Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016054/om2107sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016054/om2107Isup2.hkl |
CCDC reference: 647289
Data collection: SMART (Bruker 2003); cell refinement: SAINT (Bruker 2003); 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 1998); software used to prepare material for publication: SHELXTL.
[Fe(C5H5)(C14H16N)] | F(000) = 336 |
Mr = 319.22 | Dx = 1.338 Mg m−3 |
Triclinic, P1 | Melting point: 312 K |
a = 5.9691 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.245 (2) Å | Cell parameters from 2536 reflections |
c = 13.717 (3) Å | θ = 2.7–26.4° |
α = 93.916 (3)° | µ = 0.95 mm−1 |
β = 99.948 (3)° | T = 294 K |
γ = 105.071 (3)° | Block, yellow |
V = 792.2 (3) Å3 | 0.26 × 0.24 × 0.18 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 3191 independent reflections |
Radiation source: fine-focus sealed tube | 2763 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
φ and ω scans | θmax = 26.4°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→7 |
Tmin = 0.791, Tmax = 0.848 | k = −12→10 |
4475 measured reflections | l = −13→17 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.038P)2 + 0.2288P] where P = (Fo2 + 2Fc2)/3 |
3191 reflections | (Δ/σ)max < 0.001 |
230 parameters | Δρmax = 0.50 e Å−3 |
30 restraints | Δρmin = −0.25 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 | Occ. (<1) | |
Fe1 | 0.65307 (5) | 0.16948 (3) | 0.84974 (2) | 0.03860 (12) | |
N1 | 0.6963 (5) | 0.2796 (3) | 0.54241 (15) | 0.0739 (7) | |
C1 | 0.6095 (4) | 0.1840 (2) | 0.69990 (14) | 0.0447 (5) | |
C2 | 0.3931 (4) | 0.1749 (3) | 0.73306 (17) | 0.0546 (6) | |
H2 | 0.3084 | 0.2393 | 0.7281 | 0.066* | |
C3 | 0.3290 (4) | 0.0518 (3) | 0.77465 (18) | 0.0578 (6) | |
H3 | 0.1953 | 0.0213 | 0.8020 | 0.069* | |
C4 | 0.5030 (5) | −0.0172 (2) | 0.76765 (17) | 0.0539 (6) | |
H4 | 0.5042 | −0.1011 | 0.7895 | 0.065* | |
C5 | 0.6749 (4) | 0.0638 (2) | 0.72155 (15) | 0.0462 (5) | |
H5 | 0.8088 | 0.0420 | 0.7076 | 0.055* | |
C6 | 0.8907 (5) | 0.3452 (3) | 0.91917 (18) | 0.0665 (8) | |
H6 | 0.9565 | 0.4196 | 0.8881 | 0.080* | |
C7 | 0.6859 (5) | 0.3248 (3) | 0.95717 (17) | 0.0596 (7) | |
H7 | 0.5901 | 0.3834 | 0.9556 | 0.071* | |
C8 | 0.6467 (5) | 0.2025 (3) | 0.99804 (17) | 0.0610 (7) | |
H8 | 0.5209 | 0.1658 | 1.0287 | 0.073* | |
C9 | 0.8275 (6) | 0.1441 (3) | 0.98546 (19) | 0.0699 (8) | |
H9 | 0.8435 | 0.0618 | 1.0059 | 0.084* | |
C10 | 0.9826 (5) | 0.2326 (4) | 0.9359 (2) | 0.0764 (9) | |
H10 | 1.1189 | 0.2193 | 0.9179 | 0.092* | |
C11 | 0.7431 (5) | 0.2991 (3) | 0.65184 (16) | 0.0597 (6) | |
H11A | 0.7045 | 0.3814 | 0.6732 | 0.072* | |
H11B | 0.9111 | 0.3132 | 0.6761 | 0.072* | |
C12 | 0.7732 (5) | 0.1688 (3) | 0.50229 (19) | 0.0708 (8) | |
H12A | 0.7366 | 0.1604 | 0.4308 | 0.106* | |
H12B | 0.6933 | 0.0858 | 0.5247 | 0.106* | |
H12C | 0.9410 | 0.1865 | 0.5246 | 0.106* | |
C13 | 0.4784 (6) | 0.2861 (4) | 0.4968 (2) | 0.0562 (11) | 0.673 (5) |
H13A | 0.4352 | 0.3548 | 0.5359 | 0.067* | 0.673 (5) |
H13B | 0.3654 | 0.1995 | 0.4985 | 0.067* | 0.673 (5) |
C14 | 0.4509 (8) | 0.3185 (4) | 0.38856 (16) | 0.0422 (10) | 0.673 (5) |
C15 | 0.2280 (6) | 0.2743 (4) | 0.3271 (3) | 0.0514 (12) | 0.673 (5) |
H15A | 0.0993 | 0.2261 | 0.3518 | 0.062* | 0.673 (5) |
C16 | 0.1976 (5) | 0.3022 (5) | 0.2287 (2) | 0.0564 (13) | 0.673 (5) |
H16A | 0.0485 | 0.2726 | 0.1875 | 0.068* | 0.673 (5) |
C17 | 0.3900 (8) | 0.3742 (6) | 0.1917 (2) | 0.0554 (15) | 0.673 (5) |
H17A | 0.3696 | 0.3929 | 0.1259 | 0.066* | 0.673 (5) |
C18 | 0.6128 (6) | 0.4184 (5) | 0.2532 (3) | 0.0586 (15) | 0.673 (5) |
H18A | 0.7415 | 0.4666 | 0.2285 | 0.070* | 0.673 (5) |
C19 | 0.6433 (5) | 0.3905 (4) | 0.3516 (3) | 0.0524 (13) | 0.673 (5) |
H19A | 0.7923 | 0.4201 | 0.3927 | 0.063* | 0.673 (5) |
C13' | 0.6874 (17) | 0.3892 (7) | 0.4939 (5) | 0.075 (3) | 0.327 (5) |
H13C | 0.8490 | 0.4417 | 0.4956 | 0.090* | 0.327 (5) |
H13D | 0.6166 | 0.4453 | 0.5318 | 0.090* | 0.327 (5) |
C14' | 0.5573 (14) | 0.3673 (7) | 0.3875 (3) | 0.040 (2) | 0.327 (5) |
C15' | 0.3143 (14) | 0.3079 (8) | 0.3636 (5) | 0.055 (3) | 0.327 (5) |
H15B | 0.2338 | 0.2722 | 0.4124 | 0.066* | 0.327 (5) |
C16' | 0.1914 (9) | 0.3017 (11) | 0.2668 (7) | 0.062 (3) | 0.327 (5) |
H16B | 0.0288 | 0.2619 | 0.2509 | 0.075* | 0.327 (5) |
C17' | 0.3116 (16) | 0.3550 (13) | 0.1939 (4) | 0.054 (3) | 0.327 (5) |
H17B | 0.2294 | 0.3508 | 0.1292 | 0.065* | 0.327 (5) |
C18' | 0.5547 (16) | 0.4144 (11) | 0.2178 (5) | 0.050 (3) | 0.327 (5) |
H18B | 0.6351 | 0.4500 | 0.1690 | 0.061* | 0.327 (5) |
C19' | 0.6775 (9) | 0.4206 (7) | 0.3146 (6) | 0.046 (2) | 0.327 (5) |
H19B | 0.8402 | 0.4603 | 0.3305 | 0.055* | 0.327 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.04194 (18) | 0.04231 (18) | 0.02863 (16) | 0.01226 (13) | 0.00018 (11) | −0.00084 (11) |
N1 | 0.114 (2) | 0.0824 (16) | 0.0323 (10) | 0.0449 (15) | 0.0059 (12) | 0.0075 (10) |
C1 | 0.0503 (13) | 0.0525 (13) | 0.0272 (10) | 0.0160 (10) | −0.0028 (9) | −0.0020 (9) |
C2 | 0.0512 (14) | 0.0731 (17) | 0.0397 (12) | 0.0287 (12) | −0.0043 (10) | −0.0027 (11) |
C3 | 0.0429 (13) | 0.0747 (17) | 0.0443 (13) | 0.0026 (12) | 0.0036 (10) | −0.0047 (12) |
C4 | 0.0703 (16) | 0.0423 (12) | 0.0408 (12) | 0.0076 (11) | 0.0048 (11) | −0.0038 (10) |
C5 | 0.0501 (13) | 0.0528 (13) | 0.0344 (10) | 0.0195 (11) | 0.0012 (9) | −0.0060 (9) |
C6 | 0.0768 (19) | 0.0583 (16) | 0.0423 (13) | −0.0122 (14) | 0.0048 (12) | −0.0073 (11) |
C7 | 0.0783 (18) | 0.0553 (15) | 0.0423 (13) | 0.0214 (13) | 0.0061 (12) | −0.0105 (11) |
C8 | 0.0701 (17) | 0.0738 (17) | 0.0313 (11) | 0.0086 (14) | 0.0087 (11) | 0.0006 (11) |
C9 | 0.089 (2) | 0.0702 (18) | 0.0433 (14) | 0.0293 (16) | −0.0175 (14) | 0.0057 (12) |
C10 | 0.0425 (14) | 0.121 (3) | 0.0503 (15) | 0.0197 (16) | −0.0110 (12) | −0.0298 (16) |
C11 | 0.0812 (18) | 0.0575 (15) | 0.0338 (11) | 0.0131 (13) | 0.0032 (11) | 0.0042 (10) |
C12 | 0.081 (2) | 0.096 (2) | 0.0433 (14) | 0.0345 (17) | 0.0167 (13) | 0.0101 (14) |
C13 | 0.056 (2) | 0.074 (3) | 0.0413 (19) | 0.0184 (19) | 0.0164 (16) | 0.0092 (17) |
C14 | 0.036 (3) | 0.054 (3) | 0.0366 (19) | 0.011 (2) | 0.011 (2) | 0.0060 (18) |
C15 | 0.049 (3) | 0.068 (3) | 0.037 (3) | 0.018 (2) | 0.005 (2) | 0.004 (2) |
C16 | 0.059 (3) | 0.075 (3) | 0.038 (3) | 0.029 (2) | 0.004 (2) | 0.002 (2) |
C17 | 0.076 (4) | 0.062 (4) | 0.036 (3) | 0.030 (3) | 0.013 (2) | 0.013 (2) |
C18 | 0.068 (3) | 0.063 (3) | 0.046 (4) | 0.015 (3) | 0.010 (3) | 0.022 (3) |
C19 | 0.053 (3) | 0.054 (3) | 0.045 (3) | 0.005 (2) | 0.008 (2) | 0.012 (2) |
C13' | 0.115 (8) | 0.048 (5) | 0.034 (4) | −0.013 (5) | −0.004 (4) | 0.002 (3) |
C14' | 0.030 (5) | 0.042 (5) | 0.036 (4) | −0.009 (4) | 0.007 (4) | 0.007 (3) |
C15' | 0.033 (6) | 0.074 (6) | 0.049 (6) | −0.005 (5) | 0.012 (5) | 0.005 (5) |
C16' | 0.055 (5) | 0.067 (6) | 0.058 (7) | 0.011 (4) | 0.005 (5) | −0.008 (5) |
C17' | 0.062 (6) | 0.049 (5) | 0.045 (6) | 0.019 (5) | −0.012 (4) | 0.000 (4) |
C18' | 0.062 (6) | 0.056 (5) | 0.031 (5) | 0.016 (5) | 0.001 (5) | 0.014 (4) |
C19' | 0.053 (5) | 0.045 (5) | 0.039 (6) | 0.009 (3) | 0.006 (5) | 0.025 (5) |
Fe1—C10 | 2.029 (3) | C11—H11A | 0.9700 |
Fe1—C6 | 2.032 (2) | C11—H11B | 0.9700 |
Fe1—C9 | 2.038 (2) | C12—H12A | 0.9600 |
Fe1—C7 | 2.040 (2) | C12—H12B | 0.9600 |
Fe1—C2 | 2.042 (2) | C12—H12C | 0.9600 |
Fe1—C5 | 2.043 (2) | C13—C14 | 1.533 (4) |
Fe1—C3 | 2.046 (2) | C13—H13A | 0.9700 |
Fe1—C1 | 2.047 (2) | C13—H13B | 0.9700 |
Fe1—C8 | 2.048 (2) | C14—C15 | 1.3900 |
Fe1—C4 | 2.048 (2) | C14—C19 | 1.3900 |
N1—C13' | 1.352 (6) | C15—C16 | 1.3900 |
N1—C13 | 1.363 (4) | C15—H15A | 0.9300 |
N1—C12 | 1.441 (4) | C16—C17 | 1.3900 |
N1—C11 | 1.468 (3) | C16—H16A | 0.9300 |
C1—C5 | 1.420 (3) | C17—C18 | 1.3900 |
C1—C2 | 1.425 (3) | C17—H17A | 0.9300 |
C1—C11 | 1.503 (3) | C18—C19 | 1.3900 |
C2—C3 | 1.409 (4) | C18—H18A | 0.9300 |
C2—H2 | 0.9300 | C19—H19A | 0.9300 |
C3—C4 | 1.413 (4) | C13'—C14' | 1.502 (6) |
C3—H3 | 0.9300 | C13'—H13C | 0.9700 |
C4—C5 | 1.412 (3) | C13'—H13D | 0.9700 |
C4—H4 | 0.9300 | C14'—C15' | 1.3900 |
C5—H5 | 0.9300 | C14'—C19' | 1.3900 |
C6—C7 | 1.383 (4) | C15'—C16' | 1.3900 |
C6—C10 | 1.416 (4) | C15'—H15B | 0.9300 |
C6—H6 | 0.9300 | C16'—C17' | 1.3900 |
C7—C8 | 1.388 (4) | C16'—H16B | 0.9300 |
C7—H7 | 0.9300 | C17'—C18' | 1.3900 |
C8—C9 | 1.392 (4) | C17'—H17B | 0.9300 |
C8—H8 | 0.9300 | C18'—C19' | 1.3900 |
C9—C10 | 1.416 (4) | C18'—H18B | 0.9300 |
C9—H9 | 0.9300 | C19'—H19B | 0.9300 |
C10—H10 | 0.9300 | ||
C10—Fe1—C6 | 40.82 (13) | Fe1—C6—H6 | 125.7 |
C10—Fe1—C9 | 40.74 (13) | C6—C7—C8 | 108.9 (3) |
C6—Fe1—C9 | 68.01 (12) | C6—C7—Fe1 | 69.87 (14) |
C10—Fe1—C7 | 67.61 (12) | C8—C7—Fe1 | 70.47 (14) |
C6—Fe1—C7 | 39.71 (11) | C6—C7—H7 | 125.6 |
C9—Fe1—C7 | 67.18 (11) | C8—C7—H7 | 125.6 |
C10—Fe1—C2 | 154.82 (14) | Fe1—C7—H7 | 125.7 |
C6—Fe1—C2 | 120.07 (12) | C7—C8—C9 | 108.5 (3) |
C9—Fe1—C2 | 162.86 (12) | C7—C8—Fe1 | 69.82 (13) |
C7—Fe1—C2 | 108.46 (11) | C9—C8—Fe1 | 69.70 (14) |
C10—Fe1—C5 | 107.63 (10) | C7—C8—H8 | 125.8 |
C6—Fe1—C5 | 125.38 (11) | C9—C8—H8 | 125.8 |
C9—Fe1—C5 | 121.47 (11) | Fe1—C8—H8 | 126.3 |
C7—Fe1—C5 | 161.91 (11) | C8—C9—C10 | 107.7 (3) |
C2—Fe1—C5 | 67.93 (9) | C8—C9—Fe1 | 70.45 (14) |
C10—Fe1—C3 | 163.15 (14) | C10—C9—Fe1 | 69.27 (15) |
C6—Fe1—C3 | 155.04 (13) | C8—C9—H9 | 126.1 |
C9—Fe1—C3 | 126.50 (12) | C10—C9—H9 | 126.1 |
C7—Fe1—C3 | 121.72 (11) | Fe1—C9—H9 | 125.7 |
C2—Fe1—C3 | 40.31 (11) | C9—C10—C6 | 107.0 (3) |
C5—Fe1—C3 | 67.85 (10) | C9—C10—Fe1 | 69.99 (15) |
C10—Fe1—C1 | 119.54 (12) | C6—C10—Fe1 | 69.72 (15) |
C6—Fe1—C1 | 106.80 (10) | C9—C10—H10 | 126.5 |
C9—Fe1—C1 | 155.45 (12) | C6—C10—H10 | 126.5 |
C7—Fe1—C1 | 125.07 (10) | Fe1—C10—H10 | 125.4 |
C2—Fe1—C1 | 40.77 (9) | N1—C11—C1 | 115.4 (2) |
C5—Fe1—C1 | 40.63 (9) | N1—C11—H11A | 108.4 |
C3—Fe1—C1 | 68.39 (10) | C1—C11—H11A | 108.4 |
C10—Fe1—C8 | 67.62 (12) | N1—C11—H11B | 108.4 |
C6—Fe1—C8 | 67.07 (11) | C1—C11—H11B | 108.4 |
C9—Fe1—C8 | 39.85 (11) | H11A—C11—H11B | 107.5 |
C7—Fe1—C8 | 39.71 (11) | N1—C12—H12A | 109.5 |
C2—Fe1—C8 | 126.32 (11) | N1—C12—H12B | 109.5 |
C5—Fe1—C8 | 156.52 (11) | H12A—C12—H12B | 109.5 |
C3—Fe1—C8 | 109.63 (11) | N1—C12—H12C | 109.5 |
C1—Fe1—C8 | 162.19 (10) | H12A—C12—H12C | 109.5 |
C10—Fe1—C4 | 125.80 (12) | H12B—C12—H12C | 109.5 |
C6—Fe1—C4 | 162.72 (12) | N1—C13—C14 | 117.0 (3) |
C9—Fe1—C4 | 109.02 (11) | N1—C13—H13A | 108.0 |
C7—Fe1—C4 | 156.45 (11) | C14—C13—H13A | 108.0 |
C2—Fe1—C4 | 67.91 (11) | N1—C13—H13B | 108.0 |
C5—Fe1—C4 | 40.39 (10) | C14—C13—H13B | 108.0 |
C3—Fe1—C4 | 40.37 (10) | H13A—C13—H13B | 107.3 |
C1—Fe1—C4 | 68.42 (9) | C15—C14—C19 | 120.0 |
C8—Fe1—C4 | 122.36 (11) | C15—C14—C13 | 118.7 (3) |
C13'—N1—C13 | 63.0 (4) | C19—C14—C13 | 121.3 (3) |
C13'—N1—C12 | 122.4 (4) | C16—C15—C14 | 120.0 |
C13—N1—C12 | 115.3 (3) | C16—C15—H15A | 120.0 |
C13'—N1—C11 | 117.9 (3) | C14—C15—H15A | 120.0 |
C13—N1—C11 | 115.4 (2) | C15—C16—C17 | 120.0 |
C12—N1—C11 | 113.2 (2) | C15—C16—H16A | 120.0 |
C5—C1—C2 | 106.7 (2) | C17—C16—H16A | 120.0 |
C5—C1—C11 | 126.7 (2) | C16—C17—C18 | 120.0 |
C2—C1—C11 | 126.5 (2) | C16—C17—H17A | 120.0 |
C5—C1—Fe1 | 69.52 (12) | C18—C17—H17A | 120.0 |
C2—C1—Fe1 | 69.42 (12) | C19—C18—C17 | 120.0 |
C11—C1—Fe1 | 125.74 (15) | C19—C18—H18A | 120.0 |
C3—C2—C1 | 108.6 (2) | C17—C18—H18A | 120.0 |
C3—C2—Fe1 | 69.98 (13) | C18—C19—C14 | 120.0 |
C1—C2—Fe1 | 69.81 (12) | C18—C19—H19A | 120.0 |
C3—C2—H2 | 125.7 | C14—C19—H19A | 120.0 |
C1—C2—H2 | 125.7 | N1—C13'—C14' | 119.0 (5) |
Fe1—C2—H2 | 126.1 | N1—C13'—H13C | 107.6 |
C2—C3—C4 | 108.2 (2) | C14'—C13'—H13C | 107.6 |
C2—C3—Fe1 | 69.70 (14) | N1—C13'—H13D | 107.6 |
C4—C3—Fe1 | 69.92 (14) | C14'—C13'—H13D | 107.6 |
C2—C3—H3 | 125.9 | H13C—C13'—H13D | 107.0 |
C4—C3—H3 | 125.9 | C15'—C14'—C19' | 120.0 |
Fe1—C3—H3 | 126.0 | C15'—C14'—C13' | 120.4 (6) |
C5—C4—C3 | 107.8 (2) | C19'—C14'—C13' | 119.2 (6) |
C5—C4—Fe1 | 69.60 (12) | C14'—C15'—C16' | 120.0 |
C3—C4—Fe1 | 69.72 (13) | C14'—C15'—H15B | 120.0 |
C5—C4—H4 | 126.1 | C16'—C15'—H15B | 120.0 |
C3—C4—H4 | 126.1 | C17'—C16'—C15' | 120.0 |
Fe1—C4—H4 | 126.1 | C17'—C16'—H16B | 120.0 |
C4—C5—C1 | 108.8 (2) | C15'—C16'—H16B | 120.0 |
C4—C5—Fe1 | 70.02 (12) | C18'—C17'—C16' | 120.0 |
C1—C5—Fe1 | 69.85 (12) | C18'—C17'—H17B | 120.0 |
C4—C5—H5 | 125.6 | C16'—C17'—H17B | 120.0 |
C1—C5—H5 | 125.6 | C19'—C18'—C17' | 120.0 |
Fe1—C5—H5 | 126.1 | C19'—C18'—H18B | 120.0 |
C7—C6—C10 | 107.9 (3) | C17'—C18'—H18B | 120.0 |
C7—C6—Fe1 | 70.43 (15) | C18'—C19'—C14' | 120.0 |
C10—C6—Fe1 | 69.46 (15) | C18'—C19'—H19B | 120.0 |
C7—C6—H6 | 126.0 | C14'—C19'—H19B | 120.0 |
C10—C6—H6 | 126.0 | ||
C10—Fe1—C1—C5 | 82.77 (18) | C2—Fe1—C6—C10 | −158.33 (17) |
C6—Fe1—C1—C5 | 125.25 (16) | C5—Fe1—C6—C10 | −75.3 (2) |
C9—Fe1—C1—C5 | 51.6 (3) | C3—Fe1—C6—C10 | 169.2 (2) |
C7—Fe1—C1—C5 | 164.90 (15) | C1—Fe1—C6—C10 | −116.01 (17) |
C2—Fe1—C1—C5 | −117.9 (2) | C8—Fe1—C6—C10 | 81.79 (19) |
C3—Fe1—C1—C5 | −80.72 (15) | C4—Fe1—C6—C10 | −44.9 (4) |
C8—Fe1—C1—C5 | −167.8 (3) | C10—C6—C7—C8 | 0.3 (3) |
C4—Fe1—C1—C5 | −37.16 (14) | Fe1—C6—C7—C8 | 59.89 (17) |
C10—Fe1—C1—C2 | −159.32 (17) | C10—C6—C7—Fe1 | −59.57 (17) |
C6—Fe1—C1—C2 | −116.84 (17) | C10—Fe1—C7—C6 | 38.27 (18) |
C9—Fe1—C1—C2 | 169.5 (2) | C9—Fe1—C7—C6 | 82.6 (2) |
C7—Fe1—C1—C2 | −77.19 (18) | C2—Fe1—C7—C6 | −115.15 (18) |
C5—Fe1—C1—C2 | 117.9 (2) | C5—Fe1—C7—C6 | −39.9 (4) |
C3—Fe1—C1—C2 | 37.19 (15) | C3—Fe1—C7—C6 | −157.53 (17) |
C8—Fe1—C1—C2 | −49.9 (4) | C1—Fe1—C7—C6 | −73.0 (2) |
C4—Fe1—C1—C2 | 80.75 (16) | C8—Fe1—C7—C6 | 119.7 (2) |
C10—Fe1—C1—C11 | −38.4 (3) | C4—Fe1—C7—C6 | 167.9 (2) |
C6—Fe1—C1—C11 | 4.0 (2) | C10—Fe1—C7—C8 | −81.4 (2) |
C9—Fe1—C1—C11 | −69.6 (3) | C6—Fe1—C7—C8 | −119.7 (2) |
C7—Fe1—C1—C11 | 43.7 (3) | C9—Fe1—C7—C8 | −37.15 (18) |
C2—Fe1—C1—C11 | 120.9 (3) | C2—Fe1—C7—C8 | 125.13 (17) |
C5—Fe1—C1—C11 | −121.2 (3) | C5—Fe1—C7—C8 | −159.6 (3) |
C3—Fe1—C1—C11 | 158.1 (2) | C3—Fe1—C7—C8 | 82.76 (19) |
C8—Fe1—C1—C11 | 71.0 (4) | C1—Fe1—C7—C8 | 167.30 (15) |
C4—Fe1—C1—C11 | −158.4 (2) | C4—Fe1—C7—C8 | 48.2 (3) |
C5—C1—C2—C3 | 0.4 (2) | C6—C7—C8—C9 | −0.3 (3) |
C11—C1—C2—C3 | −179.3 (2) | Fe1—C7—C8—C9 | 59.19 (17) |
Fe1—C1—C2—C3 | −59.44 (16) | C6—C7—C8—Fe1 | −59.52 (17) |
C5—C1—C2—Fe1 | 59.80 (14) | C10—Fe1—C8—C7 | 81.4 (2) |
C11—C1—C2—Fe1 | −119.9 (2) | C6—Fe1—C8—C7 | 37.04 (18) |
C10—Fe1—C2—C3 | 165.9 (2) | C9—Fe1—C8—C7 | 119.7 (3) |
C6—Fe1—C2—C3 | −159.53 (15) | C2—Fe1—C8—C7 | −74.3 (2) |
C9—Fe1—C2—C3 | −45.4 (4) | C5—Fe1—C8—C7 | 164.2 (2) |
C7—Fe1—C2—C3 | −117.60 (16) | C3—Fe1—C8—C7 | −116.37 (18) |
C5—Fe1—C2—C3 | 81.31 (16) | C1—Fe1—C8—C7 | −36.0 (4) |
C1—Fe1—C2—C3 | 119.7 (2) | C4—Fe1—C8—C7 | −159.34 (16) |
C8—Fe1—C2—C3 | −77.18 (18) | C10—Fe1—C8—C9 | −38.25 (19) |
C4—Fe1—C2—C3 | 37.57 (15) | C6—Fe1—C8—C9 | −82.7 (2) |
C10—Fe1—C2—C1 | 46.2 (3) | C7—Fe1—C8—C9 | −119.7 (3) |
C6—Fe1—C2—C1 | 80.78 (17) | C2—Fe1—C8—C9 | 165.98 (17) |
C9—Fe1—C2—C1 | −165.1 (3) | C5—Fe1—C8—C9 | 44.5 (3) |
C7—Fe1—C2—C1 | 122.71 (15) | C3—Fe1—C8—C9 | 123.93 (19) |
C5—Fe1—C2—C1 | −38.38 (13) | C1—Fe1—C8—C9 | −155.7 (3) |
C3—Fe1—C2—C1 | −119.7 (2) | C4—Fe1—C8—C9 | 81.0 (2) |
C8—Fe1—C2—C1 | 163.13 (14) | C7—C8—C9—C10 | 0.2 (3) |
C4—Fe1—C2—C1 | −82.12 (15) | Fe1—C8—C9—C10 | 59.46 (17) |
C1—C2—C3—C4 | −0.2 (3) | C7—C8—C9—Fe1 | −59.26 (17) |
Fe1—C2—C3—C4 | −59.56 (16) | C10—Fe1—C9—C8 | 118.7 (3) |
C1—C2—C3—Fe1 | 59.34 (15) | C6—Fe1—C9—C8 | 80.11 (19) |
C10—Fe1—C3—C2 | −159.1 (3) | C7—Fe1—C9—C8 | 37.02 (17) |
C6—Fe1—C3—C2 | 45.8 (3) | C2—Fe1—C9—C8 | −41.5 (4) |
C9—Fe1—C3—C2 | 164.88 (15) | C5—Fe1—C9—C8 | −160.88 (16) |
C7—Fe1—C3—C2 | 81.19 (17) | C3—Fe1—C9—C8 | −76.4 (2) |
C5—Fe1—C3—C2 | −81.54 (15) | C1—Fe1—C9—C8 | 162.4 (2) |
C1—Fe1—C3—C2 | −37.60 (14) | C4—Fe1—C9—C8 | −118.07 (17) |
C8—Fe1—C3—C2 | 123.48 (16) | C6—Fe1—C9—C10 | −38.59 (17) |
C4—Fe1—C3—C2 | −119.3 (2) | C7—Fe1—C9—C10 | −81.69 (19) |
C10—Fe1—C3—C4 | −39.8 (4) | C2—Fe1—C9—C10 | −160.2 (3) |
C6—Fe1—C3—C4 | 165.1 (2) | C5—Fe1—C9—C10 | 80.4 (2) |
C9—Fe1—C3—C4 | −75.84 (19) | C3—Fe1—C9—C10 | 164.85 (17) |
C7—Fe1—C3—C4 | −159.53 (15) | C1—Fe1—C9—C10 | 43.7 (3) |
C2—Fe1—C3—C4 | 119.3 (2) | C8—Fe1—C9—C10 | −118.7 (2) |
C5—Fe1—C3—C4 | 37.74 (14) | C4—Fe1—C9—C10 | 123.23 (18) |
C1—Fe1—C3—C4 | 81.67 (15) | C8—C9—C10—C6 | 0.0 (3) |
C8—Fe1—C3—C4 | −117.25 (16) | Fe1—C9—C10—C6 | 60.20 (17) |
C2—C3—C4—C5 | 0.0 (3) | C8—C9—C10—Fe1 | −60.21 (17) |
Fe1—C3—C4—C5 | −59.43 (15) | C7—C6—C10—C9 | −0.2 (3) |
C2—C3—C4—Fe1 | 59.43 (16) | Fe1—C6—C10—C9 | −60.37 (17) |
C10—Fe1—C4—C5 | −74.25 (19) | C7—C6—C10—Fe1 | 60.18 (18) |
C6—Fe1—C4—C5 | −39.6 (4) | C6—Fe1—C10—C9 | 117.8 (2) |
C9—Fe1—C4—C5 | −116.56 (16) | C7—Fe1—C10—C9 | 80.53 (18) |
C7—Fe1—C4—C5 | 167.1 (2) | C2—Fe1—C10—C9 | 166.4 (2) |
C2—Fe1—C4—C5 | 81.46 (15) | C5—Fe1—C10—C9 | −118.06 (17) |
C3—Fe1—C4—C5 | 119.0 (2) | C3—Fe1—C10—C9 | −46.5 (4) |
C1—Fe1—C4—C5 | 37.38 (13) | C1—Fe1—C10—C9 | −160.74 (16) |
C8—Fe1—C4—C5 | −158.58 (15) | C8—Fe1—C10—C9 | 37.43 (17) |
C10—Fe1—C4—C3 | 166.78 (17) | C4—Fe1—C10—C9 | −77.2 (2) |
C6—Fe1—C4—C3 | −158.6 (3) | C9—Fe1—C10—C6 | −117.8 (2) |
C9—Fe1—C4—C3 | 124.47 (17) | C7—Fe1—C10—C6 | −37.25 (16) |
C7—Fe1—C4—C3 | 48.1 (3) | C2—Fe1—C10—C6 | 48.7 (3) |
C2—Fe1—C4—C3 | −37.52 (15) | C5—Fe1—C10—C6 | 124.16 (16) |
C5—Fe1—C4—C3 | −119.0 (2) | C3—Fe1—C10—C6 | −164.2 (3) |
C1—Fe1—C4—C3 | −81.60 (16) | C1—Fe1—C10—C6 | 81.49 (18) |
C8—Fe1—C4—C3 | 82.45 (18) | C8—Fe1—C10—C6 | −80.34 (17) |
C3—C4—C5—C1 | 0.2 (2) | C4—Fe1—C10—C6 | 165.03 (15) |
Fe1—C4—C5—C1 | −59.28 (14) | C13'—N1—C11—C1 | 142.5 (5) |
C3—C4—C5—Fe1 | 59.50 (15) | C13—N1—C11—C1 | 71.0 (4) |
C2—C1—C5—C4 | −0.4 (2) | C12—N1—C11—C1 | −65.0 (3) |
C11—C1—C5—C4 | 179.3 (2) | C5—C1—C11—N1 | 84.3 (3) |
Fe1—C1—C5—C4 | 59.38 (15) | C2—C1—C11—N1 | −96.1 (3) |
C2—C1—C5—Fe1 | −59.74 (14) | Fe1—C1—C11—N1 | 174.27 (17) |
C11—C1—C5—Fe1 | 119.9 (2) | C13'—N1—C13—C14 | 48.5 (5) |
C10—Fe1—C5—C4 | 125.01 (18) | C12—N1—C13—C14 | −66.6 (4) |
C6—Fe1—C5—C4 | 166.57 (16) | C11—N1—C13—C14 | 158.4 (3) |
C9—Fe1—C5—C4 | 82.53 (18) | N1—C13—C14—C15 | 154.4 (3) |
C7—Fe1—C5—C4 | −163.3 (3) | N1—C13—C14—C19 | −25.6 (5) |
C2—Fe1—C5—C4 | −81.38 (16) | C19—C14—C15—C16 | 0.0 |
C3—Fe1—C5—C4 | −37.72 (15) | C13—C14—C15—C16 | 179.9 (3) |
C1—Fe1—C5—C4 | −119.9 (2) | C14—C15—C16—C17 | 0.0 |
C8—Fe1—C5—C4 | 50.7 (3) | C15—C16—C17—C18 | 0.0 |
C10—Fe1—C5—C1 | −115.09 (17) | C16—C17—C18—C19 | 0.0 |
C6—Fe1—C5—C1 | −73.53 (18) | C17—C18—C19—C14 | 0.0 |
C9—Fe1—C5—C1 | −157.57 (16) | C15—C14—C19—C18 | 0.0 |
C7—Fe1—C5—C1 | −43.4 (4) | C13—C14—C19—C18 | −179.9 (4) |
C2—Fe1—C5—C1 | 38.51 (14) | C13—N1—C13'—C14' | −52.1 (6) |
C3—Fe1—C5—C1 | 82.18 (15) | C12—N1—C13'—C14' | 52.1 (9) |
C8—Fe1—C5—C1 | 170.6 (2) | C11—N1—C13'—C14' | −158.0 (6) |
C4—Fe1—C5—C1 | 119.9 (2) | N1—C13'—C14'—C15' | 64.6 (10) |
C10—Fe1—C6—C7 | −118.8 (2) | N1—C13'—C14'—C19' | −122.4 (7) |
C9—Fe1—C6—C7 | −80.31 (18) | C19'—C14'—C15'—C16' | 0.0 |
C2—Fe1—C6—C7 | 82.84 (18) | C13'—C14'—C15'—C16' | 172.9 (7) |
C5—Fe1—C6—C7 | 165.88 (15) | C14'—C15'—C16'—C17' | 0.0 |
C3—Fe1—C6—C7 | 50.4 (3) | C15'—C16'—C17'—C18' | 0.0 |
C1—Fe1—C6—C7 | 125.16 (16) | C16'—C17'—C18'—C19' | 0.0 |
C8—Fe1—C6—C7 | −37.04 (16) | C17'—C18'—C19'—C14' | 0.0 |
C4—Fe1—C6—C7 | −163.7 (3) | C15'—C14'—C19'—C18' | 0.0 |
C9—Fe1—C6—C10 | 38.52 (18) | C13'—C14'—C19'—C18' | −173.0 (7) |
C7—Fe1—C6—C10 | 118.8 (2) |