Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023299/hg6208sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023299/hg6208Isup2.hkl |
CCDC reference: 282377
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.
[Fe(C5H5)(C19H15ClN)] | Z = 2 |
Mr = 413.71 | F(000) = 428 |
Triclinic, P1 | Dx = 1.405 Mg m−3 |
Hall symbol: -P 1 | Melting point: 452 K |
a = 7.624 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.436 (6) Å | Cell parameters from 2965 reflections |
c = 12.791 (8) Å | θ = 2.8–27.2° |
α = 99.096 (7)° | µ = 0.92 mm−1 |
β = 98.257 (7)° | T = 293 K |
γ = 98.981 (7)° | Block, red |
V = 977.7 (10) Å3 | 0.28 × 0.20 × 0.14 mm |
Bruker APEX-II CCD area-detector diffractometer | 3397 independent reflections |
Radiation source: fine-focus sealed tube | 3037 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.619, Tmax = 0.880 | k = −7→12 |
5343 measured reflections | l = −15→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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0482P)2 + 0.1948P] where P = (Fo2 + 2Fc2)/3 |
3397 reflections | (Δ/σ)max = 0.001 |
244 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.27 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 | ||
Fe1 | 0.24721 (3) | 0.73979 (2) | 0.56830 (2) | 0.03730 (11) | |
Cl1 | 0.23605 (11) | 0.47841 (6) | 0.17107 (5) | 0.0800 (2) | |
N1 | 0.3415 (2) | 0.83248 (16) | 0.30738 (12) | 0.0459 (4) | |
C1 | 0.3057 (2) | 0.67613 (18) | 0.42066 (14) | 0.0377 (4) | |
C2 | 0.2094 (3) | 0.56906 (18) | 0.45886 (15) | 0.0418 (4) | |
H2 | 0.0928 | 0.5148 | 0.4236 | 0.050* | |
C3 | 0.3118 (3) | 0.5552 (2) | 0.55641 (16) | 0.0507 (5) | |
H3 | 0.2780 | 0.4902 | 0.6009 | 0.061* | |
C4 | 0.4692 (3) | 0.6524 (2) | 0.57937 (16) | 0.0508 (5) | |
H4 | 0.5636 | 0.6665 | 0.6429 | 0.061* | |
C5 | 0.4675 (3) | 0.7280 (2) | 0.49645 (15) | 0.0448 (4) | |
H5 | 0.5606 | 0.8021 | 0.4919 | 0.054* | |
C6 | 0.1156 (4) | 0.8916 (2) | 0.5570 (2) | 0.0638 (6) | |
H6 | 0.0885 | 0.9292 | 0.4922 | 0.077* | |
C7 | 0.0043 (3) | 0.7878 (3) | 0.5869 (2) | 0.0700 (7) | |
H7 | −0.1136 | 0.7405 | 0.5473 | 0.084* | |
C8 | 0.0927 (4) | 0.7656 (3) | 0.6844 (2) | 0.0737 (8) | |
H8 | 0.0481 | 0.6989 | 0.7249 | 0.088* | |
C9 | 0.2563 (4) | 0.8550 (3) | 0.71356 (19) | 0.0669 (7) | |
H9 | 0.3461 | 0.8616 | 0.7781 | 0.080* | |
C10 | 0.2692 (3) | 0.9333 (2) | 0.6352 (2) | 0.0611 (6) | |
H10 | 0.3694 | 1.0046 | 0.6350 | 0.073* | |
C11 | 0.2440 (2) | 0.73133 (18) | 0.32593 (14) | 0.0370 (4) | |
C12 | 0.0653 (3) | 0.6648 (2) | 0.25938 (15) | 0.0453 (5) | |
C13 | −0.0889 (3) | 0.7191 (3) | 0.2712 (2) | 0.0635 (6) | |
H13 | −0.0796 | 0.7984 | 0.3183 | 0.076* | |
C14 | −0.2552 (4) | 0.6550 (4) | 0.2129 (3) | 0.0904 (11) | |
H14 | −0.3583 | 0.6897 | 0.2224 | 0.109* | |
C15 | −0.2671 (5) | 0.5410 (4) | 0.1418 (3) | 0.1017 (13) | |
H15 | −0.3790 | 0.4995 | 0.1020 | 0.122* | |
C16 | −0.1192 (5) | 0.4857 (3) | 0.1271 (2) | 0.0890 (10) | |
H16 | −0.1294 | 0.4079 | 0.0780 | 0.107* | |
C17 | 0.0471 (3) | 0.5489 (2) | 0.18758 (17) | 0.0587 (6) | |
C18 | 0.2922 (3) | 0.89433 (19) | 0.21843 (15) | 0.0426 (4) | |
C19 | 0.2486 (3) | 1.0176 (2) | 0.23759 (17) | 0.0596 (6) | |
H19 | 0.2362 | 1.0545 | 0.3066 | 0.071* | |
C20 | 0.2228 (3) | 1.0877 (2) | 0.15480 (19) | 0.0616 (6) | |
H20 | 0.1912 | 1.1704 | 0.1692 | 0.074* | |
C21 | 0.2429 (3) | 1.0377 (2) | 0.05199 (17) | 0.0514 (5) | |
C22 | 0.2852 (3) | 0.9138 (2) | 0.03406 (18) | 0.0624 (6) | |
H22 | 0.2988 | 0.8773 | −0.0348 | 0.075* | |
C23 | 0.3085 (3) | 0.8411 (2) | 0.11597 (17) | 0.0565 (5) | |
H23 | 0.3350 | 0.7568 | 0.1011 | 0.068* | |
C24 | 0.2219 (4) | 1.1176 (3) | −0.0361 (2) | 0.0714 (7) | |
H24A | 0.1069 | 1.1448 | −0.0409 | 0.107* | |
H24B | 0.2294 | 1.0647 | −0.1034 | 0.107* | |
H24C | 0.3161 | 1.1941 | −0.0202 | 0.107* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.04337 (17) | 0.03515 (16) | 0.03705 (16) | 0.01237 (12) | 0.01000 (11) | 0.00976 (11) |
Cl1 | 0.1133 (6) | 0.0570 (4) | 0.0688 (4) | 0.0183 (4) | 0.0240 (4) | −0.0011 (3) |
N1 | 0.0500 (9) | 0.0473 (10) | 0.0391 (8) | 0.0002 (8) | 0.0041 (7) | 0.0157 (7) |
C1 | 0.0395 (10) | 0.0384 (10) | 0.0387 (10) | 0.0112 (8) | 0.0107 (8) | 0.0097 (8) |
C2 | 0.0527 (11) | 0.0338 (10) | 0.0421 (10) | 0.0114 (8) | 0.0126 (8) | 0.0090 (8) |
C3 | 0.0718 (14) | 0.0442 (11) | 0.0468 (11) | 0.0265 (11) | 0.0173 (10) | 0.0187 (9) |
C4 | 0.0548 (12) | 0.0617 (13) | 0.0426 (11) | 0.0295 (11) | 0.0054 (9) | 0.0139 (10) |
C5 | 0.0381 (10) | 0.0548 (12) | 0.0448 (11) | 0.0136 (9) | 0.0090 (8) | 0.0129 (9) |
C6 | 0.0800 (17) | 0.0533 (13) | 0.0679 (15) | 0.0406 (13) | 0.0145 (13) | 0.0112 (11) |
C7 | 0.0446 (12) | 0.0656 (16) | 0.096 (2) | 0.0194 (12) | 0.0186 (12) | −0.0124 (14) |
C8 | 0.097 (2) | 0.0609 (15) | 0.0811 (18) | 0.0248 (15) | 0.0597 (17) | 0.0171 (13) |
C9 | 0.0847 (18) | 0.0710 (16) | 0.0450 (12) | 0.0259 (14) | 0.0145 (12) | −0.0038 (11) |
C10 | 0.0732 (16) | 0.0372 (11) | 0.0724 (16) | 0.0092 (11) | 0.0224 (13) | 0.0003 (10) |
C11 | 0.0393 (9) | 0.0391 (10) | 0.0339 (9) | 0.0079 (8) | 0.0094 (7) | 0.0068 (8) |
C12 | 0.0466 (11) | 0.0513 (12) | 0.0381 (10) | −0.0001 (9) | 0.0038 (8) | 0.0207 (9) |
C13 | 0.0469 (12) | 0.0844 (17) | 0.0666 (15) | 0.0117 (12) | 0.0063 (11) | 0.0391 (13) |
C14 | 0.0484 (15) | 0.138 (3) | 0.094 (2) | 0.0071 (17) | 0.0001 (14) | 0.070 (2) |
C15 | 0.068 (2) | 0.134 (3) | 0.086 (2) | −0.032 (2) | −0.0271 (17) | 0.055 (2) |
C16 | 0.103 (2) | 0.081 (2) | 0.0592 (16) | −0.0316 (18) | −0.0179 (16) | 0.0197 (14) |
C17 | 0.0711 (15) | 0.0551 (13) | 0.0436 (11) | −0.0071 (11) | 0.0018 (10) | 0.0160 (10) |
C18 | 0.0431 (10) | 0.0432 (11) | 0.0406 (10) | −0.0010 (8) | 0.0063 (8) | 0.0148 (8) |
C19 | 0.0847 (16) | 0.0578 (14) | 0.0403 (11) | 0.0206 (12) | 0.0153 (11) | 0.0097 (10) |
C20 | 0.0796 (16) | 0.0520 (13) | 0.0590 (14) | 0.0210 (12) | 0.0134 (12) | 0.0177 (11) |
C21 | 0.0516 (12) | 0.0558 (13) | 0.0518 (12) | 0.0079 (10) | 0.0109 (9) | 0.0251 (10) |
C22 | 0.0863 (17) | 0.0665 (15) | 0.0417 (11) | 0.0190 (13) | 0.0224 (11) | 0.0170 (10) |
C23 | 0.0800 (15) | 0.0486 (12) | 0.0458 (12) | 0.0159 (11) | 0.0174 (11) | 0.0136 (10) |
C24 | 0.0772 (17) | 0.0829 (18) | 0.0661 (15) | 0.0174 (14) | 0.0169 (13) | 0.0424 (14) |
Fe1—C6 | 2.017 (2) | C8—H8 | 0.9800 |
Fe1—C7 | 2.028 (2) | C9—C10 | 1.394 (3) |
Fe1—C9 | 2.033 (2) | C9—H9 | 0.9800 |
Fe1—C8 | 2.034 (2) | C10—H10 | 0.9800 |
Fe1—C1 | 2.036 (2) | C11—C12 | 1.500 (3) |
Fe1—C10 | 2.036 (2) | C12—C17 | 1.373 (3) |
Fe1—C5 | 2.038 (2) | C12—C13 | 1.399 (3) |
Fe1—C2 | 2.038 (2) | C13—C14 | 1.385 (4) |
Fe1—C4 | 2.042 (2) | C13—H13 | 0.9300 |
Fe1—C3 | 2.050 (2) | C14—C15 | 1.361 (5) |
Cl1—C17 | 1.741 (3) | C14—H14 | 0.9300 |
N1—C11 | 1.268 (2) | C15—C16 | 1.367 (5) |
N1—C18 | 1.428 (2) | C15—H15 | 0.9300 |
C1—C5 | 1.427 (3) | C16—C17 | 1.392 (4) |
C1—C2 | 1.430 (3) | C16—H16 | 0.9300 |
C1—C11 | 1.471 (2) | C18—C23 | 1.371 (3) |
C2—C3 | 1.414 (3) | C18—C19 | 1.372 (3) |
C2—H2 | 0.9800 | C19—C20 | 1.387 (3) |
C3—C4 | 1.407 (3) | C19—H19 | 0.9300 |
C3—H3 | 0.9800 | C20—C21 | 1.375 (3) |
C4—C5 | 1.418 (3) | C20—H20 | 0.9300 |
C4—H4 | 0.9800 | C21—C22 | 1.373 (3) |
C5—H5 | 0.9800 | C21—C24 | 1.510 (3) |
C6—C10 | 1.389 (3) | C22—C23 | 1.394 (3) |
C6—C7 | 1.406 (4) | C22—H22 | 0.9300 |
C6—H6 | 0.9800 | C23—H23 | 0.9300 |
C7—C8 | 1.401 (4) | C24—H24A | 0.9600 |
C7—H7 | 0.9800 | C24—H24B | 0.9600 |
C8—C9 | 1.399 (4) | C24—H24C | 0.9600 |
C6—Fe1—C7 | 40.68 (11) | C10—C6—C7 | 108.6 (2) |
C6—Fe1—C9 | 67.51 (11) | C10—C6—Fe1 | 70.71 (13) |
C7—Fe1—C9 | 67.82 (11) | C7—C6—Fe1 | 70.11 (13) |
C6—Fe1—C8 | 67.78 (11) | C10—C6—H6 | 125.7 |
C7—Fe1—C8 | 40.33 (11) | C7—C6—H6 | 125.7 |
C9—Fe1—C8 | 40.23 (11) | Fe1—C6—H6 | 125.7 |
C6—Fe1—C1 | 107.66 (9) | C8—C7—C6 | 107.2 (2) |
C7—Fe1—C1 | 121.80 (10) | C8—C7—Fe1 | 70.06 (14) |
C9—Fe1—C1 | 160.43 (10) | C6—C7—Fe1 | 69.21 (13) |
C8—Fe1—C1 | 157.52 (11) | C8—C7—H7 | 126.4 |
C6—Fe1—C10 | 40.08 (10) | C6—C7—H7 | 126.4 |
C7—Fe1—C10 | 67.90 (10) | Fe1—C7—H7 | 126.4 |
C9—Fe1—C10 | 40.08 (10) | C9—C8—C7 | 108.1 (2) |
C8—Fe1—C10 | 67.56 (10) | C9—C8—Fe1 | 69.83 (13) |
C1—Fe1—C10 | 124.09 (9) | C7—C8—Fe1 | 69.60 (14) |
C6—Fe1—C5 | 119.95 (10) | C9—C8—H8 | 126.0 |
C7—Fe1—C5 | 156.16 (11) | C7—C8—H8 | 126.0 |
C9—Fe1—C5 | 123.42 (10) | Fe1—C8—H8 | 126.0 |
C8—Fe1—C5 | 160.78 (11) | C10—C9—C8 | 108.2 (2) |
C1—Fe1—C5 | 41.02 (8) | C10—C9—Fe1 | 70.07 (13) |
C10—Fe1—C5 | 106.16 (9) | C8—C9—Fe1 | 69.94 (14) |
C6—Fe1—C2 | 126.37 (10) | C10—C9—H9 | 125.9 |
C7—Fe1—C2 | 109.33 (10) | C8—C9—H9 | 125.9 |
C9—Fe1—C2 | 156.85 (10) | Fe1—C9—H9 | 125.9 |
C8—Fe1—C2 | 122.58 (10) | C6—C10—C9 | 107.9 (2) |
C1—Fe1—C2 | 41.11 (7) | C6—C10—Fe1 | 69.21 (13) |
C10—Fe1—C2 | 162.18 (9) | C9—C10—Fe1 | 69.84 (14) |
C5—Fe1—C2 | 68.88 (9) | C6—C10—H10 | 126.1 |
C6—Fe1—C4 | 154.80 (11) | C9—C10—H10 | 126.1 |
C7—Fe1—C4 | 162.50 (11) | Fe1—C10—H10 | 126.1 |
C9—Fe1—C4 | 107.32 (10) | N1—C11—C1 | 118.66 (17) |
C8—Fe1—C4 | 125.24 (11) | N1—C11—C12 | 124.55 (16) |
C1—Fe1—C4 | 68.49 (8) | C1—C11—C12 | 116.76 (16) |
C10—Fe1—C4 | 120.02 (10) | C17—C12—C13 | 118.3 (2) |
C5—Fe1—C4 | 40.68 (8) | C17—C12—C11 | 121.57 (19) |
C2—Fe1—C4 | 68.10 (9) | C13—C12—C11 | 120.1 (2) |
C6—Fe1—C3 | 163.64 (10) | C14—C13—C12 | 120.2 (3) |
C7—Fe1—C3 | 126.65 (10) | C14—C13—H13 | 119.9 |
C9—Fe1—C3 | 121.39 (10) | C12—C13—H13 | 119.9 |
C8—Fe1—C3 | 109.21 (10) | C15—C14—C13 | 119.6 (3) |
C1—Fe1—C3 | 68.58 (8) | C15—C14—H14 | 120.2 |
C10—Fe1—C3 | 155.26 (10) | C13—C14—H14 | 120.2 |
C5—Fe1—C3 | 68.41 (9) | C14—C15—C16 | 121.9 (3) |
C2—Fe1—C3 | 40.49 (8) | C14—C15—H15 | 119.0 |
C4—Fe1—C3 | 40.23 (9) | C16—C15—H15 | 119.0 |
C11—N1—C18 | 122.85 (17) | C15—C16—C17 | 118.3 (3) |
C5—C1—C2 | 107.52 (17) | C15—C16—H16 | 120.9 |
C5—C1—C11 | 125.47 (17) | C17—C16—H16 | 120.9 |
C2—C1—C11 | 126.81 (17) | C12—C17—C16 | 121.7 (3) |
C5—C1—Fe1 | 69.56 (11) | C12—C17—Cl1 | 119.55 (17) |
C2—C1—Fe1 | 69.53 (11) | C16—C17—Cl1 | 118.7 (2) |
C11—C1—Fe1 | 122.36 (13) | C23—C18—C19 | 118.92 (18) |
C3—C2—C1 | 108.03 (18) | C23—C18—N1 | 121.57 (19) |
C3—C2—Fe1 | 70.22 (12) | C19—C18—N1 | 119.03 (18) |
C1—C2—Fe1 | 69.36 (11) | C18—C19—C20 | 120.5 (2) |
C3—C2—H2 | 126.0 | C18—C19—H19 | 119.7 |
C1—C2—H2 | 126.0 | C20—C19—H19 | 119.7 |
Fe1—C2—H2 | 126.0 | C21—C20—C19 | 121.6 (2) |
C4—C3—C2 | 108.11 (17) | C21—C20—H20 | 119.2 |
C4—C3—Fe1 | 69.58 (12) | C19—C20—H20 | 119.2 |
C2—C3—Fe1 | 69.29 (11) | C22—C21—C20 | 117.11 (19) |
C4—C3—H3 | 125.9 | C22—C21—C24 | 122.0 (2) |
C2—C3—H3 | 125.9 | C20—C21—C24 | 120.9 (2) |
Fe1—C3—H3 | 125.9 | C21—C22—C23 | 122.0 (2) |
C3—C4—C5 | 108.84 (18) | C21—C22—H22 | 119.0 |
C3—C4—Fe1 | 70.19 (12) | C23—C22—H22 | 119.0 |
C5—C4—Fe1 | 69.50 (11) | C18—C23—C22 | 119.8 (2) |
C3—C4—H4 | 125.6 | C18—C23—H23 | 120.1 |
C5—C4—H4 | 125.6 | C22—C23—H23 | 120.1 |
Fe1—C4—H4 | 125.6 | C21—C24—H24A | 109.4 |
C4—C5—C1 | 107.50 (19) | C21—C24—H24B | 109.5 |
C4—C5—Fe1 | 69.82 (11) | H24A—C24—H24B | 109.5 |
C1—C5—Fe1 | 69.42 (11) | C21—C24—H24C | 109.5 |
C4—C5—H5 | 126.2 | H24A—C24—H24C | 109.5 |
C1—C5—H5 | 126.2 | H24B—C24—H24C | 109.5 |
Fe1—C5—H5 | 126.2 | ||
C6—Fe1—C1—C5 | 115.62 (14) | C10—Fe1—C6—C7 | −119.1 (2) |
C7—Fe1—C1—C5 | 157.97 (13) | C5—Fe1—C6—C7 | 161.64 (15) |
C9—Fe1—C1—C5 | 43.3 (3) | C2—Fe1—C6—C7 | 76.93 (18) |
C8—Fe1—C1—C5 | −169.9 (2) | C4—Fe1—C6—C7 | −164.57 (19) |
C10—Fe1—C1—C5 | 74.57 (14) | C3—Fe1—C6—C7 | 44.6 (4) |
C2—Fe1—C1—C5 | −118.82 (16) | C10—C6—C7—C8 | −0.4 (3) |
C4—Fe1—C1—C5 | −37.92 (12) | Fe1—C6—C7—C8 | 60.05 (16) |
C3—Fe1—C1—C5 | −81.29 (13) | C10—C6—C7—Fe1 | −60.50 (16) |
C6—Fe1—C1—C2 | −125.56 (13) | C6—Fe1—C7—C8 | −118.3 (2) |
C7—Fe1—C1—C2 | −83.21 (15) | C9—Fe1—C7—C8 | −37.47 (16) |
C9—Fe1—C1—C2 | 162.1 (2) | C1—Fe1—C7—C8 | 161.71 (14) |
C8—Fe1—C1—C2 | −51.1 (3) | C10—Fe1—C7—C8 | −80.90 (17) |
C10—Fe1—C1—C2 | −166.61 (12) | C5—Fe1—C7—C8 | −160.8 (2) |
C5—Fe1—C1—C2 | 118.82 (16) | C2—Fe1—C7—C8 | 117.93 (16) |
C4—Fe1—C1—C2 | 80.90 (13) | C4—Fe1—C7—C8 | 39.6 (4) |
C3—Fe1—C1—C2 | 37.53 (12) | C3—Fe1—C7—C8 | 75.97 (18) |
C6—Fe1—C1—C11 | −4.19 (18) | C9—Fe1—C7—C6 | 80.82 (17) |
C7—Fe1—C1—C11 | 38.16 (19) | C8—Fe1—C7—C6 | 118.3 (2) |
C9—Fe1—C1—C11 | −76.6 (3) | C1—Fe1—C7—C6 | −79.99 (17) |
C8—Fe1—C1—C11 | 70.2 (3) | C10—Fe1—C7—C6 | 37.39 (15) |
C10—Fe1—C1—C11 | −45.24 (19) | C5—Fe1—C7—C6 | −42.5 (3) |
C5—Fe1—C1—C11 | −119.8 (2) | C2—Fe1—C7—C6 | −123.77 (15) |
C2—Fe1—C1—C11 | 121.4 (2) | C4—Fe1—C7—C6 | 157.9 (3) |
C4—Fe1—C1—C11 | −157.73 (18) | C3—Fe1—C7—C6 | −165.74 (14) |
C3—Fe1—C1—C11 | 158.90 (18) | C6—C7—C8—C9 | −0.1 (3) |
C5—C1—C2—C3 | −0.4 (2) | Fe1—C7—C8—C9 | 59.45 (17) |
C11—C1—C2—C3 | −175.55 (17) | C6—C7—C8—Fe1 | −59.51 (16) |
Fe1—C1—C2—C3 | −59.81 (13) | C6—Fe1—C8—C9 | −80.96 (17) |
C5—C1—C2—Fe1 | 59.42 (13) | C7—Fe1—C8—C9 | −119.3 (2) |
C11—C1—C2—Fe1 | −115.73 (18) | C1—Fe1—C8—C9 | −163.50 (19) |
C6—Fe1—C2—C3 | −166.57 (14) | C10—Fe1—C8—C9 | −37.48 (15) |
C7—Fe1—C2—C3 | −124.28 (15) | C5—Fe1—C8—C9 | 36.9 (4) |
C9—Fe1—C2—C3 | −45.7 (3) | C2—Fe1—C8—C9 | 159.09 (14) |
C8—Fe1—C2—C3 | −81.55 (17) | C4—Fe1—C8—C9 | 74.29 (18) |
C1—Fe1—C2—C3 | 119.13 (17) | C3—Fe1—C8—C9 | 116.24 (16) |
C10—Fe1—C2—C3 | 157.9 (3) | C6—Fe1—C8—C7 | 38.32 (16) |
C5—Fe1—C2—C3 | 81.08 (13) | C9—Fe1—C8—C7 | 119.3 (2) |
C4—Fe1—C2—C3 | 37.20 (12) | C1—Fe1—C8—C7 | −44.2 (3) |
C6—Fe1—C2—C1 | 74.29 (15) | C10—Fe1—C8—C7 | 81.80 (17) |
C7—Fe1—C2—C1 | 116.58 (14) | C5—Fe1—C8—C7 | 156.1 (3) |
C9—Fe1—C2—C1 | −164.8 (2) | C2—Fe1—C8—C7 | −81.63 (17) |
C8—Fe1—C2—C1 | 159.32 (13) | C4—Fe1—C8—C7 | −166.43 (15) |
C10—Fe1—C2—C1 | 38.8 (3) | C3—Fe1—C8—C7 | −124.48 (16) |
C5—Fe1—C2—C1 | −38.06 (11) | C7—C8—C9—C10 | 0.5 (3) |
C4—Fe1—C2—C1 | −81.93 (12) | Fe1—C8—C9—C10 | 59.84 (16) |
C3—Fe1—C2—C1 | −119.13 (17) | C7—C8—C9—Fe1 | −59.31 (17) |
C1—C2—C3—C4 | 0.3 (2) | C6—Fe1—C9—C10 | −37.42 (16) |
Fe1—C2—C3—C4 | −58.93 (14) | C7—Fe1—C9—C10 | −81.57 (17) |
C1—C2—C3—Fe1 | 59.28 (13) | C8—Fe1—C9—C10 | −119.1 (2) |
C6—Fe1—C3—C4 | 161.3 (3) | C1—Fe1—C9—C10 | 42.0 (3) |
C7—Fe1—C3—C4 | −163.96 (14) | C5—Fe1—C9—C10 | 74.55 (17) |
C9—Fe1—C3—C4 | −79.55 (15) | C2—Fe1—C9—C10 | −169.0 (2) |
C8—Fe1—C3—C4 | −122.28 (15) | C4—Fe1—C9—C10 | 116.31 (16) |
C1—Fe1—C3—C4 | 81.60 (12) | C3—Fe1—C9—C10 | 158.01 (15) |
C10—Fe1—C3—C4 | −44.4 (3) | C6—Fe1—C9—C8 | 81.71 (18) |
C5—Fe1—C3—C4 | 37.35 (12) | C7—Fe1—C9—C8 | 37.57 (16) |
C2—Fe1—C3—C4 | 119.69 (17) | C1—Fe1—C9—C8 | 161.1 (2) |
C6—Fe1—C3—C2 | 41.6 (4) | C10—Fe1—C9—C8 | 119.1 (2) |
C7—Fe1—C3—C2 | 76.35 (16) | C5—Fe1—C9—C8 | −166.31 (15) |
C9—Fe1—C3—C2 | 160.77 (13) | C2—Fe1—C9—C8 | −49.9 (3) |
C8—Fe1—C3—C2 | 118.03 (15) | C4—Fe1—C9—C8 | −124.55 (16) |
C1—Fe1—C3—C2 | −38.09 (12) | C3—Fe1—C9—C8 | −82.85 (18) |
C10—Fe1—C3—C2 | −164.06 (19) | C7—C6—C10—C9 | 0.8 (3) |
C5—Fe1—C3—C2 | −82.34 (13) | Fe1—C6—C10—C9 | −59.35 (16) |
C4—Fe1—C3—C2 | −119.69 (17) | C7—C6—C10—Fe1 | 60.12 (16) |
C2—C3—C4—C5 | −0.2 (2) | C8—C9—C10—C6 | −0.8 (3) |
Fe1—C3—C4—C5 | −58.92 (14) | Fe1—C9—C10—C6 | 58.95 (16) |
C2—C3—C4—Fe1 | 58.76 (14) | C8—C9—C10—Fe1 | −59.76 (16) |
C6—Fe1—C4—C3 | −167.74 (19) | C7—Fe1—C10—C6 | −37.94 (16) |
C7—Fe1—C4—C3 | 47.5 (4) | C9—Fe1—C10—C6 | −119.3 (2) |
C9—Fe1—C4—C3 | 118.44 (14) | C8—Fe1—C10—C6 | −81.68 (18) |
C8—Fe1—C4—C3 | 77.81 (16) | C1—Fe1—C10—C6 | 76.39 (17) |
C1—Fe1—C4—C3 | −81.84 (12) | C5—Fe1—C10—C6 | 117.59 (16) |
C10—Fe1—C4—C3 | 160.25 (12) | C2—Fe1—C10—C6 | 46.5 (3) |
C5—Fe1—C4—C3 | −120.07 (18) | C4—Fe1—C10—C6 | 159.48 (14) |
C2—Fe1—C4—C3 | −37.44 (12) | C3—Fe1—C10—C6 | −169.08 (19) |
C6—Fe1—C4—C5 | −47.7 (3) | C6—Fe1—C10—C9 | 119.3 (2) |
C7—Fe1—C4—C5 | 167.6 (3) | C7—Fe1—C10—C9 | 81.36 (18) |
C9—Fe1—C4—C5 | −121.49 (15) | C8—Fe1—C10—C9 | 37.61 (16) |
C8—Fe1—C4—C5 | −162.12 (14) | C1—Fe1—C10—C9 | −164.31 (14) |
C1—Fe1—C4—C5 | 38.23 (12) | C5—Fe1—C10—C9 | −123.11 (16) |
C10—Fe1—C4—C5 | −79.68 (15) | C2—Fe1—C10—C9 | 165.8 (3) |
C2—Fe1—C4—C5 | 82.63 (14) | C4—Fe1—C10—C9 | −81.22 (17) |
C3—Fe1—C4—C5 | 120.07 (18) | C3—Fe1—C10—C9 | −49.8 (3) |
C3—C4—C5—C1 | −0.1 (2) | C18—N1—C11—C1 | −179.13 (17) |
Fe1—C4—C5—C1 | −59.43 (13) | C18—N1—C11—C12 | −1.0 (3) |
C3—C4—C5—Fe1 | 59.35 (15) | C5—C1—C11—N1 | 1.0 (3) |
C2—C1—C5—C4 | 0.3 (2) | C2—C1—C11—N1 | 175.31 (18) |
C11—C1—C5—C4 | 175.52 (17) | Fe1—C1—C11—N1 | 87.8 (2) |
Fe1—C1—C5—C4 | 59.68 (14) | C5—C1—C11—C12 | −177.31 (17) |
C2—C1—C5—Fe1 | −59.39 (13) | C2—C1—C11—C12 | −3.0 (3) |
C11—C1—C5—Fe1 | 115.84 (18) | Fe1—C1—C11—C12 | −90.5 (2) |
C6—Fe1—C5—C4 | 158.70 (14) | N1—C11—C12—C17 | 103.3 (2) |
C7—Fe1—C5—C4 | −170.8 (2) | C1—C11—C12—C17 | −78.5 (2) |
C9—Fe1—C5—C4 | 77.26 (17) | N1—C11—C12—C13 | −78.1 (3) |
C8—Fe1—C5—C4 | 49.6 (3) | C1—C11—C12—C13 | 100.1 (2) |
C1—Fe1—C5—C4 | −118.70 (18) | C17—C12—C13—C14 | 1.3 (3) |
C10—Fe1—C5—C4 | 117.51 (15) | C11—C12—C13—C14 | −177.43 (19) |
C2—Fe1—C5—C4 | −80.56 (14) | C12—C13—C14—C15 | −2.0 (4) |
C3—Fe1—C5—C4 | −36.95 (13) | C13—C14—C15—C16 | 1.2 (5) |
C6—Fe1—C5—C1 | −82.59 (14) | C14—C15—C16—C17 | 0.2 (4) |
C7—Fe1—C5—C1 | −52.1 (3) | C13—C12—C17—C16 | 0.2 (3) |
C9—Fe1—C5—C1 | −164.04 (12) | C11—C12—C17—C16 | 178.86 (19) |
C8—Fe1—C5—C1 | 168.3 (3) | C13—C12—C17—Cl1 | −179.88 (15) |
C10—Fe1—C5—C1 | −123.79 (12) | C11—C12—C17—Cl1 | −1.2 (3) |
C2—Fe1—C5—C1 | 38.14 (11) | C15—C16—C17—C12 | −0.9 (4) |
C4—Fe1—C5—C1 | 118.70 (18) | C15—C16—C17—Cl1 | 179.1 (2) |
C3—Fe1—C5—C1 | 81.75 (12) | C11—N1—C18—C23 | −76.5 (3) |
C7—Fe1—C6—C10 | 119.1 (2) | C11—N1—C18—C19 | 111.6 (2) |
C9—Fe1—C6—C10 | 37.43 (15) | C23—C18—C19—C20 | −0.5 (3) |
C8—Fe1—C6—C10 | 81.09 (18) | N1—C18—C19—C20 | 171.6 (2) |
C1—Fe1—C6—C10 | −122.36 (15) | C18—C19—C20—C21 | −1.1 (4) |
C5—Fe1—C6—C10 | −79.28 (17) | C19—C20—C21—C22 | 1.6 (4) |
C2—Fe1—C6—C10 | −163.98 (13) | C19—C20—C21—C24 | −177.4 (2) |
C4—Fe1—C6—C10 | −45.5 (3) | C20—C21—C22—C23 | −0.4 (4) |
C3—Fe1—C6—C10 | 163.7 (3) | C24—C21—C22—C23 | 178.6 (2) |
C9—Fe1—C6—C7 | −81.65 (18) | C19—C18—C23—C22 | 1.6 (3) |
C8—Fe1—C6—C7 | −38.00 (16) | N1—C18—C23—C22 | −170.3 (2) |
C1—Fe1—C6—C7 | 118.56 (16) | C21—C22—C23—C18 | −1.2 (4) |