catena-Poly[dieth-yl(2-hydroxy-ethyl)-ammonium [[tetra-μ-acetato-κO:O'-dicuprate(II)(Cu-Cu)]-μ-acetato-κO:O'] dichloro-methane solvate].

The title compound, {(C(6)H(16)NO)[Cu(2)(CH(3)COO)(5)]·CH(2)Cl(2)}(n), consists of acetate-bridged Cu(2)(CH(3)COO)(4) units that are connected via another acetate anion at each terminus to form infinite anionic [{Cu(2)(CH(3)COO)(4)}(CH(3)COO)](n) chains along [100]. The connecting acetate is hydrogen bonded to the dieth-yl(2-hydroxy-ethyl)ammonium cation, and the dichloro-methane solvent mol-ecule fills the remaining voids in the structure. The O-Cu-Cu angles along the polymeric chain are nearly linear [175.49 (5)°], but individual O-Cu-Cu-O units along the chain are bent and rotated against each other at the bridging acetate ion. Translation of each Cu(2)(CH(3)COO)(4) unit along the chain, represented by the least-squares plane of the two copper ions along with four of the acetate O atoms, rotated these units by 35.16 (3)°.

Related literature

Shahid, Mazhar, Helliwell et al. (2008 ▶) describe the study of dinuclear Cu complexes; Van Niekerk & Schoening (1953 ▶) provide X-ray evidence for Cu—Cu bonds in cupric acetate; Brown & Chidambaram (1973 ▶) report the redetermination of the structure of cupric acetate by neutron-diffraction; Shahid, Mazhar, Malik et al. (2008 ▶); Hamid et al. (2007 ▶) and Zhang et al. (2004 ▶) describe geometric parameters of organo–copper complexes.

Experimental

Crystal data

(C6H16NO)[Cu2(C2H3O2)5]·CH2Cl2

M = 625.42

Orthorhombic,

a = 17.6366 (11) Å

b = 12.1078 (8) Å

c = 11.9148 (7) Å

V = 2544.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.94 mm−1

T = 100 (2) K

0.40 × 0.40 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.657, T max = 0.830

21202 measured reflections

5939 independent reflections

5693 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.080

S = 1.08

5939 reflections

306 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.75 e Å−3

Δρmin = −0.40 e Å−3

Absolute structure: Flack (1983 ▶), 2726 Friedel pairs

Flack parameter: 0.017 (11)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; 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 I, global. DOI: 10.1107/S1600536808044048/zl2161sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808044048/zl2161Isup2.hkl

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

(C6H16NO)[Cu2(C2H3O2)5]·CH2Cl2	Dx = 1.633 Mg m−3
Mr = 625.42	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 7814 reflections
a = 17.6366 (11) Å	θ = 2.4–28.1°
b = 12.1078 (8) Å	µ = 1.94 mm−1
c = 11.9148 (7) Å	T = 100 K
V = 2544.3 (3) Å3	Plate, turquoise
Z = 4	0.40 × 0.40 × 0.10 mm
F(000) = 1288

Bruker SMART CCD area-detector diffractometer	5939 independent reflections
Radiation source: fine-focus sealed tube	5693 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −22→22
Tmin = 0.657, Tmax = 0.830	k = −16→15
21202 measured reflections	l = −15→15

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.080	w = 1/[σ2(Fo2) + (0.0393P)2 + 1.2652P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.013
5939 reflections	Δρmax = 0.75 e Å−3
306 parameters	Δρmin = −0.40 e Å−3
1 restraint	Absolute structure: Flack (1983), 2726 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.017 (11)

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
O10	1.03029 (10)	0.66475 (16)	0.5408 (2)	0.0152 (4)
C1	0.75148 (17)	0.9544 (3)	0.6165 (2)	0.0176 (6)
C2	0.77083 (18)	1.0672 (3)	0.6609 (3)	0.0206 (6)
H2A	0.7588	1.0707	0.7411	0.031*
H2B	0.7413	1.1230	0.6206	0.031*
H2C	0.8250	1.0813	0.6500	0.031*
C3	0.73249 (17)	0.8234 (2)	0.3482 (2)	0.0166 (6)
C4	0.73934 (19)	0.8662 (3)	0.2292 (3)	0.0222 (7)
H4A	0.7896	0.8478	0.1994	0.033*
H4B	0.7327	0.9465	0.2289	0.033*
H4C	0.7002	0.8319	0.1823	0.033*
C5	0.68347 (17)	0.5689 (3)	0.4849 (3)	0.0191 (6)
C6	0.66262 (19)	0.4540 (3)	0.4463 (3)	0.0283 (8)
H6A	0.7085	0.4087	0.4414	0.042*
H6B	0.6384	0.4581	0.3724	0.042*
H6C	0.6274	0.4208	0.5002	0.042*
C7	0.71363 (17)	0.6985 (3)	0.7522 (3)	0.0173 (6)
C8	0.71030 (19)	0.6623 (3)	0.8732 (3)	0.0257 (7)
H8A	0.6693	0.7017	0.9116	0.039*
H8B	0.7587	0.6791	0.9100	0.039*
H8C	0.7008	0.5826	0.8767	0.039*
C9	0.96959 (15)	0.7062 (2)	0.5798 (2)	0.0133 (6)
C10	0.97463 (17)	0.7894 (3)	0.6744 (3)	0.0189 (6)
H10A	1.0156	0.7682	0.7256	0.028*
H10B	0.9265	0.7909	0.7154	0.028*
H10C	0.9851	0.8628	0.6433	0.028*
C11	0.54065 (17)	0.9990 (3)	0.2860 (3)	0.0210 (7)
H11A	0.5795	0.9515	0.2504	0.025*
H11B	0.5183	1.0463	0.2268	0.025*
C12	0.57806 (18)	1.0711 (3)	0.3723 (3)	0.0240 (7)
H12A	0.5967	1.0253	0.4342	0.036*
H12B	0.5412	1.1246	0.4012	0.036*
H12C	0.6206	1.1106	0.3379	0.036*
C13	0.4783 (2)	0.8130 (3)	0.2850 (3)	0.0265 (7)
H13A	0.4413	0.7669	0.3262	0.032*
H13B	0.5290	0.7792	0.2947	0.032*
C14	0.4581 (2)	0.8124 (4)	0.1617 (3)	0.0350 (9)
H14A	0.4934	0.8599	0.1205	0.052*
H14B	0.4063	0.8399	0.1519	0.052*
H14C	0.4615	0.7368	0.1327	0.052*
C15	0.40137 (17)	0.9772 (3)	0.3296 (3)	0.0249 (7)
H15A	0.3913	0.9998	0.2512	0.030*
H15B	0.3635	0.9203	0.3499	0.030*
C16	0.39024 (18)	1.0753 (3)	0.4043 (3)	0.0280 (7)
H16A	0.4225	1.1365	0.3771	0.034*
H16B	0.3368	1.0996	0.3991	0.034*
C17	0.9547 (2)	0.9492 (3)	0.4356 (3)	0.0292 (8)
H17A	0.9991	0.9018	0.4520	0.035*
H17B	0.9086	0.9093	0.4601	0.035*
Cl1	0.96272 (5)	1.07456 (9)	0.51185 (9)	0.0367 (2)
Cl2	0.94975 (7)	0.97421 (9)	0.29049 (9)	0.0475 (3)
Cu1	0.647405 (16)	0.78765 (2)	0.55145 (3)	0.01289 (8)
Cu2	0.791704 (16)	0.73425 (3)	0.54933 (4)	0.01346 (8)
N1	0.47907 (14)	0.9266 (2)	0.3355 (2)	0.0182 (5)
H1	0.4905	0.9179	0.4112	0.022*
O1	0.68332 (11)	0.93608 (17)	0.59168 (18)	0.0168 (4)
O2	0.80508 (12)	0.88517 (18)	0.60953 (19)	0.0211 (5)
O3	0.66724 (12)	0.82111 (19)	0.39116 (18)	0.0184 (4)
O4	0.79321 (12)	0.79520 (19)	0.39662 (19)	0.0194 (5)
O5	0.62993 (11)	0.63224 (17)	0.51139 (19)	0.0193 (4)
O6	0.75254 (11)	0.59322 (18)	0.4873 (2)	0.0202 (5)
O7	0.77446 (12)	0.67809 (19)	0.70047 (19)	0.0212 (5)
O8	0.65654 (12)	0.7454 (2)	0.71140 (18)	0.0188 (4)
O9	0.90593 (10)	0.67911 (16)	0.5416 (2)	0.0172 (4)
O11	0.40773 (14)	1.05419 (19)	0.5170 (2)	0.0306 (6)
H11	0.3963	0.9886	0.5327	0.046*

	U11	U22	U33	U12	U13	U23
O10	0.0095 (8)	0.0212 (9)	0.0148 (10)	−0.0006 (6)	0.0011 (8)	−0.0015 (10)
C1	0.0178 (15)	0.0243 (16)	0.0107 (14)	−0.0011 (12)	0.0035 (11)	0.0009 (12)
C2	0.0197 (15)	0.0206 (16)	0.0215 (15)	−0.0048 (12)	0.0025 (13)	−0.0057 (12)
C3	0.0190 (14)	0.0160 (14)	0.0148 (14)	−0.0009 (11)	−0.0020 (12)	−0.0026 (11)
C4	0.0220 (16)	0.0293 (17)	0.0153 (15)	0.0007 (13)	0.0025 (12)	0.0042 (13)
C5	0.0186 (15)	0.0205 (15)	0.0182 (15)	0.0010 (12)	0.0025 (12)	0.0014 (12)
C6	0.0172 (16)	0.0200 (16)	0.048 (2)	−0.0038 (12)	0.0046 (15)	−0.0101 (15)
C7	0.0172 (15)	0.0179 (14)	0.0168 (15)	−0.0019 (11)	0.0000 (11)	−0.0016 (12)
C8	0.0232 (16)	0.0366 (19)	0.0173 (16)	0.0060 (14)	0.0024 (13)	0.0091 (14)
C9	0.0139 (13)	0.0139 (13)	0.0123 (15)	−0.0011 (10)	−0.0003 (10)	0.0017 (9)
C10	0.0144 (14)	0.0209 (16)	0.0213 (16)	0.0000 (11)	−0.0036 (12)	−0.0091 (12)
C11	0.0150 (15)	0.0296 (18)	0.0185 (16)	−0.0010 (12)	0.0033 (12)	0.0075 (13)
C12	0.0144 (15)	0.0294 (17)	0.0283 (17)	−0.0048 (13)	−0.0006 (13)	0.0063 (14)
C13	0.0315 (19)	0.0241 (16)	0.0240 (17)	−0.0013 (14)	−0.0016 (14)	0.0000 (14)
C14	0.040 (2)	0.043 (2)	0.0215 (17)	−0.0088 (17)	−0.0011 (16)	−0.0045 (16)
C15	0.0135 (15)	0.0404 (19)	0.0208 (16)	−0.0001 (13)	−0.0038 (12)	0.0141 (14)
C16	0.0133 (15)	0.0298 (17)	0.041 (2)	0.0028 (13)	0.0025 (14)	0.0116 (15)
C17	0.0277 (18)	0.036 (2)	0.0242 (18)	−0.0045 (14)	0.0010 (15)	0.0061 (15)
Cl1	0.0248 (4)	0.0460 (5)	0.0393 (5)	0.0034 (4)	−0.0039 (4)	−0.0083 (4)
Cl2	0.0826 (8)	0.0327 (5)	0.0272 (5)	−0.0082 (5)	0.0083 (5)	0.0062 (4)
Cu1	0.00720 (13)	0.01831 (15)	0.01316 (15)	0.00109 (10)	0.00003 (17)	−0.00089 (17)
Cu2	0.00722 (13)	0.01905 (15)	0.01411 (15)	0.00129 (10)	0.00009 (19)	−0.00129 (18)
N1	0.0148 (12)	0.0255 (14)	0.0142 (12)	−0.0033 (10)	−0.0022 (10)	0.0056 (11)
O1	0.0117 (10)	0.0184 (10)	0.0205 (10)	0.0008 (8)	−0.0007 (8)	−0.0027 (8)
O2	0.0119 (10)	0.0253 (12)	0.0260 (12)	0.0025 (9)	−0.0020 (9)	−0.0077 (10)
O3	0.0117 (10)	0.0290 (12)	0.0145 (10)	0.0008 (9)	−0.0004 (8)	0.0014 (9)
O4	0.0127 (10)	0.0295 (12)	0.0161 (11)	0.0003 (8)	0.0025 (8)	0.0018 (9)
O5	0.0123 (10)	0.0200 (10)	0.0255 (11)	−0.0005 (8)	−0.0006 (8)	−0.0045 (8)
O6	0.0103 (10)	0.0207 (11)	0.0295 (13)	−0.0016 (8)	0.0002 (9)	−0.0022 (9)
O7	0.0138 (10)	0.0317 (12)	0.0183 (11)	0.0069 (9)	0.0001 (9)	0.0054 (9)
O8	0.0153 (10)	0.0273 (12)	0.0137 (10)	0.0043 (9)	0.0023 (8)	0.0023 (9)
O9	0.0083 (8)	0.0220 (9)	0.0213 (11)	0.0002 (7)	−0.0008 (10)	−0.0075 (10)
O11	0.0310 (13)	0.0231 (11)	0.0378 (15)	−0.0031 (10)	0.0034 (11)	−0.0001 (10)

O10—C9	1.271 (3)	C12—H12A	0.9800
O10—Cu1i	2.1482 (18)	C12—H12B	0.9800
C1—O1	1.258 (4)	C12—H12C	0.9800
C1—O2	1.266 (4)	C13—N1	1.500 (4)
C1—C2	1.504 (4)	C13—C14	1.512 (5)
C2—H2A	0.9800	C13—H13A	0.9900
C2—H2B	0.9800	C13—H13B	0.9900
C2—H2C	0.9800	C14—H14A	0.9800
C3—O3	1.260 (4)	C14—H14B	0.9800
C3—O4	1.263 (4)	C14—H14C	0.9800
C3—C4	1.514 (4)	C15—C16	1.496 (5)
C4—H4A	0.9800	C15—N1	1.503 (4)
C4—H4B	0.9800	C15—H15A	0.9900
C4—H4C	0.9800	C15—H15B	0.9900
C5—O6	1.254 (4)	C16—O11	1.400 (4)
C5—O5	1.257 (4)	C16—H16A	0.9900
C5—C6	1.510 (4)	C16—H16B	0.9900
C6—H6A	0.9800	C17—Cl2	1.758 (4)
C6—H6B	0.9800	C17—Cl1	1.775 (4)
C6—H6C	0.9800	C17—H17A	0.9900
C7—O8	1.254 (4)	C17—H17B	0.9900
C7—O7	1.262 (4)	Cu1—O1	1.965 (2)
C7—C8	1.508 (4)	Cu1—O5	1.966 (2)
C8—H8A	0.9800	Cu1—O8	1.980 (2)
C8—H8B	0.9800	Cu1—O3	1.983 (2)
C8—H8C	0.9800	Cu1—O10ii	2.1482 (18)
C9—O9	1.255 (3)	Cu1—Cu2	2.6259 (4)
C9—C10	1.514 (4)	Cu2—O7	1.949 (2)
C10—H10A	0.9800	Cu2—O4	1.964 (2)
C10—H10B	0.9800	Cu2—O2	1.977 (2)
C10—H10C	0.9800	Cu2—O6	1.985 (2)
C11—C12	1.502 (5)	Cu2—O9	2.1243 (18)
C11—N1	1.515 (4)	N1—H1	0.9300
C11—H11A	0.9900	O11—H11	0.8400
C11—H11B	0.9900
C9—O10—Cu1i	133.03 (19)	C13—C14—H14C	109.5
O1—C1—O2	125.5 (3)	H14A—C14—H14C	109.5
O1—C1—C2	117.4 (3)	H14B—C14—H14C	109.5
O2—C1—C2	117.1 (3)	C16—C15—N1	114.6 (3)
C1—C2—H2A	109.5	C16—C15—H15A	108.6
C1—C2—H2B	109.5	N1—C15—H15A	108.6
H2A—C2—H2B	109.5	C16—C15—H15B	108.6
C1—C2—H2C	109.5	N1—C15—H15B	108.6
H2A—C2—H2C	109.5	H15A—C15—H15B	107.6
H2B—C2—H2C	109.5	O11—C16—C15	113.4 (3)
O3—C3—O4	125.6 (3)	O11—C16—H16A	108.9
O3—C3—C4	117.4 (3)	C15—C16—H16A	108.9
O4—C3—C4	116.9 (3)	O11—C16—H16B	108.9
C3—C4—H4A	109.5	C15—C16—H16B	108.9
C3—C4—H4B	109.5	H16A—C16—H16B	107.7
H4A—C4—H4B	109.5	Cl2—C17—Cl1	111.1 (2)
C3—C4—H4C	109.5	Cl2—C17—H17A	109.4
H4A—C4—H4C	109.5	Cl1—C17—H17A	109.4
H4B—C4—H4C	109.5	Cl2—C17—H17B	109.4
O6—C5—O5	125.5 (3)	Cl1—C17—H17B	109.4
O6—C5—C6	117.4 (3)	H17A—C17—H17B	108.0
O5—C5—C6	117.1 (3)	O1—Cu1—O5	170.19 (8)
C5—C6—H6A	109.5	O1—Cu1—O8	88.59 (10)
C5—C6—H6B	109.5	O5—Cu1—O8	89.95 (10)
H6A—C6—H6B	109.5	O1—Cu1—O3	89.50 (9)
C5—C6—H6C	109.5	O5—Cu1—O3	89.39 (10)
H6A—C6—H6C	109.5	O8—Cu1—O3	164.87 (9)
H6B—C6—H6C	109.5	O1—Cu1—O10ii	94.53 (8)
O8—C7—O7	125.6 (3)	O5—Cu1—O10ii	95.26 (8)
O8—C7—C8	118.1 (3)	O8—Cu1—O10ii	101.81 (9)
O7—C7—C8	116.3 (3)	O3—Cu1—O10ii	93.31 (9)
C7—C8—H8A	109.5	O1—Cu1—Cu2	85.13 (6)
C7—C8—H8B	109.5	O5—Cu1—Cu2	85.06 (6)
H8A—C8—H8B	109.5	O8—Cu1—Cu2	82.34 (6)
C7—C8—H8C	109.5	O3—Cu1—Cu2	82.54 (6)
H8A—C8—H8C	109.5	O10ii—Cu1—Cu2	175.83 (7)
H8B—C8—H8C	109.5	O7—Cu2—O4	171.68 (9)
O9—C9—O10	121.2 (3)	O7—Cu2—O2	90.33 (10)
O9—C9—C10	119.7 (2)	O4—Cu2—O2	89.27 (10)
O10—C9—C10	119.1 (2)	O7—Cu2—O6	89.42 (10)
C9—C10—H10A	109.5	O4—Cu2—O6	89.01 (10)
C9—C10—H10B	109.5	O2—Cu2—O6	166.35 (9)
H10A—C10—H10B	109.5	O7—Cu2—O9	94.49 (9)
C9—C10—H10C	109.5	O4—Cu2—O9	93.75 (9)
H10A—C10—H10C	109.5	O2—Cu2—O9	101.13 (8)
H10B—C10—H10C	109.5	O6—Cu2—O9	92.50 (8)
C12—C11—N1	112.6 (3)	O7—Cu2—Cu1	85.74 (6)
C12—C11—H11A	109.1	O4—Cu2—Cu1	85.95 (6)
N1—C11—H11A	109.1	O2—Cu2—Cu1	83.37 (6)
C12—C11—H11B	109.1	O6—Cu2—Cu1	83.00 (6)
N1—C11—H11B	109.1	O9—Cu2—Cu1	175.49 (5)
H11A—C11—H11B	107.8	C13—N1—C15	110.3 (3)
C11—C12—H12A	109.5	C13—N1—C11	112.4 (3)
C11—C12—H12B	109.5	C15—N1—C11	113.5 (3)
H12A—C12—H12B	109.5	C13—N1—H1	106.7
C11—C12—H12C	109.5	C15—N1—H1	106.7
H12A—C12—H12C	109.5	C11—N1—H1	106.7
H12B—C12—H12C	109.5	C1—O1—Cu1	121.79 (19)
N1—C13—C14	113.4 (3)	C1—O2—Cu2	123.1 (2)
N1—C13—H13A	108.9	C3—O3—Cu1	123.84 (19)
C14—C13—H13A	108.9	C3—O4—Cu2	120.88 (19)
N1—C13—H13B	108.9	C5—O5—Cu1	121.84 (19)
C14—C13—H13B	108.9	C5—O6—Cu2	123.3 (2)
H13A—C13—H13B	107.7	C7—O7—Cu2	121.1 (2)
C13—C14—H14A	109.5	C7—O8—Cu1	123.7 (2)
C13—C14—H14B	109.5	C9—O9—Cu2	138.64 (19)
H14A—C14—H14B	109.5	C16—O11—H11	109.5
Cu1i—O10—C9—O9	163.2 (2)	O8—Cu1—O3—C3	−7.4 (5)
Cu1i—O10—C9—C10	−17.2 (4)	O10ii—Cu1—O3—C3	169.8 (2)
N1—C15—C16—O11	−54.5 (4)	Cu2—Cu1—O3—C3	−9.9 (2)
O1—Cu1—Cu2—O7	97.97 (10)	O3—C3—O4—Cu2	3.4 (4)
O5—Cu1—Cu2—O7	−81.87 (10)	C4—C3—O4—Cu2	−178.2 (2)
O8—Cu1—Cu2—O7	8.74 (10)	O2—Cu2—O4—C3	−91.6 (2)
O3—Cu1—Cu2—O7	−171.90 (10)	O6—Cu2—O4—C3	74.9 (2)
O1—Cu1—Cu2—O4	−82.60 (9)	O9—Cu2—O4—C3	167.3 (2)
O5—Cu1—Cu2—O4	97.56 (10)	Cu1—Cu2—O4—C3	−8.2 (2)
O8—Cu1—Cu2—O4	−171.83 (10)	O6—C5—O5—Cu1	4.7 (4)
O3—Cu1—Cu2—O4	7.53 (9)	C6—C5—O5—Cu1	−175.0 (2)
O1—Cu1—Cu2—O2	7.13 (9)	O8—Cu1—O5—C5	−91.6 (2)
O5—Cu1—Cu2—O2	−172.71 (10)	O3—Cu1—O5—C5	73.3 (2)
O8—Cu1—Cu2—O2	−82.10 (10)	O10ii—Cu1—O5—C5	166.5 (2)
O3—Cu1—Cu2—O2	97.26 (10)	Cu2—Cu1—O5—C5	−9.3 (2)
O1—Cu1—Cu2—O6	−172.10 (10)	O5—C5—O6—Cu2	6.5 (4)
O5—Cu1—Cu2—O6	8.06 (9)	C6—C5—O6—Cu2	−173.8 (2)
O8—Cu1—Cu2—O6	98.67 (10)	O7—Cu2—O6—C5	75.7 (2)
O3—Cu1—Cu2—O6	−81.97 (10)	O4—Cu2—O6—C5	−96.2 (2)
C14—C13—N1—C15	62.7 (4)	O2—Cu2—O6—C5	−13.3 (6)
C14—C13—N1—C11	−65.1 (4)	O9—Cu2—O6—C5	170.1 (2)
C16—C15—N1—C13	163.9 (3)	Cu1—Cu2—O6—C5	−10.1 (2)
C16—C15—N1—C11	−68.9 (3)	O8—C7—O7—Cu2	7.2 (4)
C12—C11—N1—C13	−141.1 (3)	C8—C7—O7—Cu2	−173.0 (2)
C12—C11—N1—C15	92.8 (3)	O2—Cu2—O7—C7	72.4 (2)
O2—C1—O1—Cu1	6.5 (4)	O6—Cu2—O7—C7	−94.0 (2)
C2—C1—O1—Cu1	−171.9 (2)	O9—Cu2—O7—C7	173.6 (2)
O8—Cu1—O1—C1	73.2 (2)	Cu1—Cu2—O7—C7	−11.0 (2)
O3—Cu1—O1—C1	−91.8 (2)	O7—C7—O8—Cu1	4.9 (5)
O10ii—Cu1—O1—C1	174.9 (2)	C8—C7—O8—Cu1	−174.9 (2)
Cu2—Cu1—O1—C1	−9.2 (2)	O1—Cu1—O8—C7	−95.1 (3)
O1—C1—O2—Cu2	3.4 (4)	O5—Cu1—O8—C7	75.2 (3)
C2—C1—O2—Cu2	−178.2 (2)	O3—Cu1—O8—C7	−12.3 (6)
O7—Cu2—O2—C1	−93.5 (2)	O10ii—Cu1—O8—C7	170.5 (2)
O4—Cu2—O2—C1	78.2 (2)	Cu2—Cu1—O8—C7	−9.9 (2)
O6—Cu2—O2—C1	−4.6 (6)	O10—C9—O9—Cu2	−166.8 (2)
O9—Cu2—O2—C1	171.9 (2)	C10—C9—O9—Cu2	13.5 (5)
Cu1—Cu2—O2—C1	−7.8 (2)	O7—Cu2—O9—C9	−75.7 (3)
O4—C3—O3—Cu1	7.0 (4)	O4—Cu2—O9—C9	105.5 (3)
C4—C3—O3—Cu1	−171.4 (2)	O2—Cu2—O9—C9	15.5 (3)
O1—Cu1—O3—C3	75.3 (2)	O6—Cu2—O9—C9	−165.4 (3)
O5—Cu1—O3—C3	−94.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O10ii	0.93	1.97	2.832 (4)	153
N1—H1···O9ii	0.93	2.45	3.056 (3)	123
O11—H11···O9ii	0.84	2.04	2.840 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O10i	0.93	1.97	2.832 (4)	153
N1—H1⋯O9i	0.93	2.45	3.056 (3)	123
O11—H11⋯O9i	0.84	2.04	2.840 (3)	159

Symmetry code: (i) .