Tetra-kis(μ-2-phenyl-quinoline-4-carboxyl-ato-κ(2)O:O')bis-[(methanol-κO)copper(II)].

The title complex, [Cu(2)(C(16)H(10)NO(2))(4)(CH(3)OH)(2)], consists of centrosymmetric wheel-shaped dinuclear neutral mol-ecules in which each Cu(II) atom is coordinated in a slightly distorted square-pyramidal geometry by four O atoms of carboxyl-ate groups from different ligands at the basal plane and an O atom of a methanol mol-ecule at the axial position. In the crystal, the dinuclear complex mol-ecules are linked into one-dimensional supra-molecular columns parallel to the b axis by O-H⋯N hydrogen bonds and π-π stacking inter-actions [centroid-centroid distance = 3.7259 (11) Å].

Related literature

For the background to isonicotinic acid derivatives as polyfunctional ligands, see: Evans & Lin (2002 ▶); Aakeröy et al. (1999 ▶); Xiong et al. (2000 ▶); Qin et al. (2002 ▶); Shen et al. (2007 ▶). For the structures of related compounds, see: Bu et al. (2005 ▶); Wang et al. (2010 ▶); Ma & Lin (2008 ▶).

Experimental

Crystal data

[Cu2(C16H10NO2)4(CH4O)2]

M = 1184.16

Triclinic,

a = 8.9671 (6) Å

b = 10.5859 (7) Å

c = 14.7767 (10) Å

α = 89.800 (1)°

β = 87.348 (1)°

γ = 77.300 (1)°

V = 1366.86 (16) Å3

Z = 1

Mo Kα radiation

μ = 0.85 mm−1

T = 293 K

0.31 × 0.24 × 0.17 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.780, T max = 0.870

7266 measured reflections

4984 independent reflections

4583 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.088

S = 1.06

4984 reflections

370 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.30 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 datablock(s) I, global. DOI: 10.1107/S1600536812039839/rz5004sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039839/rz5004Isup2.hkl

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

[Cu2(C16H10NO2)4(CH4O)2]	Z = 1
Mr = 1184.16	F(000) = 610
Triclinic, P1	Dx = 1.439 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.9671 (6) Å	Cell parameters from 4273 reflections
b = 10.5859 (7) Å	θ = 2.7–25.5°
c = 14.7767 (10) Å	µ = 0.85 mm−1
α = 89.800 (1)°	T = 293 K
β = 87.348 (1)°	Block, green
γ = 77.300 (1)°	0.31 × 0.24 × 0.17 mm
V = 1366.86 (16) Å3

Bruker APEX CCD diffractometer	4984 independent reflections
Radiation source: fine-focus sealed tube	4583 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 25.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
Tmin = 0.780, Tmax = 0.870	k = −10→12
7266 measured reflections	l = −17→14

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0453P)2 + 0.8119P] where P = (Fo2 + 2Fc2)/3
4984 reflections	(Δ/σ)max = 0.002
370 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.30 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
C1	0.3269 (2)	−0.31756 (19)	0.53165 (14)	0.0228 (4)
C2	0.3333 (2)	−0.40391 (19)	0.45686 (14)	0.0232 (4)
C3	0.2708 (2)	−0.51467 (19)	0.47299 (14)	0.0232 (4)
C4	0.2167 (2)	−0.4635 (2)	0.62569 (14)	0.0245 (4)
C5	0.2661 (2)	−0.3457 (2)	0.61337 (14)	0.0252 (4)
H5	0.2569	−0.2876	0.6614	0.030*
C6	0.3893 (2)	−0.3828 (2)	0.36841 (14)	0.0283 (5)
H6	0.4318	−0.3113	0.3570	0.034*
C7	0.3817 (3)	−0.4665 (2)	0.29958 (15)	0.0343 (5)
H7	0.4211	−0.4526	0.2420	0.041*
C8	0.3147 (3)	−0.5737 (2)	0.31503 (16)	0.0345 (5)
H8	0.3066	−0.6281	0.2671	0.041*
C9	0.2618 (2)	−0.5980 (2)	0.39974 (15)	0.0290 (5)
H9	0.2195	−0.6699	0.4095	0.035*
C10	0.1622 (2)	−0.5001 (2)	0.71649 (14)	0.0280 (5)
C11	0.2097 (3)	−0.6262 (2)	0.74798 (16)	0.0352 (5)
H11	0.2781	−0.6872	0.7126	0.042*
C12	0.1557 (3)	−0.6609 (2)	0.83149 (17)	0.0424 (6)
H12	0.1883	−0.7450	0.8524	0.051*
C13	0.0531 (3)	−0.5706 (3)	0.88392 (17)	0.0448 (6)
H13	0.0158	−0.5943	0.9397	0.054*
C14	0.0061 (3)	−0.4456 (3)	0.85373 (17)	0.0437 (6)
H14	−0.0631	−0.3853	0.8891	0.052*
C15	0.0617 (3)	−0.4093 (2)	0.77056 (16)	0.0348 (5)
H15	0.0317	−0.3242	0.7511	0.042*
C16	0.3837 (2)	−0.19459 (19)	0.52106 (13)	0.0224 (4)
C17	0.6511 (3)	−0.0701 (2)	0.75173 (14)	0.0278 (5)
C18	0.7991 (3)	−0.0616 (2)	0.77910 (15)	0.0302 (5)
C19	0.8346 (3)	−0.0995 (2)	0.86945 (15)	0.0319 (5)
C20	0.6033 (3)	−0.1580 (2)	0.89854 (15)	0.0312 (5)
C21	0.5550 (3)	−0.1164 (2)	0.81085 (15)	0.0299 (5)
H21	0.4578	−0.1209	0.7938	0.036*
C22	0.9081 (3)	−0.0138 (3)	0.72450 (17)	0.0404 (6)
H22	0.8868	0.0109	0.6652	0.049*
C23	1.0445 (3)	−0.0034 (3)	0.75807 (19)	0.0499 (7)
H23	1.1148	0.0287	0.7216	0.060*
C24	1.0790 (3)	−0.0408 (3)	0.84710 (19)	0.0492 (7)
H24	1.1718	−0.0328	0.8694	0.059*
C25	0.9774 (3)	−0.0891 (3)	0.90132 (17)	0.0419 (6)
H25	1.0026	−0.1153	0.9599	0.050*
C26	0.5958 (2)	−0.0336 (2)	0.65834 (14)	0.0261 (4)
C27	0.5007 (3)	−0.2130 (2)	0.96154 (16)	0.0369 (5)
C28	0.4088 (4)	−0.2913 (3)	0.9297 (2)	0.0595 (8)
H28	0.4114	−0.3103	0.8682	0.071*
C29	0.3129 (4)	−0.3413 (4)	0.9894 (2)	0.0801 (12)
H29	0.2533	−0.3954	0.9681	0.096*
C30	0.3061 (4)	−0.3108 (4)	1.0805 (2)	0.0723 (11)
H30	0.2397	−0.3424	1.1203	0.087*
C31	0.3971 (4)	−0.2339 (3)	1.1124 (2)	0.0565 (8)
H31	0.3928	−0.2142	1.1739	0.068*
C32	0.4952 (3)	−0.1857 (3)	1.05379 (17)	0.0436 (6)
H32	0.5577	−0.1347	1.0761	0.052*
C33	0.0245 (3)	0.1999 (3)	0.5450 (2)	0.0491 (7)
H33A	−0.0514	0.2706	0.5706	0.074*
H33B	−0.0003	0.1194	0.5629	0.074*
H33C	0.0268	0.2059	0.4801	0.074*
N1	0.21783 (19)	−0.54469 (16)	0.55746 (12)	0.0247 (4)
N2	0.7381 (2)	−0.14840 (18)	0.92751 (12)	0.0331 (4)
O1	0.29567 (17)	−0.09218 (14)	0.55023 (10)	0.0291 (3)
O2	0.51543 (16)	−0.20471 (13)	0.48438 (10)	0.0278 (3)
O3	0.46126 (18)	0.03347 (15)	0.65482 (10)	0.0324 (4)
O4	0.68533 (17)	−0.07591 (14)	0.59207 (10)	0.0290 (3)
O5	0.17001 (16)	0.20531 (13)	0.57646 (10)	0.0267 (3)
H1	0.1821	0.2812	0.5735	0.040*
Cu1	0.37041 (3)	0.06756 (2)	0.536332 (16)	0.02076 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0185 (10)	0.0188 (10)	0.0312 (11)	−0.0041 (8)	−0.0020 (8)	0.0042 (8)
C2	0.0184 (10)	0.0210 (10)	0.0294 (11)	−0.0027 (8)	−0.0018 (8)	0.0023 (8)
C3	0.0211 (10)	0.0192 (10)	0.0289 (11)	−0.0039 (8)	−0.0009 (8)	0.0037 (8)
C4	0.0215 (10)	0.0228 (10)	0.0294 (11)	−0.0054 (8)	0.0007 (8)	0.0041 (9)
C5	0.0249 (10)	0.0215 (10)	0.0300 (11)	−0.0072 (8)	0.0002 (8)	−0.0004 (8)
C6	0.0291 (11)	0.0263 (11)	0.0306 (11)	−0.0087 (9)	0.0003 (9)	0.0064 (9)
C7	0.0412 (13)	0.0353 (13)	0.0270 (11)	−0.0105 (10)	0.0009 (10)	0.0058 (10)
C8	0.0444 (14)	0.0293 (12)	0.0307 (12)	−0.0092 (10)	−0.0045 (10)	−0.0011 (9)
C9	0.0319 (12)	0.0217 (11)	0.0346 (12)	−0.0084 (9)	−0.0024 (9)	0.0014 (9)
C10	0.0296 (11)	0.0281 (11)	0.0295 (11)	−0.0138 (9)	0.0000 (9)	0.0024 (9)
C11	0.0423 (13)	0.0311 (12)	0.0334 (12)	−0.0110 (10)	0.0007 (10)	0.0048 (10)
C12	0.0583 (16)	0.0334 (13)	0.0397 (14)	−0.0194 (12)	−0.0022 (12)	0.0114 (11)
C13	0.0576 (16)	0.0556 (17)	0.0287 (12)	−0.0297 (14)	0.0042 (11)	0.0051 (11)
C14	0.0470 (15)	0.0501 (16)	0.0350 (13)	−0.0152 (12)	0.0101 (11)	−0.0041 (12)
C15	0.0375 (13)	0.0330 (12)	0.0343 (12)	−0.0090 (10)	0.0020 (10)	0.0009 (10)
C16	0.0232 (10)	0.0210 (10)	0.0238 (10)	−0.0066 (8)	−0.0026 (8)	0.0043 (8)
C17	0.0334 (12)	0.0252 (11)	0.0253 (11)	−0.0071 (9)	−0.0021 (9)	−0.0008 (9)
C18	0.0335 (12)	0.0291 (12)	0.0292 (11)	−0.0094 (9)	−0.0018 (9)	−0.0017 (9)
C19	0.0353 (12)	0.0314 (12)	0.0297 (12)	−0.0085 (10)	−0.0021 (9)	−0.0012 (9)
C20	0.0343 (12)	0.0312 (12)	0.0275 (11)	−0.0062 (10)	−0.0012 (9)	0.0023 (9)
C21	0.0323 (12)	0.0311 (12)	0.0277 (11)	−0.0094 (9)	−0.0027 (9)	0.0010 (9)
C22	0.0442 (14)	0.0494 (15)	0.0327 (13)	−0.0213 (12)	−0.0010 (10)	0.0026 (11)
C23	0.0461 (15)	0.0695 (19)	0.0427 (15)	−0.0320 (14)	0.0009 (12)	0.0010 (13)
C24	0.0397 (14)	0.0660 (19)	0.0484 (16)	−0.0247 (13)	−0.0077 (12)	−0.0021 (14)
C25	0.0427 (14)	0.0529 (16)	0.0327 (13)	−0.0145 (12)	−0.0095 (11)	−0.0011 (11)
C26	0.0336 (12)	0.0224 (10)	0.0256 (11)	−0.0129 (9)	−0.0026 (9)	0.0018 (8)
C27	0.0363 (13)	0.0426 (14)	0.0313 (12)	−0.0074 (11)	−0.0031 (10)	0.0125 (10)
C28	0.0622 (19)	0.086 (2)	0.0424 (16)	−0.0414 (17)	−0.0137 (14)	0.0240 (15)
C29	0.070 (2)	0.128 (3)	0.065 (2)	−0.066 (2)	−0.0248 (17)	0.046 (2)
C30	0.0505 (18)	0.112 (3)	0.061 (2)	−0.0313 (19)	−0.0030 (15)	0.049 (2)
C31	0.0649 (19)	0.0587 (18)	0.0397 (15)	−0.0031 (15)	0.0116 (14)	0.0182 (13)
C32	0.0526 (16)	0.0404 (14)	0.0356 (13)	−0.0065 (12)	0.0034 (11)	0.0096 (11)
C33	0.0239 (12)	0.0522 (16)	0.0721 (19)	−0.0098 (11)	−0.0035 (12)	0.0147 (14)
N1	0.0232 (9)	0.0217 (9)	0.0299 (9)	−0.0066 (7)	0.0005 (7)	0.0035 (7)
N2	0.0389 (11)	0.0341 (11)	0.0266 (10)	−0.0081 (9)	−0.0031 (8)	0.0025 (8)
O1	0.0305 (8)	0.0200 (7)	0.0375 (9)	−0.0089 (6)	0.0078 (6)	0.0006 (6)
O2	0.0236 (7)	0.0204 (7)	0.0407 (9)	−0.0085 (6)	0.0020 (6)	0.0017 (6)
O3	0.0341 (9)	0.0381 (9)	0.0232 (8)	−0.0040 (7)	−0.0006 (6)	0.0037 (7)
O4	0.0327 (8)	0.0311 (8)	0.0232 (7)	−0.0068 (7)	−0.0026 (6)	0.0011 (6)
O5	0.0229 (7)	0.0185 (7)	0.0385 (8)	−0.0044 (6)	−0.0001 (6)	0.0005 (6)
Cu1	0.02186 (14)	0.01805 (14)	0.02282 (14)	−0.00599 (10)	0.00180 (9)	0.00185 (9)

C1—C5	1.361 (3)	C20—N2	1.325 (3)
C1—C2	1.428 (3)	C20—C21	1.423 (3)
C1—C16	1.504 (3)	C20—C27	1.485 (3)
C2—C6	1.413 (3)	C21—H21	0.9300
C2—C3	1.421 (3)	C22—C23	1.367 (4)
C3—N1	1.376 (3)	C22—H22	0.9300
C3—C9	1.415 (3)	C23—C24	1.401 (4)
C4—N1	1.325 (3)	C23—H23	0.9300
C4—C5	1.421 (3)	C24—C25	1.367 (4)
C4—C10	1.486 (3)	C24—H24	0.9300
C5—H5	0.9300	C25—H25	0.9300
C6—C7	1.365 (3)	C26—O4	1.256 (3)
C6—H6	0.9300	C26—O3	1.261 (3)
C7—C8	1.409 (3)	C27—C28	1.388 (4)
C7—H7	0.9300	C27—C32	1.391 (3)
C8—C9	1.362 (3)	C28—C29	1.387 (4)
C8—H8	0.9300	C28—H28	0.9300
C9—H9	0.9300	C29—C30	1.380 (5)
C10—C15	1.390 (3)	C29—H29	0.9300
C10—C11	1.394 (3)	C30—C31	1.372 (5)
C11—C12	1.383 (3)	C30—H30	0.9300
C11—H11	0.9300	C31—C32	1.381 (4)
C12—C13	1.383 (4)	C31—H31	0.9300
C12—H12	0.9300	C32—H32	0.9300
C13—C14	1.377 (4)	C33—O5	1.418 (3)
C13—H13	0.9300	C33—H33A	0.9600
C14—C15	1.390 (3)	C33—H33B	0.9600
C14—H14	0.9300	C33—H33C	0.9600
C15—H15	0.9300	O1—Cu1	1.9581 (14)
C16—O1	1.257 (2)	O2—Cu1i	1.9674 (13)
C16—O2	1.260 (2)	O3—Cu1	1.9641 (15)
C17—C21	1.363 (3)	O4—Cu1i	1.9812 (14)
C17—C18	1.427 (3)	O5—Cu1	2.1125 (14)
C17—C26	1.508 (3)	O5—H1	0.8340
C18—C22	1.416 (3)	Cu1—O2i	1.9674 (14)
C18—C19	1.423 (3)	Cu1—O4i	1.9812 (14)
C19—N2	1.370 (3)	Cu1—Cu1i	2.6303 (5)
C19—C25	1.411 (3)
C5—C1—C2	119.56 (18)	C23—C22—C18	120.7 (2)
C5—C1—C16	119.45 (18)	C23—C22—H22	119.7
C2—C1—C16	120.98 (17)	C18—C22—H22	119.7
C6—C2—C3	118.79 (19)	C22—C23—C24	120.4 (2)
C6—C2—C1	124.56 (18)	C22—C23—H23	119.8
C3—C2—C1	116.57 (18)	C24—C23—H23	119.8
N1—C3—C9	118.14 (18)	C25—C24—C23	120.5 (2)
N1—C3—C2	122.63 (18)	C25—C24—H24	119.8
C9—C3—C2	119.23 (19)	C23—C24—H24	119.8
N1—C4—C5	121.68 (19)	C24—C25—C19	120.7 (2)
N1—C4—C10	117.63 (18)	C24—C25—H25	119.6
C5—C4—C10	120.69 (19)	C19—C25—H25	119.6
C1—C5—C4	120.35 (19)	O4—C26—O3	126.5 (2)
C1—C5—H5	119.8	O4—C26—C17	117.32 (19)
C4—C5—H5	119.8	O3—C26—C17	116.17 (19)
C7—C6—C2	120.5 (2)	C28—C27—C32	119.1 (2)
C7—C6—H6	119.7	C28—C27—C20	120.9 (2)
C2—C6—H6	119.7	C32—C27—C20	120.0 (2)
C6—C7—C8	120.6 (2)	C29—C28—C27	120.2 (3)
C6—C7—H7	119.7	C29—C28—H28	119.9
C8—C7—H7	119.7	C27—C28—H28	119.9
C9—C8—C7	120.4 (2)	C30—C29—C28	120.0 (3)
C9—C8—H8	119.8	C30—C29—H29	120.0
C7—C8—H8	119.8	C28—C29—H29	120.0
C8—C9—C3	120.4 (2)	C31—C30—C29	120.0 (3)
C8—C9—H9	119.8	C31—C30—H30	120.0
C3—C9—H9	119.8	C29—C30—H30	120.0
C15—C10—C11	119.2 (2)	C30—C31—C32	120.4 (3)
C15—C10—C4	120.3 (2)	C30—C31—H31	119.8
C11—C10—C4	120.4 (2)	C32—C31—H31	119.8
C12—C11—C10	120.3 (2)	C31—C32—C27	120.2 (3)
C12—C11—H11	119.8	C31—C32—H32	119.9
C10—C11—H11	119.8	C27—C32—H32	119.9
C11—C12—C13	120.0 (2)	O5—C33—H33A	109.5
C11—C12—H12	120.0	O5—C33—H33B	109.5
C13—C12—H12	120.0	H33A—C33—H33B	109.5
C14—C13—C12	120.2 (2)	O5—C33—H33C	109.5
C14—C13—H13	119.9	H33A—C33—H33C	109.5
C12—C13—H13	119.9	H33B—C33—H33C	109.5
C13—C14—C15	120.2 (2)	C4—N1—C3	118.90 (17)
C13—C14—H14	119.9	C20—N2—C19	118.18 (19)
C15—C14—H14	119.9	C16—O1—Cu1	116.67 (13)
C14—C15—C10	120.0 (2)	C16—O2—Cu1i	128.06 (13)
C14—C15—H15	120.0	C26—O3—Cu1	119.04 (14)
C10—C15—H15	120.0	C26—O4—Cu1i	125.28 (14)
O1—C16—O2	126.46 (18)	C33—O5—Cu1	122.05 (15)
O1—C16—C1	116.89 (17)	C33—O5—H1	109.7
O2—C16—C1	116.64 (17)	Cu1—O5—H1	112.6
C21—C17—C18	119.5 (2)	O1—Cu1—O3	88.25 (7)
C21—C17—C26	117.53 (19)	O1—Cu1—O2i	168.60 (6)
C18—C17—C26	122.98 (19)	O3—Cu1—O2i	89.51 (6)
C22—C18—C19	118.7 (2)	O1—Cu1—O4i	89.50 (6)
C22—C18—C17	124.8 (2)	O3—Cu1—O4i	168.63 (6)
C19—C18—C17	116.4 (2)	O2i—Cu1—O4i	90.51 (6)
N2—C19—C25	117.6 (2)	O1—Cu1—O5	100.09 (6)
N2—C19—C18	123.4 (2)	O3—Cu1—O5	99.20 (6)
C25—C19—C18	119.0 (2)	O2i—Cu1—O5	91.30 (6)
N2—C20—C21	122.3 (2)	O4i—Cu1—O5	92.17 (6)
N2—C20—C27	117.7 (2)	O1—Cu1—Cu1i	89.46 (4)
C21—C20—C27	120.0 (2)	O3—Cu1—Cu1i	87.46 (5)
C17—C21—C20	120.1 (2)	O2i—Cu1—Cu1i	79.27 (4)
C17—C21—H21	119.9	O4i—Cu1—Cu1i	81.37 (5)
C20—C21—H21	119.9	O5—Cu1—Cu1i	168.47 (4)
C5—C1—C2—C6	178.0 (2)	C23—C24—C25—C19	−1.4 (4)
C16—C1—C2—C6	−0.9 (3)	N2—C19—C25—C24	−179.8 (2)
C5—C1—C2—C3	1.4 (3)	C18—C19—C25—C24	1.3 (4)
C16—C1—C2—C3	−177.41 (17)	C21—C17—C26—O4	−131.5 (2)
C6—C2—C3—N1	178.03 (19)	C18—C17—C26—O4	46.7 (3)
C1—C2—C3—N1	−5.2 (3)	C21—C17—C26—O3	46.2 (3)
C6—C2—C3—C9	−2.1 (3)	C18—C17—C26—O3	−135.6 (2)
C1—C2—C3—C9	174.67 (18)	N2—C20—C27—C28	−143.6 (3)
C2—C1—C5—C4	3.3 (3)	C21—C20—C27—C28	37.0 (4)
C16—C1—C5—C4	−177.83 (18)	N2—C20—C27—C32	36.8 (3)
N1—C4—C5—C1	−4.8 (3)	C21—C20—C27—C32	−142.6 (2)
C10—C4—C5—C1	174.91 (19)	C32—C27—C28—C29	0.0 (5)
C3—C2—C6—C7	0.8 (3)	C20—C27—C28—C29	−179.6 (3)
C1—C2—C6—C7	−175.6 (2)	C27—C28—C29—C30	1.5 (6)
C2—C6—C7—C8	1.4 (3)	C28—C29—C30—C31	−1.8 (6)
C6—C7—C8—C9	−2.5 (4)	C29—C30—C31—C32	0.5 (5)
C7—C8—C9—C3	1.2 (3)	C30—C31—C32—C27	1.0 (4)
N1—C3—C9—C8	−179.0 (2)	C28—C27—C32—C31	−1.2 (4)
C2—C3—C9—C8	1.1 (3)	C20—C27—C32—C31	178.4 (2)
N1—C4—C10—C15	−135.3 (2)	C5—C4—N1—C3	1.1 (3)
C5—C4—C10—C15	45.0 (3)	C10—C4—N1—C3	−178.63 (18)
N1—C4—C10—C11	44.0 (3)	C9—C3—N1—C4	−175.89 (19)
C5—C4—C10—C11	−135.8 (2)	C2—C3—N1—C4	4.0 (3)
C15—C10—C11—C12	1.0 (3)	C21—C20—N2—C19	−1.6 (3)
C4—C10—C11—C12	−178.3 (2)	C27—C20—N2—C19	179.0 (2)
C10—C11—C12—C13	0.5 (4)	C25—C19—N2—C20	179.6 (2)
C11—C12—C13—C14	−0.8 (4)	C18—C19—N2—C20	−1.6 (3)
C12—C13—C14—C15	−0.2 (4)	O2—C16—O1—Cu1	0.5 (3)
C13—C14—C15—C10	1.6 (4)	C1—C16—O1—Cu1	179.94 (13)
C11—C10—C15—C14	−2.0 (3)	O1—C16—O2—Cu1i	2.0 (3)
C4—C10—C15—C14	177.2 (2)	C1—C16—O2—Cu1i	−177.45 (13)
C5—C1—C16—O1	−48.6 (3)	O4—C26—O3—Cu1	5.0 (3)
C2—C1—C16—O1	130.2 (2)	C17—C26—O3—Cu1	−172.51 (13)
C5—C1—C16—O2	130.9 (2)	O3—C26—O4—Cu1i	−8.3 (3)
C2—C1—C16—O2	−50.3 (3)	C17—C26—O4—Cu1i	169.13 (13)
C21—C17—C18—C22	−179.1 (2)	C16—O1—Cu1—O3	−89.21 (15)
C26—C17—C18—C22	2.7 (4)	C16—O1—Cu1—O2i	−10.4 (4)
C21—C17—C18—C19	−1.8 (3)	C16—O1—Cu1—O4i	79.64 (15)
C26—C17—C18—C19	179.97 (19)	C16—O1—Cu1—O5	171.75 (15)
C22—C18—C19—N2	−179.2 (2)	C16—O1—Cu1—Cu1i	−1.74 (15)
C17—C18—C19—N2	3.3 (3)	C26—O3—Cu1—O1	89.18 (16)
C22—C18—C19—C25	−0.4 (3)	C26—O3—Cu1—O2i	−79.64 (16)
C17—C18—C19—C25	−177.9 (2)	C26—O3—Cu1—O4i	10.5 (4)
C18—C17—C21—C20	−1.1 (3)	C26—O3—Cu1—O5	−170.88 (15)
C26—C17—C21—C20	177.21 (19)	C26—O3—Cu1—Cu1i	−0.36 (15)
N2—C20—C21—C17	3.0 (3)	C33—O5—Cu1—O1	−45.20 (18)
C27—C20—C21—C17	−177.7 (2)	C33—O5—Cu1—O3	−135.05 (17)
C19—C18—C22—C23	−0.4 (4)	C33—O5—Cu1—O2i	135.23 (17)
C17—C18—C22—C23	176.8 (2)	C33—O5—Cu1—O4i	44.68 (17)
C18—C22—C23—C24	0.4 (4)	C33—O5—Cu1—Cu1i	100.3 (2)
C22—C23—C24—C25	0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1···N1ii	0.83	1.95	2.784 (2)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1⋯N1i	0.83	1.95	2.784 (2)	176

Symmetry code: (i) .