In the title compound,
catena-poly[(5,12-dimethyl-7,14-diphenyl-1,4,8,11-tetracyclotetradecane)copper(II) bis[[(5,12-dimethyl-7,14-diphenyl-1,4,8,11-tetracyclotetradecane)copper(II)]-μ-oxalato-[(acetonitrile)copper(II)]-μ-oxalato] diperchlorate], [Cu(C
24N
4H
36)][Cu
4(C
2O
4)
4(C
24N
4H
36)
2(CH
3CN)
2](ClO
4)
2, the {(CuC
24N
4H
36)-μ-[Cu(C
2O
4)
2(CH
3CN)]}
2n component is a one-dimensional chain polymeric complex of copper(II) bridged by [Cu(C
2O
4)
2(CH
3CN)]
2−. In the structure, there are three types of copper(II) coordination environment. The coordination environment around the Cu
II atom in (Cu
L)
2+ of the polymer (
L is 5,12-dimethyl-7,14-diphenyl-1,4,8,11-tetracyclotetradecane) is an elongated octahedron, the Cu
II atom in [Cu(C
2O
4)
2(CH
3CN)]
2− exhibits a square-based pyramidal geometry, while the Cu
II atom in the (Cu
L)
2+ counter-cation exhibits a square-planar geometry. The Cu atoms coordinated by
L lie on inversion centers. The Cu
Cu distances are 6.092 (4) and 5.551 (4) Å.
Supporting information
CCDC reference: 255465
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.010 Å
- R factor = 0.064
- wR factor = 0.174
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.66 Ratio
PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors for N7
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.37 Ratio
PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 3.01 Ratio
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for O3
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for O7
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C18
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C41
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for Cl
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.54 Ang.
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C3 - C4 ... 1.53 Ang.
PLAT416_ALERT_2_C Short Intra D-H..H-D H1 .. H2 .. 1.90 Ang.
PLAT416_ALERT_2_C Short Intra D-H..H-D H3 .. H4 .. 1.93 Ang.
PLAT416_ALERT_2_C Short Intra D-H..H-D H5 .. H6 .. 1.90 Ang.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
12 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.
catena-poly[(5,12-dimethyl-7,14-diphenyl-1,4,8,11-
tetracyclotetradecane)copper(II) bis[[(5,12-dimethyl-7,14-diphenyl-1,4,8,11-
tetracyclotetradecane)copper(II)]-µ-oxalato-[(acetonitrile)copper(II)]-µ-
oxalato] diperchlorate]
top
Crystal data top
[Cu(C24H36N4)][Cu4(C2O4)4(C24H36N4)2(C2H3N)2](ClO4)2 | Z = 1 |
Mr = 2092.54 | F(000) = 1087 |
Triclinic, P1 | Dx = 1.484 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.2419 (5) Å | Cell parameters from 5807 reflections |
b = 14.5966 (7) Å | θ = 1.6–25.1° |
c = 15.8730 (8) Å | µ = 1.26 mm−1 |
α = 64.8130 (12)° | T = 293 K |
β = 86.6890 (12)° | Block, purple |
γ = 81.0760 (12)° | 0.60 × 0.44 × 0.20 mm |
V = 2328.38 (19) Å3 | |
Data collection top
Siemens SMART CCD diffractometer | 8044 independent reflections |
Radiation source: fine-focus sealed tube | 6479 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 25.1°, θmin = 1.6° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.523, Tmax = 0.777 | k = −17→16 |
11947 measured reflections | l = −18→15 |
Refinement top
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.174 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0656P)2 + 10.7785P] where P = (Fo2 + 2Fc2)/3 |
8044 reflections | (Δ/σ)max = 0.002 |
587 parameters | Δρmax = 0.97 e Å−3 |
0 restraints | Δρmin = −0.67 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.17874 (7) | 0.26092 (5) | 0.31421 (5) | 0.0520 (2) | |
Cu2 | 0.5000 | 0.5000 | 0.0000 | 0.0344 (2) | |
Cu3 | 0.0000 | 0.5000 | 0.5000 | 0.0362 (2) | |
Cu4 | 0.5000 | 0.0000 | 0.5000 | 0.0415 (2) | |
O1 | 0.3084 (3) | 0.1886 (3) | 0.2688 (3) | 0.0449 (9) | |
O2 | 0.1935 (4) | 0.3761 (3) | 0.1963 (3) | 0.0606 (12) | |
O3 | 0.3242 (4) | 0.4260 (3) | 0.0816 (3) | 0.0541 (10) | |
O4 | 0.4422 (4) | 0.2265 (3) | 0.1551 (3) | 0.0708 (14) | |
O5 | 0.1784 (4) | 0.1492 (3) | 0.4358 (3) | 0.0528 (10) | |
O6 | 0.0752 (4) | 0.3403 (3) | 0.3701 (3) | 0.0589 (12) | |
O7 | 0.0394 (5) | 0.3300 (3) | 0.5135 (3) | 0.0653 (13) | |
O8 | 0.1229 (4) | 0.1223 (3) | 0.5797 (3) | 0.0627 (12) | |
N1 | 0.5816 (4) | 0.4676 (3) | 0.1248 (3) | 0.0388 (10) | |
H1 | 0.5235 | 0.4430 | 0.1125 | 0.047* | |
N2 | 0.4248 (4) | 0.6344 (3) | 0.0027 (3) | 0.0344 (9) | |
H2 | 0.4820 | 0.6199 | −0.0300 | 0.041* | |
N3 | −0.0586 (4) | 0.5464 (3) | 0.3666 (3) | 0.0394 (10) | |
H3 | −0.0146 | 0.4922 | 0.4044 | 0.047* | |
N4 | −0.1738 (4) | 0.4728 (4) | 0.5382 (3) | 0.0451 (11) | |
H4 | −0.1367 | 0.5206 | 0.5369 | 0.054* | |
N5 | 0.3327 (4) | −0.0423 (3) | 0.5379 (3) | 0.0400 (10) | |
H5 | 0.3582 | 0.0134 | 0.5001 | 0.048* | |
N6 | 0.5084 (4) | 0.0009 (4) | 0.6265 (3) | 0.0414 (10) | |
H6 | 0.5469 | −0.0432 | 0.6085 | 0.050* | |
C1 | 0.3535 (5) | 0.2501 (4) | 0.1939 (4) | 0.0413 (12) | |
C2 | 0.2879 (5) | 0.3608 (4) | 0.1524 (4) | 0.0417 (12) | |
C3 | 0.1292 (5) | 0.1782 (4) | 0.4974 (4) | 0.0436 (13) | |
C4 | 0.0768 (5) | 0.2918 (4) | 0.4597 (4) | 0.0444 (13) | |
C5 | 0.7575 (7) | 0.3952 (5) | 0.2335 (5) | 0.0638 (18) | |
H5A | 0.7517 | 0.4585 | 0.2395 | 0.096* | |
H5B | 0.8404 | 0.3649 | 0.2383 | 0.096* | |
H5C | 0.7125 | 0.3494 | 0.2822 | 0.096* | |
C6 | 0.7071 (5) | 0.4154 (4) | 0.1401 (4) | 0.0426 (12) | |
H6A | 0.7566 | 0.4602 | 0.0919 | 0.051* | |
C7 | 0.5655 (6) | 0.5664 (4) | 0.1326 (4) | 0.0500 (14) | |
H7A | 0.6250 | 0.6080 | 0.0952 | 0.060* | |
H7B | 0.5761 | 0.5544 | 0.1969 | 0.060* | |
C8 | 0.4408 (6) | 0.6210 (4) | 0.0990 (4) | 0.0478 (14) | |
H8A | 0.3814 | 0.5814 | 0.1390 | 0.057* | |
H8B | 0.4295 | 0.6872 | 0.1011 | 0.057* | |
C9 | 0.2990 (5) | 0.6757 (4) | −0.0316 (4) | 0.0391 (12) | |
H9A | 0.2474 | 0.6269 | 0.0097 | 0.047* | |
C10 | 0.2833 (5) | 0.6843 (4) | −0.1289 (4) | 0.0424 (12) | |
H10A | 0.3434 | 0.7235 | −0.1684 | 0.051* | |
H10B | 0.2050 | 0.7234 | −0.1523 | 0.051* | |
C11 | 0.2566 (5) | 0.7780 (4) | −0.0270 (4) | 0.0378 (11) | |
C12 | 0.3131 (5) | 0.8631 (4) | −0.0782 (4) | 0.0467 (13) | |
H12A | 0.3794 | 0.8570 | −0.1143 | 0.056* | |
C13 | 0.2728 (6) | 0.9559 (4) | −0.0764 (5) | 0.0535 (15) | |
H13A | 0.3101 | 1.0125 | −0.1127 | 0.064* | |
C14 | 0.1765 (6) | 0.9654 (5) | −0.0205 (5) | 0.0573 (16) | |
H14A | 0.1493 | 1.0279 | −0.0185 | 0.069* | |
C15 | 0.1215 (6) | 0.8800 (5) | 0.0324 (5) | 0.0593 (17) | |
H15A | 0.0576 | 0.8848 | 0.0710 | 0.071* | |
C16 | 0.1617 (5) | 0.7883 (5) | 0.0275 (4) | 0.0499 (14) | |
H16A | 0.1232 | 0.7320 | 0.0623 | 0.060* | |
C17 | −0.3141 (8) | 0.3579 (8) | 0.6445 (6) | 0.095 (3) | |
H17A | −0.3473 | 0.3534 | 0.5922 | 0.143* | |
H17B | −0.3606 | 0.4128 | 0.6552 | 0.143* | |
H17C | −0.3163 | 0.2947 | 0.6987 | 0.143* | |
C18 | −0.1855 (6) | 0.3780 (5) | 0.6244 (4) | 0.0526 (15) | |
H18A | −0.1405 | 0.3203 | 0.6144 | 0.063* | |
C19 | −0.2314 (6) | 0.4769 (6) | 0.4558 (4) | 0.0547 (16) | |
H19A | −0.3183 | 0.4881 | 0.4612 | 0.066* | |
H19B | −0.2086 | 0.4127 | 0.4506 | 0.066* | |
C20 | −0.1911 (5) | 0.5637 (5) | 0.3706 (4) | 0.0494 (14) | |
H20A | −0.2256 | 0.5662 | 0.3150 | 0.059* | |
H20B | −0.2180 | 0.6283 | 0.3742 | 0.059* | |
C21 | −0.0096 (5) | 0.6326 (4) | 0.2903 (4) | 0.0415 (12) | |
H21A | −0.0390 | 0.6948 | 0.2990 | 0.050* | |
C22 | 0.1266 (5) | 0.6178 (5) | 0.2935 (4) | 0.0520 (15) | |
H22A | 0.1541 | 0.6698 | 0.2368 | 0.062* | |
H22B | 0.1560 | 0.5520 | 0.2930 | 0.062* | |
C23 | −0.0543 (5) | 0.6486 (4) | 0.1960 (4) | 0.0456 (13) | |
C24 | −0.1325 (6) | 0.7330 (5) | 0.1428 (5) | 0.0605 (17) | |
H24A | −0.1618 | 0.7807 | 0.1661 | 0.073* | |
C25 | −0.1692 (8) | 0.7495 (7) | 0.0553 (6) | 0.082 (2) | |
H25A | −0.2222 | 0.8079 | 0.0206 | 0.099* | |
C26 | −0.1282 (10) | 0.6809 (9) | 0.0200 (6) | 0.097 (3) | |
H26A | −0.1520 | 0.6922 | −0.0392 | 0.116* | |
C27 | −0.0509 (9) | 0.5941 (8) | 0.0728 (6) | 0.083 (3) | |
H27A | −0.0232 | 0.5463 | 0.0492 | 0.100* | |
C28 | −0.0143 (7) | 0.5773 (5) | 0.1601 (4) | 0.0577 (16) | |
H28A | 0.0373 | 0.5182 | 0.1952 | 0.069* | |
C29 | 0.1548 (6) | −0.1201 (6) | 0.5292 (5) | 0.0669 (19) | |
H29A | 0.1425 | −0.1396 | 0.5946 | 0.100* | |
H29B | 0.1299 | −0.1702 | 0.5124 | 0.100* | |
H29C | 0.1082 | −0.0546 | 0.4944 | 0.100* | |
C30 | 0.2875 (5) | −0.1136 (4) | 0.5072 (4) | 0.0484 (14) | |
H30A | 0.3326 | −0.1819 | 0.5417 | 0.058* | |
C31 | 0.3293 (6) | −0.0767 (5) | 0.6397 (4) | 0.0544 (15) | |
H31A | 0.3734 | −0.1451 | 0.6702 | 0.065* | |
H31B | 0.2467 | −0.0783 | 0.6609 | 0.065* | |
C32 | 0.3850 (5) | −0.0039 (5) | 0.6633 (4) | 0.0540 (15) | |
H32A | 0.3376 | 0.0635 | 0.6361 | 0.065* | |
H32B | 0.3869 | −0.0269 | 0.7303 | 0.065* | |
C33 | 0.5589 (5) | 0.0900 (4) | 0.6241 (4) | 0.0465 (13) | |
H33A | 0.5150 | 0.1516 | 0.5758 | 0.056* | |
C34 | 0.6909 (5) | 0.0838 (5) | 0.5956 (4) | 0.0502 (14) | |
H34A | 0.7291 | 0.1279 | 0.6139 | 0.060* | |
H34B | 0.7302 | 0.0143 | 0.6301 | 0.060* | |
C35 | 0.5419 (5) | 0.1005 (5) | 0.7151 (4) | 0.0497 (14) | |
C36 | 0.5977 (7) | 0.0263 (5) | 0.7964 (5) | 0.0611 (17) | |
H36A | 0.6438 | −0.0323 | 0.7962 | 0.073* | |
C37 | 0.5846 (8) | 0.0399 (6) | 0.8780 (5) | 0.074 (2) | |
H37A | 0.6222 | −0.0098 | 0.9325 | 0.088* | |
C38 | 0.5166 (8) | 0.1259 (7) | 0.8788 (6) | 0.077 (2) | |
H38A | 0.5089 | 0.1345 | 0.9338 | 0.092* | |
C39 | 0.4603 (7) | 0.1989 (6) | 0.7998 (6) | 0.072 (2) | |
H39A | 0.4138 | 0.2570 | 0.8009 | 0.086* | |
C40 | 0.4725 (6) | 0.1864 (5) | 0.7180 (5) | 0.0596 (16) | |
H40A | 0.4337 | 0.2363 | 0.6642 | 0.072* | |
Cl | 0.43084 (17) | 0.33701 (19) | 0.39798 (13) | 0.0821 (6) | |
O11 | 0.4042 (16) | 0.4065 (13) | 0.3115 (7) | 0.270 (8) | |
O12 | 0.3374 (9) | 0.3444 (8) | 0.4529 (9) | 0.196 (5) | |
O13 | 0.4452 (7) | 0.2321 (8) | 0.4072 (8) | 0.156 (4) | |
O14 | 0.5311 (8) | 0.3504 (6) | 0.4354 (7) | 0.133 (3) | |
C42 | 0.0119 (12) | 0.0242 (10) | 0.2242 (8) | 0.127 (4) | |
H42A | 0.0882 | −0.0028 | 0.2074 | 0.191* | |
H42B | −0.0456 | 0.0428 | 0.1752 | 0.191* | |
H42C | −0.0155 | −0.0268 | 0.2806 | 0.191* | |
N7 | 0.0320 (8) | 0.1820 (8) | 0.2514 (6) | 0.104 (3) | |
C41 | 0.0249 (8) | 0.1129 (10) | 0.2385 (6) | 0.087 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0657 (5) | 0.0351 (4) | 0.0417 (4) | 0.0026 (3) | 0.0212 (3) | −0.0090 (3) |
Cu2 | 0.0440 (5) | 0.0303 (4) | 0.0289 (4) | −0.0032 (4) | 0.0016 (4) | −0.0134 (4) |
Cu3 | 0.0359 (5) | 0.0401 (5) | 0.0300 (4) | −0.0084 (4) | 0.0094 (3) | −0.0124 (4) |
Cu4 | 0.0307 (5) | 0.0526 (6) | 0.0296 (5) | −0.0034 (4) | 0.0047 (3) | −0.0079 (4) |
O1 | 0.050 (2) | 0.0340 (19) | 0.041 (2) | −0.0023 (16) | 0.0137 (17) | −0.0090 (16) |
O2 | 0.071 (3) | 0.042 (2) | 0.050 (2) | 0.007 (2) | 0.021 (2) | −0.0094 (19) |
O3 | 0.060 (3) | 0.045 (2) | 0.045 (2) | −0.0089 (19) | 0.0119 (19) | −0.0090 (19) |
O4 | 0.065 (3) | 0.052 (3) | 0.073 (3) | −0.002 (2) | 0.040 (2) | −0.013 (2) |
O5 | 0.065 (3) | 0.034 (2) | 0.047 (2) | 0.0045 (18) | 0.0161 (19) | −0.0104 (17) |
O6 | 0.079 (3) | 0.037 (2) | 0.045 (2) | 0.010 (2) | 0.019 (2) | −0.0112 (18) |
O7 | 0.094 (4) | 0.049 (2) | 0.050 (3) | −0.004 (2) | 0.027 (2) | −0.024 (2) |
O8 | 0.073 (3) | 0.053 (3) | 0.042 (2) | 0.002 (2) | 0.009 (2) | −0.006 (2) |
N1 | 0.046 (3) | 0.039 (2) | 0.035 (2) | −0.0070 (19) | −0.0015 (19) | −0.0188 (19) |
N2 | 0.041 (2) | 0.030 (2) | 0.032 (2) | 0.0004 (17) | 0.0030 (17) | −0.0145 (18) |
N3 | 0.045 (2) | 0.038 (2) | 0.028 (2) | −0.0041 (19) | 0.0071 (18) | −0.0077 (18) |
N4 | 0.042 (3) | 0.049 (3) | 0.040 (3) | −0.017 (2) | 0.011 (2) | −0.013 (2) |
N5 | 0.033 (2) | 0.043 (2) | 0.038 (2) | −0.0102 (19) | 0.0096 (18) | −0.011 (2) |
N6 | 0.035 (2) | 0.047 (3) | 0.037 (2) | −0.0026 (19) | 0.0049 (18) | −0.015 (2) |
C1 | 0.041 (3) | 0.038 (3) | 0.041 (3) | −0.010 (2) | 0.008 (2) | −0.011 (2) |
C2 | 0.051 (3) | 0.031 (3) | 0.039 (3) | −0.010 (2) | 0.009 (2) | −0.010 (2) |
C3 | 0.042 (3) | 0.039 (3) | 0.042 (3) | −0.004 (2) | 0.007 (2) | −0.011 (3) |
C4 | 0.050 (3) | 0.034 (3) | 0.040 (3) | −0.006 (2) | 0.015 (2) | −0.010 (2) |
C5 | 0.069 (4) | 0.061 (4) | 0.067 (4) | 0.004 (3) | −0.020 (3) | −0.034 (4) |
C6 | 0.045 (3) | 0.040 (3) | 0.040 (3) | −0.010 (2) | 0.000 (2) | −0.013 (2) |
C7 | 0.070 (4) | 0.047 (3) | 0.040 (3) | −0.002 (3) | −0.010 (3) | −0.026 (3) |
C8 | 0.067 (4) | 0.038 (3) | 0.042 (3) | −0.002 (3) | 0.001 (3) | −0.022 (3) |
C9 | 0.047 (3) | 0.033 (3) | 0.036 (3) | −0.011 (2) | 0.011 (2) | −0.013 (2) |
C10 | 0.044 (3) | 0.035 (3) | 0.042 (3) | 0.000 (2) | −0.003 (2) | −0.012 (2) |
C11 | 0.038 (3) | 0.037 (3) | 0.037 (3) | −0.004 (2) | 0.007 (2) | −0.016 (2) |
C12 | 0.049 (3) | 0.038 (3) | 0.049 (3) | −0.009 (2) | 0.016 (3) | −0.017 (3) |
C13 | 0.052 (4) | 0.037 (3) | 0.066 (4) | −0.008 (3) | 0.011 (3) | −0.017 (3) |
C14 | 0.057 (4) | 0.046 (3) | 0.076 (4) | 0.008 (3) | −0.002 (3) | −0.037 (3) |
C15 | 0.053 (4) | 0.056 (4) | 0.074 (4) | −0.004 (3) | 0.019 (3) | −0.035 (3) |
C16 | 0.045 (3) | 0.051 (3) | 0.051 (3) | −0.011 (3) | 0.015 (3) | −0.020 (3) |
C17 | 0.075 (5) | 0.139 (8) | 0.065 (5) | −0.065 (6) | 0.018 (4) | −0.023 (5) |
C18 | 0.053 (3) | 0.062 (4) | 0.036 (3) | −0.021 (3) | 0.008 (3) | −0.011 (3) |
C19 | 0.045 (3) | 0.082 (5) | 0.039 (3) | −0.025 (3) | 0.006 (3) | −0.023 (3) |
C20 | 0.044 (3) | 0.067 (4) | 0.035 (3) | −0.011 (3) | 0.001 (2) | −0.018 (3) |
C21 | 0.048 (3) | 0.034 (3) | 0.039 (3) | −0.007 (2) | 0.007 (2) | −0.013 (2) |
C22 | 0.052 (3) | 0.058 (4) | 0.036 (3) | −0.016 (3) | 0.012 (3) | −0.009 (3) |
C23 | 0.052 (3) | 0.044 (3) | 0.036 (3) | −0.014 (3) | 0.008 (2) | −0.011 (2) |
C24 | 0.060 (4) | 0.054 (4) | 0.057 (4) | −0.009 (3) | −0.001 (3) | −0.013 (3) |
C25 | 0.083 (6) | 0.085 (6) | 0.061 (5) | −0.024 (5) | −0.026 (4) | −0.007 (4) |
C26 | 0.124 (8) | 0.125 (8) | 0.048 (4) | −0.077 (7) | −0.003 (5) | −0.022 (5) |
C27 | 0.110 (7) | 0.103 (7) | 0.066 (5) | −0.058 (6) | 0.026 (5) | −0.053 (5) |
C28 | 0.076 (4) | 0.053 (4) | 0.049 (4) | −0.019 (3) | 0.014 (3) | −0.025 (3) |
C29 | 0.052 (4) | 0.080 (5) | 0.076 (5) | −0.031 (4) | 0.022 (3) | −0.036 (4) |
C30 | 0.044 (3) | 0.042 (3) | 0.051 (3) | −0.007 (2) | 0.008 (3) | −0.012 (3) |
C31 | 0.047 (3) | 0.065 (4) | 0.039 (3) | −0.011 (3) | 0.013 (3) | −0.011 (3) |
C32 | 0.048 (3) | 0.075 (4) | 0.031 (3) | −0.011 (3) | 0.010 (2) | −0.015 (3) |
C33 | 0.045 (3) | 0.041 (3) | 0.041 (3) | 0.002 (2) | 0.005 (2) | −0.009 (2) |
C34 | 0.050 (3) | 0.048 (3) | 0.051 (3) | −0.010 (3) | 0.003 (3) | −0.018 (3) |
C35 | 0.050 (3) | 0.048 (3) | 0.050 (3) | −0.012 (3) | 0.012 (3) | −0.018 (3) |
C36 | 0.072 (4) | 0.060 (4) | 0.049 (4) | −0.007 (3) | 0.004 (3) | −0.021 (3) |
C37 | 0.094 (6) | 0.077 (5) | 0.051 (4) | −0.023 (4) | 0.003 (4) | −0.024 (4) |
C38 | 0.096 (6) | 0.093 (6) | 0.063 (5) | −0.046 (5) | 0.019 (4) | −0.047 (5) |
C39 | 0.081 (5) | 0.070 (5) | 0.086 (6) | −0.024 (4) | 0.021 (4) | −0.051 (5) |
C40 | 0.057 (4) | 0.056 (4) | 0.068 (4) | −0.008 (3) | 0.011 (3) | −0.029 (3) |
Cl | 0.0588 (11) | 0.1196 (17) | 0.0567 (10) | 0.0272 (11) | −0.0079 (8) | −0.0388 (11) |
O11 | 0.328 (19) | 0.332 (19) | 0.075 (6) | −0.089 (15) | −0.038 (9) | 0.003 (9) |
O12 | 0.144 (8) | 0.151 (8) | 0.275 (14) | −0.002 (6) | 0.110 (9) | −0.094 (9) |
O13 | 0.114 (6) | 0.192 (9) | 0.230 (10) | 0.041 (6) | −0.062 (6) | −0.165 (9) |
O14 | 0.147 (7) | 0.103 (5) | 0.166 (8) | −0.011 (5) | −0.041 (6) | −0.071 (5) |
C42 | 0.136 (10) | 0.160 (12) | 0.104 (8) | −0.054 (9) | 0.012 (7) | −0.064 (8) |
N7 | 0.089 (6) | 0.120 (7) | 0.101 (6) | −0.011 (5) | 0.007 (5) | −0.046 (6) |
C41 | 0.068 (5) | 0.122 (8) | 0.070 (5) | −0.013 (5) | −0.002 (4) | −0.039 (6) |
Geometric parameters (Å, º) top
Cu1—O5 | 1.925 (4) | C14—C15 | 1.389 (9) |
Cu1—O2 | 1.931 (4) | C14—H14A | 0.9300 |
Cu1—O1 | 1.952 (4) | C15—C16 | 1.378 (9) |
Cu1—O6 | 1.955 (4) | C15—H15A | 0.9300 |
Cu2—N2i | 2.029 (4) | C16—H16A | 0.9300 |
Cu2—N2 | 2.029 (4) | C17—C18 | 1.510 (9) |
Cu2—N1i | 2.065 (4) | C17—H17A | 0.9600 |
Cu2—N1 | 2.065 (4) | C17—H17B | 0.9600 |
Cu2—O3 | 2.434 (4) | C17—H17C | 0.9600 |
Cu2—O3i | 2.434 (4) | C18—C22ii | 1.523 (9) |
Cu3—N3 | 2.044 (4) | C18—H18A | 0.9800 |
Cu3—N3ii | 2.044 (4) | C19—C20 | 1.513 (8) |
Cu3—N4ii | 2.059 (4) | C19—H19A | 0.9700 |
Cu3—N4 | 2.059 (4) | C19—H19B | 0.9700 |
Cu3—O7 | 2.371 (4) | C20—H20A | 0.9700 |
Cu3—O7ii | 2.371 (4) | C20—H20B | 0.9700 |
Cu4—N6 | 2.022 (5) | C21—C22 | 1.514 (8) |
Cu4—N6iii | 2.022 (5) | C21—C23 | 1.516 (8) |
Cu4—N5iii | 2.048 (4) | C21—H21A | 0.9800 |
Cu4—N5 | 2.048 (4) | C22—C18ii | 1.523 (9) |
O1—C1 | 1.280 (6) | C22—H22A | 0.9700 |
O2—C2 | 1.280 (7) | C22—H22B | 0.9700 |
O3—C2 | 1.221 (6) | C23—C24 | 1.366 (9) |
O4—C1 | 1.223 (7) | C23—C28 | 1.393 (9) |
O5—C3 | 1.287 (7) | C24—C25 | 1.380 (11) |
O6—C4 | 1.291 (7) | C24—H24A | 0.9300 |
O7—C4 | 1.227 (7) | C25—C26 | 1.355 (14) |
O8—C3 | 1.215 (7) | C25—H25A | 0.9300 |
N1—C6 | 1.476 (7) | C26—C27 | 1.379 (14) |
N1—C7 | 1.484 (7) | C26—H26A | 0.9300 |
N1—H1 | 0.8600 | C27—C28 | 1.376 (11) |
N2—C8 | 1.474 (7) | C27—H27A | 0.9300 |
N2—C9 | 1.485 (7) | C28—H28A | 0.9300 |
N2—H2 | 0.8600 | C29—C30 | 1.520 (8) |
N3—C20 | 1.473 (7) | C29—H29A | 0.9600 |
N3—C21 | 1.482 (7) | C29—H29B | 0.9600 |
N3—H3 | 0.8600 | C29—H29C | 0.9600 |
N4—C19 | 1.467 (7) | C30—C34iii | 1.515 (8) |
N4—C18 | 1.492 (7) | C30—H30A | 0.9800 |
N4—H4 | 0.8600 | C31—C32 | 1.494 (9) |
N5—C31 | 1.474 (7) | C31—H31A | 0.9700 |
N5—C30 | 1.485 (8) | C31—H31B | 0.9700 |
N5—H5 | 0.8600 | C32—H32A | 0.9700 |
N6—C32 | 1.473 (7) | C32—H32B | 0.9700 |
N6—C33 | 1.484 (8) | C33—C35 | 1.513 (8) |
N6—H6 | 0.8600 | C33—C34 | 1.527 (8) |
C1—C2 | 1.539 (7) | C33—H33A | 0.9800 |
C3—C4 | 1.532 (8) | C34—C30iii | 1.515 (8) |
C5—C6 | 1.510 (8) | C34—H34A | 0.9700 |
C5—H5A | 0.9600 | C34—H34B | 0.9700 |
C5—H5B | 0.9600 | C35—C36 | 1.388 (9) |
C5—H5C | 0.9600 | C35—C40 | 1.388 (9) |
C6—C10i | 1.527 (8) | C36—C37 | 1.387 (10) |
C6—H6A | 0.9800 | C36—H36A | 0.9300 |
C7—C8 | 1.505 (9) | C37—C38 | 1.370 (12) |
C7—H7A | 0.9700 | C37—H37A | 0.9300 |
C7—H7B | 0.9700 | C38—C39 | 1.362 (12) |
C8—H8A | 0.9700 | C38—H38A | 0.9300 |
C8—H8B | 0.9700 | C39—C40 | 1.382 (10) |
C9—C10 | 1.514 (8) | C39—H39A | 0.9300 |
C9—C11 | 1.525 (7) | C40—H40A | 0.9300 |
C9—H9A | 0.9800 | Cl—O11 | 1.331 (11) |
C10—C6i | 1.527 (8) | Cl—O12 | 1.347 (9) |
C10—H10A | 0.9700 | Cl—O14 | 1.381 (8) |
C10—H10B | 0.9700 | Cl—O13 | 1.458 (9) |
C11—C16 | 1.366 (7) | C42—C41 | 1.436 (16) |
C11—C12 | 1.391 (7) | C42—H42A | 0.9600 |
C12—C13 | 1.372 (8) | C42—H42B | 0.9600 |
C12—H12A | 0.9300 | C42—H42C | 0.9600 |
C13—C14 | 1.387 (9) | N7—C41 | 1.126 (12) |
C13—H13A | 0.9300 | | |
| | | |
O5—Cu1—O2 | 174.2 (2) | C13—C12—H12A | 119.4 |
O5—Cu1—O1 | 93.82 (15) | C11—C12—H12A | 119.4 |
O2—Cu1—O1 | 84.99 (16) | C12—C13—C14 | 120.1 (6) |
O5—Cu1—O6 | 84.96 (16) | C12—C13—H13A | 120.0 |
O2—Cu1—O6 | 95.06 (17) | C14—C13—H13A | 120.0 |
O1—Cu1—O6 | 168.5 (2) | C13—C14—C15 | 118.9 (5) |
N2i—Cu2—N2 | 180.0 (2) | C13—C14—H14A | 120.5 |
N2i—Cu2—N1i | 86.28 (17) | C15—C14—H14A | 120.5 |
N2—Cu2—N1i | 93.72 (17) | C16—C15—C14 | 119.8 (6) |
N2i—Cu2—N1 | 93.72 (17) | C16—C15—H15A | 120.1 |
N2—Cu2—N1 | 86.28 (17) | C14—C15—H15A | 120.1 |
N1i—Cu2—N1 | 180.0 | C11—C16—C15 | 121.7 (6) |
N2i—Cu2—O3 | 91.62 (15) | C11—C16—H16A | 119.1 |
N2—Cu2—O3 | 88.38 (15) | C15—C16—H16A | 119.1 |
N1i—Cu2—O3 | 89.15 (16) | C18—C17—H17A | 109.5 |
N1—Cu2—O3 | 90.85 (16) | C18—C17—H17B | 109.5 |
N2i—Cu2—O3i | 88.38 (15) | H17A—C17—H17B | 109.5 |
N2—Cu2—O3i | 91.62 (15) | C18—C17—H17C | 109.5 |
N1i—Cu2—O3i | 90.85 (16) | H17A—C17—H17C | 109.5 |
N1—Cu2—O3i | 89.15 (16) | H17B—C17—H17C | 109.5 |
O3—Cu2—O3i | 180.0 (2) | N4—C18—C17 | 112.8 (6) |
N3—Cu3—N3ii | 180.000 (1) | N4—C18—C22ii | 110.0 (5) |
N3—Cu3—N4ii | 94.35 (18) | C17—C18—C22ii | 111.8 (5) |
N3ii—Cu3—N4ii | 85.65 (18) | N4—C18—H18A | 107.3 |
N3—Cu3—N4 | 85.65 (18) | C17—C18—H18A | 107.3 |
N3ii—Cu3—N4 | 94.35 (18) | C22ii—C18—H18A | 107.3 |
N4ii—Cu3—N4 | 180.000 (1) | N4—C19—C20 | 108.5 (5) |
N3—Cu3—O7 | 88.68 (17) | N4—C19—H19A | 110.0 |
N3ii—Cu3—O7 | 91.32 (17) | C20—C19—H19A | 110.0 |
N4ii—Cu3—O7 | 93.42 (18) | N4—C19—H19B | 110.0 |
N4—Cu3—O7 | 86.58 (18) | C20—C19—H19B | 110.0 |
N3—Cu3—O7ii | 91.32 (17) | H19A—C19—H19B | 108.4 |
N3ii—Cu3—O7ii | 88.68 (17) | N3—C20—C19 | 108.6 (5) |
N4ii—Cu3—O7ii | 86.58 (18) | N3—C20—H20A | 110.0 |
N4—Cu3—O7ii | 93.42 (18) | C19—C20—H20A | 110.0 |
O7—Cu3—O7ii | 180.0 (2) | N3—C20—H20B | 110.0 |
N6—Cu4—N6iii | 180.000 (1) | C19—C20—H20B | 110.0 |
N6—Cu4—N5iii | 93.74 (18) | H20A—C20—H20B | 108.4 |
N6iii—Cu4—N5iii | 86.26 (18) | N3—C21—C22 | 111.5 (4) |
N6—Cu4—N5 | 86.26 (18) | N3—C21—C23 | 111.3 (4) |
N6iii—Cu4—N5 | 93.74 (18) | C22—C21—C23 | 110.8 (5) |
N5iii—Cu4—N5 | 180.0 (3) | N3—C21—H21A | 107.7 |
C1—O1—Cu1 | 111.2 (3) | C22—C21—H21A | 107.7 |
C2—O2—Cu1 | 112.2 (3) | C23—C21—H21A | 107.7 |
C2—O3—Cu2 | 145.5 (4) | C21—C22—C18ii | 117.3 (5) |
C3—O5—Cu1 | 112.5 (3) | C21—C22—H22A | 108.0 |
C4—O6—Cu1 | 110.7 (3) | C18ii—C22—H22A | 108.0 |
C4—O7—Cu3 | 134.0 (4) | C21—C22—H22B | 108.0 |
C6—N1—C7 | 113.4 (4) | C18ii—C22—H22B | 108.0 |
C6—N1—Cu2 | 117.6 (3) | H22A—C22—H22B | 107.2 |
C7—N1—Cu2 | 105.0 (3) | C24—C23—C28 | 117.7 (6) |
C6—N1—H1 | 123.3 | C24—C23—C21 | 122.0 (6) |
C7—N1—H1 | 123.3 | C28—C23—C21 | 120.3 (5) |
Cu2—N1—H1 | 48.9 | C23—C24—C25 | 121.9 (7) |
C8—N2—C9 | 112.5 (4) | C23—C24—H24A | 119.0 |
C8—N2—Cu2 | 105.7 (3) | C25—C24—H24A | 119.0 |
C9—N2—Cu2 | 118.2 (3) | C26—C25—C24 | 120.1 (8) |
C8—N2—H2 | 123.8 | C26—C25—H25A | 119.9 |
C9—N2—H2 | 123.8 | C24—C25—H25A | 119.9 |
Cu2—N2—H2 | 48.0 | C25—C26—C27 | 119.3 (8) |
C20—N3—C21 | 112.6 (4) | C25—C26—H26A | 120.4 |
C20—N3—Cu3 | 105.5 (3) | C27—C26—H26A | 120.4 |
C21—N3—Cu3 | 119.2 (3) | C28—C27—C26 | 120.7 (8) |
C20—N3—H3 | 123.7 | C28—C27—H27A | 119.6 |
C21—N3—H3 | 123.7 | C26—C27—H27A | 119.6 |
Cu3—N3—H3 | 47.1 | C27—C28—C23 | 120.3 (7) |
C19—N4—C18 | 113.9 (5) | C27—C28—H28A | 119.9 |
C19—N4—Cu3 | 106.0 (3) | C23—C28—H28A | 119.9 |
C18—N4—Cu3 | 115.3 (4) | C30—C29—H29A | 109.5 |
C19—N4—H4 | 123.1 | C30—C29—H29B | 109.5 |
C18—N4—H4 | 123.1 | H29A—C29—H29B | 109.5 |
Cu3—N4—H4 | 49.8 | C30—C29—H29C | 109.5 |
C31—N5—C30 | 113.0 (4) | H29A—C29—H29C | 109.5 |
C31—N5—Cu4 | 104.8 (3) | H29B—C29—H29C | 109.5 |
C30—N5—Cu4 | 120.8 (3) | N5—C30—C34iii | 111.3 (5) |
C31—N5—H5 | 123.5 | N5—C30—C29 | 111.6 (5) |
C30—N5—H5 | 123.5 | C34iii—C30—C29 | 110.3 (5) |
Cu4—N5—H5 | 45.9 | N5—C30—H30A | 107.8 |
C32—N6—C33 | 112.6 (5) | C34iii—C30—H30A | 107.8 |
C32—N6—Cu4 | 106.0 (3) | C29—C30—H30A | 107.8 |
C33—N6—Cu4 | 113.4 (3) | N5—C31—C32 | 108.6 (5) |
C32—N6—H6 | 123.7 | N5—C31—H31A | 110.0 |
C33—N6—H6 | 123.7 | C32—C31—H31A | 110.0 |
Cu4—N6—H6 | 52.7 | N5—C31—H31B | 110.0 |
O4—C1—O1 | 124.7 (5) | C32—C31—H31B | 110.0 |
O4—C1—C2 | 119.8 (5) | H31A—C31—H31B | 108.4 |
O1—C1—C2 | 115.5 (5) | N6—C32—C31 | 109.0 (5) |
O3—C2—O2 | 124.5 (5) | N6—C32—H32A | 109.9 |
O3—C2—C1 | 120.9 (5) | C31—C32—H32A | 109.9 |
O2—C2—C1 | 114.6 (4) | N6—C32—H32B | 109.9 |
O8—C3—O5 | 124.6 (5) | C31—C32—H32B | 109.9 |
O8—C3—C4 | 120.6 (5) | H32A—C32—H32B | 108.3 |
O5—C3—C4 | 114.8 (5) | N6—C33—C35 | 112.4 (4) |
O7—C4—O6 | 124.9 (5) | N6—C33—C34 | 109.8 (5) |
O7—C4—C3 | 120.3 (5) | C35—C33—C34 | 112.1 (5) |
O6—C4—C3 | 114.8 (5) | N6—C33—H33A | 107.4 |
C6—C5—H5A | 109.5 | C35—C33—H33A | 107.4 |
C6—C5—H5B | 109.5 | C34—C33—H33A | 107.4 |
H5A—C5—H5B | 109.5 | C30iii—C34—C33 | 115.3 (5) |
C6—C5—H5C | 109.5 | C30iii—C34—H34A | 108.4 |
H5A—C5—H5C | 109.5 | C33—C34—H34A | 108.4 |
H5B—C5—H5C | 109.5 | C30iii—C34—H34B | 108.4 |
N1—C6—C5 | 113.0 (5) | C33—C34—H34B | 108.4 |
N1—C6—C10i | 110.2 (4) | H34A—C34—H34B | 107.5 |
C5—C6—C10i | 110.3 (5) | C36—C35—C40 | 118.6 (6) |
N1—C6—H6A | 107.7 | C36—C35—C33 | 121.0 (6) |
C5—C6—H6A | 107.7 | C40—C35—C33 | 120.3 (6) |
C10i—C6—H6A | 107.7 | C37—C36—C35 | 119.8 (7) |
N1—C7—C8 | 108.6 (5) | C37—C36—H36A | 120.1 |
N1—C7—H7A | 110.0 | C35—C36—H36A | 120.1 |
C8—C7—H7A | 110.0 | C38—C37—C36 | 120.4 (8) |
N1—C7—H7B | 110.0 | C38—C37—H37A | 119.8 |
C8—C7—H7B | 110.0 | C36—C37—H37A | 119.8 |
H7A—C7—H7B | 108.4 | C39—C38—C37 | 120.5 (7) |
N2—C8—C7 | 109.1 (5) | C39—C38—H38A | 119.8 |
N2—C8—H8A | 109.9 | C37—C38—H38A | 119.8 |
C7—C8—H8A | 109.9 | C38—C39—C40 | 119.7 (7) |
N2—C8—H8B | 109.9 | C38—C39—H39A | 120.1 |
C7—C8—H8B | 109.9 | C40—C39—H39A | 120.1 |
H8A—C8—H8B | 108.3 | C39—C40—C35 | 120.9 (7) |
N2—C9—C10 | 111.6 (4) | C39—C40—H40A | 119.5 |
N2—C9—C11 | 111.9 (4) | C35—C40—H40A | 119.5 |
C10—C9—C11 | 111.0 (4) | O11—Cl—O12 | 108.3 (10) |
N2—C9—H9A | 107.4 | O11—Cl—O14 | 113.9 (9) |
C10—C9—H9A | 107.4 | O12—Cl—O14 | 106.8 (8) |
C11—C9—H9A | 107.4 | O11—Cl—O13 | 113.2 (9) |
C9—C10—C6i | 117.1 (4) | O12—Cl—O13 | 105.2 (7) |
C9—C10—H10A | 108.0 | O14—Cl—O13 | 108.9 (4) |
C6i—C10—H10A | 108.0 | C41—C42—H42A | 109.5 |
C9—C10—H10B | 108.0 | C41—C42—H42B | 109.5 |
C6i—C10—H10B | 108.0 | H42A—C42—H42B | 109.5 |
H10A—C10—H10B | 107.3 | C41—C42—H42C | 109.5 |
C16—C11—C12 | 118.2 (5) | H42A—C42—H42C | 109.5 |
C16—C11—C9 | 120.8 (5) | H42B—C42—H42C | 109.5 |
C12—C11—C9 | 121.1 (5) | N7—C41—C42 | 177.9 (12) |
C13—C12—C11 | 121.2 (5) | | |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C42—H42C···O8iv | 0.96 | 2.43 | 3.369 (13) | 166 |
C33—H33A···O13 | 0.98 | 2.54 | 3.376 (12) | 144 |
Symmetry code: (iv) −x, −y, −z+1. |