Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805011451/sg6003sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805011451/sg6003Isup2.hkl |
CCDC reference: 274622
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[Cu(C36H36N4O4)(ClO4)](ClO4)·C3H7N | F(000) = 1916 |
Mr = 924.22 | Dx = 1.524 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1784 reflections |
a = 9.717 (2) Å | θ = 2.0–25.5° |
b = 27.863 (3) Å | µ = 0.75 mm−1 |
c = 14.902 (5) Å | T = 293 K |
β = 93.06 (2)° | Prism, yellow |
V = 4028.9 (16) Å3 | 0.32 × 0.26 × 0.24 mm |
Z = 4 |
Bruker SMART Apex CCD area-detector diffractometer | 7914 independent reflections |
Radiation source: sealed tube | 6113 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 26.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→11 |
Tmin = 0.79, Tmax = 0.84 | k = −16→34 |
17136 measured reflections | l = −14→18 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0743P)2 + 0.9397P] where P = (Fo2 + 2Fc2)/3 |
7914 reflections | (Δ/σ)max < 0.001 |
543 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.75 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 6.5772 (0.0074) x + 2.3014 (0.0251) y + 11.4232 (0.0100) z = 6.3059 (0.0252) * -0.0459 (0.0011) Cu1 * 0.0308 (0.0013) O1 * -0.0071 (0.0013) O2 * -0.0075 (0.0013) N1 * 0.0298 (0.0013) N2 Rms deviation of fitted atoms = 0.0285 |
x | y | z | Uiso*/Ueq | ||
C1 | −0.2009 (3) | 0.93373 (13) | −0.0449 (2) | 0.0252 (7) | |
H1 | −0.2721 | 0.9426 | −0.0857 | 0.030* | |
C2 | −0.0599 (3) | 0.94964 (13) | −0.0459 (2) | 0.0265 (7) | |
H2 | −0.0236 | 0.9705 | −0.0872 | 0.032* | |
C3 | 0.0129 (3) | 0.92754 (12) | 0.0278 (2) | 0.0221 (7) | |
H3 | 0.1061 | 0.9310 | 0.0441 | 0.026* | |
C4 | −0.0809 (3) | 0.89987 (13) | 0.0708 (2) | 0.0262 (7) | |
C5 | −0.0688 (4) | 0.86921 (13) | 0.1487 (2) | 0.0280 (8) | |
H5C | 0.0226 | 0.8552 | 0.1494 | 0.034* | |
H5D | −0.1346 | 0.8431 | 0.1416 | 0.034* | |
C6 | −0.0705 (3) | 0.85641 (13) | 0.3122 (2) | 0.0271 (8) | |
H6A | −0.1499 | 0.8355 | 0.3039 | 0.033* | |
H6B | −0.0807 | 0.8736 | 0.3681 | 0.033* | |
C7 | 0.0605 (3) | 0.82299 (14) | 0.3266 (3) | 0.0305 (8) | |
H7A | 0.0370 | 0.7931 | 0.3554 | 0.037* | |
H7B | 0.0880 | 0.8151 | 0.2667 | 0.037* | |
C8 | 0.3134 (4) | 0.82592 (14) | 0.3435 (3) | 0.0319 (8) | |
H8A | 0.3203 | 0.8326 | 0.2800 | 0.038* | |
H8B | 0.3900 | 0.8418 | 0.3756 | 0.038* | |
C9 | 0.3259 (4) | 0.77561 (14) | 0.3573 (2) | 0.0294 (8) | |
C10 | 0.2920 (4) | 0.73485 (14) | 0.3015 (3) | 0.0309 (8) | |
H10 | 0.2513 | 0.7357 | 0.2436 | 0.037* | |
C11 | 0.3319 (3) | 0.69274 (12) | 0.3508 (2) | 0.0236 (7) | |
H11 | 0.3208 | 0.6612 | 0.3312 | 0.028* | |
C12 | 0.3916 (3) | 0.70776 (12) | 0.4351 (2) | 0.0226 (7) | |
H12 | 0.4273 | 0.6876 | 0.4804 | 0.027* | |
C13 | 0.1660 (3) | 0.84519 (13) | 0.4718 (2) | 0.0258 (7) | |
H13A | 0.0711 | 0.8525 | 0.4836 | 0.031* | |
H13B | 0.1849 | 0.8127 | 0.4926 | 0.031* | |
C14 | 0.2562 (4) | 0.87831 (14) | 0.5239 (2) | 0.0292 (8) | |
C15 | 0.3530 (3) | 0.86246 (13) | 0.5908 (2) | 0.0246 (7) | |
H15 | 0.3612 | 0.8298 | 0.6032 | 0.030* | |
C16 | 0.4361 (3) | 0.89495 (13) | 0.6385 (2) | 0.0257 (7) | |
C17 | 0.4235 (3) | 0.94392 (12) | 0.6198 (2) | 0.0248 (7) | |
H17 | 0.4794 | 0.9658 | 0.6517 | 0.030* | |
C18 | 0.3288 (3) | 0.95994 (13) | 0.5545 (2) | 0.0265 (8) | |
C19 | 0.2454 (3) | 0.92719 (13) | 0.5073 (2) | 0.0261 (7) | |
C20 | 0.5378 (4) | 0.87720 (15) | 0.7135 (3) | 0.0335 (9) | |
H20A | 0.6293 | 0.8874 | 0.7012 | 0.050* | |
H20B | 0.5348 | 0.8428 | 0.7163 | 0.050* | |
H20C | 0.5129 | 0.8903 | 0.7700 | 0.050* | |
C21 | 0.3242 (4) | 1.01129 (14) | 0.5421 (3) | 0.0323 (8) | |
H21 | 0.3858 | 1.0294 | 0.5779 | 0.039* | |
C22 | 0.2456 (4) | 1.08476 (14) | 0.4744 (2) | 0.0286 (8) | |
C23 | 0.3324 (4) | 1.11602 (15) | 0.5223 (3) | 0.0325 (8) | |
H23 | 0.3997 | 1.1040 | 0.5630 | 0.039* | |
C24 | 0.3194 (4) | 1.16523 (15) | 0.5098 (3) | 0.0311 (8) | |
H24 | 0.3779 | 1.1861 | 0.5421 | 0.037* | |
C25 | 0.2188 (4) | 1.18335 (14) | 0.4488 (2) | 0.0296 (8) | |
H25 | 0.2106 | 1.2163 | 0.4397 | 0.035* | |
C26 | 0.1343 (4) | 1.15296 (13) | 0.4036 (2) | 0.0280 (8) | |
H26 | 0.0665 | 1.1648 | 0.3631 | 0.034* | |
C27 | 0.1446 (4) | 1.10234 (13) | 0.4146 (2) | 0.0255 (7) | |
C28 | −0.0385 (4) | 1.07764 (13) | 0.3044 (2) | 0.0283 (8) | |
H28 | −0.0490 | 1.1102 | 0.2922 | 0.034* | |
C29 | −0.1226 (4) | 1.04769 (13) | 0.2560 (2) | 0.0295 (8) | |
C30 | −0.2101 (4) | 1.06826 (15) | 0.1891 (2) | 0.0322 (8) | |
H30 | −0.2076 | 1.1012 | 0.1789 | 0.039* | |
C31 | −0.3017 (4) | 1.03928 (13) | 0.1372 (2) | 0.0286 (8) | |
C32 | −0.3019 (4) | 0.99021 (14) | 0.1513 (3) | 0.0306 (8) | |
H32 | −0.3600 | 0.9707 | 0.1156 | 0.037* | |
C33 | −0.2157 (3) | 0.96983 (13) | 0.2184 (2) | 0.0249 (7) | |
C34 | −0.1260 (4) | 0.99819 (13) | 0.2688 (2) | 0.0269 (7) | |
C35 | −0.2213 (4) | 0.91738 (13) | 0.2429 (2) | 0.0276 (8) | |
H35A | −0.2870 | 0.9013 | 0.2017 | 0.033* | |
H35B | −0.2541 | 0.9143 | 0.3029 | 0.033* | |
C36 | −0.3933 (4) | 1.05836 (14) | 0.0639 (2) | 0.0325 (8) | |
H36A | −0.4809 | 1.0661 | 0.0870 | 0.049* | |
H36B | −0.4058 | 1.0347 | 0.0174 | 0.049* | |
H36C | −0.3533 | 1.0867 | 0.0397 | 0.049* | |
C37 | 0.4832 (4) | 0.84587 (15) | 0.0831 (3) | 0.0375 (9) | |
H37A | 0.4966 | 0.8742 | 0.0479 | 0.056* | |
H37B | 0.5712 | 0.8327 | 0.1024 | 0.056* | |
H37C | 0.4330 | 0.8540 | 0.1347 | 0.056* | |
C38 | 0.4688 (4) | 0.78517 (16) | −0.0397 (3) | 0.0399 (10) | |
H38A | 0.4724 | 0.8026 | −0.0951 | 0.060* | |
H38B | 0.4188 | 0.7558 | −0.0501 | 0.060* | |
H38C | 0.5608 | 0.7780 | −0.0169 | 0.060* | |
C39 | 0.2577 (4) | 0.80581 (13) | 0.0385 (2) | 0.0276 (8) | |
H39 | 0.2093 | 0.7942 | −0.0125 | 0.033* | |
Cl1 | 0.31789 (9) | 0.95423 (3) | 0.24048 (6) | 0.02622 (19) | |
Cl2 | 0.70596 (8) | 0.74491 (3) | 0.22272 (5) | 0.02455 (19) | |
Cu1 | 0.10210 (4) | 1.003902 (14) | 0.40453 (3) | 0.02437 (13) | |
N1 | 0.0573 (3) | 1.06757 (11) | 0.36926 (19) | 0.0261 (6) | |
N2 | 0.2435 (3) | 1.03449 (12) | 0.4864 (2) | 0.0338 (7) | |
N3 | −0.0804 (3) | 0.89212 (11) | 0.2396 (2) | 0.0303 (7) | |
N4 | 0.1815 (3) | 0.84695 (11) | 0.3735 (2) | 0.0279 (7) | |
N5 | 0.4004 (3) | 0.81387 (11) | 0.0250 (2) | 0.0289 (7) | |
O1 | −0.0440 (2) | 0.97528 (9) | 0.33290 (15) | 0.0233 (5) | |
H1A | −0.0033 | 0.9484 | 0.3027 | 0.028* | |
O2 | 0.1470 (2) | 0.93968 (9) | 0.44671 (15) | 0.0242 (5) | |
H2B | 0.1647 | 0.9213 | 0.3932 | 0.029* | |
O3 | −0.2124 (2) | 0.90239 (9) | 0.02836 (16) | 0.0248 (5) | |
O4 | 0.3879 (2) | 0.75839 (8) | 0.43880 (16) | 0.0272 (5) | |
O5 | 0.2721 (2) | 1.00169 (9) | 0.26882 (17) | 0.0289 (6) | |
O6 | 0.3663 (3) | 0.96044 (10) | 0.15609 (17) | 0.0335 (6) | |
O7 | 0.2016 (2) | 0.92078 (9) | 0.23772 (17) | 0.0286 (5) | |
O8 | 0.4193 (2) | 0.93619 (8) | 0.30244 (16) | 0.0259 (5) | |
O9 | 0.6513 (3) | 0.78369 (11) | 0.2674 (2) | 0.0420 (7) | |
O10 | 0.8474 (2) | 0.74792 (10) | 0.22660 (17) | 0.0319 (6) | |
O11 | 0.6653 (3) | 0.70062 (11) | 0.24467 (18) | 0.0365 (6) | |
O12 | 0.6573 (3) | 0.74450 (10) | 0.13739 (18) | 0.0358 (6) | |
O13 | 0.1864 (3) | 0.81083 (10) | 0.10146 (18) | 0.0370 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0225 (15) | 0.0254 (18) | 0.0285 (19) | 0.0038 (14) | 0.0081 (13) | 0.0000 (15) |
C2 | 0.0240 (16) | 0.0262 (19) | 0.0306 (19) | 0.0048 (14) | 0.0119 (14) | −0.0029 (15) |
C3 | 0.0261 (15) | 0.0195 (17) | 0.0221 (16) | 0.0016 (13) | 0.0140 (13) | 0.0009 (13) |
C4 | 0.0256 (16) | 0.0244 (18) | 0.0296 (18) | 0.0028 (14) | 0.0090 (14) | 0.0014 (15) |
C5 | 0.0265 (16) | 0.028 (2) | 0.0307 (19) | −0.0052 (15) | 0.0084 (14) | −0.0018 (15) |
C6 | 0.0257 (16) | 0.0249 (18) | 0.0318 (19) | −0.0025 (14) | 0.0115 (14) | −0.0031 (15) |
C7 | 0.0270 (17) | 0.034 (2) | 0.032 (2) | −0.0023 (15) | 0.0121 (15) | −0.0094 (17) |
C8 | 0.0344 (18) | 0.028 (2) | 0.035 (2) | 0.0063 (16) | 0.0140 (16) | −0.0026 (16) |
C9 | 0.0377 (18) | 0.0203 (18) | 0.0307 (19) | 0.0021 (15) | 0.0078 (15) | 0.0018 (15) |
C10 | 0.0349 (18) | 0.028 (2) | 0.0292 (19) | −0.0034 (15) | −0.0058 (15) | −0.0010 (16) |
C11 | 0.0322 (17) | 0.0171 (17) | 0.0219 (17) | 0.0002 (14) | 0.0044 (13) | 0.0017 (13) |
C12 | 0.0281 (16) | 0.0177 (16) | 0.0230 (17) | −0.0034 (13) | 0.0103 (13) | 0.0010 (14) |
C13 | 0.0284 (16) | 0.0231 (18) | 0.0266 (19) | 0.0009 (14) | 0.0077 (14) | −0.0004 (14) |
C14 | 0.0279 (17) | 0.030 (2) | 0.0290 (19) | −0.0021 (15) | −0.0057 (14) | 0.0006 (15) |
C15 | 0.0261 (16) | 0.0208 (17) | 0.0268 (18) | 0.0007 (13) | 0.0007 (13) | 0.0008 (14) |
C16 | 0.0260 (16) | 0.0230 (18) | 0.0274 (18) | 0.0046 (14) | −0.0066 (14) | 0.0057 (15) |
C17 | 0.0301 (16) | 0.0209 (17) | 0.0239 (17) | 0.0040 (14) | 0.0060 (13) | 0.0007 (14) |
C18 | 0.0264 (16) | 0.0246 (19) | 0.0295 (19) | 0.0041 (14) | 0.0102 (14) | 0.0012 (15) |
C19 | 0.0277 (16) | 0.0262 (19) | 0.0246 (18) | 0.0081 (14) | 0.0050 (13) | 0.0007 (15) |
C20 | 0.0359 (18) | 0.035 (2) | 0.0287 (19) | 0.0185 (17) | −0.0065 (15) | 0.0096 (17) |
C21 | 0.0392 (19) | 0.026 (2) | 0.033 (2) | 0.0012 (16) | 0.0044 (16) | −0.0006 (16) |
C22 | 0.0326 (18) | 0.0263 (19) | 0.0281 (19) | −0.0029 (15) | 0.0130 (15) | 0.0010 (15) |
C23 | 0.0311 (18) | 0.035 (2) | 0.032 (2) | −0.0048 (16) | 0.0069 (15) | −0.0014 (17) |
C24 | 0.0263 (16) | 0.035 (2) | 0.031 (2) | −0.0034 (15) | −0.0044 (15) | −0.0052 (17) |
C25 | 0.0309 (17) | 0.0250 (19) | 0.034 (2) | 0.0000 (15) | 0.0097 (15) | −0.0016 (16) |
C26 | 0.0324 (17) | 0.0243 (18) | 0.0282 (19) | 0.0044 (15) | 0.0090 (14) | −0.0013 (15) |
C27 | 0.0309 (16) | 0.0193 (17) | 0.0270 (18) | −0.0012 (14) | 0.0069 (14) | 0.0026 (14) |
C28 | 0.0332 (18) | 0.0251 (19) | 0.0278 (19) | 0.0059 (15) | 0.0131 (15) | 0.0031 (15) |
C29 | 0.043 (2) | 0.0207 (17) | 0.0254 (18) | 0.0017 (16) | 0.0089 (15) | 0.0019 (15) |
C30 | 0.042 (2) | 0.0260 (19) | 0.0289 (19) | −0.0001 (16) | 0.0066 (16) | 0.0016 (16) |
C31 | 0.0304 (17) | 0.0219 (18) | 0.033 (2) | 0.0075 (15) | 0.0003 (15) | 0.0002 (15) |
C32 | 0.0312 (17) | 0.027 (2) | 0.033 (2) | −0.0012 (15) | −0.0074 (15) | 0.0010 (15) |
C33 | 0.0256 (16) | 0.0203 (17) | 0.0295 (18) | 0.0031 (14) | 0.0085 (13) | 0.0028 (15) |
C34 | 0.0301 (16) | 0.0239 (18) | 0.0274 (18) | 0.0028 (15) | 0.0079 (14) | −0.0010 (15) |
C35 | 0.0316 (17) | 0.0231 (18) | 0.0287 (19) | −0.0055 (15) | 0.0080 (15) | −0.0001 (15) |
C36 | 0.0334 (18) | 0.033 (2) | 0.030 (2) | 0.0151 (17) | −0.0082 (15) | 0.0045 (17) |
C37 | 0.040 (2) | 0.033 (2) | 0.042 (2) | −0.0074 (17) | 0.0188 (17) | −0.0075 (18) |
C38 | 0.039 (2) | 0.040 (2) | 0.041 (2) | −0.0039 (18) | 0.0125 (18) | −0.0038 (19) |
C39 | 0.0326 (17) | 0.0213 (18) | 0.0298 (19) | 0.0002 (15) | 0.0109 (15) | 0.0010 (15) |
Cl1 | 0.0331 (4) | 0.0150 (4) | 0.0313 (4) | −0.0001 (3) | 0.0087 (3) | 0.0013 (3) |
Cl2 | 0.0320 (4) | 0.0167 (4) | 0.0258 (4) | 0.0003 (3) | 0.0087 (3) | 0.0001 (3) |
Cu1 | 0.0325 (2) | 0.0163 (2) | 0.0251 (2) | 0.00019 (17) | 0.00895 (17) | −0.00022 (17) |
N1 | 0.0342 (15) | 0.0205 (14) | 0.0250 (15) | 0.0017 (13) | 0.0147 (12) | 0.0004 (13) |
N2 | 0.0283 (15) | 0.0354 (19) | 0.0371 (18) | −0.0023 (14) | −0.0032 (13) | −0.0010 (15) |
N3 | 0.0343 (15) | 0.0253 (16) | 0.0321 (17) | −0.0029 (13) | 0.0089 (13) | −0.0030 (13) |
N4 | 0.0258 (14) | 0.0278 (16) | 0.0313 (17) | 0.0010 (12) | 0.0111 (12) | −0.0009 (13) |
N5 | 0.0286 (14) | 0.0281 (17) | 0.0310 (16) | −0.0049 (13) | 0.0123 (12) | −0.0086 (14) |
O1 | 0.0265 (11) | 0.0221 (12) | 0.0226 (12) | 0.0020 (10) | 0.0132 (9) | 0.0047 (10) |
O2 | 0.0226 (11) | 0.0269 (13) | 0.0232 (12) | 0.0058 (10) | 0.0022 (9) | −0.0003 (10) |
O3 | 0.0241 (11) | 0.0238 (13) | 0.0269 (13) | −0.0006 (10) | 0.0064 (9) | −0.0020 (10) |
O4 | 0.0324 (12) | 0.0189 (12) | 0.0318 (13) | −0.0020 (10) | 0.0148 (10) | 0.0003 (10) |
O5 | 0.0323 (12) | 0.0231 (13) | 0.0330 (14) | −0.0048 (10) | 0.0166 (10) | −0.0098 (11) |
O6 | 0.0362 (13) | 0.0329 (15) | 0.0325 (14) | −0.0047 (12) | 0.0119 (11) | −0.0025 (12) |
O7 | 0.0349 (13) | 0.0216 (13) | 0.0303 (14) | −0.0027 (10) | 0.0114 (10) | 0.0036 (10) |
O8 | 0.0340 (12) | 0.0162 (12) | 0.0281 (13) | 0.0040 (10) | 0.0069 (10) | 0.0021 (10) |
O9 | 0.0335 (14) | 0.0434 (17) | 0.0501 (18) | −0.0146 (13) | 0.0101 (12) | −0.0101 (14) |
O10 | 0.0289 (12) | 0.0329 (14) | 0.0350 (14) | −0.0019 (11) | 0.0135 (10) | −0.0048 (12) |
O11 | 0.0302 (13) | 0.0414 (17) | 0.0383 (16) | −0.0032 (12) | 0.0055 (11) | 0.0017 (13) |
O12 | 0.0306 (13) | 0.0405 (17) | 0.0369 (15) | −0.0012 (12) | 0.0059 (11) | −0.0014 (13) |
O13 | 0.0490 (15) | 0.0307 (15) | 0.0327 (15) | 0.0034 (12) | 0.0154 (12) | 0.0029 (12) |
C1—O3 | 1.407 (4) | C23—H23 | 0.9300 |
C1—C2 | 1.441 (5) | C24—C25 | 1.393 (5) |
C1—H1 | 0.9300 | C24—H24 | 0.9300 |
C2—C3 | 1.415 (5) | C25—C26 | 1.337 (5) |
C2—H2 | 0.9300 | C25—H25 | 0.9300 |
C3—C4 | 1.377 (5) | C26—C27 | 1.423 (5) |
C3—H3 | 0.9300 | C26—H26 | 0.9300 |
C4—O3 | 1.396 (4) | C27—N1 | 1.433 (5) |
C4—C5 | 1.441 (5) | C28—N1 | 1.335 (5) |
C5—N3 | 1.507 (4) | C28—C29 | 1.350 (5) |
C5—H5C | 0.9700 | C28—H28 | 0.9300 |
C5—H5D | 0.9700 | C29—C34 | 1.393 (5) |
C6—N3 | 1.470 (5) | C29—C30 | 1.398 (5) |
C6—C7 | 1.583 (5) | C30—C31 | 1.403 (5) |
C6—H6A | 0.9700 | C30—H30 | 0.9300 |
C6—H6B | 0.9700 | C31—C32 | 1.383 (5) |
C7—N4 | 1.493 (5) | C31—C36 | 1.471 (5) |
C7—H7A | 0.9700 | C32—C33 | 1.392 (5) |
C7—H7B | 0.9700 | C32—H32 | 0.9300 |
C8—C9 | 1.421 (5) | C33—C34 | 1.370 (5) |
C8—N4 | 1.499 (4) | C33—C35 | 1.508 (5) |
C8—H8A | 0.9700 | C34—O1 | 1.369 (4) |
C8—H8B | 0.9700 | C35—N3 | 1.542 (5) |
C9—O4 | 1.410 (4) | C35—H35A | 0.9700 |
C9—C10 | 1.436 (5) | C35—H35B | 0.9700 |
C10—C11 | 1.427 (5) | C36—H36A | 0.9600 |
C10—H10 | 0.9300 | C36—H36B | 0.9600 |
C11—C12 | 1.419 (5) | C36—H36C | 0.9600 |
C11—H11 | 0.9300 | C37—N5 | 1.456 (5) |
C12—O4 | 1.412 (4) | C37—H37A | 0.9600 |
C12—H12 | 0.9300 | C37—H37B | 0.9600 |
C13—C14 | 1.466 (5) | C37—H37C | 0.9600 |
C13—N4 | 1.482 (4) | C38—N5 | 1.441 (5) |
C13—H13A | 0.9700 | C38—H38A | 0.9600 |
C13—H13B | 0.9700 | C38—H38B | 0.9600 |
C14—C19 | 1.387 (5) | C38—H38C | 0.9600 |
C14—C15 | 1.405 (5) | C39—O13 | 1.204 (4) |
C15—C16 | 1.384 (5) | C39—N5 | 1.430 (4) |
C15—H15 | 0.9300 | C39—H39 | 0.9300 |
C16—C17 | 1.397 (5) | Cl1—O6 | 1.377 (3) |
C16—C20 | 1.534 (4) | Cl1—O8 | 1.407 (3) |
C17—C18 | 1.377 (5) | Cl1—O7 | 1.464 (3) |
C17—H17 | 0.9300 | Cl1—O5 | 1.465 (2) |
C18—C19 | 1.387 (5) | Cl2—O12 | 1.333 (3) |
C18—C21 | 1.443 (5) | Cl2—O11 | 1.342 (3) |
C19—O2 | 1.327 (4) | Cl2—O10 | 1.375 (3) |
C20—H20A | 0.9600 | Cl2—O9 | 1.389 (3) |
C20—H20B | 0.9600 | Cu1—N1 | 1.894 (3) |
C20—H20C | 0.9600 | Cu1—O1 | 1.905 (2) |
C21—N2 | 1.285 (5) | Cu1—O2 | 1.938 (2) |
C21—H21 | 0.9300 | Cu1—N2 | 1.981 (3) |
C22—C27 | 1.380 (5) | Cu1—O5 | 2.679 (2) |
C22—C23 | 1.384 (5) | O1—H1A | 0.9700 |
C22—N2 | 1.412 (5) | O2—H2B | 0.9700 |
C23—C24 | 1.389 (5) | ||
O3—C1—C2 | 108.3 (3) | C25—C26—H26 | 119.8 |
O3—C1—H1 | 125.9 | C27—C26—H26 | 118.0 |
C2—C1—H1 | 125.9 | C22—C27—C26 | 118.0 (3) |
C3—C2—C1 | 107.1 (3) | C22—C27—N1 | 116.6 (3) |
C3—C2—H2 | 126.4 | C26—C27—N1 | 125.4 (3) |
C1—C2—H2 | 126.4 | N1—C28—C29 | 129.5 (4) |
C4—C3—C2 | 106.8 (3) | N1—C28—H28 | 114.3 |
C4—C3—H3 | 126.6 | C29—C28—H28 | 116.2 |
C2—C3—H3 | 126.6 | C28—C29—C34 | 123.8 (4) |
C3—C4—O3 | 111.9 (3) | C28—C29—C30 | 117.1 (3) |
C3—C4—C5 | 132.7 (3) | C34—C29—C30 | 119.0 (4) |
O3—C4—C5 | 115.3 (3) | C29—C30—C31 | 120.1 (4) |
C4—C5—N3 | 117.8 (3) | C29—C30—H30 | 120.0 |
C4—C5—H5C | 106.5 | C31—C30—H30 | 120.0 |
N3—C5—H5C | 105.8 | C32—C31—C30 | 119.4 (3) |
C4—C5—H5D | 109.4 | C32—C31—C36 | 117.6 (3) |
N3—C5—H5D | 109.5 | C30—C31—C36 | 122.8 (3) |
H5C—C5—H5D | 107.3 | C31—C32—C33 | 120.4 (3) |
N3—C6—C7 | 121.2 (3) | C31—C32—H32 | 119.8 |
N3—C6—H6A | 107.0 | C33—C32—H32 | 119.8 |
C7—C6—H6A | 107.0 | C34—C33—C32 | 120.0 (3) |
N3—C6—H6B | 107.0 | C34—C33—C35 | 117.2 (3) |
C7—C6—H6B | 107.0 | C32—C33—C35 | 122.8 (3) |
H6A—C6—H6B | 106.8 | O1—C34—C33 | 116.3 (3) |
N4—C7—C6 | 114.1 (3) | O1—C34—C29 | 122.7 (3) |
N4—C7—H7A | 112.1 | C33—C34—C29 | 121.0 (3) |
C6—C7—H7A | 111.0 | C33—C35—N3 | 113.0 (3) |
N4—C7—H7B | 106.4 | C33—C35—H35A | 109.0 |
C6—C7—H7B | 105.5 | N3—C35—H35A | 109.0 |
H7A—C7—H7B | 107.3 | C33—C35—H35B | 109.0 |
C9—C8—N4 | 114.2 (3) | N3—C35—H35B | 109.0 |
C9—C8—H8A | 108.7 | H35A—C35—H35B | 107.8 |
N4—C8—H8A | 108.7 | C31—C36—H36A | 109.1 |
C9—C8—H8B | 108.7 | C31—C36—H36B | 109.6 |
N4—C8—H8B | 108.7 | H36A—C36—H36B | 109.5 |
H8A—C8—H8B | 107.6 | C31—C36—H36C | 109.6 |
O4—C9—C8 | 119.3 (3) | H36A—C36—H36C | 109.5 |
O4—C9—C10 | 107.7 (3) | H36B—C36—H36C | 109.5 |
C8—C9—C10 | 132.9 (4) | N5—C37—H37A | 105.3 |
C11—C10—C9 | 107.7 (3) | N5—C37—H37B | 113.5 |
C11—C10—H10 | 126.1 | H37A—C37—H37B | 109.5 |
C9—C10—H10 | 126.1 | N5—C37—H37C | 109.4 |
C12—C11—C10 | 107.5 (3) | H37A—C37—H37C | 109.5 |
C12—C11—H11 | 126.3 | H37B—C37—H37C | 109.5 |
C10—C11—H11 | 126.3 | N5—C38—H38A | 109.5 |
O4—C12—C11 | 108.6 (3) | N5—C38—H38B | 109.5 |
O4—C12—H12 | 125.7 | H38A—C38—H38B | 109.5 |
C11—C12—H12 | 125.7 | N5—C38—H38C | 109.5 |
C14—C13—N4 | 114.4 (3) | H38A—C38—H38C | 109.5 |
C14—C13—H13A | 108.7 | H38B—C38—H38C | 109.5 |
N4—C13—H13A | 108.7 | O13—C39—N5 | 134.0 (4) |
C14—C13—H13B | 108.7 | O13—C39—H39 | 113.0 |
N4—C13—H13B | 108.7 | N5—C39—H39 | 113.0 |
H13A—C13—H13B | 107.6 | O6—Cl1—O8 | 112.53 (16) |
C19—C14—C15 | 118.4 (3) | O6—Cl1—O7 | 110.80 (16) |
C19—C14—C13 | 119.1 (3) | O8—Cl1—O7 | 107.67 (15) |
C15—C14—C13 | 122.4 (3) | O6—Cl1—O5 | 105.88 (16) |
C16—C15—C14 | 120.6 (3) | O8—Cl1—O5 | 110.25 (15) |
C16—C15—H15 | 119.7 | O7—Cl1—O5 | 109.70 (14) |
C14—C15—H15 | 119.7 | O12—Cl2—O11 | 97.51 (18) |
C15—C16—C17 | 119.6 (3) | O12—Cl2—O10 | 110.09 (16) |
C15—C16—C20 | 119.9 (3) | O11—Cl2—O10 | 110.63 (17) |
C17—C16—C20 | 120.4 (3) | O12—Cl2—O9 | 109.78 (18) |
C18—C17—C16 | 120.3 (3) | O11—Cl2—O9 | 118.27 (17) |
C18—C17—H17 | 119.8 | O10—Cl2—O9 | 109.83 (16) |
C16—C17—H17 | 119.8 | N1—Cu1—O1 | 94.77 (12) |
C17—C18—C19 | 119.7 (3) | N1—Cu1—O2 | 177.19 (11) |
C17—C18—C21 | 115.3 (3) | O1—Cu1—O2 | 86.75 (10) |
C19—C18—C21 | 125.0 (3) | N1—Cu1—N2 | 84.82 (14) |
O2—C19—C18 | 123.6 (3) | O1—Cu1—N2 | 175.49 (12) |
O2—C19—C14 | 115.1 (3) | O2—Cu1—N2 | 93.49 (12) |
C18—C19—C14 | 121.3 (3) | C28—N1—C27 | 124.9 (3) |
C16—C20—H20A | 109.5 | C28—N1—Cu1 | 122.6 (3) |
C16—C20—H20B | 109.5 | C27—N1—Cu1 | 112.4 (2) |
H20A—C20—H20B | 109.5 | C21—N2—C22 | 124.6 (3) |
C16—C20—H20C | 109.5 | C21—N2—Cu1 | 124.1 (3) |
H20A—C20—H20C | 109.5 | C22—N2—Cu1 | 111.3 (2) |
H20B—C20—H20C | 109.5 | C6—N3—C5 | 111.7 (3) |
N2—C21—C18 | 126.6 (4) | C6—N3—C35 | 108.0 (3) |
N2—C21—H21 | 116.7 | C5—N3—C35 | 109.3 (3) |
C18—C21—H21 | 116.7 | C13—N4—C7 | 109.2 (3) |
C27—C22—C23 | 120.2 (4) | C13—N4—C8 | 114.5 (3) |
C27—C22—N2 | 114.8 (3) | C7—N4—C8 | 110.5 (3) |
C23—C22—N2 | 124.9 (3) | C39—N5—C38 | 119.5 (3) |
C22—C23—C24 | 120.2 (4) | C39—N5—C37 | 121.5 (3) |
C22—C23—H23 | 119.9 | C38—N5—C37 | 118.5 (3) |
C24—C23—H23 | 119.9 | C34—O1—Cu1 | 125.8 (2) |
C23—C24—C25 | 120.1 (3) | C34—O1—H1A | 105.9 |
C23—C24—H24 | 119.9 | Cu1—O1—H1A | 105.9 |
C25—C24—H24 | 119.9 | C19—O2—Cu1 | 127.2 (2) |
C26—C25—C24 | 119.3 (4) | C19—O2—H2B | 105.5 |
C26—C25—H25 | 120.3 | Cu1—O2—H2B | 105.5 |
C24—C25—H25 | 120.3 | C4—O3—C1 | 105.9 (2) |
C25—C26—C27 | 122.1 (4) | C9—O4—C12 | 108.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N3 | 0.97 | 1.96 | 2.716 (4) | 133 |
O1—H1A···O7 | 0.97 | 2.39 | 3.221 (3) | 144 |
O2—H2B···N4 | 0.97 | 2.10 | 2.832 (4) | 131 |
O2—H2B···O7 | 0.97 | 2.36 | 3.230 (3) | 148 |