cis-Bis[1,1-dibenzyl-3-(furan-2-yl-carbonyl)thio-ureato-κO,S]copper(II).

In the title compound, [Cu(C(20)H(17)N(2)O(2)S)(2)], the Cu(II) atom is coordinated by the S and O atoms of two 1,1-dibenzyl-3-(furan-2-ylcarbon-yl)thio-ureate ligands in a distorted square-planar geometry. The two O and two S atoms are mutually cis to each other. The Cu-S and Cu-O bond lengths lie within the ranges of those found in related structures. The dihedral angle between the planes of the two chelating rings is 26.15 (6)°.

Related literature

For general background, see: Arslan et al. (2003 ▶). For synthesis details, see: Nagasawa & Mitsunobu (1981 ▶). For related structures, see: Binzet et al. (2006 ▶); Gomes et al. (2007 ▶); Pérez et al. (2011 ▶).

Experimental

Crystal data

[Cu(C20H17N2O2S)2]

M = 762.37

Monoclinic,

a = 18.8390 (3) Å

b = 10.8730 (2) Å

c = 19.6200 (3) Å

β = 114.748 (1)°

V = 3649.79 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.76 mm−1

T = 293 K

0.49 × 0.44 × 0.39 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: gaussian (Coppens et al., 1965 ▶) T min = 0.779, T max = 0.886

21982 measured reflections

7413 independent reflections

6761 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.122

S = 1.07

7413 reflections

460 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.39 e Å−3

Data collection: COLLECT (Enraf–Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶), SCALEPACK and SORTAV (Blessing, 1987 ▶, 1989 ▶); 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, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681101422X/bt5517sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101422X/bt5517Isup2.hkl

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

[Cu(C20H17N2O2S)2]	F(000) = 1580
Mr = 762.37	Dx = 1.387 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 22283 reflections
a = 18.8390 (3) Å	θ = 2.9–26.7°
b = 10.8730 (2) Å	µ = 0.76 mm−1
c = 19.6200 (3) Å	T = 293 K
β = 114.748 (1)°	Prism, blue
V = 3649.79 (10) Å3	0.49 × 0.44 × 0.39 mm
Z = 4

Nonius KappaCCD area-detector diffractometer	7413 independent reflections
Radiation source: Enraf–Nonius FR590	6761 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 9 pixels mm-1	θmax = 26.7°, θmin = 3.0°
CCD rotation images, thick slices scans	h = −23→23
Absorption correction: gaussian (Coppens et al., 1965)	k = −13→13
Tmin = 0.779, Tmax = 0.886	l = −24→24
21982 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0633P)2 + 1.1325P] where P = (Fo2 + 2Fc2)/3
7413 reflections	(Δ/σ)max = 0.001
460 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.508045 (16)	0.07839 (3)	0.297423 (16)	0.04477 (11)
S2	0.59888 (4)	0.07792 (6)	0.25262 (4)	0.05644 (19)
S1	0.53343 (5)	0.27665 (7)	0.32023 (5)	0.0707 (2)
O1	0.45058 (10)	0.06749 (15)	0.35857 (10)	0.0493 (4)
O2	0.46288 (11)	−0.07565 (18)	0.25155 (12)	0.0641 (5)
O3	0.39877 (11)	−0.02783 (16)	0.45314 (11)	0.0570 (4)
O4	0.35836 (12)	−0.2514 (2)	0.18813 (13)	0.0763 (6)
N1	0.44597 (11)	0.26752 (17)	0.40284 (11)	0.0424 (4)
N2	0.47257 (11)	0.45499 (18)	0.36697 (11)	0.0429 (4)
N3	0.53966 (11)	−0.14815 (18)	0.19153 (11)	0.0447 (4)
N4	0.65912 (11)	−0.09441 (17)	0.19891 (11)	0.0425 (4)
C1	0.43832 (12)	0.1451 (2)	0.39995 (12)	0.0395 (5)
C2	0.47889 (13)	0.3315 (2)	0.36579 (13)	0.0420 (5)
C3	0.40694 (13)	0.0971 (2)	0.45135 (13)	0.0415 (5)
C4	0.38350 (16)	0.1503 (3)	0.50008 (15)	0.0574 (7)
H4	0.3837	0.234	0.51	0.069*
C5	0.35819 (19)	0.0537 (3)	0.53378 (17)	0.0668 (8)
H5	0.338	0.0618	0.5695	0.08*
C6	0.36918 (17)	−0.0499 (3)	0.50399 (17)	0.0626 (7)
H6	0.358	−0.1279	0.5165	0.075*
C7	0.43616 (13)	0.5172 (2)	0.41091 (12)	0.0422 (5)
H7A	0.4716	0.58	0.4417	0.051*
H7B	0.4291	0.4577	0.4444	0.051*
C8	0.35843 (13)	0.5760 (2)	0.36437 (12)	0.0414 (5)
C9	0.29283 (14)	0.5045 (3)	0.32657 (14)	0.0545 (6)
H9	0.2976	0.4193	0.3272	0.065*
C10	0.22047 (16)	0.5575 (3)	0.28797 (17)	0.0673 (8)
H10	0.1768	0.5086	0.2627	0.081*
C11	0.21354 (17)	0.6836 (3)	0.28721 (16)	0.0685 (8)
H11	0.1648	0.72	0.2616	0.082*
C12	0.27814 (18)	0.7558 (3)	0.32403 (17)	0.0681 (8)
H12	0.2732	0.8409	0.3231	0.082*
C13	0.35041 (16)	0.7019 (2)	0.36246 (15)	0.0540 (6)
H13	0.3941	0.7512	0.3873	0.065*
C14	0.50761 (15)	0.5373 (2)	0.33057 (14)	0.0495 (6)
H14A	0.4777	0.6131	0.3175	0.059*
H14B	0.5031	0.4993	0.2842	0.059*
C15	0.59256 (15)	0.5687 (2)	0.37715 (14)	0.0465 (5)
C16	0.63705 (15)	0.5165 (2)	0.44601 (14)	0.0533 (6)
H16	0.615	0.4577	0.4658	0.064*
C17	0.71447 (18)	0.5511 (3)	0.48607 (18)	0.0709 (8)
H17	0.7439	0.516	0.5327	0.085*
C18	0.7477 (2)	0.6370 (4)	0.4571 (2)	0.0827 (10)
H18	0.7994	0.6608	0.4842	0.099*
C19	0.7043 (2)	0.6874 (3)	0.3881 (2)	0.0791 (10)
H19	0.727	0.7445	0.368	0.095*
C20	0.62787 (18)	0.6542 (3)	0.34867 (18)	0.0621 (7)
H20	0.599	0.6895	0.302	0.075*
C21	0.47872 (13)	−0.1453 (2)	0.20874 (13)	0.0441 (5)
C22	0.59750 (13)	−0.0648 (2)	0.21315 (12)	0.0405 (5)
C23	0.42344 (14)	−0.2456 (2)	0.17448 (13)	0.0491 (6)
C24	0.42619 (19)	−0.3425 (3)	0.13331 (16)	0.0645 (7)
H24	0.4649	−0.3597	0.1169	0.077*
C25	0.3587 (2)	−0.4131 (3)	0.1198 (2)	0.0890 (11)
H25	0.3443	−0.4861	0.0927	0.107*
C26	0.3200 (2)	−0.3554 (4)	0.1530 (2)	0.0917 (12)
H26	0.2728	−0.3822	0.1524	0.11*
C27	0.66466 (15)	−0.2122 (2)	0.16429 (13)	0.0476 (6)
H27A	0.628	−0.2702	0.1693	0.057*
H27B	0.7168	−0.2456	0.191	0.057*
C28	0.64762 (15)	−0.1988 (2)	0.08239 (14)	0.0484 (6)
C29	0.57841 (18)	−0.1499 (3)	0.03292 (17)	0.0744 (9)
H29	0.5418	−0.1239	0.0501	0.089*
C30	0.5620 (2)	−0.1384 (4)	−0.04314 (18)	0.0916 (11)
H30	0.5149	−0.104	−0.0762	0.11*
C31	0.6151 (2)	−0.1776 (4)	−0.06883 (19)	0.0873 (11)
H31	0.6042	−0.1704	−0.1195	0.105*
C32	0.6840 (2)	−0.2271 (3)	−0.02047 (19)	0.0816 (10)
H32	0.7201	−0.2543	−0.0381	0.098*
C33	0.70071 (19)	−0.2372 (3)	0.05522 (17)	0.0648 (7)
H33	0.7483	−0.2703	0.0881	0.078*
C34	0.72555 (14)	−0.0120 (2)	0.21270 (13)	0.0453 (5)
H34A	0.7097	0.0719	0.2159	0.054*
H34B	0.7394	−0.0166	0.1704	0.054*
C35	0.79670 (14)	−0.0422 (2)	0.28359 (14)	0.0452 (5)
C36	0.79724 (17)	−0.0283 (3)	0.35352 (16)	0.0621 (7)
H36	0.7525	−0.0007	0.3577	0.074*
C37	0.8635 (2)	−0.0550 (3)	0.41754 (18)	0.0785 (9)
H37	0.8628	−0.0459	0.4644	0.094*
C38	0.9302 (2)	−0.0947 (3)	0.4126 (2)	0.0787 (9)
H38	0.9748	−0.1119	0.4558	0.094*
C39	0.93044 (19)	−0.1087 (4)	0.3436 (2)	0.0822 (10)
H39	0.9754	−0.136	0.3397	0.099*
C40	0.86415 (17)	−0.0825 (3)	0.27935 (18)	0.0648 (8)
H40	0.865	−0.0922	0.2326	0.078*

	U11	U22	U33	U12	U13	U23
Cu	0.04319 (18)	0.04824 (19)	0.04929 (19)	0.00021 (12)	0.02570 (14)	−0.01030 (13)
S2	0.0615 (4)	0.0452 (4)	0.0818 (5)	−0.0050 (3)	0.0489 (4)	−0.0158 (3)
S1	0.0980 (6)	0.0474 (4)	0.1073 (6)	−0.0094 (4)	0.0828 (5)	−0.0144 (4)
O1	0.0552 (10)	0.0469 (9)	0.0563 (10)	−0.0054 (7)	0.0336 (8)	−0.0133 (8)
O2	0.0590 (11)	0.0696 (13)	0.0804 (13)	−0.0178 (9)	0.0454 (10)	−0.0342 (10)
O3	0.0683 (11)	0.0439 (9)	0.0703 (12)	−0.0069 (8)	0.0403 (10)	−0.0053 (9)
O4	0.0626 (12)	0.0881 (16)	0.0874 (15)	−0.0211 (11)	0.0405 (11)	−0.0213 (12)
N1	0.0440 (10)	0.0412 (10)	0.0481 (10)	0.0014 (8)	0.0252 (9)	−0.0018 (9)
N2	0.0474 (11)	0.0409 (10)	0.0433 (10)	0.0041 (8)	0.0218 (9)	0.0028 (8)
N3	0.0473 (11)	0.0462 (11)	0.0446 (10)	−0.0001 (9)	0.0233 (9)	−0.0041 (9)
N4	0.0487 (11)	0.0396 (10)	0.0472 (11)	0.0025 (8)	0.0279 (9)	−0.0029 (8)
C1	0.0328 (11)	0.0457 (13)	0.0402 (11)	0.0035 (9)	0.0154 (9)	−0.0033 (10)
C2	0.0432 (12)	0.0420 (12)	0.0429 (12)	0.0009 (9)	0.0202 (10)	−0.0027 (10)
C3	0.0412 (12)	0.0375 (12)	0.0477 (12)	−0.0010 (9)	0.0204 (10)	−0.0025 (10)
C4	0.0742 (18)	0.0493 (14)	0.0653 (16)	0.0050 (13)	0.0456 (15)	−0.0022 (13)
C5	0.080 (2)	0.073 (2)	0.0662 (18)	0.0004 (15)	0.0490 (16)	0.0085 (15)
C6	0.0674 (18)	0.0558 (16)	0.0739 (19)	−0.0076 (13)	0.0389 (15)	0.0094 (14)
C7	0.0445 (12)	0.0419 (12)	0.0371 (11)	0.0055 (10)	0.0140 (10)	−0.0031 (10)
C8	0.0432 (12)	0.0443 (13)	0.0358 (11)	0.0047 (10)	0.0157 (10)	−0.0013 (9)
C9	0.0476 (14)	0.0512 (15)	0.0579 (15)	0.0003 (11)	0.0153 (12)	−0.0010 (12)
C10	0.0427 (14)	0.083 (2)	0.0657 (18)	−0.0004 (14)	0.0126 (13)	0.0011 (16)
C11	0.0495 (16)	0.090 (2)	0.0579 (16)	0.0248 (15)	0.0144 (13)	0.0093 (16)
C12	0.075 (2)	0.0539 (16)	0.0663 (18)	0.0252 (15)	0.0209 (15)	0.0085 (14)
C13	0.0550 (15)	0.0451 (14)	0.0536 (14)	0.0078 (11)	0.0145 (12)	−0.0023 (12)
C14	0.0591 (15)	0.0446 (13)	0.0481 (13)	0.0048 (11)	0.0258 (12)	0.0084 (11)
C15	0.0572 (14)	0.0372 (12)	0.0530 (14)	0.0043 (10)	0.0309 (12)	−0.0026 (10)
C16	0.0573 (15)	0.0509 (15)	0.0557 (14)	0.0048 (12)	0.0277 (13)	−0.0016 (12)
C17	0.0568 (17)	0.080 (2)	0.0663 (18)	0.0095 (15)	0.0166 (15)	−0.0163 (16)
C18	0.0609 (19)	0.083 (2)	0.113 (3)	−0.0150 (17)	0.045 (2)	−0.037 (2)
C19	0.085 (2)	0.0617 (19)	0.115 (3)	−0.0185 (17)	0.066 (2)	−0.0185 (19)
C20	0.079 (2)	0.0470 (15)	0.0763 (18)	−0.0002 (13)	0.0483 (16)	0.0032 (13)
C21	0.0447 (12)	0.0476 (13)	0.0416 (12)	−0.0001 (10)	0.0198 (10)	−0.0043 (10)
C22	0.0472 (12)	0.0414 (12)	0.0390 (11)	0.0047 (10)	0.0240 (10)	0.0021 (9)
C23	0.0489 (14)	0.0550 (15)	0.0448 (13)	−0.0050 (11)	0.0210 (11)	−0.0044 (11)
C24	0.082 (2)	0.0624 (17)	0.0602 (16)	−0.0189 (15)	0.0406 (15)	−0.0195 (14)
C25	0.111 (3)	0.082 (2)	0.072 (2)	−0.044 (2)	0.037 (2)	−0.0325 (18)
C26	0.076 (2)	0.110 (3)	0.088 (2)	−0.046 (2)	0.032 (2)	−0.019 (2)
C27	0.0567 (14)	0.0395 (12)	0.0550 (14)	0.0068 (10)	0.0316 (12)	−0.0018 (11)
C28	0.0561 (14)	0.0446 (13)	0.0512 (13)	−0.0004 (11)	0.0290 (12)	−0.0095 (11)
C29	0.0671 (19)	0.098 (2)	0.0580 (17)	0.0151 (17)	0.0262 (15)	−0.0092 (17)
C30	0.084 (2)	0.122 (3)	0.0528 (18)	0.013 (2)	0.0128 (17)	−0.0080 (19)
C31	0.112 (3)	0.101 (3)	0.0537 (17)	−0.017 (2)	0.040 (2)	−0.0148 (18)
C32	0.104 (3)	0.093 (2)	0.074 (2)	−0.003 (2)	0.062 (2)	−0.0129 (19)
C33	0.0751 (19)	0.0673 (18)	0.0683 (17)	0.0095 (15)	0.0461 (15)	0.0000 (14)
C34	0.0550 (14)	0.0404 (12)	0.0544 (13)	−0.0022 (10)	0.0366 (12)	−0.0017 (11)
C35	0.0531 (14)	0.0383 (12)	0.0527 (13)	−0.0045 (10)	0.0305 (12)	−0.0040 (10)
C36	0.0674 (17)	0.0714 (18)	0.0568 (15)	0.0016 (14)	0.0353 (14)	−0.0061 (14)
C37	0.086 (2)	0.095 (3)	0.0522 (17)	0.0030 (19)	0.0257 (17)	−0.0060 (16)
C38	0.069 (2)	0.076 (2)	0.071 (2)	0.0052 (16)	0.0100 (17)	−0.0041 (16)
C39	0.0589 (19)	0.097 (3)	0.087 (2)	0.0159 (17)	0.0274 (18)	−0.005 (2)
C40	0.0599 (17)	0.079 (2)	0.0643 (17)	0.0119 (14)	0.0345 (15)	−0.0024 (14)

Cu—O1	1.9269 (16)	C15—C16	1.379 (4)
Cu—S1	2.2128 (8)	C15—C20	1.389 (4)
O1—C1	1.257 (3)	C16—C17	1.388 (4)
N1—C1	1.338 (3)	C16—H16	0.93
Cu—O2	1.9230 (18)	C17—C18	1.373 (5)
Cu—S2	2.2272 (7)	C17—H17	0.93
S1—C2	1.726 (2)	C18—C19	1.369 (5)
S2—C22	1.730 (2)	C18—H18	0.93
O2—C21	1.256 (3)	C19—C20	1.367 (5)
O3—C6	1.353 (3)	C19—H19	0.93
O3—C3	1.369 (3)	C20—H20	0.93
O4—C23	1.362 (3)	C21—C23	1.462 (3)
O4—C26	1.364 (4)	C23—C24	1.342 (4)
N1—C2	1.332 (3)	C24—C25	1.412 (4)
N2—C2	1.349 (3)	C24—H24	0.93
N2—C14	1.463 (3)	C25—C26	1.322 (5)
N2—C7	1.472 (3)	C25—H25	0.93
N3—C21	1.326 (3)	C26—H26	0.93
N3—C22	1.342 (3)	C27—C28	1.508 (3)
N4—C22	1.342 (3)	C27—H27A	0.97
N4—C34	1.470 (3)	C27—H27B	0.97
N4—C27	1.474 (3)	C28—C29	1.366 (4)
C1—C3	1.462 (3)	C28—C33	1.380 (4)
C3—C4	1.341 (3)	C29—C30	1.397 (4)
C4—C5	1.425 (4)	C29—H29	0.93
C4—H4	0.93	C30—C31	1.364 (5)
C5—C6	1.325 (4)	C30—H30	0.93
C5—H5	0.93	C31—C32	1.358 (5)
C6—H6	0.93	C31—H31	0.93
C7—C8	1.506 (3)	C32—C33	1.388 (4)
C7—H7A	0.97	C32—H32	0.93
C7—H7B	0.97	C33—H33	0.93
C8—C13	1.376 (3)	C34—C35	1.509 (3)
C8—C9	1.384 (3)	C34—H34A	0.97
C9—C10	1.379 (4)	C34—H34B	0.97
C9—H9	0.93	C35—C40	1.379 (4)
C10—C11	1.376 (4)	C35—C36	1.376 (3)
C10—H10	0.93	C36—C37	1.381 (4)
C11—C12	1.372 (4)	C36—H36	0.93
C11—H11	0.93	C37—C38	1.370 (5)
C12—C13	1.380 (4)	C37—H37	0.93
C12—H12	0.93	C38—C39	1.365 (5)
C13—H13	0.93	C38—H38	0.93
C14—C15	1.513 (4)	C39—C40	1.382 (5)
C14—H14A	0.97	C39—H39	0.93
C14—H14B	0.97	C40—H40	0.93
O2—Cu—O1	89.08 (7)	C16—C17—H17	119.9
O2—Cu—S1	163.52 (7)	C19—C18—C17	119.6 (3)
O1—Cu—S1	93.68 (5)	C19—C18—H18	120.2
O2—Cu—S2	94.35 (5)	C17—C18—H18	120.2
O1—Cu—S2	166.02 (6)	C18—C19—C20	120.4 (3)
S1—Cu—S2	86.86 (2)	C18—C19—H19	119.8
C22—S2—Cu	107.99 (8)	C20—C19—H19	119.8
C2—S1—Cu	108.45 (8)	C19—C20—C15	121.1 (3)
C1—O1—Cu	131.58 (15)	C19—C20—H20	119.4
C21—O2—Cu	130.97 (16)	C15—C20—H20	119.4
C6—O3—C3	106.3 (2)	O2—C21—N3	131.1 (2)
C23—O4—C26	105.7 (2)	O2—C21—C23	115.7 (2)
C2—N1—C1	124.29 (19)	N3—C21—C23	113.0 (2)
C2—N2—C14	122.62 (19)	N3—C22—N4	115.52 (19)
C2—N2—C7	122.24 (19)	N3—C22—S2	127.25 (17)
C14—N2—C7	114.91 (19)	N4—C22—S2	117.15 (17)
C21—N3—C22	125.4 (2)	C24—C23—O4	110.3 (2)
C22—N4—C34	124.03 (19)	C24—C23—C21	131.5 (2)
C22—N4—C27	122.60 (19)	O4—C23—C21	118.1 (2)
C34—N4—C27	113.32 (18)	C23—C24—C25	106.4 (3)
O1—C1—N1	130.5 (2)	C23—C24—H24	126.8
O1—C1—C3	116.3 (2)	C25—C24—H24	126.8
N1—C1—C3	113.16 (19)	C26—C25—C24	106.8 (3)
N1—C2—N2	116.5 (2)	C26—C25—H25	126.6
N1—C2—S1	128.01 (18)	C24—C25—H25	126.6
N2—C2—S1	115.40 (17)	C25—C26—O4	110.9 (3)
C4—C3—O3	109.6 (2)	C25—C26—H26	124.5
C4—C3—C1	133.4 (2)	O4—C26—H26	124.5
O3—C3—C1	116.99 (19)	N4—C27—C28	112.5 (2)
C3—C4—C5	106.7 (2)	N4—C27—H27A	109.1
C3—C4—H4	126.7	C28—C27—H27A	109.1
C5—C4—H4	126.7	N4—C27—H27B	109.1
C6—C5—C4	106.1 (2)	C28—C27—H27B	109.1
C6—C5—H5	126.9	H27A—C27—H27B	107.8
C4—C5—H5	126.9	C29—C28—C33	118.3 (3)
C5—C6—O3	111.3 (2)	C29—C28—C27	120.6 (2)
C5—C6—H6	124.4	C33—C28—C27	121.1 (2)
O3—C6—H6	124.4	C28—C29—C30	120.8 (3)
N2—C7—C8	114.41 (18)	C28—C29—H29	119.6
N2—C7—H7A	108.7	C30—C29—H29	119.6
C8—C7—H7A	108.7	C31—C30—C29	119.9 (3)
N2—C7—H7B	108.7	C31—C30—H30	120.1
C8—C7—H7B	108.7	C29—C30—H30	120.1
H7A—C7—H7B	107.6	C32—C31—C30	120.0 (3)
C13—C8—C9	118.8 (2)	C32—C31—H31	120
C13—C8—C7	120.5 (2)	C30—C31—H31	120
C9—C8—C7	120.6 (2)	C31—C32—C33	120.1 (3)
C10—C9—C8	121.0 (3)	C31—C32—H32	120
C10—C9—H9	119.5	C33—C32—H32	120
C8—C9—H9	119.5	C28—C33—C32	120.9 (3)
C11—C10—C9	119.4 (3)	C28—C33—H33	119.6
C11—C10—H10	120.3	C32—C33—H33	119.6
C9—C10—H10	120.3	N4—C34—C35	113.34 (19)
C12—C11—C10	120.3 (3)	N4—C34—H34A	108.9
C12—C11—H11	119.8	C35—C34—H34A	108.9
C10—C11—H11	119.8	N4—C34—H34B	108.9
C11—C12—C13	119.9 (3)	C35—C34—H34B	108.9
C11—C12—H12	120	H34A—C34—H34B	107.7
C13—C12—H12	120	C40—C35—C36	118.2 (3)
C12—C13—C8	120.6 (3)	C40—C35—C34	119.9 (2)
C12—C13—H13	119.7	C36—C35—C34	121.9 (2)
C8—C13—H13	119.7	C35—C36—C37	120.7 (3)
N2—C14—C15	115.0 (2)	C35—C36—H36	119.6
N2—C14—H14A	108.5	C37—C36—H36	119.6
C15—C14—H14A	108.5	C38—C37—C36	120.5 (3)
N2—C14—H14B	108.5	C38—C37—H37	119.7
C15—C14—H14B	108.5	C36—C37—H37	119.7
H14A—C14—H14B	107.5	C39—C38—C37	119.3 (3)
C16—C15—C20	118.2 (3)	C39—C38—H38	120.3
C16—C15—C14	123.7 (2)	C37—C38—H38	120.3
C20—C15—C14	118.1 (2)	C38—C39—C40	120.3 (3)
C15—C16—C17	120.5 (3)	C38—C39—H39	119.9
C15—C16—H16	119.8	C40—C39—H39	119.9
C17—C16—H16	119.8	C35—C40—C39	120.9 (3)
C18—C17—C16	120.2 (3)	C35—C40—H40	119.5
C18—C17—H17	119.9	C39—C40—H40	119.5
O2—Cu—S2—C22	−9.59 (11)	C15—C16—C17—C18	−0.6 (4)
O1—Cu—S2—C22	94.2 (2)	C16—C17—C18—C19	−0.7 (5)
S1—Cu—S2—C22	−173.12 (9)	C17—C18—C19—C20	1.1 (5)
O2—Cu—S1—C2	89.5 (2)	C18—C19—C20—C15	−0.3 (5)
O1—Cu—S1—C2	−9.81 (11)	C16—C15—C20—C19	−0.9 (4)
S2—Cu—S1—C2	−175.82 (9)	C14—C15—C20—C19	179.6 (3)
O2—Cu—O1—C1	−168.3 (2)	Cu—O2—C21—N3	13.8 (4)
S1—Cu—O1—C1	−4.5 (2)	Cu—O2—C21—C23	−170.15 (19)
S2—Cu—O1—C1	87.3 (3)	C22—N3—C21—O2	−6.4 (4)
O1—Cu—O2—C21	−169.5 (3)	C22—N3—C21—C23	177.5 (2)
S1—Cu—O2—C21	90.5 (3)	C21—N3—C22—N4	170.6 (2)
S2—Cu—O2—C21	−3.1 (3)	C21—N3—C22—S2	−12.8 (4)
Cu—O1—C1—N1	16.9 (4)	C34—N4—C22—N3	175.0 (2)
Cu—O1—C1—C3	−166.58 (16)	C27—N4—C22—N3	−2.1 (3)
C2—N1—C1—O1	−8.8 (4)	C34—N4—C22—S2	−1.9 (3)
C2—N1—C1—C3	174.5 (2)	C27—N4—C22—S2	−179.00 (17)
C1—N1—C2—N2	171.5 (2)	Cu—S2—C22—N3	18.8 (2)
C1—N1—C2—S1	−12.3 (3)	Cu—S2—C22—N4	−164.70 (15)
C14—N2—C2—N1	178.3 (2)	C26—O4—C23—C24	−0.7 (3)
C7—N2—C2—N1	4.1 (3)	C26—O4—C23—C21	−177.1 (3)
C14—N2—C2—S1	1.6 (3)	O2—C21—C23—C24	−172.0 (3)
C7—N2—C2—S1	−172.62 (16)	N3—C21—C23—C24	4.8 (4)
Cu—S1—C2—N1	19.6 (2)	O2—C21—C23—O4	3.4 (4)
Cu—S1—C2—N2	−164.11 (15)	N3—C21—C23—O4	−179.8 (2)
C6—O3—C3—C4	0.4 (3)	O4—C23—C24—C25	0.4 (4)
C6—O3—C3—C1	180.0 (2)	C21—C23—C24—C25	176.1 (3)
O1—C1—C3—C4	−176.3 (3)	C23—C24—C25—C26	0.1 (4)
N1—C1—C3—C4	0.8 (4)	C24—C25—C26—O4	−0.5 (5)
O1—C1—C3—O3	4.2 (3)	C23—O4—C26—C25	0.8 (4)
N1—C1—C3—O3	−178.7 (2)	C22—N4—C27—C28	103.0 (3)
O3—C3—C4—C5	−0.8 (3)	C34—N4—C27—C28	−74.3 (3)
C1—C3—C4—C5	179.7 (3)	N4—C27—C28—C29	−56.7 (3)
C3—C4—C5—C6	0.9 (3)	N4—C27—C28—C33	124.3 (3)
C4—C5—C6—O3	−0.7 (4)	C33—C28—C29—C30	−0.3 (5)
C3—O3—C6—C5	0.2 (3)	C27—C28—C29—C30	−179.4 (3)
C2—N2—C7—C8	−109.9 (2)	C28—C29—C30—C31	0.7 (6)
C14—N2—C7—C8	75.5 (3)	C29—C30—C31—C32	−0.4 (6)
N2—C7—C8—C13	−112.8 (3)	C30—C31—C32—C33	−0.4 (6)
N2—C7—C8—C9	71.2 (3)	C29—C28—C33—C32	−0.4 (5)
C13—C8—C9—C10	−0.4 (4)	C27—C28—C33—C32	178.6 (3)
C7—C8—C9—C10	175.6 (2)	C31—C32—C33—C28	0.8 (5)
C8—C9—C10—C11	−0.1 (4)	C22—N4—C34—C35	101.4 (3)
C9—C10—C11—C12	0.5 (5)	C27—N4—C34—C35	−81.2 (2)
C10—C11—C12—C13	−0.4 (5)	N4—C34—C35—C40	114.7 (3)
C11—C12—C13—C8	−0.1 (4)	N4—C34—C35—C36	−66.7 (3)
C9—C8—C13—C12	0.5 (4)	C40—C35—C36—C37	−0.5 (4)
C7—C8—C13—C12	−175.5 (2)	C34—C35—C36—C37	−179.1 (3)
C2—N2—C14—C15	−84.6 (3)	C35—C36—C37—C38	0.6 (5)
C7—N2—C14—C15	89.9 (2)	C36—C37—C38—C39	−0.5 (6)
N2—C14—C15—C16	5.7 (3)	C37—C38—C39—C40	0.3 (6)
N2—C14—C15—C20	−174.8 (2)	C36—C35—C40—C39	0.2 (5)
C20—C15—C16—C17	1.4 (4)	C34—C35—C40—C39	178.9 (3)
C14—C15—C16—C17	−179.1 (2)	C38—C39—C40—C35	−0.2 (5)