Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804002867/tk6150sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804002867/tk6150Isup2.hkl |
CCDC reference: 236031
Data collection: Siemens P3R3 software; cell refinement: Siemens P3R3 software; data reduction: SHELXTL-Plus (Sheldrick, 1994); program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldick, 1994); software used to prepare material for publication: SHELXL97.
[In(C2H5)(C14H13N2)2] | Z = 2 |
Mr = 562.41 | F(000) = 576 |
Triclinic, P1 | Dx = 1.392 Mg m−3 |
a = 10.056 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.014 (7) Å | Cell parameters from 18 reflections |
c = 12.842 (8) Å | θ = 10–11° |
α = 107.11 (5)° | µ = 0.91 mm−1 |
β = 94.83 (5)° | T = 240 K |
γ = 111.92 (4)° | Block, colourless |
V = 1342.3 (15) Å3 | 0.37 × 0.35 × 0.27 mm |
Siemens P3/R3 diffractometer | Rint = 0.076 |
ω–2θ scans | θmax = 24.1°, θmin = 2.1° |
Absorption correction: gaussian (Alcock, 1970) | h = 0→11 |
Tmin = 0.731, Tmax = 0.792 | k = −13→12 |
4504 measured reflections | l = −14→14 |
4232 independent reflections | 3 standard reflections every 200 reflections |
3640 reflections with I > 2σ(I) | intensity decay: 6% |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0878P)2 + 0.2286P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.124 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 1.15 e Å−3 |
4232 reflections | Δρmin = −1.23 e Å−3 |
319 parameters |
Experimental. The temperature of the crystal was controlled using the Oxford Cryosystem Cryostream Cooler (Cosier & Glazer, 1986). Due to the fact that the crystals were unstable and did not diffract strongly at high angles, the data were only collected to θmax of 24.1° |
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. |
x | y | z | Uiso*/Ueq | ||
In1 | 0.12291 (4) | 0.15701 (3) | 0.33165 (3) | 0.03694 (15) | |
N1 | 0.1313 (5) | 0.0015 (4) | 0.1834 (3) | 0.0417 (10) | |
N2 | 0.3051 (4) | 0.1979 (4) | 0.2382 (3) | 0.0404 (9) | |
N3 | 0.0604 (5) | 0.3194 (4) | 0.3226 (4) | 0.0417 (9) | |
N4 | −0.1098 (5) | 0.1197 (4) | 0.2709 (4) | 0.0418 (10) | |
C1 | 0.0576 (5) | −0.1319 (5) | 0.1198 (4) | 0.0407 (11) | |
C2 | 0.0503 (6) | −0.2185 (5) | 0.1722 (5) | 0.0517 (13) | |
H2 | 0.0992 | −0.1887 | 0.2472 | 0.062* | |
C3 | −0.0285 (8) | −0.3491 (6) | 0.1153 (6) | 0.0664 (17) | |
H3 | −0.0321 | −0.4074 | 0.1515 | 0.08* | |
C4 | −0.1017 (7) | −0.3935 (6) | 0.0052 (6) | 0.0678 (18) | |
H4 | −0.1557 | −0.4819 | −0.0335 | 0.081* | |
C5 | −0.0950 (7) | −0.3073 (6) | −0.0474 (5) | 0.0625 (16) | |
H5 | −0.1455 | −0.3371 | −0.122 | 0.075* | |
C6 | −0.0140 (6) | −0.1765 (5) | 0.0092 (5) | 0.0516 (13) | |
H6 | −0.0079 | −0.1183 | −0.0277 | 0.062* | |
C7 | 0.2542 (5) | 0.0804 (5) | 0.1657 (4) | 0.0384 (11) | |
C8 | 0.3277 (6) | 0.0363 (5) | 0.0746 (5) | 0.0483 (13) | |
H8A | 0.2862 | 0.0414 | 0.006 | 0.072* | |
H8B | 0.312 | −0.0516 | 0.0627 | 0.072* | |
H8C | 0.4323 | 0.0908 | 0.0962 | 0.072* | |
C9 | 0.4351 (5) | 0.3033 (5) | 0.2430 (4) | 0.0410 (11) | |
C10 | 0.4667 (6) | 0.3394 (5) | 0.1516 (5) | 0.0497 (13) | |
H10 | 0.4046 | 0.289 | 0.0806 | 0.06* | |
C11 | 0.5897 (7) | 0.4498 (6) | 0.1647 (5) | 0.0578 (15) | |
H11 | 0.6119 | 0.4723 | 0.102 | 0.069* | |
C12 | 0.6793 (6) | 0.5264 (5) | 0.2681 (6) | 0.0572 (15) | |
H12 | 0.7606 | 0.6023 | 0.2764 | 0.069* | |
C13 | 0.6495 (6) | 0.4917 (5) | 0.3604 (5) | 0.0526 (14) | |
H13 | 0.711 | 0.5435 | 0.4313 | 0.063* | |
C14 | 0.5287 (6) | 0.3804 (5) | 0.3474 (4) | 0.0438 (12) | |
H14 | 0.5094 | 0.3564 | 0.4098 | 0.053* | |
C15 | −0.2522 (6) | 0.0191 (5) | 0.2433 (4) | 0.0412 (11) | |
C16 | −0.2677 (7) | −0.1050 (5) | 0.1908 (5) | 0.0526 (14) | |
H16 | −0.1861 | −0.1195 | 0.1713 | 0.063* | |
C17 | −0.4043 (8) | −0.2089 (6) | 0.1666 (5) | 0.0630 (16) | |
H17 | −0.4138 | −0.293 | 0.1318 | 0.076* | |
C18 | −0.5247 (7) | −0.1882 (7) | 0.1939 (5) | 0.0670 (18) | |
H18 | −0.6169 | −0.2578 | 0.1755 | 0.08* | |
C19 | −0.5100 (7) | −0.0663 (7) | 0.2478 (6) | 0.0641 (16) | |
H19 | −0.5922 | −0.0525 | 0.2671 | 0.077* | |
C20 | −0.3743 (6) | 0.0372 (6) | 0.2742 (5) | 0.0504 (13) | |
H20 | −0.3647 | 0.1203 | 0.3132 | 0.061* | |
C21 | −0.0809 (6) | 0.2392 (5) | 0.2766 (4) | 0.0428 (12) | |
C22 | −0.1887 (6) | 0.2766 (6) | 0.2218 (5) | 0.0528 (14) | |
H22A | −0.1362 | 0.3427 | 0.1929 | 0.079* | |
H22B | −0.2388 | 0.3089 | 0.2764 | 0.079* | |
H22C | −0.2602 | 0.2021 | 0.161 | 0.079* | |
C23 | 0.1225 (6) | 0.4534 (4) | 0.3489 (4) | 0.0402 (11) | |
C24 | 0.2687 (6) | 0.5140 (5) | 0.3427 (4) | 0.0474 (12) | |
H24 | 0.3199 | 0.464 | 0.3159 | 0.057* | |
C25 | 0.3398 (6) | 0.6456 (5) | 0.3751 (5) | 0.0525 (13) | |
H25 | 0.438 | 0.684 | 0.3696 | 0.063* | |
C26 | 0.2668 (7) | 0.7215 (5) | 0.4157 (5) | 0.0568 (15) | |
H26 | 0.3156 | 0.8113 | 0.4395 | 0.068* | |
C27 | 0.1224 (8) | 0.6636 (6) | 0.4206 (5) | 0.0610 (16) | |
H27 | 0.0718 | 0.7147 | 0.4459 | 0.073* | |
C28 | 0.0485 (7) | 0.5299 (5) | 0.3886 (5) | 0.0503 (13) | |
H28 | −0.0499 | 0.492 | 0.3939 | 0.06* | |
C29 | 0.1903 (7) | 0.1478 (6) | 0.4917 (4) | 0.0538 (14) | |
H29A | 0.2563 | 0.2343 | 0.5426 | 0.065* | |
H29B | 0.1035 | 0.1178 | 0.5228 | 0.065* | |
C30 | 0.2663 (10) | 0.0614 (8) | 0.4864 (6) | 0.087 (2) | |
H30A | 0.1965 | −0.0269 | 0.4475 | 0.13* | |
H30B | 0.3073 | 0.0717 | 0.5616 | 0.13* | |
H30C | 0.3447 | 0.0832 | 0.4468 | 0.13* |
U11 | U22 | U33 | U12 | U13 | U23 | |
In1 | 0.0373 (2) | 0.0339 (2) | 0.0448 (2) | 0.01784 (15) | 0.00913 (15) | 0.01713 (15) |
N1 | 0.041 (2) | 0.041 (2) | 0.044 (2) | 0.018 (2) | 0.0085 (19) | 0.0137 (19) |
N2 | 0.040 (2) | 0.032 (2) | 0.046 (2) | 0.0146 (18) | 0.0126 (19) | 0.0108 (18) |
N3 | 0.042 (2) | 0.035 (2) | 0.055 (2) | 0.0193 (19) | 0.014 (2) | 0.0197 (19) |
N4 | 0.039 (2) | 0.036 (2) | 0.053 (2) | 0.0178 (19) | 0.0094 (19) | 0.0168 (19) |
C1 | 0.036 (3) | 0.040 (3) | 0.047 (3) | 0.019 (2) | 0.011 (2) | 0.013 (2) |
C2 | 0.052 (3) | 0.045 (3) | 0.056 (3) | 0.017 (3) | 0.009 (3) | 0.018 (3) |
C3 | 0.079 (5) | 0.039 (3) | 0.083 (5) | 0.020 (3) | 0.028 (4) | 0.027 (3) |
C4 | 0.057 (4) | 0.039 (3) | 0.079 (5) | 0.004 (3) | 0.020 (3) | 0.001 (3) |
C5 | 0.053 (4) | 0.062 (4) | 0.054 (3) | 0.019 (3) | 0.007 (3) | 0.004 (3) |
C6 | 0.052 (3) | 0.053 (3) | 0.052 (3) | 0.024 (3) | 0.010 (3) | 0.018 (3) |
C7 | 0.035 (3) | 0.043 (3) | 0.045 (3) | 0.022 (2) | 0.003 (2) | 0.021 (2) |
C8 | 0.050 (3) | 0.049 (3) | 0.054 (3) | 0.028 (3) | 0.019 (3) | 0.016 (2) |
C9 | 0.034 (3) | 0.039 (3) | 0.053 (3) | 0.021 (2) | 0.012 (2) | 0.014 (2) |
C10 | 0.053 (3) | 0.050 (3) | 0.048 (3) | 0.022 (3) | 0.009 (2) | 0.020 (2) |
C11 | 0.067 (4) | 0.051 (3) | 0.070 (4) | 0.030 (3) | 0.026 (3) | 0.032 (3) |
C12 | 0.045 (3) | 0.037 (3) | 0.085 (4) | 0.014 (3) | 0.019 (3) | 0.019 (3) |
C13 | 0.042 (3) | 0.046 (3) | 0.063 (3) | 0.021 (3) | 0.006 (3) | 0.008 (3) |
C14 | 0.045 (3) | 0.038 (3) | 0.052 (3) | 0.022 (2) | 0.012 (2) | 0.013 (2) |
C15 | 0.040 (3) | 0.047 (3) | 0.044 (3) | 0.023 (2) | 0.008 (2) | 0.019 (2) |
C16 | 0.052 (3) | 0.049 (3) | 0.063 (3) | 0.022 (3) | 0.020 (3) | 0.025 (3) |
C17 | 0.074 (4) | 0.044 (3) | 0.065 (4) | 0.017 (3) | 0.015 (3) | 0.021 (3) |
C18 | 0.048 (4) | 0.068 (4) | 0.072 (4) | 0.003 (3) | 0.001 (3) | 0.037 (3) |
C19 | 0.045 (3) | 0.084 (5) | 0.075 (4) | 0.029 (3) | 0.017 (3) | 0.041 (4) |
C20 | 0.048 (3) | 0.055 (3) | 0.057 (3) | 0.026 (3) | 0.016 (3) | 0.026 (3) |
C21 | 0.044 (3) | 0.051 (3) | 0.050 (3) | 0.031 (3) | 0.017 (2) | 0.022 (2) |
C22 | 0.049 (3) | 0.061 (3) | 0.063 (3) | 0.033 (3) | 0.009 (3) | 0.029 (3) |
C23 | 0.048 (3) | 0.036 (3) | 0.045 (3) | 0.022 (2) | 0.011 (2) | 0.020 (2) |
C24 | 0.044 (3) | 0.047 (3) | 0.055 (3) | 0.023 (2) | 0.009 (2) | 0.019 (2) |
C25 | 0.045 (3) | 0.047 (3) | 0.060 (3) | 0.013 (3) | 0.006 (3) | 0.022 (3) |
C26 | 0.064 (4) | 0.043 (3) | 0.063 (4) | 0.021 (3) | 0.004 (3) | 0.021 (3) |
C27 | 0.080 (5) | 0.054 (3) | 0.064 (4) | 0.044 (3) | 0.017 (3) | 0.019 (3) |
C28 | 0.054 (3) | 0.054 (3) | 0.056 (3) | 0.031 (3) | 0.020 (3) | 0.025 (3) |
C29 | 0.067 (4) | 0.059 (3) | 0.038 (3) | 0.029 (3) | 0.009 (3) | 0.018 (3) |
C30 | 0.128 (7) | 0.093 (5) | 0.062 (4) | 0.074 (5) | 0.002 (4) | 0.029 (4) |
In1—C29 | 2.157 (5) | C13—C14 | 1.383 (8) |
In1—N4 | 2.234 (4) | C13—H13 | 0.94 |
In1—N2 | 2.255 (4) | C14—H14 | 0.94 |
In1—N1 | 2.274 (4) | C15—C16 | 1.385 (8) |
In1—N3 | 2.292 (4) | C15—C20 | 1.393 (7) |
N1—C7 | 1.333 (6) | C16—C17 | 1.401 (9) |
N1—C1 | 1.424 (6) | C16—H16 | 0.94 |
N2—C7 | 1.315 (6) | C17—C18 | 1.377 (9) |
N2—C9 | 1.422 (6) | C17—H17 | 0.94 |
N3—C21 | 1.341 (7) | C18—C19 | 1.368 (10) |
N3—C23 | 1.411 (6) | C18—H18 | 0.94 |
N4—C21 | 1.331 (6) | C19—C20 | 1.390 (8) |
N4—C15 | 1.417 (7) | C19—H19 | 0.94 |
C1—C2 | 1.380 (7) | C20—H20 | 0.94 |
C1—C6 | 1.384 (8) | C21—C22 | 1.515 (7) |
C2—C3 | 1.387 (8) | C22—H22A | 0.97 |
C2—H2 | 0.94 | C22—H22B | 0.97 |
C3—C4 | 1.383 (10) | C22—H22C | 0.97 |
C3—H3 | 0.94 | C23—C24 | 1.397 (7) |
C4—C5 | 1.379 (10) | C23—C28 | 1.399 (7) |
C4—H4 | 0.94 | C24—C25 | 1.379 (8) |
C5—C6 | 1.390 (8) | C24—H24 | 0.94 |
C5—H5 | 0.94 | C25—C26 | 1.388 (8) |
C6—H6 | 0.94 | C25—H25 | 0.94 |
C7—C8 | 1.507 (7) | C26—C27 | 1.373 (9) |
C8—H8A | 0.97 | C26—H26 | 0.94 |
C8—H8B | 0.97 | C27—C28 | 1.404 (8) |
C8—H8C | 0.97 | C27—H27 | 0.94 |
C9—C10 | 1.388 (7) | C28—H28 | 0.94 |
C9—C14 | 1.395 (7) | C29—C30 | 1.492 (9) |
C10—C11 | 1.388 (8) | C29—H29A | 0.98 |
C10—H10 | 0.94 | C29—H29B | 0.98 |
C11—C12 | 1.371 (9) | C30—H30A | 0.97 |
C11—H11 | 0.94 | C30—H30B | 0.97 |
C12—C13 | 1.388 (9) | C30—H30C | 0.97 |
C12—H12 | 0.94 | ||
C29—In1—N4 | 120.3 (2) | C14—C13—H13 | 120.2 |
C29—In1—N2 | 113.2 (2) | C12—C13—H13 | 120.2 |
N4—In1—N2 | 126.51 (16) | C13—C14—C9 | 120.9 (5) |
C29—In1—N1 | 114.18 (19) | C13—C14—H14 | 119.5 |
N4—In1—N1 | 96.12 (16) | C9—C14—H14 | 119.5 |
N2—In1—N1 | 58.22 (15) | C16—C15—C20 | 118.3 (5) |
C29—In1—N3 | 119.96 (19) | C16—C15—N4 | 117.8 (5) |
N4—In1—N3 | 58.75 (15) | C20—C15—N4 | 123.6 (5) |
N2—In1—N3 | 96.83 (15) | C15—C16—C17 | 120.4 (6) |
N1—In1—N3 | 125.80 (15) | C15—C16—H16 | 119.8 |
C7—N1—C1 | 123.8 (4) | C17—C16—H16 | 119.8 |
C7—N1—In1 | 93.9 (3) | C18—C17—C16 | 120.1 (6) |
C1—N1—In1 | 142.3 (3) | C18—C17—H17 | 120 |
C7—N2—C9 | 126.3 (4) | C16—C17—H17 | 120 |
C7—N2—In1 | 95.3 (3) | C19—C18—C17 | 120.0 (6) |
C9—N2—In1 | 138.4 (3) | C19—C18—H18 | 120 |
C21—N3—C23 | 126.0 (4) | C17—C18—H18 | 120 |
C21—N3—In1 | 92.8 (3) | C18—C19—C20 | 120.3 (6) |
C23—N3—In1 | 141.1 (3) | C18—C19—H19 | 119.9 |
C21—N4—C15 | 125.1 (4) | C20—C19—H19 | 119.9 |
C21—N4—In1 | 95.7 (3) | C19—C20—C15 | 120.8 (6) |
C15—N4—In1 | 138.9 (3) | C19—C20—H20 | 119.6 |
C2—C1—C6 | 119.4 (5) | C15—C20—H20 | 119.6 |
C2—C1—N1 | 118.7 (5) | N4—C21—N3 | 112.4 (4) |
C6—C1—N1 | 121.8 (5) | N4—C21—C22 | 123.8 (5) |
C1—C2—C3 | 120.6 (6) | N3—C21—C22 | 123.2 (5) |
C1—C2—H2 | 119.7 | C21—C22—H22A | 109.5 |
C3—C2—H2 | 119.7 | C21—C22—H22B | 109.5 |
C4—C3—C2 | 120.0 (6) | H22A—C22—H22B | 109.5 |
C4—C3—H3 | 120 | C21—C22—H22C | 109.5 |
C2—C3—H3 | 120 | H22A—C22—H22C | 109.5 |
C5—C4—C3 | 119.6 (6) | H22B—C22—H22C | 109.5 |
C5—C4—H4 | 120.2 | C24—C23—C28 | 118.2 (5) |
C3—C4—H4 | 120.2 | C24—C23—N3 | 118.4 (4) |
C4—C5—C6 | 120.4 (6) | C28—C23—N3 | 123.2 (5) |
C4—C5—H5 | 119.8 | C25—C24—C23 | 121.5 (5) |
C6—C5—H5 | 119.8 | C25—C24—H24 | 119.2 |
C1—C6—C5 | 120.0 (6) | C23—C24—H24 | 119.2 |
C1—C6—H6 | 120 | C24—C25—C26 | 120.2 (6) |
C5—C6—H6 | 120 | C24—C25—H25 | 119.9 |
N2—C7—N1 | 112.6 (4) | C26—C25—H25 | 119.9 |
N2—C7—C8 | 124.6 (5) | C27—C26—C25 | 119.1 (5) |
N1—C7—C8 | 122.8 (5) | C27—C26—H26 | 120.5 |
C7—C8—H8A | 109.5 | C25—C26—H26 | 120.5 |
C7—C8—H8B | 109.5 | C26—C27—C28 | 121.5 (6) |
H8A—C8—H8B | 109.5 | C26—C27—H27 | 119.3 |
C7—C8—H8C | 109.5 | C28—C27—H27 | 119.3 |
H8A—C8—H8C | 109.5 | C23—C28—C27 | 119.5 (5) |
H8B—C8—H8C | 109.5 | C23—C28—H28 | 120.3 |
C10—C9—C14 | 118.7 (5) | C27—C28—H28 | 120.3 |
C10—C9—N2 | 123.4 (5) | C30—C29—In1 | 113.6 (4) |
C14—C9—N2 | 117.7 (5) | C30—C29—H29A | 108.9 |
C11—C10—C9 | 120.1 (5) | In1—C29—H29A | 108.9 |
C11—C10—H10 | 119.9 | C30—C29—H29B | 108.9 |
C9—C10—H10 | 119.9 | In1—C29—H29B | 108.9 |
C12—C11—C10 | 120.8 (6) | H29A—C29—H29B | 107.7 |
C12—C11—H11 | 119.6 | C29—C30—H30A | 109.5 |
C10—C11—H11 | 119.6 | C29—C30—H30B | 109.5 |
C11—C12—C13 | 119.9 (5) | H30A—C30—H30B | 109.5 |
C11—C12—H12 | 120.1 | C29—C30—H30C | 109.5 |
C13—C12—H12 | 120.1 | H30A—C30—H30C | 109.5 |
C14—C13—C12 | 119.6 (5) | H30B—C30—H30C | 109.5 |
C29—In1—N1—C7 | −103.9 (3) | C1—N1—C7—C8 | 0.7 (7) |
N4—In1—N1—C7 | 129.0 (3) | In1—N1—C7—C8 | 178.9 (4) |
N2—In1—N1—C7 | −0.6 (3) | C7—N2—C9—C10 | 51.3 (7) |
N3—In1—N1—C7 | 73.5 (3) | In1—N2—C9—C10 | −129.2 (5) |
C29—In1—N1—C1 | 73.6 (6) | C7—N2—C9—C14 | −134.6 (5) |
N4—In1—N1—C1 | −53.5 (5) | In1—N2—C9—C14 | 45.0 (7) |
N2—In1—N1—C1 | 176.9 (6) | C14—C9—C10—C11 | 0.4 (8) |
N3—In1—N1—C1 | −109.1 (5) | N2—C9—C10—C11 | 174.5 (5) |
C29—In1—N2—C7 | 105.6 (3) | C9—C10—C11—C12 | −1.9 (9) |
N4—In1—N2—C7 | −71.8 (3) | C10—C11—C12—C13 | 1.9 (9) |
N1—In1—N2—C7 | 0.6 (3) | C11—C12—C13—C14 | −0.6 (8) |
N3—In1—N2—C7 | −127.6 (3) | C12—C13—C14—C9 | −0.8 (8) |
C29—In1—N2—C9 | −74.0 (5) | C10—C9—C14—C13 | 0.9 (7) |
N4—In1—N2—C9 | 108.6 (5) | N2—C9—C14—C13 | −173.6 (4) |
N1—In1—N2—C9 | −179.0 (6) | C21—N4—C15—C16 | 150.4 (5) |
N3—In1—N2—C9 | 52.7 (5) | In1—N4—C15—C16 | −37.3 (7) |
C29—In1—N3—C21 | −112.9 (3) | C21—N4—C15—C20 | −35.1 (8) |
N4—In1—N3—C21 | −3.5 (3) | In1—N4—C15—C20 | 137.3 (5) |
N2—In1—N3—C21 | 125.4 (3) | C20—C15—C16—C17 | 1.9 (8) |
N1—In1—N3—C21 | 70.0 (3) | N4—C15—C16—C17 | 176.7 (5) |
C29—In1—N3—C23 | 66.9 (6) | C15—C16—C17—C18 | 0.7 (9) |
N4—In1—N3—C23 | 176.2 (6) | C16—C17—C18—C19 | −2.0 (10) |
N2—In1—N3—C23 | −54.8 (5) | C17—C18—C19—C20 | 0.7 (10) |
N1—In1—N3—C23 | −110.3 (5) | C18—C19—C20—C15 | 2.0 (9) |
C29—In1—N4—C21 | 112.4 (3) | C16—C15—C20—C19 | −3.2 (8) |
N2—In1—N4—C21 | −70.4 (3) | N4—C15—C20—C19 | −177.8 (5) |
N1—In1—N4—C21 | −125.0 (3) | C15—N4—C21—N3 | 169.3 (4) |
N3—In1—N4—C21 | 3.6 (3) | In1—N4—C21—N3 | −5.7 (5) |
C29—In1—N4—C15 | −61.4 (5) | C15—N4—C21—C22 | −19.4 (8) |
N2—In1—N4—C15 | 115.9 (5) | In1—N4—C21—C22 | 165.6 (4) |
N1—In1—N4—C15 | 61.3 (5) | C23—N3—C21—N4 | −174.3 (4) |
N3—In1—N4—C15 | −170.1 (6) | In1—N3—C21—N4 | 5.5 (4) |
C7—N1—C1—C2 | 114.7 (6) | C23—N3—C21—C22 | 14.3 (8) |
In1—N1—C1—C2 | −62.2 (7) | In1—N3—C21—C22 | −165.9 (5) |
C7—N1—C1—C6 | −69.2 (7) | C21—N3—C23—C24 | −148.5 (5) |
In1—N1—C1—C6 | 113.8 (6) | In1—N3—C23—C24 | 31.8 (8) |
C6—C1—C2—C3 | −0.3 (9) | C21—N3—C23—C28 | 36.4 (8) |
N1—C1—C2—C3 | 175.8 (5) | In1—N3—C23—C28 | −143.4 (5) |
C1—C2—C3—C4 | −0.6 (10) | C28—C23—C24—C25 | 0.3 (8) |
C2—C3—C4—C5 | 0.4 (10) | N3—C23—C24—C25 | −175.1 (5) |
C3—C4—C5—C6 | 0.6 (10) | C23—C24—C25—C26 | 0.5 (9) |
C2—C1—C6—C5 | 1.4 (8) | C24—C25—C26—C27 | −1.5 (9) |
N1—C1—C6—C5 | −174.6 (5) | C25—C26—C27—C28 | 1.9 (9) |
C4—C5—C6—C1 | −1.6 (9) | C24—C23—C28—C27 | 0.1 (8) |
C9—N2—C7—N1 | 178.7 (4) | N3—C23—C28—C27 | 175.3 (5) |
In1—N2—C7—N1 | −1.0 (4) | C26—C27—C28—C23 | −1.2 (9) |
C9—N2—C7—C8 | 0.9 (8) | N4—In1—C29—C30 | 127.0 (5) |
In1—N2—C7—C8 | −178.8 (4) | N2—In1—C29—C30 | −50.6 (6) |
C1—N1—C7—N2 | −177.2 (4) | N1—In1—C29—C30 | 13.6 (6) |
In1—N1—C7—N2 | 1.0 (4) | N3—In1—C29—C30 | −163.9 (5) |