Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011973/hg6037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011973/hg6037Isup2.hkl |
CCDC reference: 242280
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker,1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Cu(C22H24N6O2)] | F(000) = 972 |
Mr = 468.01 | Dx = 1.523 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2yn | Cell parameters from 755 reflections |
a = 13.178 (7) Å | θ = 2.5–23.1° |
b = 11.587 (6) Å | µ = 1.10 mm−1 |
c = 14.516 (7) Å | T = 293 K |
β = 112.949 (8)° | Block, green |
V = 2041.0 (18) Å3 | 0.26 × 0.24 × 0.20 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 4174 independent reflections |
Radiation source: fine-focus sealed tube | 2632 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
φ and ω scans | θmax = 26.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→16 |
Tmin = 0.650, Tmax = 0.802 | k = −13→14 |
11388 measured reflections | l = −18→16 |
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)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.138 | w = 1/[σ2(Fo2) + (0.0669P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.002 |
4174 reflections | Δρmax = 0.60 e Å−3 |
281 parameters | Δρmin = −0.57 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0131 (10) |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.42186 (4) | 0.17408 (5) | 0.36350 (3) | 0.0294 (2) | |
N1 | 0.3908 (3) | 0.2070 (3) | 0.4848 (2) | 0.0279 (8) | |
N2 | 0.5712 (3) | 0.1472 (3) | 0.4628 (2) | 0.0288 (8) | |
N3 | 0.4982 (3) | 0.3030 (3) | 0.2797 (2) | 0.0322 (8) | |
N5 | 0.4247 (3) | 0.0713 (3) | 0.2435 (2) | 0.0292 (8) | |
H5 | 0.4512 | 0.0008 | 0.2692 | 0.035* | |
N6 | 0.2670 (3) | 0.1939 (3) | 0.2766 (2) | 0.0294 (8) | |
N4 | 0.5996 (3) | 0.4019 (4) | 0.4246 (3) | 0.0527 (11) | |
H4A | 0.6419 | 0.4050 | 0.4871 | 0.063* | |
O1 | 0.4624 (2) | 0.1405 (3) | 0.6496 (2) | 0.0385 (8) | |
O2 | 0.6506 (2) | 0.0813 (3) | 0.6268 (2) | 0.0399 (8) | |
C1 | 0.4667 (3) | 0.1574 (3) | 0.5669 (3) | 0.0271 (9) | |
C2 | 0.5737 (3) | 0.1209 (4) | 0.5534 (3) | 0.0287 (9) | |
C3 | 0.6688 (3) | 0.1400 (4) | 0.4429 (3) | 0.0317 (10) | |
C4 | 0.7420 (3) | 0.0474 (4) | 0.4748 (3) | 0.0387 (11) | |
H4 | 0.7295 | −0.0110 | 0.5131 | 0.046* | |
C5 | 0.8331 (4) | 0.0420 (5) | 0.4500 (4) | 0.0551 (14) | |
H5A | 0.8804 | −0.0210 | 0.4701 | 0.066* | |
C6 | 0.8542 (4) | 0.1293 (5) | 0.3959 (4) | 0.0605 (16) | |
H6 | 0.9160 | 0.1260 | 0.3799 | 0.073* | |
C7 | 0.7834 (4) | 0.2216 (5) | 0.3654 (4) | 0.0522 (14) | |
H7 | 0.7987 | 0.2809 | 0.3297 | 0.063* | |
C8 | 0.6894 (3) | 0.2287 (4) | 0.3866 (3) | 0.0371 (11) | |
C9 | 0.6140 (3) | 0.3315 (4) | 0.3484 (3) | 0.0405 (11) | |
H9 | 0.6455 | 0.3807 | 0.3113 | 0.049* | |
C10 | 0.4971 (4) | 0.4673 (4) | 0.3729 (4) | 0.0532 (13) | |
H10A | 0.5129 | 0.5489 | 0.3713 | 0.064* | |
H10B | 0.4471 | 0.4575 | 0.4067 | 0.064* | |
C11 | 0.4466 (4) | 0.4181 (4) | 0.2666 (3) | 0.0431 (12) | |
H11A | 0.3670 | 0.4123 | 0.2432 | 0.052* | |
H11B | 0.4654 | 0.4648 | 0.2201 | 0.052* | |
C12 | 0.4894 (4) | 0.2478 (4) | 0.1861 (3) | 0.0417 (12) | |
H12A | 0.5477 | 0.2762 | 0.1670 | 0.050* | |
H12B | 0.4194 | 0.2682 | 0.1334 | 0.050* | |
C13 | 0.4979 (4) | 0.1171 (4) | 0.1967 (3) | 0.0391 (11) | |
H13A | 0.4782 | 0.0825 | 0.1312 | 0.047* | |
H13B | 0.5734 | 0.0959 | 0.2372 | 0.047* | |
C14 | 0.3085 (3) | 0.0550 (4) | 0.1735 (3) | 0.0340 (10) | |
H14A | 0.2776 | −0.0114 | 0.1940 | 0.041* | |
H14B | 0.3055 | 0.0404 | 0.1067 | 0.041* | |
C15 | 0.2415 (3) | 0.1608 (4) | 0.1723 (3) | 0.0329 (10) | |
H15A | 0.2602 | 0.2232 | 0.1372 | 0.039* | |
H15B | 0.1635 | 0.1442 | 0.1385 | 0.039* | |
C16 | 0.1885 (3) | 0.2250 (4) | 0.3012 (3) | 0.0304 (10) | |
H16 | 0.1182 | 0.2246 | 0.2508 | 0.037* | |
C17 | 0.1973 (3) | 0.2613 (4) | 0.4000 (3) | 0.0302 (10) | |
C18 | 0.1001 (4) | 0.3081 (4) | 0.4035 (3) | 0.0399 (11) | |
H18 | 0.0363 | 0.3099 | 0.3454 | 0.048* | |
C19 | 0.0974 (4) | 0.3510 (4) | 0.4902 (4) | 0.0475 (13) | |
H19 | 0.0328 | 0.3817 | 0.4914 | 0.057* | |
C20 | 0.1928 (4) | 0.3478 (4) | 0.5763 (4) | 0.0496 (13) | |
H20 | 0.1922 | 0.3783 | 0.6354 | 0.060* | |
C21 | 0.2886 (4) | 0.3002 (4) | 0.5762 (3) | 0.0407 (11) | |
H21 | 0.3511 | 0.2979 | 0.6354 | 0.049* | |
C22 | 0.2936 (3) | 0.2551 (3) | 0.4882 (3) | 0.0300 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0237 (3) | 0.0419 (3) | 0.0213 (3) | 0.0024 (2) | 0.0073 (2) | 0.0005 (2) |
N1 | 0.0225 (18) | 0.036 (2) | 0.0238 (18) | 0.0000 (15) | 0.0073 (14) | 0.0022 (14) |
N2 | 0.0212 (18) | 0.036 (2) | 0.0265 (18) | −0.0016 (14) | 0.0063 (14) | 0.0007 (15) |
N3 | 0.0301 (19) | 0.037 (2) | 0.0279 (19) | 0.0009 (15) | 0.0092 (15) | 0.0030 (15) |
N5 | 0.0317 (19) | 0.034 (2) | 0.0210 (17) | 0.0036 (15) | 0.0087 (15) | 0.0051 (15) |
N6 | 0.0266 (19) | 0.037 (2) | 0.0216 (17) | 0.0024 (15) | 0.0058 (14) | 0.0024 (15) |
N4 | 0.046 (2) | 0.054 (3) | 0.037 (2) | 0.003 (2) | −0.0062 (19) | −0.007 (2) |
O1 | 0.0382 (18) | 0.053 (2) | 0.0251 (16) | 0.0018 (14) | 0.0138 (13) | 0.0037 (13) |
O2 | 0.0297 (17) | 0.054 (2) | 0.0287 (16) | 0.0045 (14) | 0.0035 (13) | 0.0102 (15) |
C1 | 0.025 (2) | 0.026 (2) | 0.027 (2) | −0.0062 (17) | 0.0074 (17) | −0.0016 (18) |
C2 | 0.026 (2) | 0.029 (2) | 0.025 (2) | −0.0042 (18) | 0.0035 (18) | 0.0014 (18) |
C3 | 0.025 (2) | 0.040 (3) | 0.027 (2) | −0.0044 (18) | 0.0067 (18) | −0.0038 (18) |
C4 | 0.028 (2) | 0.044 (3) | 0.040 (3) | 0.000 (2) | 0.009 (2) | 0.001 (2) |
C5 | 0.033 (3) | 0.064 (4) | 0.069 (4) | 0.011 (2) | 0.020 (3) | 0.004 (3) |
C6 | 0.030 (3) | 0.084 (4) | 0.076 (4) | 0.002 (3) | 0.030 (3) | 0.007 (3) |
C7 | 0.032 (3) | 0.067 (4) | 0.061 (3) | −0.001 (2) | 0.022 (2) | 0.014 (3) |
C8 | 0.029 (2) | 0.043 (3) | 0.037 (3) | −0.006 (2) | 0.011 (2) | 0.002 (2) |
C9 | 0.033 (3) | 0.046 (3) | 0.040 (3) | −0.004 (2) | 0.012 (2) | 0.006 (2) |
C10 | 0.055 (3) | 0.039 (3) | 0.060 (3) | 0.002 (2) | 0.016 (3) | −0.002 (3) |
C11 | 0.041 (3) | 0.042 (3) | 0.044 (3) | 0.004 (2) | 0.014 (2) | 0.009 (2) |
C12 | 0.044 (3) | 0.057 (3) | 0.028 (2) | −0.006 (2) | 0.019 (2) | 0.004 (2) |
C13 | 0.041 (3) | 0.052 (3) | 0.033 (2) | −0.005 (2) | 0.023 (2) | −0.009 (2) |
C14 | 0.035 (2) | 0.038 (3) | 0.027 (2) | −0.0020 (19) | 0.0093 (19) | −0.0038 (19) |
C15 | 0.029 (2) | 0.041 (3) | 0.024 (2) | 0.0011 (19) | 0.0041 (17) | −0.0010 (19) |
C16 | 0.024 (2) | 0.035 (2) | 0.027 (2) | 0.0026 (18) | 0.0048 (18) | 0.0045 (19) |
C17 | 0.029 (2) | 0.033 (3) | 0.030 (2) | 0.0006 (18) | 0.0132 (19) | 0.0038 (19) |
C18 | 0.033 (2) | 0.050 (3) | 0.040 (3) | 0.003 (2) | 0.018 (2) | 0.010 (2) |
C19 | 0.039 (3) | 0.066 (4) | 0.050 (3) | 0.013 (2) | 0.031 (2) | 0.010 (3) |
C20 | 0.056 (3) | 0.061 (4) | 0.042 (3) | 0.004 (3) | 0.031 (3) | −0.006 (2) |
C21 | 0.038 (3) | 0.054 (3) | 0.032 (2) | 0.000 (2) | 0.016 (2) | −0.006 (2) |
C22 | 0.033 (2) | 0.029 (2) | 0.033 (2) | −0.0053 (18) | 0.0175 (19) | 0.0019 (19) |
Cu1—N6 | 1.950 (3) | C7—C8 | 1.390 (6) |
Cu1—N2 | 1.958 (3) | C7—H7 | 0.9300 |
Cu1—N1 | 1.994 (3) | C8—C9 | 1.511 (6) |
Cu1—N5 | 2.122 (3) | C9—H9 | 0.9800 |
Cu1—N3 | 2.383 (3) | C10—C11 | 1.533 (6) |
N1—C1 | 1.349 (5) | C10—H10A | 0.9700 |
N1—C22 | 1.415 (5) | C10—H10B | 0.9700 |
N2—C2 | 1.338 (5) | C11—H11A | 0.9700 |
N2—C3 | 1.427 (5) | C11—H11B | 0.9700 |
N3—C12 | 1.465 (5) | C12—C13 | 1.522 (7) |
N3—C11 | 1.475 (6) | C12—H12A | 0.9700 |
N3—C9 | 1.498 (5) | C12—H12B | 0.9700 |
N5—C13 | 1.478 (5) | C13—H13A | 0.9700 |
N5—C14 | 1.483 (5) | C13—H13B | 0.9700 |
N5—H5 | 0.9100 | C14—C15 | 1.507 (6) |
N6—C16 | 1.271 (5) | C14—H14A | 0.9700 |
N6—C15 | 1.468 (5) | C14—H14B | 0.9700 |
N4—C9 | 1.446 (6) | C15—H15A | 0.9700 |
N4—C10 | 1.473 (6) | C15—H15B | 0.9700 |
N4—H4A | 0.8600 | C16—C17 | 1.456 (6) |
O1—C1 | 1.239 (5) | C16—H16 | 0.9300 |
O2—C2 | 1.237 (5) | C17—C22 | 1.409 (5) |
C1—C2 | 1.556 (6) | C17—C18 | 1.410 (6) |
C3—C4 | 1.396 (6) | C18—C19 | 1.366 (6) |
C3—C8 | 1.404 (6) | C18—H18 | 0.9300 |
C4—C5 | 1.383 (6) | C19—C20 | 1.385 (7) |
C4—H4 | 0.9300 | C19—H19 | 0.9300 |
C5—C6 | 1.375 (7) | C20—C21 | 1.379 (6) |
C5—H5A | 0.9300 | C20—H20 | 0.9300 |
C6—C7 | 1.374 (7) | C21—C22 | 1.405 (6) |
C6—H6 | 0.9300 | C21—H21 | 0.9300 |
N6—Cu1—N2 | 173.14 (14) | N4—C9—H9 | 107.6 |
N6—Cu1—N1 | 91.47 (13) | N3—C9—H9 | 107.6 |
N2—Cu1—N1 | 82.72 (13) | C8—C9—H9 | 107.6 |
N6—Cu1—N5 | 83.33 (13) | N4—C10—C11 | 105.9 (4) |
N2—Cu1—N5 | 100.43 (13) | N4—C10—H10A | 110.6 |
N1—Cu1—N5 | 155.18 (14) | C11—C10—H10A | 110.6 |
N6—Cu1—N3 | 98.02 (13) | N4—C10—H10B | 110.6 |
N2—Cu1—N3 | 88.42 (13) | C11—C10—H10B | 110.6 |
N1—Cu1—N3 | 127.12 (13) | H10A—C10—H10B | 108.7 |
N5—Cu1—N3 | 77.69 (13) | N3—C11—C10 | 102.1 (4) |
C1—N1—C22 | 120.5 (3) | N3—C11—H11A | 111.4 |
C1—N1—Cu1 | 111.2 (3) | C10—C11—H11A | 111.4 |
C22—N1—Cu1 | 127.3 (3) | N3—C11—H11B | 111.4 |
C2—N2—C3 | 120.5 (3) | C10—C11—H11B | 111.4 |
C2—N2—Cu1 | 113.1 (3) | H11A—C11—H11B | 109.2 |
C3—N2—Cu1 | 125.9 (3) | N3—C12—C13 | 111.4 (3) |
C12—N3—C11 | 114.2 (3) | N3—C12—H12A | 109.4 |
C12—N3—C9 | 113.9 (3) | C13—C12—H12A | 109.4 |
C11—N3—C9 | 100.7 (3) | N3—C12—H12B | 109.4 |
C12—N3—Cu1 | 107.6 (3) | C13—C12—H12B | 109.4 |
C11—N3—Cu1 | 111.5 (3) | H12A—C12—H12B | 108.0 |
C9—N3—Cu1 | 108.7 (2) | N5—C13—C12 | 111.6 (3) |
C13—N5—C14 | 114.5 (3) | N5—C13—H13A | 109.3 |
C13—N5—Cu1 | 113.5 (3) | C12—C13—H13A | 109.3 |
C14—N5—Cu1 | 106.9 (2) | N5—C13—H13B | 109.3 |
C13—N5—H5 | 107.2 | C12—C13—H13B | 109.3 |
C14—N5—H5 | 107.2 | H13A—C13—H13B | 108.0 |
Cu1—N5—H5 | 107.2 | N5—C14—C15 | 110.3 (3) |
C16—N6—C15 | 118.7 (3) | N5—C14—H14A | 109.6 |
C16—N6—Cu1 | 127.8 (3) | C15—C14—H14A | 109.6 |
C15—N6—Cu1 | 113.4 (3) | N5—C14—H14B | 109.6 |
C9—N4—C10 | 105.6 (4) | C15—C14—H14B | 109.6 |
C9—N4—H4A | 127.2 | H14A—C14—H14B | 108.1 |
C10—N4—H4A | 127.2 | N6—C15—C14 | 107.7 (3) |
O1—C1—N1 | 128.6 (4) | N6—C15—H15A | 110.2 |
O1—C1—C2 | 117.7 (3) | C14—C15—H15A | 110.2 |
N1—C1—C2 | 113.7 (3) | N6—C15—H15B | 110.2 |
O2—C2—N2 | 129.0 (4) | C14—C15—H15B | 110.2 |
O2—C2—C1 | 118.1 (4) | H15A—C15—H15B | 108.5 |
N2—C2—C1 | 112.6 (3) | N6—C16—C17 | 126.7 (4) |
C4—C3—C8 | 119.4 (4) | N6—C16—H16 | 116.6 |
C4—C3—N2 | 122.6 (4) | C17—C16—H16 | 116.6 |
C8—C3—N2 | 118.0 (4) | C22—C17—C18 | 119.7 (4) |
C5—C4—C3 | 120.4 (4) | C22—C17—C16 | 125.3 (4) |
C5—C4—H4 | 119.8 | C18—C17—C16 | 115.0 (4) |
C3—C4—H4 | 119.8 | C19—C18—C17 | 121.5 (4) |
C6—C5—C4 | 120.4 (5) | C19—C18—H18 | 119.3 |
C6—C5—H5A | 119.8 | C17—C18—H18 | 119.3 |
C4—C5—H5A | 119.8 | C18—C19—C20 | 118.8 (4) |
C7—C6—C5 | 119.5 (5) | C18—C19—H19 | 120.6 |
C7—C6—H6 | 120.2 | C20—C19—H19 | 120.6 |
C5—C6—H6 | 120.2 | C21—C20—C19 | 121.3 (4) |
C6—C7—C8 | 121.8 (5) | C21—C20—H20 | 119.4 |
C6—C7—H7 | 119.1 | C19—C20—H20 | 119.4 |
C8—C7—H7 | 119.1 | C20—C21—C22 | 121.1 (4) |
C7—C8—C3 | 118.5 (4) | C20—C21—H21 | 119.4 |
C7—C8—C9 | 118.7 (4) | C22—C21—H21 | 119.4 |
C3—C8—C9 | 122.8 (4) | C21—C22—C17 | 117.5 (4) |
N4—C9—N3 | 103.3 (3) | C21—C22—N1 | 122.7 (4) |
N4—C9—C8 | 115.3 (4) | C17—C22—N1 | 119.7 (4) |
N3—C9—C8 | 115.1 (4) | ||
N6—Cu1—N1—C1 | 154.4 (3) | N2—C3—C4—C5 | 177.3 (4) |
N2—Cu1—N1—C1 | −21.9 (3) | C3—C4—C5—C6 | 1.8 (8) |
N5—Cu1—N1—C1 | 77.2 (4) | C4—C5—C6—C7 | −0.7 (8) |
N3—Cu1—N1—C1 | −104.4 (3) | C5—C6—C7—C8 | −0.9 (9) |
N6—Cu1—N1—C22 | −13.6 (3) | C6—C7—C8—C3 | 1.6 (8) |
N2—Cu1—N1—C22 | 170.1 (3) | C6—C7—C8—C9 | −178.5 (5) |
N5—Cu1—N1—C22 | −90.8 (4) | C4—C3—C8—C7 | −0.5 (6) |
N3—Cu1—N1—C22 | 87.6 (3) | N2—C3—C8—C7 | −179.0 (4) |
N1—Cu1—N2—C2 | 23.0 (3) | C4—C3—C8—C9 | 179.5 (4) |
N5—Cu1—N2—C2 | −132.1 (3) | N2—C3—C8—C9 | 1.0 (6) |
N3—Cu1—N2—C2 | 150.8 (3) | C10—N4—C9—N3 | −33.6 (5) |
N1—Cu1—N2—C3 | −165.1 (3) | C10—N4—C9—C8 | −160.1 (4) |
N5—Cu1—N2—C3 | 39.9 (3) | C12—N3—C9—N4 | 170.2 (3) |
N3—Cu1—N2—C3 | −37.3 (3) | C11—N3—C9—N4 | 47.5 (4) |
N6—Cu1—N3—C12 | −73.0 (3) | Cu1—N3—C9—N4 | −69.8 (3) |
N2—Cu1—N3—C12 | 109.3 (3) | C12—N3—C9—C8 | −63.3 (5) |
N1—Cu1—N3—C12 | −171.0 (2) | C11—N3—C9—C8 | 174.0 (4) |
N5—Cu1—N3—C12 | 8.3 (3) | Cu1—N3—C9—C8 | 56.7 (4) |
N6—Cu1—N3—C11 | 53.0 (3) | C7—C8—C9—N4 | −119.6 (5) |
N2—Cu1—N3—C11 | −124.7 (3) | C3—C8—C9—N4 | 60.3 (6) |
N1—Cu1—N3—C11 | −45.0 (3) | C7—C8—C9—N3 | 120.2 (5) |
N5—Cu1—N3—C11 | 134.3 (3) | C3—C8—C9—N3 | −59.8 (6) |
N6—Cu1—N3—C9 | 163.1 (3) | C9—N4—C10—C11 | 7.4 (5) |
N2—Cu1—N3—C9 | −14.5 (3) | C12—N3—C11—C10 | −163.9 (4) |
N1—Cu1—N3—C9 | 65.1 (3) | C9—N3—C11—C10 | −41.4 (4) |
N5—Cu1—N3—C9 | −115.5 (3) | Cu1—N3—C11—C10 | 73.8 (4) |
N6—Cu1—N5—C13 | 117.0 (3) | N4—C10—C11—N3 | 21.8 (5) |
N2—Cu1—N5—C13 | −68.8 (3) | C11—N3—C12—C13 | −155.8 (4) |
N1—Cu1—N5—C13 | −164.1 (3) | C9—N3—C12—C13 | 89.2 (4) |
N3—Cu1—N5—C13 | 17.2 (3) | Cu1—N3—C12—C13 | −31.4 (4) |
N6—Cu1—N5—C14 | −10.3 (2) | C14—N5—C13—C12 | 82.5 (4) |
N2—Cu1—N5—C14 | 163.9 (2) | Cu1—N5—C13—C12 | −40.7 (4) |
N1—Cu1—N5—C14 | 68.7 (4) | N3—C12—C13—N5 | 48.5 (5) |
N3—Cu1—N5—C14 | −110.1 (3) | C13—N5—C14—C15 | −92.9 (4) |
N1—Cu1—N6—C16 | 4.4 (4) | Cu1—N5—C14—C15 | 33.8 (4) |
N5—Cu1—N6—C16 | 160.0 (4) | C16—N6—C15—C14 | −137.8 (4) |
N3—Cu1—N6—C16 | −123.5 (4) | Cu1—N6—C15—C14 | 38.5 (4) |
N1—Cu1—N6—C15 | −171.5 (3) | N5—C14—C15—N6 | −47.4 (4) |
N5—Cu1—N6—C15 | −15.9 (3) | C15—N6—C16—C17 | −179.6 (4) |
N3—Cu1—N6—C15 | 60.6 (3) | Cu1—N6—C16—C17 | 4.7 (6) |
C22—N1—C1—O1 | 4.3 (6) | N6—C16—C17—C22 | −7.9 (7) |
Cu1—N1—C1—O1 | −164.7 (3) | N6—C16—C17—C18 | 170.7 (4) |
C22—N1—C1—C2 | −173.9 (3) | C22—C17—C18—C19 | 1.9 (7) |
Cu1—N1—C1—C2 | 17.2 (4) | C16—C17—C18—C19 | −176.8 (4) |
C3—N2—C2—O2 | −5.4 (7) | C17—C18—C19—C20 | −0.1 (7) |
Cu1—N2—C2—O2 | 167.0 (4) | C18—C19—C20—C21 | −1.4 (7) |
C3—N2—C2—C1 | 168.4 (3) | C19—C20—C21—C22 | 1.2 (7) |
Cu1—N2—C2—C1 | −19.2 (4) | C20—C21—C22—C17 | 0.6 (6) |
O1—C1—C2—O2 | −2.9 (6) | C20—C21—C22—N1 | 179.1 (4) |
N1—C1—C2—O2 | 175.5 (4) | C18—C17—C22—C21 | −2.1 (6) |
O1—C1—C2—N2 | −177.5 (4) | C16—C17—C22—C21 | 176.5 (4) |
N1—C1—C2—N2 | 0.9 (5) | C18—C17—C22—N1 | 179.4 (4) |
C2—N2—C3—C4 | 43.7 (6) | C16—C17—C22—N1 | −2.1 (6) |
Cu1—N2—C3—C4 | −127.7 (4) | C1—N1—C22—C21 | 28.5 (6) |
C2—N2—C3—C8 | −137.9 (4) | Cu1—N1—C22—C21 | −164.5 (3) |
Cu1—N2—C3—C8 | 50.7 (5) | C1—N1—C22—C17 | −153.0 (4) |
C8—C3—C4—C5 | −1.1 (7) | Cu1—N1—C22—C17 | 14.0 (5) |