0.1850	0.2578	0.115*
C21	0.2588 (2)	−0.1131 (2)	0.46299 (15)	0.0758 (8)
H21A	0.2788	−0.0594	0.5012	0.114*
H21B	0.3241	−0.1269	0.4438	0.114*
H21C	0.2420	−0.1693	0.4907	0.114*
Cu1	0.393606 (19)	0.039255 (19)	0.259878 (16)	0.03997 (8)
Cu2	0.18605 (2)	0.039242 (19)	0.329566 (15)	0.03923 (8)
N1	0.01670 (14)	0.06201 (12)	0.27351 (11)	0.0400 (4)
N2	0.39640 (14)	0.06200 (12)	0.14674 (11)	0.0410 (4)
N3	0.50620 (14)	−0.08561 (13)	0.27594 (12)	0.0481 (5)
N4	0.15297 (16)	−0.08803 (13)	0.39072 (11)	0.0458 (4)
N5	0.20263 (17)	0.14220 (15)	0.42418 (12)	0.0598 (5)
N6	0.52528 (17)	0.14212 (14)	0.31649 (12)	0.0591 (5)
O1	0.21794 (10)	0.06199 (10)	0.22147 (7)	0.0381 (3)
O11	0.35320 (12)	0.01574 (12)	0.35888 (9)	0.0573 (4)
H11O	0.3851	0.0662	0.3891	0.086*
S3	0.71742 (6)	0.26265 (5)	0.33508 (5)	0.0685 (2)
S4	0.14334 (6)	0.27589 (5)	0.52589 (5)	0.0684 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0350 (10)	0.0254 (10)	0.0345 (11)	−0.0008 (9)	0.0086 (9)	−0.0019 (8)
C2	0.0327 (10)	0.0315 (12)	0.0382 (12)	0.0025 (9)	0.0091 (9)	−0.0039 (9)
C3	0.0379 (11)	0.0365 (13)	0.0444 (13)	0.0055 (9)	0.0038 (10)	−0.0006 (10)
C4	0.0490 (13)	0.0328 (12)	0.0434 (13)	0.0036 (10)	0.0002 (10)	0.0027 (10)
C5	0.0584 (13)	0.0356 (12)	0.0363 (12)	−0.0050 (10)	0.0159 (11)	0.0030 (10)
C6	0.0384 (11)	0.0321 (12)	0.0341 (12)	−0.0051 (9)	0.0111 (9)	−0.0007 (9)
C7	0.0433 (12)	0.0416 (14)	0.0453 (14)	−0.0067 (10)	0.0128 (10)	0.0003 (10)
C8	0.0478 (12)	0.0384 (13)	0.0411 (13)	0.0020 (10)	0.0146 (10)	0.0015 (10)
C9	0.0562 (14)	0.0405 (14)	0.0452 (14)	−0.0060 (11)	0.0280 (12)	0.0002 (11)
C10	0.0714 (16)	0.0580 (15)	0.0468 (15)	0.0076 (13)	−0.0022 (12)	0.0128 (12)
C11	0.0291 (10)	0.0436 (14)	0.0554 (15)	0.0029 (9)	0.0128 (10)	−0.0073 (11)
C12	0.0412 (12)	0.085 (2)	0.0581 (16)	−0.0022 (12)	0.0274 (12)	−0.0124 (14)
C13	0.0553 (14)	0.095 (2)	0.0505 (15)	−0.0254 (14)	0.0273 (13)	−0.0086 (15)
C14	0.0776 (17)	0.0796 (19)	0.0455 (14)	−0.0293 (15)	0.0327 (13)	−0.0004 (13)
C15	0.114 (2)	0.0416 (15)	0.0677 (18)	−0.0107 (15)	0.0310 (16)	−0.0073 (13)
C16	0.0427 (13)	0.0769 (19)	0.0657 (17)	−0.0077 (12)	0.0334 (12)	−0.0049 (14)
C17	0.0498 (14)	0.085 (2)	0.087 (2)	0.0089 (14)	0.0366 (14)	−0.0185 (17)
C18	0.0357 (12)	0.0666 (18)	0.093 (2)	0.0151 (11)	0.0181 (13)	−0.0157 (15)
C19	0.0664 (16)	0.076 (2)	0.075 (2)	0.0375 (15)	0.0012 (14)	0.0123 (15)
C20	0.0779 (18)	0.0373 (15)	0.101 (2)	−0.0023 (13)	0.0113 (16)	−0.0058 (14)
C21	0.0828 (18)	0.083 (2)	0.0554 (17)	−0.0027 (16)	0.0153 (14)	0.0322 (15)
Cu1	0.02982 (13)	0.04586 (17)	0.04599 (17)	0.00438 (11)	0.01494 (12)	0.00773 (12)
Cu2	0.03448 (14)	0.04623 (17)	0.03978 (16)	0.00297 (11)	0.01607 (12)	0.00696 (12)
N1	0.0343 (9)	0.0452 (11)	0.0451 (11)	0.0004 (8)	0.0195 (8)	−0.0037 (9)
N2	0.0367 (9)	0.0420 (11)	0.0504 (11)	−0.0031 (8)	0.0228 (9)	−0.0003 (9)
N3	0.0358 (9)	0.0421 (12)	0.0599 (12)	0.0092 (8)	0.0072 (9)	−0.0043 (9)
N4	0.0599 (11)	0.0428 (11)	0.0362 (10)	−0.0100 (9)	0.0181 (9)	0.0030 (9)
N5	0.0654 (12)	0.0523 (14)	0.0605 (13)	−0.0079 (10)	0.0194 (11)	−0.0186 (11)
N6	0.0564 (12)	0.0493 (13)	0.0695 (14)	−0.0145 (10)	0.0181 (10)	−0.0130 (10)
O1	0.0266 (7)	0.0572 (9)	0.0299 (8)	0.0025 (6)	0.0084 (6)	0.0034 (6)
O11	0.0382 (8)	0.0844 (12)	0.0495 (10)	0.0098 (8)	0.0148 (7)	0.0199 (8)
S3	0.0648 (4)	0.0720 (5)	0.0766 (5)	−0.0241 (3)	0.0340 (4)	0.0000 (4)
S4	0.0654 (4)	0.0669 (5)	0.0845 (5)	−0.0065 (3)	0.0405 (4)	−0.0248 (4)

C1—O1	1.3168 (19)	C15—H15B	0.9600
C1—C6	1.416 (3)	C15—H15C	0.9600
C1—C2	1.419 (2)	C16—N2	1.477 (2)
C2—C3	1.400 (3)	C16—C17	1.510 (3)
C2—C11	1.439 (3)	C16—H16A	0.9700
C3—C4	1.377 (3)	C16—H16B	0.9700
C3—H3	0.9300	C17—C18	1.500 (3)
C4—C5	1.370 (3)	C17—H17A	0.9700
C4—C10	1.514 (2)	C17—H17B	0.9700
C5—C6	1.400 (3)	C18—N3	1.489 (3)
C5—H5	0.9300	C18—H18A	0.9700
C6—C9	1.446 (3)	C18—H18B	0.9700
C7—N5	1.151 (3)	C19—N3	1.477 (3)
C7—S4	1.621 (2)	C19—H19A	0.9600
C8—N6	1.151 (2)	C19—H19B	0.9600
C8—S3	1.616 (2)	C19—H19C	0.9600
C9—N2	1.279 (3)	C20—N3	1.474 (3)
C9—H9	0.9300	C20—H20A	0.9600
C10—H10A	0.9600	C20—H20B	0.9600
C10—H10B	0.9600	C20—H20C	0.9600
C10—H10C	0.9600	C21—N4	1.483 (3)
C11—N1	1.281 (3)	C21—H21A	0.9600
C11—H11	0.9300	C21—H21B	0.9600
C12—N1	1.482 (2)	C21—H21C	0.9600
C12—C13	1.499 (3)	Cu1—O11	1.9255 (15)
C12—H12A	0.9700	Cu1—N2	1.9587 (17)
C12—H12B	0.9700	Cu1—O1	2.0085 (12)
C13—C14	1.499 (3)	Cu1—N6	2.0985 (19)
C13—H13A	0.9700	Cu1—N3	2.1437 (17)
C13—H13B	0.9700	Cu2—O11	1.9219 (14)
C14—N4	1.492 (3)	Cu2—N1	1.9577 (16)
C14—H14A	0.9700	Cu2—O1	2.0203 (12)
C14—H14B	0.9700	Cu2—N5	2.101 (2)
C15—N4	1.470 (3)	Cu2—N4	2.1384 (17)
C15—H15A	0.9600	O11—H11O	0.8715
O1—C1—C6	121.49 (17)	N3—C18—H18A	108.3
O1—C1—C2	120.93 (18)	C17—C18—H18A	108.3
C6—C1—C2	117.58 (16)	N3—C18—H18B	108.3
C3—C2—C1	119.27 (18)	C17—C18—H18B	108.3
C3—C2—C11	116.95 (17)	H18A—C18—H18B	107.4
C1—C2—C11	123.78 (18)	N3—C19—H19A	109.5
C4—C3—C2	123.35 (18)	N3—C19—H19B	109.5
C4—C3—H3	118.3	H19A—C19—H19B	109.5
C2—C3—H3	118.3	N3—C19—H19C	109.5
C5—C4—C3	116.88 (18)	H19A—C19—H19C	109.5
C5—C4—C10	121.9 (2)	H19B—C19—H19C	109.5
C3—C4—C10	121.2 (2)	N3—C20—H20A	109.5
C4—C5—C6	123.2 (2)	N3—C20—H20B	109.5
C4—C5—H5	118.4	H20A—C20—H20B	109.5
C6—C5—H5	118.4	N3—C20—H20C	109.5
C5—C6—C1	119.72 (18)	H20A—C20—H20C	109.5
C5—C6—C9	117.17 (19)	H20B—C20—H20C	109.5
C1—C6—C9	123.11 (18)	N4—C21—H21A	109.5
N5—C7—S4	179.1 (2)	N4—C21—H21B	109.5
N6—C8—S3	179.6 (2)	H21A—C21—H21B	109.5
N2—C9—C6	129.14 (19)	N4—C21—H21C	109.5
N2—C9—H9	115.4	H21A—C21—H21C	109.5
C6—C9—H9	115.4	H21B—C21—H21C	109.5
C4—C10—H10A	109.5	O11—Cu1—N2	167.19 (6)
C4—C10—H10B	109.5	O11—Cu1—O1	76.72 (5)
H10A—C10—H10B	109.5	N2—Cu1—O1	90.78 (6)
C4—C10—H10C	109.5	O11—Cu1—N6	94.66 (7)
H10A—C10—H10C	109.5	N2—Cu1—N6	95.00 (7)
H10B—C10—H10C	109.5	O1—Cu1—N6	126.15 (7)
N1—C11—C2	129.00 (18)	O11—Cu1—N3	94.82 (7)
N1—C11—H11	115.5	N2—Cu1—N3	92.17 (7)
C2—C11—H11	115.5	O1—Cu1—N3	135.42 (6)
N1—C12—C13	111.92 (19)	N6—Cu1—N3	97.86 (7)
N1—C12—H12A	109.2	O11—Cu2—N1	166.83 (7)
C13—C12—H12A	109.2	O11—Cu2—O1	76.52 (5)
N1—C12—H12B	109.2	N1—Cu2—O1	90.62 (6)
C13—C12—H12B	109.2	O11—Cu2—N5	95.13 (7)
H12A—C12—H12B	107.9	N1—Cu2—N5	94.81 (7)
C12—C13—C14	114.5 (2)	O1—Cu2—N5	126.34 (7)
C12—C13—H13A	108.6	O11—Cu2—N4	94.66 (7)
C14—C13—H13A	108.6	N1—Cu2—N4	92.19 (7)
C12—C13—H13B	108.6	O1—Cu2—N4	133.61 (6)
C14—C13—H13B	108.6	N5—Cu2—N4	99.53 (7)
H13A—C13—H13B	107.6	C11—N1—C12	116.86 (17)
N4—C14—C13	115.60 (18)	C11—N1—Cu2	125.65 (14)
N4—C14—H14A	108.4	C12—N1—Cu2	117.46 (14)
C13—C14—H14A	108.4	C9—N2—C16	116.05 (18)
N4—C14—H14B	108.4	C9—N2—Cu1	125.50 (14)
C13—C14—H14B	108.4	C16—N2—Cu1	118.35 (15)
H14A—C14—H14B	107.4	C20—N3—C19	108.8 (2)
N4—C15—H15A	109.5	C20—N3—C18	110.60 (19)
N4—C15—H15B	109.5	C19—N3—C18	107.21 (18)
H15A—C15—H15B	109.5	C20—N3—Cu1	108.21 (13)
N4—C15—H15C	109.5	C19—N3—Cu1	110.66 (14)
H15A—C15—H15C	109.5	C18—N3—Cu1	111.32 (14)
H15B—C15—H15C	109.5	C15—N4—C21	109.2 (2)
N2—C16—C17	112.44 (19)	C15—N4—C14	110.47 (19)
N2—C16—H16A	109.1	C21—N4—C14	107.06 (18)
C17—C16—H16A	109.1	C15—N4—Cu2	107.68 (14)
N2—C16—H16B	109.1	C21—N4—Cu2	110.35 (14)
C17—C16—H16B	109.1	C14—N4—Cu2	112.04 (14)
H16A—C16—H16B	107.8	C7—N5—Cu2	160.80 (18)
C18—C17—C16	115.2 (2)	C8—N6—Cu1	157.66 (19)
C18—C17—H17A	108.5	C1—O1—Cu1	129.96 (12)
C16—C17—H17A	108.5	C1—O1—Cu2	130.01 (12)
C18—C17—H17B	108.5	Cu1—O1—Cu2	100.02 (5)
C16—C17—H17B	108.5	Cu2—O11—Cu1	106.70 (6)
H17A—C17—H17B	107.5	Cu2—O11—H11O	103.5
N3—C18—C17	115.82 (18)	Cu1—O11—H11O	101.1
O1—C1—C2—C3	178.85 (17)	N6—Cu1—N3—C19	67.38 (16)
C6—C1—C2—C3	−1.3 (3)	O11—Cu1—N3—C18	−147.13 (15)
O1—C1—C2—C11	−1.0 (3)	N2—Cu1—N3—C18	43.61 (15)
C6—C1—C2—C11	178.84 (19)	O1—Cu1—N3—C18	136.92 (14)
C1—C2—C3—C4	−0.2 (3)	N6—Cu1—N3—C18	−51.74 (16)
C11—C2—C3—C4	179.66 (19)	C13—C14—N4—C15	−63.7 (3)
C2—C3—C4—C5	1.5 (3)	C13—C14—N4—C21	177.5 (2)
C2—C3—C4—C10	179.94 (19)	C13—C14—N4—Cu2	56.4 (2)
C3—C4—C5—C6	−1.3 (3)	O11—Cu2—N4—C15	−89.45 (16)
C10—C4—C5—C6	−179.73 (19)	N1—Cu2—N4—C15	79.30 (16)
C4—C5—C6—C1	−0.2 (3)	O1—Cu2—N4—C15	−13.65 (19)
C4—C5—C6—C9	179.91 (19)	N5—Cu2—N4—C15	174.54 (16)
O1—C1—C6—C5	−178.67 (17)	O11—Cu2—N4—C21	29.70 (16)
C2—C1—C6—C5	1.5 (3)	N1—Cu2—N4—C21	−161.55 (16)
O1—C1—C6—C9	1.2 (3)	O1—Cu2—N4—C21	105.50 (16)
C2—C1—C6—C9	−178.60 (19)	N5—Cu2—N4—C21	−66.30 (17)
C5—C6—C9—N2	179.3 (2)	O11—Cu2—N4—C14	148.89 (14)
C1—C6—C9—N2	−0.5 (4)	N1—Cu2—N4—C14	−42.37 (15)
C3—C2—C11—N1	−179.7 (2)	O1—Cu2—N4—C14	−135.31 (13)
C1—C2—C11—N1	0.1 (4)	N5—Cu2—N4—C14	52.88 (15)
N1—C12—C13—C14	66.9 (3)	S4—C7—N5—Cu2	103 (13)
C12—C13—C14—N4	−67.0 (3)	O11—Cu2—N5—C7	−179.4 (6)
N2—C16—C17—C18	−63.9 (3)	N1—Cu2—N5—C7	9.3 (6)
C16—C17—C18—N3	66.5 (3)	O1—Cu2—N5—C7	103.6 (6)
C2—C11—N1—C12	179.1 (2)	N4—Cu2—N5—C7	−83.8 (6)
C2—C11—N1—Cu2	1.3 (3)	S3—C8—N6—Cu1	117 (30)
C13—C12—N1—C11	118.7 (2)	O11—Cu1—N6—C8	165.6 (5)
C13—C12—N1—Cu2	−63.2 (2)	N2—Cu1—N6—C8	−22.9 (5)
O11—Cu2—N1—C11	−13.7 (4)	O1—Cu1—N6—C8	−117.5 (5)
O1—Cu2—N1—C11	−1.36 (18)	N3—Cu1—N6—C8	70.0 (5)
N5—Cu2—N1—C11	125.20 (19)	C6—C1—O1—Cu1	−0.5 (2)
N4—Cu2—N1—C11	−135.05 (18)	C2—C1—O1—Cu1	179.35 (13)
O11—Cu2—N1—C12	168.5 (3)	C6—C1—O1—Cu2	−179.45 (13)
O1—Cu2—N1—C12	−179.19 (15)	C2—C1—O1—Cu2	0.4 (2)
N5—Cu2—N1—C12	−52.63 (16)	O11—Cu1—O1—C1	−177.76 (16)
N4—Cu2—N1—C12	47.12 (16)	N2—Cu1—O1—C1	−0.57 (16)
C6—C9—N2—C16	−177.2 (2)	N6—Cu1—O1—C1	96.20 (16)
C6—C9—N2—Cu1	−0.9 (3)	N3—Cu1—O1—C1	−94.45 (17)
C17—C16—N2—C9	−122.6 (2)	O11—Cu1—O1—Cu2	1.45 (6)
C17—C16—N2—Cu1	60.8 (2)	N2—Cu1—O1—Cu2	178.65 (6)
O11—Cu1—N2—C9	13.6 (4)	N6—Cu1—O1—Cu2	−84.59 (9)
O1—Cu1—N2—C9	1.19 (19)	N3—Cu1—O1—Cu2	84.76 (10)
N6—Cu1—N2—C9	−125.21 (18)	O11—Cu2—O1—C1	177.76 (16)
N3—Cu1—N2—C9	136.69 (18)	N1—Cu2—O1—C1	0.62 (16)
O11—Cu1—N2—C16	−170.1 (3)	N5—Cu2—O1—C1	−95.81 (16)
O1—Cu1—N2—C16	177.44 (15)	N4—Cu2—O1—C1	94.24 (16)
N6—Cu1—N2—C16	51.04 (16)	O11—Cu2—O1—Cu1	−1.46 (6)
N3—Cu1—N2—C16	−47.05 (16)	N1—Cu2—O1—Cu1	−178.59 (7)
C17—C18—N3—C20	62.5 (3)	N5—Cu2—O1—Cu1	84.98 (9)
C17—C18—N3—C19	−179.0 (2)	N4—Cu2—O1—Cu1	−84.97 (9)
C17—C18—N3—Cu1	−57.8 (2)	N1—Cu2—O11—Cu1	14.2 (4)
O11—Cu1—N3—C20	91.13 (16)	O1—Cu2—O11—Cu1	1.56 (7)
N2—Cu1—N3—C20	−78.13 (16)	N5—Cu2—O11—Cu1	−124.62 (9)
O1—Cu1—N3—C20	15.2 (2)	N4—Cu2—O11—Cu1	135.36 (8)
N6—Cu1—N3—C20	−173.48 (16)	N2—Cu1—O11—Cu2	−14.3 (4)
O11—Cu1—N3—C19	−28.01 (16)	O1—Cu1—O11—Cu2	−1.57 (7)
N2—Cu1—N3—C19	162.73 (16)	N6—Cu1—O11—Cu2	124.51 (8)
O1—Cu1—N3—C19	−103.96 (16)	N3—Cu1—O11—Cu2	−137.17 (8)