The Cu atom in the title complex, [Cu(C25H20N3O2)2(H2O)], has a distorted trigonal-bipyramidal coordination environment, with two O atoms of the pyrazolone rings and a water O atom in the equatorial plane and two N atoms in axial positions [N—Cu—N = 159.34 (16)°]. The complex occupies a special position on a twofold axis running through the Cu atom and the water O atom. The Cu—O(H2O) bond [2.549 (4) Å] is substantially longer than the rest of the bonds in the coordination polyhedron [Cu—O = 1.919 (2) Å and Cu—N = 1.990 (3) Å]. The pyrazolone ring is almost coplanar with the adjacent chelate ring, the dihedral angle formed by the mean plane of the pyrazolone ring and the planar part of the chelate ring being 2.91 (3)°.
Supporting information
CCDC reference: 206745
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- H-atom completeness 96%
- R factor = 0.055
- wR factor = 0.096
- Data-to-parameter ratio = 10.4
checkCIF results
No syntax errors found
Structure: I
------------
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_031 Alert C Refined Extinction Parameter within Range .... 2.67 Sigma
PLAT_733 Alert C Torsion Calc -94.5(5), Rep -94.5(2) .... 2.50 su-Ratio
N3 -CU1 -N3 -C21 2.556 1.555 1.555 1.555
General Notes
FORMU_01 There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C50 H42 Cu1 N6 O5
Atom count from the _atom_site data: C50 H40 Cu1 N6 O5
CELLZ_01
From the CIF: _cell_formula_units_Z 4
From the CIF: _chemical_formula_sum C50 H42 Cu1 N6 O5
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 200.00 200.00 0.00
H 168.00 160.00 8.00
Cu 4.00 4.00 0.00
N 24.00 24.00 0.00
O 20.00 20.00 0.00
Difference between formula and atom_site contents detected.
WARNING: H atoms missing from atom site list. Is this intentional?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
[Cu(C25H20N3O2)2(H2O)] | F(000) = 1804 |
Mr = 870.35 | Dx = 1.359 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -c_2yc | Cell parameters from 790 reflections |
a = 22.652 (6) Å | θ = 2.3–20.9° |
b = 16.228 (5) Å | µ = 0.57 mm−1 |
c = 15.250 (5) Å | T = 293 K |
β = 130.636 (14)° | Block, dark brown |
V = 4254 (2) Å3 | 0.28 × 0.25 × 0.22 mm |
Z = 4 | |
Data collection top
Bruker SMART 1000 CCD area-detector diffractometer | 2050 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.085 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
φ and ω scans | h = −26→25 |
8399 measured reflections | k = −17→19 |
3765 independent reflections | l = −9→18 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | All H-atom parameters refined |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0266P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max = 0.001 |
3765 reflections | Δρmax = 0.27 e Å−3 |
362 parameters | Δρmin = −0.27 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: 0.00032 (12) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.0000 | 0.09200 (4) | 0.7500 | 0.0401 (2) | |
O1 | −0.09991 (13) | 0.05602 (14) | 0.6943 (2) | 0.0406 (7) | |
O2 | 0.40733 (17) | 0.17267 (19) | 1.2790 (3) | 0.0750 (10) | |
O3 | 0.0000 | 0.2490 (3) | 0.7500 | 0.1107 (19) | |
N1 | −0.20429 (16) | 0.08790 (18) | 0.6838 (3) | 0.0391 (7) | |
N2 | −0.21891 (19) | 0.12959 (18) | 0.7478 (3) | 0.0478 (9) | |
N3 | 0.03848 (16) | 0.11400 (16) | 0.9081 (2) | 0.0377 (8) | |
C1 | −0.1266 (2) | 0.0878 (2) | 0.7393 (3) | 0.0358 (9) | |
C2 | −0.0889 (2) | 0.1281 (2) | 0.8451 (3) | 0.0368 (9) | |
C3 | −0.1504 (2) | 0.1537 (2) | 0.8425 (4) | 0.0443 (10) | |
C4 | −0.1472 (4) | 0.2012 (5) | 0.9301 (6) | 0.0728 (17) | |
H41 | −0.131 (3) | 0.171 (3) | 0.988 (4) | 0.08 (2)* | |
H42 | −0.197 (2) | 0.220 (2) | 0.897 (4) | 0.084 (17)* | |
H43 | −0.115 (3) | 0.251 (3) | 0.956 (4) | 0.099 (19)* | |
C5 | −0.0068 (2) | 0.1357 (2) | 0.9301 (3) | 0.0368 (9) | |
C6 | 0.3683 (3) | 0.1221 (3) | 1.2788 (4) | 0.0589 (13) | |
C7 | 0.4042 (4) | 0.0625 (6) | 1.3743 (7) | 0.100 (3) | |
H71 | 0.385 (3) | 0.065 (3) | 1.411 (5) | 0.11 (2)* | |
H72 | 0.452 (3) | 0.067 (3) | 1.417 (4) | 0.088 (19)* | |
H73 | 0.400 (3) | 0.007 (3) | 1.354 (5) | 0.13 (3)* | |
C11 | −0.2661 (2) | 0.0499 (2) | 0.5792 (3) | 0.0402 (10) | |
C12 | −0.3402 (3) | 0.0829 (3) | 0.5114 (4) | 0.0542 (12) | |
H12 | −0.343 (2) | 0.130 (2) | 0.543 (3) | 0.052 (13)* | |
C13 | −0.4011 (3) | 0.0454 (4) | 0.4109 (5) | 0.0671 (14) | |
H13 | −0.451 (2) | 0.070 (2) | 0.369 (3) | 0.067 (14)* | |
C14 | −0.3895 (3) | −0.0247 (4) | 0.3758 (5) | 0.0816 (17) | |
H14 | −0.429 (2) | −0.046 (2) | 0.304 (4) | 0.069 (14)* | |
C15 | −0.3166 (3) | −0.0573 (4) | 0.4415 (5) | 0.0917 (19) | |
H15 | −0.307 (3) | −0.107 (3) | 0.418 (4) | 0.096 (18)* | |
C16 | −0.2551 (3) | −0.0209 (3) | 0.5427 (5) | 0.0707 (15) | |
H16 | −0.208 (2) | −0.045 (2) | 0.588 (3) | 0.062 (13)* | |
C21 | 0.1214 (2) | 0.1153 (2) | 1.0021 (3) | 0.0393 (10) | |
C22 | 0.1663 (3) | 0.1778 (3) | 1.0095 (4) | 0.0464 (11) | |
H22 | 0.1427 (19) | 0.219 (2) | 0.955 (3) | 0.044 (12)* | |
C23 | 0.2449 (3) | 0.1792 (3) | 1.0989 (4) | 0.0498 (12) | |
H23 | 0.2729 (19) | 0.221 (2) | 1.105 (3) | 0.041 (11)* | |
C24 | 0.2823 (2) | 0.1187 (2) | 1.1824 (3) | 0.0455 (10) | |
C25 | 0.2372 (3) | 0.0554 (3) | 1.1733 (4) | 0.0569 (12) | |
H25 | 0.260 (2) | 0.012 (2) | 1.224 (3) | 0.056 (13)* | |
C26 | 0.1581 (3) | 0.0540 (3) | 1.0834 (4) | 0.0528 (12) | |
H26 | 0.1270 (19) | 0.014 (2) | 1.074 (3) | 0.048 (12)* | |
C31 | 0.0281 (2) | 0.1687 (2) | 1.0465 (3) | 0.0385 (9) | |
C32 | 0.0365 (2) | 0.1214 (3) | 1.1283 (4) | 0.0490 (11) | |
H32 | 0.020 (2) | 0.066 (2) | 1.112 (3) | 0.057 (13)* | |
C33 | 0.0701 (3) | 0.1527 (4) | 1.2355 (4) | 0.0612 (13) | |
H33 | 0.122 (3) | 0.255 (3) | 1.342 (4) | 0.100 (16)* | |
C34 | 0.0953 (3) | 0.2324 (4) | 1.2616 (5) | 0.0783 (16) | |
H34 | 0.071 (2) | 0.117 (2) | 1.283 (3) | 0.070 (15)* | |
C35 | 0.0886 (3) | 0.2803 (4) | 1.1821 (5) | 0.0844 (18) | |
H35 | 0.105 (2) | 0.335 (3) | 1.195 (4) | 0.083 (16)* | |
C36 | 0.0553 (3) | 0.2490 (3) | 1.0747 (4) | 0.0613 (13) | |
H36 | 0.044 (2) | 0.278 (2) | 1.015 (3) | 0.068 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0367 (4) | 0.0523 (5) | 0.0338 (5) | 0.000 | 0.0241 (4) | 0.000 |
O1 | 0.0370 (15) | 0.0500 (16) | 0.0376 (17) | −0.0061 (12) | 0.0256 (15) | −0.0079 (12) |
O2 | 0.052 (2) | 0.091 (2) | 0.078 (3) | −0.0309 (18) | 0.041 (2) | −0.0203 (19) |
O3 | 0.150 (5) | 0.071 (3) | 0.161 (6) | 0.000 | 0.123 (5) | 0.000 |
N1 | 0.0343 (19) | 0.0456 (19) | 0.035 (2) | −0.0032 (17) | 0.0217 (18) | −0.0022 (18) |
N2 | 0.050 (2) | 0.049 (2) | 0.056 (2) | −0.0067 (17) | 0.039 (2) | −0.0063 (18) |
N3 | 0.0326 (18) | 0.049 (2) | 0.0333 (19) | −0.0104 (15) | 0.0221 (18) | −0.0074 (15) |
C1 | 0.036 (2) | 0.032 (2) | 0.040 (2) | −0.001 (2) | 0.025 (2) | 0.004 (2) |
C2 | 0.041 (2) | 0.035 (2) | 0.040 (3) | −0.0086 (18) | 0.029 (2) | −0.0060 (19) |
C3 | 0.051 (3) | 0.043 (2) | 0.049 (3) | −0.007 (2) | 0.038 (3) | −0.007 (2) |
C4 | 0.068 (4) | 0.089 (5) | 0.082 (5) | −0.006 (4) | 0.058 (4) | −0.018 (4) |
C5 | 0.048 (3) | 0.032 (2) | 0.036 (2) | −0.0113 (19) | 0.030 (2) | −0.0016 (18) |
C6 | 0.041 (3) | 0.083 (4) | 0.046 (3) | −0.014 (3) | 0.025 (3) | −0.017 (3) |
C7 | 0.048 (4) | 0.145 (9) | 0.063 (5) | −0.009 (4) | 0.017 (4) | 0.019 (5) |
C11 | 0.036 (3) | 0.044 (2) | 0.038 (3) | −0.004 (2) | 0.023 (2) | 0.003 (2) |
C12 | 0.045 (3) | 0.060 (3) | 0.054 (3) | −0.001 (3) | 0.031 (3) | −0.004 (3) |
C13 | 0.036 (3) | 0.093 (4) | 0.056 (4) | 0.005 (3) | 0.023 (3) | 0.009 (3) |
C14 | 0.035 (3) | 0.124 (5) | 0.047 (4) | −0.013 (3) | 0.010 (3) | −0.020 (4) |
C15 | 0.053 (4) | 0.097 (4) | 0.089 (5) | −0.012 (3) | 0.031 (4) | −0.049 (4) |
C16 | 0.033 (3) | 0.069 (4) | 0.068 (4) | 0.001 (3) | 0.014 (3) | −0.019 (3) |
C21 | 0.042 (2) | 0.049 (3) | 0.032 (2) | −0.013 (2) | 0.026 (2) | −0.011 (2) |
C22 | 0.049 (3) | 0.047 (3) | 0.043 (3) | −0.011 (2) | 0.029 (3) | 0.000 (2) |
C23 | 0.050 (3) | 0.054 (3) | 0.050 (3) | −0.026 (3) | 0.035 (3) | −0.012 (2) |
C24 | 0.046 (3) | 0.055 (3) | 0.039 (3) | −0.013 (2) | 0.030 (2) | −0.006 (2) |
C25 | 0.048 (3) | 0.064 (3) | 0.049 (3) | −0.009 (3) | 0.028 (3) | 0.010 (3) |
C26 | 0.040 (3) | 0.063 (3) | 0.045 (3) | −0.017 (2) | 0.024 (3) | 0.006 (2) |
C31 | 0.042 (2) | 0.040 (2) | 0.038 (3) | −0.010 (2) | 0.029 (2) | −0.008 (2) |
C32 | 0.058 (3) | 0.051 (3) | 0.043 (3) | −0.008 (2) | 0.036 (3) | −0.001 (2) |
C33 | 0.067 (3) | 0.080 (4) | 0.045 (3) | 0.005 (3) | 0.040 (3) | 0.004 (3) |
C34 | 0.092 (4) | 0.088 (4) | 0.048 (4) | −0.024 (3) | 0.043 (4) | −0.026 (3) |
C35 | 0.126 (5) | 0.065 (4) | 0.073 (4) | −0.036 (4) | 0.070 (4) | −0.030 (3) |
C36 | 0.081 (4) | 0.059 (3) | 0.050 (3) | −0.017 (3) | 0.045 (3) | −0.008 (3) |
Geometric parameters (Å, º) top
Cu1—O1i | 1.919 (2) | C12—H12 | 0.93 (3) |
Cu1—O1 | 1.919 (2) | C13—C14 | 1.353 (7) |
Cu1—N3i | 1.990 (3) | C13—H13 | 0.95 (4) |
Cu1—N3 | 1.990 (3) | C14—C15 | 1.363 (7) |
Cu1—O3 | 2.549 (4) | C14—H14 | 0.92 (4) |
O1—C1 | 1.282 (4) | C15—C16 | 1.368 (6) |
O2—C6 | 1.205 (4) | C15—H15 | 0.95 (4) |
N1—C1 | 1.368 (4) | C16—H16 | 0.90 (4) |
N1—N2 | 1.393 (4) | C21—C26 | 1.370 (5) |
N1—C11 | 1.406 (4) | C21—C22 | 1.387 (5) |
N2—C3 | 1.314 (5) | C22—C23 | 1.368 (6) |
N3—C5 | 1.319 (4) | C22—H22 | 0.91 (3) |
N3—C21 | 1.441 (4) | C23—C24 | 1.378 (5) |
C1—C2 | 1.401 (5) | C23—H23 | 0.89 (3) |
C2—C5 | 1.419 (5) | C24—C25 | 1.390 (5) |
C2—C3 | 1.429 (5) | C25—C26 | 1.375 (6) |
C3—C4 | 1.504 (6) | C25—H25 | 0.92 (3) |
C4—H41 | 0.86 (4) | C26—H26 | 0.90 (3) |
C4—H42 | 0.93 (4) | C31—C32 | 1.370 (5) |
C4—H43 | 0.98 (5) | C31—C36 | 1.385 (5) |
C5—C31 | 1.494 (5) | C32—C33 | 1.375 (6) |
C6—C7 | 1.475 (8) | C32—H32 | 0.94 (3) |
C6—C24 | 1.493 (5) | C33—C34 | 1.364 (6) |
C7—H71 | 0.91 (5) | C33—H34 | 0.92 (4) |
C7—H72 | 0.83 (4) | C34—C35 | 1.364 (7) |
C7—H73 | 0.93 (5) | C34—H33 | 1.02 (4) |
C11—C16 | 1.368 (5) | C35—C36 | 1.378 (6) |
C11—C12 | 1.382 (5) | C35—H35 | 0.94 (4) |
C12—C13 | 1.367 (6) | C36—H36 | 0.90 (4) |
| | | |
O1i—Cu1—O1 | 144.56 (14) | C14—C13—C12 | 120.3 (5) |
O1i—Cu1—N3i | 92.89 (10) | C14—C13—H13 | 123 (2) |
O1—Cu1—N3i | 93.37 (11) | C12—C13—H13 | 117 (2) |
O1—Cu1—O3 | 107.72 (12) | C13—C14—C15 | 119.3 (5) |
N3—Cu1—O3i | 79.67 (9) | C13—C14—H14 | 120 (3) |
O1i—Cu1—N3 | 93.37 (11) | C15—C14—H14 | 120 (3) |
O1—Cu1—N3 | 92.89 (10) | C14—C15—C16 | 121.2 (6) |
N3i—Cu1—N3 | 159.34 (16) | C14—C15—H15 | 120 (3) |
C1—O1—Cu1 | 118.2 (2) | C16—C15—H15 | 118 (3) |
C1—N1—N2 | 111.3 (3) | C15—C16—C11 | 120.1 (5) |
C1—N1—C11 | 129.1 (3) | C15—C16—H16 | 120 (3) |
N2—N1—C11 | 119.5 (3) | C11—C16—H16 | 119 (3) |
C3—N2—N1 | 105.3 (3) | C26—C21—C22 | 118.5 (4) |
C5—N3—C21 | 118.0 (3) | C26—C21—N3 | 121.3 (3) |
C5—N3—Cu1 | 123.8 (2) | C22—C21—N3 | 120.2 (4) |
C21—N3—Cu1 | 117.8 (2) | C23—C22—C21 | 120.2 (4) |
O1—C1—N1 | 122.3 (3) | C23—C22—H22 | 120 (2) |
O1—C1—C2 | 131.0 (3) | C21—C22—H22 | 119 (2) |
N1—C1—C2 | 106.7 (3) | C22—C23—C24 | 121.8 (4) |
C1—C2—C5 | 123.2 (3) | C22—C23—H23 | 120 (2) |
C1—C2—C3 | 104.5 (3) | C24—C23—H23 | 119 (2) |
C5—C2—C3 | 132.3 (4) | C23—C24—C25 | 117.7 (4) |
N2—C3—C2 | 112.1 (3) | C23—C24—C6 | 120.4 (4) |
N2—C3—C4 | 117.9 (4) | C25—C24—C6 | 122.0 (4) |
C2—C3—C4 | 130.0 (4) | C26—C25—C24 | 120.6 (4) |
C3—C4—H41 | 111 (3) | C26—C25—H25 | 118 (2) |
C3—C4—H42 | 110 (3) | C24—C25—H25 | 121 (2) |
H41—C4—H42 | 108 (4) | C21—C26—C25 | 121.2 (4) |
C3—C4—H43 | 112 (3) | C21—C26—H26 | 116 (2) |
H41—C4—H43 | 111 (5) | C25—C26—H26 | 123 (2) |
H42—C4—H43 | 106 (4) | C32—C31—C36 | 118.4 (4) |
N3—C5—C2 | 121.2 (3) | C32—C31—C5 | 122.3 (4) |
N3—C5—C31 | 120.0 (3) | C36—C31—C5 | 119.3 (4) |
C2—C5—C31 | 118.8 (3) | C31—C32—C33 | 121.1 (5) |
O2—C6—C7 | 120.8 (5) | C31—C32—H32 | 120 (2) |
O2—C6—C24 | 120.8 (4) | C33—C32—H32 | 119 (2) |
C7—C6—C24 | 118.3 (5) | C34—C33—C32 | 120.0 (5) |
C6—C7—H71 | 114 (4) | C34—C33—H34 | 125 (3) |
C6—C7—H72 | 108 (3) | C32—C33—H34 | 115 (3) |
H71—C7—H72 | 115 (5) | C33—C34—C35 | 119.8 (5) |
C6—C7—H73 | 116 (4) | C33—C34—H33 | 120 (3) |
H71—C7—H73 | 106 (5) | C35—C34—H33 | 120 (3) |
H72—C7—H73 | 98 (5) | C34—C35—C36 | 120.3 (5) |
C16—C11—C12 | 118.3 (4) | C34—C35—H35 | 124 (3) |
C16—C11—N1 | 121.3 (4) | C36—C35—H35 | 116 (3) |
C12—C11—N1 | 120.4 (4) | C35—C36—C31 | 120.3 (5) |
C13—C12—C11 | 120.9 (5) | C35—C36—H36 | 125 (3) |
C13—C12—H12 | 126 (2) | C31—C36—H36 | 114 (3) |
C11—C12—H12 | 113 (2) | | |
| | | |
O1i—Cu1—O1—C1 | 130.6 (2) | C16—C11—C12—C13 | 0.6 (6) |
N3i—Cu1—O1—C1 | −129.6 (2) | N1—C11—C12—C13 | −178.4 (4) |
N3—Cu1—O1—C1 | 30.7 (3) | C11—C12—C13—C14 | −0.4 (7) |
C1—N1—N2—C3 | −0.8 (4) | C12—C13—C14—C15 | −0.3 (8) |
C11—N1—N2—C3 | 176.4 (3) | C13—C14—C15—C16 | 0.8 (9) |
O1i—Cu1—N3—C5 | −174.4 (3) | C14—C15—C16—C11 | −0.6 (9) |
O1—Cu1—N3—C5 | −29.3 (3) | C12—C11—C16—C15 | −0.1 (7) |
N3i—Cu1—N3—C5 | 78.2 (3) | N1—C11—C16—C15 | 178.9 (4) |
O1i—Cu1—N3—C21 | 12.9 (3) | C5—N3—C21—C26 | 77.3 (4) |
O1—Cu1—N3—C21 | 158.0 (2) | Cu1—N3—C21—C26 | −109.6 (3) |
N3i—Cu1—N3—C21 | −94.5 (2) | C5—N3—C21—C22 | −105.1 (4) |
Cu1—O1—C1—N1 | 158.2 (3) | Cu1—N3—C21—C22 | 68.1 (4) |
Cu1—O1—C1—C2 | −20.7 (5) | C26—C21—C22—C23 | −2.5 (5) |
N2—N1—C1—O1 | −177.0 (3) | N3—C21—C22—C23 | 179.8 (3) |
C11—N1—C1—O1 | 6.2 (6) | C21—C22—C23—C24 | 1.5 (6) |
N2—N1—C1—C2 | 2.2 (4) | C22—C23—C24—C25 | −0.3 (6) |
C11—N1—C1—C2 | −174.7 (3) | C22—C23—C24—C6 | 180.0 (4) |
O1—C1—C2—C5 | −4.8 (6) | O2—C6—C24—C23 | −7.7 (6) |
N1—C1—C2—C5 | 176.1 (3) | C7—C6—C24—C23 | 171.9 (6) |
O1—C1—C2—C3 | 176.5 (4) | O2—C6—C24—C25 | 172.5 (4) |
N1—C1—C2—C3 | −2.6 (4) | C7—C6—C24—C25 | −7.9 (7) |
N1—N2—C3—C2 | −0.9 (4) | C23—C24—C25—C26 | 0.2 (6) |
N1—N2—C3—C4 | 180.0 (4) | C6—C24—C25—C26 | 180.0 (4) |
C1—C2—C3—N2 | 2.2 (4) | C22—C21—C26—C25 | 2.5 (6) |
C5—C2—C3—N2 | −176.3 (4) | N3—C21—C26—C25 | −179.8 (4) |
C1—C2—C3—C4 | −178.8 (5) | C24—C25—C26—C21 | −1.4 (7) |
C5—C2—C3—C4 | 2.7 (8) | N3—C5—C31—C32 | −101.6 (4) |
C21—N3—C5—C2 | −173.6 (3) | C2—C5—C31—C32 | 78.1 (5) |
Cu1—N3—C5—C2 | 13.7 (4) | N3—C5—C31—C36 | 76.4 (5) |
C21—N3—C5—C31 | 6.1 (5) | C2—C5—C31—C36 | −103.9 (4) |
Cu1—N3—C5—C31 | −166.6 (2) | C36—C31—C32—C33 | 0.8 (6) |
C1—C2—C5—N3 | 8.6 (5) | C5—C31—C32—C33 | 178.8 (4) |
C3—C2—C5—N3 | −173.1 (3) | C31—C32—C33—C34 | 0.5 (7) |
C1—C2—C5—C31 | −171.1 (3) | C32—C33—C34—C35 | −1.5 (8) |
C3—C2—C5—C31 | 7.2 (6) | C33—C34—C35—C36 | 1.2 (9) |
C1—N1—C11—C16 | 29.3 (6) | C34—C35—C36—C31 | 0.2 (8) |
N2—N1—C11—C16 | −147.4 (4) | C32—C31—C36—C35 | −1.1 (7) |
C1—N1—C11—C12 | −151.7 (4) | C5—C31—C36—C35 | −179.2 (4) |
N2—N1—C11—C12 | 31.7 (5) | | |
Symmetry code: (i) −x, y, −z+3/2. |