Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805000280/ob6467sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805000280/ob6467Isup2.hkl |
CCDC reference: 263535
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.
[Cu(C13H15BrNO)2] | F(000) = 2520 |
Mr = 625.88 | Dx = 1.621 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 10170 reflections |
a = 14.996 (1) Å | θ = 2.6–22.8° |
b = 13.597 (1) Å | µ = 3.99 mm−1 |
c = 25.156 (2) Å | T = 298 K |
V = 5129.3 (7) Å3 | Block, blue |
Z = 8 | 0.22 × 0.21 × 0.18 mm |
Bruker APEX area-detector diffractometer | 5866 independent reflections |
Radiation source: fine-focus sealed tube | 4083 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
φ and ω scans | θmax = 27.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→19 |
Tmin = 0.433, Tmax = 0.487 | k = −17→17 |
56364 measured reflections | l = −32→32 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0513P)2 + 4.6248P] where P = (Fo2 + 2Fc2)/3 |
5866 reflections | (Δ/σ)max < 0.001 |
298 parameters | Δρmax = 0.71 e Å−3 |
0 restraints | Δρmin = −0.36 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 | ||
Cu1 | 0.14073 (3) | 0.58035 (3) | 0.307450 (17) | 0.04668 (13) | |
Br1 | −0.11579 (4) | 0.89451 (4) | 0.48997 (2) | 0.0925 (2) | |
Br2 | 0.32284 (3) | 0.25746 (4) | 0.101200 (18) | 0.07509 (16) | |
O1 | 0.15852 (17) | 0.66642 (19) | 0.36704 (11) | 0.0614 (7) | |
O2 | 0.21850 (17) | 0.58901 (17) | 0.24711 (11) | 0.0570 (6) | |
N1 | 0.01424 (19) | 0.6249 (2) | 0.29250 (11) | 0.0459 (6) | |
N2 | 0.1724 (2) | 0.4384 (2) | 0.32252 (12) | 0.0487 (7) | |
C1 | 0.0055 (2) | 0.7203 (2) | 0.37494 (14) | 0.0470 (8) | |
C2 | 0.0948 (3) | 0.7099 (2) | 0.39320 (14) | 0.0507 (9) | |
C3 | 0.1138 (3) | 0.7531 (3) | 0.44319 (16) | 0.0601 (10) | |
H3 | 0.1704 | 0.7448 | 0.4575 | 0.072* | |
C4 | 0.0533 (3) | 0.8060 (3) | 0.47094 (15) | 0.0645 (11) | |
H4 | 0.0692 | 0.8343 | 0.5032 | 0.077* | |
C5 | −0.0319 (3) | 0.8180 (3) | 0.45154 (14) | 0.0600 (10) | |
C6 | −0.0558 (3) | 0.7753 (3) | 0.40463 (14) | 0.0548 (9) | |
H6 | −0.1138 | 0.7829 | 0.3921 | 0.066* | |
C7 | −0.0266 (2) | 0.6806 (3) | 0.32519 (14) | 0.0490 (8) | |
H7 | −0.0845 | 0.6978 | 0.3158 | 0.059* | |
C8 | −0.0334 (2) | 0.5972 (2) | 0.24355 (14) | 0.0481 (8) | |
H8 | −0.0970 | 0.6116 | 0.2483 | 0.058* | |
C9 | −0.0232 (3) | 0.4892 (3) | 0.23293 (15) | 0.0550 (9) | |
H9A | −0.0501 | 0.4520 | 0.2616 | 0.066* | |
H9B | 0.0397 | 0.4725 | 0.2315 | 0.066* | |
C10 | −0.0674 (3) | 0.4616 (3) | 0.18054 (16) | 0.0677 (11) | |
H10A | −0.0576 | 0.3923 | 0.1735 | 0.081* | |
H10B | −0.1312 | 0.4724 | 0.1833 | 0.081* | |
C11 | −0.0309 (3) | 0.5213 (4) | 0.13520 (17) | 0.0766 (13) | |
H11A | 0.0321 | 0.5072 | 0.1308 | 0.092* | |
H11B | −0.0613 | 0.5032 | 0.1026 | 0.092* | |
C12 | −0.0435 (4) | 0.6289 (3) | 0.14551 (16) | 0.0788 (13) | |
H12A | −0.1067 | 0.6438 | 0.1474 | 0.095* | |
H12B | −0.0181 | 0.6664 | 0.1164 | 0.095* | |
C13 | 0.0015 (3) | 0.6589 (3) | 0.19768 (15) | 0.0667 (11) | |
H13A | 0.0655 | 0.6502 | 0.1946 | 0.080* | |
H13B | −0.0100 | 0.7279 | 0.2047 | 0.080* | |
C14 | 0.2364 (2) | 0.4137 (2) | 0.23458 (13) | 0.0463 (8) | |
C15 | 0.2394 (2) | 0.5131 (3) | 0.21718 (15) | 0.0511 (8) | |
C16 | 0.2703 (3) | 0.5295 (3) | 0.16496 (15) | 0.0598 (10) | |
H16 | 0.2748 | 0.5939 | 0.1529 | 0.072* | |
C17 | 0.2937 (3) | 0.4556 (3) | 0.13154 (16) | 0.0606 (10) | |
H17 | 0.3119 | 0.4695 | 0.0970 | 0.073* | |
C18 | 0.2903 (2) | 0.3594 (3) | 0.14933 (14) | 0.0533 (9) | |
C19 | 0.2636 (2) | 0.3378 (3) | 0.19992 (14) | 0.0506 (8) | |
H19 | 0.2634 | 0.2728 | 0.2116 | 0.061* | |
C20 | 0.2090 (2) | 0.3838 (3) | 0.28718 (14) | 0.0479 (8) | |
H20 | 0.2190 | 0.3184 | 0.2963 | 0.058* | |
C21 | 0.1532 (2) | 0.3957 (3) | 0.37550 (15) | 0.0524 (9) | |
H21 | 0.1624 | 0.3244 | 0.3739 | 0.063* | |
C22 | 0.2179 (3) | 0.4392 (3) | 0.41604 (15) | 0.0623 (10) | |
H22A | 0.2783 | 0.4196 | 0.4071 | 0.075* | |
H22B | 0.2148 | 0.5104 | 0.4146 | 0.075* | |
C23 | 0.1958 (3) | 0.4045 (4) | 0.47222 (17) | 0.0718 (12) | |
H23A | 0.2062 | 0.3343 | 0.4749 | 0.086* | |
H23B | 0.2349 | 0.4372 | 0.4974 | 0.086* | |
C24 | 0.1004 (3) | 0.4265 (3) | 0.48611 (16) | 0.0695 (11) | |
H24A | 0.0913 | 0.4972 | 0.4866 | 0.083* | |
H24B | 0.0874 | 0.4014 | 0.5214 | 0.083* | |
C25 | 0.0368 (3) | 0.3798 (3) | 0.44595 (15) | 0.0632 (10) | |
H25A | 0.0428 | 0.3088 | 0.4472 | 0.076* | |
H25B | −0.0242 | 0.3963 | 0.4552 | 0.076* | |
C26 | 0.0569 (2) | 0.4158 (3) | 0.39027 (15) | 0.0553 (9) | |
H26A | 0.0455 | 0.4859 | 0.3882 | 0.066* | |
H26B | 0.0179 | 0.3830 | 0.3652 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0432 (2) | 0.0422 (2) | 0.0546 (3) | 0.00269 (18) | −0.00131 (19) | 0.00353 (18) |
Br1 | 0.1117 (4) | 0.1014 (4) | 0.0645 (3) | 0.0186 (3) | 0.0050 (3) | −0.0281 (3) |
Br2 | 0.0868 (3) | 0.0790 (3) | 0.0595 (3) | 0.0036 (2) | 0.0212 (2) | −0.0054 (2) |
O1 | 0.0514 (15) | 0.0595 (16) | 0.0733 (17) | 0.0029 (12) | −0.0118 (13) | −0.0114 (14) |
O2 | 0.0548 (15) | 0.0453 (13) | 0.0707 (17) | 0.0006 (11) | 0.0149 (13) | 0.0049 (13) |
N1 | 0.0473 (16) | 0.0439 (15) | 0.0466 (16) | 0.0006 (13) | −0.0042 (13) | −0.0016 (13) |
N2 | 0.0486 (16) | 0.0473 (16) | 0.0503 (16) | 0.0024 (13) | 0.0085 (13) | 0.0088 (13) |
C1 | 0.055 (2) | 0.0423 (18) | 0.0437 (18) | −0.0041 (15) | −0.0040 (16) | 0.0006 (14) |
C2 | 0.058 (2) | 0.0397 (18) | 0.054 (2) | −0.0064 (16) | −0.0105 (18) | 0.0054 (16) |
C3 | 0.063 (2) | 0.059 (2) | 0.059 (2) | −0.009 (2) | −0.0195 (19) | 0.0007 (18) |
C4 | 0.086 (3) | 0.064 (2) | 0.044 (2) | −0.011 (2) | −0.014 (2) | −0.0029 (18) |
C5 | 0.079 (3) | 0.057 (2) | 0.044 (2) | 0.000 (2) | 0.0040 (19) | −0.0039 (16) |
C6 | 0.059 (2) | 0.057 (2) | 0.048 (2) | −0.0005 (18) | −0.0051 (17) | −0.0019 (17) |
C7 | 0.049 (2) | 0.0474 (19) | 0.050 (2) | 0.0013 (16) | −0.0056 (16) | 0.0001 (16) |
C8 | 0.0442 (19) | 0.052 (2) | 0.0485 (19) | 0.0037 (15) | −0.0070 (15) | −0.0056 (15) |
C9 | 0.058 (2) | 0.050 (2) | 0.056 (2) | −0.0034 (17) | −0.0017 (17) | −0.0017 (16) |
C10 | 0.075 (3) | 0.060 (2) | 0.068 (3) | −0.005 (2) | −0.007 (2) | −0.021 (2) |
C11 | 0.075 (3) | 0.102 (4) | 0.053 (2) | −0.003 (3) | −0.001 (2) | −0.021 (2) |
C12 | 0.099 (4) | 0.084 (3) | 0.054 (2) | −0.014 (3) | −0.013 (2) | 0.005 (2) |
C13 | 0.087 (3) | 0.060 (2) | 0.053 (2) | −0.009 (2) | −0.016 (2) | 0.0085 (19) |
C14 | 0.0397 (18) | 0.0503 (19) | 0.0489 (19) | −0.0009 (15) | 0.0046 (15) | 0.0061 (15) |
C15 | 0.0385 (18) | 0.056 (2) | 0.059 (2) | −0.0003 (16) | 0.0013 (16) | 0.0106 (17) |
C16 | 0.063 (2) | 0.059 (2) | 0.058 (2) | −0.0011 (19) | 0.0075 (19) | 0.0153 (19) |
C17 | 0.057 (2) | 0.075 (3) | 0.049 (2) | −0.001 (2) | 0.0075 (18) | 0.016 (2) |
C18 | 0.051 (2) | 0.062 (2) | 0.046 (2) | 0.0010 (18) | 0.0053 (16) | 0.0005 (17) |
C19 | 0.045 (2) | 0.056 (2) | 0.051 (2) | 0.0002 (16) | 0.0037 (15) | 0.0067 (17) |
C20 | 0.0452 (18) | 0.0463 (18) | 0.052 (2) | 0.0003 (15) | 0.0082 (16) | 0.0091 (16) |
C21 | 0.058 (2) | 0.0463 (19) | 0.052 (2) | 0.0029 (16) | 0.0124 (17) | 0.0103 (16) |
C22 | 0.049 (2) | 0.080 (3) | 0.058 (2) | 0.004 (2) | 0.0031 (18) | 0.017 (2) |
C23 | 0.067 (3) | 0.095 (3) | 0.053 (2) | 0.004 (2) | 0.002 (2) | 0.013 (2) |
C24 | 0.080 (3) | 0.076 (3) | 0.053 (2) | 0.003 (2) | 0.017 (2) | −0.002 (2) |
C25 | 0.059 (2) | 0.070 (2) | 0.061 (2) | −0.002 (2) | 0.0202 (19) | −0.003 (2) |
C26 | 0.052 (2) | 0.057 (2) | 0.057 (2) | −0.0049 (17) | 0.0062 (17) | 0.0016 (17) |
Cu1—O2 | 1.918 (3) | C11—H11B | 0.9700 |
Cu1—O1 | 1.920 (3) | C12—C13 | 1.531 (5) |
Cu1—N2 | 2.024 (3) | C12—H12A | 0.9700 |
Cu1—N1 | 2.027 (3) | C12—H12B | 0.9700 |
Br1—C5 | 1.898 (4) | C13—H13A | 0.9700 |
Br2—C18 | 1.904 (4) | C13—H13B | 0.9700 |
O1—C2 | 1.302 (4) | C14—C19 | 1.411 (5) |
O2—C15 | 1.316 (4) | C14—C15 | 1.421 (5) |
N1—C7 | 1.274 (4) | C14—C20 | 1.444 (5) |
N1—C8 | 1.473 (4) | C15—C16 | 1.411 (5) |
N2—C20 | 1.282 (4) | C16—C17 | 1.356 (5) |
N2—C21 | 1.482 (4) | C16—H16 | 0.9300 |
C1—C6 | 1.401 (5) | C17—C18 | 1.384 (5) |
C1—C2 | 1.423 (5) | C17—H17 | 0.9300 |
C1—C7 | 1.446 (5) | C18—C19 | 1.366 (5) |
C2—C3 | 1.417 (5) | C19—H19 | 0.9300 |
C3—C4 | 1.351 (6) | C20—H20 | 0.9300 |
C3—H3 | 0.9300 | C21—C26 | 1.515 (5) |
C4—C5 | 1.377 (6) | C21—C22 | 1.526 (6) |
C4—H4 | 0.9300 | C21—H21 | 0.9800 |
C5—C6 | 1.363 (5) | C22—C23 | 1.526 (5) |
C6—H6 | 0.9300 | C22—H22A | 0.9700 |
C7—H7 | 0.9300 | C22—H22B | 0.9700 |
C8—C9 | 1.501 (5) | C23—C24 | 1.504 (6) |
C8—C13 | 1.520 (5) | C23—H23A | 0.9700 |
C8—H8 | 0.9800 | C23—H23B | 0.9700 |
C9—C10 | 1.522 (5) | C24—C25 | 1.528 (6) |
C9—H9A | 0.9700 | C24—H24A | 0.9700 |
C9—H9B | 0.9700 | C24—H24B | 0.9700 |
C10—C11 | 1.503 (6) | C25—C26 | 1.514 (5) |
C10—H10A | 0.9700 | C25—H25A | 0.9700 |
C10—H10B | 0.9700 | C25—H25B | 0.9700 |
C11—C12 | 1.499 (7) | C26—H26A | 0.9700 |
C11—H11A | 0.9700 | C26—H26B | 0.9700 |
O2—Cu1—O1 | 119.73 (12) | H12A—C12—H12B | 108.1 |
O2—Cu1—N2 | 93.69 (11) | C8—C13—C12 | 110.6 (3) |
O1—Cu1—N2 | 113.74 (12) | C8—C13—H13A | 109.5 |
O2—Cu1—N1 | 113.83 (11) | C12—C13—H13A | 109.5 |
O1—Cu1—N1 | 95.32 (11) | C8—C13—H13B | 109.5 |
N2—Cu1—N1 | 122.65 (12) | C12—C13—H13B | 109.5 |
C2—O1—Cu1 | 124.7 (2) | H13A—C13—H13B | 108.1 |
C15—O2—Cu1 | 123.3 (2) | C19—C14—C15 | 119.8 (3) |
C7—N1—C8 | 117.3 (3) | C19—C14—C20 | 116.2 (3) |
C7—N1—Cu1 | 120.5 (2) | C15—C14—C20 | 124.0 (3) |
C8—N1—Cu1 | 122.2 (2) | O2—C15—C16 | 119.1 (3) |
C20—N2—C21 | 118.7 (3) | O2—C15—C14 | 124.2 (3) |
C20—N2—Cu1 | 121.5 (2) | C16—C15—C14 | 116.6 (3) |
C21—N2—Cu1 | 119.8 (2) | C17—C16—C15 | 123.0 (4) |
C6—C1—C2 | 119.9 (3) | C17—C16—H16 | 118.5 |
C6—C1—C7 | 116.3 (3) | C15—C16—H16 | 118.5 |
C2—C1—C7 | 123.7 (3) | C16—C17—C18 | 119.3 (3) |
O1—C2—C3 | 119.3 (3) | C16—C17—H17 | 120.3 |
O1—C2—C1 | 124.9 (3) | C18—C17—H17 | 120.3 |
C3—C2—C1 | 115.7 (4) | C19—C18—C17 | 121.1 (4) |
C4—C3—C2 | 123.0 (4) | C19—C18—Br2 | 120.7 (3) |
C4—C3—H3 | 118.5 | C17—C18—Br2 | 118.2 (3) |
C2—C3—H3 | 118.5 | C18—C19—C14 | 120.2 (3) |
C3—C4—C5 | 120.2 (4) | C18—C19—H19 | 119.9 |
C3—C4—H4 | 119.9 | C14—C19—H19 | 119.9 |
C5—C4—H4 | 119.9 | N2—C20—C14 | 126.4 (3) |
C6—C5—C4 | 120.1 (4) | N2—C20—H20 | 116.8 |
C6—C5—Br1 | 120.0 (3) | C14—C20—H20 | 116.8 |
C4—C5—Br1 | 120.0 (3) | N2—C21—C26 | 109.5 (3) |
C5—C6—C1 | 121.1 (4) | N2—C21—C22 | 109.1 (3) |
C5—C6—H6 | 119.5 | C26—C21—C22 | 111.8 (3) |
C1—C6—H6 | 119.5 | N2—C21—H21 | 108.8 |
N1—C7—C1 | 128.4 (3) | C26—C21—H21 | 108.8 |
N1—C7—H7 | 115.8 | C22—C21—H21 | 108.8 |
C1—C7—H7 | 115.8 | C23—C22—C21 | 111.2 (3) |
N1—C8—C9 | 110.5 (3) | C23—C22—H22A | 109.4 |
N1—C8—C13 | 109.0 (3) | C21—C22—H22A | 109.4 |
C9—C8—C13 | 111.7 (3) | C23—C22—H22B | 109.4 |
N1—C8—H8 | 108.5 | C21—C22—H22B | 109.4 |
C9—C8—H8 | 108.5 | H22A—C22—H22B | 108.0 |
C13—C8—H8 | 108.5 | C24—C23—C22 | 111.1 (4) |
C8—C9—C10 | 110.5 (3) | C24—C23—H23A | 109.4 |
C8—C9—H9A | 109.5 | C22—C23—H23A | 109.4 |
C10—C9—H9A | 109.5 | C24—C23—H23B | 109.4 |
C8—C9—H9B | 109.5 | C22—C23—H23B | 109.4 |
C10—C9—H9B | 109.5 | H23A—C23—H23B | 108.0 |
H9A—C9—H9B | 108.1 | C23—C24—C25 | 111.0 (3) |
C11—C10—C9 | 111.4 (3) | C23—C24—H24A | 109.4 |
C11—C10—H10A | 109.3 | C25—C24—H24A | 109.4 |
C9—C10—H10A | 109.3 | C23—C24—H24B | 109.4 |
C11—C10—H10B | 109.3 | C25—C24—H24B | 109.4 |
C9—C10—H10B | 109.3 | H24A—C24—H24B | 108.0 |
H10A—C10—H10B | 108.0 | C26—C25—C24 | 110.6 (3) |
C12—C11—C10 | 110.5 (4) | C26—C25—H25A | 109.5 |
C12—C11—H11A | 109.5 | C24—C25—H25A | 109.5 |
C10—C11—H11A | 109.5 | C26—C25—H25B | 109.5 |
C12—C11—H11B | 109.5 | C24—C25—H25B | 109.5 |
C10—C11—H11B | 109.5 | H25A—C25—H25B | 108.1 |
H11A—C11—H11B | 108.1 | C25—C26—C21 | 111.0 (3) |
C11—C12—C13 | 110.7 (4) | C25—C26—H26A | 109.4 |
C11—C12—H12A | 109.5 | C21—C26—H26A | 109.4 |
C13—C12—H12A | 109.5 | C25—C26—H26B | 109.4 |
C11—C12—H12B | 109.5 | C21—C26—H26B | 109.4 |
C13—C12—H12B | 109.5 | H26A—C26—H26B | 108.0 |
O2—Cu1—O1—C2 | 138.7 (3) | Cu1—N1—C8—C13 | −76.2 (3) |
N2—Cu1—O1—C2 | −111.9 (3) | N1—C8—C9—C10 | −176.4 (3) |
N1—Cu1—O1—C2 | 17.3 (3) | C13—C8—C9—C10 | −54.9 (4) |
O1—Cu1—O2—C15 | 148.6 (3) | C8—C9—C10—C11 | 56.3 (5) |
N2—Cu1—O2—C15 | 28.5 (3) | C9—C10—C11—C12 | −57.9 (5) |
N1—Cu1—O2—C15 | −99.8 (3) | C10—C11—C12—C13 | 57.5 (5) |
O2—Cu1—N1—C7 | −135.4 (3) | N1—C8—C13—C12 | 177.4 (3) |
O1—Cu1—N1—C7 | −9.6 (3) | C9—C8—C13—C12 | 55.1 (5) |
N2—Cu1—N1—C7 | 113.1 (3) | C11—C12—C13—C8 | −56.1 (5) |
O2—Cu1—N1—C8 | 43.0 (3) | Cu1—O2—C15—C16 | 158.5 (3) |
O1—Cu1—N1—C8 | 168.9 (2) | Cu1—O2—C15—C14 | −24.1 (5) |
N2—Cu1—N1—C8 | −68.5 (3) | C19—C14—C15—O2 | −177.5 (3) |
O2—Cu1—N2—C20 | −18.3 (3) | C20—C14—C15—O2 | 0.7 (5) |
O1—Cu1—N2—C20 | −143.1 (3) | C19—C14—C15—C16 | 0.0 (5) |
N1—Cu1—N2—C20 | 103.2 (3) | C20—C14—C15—C16 | 178.2 (3) |
O2—Cu1—N2—C21 | 161.6 (3) | O2—C15—C16—C17 | 179.7 (4) |
O1—Cu1—N2—C21 | 36.8 (3) | C14—C15—C16—C17 | 2.0 (6) |
N1—Cu1—N2—C21 | −76.9 (3) | C15—C16—C17—C18 | −2.1 (6) |
Cu1—O1—C2—C3 | 165.7 (3) | C16—C17—C18—C19 | 0.1 (6) |
Cu1—O1—C2—C1 | −16.0 (5) | C16—C17—C18—Br2 | 179.6 (3) |
C6—C1—C2—O1 | −174.9 (3) | C17—C18—C19—C14 | 1.9 (6) |
C7—C1—C2—O1 | 2.1 (6) | Br2—C18—C19—C14 | −177.6 (3) |
C6—C1—C2—C3 | 3.4 (5) | C15—C14—C19—C18 | −1.9 (5) |
C7—C1—C2—C3 | −179.5 (3) | C20—C14—C19—C18 | 179.7 (3) |
O1—C2—C3—C4 | 174.8 (4) | C21—N2—C20—C14 | −176.8 (3) |
C1—C2—C3—C4 | −3.7 (5) | Cu1—N2—C20—C14 | 3.1 (5) |
C2—C3—C4—C5 | 1.5 (6) | C19—C14—C20—N2 | −171.2 (3) |
C3—C4—C5—C6 | 1.0 (6) | C15—C14—C20—N2 | 10.5 (6) |
C3—C4—C5—Br1 | −178.7 (3) | C20—N2—C21—C26 | −129.2 (3) |
C4—C5—C6—C1 | −1.1 (6) | Cu1—N2—C21—C26 | 50.9 (4) |
Br1—C5—C6—C1 | 178.6 (3) | C20—N2—C21—C22 | 108.1 (4) |
C2—C1—C6—C5 | −1.2 (5) | Cu1—N2—C21—C22 | −71.7 (3) |
C7—C1—C6—C5 | −178.5 (3) | N2—C21—C22—C23 | 175.0 (3) |
C8—N1—C7—C1 | −178.3 (3) | C26—C21—C22—C23 | 53.7 (4) |
Cu1—N1—C7—C1 | 0.3 (5) | C21—C22—C23—C24 | −54.7 (5) |
C6—C1—C7—N1 | −176.5 (4) | C22—C23—C24—C25 | 56.7 (5) |
C2—C1—C7—N1 | 6.4 (6) | C23—C24—C25—C26 | −57.7 (5) |
C7—N1—C8—C9 | −134.6 (3) | C24—C25—C26—C21 | 56.4 (4) |
Cu1—N1—C8—C9 | 46.9 (4) | N2—C21—C26—C25 | −175.8 (3) |
C7—N1—C8—C13 | 102.3 (4) | C22—C21—C26—C25 | −54.8 (4) |