In the title complex, [Cu(C
22H
26N
2O
6)], the coordination geometry about the Cu atom is a 6–5–6 chelate ring structure with a tetrahedrally distorted square plane formed by the four-coordinate N
2O
2 donor set of the Schiff base imine–phenol ligand. The crystal packing is stabilized by intermolecular O—H
O and C—H
O hydrogen bonds.
Supporting information
CCDC reference: 258641
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.108
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.91
Alert level B
PLAT412_ALERT_2_B Short Intra XH3 .. XHn H10C .. H11B .. 1.78 Ang.
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 27.99
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 4633
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 5091
Completeness (_total/calc) 91.00%
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
[
N,
N'-Bis(1-{[2-oxido-4-(2-hydroxyethoxy)phenyl]methyl}ethylidene)ethane- 1,2-diamine]copper(II)
top
Crystal data top
[Cu(C22H26N2O6)] | F(000) = 996 |
Mr = 477.99 | Dx = 1.505 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4421 reflections |
a = 11.8535 (7) Å | θ = 2.4–27.2° |
b = 8.6424 (5) Å | µ = 1.08 mm−1 |
c = 21.0047 (13) Å | T = 293 K |
β = 101.451 (1)° | Block, red |
V = 2108.9 (2) Å3 | 0.24 × 0.20 × 0.16 mm |
Z = 4 | |
Data collection top
CCD Aread Detector diffractometer | 3861 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 28.0°, θmin = 1.8° |
ω scans | h = −15→15 |
12545 measured reflections | k = −11→10 |
4633 independent reflections | l = −27→18 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0651P)2 + 0.3364P] where P = (Fo2 + 2Fc2)/3 |
4633 reflections | (Δ/σ)max < 0.001 |
284 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.31 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 | 0.66442 (2) | 0.90832 (3) | 0.012539 (13) | 0.02912 (10) | |
O3 | 0.59352 (13) | 0.78568 (18) | 0.06756 (7) | 0.0356 (4) | |
N2 | 0.74827 (16) | 1.0227 (2) | −0.04260 (9) | 0.0337 (4) | |
O2 | 0.32000 (14) | 0.4692 (2) | 0.14096 (8) | 0.0428 (4) | |
O6 | 1.24551 (14) | 1.1275 (2) | 0.34100 (8) | 0.0407 (4) | |
H6 | 1.2865 | 1.1709 | 0.3719 | 0.061* | |
O5 | 1.06829 (13) | 1.20756 (19) | 0.23378 (8) | 0.0414 (4) | |
N1 | 0.55310 (15) | 0.8545 (2) | −0.06422 (9) | 0.0302 (4) | |
C6 | 0.43390 (17) | 0.6888 (2) | −0.01277 (11) | 0.0294 (4) | |
C15 | 0.89045 (18) | 1.1376 (3) | 0.04227 (11) | 0.0325 (5) | |
O4 | 0.76989 (14) | 0.9605 (2) | 0.08786 (8) | 0.0467 (4) | |
C9 | 0.46362 (17) | 0.7639 (2) | −0.06943 (11) | 0.0292 (4) | |
C19 | 0.91626 (19) | 1.0816 (3) | 0.15816 (12) | 0.0368 (5) | |
H19 | 0.8943 | 1.0269 | 0.1918 | 0.044* | |
C7 | 0.49759 (17) | 0.7058 (2) | 0.05142 (11) | 0.0287 (4) | |
O1 | 0.34704 (17) | 0.2430 (2) | 0.24268 (9) | 0.0532 (5) | |
H1 | 0.3120 | 0.1889 | 0.2643 | 0.080* | |
C1 | 0.3189 (2) | 0.3999 (3) | 0.24973 (12) | 0.0416 (6) | |
H1A | 0.3442 | 0.4315 | 0.2946 | 0.050* | |
H1B | 0.2362 | 0.4136 | 0.2380 | 0.050* | |
C20 | 0.85558 (18) | 1.0586 (2) | 0.09422 (12) | 0.0333 (5) | |
C8 | 0.45888 (18) | 0.6341 (2) | 0.10316 (11) | 0.0327 (5) | |
H8 | 0.4999 | 0.6483 | 0.1453 | 0.039* | |
C21 | 1.0517 (2) | 1.1002 (3) | 0.28285 (13) | 0.0453 (6) | |
H21A | 1.0699 | 0.9962 | 0.2707 | 0.054* | |
H21B | 0.9720 | 1.1020 | 0.2877 | 0.054* | |
C2 | 0.3765 (2) | 0.4966 (3) | 0.20676 (11) | 0.0437 (6) | |
H2A | 0.3712 | 0.6052 | 0.2174 | 0.052* | |
H2B | 0.4573 | 0.4690 | 0.2127 | 0.052* | |
C3 | 0.36158 (18) | 0.5431 (2) | 0.09285 (11) | 0.0328 (5) | |
C18 | 1.00704 (18) | 1.1827 (2) | 0.17217 (12) | 0.0342 (5) | |
C17 | 1.0401 (2) | 1.2659 (3) | 0.12217 (12) | 0.0412 (6) | |
H17 | 1.1002 | 1.3367 | 0.1312 | 0.049* | |
C11 | 0.5761 (2) | 0.9410 (3) | −0.12052 (11) | 0.0358 (5) | |
H11A | 0.5297 | 1.0343 | −0.1264 | 0.043* | |
H11B | 0.5548 | 0.8784 | −0.1594 | 0.043* | |
C16 | 0.9836 (2) | 1.2425 (3) | 0.05989 (12) | 0.0409 (6) | |
H16 | 1.0073 | 1.2983 | 0.0271 | 0.049* | |
C5 | 0.33464 (18) | 0.5934 (3) | −0.02053 (12) | 0.0364 (5) | |
H5 | 0.2913 | 0.5792 | −0.0621 | 0.044* | |
C14 | 0.8947 (2) | 1.1811 (3) | −0.07770 (12) | 0.0481 (6) | |
H14A | 0.8950 | 1.1072 | −0.1118 | 0.072* | |
H14B | 0.9723 | 1.2103 | −0.0590 | 0.072* | |
H14C | 0.8520 | 1.2711 | −0.0952 | 0.072* | |
C4 | 0.29978 (18) | 0.5216 (3) | 0.03012 (12) | 0.0374 (5) | |
H4 | 0.2349 | 0.4585 | 0.0226 | 0.045* | |
C12 | 0.7020 (2) | 0.9836 (3) | −0.11093 (11) | 0.0431 (6) | |
H12A | 0.7448 | 0.8975 | −0.1238 | 0.052* | |
H12B | 0.7110 | 1.0714 | −0.1382 | 0.052* | |
C13 | 0.83895 (18) | 1.1099 (3) | −0.02585 (12) | 0.0330 (5) | |
C10 | 0.3866 (2) | 0.7380 (3) | −0.13453 (12) | 0.0435 (6) | |
H10A | 0.3196 | 0.8023 | −0.1384 | 0.065* | |
H10B | 0.3637 | 0.6313 | −0.1385 | 0.065* | |
H10C | 0.4274 | 0.7637 | −0.1683 | 0.065* | |
C22 | 1.1289 (2) | 1.1452 (3) | 0.34539 (12) | 0.0429 (6) | |
H22A | 1.1145 | 1.2521 | 0.3554 | 0.052* | |
H22B | 1.1124 | 1.0810 | 0.3803 | 0.052* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.02965 (16) | 0.03492 (16) | 0.02126 (17) | −0.00151 (9) | 0.00140 (12) | 0.00043 (10) |
O3 | 0.0348 (8) | 0.0447 (9) | 0.0238 (8) | −0.0117 (6) | −0.0024 (7) | 0.0031 (7) |
N2 | 0.0358 (9) | 0.0421 (10) | 0.0232 (10) | 0.0011 (8) | 0.0056 (8) | 0.0009 (8) |
O2 | 0.0404 (9) | 0.0591 (10) | 0.0275 (9) | −0.0199 (8) | 0.0036 (8) | −0.0032 (8) |
O6 | 0.0370 (8) | 0.0518 (10) | 0.0294 (10) | −0.0025 (7) | −0.0027 (7) | −0.0016 (7) |
O5 | 0.0391 (8) | 0.0478 (9) | 0.0322 (10) | −0.0137 (7) | −0.0050 (8) | 0.0038 (7) |
N1 | 0.0342 (9) | 0.0330 (9) | 0.0215 (10) | 0.0041 (7) | 0.0009 (8) | −0.0022 (7) |
C6 | 0.0308 (10) | 0.0289 (10) | 0.0254 (12) | 0.0029 (8) | −0.0015 (9) | −0.0043 (8) |
C15 | 0.0293 (10) | 0.0377 (11) | 0.0295 (13) | 0.0025 (8) | 0.0031 (10) | 0.0031 (9) |
O4 | 0.0423 (9) | 0.0662 (11) | 0.0272 (10) | −0.0244 (8) | −0.0035 (8) | 0.0082 (8) |
C9 | 0.0312 (10) | 0.0302 (10) | 0.0230 (11) | 0.0072 (8) | −0.0026 (9) | −0.0036 (8) |
C19 | 0.0313 (11) | 0.0484 (13) | 0.0293 (13) | −0.0075 (9) | 0.0030 (10) | 0.0034 (10) |
C7 | 0.0278 (9) | 0.0297 (10) | 0.0268 (12) | 0.0015 (7) | 0.0009 (9) | −0.0015 (8) |
O1 | 0.0689 (13) | 0.0542 (11) | 0.0426 (12) | −0.0006 (9) | 0.0263 (10) | −0.0005 (9) |
C1 | 0.0419 (13) | 0.0554 (15) | 0.0292 (14) | −0.0126 (10) | 0.0113 (11) | −0.0103 (11) |
C20 | 0.0287 (10) | 0.0398 (12) | 0.0302 (13) | −0.0030 (8) | 0.0029 (10) | 0.0019 (9) |
C8 | 0.0319 (11) | 0.0374 (11) | 0.0257 (12) | −0.0031 (8) | −0.0019 (9) | −0.0032 (9) |
C21 | 0.0421 (13) | 0.0551 (15) | 0.0339 (15) | −0.0160 (10) | −0.0037 (12) | 0.0058 (11) |
C2 | 0.0445 (13) | 0.0553 (15) | 0.0317 (14) | −0.0175 (11) | 0.0089 (11) | −0.0088 (11) |
C3 | 0.0299 (10) | 0.0369 (11) | 0.0309 (13) | −0.0023 (8) | 0.0045 (10) | −0.0031 (9) |
C18 | 0.0293 (10) | 0.0374 (11) | 0.0334 (13) | −0.0018 (8) | −0.0003 (10) | 0.0007 (10) |
C17 | 0.0363 (12) | 0.0424 (13) | 0.0422 (16) | −0.0108 (9) | 0.0010 (11) | 0.0047 (11) |
C11 | 0.0445 (13) | 0.0405 (12) | 0.0202 (12) | 0.0009 (9) | 0.0009 (10) | 0.0004 (9) |
C16 | 0.0398 (12) | 0.0450 (13) | 0.0374 (15) | −0.0070 (10) | 0.0065 (11) | 0.0095 (11) |
C5 | 0.0314 (11) | 0.0448 (13) | 0.0280 (14) | 0.0000 (9) | −0.0059 (10) | −0.0067 (10) |
C14 | 0.0475 (14) | 0.0653 (17) | 0.0341 (15) | −0.0074 (12) | 0.0144 (12) | 0.0046 (12) |
C4 | 0.0301 (11) | 0.0452 (12) | 0.0344 (14) | −0.0082 (9) | 0.0008 (10) | −0.0065 (10) |
C12 | 0.0455 (13) | 0.0608 (15) | 0.0230 (13) | −0.0022 (11) | 0.0071 (11) | −0.0007 (11) |
C13 | 0.0333 (11) | 0.0371 (11) | 0.0305 (13) | 0.0048 (8) | 0.0109 (10) | 0.0041 (9) |
C10 | 0.0455 (13) | 0.0504 (14) | 0.0284 (14) | −0.0070 (10) | −0.0078 (11) | 0.0034 (11) |
C22 | 0.0388 (12) | 0.0561 (14) | 0.0313 (14) | −0.0096 (10) | 0.0005 (11) | −0.0003 (11) |
Geometric parameters (Å, º) top
Cu1—O4 | 1.867 (2) | C1—H1B | 0.9700 |
Cu1—O3 | 1.885 (2) | C8—C3 | 1.377 (3) |
Cu1—N1 | 1.927 (2) | C8—H8 | 0.9300 |
Cu1—N2 | 1.940 (2) | C21—C22 | 1.496 (3) |
O3—C7 | 1.316 (2) | C21—H21A | 0.9700 |
N2—C13 | 1.302 (3) | C21—H21B | 0.9700 |
N2—C12 | 1.471 (3) | C2—H2A | 0.9700 |
O2—C3 | 1.368 (3) | C2—H2B | 0.9700 |
O2—C2 | 1.431 (3) | C3—C4 | 1.387 (3) |
O6—C22 | 1.411 (3) | C18—C17 | 1.391 (3) |
O6—H6 | 0.8200 | C17—C16 | 1.361 (3) |
O5—C18 | 1.369 (3) | C17—H17 | 0.9300 |
O5—C21 | 1.429 (3) | C11—C12 | 1.511 (3) |
N1—C9 | 1.306 (3) | C11—H11A | 0.9700 |
N1—C11 | 1.469 (3) | C11—H11B | 0.9700 |
C6—C7 | 1.416 (3) | C16—H16 | 0.9300 |
C6—C5 | 1.419 (3) | C5—C4 | 1.365 (3) |
C6—C9 | 1.459 (3) | C5—H5 | 0.9300 |
C15—C20 | 1.417 (3) | C14—C13 | 1.512 (3) |
C15—C16 | 1.420 (3) | C14—H14A | 0.9600 |
C15—C13 | 1.460 (3) | C14—H14B | 0.9600 |
O4—C20 | 1.309 (3) | C14—H14C | 0.9600 |
C9—C10 | 1.502 (3) | C4—H4 | 0.9300 |
C19—C18 | 1.372 (3) | C12—H12A | 0.9700 |
C19—C20 | 1.406 (3) | C12—H12B | 0.9700 |
C19—H19 | 0.9300 | C10—H10A | 0.9600 |
C7—C8 | 1.405 (3) | C10—H10B | 0.9600 |
O1—C1 | 1.410 (3) | C10—H10C | 0.9600 |
O1—H1 | 0.8200 | C22—H22A | 0.9700 |
C1—C2 | 1.492 (3) | C22—H22B | 0.9700 |
C1—H1A | 0.9700 | | |
| | | |
O4—Cu1—O3 | 85.5 (1) | O2—C2—H2B | 110.1 |
O4—Cu1—N1 | 178.8 (1) | C1—C2—H2B | 110.1 |
O3—Cu1—N1 | 93.6 (1) | H2A—C2—H2B | 108.4 |
O4—Cu1—N2 | 92.7 (1) | O2—C3—C8 | 124.3 (2) |
O3—Cu1—N2 | 175.2 (1) | O2—C3—C4 | 116.07 (19) |
N1—Cu1—N2 | 88.3 (1) | C8—C3—C4 | 119.6 (2) |
C7—O3—Cu1 | 127.22 (14) | O5—C18—C19 | 123.3 (2) |
C13—N2—C12 | 121.65 (19) | O5—C18—C17 | 117.16 (19) |
C13—N2—Cu1 | 128.80 (16) | C19—C18—C17 | 119.6 (2) |
C12—N2—Cu1 | 109.23 (14) | C16—C17—C18 | 119.4 (2) |
C3—O2—C2 | 117.92 (17) | C16—C17—H17 | 120.3 |
C22—O6—H6 | 109.5 | C18—C17—H17 | 120.3 |
C18—O5—C21 | 117.17 (17) | N1—C11—C12 | 110.67 (19) |
C9—N1—C11 | 121.01 (19) | N1—C11—H11A | 109.5 |
C9—N1—Cu1 | 128.68 (16) | C12—C11—H11A | 109.5 |
C11—N1—Cu1 | 110.18 (14) | N1—C11—H11B | 109.5 |
C7—C6—C5 | 116.3 (2) | C12—C11—H11B | 109.5 |
C7—C6—C9 | 124.13 (19) | H11A—C11—H11B | 108.1 |
C5—C6—C9 | 119.6 (2) | C17—C16—C15 | 123.7 (2) |
C20—C15—C16 | 116.0 (2) | C17—C16—H16 | 118.2 |
C20—C15—C13 | 123.2 (2) | C15—C16—H16 | 118.2 |
C16—C15—C13 | 120.8 (2) | C4—C5—C6 | 123.2 (2) |
C20—O4—Cu1 | 128.21 (16) | C4—C5—H5 | 118.4 |
N1—C9—C6 | 121.5 (2) | C6—C5—H5 | 118.4 |
N1—C9—C10 | 120.2 (2) | C13—C14—H14A | 109.5 |
C6—C9—C10 | 118.33 (19) | C13—C14—H14B | 109.5 |
C18—C19—C20 | 121.7 (2) | H14A—C14—H14B | 109.5 |
C18—C19—H19 | 119.1 | C13—C14—H14C | 109.5 |
C20—C19—H19 | 119.1 | H14A—C14—H14C | 109.5 |
O3—C7—C8 | 115.49 (19) | H14B—C14—H14C | 109.5 |
O3—C7—C6 | 124.7 (2) | C5—C4—C3 | 119.7 (2) |
C8—C7—C6 | 119.77 (19) | C5—C4—H4 | 120.2 |
C1—O1—H1 | 109.5 | C3—C4—H4 | 120.2 |
O1—C1—C2 | 109.2 (2) | N2—C12—C11 | 110.70 (18) |
O1—C1—H1A | 109.8 | N2—C12—H12A | 109.5 |
C2—C1—H1A | 109.8 | C11—C12—H12A | 109.5 |
O1—C1—H1B | 109.8 | N2—C12—H12B | 109.5 |
C2—C1—H1B | 109.8 | C11—C12—H12B | 109.5 |
H1A—C1—H1B | 108.3 | H12A—C12—H12B | 108.1 |
O4—C20—C19 | 115.4 (2) | N2—C13—C15 | 121.5 (2) |
O4—C20—C15 | 124.9 (2) | N2—C13—C14 | 119.7 (2) |
C19—C20—C15 | 119.7 (2) | C15—C13—C14 | 118.8 (2) |
C3—C8—C7 | 121.5 (2) | C9—C10—H10A | 109.5 |
C3—C8—H8 | 119.3 | C9—C10—H10B | 109.5 |
C7—C8—H8 | 119.3 | H10A—C10—H10B | 109.5 |
O5—C21—C22 | 108.45 (19) | C9—C10—H10C | 109.5 |
O5—C21—H21A | 110.0 | H10A—C10—H10C | 109.5 |
C22—C21—H21A | 110.0 | H10B—C10—H10C | 109.5 |
O5—C21—H21B | 110.0 | O6—C22—C21 | 110.5 (2) |
C22—C21—H21B | 110.0 | O6—C22—H22A | 109.5 |
H21A—C21—H21B | 108.4 | C21—C22—H22A | 109.5 |
O2—C2—C1 | 108.00 (18) | O6—C22—H22B | 109.5 |
O2—C2—H2A | 110.1 | C21—C22—H22B | 109.5 |
C1—C2—H2A | 110.1 | H22A—C22—H22B | 108.1 |
| | | |
O4—Cu1—O3—C7 | 175.98 (18) | C18—O5—C21—C22 | 178.13 (19) |
N1—Cu1—O3—C7 | −3.31 (18) | C3—O2—C2—C1 | −178.0 (2) |
O4—Cu1—N2—C13 | −4.7 (2) | O1—C1—C2—O2 | 71.4 (3) |
N1—Cu1—N2—C13 | 174.6 (2) | C2—O2—C3—C8 | 4.5 (3) |
O4—Cu1—N2—C12 | 168.68 (16) | C2—O2—C3—C4 | −175.9 (2) |
N1—Cu1—N2—C12 | −11.96 (15) | C7—C8—C3—O2 | 179.4 (2) |
O3—Cu1—N1—C9 | 0.24 (18) | C7—C8—C3—C4 | −0.2 (3) |
N2—Cu1—N1—C9 | 175.83 (18) | C21—O5—C18—C19 | 13.3 (3) |
O3—Cu1—N1—C11 | 176.09 (14) | C21—O5—C18—C17 | −166.9 (2) |
N2—Cu1—N1—C11 | −8.33 (14) | C20—C19—C18—O5 | −179.7 (2) |
O3—Cu1—O4—C20 | −176.2 (2) | C20—C19—C18—C17 | 0.4 (3) |
N2—Cu1—O4—C20 | 8.2 (2) | O5—C18—C17—C16 | 178.5 (2) |
C11—N1—C9—C6 | −174.21 (17) | C19—C18—C17—C16 | −1.7 (3) |
Cu1—N1—C9—C6 | 1.2 (3) | C9—N1—C11—C12 | −157.3 (2) |
C11—N1—C9—C10 | 4.2 (3) | Cu1—N1—C11—C12 | 26.5 (2) |
Cu1—N1—C9—C10 | 179.64 (15) | C18—C17—C16—C15 | 0.6 (4) |
C7—C6—C9—N1 | −0.3 (3) | C20—C15—C16—C17 | 1.7 (3) |
C5—C6—C9—N1 | 178.83 (19) | C13—C15—C16—C17 | −175.6 (2) |
C7—C6—C9—C10 | −178.7 (2) | C7—C6—C5—C4 | 0.5 (3) |
C5—C6—C9—C10 | 0.4 (3) | C9—C6—C5—C4 | −178.7 (2) |
Cu1—O3—C7—C8 | −175.07 (14) | C6—C5—C4—C3 | 1.3 (3) |
Cu1—O3—C7—C6 | 5.0 (3) | O2—C3—C4—C5 | 179.0 (2) |
C5—C6—C7—O3 | 177.90 (19) | C8—C3—C4—C5 | −1.4 (3) |
C9—C6—C7—O3 | −2.9 (3) | C13—N2—C12—C11 | −156.8 (2) |
C5—C6—C7—C8 | −2.1 (3) | Cu1—N2—C12—C11 | 29.3 (2) |
C9—C6—C7—C8 | 177.11 (18) | N1—C11—C12—N2 | −36.9 (3) |
Cu1—O4—C20—C19 | 176.01 (16) | C12—N2—C13—C15 | −174.7 (2) |
Cu1—O4—C20—C15 | −5.1 (3) | Cu1—N2—C13—C15 | −2.0 (3) |
C18—C19—C20—O4 | −179.1 (2) | C12—N2—C13—C14 | 3.7 (3) |
C18—C19—C20—C15 | 2.0 (3) | Cu1—N2—C13—C14 | 176.38 (16) |
C16—C15—C20—O4 | 178.2 (2) | C20—C15—C13—N2 | 8.0 (3) |
C13—C15—C20—O4 | −4.5 (4) | C16—C15—C13—N2 | −174.9 (2) |
C16—C15—C20—C19 | −2.9 (3) | C20—C15—C13—C14 | −170.4 (2) |
C13—C15—C20—C19 | 174.3 (2) | C16—C15—C13—C14 | 6.7 (3) |
O3—C7—C8—C3 | −178.01 (19) | O5—C21—C22—O6 | −65.8 (3) |
C6—C7—C8—C3 | 1.9 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11B···O1i | 0.97 | 2.52 | 3.297 (3) | 138 |
O1—H1···O6ii | 0.82 | 2.00 | 2.775 (2) | 157 |
O6—H6···O3iii | 0.82 | 1.98 | 2.783 (2) | 168 |
C22—H22A···O4iii | 0.97 | 2.43 | 3.188 (3) | 135 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y−1, z; (iii) −x+2, y+1/2, −z+1/2. |