(Acetato-κO)bis-(2,2'-bipyridyl-κN,N')copper(II)-ethyl sulfate-methyl sulfate (1/0.5/0.5).

In the title complex, [Cu(C(2)H(3)O(2))(C(10)H(8)N(2))(2)](CH(3)CH(2)OSO(3))(0.5)(CH(3)OSO(3))(0.5), the Cu(II) ion is bis-chelated by two 2,2'-bipyridine lignds and coordinated by an O atom of an acetate ligand in a CuN(4)O disorted square-pyramidal environment. In the structure, equal amounts of methyl sulfate and ethyl sulfate anions are disordered on the same crystallographic sites. The crystal structure is stabilized by weak inter-molecular C-H⋯O inter-actions.

Related literature

For genernal background to supra­molecular assembly and crystal engineering, see: Aakeröy et al. (1998 ▶); Batten & Robson (1998 ▶); Yaghi et al. (1998 ▶); Kitagawa et al. (2004 ▶); Lu et al. (2006 ▶). For related strutures, see: Akrivos et al. (1994 ▶); Blake et al. (2000 ▶); Belokon et al. (2002 ▶); Lopez-Sandoval et al. (2004 ▶).

Experimental

Crystal data

[Cu(C2H3O2)(C10H8N2)2](C2H5O4S)0.5(CH3O4S)0.5

M = 553.06

Triclinic,

a = 7.1314 (7) Å

b = 13.1173 (13) Å

c = 13.2783 (14) Å

α = 91.875 (1)°

β = 104.673 (1)°

γ = 101.162 (1)°

V = 1174.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.07 mm−1

T = 291 (2) K

0.36 × 0.27 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.703, T max = 0.800

8803 measured reflections

4347 independent reflections

3848 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.076

S = 1.04

4347 reflections

331 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037331/lh2732sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037331/lh2732Isup2.hkl

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

[Cu(C2H3O2)(C10H8N2)2](C2H5O4S)0.5(CH3O4S)0.5	Z = 2
Mr = 553.06	F000 = 570
Triclinic, P1	Dx = 1.564 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.1314 (7) Å	Cell parameters from 4397 reflections
b = 13.1173 (13) Å	θ = 2.3–28.1º
c = 13.2783 (14) Å	µ = 1.07 mm−1
α = 91.875 (1)º	T = 291 (2) K
β = 104.673 (1)º	Block, green
γ = 101.162 (1)º	0.36 × 0.27 × 0.22 mm
V = 1174.5 (2) Å3

Bruker SMART CCD area-detector diffractometer	4347 independent reflections
Radiation source: fine-focus sealed tube	3848 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.015
T = 291(2) K	θmax = 25.5º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.703, Tmax = 0.800	k = −15→15
8803 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H-atom parameters constrained
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0354P)2 + 0.5539P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
4347 reflections	Δρmax = 0.55 e Å−3
331 parameters	Δρmin = −0.25 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
Cu1	0.69835 (4)	0.608241 (18)	0.760447 (18)	0.03168 (9)
O1	0.8543 (2)	0.52120 (12)	0.84602 (12)	0.0433 (4)
O2	0.9954 (3)	0.51379 (14)	0.71558 (14)	0.0550 (4)
N1	0.5337 (2)	0.67731 (13)	0.64598 (13)	0.0317 (4)
N2	0.4968 (2)	0.48175 (13)	0.68357 (13)	0.0323 (4)
N3	0.6247 (3)	0.68159 (15)	0.89221 (14)	0.0383 (4)
N4	0.9261 (2)	0.73567 (13)	0.80779 (13)	0.0326 (4)
C1	0.4895 (3)	0.38259 (17)	0.70852 (18)	0.0415 (5)
H1A	0.5772	0.3699	0.7694	0.050*
C2	0.3570 (3)	0.29897 (18)	0.6473 (2)	0.0461 (6)
H2A	0.3552	0.2313	0.6666	0.055*
C3	0.2279 (3)	0.31788 (17)	0.55725 (19)	0.0430 (5)
H3A	0.1371	0.2629	0.5149	0.052*
C4	0.2337 (3)	0.41910 (16)	0.52997 (17)	0.0365 (5)
H4A	0.1480	0.4329	0.4689	0.044*
C5	0.3697 (3)	0.49981 (15)	0.59519 (15)	0.0289 (4)
C6	0.3895 (3)	0.61088 (15)	0.57390 (15)	0.0284 (4)
C7	0.2728 (3)	0.64571 (17)	0.48789 (16)	0.0362 (5)
H7A	0.1754	0.5988	0.4389	0.043*
C8	0.3031 (3)	0.75132 (18)	0.47579 (18)	0.0434 (5)
H8A	0.2278	0.7761	0.4176	0.052*
C9	0.4454 (4)	0.81974 (18)	0.55037 (19)	0.0469 (6)
H9A	0.4651	0.8912	0.5443	0.056*
C10	0.5578 (3)	0.78016 (16)	0.63401 (18)	0.0403 (5)
H10A	0.6543	0.8263	0.6843	0.048*
C11	0.9728 (3)	0.48732 (17)	0.80077 (19)	0.0424 (5)
C12	1.0787 (4)	0.4086 (2)	0.8584 (3)	0.0645 (8)
H12A	1.1963	0.4071	0.8362	0.097*
H12B	0.9929	0.3408	0.8434	0.097*
H12C	1.1144	0.4280	0.9322	0.097*
C13	1.0729 (3)	0.75999 (18)	0.76051 (18)	0.0424 (5)
H13A	1.0669	0.7195	0.7005	0.051*
C14	1.2314 (4)	0.84204 (19)	0.7971 (2)	0.0516 (6)
H14A	1.3283	0.8584	0.7613	0.062*
C15	1.2432 (4)	0.89909 (19)	0.8875 (2)	0.0531 (7)
H15A	1.3504	0.9541	0.9147	0.064*
C16	1.0960 (4)	0.87503 (18)	0.93812 (19)	0.0467 (6)
H16A	1.1037	0.9132	0.9999	0.056*
C17	0.9355 (3)	0.79297 (16)	0.89594 (15)	0.0338 (5)
C18	0.7654 (3)	0.76315 (16)	0.94229 (16)	0.0358 (5)
C19	0.7519 (4)	0.8162 (2)	1.03148 (18)	0.0531 (6)
H19A	0.8519	0.8722	1.0654	0.064*
C20	0.5900 (5)	0.7851 (3)	1.0690 (2)	0.0658 (8)
H20A	0.5784	0.8202	1.1284	0.079*
C21	0.4449 (5)	0.7017 (3)	1.0183 (2)	0.0660 (8)
H21A	0.3340	0.6793	1.0428	0.079*
C22	0.4667 (4)	0.6515 (2)	0.9297 (2)	0.0532 (6)
H22A	0.3684	0.5951	0.8951	0.064*
S1	0.65876 (9)	0.06973 (4)	0.75424 (4)	0.04017 (14)
O3	0.7495 (3)	0.17515 (13)	0.79359 (16)	0.0663 (5)
O4	0.4498 (3)	0.05525 (16)	0.70285 (18)	0.0724 (6)
O5	0.7039 (3)	−0.00602 (14)	0.82714 (14)	0.0622 (5)
O6	0.7439 (3)	0.04364 (14)	0.65787 (13)	0.0530 (4)
C23A	0.9552 (16)	0.054 (5)	0.690 (4)	0.066 (4)	0.50
H23A	1.0010	0.0371	0.6304	0.099*	0.50
H23B	0.9895	0.0082	0.7426	0.099*	0.50
H23C	1.0165	0.1250	0.7167	0.099*	0.50
C23B	0.9520 (17)	0.047 (5)	0.674 (4)	0.066 (4)	0.50
H23D	0.9971	0.0023	0.7275	0.079*	0.50
H23E	1.0274	0.1176	0.6951	0.079*	0.50
C24B	0.9788 (9)	0.0102 (6)	0.5741 (5)	0.0774 (19)	0.50
H24A	1.1174	0.0151	0.5804	0.116*	0.50
H24B	0.9268	0.0526	0.5207	0.116*	0.50
H24C	0.9097	−0.0610	0.5558	0.116*	0.50

	U11	U22	U33	U12	U13	U23
Cu1	0.03401 (15)	0.02954 (14)	0.02825 (14)	0.00588 (10)	0.00340 (10)	−0.00086 (10)
O1	0.0449 (9)	0.0416 (9)	0.0391 (9)	0.0128 (7)	0.0004 (7)	0.0030 (7)
O2	0.0610 (11)	0.0528 (11)	0.0479 (10)	0.0116 (9)	0.0098 (9)	−0.0044 (8)
N1	0.0361 (9)	0.0272 (9)	0.0297 (9)	0.0068 (7)	0.0056 (7)	−0.0029 (7)
N2	0.0332 (9)	0.0299 (9)	0.0330 (9)	0.0052 (7)	0.0081 (7)	0.0034 (7)
N3	0.0376 (10)	0.0447 (11)	0.0345 (10)	0.0115 (8)	0.0108 (8)	0.0041 (8)
N4	0.0324 (9)	0.0318 (9)	0.0307 (9)	0.0053 (7)	0.0049 (7)	−0.0002 (7)
C1	0.0423 (12)	0.0370 (12)	0.0442 (13)	0.0056 (10)	0.0103 (10)	0.0123 (10)
C2	0.0457 (13)	0.0294 (12)	0.0638 (16)	0.0025 (10)	0.0192 (12)	0.0098 (11)
C3	0.0388 (12)	0.0316 (12)	0.0538 (14)	−0.0026 (9)	0.0121 (11)	−0.0040 (10)
C4	0.0331 (11)	0.0356 (11)	0.0376 (12)	0.0030 (9)	0.0074 (9)	−0.0022 (9)
C5	0.0261 (10)	0.0302 (10)	0.0311 (10)	0.0043 (8)	0.0104 (8)	0.0005 (8)
C6	0.0262 (10)	0.0290 (10)	0.0306 (10)	0.0052 (8)	0.0093 (8)	−0.0011 (8)
C7	0.0314 (11)	0.0385 (12)	0.0352 (11)	0.0056 (9)	0.0041 (9)	0.0013 (9)
C8	0.0429 (13)	0.0426 (13)	0.0423 (13)	0.0132 (10)	0.0030 (10)	0.0099 (10)
C9	0.0539 (14)	0.0297 (12)	0.0549 (15)	0.0116 (10)	0.0082 (12)	0.0057 (10)
C10	0.0444 (12)	0.0278 (11)	0.0433 (13)	0.0065 (9)	0.0037 (10)	−0.0039 (9)
C11	0.0365 (12)	0.0317 (11)	0.0480 (14)	0.0029 (9)	−0.0045 (10)	−0.0050 (10)
C12	0.0500 (15)	0.0452 (15)	0.095 (2)	0.0167 (12)	0.0066 (15)	0.0143 (15)
C13	0.0427 (13)	0.0403 (12)	0.0444 (13)	0.0061 (10)	0.0141 (10)	0.0037 (10)
C14	0.0409 (13)	0.0444 (14)	0.0699 (17)	0.0048 (11)	0.0175 (12)	0.0134 (12)
C15	0.0389 (13)	0.0372 (13)	0.0699 (18)	−0.0023 (10)	−0.0019 (12)	0.0053 (12)
C16	0.0533 (14)	0.0340 (12)	0.0420 (13)	0.0071 (10)	−0.0044 (11)	−0.0055 (10)
C17	0.0393 (11)	0.0297 (11)	0.0295 (10)	0.0118 (9)	0.0004 (9)	0.0029 (8)
C18	0.0480 (13)	0.0343 (11)	0.0267 (10)	0.0174 (10)	0.0059 (9)	0.0039 (8)
C19	0.0791 (18)	0.0499 (15)	0.0360 (13)	0.0268 (13)	0.0160 (13)	−0.0002 (11)
C20	0.092 (2)	0.081 (2)	0.0448 (15)	0.0477 (19)	0.0317 (16)	0.0100 (14)
C21	0.0636 (18)	0.101 (2)	0.0576 (17)	0.0440 (18)	0.0362 (15)	0.0336 (17)
C22	0.0437 (14)	0.0680 (18)	0.0526 (15)	0.0148 (12)	0.0176 (12)	0.0150 (13)
S1	0.0482 (3)	0.0304 (3)	0.0421 (3)	0.0057 (2)	0.0144 (3)	0.0001 (2)
O3	0.0808 (13)	0.0359 (10)	0.0769 (13)	−0.0036 (9)	0.0255 (11)	−0.0142 (9)
O4	0.0535 (11)	0.0638 (13)	0.0943 (16)	0.0101 (10)	0.0111 (11)	0.0104 (11)
O5	0.0844 (14)	0.0543 (11)	0.0475 (10)	0.0122 (10)	0.0173 (9)	0.0154 (9)
O6	0.0659 (11)	0.0516 (10)	0.0441 (9)	0.0147 (9)	0.0175 (8)	0.0019 (8)
C23A	0.0588 (18)	0.083 (7)	0.068 (10)	0.029 (2)	0.0290 (18)	0.013 (7)
C23B	0.0588 (18)	0.083 (7)	0.068 (10)	0.029 (2)	0.0290 (18)	0.013 (7)
C24B	0.064 (4)	0.094 (5)	0.080 (4)	0.021 (3)	0.028 (3)	−0.013 (4)

Cu1—O1	1.9411 (15)	C12—H12B	0.9600
Cu1—N2	2.0207 (17)	C12—H12C	0.9600
Cu1—N1	2.0266 (17)	C13—C14	1.374 (3)
Cu1—N4	2.0471 (17)	C13—H13A	0.9300
Cu1—N3	2.1940 (18)	C14—C15	1.369 (4)
O1—C11	1.287 (3)	C14—H14A	0.9300
O2—C11	1.234 (3)	C15—C16	1.377 (4)
N1—C10	1.346 (3)	C15—H15A	0.9300
N1—C6	1.354 (2)	C16—C17	1.393 (3)
N2—C1	1.347 (3)	C16—H16A	0.9300
N2—C5	1.348 (3)	C17—C18	1.488 (3)
N3—C18	1.339 (3)	C18—C19	1.388 (3)
N3—C22	1.341 (3)	C19—C20	1.367 (4)
N4—C13	1.345 (3)	C19—H19A	0.9300
N4—C17	1.350 (3)	C20—C21	1.372 (4)
C1—C2	1.381 (3)	C20—H20A	0.9300
C1—H1A	0.9300	C21—C22	1.386 (4)
C2—C3	1.374 (3)	C21—H21A	0.9300
C2—H2A	0.9300	C22—H22A	0.9300
C3—C4	1.383 (3)	S1—O3	1.4279 (18)
C3—H3A	0.9300	S1—O5	1.4341 (18)
C4—C5	1.389 (3)	S1—O4	1.445 (2)
C4—H4A	0.9300	S1—O6	1.6026 (17)
C5—C6	1.480 (3)	O6—C23A	1.436 (7)
C6—C7	1.380 (3)	O6—C23B	1.438 (7)
C7—C8	1.381 (3)	C23A—H23A	0.9600
C7—H7A	0.9300	C23A—H23B	0.9600
C8—C9	1.377 (3)	C23A—H23C	0.9600
C8—H8A	0.9300	C23B—C24B	1.46 (5)
C9—C10	1.376 (3)	C23B—H23D	0.9700
C9—H9A	0.9300	C23B—H23E	0.9700
C10—H10A	0.9300	C24B—H24A	0.9600
C11—C12	1.511 (3)	C24B—H24B	0.9600
C12—H12A	0.9600	C24B—H24C	0.9600
O1—Cu1—N2	91.45 (7)	H12A—C12—H12B	109.5
O1—Cu1—N1	167.87 (6)	C11—C12—H12C	109.5
N2—Cu1—N1	80.14 (7)	H12A—C12—H12C	109.5
O1—Cu1—N4	91.03 (7)	H12B—C12—H12C	109.5
N2—Cu1—N4	166.61 (7)	N4—C13—C14	122.8 (2)
N1—Cu1—N4	95.20 (7)	N4—C13—H13A	118.6
O1—Cu1—N3	94.44 (7)	C14—C13—H13A	118.6
N2—Cu1—N3	115.38 (7)	C15—C14—C13	118.3 (2)
N1—Cu1—N3	97.05 (7)	C15—C14—H14A	120.8
N4—Cu1—N3	77.52 (7)	C13—C14—H14A	120.8
C11—O1—Cu1	112.76 (15)	C14—C15—C16	120.0 (2)
C10—N1—C6	118.32 (18)	C14—C15—H15A	120.0
C10—N1—Cu1	126.67 (14)	C16—C15—H15A	120.0
C6—N1—Cu1	114.99 (13)	C15—C16—C17	119.3 (2)
C1—N2—C5	118.53 (18)	C15—C16—H16A	120.3
C1—N2—Cu1	125.94 (15)	C17—C16—H16A	120.3
C5—N2—Cu1	115.32 (13)	N4—C17—C16	120.6 (2)
C18—N3—C22	118.5 (2)	N4—C17—C18	115.85 (18)
C18—N3—Cu1	113.03 (14)	C16—C17—C18	123.6 (2)
C22—N3—Cu1	128.37 (17)	N3—C18—C19	121.8 (2)
C13—N4—C17	118.92 (18)	N3—C18—C17	115.71 (18)
C13—N4—Cu1	123.50 (14)	C19—C18—C17	122.5 (2)
C17—N4—Cu1	117.38 (14)	C20—C19—C18	119.3 (3)
N2—C1—C2	122.6 (2)	C20—C19—H19A	120.3
N2—C1—H1A	118.7	C18—C19—H19A	120.3
C2—C1—H1A	118.7	C19—C20—C21	119.4 (3)
C3—C2—C1	118.6 (2)	C19—C20—H20A	120.3
C3—C2—H2A	120.7	C21—C20—H20A	120.3
C1—C2—H2A	120.7	C20—C21—C22	118.7 (3)
C2—C3—C4	119.7 (2)	C20—C21—H21A	120.6
C2—C3—H3A	120.2	C22—C21—H21A	120.6
C4—C3—H3A	120.2	N3—C22—C21	122.3 (3)
C3—C4—C5	118.9 (2)	N3—C22—H22A	118.9
C3—C4—H4A	120.5	C21—C22—H22A	118.9
C5—C4—H4A	120.5	O3—S1—O5	114.52 (12)
N2—C5—C4	121.65 (18)	O3—S1—O4	113.33 (13)
N2—C5—C6	114.68 (17)	O5—S1—O4	113.34 (12)
C4—C5—C6	123.66 (18)	O3—S1—O6	107.18 (11)
N1—C6—C7	121.76 (18)	O5—S1—O6	106.19 (11)
N1—C6—C5	114.55 (17)	O4—S1—O6	100.85 (12)
C7—C6—C5	123.69 (18)	C23A—O6—S1	111.6 (19)
C6—C7—C8	119.0 (2)	C23B—O6—S1	120.4 (18)
C6—C7—H7A	120.5	O6—C23A—H23A	109.5
C8—C7—H7A	120.5	O6—C23A—H23B	109.5
C9—C8—C7	119.6 (2)	O6—C23A—H23C	109.5
C9—C8—H8A	120.2	O6—C23B—C24B	107 (2)
C7—C8—H8A	120.2	O6—C23B—H23D	110.3
C10—C9—C8	118.6 (2)	C24B—C23B—H23D	110.3
C10—C9—H9A	120.7	O6—C23B—H23E	110.3
C8—C9—H9A	120.7	C24B—C23B—H23E	110.3
N1—C10—C9	122.6 (2)	H23D—C23B—H23E	108.6
N1—C10—H10A	118.7	C23B—C24B—H24A	109.5
C9—C10—H10A	118.7	C23B—C24B—H24B	109.5
O2—C11—O1	123.5 (2)	H24A—C24B—H24B	109.5
O2—C11—C12	121.8 (2)	C23B—C24B—H24C	109.5
O1—C11—C12	114.7 (2)	H24A—C24B—H24C	109.5
C11—C12—H12A	109.5	H24B—C24B—H24C	109.5
C11—C12—H12B	109.5
N2—Cu1—O1—C11	83.73 (15)	C10—N1—C6—C5	−178.14 (18)
N1—Cu1—O1—C11	37.9 (4)	Cu1—N1—C6—C5	3.6 (2)
N4—Cu1—O1—C11	−83.11 (15)	N2—C5—C6—N1	0.6 (2)
N3—Cu1—O1—C11	−160.68 (15)	C4—C5—C6—N1	−178.70 (18)
O1—Cu1—N1—C10	−136.1 (3)	N2—C5—C6—C7	−179.65 (18)
N2—Cu1—N1—C10	177.24 (19)	C4—C5—C6—C7	1.0 (3)
N4—Cu1—N1—C10	−15.43 (18)	N1—C6—C7—C8	−0.6 (3)
N3—Cu1—N1—C10	62.60 (18)	C5—C6—C7—C8	179.67 (19)
O1—Cu1—N1—C6	42.0 (4)	C6—C7—C8—C9	−1.4 (3)
N2—Cu1—N1—C6	−4.66 (13)	C7—C8—C9—C10	1.8 (4)
N4—Cu1—N1—C6	162.67 (14)	C6—N1—C10—C9	−1.7 (3)
N3—Cu1—N1—C6	−119.29 (14)	Cu1—N1—C10—C9	176.35 (17)
O1—Cu1—N2—C1	8.46 (18)	C8—C9—C10—N1	−0.2 (4)
N1—Cu1—N2—C1	179.67 (18)	Cu1—O1—C11—O2	5.2 (3)
N4—Cu1—N2—C1	109.1 (3)	Cu1—O1—C11—C12	−172.77 (16)
N3—Cu1—N2—C1	−87.15 (18)	C17—N4—C13—C14	−1.1 (3)
O1—Cu1—N2—C5	−166.17 (14)	Cu1—N4—C13—C14	−175.82 (17)
N1—Cu1—N2—C5	5.04 (14)	N4—C13—C14—C15	2.3 (4)
N4—Cu1—N2—C5	−65.5 (3)	C13—C14—C15—C16	−1.4 (4)
N3—Cu1—N2—C5	98.22 (14)	C14—C15—C16—C17	−0.5 (4)
O1—Cu1—N3—C18	84.49 (15)	C13—N4—C17—C16	−0.9 (3)
N2—Cu1—N3—C18	178.22 (13)	Cu1—N4—C17—C16	174.12 (15)
N1—Cu1—N3—C18	−99.38 (14)	C13—N4—C17—C18	178.51 (18)
N4—Cu1—N3—C18	−5.59 (14)	Cu1—N4—C17—C18	−6.4 (2)
O1—Cu1—N3—C22	−91.6 (2)	C15—C16—C17—N4	1.7 (3)
N2—Cu1—N3—C22	2.1 (2)	C15—C16—C17—C18	−177.7 (2)
N1—Cu1—N3—C22	84.5 (2)	C22—N3—C18—C19	0.4 (3)
N4—Cu1—N3—C22	178.3 (2)	Cu1—N3—C18—C19	−176.14 (17)
O1—Cu1—N4—C13	86.96 (17)	C22—N3—C18—C17	−179.43 (19)
N2—Cu1—N4—C13	−13.7 (4)	Cu1—N3—C18—C17	4.0 (2)
N1—Cu1—N4—C13	−82.63 (17)	N4—C17—C18—N3	1.3 (3)
N3—Cu1—N4—C13	−178.72 (18)	C16—C17—C18—N3	−179.33 (19)
O1—Cu1—N4—C17	−87.84 (15)	N4—C17—C18—C19	−178.58 (19)
N2—Cu1—N4—C17	171.5 (2)	C16—C17—C18—C19	0.8 (3)
N1—Cu1—N4—C17	102.57 (15)	N3—C18—C19—C20	−0.6 (4)
N3—Cu1—N4—C17	6.48 (14)	C17—C18—C19—C20	179.3 (2)
C5—N2—C1—C2	−0.1 (3)	C18—C19—C20—C21	0.5 (4)
Cu1—N2—C1—C2	−174.60 (17)	C19—C20—C21—C22	−0.3 (4)
N2—C1—C2—C3	0.2 (4)	C18—N3—C22—C21	−0.2 (4)
C1—C2—C3—C4	0.2 (3)	Cu1—N3—C22—C21	175.77 (18)
C2—C3—C4—C5	−0.6 (3)	C20—C21—C22—N3	0.1 (4)
C1—N2—C5—C4	−0.3 (3)	O3—S1—O6—C23A	60 (3)
Cu1—N2—C5—C4	174.78 (15)	O5—S1—O6—C23A	−62 (3)
C1—N2—C5—C6	−179.62 (17)	O4—S1—O6—C23A	179 (3)
Cu1—N2—C5—C6	−4.6 (2)	O3—S1—O6—C23B	62 (3)
C3—C4—C5—N2	0.6 (3)	O5—S1—O6—C23B	−61 (3)
C3—C4—C5—C6	179.90 (19)	O4—S1—O6—C23B	−179 (3)
C10—N1—C6—C7	2.1 (3)	S1—O6—C23B—C24B	175 (2)
Cu1—N1—C6—C7	−176.14 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O5i	0.93	2.49	3.339 (3)	151
C12—H12B···O3	0.96	2.46	3.414 (3)	174
C8—H8A···O6ii	0.93	2.59	3.295 (3)	133
C7—H7A···O2ii	0.93	2.39	3.286 (3)	162
C4—H4A···O2ii	0.93	2.58	3.482 (3)	163
C2—H2A···O4	0.93	2.56	3.454 (3)	162
C1—H1A···O1	0.93	2.49	2.992 (3)	114

Cu1—O1	1.9411 (15)
Cu1—N2	2.0207 (17)
Cu1—N1	2.0266 (17)
Cu1—N4	2.0471 (17)
Cu1—N3	2.1940 (18)

O1—Cu1—N2	91.45 (7)
O1—Cu1—N1	167.87 (6)
N2—Cu1—N1	80.14 (7)
O1—Cu1—N4	91.03 (7)
N2—Cu1—N4	166.61 (7)
N1—Cu1—N4	95.20 (7)
O1—Cu1—N3	94.44 (7)
N2—Cu1—N3	115.38 (7)
N1—Cu1—N3	97.05 (7)
N4—Cu1—N3	77.52 (7)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O5i	0.93	2.49	3.339 (3)	151
C12—H12B⋯O3	0.96	2.46	3.414 (3)	174
C8—H8A⋯O6ii	0.93	2.59	3.295 (3)	133
C7—H7A⋯O2ii	0.93	2.39	3.286 (3)	162
C4—H4A⋯O2ii	0.93	2.58	3.482 (3)	163
C2—H2A⋯O4	0.93	2.56	3.454 (3)	162
C1—H1A⋯O1	0.93	2.49	2.992 (3)	114

Symmetry codes: (i) ; (ii) .