Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806004740/xu6108sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806004740/xu6108Isup2.hkl |
CCDC reference: 601274
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[Fe(C5H5)(C16H20N)] | F(000) = 368 |
Mr = 347.27 | Dx = 1.297 Mg m−3 |
Monoclinic, P21 | Melting point: 198 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 5.8833 (12) Å | Cell parameters from 714 reflections |
b = 10.748 (2) Å | θ = 2.1–12.4° |
c = 14.191 (3) Å | µ = 0.85 mm−1 |
β = 97.82 (3)° | T = 291 K |
V = 889.0 (3) Å3 | Block, orange |
Z = 2 | 0.20 × 0.18 × 0.16 mm |
Bruker SMART APEX CCD area-detector diffractometer | 3239 independent reflections |
Radiation source: sealed tube | 2928 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
φ and ω scans | θmax = 26.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −7→7 |
Tmin = 0.849, Tmax = 0.876 | k = −13→13 |
5026 measured reflections | l = −17→17 |
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)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0644P)2 + 0.55P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3239 reflections | Δρmax = 0.33 e Å−3 |
208 parameters | Δρmin = −0.45 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1394 Friedel Pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.06 (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 | 0.51940 (10) | 0.85961 (7) | 0.36379 (4) | 0.02886 (18) | |
N1 | 0.2664 (7) | 0.8054 (4) | 0.0590 (3) | 0.0275 (8) | |
C1 | 0.5643 (8) | 0.6780 (5) | 0.4086 (4) | 0.0347 (11) | |
H1A | 0.5067 | 0.6045 | 0.3720 | 0.042* | |
C2 | 0.7782 (8) | 0.7338 (5) | 0.4062 (4) | 0.0346 (11) | |
H2A | 0.8963 | 0.7060 | 0.3684 | 0.041* | |
C3 | 0.7931 (8) | 0.8328 (4) | 0.4657 (3) | 0.0353 (13) | |
H3A | 0.9256 | 0.8885 | 0.4786 | 0.042* | |
C4 | 0.5879 (8) | 0.8430 (5) | 0.5065 (3) | 0.0339 (12) | |
H4A | 0.5544 | 0.9044 | 0.5537 | 0.041* | |
C5 | 0.4451 (8) | 0.7451 (5) | 0.4694 (4) | 0.0324 (11) | |
H5A | 0.2919 | 0.7259 | 0.4853 | 0.039* | |
C6 | 0.2194 (9) | 0.9202 (5) | 0.2888 (3) | 0.0367 (11) | |
H6A | 0.0651 | 0.8931 | 0.2984 | 0.044* | |
C7 | 0.3422 (9) | 1.0221 (5) | 0.3355 (4) | 0.0377 (12) | |
H7A | 0.2880 | 1.0781 | 0.3822 | 0.045* | |
C8 | 0.5540 (8) | 1.0272 (5) | 0.3020 (4) | 0.0363 (12) | |
H8A | 0.6756 | 1.0878 | 0.3215 | 0.044* | |
C9 | 0.5625 (11) | 0.9327 (6) | 0.2342 (4) | 0.0436 (13) | |
H9A | 0.6925 | 0.9159 | 0.1995 | 0.052* | |
C10 | 0.3585 (7) | 0.8649 (7) | 0.2256 (3) | 0.0358 (10) | |
C11 | 0.3029 (9) | 0.7548 (4) | 0.1581 (4) | 0.0332 (11) | |
H11A | 0.4410 | 0.7029 | 0.1633 | 0.040* | |
C12 | 0.2412 (10) | 0.7068 (5) | −0.0155 (4) | 0.0393 (12) | |
H12A | 0.1013 | 0.6593 | −0.0101 | 0.047* | |
C13 | 0.2191 (10) | 0.7653 (4) | −0.1136 (4) | 0.0377 (12) | |
C14 | 0.3994 (10) | 0.8343 (5) | −0.1411 (4) | 0.0423 (14) | |
H14A | 0.5363 | 0.8423 | −0.1003 | 0.051* | |
C15 | 0.3729 (9) | 0.8921 (4) | −0.2313 (4) | 0.0359 (12) | |
H15A | 0.4892 | 0.9429 | −0.2479 | 0.043* | |
C16 | 0.1785 (9) | 0.8744 (7) | −0.2943 (4) | 0.0438 (13) | |
H16A | 0.1635 | 0.9111 | −0.3542 | 0.053* | |
C17 | 0.0063 (9) | 0.8021 (5) | −0.2684 (4) | 0.0378 (12) | |
H17A | −0.1245 | 0.7875 | −0.3117 | 0.045* | |
C18 | 0.0249 (10) | 0.7501 (6) | −0.1780 (4) | 0.0442 (13) | |
H18A | −0.0968 | 0.7040 | −0.1608 | 0.053* | |
C19 | 0.1104 (9) | 0.6728 (6) | 0.1846 (4) | 0.0401 (12) | |
H19A | 0.0832 | 0.6058 | 0.1397 | 0.060* | |
H19B | −0.0269 | 0.7214 | 0.1834 | 0.060* | |
H19C | 0.1533 | 0.6395 | 0.2472 | 0.060* | |
C20 | 0.0696 (8) | 0.8911 (4) | 0.0445 (4) | 0.0340 (12) | |
H20A | 0.0516 | 0.9223 | −0.0194 | 0.051* | |
H20B | 0.0959 | 0.9593 | 0.0883 | 0.051* | |
H20C | −0.0671 | 0.8476 | 0.0553 | 0.051* | |
C21 | 0.4457 (10) | 0.6173 (6) | −0.0029 (5) | 0.0480 (16) | |
H21A | 0.4610 | 0.5814 | 0.0596 | 0.072* | |
H21B | 0.5832 | 0.6620 | −0.0107 | 0.072* | |
H21C | 0.4211 | 0.5525 | −0.0497 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0291 (3) | 0.0301 (3) | 0.0258 (3) | 0.0066 (4) | −0.0020 (2) | 0.0019 (3) |
N1 | 0.027 (2) | 0.0238 (18) | 0.030 (2) | 0.0010 (15) | −0.0032 (16) | −0.0030 (16) |
C1 | 0.032 (3) | 0.040 (3) | 0.030 (2) | 0.016 (2) | −0.0055 (19) | 0.012 (2) |
C2 | 0.028 (2) | 0.041 (3) | 0.034 (3) | 0.012 (2) | −0.0011 (19) | 0.012 (2) |
C3 | 0.030 (2) | 0.033 (3) | 0.037 (2) | 0.0006 (19) | −0.0142 (18) | 0.013 (2) |
C4 | 0.041 (2) | 0.027 (3) | 0.032 (2) | 0.019 (2) | −0.0020 (17) | 0.003 (2) |
C5 | 0.032 (3) | 0.033 (3) | 0.035 (3) | 0.016 (2) | 0.015 (2) | 0.014 (2) |
C6 | 0.039 (3) | 0.041 (3) | 0.029 (2) | 0.013 (2) | 0.001 (2) | 0.000 (2) |
C7 | 0.034 (3) | 0.045 (3) | 0.029 (3) | 0.016 (2) | −0.012 (2) | −0.011 (2) |
C8 | 0.027 (2) | 0.045 (3) | 0.035 (3) | −0.012 (2) | −0.004 (2) | 0.006 (2) |
C9 | 0.056 (3) | 0.049 (3) | 0.024 (2) | −0.010 (3) | −0.001 (2) | 0.007 (2) |
C10 | 0.034 (2) | 0.044 (3) | 0.027 (2) | −0.003 (3) | −0.0022 (16) | −0.012 (3) |
C11 | 0.044 (3) | 0.020 (2) | 0.035 (3) | −0.0041 (19) | 0.000 (2) | 0.0043 (19) |
C12 | 0.048 (3) | 0.034 (3) | 0.035 (3) | 0.002 (2) | 0.004 (2) | 0.002 (2) |
C13 | 0.054 (3) | 0.019 (2) | 0.038 (3) | 0.003 (2) | −0.001 (2) | −0.0070 (19) |
C14 | 0.054 (3) | 0.039 (4) | 0.031 (2) | −0.007 (2) | −0.004 (2) | −0.003 (2) |
C15 | 0.045 (3) | 0.026 (3) | 0.042 (3) | −0.0106 (19) | 0.024 (2) | 0.0038 (19) |
C16 | 0.043 (3) | 0.045 (4) | 0.043 (3) | 0.009 (3) | 0.004 (2) | 0.012 (3) |
C17 | 0.036 (3) | 0.034 (3) | 0.037 (3) | 0.011 (2) | −0.017 (2) | −0.003 (2) |
C18 | 0.045 (3) | 0.049 (3) | 0.036 (3) | −0.005 (3) | −0.008 (2) | −0.002 (2) |
C19 | 0.035 (3) | 0.049 (3) | 0.036 (3) | −0.008 (2) | 0.003 (2) | 0.007 (2) |
C20 | 0.031 (2) | 0.032 (3) | 0.035 (2) | 0.0161 (18) | −0.0075 (18) | 0.0015 (18) |
C21 | 0.055 (5) | 0.047 (3) | 0.038 (3) | 0.024 (3) | −0.007 (3) | −0.017 (2) |
Fe1—C4 | 2.018 (5) | C8—H8A | 0.9800 |
Fe1—C8 | 2.026 (5) | C9—C10 | 1.396 (8) |
Fe1—C5 | 2.032 (5) | C9—H9A | 0.9800 |
Fe1—C3 | 2.033 (4) | C10—C11 | 1.529 (8) |
Fe1—C6 | 2.039 (5) | C11—C19 | 1.522 (7) |
Fe1—C7 | 2.046 (5) | C11—H11A | 0.9800 |
Fe1—C9 | 2.048 (5) | C12—C13 | 1.517 (7) |
Fe1—C1 | 2.058 (5) | C12—C21 | 1.532 (7) |
Fe1—C10 | 2.059 (4) | C12—H12A | 0.9800 |
Fe1—C2 | 2.064 (5) | C13—C18 | 1.372 (8) |
N1—C20 | 1.472 (6) | C13—C14 | 1.393 (8) |
N1—C12 | 1.489 (6) | C14—C15 | 1.412 (7) |
N1—C11 | 1.497 (6) | C14—H14A | 0.9300 |
C1—C5 | 1.386 (7) | C15—C16 | 1.367 (8) |
C1—C2 | 1.398 (8) | C15—H15A | 0.9300 |
C1—H1A | 0.9800 | C16—C17 | 1.366 (8) |
C2—C3 | 1.355 (8) | C16—H16A | 0.9300 |
C2—H2A | 0.9800 | C17—C18 | 1.390 (8) |
C3—C4 | 1.412 (7) | C17—H17A | 0.9300 |
C3—H3A | 0.9800 | C18—H18A | 0.9300 |
C4—C5 | 1.404 (8) | C19—H19A | 0.9600 |
C4—H4A | 0.9800 | C19—H19B | 0.9600 |
C5—H5A | 0.9800 | C19—H19C | 0.9600 |
C6—C10 | 1.424 (7) | C20—H20A | 0.9600 |
C6—C7 | 1.425 (8) | C20—H20B | 0.9600 |
C6—H6A | 0.9800 | C20—H20C | 0.9600 |
C7—C8 | 1.394 (8) | C21—H21A | 0.9600 |
C7—H7A | 0.9800 | C21—H21B | 0.9600 |
C8—C9 | 1.404 (8) | C21—H21C | 0.9600 |
C4—Fe1—C8 | 119.7 (2) | C10—C6—C7 | 108.4 (5) |
C4—Fe1—C5 | 40.6 (2) | C10—C6—Fe1 | 70.4 (3) |
C8—Fe1—C5 | 154.5 (2) | C7—C6—Fe1 | 69.8 (3) |
C4—Fe1—C3 | 40.8 (2) | C10—C6—H6A | 125.8 |
C8—Fe1—C3 | 108.51 (19) | C7—C6—H6A | 125.8 |
C5—Fe1—C3 | 67.6 (2) | Fe1—C6—H6A | 125.8 |
C4—Fe1—C6 | 126.3 (2) | C8—C7—C6 | 107.0 (5) |
C8—Fe1—C6 | 67.7 (2) | C8—C7—Fe1 | 69.2 (3) |
C5—Fe1—C6 | 108.7 (2) | C6—C7—Fe1 | 69.3 (3) |
C3—Fe1—C6 | 164.1 (2) | C8—C7—H7A | 126.5 |
C4—Fe1—C7 | 107.4 (2) | C6—C7—H7A | 126.5 |
C8—Fe1—C7 | 40.0 (2) | Fe1—C7—H7A | 126.5 |
C5—Fe1—C7 | 120.5 (2) | C7—C8—C9 | 108.8 (5) |
C3—Fe1—C7 | 126.4 (2) | C7—C8—Fe1 | 70.8 (3) |
C6—Fe1—C7 | 40.8 (2) | C9—C8—Fe1 | 70.7 (3) |
C4—Fe1—C9 | 154.6 (2) | C7—C8—H8A | 125.6 |
C8—Fe1—C9 | 40.3 (2) | C9—C8—H8A | 125.6 |
C5—Fe1—C9 | 163.8 (2) | Fe1—C8—H8A | 125.6 |
C3—Fe1—C9 | 120.7 (2) | C10—C9—C8 | 109.1 (5) |
C6—Fe1—C9 | 67.3 (2) | C10—C9—Fe1 | 70.6 (3) |
C7—Fe1—C9 | 67.5 (2) | C8—C9—Fe1 | 69.0 (3) |
C4—Fe1—C1 | 66.8 (2) | C10—C9—H9A | 125.5 |
C8—Fe1—C1 | 163.8 (2) | C8—C9—H9A | 125.5 |
C5—Fe1—C1 | 39.6 (2) | Fe1—C9—H9A | 125.5 |
C3—Fe1—C1 | 65.8 (2) | C9—C10—C6 | 106.8 (6) |
C6—Fe1—C1 | 122.0 (2) | C9—C10—C11 | 124.6 (5) |
C7—Fe1—C1 | 155.6 (2) | C6—C10—C11 | 128.7 (5) |
C9—Fe1—C1 | 127.9 (2) | C9—C10—Fe1 | 69.7 (3) |
C4—Fe1—C10 | 164.00 (19) | C6—C10—Fe1 | 68.9 (3) |
C8—Fe1—C10 | 67.9 (3) | C11—C10—Fe1 | 127.3 (5) |
C5—Fe1—C10 | 127.0 (3) | N1—C11—C19 | 115.2 (4) |
C3—Fe1—C10 | 153.9 (2) | N1—C11—C10 | 107.4 (4) |
C6—Fe1—C10 | 40.7 (2) | C19—C11—C10 | 113.4 (4) |
C7—Fe1—C10 | 68.5 (2) | N1—C11—H11A | 106.8 |
C9—Fe1—C10 | 39.7 (2) | C19—C11—H11A | 106.8 |
C1—Fe1—C10 | 110.1 (3) | C10—C11—H11A | 106.8 |
C4—Fe1—C2 | 67.1 (2) | N1—C12—C13 | 110.1 (4) |
C8—Fe1—C2 | 126.5 (2) | N1—C12—C21 | 111.3 (4) |
C5—Fe1—C2 | 67.19 (19) | C13—C12—C21 | 109.6 (5) |
C3—Fe1—C2 | 38.6 (2) | N1—C12—H12A | 108.6 |
C6—Fe1—C2 | 155.9 (2) | C13—C12—H12A | 108.6 |
C7—Fe1—C2 | 162.3 (2) | C21—C12—H12A | 108.6 |
C9—Fe1—C2 | 109.7 (2) | C18—C13—C14 | 118.3 (5) |
C1—Fe1—C2 | 39.6 (2) | C18—C13—C12 | 121.4 (5) |
C10—Fe1—C2 | 121.4 (2) | C14—C13—C12 | 120.3 (5) |
C20—N1—C12 | 110.3 (4) | C13—C14—C15 | 119.6 (5) |
C20—N1—C11 | 111.6 (4) | C13—C14—H14A | 120.2 |
C12—N1—C11 | 113.3 (4) | C15—C14—H14A | 120.2 |
C5—C1—C2 | 109.0 (5) | C16—C15—C14 | 120.7 (5) |
C5—C1—Fe1 | 69.2 (3) | C16—C15—H15A | 119.6 |
C2—C1—Fe1 | 70.4 (3) | C14—C15—H15A | 119.6 |
C5—C1—H1A | 125.5 | C17—C16—C15 | 119.2 (5) |
C2—C1—H1A | 125.5 | C17—C16—H16A | 120.4 |
Fe1—C1—H1A | 125.5 | C15—C16—H16A | 120.4 |
C3—C2—C1 | 107.7 (5) | C16—C17—C18 | 120.6 (5) |
C3—C2—Fe1 | 69.5 (3) | C16—C17—H17A | 119.7 |
C1—C2—Fe1 | 70.0 (3) | C18—C17—H17A | 119.7 |
C3—C2—H2A | 126.2 | C13—C18—C17 | 121.4 (6) |
C1—C2—H2A | 126.2 | C13—C18—H18A | 119.3 |
Fe1—C2—H2A | 126.2 | C17—C18—H18A | 119.3 |
C2—C3—C4 | 109.2 (5) | C11—C19—H19A | 109.5 |
C2—C3—Fe1 | 71.9 (3) | C11—C19—H19B | 109.5 |
C4—C3—Fe1 | 69.0 (3) | H19A—C19—H19B | 109.5 |
C2—C3—H3A | 125.4 | C11—C19—H19C | 109.5 |
C4—C3—H3A | 125.4 | H19A—C19—H19C | 109.5 |
Fe1—C3—H3A | 125.4 | H19B—C19—H19C | 109.5 |
C5—C4—C3 | 106.9 (4) | N1—C20—H20A | 109.5 |
C5—C4—Fe1 | 70.3 (3) | N1—C20—H20B | 109.5 |
C3—C4—Fe1 | 70.2 (3) | H20A—C20—H20B | 109.5 |
C5—C4—H4A | 126.5 | N1—C20—H20C | 109.5 |
C3—C4—H4A | 126.5 | H20A—C20—H20C | 109.5 |
Fe1—C4—H4A | 126.5 | H20B—C20—H20C | 109.5 |
C1—C5—C4 | 107.2 (4) | C12—C21—H21A | 109.5 |
C1—C5—Fe1 | 71.2 (3) | C12—C21—H21B | 109.5 |
C4—C5—Fe1 | 69.2 (3) | H21A—C21—H21B | 109.5 |
C1—C5—H5A | 126.4 | C12—C21—H21C | 109.5 |
C4—C5—H5A | 126.4 | H21A—C21—H21C | 109.5 |
Fe1—C5—H5A | 126.4 | H21B—C21—H21C | 109.5 |
C4—Fe1—C1—C5 | 38.8 (3) | C5—Fe1—C7—C8 | 158.0 (3) |
C8—Fe1—C1—C5 | 156.1 (7) | C3—Fe1—C7—C8 | 74.7 (4) |
C3—Fe1—C1—C5 | 83.5 (3) | C6—Fe1—C7—C8 | −118.5 (4) |
C6—Fe1—C1—C5 | −80.7 (4) | C9—Fe1—C7—C8 | −37.8 (3) |
C7—Fe1—C1—C5 | −42.3 (6) | C1—Fe1—C7—C8 | −172.1 (5) |
C9—Fe1—C1—C5 | −165.4 (3) | C10—Fe1—C7—C8 | −80.7 (3) |
C10—Fe1—C1—C5 | −124.3 (3) | C2—Fe1—C7—C8 | 46.7 (8) |
C2—Fe1—C1—C5 | 120.4 (5) | C4—Fe1—C7—C6 | −125.9 (3) |
C4—Fe1—C1—C2 | −81.5 (3) | C8—Fe1—C7—C6 | 118.5 (4) |
C8—Fe1—C1—C2 | 35.7 (9) | C5—Fe1—C7—C6 | −83.5 (3) |
C5—Fe1—C1—C2 | −120.4 (5) | C3—Fe1—C7—C6 | −166.9 (3) |
C3—Fe1—C1—C2 | −36.8 (3) | C9—Fe1—C7—C6 | 80.7 (3) |
C6—Fe1—C1—C2 | 159.0 (3) | C1—Fe1—C7—C6 | −53.7 (6) |
C7—Fe1—C1—C2 | −162.6 (4) | C10—Fe1—C7—C6 | 37.7 (3) |
C9—Fe1—C1—C2 | 74.2 (4) | C2—Fe1—C7—C6 | 165.1 (6) |
C10—Fe1—C1—C2 | 115.4 (3) | C6—C7—C8—C9 | 1.4 (6) |
C5—C1—C2—C3 | 0.9 (5) | Fe1—C7—C8—C9 | 60.7 (4) |
Fe1—C1—C2—C3 | 59.5 (3) | C6—C7—C8—Fe1 | −59.3 (4) |
C5—C1—C2—Fe1 | −58.6 (3) | C4—Fe1—C8—C7 | −81.8 (3) |
C4—Fe1—C2—C3 | −38.0 (3) | C5—Fe1—C8—C7 | −48.5 (6) |
C8—Fe1—C2—C3 | 72.9 (4) | C3—Fe1—C8—C7 | −125.1 (3) |
C5—Fe1—C2—C3 | −82.2 (4) | C6—Fe1—C8—C7 | 38.4 (3) |
C6—Fe1—C2—C3 | −167.0 (5) | C9—Fe1—C8—C7 | 119.0 (4) |
C7—Fe1—C2—C3 | 37.2 (8) | C1—Fe1—C8—C7 | 168.3 (7) |
C9—Fe1—C2—C3 | 114.9 (3) | C10—Fe1—C8—C7 | 82.5 (3) |
C1—Fe1—C2—C3 | −118.8 (5) | C2—Fe1—C8—C7 | −164.0 (3) |
C10—Fe1—C2—C3 | 157.3 (3) | C4—Fe1—C8—C9 | 159.2 (3) |
C4—Fe1—C2—C1 | 80.8 (3) | C5—Fe1—C8—C9 | −167.5 (5) |
C8—Fe1—C2—C1 | −168.3 (3) | C3—Fe1—C8—C9 | 115.9 (4) |
C5—Fe1—C2—C1 | 36.6 (3) | C6—Fe1—C8—C9 | −80.6 (4) |
C3—Fe1—C2—C1 | 118.8 (5) | C7—Fe1—C8—C9 | −119.0 (4) |
C6—Fe1—C2—C1 | −48.2 (6) | C1—Fe1—C8—C9 | 49.3 (9) |
C7—Fe1—C2—C1 | 156.1 (6) | C10—Fe1—C8—C9 | −36.5 (3) |
C9—Fe1—C2—C1 | −126.3 (3) | C2—Fe1—C8—C9 | 77.0 (4) |
C10—Fe1—C2—C1 | −83.9 (4) | C7—C8—C9—C10 | −1.4 (6) |
C1—C2—C3—C4 | −0.6 (5) | Fe1—C8—C9—C10 | 59.4 (4) |
Fe1—C2—C3—C4 | 59.2 (3) | C7—C8—C9—Fe1 | −60.8 (4) |
C1—C2—C3—Fe1 | −59.8 (3) | C4—Fe1—C9—C10 | −166.4 (5) |
C4—Fe1—C3—C2 | 119.8 (5) | C8—Fe1—C9—C10 | −120.4 (5) |
C8—Fe1—C3—C2 | −125.9 (3) | C5—Fe1—C9—C10 | 40.0 (10) |
C5—Fe1—C3—C2 | 81.0 (3) | C3—Fe1—C9—C10 | 157.0 (4) |
C6—Fe1—C3—C2 | 160.5 (7) | C6—Fe1—C9—C10 | −38.5 (4) |
C7—Fe1—C3—C2 | −166.8 (3) | C7—Fe1—C9—C10 | −82.9 (4) |
C9—Fe1—C3—C2 | −83.3 (4) | C1—Fe1—C9—C10 | 75.1 (5) |
C1—Fe1—C3—C2 | 37.8 (3) | C2—Fe1—C9—C10 | 115.8 (4) |
C10—Fe1—C3—C2 | −48.6 (7) | C4—Fe1—C9—C8 | −45.9 (7) |
C8—Fe1—C3—C4 | 114.3 (3) | C5—Fe1—C9—C8 | 160.4 (7) |
C5—Fe1—C3—C4 | −38.7 (3) | C3—Fe1—C9—C8 | −82.6 (4) |
C6—Fe1—C3—C4 | 40.7 (9) | C6—Fe1—C9—C8 | 81.9 (4) |
C7—Fe1—C3—C4 | 73.4 (4) | C7—Fe1—C9—C8 | 37.5 (3) |
C9—Fe1—C3—C4 | 156.9 (3) | C1—Fe1—C9—C8 | −164.5 (3) |
C1—Fe1—C3—C4 | −82.0 (3) | C10—Fe1—C9—C8 | 120.4 (5) |
C10—Fe1—C3—C4 | −168.4 (6) | C2—Fe1—C9—C8 | −123.8 (3) |
C2—Fe1—C3—C4 | −119.8 (5) | C8—C9—C10—C6 | 0.8 (7) |
C2—C3—C4—C5 | 0.1 (5) | Fe1—C9—C10—C6 | 59.2 (4) |
Fe1—C3—C4—C5 | 61.0 (3) | C8—C9—C10—C11 | 179.6 (5) |
C2—C3—C4—Fe1 | −60.9 (3) | Fe1—C9—C10—C11 | −122.0 (6) |
C8—Fe1—C4—C5 | 158.6 (3) | C8—C9—C10—Fe1 | −58.4 (4) |
C3—Fe1—C4—C5 | −117.2 (4) | C7—C6—C10—C9 | 0.0 (6) |
C6—Fe1—C4—C5 | 75.7 (4) | Fe1—C6—C10—C9 | −59.7 (4) |
C7—Fe1—C4—C5 | 116.8 (3) | C7—C6—C10—C11 | −178.7 (5) |
C9—Fe1—C4—C5 | −169.0 (5) | Fe1—C6—C10—C11 | 121.6 (7) |
C1—Fe1—C4—C5 | −37.9 (3) | C7—C6—C10—Fe1 | 59.7 (4) |
C10—Fe1—C4—C5 | 44.1 (12) | C4—Fe1—C10—C9 | 158.5 (9) |
C2—Fe1—C4—C5 | −81.2 (3) | C8—Fe1—C10—C9 | 37.0 (4) |
C8—Fe1—C4—C3 | −84.2 (3) | C5—Fe1—C10—C9 | −167.0 (4) |
C5—Fe1—C4—C3 | 117.2 (4) | C3—Fe1—C10—C9 | −50.0 (8) |
C6—Fe1—C4—C3 | −167.2 (3) | C6—Fe1—C10—C9 | 118.2 (6) |
C7—Fe1—C4—C3 | −126.1 (3) | C7—Fe1—C10—C9 | 80.3 (4) |
C9—Fe1—C4—C3 | −51.8 (7) | C1—Fe1—C10—C9 | −125.8 (4) |
C1—Fe1—C4—C3 | 79.3 (3) | C2—Fe1—C10—C9 | −83.3 (5) |
C10—Fe1—C4—C3 | 161.3 (10) | C4—Fe1—C10—C6 | 40.3 (13) |
C2—Fe1—C4—C3 | 36.0 (3) | C8—Fe1—C10—C6 | −81.1 (4) |
C2—C1—C5—C4 | −0.8 (5) | C5—Fe1—C10—C6 | 74.8 (5) |
Fe1—C1—C5—C4 | −60.1 (3) | C3—Fe1—C10—C6 | −168.2 (4) |
C2—C1—C5—Fe1 | 59.3 (3) | C7—Fe1—C10—C6 | −37.9 (4) |
C3—C4—C5—C1 | 0.5 (5) | C9—Fe1—C10—C6 | −118.2 (6) |
Fe1—C4—C5—C1 | 61.4 (3) | C1—Fe1—C10—C6 | 116.1 (4) |
C3—C4—C5—Fe1 | −61.0 (3) | C2—Fe1—C10—C6 | 158.6 (3) |
C4—Fe1—C5—C1 | −117.6 (4) | C4—Fe1—C10—C11 | −83.0 (11) |
C8—Fe1—C5—C1 | −164.8 (4) | C8—Fe1—C10—C11 | 155.6 (5) |
C3—Fe1—C5—C1 | −78.6 (3) | C5—Fe1—C10—C11 | −48.4 (5) |
C6—Fe1—C5—C1 | 117.9 (3) | C3—Fe1—C10—C11 | 68.6 (7) |
C7—Fe1—C5—C1 | 161.2 (3) | C6—Fe1—C10—C11 | −123.3 (6) |
C9—Fe1—C5—C1 | 45.4 (9) | C7—Fe1—C10—C11 | −161.1 (5) |
C10—Fe1—C5—C1 | 76.3 (4) | C9—Fe1—C10—C11 | 118.6 (6) |
C2—Fe1—C5—C1 | −36.7 (3) | C1—Fe1—C10—C11 | −7.2 (4) |
C8—Fe1—C5—C4 | −47.2 (5) | C2—Fe1—C10—C11 | 35.3 (5) |
C3—Fe1—C5—C4 | 39.0 (3) | C20—N1—C11—C19 | 64.9 (5) |
C6—Fe1—C5—C4 | −124.5 (3) | C12—N1—C11—C19 | −60.3 (6) |
C7—Fe1—C5—C4 | −81.2 (3) | C20—N1—C11—C10 | −62.5 (5) |
C9—Fe1—C5—C4 | 162.9 (8) | C12—N1—C11—C10 | 172.3 (4) |
C1—Fe1—C5—C4 | 117.6 (4) | C9—C10—C11—N1 | −70.3 (7) |
C10—Fe1—C5—C4 | −166.1 (3) | C6—C10—C11—N1 | 108.2 (7) |
C2—Fe1—C5—C4 | 80.9 (3) | Fe1—C10—C11—N1 | −160.0 (3) |
C4—Fe1—C6—C10 | −167.2 (4) | C9—C10—C11—C19 | 161.3 (6) |
C8—Fe1—C6—C10 | 81.5 (4) | C6—C10—C11—C19 | −20.2 (8) |
C5—Fe1—C6—C10 | −125.6 (4) | Fe1—C10—C11—C19 | 71.6 (5) |
C3—Fe1—C6—C10 | 160.8 (7) | C20—N1—C12—C13 | 57.5 (5) |
C7—Fe1—C6—C10 | 119.1 (5) | C11—N1—C12—C13 | −176.6 (4) |
C9—Fe1—C6—C10 | 37.7 (4) | C20—N1—C12—C21 | 179.2 (5) |
C1—Fe1—C6—C10 | −83.9 (4) | C11—N1—C12—C21 | −54.9 (6) |
C2—Fe1—C6—C10 | −49.9 (7) | N1—C12—C13—C18 | −117.6 (6) |
C4—Fe1—C6—C7 | 73.6 (4) | C21—C12—C13—C18 | 119.6 (6) |
C8—Fe1—C6—C7 | −37.7 (3) | N1—C12—C13—C14 | 63.7 (6) |
C5—Fe1—C6—C7 | 115.3 (3) | C21—C12—C13—C14 | −59.1 (6) |
C3—Fe1—C6—C7 | 41.7 (9) | C18—C13—C14—C15 | 3.6 (8) |
C9—Fe1—C6—C7 | −81.5 (4) | C12—C13—C14—C15 | −177.6 (5) |
C1—Fe1—C6—C7 | 156.9 (3) | C13—C14—C15—C16 | −4.4 (8) |
C10—Fe1—C6—C7 | −119.1 (5) | C14—C15—C16—C17 | 1.5 (9) |
C2—Fe1—C6—C7 | −169.0 (5) | C15—C16—C17—C18 | 2.0 (9) |
C10—C6—C7—C8 | −0.9 (6) | C14—C13—C18—C17 | −0.2 (8) |
Fe1—C6—C7—C8 | 59.2 (4) | C12—C13—C18—C17 | −178.9 (5) |
C10—C6—C7—Fe1 | −60.1 (4) | C16—C17—C18—C13 | −2.7 (9) |
C4—Fe1—C7—C8 | 115.7 (3) |