Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033593/ci6661sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033593/ci6661Isup2.hkl |
CCDC reference: 241542
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
[Cu2(C11H14N2O2)(C11H15N2O2)]ClO4·CH4O | F(000) = 1384 |
Mr = 672.06 | Dx = 1.621 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1002 reflections |
a = 12.479 (3) Å | θ = 3.1–25.8° |
b = 15.731 (4) Å | µ = 1.70 mm−1 |
c = 14.274 (4) Å | T = 294 K |
β = 100.590 (4)° | Block, blue |
V = 2754.5 (13) Å3 | 0.24 × 0.20 × 0.16 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 5622 independent reflections |
Radiation source: fine-focus sealed tube | 3994 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
φ and ω scans | θmax = 26.4°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→15 |
Tmin = 0.568, Tmax = 0.762 | k = −19→19 |
15671 measured reflections | l = −17→15 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0651P)2 + 0.0776P] where P = (Fo2 + 2Fc2)/3 |
5622 reflections | (Δ/σ)max = 0.003 |
410 parameters | Δρmax = 0.79 e Å−3 |
48 restraints | Δρmin = −0.43 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cu1 | 1.07496 (4) | 0.22159 (3) | 0.27019 (3) | 0.03698 (15) | |
Cu2 | 0.87922 (4) | 0.32670 (3) | 0.31201 (3) | 0.03805 (16) | |
O1 | 0.9230 (2) | 0.20327 (19) | 0.2210 (2) | 0.0475 (7) | |
O2 | 1.1016 (2) | 0.3462 (2) | 0.18224 (19) | 0.0476 (7) | |
H2B | 1.0367 | 0.3746 | 0.1902 | 0.057* | |
O3 | 0.9139 (2) | 0.40634 (18) | 0.22139 (19) | 0.0440 (7) | |
O4 | 1.0291 (2) | 0.29745 (17) | 0.36490 (17) | 0.0379 (6) | |
N1 | 1.1200 (3) | 0.1243 (2) | 0.2046 (2) | 0.0409 (8) | |
N2 | 1.2361 (3) | 0.2388 (2) | 0.3165 (2) | 0.0449 (8) | |
H2A | 1.2524 | 0.2601 | 0.3782 | 0.054* | |
N3 | 0.7240 (3) | 0.3349 (2) | 0.2679 (2) | 0.0426 (8) | |
N4 | 0.8396 (3) | 0.2661 (2) | 0.4232 (2) | 0.0469 (9) | |
H4A | 0.8318 | 0.3028 | 0.4746 | 0.056* | |
C1 | 0.8792 (3) | 0.1428 (3) | 0.1620 (3) | 0.0393 (9) | |
C2 | 0.7662 (4) | 0.1440 (3) | 0.1266 (3) | 0.0488 (11) | |
H2 | 0.7244 | 0.1880 | 0.1444 | 0.059* | |
C3 | 0.7161 (4) | 0.0819 (3) | 0.0666 (3) | 0.0542 (12) | |
H3 | 0.6413 | 0.0846 | 0.0443 | 0.065* | |
C4 | 0.7756 (4) | 0.0151 (3) | 0.0387 (3) | 0.0602 (13) | |
H4 | 0.7413 | −0.0269 | −0.0019 | 0.072* | |
C5 | 0.8853 (4) | 0.0121 (3) | 0.0716 (3) | 0.0534 (12) | |
H5 | 0.9252 | −0.0330 | 0.0537 | 0.064* | |
C6 | 0.9401 (3) | 0.0759 (2) | 0.1323 (3) | 0.0380 (9) | |
C7 | 1.0570 (4) | 0.0700 (3) | 0.1564 (3) | 0.0419 (10) | |
H7 | 1.0894 | 0.0223 | 0.1350 | 0.050* | |
C8 | 1.2395 (4) | 0.1138 (3) | 0.2160 (3) | 0.0535 (12) | |
H8A | 1.2657 | 0.1399 | 0.1629 | 0.064* | |
H8B | 1.2582 | 0.0539 | 0.2178 | 0.064* | |
C9 | 1.2911 (4) | 0.1563 (3) | 0.3085 (3) | 0.0569 (12) | |
H9A | 1.2836 | 0.1201 | 0.3620 | 0.068* | |
H9B | 1.3681 | 0.1654 | 0.3095 | 0.068* | |
C10 | 1.2789 (4) | 0.3079 (3) | 0.2608 (3) | 0.0573 (12) | |
H10A | 1.3470 | 0.3295 | 0.2968 | 0.069* | |
H10B | 1.2932 | 0.2850 | 0.2012 | 0.069* | |
C11 | 1.1982 (4) | 0.3787 (3) | 0.2407 (3) | 0.0525 (11) | |
H11A | 1.1815 | 0.4006 | 0.2999 | 0.063* | |
H11B | 1.2281 | 0.4247 | 0.2082 | 0.063* | |
C12 | 0.8454 (4) | 0.4375 (3) | 0.1476 (3) | 0.0416 (10) | |
C13 | 0.8884 (4) | 0.4912 (3) | 0.0848 (3) | 0.0521 (11) | |
H13 | 0.9624 | 0.5040 | 0.0966 | 0.063* | |
C14 | 0.8214 (5) | 0.5252 (3) | 0.0054 (3) | 0.0630 (14) | |
H14 | 0.8508 | 0.5610 | −0.0350 | 0.076* | |
C15 | 0.7120 (5) | 0.5066 (3) | −0.0144 (3) | 0.0685 (15) | |
H15 | 0.6683 | 0.5284 | −0.0689 | 0.082* | |
C16 | 0.6671 (4) | 0.4558 (3) | 0.0466 (3) | 0.0596 (13) | |
H16 | 0.5927 | 0.4445 | 0.0334 | 0.072* | |
C17 | 0.7318 (4) | 0.4205 (3) | 0.1287 (3) | 0.0428 (10) | |
C18 | 0.6773 (4) | 0.3715 (3) | 0.1909 (3) | 0.0453 (10) | |
H18 | 0.6021 | 0.3658 | 0.1738 | 0.054* | |
C19 | 0.6594 (4) | 0.2907 (3) | 0.3293 (3) | 0.0568 (13) | |
H19A | 0.5974 | 0.2625 | 0.2909 | 0.068* | |
H19B | 0.6326 | 0.3310 | 0.3711 | 0.068* | |
C20 | 0.7335 (4) | 0.2264 (3) | 0.3872 (3) | 0.0602 (13) | |
H20A | 0.7013 | 0.2067 | 0.4401 | 0.072* | |
H20B | 0.7431 | 0.1778 | 0.3477 | 0.072* | |
C21 | 0.9328 (4) | 0.2115 (3) | 0.4622 (3) | 0.0563 (12) | |
H21A | 0.9310 | 0.1597 | 0.4250 | 0.068* | |
H21B | 0.9303 | 0.1962 | 0.5276 | 0.068* | |
C22 | 1.0345 (4) | 0.2609 (3) | 0.4577 (3) | 0.0472 (11) | |
H22A | 1.0434 | 0.3056 | 0.5052 | 0.057* | |
H22B | 1.0973 | 0.2235 | 0.4718 | 0.057* | |
Cl1 | 0.43492 (10) | 0.22710 (9) | 0.04127 (9) | 0.0650 (4) | |
O5 | 0.4856 (4) | 0.2075 (3) | 0.1354 (3) | 0.1128 (16) | |
O6 | 0.3248 (7) | 0.1999 (9) | 0.0176 (8) | 0.059 (4) | 0.352 (4) |
O7 | 0.4242 (14) | 0.3244 (4) | 0.0538 (11) | 0.135 (7) | 0.352 (4) |
O8 | 0.4937 (11) | 0.2162 (13) | −0.0304 (7) | 0.117 (7) | 0.352 (4) |
O6A | 0.3235 (5) | 0.2463 (8) | 0.0287 (6) | 0.070 (4) | 0.524 (14) |
O7A | 0.4934 (10) | 0.2822 (9) | −0.0073 (8) | 0.128 (6) | 0.524 (14) |
O8A | 0.4408 (11) | 0.1408 (6) | −0.0068 (8) | 0.151 (6) | 0.524 (14) |
O6B | 0.359 (2) | 0.2963 (15) | 0.0433 (13) | 0.049 (9) | 0.124 (14) |
O7B | 0.5137 (13) | 0.2527 (16) | −0.0146 (11) | 0.042 (10) | 0.124 (14) |
O8B | 0.376 (2) | 0.1541 (12) | −0.0021 (12) | 0.060 (11) | 0.124 (14) |
O9 | 0.4584 (7) | 0.0032 (6) | 0.1707 (7) | 0.220 (4) | |
H9 | 0.4521 | 0.0395 | 0.1260 | 0.264* | |
C23 | 0.5387 (8) | 0.0205 (9) | 0.2425 (7) | 0.196 (7) | |
H23A | 0.5513 | 0.0807 | 0.2456 | 0.295* | |
H23B | 0.6038 | −0.0081 | 0.2328 | 0.295* | |
H23C | 0.5194 | 0.0013 | 0.3010 | 0.295* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0358 (3) | 0.0442 (3) | 0.0318 (3) | 0.0010 (2) | 0.0083 (2) | −0.0024 (2) |
Cu2 | 0.0414 (3) | 0.0421 (3) | 0.0328 (3) | 0.0016 (2) | 0.0126 (2) | 0.0052 (2) |
O1 | 0.0391 (16) | 0.0512 (18) | 0.0524 (18) | −0.0001 (14) | 0.0088 (14) | −0.0159 (14) |
O2 | 0.0427 (17) | 0.0612 (19) | 0.0389 (16) | −0.0016 (14) | 0.0072 (13) | 0.0063 (13) |
O3 | 0.0450 (17) | 0.0457 (17) | 0.0426 (16) | 0.0011 (13) | 0.0114 (13) | 0.0107 (13) |
O4 | 0.0453 (16) | 0.0437 (15) | 0.0255 (13) | 0.0004 (13) | 0.0090 (12) | −0.0002 (11) |
N1 | 0.041 (2) | 0.047 (2) | 0.0364 (19) | 0.0082 (16) | 0.0110 (15) | 0.0004 (15) |
N2 | 0.042 (2) | 0.059 (2) | 0.0332 (18) | −0.0006 (17) | 0.0058 (15) | 0.0023 (16) |
N3 | 0.043 (2) | 0.049 (2) | 0.0393 (19) | 0.0018 (16) | 0.0167 (16) | 0.0020 (16) |
N4 | 0.053 (2) | 0.056 (2) | 0.0359 (19) | 0.0004 (18) | 0.0182 (17) | 0.0044 (16) |
C1 | 0.046 (2) | 0.041 (2) | 0.031 (2) | −0.0058 (19) | 0.0104 (18) | −0.0008 (17) |
C2 | 0.045 (3) | 0.055 (3) | 0.046 (2) | 0.000 (2) | 0.009 (2) | −0.004 (2) |
C3 | 0.051 (3) | 0.067 (3) | 0.044 (2) | −0.012 (2) | 0.007 (2) | −0.003 (2) |
C4 | 0.072 (4) | 0.060 (3) | 0.049 (3) | −0.021 (3) | 0.011 (3) | −0.013 (2) |
C5 | 0.072 (3) | 0.042 (3) | 0.048 (3) | −0.003 (2) | 0.017 (2) | −0.006 (2) |
C6 | 0.048 (3) | 0.036 (2) | 0.030 (2) | −0.0019 (18) | 0.0106 (18) | 0.0016 (16) |
C7 | 0.058 (3) | 0.036 (2) | 0.034 (2) | 0.008 (2) | 0.016 (2) | 0.0009 (17) |
C8 | 0.044 (3) | 0.063 (3) | 0.056 (3) | 0.008 (2) | 0.016 (2) | −0.001 (2) |
C9 | 0.041 (3) | 0.077 (3) | 0.051 (3) | 0.014 (2) | 0.006 (2) | 0.009 (2) |
C10 | 0.040 (3) | 0.078 (3) | 0.054 (3) | −0.010 (2) | 0.010 (2) | 0.006 (2) |
C11 | 0.055 (3) | 0.055 (3) | 0.048 (3) | −0.012 (2) | 0.011 (2) | 0.003 (2) |
C12 | 0.053 (3) | 0.037 (2) | 0.036 (2) | 0.0087 (19) | 0.012 (2) | 0.0017 (17) |
C13 | 0.064 (3) | 0.047 (3) | 0.049 (3) | 0.007 (2) | 0.021 (2) | 0.012 (2) |
C14 | 0.088 (4) | 0.059 (3) | 0.047 (3) | 0.010 (3) | 0.023 (3) | 0.017 (2) |
C15 | 0.090 (4) | 0.071 (4) | 0.042 (3) | 0.014 (3) | 0.006 (3) | 0.017 (2) |
C16 | 0.062 (3) | 0.064 (3) | 0.050 (3) | 0.013 (3) | 0.003 (2) | 0.002 (2) |
C17 | 0.054 (3) | 0.039 (2) | 0.035 (2) | 0.0092 (19) | 0.0100 (19) | −0.0011 (17) |
C18 | 0.044 (3) | 0.049 (3) | 0.044 (2) | 0.004 (2) | 0.010 (2) | −0.006 (2) |
C19 | 0.048 (3) | 0.073 (3) | 0.053 (3) | −0.007 (2) | 0.020 (2) | 0.006 (2) |
C20 | 0.060 (3) | 0.067 (3) | 0.057 (3) | −0.013 (3) | 0.022 (2) | 0.015 (2) |
C21 | 0.064 (3) | 0.064 (3) | 0.043 (3) | 0.006 (2) | 0.016 (2) | 0.022 (2) |
C22 | 0.058 (3) | 0.057 (3) | 0.027 (2) | 0.004 (2) | 0.0108 (19) | 0.0024 (18) |
Cl1 | 0.0441 (7) | 0.0989 (11) | 0.0511 (7) | 0.0022 (7) | 0.0067 (5) | 0.0107 (7) |
O5 | 0.089 (3) | 0.169 (5) | 0.068 (3) | 0.000 (3) | −0.017 (2) | 0.019 (3) |
O6 | 0.060 (8) | 0.066 (9) | 0.051 (6) | −0.020 (7) | 0.009 (5) | −0.009 (7) |
O7 | 0.102 (12) | 0.055 (8) | 0.23 (2) | 0.007 (8) | −0.013 (13) | −0.008 (10) |
O8 | 0.109 (13) | 0.16 (2) | 0.105 (12) | −0.017 (14) | 0.070 (10) | −0.025 (12) |
O6A | 0.048 (5) | 0.100 (11) | 0.059 (5) | 0.013 (5) | 0.003 (4) | 0.008 (6) |
O7A | 0.101 (9) | 0.146 (14) | 0.157 (11) | 0.004 (9) | 0.072 (8) | 0.042 (9) |
O8A | 0.088 (10) | 0.150 (11) | 0.205 (13) | 0.012 (8) | 0.002 (8) | −0.096 (10) |
O6B | 0.051 (13) | 0.049 (13) | 0.056 (12) | 0.011 (9) | 0.033 (9) | 0.013 (9) |
O7B | 0.055 (13) | 0.030 (12) | 0.053 (12) | 0.013 (9) | 0.037 (9) | −0.011 (8) |
O8B | 0.060 (14) | 0.059 (14) | 0.062 (13) | −0.012 (9) | 0.016 (9) | −0.019 (9) |
O9 | 0.191 (9) | 0.214 (8) | 0.260 (10) | −0.042 (7) | 0.053 (7) | 0.062 (8) |
C23 | 0.085 (6) | 0.320 (18) | 0.175 (11) | 0.017 (9) | 0.000 (7) | 0.117 (11) |
Cu1—O1 | 1.920 (3) | C10—H10A | 0.97 |
Cu1—N1 | 1.931 (3) | C10—H10B | 0.97 |
Cu1—O4 | 1.966 (3) | C11—H11A | 0.97 |
Cu1—N2 | 2.017 (4) | C11—H11B | 0.97 |
Cu1—O2 | 2.384 (3) | C12—C13 | 1.408 (6) |
Cu2—O3 | 1.907 (3) | C12—C17 | 1.419 (6) |
Cu2—N3 | 1.928 (4) | C13—C14 | 1.385 (6) |
Cu2—O4 | 1.939 (3) | C13—H13 | 0.93 |
Cu2—N4 | 1.991 (3) | C14—C15 | 1.374 (7) |
O1—C1 | 1.320 (5) | C14—H14 | 0.93 |
O2—C11 | 1.429 (5) | C15—C16 | 1.373 (7) |
O2—H2B | 0.95 | C15—H15 | 0.93 |
O3—C12 | 1.322 (5) | C16—C17 | 1.409 (6) |
O4—C22 | 1.434 (4) | C16—H16 | 0.93 |
N1—C7 | 1.274 (5) | C17—C18 | 1.438 (6) |
N1—C8 | 1.479 (5) | C18—H18 | 0.93 |
N2—C9 | 1.483 (6) | C19—C20 | 1.510 (7) |
N2—C10 | 1.502 (6) | C19—H19A | 0.97 |
N2—H2A | 0.93 | C19—H19B | 0.97 |
N3—C18 | 1.282 (5) | C20—H20A | 0.97 |
N3—C19 | 1.471 (5) | C20—H20B | 0.97 |
N4—C20 | 1.468 (6) | C21—C22 | 1.500 (6) |
N4—C21 | 1.470 (6) | C21—H21A | 0.97 |
N4—H4A | 0.95 | C21—H21B | 0.97 |
C1—C2 | 1.409 (6) | C22—H22A | 0.97 |
C1—C6 | 1.409 (6) | C22—H22B | 0.97 |
C2—C3 | 1.372 (6) | Cl1—O8 | 1.375 (7) |
C2—H2 | 0.93 | Cl1—O7A | 1.396 (6) |
C3—C4 | 1.386 (7) | Cl1—O6A | 1.402 (6) |
C3—H3 | 0.93 | Cl1—O5 | 1.411 (3) |
C4—C5 | 1.364 (7) | Cl1—O6 | 1.420 (7) |
C4—H4 | 0.93 | Cl1—O7B | 1.433 (8) |
C5—C6 | 1.416 (6) | Cl1—O8B | 1.442 (8) |
C5—H5 | 0.93 | Cl1—O6B | 1.451 (9) |
C6—C7 | 1.438 (6) | Cl1—O8A | 1.529 (6) |
C7—H7 | 0.93 | Cl1—O7 | 1.549 (7) |
C8—C9 | 1.514 (6) | O9—C23 | 1.323 (8) |
C8—H8A | 0.97 | O9—H9 | 0.85 |
C8—H8B | 0.97 | C23—H23A | 0.96 |
C9—H9A | 0.97 | C23—H23B | 0.96 |
C9—H9B | 0.97 | C23—H23C | 0.96 |
C10—C11 | 1.493 (7) | ||
O1—Cu1—N1 | 93.42 (13) | N2—C10—H10B | 109.6 |
O1—Cu1—O4 | 87.13 (11) | H10A—C10—H10B | 108.1 |
N1—Cu1—O4 | 164.18 (12) | O2—C11—C10 | 108.2 (4) |
O1—Cu1—N2 | 177.47 (13) | O2—C11—H11A | 110.1 |
N1—Cu1—N2 | 84.46 (15) | C10—C11—H11A | 110.1 |
O4—Cu1—N2 | 95.29 (13) | O2—C11—H11B | 110.1 |
O1—Cu1—O2 | 98.92 (12) | C10—C11—H11B | 110.1 |
N1—Cu1—O2 | 108.38 (12) | H11A—C11—H11B | 108.4 |
O4—Cu1—O2 | 87.10 (11) | O3—C12—C13 | 117.6 (4) |
N2—Cu1—O2 | 80.49 (12) | O3—C12—C17 | 124.0 (4) |
O3—Cu2—N3 | 94.26 (13) | C13—C12—C17 | 118.4 (4) |
O3—Cu2—O4 | 95.56 (11) | C14—C13—C12 | 120.6 (5) |
N3—Cu2—O4 | 169.18 (13) | C14—C13—H13 | 119.7 |
O3—Cu2—N4 | 167.53 (14) | C12—C13—H13 | 119.7 |
N3—Cu2—N4 | 84.87 (14) | C15—C14—C13 | 120.9 (5) |
O4—Cu2—N4 | 86.50 (13) | C15—C14—H14 | 119.5 |
C1—O1—Cu1 | 127.4 (3) | C13—C14—H14 | 119.5 |
C11—O2—Cu1 | 99.8 (2) | C16—C15—C14 | 119.9 (5) |
C11—O2—H2B | 114.1 | C16—C15—H15 | 120.0 |
Cu1—O2—H2B | 96.8 | C14—C15—H15 | 120.0 |
C12—O3—Cu2 | 126.1 (3) | C15—C16—C17 | 121.2 (5) |
C22—O4—Cu2 | 109.5 (2) | C15—C16—H16 | 119.4 |
C22—O4—Cu1 | 114.9 (2) | C17—C16—H16 | 119.4 |
Cu2—O4—Cu1 | 104.96 (12) | C16—C17—C12 | 119.0 (4) |
C7—N1—C8 | 119.6 (4) | C16—C17—C18 | 117.5 (4) |
C7—N1—Cu1 | 126.0 (3) | C12—C17—C18 | 123.5 (4) |
C8—N1—Cu1 | 114.4 (3) | N3—C18—C17 | 125.3 (4) |
C9—N2—C10 | 112.3 (3) | N3—C18—H18 | 117.3 |
C9—N2—Cu1 | 107.8 (3) | C17—C18—H18 | 117.3 |
C10—N2—Cu1 | 110.7 (3) | N3—C19—C20 | 107.1 (4) |
C9—N2—H2A | 111.4 | N3—C19—H19A | 110.3 |
C10—N2—H2A | 101.7 | C20—C19—H19A | 110.3 |
Cu1—N2—H2A | 112.9 | N3—C19—H19B | 110.3 |
C18—N3—C19 | 120.7 (4) | C20—C19—H19B | 110.3 |
C18—N3—Cu2 | 125.5 (3) | H19A—C19—H19B | 108.5 |
C19—N3—Cu2 | 113.7 (3) | N4—C20—C19 | 109.2 (4) |
C20—N4—C21 | 118.9 (4) | N4—C20—H20A | 109.8 |
C20—N4—Cu2 | 105.3 (3) | C19—C20—H20A | 109.8 |
C21—N4—Cu2 | 106.6 (3) | N4—C20—H20B | 109.8 |
C20—N4—H4A | 108.3 | C19—C20—H20B | 109.8 |
C21—N4—H4A | 104.4 | H20A—C20—H20B | 108.3 |
Cu2—N4—H4A | 113.5 | N4—C21—C22 | 107.4 (4) |
O1—C1—C2 | 119.3 (4) | N4—C21—H21A | 110.2 |
O1—C1—C6 | 123.2 (4) | C22—C21—H21A | 110.2 |
C2—C1—C6 | 117.5 (4) | N4—C21—H21B | 110.2 |
C3—C2—C1 | 121.8 (4) | C22—C21—H21B | 110.2 |
C3—C2—H2 | 119.1 | H21A—C21—H21B | 108.5 |
C1—C2—H2 | 119.1 | O4—C22—C21 | 110.5 (3) |
C2—C3—C4 | 120.8 (5) | O4—C22—H22A | 109.5 |
C2—C3—H3 | 119.6 | C21—C22—H22A | 109.5 |
C4—C3—H3 | 119.6 | O4—C22—H22B | 109.5 |
C5—C4—C3 | 118.9 (4) | C21—C22—H22B | 109.5 |
C5—C4—H4 | 120.5 | H22A—C22—H22B | 108.1 |
C3—C4—H4 | 120.5 | O7A—Cl1—O6A | 113.5 (5) |
C4—C5—C6 | 121.8 (4) | O8—Cl1—O5 | 118.4 (6) |
C4—C5—H5 | 119.1 | O7A—Cl1—O5 | 115.2 (5) |
C6—C5—H5 | 119.1 | O6A—Cl1—O5 | 115.5 (4) |
C1—C6—C5 | 119.1 (4) | O8—Cl1—O6 | 114.3 (6) |
C1—C6—C7 | 123.7 (4) | O5—Cl1—O6 | 113.9 (5) |
C5—C6—C7 | 117.1 (4) | O5—Cl1—O7B | 111.0 (7) |
N1—C7—C6 | 125.7 (4) | O5—Cl1—O8B | 109.8 (7) |
N1—C7—H7 | 117.1 | O7B—Cl1—O8B | 109.5 (8) |
C6—C7—H7 | 117.1 | O5—Cl1—O6B | 109.0 (7) |
N1—C8—C9 | 107.8 (3) | O7B—Cl1—O6B | 108.7 (7) |
N1—C8—H8A | 110.1 | O8B—Cl1—O6B | 108.7 (8) |
C9—C8—H8A | 110.1 | O7A—Cl1—O8A | 104.8 (6) |
N1—C8—H8B | 110.1 | O6A—Cl1—O8A | 105.2 (5) |
C9—C8—H8B | 110.1 | O5—Cl1—O8A | 100.5 (5) |
H8A—C8—H8B | 108.5 | O8—Cl1—O7 | 106.1 (6) |
N2—C9—C8 | 109.0 (4) | O5—Cl1—O7 | 98.0 (5) |
N2—C9—H9A | 109.9 | O6—Cl1—O7 | 103.0 (6) |
C8—C9—H9A | 109.9 | C23—O9—H9 | 113.3 |
N2—C9—H9B | 109.9 | O9—C23—H23A | 109.5 |
C8—C9—H9B | 109.9 | O9—C23—H23B | 109.5 |
H9A—C9—H9B | 108.3 | H23A—C23—H23B | 109.5 |
C11—C10—N2 | 110.4 (4) | O9—C23—H23C | 109.5 |
C11—C10—H10A | 109.6 | H23A—C23—H23C | 109.5 |
N2—C10—H10A | 109.6 | H23B—C23—H23C | 109.5 |
C11—C10—H10B | 109.6 | ||
N1—Cu1—O1—C1 | −1.1 (3) | O1—C1—C2—C3 | −178.8 (4) |
O4—Cu1—O1—C1 | −165.2 (3) | C6—C1—C2—C3 | 1.0 (6) |
O2—Cu1—O1—C1 | 108.1 (3) | C1—C2—C3—C4 | 0.1 (7) |
O1—Cu1—O2—C11 | 159.5 (2) | C2—C3—C4—C5 | −0.2 (7) |
N1—Cu1—O2—C11 | −103.8 (3) | C3—C4—C5—C6 | −0.9 (7) |
O4—Cu1—O2—C11 | 72.9 (3) | O1—C1—C6—C5 | 177.7 (4) |
N2—Cu1—O2—C11 | −23.0 (3) | C2—C1—C6—C5 | −2.1 (6) |
N3—Cu2—O3—C12 | −10.4 (3) | O1—C1—C6—C7 | −5.3 (6) |
O4—Cu2—O3—C12 | 165.1 (3) | C2—C1—C6—C7 | 174.9 (4) |
N4—Cu2—O3—C12 | −95.9 (7) | C4—C5—C6—C1 | 2.1 (6) |
O3—Cu2—O4—C22 | 159.6 (2) | C4—C5—C6—C7 | −175.1 (4) |
N3—Cu2—O4—C22 | −45.2 (7) | C8—N1—C7—C6 | −174.1 (4) |
N4—Cu2—O4—C22 | −8.0 (3) | Cu1—N1—C7—C6 | 7.7 (6) |
O3—Cu2—O4—Cu1 | −76.53 (14) | C1—C6—C7—N1 | −2.0 (6) |
N3—Cu2—O4—Cu1 | 78.7 (6) | C5—C6—C7—N1 | 175.1 (4) |
N4—Cu2—O4—Cu1 | 115.81 (15) | C7—N1—C8—C9 | −153.0 (4) |
O1—Cu1—O4—C22 | 101.1 (3) | Cu1—N1—C8—C9 | 25.4 (4) |
N1—Cu1—O4—C22 | 8.7 (6) | C10—N2—C9—C8 | −81.5 (5) |
N2—Cu1—O4—C22 | −79.6 (3) | Cu1—N2—C9—C8 | 40.7 (4) |
O2—Cu1—O4—C22 | −159.8 (3) | N1—C8—C9—N2 | −42.9 (5) |
O1—Cu1—O4—Cu2 | −19.18 (14) | C9—N2—C10—C11 | 159.3 (4) |
N1—Cu1—O4—Cu2 | −111.6 (5) | Cu1—N2—C10—C11 | 38.8 (4) |
N2—Cu1—O4—Cu2 | 160.07 (14) | Cu1—O2—C11—C10 | 49.1 (3) |
O2—Cu1—O4—Cu2 | 79.91 (12) | N2—C10—C11—O2 | −63.1 (5) |
O1—Cu1—N1—C7 | −5.6 (4) | Cu2—O3—C12—C13 | −175.6 (3) |
O4—Cu1—N1—C7 | 85.9 (6) | Cu2—O3—C12—C17 | 4.9 (6) |
N2—Cu1—N1—C7 | 175.8 (4) | O3—C12—C13—C14 | 179.2 (4) |
O2—Cu1—N1—C7 | −106.2 (3) | C17—C12—C13—C14 | −1.2 (6) |
O1—Cu1—N1—C8 | 176.1 (3) | C12—C13—C14—C15 | −0.7 (7) |
O4—Cu1—N1—C8 | −92.4 (5) | C13—C14—C15—C16 | 2.0 (8) |
N2—Cu1—N1—C8 | −2.5 (3) | C14—C15—C16—C17 | −1.3 (8) |
O2—Cu1—N1—C8 | 75.6 (3) | C15—C16—C17—C12 | −0.6 (7) |
N1—Cu1—N2—C9 | −21.5 (3) | C15—C16—C17—C18 | 177.1 (4) |
O4—Cu1—N2—C9 | 142.6 (3) | O3—C12—C17—C16 | −178.6 (4) |
O2—Cu1—N2—C9 | −131.2 (3) | C13—C12—C17—C16 | 1.9 (6) |
N1—Cu1—N2—C10 | 101.7 (3) | O3—C12—C17—C18 | 3.9 (6) |
O4—Cu1—N2—C10 | −94.2 (3) | C13—C12—C17—C18 | −175.7 (4) |
O2—Cu1—N2—C10 | −8.1 (3) | C19—N3—C18—C17 | 176.1 (4) |
O3—Cu2—N3—C18 | 11.4 (4) | Cu2—N3—C18—C17 | −6.9 (6) |
O4—Cu2—N3—C18 | −143.9 (5) | C16—C17—C18—N3 | 179.7 (4) |
N4—Cu2—N3—C18 | 178.9 (4) | C12—C17—C18—N3 | −2.7 (7) |
O3—Cu2—N3—C19 | −171.4 (3) | C18—N3—C19—C20 | 156.8 (4) |
O4—Cu2—N3—C19 | 33.4 (8) | Cu2—N3—C19—C20 | −20.5 (5) |
N4—Cu2—N3—C19 | −3.9 (3) | C21—N4—C20—C19 | −165.9 (4) |
O3—Cu2—N4—C20 | 114.4 (6) | Cu2—N4—C20—C19 | −46.5 (4) |
N3—Cu2—N4—C20 | 27.8 (3) | N3—C19—C20—N4 | 44.2 (5) |
O4—Cu2—N4—C20 | −145.6 (3) | C20—N4—C21—C22 | 158.4 (4) |
O3—Cu2—N4—C21 | −118.4 (6) | Cu2—N4—C21—C22 | 39.7 (4) |
N3—Cu2—N4—C21 | 155.1 (3) | Cu2—O4—C22—C21 | 33.0 (4) |
O4—Cu2—N4—C21 | −18.4 (3) | Cu1—O4—C22—C21 | −84.8 (4) |
Cu1—O1—C1—C2 | −174.2 (3) | N4—C21—C22—O4 | −48.9 (5) |
Cu1—O1—C1—C6 | 6.0 (6) |