Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827011103335X/bg3141sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827011103335X/bg3141Isup2.hkl |
CCDC reference: 846633
For the preparation of the title compound, Cu(4-ClC6H4CO2)2.2H2O (0.001 mol, 0.411 g) was dissolved in methanol (50 ml) and treated with a 2-pyridylmethanol (0.001 mol, 0.10 ml) in a 1:1 molar ratio. The mixture was stirred and left to stand at room temperature, giving a microcrystalline compound, (I) (yield 85%). Analysis, found: C 52.45, H 3.71, N 4.68, Cu 10.78%; calculated: C 52.67, H 3.74, N 4.73, Cu 10.72%.
For convenience, the structure was refined in the nonconventional monoclinic space group I2/a, a variant of C2/c. H atoms were positioned in ideal positions, with C—H = 0.95 Å for aromatic H atoms and C—H = 0.99 Å for methylene H atoms, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
Data collection: CrysAlis CCD (Agilent, 2011); cell refinement: CrysAlis RED (Agilent, 2011); data reduction: CrysAlis RED (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
[Cu4(C7H4ClO2)4(C6H6NO)4] | F(000) = 5280 |
Mr = 1308.84 | Dx = 1.649 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -I2ya | Cell parameters from 15652 reflections |
a = 20.326 (6) Å | θ = 4.1–26.4° |
b = 14.184 (4) Å | µ = 1.86 mm−1 |
c = 36.696 (13) Å | T = 100 K |
β = 94.89 (3)° | Block, blue |
V = 10541 (6) Å3 | 0.45 × 0.35 × 0.25 mm |
Z = 8 |
Kuma KM-4 CCD area-detector diffractometer | 12348 independent reflections |
Radiation source: fine-focus sealed tube | 8586 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ω scans | θmax = 28.0°, θmin = 3.1° |
Absorption correction: analytical CrysAlis RED (Agilent, 2011) | h = −26→25 |
Tmin = 0.467, Tmax = 0.659 | k = −18→15 |
36942 measured reflections | l = −47→48 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.069 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0273P)2] where P = (Fo2 + 2Fc2)/3 |
12348 reflections | (Δ/σ)max = 0.001 |
685 parameters | Δρmax = 0.56 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
[Cu4(C7H4ClO2)4(C6H6NO)4] | V = 10541 (6) Å3 |
Mr = 1308.84 | Z = 8 |
Monoclinic, I2/a | Mo Kα radiation |
a = 20.326 (6) Å | µ = 1.86 mm−1 |
b = 14.184 (4) Å | T = 100 K |
c = 36.696 (13) Å | 0.45 × 0.35 × 0.25 mm |
β = 94.89 (3)° |
Kuma KM-4 CCD area-detector diffractometer | 12348 independent reflections |
Absorption correction: analytical CrysAlis RED (Agilent, 2011) | 8586 reflections with I > 2σ(I) |
Tmin = 0.467, Tmax = 0.659 | Rint = 0.042 |
36942 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.069 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.56 e Å−3 |
12348 reflections | Δρmin = −0.37 e Å−3 |
685 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | 0.321708 (14) | 0.19660 (2) | 0.145333 (8) | 0.01399 (7) | |
Cu2 | 0.172604 (14) | 0.15840 (2) | 0.149733 (9) | 0.01421 (7) | |
Cu3 | 0.251005 (14) | −0.01901 (2) | 0.168529 (9) | 0.01625 (8) | |
Cu4 | 0.248200 (14) | 0.03960 (2) | 0.085878 (8) | 0.01476 (7) | |
Cl1 | 0.07200 (4) | −0.13643 (6) | 0.36502 (2) | 0.0480 (2) | |
Cl2 | 0.28524 (4) | −0.54799 (5) | 0.04864 (2) | 0.0377 (2) | |
Cl3 | 0.58565 (4) | 0.53772 (5) | 0.03306 (3) | 0.0466 (2) | |
Cl4 | 0.11609 (3) | 0.75859 (4) | 0.16230 (2) | 0.02843 (17) | |
N1 | 0.19854 (9) | 0.10296 (14) | 0.04387 (6) | 0.0151 (5) | |
N2 | 0.09070 (9) | 0.15129 (14) | 0.11565 (6) | 0.0151 (5) | |
N3 | 0.33718 (10) | −0.06416 (14) | 0.19326 (6) | 0.0168 (5) | |
N4 | 0.38097 (9) | 0.18916 (14) | 0.19124 (6) | 0.0166 (5) | |
O1 | 0.20152 (8) | −0.04537 (12) | 0.20958 (5) | 0.0199 (4) | |
O2 | 0.13169 (8) | 0.07973 (12) | 0.20791 (5) | 0.0208 (4) | |
O3 | 0.22882 (8) | −0.08900 (12) | 0.07075 (5) | 0.0214 (4) | |
O4 | 0.32410 (8) | −0.07975 (12) | 0.04492 (5) | 0.0213 (4) | |
O5 | 0.38188 (8) | 0.26767 (12) | 0.11857 (5) | 0.0203 (4) | |
O6 | 0.45019 (9) | 0.15279 (12) | 0.10350 (5) | 0.0284 (5) | |
O7 | 0.26769 (8) | 0.34054 (11) | 0.15833 (5) | 0.0184 (4) | |
O8 | 0.16155 (8) | 0.29213 (11) | 0.15717 (5) | 0.0169 (4) | |
O9 | 0.25907 (8) | 0.16896 (11) | 0.10365 (5) | 0.0155 (4) | |
O10 | 0.17805 (8) | 0.02630 (11) | 0.13490 (5) | 0.0147 (4) | |
O11 | 0.30427 (8) | −0.00018 (13) | 0.12861 (5) | 0.0231 (4) | |
O12 | 0.25878 (8) | 0.14146 (11) | 0.17749 (4) | 0.0137 (4) | |
C1 | 0.15632 (12) | 0.00712 (18) | 0.22191 (7) | 0.0174 (6) | |
C2 | 0.13435 (11) | −0.02832 (18) | 0.25776 (7) | 0.0169 (6) | |
C3 | 0.10787 (12) | 0.03335 (19) | 0.28212 (7) | 0.0223 (6) | |
H3 | 0.1026 | 0.0981 | 0.2759 | 0.027* | |
C4 | 0.08910 (13) | 0.0014 (2) | 0.31533 (8) | 0.0284 (7) | |
H4 | 0.0720 | 0.0440 | 0.3322 | 0.034* | |
C5 | 0.09567 (13) | −0.0933 (2) | 0.32359 (8) | 0.0267 (7) | |
C6 | 0.12189 (12) | −0.1563 (2) | 0.29993 (7) | 0.0232 (6) | |
H6 | 0.1259 | −0.2212 | 0.3061 | 0.028* | |
C7 | 0.14219 (12) | −0.12340 (18) | 0.26729 (7) | 0.0185 (6) | |
H7 | 0.1616 | −0.1656 | 0.2512 | 0.022* | |
C8 | 0.27802 (12) | −0.12528 (17) | 0.05599 (7) | 0.0170 (6) | |
C9 | 0.27837 (12) | −0.23096 (17) | 0.05356 (7) | 0.0156 (5) | |
C10 | 0.23666 (13) | −0.28507 (18) | 0.07324 (7) | 0.0216 (6) | |
H10 | 0.2063 | −0.2546 | 0.0876 | 0.026* | |
C11 | 0.23862 (13) | −0.38291 (18) | 0.07222 (8) | 0.0260 (7) | |
H11 | 0.2104 | −0.4195 | 0.0859 | 0.031* | |
C12 | 0.28267 (13) | −0.42573 (17) | 0.05074 (8) | 0.0227 (6) | |
C13 | 0.32484 (13) | −0.37383 (18) | 0.03076 (8) | 0.0255 (6) | |
H13 | 0.3548 | −0.4046 | 0.0162 | 0.031* | |
C14 | 0.32252 (12) | −0.27655 (17) | 0.03238 (7) | 0.0191 (6) | |
H14 | 0.3514 | −0.2403 | 0.0189 | 0.023* | |
C15 | 0.43223 (12) | 0.23529 (19) | 0.10404 (7) | 0.0180 (6) | |
C16 | 0.47073 (11) | 0.31099 (17) | 0.08591 (7) | 0.0158 (5) | |
C17 | 0.44898 (12) | 0.40398 (18) | 0.08487 (7) | 0.0203 (6) | |
H17 | 0.4096 | 0.4199 | 0.0957 | 0.024* | |
C18 | 0.48363 (13) | 0.47357 (19) | 0.06835 (8) | 0.0255 (6) | |
H18 | 0.4682 | 0.5368 | 0.0675 | 0.031* | |
C19 | 0.54142 (14) | 0.44932 (19) | 0.05304 (8) | 0.0271 (7) | |
C20 | 0.56378 (13) | 0.35749 (19) | 0.05338 (8) | 0.0269 (7) | |
H20 | 0.6030 | 0.3417 | 0.0424 | 0.032* | |
C21 | 0.52833 (12) | 0.28846 (19) | 0.06998 (7) | 0.0220 (6) | |
H21 | 0.5436 | 0.2251 | 0.0705 | 0.026* | |
C22 | 0.20744 (12) | 0.35513 (17) | 0.15826 (7) | 0.0152 (5) | |
C23 | 0.18322 (12) | 0.45549 (17) | 0.15953 (7) | 0.0154 (5) | |
C24 | 0.11650 (12) | 0.47828 (18) | 0.15296 (7) | 0.0200 (6) | |
H24 | 0.0849 | 0.4294 | 0.1483 | 0.024* | |
C25 | 0.09584 (13) | 0.57095 (18) | 0.15311 (7) | 0.0217 (6) | |
H25 | 0.0505 | 0.5861 | 0.1477 | 0.026* | |
C26 | 0.14157 (12) | 0.64149 (17) | 0.16116 (7) | 0.0183 (6) | |
C27 | 0.20788 (13) | 0.62107 (18) | 0.16808 (8) | 0.0225 (6) | |
H27 | 0.2390 | 0.6702 | 0.1734 | 0.027* | |
C28 | 0.22851 (12) | 0.52789 (17) | 0.16716 (8) | 0.0212 (6) | |
H28 | 0.2741 | 0.5134 | 0.1718 | 0.025* | |
C29 | 0.20183 (11) | 0.19743 (17) | 0.04503 (7) | 0.0144 (5) | |
C30 | 0.16989 (12) | 0.25268 (18) | 0.01766 (7) | 0.0191 (6) | |
H30 | 0.1733 | 0.3194 | 0.0186 | 0.023* | |
C31 | 0.13333 (13) | 0.20947 (19) | −0.01081 (7) | 0.0240 (6) | |
H31 | 0.1099 | 0.2462 | −0.0293 | 0.029* | |
C32 | 0.13084 (13) | 0.11153 (19) | −0.01232 (8) | 0.0244 (6) | |
H32 | 0.1068 | 0.0802 | −0.0321 | 0.029* | |
C33 | 0.16414 (12) | 0.06081 (18) | 0.01564 (7) | 0.0192 (6) | |
H33 | 0.1626 | −0.0061 | 0.0148 | 0.023* | |
C34 | 0.24319 (12) | 0.23848 (17) | 0.07699 (7) | 0.0175 (6) | |
H34A | 0.2843 | 0.2650 | 0.0685 | 0.021* | |
H34B | 0.2187 | 0.2903 | 0.0878 | 0.021* | |
C35 | 0.07158 (11) | 0.06261 (17) | 0.10704 (7) | 0.0150 (5) | |
C36 | 0.01649 (12) | 0.04443 (18) | 0.08308 (7) | 0.0185 (6) | |
H36 | 0.0029 | −0.0187 | 0.0780 | 0.022* | |
C37 | −0.01842 (12) | 0.11878 (19) | 0.06663 (8) | 0.0232 (6) | |
H37 | −0.0561 | 0.1077 | 0.0501 | 0.028* | |
C38 | 0.00265 (13) | 0.20984 (19) | 0.07475 (8) | 0.0235 (6) | |
H38 | −0.0200 | 0.2621 | 0.0634 | 0.028* | |
C39 | 0.05655 (12) | 0.22408 (18) | 0.09944 (7) | 0.0206 (6) | |
H39 | 0.0702 | 0.2868 | 0.1053 | 0.025* | |
C40 | 0.11496 (12) | −0.01273 (17) | 0.12590 (7) | 0.0174 (6) | |
H40A | 0.0957 | −0.0344 | 0.1483 | 0.021* | |
H40B | 0.1183 | −0.0675 | 0.1095 | 0.021* | |
C41 | 0.38646 (12) | −0.06471 (16) | 0.17093 (7) | 0.0153 (5) | |
C42 | 0.45083 (12) | −0.08422 (18) | 0.18416 (7) | 0.0216 (6) | |
H42 | 0.4849 | −0.0860 | 0.1680 | 0.026* | |
C43 | 0.46534 (13) | −0.10112 (19) | 0.22109 (8) | 0.0267 (7) | |
H43 | 0.5094 | −0.1132 | 0.2307 | 0.032* | |
C44 | 0.41438 (14) | −0.10007 (19) | 0.24378 (8) | 0.0278 (7) | |
H44 | 0.4230 | −0.1119 | 0.2692 | 0.033* | |
C45 | 0.35123 (13) | −0.08179 (18) | 0.22918 (7) | 0.0225 (6) | |
H45 | 0.3164 | −0.0815 | 0.2449 | 0.027* | |
C46 | 0.36629 (12) | −0.04307 (18) | 0.13153 (7) | 0.0188 (6) | |
H46A | 0.3991 | −0.0005 | 0.1217 | 0.023* | |
H46B | 0.3647 | −0.1020 | 0.1170 | 0.023* | |
C47 | 0.34802 (12) | 0.18031 (17) | 0.22111 (7) | 0.0167 (6) | |
C48 | 0.38067 (13) | 0.17772 (18) | 0.25589 (7) | 0.0231 (6) | |
H48 | 0.3565 | 0.1720 | 0.2768 | 0.028* | |
C49 | 0.44875 (13) | 0.1836 (2) | 0.25964 (8) | 0.0296 (7) | |
H49 | 0.4720 | 0.1824 | 0.2832 | 0.036* | |
C50 | 0.48260 (13) | 0.19111 (19) | 0.22876 (8) | 0.0271 (7) | |
H50 | 0.5295 | 0.1937 | 0.2308 | 0.032* | |
C51 | 0.44757 (12) | 0.19488 (19) | 0.19485 (8) | 0.0224 (6) | |
H51 | 0.4708 | 0.2016 | 0.1736 | 0.027* | |
C52 | 0.27400 (12) | 0.17359 (18) | 0.21355 (7) | 0.0174 (6) | |
H52A | 0.2560 | 0.1293 | 0.2310 | 0.021* | |
H52B | 0.2538 | 0.2362 | 0.2167 | 0.021* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.01327 (14) | 0.01641 (17) | 0.01226 (17) | −0.00140 (12) | 0.00100 (12) | 0.00034 (13) |
Cu2 | 0.01340 (15) | 0.01254 (16) | 0.01638 (17) | 0.00052 (12) | −0.00054 (13) | −0.00110 (13) |
Cu3 | 0.01602 (15) | 0.01858 (17) | 0.01444 (17) | 0.00356 (13) | 0.00290 (13) | 0.00390 (13) |
Cu4 | 0.01772 (15) | 0.01320 (16) | 0.01318 (17) | 0.00187 (12) | 0.00023 (13) | 0.00101 (13) |
Cl1 | 0.0546 (5) | 0.0665 (6) | 0.0259 (5) | 0.0024 (4) | 0.0212 (4) | 0.0124 (4) |
Cl2 | 0.0392 (4) | 0.0127 (4) | 0.0598 (6) | 0.0013 (3) | −0.0030 (4) | −0.0021 (3) |
Cl3 | 0.0514 (5) | 0.0334 (5) | 0.0597 (6) | −0.0126 (4) | 0.0312 (5) | 0.0065 (4) |
Cl4 | 0.0319 (4) | 0.0148 (4) | 0.0385 (5) | 0.0058 (3) | 0.0021 (3) | −0.0002 (3) |
N1 | 0.0164 (11) | 0.0157 (12) | 0.0131 (12) | 0.0030 (9) | 0.0016 (9) | −0.0010 (9) |
N2 | 0.0175 (11) | 0.0115 (11) | 0.0166 (12) | 0.0003 (9) | 0.0030 (9) | −0.0004 (9) |
N3 | 0.0198 (11) | 0.0166 (12) | 0.0139 (12) | 0.0035 (9) | 0.0016 (9) | 0.0027 (9) |
N4 | 0.0157 (10) | 0.0177 (12) | 0.0161 (12) | −0.0013 (9) | −0.0007 (9) | 0.0003 (9) |
O1 | 0.0223 (9) | 0.0194 (10) | 0.0190 (10) | 0.0035 (8) | 0.0085 (8) | 0.0029 (8) |
O2 | 0.0211 (9) | 0.0218 (10) | 0.0199 (11) | 0.0022 (8) | 0.0043 (8) | 0.0012 (8) |
O3 | 0.0230 (9) | 0.0153 (10) | 0.0265 (11) | 0.0030 (8) | 0.0059 (8) | 0.0006 (8) |
O4 | 0.0245 (10) | 0.0172 (10) | 0.0222 (11) | −0.0041 (8) | 0.0023 (8) | 0.0027 (8) |
O5 | 0.0190 (9) | 0.0208 (10) | 0.0216 (11) | −0.0015 (8) | 0.0052 (8) | 0.0042 (8) |
O6 | 0.0356 (11) | 0.0168 (11) | 0.0347 (13) | −0.0014 (9) | 0.0146 (10) | 0.0000 (9) |
O7 | 0.0155 (9) | 0.0148 (9) | 0.0248 (11) | 0.0008 (7) | 0.0011 (8) | −0.0014 (8) |
O8 | 0.0153 (9) | 0.0144 (9) | 0.0208 (11) | −0.0014 (7) | −0.0001 (8) | −0.0018 (7) |
O9 | 0.0215 (9) | 0.0116 (9) | 0.0129 (10) | −0.0010 (7) | −0.0024 (8) | 0.0039 (7) |
O10 | 0.0148 (8) | 0.0135 (9) | 0.0154 (10) | −0.0008 (7) | −0.0001 (7) | 0.0027 (7) |
O11 | 0.0195 (9) | 0.0359 (12) | 0.0144 (10) | 0.0114 (8) | 0.0042 (8) | 0.0087 (8) |
O12 | 0.0150 (8) | 0.0175 (9) | 0.0086 (9) | 0.0010 (7) | −0.0001 (7) | 0.0004 (7) |
C1 | 0.0148 (12) | 0.0174 (14) | 0.0199 (15) | −0.0046 (11) | 0.0005 (11) | 0.0007 (11) |
C2 | 0.0102 (11) | 0.0251 (15) | 0.0153 (14) | −0.0012 (11) | −0.0001 (10) | −0.0006 (11) |
C3 | 0.0187 (13) | 0.0285 (16) | 0.0194 (15) | 0.0002 (12) | 0.0000 (11) | −0.0008 (12) |
C4 | 0.0206 (14) | 0.046 (2) | 0.0194 (16) | 0.0066 (13) | 0.0038 (12) | −0.0070 (14) |
C5 | 0.0208 (14) | 0.045 (2) | 0.0150 (16) | −0.0037 (13) | 0.0042 (12) | 0.0050 (13) |
C6 | 0.0217 (14) | 0.0272 (16) | 0.0202 (16) | −0.0066 (12) | −0.0010 (12) | 0.0043 (12) |
C7 | 0.0155 (12) | 0.0243 (15) | 0.0152 (15) | −0.0065 (11) | −0.0012 (11) | −0.0034 (11) |
C8 | 0.0230 (13) | 0.0175 (14) | 0.0096 (14) | −0.0016 (11) | −0.0043 (11) | 0.0009 (11) |
C9 | 0.0179 (12) | 0.0134 (13) | 0.0148 (14) | 0.0008 (10) | −0.0029 (11) | −0.0007 (10) |
C10 | 0.0267 (14) | 0.0190 (15) | 0.0195 (16) | 0.0013 (11) | 0.0045 (12) | 0.0001 (11) |
C11 | 0.0288 (15) | 0.0203 (16) | 0.0293 (18) | −0.0024 (12) | 0.0061 (13) | 0.0051 (12) |
C12 | 0.0255 (14) | 0.0113 (14) | 0.0301 (17) | 0.0027 (11) | −0.0044 (13) | 0.0006 (12) |
C13 | 0.0259 (15) | 0.0221 (15) | 0.0288 (17) | 0.0026 (12) | 0.0034 (13) | −0.0064 (13) |
C14 | 0.0206 (13) | 0.0194 (15) | 0.0171 (15) | −0.0011 (11) | 0.0009 (11) | 0.0004 (11) |
C15 | 0.0164 (13) | 0.0235 (16) | 0.0136 (14) | −0.0038 (11) | −0.0016 (11) | −0.0033 (11) |
C16 | 0.0160 (12) | 0.0180 (14) | 0.0131 (14) | −0.0039 (11) | −0.0014 (10) | 0.0001 (11) |
C17 | 0.0200 (13) | 0.0227 (15) | 0.0182 (15) | −0.0032 (11) | 0.0024 (11) | −0.0011 (11) |
C18 | 0.0306 (15) | 0.0207 (15) | 0.0257 (17) | −0.0001 (12) | 0.0057 (13) | 0.0020 (12) |
C19 | 0.0327 (16) | 0.0280 (17) | 0.0218 (16) | −0.0107 (13) | 0.0092 (13) | 0.0036 (12) |
C20 | 0.0194 (14) | 0.0309 (17) | 0.0320 (18) | −0.0013 (12) | 0.0122 (13) | −0.0006 (13) |
C21 | 0.0236 (14) | 0.0209 (15) | 0.0218 (16) | 0.0002 (11) | 0.0036 (12) | −0.0024 (12) |
C22 | 0.0213 (13) | 0.0173 (14) | 0.0070 (13) | 0.0001 (11) | 0.0010 (10) | −0.0012 (10) |
C23 | 0.0176 (12) | 0.0139 (13) | 0.0151 (14) | 0.0002 (10) | 0.0024 (10) | 0.0017 (10) |
C24 | 0.0176 (13) | 0.0184 (14) | 0.0231 (16) | −0.0033 (11) | −0.0033 (11) | −0.0028 (11) |
C25 | 0.0188 (13) | 0.0209 (15) | 0.0247 (16) | 0.0034 (11) | −0.0026 (12) | 0.0014 (12) |
C26 | 0.0260 (14) | 0.0124 (14) | 0.0167 (15) | 0.0036 (11) | 0.0031 (11) | 0.0000 (11) |
C27 | 0.0220 (14) | 0.0152 (14) | 0.0300 (17) | −0.0040 (11) | −0.0002 (12) | −0.0021 (12) |
C28 | 0.0152 (12) | 0.0190 (15) | 0.0287 (17) | 0.0019 (11) | −0.0015 (12) | 0.0011 (12) |
C29 | 0.0165 (12) | 0.0159 (13) | 0.0112 (13) | 0.0036 (10) | 0.0049 (10) | −0.0010 (10) |
C30 | 0.0239 (14) | 0.0171 (14) | 0.0162 (15) | 0.0056 (11) | 0.0004 (12) | 0.0010 (11) |
C31 | 0.0267 (15) | 0.0289 (17) | 0.0159 (15) | 0.0097 (12) | −0.0014 (12) | 0.0040 (12) |
C32 | 0.0261 (15) | 0.0288 (17) | 0.0169 (16) | 0.0038 (12) | −0.0059 (12) | −0.0051 (12) |
C33 | 0.0232 (14) | 0.0148 (14) | 0.0193 (15) | 0.0004 (11) | 0.0002 (12) | −0.0052 (11) |
C34 | 0.0241 (14) | 0.0142 (14) | 0.0142 (15) | 0.0022 (11) | 0.0012 (11) | 0.0033 (11) |
C35 | 0.0115 (12) | 0.0178 (14) | 0.0163 (14) | −0.0027 (10) | 0.0049 (10) | −0.0010 (11) |
C36 | 0.0174 (13) | 0.0157 (14) | 0.0224 (15) | −0.0055 (11) | 0.0022 (11) | −0.0019 (11) |
C37 | 0.0152 (13) | 0.0301 (17) | 0.0233 (17) | −0.0021 (12) | −0.0041 (12) | −0.0015 (13) |
C38 | 0.0213 (14) | 0.0201 (15) | 0.0278 (17) | 0.0086 (12) | −0.0045 (12) | 0.0002 (12) |
C39 | 0.0212 (14) | 0.0154 (14) | 0.0250 (16) | 0.0003 (11) | 0.0003 (12) | −0.0010 (11) |
C40 | 0.0204 (13) | 0.0132 (13) | 0.0182 (15) | −0.0011 (11) | −0.0014 (11) | 0.0017 (11) |
C41 | 0.0213 (13) | 0.0084 (13) | 0.0161 (14) | 0.0000 (10) | 0.0010 (11) | 0.0002 (10) |
C42 | 0.0207 (14) | 0.0216 (15) | 0.0225 (16) | 0.0000 (11) | 0.0026 (12) | 0.0008 (12) |
C43 | 0.0222 (14) | 0.0280 (16) | 0.0285 (18) | 0.0029 (12) | −0.0062 (13) | 0.0030 (13) |
C44 | 0.0345 (16) | 0.0306 (17) | 0.0173 (16) | 0.0046 (13) | −0.0034 (13) | 0.0026 (12) |
C45 | 0.0271 (15) | 0.0227 (15) | 0.0177 (16) | 0.0057 (12) | 0.0032 (12) | 0.0035 (12) |
C46 | 0.0200 (13) | 0.0205 (15) | 0.0159 (15) | 0.0042 (11) | 0.0018 (11) | 0.0031 (11) |
C47 | 0.0184 (13) | 0.0134 (14) | 0.0178 (15) | 0.0002 (10) | −0.0009 (11) | −0.0019 (11) |
C48 | 0.0262 (14) | 0.0279 (16) | 0.0150 (15) | 0.0013 (12) | 0.0001 (12) | −0.0013 (12) |
C49 | 0.0278 (15) | 0.0385 (19) | 0.0207 (17) | −0.0019 (13) | −0.0091 (13) | 0.0007 (13) |
C50 | 0.0174 (13) | 0.0342 (17) | 0.0283 (18) | −0.0022 (12) | −0.0061 (13) | −0.0003 (13) |
C51 | 0.0171 (13) | 0.0284 (16) | 0.0216 (16) | −0.0018 (12) | 0.0013 (12) | 0.0001 (12) |
C52 | 0.0183 (13) | 0.0216 (15) | 0.0124 (14) | 0.0018 (11) | 0.0018 (11) | 0.0019 (11) |
Cu1—O5 | 1.919 (2) | C12—C13 | 1.386 (4) |
Cu1—O9 | 1.945 (2) | C13—C14 | 1.382 (3) |
Cu1—O12 | 1.974 (2) | C13—H13 | 0.9500 |
Cu1—N4 | 1.988 (2) | C14—H14 | 0.9500 |
Cu1—O7 | 2.385 (2) | C15—C16 | 1.515 (3) |
Cu1—O11 | 2.873 (2) | C16—C21 | 1.389 (3) |
Cu1—Cu2 | 3.096 (1) | C16—C17 | 1.391 (3) |
Cu1—Cu4 | 3.376 (1) | C17—C18 | 1.382 (3) |
Cu1—Cu3 | 3.514 (1) | C17—H17 | 0.9500 |
Cu2—O8 | 1.932 (2) | C18—C19 | 1.388 (4) |
Cu2—O10 | 1.957 (2) | C18—H18 | 0.9500 |
Cu2—O12 | 1.965 (2) | C19—C20 | 1.379 (4) |
Cu2—N2 | 1.998 (2) | C20—C21 | 1.387 (4) |
Cu2—O9 | 2.545 (2) | C20—H20 | 0.9500 |
Cu2—O2 | 2.607 (2) | C21—H21 | 0.9500 |
Cu2—Cu3 | 3.027 (1) | C22—C23 | 1.508 (3) |
Cu2—Cu4 | 3.362 (1) | C23—C28 | 1.392 (3) |
Cu3—O11 | 1.913 (2) | C23—C24 | 1.395 (3) |
Cu3—O1 | 1.918 (2) | C24—C25 | 1.380 (3) |
Cu3—O10 | 1.955 (2) | C24—H24 | 0.9500 |
Cu3—N3 | 2.008 (2) | C25—C26 | 1.380 (3) |
Cu3—O12 | 2.303 (2) | C25—H25 | 0.9500 |
Cu3—Cu4 | 3.141 (1) | C26—C27 | 1.381 (3) |
Cu4—O3 | 1.937 (2) | C27—C28 | 1.388 (3) |
Cu4—O11 | 1.942 (2) | C27—H27 | 0.9500 |
Cu4—O9 | 1.954 (2) | C28—H28 | 0.9500 |
Cu4—N1 | 1.984 (2) | C29—C30 | 1.390 (3) |
Cu4—O10 | 2.396 (2) | C29—C34 | 1.501 (4) |
Cu4—O4 | 2.811 (2) | C30—C31 | 1.373 (4) |
Cl1—C5 | 1.744 (3) | C30—H30 | 0.9500 |
Cl2—C12 | 1.737 (3) | C31—C32 | 1.391 (4) |
Cl3—C19 | 1.741 (3) | C31—H31 | 0.9500 |
Cl4—C26 | 1.741 (2) | C32—C33 | 1.382 (4) |
N1—C33 | 1.340 (3) | C32—H32 | 0.9500 |
N1—C29 | 1.342 (3) | C33—H33 | 0.9500 |
N2—C35 | 1.346 (3) | C34—H34A | 0.9900 |
N2—C39 | 1.353 (3) | C34—H34B | 0.9900 |
N3—C41 | 1.347 (3) | C35—C36 | 1.388 (3) |
N3—C45 | 1.348 (3) | C35—C40 | 1.515 (3) |
N4—C47 | 1.339 (3) | C36—C37 | 1.381 (4) |
N4—C51 | 1.351 (3) | C36—H36 | 0.9500 |
O1—C1 | 1.294 (3) | C37—C38 | 1.385 (4) |
O2—C1 | 1.237 (3) | C37—H37 | 0.9500 |
O3—C8 | 1.285 (3) | C38—C39 | 1.376 (4) |
O4—C8 | 1.235 (3) | C38—H38 | 0.9500 |
O5—C15 | 1.279 (3) | C39—H39 | 0.9500 |
O6—C15 | 1.226 (3) | C40—H40A | 0.9900 |
O7—C22 | 1.242 (3) | C40—H40B | 0.9900 |
O8—C22 | 1.290 (3) | C41—C42 | 1.384 (3) |
O9—C34 | 1.407 (3) | C41—C46 | 1.501 (3) |
O10—C40 | 1.410 (3) | C42—C43 | 1.383 (4) |
O11—C46 | 1.396 (3) | C42—H42 | 0.9500 |
O12—C52 | 1.409 (3) | C43—C44 | 1.383 (4) |
C1—C2 | 1.511 (3) | C43—H43 | 0.9500 |
C2—C3 | 1.391 (3) | C44—C45 | 1.373 (4) |
C2—C7 | 1.399 (3) | C44—H44 | 0.9500 |
C3—C4 | 1.384 (4) | C45—H45 | 0.9500 |
C3—H3 | 0.9500 | C46—H46A | 0.9900 |
C4—C5 | 1.382 (4) | C46—H46B | 0.9900 |
C4—H4 | 0.9500 | C47—C48 | 1.388 (4) |
C5—C6 | 1.383 (4) | C47—C52 | 1.509 (3) |
C6—C7 | 1.381 (3) | C48—C49 | 1.381 (4) |
C6—H6 | 0.9500 | C48—H48 | 0.9500 |
C7—H7 | 0.9500 | C49—C50 | 1.379 (4) |
C8—C9 | 1.502 (3) | C49—H49 | 0.9500 |
C9—C10 | 1.390 (3) | C50—C51 | 1.381 (4) |
C9—C14 | 1.395 (3) | C50—H50 | 0.9500 |
C10—C11 | 1.389 (3) | C51—H51 | 0.9500 |
C10—H10 | 0.9500 | C52—H52A | 0.9900 |
C11—C12 | 1.383 (4) | C52—H52B | 0.9900 |
C11—H11 | 0.9500 | ||
O5—Cu1—O9 | 96.11 (8) | C52—O12—Cu1 | 109.37 (14) |
O5—Cu1—O12 | 171.05 (7) | Cu2—O12—Cu1 | 103.65 (8) |
O9—Cu1—O12 | 88.64 (7) | C52—O12—Cu3 | 117.43 (14) |
O5—Cu1—N4 | 95.45 (8) | Cu2—O12—Cu3 | 89.97 (6) |
O9—Cu1—N4 | 164.64 (7) | Cu1—O12—Cu3 | 110.25 (7) |
O12—Cu1—N4 | 81.32 (8) | O2—C1—O1 | 127.4 (2) |
O5—Cu1—O7 | 88.68 (7) | O2—C1—C2 | 119.9 (2) |
O9—Cu1—O7 | 92.76 (7) | O1—C1—C2 | 112.6 (2) |
O12—Cu1—O7 | 83.50 (6) | C3—C2—C7 | 119.2 (2) |
N4—Cu1—O7 | 97.58 (7) | C3—C2—C1 | 120.6 (2) |
O5—Cu1—O11 | 118.26 (6) | C7—C2—C1 | 120.2 (2) |
O9—Cu1—O11 | 64.89 (6) | C4—C3—C2 | 120.7 (3) |
O12—Cu1—O11 | 70.64 (6) | C4—C3—H3 | 119.6 |
N4—Cu1—O11 | 100.61 (7) | C2—C3—H3 | 119.6 |
O7—Cu1—O11 | 145.45 (5) | C5—C4—C3 | 118.8 (3) |
O5—Cu1—Cu2 | 142.00 (6) | C5—C4—H4 | 120.6 |
O9—Cu1—Cu2 | 55.09 (5) | C3—C4—H4 | 120.6 |
O12—Cu1—Cu2 | 38.06 (5) | C4—C5—C6 | 121.7 (3) |
N4—Cu1—Cu2 | 118.13 (6) | C4—C5—Cl1 | 120.2 (2) |
O7—Cu1—Cu2 | 70.74 (4) | C6—C5—Cl1 | 118.1 (2) |
O11—Cu1—Cu2 | 74.79 (3) | C5—C6—C7 | 119.1 (3) |
O5—Cu1—Cu4 | 106.38 (6) | C5—C6—H6 | 120.5 |
O9—Cu1—Cu4 | 30.08 (5) | C7—C6—H6 | 120.5 |
O12—Cu1—Cu4 | 81.46 (5) | C6—C7—C2 | 120.4 (2) |
N4—Cu1—Cu4 | 135.67 (6) | C6—C7—H7 | 119.8 |
O7—Cu1—Cu4 | 120.53 (5) | C2—C7—H7 | 119.8 |
O11—Cu1—Cu4 | 35.05 (4) | O4—C8—O3 | 124.7 (2) |
Cu2—Cu1—Cu4 | 62.42 (2) | O4—C8—C9 | 119.7 (2) |
O5—Cu1—Cu3 | 150.79 (5) | O3—C8—C9 | 115.6 (2) |
O9—Cu1—Cu3 | 76.19 (5) | C10—C9—C14 | 118.9 (2) |
O12—Cu1—Cu3 | 37.94 (5) | C10—C9—C8 | 120.9 (2) |
N4—Cu1—Cu3 | 88.82 (6) | C14—C9—C8 | 120.2 (2) |
O7—Cu1—Cu3 | 119.45 (5) | C11—C10—C9 | 121.2 (2) |
O11—Cu1—Cu3 | 32.95 (4) | C11—C10—H10 | 119.4 |
Cu4—Cu1—Cu3 | 54.19 (2) | C9—C10—H10 | 119.4 |
O8—Cu2—O10 | 171.59 (7) | C12—C11—C10 | 118.4 (2) |
O8—Cu2—O12 | 98.98 (7) | C12—C11—H11 | 120.8 |
O10—Cu2—O12 | 87.60 (7) | C10—C11—H11 | 120.8 |
O8—Cu2—N2 | 92.13 (7) | C11—C12—C13 | 121.9 (2) |
O10—Cu2—N2 | 80.87 (7) | C11—C12—Cl2 | 119.2 (2) |
O12—Cu2—N2 | 167.71 (7) | C13—C12—Cl2 | 119.0 (2) |
O8—Cu2—O9 | 97.54 (6) | C14—C13—C12 | 118.9 (2) |
O10—Cu2—O9 | 79.22 (6) | C14—C13—H13 | 120.6 |
O12—Cu2—O9 | 73.51 (6) | C12—C13—H13 | 120.6 |
N2—Cu2—O9 | 99.96 (7) | C13—C14—C9 | 120.8 (2) |
O8—Cu2—O2 | 104.80 (7) | C13—C14—H14 | 119.6 |
O10—Cu2—O2 | 81.23 (6) | C9—C14—H14 | 119.6 |
O12—Cu2—O2 | 81.69 (6) | O6—C15—O5 | 126.8 (2) |
N2—Cu2—O2 | 100.60 (7) | O6—C15—C16 | 120.2 (2) |
O9—Cu2—O2 | 148.85 (5) | O5—C15—C16 | 113.0 (2) |
O8—Cu2—Cu3 | 148.14 (5) | C21—C16—C17 | 118.9 (2) |
O10—Cu2—Cu3 | 39.30 (5) | C21—C16—C15 | 120.5 (2) |
O12—Cu2—Cu3 | 49.56 (5) | C17—C16—C15 | 120.6 (2) |
N2—Cu2—Cu3 | 119.68 (6) | C18—C17—C16 | 121.1 (2) |
O9—Cu2—Cu3 | 79.65 (4) | C18—C17—H17 | 119.5 |
O2—Cu2—Cu3 | 69.88 (4) | C16—C17—H17 | 119.5 |
O8—Cu2—Cu1 | 87.81 (5) | C17—C18—C19 | 118.8 (3) |
O10—Cu2—Cu1 | 94.26 (5) | C17—C18—H18 | 120.6 |
O12—Cu2—Cu1 | 38.29 (5) | C19—C18—H18 | 120.6 |
N2—Cu2—Cu1 | 138.02 (6) | C20—C19—C18 | 121.3 (2) |
O9—Cu2—Cu1 | 38.80 (4) | C20—C19—Cl3 | 120.2 (2) |
O2—Cu2—Cu1 | 119.97 (5) | C18—C19—Cl3 | 118.5 (2) |
Cu3—Cu2—Cu1 | 70.045 (18) | C19—C20—C21 | 119.2 (2) |
O8—Cu2—Cu4 | 130.99 (5) | C19—C20—H20 | 120.4 |
O10—Cu2—Cu4 | 44.46 (5) | C21—C20—H20 | 120.4 |
O12—Cu2—Cu4 | 81.95 (5) | C20—C21—C16 | 120.7 (2) |
N2—Cu2—Cu4 | 86.81 (6) | C20—C21—H21 | 119.7 |
O9—Cu2—Cu4 | 35.31 (4) | C16—C21—H21 | 119.7 |
O2—Cu2—Cu4 | 123.56 (4) | O7—C22—O8 | 126.5 (2) |
Cu3—Cu2—Cu4 | 58.609 (19) | O7—C22—C23 | 118.8 (2) |
Cu1—Cu2—Cu4 | 62.86 (2) | O8—C22—C23 | 114.7 (2) |
O11—Cu3—O1 | 175.93 (7) | C28—C23—C24 | 118.7 (2) |
O11—Cu3—O10 | 85.36 (7) | C28—C23—C22 | 119.4 (2) |
O1—Cu3—O10 | 98.02 (7) | C24—C23—C22 | 121.9 (2) |
O11—Cu3—N3 | 82.06 (8) | C25—C24—C23 | 120.8 (2) |
O1—Cu3—N3 | 94.50 (8) | C25—C24—H24 | 119.6 |
O10—Cu3—N3 | 167.33 (7) | C23—C24—H24 | 119.6 |
O11—Cu3—O12 | 86.27 (7) | C26—C25—C24 | 119.5 (2) |
O1—Cu3—O12 | 96.58 (6) | C26—C25—H25 | 120.3 |
O10—Cu3—O12 | 78.72 (6) | C24—C25—H25 | 120.3 |
N3—Cu3—O12 | 101.78 (7) | C25—C26—C27 | 121.1 (2) |
O11—Cu3—Cu2 | 91.76 (5) | C25—C26—Cl4 | 120.0 (2) |
O1—Cu3—Cu2 | 92.29 (5) | C27—C26—Cl4 | 118.9 (2) |
O10—Cu3—Cu2 | 39.34 (5) | C26—C27—C28 | 119.2 (2) |
N3—Cu3—Cu2 | 142.22 (6) | C26—C27—H27 | 120.4 |
O12—Cu3—Cu2 | 40.47 (4) | C28—C27—H27 | 120.4 |
O11—Cu3—Cu4 | 35.75 (5) | C27—C28—C23 | 120.8 (2) |
O1—Cu3—Cu4 | 147.40 (6) | C27—C28—H28 | 119.6 |
O10—Cu3—Cu4 | 49.69 (5) | C23—C28—H28 | 119.6 |
N3—Cu3—Cu4 | 117.66 (6) | N1—C29—C30 | 121.4 (2) |
O12—Cu3—Cu4 | 82.63 (4) | N1—C29—C34 | 115.8 (2) |
Cu2—Cu3—Cu4 | 66.044 (18) | C30—C29—C34 | 122.8 (2) |
O11—Cu3—Cu1 | 54.78 (6) | C31—C30—C29 | 119.1 (2) |
O1—Cu3—Cu1 | 127.77 (5) | C31—C30—H30 | 120.4 |
O10—Cu3—Cu1 | 82.24 (5) | C29—C30—H30 | 120.4 |
N3—Cu3—Cu1 | 91.61 (6) | C30—C31—C32 | 119.4 (3) |
O12—Cu3—Cu1 | 31.81 (4) | C30—C31—H31 | 120.3 |
Cu2—Cu3—Cu1 | 55.91 (2) | C32—C31—H31 | 120.3 |
Cu4—Cu3—Cu1 | 60.652 (15) | C33—C32—C31 | 118.4 (3) |
O3—Cu4—O11 | 92.79 (8) | C33—C32—H32 | 120.8 |
O3—Cu4—O9 | 173.96 (7) | C31—C32—H32 | 120.8 |
O11—Cu4—O9 | 87.79 (8) | N1—C33—C32 | 122.1 (2) |
O3—Cu4—N1 | 97.26 (8) | N1—C33—H33 | 118.9 |
O11—Cu4—N1 | 169.58 (8) | C32—C33—H33 | 118.9 |
O9—Cu4—N1 | 82.51 (8) | O9—C34—C29 | 110.6 (2) |
O3—Cu4—O10 | 91.23 (6) | O9—C34—H34A | 109.5 |
O11—Cu4—O10 | 73.55 (7) | C29—C34—H34A | 109.5 |
O9—Cu4—O10 | 83.16 (6) | O9—C34—H34B | 109.5 |
N1—Cu4—O10 | 108.85 (7) | C29—C34—H34B | 109.5 |
O3—Cu4—O4 | 52.20 (6) | H34A—C34—H34B | 108.1 |
O11—Cu4—O4 | 86.89 (7) | N2—C35—C36 | 121.6 (2) |
O9—Cu4—O4 | 133.84 (6) | N2—C35—C40 | 114.0 (2) |
N1—Cu4—O4 | 97.09 (7) | C36—C35—C40 | 124.4 (2) |
O10—Cu4—O4 | 137.97 (5) | C37—C36—C35 | 119.5 (2) |
O3—Cu4—Cu3 | 90.80 (6) | C37—C36—H36 | 120.3 |
O11—Cu4—Cu3 | 35.14 (5) | C35—C36—H36 | 120.3 |
O9—Cu4—Cu3 | 86.21 (5) | C36—C37—C38 | 118.7 (3) |
N1—Cu4—Cu3 | 146.75 (6) | C36—C37—H37 | 120.7 |
O10—Cu4—Cu3 | 38.48 (4) | C38—C37—H37 | 120.7 |
O4—Cu4—Cu3 | 113.04 (4) | C39—C38—C37 | 119.5 (2) |
O3—Cu4—Cu2 | 125.29 (5) | C39—C38—H38 | 120.2 |
O11—Cu4—Cu2 | 81.63 (6) | C37—C38—H38 | 120.2 |
O9—Cu4—Cu2 | 48.85 (5) | N2—C39—C38 | 121.8 (2) |
N1—Cu4—Cu2 | 94.70 (6) | N2—C39—H39 | 119.1 |
O10—Cu4—Cu2 | 34.89 (4) | C38—C39—H39 | 119.1 |
O4—Cu4—Cu2 | 168.17 (4) | O10—C40—C35 | 108.20 (19) |
Cu3—Cu4—Cu2 | 55.35 (2) | O10—C40—H40A | 110.1 |
O3—Cu4—Cu1 | 150.96 (6) | C35—C40—H40A | 110.1 |
O11—Cu4—Cu1 | 58.19 (6) | O10—C40—H40B | 110.1 |
O9—Cu4—Cu1 | 29.93 (5) | C35—C40—H40B | 110.1 |
N1—Cu4—Cu1 | 111.79 (6) | H40A—C40—H40B | 108.4 |
O10—Cu4—Cu1 | 79.96 (4) | N3—C41—C42 | 121.2 (2) |
O4—Cu4—Cu1 | 120.67 (4) | N3—C41—C46 | 115.4 (2) |
Cu3—Cu4—Cu1 | 65.16 (2) | C42—C41—C46 | 123.5 (2) |
Cu2—Cu4—Cu1 | 54.716 (19) | C43—C42—C41 | 119.6 (2) |
C33—N1—C29 | 119.4 (2) | C43—C42—H42 | 120.2 |
C33—N1—Cu4 | 126.58 (17) | C41—C42—H42 | 120.2 |
C29—N1—Cu4 | 114.01 (16) | C42—C43—C44 | 118.7 (3) |
C35—N2—C39 | 118.9 (2) | C42—C43—H43 | 120.7 |
C35—N2—Cu2 | 113.75 (16) | C44—C43—H43 | 120.7 |
C39—N2—Cu2 | 127.27 (17) | C45—C44—C43 | 119.4 (3) |
C41—N3—C45 | 119.2 (2) | C45—C44—H44 | 120.3 |
C41—N3—Cu3 | 113.09 (17) | C43—C44—H44 | 120.3 |
C45—N3—Cu3 | 127.23 (17) | N3—C45—C44 | 122.0 (2) |
C47—N4—C51 | 119.5 (2) | N3—C45—H45 | 119.0 |
C47—N4—Cu1 | 112.93 (16) | C44—C45—H45 | 119.0 |
C51—N4—Cu1 | 127.54 (18) | O11—C46—C41 | 109.5 (2) |
C1—O1—Cu3 | 126.73 (16) | O11—C46—H46A | 109.8 |
C1—O2—Cu2 | 123.38 (15) | C41—C46—H46A | 109.8 |
C8—O3—Cu4 | 110.58 (15) | O11—C46—H46B | 109.8 |
C8—O4—Cu4 | 70.90 (14) | C41—C46—H46B | 109.8 |
C15—O5—Cu1 | 126.33 (17) | H46A—C46—H46B | 108.2 |
C22—O7—Cu1 | 127.79 (16) | N4—C47—C48 | 121.5 (2) |
C22—O8—Cu2 | 126.29 (15) | N4—C47—C52 | 114.6 (2) |
C34—O9—Cu1 | 120.10 (15) | C48—C47—C52 | 123.9 (2) |
C34—O9—Cu4 | 114.42 (15) | C49—C48—C47 | 119.1 (3) |
Cu1—O9—Cu4 | 119.99 (8) | C49—C48—H48 | 120.5 |
C34—O9—Cu2 | 111.89 (14) | C47—C48—H48 | 120.5 |
Cu1—O9—Cu2 | 86.11 (7) | C48—C49—C50 | 119.2 (3) |
Cu4—O9—Cu2 | 95.84 (6) | C48—C49—H49 | 120.4 |
C40—O10—Cu3 | 130.13 (14) | C50—C49—H49 | 120.4 |
C40—O10—Cu2 | 111.67 (13) | C51—C50—C49 | 119.2 (2) |
Cu3—O10—Cu2 | 101.36 (8) | C51—C50—H50 | 120.4 |
C40—O10—Cu4 | 116.27 (14) | C49—C50—H50 | 120.4 |
Cu3—O10—Cu4 | 91.83 (6) | N4—C51—C50 | 121.4 (2) |
Cu2—O10—Cu4 | 100.65 (6) | N4—C51—H51 | 119.3 |
C46—O11—Cu3 | 116.54 (15) | C50—C51—H51 | 119.3 |
C46—O11—Cu4 | 130.74 (16) | O12—C52—C47 | 109.19 (19) |
Cu3—O11—Cu4 | 109.11 (8) | O12—C52—H52A | 109.8 |
C46—O11—Cu1 | 108.23 (15) | C47—C52—H52A | 109.8 |
Cu3—O11—Cu1 | 92.27 (7) | O12—C52—H52B | 109.8 |
Cu4—O11—Cu1 | 86.76 (6) | C47—C52—H52B | 109.8 |
C52—O12—Cu2 | 124.21 (14) | H52A—C52—H52B | 108.3 |
O5—Cu1—Cu2—O8 | −57.95 (10) | O9—Cu2—O2—C1 | −11.1 (3) |
O9—Cu1—Cu2—O8 | −104.91 (8) | Cu3—Cu2—O2—C1 | 1.48 (18) |
O12—Cu1—Cu2—O8 | 107.50 (9) | Cu1—Cu2—O2—C1 | −49.4 (2) |
N4—Cu1—Cu2—O8 | 91.29 (8) | Cu4—Cu2—O2—C1 | 26.1 (2) |
O7—Cu1—Cu2—O8 | 2.92 (7) | N1—Cu4—O3—C8 | 100.68 (17) |
O11—Cu1—Cu2—O8 | −174.63 (6) | O10—Cu4—O3—C8 | −150.15 (17) |
Cu4—Cu1—Cu2—O8 | −139.22 (5) | O4—Cu4—O3—C8 | 7.31 (15) |
Cu3—Cu1—Cu2—O8 | 156.66 (5) | Cu3—Cu4—O3—C8 | −111.66 (17) |
O5—Cu1—Cu2—O10 | 113.88 (10) | Cu2—Cu4—O3—C8 | −158.28 (14) |
O9—Cu1—Cu2—O10 | 66.92 (8) | Cu1—Cu4—O3—C8 | −78.8 (2) |
O12—Cu1—Cu2—O10 | −80.67 (9) | O3—Cu4—O4—C8 | −7.54 (15) |
N4—Cu1—Cu2—O10 | −96.88 (8) | O11—Cu4—O4—C8 | 88.42 (16) |
O7—Cu1—Cu2—O10 | 174.75 (7) | O9—Cu4—O4—C8 | 172.35 (15) |
O11—Cu1—Cu2—O10 | −2.80 (6) | N1—Cu4—O4—C8 | −101.25 (16) |
Cu4—Cu1—Cu2—O10 | 32.61 (5) | O10—Cu4—O4—C8 | 27.38 (18) |
Cu3—Cu1—Cu2—O10 | −31.51 (5) | Cu3—Cu4—O4—C8 | 64.36 (15) |
O5—Cu1—Cu2—O12 | −165.45 (12) | Cu2—Cu4—O4—C8 | 74.6 (2) |
O9—Cu1—Cu2—O12 | 147.59 (10) | Cu1—Cu4—O4—C8 | 138.18 (14) |
N4—Cu1—Cu2—O12 | −16.21 (10) | N4—Cu1—O5—C15 | 77.7 (2) |
O7—Cu1—Cu2—O12 | −104.58 (9) | O7—Cu1—O5—C15 | 175.2 (2) |
O11—Cu1—Cu2—O12 | 77.87 (8) | O11—Cu1—O5—C15 | −27.4 (2) |
Cu4—Cu1—Cu2—O12 | 113.28 (8) | Cu2—Cu1—O5—C15 | −129.23 (18) |
Cu3—Cu1—Cu2—O12 | 49.16 (7) | Cu4—Cu1—O5—C15 | −63.3 (2) |
O5—Cu1—Cu2—N2 | 32.80 (12) | Cu3—Cu1—O5—C15 | −19.6 (3) |
O9—Cu1—Cu2—N2 | −14.16 (10) | O5—Cu1—O7—C22 | 139.1 (2) |
O12—Cu1—Cu2—N2 | −161.75 (11) | O9—Cu1—O7—C22 | 43.0 (2) |
N4—Cu1—Cu2—N2 | −177.96 (11) | O12—Cu1—O7—C22 | −45.3 (2) |
O7—Cu1—Cu2—N2 | 93.67 (10) | N4—Cu1—O7—C22 | −125.6 (2) |
O11—Cu1—Cu2—N2 | −83.88 (9) | O11—Cu1—O7—C22 | −4.2 (3) |
Cu4—Cu1—Cu2—N2 | −48.48 (9) | Cu2—Cu1—O7—C22 | −8.39 (19) |
Cu3—Cu1—Cu2—N2 | −112.59 (9) | Cu4—Cu1—O7—C22 | 30.8 (2) |
O5—Cu1—Cu2—O9 | 46.96 (11) | Cu3—Cu1—O7—C22 | −32.7 (2) |
O12—Cu1—Cu2—O9 | −147.59 (10) | N4—Cu1—O9—C34 | −178.6 (3) |
N4—Cu1—Cu2—O9 | −163.80 (9) | O7—Cu1—O9—C34 | 48.98 (17) |
O7—Cu1—Cu2—O9 | 107.83 (7) | O11—Cu1—O9—C34 | −158.39 (18) |
O11—Cu1—Cu2—O9 | −69.72 (7) | Cu2—Cu1—O9—C34 | 113.11 (17) |
Cu4—Cu1—Cu2—O9 | −34.32 (6) | Cu4—Cu1—O9—C34 | −152.4 (2) |
Cu3—Cu1—Cu2—O9 | −98.43 (6) | Cu3—Cu1—O9—C34 | 168.65 (17) |
O5—Cu1—Cu2—O2 | −163.79 (10) | O5—Cu1—O9—Cu4 | 112.41 (9) |
O9—Cu1—Cu2—O2 | 149.24 (7) | O12—Cu1—O9—Cu4 | −75.20 (9) |
O12—Cu1—Cu2—O2 | 1.65 (9) | N4—Cu1—O9—Cu4 | −26.2 (3) |
N4—Cu1—Cu2—O2 | −14.55 (8) | O7—Cu1—O9—Cu4 | −158.62 (9) |
O7—Cu1—Cu2—O2 | −102.93 (7) | O11—Cu1—O9—Cu4 | −6.00 (7) |
O11—Cu1—Cu2—O2 | 79.52 (6) | Cu2—Cu1—O9—Cu4 | −94.50 (9) |
Cu4—Cu1—Cu2—O2 | 114.93 (5) | Cu3—Cu1—O9—Cu4 | −38.95 (7) |
Cu3—Cu1—Cu2—O2 | 50.82 (5) | O5—Cu1—O9—Cu2 | −153.10 (6) |
O5—Cu1—Cu2—Cu3 | 145.39 (9) | O12—Cu1—O9—Cu2 | 19.30 (6) |
O9—Cu1—Cu2—Cu3 | 98.43 (6) | N4—Cu1—O9—Cu2 | 68.3 (3) |
O12—Cu1—Cu2—Cu3 | −49.16 (7) | O7—Cu1—O9—Cu2 | −64.13 (5) |
N4—Cu1—Cu2—Cu3 | −65.37 (7) | O11—Cu1—O9—Cu2 | 88.50 (5) |
O7—Cu1—Cu2—Cu3 | −153.75 (5) | Cu4—Cu1—O9—Cu2 | 94.50 (9) |
O11—Cu1—Cu2—Cu3 | 28.71 (4) | Cu3—Cu1—O9—Cu2 | 55.54 (3) |
Cu4—Cu1—Cu2—Cu3 | 64.11 (2) | O11—Cu4—O9—C34 | 161.93 (16) |
O5—Cu1—Cu2—Cu4 | 81.28 (9) | N1—Cu4—O9—C34 | −14.26 (15) |
O9—Cu1—Cu2—Cu4 | 34.32 (6) | O10—Cu4—O9—C34 | −124.38 (16) |
O12—Cu1—Cu2—Cu4 | −113.28 (8) | O4—Cu4—O9—C34 | 78.39 (17) |
N4—Cu1—Cu2—Cu4 | −129.48 (7) | Cu3—Cu4—O9—C34 | −162.91 (15) |
O7—Cu1—Cu2—Cu4 | 142.14 (5) | Cu2—Cu4—O9—C34 | −117.26 (17) |
O11—Cu1—Cu2—Cu4 | −35.41 (4) | Cu1—Cu4—O9—C34 | 153.9 (2) |
Cu3—Cu1—Cu2—Cu4 | −64.11 (2) | O11—Cu4—O9—Cu1 | 8.06 (9) |
O8—Cu2—Cu3—O11 | −92.74 (11) | N1—Cu4—O9—Cu1 | −168.14 (10) |
O10—Cu2—Cu3—O11 | 80.48 (9) | O10—Cu4—O9—Cu1 | 81.74 (9) |
O12—Cu2—Cu3—O11 | −82.17 (9) | O4—Cu4—O9—Cu1 | −75.49 (12) |
N2—Cu2—Cu3—O11 | 90.54 (9) | Cu3—Cu4—O9—Cu1 | 43.21 (8) |
O9—Cu2—Cu3—O11 | −5.09 (7) | Cu2—Cu4—O9—Cu1 | 88.87 (9) |
O2—Cu2—Cu3—O11 | −178.49 (7) | O11—Cu4—O9—Cu2 | −80.81 (7) |
Cu1—Cu2—Cu3—O11 | −44.15 (6) | N1—Cu4—O9—Cu2 | 102.99 (7) |
Cu4—Cu2—Cu3—O11 | 25.55 (6) | O10—Cu4—O9—Cu2 | −7.12 (5) |
O8—Cu2—Cu3—O1 | 86.90 (11) | O4—Cu4—O9—Cu2 | −164.36 (6) |
O10—Cu2—Cu3—O1 | −99.88 (9) | Cu3—Cu4—O9—Cu2 | −45.66 (5) |
O12—Cu2—Cu3—O1 | 97.47 (8) | Cu1—Cu4—O9—Cu2 | −88.87 (9) |
N2—Cu2—Cu3—O1 | −89.82 (9) | O8—Cu2—O9—C34 | −44.04 (16) |
O9—Cu2—Cu3—O1 | 174.55 (7) | O10—Cu2—O9—C34 | 128.09 (16) |
O2—Cu2—Cu3—O1 | 1.14 (7) | O12—Cu2—O9—C34 | −141.22 (16) |
Cu1—Cu2—Cu3—O1 | 135.49 (6) | N2—Cu2—O9—C34 | 49.48 (16) |
Cu4—Cu2—Cu3—O1 | −154.81 (6) | O2—Cu2—O9—C34 | −179.87 (14) |
O8—Cu2—Cu3—O10 | −173.22 (12) | Cu3—Cu2—O9—C34 | 168.10 (15) |
O12—Cu2—Cu3—O10 | −162.66 (9) | Cu1—Cu2—O9—C34 | −120.96 (16) |
N2—Cu2—Cu3—O10 | 10.06 (10) | Cu4—Cu2—O9—C34 | 119.27 (17) |
O9—Cu2—Cu3—O10 | −85.58 (8) | O8—Cu2—O9—Cu1 | 76.92 (7) |
O2—Cu2—Cu3—O10 | 101.02 (9) | O10—Cu2—O9—Cu1 | −110.95 (7) |
Cu1—Cu2—Cu3—O10 | −124.63 (7) | O12—Cu2—O9—Cu1 | −20.26 (6) |
Cu4—Cu2—Cu3—O10 | −54.93 (7) | N2—Cu2—O9—Cu1 | 170.44 (7) |
O8—Cu2—Cu3—N3 | −13.46 (14) | O2—Cu2—O9—Cu1 | −58.90 (12) |
O10—Cu2—Cu3—N3 | 159.77 (12) | Cu3—Cu2—O9—Cu1 | −70.94 (5) |
O12—Cu2—Cu3—N3 | −2.89 (11) | Cu4—Cu2—O9—Cu1 | −119.77 (8) |
N2—Cu2—Cu3—N3 | 169.83 (11) | O8—Cu2—O9—Cu4 | −163.31 (7) |
O9—Cu2—Cu3—N3 | 74.19 (10) | O10—Cu2—O9—Cu4 | 8.83 (7) |
O2—Cu2—Cu3—N3 | −99.21 (11) | O12—Cu2—O9—Cu4 | 99.51 (7) |
Cu1—Cu2—Cu3—N3 | 35.13 (10) | N2—Cu2—O9—Cu4 | −69.79 (8) |
Cu4—Cu2—Cu3—N3 | 104.84 (10) | O2—Cu2—O9—Cu4 | 60.87 (13) |
O8—Cu2—Cu3—O12 | −10.57 (11) | Cu3—Cu2—O9—Cu4 | 48.83 (5) |
O10—Cu2—Cu3—O12 | 162.66 (9) | Cu1—Cu2—O9—Cu4 | 119.77 (8) |
N2—Cu2—Cu3—O12 | 172.72 (9) | O11—Cu3—O10—C40 | 130.1 (2) |
O9—Cu2—Cu3—O12 | 77.08 (7) | O1—Cu3—O10—C40 | −47.7 (2) |
O2—Cu2—Cu3—O12 | −96.32 (8) | N3—Cu3—O10—C40 | 123.6 (3) |
Cu1—Cu2—Cu3—O12 | 38.02 (6) | O12—Cu3—O10—C40 | −142.83 (19) |
Cu4—Cu2—Cu3—O12 | 107.73 (6) | Cu2—Cu3—O10—C40 | −131.4 (2) |
O8—Cu2—Cu3—Cu4 | −118.29 (10) | Cu4—Cu3—O10—C40 | 127.3 (2) |
O10—Cu2—Cu3—Cu4 | 54.93 (7) | Cu1—Cu3—O10—C40 | −174.90 (19) |
O12—Cu2—Cu3—Cu4 | −107.73 (6) | O11—Cu3—O10—Cu2 | −98.50 (8) |
N2—Cu2—Cu3—Cu4 | 64.99 (7) | O1—Cu3—O10—Cu2 | 83.78 (8) |
O9—Cu2—Cu3—Cu4 | −30.65 (4) | N3—Cu3—O10—Cu2 | −104.9 (3) |
O2—Cu2—Cu3—Cu4 | 155.95 (4) | O12—Cu3—O10—Cu2 | −11.38 (6) |
Cu1—Cu2—Cu3—Cu4 | −69.70 (3) | Cu4—Cu3—O10—Cu2 | −101.24 (7) |
O8—Cu2—Cu3—Cu1 | −48.59 (10) | Cu1—Cu3—O10—Cu2 | −43.45 (5) |
O10—Cu2—Cu3—Cu1 | 124.63 (7) | O11—Cu3—O10—Cu4 | 2.74 (7) |
O12—Cu2—Cu3—Cu1 | −38.02 (6) | O1—Cu3—O10—Cu4 | −174.98 (6) |
N2—Cu2—Cu3—Cu1 | 134.69 (7) | N3—Cu3—O10—Cu4 | −3.7 (4) |
O9—Cu2—Cu3—Cu1 | 39.06 (4) | O12—Cu3—O10—Cu4 | 89.86 (6) |
O2—Cu2—Cu3—Cu1 | −134.35 (5) | Cu2—Cu3—O10—Cu4 | 101.24 (7) |
Cu4—Cu2—Cu3—Cu1 | 69.70 (3) | Cu1—Cu3—O10—Cu4 | 57.79 (4) |
O5—Cu1—Cu3—O11 | −12.68 (13) | O12—Cu2—O10—C40 | 155.05 (15) |
O9—Cu1—Cu3—O11 | 64.90 (8) | N2—Cu2—O10—C40 | −29.23 (15) |
O12—Cu1—Cu3—O11 | 170.89 (10) | O9—Cu2—O10—C40 | −131.29 (16) |
N4—Cu1—Cu3—O11 | −111.76 (9) | O2—Cu2—O10—C40 | 73.09 (15) |
O7—Cu1—Cu3—O11 | 150.21 (8) | Cu3—Cu2—O10—C40 | 141.93 (18) |
Cu2—Cu1—Cu3—O11 | 121.55 (7) | Cu1—Cu2—O10—C40 | −167.22 (14) |
Cu4—Cu1—Cu3—O11 | 42.03 (7) | Cu4—Cu2—O10—C40 | −124.01 (17) |
O5—Cu1—Cu3—O1 | 163.38 (13) | O12—Cu2—O10—Cu3 | 13.12 (7) |
O9—Cu1—Cu3—O1 | −119.04 (9) | N2—Cu2—O10—Cu3 | −171.16 (8) |
O12—Cu1—Cu3—O1 | −13.05 (10) | O9—Cu2—O10—Cu3 | 86.79 (7) |
N4—Cu1—Cu3—O1 | 64.30 (9) | O2—Cu2—O10—Cu3 | −68.84 (7) |
O7—Cu1—Cu3—O1 | −33.73 (9) | Cu1—Cu2—O10—Cu3 | 50.85 (6) |
O11—Cu1—Cu3—O1 | 176.06 (9) | Cu4—Cu2—O10—Cu3 | 94.06 (8) |
Cu2—Cu1—Cu3—O1 | −62.39 (7) | O12—Cu2—O10—Cu4 | −80.94 (7) |
Cu4—Cu1—Cu3—O1 | −141.91 (7) | N2—Cu2—O10—Cu4 | 94.78 (8) |
O5—Cu1—Cu3—O10 | −102.47 (12) | O9—Cu2—O10—Cu4 | −7.28 (6) |
O9—Cu1—Cu3—O10 | −24.89 (7) | O2—Cu2—O10—Cu4 | −162.90 (7) |
O12—Cu1—Cu3—O10 | 81.11 (9) | Cu3—Cu2—O10—Cu4 | −94.06 (8) |
N4—Cu1—Cu3—O10 | 158.46 (7) | Cu1—Cu2—O10—Cu4 | −43.21 (6) |
O7—Cu1—Cu3—O10 | 60.42 (7) | O3—Cu4—O10—C40 | −47.56 (15) |
O11—Cu1—Cu3—O10 | −89.78 (8) | O11—Cu4—O10—C40 | −140.11 (16) |
Cu2—Cu1—Cu3—O10 | 31.77 (5) | O9—Cu4—O10—C40 | 130.18 (15) |
Cu4—Cu1—Cu3—O10 | −47.75 (5) | N1—Cu4—O10—C40 | 50.54 (16) |
O5—Cu1—Cu3—N3 | 66.42 (13) | O4—Cu4—O10—C40 | −74.46 (17) |
O9—Cu1—Cu3—N3 | 144.00 (8) | Cu3—Cu4—O10—C40 | −137.30 (17) |
O12—Cu1—Cu3—N3 | −110.01 (10) | Cu2—Cu4—O10—C40 | 120.79 (17) |
N4—Cu1—Cu3—N3 | −32.65 (8) | Cu1—Cu4—O10—C40 | 160.28 (15) |
O7—Cu1—Cu3—N3 | −130.69 (8) | O3—Cu4—O10—Cu3 | 89.74 (7) |
O11—Cu1—Cu3—N3 | 79.10 (9) | O11—Cu4—O10—Cu3 | −2.81 (7) |
Cu2—Cu1—Cu3—N3 | −159.35 (6) | O9—Cu4—O10—Cu3 | −92.52 (7) |
Cu4—Cu1—Cu3—N3 | 121.13 (6) | N1—Cu4—O10—Cu3 | −172.17 (7) |
O5—Cu1—Cu3—O12 | 176.43 (14) | O4—Cu4—O10—Cu3 | 62.84 (10) |
O9—Cu1—Cu3—O12 | −105.99 (9) | Cu2—Cu4—O10—Cu3 | −101.91 (8) |
N4—Cu1—Cu3—O12 | 77.36 (10) | Cu1—Cu4—O10—Cu3 | −62.42 (5) |
O7—Cu1—Cu3—O12 | −20.68 (9) | O3—Cu4—O10—Cu2 | −168.35 (8) |
O11—Cu1—Cu3—O12 | −170.89 (10) | O11—Cu4—O10—Cu2 | 99.11 (8) |
Cu2—Cu1—Cu3—O12 | −49.34 (8) | O9—Cu4—O10—Cu2 | 9.40 (7) |
Cu4—Cu1—Cu3—O12 | −128.86 (8) | N1—Cu4—O10—Cu2 | −70.25 (9) |
O5—Cu1—Cu3—Cu2 | −134.23 (12) | O4—Cu4—O10—Cu2 | 164.76 (6) |
O9—Cu1—Cu3—Cu2 | −56.65 (5) | Cu3—Cu4—O10—Cu2 | 101.91 (8) |
O12—Cu1—Cu3—Cu2 | 49.34 (8) | Cu1—Cu4—O10—Cu2 | 39.49 (5) |
N4—Cu1—Cu3—Cu2 | 126.70 (6) | O10—Cu3—O11—C46 | −164.53 (18) |
O7—Cu1—Cu3—Cu2 | 28.66 (5) | N3—Cu3—O11—C46 | 14.04 (18) |
O11—Cu1—Cu3—Cu2 | −121.55 (7) | O12—Cu3—O11—C46 | 116.50 (18) |
Cu4—Cu1—Cu3—Cu2 | −79.52 (3) | Cu2—Cu3—O11—C46 | 156.62 (17) |
O5—Cu1—Cu3—Cu4 | −54.71 (11) | Cu4—Cu3—O11—C46 | −160.9 (2) |
O9—Cu1—Cu3—Cu4 | 22.87 (5) | Cu1—Cu3—O11—C46 | 111.70 (19) |
O12—Cu1—Cu3—Cu4 | 128.86 (8) | O10—Cu3—O11—Cu4 | −3.58 (9) |
N4—Cu1—Cu3—Cu4 | −153.79 (6) | N3—Cu3—O11—Cu4 | 174.99 (10) |
O7—Cu1—Cu3—Cu4 | 108.18 (6) | O12—Cu3—O11—Cu4 | −82.55 (9) |
O11—Cu1—Cu3—Cu4 | −42.03 (7) | Cu2—Cu3—O11—Cu4 | −42.43 (8) |
Cu2—Cu1—Cu3—Cu4 | 79.52 (3) | Cu1—Cu3—O11—Cu4 | −87.35 (8) |
O11—Cu3—Cu4—O3 | 93.72 (11) | O10—Cu3—O11—Cu1 | 83.77 (6) |
O1—Cu3—Cu4—O3 | −81.71 (11) | N3—Cu3—O11—Cu1 | −97.66 (7) |
O10—Cu3—Cu4—O3 | −90.97 (8) | O12—Cu3—O11—Cu1 | 4.80 (5) |
N3—Cu3—Cu4—O3 | 88.11 (8) | Cu2—Cu3—O11—Cu1 | 44.92 (4) |
O12—Cu3—Cu4—O3 | −172.41 (6) | Cu4—Cu3—O11—Cu1 | 87.35 (8) |
Cu2—Cu3—Cu4—O3 | −133.85 (5) | O3—Cu4—O11—C46 | 69.9 (2) |
Cu1—Cu3—Cu4—O3 | 163.14 (5) | O9—Cu4—O11—C46 | −116.1 (2) |
O1—Cu3—Cu4—O11 | −175.42 (14) | N1—Cu4—O11—C46 | −94.8 (5) |
O10—Cu3—Cu4—O11 | 175.32 (11) | O10—Cu4—O11—C46 | 160.4 (2) |
N3—Cu3—Cu4—O11 | −5.60 (11) | O4—Cu4—O11—C46 | 18.0 (2) |
O12—Cu3—Cu4—O11 | 93.87 (10) | Cu3—Cu4—O11—C46 | 157.3 (3) |
Cu2—Cu3—Cu4—O11 | 132.44 (10) | Cu2—Cu4—O11—C46 | −164.8 (2) |
Cu1—Cu3—Cu4—O11 | 69.43 (10) | Cu1—Cu4—O11—C46 | −111.4 (2) |
O11—Cu3—Cu4—O9 | −91.54 (11) | O3—Cu4—O11—Cu3 | −87.42 (9) |
O1—Cu3—Cu4—O9 | 93.03 (11) | O9—Cu4—O11—Cu3 | 86.56 (9) |
O10—Cu3—Cu4—O9 | 83.77 (8) | N1—Cu4—O11—Cu3 | 107.9 (4) |
N3—Cu3—Cu4—O9 | −97.14 (8) | O10—Cu4—O11—Cu3 | 3.04 (7) |
O12—Cu3—Cu4—O9 | 2.33 (6) | O4—Cu4—O11—Cu3 | −139.31 (9) |
Cu2—Cu3—Cu4—O9 | 40.90 (5) | Cu2—Cu4—O11—Cu3 | 37.85 (7) |
Cu1—Cu3—Cu4—O9 | −22.12 (5) | Cu1—Cu4—O11—Cu3 | 91.28 (8) |
O11—Cu3—Cu4—N1 | −161.71 (14) | O3—Cu4—O11—Cu1 | −178.70 (6) |
O1—Cu3—Cu4—N1 | 22.87 (15) | O9—Cu4—O11—Cu1 | −4.72 (5) |
O10—Cu3—Cu4—N1 | 13.61 (12) | N1—Cu4—O11—Cu1 | 16.6 (4) |
N3—Cu3—Cu4—N1 | −167.31 (13) | O10—Cu4—O11—Cu1 | −88.24 (5) |
O12—Cu3—Cu4—N1 | −67.84 (12) | O4—Cu4—O11—Cu1 | 129.41 (5) |
Cu2—Cu3—Cu4—N1 | −29.27 (11) | Cu3—Cu4—O11—Cu1 | −91.28 (8) |
Cu1—Cu3—Cu4—N1 | −92.28 (11) | Cu2—Cu4—O11—Cu1 | −53.43 (3) |
O11—Cu3—Cu4—O10 | −175.32 (11) | O5—Cu1—O11—C46 | 54.07 (16) |
O1—Cu3—Cu4—O10 | 9.26 (11) | O9—Cu1—O11—C46 | 137.27 (16) |
N3—Cu3—Cu4—O10 | 179.08 (9) | O12—Cu1—O11—C46 | −124.86 (16) |
O12—Cu3—Cu4—O10 | −81.44 (7) | N4—Cu1—O11—C46 | −48.07 (16) |
Cu2—Cu3—Cu4—O10 | −42.88 (6) | O7—Cu1—O11—C46 | −168.65 (14) |
Cu1—Cu3—Cu4—O10 | −105.89 (6) | Cu2—Cu1—O11—C46 | −164.57 (15) |
O11—Cu3—Cu4—O4 | 45.02 (10) | Cu4—Cu1—O11—C46 | 132.04 (17) |
O1—Cu3—Cu4—O4 | −130.40 (10) | Cu3—Cu1—O11—C46 | −118.94 (17) |
O10—Cu3—Cu4—O4 | −139.66 (7) | O5—Cu1—O11—Cu3 | 173.01 (7) |
N3—Cu3—Cu4—O4 | 39.42 (8) | O9—Cu1—O11—Cu3 | −103.79 (8) |
O12—Cu3—Cu4—O4 | 138.90 (6) | O12—Cu1—O11—Cu3 | −5.92 (6) |
Cu2—Cu3—Cu4—O4 | 177.46 (4) | N4—Cu1—O11—Cu3 | 70.86 (8) |
Cu1—Cu3—Cu4—O4 | 114.45 (4) | O7—Cu1—O11—Cu3 | −49.72 (13) |
O11—Cu3—Cu4—Cu2 | −132.44 (10) | Cu2—Cu1—O11—Cu3 | −45.63 (5) |
O1—Cu3—Cu4—Cu2 | 52.14 (10) | Cu4—Cu1—O11—Cu3 | −109.03 (8) |
O10—Cu3—Cu4—Cu2 | 42.88 (6) | O5—Cu1—O11—Cu4 | −77.96 (8) |
N3—Cu3—Cu4—Cu2 | −138.04 (7) | O9—Cu1—O11—Cu4 | 5.23 (6) |
O12—Cu3—Cu4—Cu2 | −38.57 (4) | O12—Cu1—O11—Cu4 | 103.10 (7) |
Cu1—Cu3—Cu4—Cu2 | −63.01 (2) | N4—Cu1—O11—Cu4 | 179.89 (7) |
O11—Cu3—Cu4—Cu1 | −69.43 (10) | O7—Cu1—O11—Cu4 | 59.31 (12) |
O1—Cu3—Cu4—Cu1 | 115.15 (10) | Cu2—Cu1—O11—Cu4 | 63.39 (5) |
O10—Cu3—Cu4—Cu1 | 105.89 (6) | Cu3—Cu1—O11—Cu4 | 109.03 (8) |
N3—Cu3—Cu4—Cu1 | −75.03 (7) | O8—Cu2—O12—C52 | 50.54 (18) |
O12—Cu3—Cu4—Cu1 | 24.45 (4) | O10—Cu2—O12—C52 | −134.73 (17) |
Cu2—Cu3—Cu4—Cu1 | 63.01 (2) | N2—Cu2—O12—C52 | −155.0 (3) |
O8—Cu2—Cu4—O3 | −155.94 (9) | O9—Cu2—O12—C52 | 145.81 (18) |
O10—Cu2—Cu4—O3 | 14.32 (10) | O2—Cu2—O12—C52 | −53.25 (17) |
O12—Cu2—Cu4—O3 | 109.13 (8) | Cu3—Cu2—O12—C52 | −123.84 (18) |
N2—Cu2—Cu4—O3 | −65.88 (9) | Cu1—Cu2—O12—C52 | 125.3 (2) |
O9—Cu2—Cu4—O3 | −178.11 (9) | Cu4—Cu2—O12—C52 | −179.04 (17) |
O2—Cu2—Cu4—O3 | 34.73 (8) | O8—Cu2—O12—Cu1 | −74.76 (8) |
Cu3—Cu2—Cu4—O3 | 62.07 (7) | O10—Cu2—O12—Cu1 | 99.97 (8) |
Cu1—Cu2—Cu4—O3 | 144.22 (7) | N2—Cu2—O12—Cu1 | 79.7 (4) |
O8—Cu2—Cu4—O11 | 116.57 (9) | O9—Cu2—O12—Cu1 | 20.50 (6) |
O10—Cu2—Cu4—O11 | −73.17 (9) | O2—Cu2—O12—Cu1 | −178.55 (8) |
O12—Cu2—Cu4—O11 | 21.64 (7) | Cu3—Cu2—O12—Cu1 | 110.86 (8) |
N2—Cu2—Cu4—O11 | −153.37 (8) | Cu4—Cu2—O12—Cu1 | 55.65 (6) |
O9—Cu2—Cu4—O11 | 94.40 (9) | O8—Cu2—O12—Cu3 | 174.38 (6) |
O2—Cu2—Cu4—O11 | −52.76 (7) | O10—Cu2—O12—Cu3 | −10.89 (6) |
Cu3—Cu2—Cu4—O11 | −25.42 (5) | N2—Cu2—O12—Cu3 | −31.2 (4) |
Cu1—Cu2—Cu4—O11 | 56.73 (6) | O9—Cu2—O12—Cu3 | −90.36 (6) |
O8—Cu2—Cu4—O9 | 22.17 (9) | O2—Cu2—O12—Cu3 | 70.59 (5) |
O10—Cu2—Cu4—O9 | −167.57 (9) | Cu1—Cu2—O12—Cu3 | −110.86 (8) |
O12—Cu2—Cu4—O9 | −72.76 (8) | Cu4—Cu2—O12—Cu3 | −55.21 (4) |
N2—Cu2—Cu4—O9 | 112.22 (9) | O9—Cu1—O12—C52 | −160.41 (15) |
O2—Cu2—Cu4—O9 | −147.16 (8) | N4—Cu1—O12—C52 | 31.25 (15) |
Cu3—Cu2—Cu4—O9 | −119.83 (7) | O7—Cu1—O12—C52 | −67.47 (14) |
Cu1—Cu2—Cu4—O9 | −37.67 (6) | O11—Cu1—O12—C52 | 135.80 (15) |
O8—Cu2—Cu4—N1 | −53.61 (9) | Cu2—Cu1—O12—C52 | −134.33 (17) |
O10—Cu2—Cu4—N1 | 116.65 (9) | Cu4—Cu1—O12—C52 | 170.25 (14) |
O12—Cu2—Cu4—N1 | −148.54 (8) | Cu3—Cu1—O12—C52 | 130.56 (17) |
N2—Cu2—Cu4—N1 | 36.44 (8) | O9—Cu1—O12—Cu2 | −26.08 (8) |
O9—Cu2—Cu4—N1 | −75.78 (9) | N4—Cu1—O12—Cu2 | 165.58 (9) |
O2—Cu2—Cu4—N1 | 137.06 (7) | O7—Cu1—O12—Cu2 | 66.86 (7) |
Cu3—Cu2—Cu4—N1 | 164.40 (6) | O11—Cu1—O12—Cu2 | −89.87 (7) |
Cu1—Cu2—Cu4—N1 | −113.45 (6) | Cu4—Cu1—O12—Cu2 | −55.42 (6) |
O8—Cu2—Cu4—O10 | −170.26 (10) | Cu3—Cu1—O12—Cu2 | −95.11 (9) |
O12—Cu2—Cu4—O10 | 94.81 (8) | O9—Cu1—O12—Cu3 | 69.03 (8) |
N2—Cu2—Cu4—O10 | −80.21 (9) | N4—Cu1—O12—Cu3 | −99.31 (9) |
O9—Cu2—Cu4—O10 | 167.57 (9) | O7—Cu1—O12—Cu3 | 161.97 (8) |
O2—Cu2—Cu4—O10 | 20.41 (8) | O11—Cu1—O12—Cu3 | 5.24 (6) |
Cu3—Cu2—Cu4—O10 | 47.74 (7) | Cu2—Cu1—O12—Cu3 | 95.11 (9) |
Cu1—Cu2—Cu4—O10 | 129.90 (7) | Cu4—Cu1—O12—Cu3 | 39.69 (6) |
O8—Cu2—Cu4—O4 | 130.53 (18) | O11—Cu3—O12—C52 | −133.60 (15) |
O10—Cu2—Cu4—O4 | −59.21 (19) | O1—Cu3—O12—C52 | 43.50 (16) |
O12—Cu2—Cu4—O4 | 35.60 (18) | O10—Cu3—O12—C52 | 140.40 (15) |
N2—Cu2—Cu4—O4 | −139.41 (18) | N3—Cu3—O12—C52 | −52.51 (16) |
O9—Cu2—Cu4—O4 | 108.36 (19) | Cu2—Cu3—O12—C52 | 129.29 (17) |
O2—Cu2—Cu4—O4 | −38.80 (18) | Cu4—Cu3—O12—C52 | −169.34 (15) |
Cu3—Cu2—Cu4—O4 | −11.46 (17) | Cu1—Cu3—O12—C52 | −126.15 (18) |
Cu1—Cu2—Cu4—O4 | 70.69 (17) | O11—Cu3—O12—Cu2 | 97.11 (8) |
O8—Cu2—Cu4—Cu3 | 141.99 (7) | O1—Cu3—O12—Cu2 | −85.79 (8) |
O10—Cu2—Cu4—Cu3 | −47.74 (7) | O10—Cu3—O12—Cu2 | 11.11 (6) |
O12—Cu2—Cu4—Cu3 | 47.06 (5) | N3—Cu3—O12—Cu2 | 178.19 (7) |
N2—Cu2—Cu4—Cu3 | −127.95 (6) | Cu4—Cu3—O12—Cu2 | 61.37 (5) |
O9—Cu2—Cu4—Cu3 | 119.83 (7) | Cu1—Cu3—O12—Cu2 | 104.56 (9) |
O2—Cu2—Cu4—Cu3 | −27.33 (5) | O11—Cu3—O12—Cu1 | −7.45 (8) |
Cu1—Cu2—Cu4—Cu3 | 82.15 (3) | O1—Cu3—O12—Cu1 | 169.65 (8) |
O8—Cu2—Cu4—Cu1 | 59.84 (7) | O10—Cu3—O12—Cu1 | −93.45 (9) |
O10—Cu2—Cu4—Cu1 | −129.90 (7) | N3—Cu3—O12—Cu1 | 73.63 (9) |
O12—Cu2—Cu4—Cu1 | −35.09 (5) | Cu2—Cu3—O12—Cu1 | −104.56 (9) |
N2—Cu2—Cu4—Cu1 | 149.90 (6) | Cu4—Cu3—O12—Cu1 | −43.19 (6) |
O9—Cu2—Cu4—Cu1 | 37.67 (6) | Cu2—O2—C1—O1 | −5.4 (4) |
O2—Cu2—Cu4—Cu1 | −109.49 (5) | Cu2—O2—C1—C2 | 173.78 (15) |
Cu3—Cu2—Cu4—Cu1 | −82.15 (3) | Cu3—O1—C1—O2 | 7.3 (4) |
O5—Cu1—Cu4—O3 | 118.79 (12) | Cu3—O1—C1—C2 | −171.87 (16) |
O9—Cu1—Cu4—O3 | −167.84 (14) | O2—C1—C2—C3 | −25.0 (4) |
O12—Cu1—Cu4—O3 | −65.63 (11) | O1—C1—C2—C3 | 154.3 (2) |
N4—Cu1—Cu4—O3 | 2.52 (13) | O2—C1—C2—C7 | 156.8 (2) |
O7—Cu1—Cu4—O3 | −142.84 (11) | O1—C1—C2—C7 | −23.9 (3) |
O11—Cu1—Cu4—O3 | 2.67 (11) | C7—C2—C3—C4 | −0.3 (4) |
Cu2—Cu1—Cu4—O3 | −100.57 (11) | C1—C2—C3—C4 | −178.5 (2) |
Cu3—Cu1—Cu4—O3 | −36.68 (10) | C2—C3—C4—C5 | −1.5 (4) |
O5—Cu1—Cu4—O11 | 116.12 (8) | C3—C4—C5—C6 | 1.6 (4) |
O9—Cu1—Cu4—O11 | −170.51 (11) | C3—C4—C5—Cl1 | −179.5 (2) |
O12—Cu1—Cu4—O11 | −68.31 (7) | C4—C5—C6—C7 | 0.2 (4) |
N4—Cu1—Cu4—O11 | −0.16 (10) | Cl1—C5—C6—C7 | −178.7 (2) |
O7—Cu1—Cu4—O11 | −145.51 (8) | C5—C6—C7—C2 | −2.1 (4) |
Cu2—Cu1—Cu4—O11 | −103.25 (6) | C3—C2—C7—C6 | 2.1 (4) |
Cu3—Cu1—Cu4—O11 | −39.35 (6) | C1—C2—C7—C6 | −179.7 (2) |
O5—Cu1—Cu4—O9 | −73.37 (11) | Cu4—O4—C8—O3 | 11.0 (2) |
O12—Cu1—Cu4—O9 | 102.21 (11) | Cu4—O4—C8—C9 | −167.2 (2) |
N4—Cu1—Cu4—O9 | 170.36 (12) | Cu4—O3—C8—O4 | −16.2 (3) |
O7—Cu1—Cu4—O9 | 25.00 (11) | Cu4—O3—C8—C9 | 162.05 (17) |
O11—Cu1—Cu4—O9 | 170.51 (11) | O4—C8—C9—C10 | 164.5 (2) |
Cu2—Cu1—Cu4—O9 | 67.27 (10) | O3—C8—C9—C10 | −13.8 (4) |
Cu3—Cu1—Cu4—O9 | 131.16 (10) | O4—C8—C9—C14 | −13.2 (4) |
O5—Cu1—Cu4—N1 | −60.69 (8) | O3—C8—C9—C14 | 168.5 (2) |
O9—Cu1—Cu4—N1 | 12.67 (11) | C14—C9—C10—C11 | 0.3 (4) |
O12—Cu1—Cu4—N1 | 114.88 (8) | C8—C9—C10—C11 | −177.4 (2) |
N4—Cu1—Cu4—N1 | −176.97 (10) | C9—C10—C11—C12 | −0.7 (4) |
O7—Cu1—Cu4—N1 | 37.68 (8) | C10—C11—C12—C13 | 0.7 (4) |
O11—Cu1—Cu4—N1 | −176.81 (8) | C10—C11—C12—Cl2 | −179.2 (2) |
Cu2—Cu1—Cu4—N1 | 79.94 (6) | C11—C12—C13—C14 | −0.1 (4) |
Cu3—Cu1—Cu4—N1 | 143.84 (6) | Cl2—C12—C13—C14 | 179.8 (2) |
O5—Cu1—Cu4—O10 | −167.10 (7) | C12—C13—C14—C9 | −0.3 (4) |
O9—Cu1—Cu4—O10 | −93.74 (10) | C10—C9—C14—C13 | 0.2 (4) |
O12—Cu1—Cu4—O10 | 8.47 (6) | C8—C9—C14—C13 | 178.0 (2) |
N4—Cu1—Cu4—O10 | 76.62 (9) | Cu1—O5—C15—O6 | 2.5 (4) |
O7—Cu1—Cu4—O10 | −68.73 (6) | Cu1—O5—C15—C16 | −178.09 (15) |
O11—Cu1—Cu4—O10 | 76.78 (7) | O6—C15—C16—C21 | −2.9 (4) |
Cu2—Cu1—Cu4—O10 | −26.47 (4) | O5—C15—C16—C21 | 177.6 (2) |
Cu3—Cu1—Cu4—O10 | 37.43 (4) | O6—C15—C16—C17 | 176.9 (2) |
O5—Cu1—Cu4—O4 | 52.36 (7) | O5—C15—C16—C17 | −2.6 (3) |
O9—Cu1—Cu4—O4 | 125.73 (10) | C21—C16—C17—C18 | 0.0 (4) |
O12—Cu1—Cu4—O4 | −132.07 (6) | C15—C16—C17—C18 | −179.9 (2) |
N4—Cu1—Cu4—O4 | −63.92 (9) | C16—C17—C18—C19 | −0.7 (4) |
O7—Cu1—Cu4—O4 | 150.73 (6) | C17—C18—C19—C20 | 1.4 (4) |
O11—Cu1—Cu4—O4 | −63.76 (7) | C17—C18—C19—Cl3 | −178.8 (2) |
Cu2—Cu1—Cu4—O4 | −167.01 (4) | C18—C19—C20—C21 | −1.2 (4) |
Cu3—Cu1—Cu4—O4 | −103.11 (5) | Cl3—C19—C20—C21 | 179.0 (2) |
O5—Cu1—Cu4—Cu3 | 155.47 (5) | C19—C20—C21—C16 | 0.4 (4) |
O9—Cu1—Cu4—Cu3 | −131.16 (10) | C17—C16—C21—C20 | 0.2 (4) |
O12—Cu1—Cu4—Cu3 | −28.96 (5) | C15—C16—C21—C20 | −179.9 (2) |
N4—Cu1—Cu4—Cu3 | 39.19 (8) | Cu1—O7—C22—O8 | 12.6 (4) |
O7—Cu1—Cu4—Cu3 | −106.16 (5) | Cu1—O7—C22—C23 | −167.39 (15) |
O11—Cu1—Cu4—Cu3 | 39.35 (6) | Cu2—O8—C22—O7 | −7.6 (4) |
Cu2—Cu1—Cu4—Cu3 | −63.90 (2) | Cu2—O8—C22—C23 | 172.40 (15) |
O5—Cu1—Cu4—Cu2 | −140.64 (6) | O7—C22—C23—C28 | −11.1 (4) |
O9—Cu1—Cu4—Cu2 | −67.27 (10) | O8—C22—C23—C28 | 168.9 (2) |
O12—Cu1—Cu4—Cu2 | 34.94 (5) | O7—C22—C23—C24 | 168.3 (2) |
N4—Cu1—Cu4—Cu2 | 103.09 (8) | O8—C22—C23—C24 | −11.7 (3) |
O7—Cu1—Cu4—Cu2 | −42.27 (5) | C28—C23—C24—C25 | 1.6 (4) |
O11—Cu1—Cu4—Cu2 | 103.25 (6) | C22—C23—C24—C25 | −177.9 (2) |
Cu3—Cu1—Cu4—Cu2 | 63.90 (2) | C23—C24—C25—C26 | −2.3 (4) |
O3—Cu4—N1—C33 | 0.2 (2) | C24—C25—C26—C27 | 1.8 (4) |
O11—Cu4—N1—C33 | 164.8 (3) | C24—C25—C26—Cl4 | −178.8 (2) |
O9—Cu4—N1—C33 | −173.7 (2) | C25—C26—C27—C28 | −0.5 (4) |
O10—Cu4—N1—C33 | −93.6 (2) | Cl4—C26—C27—C28 | −179.9 (2) |
O4—Cu4—N1—C33 | 52.8 (2) | C26—C27—C28—C23 | −0.3 (4) |
Cu3—Cu4—N1—C33 | −102.5 (2) | C24—C23—C28—C27 | −0.3 (4) |
Cu2—Cu4—N1—C33 | −126.33 (19) | C22—C23—C28—C27 | 179.2 (2) |
Cu1—Cu4—N1—C33 | 179.92 (18) | C33—N1—C29—C30 | 0.5 (3) |
O3—Cu4—N1—C29 | −179.20 (15) | Cu4—N1—C29—C30 | 179.89 (18) |
O11—Cu4—N1—C29 | −14.6 (5) | C33—N1—C29—C34 | −178.1 (2) |
O9—Cu4—N1—C29 | 6.89 (15) | Cu4—N1—C29—C34 | 1.3 (2) |
O10—Cu4—N1—C29 | 87.00 (16) | N1—C29—C30—C31 | 1.1 (4) |
O4—Cu4—N1—C29 | −126.55 (15) | C34—C29—C30—C31 | 179.6 (2) |
Cu3—Cu4—N1—C29 | 78.10 (19) | C29—C30—C31—C32 | −2.2 (4) |
Cu2—Cu4—N1—C29 | 54.30 (15) | C30—C31—C32—C33 | 1.7 (4) |
Cu1—Cu4—N1—C29 | 0.55 (17) | C29—N1—C33—C32 | −1.0 (4) |
O8—Cu2—N2—C35 | −169.97 (16) | Cu4—N1—C33—C32 | 179.70 (18) |
O10—Cu2—N2—C35 | 14.73 (15) | C31—C32—C33—N1 | −0.1 (4) |
O12—Cu2—N2—C35 | 35.2 (4) | Cu1—O9—C34—C29 | 171.94 (14) |
O9—Cu2—N2—C35 | 91.98 (16) | Cu4—O9—C34—C29 | 18.1 (2) |
O2—Cu2—N2—C35 | −64.48 (16) | Cu2—O9—C34—C29 | −89.53 (19) |
Cu3—Cu2—N2—C35 | 8.29 (18) | N1—C29—C34—O9 | −12.6 (3) |
Cu1—Cu2—N2—C35 | 100.94 (16) | C30—C29—C34—O9 | 168.9 (2) |
Cu4—Cu2—N2—C35 | 59.08 (15) | C39—N2—C35—C36 | −2.4 (3) |
O8—Cu2—N2—C39 | 14.2 (2) | Cu2—N2—C35—C36 | −178.61 (18) |
O10—Cu2—N2—C39 | −161.1 (2) | C39—N2—C35—C40 | 178.0 (2) |
O12—Cu2—N2—C39 | −140.5 (3) | Cu2—N2—C35—C40 | 1.8 (2) |
O9—Cu2—N2—C39 | −83.8 (2) | N2—C35—C36—C37 | 2.3 (4) |
O2—Cu2—N2—C39 | 119.7 (2) | C40—C35—C36—C37 | −178.2 (2) |
Cu3—Cu2—N2—C39 | −167.50 (18) | C35—C36—C37—C38 | −0.3 (4) |
Cu1—Cu2—N2—C39 | −74.9 (2) | C36—C37—C38—C39 | −1.4 (4) |
Cu4—Cu2—N2—C39 | −116.7 (2) | C35—N2—C39—C38 | 0.6 (4) |
O11—Cu3—N3—C41 | −3.42 (17) | Cu2—N2—C39—C38 | 176.25 (19) |
O1—Cu3—N3—C41 | 174.41 (17) | C37—C38—C39—N2 | 1.3 (4) |
O10—Cu3—N3—C41 | 3.1 (5) | Cu3—O10—C40—C35 | 164.39 (15) |
O12—Cu3—N3—C41 | −87.90 (17) | Cu2—O10—C40—C35 | 36.6 (2) |
Cu2—Cu3—N3—C41 | −85.99 (19) | Cu4—O10—C40—C35 | −78.1 (2) |
Cu4—Cu3—N3—C41 | −0.12 (19) | N2—C35—C40—O10 | −24.8 (3) |
Cu1—Cu3—N3—C41 | −57.51 (17) | C36—C35—C40—O10 | 155.6 (2) |
O11—Cu3—N3—C45 | 168.1 (2) | C45—N3—C41—C42 | 0.9 (4) |
O1—Cu3—N3—C45 | −14.0 (2) | Cu3—N3—C41—C42 | 173.16 (18) |
O10—Cu3—N3—C45 | 174.6 (3) | C45—N3—C41—C46 | −179.2 (2) |
O12—Cu3—N3—C45 | 83.7 (2) | Cu3—N3—C41—C46 | −6.9 (3) |
Cu2—Cu3—N3—C45 | 85.6 (2) | N3—C41—C42—C43 | −1.7 (4) |
Cu4—Cu3—N3—C45 | 171.44 (19) | C46—C41—C42—C43 | 178.4 (2) |
Cu1—Cu3—N3—C45 | 114.0 (2) | C41—C42—C43—C44 | 1.4 (4) |
O5—Cu1—N4—C47 | 153.00 (17) | C42—C43—C44—C45 | −0.4 (4) |
O9—Cu1—N4—C47 | −68.3 (4) | C41—N3—C45—C44 | 0.2 (4) |
O12—Cu1—N4—C47 | −18.59 (16) | Cu3—N3—C45—C44 | −170.9 (2) |
O7—Cu1—N4—C47 | 63.60 (17) | C43—C44—C45—N3 | −0.4 (4) |
O11—Cu1—N4—C47 | −86.89 (17) | Cu3—O11—C46—C41 | −20.5 (3) |
Cu2—Cu1—N4—C47 | −8.57 (19) | Cu4—O11—C46—C41 | −176.52 (15) |
Cu4—Cu1—N4—C47 | −86.79 (18) | Cu1—O11—C46—C41 | 81.64 (19) |
Cu3—Cu1—N4—C47 | −55.96 (16) | N3—C41—C46—O11 | 17.4 (3) |
O5—Cu1—N4—C51 | −24.9 (2) | C42—C41—C46—O11 | −162.6 (2) |
O9—Cu1—N4—C51 | 113.8 (3) | C51—N4—C47—C48 | 0.6 (4) |
O12—Cu1—N4—C51 | 163.5 (2) | Cu1—N4—C47—C48 | −177.45 (19) |
O7—Cu1—N4—C51 | −114.3 (2) | C51—N4—C47—C52 | −179.4 (2) |
O11—Cu1—N4—C51 | 95.2 (2) | Cu1—N4—C47—C52 | 2.6 (3) |
Cu2—Cu1—N4—C51 | 173.57 (19) | N4—C47—C48—C49 | −0.6 (4) |
Cu4—Cu1—N4—C51 | 95.3 (2) | C52—C47—C48—C49 | 179.4 (2) |
Cu3—Cu1—N4—C51 | 126.2 (2) | C47—C48—C49—C50 | −0.5 (4) |
O10—Cu3—O1—C1 | −43.6 (2) | C48—C49—C50—C51 | 1.5 (4) |
N3—Cu3—O1—C1 | 138.3 (2) | C47—N4—C51—C50 | 0.5 (4) |
O12—Cu3—O1—C1 | 35.9 (2) | Cu1—N4—C51—C50 | 178.21 (19) |
Cu2—Cu3—O1—C1 | −4.5 (2) | C49—C50—C51—N4 | −1.5 (4) |
Cu4—Cu3—O1—C1 | −50.7 (2) | Cu2—O12—C52—C47 | −159.90 (15) |
Cu1—Cu3—O1—C1 | 42.8 (2) | Cu1—O12—C52—C47 | −37.1 (2) |
O8—Cu2—O2—C1 | −145.54 (19) | Cu3—O12—C52—C47 | 89.48 (19) |
O10—Cu2—O2—C1 | 40.46 (19) | N4—C47—C52—O12 | 23.0 (3) |
O12—Cu2—O2—C1 | −48.38 (19) | C48—C47—C52—O12 | −157.0 (2) |
N2—Cu2—O2—C1 | 119.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C34—H34A···O5 | 0.99 | 2.59 | 3.116 (3) | 114 |
C39—H39···O8 | 0.95 | 2.55 | 3.034 (3) | 112 |
C46—H46A···O6 | 0.99 | 2.52 | 3.462 (3) | 158 |
C33—H33···O4i | 0.95 | 2.46 | 3.010 (3) | 117 |
C36—H36···O6ii | 0.95 | 2.41 | 3.221 (3) | 143 |
C37—H37···O4ii | 0.95 | 2.46 | 3.279 (3) | 145 |
C48—H48···O8iii | 0.95 | 2.53 | 3.401 (3) | 152 |
C30—H30···Cl3iv | 0.95 | 2.78 | 3.501 (3) | 134 |
C34—H34A···Cl2v | 0.99 | 2.75 | 3.337 (3) | 118 |
Symmetry codes: (i) −x+1/2, y, −z; (ii) x−1/2, −y, z; (iii) −x+1/2, −y+1/2, −z+1/2; (iv) x−1/2, −y+1, z; (v) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Cu4(C7H4ClO2)4(C6H6NO)4] |
Mr | 1308.84 |
Crystal system, space group | Monoclinic, I2/a |
Temperature (K) | 100 |
a, b, c (Å) | 20.326 (6), 14.184 (4), 36.696 (13) |
β (°) | 94.89 (3) |
V (Å3) | 10541 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.86 |
Crystal size (mm) | 0.45 × 0.35 × 0.25 |
Data collection | |
Diffractometer | Kuma KM-4 CCD area-detector diffractometer |
Absorption correction | Analytical CrysAlis RED (Agilent, 2011) |
Tmin, Tmax | 0.467, 0.659 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 36942, 12348, 8586 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.660 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.069, 1.02 |
No. of reflections | 12348 |
No. of parameters | 685 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.56, −0.37 |
Computer programs: CrysAlis CCD (Agilent, 2011), CrysAlis RED (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C34—H34A···O5 | 0.99 | 2.59 | 3.116 (3) | 114 |
C39—H39···O8 | 0.95 | 2.55 | 3.034 (3) | 112 |
C46—H46A···O6 | 0.99 | 2.52 | 3.462 (3) | 158 |
C33—H33···O4i | 0.95 | 2.46 | 3.010 (3) | 117 |
C36—H36···O6ii | 0.95 | 2.41 | 3.221 (3) | 143 |
C37—H37···O4ii | 0.95 | 2.46 | 3.279 (3) | 145 |
C48—H48···O8iii | 0.95 | 2.53 | 3.401 (3) | 152 |
C30—H30···Cl3iv | 0.95 | 2.78 | 3.501 (3) | 134 |
C34—H34A···Cl2v | 0.99 | 2.75 | 3.337 (3) | 118 |
Symmetry codes: (i) −x+1/2, y, −z; (ii) x−1/2, −y, z; (iii) −x+1/2, −y+1/2, −z+1/2; (iv) x−1/2, −y+1, z; (v) x, y+1, z. |
Much attention has been devoted in the past 20 years to the preparation and characterization of multinuclear metal complexes (Oshio & Ichida, 1995). These metal complexes have been prepared with the aim of providing new functional materials such as single-molecule magnets or catalysts (Sessoli et al., 1993). In these complexes, the bridging ligands may provide superexchange pathways between the metal centres. Several tetrameric transition metal complexes with µ3-bridging 2-pyridylmethanolate anions have been crystallographicaly studied. These complexes form cubane-like core structures (Clemente-Juan et al., 2000, 2002; Efthymiou et al., 2009; Escuer et al., 1999; Lecren et al., 2008; Wang et al., 2010; Yang et al., 2003, 2005, 2006; Zhang et al., 2010).
In this paper, we present an interesting structure, a tetrameric copper(II) complex, bis(µ-4-chlorobenzoato)(4-chlorobenzoato)(4-chlorobenzoato)tetrakis(µ3-2-pyridylmethanolato)tetracopper(II), (I). The full tetrameric molecule defining the asymmetric unit is shown in Fig. 1. The four Cu2+ cations and four µ3-bridging methanolate O atoms of the 2-pyridylmethanolate ligands form a deformed cubane-like Cu4O4 core (Fig. 2). The distances between pairs of Cu2+ cations are in the range 3.0266 (11)–3.5144 (13) Å. The Cu1···Cu2 and Cu2···Cu3 pairs are also connected by three atoms (O—C—O) of two bridging 4-chlorobenzoate ligands (Fig. 2). Each Cu2+ ion is coordinated in a different coordination environment.
The Cu1 cation lies in the centre of a 4+1+1 coordination polyhedron. The tetragonal plane is formed by one pyridine N and one methanolate O atom from a chelating 2-pyridylmethanolate anion [Cu1—N4 = 1.988 (2) Å and Cu1—O12 = 1.974 (2) Å], one carboxylate O atom from a monodentate 4-chlorobenzoate anion [Cu1—O5 = 1.915 (2) Å] and one methanolate O atom from a neighbouring bridging 2-pyridylmethanolate anion [Cu1—O9 = 1.945 (2) Å]. The axial positions of the coordination polyhedron are occupied by one carboxylate O atom from a bridging 4-chlorobenzoate anion [Cu1—O7 = 2.385 (2) Å] and one methanolate O atom from a second neighbouring bridging 2-pyridylmethanolate anion [Cu1—O11 = 2.873 (2) Å].
The coordination environment around Cu2 is of tetragonal–bipyramidal (4+2) geometry. The tetragonal plane is built up by one pyridine N and one methanolate O atom from a chelating 2-pyridylmethanolate anion [Cu2—N2 = 1.998 (2) Å and Cu2—O10 = 1.957 (2) Å], one carboxylate O atom from a bridging 4-chlorobenzoate anion [Cu2—O8 = 1.932 (2) Å] and one methanolate O atom from a neighbouring bridging 2-pyridylmethanolate anion [Cu2—O12 = 1.965 (2) Å]. The axial positions of the tetragonal bipyramid are occupied by one carboxylate O atom from a second bridging 4-chlorobenzoate anion [Cu2—O7 = 2.607 (2) Å] and one methanolate O atom from a second neighbouring bridging 2-pyridylmethanolate anion [Cu2—O9 = 2.545 (2) Å].
The Cu3 cation is coordinated in a tetragonal–pyramidal (4+1) geometry. The tetragonal plane is formed by one pyridine N and one methanolate O atom from a chelating 2-pyridylmethanolate anion [Cu3—N3 = 2.008 (2) Å and Cu3—O11 = 1.913 (2) Å], one carboxylate O atom from a bridging 4-chlorobenzoate anion [Cu3—O1 = 1.918 (2) Å] and one methanolate O atom from a neighbouring bridging 2-pyridylmethanolate anion [Cu3—O10 = 1.955 (2) Å]. The top of the tetragonal plane is occupied by one methanolate O atom from a second neighbouring bridging 2-pyridylmethanolate anion [Cu3—O12 = 2.303 (2) Å]. For this type of five-coordinate structure, the parameter τ [τ = (α - β)/60, where α and β are the equatorial angles] was introduced by Addison et al. (1984). The value of τ ranges from 0 for perfectly tetragonal–pyramidal geometry to 1 for perfectly trigonal–bipyramidal geometry. In this case, τ = 0.14, which favours the descriptions as a tetragonal–pyramidal geometry.
The coordination polyhedron around Cu4 has 4+1+1 geometry. The Cu4 cation is coordinated by one pyridine N and one methanolate O atom from a chelating 2-pyridylmethanolate anion [Cu4—N1 = 1.984 (2) Å and Cu4—O9 = 1.954 (2) Å], one carboxylate O atom from a chelating 4-chlorobenzoate anion [Cu4—O3 = 1.937 (2) Å] and one methanolate O atom from a neighbouring bridging 2-pyridylmethanolate anion [Cu4—O11 = 1.942 (2) Å] in the equatorial plane. The next two positions of the coordination polyhedron are occupied by one methanolate O atom from a neighbouring bridging 2-pyridylmethanolate anion [Cu4—O10 = 2.396 (2) Å] and one carboxylate O atom from a chelating 4-chlorobenzoate anion [Cu4—O4 = 2.937 (2) Å].
The packing in (I) is rather complex; the crystal structure does not contain medium–strong hydrogen bonds but the molecules are linked through weak C—H···O and C—H···Cl hydrogen-bonding interactions (Gilli & Gilli, 2009). The molecular structure is stabilized by three weak intramolecular C—H···O hydrogen bonds (entries 1–3 in Table 1). The complex molecules are in turn connected through weak intermolecular C—H···O hydrogen bonds (entries 4–7 in Table 1) and weak C—H···Cl hydrogen bonds (entries 8–9 in Table 1). These weak contacts are further reinforced by a C—H···π interaction (Suezawa et al. 2002), viz. C28—H28···Cg1vi [Cg1 is the centroid of the C2–C7 ring; symmetry code: (vi) -x + 1/2, -y + 1/2, -z + 1/2], with C28···Cg1 = 2.62 Å and a shortest H28···C4vi distance of 2.788 (3) Å.
This communication reports the second known example of a tetragonal cubane-like copper(II) complex with µ3-bridging 2-pyridylmethanolate anions, the first being that reported by Ang et al. (2004). However, while in this latter complex all four Cu2+ cations show the same type of coordination polyhedra, the title compound, as already described, does not. Examples of both types can be found among the reports in the literature dealing with cubane-like tetramers of different transition metals (nickel, iron and zinc) and µ3-bridging 2-pyridylmethanolate anions. Thus, in the two cubane-like tetrameric nickel(II) complexes reported by Zhang et al. (2010) and Efthymiou et al. (2009), all NiII cations have a similar coordination, with the metal centres being connected via four µ3-bridging 2-pyridylmethanolate anions. Different coordinations, on the other hand, can be found in the nickel(II) complex reported by Clemente-Juan et al. (2000) and the two iron(II) complexes reported by Clemente-Juan et al. (2002), where only one µ3-bridging 2-pyridylmethanolate anion connects three of the four metal centres; the remaining bridges linking the metal ions are provided by different ligands.
All the cases discussed so far correspond to cubane-like complexes without internal crystallographic symmetry, but there are, in addition, reported examples of tetrameric cubane-like metal complexes presenting a higher degree of symmetry in tetragonal space groups where only one-quarter of the molecule is independent, such as those presented by Wang et al. (2010), Yang et al. (2003, 2005, 2006) and Escuer et al. (1999).
Since the bridging ligands in cubane-like complexes may often provide superexchange pathways between metal centres, magnetic susceptibility measurements in (I) are underway.