Intermolecular interaction energies and magnetic properties of spin-isolated multinuclear Cu^II complexes

Dinuclear Cu^II complexes with 3,5-di­nitro­benzoates and 2,2′-bi­pyridine (2) or 1,10-phenanthroline (3) were synthesized and characterized. A complete energy framework analysis using the HF/3-21G energy model was performed which found that dispersion forces and C—H...O interactions are responsible for the crystal structure features. The magnetic properties of the complexes show a weak magnetic exchange between spins, resulting in low exchange constants of −2.72 (1) cm⁻¹ and −1.10 (1) cm⁻¹ for complexes (2) and (3), respectively. This results from the low overlap between magnetic orbitals induced by 3,5-di­nitro­benzoate bridges and the arrangement of the magnetic orbitals. Consequently, the dinuclear complexes (2) and (3) behave as spin-isolated multinuclear Cu^II species in contrast to the trinuclear complex with similar ligands.

Computing details

For both structures, data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01); cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01); data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01); program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(complex_2)

Crystal data

C24H14CuN6O12	F(000) = 1300
Mr = 641.95	Dx = 1.695 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.2998 (18) Å	Cell parameters from 6816 reflections
b = 25.770 (3) Å	θ = 3.9–26.3°
c = 9.3086 (12) Å	µ = 0.95 mm^−1
β = 111.894 (16)°	T = 298 K
V = 2515.2 (6) Å^3	Parallelepiped, blue
Z = 4	0.20 × 0.10 × 0.07 mm

Data collection

SuperNova, Dual, Cu at zero, Atlas diffractometer	5134 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4104 reflections with I > 2σ(I)
Detector resolution: 5.3072 pixels mm^-1	Rint = 0.068
ω scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −13→14
Tmin = 0.555, Tmax = 1.000	k = −32→31
27634 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0598P)^2 + 1.8006P] where P = (Fo^2 + 2Fc^2)/3
5134 reflections	(Δ/σ)max = 0.001
388 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.94 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.11627 (4)	0.46640 (2)	0.24959 (4)	0.04010 (14)
O2	0.2189 (2)	0.41767 (9)	0.1908 (3)	0.0541 (6)
C3	0.2233 (3)	0.36959 (13)	0.2312 (3)	0.0440 (7)
O4	0.1716 (2)	0.34993 (10)	0.3117 (3)	0.0579 (6)
C5	0.3054 (3)	0.33666 (11)	0.1708 (3)	0.0372 (6)
C6	0.3869 (3)	0.35960 (11)	0.1091 (3)	0.0392 (6)
H6	0.390572	0.395526	0.102160	0.047*
C7	0.4623 (3)	0.32838 (11)	0.0583 (3)	0.0378 (6)
N8	0.5525 (3)	0.35243 (11)	−0.0009 (3)	0.0530 (7)
O9	0.5603 (3)	0.39951 (10)	−0.0017 (3)	0.0714 (8)
O10	0.6149 (3)	0.32362 (12)	−0.0499 (5)	0.0908 (10)
C11	0.4595 (3)	0.27497 (11)	0.0643 (3)	0.0374 (6)
H11	0.510382	0.254470	0.028389	0.045*
C12	0.3775 (3)	0.25353 (10)	0.1263 (3)	0.0360 (6)
C13	0.3020 (3)	0.28265 (11)	0.1811 (3)	0.0382 (6)
H13	0.249281	0.266730	0.224481	0.046*
N14	0.3770 (2)	0.19626 (10)	0.1397 (3)	0.0446 (6)
O15	0.3129 (3)	0.17741 (9)	0.2061 (3)	0.0612 (7)
O16	0.4423 (3)	0.17108 (9)	0.0858 (3)	0.0667 (7)
O17	0.1540 (2)	0.52358 (8)	0.0864 (3)	0.0481 (5)
C18	0.1123 (3)	0.56504 (11)	0.0185 (3)	0.0393 (6)
O19	0.0407 (2)	0.56988 (8)	−0.1222 (2)	0.0492 (5)
C20	0.1482 (3)	0.61526 (11)	0.1082 (3)	0.0363 (6)
C21	0.0967 (3)	0.66260 (11)	0.0413 (3)	0.0403 (7)
H21	0.040841	0.664225	−0.061477	0.048*
C22	0.1298 (3)	0.70676 (12)	0.1298 (4)	0.0432 (7)
N23	0.0753 (3)	0.75735 (11)	0.0615 (4)	0.0609 (8)
O24	0.1097 (3)	0.79587 (11)	0.1414 (4)	0.0964 (11)
O25	0.0013 (3)	0.75777 (11)	−0.0728 (4)	0.0863 (10)
C26	0.2109 (3)	0.70671 (12)	0.2820 (4)	0.0456 (7)
H26	0.231580	0.737097	0.340007	0.055*
C27	0.2600 (3)	0.65951 (12)	0.3446 (3)	0.0425 (7)
C28	0.2306 (3)	0.61403 (12)	0.2608 (3)	0.0391 (6)
H28	0.266011	0.582771	0.306919	0.047*
N29	0.3444 (3)	0.65761 (13)	0.5079 (3)	0.0604 (8)
O30	0.3910 (3)	0.61569 (12)	0.5606 (3)	0.0884 (11)
O31	0.3642 (3)	0.69830 (12)	0.5811 (3)	0.0812 (9)
N32	0.0308 (2)	0.52430 (9)	0.3153 (3)	0.0373 (5)
C33	−0.0765 (3)	0.54757 (12)	0.2245 (4)	0.0448 (7)
H33	−0.119066	0.535075	0.124689	0.054*
C34	−0.1259 (3)	0.58974 (13)	0.2748 (4)	0.0520 (8)
H34	−0.200243	0.605627	0.208877	0.062*
C35	−0.0649 (3)	0.60805 (13)	0.4223 (4)	0.0534 (8)
H35	−0.097977	0.635884	0.458820	0.064*
C36	0.0465 (3)	0.58434 (12)	0.5152 (4)	0.0468 (7)
H36	0.089916	0.596229	0.615533	0.056*
C37	0.0937 (3)	0.54269 (11)	0.4589 (3)	0.0382 (6)
C38	0.2149 (3)	0.51622 (11)	0.5436 (3)	0.0411 (7)
N39	0.2498 (3)	0.48097 (10)	0.4601 (3)	0.0437 (6)
C40	0.3605 (4)	0.45598 (14)	0.5244 (4)	0.0572 (9)
H40	0.383658	0.431631	0.465878	0.069*
C41	0.4414 (4)	0.46515 (16)	0.6746 (5)	0.0732 (12)
H41	0.518549	0.447580	0.717550	0.088*
C42	0.4049 (4)	0.50104 (16)	0.7594 (4)	0.0718 (12)
H42	0.457851	0.507829	0.861243	0.086*
C43	0.2918 (4)	0.52679 (13)	0.6955 (4)	0.0566 (9)
H43	0.266866	0.550947	0.752983	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0517 (3)	0.0327 (2)	0.0362 (2)	0.00711 (15)	0.01666 (18)	−0.00482 (14)
O2	0.0697 (15)	0.0379 (13)	0.0596 (14)	0.0125 (11)	0.0299 (12)	−0.0038 (10)
C3	0.0458 (17)	0.0474 (19)	0.0378 (15)	0.0091 (14)	0.0142 (14)	−0.0045 (13)
O4	0.0689 (16)	0.0586 (15)	0.0575 (14)	0.0149 (12)	0.0364 (13)	0.0035 (12)
C5	0.0410 (15)	0.0368 (16)	0.0322 (13)	0.0047 (12)	0.0119 (12)	−0.0018 (11)
C6	0.0470 (17)	0.0307 (15)	0.0364 (14)	0.0023 (12)	0.0117 (13)	−0.0014 (11)
C7	0.0405 (16)	0.0378 (16)	0.0357 (14)	−0.0030 (12)	0.0148 (12)	0.0006 (12)
N8	0.0572 (17)	0.0471 (17)	0.0602 (17)	−0.0060 (13)	0.0282 (15)	0.0035 (13)
O9	0.099 (2)	0.0444 (15)	0.0857 (19)	−0.0183 (14)	0.0518 (17)	0.0000 (13)
O10	0.095 (2)	0.0670 (19)	0.151 (3)	0.0042 (16)	0.093 (2)	0.0061 (19)
C11	0.0411 (16)	0.0336 (15)	0.0369 (15)	0.0039 (12)	0.0137 (13)	−0.0028 (11)
C12	0.0395 (15)	0.0292 (14)	0.0349 (14)	−0.0005 (11)	0.0089 (12)	−0.0015 (11)
C13	0.0402 (15)	0.0377 (16)	0.0358 (14)	−0.0009 (12)	0.0131 (12)	−0.0003 (12)
N14	0.0477 (15)	0.0305 (13)	0.0514 (15)	−0.0012 (11)	0.0137 (13)	−0.0004 (11)
O15	0.0729 (17)	0.0421 (13)	0.0744 (17)	−0.0098 (12)	0.0342 (14)	0.0062 (12)
O16	0.0761 (17)	0.0344 (13)	0.099 (2)	0.0059 (12)	0.0427 (16)	−0.0080 (13)
O17	0.0688 (15)	0.0327 (11)	0.0468 (12)	0.0065 (10)	0.0263 (11)	0.0017 (9)
C18	0.0479 (17)	0.0360 (16)	0.0397 (15)	−0.0020 (13)	0.0229 (13)	−0.0028 (12)
O19	0.0638 (14)	0.0386 (12)	0.0379 (11)	−0.0033 (10)	0.0105 (10)	−0.0041 (9)
C20	0.0390 (15)	0.0354 (15)	0.0370 (14)	−0.0020 (12)	0.0171 (12)	−0.0018 (12)
C21	0.0400 (16)	0.0391 (16)	0.0403 (15)	0.0014 (12)	0.0131 (13)	0.0004 (12)
C22	0.0452 (17)	0.0334 (16)	0.0529 (18)	0.0007 (13)	0.0204 (14)	0.0011 (13)
N23	0.0613 (19)	0.0352 (16)	0.079 (2)	0.0037 (13)	0.0180 (17)	0.0033 (15)
O24	0.116 (3)	0.0369 (15)	0.115 (3)	0.0074 (16)	0.018 (2)	−0.0110 (16)
O25	0.088 (2)	0.0504 (16)	0.090 (2)	0.0120 (15)	−0.0013 (18)	0.0147 (15)
C26	0.0503 (18)	0.0385 (17)	0.0492 (17)	−0.0087 (14)	0.0201 (15)	−0.0085 (14)
C27	0.0442 (17)	0.0452 (18)	0.0351 (14)	−0.0119 (13)	0.0114 (13)	−0.0011 (13)
C28	0.0414 (15)	0.0354 (15)	0.0402 (15)	−0.0037 (12)	0.0146 (12)	0.0048 (12)
N29	0.0660 (19)	0.068 (2)	0.0373 (14)	−0.0287 (16)	0.0083 (14)	0.0013 (15)
O30	0.103 (2)	0.073 (2)	0.0539 (16)	−0.0329 (18)	−0.0110 (15)	0.0205 (14)
O31	0.105 (2)	0.083 (2)	0.0445 (14)	−0.0330 (17)	0.0156 (14)	−0.0208 (14)
N32	0.0509 (14)	0.0298 (12)	0.0350 (12)	−0.0001 (10)	0.0205 (11)	−0.0046 (9)
C33	0.0513 (18)	0.0395 (17)	0.0419 (16)	0.0058 (14)	0.0156 (14)	−0.0032 (13)
C34	0.059 (2)	0.0413 (18)	0.058 (2)	0.0120 (15)	0.0246 (17)	−0.0047 (15)
C35	0.071 (2)	0.0375 (17)	0.062 (2)	0.0052 (16)	0.0365 (18)	−0.0119 (15)
C36	0.066 (2)	0.0356 (16)	0.0428 (16)	−0.0056 (15)	0.0255 (15)	−0.0099 (13)
C37	0.0538 (18)	0.0292 (14)	0.0364 (14)	−0.0051 (12)	0.0223 (13)	−0.0006 (11)
C38	0.0582 (19)	0.0274 (14)	0.0381 (15)	−0.0063 (13)	0.0185 (14)	0.0001 (12)
N39	0.0509 (15)	0.0370 (14)	0.0401 (13)	0.0023 (12)	0.0136 (12)	0.0002 (11)
C40	0.063 (2)	0.0467 (19)	0.054 (2)	0.0075 (17)	0.0135 (17)	−0.0007 (16)
C41	0.074 (3)	0.066 (3)	0.060 (2)	0.012 (2)	0.002 (2)	0.0064 (19)
C42	0.089 (3)	0.061 (2)	0.0407 (19)	−0.005 (2)	−0.0035 (19)	0.0022 (17)
C43	0.080 (3)	0.0450 (19)	0.0394 (17)	−0.0029 (17)	0.0159 (17)	−0.0004 (14)

Geometric parameters (Å, º)

Cu1—O2	1.922 (2)	C22—N23	1.480 (4)
Cu1—O19^i	1.964 (2)	N23—O24	1.214 (4)
Cu1—N32	1.993 (2)	N23—O25	1.217 (4)
Cu1—N39	2.014 (3)	C26—C27	1.373 (4)
Cu1—O17	2.268 (2)	C26—H26	0.9300
O2—C3	1.290 (4)	C27—C28	1.378 (4)
C3—O4	1.220 (4)	C27—N29	1.464 (4)
C3—C5	1.512 (4)	C28—H28	0.9300
C5—C6	1.386 (4)	N29—O30	1.222 (4)
C5—C13	1.397 (4)	N29—O31	1.225 (4)
C6—C7	1.378 (4)	N32—C33	1.334 (4)
C6—H6	0.9300	N32—C37	1.345 (4)
C7—C11	1.378 (4)	C33—C34	1.381 (4)
C7—N8	1.464 (4)	C33—H33	0.9300
N8—O9	1.217 (4)	C34—C35	1.370 (5)
N8—O10	1.223 (4)	C34—H34	0.9300
C11—C12	1.376 (4)	C35—C36	1.376 (5)
C11—H11	0.9300	C35—H35	0.9300
C12—C13	1.370 (4)	C36—C37	1.385 (4)
C12—N14	1.481 (4)	C36—H36	0.9300
C13—H13	0.9300	C37—C38	1.469 (4)
N14—O15	1.215 (3)	C38—N39	1.346 (4)
N14—O16	1.222 (4)	C38—C43	1.383 (4)
O17—C18	1.241 (4)	N39—C40	1.333 (4)
C18—O19	1.263 (3)	C40—C41	1.376 (5)
C18—C20	1.511 (4)	C40—H40	0.9300
C20—C28	1.379 (4)	C41—C42	1.375 (6)
C20—C21	1.395 (4)	C41—H41	0.9300
C21—C22	1.373 (4)	C42—C43	1.364 (6)
C21—H21	0.9300	C42—H42	0.9300
C22—C26	1.371 (4)	C43—H43	0.9300
O2—Cu1—O19^i	91.24 (10)	O24—N23—O25	124.2 (3)
O2—Cu1—N32	171.55 (10)	O24—N23—C22	118.0 (3)
O19^i—Cu1—N32	96.33 (10)	O25—N23—C22	117.7 (3)
O2—Cu1—N39	94.94 (10)	C22—C26—C27	116.6 (3)
O19^i—Cu1—N39	148.97 (10)	C22—C26—H26	121.7
N32—Cu1—N39	80.48 (10)	C27—C26—H26	121.7
O2—Cu1—O17	87.12 (9)	C26—C27—C28	122.7 (3)
O19^i—Cu1—O17	104.94 (9)	C26—C27—N29	118.3 (3)
N32—Cu1—O17	87.30 (9)	C28—C27—N29	119.0 (3)
N39—Cu1—O17	105.72 (10)	C27—C28—C20	119.4 (3)
C3—O2—Cu1	120.5 (2)	C27—C28—H28	120.3
O4—C3—O2	127.0 (3)	C20—C28—H28	120.3
O4—C3—C5	119.8 (3)	O30—N29—O31	124.9 (3)
O2—C3—C5	113.2 (3)	O30—N29—C27	117.6 (3)
C6—C5—C13	119.6 (3)	O31—N29—C27	117.5 (3)
C6—C5—C3	120.6 (3)	C33—N32—C37	119.3 (3)
C13—C5—C3	119.8 (3)	C33—N32—Cu1	124.9 (2)
C7—C6—C5	119.0 (3)	C37—N32—Cu1	115.6 (2)
C7—C6—H6	120.5	N32—C33—C34	121.7 (3)
C5—C6—H6	120.5	N32—C33—H33	119.1
C6—C7—C11	122.8 (3)	C34—C33—H33	119.1
C6—C7—N8	119.2 (3)	C35—C34—C33	119.6 (3)
C11—C7—N8	117.9 (3)	C35—C34—H34	120.2
O9—N8—O10	123.4 (3)	C33—C34—H34	120.2
O9—N8—C7	119.1 (3)	C34—C35—C36	118.5 (3)
O10—N8—C7	117.5 (3)	C34—C35—H35	120.7
C12—C11—C7	116.6 (3)	C36—C35—H35	120.7
C12—C11—H11	121.7	C35—C36—C37	119.8 (3)
C7—C11—H11	121.7	C35—C36—H36	120.1
C13—C12—C11	123.1 (3)	C37—C36—H36	120.1
C13—C12—N14	119.4 (3)	N32—C37—C36	120.9 (3)
C11—C12—N14	117.4 (3)	N32—C37—C38	114.3 (3)
C12—C13—C5	118.9 (3)	C36—C37—C38	124.8 (3)
C12—C13—H13	120.6	N39—C38—C43	121.0 (3)
C5—C13—H13	120.6	N39—C38—C37	114.8 (3)
O15—N14—O16	124.2 (3)	C43—C38—C37	124.2 (3)
O15—N14—C12	117.6 (3)	C40—N39—C38	119.7 (3)
O16—N14—C12	118.2 (3)	C40—N39—Cu1	125.7 (2)
C18—O17—Cu1	140.3 (2)	C38—N39—Cu1	114.4 (2)
O17—C18—O19	126.0 (3)	N39—C40—C41	122.0 (4)
O17—C18—C20	118.9 (3)	N39—C40—H40	119.0
O19—C18—C20	115.1 (3)	C41—C40—H40	119.0
C18—O19—Cu1^i	131.6 (2)	C42—C41—C40	118.1 (4)
C28—C20—C21	119.3 (3)	C42—C41—H41	121.0
C28—C20—C18	119.3 (3)	C40—C41—H41	121.0
C21—C20—C18	121.4 (3)	C43—C42—C41	120.7 (3)
C22—C21—C20	118.8 (3)	C43—C42—H42	119.7
C22—C21—H21	120.6	C41—C42—H42	119.7
C20—C21—H21	120.6	C42—C43—C38	118.6 (4)
C26—C22—C21	123.2 (3)	C42—C43—H43	120.7
C26—C22—N23	117.1 (3)	C38—C43—H43	120.7
C21—C22—N23	119.7 (3)
Cu1—O2—C3—O4	−3.1 (5)	C26—C22—N23—O25	−178.7 (3)
Cu1—O2—C3—C5	178.24 (18)	C21—C22—N23—O25	0.4 (5)
O4—C3—C5—C6	−165.7 (3)	C21—C22—C26—C27	0.4 (5)
O2—C3—C5—C6	13.1 (4)	N23—C22—C26—C27	179.5 (3)
O4—C3—C5—C13	12.5 (4)	C22—C26—C27—C28	−0.1 (5)
O2—C3—C5—C13	−168.7 (3)	C22—C26—C27—N29	−178.4 (3)
C13—C5—C6—C7	0.4 (4)	C26—C27—C28—C20	−0.3 (5)
C3—C5—C6—C7	178.6 (3)	N29—C27—C28—C20	178.1 (3)
C5—C6—C7—C11	0.8 (4)	C21—C20—C28—C27	0.2 (4)
C5—C6—C7—N8	−177.4 (3)	C18—C20—C28—C27	−177.7 (3)
C6—C7—N8—O9	1.2 (4)	C26—C27—N29—O30	−177.5 (3)
C11—C7—N8—O9	−177.1 (3)	C28—C27—N29—O30	4.1 (5)
C6—C7—N8—O10	−177.6 (3)	C26—C27—N29—O31	1.6 (5)
C11—C7—N8—O10	4.1 (5)	C28—C27—N29—O31	−176.8 (3)
C6—C7—C11—C12	−0.8 (4)	C37—N32—C33—C34	−0.9 (5)
N8—C7—C11—C12	177.5 (3)	Cu1—N32—C33—C34	−175.7 (3)
C7—C11—C12—C13	−0.4 (4)	N32—C33—C34—C35	−0.9 (5)
C7—C11—C12—N14	−177.5 (2)	C33—C34—C35—C36	1.5 (5)
C11—C12—C13—C5	1.6 (4)	C34—C35—C36—C37	−0.4 (5)
N14—C12—C13—C5	178.6 (2)	C33—N32—C37—C36	2.0 (4)
C6—C5—C13—C12	−1.5 (4)	Cu1—N32—C37—C36	177.3 (2)
C3—C5—C13—C12	−179.7 (3)	C33—N32—C37—C38	−175.9 (3)
C13—C12—N14—O15	−3.3 (4)	Cu1—N32—C37—C38	−0.6 (3)
C11—C12—N14—O15	173.9 (3)	C35—C36—C37—N32	−1.4 (5)
C13—C12—N14—O16	177.9 (3)	C35—C36—C37—C38	176.3 (3)
C11—C12—N14—O16	−4.9 (4)	N32—C37—C38—N39	5.6 (4)
Cu1—O17—C18—O19	−101.0 (4)	C36—C37—C38—N39	−172.2 (3)
Cu1—O17—C18—C20	79.1 (4)	N32—C37—C38—C43	−176.4 (3)
O17—C18—O19—Cu1^i	47.8 (5)	C36—C37—C38—C43	5.8 (5)
C20—C18—O19—Cu1^i	−132.3 (2)	C43—C38—N39—C40	−0.4 (5)
O17—C18—C20—C28	2.7 (4)	C37—C38—N39—C40	177.7 (3)
O19—C18—C20—C28	−177.2 (3)	C43—C38—N39—Cu1	174.1 (2)
O17—C18—C20—C21	−175.2 (3)	C37—C38—N39—Cu1	−7.8 (3)
O19—C18—C20—C21	4.9 (4)	C38—N39—C40—C41	−0.2 (6)
C28—C20—C21—C22	0.1 (4)	Cu1—N39—C40—C41	−173.9 (3)
C18—C20—C21—C22	178.0 (3)	N39—C40—C41—C42	0.4 (7)
C20—C21—C22—C26	−0.5 (5)	C40—C41—C42—C43	−0.2 (7)
C20—C21—C22—N23	−179.5 (3)	C41—C42—C43—C38	−0.3 (6)
C26—C22—N23—O24	3.2 (5)	N39—C38—C43—C42	0.6 (5)
C21—C22—N23—O24	−177.7 (4)	C37—C38—C43—C42	−177.3 (3)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O31^ii	0.93	2.49	3.422 (4)	177
C33—H33···O17^i	0.93	2.39	3.258 (4)	155
C34—H34···O15^iii	0.93	2.53	3.144 (4)	123
C40—H40···O2	0.93	2.57	3.077 (4)	115

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2.

(complex_3)

Crystal data

C52H28Cu2N12O24	F(000) = 1348
Mr = 1331.96	Dx = 1.674 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.285 (3) Å	Cell parameters from 5709 reflections
b = 26.650 (3) Å	θ = 3.8–25.3°
c = 9.4293 (17) Å	µ = 0.91 mm^−1
β = 111.31 (2)°	T = 298 K
V = 2642.0 (9) Å^3	Parallelepiped, green
Z = 2	0.31 × 0.13 × 0.12 mm

Data collection

SuperNova, Dual, Cu at zero, Atlas diffractometer	5807 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4274 reflections with I > 2σ(I)
Detector resolution: 5.3072 pixels mm^-1	Rint = 0.074
ω scans	θmax = 27.1°, θmin = 3.1°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −14→14
Tmin = 0.753, Tmax = 1.000	k = −34→34
29258 measured reflections	l = −11→12

Refinement

Refinement on F^2	21 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.148	w = 1/[σ^2(Fo^2) + (0.0572P)^2 + 2.8913P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
5807 reflections	Δρmax = 0.47 e Å^−3
406 parameters	Δρmin = −0.31 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.61548 (4)	0.46516 (2)	0.23182 (5)	0.04740 (16)
O1	0.7260 (3)	0.41806 (9)	0.1880 (3)	0.0603 (7)
N1	0.5190 (3)	0.51969 (10)	0.2919 (3)	0.0425 (6)
C1	0.8523 (4)	0.45665 (15)	0.5165 (5)	0.0634 (11)
H1	0.879206	0.430903	0.468719	0.076*
N2	0.7419 (3)	0.47869 (10)	0.4432 (3)	0.0494 (7)
O2	0.6584 (3)	0.35422 (11)	0.2955 (3)	0.0684 (8)
C2	0.9295 (5)	0.47087 (18)	0.6632 (5)	0.0734 (12)
H2	1.006745	0.454696	0.711794	0.088*
C3	0.8916 (4)	0.50891 (17)	0.7364 (5)	0.0687 (11)
H3	0.943094	0.518598	0.834168	0.082*
O3	0.7898 (3)	0.18336 (10)	0.2043 (3)	0.0655 (7)
C4	0.7756 (4)	0.53266 (13)	0.6625 (4)	0.0538 (9)
O4	0.9170 (3)	0.17317 (10)	0.0828 (4)	0.0753 (9)
C5	0.7027 (4)	0.51592 (12)	0.5156 (4)	0.0449 (8)
O5	1.1041 (4)	0.31681 (13)	−0.0607 (5)	0.0969 (12)
C6	0.7244 (4)	0.57286 (14)	0.7256 (5)	0.0608 (10)
H6	0.770213	0.583872	0.823904	0.073*
O6	1.0337 (3)	0.39094 (11)	−0.0458 (4)	0.0742 (8)
C7	0.6135 (4)	0.59472 (13)	0.6472 (4)	0.0575 (10)
H7	0.583840	0.620583	0.691653	0.069*
O7	0.6778 (3)	0.52517 (8)	0.1029 (3)	0.0556 (7)
C8	0.5396 (4)	0.57896 (12)	0.4957 (4)	0.0474 (8)
O8	0.5273 (3)	0.56827 (9)	−0.0773 (3)	0.0612 (7)
C9	0.5839 (3)	0.53850 (10)	0.4325 (4)	0.0420 (8)
O9	0.5121 (5)	0.75087 (14)	−0.0421 (6)	0.1277 (16)
C10	0.4239 (4)	0.60081 (13)	0.4074 (5)	0.0569 (10)
H10	0.391034	0.627535	0.444881	0.068*
O10	0.6233 (5)	0.78758 (13)	0.1599 (6)	0.1428 (18)
C11	0.3599 (4)	0.58228 (13)	0.2651 (4)	0.0568 (10)
H11	0.283196	0.596715	0.204177	0.068*
O11	0.8892 (4)	0.69340 (13)	0.5919 (4)	0.0917 (11)
C12	0.4097 (4)	0.54124 (12)	0.2100 (4)	0.0502 (9)
H12	0.364315	0.528945	0.113044	0.060*
O12	0.9242 (3)	0.61452 (13)	0.5659 (4)	0.0828 (10)
C13	0.7194 (4)	0.37156 (13)	0.2225 (4)	0.0515 (9)
C14	0.7975 (3)	0.33686 (12)	0.1631 (4)	0.0411 (7)
C15	0.7897 (3)	0.28520 (12)	0.1769 (4)	0.0425 (7)
H15	0.736519	0.271391	0.222255	0.051*
C16	0.8623 (3)	0.25469 (11)	0.1219 (4)	0.0407 (7)
N17	0.8560 (3)	0.19963 (10)	0.1366 (4)	0.0517 (7)
C18	0.9427 (3)	0.27291 (12)	0.0547 (4)	0.0425 (7)
H18	0.990609	0.251684	0.018262	0.051*
C19	0.9489 (3)	0.32459 (12)	0.0439 (4)	0.0419 (7)
C20	0.8776 (3)	0.35668 (12)	0.0963 (4)	0.0433 (8)
H20	0.883439	0.391227	0.086609	0.052*
N21	1.0354 (3)	0.34570 (13)	−0.0260 (4)	0.0578 (8)
C22	0.6192 (4)	0.56420 (12)	0.0452 (4)	0.0457 (8)
C23	0.6601 (3)	0.61316 (11)	0.1328 (4)	0.0428 (8)
C24	0.6051 (4)	0.65855 (12)	0.0682 (4)	0.0505 (8)
H24	0.544974	0.659727	−0.030182	0.061*
C25	0.6423 (4)	0.70190 (13)	0.1545 (5)	0.0579 (10)
N26	0.5874 (5)	0.75007 (13)	0.0859 (6)	0.0956 (13)
C27	0.7277 (4)	0.70213 (14)	0.3009 (5)	0.0588 (10)
H27	0.749843	0.731598	0.357227	0.071*
C28	0.7795 (3)	0.65654 (13)	0.3608 (4)	0.0491 (8)
N29	0.8709 (3)	0.65450 (14)	0.5182 (4)	0.0648 (9)
C30	0.7485 (3)	0.61223 (12)	0.2783 (4)	0.0449 (8)
H30	0.787224	0.582226	0.321107	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0634 (3)	0.0308 (2)	0.0535 (3)	0.00843 (18)	0.0278 (2)	−0.00385 (17)
O1	0.0796 (19)	0.0341 (12)	0.0787 (18)	0.0108 (12)	0.0424 (15)	−0.0058 (12)
N1	0.0550 (18)	0.0317 (13)	0.0473 (15)	0.0034 (12)	0.0264 (13)	−0.0004 (11)
C1	0.072 (3)	0.052 (2)	0.070 (3)	0.016 (2)	0.030 (2)	0.0049 (19)
N2	0.0587 (19)	0.0370 (14)	0.0558 (17)	0.0062 (13)	0.0249 (15)	0.0033 (13)
O2	0.081 (2)	0.0595 (17)	0.083 (2)	0.0182 (15)	0.0513 (17)	0.0035 (15)
C2	0.068 (3)	0.075 (3)	0.072 (3)	0.016 (2)	0.019 (2)	0.006 (2)
C3	0.071 (3)	0.067 (3)	0.060 (2)	−0.009 (2)	0.014 (2)	−0.001 (2)
O3	0.080 (2)	0.0424 (14)	0.0769 (19)	−0.0088 (13)	0.0316 (16)	0.0067 (13)
C4	0.067 (3)	0.0430 (19)	0.056 (2)	−0.0080 (17)	0.0278 (19)	0.0016 (16)
O4	0.095 (2)	0.0348 (13)	0.108 (2)	0.0104 (14)	0.050 (2)	−0.0080 (14)
C5	0.059 (2)	0.0309 (15)	0.0513 (19)	−0.0047 (15)	0.0281 (17)	−0.0003 (14)
O5	0.093 (3)	0.082 (2)	0.152 (3)	0.011 (2)	0.087 (3)	0.012 (2)
C6	0.084 (3)	0.047 (2)	0.054 (2)	−0.016 (2)	0.027 (2)	−0.0135 (17)
O6	0.088 (2)	0.0587 (18)	0.084 (2)	−0.0167 (16)	0.0415 (18)	0.0071 (15)
C7	0.086 (3)	0.0352 (17)	0.060 (2)	−0.0097 (19)	0.037 (2)	−0.0099 (16)
O7	0.0774 (19)	0.0313 (12)	0.0679 (16)	0.0072 (12)	0.0382 (14)	0.0002 (11)
C8	0.068 (2)	0.0273 (15)	0.058 (2)	−0.0025 (15)	0.0362 (19)	−0.0029 (14)
O8	0.079 (2)	0.0409 (13)	0.0593 (16)	−0.0021 (13)	0.0196 (15)	−0.0120 (11)
C9	0.061 (2)	0.0244 (14)	0.0525 (19)	−0.0069 (14)	0.0342 (17)	−0.0031 (13)
O9	0.123 (3)	0.0556 (19)	0.153 (3)	0.015 (2)	−0.011 (2)	0.015 (2)
C10	0.081 (3)	0.0320 (17)	0.071 (3)	0.0083 (18)	0.043 (2)	−0.0005 (16)
O10	0.152 (4)	0.0388 (17)	0.185 (4)	0.013 (2)	−0.001 (3)	−0.018 (2)
C11	0.071 (3)	0.0388 (18)	0.063 (2)	0.0169 (18)	0.027 (2)	0.0031 (16)
O11	0.113 (3)	0.086 (2)	0.069 (2)	−0.033 (2)	0.0243 (19)	−0.0220 (18)
C12	0.058 (2)	0.0396 (18)	0.057 (2)	0.0064 (16)	0.0257 (18)	−0.0019 (15)
O12	0.084 (2)	0.076 (2)	0.074 (2)	−0.0159 (18)	0.0115 (17)	0.0155 (17)
C13	0.057 (2)	0.0416 (18)	0.058 (2)	0.0098 (17)	0.0237 (18)	−0.0066 (16)
C14	0.0472 (19)	0.0355 (16)	0.0407 (17)	0.0057 (14)	0.0163 (14)	−0.0033 (13)
C15	0.0463 (19)	0.0378 (16)	0.0446 (18)	0.0022 (14)	0.0180 (15)	0.0026 (13)
C16	0.0445 (19)	0.0294 (15)	0.0435 (17)	0.0035 (13)	0.0102 (14)	−0.0015 (12)
N17	0.0567 (19)	0.0338 (15)	0.0599 (19)	0.0013 (14)	0.0157 (16)	0.0001 (13)
C18	0.0464 (19)	0.0369 (16)	0.0447 (18)	0.0079 (14)	0.0172 (15)	−0.0043 (13)
C19	0.0432 (18)	0.0399 (17)	0.0424 (17)	−0.0025 (14)	0.0156 (14)	−0.0014 (13)
C20	0.053 (2)	0.0295 (15)	0.0452 (18)	0.0027 (14)	0.0158 (15)	0.0011 (13)
N21	0.059 (2)	0.055 (2)	0.063 (2)	−0.0055 (16)	0.0267 (16)	0.0022 (15)
C22	0.058 (2)	0.0336 (16)	0.056 (2)	−0.0028 (15)	0.0329 (19)	−0.0038 (15)
C23	0.050 (2)	0.0317 (15)	0.056 (2)	−0.0022 (14)	0.0302 (17)	−0.0024 (14)
C24	0.049 (2)	0.0374 (17)	0.064 (2)	0.0006 (15)	0.0191 (17)	−0.0031 (15)
C25	0.057 (2)	0.0303 (17)	0.087 (3)	0.0031 (16)	0.027 (2)	−0.0022 (17)
N26	0.091 (3)	0.0337 (16)	0.139 (3)	0.0065 (18)	0.013 (2)	−0.002 (2)
C27	0.062 (3)	0.043 (2)	0.077 (3)	−0.0106 (18)	0.031 (2)	−0.0157 (18)
C28	0.048 (2)	0.049 (2)	0.056 (2)	−0.0107 (16)	0.0254 (17)	−0.0039 (16)
N29	0.065 (2)	0.067 (2)	0.061 (2)	−0.0238 (19)	0.0216 (17)	−0.0059 (18)
C30	0.047 (2)	0.0381 (17)	0.055 (2)	−0.0032 (15)	0.0260 (17)	0.0021 (15)

Geometric parameters (Å, º)

Cu1—O1	1.917 (2)	C10—C11	1.365 (5)
Cu1—O8^i	1.951 (3)	C10—H10	0.9300
Cu1—N1	2.016 (3)	O10—N26	1.202 (5)
Cu1—N2	2.018 (3)	C11—C12	1.412 (5)
Cu1—O7	2.269 (2)	C11—H11	0.9300
O1—C13	1.290 (4)	O11—N29	1.223 (4)
N1—C12	1.325 (5)	C12—H12	0.9300
N1—C9	1.357 (4)	O12—N29	1.226 (5)
C1—N2	1.323 (5)	C13—C14	1.518 (5)
C1—C2	1.392 (6)	C14—C20	1.380 (5)
C1—H1	0.9300	C14—C15	1.389 (4)
N2—C5	1.366 (4)	C15—C16	1.382 (5)
O2—C13	1.226 (4)	C15—H15	0.9300
C2—C3	1.379 (6)	C16—C18	1.372 (5)
C2—H2	0.9300	C16—N17	1.478 (4)
C3—C4	1.392 (6)	C18—C19	1.385 (4)
C3—H3	0.9300	C18—H18	0.9300
O3—N17	1.225 (4)	C19—C20	1.383 (4)
C4—C5	1.402 (5)	C19—N21	1.473 (4)
C4—C6	1.443 (5)	C20—H20	0.9300
O4—N17	1.218 (4)	C22—C23	1.524 (4)
C5—C9	1.418 (5)	C23—C30	1.372 (5)
O5—N21	1.219 (4)	C23—C24	1.394 (5)
C6—C7	1.334 (6)	C24—C25	1.387 (5)
C6—H6	0.9300	C24—H24	0.9300
O6—N21	1.219 (4)	C25—C27	1.367 (6)
C7—C8	1.430 (5)	C25—N26	1.469 (5)
C7—H7	0.9300	C27—C28	1.377 (5)
O7—C22	1.246 (4)	C27—H27	0.9300
C8—C10	1.395 (5)	C28—C30	1.387 (5)
C8—C9	1.409 (4)	C28—N29	1.469 (5)
O8—C22	1.246 (4)	C30—H30	0.9300
O9—N26	1.197 (6)
O1—Cu1—O8^i	88.00 (12)	O2—C13—O1	126.8 (3)
O1—Cu1—N1	172.85 (12)	O2—C13—C14	119.8 (3)
O8^i—Cu1—N1	98.94 (12)	O1—C13—C14	113.4 (3)
O1—Cu1—N2	92.76 (12)	C20—C14—C15	119.8 (3)
O8^i—Cu1—N2	156.19 (12)	C20—C14—C13	120.0 (3)
N1—Cu1—N2	81.60 (12)	C15—C14—C13	120.3 (3)
O1—Cu1—O7	89.63 (10)	C16—C15—C14	118.8 (3)
O8^i—Cu1—O7	104.73 (11)	C16—C15—H15	120.6
N1—Cu1—O7	86.93 (10)	C14—C15—H15	120.6
N2—Cu1—O7	99.07 (11)	C18—C16—C15	123.2 (3)
C13—O1—Cu1	118.2 (2)	C18—C16—N17	117.2 (3)
C12—N1—C9	117.9 (3)	C15—C16—N17	119.6 (3)
C12—N1—Cu1	129.2 (2)	O4—N17—O3	123.8 (3)
C9—N1—Cu1	112.7 (2)	O4—N17—C16	118.8 (3)
N2—C1—C2	121.9 (4)	O3—N17—C16	117.3 (3)
N2—C1—H1	119.0	C16—C18—C19	116.5 (3)
C2—C1—H1	119.0	C16—C18—H18	121.8
C1—N2—C5	118.4 (3)	C19—C18—H18	121.8
C1—N2—Cu1	129.1 (3)	C20—C19—C18	122.5 (3)
C5—N2—Cu1	112.5 (2)	C20—C19—N21	119.3 (3)
C3—C2—C1	120.1 (4)	C18—C19—N21	118.2 (3)
C3—C2—H2	120.0	C14—C20—C19	119.3 (3)
C1—C2—H2	120.0	C14—C20—H20	120.4
C2—C3—C4	119.4 (4)	C19—C20—H20	120.4
C2—C3—H3	120.3	O6—N21—O5	124.0 (3)
C4—C3—H3	120.3	O6—N21—C19	118.0 (3)
C3—C4—C5	117.2 (4)	O5—N21—C19	117.9 (3)
C3—C4—C6	125.2 (4)	O8—C22—O7	127.5 (3)
C5—C4—C6	117.7 (4)	O8—C22—C23	114.5 (3)
N2—C5—C4	123.0 (3)	O7—C22—C23	118.0 (3)
N2—C5—C9	116.4 (3)	C30—C23—C24	119.9 (3)
C4—C5—C9	120.5 (3)	C30—C23—C22	119.6 (3)
C7—C6—C4	122.1 (4)	C24—C23—C22	120.5 (3)
C7—C6—H6	119.0	C25—C24—C23	118.3 (4)
C4—C6—H6	119.0	C25—C24—H24	120.8
C6—C7—C8	120.9 (3)	C23—C24—H24	120.8
C6—C7—H7	119.5	C27—C25—C24	123.2 (3)
C8—C7—H7	119.5	C27—C25—N26	118.1 (4)
C22—O7—Cu1	127.1 (2)	C24—C25—N26	118.7 (4)
C10—C8—C9	117.8 (3)	O9—N26—O10	122.4 (4)
C10—C8—C7	123.6 (3)	O9—N26—C25	119.4 (4)
C9—C8—C7	118.6 (3)	O10—N26—C25	118.1 (5)
C22—O8—Cu1^i	146.7 (2)	C25—C27—C28	116.7 (3)
N1—C9—C8	123.2 (3)	C25—C27—H27	121.7
N1—C9—C5	116.7 (3)	C28—C27—H27	121.7
C8—C9—C5	120.1 (3)	C27—C28—C30	122.6 (4)
C11—C10—C8	118.8 (3)	C27—C28—N29	119.0 (3)
C11—C10—H10	120.6	C30—C28—N29	118.5 (3)
C8—C10—H10	120.6	O11—N29—O12	124.7 (4)
C10—C11—C12	120.2 (4)	O11—N29—C28	117.0 (4)
C10—C11—H11	119.9	O12—N29—C28	118.3 (3)
C12—C11—H11	119.9	C23—C30—C28	119.2 (3)
N1—C12—C11	122.2 (3)	C23—C30—H30	120.4
N1—C12—H12	118.9	C28—C30—H30	120.4
C11—C12—H12	118.9
C2—C1—N2—C5	−1.0 (6)	C14—C15—C16—N17	179.5 (3)
C2—C1—N2—Cu1	179.5 (3)	C18—C16—N17—O4	−3.3 (5)
N2—C1—C2—C3	0.1 (7)	C15—C16—N17—O4	177.4 (3)
C1—C2—C3—C4	0.3 (7)	C18—C16—N17—O3	175.9 (3)
C2—C3—C4—C5	0.3 (6)	C15—C16—N17—O3	−3.3 (5)
C2—C3—C4—C6	−180.0 (4)	C15—C16—C18—C19	0.1 (5)
C1—N2—C5—C4	1.6 (5)	N17—C16—C18—C19	−179.1 (3)
Cu1—N2—C5—C4	−178.8 (3)	C16—C18—C19—C20	−0.6 (5)
C1—N2—C5—C9	179.9 (3)	C16—C18—C19—N21	179.3 (3)
Cu1—N2—C5—C9	−0.5 (4)	C15—C14—C20—C19	0.0 (5)
C3—C4—C5—N2	−1.3 (5)	C13—C14—C20—C19	179.5 (3)
C6—C4—C5—N2	179.0 (3)	C18—C19—C20—C14	0.5 (5)
C3—C4—C5—C9	−179.5 (3)	N21—C19—C20—C14	−179.4 (3)
C6—C4—C5—C9	0.8 (5)	C20—C19—N21—O6	−5.5 (5)
C3—C4—C6—C7	178.6 (4)	C18—C19—N21—O6	174.6 (3)
C5—C4—C6—C7	−1.7 (6)	C20—C19—N21—O5	174.6 (4)
C4—C6—C7—C8	0.2 (6)	C18—C19—N21—O5	−5.4 (5)
C6—C7—C8—C10	−179.1 (4)	Cu1^i—O8—C22—O7	22.9 (7)
C6—C7—C8—C9	2.3 (5)	Cu1^i—O8—C22—C23	−155.7 (3)
C12—N1—C9—C8	1.2 (5)	Cu1—O7—C22—O8	−78.7 (4)
Cu1—N1—C9—C8	176.0 (2)	Cu1—O7—C22—C23	99.9 (3)
C12—N1—C9—C5	−177.8 (3)	O8—C22—C23—C30	171.2 (3)
Cu1—N1—C9—C5	−3.0 (3)	O7—C22—C23—C30	−7.6 (5)
C10—C8—C9—N1	−0.9 (5)	O8—C22—C23—C24	−6.6 (5)
C7—C8—C9—N1	177.9 (3)	O7—C22—C23—C24	174.7 (3)
C10—C8—C9—C5	178.1 (3)	C30—C23—C24—C25	0.1 (5)
C7—C8—C9—C5	−3.2 (5)	C22—C23—C24—C25	177.8 (3)
N2—C5—C9—N1	2.3 (4)	C23—C24—C25—C27	−1.7 (6)
C4—C5—C9—N1	−179.3 (3)	C23—C24—C25—N26	178.4 (4)
N2—C5—C9—C8	−176.7 (3)	C27—C25—N26—O9	−179.8 (5)
C4—C5—C9—C8	1.7 (5)	C24—C25—N26—O9	0.1 (8)
C9—C8—C10—C11	−0.2 (5)	C27—C25—N26—O10	2.4 (7)
C7—C8—C10—C11	−178.8 (3)	C24—C25—N26—O10	−177.7 (5)
C8—C10—C11—C12	0.9 (6)	C24—C25—C27—C28	1.4 (6)
C9—N1—C12—C11	−0.4 (5)	N26—C25—C27—C28	−178.7 (4)
Cu1—N1—C12—C11	−174.3 (3)	C25—C27—C28—C30	0.5 (6)
C10—C11—C12—N1	−0.6 (6)	C25—C27—C28—N29	−179.4 (3)
Cu1—O1—C13—O2	−8.0 (6)	C27—C28—N29—O11	5.3 (5)
Cu1—O1—C13—C14	172.0 (2)	C30—C28—N29—O11	−174.6 (3)
O2—C13—C14—C20	−172.6 (3)	C27—C28—N29—O12	−174.0 (4)
O1—C13—C14—C20	7.4 (5)	C30—C28—N29—O12	6.1 (5)
O2—C13—C14—C15	6.9 (5)	C24—C23—C30—C28	1.7 (5)
O1—C13—C14—C15	−173.2 (3)	C22—C23—C30—C28	−176.0 (3)
C20—C14—C15—C16	−0.4 (5)	C27—C28—C30—C23	−2.0 (5)
C13—C14—C15—C16	−179.9 (3)	N29—C28—C30—C23	177.8 (3)
C14—C15—C16—C18	0.4 (5)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O7^i	0.93	2.40	3.270 (4)	156

Symmetry code: (i) −x+1, −y+1, −z.