Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028868/is2053sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028868/is2053Isup2.hkl |
CCDC reference: 621376
Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Cu(C21H30N10)](ClO4)2 | F(000) = 706 |
Mr = 684.99 | Dx = 1.560 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 3045 reflections |
a = 10.7278 (6) Å | θ = 1.0–27.5° |
b = 13.8859 (6) Å | µ = 1.00 mm−1 |
c = 11.1108 (7) Å | T = 293 K |
β = 118.220 (2)° | Thin plate, green |
V = 1458.39 (14) Å3 | 0.23 × 0.11 × 0.04 mm |
Z = 2 |
Nonius KappaCCD diffractometer | 5771 independent reflections |
Radiation source: fine-focus sealed tube | 4982 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.000 |
φ and ω scans | θmax = 27.0°, θmin = 2.1° |
Absorption correction: multi-scan (DENZO; Otwinowski & Minor, 1997) | h = −13→12 |
Tmin = 0.804, Tmax = 0.961 | k = −15→17 |
5771 measured reflections | l = 0→14 |
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)] = 0.082 | H-atom parameters constrained |
wR(F2) = 0.244 | w = 1/[σ2(Fo2) + (0.1344P)2 + 6.0122P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
5771 reflections | Δρmax = 2.16 e Å−3 |
382 parameters | Δρmin = −0.94 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2461 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.06 (3) |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
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 | ||
Cu | 0.35175 (10) | 0.16513 (7) | 0.16139 (10) | 0.0348 (3) | |
Cl1 | 0.3518 (2) | 0.75204 (17) | 0.1958 (2) | 0.0393 (5) | |
O1 | 0.2727 (8) | 0.8092 (7) | 0.0764 (7) | 0.060 (2) | |
O2 | 0.5000 (8) | 0.7789 (8) | 0.2568 (8) | 0.071 (3) | |
O3 | 0.3341 (10) | 0.6544 (8) | 0.1575 (9) | 0.072 (2) | |
O4 | 0.2977 (8) | 0.7666 (6) | 0.2902 (7) | 0.0501 (16) | |
Cl2 | 0.9861 (2) | 0.31374 (16) | 0.4828 (2) | 0.0417 (5) | |
O5 | 0.9879 (11) | 0.2126 (6) | 0.4997 (10) | 0.065 (2) | |
O6 | 0.8530 (10) | 0.3421 (7) | 0.3644 (10) | 0.072 (2) | |
O7 | 1.1014 (11) | 0.3401 (9) | 0.4621 (11) | 0.081 (3) | |
O8 | 0.9971 (10) | 0.3561 (7) | 0.6057 (9) | 0.066 (2) | |
N1 | 0.3244 (7) | 0.3992 (6) | 0.1518 (7) | 0.0348 (15) | |
N2 | 0.1311 (8) | 0.2471 (5) | 0.0551 (8) | 0.0348 (15) | |
N3 | 0.2336 (7) | 0.0902 (6) | −0.0143 (7) | 0.0347 (15) | |
N4 | 0.1334 (9) | −0.0061 (6) | −0.1878 (8) | 0.0452 (19) | |
NH4 | 0.1218 | −0.0538 | −0.2416 | 0.054* | |
N5 | 0.4279 (8) | 0.2419 (6) | 0.3413 (7) | 0.0371 (16) | |
N6 | 0.2884 (9) | 0.0781 (6) | 0.2682 (8) | 0.0415 (17) | |
N7 | 0.2104 (8) | −0.0162 (5) | 0.3739 (8) | 0.0392 (17) | |
NH7 | 0.1694 | −0.0646 | 0.3886 | 0.047* | |
N8 | 0.4532 (7) | 0.2428 (5) | 0.0779 (7) | 0.0331 (14) | |
N9 | 0.5639 (9) | 0.0705 (7) | 0.2250 (9) | 0.0468 (19) | |
N10 | 0.7760 (9) | 0.0064 (6) | 0.2869 (9) | 0.049 (2) | |
NH10 | 0.8462 | −0.0328 | 0.3238 | 0.058* | |
C1 | 0.1762 (9) | 0.4209 (6) | 0.0785 (10) | 0.039 (2) | |
H1A | 0.1483 | 0.4306 | −0.0173 | 0.047* | |
H1B | 0.1572 | 0.4799 | 0.1138 | 0.047* | |
C2 | 0.0905 (10) | 0.3384 (6) | 0.0938 (10) | 0.0389 (19) | |
H2A | 0.1079 | 0.3349 | 0.1876 | 0.047* | |
H2B | −0.0096 | 0.3500 | 0.0358 | 0.047* | |
C3 | 0.0493 (10) | 0.2091 (7) | −0.0594 (10) | 0.042 (2) | |
H3 | −0.0394 | 0.2350 | −0.1163 | 0.050* | |
C4 | 0.0999 (10) | 0.1230 (6) | −0.0981 (9) | 0.0358 (18) | |
C5 | 0.2504 (12) | 0.0109 (8) | −0.0703 (11) | 0.047 (2) | |
H5 | 0.3311 | −0.0273 | −0.0335 | 0.057* | |
C6 | 0.0337 (11) | 0.0648 (7) | −0.2100 (10) | 0.044 (2) | |
C7 | −0.1038 (12) | 0.0664 (8) | −0.3311 (10) | 0.048 (2) | |
H7A | −0.1555 | 0.1221 | −0.3286 | 0.073* | |
H7B | −0.1555 | 0.0093 | −0.3336 | 0.073* | |
H7C | −0.0913 | 0.0689 | −0.4111 | 0.073* | |
C8 | 0.3981 (11) | 0.4161 (6) | 0.2982 (10) | 0.042 (2) | |
H8A | 0.3296 | 0.4215 | 0.3316 | 0.050* | |
H8B | 0.4493 | 0.4765 | 0.3166 | 0.050* | |
C9 | 0.5028 (10) | 0.3341 (7) | 0.3750 (10) | 0.0388 (19) | |
H9A | 0.5775 | 0.3328 | 0.3493 | 0.047* | |
H9B | 0.5456 | 0.3452 | 0.4727 | 0.047* | |
C10 | 0.3916 (9) | 0.2074 (7) | 0.4277 (10) | 0.0391 (19) | |
H10 | 0.4124 | 0.2390 | 0.5089 | 0.047* | |
C11 | 0.3167 (9) | 0.1168 (7) | 0.3915 (9) | 0.0357 (18) | |
C12 | 0.2249 (11) | −0.0043 (7) | 0.2598 (11) | 0.045 (2) | |
H12 | 0.1947 | −0.0476 | 0.1874 | 0.054* | |
C13 | 0.2671 (10) | 0.0558 (7) | 0.4587 (10) | 0.042 (2) | |
C14 | 0.2707 (11) | 0.0662 (9) | 0.5940 (10) | 0.050 (2) | |
H14A | 0.1890 | 0.1015 | 0.5829 | 0.075* | |
H14B | 0.3548 | 0.1002 | 0.6556 | 0.075* | |
H14C | 0.2705 | 0.0035 | 0.6304 | 0.075* | |
C15 | 0.4061 (10) | 0.4159 (6) | 0.0797 (9) | 0.0377 (19) | |
H15A | 0.5042 | 0.4280 | 0.1452 | 0.045* | |
H15B | 0.3697 | 0.4722 | 0.0216 | 0.045* | |
C16 | 0.3967 (9) | 0.3279 (6) | −0.0075 (9) | 0.0361 (18) | |
H16A | 0.2988 | 0.3166 | −0.0742 | 0.043* | |
H16B | 0.4497 | 0.3401 | −0.0565 | 0.043* | |
C17 | 0.5776 (9) | 0.2120 (6) | 0.1023 (9) | 0.0345 (17) | |
H17 | 0.6270 | 0.2464 | 0.0666 | 0.041* | |
C18 | 0.6407 (10) | 0.1292 (7) | 0.1802 (9) | 0.0383 (19) | |
C19 | 0.6519 (11) | −0.0046 (7) | 0.2894 (11) | 0.047 (2) | |
H19 | 0.6299 | −0.0562 | 0.3295 | 0.057* | |
C20 | 0.7748 (9) | 0.0885 (7) | 0.2175 (9) | 0.0371 (18) | |
C21 | 0.8930 (11) | 0.1212 (9) | 0.1942 (11) | 0.050 (2) | |
H21A | 0.9802 | 0.1169 | 0.2780 | 0.075* | |
H21B | 0.8772 | 0.1868 | 0.1631 | 0.075* | |
H21C | 0.8983 | 0.0812 | 0.1263 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu | 0.0387 (5) | 0.0269 (5) | 0.0374 (5) | −0.0012 (4) | 0.0169 (4) | 0.0011 (5) |
Cl1 | 0.0420 (11) | 0.0331 (12) | 0.0406 (10) | 0.0007 (8) | 0.0176 (9) | 0.0029 (9) |
O1 | 0.060 (4) | 0.082 (6) | 0.040 (3) | 0.018 (4) | 0.027 (3) | 0.008 (4) |
O2 | 0.037 (4) | 0.114 (8) | 0.053 (4) | −0.010 (4) | 0.014 (3) | 0.016 (5) |
O3 | 0.098 (6) | 0.040 (5) | 0.082 (5) | 0.013 (5) | 0.045 (5) | 0.001 (4) |
O4 | 0.055 (4) | 0.048 (4) | 0.047 (3) | −0.006 (3) | 0.025 (3) | 0.000 (3) |
Cl2 | 0.0505 (12) | 0.0200 (10) | 0.0524 (12) | 0.0009 (8) | 0.0225 (10) | 0.0008 (9) |
O5 | 0.087 (6) | 0.023 (4) | 0.080 (6) | 0.000 (3) | 0.035 (5) | −0.004 (3) |
O6 | 0.065 (5) | 0.064 (6) | 0.073 (5) | 0.006 (4) | 0.020 (4) | 0.021 (5) |
O7 | 0.091 (7) | 0.086 (7) | 0.094 (7) | −0.015 (6) | 0.065 (6) | −0.003 (6) |
O8 | 0.077 (6) | 0.057 (6) | 0.074 (5) | 0.002 (4) | 0.043 (5) | −0.013 (4) |
N1 | 0.034 (4) | 0.023 (4) | 0.040 (4) | 0.004 (3) | 0.012 (3) | 0.005 (3) |
N2 | 0.040 (4) | 0.014 (3) | 0.050 (4) | −0.002 (3) | 0.022 (3) | −0.006 (3) |
N3 | 0.034 (4) | 0.030 (4) | 0.038 (4) | 0.002 (3) | 0.015 (3) | 0.000 (3) |
N4 | 0.062 (5) | 0.036 (5) | 0.046 (4) | −0.008 (4) | 0.033 (4) | −0.006 (3) |
N5 | 0.040 (4) | 0.027 (4) | 0.038 (4) | 0.001 (3) | 0.013 (3) | 0.006 (3) |
N6 | 0.042 (4) | 0.036 (5) | 0.046 (4) | 0.000 (3) | 0.020 (3) | 0.003 (3) |
N7 | 0.039 (4) | 0.020 (4) | 0.052 (4) | −0.008 (3) | 0.015 (3) | 0.001 (3) |
N8 | 0.036 (3) | 0.021 (4) | 0.042 (4) | −0.005 (3) | 0.019 (3) | −0.005 (3) |
N9 | 0.051 (5) | 0.044 (5) | 0.045 (4) | −0.004 (4) | 0.023 (4) | 0.000 (4) |
N10 | 0.049 (5) | 0.031 (5) | 0.049 (4) | 0.010 (4) | 0.009 (4) | −0.001 (4) |
C1 | 0.041 (5) | 0.020 (4) | 0.051 (5) | 0.002 (3) | 0.017 (4) | −0.004 (4) |
C2 | 0.041 (5) | 0.014 (4) | 0.057 (5) | 0.006 (3) | 0.020 (4) | 0.001 (4) |
C3 | 0.044 (5) | 0.036 (5) | 0.047 (5) | −0.005 (4) | 0.023 (4) | −0.002 (4) |
C4 | 0.047 (5) | 0.018 (4) | 0.044 (5) | −0.002 (3) | 0.023 (4) | 0.001 (3) |
C5 | 0.056 (6) | 0.041 (6) | 0.053 (5) | −0.003 (4) | 0.032 (5) | −0.002 (4) |
C6 | 0.060 (6) | 0.031 (5) | 0.052 (5) | −0.013 (4) | 0.035 (5) | −0.002 (4) |
C7 | 0.060 (6) | 0.038 (6) | 0.037 (5) | −0.018 (5) | 0.015 (4) | −0.011 (4) |
C8 | 0.056 (6) | 0.014 (4) | 0.052 (5) | −0.007 (4) | 0.022 (4) | −0.006 (4) |
C9 | 0.043 (5) | 0.030 (5) | 0.044 (5) | −0.007 (4) | 0.021 (4) | −0.001 (4) |
C10 | 0.035 (4) | 0.040 (5) | 0.044 (5) | 0.005 (4) | 0.020 (4) | 0.002 (4) |
C11 | 0.034 (4) | 0.030 (5) | 0.041 (4) | 0.010 (3) | 0.016 (4) | 0.012 (4) |
C12 | 0.060 (6) | 0.020 (5) | 0.063 (6) | −0.003 (4) | 0.037 (5) | 0.001 (4) |
C13 | 0.041 (5) | 0.040 (5) | 0.050 (5) | 0.011 (4) | 0.024 (4) | 0.008 (4) |
C14 | 0.049 (6) | 0.057 (7) | 0.046 (5) | 0.010 (5) | 0.025 (5) | 0.015 (5) |
C15 | 0.044 (5) | 0.022 (4) | 0.044 (4) | 0.014 (3) | 0.018 (4) | 0.011 (4) |
C16 | 0.036 (4) | 0.021 (4) | 0.046 (5) | 0.004 (3) | 0.015 (4) | 0.002 (3) |
C17 | 0.040 (4) | 0.026 (4) | 0.039 (4) | −0.002 (3) | 0.020 (4) | 0.000 (3) |
C18 | 0.040 (5) | 0.033 (5) | 0.041 (4) | 0.001 (3) | 0.018 (4) | −0.001 (3) |
C19 | 0.062 (6) | 0.021 (5) | 0.054 (5) | −0.001 (4) | 0.024 (5) | 0.000 (4) |
C20 | 0.041 (5) | 0.025 (5) | 0.038 (4) | 0.006 (3) | 0.014 (4) | −0.005 (3) |
C21 | 0.043 (5) | 0.052 (6) | 0.055 (6) | 0.006 (4) | 0.023 (4) | −0.003 (5) |
Cu—N2 | 2.377 (7) | C1—H1A | 0.9700 |
Cu—N3 | 2.040 (7) | C1—H1B | 0.9700 |
Cu—N5 | 2.062 (8) | C2—H2A | 0.9700 |
Cu—N6 | 2.022 (8) | C2—H2B | 0.9700 |
Cu—N8 | 2.041 (7) | C3—C4 | 1.459 (13) |
Cu—N9 | 2.426 (9) | C3—H3 | 0.9300 |
Cl1—O3 | 1.406 (12) | C4—C6 | 1.368 (13) |
Cl1—O1 | 1.430 (8) | C5—H5 | 0.9300 |
Cl1—O4 | 1.433 (7) | C6—C7 | 1.452 (15) |
Cl1—O2 | 1.451 (8) | C7—H7A | 0.9600 |
Cl2—O7 | 1.409 (9) | C7—H7B | 0.9600 |
Cl2—O5 | 1.416 (9) | C7—H7C | 0.9600 |
Cl2—O8 | 1.440 (9) | C8—C9 | 1.542 (13) |
Cl2—O6 | 1.465 (9) | C8—H8A | 0.9700 |
N1—C1 | 1.434 (11) | C8—H8B | 0.9700 |
N1—C8 | 1.452 (12) | C9—H9A | 0.9700 |
N1—C15 | 1.459 (12) | C9—H9B | 0.9700 |
N2—C3 | 1.269 (12) | C10—C11 | 1.444 (13) |
N2—C2 | 1.469 (10) | C10—H10 | 0.9300 |
N3—C5 | 1.318 (13) | C11—C13 | 1.390 (13) |
N3—C4 | 1.368 (12) | C12—H12 | 0.9300 |
N4—C5 | 1.337 (14) | C13—C14 | 1.493 (14) |
N4—C6 | 1.388 (14) | C14—H14A | 0.9600 |
N4—NH4 | 0.8600 | C14—H14B | 0.9600 |
N5—C10 | 1.287 (12) | C14—H14C | 0.9600 |
N5—C9 | 1.463 (12) | C15—C16 | 1.534 (13) |
N6—C12 | 1.313 (13) | C15—H15A | 0.9700 |
N6—C11 | 1.366 (12) | C15—H15B | 0.9700 |
N7—C13 | 1.309 (13) | C16—H16A | 0.9700 |
N7—C12 | 1.359 (12) | C16—H16B | 0.9700 |
N7—NH7 | 0.8600 | C17—C18 | 1.406 (13) |
N8—C17 | 1.302 (11) | C17—H17 | 0.9300 |
N8—C16 | 1.455 (11) | C18—C20 | 1.413 (12) |
N9—C19 | 1.361 (14) | C19—H19 | 0.9300 |
N9—C18 | 1.407 (13) | C20—C21 | 1.481 (14) |
N10—C19 | 1.353 (15) | C21—H21A | 0.9600 |
N10—C20 | 1.373 (14) | C21—H21B | 0.9600 |
N10—NH10 | 0.8600 | C21—H21C | 0.9600 |
C1—C2 | 1.528 (13) | ||
N2—Cu—N3 | 75.3 (3) | C6—C4—C3 | 130.3 (9) |
N2—Cu—N5 | 94.5 (3) | N3—C5—N4 | 109.6 (9) |
N2—Cu—N6 | 92.6 (3) | N3—C5—H5 | 125.2 |
N2—Cu—N8 | 98.1 (3) | N4—C5—H5 | 125.2 |
N2—Cu—N9 | 168.8 (3) | C4—C6—N4 | 103.5 (9) |
N3—Cu—N5 | 166.7 (3) | C4—C6—C7 | 134.1 (10) |
N3—Cu—N6 | 91.6 (3) | N4—C6—C7 | 122.4 (9) |
N3—Cu—N8 | 93.3 (3) | C6—C7—H7A | 109.5 |
N3—Cu—N9 | 94.3 (3) | C6—C7—H7B | 109.5 |
N5—Cu—N6 | 80.2 (3) | H7A—C7—H7B | 109.5 |
N5—Cu—N8 | 96.6 (3) | C6—C7—H7C | 109.5 |
N5—Cu—N9 | 96.3 (3) | H7A—C7—H7C | 109.5 |
N6—Cu—N8 | 169.0 (3) | H7B—C7—H7C | 109.5 |
N6—Cu—N9 | 92.0 (3) | N1—C8—C9 | 111.7 (8) |
N8—Cu—N9 | 77.9 (3) | N1—C8—H8A | 109.3 |
O3—Cl1—O1 | 108.6 (6) | C9—C8—H8A | 109.3 |
O3—Cl1—O4 | 108.3 (5) | N1—C8—H8B | 109.3 |
O1—Cl1—O4 | 109.4 (4) | C9—C8—H8B | 109.3 |
O3—Cl1—O2 | 110.6 (6) | H8A—C8—H8B | 107.9 |
O1—Cl1—O2 | 109.2 (5) | N5—C9—C8 | 109.6 (7) |
O4—Cl1—O2 | 110.8 (5) | N5—C9—H9A | 109.7 |
O7—Cl2—O5 | 108.7 (7) | C8—C9—H9A | 109.7 |
O7—Cl2—O8 | 111.4 (6) | N5—C9—H9B | 109.7 |
O5—Cl2—O8 | 106.8 (6) | C8—C9—H9B | 109.7 |
O7—Cl2—O6 | 110.0 (6) | H9A—C9—H9B | 108.2 |
O5—Cl2—O6 | 109.4 (6) | N5—C10—C11 | 116.2 (9) |
O8—Cl2—O6 | 110.5 (6) | N5—C10—H10 | 121.9 |
C1—N1—C8 | 118.2 (8) | C11—C10—H10 | 121.9 |
C1—N1—C15 | 116.6 (7) | N6—C11—C13 | 109.8 (9) |
C8—N1—C15 | 116.0 (7) | N6—C11—C10 | 116.9 (8) |
C3—N2—C2 | 119.5 (8) | C13—C11—C10 | 133.2 (9) |
C3—N2—Cu | 110.7 (6) | N6—C12—N7 | 108.9 (9) |
C2—N2—Cu | 129.1 (6) | N6—C12—H12 | 125.6 |
C5—N3—C4 | 106.9 (8) | N7—C12—H12 | 125.6 |
C5—N3—Cu | 135.7 (7) | N7—C13—C11 | 104.2 (9) |
C4—N3—Cu | 117.3 (6) | N7—C13—C14 | 125.4 (9) |
C5—N4—C6 | 109.6 (8) | C11—C13—C14 | 130.4 (10) |
C5—N4—NH4 | 125.2 | C13—C14—H14A | 109.5 |
C6—N4—NH4 | 125.2 | C13—C14—H14B | 109.5 |
C10—N5—C9 | 117.2 (8) | H14A—C14—H14B | 109.5 |
C10—N5—Cu | 114.2 (7) | C13—C14—H14C | 109.5 |
C9—N5—Cu | 128.2 (6) | H14A—C14—H14C | 109.5 |
C12—N6—C11 | 106.0 (8) | H14B—C14—H14C | 109.5 |
C12—N6—Cu | 141.8 (7) | N1—C15—C16 | 110.1 (8) |
C11—N6—Cu | 112.2 (6) | N1—C15—H15A | 109.6 |
C13—N7—C12 | 111.1 (8) | C16—C15—H15A | 109.6 |
C13—N7—NH7 | 124.5 | N1—C15—H15B | 109.6 |
C12—N7—NH7 | 124.5 | C16—C15—H15B | 109.6 |
C17—N8—C16 | 118.2 (7) | H15A—C15—H15B | 108.2 |
C17—N8—Cu | 116.5 (6) | N8—C16—C15 | 110.6 (7) |
C16—N8—Cu | 125.3 (5) | N8—C16—H16A | 109.5 |
C19—N9—C18 | 104.7 (8) | C15—C16—H16A | 109.5 |
C19—N9—Cu | 152.9 (7) | N8—C16—H16B | 109.5 |
C18—N9—Cu | 102.0 (6) | C15—C16—H16B | 109.5 |
C19—N10—C20 | 111.0 (8) | H16A—C16—H16B | 108.1 |
C19—N10—NH10 | 124.5 | N8—C17—C18 | 123.0 (8) |
C20—N10—NH10 | 124.5 | N8—C17—H17 | 118.5 |
N1—C1—C2 | 110.0 (7) | C18—C17—H17 | 118.5 |
N1—C1—H1A | 109.7 | C17—C18—N9 | 120.0 (8) |
C2—C1—H1A | 109.7 | C17—C18—C20 | 129.4 (9) |
N1—C1—H1B | 109.7 | N9—C18—C20 | 110.5 (8) |
C2—C1—H1B | 109.7 | N10—C19—N9 | 110.3 (9) |
H1A—C1—H1B | 108.2 | N10—C19—H19 | 124.8 |
N2—C2—C1 | 109.8 (7) | N9—C19—H19 | 124.8 |
N2—C2—H2A | 109.7 | N10—C20—C18 | 103.6 (8) |
C1—C2—H2A | 109.7 | N10—C20—C21 | 124.9 (9) |
N2—C2—H2B | 109.7 | C18—C20—C21 | 131.5 (9) |
C1—C2—H2B | 109.7 | C20—C21—H21A | 109.5 |
H2A—C2—H2B | 108.2 | C20—C21—H21B | 109.5 |
N2—C3—C4 | 117.3 (9) | H21A—C21—H21B | 109.5 |
N2—C3—H3 | 121.3 | C20—C21—H21C | 109.5 |
C4—C3—H3 | 121.3 | H21A—C21—H21C | 109.5 |
N3—C4—C6 | 110.4 (8) | H21B—C21—H21C | 109.5 |
N3—C4—C3 | 119.3 (8) | ||
N6—Cu—N2—C3 | −93.6 (7) | Cu—N2—C2—C1 | 64.9 (10) |
N3—Cu—N2—C3 | −2.6 (6) | N1—C1—C2—N2 | −52.9 (10) |
N8—Cu—N2—C3 | 88.7 (6) | C2—N2—C3—C4 | 174.8 (8) |
N5—Cu—N2—C3 | −173.9 (6) | Cu—N2—C3—C4 | 3.7 (10) |
N9—Cu—N2—C3 | 20.5 (18) | C5—N3—C4—C6 | −1.8 (10) |
N6—Cu—N2—C2 | 96.5 (7) | Cu—N3—C4—C6 | −179.1 (6) |
N3—Cu—N2—C2 | −172.6 (8) | C5—N3—C4—C3 | 178.0 (8) |
N8—Cu—N2—C2 | −81.2 (7) | Cu—N3—C4—C3 | 0.6 (10) |
N5—Cu—N2—C2 | 16.1 (7) | N2—C3—C4—N3 | −3.2 (12) |
N9—Cu—N2—C2 | −149.5 (13) | N2—C3—C4—C6 | 176.4 (9) |
N6—Cu—N3—C5 | −83.1 (10) | C4—N3—C5—N4 | 1.5 (11) |
N8—Cu—N3—C5 | 87.1 (10) | Cu—N3—C5—N4 | 178.1 (6) |
N5—Cu—N3—C5 | −134.3 (13) | C6—N4—C5—N3 | −0.8 (11) |
N2—Cu—N3—C5 | −175.4 (10) | N3—C4—C6—N4 | 1.3 (10) |
N9—Cu—N3—C5 | 9.0 (10) | C3—C4—C6—N4 | −178.4 (9) |
N6—Cu—N3—C4 | 93.2 (7) | N3—C4—C6—C7 | −177.9 (10) |
N8—Cu—N3—C4 | −96.6 (6) | C3—C4—C6—C7 | 2.4 (18) |
N5—Cu—N3—C4 | 42.0 (17) | C5—N4—C6—C4 | −0.3 (10) |
N2—Cu—N3—C4 | 1.0 (6) | C5—N4—C6—C7 | 179.0 (9) |
N9—Cu—N3—C4 | −174.7 (6) | C1—N1—C8—C9 | 138.9 (8) |
N6—Cu—N5—C10 | −6.0 (6) | C15—N1—C8—C9 | −75.5 (9) |
N3—Cu—N5—C10 | 46.3 (17) | C10—N5—C9—C8 | −99.4 (9) |
N8—Cu—N5—C10 | −175.4 (6) | Cu—N5—C9—C8 | 73.2 (9) |
N2—Cu—N5—C10 | 85.9 (6) | N1—C8—C9—N5 | −55.6 (10) |
N9—Cu—N5—C10 | −96.9 (7) | C9—N5—C10—C11 | 179.5 (7) |
N6—Cu—N5—C9 | −178.7 (8) | Cu—N5—C10—C11 | 5.9 (10) |
N3—Cu—N5—C9 | −126.4 (13) | C12—N6—C11—C13 | −0.6 (10) |
N8—Cu—N5—C9 | 11.9 (7) | Cu—N6—C11—C13 | 178.1 (6) |
N2—Cu—N5—C9 | −86.8 (7) | C12—N6—C11—C10 | 178.0 (8) |
N9—Cu—N5—C9 | 90.4 (7) | Cu—N6—C11—C10 | −3.3 (9) |
N3—Cu—N6—C12 | 13.2 (12) | N5—C10—C11—N6 | −1.8 (11) |
N8—Cu—N6—C12 | −103.4 (19) | N5—C10—C11—C13 | 176.5 (9) |
N5—Cu—N6—C12 | −177.3 (12) | C11—N6—C12—N7 | 1.5 (11) |
N2—Cu—N6—C12 | 88.6 (12) | Cu—N6—C12—N7 | −176.6 (8) |
N9—Cu—N6—C12 | −81.2 (12) | C13—N7—C12—N6 | −1.9 (12) |
N3—Cu—N6—C11 | −164.7 (6) | C12—N7—C13—C11 | 1.4 (10) |
N8—Cu—N6—C11 | 78.6 (19) | C12—N7—C13—C14 | −179.9 (9) |
N5—Cu—N6—C11 | 4.8 (6) | N6—C11—C13—N7 | −0.5 (10) |
N2—Cu—N6—C11 | −89.4 (6) | C10—C11—C13—N7 | −178.8 (9) |
N9—Cu—N6—C11 | 100.9 (6) | N6—C11—C13—C14 | −179.1 (9) |
N6—Cu—N8—C17 | 19 (2) | C10—C11—C13—C14 | 2.6 (17) |
N3—Cu—N8—C17 | −97.6 (6) | C1—N1—C15—C16 | −85.4 (9) |
N5—Cu—N8—C17 | 91.2 (6) | C8—N1—C15—C16 | 128.4 (8) |
N2—Cu—N8—C17 | −173.3 (6) | C17—N8—C16—C15 | −104.7 (9) |
N9—Cu—N8—C17 | −3.9 (6) | Cu—N8—C16—C15 | 76.4 (8) |
N6—Cu—N8—C16 | −162.2 (15) | N1—C15—C16—N8 | −60.3 (9) |
N3—Cu—N8—C16 | 81.4 (7) | C16—N8—C17—C18 | −178.2 (8) |
N5—Cu—N8—C16 | −89.8 (7) | Cu—N8—C17—C18 | 0.8 (11) |
N2—Cu—N8—C16 | 5.7 (7) | N8—C17—C18—N9 | 5.9 (14) |
N9—Cu—N8—C16 | 175.1 (7) | N8—C17—C18—C20 | −178.5 (9) |
N6—Cu—N9—C19 | 0.8 (16) | C19—N9—C18—C17 | 176.7 (8) |
N3—Cu—N9—C19 | −91.0 (16) | Cu—N9—C18—C17 | −7.8 (10) |
N8—Cu—N9—C19 | 176.6 (16) | C19—N9—C18—C20 | 0.3 (11) |
N5—Cu—N9—C19 | 81.1 (16) | Cu—N9—C18—C20 | 175.9 (6) |
N2—Cu—N9—C19 | −113.3 (18) | C20—N10—C19—N9 | −1.4 (12) |
N6—Cu—N9—C18 | −169.8 (6) | C18—N9—C19—N10 | 0.6 (11) |
N3—Cu—N9—C18 | 98.5 (6) | Cu—N9—C19—N10 | −169.8 (11) |
N8—Cu—N9—C18 | 6.0 (6) | C19—N10—C20—C18 | 1.6 (10) |
N5—Cu—N9—C18 | −89.4 (6) | C19—N10—C20—C21 | −179.1 (9) |
N2—Cu—N9—C18 | 76.2 (16) | C17—C18—C20—N10 | −177.0 (9) |
C8—N1—C1—C2 | −81.2 (9) | N9—C18—C20—N10 | −1.1 (10) |
C15—N1—C1—C2 | 133.3 (8) | C17—C18—C20—C21 | 3.7 (17) |
C3—N2—C2—C1 | −104.3 (9) | N9—C18—C20—C21 | 179.6 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—NH4···O6i | 0.86 | 2.09 | 2.930 (13) | 165 |
N7—NH7···O8ii | 0.86 | 2.12 | 2.937 (14) | 157 |
N10—NH10···O8iii | 0.86 | 2.14 | 2.993 (14) | 172 |
Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x+1, y−1/2, −z+1; (iii) −x+2, y−1/2, −z+1. |