metal-organic compounds
Tetrakis[μ3-2-(piperidin-1-yl)ethanolato]tetrakis[chloridocopper(II)]
aHefei University of Technology, Hefei, People's Republic of China
*Correspondence e-mail: luomei@pku.edu.cn
In the title tetranuclear compound, [Cu4(C7H14NO)4Cl4], each CuII cation is N,O-chelated by a piperidineethanolate anion and coordinated by a Cl− anion and two O atoms from neighboring piperidineethanolate anions in a distorted NO3Cl square-pyramidal geometry. The deprotonated hydroxyl groups of the piperidineethanolate anions bridge CuII cations, forming the tetranuclear complex. All piperidine rings display a chair conformation. In the crystal, there are no significant intermolecular interactions present. The crystal studied was an refined with a minor component of 0.18 (5).
CCDC reference: 998731
Related literature
For related metal complexes with piperidineethanolate as a chelating ligand, see: Yilmaz et al. (2010); Hamamci et al. (2008).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 998731
10.1107/S1600536814009052/xu5784sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814009052/xu5784Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814009052/xu5784Isup3.cdx
1-(2-Hydroxyethyl)piperidine (1.292 g, 10 mmol) was added to a methanol solution (50 ml) of CuCl2.2H2O (0.853 g, 5 mmol). The mixture was refluxed for 48 h. The filtrate was slowly evaporated, the blue single crystals were obtained after a day.
H atoms were placed in calculated positions with C—H = 0.97 Å, and refined in riding mode with Uiso(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The structure of the title compound with displacement ellipsoids drawn at the 50% probability level. |
[Cu4(C7H14NO)4Cl4] | Dx = 1.609 Mg m−3 |
Mr = 908.72 | Cu Kα radiation, λ = 1.54178 Å |
Tetragonal, P41212 | Cell parameters from 9940 reflections |
Hall symbol: P 4abw 2nw | θ = 3.9–68.8° |
a = 13.9016 (2) Å | µ = 5.47 mm−1 |
c = 38.8340 (9) Å | T = 293 K |
V = 7504.8 (3) Å3 | Prism, blue |
Z = 8 | 0.16 × 0.12 × 0.08 mm |
F(000) = 3744 |
Bruker APEXII CCD diffractometer | 6547 reflections with I > 2σ(I) |
ϕ and ω scans | Rint = 0.066 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 69.7°, θmin = 3.4° |
Tmin = 0.569, Tmax = 0.753 | h = −16→16 |
66705 measured reflections | k = −16→15 |
6976 independent reflections | l = −45→46 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.068 | H-atom parameters constrained |
wR(F2) = 0.182 | w = 1/[σ2(Fo2) + (0.0407P)2 + 55.9102P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max = 0.001 |
6976 reflections | Δρmax = 0.93 e Å−3 |
398 parameters | Δρmin = −0.81 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 2913 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.18 (5) |
[Cu4(C7H14NO)4Cl4] | Z = 8 |
Mr = 908.72 | Cu Kα radiation |
Tetragonal, P41212 | µ = 5.47 mm−1 |
a = 13.9016 (2) Å | T = 293 K |
c = 38.8340 (9) Å | 0.16 × 0.12 × 0.08 mm |
V = 7504.8 (3) Å3 |
Bruker APEXII CCD diffractometer | 6976 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 6547 reflections with I > 2σ(I) |
Tmin = 0.569, Tmax = 0.753 | Rint = 0.066 |
66705 measured reflections |
R[F2 > 2σ(F2)] = 0.068 | H-atom parameters constrained |
wR(F2) = 0.182 | w = 1/[σ2(Fo2) + (0.0407P)2 + 55.9102P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | Δρmax = 0.93 e Å−3 |
6976 reflections | Δρmin = −0.81 e Å−3 |
398 parameters | Absolute structure: Flack (1983), 2913 Friedel pairs |
0 restraints | Absolute structure parameter: 0.18 (5) |
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. |
Refinement. Refined as a 2-component inversion twin. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.03847 (9) | 0.68690 (8) | −0.03396 (3) | 0.0359 (3) | |
Cu2 | 0.19814 (9) | 0.54936 (8) | −0.03808 (3) | 0.0352 (3) | |
Cu3 | 0.19184 (8) | 0.68392 (9) | 0.03586 (3) | 0.0336 (3) | |
Cu4 | 0.05180 (8) | 0.52599 (8) | 0.03383 (4) | 0.0366 (3) | |
Cl1 | 0.02892 (19) | 0.84482 (16) | −0.04415 (7) | 0.0529 (6) | |
Cl2 | 0.20776 (19) | 0.39762 (16) | −0.05687 (8) | 0.0545 (6) | |
Cl3 | 0.34843 (16) | 0.68975 (19) | 0.04958 (7) | 0.0502 (6) | |
Cl4 | −0.10283 (18) | 0.5147 (2) | 0.04883 (9) | 0.0632 (8) | |
N1 | 0.3352 (5) | 0.5899 (5) | −0.05397 (18) | 0.0368 (16) | |
N2 | −0.0955 (6) | 0.6526 (5) | −0.0528 (2) | 0.0417 (18) | |
N3 | 0.1545 (5) | 0.8161 (5) | 0.05649 (18) | 0.0341 (15) | |
N4 | 0.0914 (5) | 0.3890 (5) | 0.04787 (19) | 0.0361 (16) | |
O1 | 0.1787 (4) | 0.6858 (4) | −0.02744 (15) | 0.0325 (12) | |
O2 | 0.0590 (4) | 0.5475 (4) | −0.02994 (15) | 0.0370 (13) | |
O3 | 0.0527 (4) | 0.6684 (4) | 0.02958 (17) | 0.0394 (14) | |
O4 | 0.1893 (4) | 0.5442 (4) | 0.02558 (15) | 0.0346 (12) | |
C1 | 0.2455 (6) | 0.7412 (6) | −0.0465 (2) | 0.040 (2) | |
H1A | 0.2478 | 0.8062 | −0.0374 | 0.048* | |
H1B | 0.2257 | 0.7445 | −0.0704 | 0.048* | |
C2 | 0.3414 (6) | 0.6967 (6) | −0.0440 (2) | 0.0364 (19) | |
H2A | 0.3656 | 0.7027 | −0.0207 | 0.044* | |
H2B | 0.3857 | 0.7296 | −0.0593 | 0.044* | |
C3 | 0.3439 (7) | 0.5788 (7) | −0.0916 (2) | 0.042 (2) | |
H3A | 0.2995 | 0.6228 | −0.1027 | 0.050* | |
H3B | 0.3252 | 0.5139 | −0.0979 | 0.050* | |
C4 | 0.4451 (8) | 0.5979 (8) | −0.1053 (3) | 0.051 (2) | |
H4A | 0.4479 | 0.5813 | −0.1295 | 0.062* | |
H4B | 0.4597 | 0.6659 | −0.1031 | 0.062* | |
C5 | 0.5196 (7) | 0.5397 (8) | −0.0857 (2) | 0.050 (2) | |
H5A | 0.5836 | 0.5577 | −0.0932 | 0.060* | |
H5B | 0.5106 | 0.4718 | −0.0904 | 0.060* | |
C6 | 0.5095 (5) | 0.5583 (8) | −0.0469 (2) | 0.043 (2) | |
H6A | 0.5560 | 0.5198 | −0.0344 | 0.051* | |
H6B | 0.5221 | 0.6255 | −0.0420 | 0.051* | |
C7 | 0.4089 (6) | 0.5323 (7) | −0.0357 (2) | 0.040 (2) | |
H7A | 0.3977 | 0.4646 | −0.0401 | 0.048* | |
H7B | 0.4028 | 0.5430 | −0.0111 | 0.048* | |
C8 | −0.0104 (7) | 0.4958 (6) | −0.0498 (3) | 0.046 (2) | |
H8A | −0.0158 | 0.4302 | −0.0415 | 0.055* | |
H8B | 0.0084 | 0.4944 | −0.0738 | 0.055* | |
C9 | −0.1069 (6) | 0.5489 (6) | −0.0455 (3) | 0.041 (2) | |
H9A | −0.1540 | 0.5217 | −0.0612 | 0.050* | |
H9B | −0.1304 | 0.5404 | −0.0222 | 0.050* | |
C10 | −0.1754 (6) | 0.7091 (7) | −0.0363 (3) | 0.044 (2) | |
H10A | −0.1600 | 0.7771 | −0.0376 | 0.053* | |
H10B | −0.1791 | 0.6918 | −0.0121 | 0.053* | |
C11 | −0.2722 (7) | 0.6925 (9) | −0.0527 (4) | 0.072 (4) | |
H11A | −0.3205 | 0.7310 | −0.0411 | 0.087* | |
H11B | −0.2900 | 0.6253 | −0.0504 | 0.087* | |
C12 | −0.2676 (9) | 0.7200 (9) | −0.0907 (4) | 0.074 (4) | |
H12A | −0.3292 | 0.7074 | −0.1016 | 0.089* | |
H12B | −0.2537 | 0.7881 | −0.0930 | 0.089* | |
C13 | −0.1893 (10) | 0.6614 (9) | −0.1083 (3) | 0.068 (3) | |
H13A | −0.1835 | 0.6819 | −0.1321 | 0.082* | |
H13B | −0.2074 | 0.5940 | −0.1082 | 0.082* | |
C14 | −0.0920 (7) | 0.6728 (7) | −0.0904 (2) | 0.047 (2) | |
H14A | −0.0461 | 0.6296 | −0.1011 | 0.056* | |
H14B | −0.0692 | 0.7380 | −0.0939 | 0.056* | |
C15 | 0.0002 (7) | 0.7326 (6) | 0.0510 (3) | 0.048 (2) | |
H15A | −0.0012 | 0.7091 | 0.0745 | 0.058* | |
H15B | −0.0654 | 0.7390 | 0.0428 | 0.058* | |
C16 | 0.0504 (7) | 0.8256 (7) | 0.0492 (3) | 0.048 (2) | |
H16A | 0.0220 | 0.8695 | 0.0657 | 0.057* | |
H16B | 0.0419 | 0.8530 | 0.0264 | 0.057* | |
C17 | 0.2152 (7) | 0.8908 (6) | 0.0417 (2) | 0.040 (2) | |
H17A | 0.2016 | 0.8962 | 0.0172 | 0.047* | |
H17B | 0.2822 | 0.8726 | 0.0442 | 0.047* | |
C18 | 0.1989 (8) | 0.9886 (7) | 0.0588 (3) | 0.055 (3) | |
H18A | 0.2402 | 1.0364 | 0.0482 | 0.066* | |
H18B | 0.1326 | 1.0085 | 0.0555 | 0.066* | |
C19 | 0.2207 (8) | 0.9825 (8) | 0.0970 (3) | 0.058 (3) | |
H19A | 0.2888 | 0.9703 | 0.1004 | 0.069* | |
H19B | 0.2048 | 1.0430 | 0.1080 | 0.069* | |
C20 | 0.1625 (8) | 0.9022 (7) | 0.1127 (3) | 0.050 (2) | |
H20A | 0.1810 | 0.8947 | 0.1367 | 0.060* | |
H20B | 0.0949 | 0.9196 | 0.1122 | 0.060* | |
C21 | 0.1757 (7) | 0.8089 (7) | 0.0946 (2) | 0.041 (2) | |
H21A | 0.1336 | 0.7612 | 0.1048 | 0.050* | |
H21B | 0.2415 | 0.7873 | 0.0977 | 0.050* | |
C22 | 0.2464 (7) | 0.4756 (7) | 0.0441 (3) | 0.048 (2) | |
H22A | 0.2485 | 0.4913 | 0.0684 | 0.057* | |
H22B | 0.3115 | 0.4738 | 0.0352 | 0.057* | |
C23 | 0.1969 (6) | 0.3820 (7) | 0.0384 (3) | 0.043 (2) | |
H23A | 0.2274 | 0.3326 | 0.0522 | 0.052* | |
H23B | 0.2028 | 0.3637 | 0.0143 | 0.052* | |
C24 | 0.0357 (8) | 0.3141 (7) | 0.0299 (3) | 0.051 (2) | |
H24A | 0.0519 | 0.3168 | 0.0056 | 0.061* | |
H24B | −0.0320 | 0.3298 | 0.0320 | 0.061* | |
C25 | 0.0498 (10) | 0.2113 (9) | 0.0421 (3) | 0.068 (3) | |
H25A | 0.0042 | 0.1698 | 0.0304 | 0.082* | |
H25B | 0.1141 | 0.1901 | 0.0360 | 0.082* | |
C26 | 0.0364 (8) | 0.2022 (7) | 0.0800 (3) | 0.055 (3) | |
H26A | 0.0553 | 0.1381 | 0.0872 | 0.066* | |
H26B | −0.0310 | 0.2108 | 0.0856 | 0.066* | |
C27 | 0.0955 (9) | 0.2757 (8) | 0.0991 (3) | 0.054 (3) | |
H27A | 0.1632 | 0.2599 | 0.0967 | 0.065* | |
H27B | 0.0795 | 0.2731 | 0.1234 | 0.065* | |
C28 | 0.0785 (7) | 0.3783 (7) | 0.0857 (2) | 0.044 (2) | |
H28A | 0.0137 | 0.3978 | 0.0917 | 0.053* | |
H28B | 0.1227 | 0.4216 | 0.0973 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0306 (6) | 0.0252 (6) | 0.0519 (7) | 0.0000 (5) | −0.0094 (6) | 0.0002 (6) |
Cu2 | 0.0311 (6) | 0.0219 (6) | 0.0527 (7) | 0.0011 (5) | −0.0025 (6) | −0.0030 (5) |
Cu3 | 0.0254 (6) | 0.0291 (6) | 0.0463 (7) | 0.0015 (5) | −0.0030 (5) | −0.0041 (5) |
Cu4 | 0.0252 (6) | 0.0267 (6) | 0.0578 (8) | −0.0005 (5) | −0.0042 (6) | 0.0029 (6) |
Cl1 | 0.0513 (14) | 0.0268 (10) | 0.0807 (17) | 0.0015 (9) | −0.0163 (12) | 0.0049 (11) |
Cl2 | 0.0510 (14) | 0.0273 (11) | 0.0854 (18) | −0.0012 (10) | 0.0042 (12) | −0.0133 (11) |
Cl3 | 0.0267 (10) | 0.0533 (14) | 0.0706 (15) | 0.0043 (10) | −0.0088 (10) | −0.0159 (12) |
Cl4 | 0.0335 (12) | 0.0500 (14) | 0.106 (2) | −0.0035 (10) | 0.0059 (13) | 0.0126 (14) |
N1 | 0.038 (4) | 0.036 (4) | 0.036 (4) | −0.010 (3) | −0.003 (3) | −0.001 (3) |
N2 | 0.043 (4) | 0.027 (4) | 0.055 (4) | −0.007 (3) | −0.018 (4) | 0.002 (3) |
N3 | 0.043 (4) | 0.021 (3) | 0.038 (4) | 0.000 (3) | −0.002 (3) | −0.004 (3) |
N4 | 0.026 (4) | 0.034 (4) | 0.048 (4) | −0.008 (3) | −0.001 (3) | 0.002 (3) |
O1 | 0.025 (3) | 0.025 (3) | 0.047 (3) | 0.008 (2) | −0.003 (2) | 0.001 (2) |
O2 | 0.031 (3) | 0.026 (3) | 0.054 (3) | 0.010 (2) | −0.011 (3) | −0.008 (3) |
O3 | 0.025 (3) | 0.026 (3) | 0.067 (4) | 0.009 (2) | 0.002 (3) | −0.005 (3) |
O4 | 0.028 (3) | 0.026 (3) | 0.050 (3) | 0.008 (2) | −0.005 (2) | 0.005 (2) |
C1 | 0.034 (5) | 0.027 (4) | 0.058 (5) | −0.004 (3) | 0.022 (4) | 0.003 (4) |
C2 | 0.026 (4) | 0.039 (5) | 0.044 (5) | −0.006 (4) | 0.002 (3) | −0.011 (4) |
C3 | 0.038 (5) | 0.039 (5) | 0.049 (5) | 0.006 (4) | −0.002 (4) | −0.002 (4) |
C4 | 0.058 (6) | 0.050 (6) | 0.046 (5) | 0.000 (5) | 0.008 (5) | 0.005 (4) |
C5 | 0.042 (5) | 0.057 (6) | 0.052 (6) | 0.011 (5) | 0.005 (4) | −0.008 (5) |
C6 | 0.010 (4) | 0.053 (6) | 0.064 (6) | 0.005 (3) | 0.001 (4) | 0.013 (5) |
C7 | 0.024 (4) | 0.049 (5) | 0.048 (5) | −0.009 (4) | 0.004 (4) | 0.005 (4) |
C8 | 0.043 (5) | 0.023 (4) | 0.071 (6) | −0.004 (4) | −0.022 (5) | −0.002 (4) |
C9 | 0.027 (4) | 0.028 (4) | 0.068 (6) | 0.006 (3) | −0.021 (4) | 0.005 (4) |
C10 | 0.021 (4) | 0.039 (5) | 0.072 (6) | 0.003 (3) | 0.001 (4) | −0.008 (5) |
C11 | 0.032 (5) | 0.063 (7) | 0.121 (11) | 0.027 (5) | −0.018 (6) | −0.035 (7) |
C12 | 0.058 (7) | 0.049 (6) | 0.115 (11) | 0.015 (5) | −0.044 (7) | 0.003 (7) |
C13 | 0.083 (9) | 0.053 (7) | 0.068 (7) | −0.001 (6) | −0.037 (7) | 0.004 (5) |
C14 | 0.053 (6) | 0.038 (5) | 0.050 (5) | −0.005 (4) | −0.008 (4) | 0.002 (4) |
C15 | 0.038 (5) | 0.026 (4) | 0.080 (7) | 0.003 (4) | −0.002 (5) | −0.012 (5) |
C16 | 0.047 (5) | 0.034 (5) | 0.062 (6) | 0.023 (4) | −0.010 (5) | −0.020 (4) |
C17 | 0.052 (6) | 0.029 (4) | 0.038 (5) | 0.005 (4) | 0.012 (4) | −0.002 (4) |
C18 | 0.049 (6) | 0.034 (5) | 0.083 (7) | −0.010 (4) | 0.003 (5) | 0.005 (5) |
C19 | 0.060 (6) | 0.048 (6) | 0.065 (6) | −0.005 (5) | −0.005 (5) | −0.022 (5) |
C20 | 0.057 (6) | 0.047 (6) | 0.046 (5) | −0.008 (5) | −0.004 (5) | −0.016 (4) |
C21 | 0.046 (5) | 0.041 (5) | 0.037 (4) | −0.008 (4) | 0.000 (4) | −0.001 (4) |
C22 | 0.030 (5) | 0.040 (5) | 0.073 (7) | 0.013 (4) | −0.012 (4) | 0.010 (5) |
C23 | 0.021 (4) | 0.048 (5) | 0.060 (6) | 0.018 (4) | 0.007 (4) | 0.007 (4) |
C24 | 0.055 (6) | 0.046 (5) | 0.051 (5) | −0.011 (5) | −0.004 (5) | 0.004 (5) |
C25 | 0.065 (8) | 0.069 (8) | 0.070 (7) | 0.034 (6) | 0.013 (6) | 0.001 (6) |
C26 | 0.048 (6) | 0.043 (6) | 0.073 (7) | 0.009 (5) | 0.004 (5) | 0.016 (5) |
C27 | 0.071 (7) | 0.044 (6) | 0.048 (6) | 0.006 (5) | −0.004 (5) | 0.013 (4) |
C28 | 0.048 (5) | 0.038 (5) | 0.046 (5) | −0.001 (4) | −0.009 (4) | −0.009 (4) |
Cu1—O2 | 1.965 (6) | C8—H8B | 0.9700 |
Cu1—O1 | 1.965 (5) | C9—H9A | 0.9700 |
Cu1—N2 | 2.058 (7) | C9—H9B | 0.9700 |
Cu1—Cl1 | 2.235 (2) | C10—C11 | 1.507 (13) |
Cu1—Cu2 | 2.9341 (17) | C10—H10A | 0.9700 |
Cu2—O2 | 1.960 (6) | C10—H10B | 0.9700 |
Cu2—O1 | 1.960 (5) | C11—C12 | 1.529 (19) |
Cu2—N1 | 2.081 (7) | C11—H11A | 0.9700 |
Cu2—Cl2 | 2.236 (2) | C11—H11B | 0.9700 |
Cu3—O3 | 1.961 (6) | C12—C13 | 1.522 (18) |
Cu3—O4 | 1.983 (6) | C12—H12A | 0.9700 |
Cu3—N3 | 2.070 (7) | C12—H12B | 0.9700 |
Cu3—Cl3 | 2.242 (2) | C13—C14 | 1.528 (15) |
Cu3—Cu4 | 2.9354 (17) | C13—H13A | 0.9700 |
Cu4—O4 | 1.954 (6) | C13—H13B | 0.9700 |
Cu4—O3 | 1.986 (6) | C14—H14A | 0.9700 |
Cu4—N4 | 2.057 (7) | C14—H14B | 0.9700 |
Cu4—Cl4 | 2.233 (3) | C15—C16 | 1.472 (13) |
N1—C3 | 1.476 (11) | C15—H15A | 0.9700 |
N1—C7 | 1.482 (12) | C15—H15B | 0.9700 |
N1—C2 | 1.536 (11) | C16—H16A | 0.9700 |
N2—C9 | 1.478 (11) | C16—H16B | 0.9700 |
N2—C14 | 1.488 (12) | C17—C18 | 1.532 (13) |
N2—C10 | 1.505 (12) | C17—H17A | 0.9700 |
N3—C17 | 1.457 (11) | C17—H17B | 0.9700 |
N3—C16 | 1.480 (12) | C18—C19 | 1.514 (15) |
N3—C21 | 1.512 (11) | C18—H18A | 0.9700 |
N4—C24 | 1.474 (12) | C18—H18B | 0.9700 |
N4—C28 | 1.488 (12) | C19—C20 | 1.508 (15) |
N4—C23 | 1.515 (10) | C19—H19A | 0.9700 |
O1—C1 | 1.416 (9) | C19—H19B | 0.9700 |
O2—C8 | 1.429 (10) | C20—C21 | 1.488 (13) |
O3—C15 | 1.421 (11) | C20—H20A | 0.9700 |
O4—C22 | 1.434 (10) | C20—H20B | 0.9700 |
C1—C2 | 1.473 (12) | C21—H21A | 0.9700 |
C1—H1A | 0.9700 | C21—H21B | 0.9700 |
C1—H1B | 0.9700 | C22—C23 | 1.489 (14) |
C2—H2A | 0.9700 | C22—H22A | 0.9700 |
C2—H2B | 0.9700 | C22—H22B | 0.9700 |
C3—C4 | 1.526 (14) | C23—H23A | 0.9700 |
C3—H3A | 0.9700 | C23—H23B | 0.9700 |
C3—H3B | 0.9700 | C24—C25 | 1.518 (15) |
C4—C5 | 1.519 (14) | C24—H24A | 0.9700 |
C4—H4A | 0.9700 | C24—H24B | 0.9700 |
C4—H4B | 0.9700 | C25—C26 | 1.488 (15) |
C5—C6 | 1.533 (13) | C25—H25A | 0.9700 |
C5—H5A | 0.9700 | C25—H25B | 0.9700 |
C5—H5B | 0.9700 | C26—C27 | 1.508 (15) |
C6—C7 | 1.510 (11) | C26—H26A | 0.9700 |
C6—H6A | 0.9700 | C26—H26B | 0.9700 |
C6—H6B | 0.9700 | C27—C28 | 1.536 (13) |
C7—H7A | 0.9700 | C27—H27A | 0.9700 |
C7—H7B | 0.9700 | C27—H27B | 0.9700 |
C8—C9 | 1.540 (12) | C28—H28A | 0.9700 |
C8—H8A | 0.9700 | C28—H28B | 0.9700 |
O2—Cu1—O1 | 80.7 (2) | C9—C8—H8B | 110.4 |
O2—Cu1—N2 | 86.1 (3) | H8A—C8—H8B | 108.6 |
O1—Cu1—N2 | 160.3 (3) | N2—C9—C8 | 110.7 (7) |
O2—Cu1—Cl1 | 172.5 (2) | N2—C9—H9A | 109.5 |
O1—Cu1—Cl1 | 95.13 (18) | C8—C9—H9A | 109.5 |
N2—Cu1—Cl1 | 96.4 (2) | N2—C9—H9B | 109.5 |
O2—Cu1—Cu2 | 41.55 (17) | C8—C9—H9B | 109.5 |
O1—Cu1—Cu2 | 41.56 (16) | H9A—C9—H9B | 108.1 |
N2—Cu1—Cu2 | 121.0 (2) | N2—C10—C11 | 113.4 (8) |
Cl1—Cu1—Cu2 | 132.50 (9) | N2—C10—H10A | 108.9 |
O2—Cu2—O1 | 80.9 (2) | C11—C10—H10A | 108.9 |
O2—Cu2—N1 | 162.8 (3) | N2—C10—H10B | 108.9 |
O1—Cu2—N1 | 85.8 (3) | C11—C10—H10B | 108.9 |
O2—Cu2—Cl2 | 95.71 (18) | H10A—C10—H10B | 107.7 |
O1—Cu2—Cl2 | 171.88 (19) | C10—C11—C12 | 109.5 (11) |
N1—Cu2—Cl2 | 96.0 (2) | C10—C11—H11A | 109.8 |
O2—Cu2—Cu1 | 41.67 (16) | C12—C11—H11A | 109.8 |
O1—Cu2—Cu1 | 41.69 (16) | C10—C11—H11B | 109.8 |
N1—Cu2—Cu1 | 122.2 (2) | C12—C11—H11B | 109.8 |
Cl2—Cu2—Cu1 | 132.67 (9) | H11A—C11—H11B | 108.2 |
O3—Cu3—O4 | 81.3 (2) | C13—C12—C11 | 109.2 (9) |
O3—Cu3—N3 | 84.2 (3) | C13—C12—H12A | 109.8 |
O4—Cu3—N3 | 160.5 (3) | C11—C12—H12A | 109.8 |
O3—Cu3—Cl3 | 172.2 (2) | C13—C12—H12B | 109.8 |
O4—Cu3—Cl3 | 95.78 (18) | C11—C12—H12B | 109.8 |
N3—Cu3—Cl3 | 96.9 (2) | H12A—C12—H12B | 108.3 |
O3—Cu3—Cu4 | 42.29 (16) | C12—C13—C14 | 112.0 (9) |
O4—Cu3—Cu4 | 41.42 (17) | C12—C13—H13A | 109.2 |
N3—Cu3—Cu4 | 120.5 (2) | C14—C13—H13A | 109.2 |
Cl3—Cu3—Cu4 | 132.62 (9) | C12—C13—H13B | 109.2 |
O4—Cu4—O3 | 81.4 (2) | C14—C13—H13B | 109.2 |
O4—Cu4—N4 | 84.4 (2) | H13A—C13—H13B | 107.9 |
O3—Cu4—N4 | 160.6 (3) | N2—C14—C13 | 113.4 (9) |
O4—Cu4—Cl4 | 173.4 (2) | N2—C14—H14A | 108.9 |
O3—Cu4—Cl4 | 95.61 (18) | C13—C14—H14A | 108.9 |
N4—Cu4—Cl4 | 97.1 (2) | N2—C14—H14B | 108.9 |
O4—Cu4—Cu3 | 42.17 (16) | C13—C14—H14B | 108.9 |
O3—Cu4—Cu3 | 41.63 (16) | H14A—C14—H14B | 107.7 |
N4—Cu4—Cu3 | 120.5 (2) | O3—C15—C16 | 106.3 (8) |
Cl4—Cu4—Cu3 | 133.15 (9) | O3—C15—H15A | 110.5 |
C3—N1—C7 | 111.3 (7) | C16—C15—H15A | 110.5 |
C3—N1—C2 | 110.2 (7) | O3—C15—H15B | 110.5 |
C7—N1—C2 | 111.3 (7) | C16—C15—H15B | 110.5 |
C3—N1—Cu2 | 109.9 (5) | H15A—C15—H15B | 108.7 |
C7—N1—Cu2 | 110.1 (5) | C15—C16—N3 | 112.1 (7) |
C2—N1—Cu2 | 103.8 (5) | C15—C16—H16A | 109.2 |
C9—N2—C14 | 112.1 (7) | N3—C16—H16A | 109.2 |
C9—N2—C10 | 110.3 (7) | C15—C16—H16B | 109.2 |
C14—N2—C10 | 110.2 (7) | N3—C16—H16B | 109.2 |
C9—N2—Cu1 | 104.8 (5) | H16A—C16—H16B | 107.9 |
C14—N2—Cu1 | 106.1 (6) | N3—C17—C18 | 112.0 (7) |
C10—N2—Cu1 | 113.2 (5) | N3—C17—H17A | 109.2 |
C17—N3—C16 | 115.2 (7) | C18—C17—H17A | 109.2 |
C17—N3—C21 | 108.7 (7) | N3—C17—H17B | 109.2 |
C16—N3—C21 | 112.6 (7) | C18—C17—H17B | 109.2 |
C17—N3—Cu3 | 109.6 (5) | H17A—C17—H17B | 107.9 |
C16—N3—Cu3 | 104.5 (5) | C19—C18—C17 | 110.3 (9) |
C21—N3—Cu3 | 105.7 (5) | C19—C18—H18A | 109.6 |
C24—N4—C28 | 109.5 (7) | C17—C18—H18A | 109.6 |
C24—N4—C23 | 110.4 (8) | C19—C18—H18B | 109.6 |
C28—N4—C23 | 110.6 (7) | C17—C18—H18B | 109.6 |
C24—N4—Cu4 | 112.8 (6) | H18A—C18—H18B | 108.1 |
C28—N4—Cu4 | 108.8 (5) | C20—C19—C18 | 109.3 (8) |
C23—N4—Cu4 | 104.7 (5) | C20—C19—H19A | 109.8 |
C1—O1—Cu2 | 109.0 (5) | C18—C19—H19A | 109.8 |
C1—O1—Cu1 | 125.4 (5) | C20—C19—H19B | 109.8 |
Cu2—O1—Cu1 | 96.7 (2) | C18—C19—H19B | 109.8 |
C8—O2—Cu2 | 125.9 (6) | H19A—C19—H19B | 108.3 |
C8—O2—Cu1 | 110.8 (5) | C21—C20—C19 | 112.7 (9) |
Cu2—O2—Cu1 | 96.8 (3) | C21—C20—H20A | 109.1 |
C15—O3—Cu3 | 111.4 (5) | C19—C20—H20A | 109.1 |
C15—O3—Cu4 | 125.0 (6) | C21—C20—H20B | 109.1 |
Cu3—O3—Cu4 | 96.1 (2) | C19—C20—H20B | 109.1 |
C22—O4—Cu4 | 111.9 (5) | H20A—C20—H20B | 107.8 |
C22—O4—Cu3 | 122.7 (6) | C20—C21—N3 | 112.5 (8) |
Cu4—O4—Cu3 | 96.4 (2) | C20—C21—H21A | 109.1 |
O1—C1—C2 | 109.4 (7) | N3—C21—H21A | 109.1 |
O1—C1—H1A | 109.8 | C20—C21—H21B | 109.1 |
C2—C1—H1A | 109.8 | N3—C21—H21B | 109.1 |
O1—C1—H1B | 109.8 | H21A—C21—H21B | 107.8 |
C2—C1—H1B | 109.8 | O4—C22—C23 | 104.5 (7) |
H1A—C1—H1B | 108.2 | O4—C22—H22A | 110.8 |
C1—C2—N1 | 109.8 (7) | C23—C22—H22A | 110.8 |
C1—C2—H2A | 109.7 | O4—C22—H22B | 110.8 |
N1—C2—H2A | 109.7 | C23—C22—H22B | 110.8 |
C1—C2—H2B | 109.7 | H22A—C22—H22B | 108.9 |
N1—C2—H2B | 109.7 | C22—C23—N4 | 110.8 (7) |
H2A—C2—H2B | 108.2 | C22—C23—H23A | 109.5 |
N1—C3—C4 | 113.6 (8) | N4—C23—H23A | 109.5 |
N1—C3—H3A | 108.8 | C22—C23—H23B | 109.5 |
C4—C3—H3A | 108.8 | N4—C23—H23B | 109.5 |
N1—C3—H3B | 108.8 | H23A—C23—H23B | 108.1 |
C4—C3—H3B | 108.8 | N4—C24—C25 | 116.7 (9) |
H3A—C3—H3B | 107.7 | N4—C24—H24A | 108.1 |
C5—C4—C3 | 111.2 (8) | C25—C24—H24A | 108.1 |
C5—C4—H4A | 109.4 | N4—C24—H24B | 108.1 |
C3—C4—H4A | 109.4 | C25—C24—H24B | 108.1 |
C5—C4—H4B | 109.4 | H24A—C24—H24B | 107.3 |
C3—C4—H4B | 109.4 | C26—C25—C24 | 111.9 (9) |
H4A—C4—H4B | 108.0 | C26—C25—H25A | 109.2 |
C4—C5—C6 | 109.9 (8) | C24—C25—H25A | 109.2 |
C4—C5—H5A | 109.7 | C26—C25—H25B | 109.2 |
C6—C5—H5A | 109.7 | C24—C25—H25B | 109.2 |
C4—C5—H5B | 109.7 | H25A—C25—H25B | 107.9 |
C6—C5—H5B | 109.7 | C25—C26—C27 | 111.1 (10) |
H5A—C5—H5B | 108.2 | C25—C26—H26A | 109.4 |
C7—C6—C5 | 109.2 (8) | C27—C26—H26A | 109.4 |
C7—C6—H6A | 109.8 | C25—C26—H26B | 109.4 |
C5—C6—H6A | 109.8 | C27—C26—H26B | 109.4 |
C7—C6—H6B | 109.8 | H26A—C26—H26B | 108.0 |
C5—C6—H6B | 109.8 | C26—C27—C28 | 112.3 (8) |
H6A—C6—H6B | 108.3 | C26—C27—H27A | 109.1 |
N1—C7—C6 | 111.9 (7) | C28—C27—H27A | 109.1 |
N1—C7—H7A | 109.2 | C26—C27—H27B | 109.1 |
C6—C7—H7A | 109.2 | C28—C27—H27B | 109.1 |
N1—C7—H7B | 109.2 | H27A—C27—H27B | 107.9 |
C6—C7—H7B | 109.2 | N4—C28—C27 | 114.0 (8) |
H7A—C7—H7B | 107.9 | N4—C28—H28A | 108.7 |
O2—C8—C9 | 106.9 (7) | C27—C28—H28A | 108.7 |
O2—C8—H8A | 110.4 | N4—C28—H28B | 108.7 |
C9—C8—H8A | 110.4 | C27—C28—H28B | 108.7 |
O2—C8—H8B | 110.4 | H28A—C28—H28B | 107.6 |
O1—Cu1—Cu2—O2 | 154.7 (4) | N2—Cu1—O2—C8 | 16.2 (6) |
N2—Cu1—Cu2—O2 | −37.2 (4) | Cl1—Cu1—O2—C8 | −93.1 (16) |
Cl1—Cu1—Cu2—O2 | −173.6 (3) | Cu2—Cu1—O2—C8 | −132.6 (7) |
O2—Cu1—Cu2—O1 | −154.7 (4) | O1—Cu1—O2—Cu2 | −16.7 (2) |
N2—Cu1—Cu2—O1 | 168.2 (4) | N2—Cu1—O2—Cu2 | 148.7 (3) |
Cl1—Cu1—Cu2—O1 | 31.7 (3) | Cl1—Cu1—O2—Cu2 | 39.4 (16) |
O2—Cu1—Cu2—N1 | 172.0 (3) | O4—Cu3—O3—C15 | 147.7 (6) |
O1—Cu1—Cu2—N1 | −33.3 (3) | N3—Cu3—O3—C15 | −19.1 (6) |
N2—Cu1—Cu2—N1 | 134.9 (4) | Cl3—Cu3—O3—C15 | 79.0 (15) |
Cl1—Cu1—Cu2—N1 | −1.5 (3) | Cu4—Cu3—O3—C15 | 131.4 (7) |
O2—Cu1—Cu2—Cl2 | 33.7 (3) | O4—Cu3—O3—Cu4 | 16.3 (2) |
O1—Cu1—Cu2—Cl2 | −171.6 (3) | N3—Cu3—O3—Cu4 | −150.5 (3) |
N2—Cu1—Cu2—Cl2 | −3.5 (3) | Cl3—Cu3—O3—Cu4 | −52.4 (15) |
Cl1—Cu1—Cu2—Cl2 | −139.90 (16) | O4—Cu4—O3—C15 | −138.1 (7) |
O3—Cu3—Cu4—O4 | 155.2 (4) | N4—Cu4—O3—C15 | −94.8 (10) |
N3—Cu3—Cu4—O4 | −170.2 (3) | Cl4—Cu4—O3—C15 | 36.0 (7) |
Cl3—Cu3—Cu4—O4 | −33.2 (3) | Cu3—Cu4—O3—C15 | −121.5 (8) |
O4—Cu3—Cu4—O3 | −155.2 (4) | O4—Cu4—O3—Cu3 | −16.6 (3) |
N3—Cu3—Cu4—O3 | 34.6 (4) | N4—Cu4—O3—Cu3 | 26.6 (10) |
Cl3—Cu3—Cu4—O3 | 171.6 (3) | Cl4—Cu4—O3—Cu3 | 157.5 (2) |
O3—Cu3—Cu4—N4 | −170.0 (4) | O3—Cu4—O4—C22 | 145.5 (6) |
O4—Cu3—Cu4—N4 | 34.8 (3) | N4—Cu4—O4—C22 | −21.3 (6) |
N3—Cu3—Cu4—N4 | −135.4 (3) | Cl4—Cu4—O4—C22 | 82.0 (17) |
Cl3—Cu3—Cu4—N4 | 1.6 (3) | Cu3—Cu4—O4—C22 | 129.1 (7) |
O3—Cu3—Cu4—Cl4 | −31.5 (3) | O3—Cu4—O4—Cu3 | 16.4 (2) |
O4—Cu3—Cu4—Cl4 | 173.4 (3) | N4—Cu4—O4—Cu3 | −150.4 (3) |
N3—Cu3—Cu4—Cl4 | 3.2 (3) | Cl4—Cu4—O4—Cu3 | −47.1 (17) |
Cl3—Cu3—Cu4—Cl4 | 140.15 (16) | O3—Cu3—O4—C22 | −137.8 (7) |
O2—Cu2—N1—C3 | −72.1 (11) | N3—Cu3—O4—C22 | −95.2 (10) |
O1—Cu2—N1—C3 | −111.7 (6) | Cl3—Cu3—O4—C22 | 34.9 (7) |
Cl2—Cu2—N1—C3 | 60.4 (6) | Cu4—Cu3—O4—C22 | −121.2 (7) |
Cu1—Cu2—N1—C3 | −90.2 (6) | O3—Cu3—O4—Cu4 | −16.6 (2) |
O2—Cu2—N1—C7 | 165.0 (8) | N3—Cu3—O4—Cu4 | 26.0 (9) |
O1—Cu2—N1—C7 | 125.4 (6) | Cl3—Cu3—O4—Cu4 | 156.08 (19) |
Cl2—Cu2—N1—C7 | −62.6 (6) | Cu2—O1—C1—C2 | −45.4 (8) |
Cu1—Cu2—N1—C7 | 146.9 (5) | Cu1—O1—C1—C2 | −158.8 (5) |
O2—Cu2—N1—C2 | 45.8 (11) | O1—C1—C2—N1 | 52.2 (10) |
O1—Cu2—N1—C2 | 6.2 (5) | C3—N1—C2—C1 | 85.9 (9) |
Cl2—Cu2—N1—C2 | 178.2 (5) | C7—N1—C2—C1 | −150.2 (7) |
Cu1—Cu2—N1—C2 | 27.6 (6) | Cu2—N1—C2—C1 | −31.7 (8) |
O2—Cu1—N2—C9 | 11.8 (6) | C7—N1—C3—C4 | −52.3 (10) |
O1—Cu1—N2—C9 | 59.4 (11) | C2—N1—C3—C4 | 71.6 (10) |
Cl1—Cu1—N2—C9 | −175.2 (6) | Cu2—N1—C3—C4 | −174.6 (6) |
Cu2—Cu1—N2—C9 | 35.5 (7) | N1—C3—C4—C5 | 51.6 (11) |
O2—Cu1—N2—C14 | −106.9 (6) | C3—C4—C5—C6 | −53.8 (12) |
O1—Cu1—N2—C14 | −59.4 (10) | C4—C5—C6—C7 | 58.0 (11) |
Cl1—Cu1—N2—C14 | 66.0 (6) | C3—N1—C7—C6 | 56.8 (10) |
Cu2—Cu1—N2—C14 | −83.2 (6) | C2—N1—C7—C6 | −66.5 (10) |
O2—Cu1—N2—C10 | 132.1 (6) | Cu2—N1—C7—C6 | 179.0 (7) |
O1—Cu1—N2—C10 | 179.7 (7) | C5—C6—C7—N1 | −59.9 (10) |
Cl1—Cu1—N2—C10 | −55.0 (6) | Cu2—O2—C8—C9 | −154.7 (6) |
Cu2—Cu1—N2—C10 | 155.8 (5) | Cu1—O2—C8—C9 | −39.2 (9) |
O3—Cu3—N3—C17 | −132.6 (6) | C14—N2—C9—C8 | 78.3 (9) |
O4—Cu3—N3—C17 | −174.8 (7) | C10—N2—C9—C8 | −158.4 (8) |
Cl3—Cu3—N3—C17 | 55.2 (6) | Cu1—N2—C9—C8 | −36.2 (9) |
Cu4—Cu3—N3—C17 | −155.2 (5) | O2—C8—C9—N2 | 51.1 (10) |
O3—Cu3—N3—C16 | −8.6 (6) | C9—N2—C10—C11 | −69.4 (11) |
O4—Cu3—N3—C16 | −50.8 (11) | C14—N2—C10—C11 | 54.9 (11) |
Cl3—Cu3—N3—C16 | 179.2 (6) | Cu1—N2—C10—C11 | 173.6 (8) |
Cu4—Cu3—N3—C16 | −31.2 (6) | N2—C10—C11—C12 | −58.9 (12) |
O3—Cu3—N3—C21 | 110.4 (6) | C10—C11—C12—C13 | 57.6 (12) |
O4—Cu3—N3—C21 | 68.2 (10) | C11—C12—C13—C14 | −55.2 (13) |
Cl3—Cu3—N3—C21 | −61.8 (5) | C9—N2—C14—C13 | 72.3 (10) |
Cu4—Cu3—N3—C21 | 87.8 (5) | C10—N2—C14—C13 | −51.0 (10) |
O4—Cu4—N4—C24 | −128.1 (6) | Cu1—N2—C14—C13 | −173.9 (7) |
O3—Cu4—N4—C24 | −171.0 (7) | C12—C13—C14—N2 | 53.1 (12) |
Cl4—Cu4—N4—C24 | 58.3 (6) | Cu3—O3—C15—C16 | 42.3 (9) |
Cu3—Cu4—N4—C24 | −150.8 (5) | Cu4—O3—C15—C16 | 156.7 (6) |
O4—Cu4—N4—C28 | 110.1 (6) | O3—C15—C16—N3 | −51.6 (11) |
O3—Cu4—N4—C28 | 67.2 (10) | C17—N3—C16—C15 | 155.0 (8) |
Cl4—Cu4—N4—C28 | −63.4 (6) | C21—N3—C16—C15 | −79.6 (10) |
Cu3—Cu4—N4—C28 | 87.5 (5) | Cu3—N3—C16—C15 | 34.7 (10) |
O4—Cu4—N4—C23 | −8.1 (6) | C16—N3—C17—C18 | 69.0 (10) |
O3—Cu4—N4—C23 | −51.0 (11) | C21—N3—C17—C18 | −58.5 (10) |
Cl4—Cu4—N4—C23 | 178.4 (5) | Cu3—N3—C17—C18 | −173.6 (7) |
Cu3—Cu4—N4—C23 | −30.7 (6) | N3—C17—C18—C19 | 59.5 (11) |
O2—Cu2—O1—C1 | −147.9 (6) | C17—C18—C19—C20 | −54.4 (12) |
N1—Cu2—O1—C1 | 21.1 (6) | C18—C19—C20—C21 | 53.5 (13) |
Cl2—Cu2—O1—C1 | −82.0 (15) | C19—C20—C21—N3 | −55.0 (12) |
Cu1—Cu2—O1—C1 | −131.2 (6) | C17—N3—C21—C20 | 56.3 (10) |
O2—Cu2—O1—Cu1 | −16.7 (2) | C16—N3—C21—C20 | −72.6 (10) |
N1—Cu2—O1—Cu1 | 152.2 (3) | Cu3—N3—C21—C20 | 173.9 (7) |
Cl2—Cu2—O1—Cu1 | 49.2 (15) | Cu4—O4—C22—C23 | 45.1 (9) |
O2—Cu1—O1—C1 | 135.8 (6) | Cu3—O4—C22—C23 | 158.7 (6) |
N2—Cu1—O1—C1 | 87.6 (10) | O4—C22—C23—N4 | −53.0 (10) |
Cl1—Cu1—O1—C1 | −38.0 (6) | C24—N4—C23—C22 | 157.2 (8) |
Cu2—Cu1—O1—C1 | 119.1 (7) | C28—N4—C23—C22 | −81.5 (9) |
O2—Cu1—O1—Cu2 | 16.7 (2) | Cu4—N4—C23—C22 | 35.5 (9) |
N2—Cu1—O1—Cu2 | −31.5 (9) | C28—N4—C24—C25 | −50.4 (11) |
Cl1—Cu1—O1—Cu2 | −157.1 (2) | C23—N4—C24—C25 | 71.5 (11) |
O1—Cu2—O2—C8 | 138.5 (7) | Cu4—N4—C24—C25 | −171.7 (7) |
N1—Cu2—O2—C8 | 98.5 (10) | N4—C24—C25—C26 | 52.0 (14) |
Cl2—Cu2—O2—C8 | −34.0 (6) | C24—C25—C26—C27 | −50.6 (13) |
Cu1—Cu2—O2—C8 | 121.8 (7) | C25—C26—C27—C28 | 52.0 (12) |
O1—Cu2—O2—Cu1 | 16.7 (2) | C24—N4—C28—C27 | 50.2 (11) |
N1—Cu2—O2—Cu1 | −23.3 (10) | C23—N4—C28—C27 | −71.7 (10) |
Cl2—Cu2—O2—Cu1 | −155.8 (2) | Cu4—N4—C28—C27 | 173.9 (7) |
O1—Cu1—O2—C8 | −149.3 (6) | C26—C27—C28—N4 | −53.0 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···Cl3 | 0.97 | 2.75 | 3.638 (9) | 153 |
C2—H2B···Cl4i | 0.97 | 2.97 | 3.689 (9) | 132 |
C3—H3B···Cl2 | 0.97 | 2.80 | 3.428 (10) | 124 |
C7—H7A···Cl2 | 0.97 | 2.87 | 3.464 (9) | 120 |
C9—H9B···Cl4 | 0.97 | 2.81 | 3.696 (11) | 153 |
C10—H10A···Cl1 | 0.97 | 2.80 | 3.423 (9) | 123 |
C14—H14B···Cl1 | 0.97 | 2.79 | 3.432 (10) | 124 |
C16—H16B···Cl1 | 0.97 | 2.75 | 3.647 (11) | 154 |
C17—H17B···Cl3 | 0.97 | 2.71 | 3.367 (9) | 125 |
C21—H21B···Cl3 | 0.97 | 2.75 | 3.400 (10) | 125 |
C23—H23A···Cl2ii | 0.97 | 2.94 | 3.765 (9) | 144 |
C23—H23B···Cl2 | 0.97 | 2.81 | 3.708 (10) | 155 |
C24—H24B···Cl4 | 0.97 | 2.83 | 3.469 (11) | 124 |
C28—H28A···Cl4 | 0.97 | 2.84 | 3.465 (10) | 123 |
Symmetry codes: (i) y, x+1, −z; (ii) y, x, −z. |
Experimental details
Crystal data | |
Chemical formula | [Cu4(C7H14NO)4Cl4] |
Mr | 908.72 |
Crystal system, space group | Tetragonal, P41212 |
Temperature (K) | 293 |
a, c (Å) | 13.9016 (2), 38.8340 (9) |
V (Å3) | 7504.8 (3) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 5.47 |
Crystal size (mm) | 0.16 × 0.12 × 0.08 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.569, 0.753 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 66705, 6976, 6547 |
Rint | 0.066 |
(sin θ/λ)max (Å−1) | 0.608 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.182, 1.17 |
No. of reflections | 6976 |
No. of parameters | 398 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0407P)2 + 55.9102P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.93, −0.81 |
Absolute structure | Flack (1983), 2913 Friedel pairs |
Absolute structure parameter | 0.18 (5) |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).
Acknowledgements
This work was supported financially by Hefei University of Technology, China.
References
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hamamci, S., Yilmaz, V. T. & Buyukgungor, O. (2008). Z. Naturforsch. Teil B, 63, 139–142. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yilmaz, V. T., Soyer, E. & Buyukgungor, O. (2010). Polyhedron, 29, 920–924. Web of Science CSD CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The piperidineethanol chelated metal complexes have been synthesized and their crystal structures have been reported previously (Hamamci et al., 2008; Yilmaz et al. 2010). We report here the structure of the title tetranuclear complex, a CuII complex N,O-chelated by the deprotonated piperidineethanol anion.
The molecular structure is shown in Fig. 1. Each CuII cation is N,O-chelated by a piperidineethnolate anion and coordinated by a Cl- anion and two O atoms from neighboring piperidineethanolate anions in a distorted NO3Cl square-pyramidal geometry. The Cu—O bond distances in the apical direction are significantly longer than those in the basal planes. The deprotonated hydroxyl groups of piperidineethanolate anions bridge the CuII cations to form the tetranuclear complex. The piperidine ring displays a chair conformation.
In the crystal, there are no significant intermolecular interactions present.