catena-Poly[triethyl-ammonium [[tetra-μ-acetato-κ(8)O:O'-dicuprate(II)]-μ-acetato-κ(2)O:O'] tetra-hydro-furan monosolvate].

In the title compound, {[(C(2)H(5))(3)NH][Cu(2)(CH(3)COO)(5)]·C(4)H(8)O}(n), the two different Cu(II) atoms are coordinated in a pseudo-square-pyramidal environment by five O atoms from the acetate ligands. Neighbouring pairs of Cu(II) atoms are linked by four basally coordinating bridging acetate ligands as in the crystal structure of copper acetate monohydrate. The fifth, apically coordinating ligand links two of the dicopper tetra-acetate paddlewheel-units together, thus building a linear coordination polymer which extends along [10-1]. Each apical acetate ligand is linked by an N-H⋯O hydrogen bond to a triethyl-ammonium cation. Weak C-H⋯O hydrogen bonding interactions also occur.

Related literature

For the crystal structure of dicoppertetra­acetate dihydrate, see: van Niekerk & Schoening (1953 ▶); de Meester et al. (1973 ▶). For copper-based coordination polymers, see: Furukawa et al. (2008 ▶). The title compound was obtained as a minor byproduct in the synthesis of a copper–salene compound, see: Kleij et al. (2005 ▶).

Experimental

Crystal data

(C6H16N)[Cu2(C2H3O2)5]·C4H8O

M = 596.60

Monoclinic,

a = 12.1520 (2) Å

b = 12.2726 (2) Å

c = 18.7306 (3) Å

β = 112.956 (1)°

V = 2572.19 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.71 mm−1

T = 100 K

0.25 × 0.09 × 0.06 mm

Data collection

Bruker APEX II CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.681, T max = 0.747

102874 measured reflections

4713 independent reflections

4047 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.062

S = 1.13

4713 reflections

319 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrik, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrik, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812033405/hp2044sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033405/hp2044Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033405/hp2044Isup3.mol

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

(C6H16N)[Cu2(C2H3O2)5]·C4H8O	F(000) = 1248
Mr = 596.60	Dx = 1.541 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9902 reflections
a = 12.1520 (2) Å	θ = 2.4–34.0°
b = 12.2726 (2) Å	µ = 1.71 mm−1
c = 18.7306 (3) Å	T = 100 K
β = 112.956 (1)°	Block, clear dark blue
V = 2572.19 (7) Å3	0.25 × 0.09 × 0.06 mm
Z = 4

Bruker APEX II CCD area-detector diffractometer	4713 independent reflections
Radiation source: micro-focus	4047 reflections with I > 2σ(I)
Multi-layer optics monochromator	Rint = 0.040
Detector resolution: 8 pixels mm-1	θmax = 25.4°, θmin = 1.8°
ω and φ scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.681, Tmax = 0.747	l = −22→22
102874 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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0203P)2 + 2.3331P] where P = (Fo2 + 2Fc2)/3
4713 reflections	(Δ/σ)max = 0.004
319 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Experimental. Absorption correction: SADABS-2008/1 (Bruker, 2009) was used for absorption correction. wR2(int) was 0.1027 before and 0.0524 after correction. The Ratio of minimum to maximum transmission is 0.9107. The λ/2 correction factor is 0.0000.

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
Cu1	0.58451 (2)	0.505128 (19)	0.570813 (12)	0.01381 (7)
Cu2	0.937948 (19)	0.502200 (18)	0.923936 (12)	0.01216 (7)
O1	0.45990 (12)	0.43975 (12)	0.59966 (8)	0.0217 (3)
O2	0.51683 (14)	0.65182 (12)	0.57030 (8)	0.0275 (4)
O3	0.31686 (13)	0.43082 (15)	0.48086 (8)	0.0336 (4)
O4	0.62799 (13)	0.35832 (13)	0.54785 (9)	0.0295 (4)
O5	0.72384 (12)	0.52443 (11)	0.68184 (7)	0.0169 (3)
O6	0.85592 (12)	0.52508 (11)	0.80224 (7)	0.0154 (3)
O7	0.80423 (12)	0.54543 (12)	0.95269 (8)	0.0211 (3)
O8	0.90257 (13)	0.34674 (11)	0.93393 (8)	0.0203 (3)
O9	1.09120 (12)	0.45715 (12)	0.91883 (8)	0.0211 (3)
O10	0.99288 (13)	0.65590 (11)	0.93776 (8)	0.0203 (3)
C1	0.35629 (17)	0.41637 (16)	0.55266 (11)	0.0170 (4)
C2	0.27189 (19)	0.36747 (18)	0.58551 (12)	0.0231 (5)
H2A	0.3171	0.3447	0.6392	0.035*
H2B	0.2317	0.3041	0.5544	0.035*
H2C	0.2121	0.4219	0.5842	0.035*
C3	0.42955 (17)	0.69004 (16)	0.51461 (11)	0.0177 (4)
C4	0.3902 (2)	0.80429 (18)	0.52395 (13)	0.0259 (5)
H4A	0.3487	0.8030	0.5595	0.039*
H4B	0.3360	0.8320	0.4734	0.039*
H4C	0.4603	0.8518	0.5450	0.039*
C5	0.75337 (16)	0.49915 (14)	0.75148 (10)	0.0123 (4)
C6	0.66926 (17)	0.43909 (17)	0.77852 (11)	0.0179 (4)
H6A	0.6513	0.4842	0.8158	0.027*
H6B	0.7064	0.3708	0.8034	0.027*
H6C	0.5951	0.4230	0.7340	0.027*
C7	0.81493 (17)	0.55813 (16)	1.02184 (11)	0.0158 (4)
C8	0.70571 (18)	0.59690 (18)	1.03438 (12)	0.0210 (4)
H8A	0.6998	0.6764	1.0293	0.032*
H8B	0.7125	0.5759	1.0864	0.032*
H8C	0.6340	0.5635	0.9956	0.032*
C9	0.94290 (17)	0.30002 (16)	0.99907 (11)	0.0150 (4)
C10	0.91147 (18)	0.18182 (16)	1.00283 (12)	0.0199 (4)
H10A	0.8507	0.1762	1.0250	0.030*
H10B	0.9832	0.1416	1.0355	0.030*
H10C	0.8801	0.1508	0.9505	0.030*
N1	0.95203 (15)	0.68314 (14)	0.74095 (9)	0.0157 (3)
C11	0.89976 (19)	0.78890 (17)	0.75415 (12)	0.0216 (4)
H11A	0.9146	0.8465	0.7220	0.026*
H11B	0.9409	0.8104	0.8092	0.026*
C12	0.76660 (19)	0.78157 (18)	0.73454 (13)	0.0250 (5)
H12A	0.7520	0.7316	0.7708	0.037*
H12B	0.7260	0.7543	0.6815	0.037*
H12C	0.7357	0.8540	0.7387	0.037*
C13	0.92652 (18)	0.66676 (16)	0.65642 (11)	0.0178 (4)
H13A	0.9663	0.7252	0.6388	0.021*
H13B	0.8394	0.6730	0.6262	0.021*
C14	0.96895 (19)	0.55746 (17)	0.64007 (12)	0.0230 (5)
H14A	0.9390	0.4997	0.6639	0.034*
H14B	1.0565	0.5560	0.6618	0.034*
H14C	0.9388	0.5458	0.5839	0.034*
C15	1.08264 (18)	0.67378 (18)	0.79283 (12)	0.0208 (4)
H15A	1.1132	0.6029	0.7832	0.025*
H15B	1.0912	0.6749	0.8476	0.025*
C16	1.15768 (19)	0.76417 (18)	0.78030 (13)	0.0259 (5)
H16A	1.2415	0.7536	0.8151	0.039*
H16B	1.1296	0.8345	0.7914	0.039*
H16C	1.1506	0.7630	0.7264	0.039*
O11	0.68670 (15)	0.43535 (14)	0.26275 (10)	0.0376 (4)
C17	0.6524 (2)	0.36448 (19)	0.31112 (13)	0.0279 (5)
H17A	0.6561	0.4038	0.3582	0.034*
H17B	0.7072	0.3013	0.3274	0.034*
C18	0.52537 (19)	0.32611 (18)	0.26465 (13)	0.0255 (5)
H18A	0.4663	0.3716	0.2754	0.031*
H18B	0.5146	0.2490	0.2759	0.031*
C19	0.5144 (2)	0.34046 (19)	0.18108 (13)	0.0293 (5)
H19A	0.5431	0.2750	0.1626	0.035*
H19B	0.4308	0.3555	0.1458	0.035*
C20	0.5939 (2)	0.4374 (2)	0.18684 (15)	0.0346 (6)
H20A	0.6284	0.4327	0.1470	0.041*
H20B	0.5476	0.5059	0.1788	0.041*
H1	0.918 (2)	0.632 (2)	0.7560 (13)	0.021 (6)*

	U11	U22	U33	U12	U13	U23
Cu1	0.01246 (12)	0.01771 (13)	0.00901 (12)	−0.00095 (9)	0.00175 (9)	0.00001 (9)
Cu2	0.01315 (12)	0.01314 (12)	0.00850 (12)	−0.00060 (9)	0.00238 (9)	0.00073 (9)
O1	0.0174 (7)	0.0319 (8)	0.0128 (7)	−0.0052 (6)	0.0027 (6)	0.0026 (6)
O2	0.0324 (9)	0.0187 (8)	0.0196 (8)	0.0037 (7)	−0.0027 (7)	−0.0015 (6)
O3	0.0194 (8)	0.0648 (12)	0.0126 (7)	−0.0166 (8)	0.0020 (6)	0.0037 (8)
O4	0.0259 (8)	0.0317 (9)	0.0204 (8)	0.0122 (7)	−0.0022 (6)	−0.0061 (7)
O5	0.0154 (7)	0.0231 (7)	0.0085 (6)	−0.0025 (6)	0.0007 (5)	0.0013 (5)
O6	0.0148 (7)	0.0179 (7)	0.0096 (6)	−0.0037 (5)	0.0007 (5)	0.0013 (5)
O7	0.0167 (7)	0.0308 (8)	0.0147 (7)	0.0024 (6)	0.0050 (6)	−0.0011 (6)
O8	0.0247 (7)	0.0162 (7)	0.0137 (7)	−0.0020 (6)	0.0007 (6)	0.0017 (6)
O9	0.0178 (7)	0.0307 (8)	0.0139 (7)	0.0050 (6)	0.0051 (6)	0.0018 (6)
O10	0.0275 (8)	0.0158 (7)	0.0141 (7)	−0.0045 (6)	0.0043 (6)	0.0002 (6)
C1	0.0183 (10)	0.0164 (10)	0.0170 (10)	0.0010 (8)	0.0076 (8)	−0.0008 (8)
C2	0.0226 (11)	0.0275 (12)	0.0210 (11)	−0.0034 (9)	0.0103 (9)	0.0004 (9)
C3	0.0181 (10)	0.0191 (10)	0.0185 (10)	−0.0008 (8)	0.0101 (8)	0.0024 (8)
C4	0.0281 (12)	0.0214 (11)	0.0282 (12)	0.0028 (9)	0.0109 (10)	−0.0006 (9)
C5	0.0139 (9)	0.0083 (9)	0.0140 (9)	0.0010 (7)	0.0046 (8)	−0.0016 (7)
C6	0.0157 (10)	0.0205 (10)	0.0143 (9)	−0.0019 (8)	0.0024 (8)	0.0008 (8)
C7	0.0188 (10)	0.0113 (9)	0.0176 (10)	−0.0024 (8)	0.0074 (8)	0.0002 (8)
C8	0.0193 (10)	0.0240 (11)	0.0212 (10)	0.0010 (8)	0.0094 (9)	0.0000 (9)
C9	0.0136 (9)	0.0157 (10)	0.0156 (10)	0.0020 (8)	0.0057 (8)	0.0009 (8)
C10	0.0218 (10)	0.0161 (10)	0.0189 (10)	−0.0013 (8)	0.0047 (8)	0.0015 (8)
N1	0.0184 (8)	0.0137 (8)	0.0157 (8)	−0.0030 (7)	0.0073 (7)	−0.0003 (7)
C11	0.0292 (11)	0.0154 (10)	0.0214 (11)	−0.0020 (8)	0.0111 (9)	−0.0018 (8)
C12	0.0281 (12)	0.0214 (11)	0.0290 (12)	0.0048 (9)	0.0149 (10)	0.0011 (9)
C13	0.0208 (10)	0.0182 (10)	0.0132 (9)	−0.0015 (8)	0.0053 (8)	0.0002 (8)
C14	0.0260 (11)	0.0220 (11)	0.0224 (11)	−0.0005 (9)	0.0110 (9)	−0.0035 (9)
C15	0.0193 (10)	0.0253 (11)	0.0159 (10)	−0.0025 (9)	0.0047 (8)	0.0016 (9)
C16	0.0238 (11)	0.0251 (12)	0.0305 (12)	−0.0058 (9)	0.0124 (10)	−0.0032 (10)
O11	0.0344 (9)	0.0347 (10)	0.0437 (10)	−0.0099 (8)	0.0151 (8)	−0.0029 (8)
C17	0.0300 (12)	0.0254 (12)	0.0281 (12)	0.0035 (9)	0.0110 (10)	−0.0050 (10)
C18	0.0254 (12)	0.0222 (11)	0.0295 (12)	0.0057 (9)	0.0114 (10)	0.0024 (9)
C19	0.0284 (12)	0.0298 (12)	0.0281 (12)	0.0012 (10)	0.0091 (10)	0.0000 (10)
C20	0.0373 (14)	0.0307 (13)	0.0414 (14)	0.0035 (11)	0.0216 (12)	0.0080 (11)

Cu1—O1	1.9664 (14)	C9—O10ii	1.258 (2)
Cu1—O4	1.9717 (15)	C9—C10	1.509 (3)
Cu1—O3i	1.9738 (15)	C10—H10A	0.9800
Cu1—O2	1.9777 (15)	C10—H10B	0.9800
Cu1—O5	2.1216 (13)	C10—H10C	0.9800
Cu1—Cu1i	2.6498 (4)	N1—C13	1.504 (2)
Cu2—O7	1.9735 (14)	N1—C11	1.507 (3)
Cu2—O9	1.9804 (14)	N1—C15	1.508 (3)
Cu2—O8	1.9806 (14)	N1—H1	0.85 (2)
Cu2—O10	1.9839 (14)	C11—C12	1.516 (3)
Cu2—O6	2.1204 (13)	C11—H11A	0.9900
Cu2—Cu2ii	2.6542 (4)	C11—H11B	0.9900
O1—C1	1.256 (2)	C12—H12A	0.9800
O2—C3	1.253 (2)	C12—H12B	0.9800
O3—C1	1.252 (2)	C12—H12C	0.9800
O3—Cu1i	1.9739 (15)	C13—C14	1.511 (3)
O4—C3i	1.254 (2)	C13—H13A	0.9900
O5—C5	1.250 (2)	C13—H13B	0.9900
O6—C5	1.278 (2)	C14—H14A	0.9800
O7—C7	1.260 (2)	C14—H14B	0.9800
O8—C9	1.261 (2)	C14—H14C	0.9800
O9—C7ii	1.258 (2)	C15—C16	1.511 (3)
O10—C9ii	1.258 (2)	C15—H15A	0.9900
C1—C2	1.511 (3)	C15—H15B	0.9900
C2—H2A	0.9800	C16—H16A	0.9800
C2—H2B	0.9800	C16—H16B	0.9800
C2—H2C	0.9800	C16—H16C	0.9800
C3—O4i	1.254 (2)	O11—C20	1.429 (3)
C3—C4	1.513 (3)	O11—C17	1.430 (3)
C4—H4A	0.9800	C17—C18	1.521 (3)
C4—H4B	0.9800	C17—H17A	0.9900
C4—H4C	0.9800	C17—H17B	0.9900
C5—C6	1.499 (3)	C18—C19	1.529 (3)
C6—H6A	0.9800	C18—H18A	0.9900
C6—H6B	0.9800	C18—H18B	0.9900
C6—H6C	0.9800	C19—C20	1.510 (3)
C7—O9ii	1.258 (2)	C19—H19A	0.9900
C7—C8	1.512 (3)	C19—H19B	0.9900
C8—H8A	0.9800	C20—H20A	0.9900
C8—H8B	0.9800	C20—H20B	0.9900
C8—H8C	0.9800
O1—Cu1—O4	89.30 (7)	O10ii—C9—O8	125.38 (18)
O1—Cu1—O3i	167.73 (6)	O10ii—C9—C10	116.43 (17)
O4—Cu1—O3i	89.50 (8)	O8—C9—C10	118.18 (17)
O1—Cu1—O2	90.54 (7)	C9—C10—H10A	109.5
O4—Cu1—O2	167.71 (6)	C9—C10—H10B	109.5
O3i—Cu1—O2	88.05 (8)	H10A—C10—H10B	109.5
O1—Cu1—O5	100.48 (5)	C9—C10—H10C	109.5
O4—Cu1—O5	97.85 (6)	H10A—C10—H10C	109.5
O3i—Cu1—O5	91.78 (6)	H10B—C10—H10C	109.5
O2—Cu1—O5	94.27 (6)	C13—N1—C11	111.15 (15)
O1—Cu1—Cu1i	82.90 (4)	C13—N1—C15	113.66 (15)
O4—Cu1—Cu1i	84.68 (4)	C11—N1—C15	111.40 (16)
O3i—Cu1—Cu1i	84.83 (4)	C13—N1—H1	108.7 (15)
O2—Cu1—Cu1i	83.10 (4)	C11—N1—H1	106.9 (16)
O5—Cu1—Cu1i	175.77 (4)	C15—N1—H1	104.5 (15)
O7—Cu2—O9	167.99 (6)	N1—C11—C12	112.80 (17)
O7—Cu2—O8	90.06 (6)	N1—C11—H11A	109.0
O9—Cu2—O8	88.77 (6)	C12—C11—H11A	109.0
O7—Cu2—O10	88.84 (6)	N1—C11—H11B	109.0
O9—Cu2—O10	89.82 (6)	C12—C11—H11B	109.0
O8—Cu2—O10	167.95 (6)	H11A—C11—H11B	107.8
O7—Cu2—O6	99.55 (5)	C11—C12—H12A	109.5
O9—Cu2—O6	92.39 (5)	C11—C12—H12B	109.5
O8—Cu2—O6	101.58 (5)	H12A—C12—H12B	109.5
O10—Cu2—O6	90.44 (5)	C11—C12—H12C	109.5
O7—Cu2—Cu2ii	84.03 (4)	H12A—C12—H12C	109.5
O9—Cu2—Cu2ii	83.96 (4)	H12B—C12—H12C	109.5
O8—Cu2—Cu2ii	86.12 (4)	N1—C13—C14	112.69 (16)
O10—Cu2—Cu2ii	81.83 (4)	N1—C13—H13A	109.1
O6—Cu2—Cu2ii	171.44 (4)	C14—C13—H13A	109.1
C1—O1—Cu1	124.71 (13)	N1—C13—H13B	109.1
C3—O2—Cu1	124.07 (13)	C14—C13—H13B	109.1
C1—O3—Cu1i	122.14 (13)	H13A—C13—H13B	107.8
C3i—O4—Cu1	122.47 (13)	C13—C14—H14A	109.5
C5—O5—Cu1	142.18 (12)	C13—C14—H14B	109.5
C5—O6—Cu2	132.82 (12)	H14A—C14—H14B	109.5
C7—O7—Cu2	123.23 (13)	C13—C14—H14C	109.5
C9—O8—Cu2	120.83 (13)	H14A—C14—H14C	109.5
C7ii—O9—Cu2	123.01 (13)	H14B—C14—H14C	109.5
C9ii—O10—Cu2	125.84 (13)	N1—C15—C16	113.03 (17)
O3—C1—O1	125.42 (18)	N1—C15—H15A	109.0
O3—C1—C2	117.23 (18)	C16—C15—H15A	109.0
O1—C1—C2	117.35 (17)	N1—C15—H15B	109.0
C1—C2—H2A	109.5	C16—C15—H15B	109.0
C1—C2—H2B	109.5	H15A—C15—H15B	107.8
H2A—C2—H2B	109.5	C15—C16—H16A	109.5
C1—C2—H2C	109.5	C15—C16—H16B	109.5
H2A—C2—H2C	109.5	H16A—C16—H16B	109.5
H2B—C2—H2C	109.5	C15—C16—H16C	109.5
O2—C3—O4i	125.63 (19)	H16A—C16—H16C	109.5
O2—C3—C4	116.98 (18)	H16B—C16—H16C	109.5
O4i—C3—C4	117.39 (18)	C20—O11—C17	109.24 (17)
C3—C4—H4A	109.5	O11—C17—C18	107.89 (18)
C3—C4—H4B	109.5	O11—C17—H17A	110.1
H4A—C4—H4B	109.5	C18—C17—H17A	110.1
C3—C4—H4C	109.5	O11—C17—H17B	110.1
H4A—C4—H4C	109.5	C18—C17—H17B	110.1
H4B—C4—H4C	109.5	H17A—C17—H17B	108.4
O5—C5—O6	120.95 (17)	C17—C18—C19	102.34 (18)
O5—C5—C6	121.24 (16)	C17—C18—H18A	111.3
O6—C5—C6	117.81 (16)	C19—C18—H18A	111.3
C5—C6—H6A	109.5	C17—C18—H18B	111.3
C5—C6—H6B	109.5	C19—C18—H18B	111.3
H6A—C6—H6B	109.5	H18A—C18—H18B	109.2
C5—C6—H6C	109.5	C20—C19—C18	102.71 (19)
H6A—C6—H6C	109.5	C20—C19—H19A	111.2
H6B—C6—H6C	109.5	C18—C19—H19A	111.2
O9ii—C7—O7	125.74 (18)	C20—C19—H19B	111.2
O9ii—C7—C8	117.27 (17)	C18—C19—H19B	111.2
O7—C7—C8	116.98 (17)	H19A—C19—H19B	109.1
C7—C8—H8A	109.5	O11—C20—C19	106.94 (19)
C7—C8—H8B	109.5	O11—C20—H20A	110.3
H8A—C8—H8B	109.5	C19—C20—H20A	110.3
C7—C8—H8C	109.5	O11—C20—H20B	110.3
H8A—C8—H8C	109.5	C19—C20—H20B	110.3
H8B—C8—H8C	109.5	H20A—C20—H20B	108.6
O4—Cu1—O1—C1	−84.84 (17)	O8—Cu2—O9—C7ii	−85.90 (16)
O3i—Cu1—O1—C1	−0.4 (4)	O10—Cu2—O9—C7ii	82.13 (16)
O2—Cu1—O1—C1	82.87 (17)	O6—Cu2—O9—C7ii	172.55 (16)
O5—Cu1—O1—C1	177.31 (16)	Cu2ii—Cu2—O9—C7ii	0.33 (15)
Cu1i—Cu1—O1—C1	−0.12 (16)	O7—Cu2—O10—C9ii	83.93 (16)
O1—Cu1—O2—C3	−81.93 (17)	O9—Cu2—O10—C9ii	−84.13 (16)
O4—Cu1—O2—C3	7.2 (4)	O8—Cu2—O10—C9ii	−0.9 (4)
O3i—Cu1—O2—C3	85.87 (17)	O6—Cu2—O10—C9ii	−176.52 (16)
O5—Cu1—O2—C3	177.52 (17)	Cu2ii—Cu2—O10—C9ii	−0.21 (15)
Cu1i—Cu1—O2—C3	0.85 (16)	Cu1i—O3—C1—O1	0.0 (3)
O1—Cu1—O4—C3i	80.50 (17)	Cu1i—O3—C1—C2	179.53 (14)
O3i—Cu1—O4—C3i	−87.28 (17)	Cu1—O1—C1—O3	0.1 (3)
O2—Cu1—O4—C3i	−8.8 (4)	Cu1—O1—C1—C2	−179.43 (14)
O5—Cu1—O4—C3i	−179.01 (16)	Cu1—O2—C3—O4i	0.8 (3)
Cu1i—Cu1—O4—C3i	−2.43 (16)	Cu1—O2—C3—C4	−179.51 (14)
O1—Cu1—O5—C5	10.1 (2)	Cu1—O5—C5—O6	175.75 (13)
O4—Cu1—O5—C5	−80.6 (2)	Cu1—O5—C5—C6	−5.2 (3)
O3i—Cu1—O5—C5	−170.3 (2)	Cu2—O6—C5—O5	178.19 (12)
O2—Cu1—O5—C5	101.5 (2)	Cu2—O6—C5—C6	−0.9 (3)
Cu1i—Cu1—O5—C5	153.0 (5)	Cu2—O7—C7—O9ii	−1.9 (3)
O7—Cu2—O6—C5	−45.10 (17)	Cu2—O7—C7—C8	177.02 (13)
O9—Cu2—O6—C5	136.17 (16)	Cu2—O8—C9—O10ii	0.0 (3)
O8—Cu2—O6—C5	46.94 (17)	Cu2—O8—C9—C10	179.31 (13)
O10—Cu2—O6—C5	−133.99 (16)	C13—N1—C11—C12	78.9 (2)
Cu2ii—Cu2—O6—C5	−159.3 (2)	C15—N1—C11—C12	−153.20 (17)
O9—Cu2—O7—C7	3.0 (4)	C11—N1—C13—C14	−175.42 (17)
O8—Cu2—O7—C7	87.31 (16)	C15—N1—C13—C14	57.9 (2)
O10—Cu2—O7—C7	−80.69 (16)	C13—N1—C15—C16	66.7 (2)
O6—Cu2—O7—C7	−170.94 (15)	C11—N1—C15—C16	−59.8 (2)
Cu2ii—Cu2—O7—C7	1.21 (15)	C20—O11—C17—C18	−4.7 (2)
O7—Cu2—O8—C9	−83.88 (15)	O11—C17—C18—C19	23.3 (2)
O9—Cu2—O8—C9	84.17 (15)	C17—C18—C19—C20	−31.8 (2)
O10—Cu2—O8—C9	0.8 (4)	C17—O11—C20—C19	−16.4 (2)
O6—Cu2—O8—C9	176.36 (14)	C18—C19—C20—O11	30.4 (2)
Cu2ii—Cu2—O8—C9	0.14 (14)	O1—Cu1—Cu2—O7	−39.67 (7)
O7—Cu2—O9—C7ii	−1.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5	0.85 (2)	2.59 (2)	3.212 (2)	130.7 (19)
N1—H1···O6	0.85 (2)	1.89 (2)	2.737 (2)	173 (2)
C6—H6C···O1	0.98	2.42	3.3238 (18)	153
C13—H13B···O3i	0.99	2.51	3.2956 (19)	137
C15—H15B···O10	0.99	2.43	3.3041 (19)	147

Table 1

Selected bond lengths (Å)

Cu1—O1	1.9664 (14)
Cu1—O4	1.9717 (15)
Cu1—O3i	1.9738 (15)
Cu1—O2	1.9777 (15)
Cu1—O5	2.1216 (13)
Cu2—O7	1.9735 (14)
Cu2—O9	1.9804 (14)
Cu2—O8	1.9806 (14)
Cu2—O10	1.9839 (14)
Cu2—O6	2.1204 (13)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5	0.85 (2)	2.59 (2)	3.212 (2)	130.7 (19)
N1—H1⋯O6	0.85 (2)	1.89 (2)	2.737 (2)	173 (2)
C6—H6C⋯O1	0.98	2.42	3.3238 (18)	153
C13—H13B⋯O3i	0.99	2.51	3.2956 (19)	137
C15—H15B⋯O10	0.99	2.43	3.3041 (19)	147

Symmetry code: (i) .