(2,2'-Bi-pyridine-κ(2) N,N')tetra-kis-(dimethyl sulfoxide-κO)copper(II) bis-(perchlorate).

The title compound, [Cu(C2H6OS)4(C10H8N2)](ClO4)2, contains a Cu(II) ion with a distorted octa-hedral coordination environment, bonded by four O atoms of the monodentate dimethyl sulfoxide ligands and two N atoms of the bidentate chelating 2,2'-bi-pyridine ligand. The equatorial Cu-N and Cu-O bond lengths are in the range 1.979 (2)-1.998 (3) Å. The axial Cu-O bond distances are 2.365 (2) and 2.394 (2) Å. In the crystal, the complex cations and perchlorate anions are connected by numerous C-H⋯O hydrogen bonds, which leads to additional stabilization of the structure. The perchlorate anion is disordered over two sets of sites with a 0.716 (3):0.284 (3) occupancy ratio.

Related literature

For applications of the 2,2′-bipyridyl ligand, see: Fritsky et al. (2004 ▶, 2006 ▶); Kanderal et al. (2005 ▶). For related structures, see: Fritsky et al. (1998 ▶, 2000 ▶); Moroz et al. (2010 ▶, 2012 ▶); Sliva et al. (1997 ▶); Świątek-Kozłowska et al. (2000 ▶, 2002 ▶); Iskenderov et al. (2009 ▶); Golenya et al. (2012a ▶). For the synthesis, see: Golenya et al. (2012b ▶).

Experimental

Crystal data

[Cu(C2H6OS)4(C10H8N2)](ClO4)2

M = 731.14

Monoclinic,

a = 10.8050 (5) Å

b = 11.6470 (5) Å

c = 24.5210 (8) Å

β = 94.984 (5)°

V = 3074.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.21 mm−1

T = 120 K

0.33 × 0.23 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (MULABS; Blessing, 1995 ▶) T min = 0.747, T max = 0.862

40246 measured reflections

13140 independent reflections

6565 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.160

S = 1.07

13140 reflections

362 parameters

10 restraints

H-atom parameters constrained

Δρmax = 1.21 e Å−3

Δρmin = −0.84 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813018485/nr2046sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018485/nr2046Isup2.hkl

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

[Cu(C2H6OS)4(C10H8N2)](ClO4)2	F(000) = 1508
Mr = 731.14	Dx = 1.580 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2567 reflections
a = 10.8050 (5) Å	θ = 3.0–25.5°
b = 11.6470 (5) Å	µ = 1.21 mm−1
c = 24.5210 (8) Å	T = 120 K
β = 94.984 (5)°	Block, blue
V = 3074.2 (2) Å3	0.33 × 0.23 × 0.12 mm
Z = 4

Nonius KappaCCD diffractometer	13140 independent reflections
Radiation source: fine-focus sealed tube	6565 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.074
Detector resolution: 9 pixels mm-1	θmax = 36.7°, θmin = 3.0°
φ scans and ω scans with κ offset	h = −13→17
Absorption correction: multi-scan (MULABS; Blessing, 1995)	k = −15→19
Tmin = 0.747, Tmax = 0.862	l = −40→31
40246 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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0589P)2] where P = (Fo2 + 2Fc2)/3
13140 reflections	(Δ/σ)max < 0.001
362 parameters	Δρmax = 1.21 e Å−3
10 restraints	Δρmin = −0.84 e Å−3

Experimental. The C—H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.95(CH), 0.98(CH3) and Uiso = 1.2 or 1.5 Ueq(parent atom) for CH and CH3, respectively. One of the perchlorate anions were found to be disordered over two positions with occupancy factors 0.716/0.284. All atoms were refined with anisotropic displacement parameters except the oxygen atoms of the disordered perchlorate which were refined isotropically. Cl—O bond distances and O···O separations of both (minor and major) fractions of the disordered perchlorate anion as well as the ordered perchlorate (as a model) were restrained to have identical values. For each corresponding pair of the oxygen atoms of the disordered perchlorate anion, the isotropic displacement parameters were restrained to have identical values.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Cu1	0.01095 (4)	0.25254 (3)	0.093944 (15)	0.01663 (10)
S1	−0.22872 (8)	0.37353 (8)	0.15620 (4)	0.0260 (2)
S2	−0.10117 (8)	0.03071 (7)	0.13267 (3)	0.02201 (19)
S3	0.02546 (8)	0.21930 (7)	0.22086 (3)	0.02254 (19)
S4	0.24417 (8)	0.03374 (7)	0.06730 (3)	0.02011 (18)
O1	−0.1237 (2)	0.4013 (2)	0.12111 (10)	0.0256 (5)
O2	−0.1282 (2)	0.14612 (18)	0.10375 (9)	0.0185 (5)
O3	0.0926 (2)	0.22831 (19)	0.16856 (9)	0.0224 (5)
O4	0.1196 (2)	0.0936 (2)	0.06162 (9)	0.0225 (5)
Cl1	0.46540 (9)	0.22816 (8)	−0.07645 (4)	0.0300 (2)
O5	0.5215 (3)	0.2784 (3)	−0.12148 (12)	0.0607 (10)
O6	0.3432 (3)	0.2715 (2)	−0.07428 (13)	0.0490 (8)
O7	0.4600 (3)	0.1059 (3)	−0.08316 (15)	0.0599 (10)
O8	0.5387 (3)	0.2541 (3)	−0.02657 (11)	0.0535 (9)
Cl2_1	0.4834 (4)	0.2572 (3)	0.25477 (14)	0.0236 (7)	0.716 (3)
O9_1	0.4557 (4)	0.1434 (3)	0.26534 (16)	0.0426 (10)*	0.716 (3)
O10_1	0.4453 (6)	0.3286 (5)	0.2980 (2)	0.0806 (16)*	0.716 (3)
O11_1	0.6132 (5)	0.2703 (5)	0.2537 (2)	0.0843 (17)*	0.716 (3)
O12_1	0.4289 (5)	0.2943 (4)	0.20296 (19)	0.0643 (13)*	0.716 (3)
Cl2_2	0.4738 (9)	0.2835 (7)	0.2563 (4)	0.0217 (17)	0.284 (3)
O9_2	0.3653 (8)	0.3114 (8)	0.2807 (4)	0.0426 (10)*	0.284 (3)
O10_2	0.5733 (10)	0.2666 (10)	0.2973 (5)	0.0806 (16)*	0.284 (3)
O11_2	0.5087 (11)	0.3809 (9)	0.2254 (5)	0.0843 (17)*	0.284 (3)
O12_2	0.4559 (10)	0.1942 (8)	0.2174 (4)	0.0643 (13)*	0.284 (3)
N1	−0.0439 (2)	0.2824 (2)	0.01530 (11)	0.0165 (6)
N2	0.1453 (2)	0.3611 (2)	0.07722 (10)	0.0169 (6)
C1	−0.1461 (3)	0.2403 (3)	−0.01254 (13)	0.0199 (7)
H1	−0.2011	0.1935	0.0060	0.024*
C2	−0.1736 (3)	0.2635 (3)	−0.06822 (14)	0.0235 (7)
H2	−0.2471	0.2338	−0.0872	0.028*
C3	−0.0930 (3)	0.3302 (3)	−0.09514 (13)	0.0229 (7)
H3	−0.1093	0.3455	−0.1331	0.028*
C4	0.0120 (3)	0.3746 (3)	−0.06631 (13)	0.0227 (8)
H4	0.0682	0.4214	−0.0841	0.027*
C5	0.2357 (3)	0.4606 (3)	0.00510 (14)	0.0251 (8)
H5	0.2326	0.4815	−0.0324	0.030*
C6	0.3321 (4)	0.4966 (3)	0.04112 (15)	0.0292 (9)
H6	0.3967	0.5425	0.0287	0.035*
C7	0.3345 (3)	0.4653 (3)	0.09585 (15)	0.0243 (8)
H7	0.4001	0.4900	0.1215	0.029*
C8	0.2394 (3)	0.3976 (3)	0.11236 (14)	0.0206 (7)
H8	0.2406	0.3762	0.1498	0.025*
C9	0.0340 (3)	0.3495 (3)	−0.01083 (13)	0.0182 (7)
C10	0.1433 (3)	0.3933 (3)	0.02420 (13)	0.0183 (7)
C12	−0.3584 (3)	0.3309 (4)	0.11044 (16)	0.0356 (9)
H12A	−0.3773	0.3915	0.0832	0.053*
H12B	−0.4307	0.3181	0.1312	0.053*
H12C	−0.3382	0.2597	0.0918	0.053*
C13	−0.2864 (4)	0.5103 (4)	0.17568 (17)	0.0423 (11)
H13A	−0.2233	0.5490	0.2003	0.063*
H13B	−0.3620	0.4994	0.1945	0.063*
H13C	−0.3055	0.5575	0.1429	0.063*
C14	−0.1260 (4)	−0.0737 (3)	0.08036 (15)	0.0320 (9)
H14A	−0.2080	−0.0621	0.0608	0.048*
H14B	−0.1217	−0.1506	0.0967	0.048*
H14C	−0.0619	−0.0661	0.0547	0.048*
C15	−0.2366 (4)	0.0083 (4)	0.16771 (16)	0.0364 (10)
H15A	−0.2396	0.0655	0.1969	0.055*
H15B	−0.2342	−0.0689	0.1837	0.055*
H15C	−0.3106	0.0159	0.1419	0.055*
C16	0.0575 (4)	0.3504 (3)	0.25593 (16)	0.0404 (10)
H16A	0.1473	0.3645	0.2591	0.061*
H16B	0.0282	0.3458	0.2926	0.061*
H16C	0.0148	0.4133	0.2355	0.061*
C17	0.1207 (4)	0.1252 (3)	0.26321 (15)	0.0332 (9)
H17A	0.1133	0.0471	0.2485	0.050*
H17B	0.0939	0.1263	0.3004	0.050*
H17C	0.2074	0.1504	0.2642	0.050*
C18	0.2790 (4)	0.0049 (4)	0.13850 (14)	0.0354 (10)
H18A	0.2735	0.0762	0.1593	0.053*
H18B	0.3632	−0.0265	0.1446	0.053*
H18C	0.2192	−0.0509	0.1506	0.053*
C19	0.3605 (3)	0.1404 (3)	0.06048 (17)	0.0324 (9)
H19A	0.3422	0.1819	0.0260	0.049*
H19B	0.4420	0.1034	0.0606	0.049*
H19C	0.3612	0.1944	0.0911	0.049*

	U11	U22	U33	U12	U13	U23
Cu1	0.0172 (2)	0.01757 (19)	0.01494 (18)	−0.00310 (17)	0.00027 (14)	0.00218 (16)
S1	0.0200 (4)	0.0336 (5)	0.0251 (4)	0.0051 (4)	0.0070 (4)	0.0087 (4)
S2	0.0234 (5)	0.0188 (4)	0.0229 (4)	−0.0060 (3)	−0.0037 (3)	0.0044 (3)
S3	0.0262 (5)	0.0238 (4)	0.0173 (4)	−0.0015 (4)	0.0005 (3)	−0.0019 (3)
S4	0.0205 (4)	0.0190 (4)	0.0211 (4)	0.0024 (3)	0.0030 (3)	0.0007 (3)
O1	0.0245 (13)	0.0220 (13)	0.0321 (14)	−0.0021 (10)	0.0139 (11)	−0.0001 (10)
O2	0.0199 (12)	0.0161 (11)	0.0193 (11)	−0.0009 (9)	0.0007 (9)	0.0031 (9)
O3	0.0237 (13)	0.0249 (13)	0.0177 (11)	−0.0068 (10)	−0.0023 (10)	0.0041 (9)
O4	0.0174 (12)	0.0230 (12)	0.0267 (13)	0.0047 (10)	−0.0001 (10)	−0.0016 (10)
Cl1	0.0255 (5)	0.0340 (5)	0.0313 (5)	−0.0103 (4)	0.0071 (4)	−0.0072 (4)
O5	0.0444 (19)	0.113 (3)	0.0248 (15)	−0.0251 (19)	0.0071 (14)	0.0041 (17)
O6	0.0458 (19)	0.0425 (18)	0.061 (2)	0.0143 (15)	0.0204 (16)	0.0078 (15)
O7	0.048 (2)	0.0341 (17)	0.093 (3)	0.0076 (15)	−0.0144 (18)	−0.0270 (17)
O8	0.065 (2)	0.067 (2)	0.0276 (15)	−0.0458 (18)	0.0013 (14)	−0.0026 (15)
Cl2_1	0.0311 (11)	0.0185 (16)	0.0215 (9)	−0.0024 (11)	0.0034 (7)	0.0011 (9)
Cl2_2	0.034 (3)	0.012 (3)	0.020 (2)	0.001 (2)	0.0045 (18)	−0.0071 (19)
N1	0.0179 (14)	0.0133 (13)	0.0187 (13)	0.0033 (10)	0.0034 (11)	0.0018 (10)
N2	0.0151 (14)	0.0166 (13)	0.0190 (13)	0.0013 (11)	0.0016 (11)	−0.0001 (11)
C1	0.0211 (17)	0.0176 (16)	0.0206 (16)	0.0023 (14)	−0.0009 (13)	−0.0018 (13)
C2	0.0243 (18)	0.0236 (18)	0.0217 (16)	0.0047 (15)	−0.0028 (14)	−0.0014 (14)
C3	0.032 (2)	0.0213 (17)	0.0151 (16)	0.0091 (15)	0.0024 (14)	−0.0009 (13)
C4	0.034 (2)	0.0160 (16)	0.0196 (17)	0.0054 (14)	0.0092 (15)	0.0030 (13)
C5	0.031 (2)	0.0203 (18)	0.0255 (18)	−0.0012 (15)	0.0129 (16)	0.0001 (14)
C6	0.030 (2)	0.0202 (18)	0.040 (2)	−0.0052 (15)	0.0146 (18)	−0.0044 (16)
C7	0.0159 (17)	0.0197 (17)	0.037 (2)	−0.0009 (14)	0.0004 (15)	−0.0044 (15)
C8	0.0163 (17)	0.0185 (16)	0.0262 (17)	0.0007 (13)	−0.0024 (14)	−0.0016 (14)
C9	0.0206 (17)	0.0161 (15)	0.0188 (16)	0.0069 (13)	0.0071 (13)	0.0006 (13)
C10	0.0228 (18)	0.0118 (15)	0.0212 (16)	0.0025 (13)	0.0056 (13)	0.0009 (12)
C12	0.020 (2)	0.049 (3)	0.038 (2)	0.0017 (18)	0.0040 (17)	−0.0008 (19)
C13	0.036 (2)	0.053 (3)	0.039 (2)	0.017 (2)	0.0120 (19)	−0.005 (2)
C14	0.036 (2)	0.0224 (19)	0.037 (2)	−0.0001 (17)	−0.0006 (18)	−0.0047 (16)
C15	0.041 (2)	0.042 (2)	0.027 (2)	−0.0163 (19)	0.0094 (18)	0.0057 (17)
C16	0.054 (3)	0.034 (2)	0.032 (2)	−0.004 (2)	−0.004 (2)	−0.0119 (18)
C17	0.033 (2)	0.044 (2)	0.0229 (18)	0.0091 (19)	0.0058 (16)	0.0110 (17)
C18	0.032 (2)	0.049 (3)	0.0256 (19)	0.0172 (19)	0.0033 (17)	0.0146 (17)
C19	0.024 (2)	0.0237 (19)	0.050 (2)	0.0020 (16)	0.0091 (18)	0.0023 (17)

Cu1—O2	1.979 (2)	C3—C4	1.384 (5)
Cu1—O3	1.981 (2)	C3—H3	0.9500
Cu1—N2	1.994 (3)	C4—C9	1.392 (4)
Cu1—N1	1.998 (3)	C4—H4	0.9500
Cu1—O4	2.365 (2)	C5—C6	1.371 (5)
Cu1—O1	2.394 (2)	C5—C10	1.383 (4)
S1—O1	1.517 (2)	C5—H5	0.9500
S1—C12	1.788 (4)	C6—C7	1.389 (5)
S1—C13	1.791 (4)	C6—H6	0.9500
S2—O2	1.536 (2)	C7—C8	1.384 (5)
S2—C14	1.771 (4)	C7—H7	0.9500
S2—C15	1.779 (4)	C8—H8	0.9500
S3—O3	1.531 (2)	C9—C10	1.488 (5)
S3—C16	1.772 (4)	C12—H12A	0.9800
S3—C17	1.775 (4)	C12—H12B	0.9800
S4—O4	1.512 (2)	C12—H12C	0.9800
S4—C19	1.785 (4)	C13—H13A	0.9800
S4—C18	1.786 (4)	C13—H13B	0.9800
Cl1—O6	1.419 (3)	C13—H13C	0.9800
Cl1—O5	1.430 (3)	C14—H14A	0.9800
Cl1—O8	1.431 (3)	C14—H14B	0.9800
Cl1—O7	1.435 (3)	C14—H14C	0.9800
Cl2_1—O9_1	1.388 (5)	C15—H15A	0.9800
Cl2_1—O11_1	1.413 (7)	C15—H15B	0.9800
Cl2_1—O12_1	1.421 (6)	C15—H15C	0.9800
Cl2_1—O10_1	1.436 (6)	C16—H16A	0.9800
Cl2_2—O9_2	1.399 (9)	C16—H16B	0.9800
Cl2_2—O12_2	1.413 (8)	C16—H16C	0.9800
Cl2_2—O10_2	1.421 (10)	C17—H17A	0.9800
Cl2_2—O11_2	1.432 (9)	C17—H17B	0.9800
N1—C1	1.340 (4)	C17—H17C	0.9800
N1—C9	1.351 (4)	C18—H18A	0.9800
N2—C8	1.343 (4)	C18—H18B	0.9800
N2—C10	1.352 (4)	C18—H18C	0.9800
C1—C2	1.398 (5)	C19—H19A	0.9800
C1—H1	0.9500	C19—H19B	0.9800
C2—C3	1.377 (5)	C19—H19C	0.9800
C2—H2	0.9500
O2—Cu1—O3	94.62 (9)	C6—C5—C10	119.1 (3)
O2—Cu1—N2	174.98 (10)	C6—C5—H5	120.5
O3—Cu1—N2	90.37 (10)	C10—C5—H5	120.5
O2—Cu1—N1	93.53 (10)	C5—C6—C7	119.5 (3)
O3—Cu1—N1	170.76 (10)	C5—C6—H6	120.3
N2—Cu1—N1	81.45 (11)	C7—C6—H6	120.3
O2—Cu1—O4	87.42 (8)	C8—C7—C6	118.7 (3)
O3—Cu1—O4	90.21 (9)	C8—C7—H7	120.6
N2—Cu1—O4	92.05 (9)	C6—C7—H7	120.6
N1—Cu1—O4	85.81 (9)	N2—C8—C7	122.2 (3)
O2—Cu1—O1	86.15 (8)	N2—C8—H8	118.9
O3—Cu1—O1	94.52 (9)	C7—C8—H8	118.9
N2—Cu1—O1	93.98 (9)	N1—C9—C4	121.6 (3)
N1—Cu1—O1	90.35 (9)	N1—C9—C10	114.9 (3)
O4—Cu1—O1	172.30 (8)	C4—C9—C10	123.5 (3)
O1—S1—C12	106.68 (17)	N2—C10—C5	122.1 (3)
O1—S1—C13	104.87 (17)	N2—C10—C9	113.9 (3)
C12—S1—C13	98.2 (2)	C5—C10—C9	124.0 (3)
O2—S2—C14	104.83 (16)	S1—C12—H12A	109.5
O2—S2—C15	102.73 (17)	S1—C12—H12B	109.5
C14—S2—C15	99.78 (19)	H12A—C12—H12B	109.5
O3—S3—C16	105.11 (17)	S1—C12—H12C	109.5
O3—S3—C17	103.87 (15)	H12A—C12—H12C	109.5
C16—S3—C17	99.7 (2)	H12B—C12—H12C	109.5
O4—S4—C19	107.37 (15)	S1—C13—H13A	109.5
O4—S4—C18	106.68 (16)	S1—C13—H13B	109.5
C19—S4—C18	97.6 (2)	H13A—C13—H13B	109.5
S1—O1—Cu1	120.43 (13)	S1—C13—H13C	109.5
S2—O2—Cu1	119.24 (13)	H13A—C13—H13C	109.5
S3—O3—Cu1	125.31 (14)	H13B—C13—H13C	109.5
S4—O4—Cu1	142.59 (14)	S2—C14—H14A	109.5
O6—Cl1—O5	110.0 (2)	S2—C14—H14B	109.5
O6—Cl1—O8	109.9 (2)	H14A—C14—H14B	109.5
O5—Cl1—O8	109.46 (18)	S2—C14—H14C	109.5
O6—Cl1—O7	109.21 (19)	H14A—C14—H14C	109.5
O5—Cl1—O7	109.5 (2)	H14B—C14—H14C	109.5
O8—Cl1—O7	108.8 (2)	S2—C15—H15A	109.5
O9_1—Cl2_1—O11_1	109.7 (4)	S2—C15—H15B	109.5
O9_1—Cl2_1—O12_1	112.2 (3)	H15A—C15—H15B	109.5
O11_1—Cl2_1—O12_1	106.6 (4)	S2—C15—H15C	109.5
O9_1—Cl2_1—O10_1	109.6 (3)	H15A—C15—H15C	109.5
O11_1—Cl2_1—O10_1	107.4 (4)	H15B—C15—H15C	109.5
O12_1—Cl2_1—O10_1	111.2 (4)	S3—C16—H16A	109.5
O9_2—Cl2_2—O12_2	112.9 (7)	S3—C16—H16B	109.5
O9_2—Cl2_2—O10_2	109.9 (7)	H16A—C16—H16B	109.5
O12_2—Cl2_2—O10_2	115.2 (8)	S3—C16—H16C	109.5
O9_2—Cl2_2—O11_2	108.1 (7)	H16A—C16—H16C	109.5
O12_2—Cl2_2—O11_2	104.7 (7)	H16B—C16—H16C	109.5
O10_2—Cl2_2—O11_2	105.4 (7)	S3—C17—H17A	109.5
C1—N1—C9	119.4 (3)	S3—C17—H17B	109.5
C1—N1—Cu1	126.2 (2)	H17A—C17—H17B	109.5
C9—N1—Cu1	114.4 (2)	S3—C17—H17C	109.5
C8—N2—C10	118.5 (3)	H17A—C17—H17C	109.5
C8—N2—Cu1	126.3 (2)	H17B—C17—H17C	109.5
C10—N2—Cu1	115.0 (2)	S4—C18—H18A	109.5
N1—C1—C2	121.5 (3)	S4—C18—H18B	109.5
N1—C1—H1	119.2	H18A—C18—H18B	109.5
C2—C1—H1	119.2	S4—C18—H18C	109.5
C3—C2—C1	119.2 (3)	H18A—C18—H18C	109.5
C3—C2—H2	120.4	H18B—C18—H18C	109.5
C1—C2—H2	120.4	S4—C19—H19A	109.5
C2—C3—C4	119.4 (3)	S4—C19—H19B	109.5
C2—C3—H3	120.3	H19A—C19—H19B	109.5
C4—C3—H3	120.3	S4—C19—H19C	109.5
C3—C4—C9	118.9 (3)	H19A—C19—H19C	109.5
C3—C4—H4	120.5	H19B—C19—H19C	109.5
C9—C4—H4	120.5
C12—S1—O1—Cu1	−85.9 (2)	O1—Cu1—N1—C9	98.2 (2)
C13—S1—O1—Cu1	170.58 (18)	O2—Cu1—N2—C8	−179 (55)
O2—Cu1—O1—S1	24.70 (16)	O3—Cu1—N2—C8	−4.9 (3)
O3—Cu1—O1—S1	−69.64 (17)	N1—Cu1—N2—C8	179.4 (3)
N2—Cu1—O1—S1	−160.33 (17)	O4—Cu1—N2—C8	−95.1 (3)
N1—Cu1—O1—S1	118.21 (17)	O1—Cu1—N2—C8	89.7 (3)
O4—Cu1—O1—S1	58.2 (7)	O2—Cu1—N2—C10	−3.6 (12)
C14—S2—O2—Cu1	−109.80 (17)	O3—Cu1—N2—C10	170.5 (2)
C15—S2—O2—Cu1	146.32 (17)	N1—Cu1—N2—C10	−5.2 (2)
O3—Cu1—O2—S2	−42.44 (15)	O4—Cu1—N2—C10	80.2 (2)
N2—Cu1—O2—S2	131.6 (11)	O1—Cu1—N2—C10	−95.0 (2)
N1—Cu1—O2—S2	133.21 (15)	C9—N1—C1—C2	0.4 (5)
O4—Cu1—O2—S2	47.57 (14)	Cu1—N1—C1—C2	−177.8 (2)
O1—Cu1—O2—S2	−136.67 (15)	N1—C1—C2—C3	0.8 (5)
C16—S3—O3—Cu1	−106.8 (2)	C1—C2—C3—C4	−1.3 (5)
C17—S3—O3—Cu1	148.92 (19)	C2—C3—C4—C9	0.7 (5)
O2—Cu1—O3—S3	−41.26 (17)	C10—C5—C6—C7	−0.3 (5)
N2—Cu1—O3—S3	139.26 (17)	C5—C6—C7—C8	0.5 (5)
N1—Cu1—O3—S3	166.9 (5)	C10—N2—C8—C7	−0.9 (5)
O4—Cu1—O3—S3	−128.69 (16)	Cu1—N2—C8—C7	174.3 (2)
O1—Cu1—O3—S3	45.24 (17)	C6—C7—C8—N2	0.1 (5)
C19—S4—O4—Cu1	−49.5 (3)	C1—N1—C9—C4	−1.1 (4)
C18—S4—O4—Cu1	54.3 (3)	Cu1—N1—C9—C4	177.3 (2)
O2—Cu1—O4—S4	−133.1 (2)	C1—N1—C9—C10	179.0 (3)
O3—Cu1—O4—S4	−38.5 (2)	Cu1—N1—C9—C10	−2.7 (3)
N2—Cu1—O4—S4	51.9 (2)	C3—C4—C9—N1	0.5 (5)
N1—Cu1—O4—S4	133.1 (2)	C3—C4—C9—C10	−179.5 (3)
O1—Cu1—O4—S4	−166.6 (5)	C8—N2—C10—C5	1.1 (5)
O2—Cu1—N1—C1	2.6 (3)	Cu1—N2—C10—C5	−174.6 (2)
O3—Cu1—N1—C1	154.5 (5)	C8—N2—C10—C9	−179.1 (3)
N2—Cu1—N1—C1	−177.5 (3)	Cu1—N2—C10—C9	5.2 (3)
O4—Cu1—N1—C1	89.8 (3)	C6—C5—C10—N2	−0.5 (5)
O1—Cu1—N1—C1	−83.5 (3)	C6—C5—C10—C9	179.7 (3)
O2—Cu1—N1—C9	−175.6 (2)	N1—C9—C10—N2	−1.6 (4)
O3—Cu1—N1—C9	−23.7 (7)	C4—C9—C10—N2	178.4 (3)
N2—Cu1—N1—C9	4.2 (2)	N1—C9—C10—C5	178.1 (3)
O4—Cu1—N1—C9	−88.5 (2)	C4—C9—C10—C5	−1.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2	0.95	2.52	3.046 (4)	115
C6—H6···O8i	0.95	2.47	3.255 (5)	140
C8—H8···O3	0.95	2.42	2.946 (4)	115
C4—H4···O1ii	0.95	2.35	3.219 (4)	151
C16—H16B···O5iii	0.98	2.56	3.411 (5)	145
C17—H17B···O5iii	0.98	2.40	3.306 (5)	153
C15—H15C···O7iv	0.98	2.51	3.320 (5)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2	0.95	2.52	3.046 (4)	115
C6—H6⋯O8i	0.95	2.47	3.255 (5)	140
C8—H8⋯O3	0.95	2.42	2.946 (4)	115
C4—H4⋯O1ii	0.95	2.35	3.219 (4)	151
C16—H16B⋯O5iii	0.98	2.56	3.411 (5)	145
C17—H17B⋯O5iii	0.98	2.40	3.306 (5)	153
C15—H15C⋯O7iv	0.98	2.51	3.320 (5)	140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .