Poly[[diaqua-bis-{μ-4-[6-(4-carb-oxy-phen-yl)-4,4'-bipyridin-2-yl]benzoato-κ(2) O:N (1')}copper(II)] dimethyl-formamide tetra-solvate].

In the title compound, {[Cu(C24H15N2O4)2(H2O)2]·4C3H7NO} n , the Cu(II) ion, lying on an inversion center, is six-coordinated by two N atoms from two 4-[6-(4-carb-oxy-phen-yl)-4,4'-bipyridin-2-yl]benzoate (L) ligands, two deprotonated carboxyl-ate O atoms from two other symmetry-related L ligands and two water mol-ecules in a slightly distorted octa-hedral geometry. The Cu(II) atoms are linked by the bridging ligands into a layer parallel to (101). The presence of intra-layer O-H⋯O hydrogen bonds and π-π inter-actions between the pyridine and benzene rings [centroid-centroid distances = 3.808 (2) and 3.927 (2) Å] stabilizes the layer. Further O-H⋯O hydrogen bonds link the layers and the dimethyl-formamide solvent mol-ecules.

Related literature

For the design of metal-organic coordination polymers, see: Ge & Song (2012 ▶); Herm et al. (2011 ▶); Liu et al. (2010 ▶); Wang et al. (2010 ▶). For a related structure, see: Xia et al. (2012 ▶).

Experimental

Crystal data

[Cu(C24H15N2O4)2(H2O)2]·4C3H7NO

M = 1182.73

Monoclinic,

a = 7.7161 (17) Å

b = 17.550 (4) Å

c = 20.947 (4) Å

β = 96.800 (4)°

V = 2816.6 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.46 mm−1

T = 293 K

0.27 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.885, T max = 0.913

14622 measured reflections

5226 independent reflections

3371 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.185

S = 1.04

5226 reflections

376 parameters

H-atom parameters constrained

Δρmax = 0.93 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813006430/hy2619sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006430/hy2619Isup2.hkl

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

[Cu(C24H15N2O4)2(H2O)2]·4C3H7NO	F(000) = 1238
Mr = 1182.73	Dx = 1.395 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5226 reflections
a = 7.7161 (17) Å	θ = 1.0–26.0°
b = 17.550 (4) Å	µ = 0.46 mm−1
c = 20.947 (4) Å	T = 293 K
β = 96.800 (4)°	Block, green
V = 2816.6 (10) Å3	0.27 × 0.25 × 0.20 mm
Z = 2

Bruker APEXII CCD diffractometer	5226 independent reflections
Radiation source: fine-focus sealed tube	3371 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
φ and ω scans	θmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→7
Tmin = 0.885, Tmax = 0.913	k = −21→21
14622 measured reflections	l = −20→25

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0891P)2 + 2.0095P] where P = (Fo2 + 2Fc2)/3
5226 reflections	(Δ/σ)max < 0.001
376 parameters	Δρmax = 0.93 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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	1.0000	0.5000	0.0000	0.0362 (2)
C1	0.8452 (6)	1.2336 (2)	−0.1386 (2)	0.0432 (10)
C2	0.8060 (5)	1.1653 (2)	−0.10151 (19)	0.0347 (9)
C3	0.7251 (5)	1.1715 (2)	−0.0455 (2)	0.0369 (10)
H3	0.6854	1.2186	−0.0330	0.044*
C4	0.7040 (5)	1.1079 (2)	−0.0088 (2)	0.0350 (9)
H4	0.6517	1.1128	0.0288	0.042*
C5	0.7592 (5)	1.0363 (2)	−0.02669 (18)	0.0286 (8)
C6	0.8380 (5)	1.0305 (2)	−0.08253 (19)	0.0352 (9)
H6	0.8762	0.9832	−0.0953	0.042*
C7	0.8607 (5)	1.0943 (2)	−0.11976 (19)	0.0376 (10)
H7	0.9132	1.0894	−0.1573	0.045*
C8	0.7389 (5)	0.9695 (2)	0.01565 (19)	0.0302 (8)
C9	0.7683 (5)	0.8950 (2)	−0.00365 (18)	0.0304 (9)
H9	0.7972	0.8853	−0.0447	0.036*
C10	0.7540 (5)	0.83558 (19)	0.03927 (18)	0.0280 (8)
C11	0.7072 (5)	0.8537 (2)	0.09959 (18)	0.0314 (9)
H11	0.6958	0.8154	0.1295	0.038*
C12	0.6774 (5)	0.9291 (2)	0.11507 (18)	0.0299 (8)
C13	0.6253 (5)	0.9511 (2)	0.17864 (18)	0.0301 (9)
C14	0.5242 (5)	1.0156 (2)	0.18392 (19)	0.0358 (9)
H14	0.4924	1.0455	0.1478	0.043*
C15	0.4702 (5)	1.0358 (2)	0.24194 (19)	0.0372 (10)
H15	0.4004	1.0786	0.2445	0.045*
C16	0.5196 (5)	0.9925 (2)	0.29668 (18)	0.0312 (9)
C17	0.6242 (5)	0.9290 (2)	0.29215 (19)	0.0378 (10)
H17	0.6586	0.8998	0.3285	0.045*
C18	0.6777 (5)	0.9089 (2)	0.23352 (19)	0.0366 (9)
H18	0.7494	0.8667	0.2310	0.044*
C19	0.4600 (6)	1.0145 (2)	0.3597 (2)	0.0361 (10)
C20	0.7944 (5)	0.75539 (19)	0.02344 (17)	0.0288 (8)
C21	0.9191 (5)	0.73870 (19)	−0.01677 (18)	0.0307 (9)
H21	0.9689	0.7778	−0.0384	0.037*
C22	0.9695 (5)	0.6647 (2)	−0.02478 (19)	0.0339 (9)
H22	1.0543	0.6549	−0.0517	0.041*
C23	0.7732 (5)	0.6214 (2)	0.04100 (19)	0.0360 (9)
H23	0.7197	0.5811	0.0598	0.043*
C24	0.7177 (5)	0.6942 (2)	0.05158 (18)	0.0342 (9)
H24	0.6294	0.7025	0.0774	0.041*
C25	0.6692 (8)	0.6406 (4)	−0.1720 (3)	0.0829 (19)
H25A	0.7059	0.6773	−0.2016	0.124*
H25B	0.6144	0.5984	−0.1955	0.124*
H25C	0.7689	0.6229	−0.1442	0.124*
C26	0.5118 (8)	0.7558 (3)	−0.1443 (3)	0.0756 (16)
H26A	0.5739	0.7741	−0.1783	0.113*
H26B	0.5493	0.7833	−0.1055	0.113*
H26C	0.3889	0.7633	−0.1558	0.113*
C27	0.4770 (6)	0.6364 (3)	−0.0897 (2)	0.0543 (12)
H27	0.5082	0.5854	−0.0843	0.065*
C28	0.4517 (16)	1.2769 (5)	−0.2557 (5)	0.203 (6)
H28A	0.4153	1.2642	−0.2148	0.304*
H28B	0.5656	1.2561	−0.2586	0.304*
H28C	0.3703	1.2562	−0.2895	0.304*
C29	0.4063 (11)	1.3970 (6)	−0.2090 (4)	0.157 (4)
H29A	0.3787	1.3613	−0.1770	0.235*
H29B	0.3054	1.4274	−0.2228	0.235*
H29C	0.4999	1.4294	−0.1912	0.235*
C30	0.5028 (11)	1.3864 (4)	−0.3123 (4)	0.119 (3)
H30	0.4860	1.4387	−0.3166	0.142*
N1	0.6925 (4)	0.98644 (16)	0.07362 (15)	0.0305 (7)
N2	0.9010 (4)	0.60580 (17)	0.00477 (15)	0.0331 (8)
N3	0.5471 (5)	0.6755 (2)	−0.13415 (19)	0.0533 (10)
N4	0.4576 (6)	1.3570 (2)	−0.2622 (2)	0.0619 (11)
O1	0.5313 (4)	0.98064 (14)	0.40897 (13)	0.0395 (7)
O2	0.3418 (4)	1.06386 (16)	0.35908 (14)	0.0488 (8)
O3	0.9397 (5)	1.23445 (17)	−0.18056 (16)	0.0582 (9)
O4	0.7673 (4)	1.29571 (17)	−0.11906 (16)	0.0607 (9)
H4A	0.7916	1.3324	−0.1405	0.091*
O5	0.3740 (4)	0.6624 (2)	−0.05498 (17)	0.0651 (10)
O6	0.5670 (7)	1.3545 (2)	−0.3567 (2)	0.1082 (17)
O1W	1.3019 (4)	0.54357 (17)	0.02770 (15)	0.0552 (8)
H1A	1.3236	0.5847	0.0087	0.083*
H1B	1.2828	0.5552	0.0656	0.083*

	U11	U22	U33	U12	U13	U23
Cu1	0.0628 (5)	0.0222 (3)	0.0263 (4)	0.0050 (3)	0.0164 (3)	0.0015 (3)
C1	0.054 (3)	0.033 (2)	0.042 (3)	−0.001 (2)	0.005 (2)	0.0034 (19)
C2	0.036 (2)	0.031 (2)	0.037 (2)	−0.0049 (17)	0.0019 (18)	0.0061 (17)
C3	0.040 (2)	0.0251 (19)	0.046 (3)	0.0037 (16)	0.010 (2)	0.0004 (17)
C4	0.039 (2)	0.0273 (19)	0.041 (2)	0.0008 (17)	0.0146 (19)	0.0013 (17)
C5	0.032 (2)	0.0272 (19)	0.027 (2)	−0.0010 (16)	0.0060 (16)	0.0009 (15)
C6	0.048 (2)	0.0254 (18)	0.033 (2)	0.0009 (17)	0.0094 (19)	−0.0029 (16)
C7	0.052 (3)	0.035 (2)	0.028 (2)	−0.0037 (18)	0.0104 (19)	0.0002 (17)
C8	0.034 (2)	0.0256 (18)	0.032 (2)	0.0004 (16)	0.0066 (17)	0.0011 (16)
C9	0.037 (2)	0.0284 (19)	0.027 (2)	0.0006 (16)	0.0088 (17)	−0.0017 (16)
C10	0.033 (2)	0.0240 (18)	0.028 (2)	−0.0001 (15)	0.0067 (16)	−0.0014 (15)
C11	0.042 (2)	0.0257 (19)	0.027 (2)	0.0008 (16)	0.0090 (17)	0.0019 (16)
C12	0.036 (2)	0.0275 (19)	0.027 (2)	−0.0004 (16)	0.0085 (17)	0.0000 (16)
C13	0.038 (2)	0.0284 (19)	0.025 (2)	−0.0028 (16)	0.0074 (17)	−0.0047 (15)
C14	0.048 (2)	0.033 (2)	0.027 (2)	0.0025 (17)	0.0097 (19)	0.0007 (16)
C15	0.050 (2)	0.030 (2)	0.034 (2)	0.0050 (18)	0.0104 (19)	−0.0020 (17)
C16	0.041 (2)	0.0259 (19)	0.029 (2)	−0.0039 (16)	0.0126 (17)	−0.0045 (16)
C17	0.051 (3)	0.032 (2)	0.032 (2)	0.0009 (18)	0.0092 (19)	0.0052 (17)
C18	0.047 (2)	0.031 (2)	0.033 (2)	0.0078 (18)	0.0118 (19)	−0.0013 (17)
C19	0.050 (2)	0.026 (2)	0.035 (2)	−0.0054 (18)	0.014 (2)	−0.0043 (17)
C20	0.039 (2)	0.0239 (18)	0.024 (2)	0.0012 (16)	0.0051 (16)	−0.0003 (15)
C21	0.043 (2)	0.0225 (18)	0.029 (2)	−0.0019 (16)	0.0141 (17)	0.0005 (15)
C22	0.047 (2)	0.0275 (19)	0.030 (2)	−0.0006 (17)	0.0146 (18)	−0.0004 (16)
C23	0.052 (3)	0.028 (2)	0.030 (2)	−0.0039 (18)	0.0140 (19)	0.0014 (16)
C24	0.045 (2)	0.031 (2)	0.029 (2)	0.0012 (17)	0.0158 (18)	−0.0017 (16)
C25	0.081 (4)	0.119 (5)	0.052 (4)	0.025 (4)	0.022 (3)	0.004 (3)
C26	0.097 (4)	0.062 (3)	0.069 (4)	−0.003 (3)	0.017 (3)	0.009 (3)
C27	0.056 (3)	0.053 (3)	0.054 (3)	−0.005 (2)	0.005 (3)	−0.002 (2)
C28	0.303 (15)	0.088 (6)	0.196 (11)	−0.064 (8)	−0.057 (10)	0.066 (7)
C29	0.132 (7)	0.259 (12)	0.082 (6)	0.104 (8)	0.025 (5)	0.000 (6)
C30	0.167 (8)	0.079 (5)	0.123 (7)	0.022 (5)	0.067 (6)	0.031 (5)
N1	0.0353 (17)	0.0303 (17)	0.0272 (18)	−0.0014 (13)	0.0090 (14)	−0.0030 (13)
N2	0.049 (2)	0.0260 (16)	0.0265 (18)	0.0009 (14)	0.0128 (15)	0.0000 (13)
N3	0.054 (2)	0.062 (3)	0.046 (2)	0.000 (2)	0.0151 (19)	0.0015 (19)
N4	0.071 (3)	0.059 (3)	0.061 (3)	0.012 (2)	0.027 (2)	0.019 (2)
O1	0.0655 (19)	0.0274 (14)	0.0276 (16)	−0.0003 (13)	0.0135 (14)	−0.0001 (11)
O2	0.071 (2)	0.0377 (16)	0.0413 (19)	0.0105 (15)	0.0232 (15)	−0.0045 (13)
O3	0.082 (2)	0.0458 (19)	0.051 (2)	−0.0038 (17)	0.0217 (19)	0.0064 (15)
O4	0.081 (2)	0.0349 (17)	0.070 (2)	0.0016 (16)	0.0251 (19)	0.0134 (16)
O5	0.060 (2)	0.075 (2)	0.064 (2)	−0.0093 (18)	0.0235 (19)	−0.0012 (19)
O6	0.179 (5)	0.077 (3)	0.083 (3)	−0.005 (3)	0.075 (3)	−0.021 (2)
O1W	0.072 (2)	0.0441 (18)	0.053 (2)	−0.0041 (16)	0.0239 (17)	−0.0006 (15)

Cu1—O1i	1.980 (3)	C19—O2	1.256 (5)
Cu1—O1ii	1.980 (3)	C19—O1	1.260 (5)
Cu1—N2	2.015 (3)	C20—C21	1.383 (5)
Cu1—N2iii	2.015 (3)	C20—C24	1.390 (5)
C1—O3	1.207 (5)	C21—C22	1.371 (5)
C1—O4	1.332 (5)	C21—H21	0.9300
C1—C2	1.480 (5)	C22—N2	1.345 (5)
C2—C7	1.383 (5)	C22—H22	0.9300
C2—C3	1.398 (5)	C23—N2	1.342 (5)
C3—C4	1.375 (5)	C23—C24	1.374 (5)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.393 (5)	C24—H24	0.9300
C4—H4	0.9300	C25—N3	1.439 (6)
C5—C6	1.385 (5)	C25—H25A	0.9600
C5—C8	1.490 (5)	C25—H25B	0.9600
C6—C7	1.388 (5)	C25—H25C	0.9600
C6—H6	0.9300	C26—N3	1.447 (6)
C7—H7	0.9300	C26—H26A	0.9600
C8—N1	1.340 (5)	C26—H26B	0.9600
C8—C9	1.394 (5)	C26—H26C	0.9600
C9—C10	1.390 (5)	C27—O5	1.226 (5)
C9—H9	0.9300	C27—N3	1.323 (6)
C10—C11	1.392 (5)	C27—H27	0.9300
C10—C20	1.487 (5)	C28—N4	1.413 (9)
C11—C12	1.388 (5)	C28—H28A	0.9600
C11—H11	0.9300	C28—H28B	0.9600
C12—N1	1.343 (5)	C28—H28C	0.9600
C12—C13	1.487 (5)	C29—N4	1.411 (8)
C13—C14	1.385 (5)	C29—H29A	0.9600
C13—C18	1.387 (5)	C29—H29B	0.9600
C14—C15	1.377 (5)	C29—H29C	0.9600
C14—H14	0.9300	C30—O6	1.238 (8)
C15—C16	1.391 (5)	C30—N4	1.255 (7)
C15—H15	0.9300	C30—H30	0.9300
C16—C17	1.385 (5)	O1—Cu1iv	1.980 (3)
C16—C19	1.499 (5)	O4—H4A	0.8200
C17—C18	1.387 (5)	O1W—H1A	0.8501
C17—H17	0.9300	O1W—H1B	0.8489
C18—H18	0.9300
O1i—Cu1—O1ii	180.0	O2—C19—C16	117.9 (4)
O1i—Cu1—N2	91.16 (11)	O1—C19—C16	116.7 (4)
O1ii—Cu1—N2	88.84 (11)	C21—C20—C24	117.2 (3)
O1i—Cu1—N2iii	88.84 (11)	C21—C20—C10	121.0 (3)
O1ii—Cu1—N2iii	91.16 (11)	C24—C20—C10	121.7 (3)
N2—Cu1—N2iii	180.0	C22—C21—C20	120.2 (3)
O3—C1—O4	123.2 (4)	C22—C21—H21	119.9
O3—C1—C2	124.8 (4)	C20—C21—H21	119.9
O4—C1—C2	112.0 (4)	N2—C22—C21	122.6 (4)
C7—C2—C3	118.9 (3)	N2—C22—H22	118.7
C7—C2—C1	119.8 (4)	C21—C22—H22	118.7
C3—C2—C1	121.1 (4)	N2—C23—C24	123.0 (3)
C4—C3—C2	120.0 (4)	N2—C23—H23	118.5
C4—C3—H3	120.0	C24—C23—H23	118.5
C2—C3—H3	120.0	C23—C24—C20	119.6 (4)
C3—C4—C5	121.4 (4)	C23—C24—H24	120.2
C3—C4—H4	119.3	C20—C24—H24	120.2
C5—C4—H4	119.3	N3—C25—H25A	109.5
C6—C5—C4	118.3 (3)	N3—C25—H25B	109.5
C6—C5—C8	122.2 (3)	H25A—C25—H25B	109.5
C4—C5—C8	119.5 (3)	N3—C25—H25C	109.5
C5—C6—C7	120.8 (4)	H25A—C25—H25C	109.5
C5—C6—H6	119.6	H25B—C25—H25C	109.5
C7—C6—H6	119.6	N3—C26—H26A	109.5
C2—C7—C6	120.6 (4)	N3—C26—H26B	109.5
C2—C7—H7	119.7	H26A—C26—H26B	109.5
C6—C7—H7	119.7	N3—C26—H26C	109.5
N1—C8—C9	122.8 (3)	H26A—C26—H26C	109.5
N1—C8—C5	115.0 (3)	H26B—C26—H26C	109.5
C9—C8—C5	122.2 (3)	O5—C27—N3	124.9 (5)
C10—C9—C8	119.2 (3)	O5—C27—H27	117.6
C10—C9—H9	120.4	N3—C27—H27	117.6
C8—C9—H9	120.4	N4—C28—H28A	109.5
C9—C10—C11	117.7 (3)	N4—C28—H28B	109.5
C9—C10—C20	122.1 (3)	H28A—C28—H28B	109.5
C11—C10—C20	120.2 (3)	N4—C28—H28C	109.5
C12—C11—C10	119.9 (3)	H28A—C28—H28C	109.5
C12—C11—H11	120.1	H28B—C28—H28C	109.5
C10—C11—H11	120.1	N4—C29—H29A	109.5
N1—C12—C11	122.3 (3)	N4—C29—H29B	109.5
N1—C12—C13	115.9 (3)	H29A—C29—H29B	109.5
C11—C12—C13	121.8 (3)	N4—C29—H29C	109.5
C14—C13—C18	118.8 (3)	H29A—C29—H29C	109.5
C14—C13—C12	119.9 (3)	H29B—C29—H29C	109.5
C18—C13—C12	121.3 (3)	O6—C30—N4	128.2 (7)
C15—C14—C13	120.9 (4)	O6—C30—H30	115.9
C15—C14—H14	119.6	N4—C30—H30	115.9
C13—C14—H14	119.6	C8—N1—C12	118.2 (3)
C14—C15—C16	120.3 (4)	C23—N2—C22	117.3 (3)
C14—C15—H15	119.9	C23—N2—Cu1	121.6 (2)
C16—C15—H15	119.9	C22—N2—Cu1	120.9 (3)
C17—C16—C15	119.2 (4)	C27—N3—C25	121.1 (5)
C17—C16—C19	120.7 (4)	C27—N3—C26	121.6 (4)
C15—C16—C19	120.1 (3)	C25—N3—C26	117.3 (4)
C16—C17—C18	120.2 (4)	C30—N4—C29	125.9 (7)
C16—C17—H17	119.9	C30—N4—C28	120.2 (7)
C18—C17—H17	119.9	C29—N4—C28	113.8 (7)
C17—C18—C13	120.6 (4)	C19—O1—Cu1iv	128.1 (3)
C17—C18—H18	119.7	C1—O4—H4A	109.5
C13—C18—H18	119.7	H1A—O1W—H1B	107.4
O2—C19—O1	125.4 (4)
O3—C1—C2—C7	−8.6 (7)	C19—C16—C17—C18	179.6 (4)
O4—C1—C2—C7	173.1 (4)	C16—C17—C18—C13	−1.0 (6)
O3—C1—C2—C3	166.8 (4)	C14—C13—C18—C17	2.5 (6)
O4—C1—C2—C3	−11.4 (6)	C12—C13—C18—C17	−178.2 (3)
C7—C2—C3—C4	1.3 (6)	C17—C16—C19—O2	−167.7 (4)
C1—C2—C3—C4	−174.2 (4)	C15—C16—C19—O2	12.3 (5)
C2—C3—C4—C5	−1.1 (6)	C17—C16—C19—O1	11.0 (5)
C3—C4—C5—C6	0.6 (6)	C15—C16—C19—O1	−168.9 (4)
C3—C4—C5—C8	178.0 (4)	C9—C10—C20—C21	30.9 (6)
C4—C5—C6—C7	−0.2 (6)	C11—C10—C20—C21	−146.3 (4)
C8—C5—C6—C7	−177.6 (4)	C9—C10—C20—C24	−153.5 (4)
C3—C2—C7—C6	−1.0 (6)	C11—C10—C20—C24	29.2 (5)
C1—C2—C7—C6	174.6 (4)	C24—C20—C21—C22	−3.5 (6)
C5—C6—C7—C2	0.5 (6)	C10—C20—C21—C22	172.2 (4)
C6—C5—C8—N1	167.3 (3)	C20—C21—C22—N2	0.6 (6)
C4—C5—C8—N1	−10.0 (5)	N2—C23—C24—C20	0.7 (6)
C6—C5—C8—C9	−11.9 (6)	C21—C20—C24—C23	2.9 (6)
C4—C5—C8—C9	170.7 (4)	C10—C20—C24—C23	−172.8 (4)
N1—C8—C9—C10	−1.8 (6)	C9—C8—N1—C12	1.4 (5)
C5—C8—C9—C10	177.3 (3)	C5—C8—N1—C12	−177.9 (3)
C8—C9—C10—C11	1.2 (5)	C11—C12—N1—C8	−0.4 (5)
C8—C9—C10—C20	−176.1 (3)	C13—C12—N1—C8	−179.9 (3)
C9—C10—C11—C12	−0.3 (5)	C24—C23—N2—C22	−3.6 (6)
C20—C10—C11—C12	177.1 (3)	C24—C23—N2—Cu1	171.8 (3)
C10—C11—C12—N1	−0.1 (6)	C21—C22—N2—C23	3.0 (6)
C10—C11—C12—C13	179.4 (3)	C21—C22—N2—Cu1	−172.4 (3)
N1—C12—C13—C14	28.6 (5)	O1i—Cu1—N2—C23	−34.5 (3)
C11—C12—C13—C14	−151.0 (4)	O1ii—Cu1—N2—C23	145.5 (3)
N1—C12—C13—C18	−150.7 (4)	O1i—Cu1—N2—C22	140.8 (3)
C11—C12—C13—C18	29.8 (6)	O1ii—Cu1—N2—C22	−39.2 (3)
C18—C13—C14—C15	−2.7 (6)	O5—C27—N3—C25	179.0 (5)
C12—C13—C14—C15	178.1 (4)	O5—C27—N3—C26	2.5 (8)
C13—C14—C15—C16	1.3 (6)	O6—C30—N4—C29	171.2 (8)
C14—C15—C16—C17	0.3 (6)	O6—C30—N4—C28	−10.0 (14)
C14—C15—C16—C19	−179.8 (4)	O2—C19—O1—Cu1iv	−6.5 (6)
C15—C16—C17—C18	−0.4 (6)	C16—C19—O1—Cu1iv	174.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O2v	0.82	1.86	2.584 (4)	146
O1W—H1A···O5vi	0.85	1.98	2.808 (5)	165
O1W—H1B···O2i	0.85	1.95	2.758 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O2i	0.82	1.86	2.584 (4)	146
O1W—H1A⋯O5ii	0.85	1.98	2.808 (5)	165
O1W—H1B⋯O2iii	0.85	1.95	2.758 (4)	159

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