Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032271/cv6430sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032271/cv6430Isup2.hkl |
CCDC reference: 262258
Data collection: SMART (Bruker 1999); cell refinement: SAINT (Bruker 1999); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare,1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek 1995); software used to prepare material for publication: SHELXL97.
[Fe(C5H5)(C28H23N2O2)] | Z = 2 |
Mr = 540.42 | F(000) = 564 |
Triclinic, P1 | Dx = 1.517 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.238 (8) Å | Cell parameters from 3022 reflections |
b = 11.112 (11) Å | θ = 2.7–24.7° |
c = 12.164 (12) Å | µ = 0.68 mm−1 |
α = 93.904 (14)° | T = 163 K |
β = 100.206 (13)° | Plate, orange |
γ = 104.154 (15)° | 0.30 × 0.14 × 0.02 mm |
V = 1183.4 (19) Å3 |
Bruker SMART CCD area-detector diffractometer | 4329 independent reflections |
Radiation source: fine-focus sealed tube | 2629 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
φ and ω scans | θmax = 26.4°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker 1999) | h = −11→8 |
Tmin = 0.860, Tmax = 1.000 | k = −13→13 |
11404 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 0.89 | w = 1/[σ2(Fo2) + (0.0393P)2] where P = (Fo2 + 2Fc2)/3 |
4329 reflections | (Δ/σ)max < 0.001 |
343 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.47 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 | ||
C1 | 0.8659 (4) | 0.4778 (3) | 1.2157 (3) | 0.0208 (8) | |
C2 | 0.8919 (4) | 0.5487 (3) | 1.3147 (3) | 0.0238 (8) | |
H2 | 0.8100 | 0.5644 | 1.3426 | 0.029* | |
C3 | 1.0365 (4) | 0.5981 (3) | 1.3751 (3) | 0.0246 (9) | |
H3 | 1.0508 | 0.6455 | 1.4441 | 0.029* | |
C4 | 1.1583 (4) | 0.5801 (3) | 1.3375 (3) | 0.0212 (8) | |
N2 | 1.3053 (3) | 0.6290 (2) | 1.3963 (2) | 0.0247 (7) | |
C14 | 1.3238 (4) | 0.6723 (3) | 1.5135 (3) | 0.0332 (10) | |
H14A | 1.2528 | 0.6145 | 1.5475 | 0.040* | |
H14B | 1.3026 | 0.7535 | 1.5212 | 0.040* | |
C15 | 1.4837 (4) | 0.6819 (4) | 1.5718 (3) | 0.0408 (10) | |
H15A | 1.4978 | 0.7135 | 1.6503 | 0.049* | |
H15B | 1.5022 | 0.5996 | 1.5684 | 0.049* | |
C16 | 1.5946 (4) | 0.7672 (4) | 1.5176 (3) | 0.0458 (11) | |
H16A | 1.5848 | 0.8518 | 1.5295 | 0.055* | |
H16B | 1.6976 | 0.7668 | 1.5519 | 0.055* | |
C17 | 1.5659 (4) | 0.7263 (4) | 1.3951 (3) | 0.0397 (11) | |
H17A | 1.6328 | 0.7863 | 1.3599 | 0.048* | |
H17B | 1.5881 | 0.6461 | 1.3833 | 0.048* | |
C18 | 1.4050 (4) | 0.7157 (3) | 1.3427 (3) | 0.0291 (9) | |
H18A | 1.3842 | 0.7970 | 1.3504 | 0.035* | |
H18B | 1.3871 | 0.6871 | 1.2631 | 0.035* | |
C5 | 1.2508 (4) | 0.4626 (3) | 1.2007 (3) | 0.0224 (8) | |
H5 | 1.3493 | 0.4900 | 1.2433 | 0.027* | |
C6 | 1.2249 (4) | 0.3864 (3) | 1.1052 (3) | 0.0258 (9) | |
H6 | 1.3052 | 0.3625 | 1.0816 | 0.031* | |
C7 | 1.0796 (4) | 0.3432 (3) | 1.0421 (3) | 0.0258 (9) | |
H7 | 1.0623 | 0.2925 | 0.9746 | 0.031* | |
C8 | 0.9629 (4) | 0.3741 (3) | 1.0776 (2) | 0.0199 (8) | |
C9 | 0.9863 (4) | 0.4530 (3) | 1.1754 (2) | 0.0192 (8) | |
C10 | 1.1360 (4) | 0.5012 (3) | 1.2369 (2) | 0.0204 (8) | |
C11 | 0.7118 (4) | 0.4219 (3) | 1.1567 (3) | 0.0224 (8) | |
O11 | 0.6027 (3) | 0.4381 (2) | 1.18791 (18) | 0.0274 (6) | |
C12 | 0.8093 (4) | 0.3175 (3) | 1.0157 (3) | 0.0231 (8) | |
O12 | 0.7817 (3) | 0.2483 (2) | 0.93089 (19) | 0.0405 (7) | |
N1 | 0.6933 (3) | 0.3424 (2) | 1.0610 (2) | 0.0205 (7) | |
C13 | 0.5418 (4) | 0.2763 (3) | 1.0066 (3) | 0.0202 (8) | |
C131 | 0.4784 (4) | 0.1651 (3) | 1.0383 (3) | 0.0299 (9) | |
H131 | 0.5322 | 0.1328 | 1.0958 | 0.036* | |
C132 | 0.3366 (4) | 0.1007 (3) | 0.9863 (3) | 0.0281 (9) | |
H132 | 0.2931 | 0.0239 | 1.0086 | 0.034* | |
C133 | 0.2558 (4) | 0.1464 (3) | 0.9015 (2) | 0.0199 (8) | |
C134 | 0.3216 (3) | 0.2597 (3) | 0.8724 (2) | 0.0208 (8) | |
H134 | 0.2678 | 0.2937 | 0.8160 | 0.025* | |
C135 | 0.4641 (3) | 0.3237 (3) | 0.9241 (2) | 0.0202 (8) | |
H135 | 0.5085 | 0.4007 | 0.9026 | 0.024* | |
C21 | 0.1037 (4) | 0.0775 (3) | 0.8447 (3) | 0.0217 (8) | |
C22 | 0.0197 (4) | −0.0365 (3) | 0.8705 (3) | 0.0262 (9) | |
H22 | 0.0510 | −0.0803 | 0.9287 | 0.031* | |
C23 | −0.1183 (4) | −0.0728 (3) | 0.7940 (3) | 0.0322 (9) | |
H23 | −0.1958 | −0.1447 | 0.7927 | 0.039* | |
C24 | −0.1205 (4) | 0.0165 (3) | 0.7204 (3) | 0.0305 (9) | |
H24 | −0.1993 | 0.0147 | 0.6604 | 0.037* | |
C25 | 0.0144 (4) | 0.1086 (3) | 0.7512 (3) | 0.0255 (9) | |
H25 | 0.0415 | 0.1798 | 0.7156 | 0.031* | |
Fe1 | 0.05688 (6) | −0.05528 (5) | 0.71497 (4) | 0.02217 (16) | |
C31 | 0.2578 (4) | −0.0667 (3) | 0.6834 (3) | 0.0272 (9) | |
H31 | 0.3523 | −0.0152 | 0.7189 | 0.033* | |
C32 | 0.1829 (4) | −0.1762 (3) | 0.7180 (3) | 0.0279 (9) | |
H32 | 0.2185 | −0.2115 | 0.7811 | 0.033* | |
C33 | 0.0455 (4) | −0.2249 (3) | 0.6430 (3) | 0.0261 (9) | |
H33 | −0.0269 | −0.2985 | 0.6465 | 0.031* | |
C34 | 0.0360 (4) | −0.1439 (3) | 0.5619 (3) | 0.0295 (9) | |
H34 | −0.0446 | −0.1530 | 0.5014 | 0.035* | |
C35 | 0.1674 (4) | −0.0471 (3) | 0.5867 (3) | 0.0309 (9) | |
H35 | 0.1910 | 0.0198 | 0.5452 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.021 (2) | 0.0178 (18) | 0.0224 (18) | 0.0040 (16) | 0.0015 (16) | 0.0023 (14) |
C2 | 0.028 (2) | 0.0218 (18) | 0.0272 (19) | 0.0111 (16) | 0.0133 (17) | 0.0020 (15) |
C3 | 0.024 (2) | 0.0255 (19) | 0.0246 (18) | 0.0091 (17) | 0.0065 (17) | −0.0044 (15) |
C4 | 0.022 (2) | 0.0171 (18) | 0.0244 (18) | 0.0044 (16) | 0.0045 (16) | 0.0031 (14) |
N2 | 0.0226 (17) | 0.0278 (16) | 0.0188 (14) | −0.0009 (13) | 0.0034 (13) | −0.0006 (12) |
C14 | 0.028 (2) | 0.040 (2) | 0.0258 (19) | −0.0023 (18) | 0.0067 (17) | −0.0025 (17) |
C15 | 0.034 (2) | 0.055 (3) | 0.0254 (19) | 0.001 (2) | 0.0022 (18) | −0.0015 (18) |
C16 | 0.030 (2) | 0.062 (3) | 0.032 (2) | −0.005 (2) | 0.0017 (18) | −0.010 (2) |
C17 | 0.028 (2) | 0.048 (2) | 0.034 (2) | −0.0067 (19) | 0.0100 (18) | −0.0049 (18) |
C18 | 0.033 (2) | 0.0258 (19) | 0.0253 (18) | −0.0026 (17) | 0.0114 (17) | 0.0010 (15) |
C5 | 0.017 (2) | 0.0250 (19) | 0.0239 (18) | 0.0028 (16) | 0.0057 (15) | −0.0023 (15) |
C6 | 0.022 (2) | 0.0268 (19) | 0.0289 (19) | 0.0056 (16) | 0.0103 (16) | −0.0014 (15) |
C7 | 0.024 (2) | 0.029 (2) | 0.0224 (18) | 0.0035 (17) | 0.0062 (16) | −0.0031 (15) |
C8 | 0.019 (2) | 0.0210 (18) | 0.0212 (17) | 0.0073 (16) | 0.0053 (15) | 0.0044 (14) |
C9 | 0.022 (2) | 0.0173 (17) | 0.0196 (17) | 0.0057 (15) | 0.0052 (15) | 0.0053 (14) |
C10 | 0.021 (2) | 0.0193 (17) | 0.0216 (17) | 0.0052 (16) | 0.0053 (16) | 0.0050 (14) |
C11 | 0.029 (2) | 0.0187 (18) | 0.0250 (18) | 0.0124 (17) | 0.0106 (17) | 0.0052 (14) |
O11 | 0.0223 (15) | 0.0302 (14) | 0.0325 (14) | 0.0102 (12) | 0.0091 (11) | 0.0006 (11) |
C12 | 0.019 (2) | 0.030 (2) | 0.0224 (18) | 0.0077 (17) | 0.0086 (16) | 0.0047 (16) |
O12 | 0.0276 (16) | 0.0557 (17) | 0.0309 (14) | 0.0057 (13) | 0.0028 (12) | −0.0191 (13) |
N1 | 0.0156 (17) | 0.0240 (15) | 0.0218 (14) | 0.0065 (13) | 0.0019 (12) | 0.0030 (12) |
C13 | 0.015 (2) | 0.0238 (19) | 0.0223 (17) | 0.0072 (15) | 0.0031 (15) | 0.0015 (14) |
C131 | 0.025 (2) | 0.031 (2) | 0.032 (2) | 0.0076 (17) | −0.0048 (17) | 0.0125 (16) |
C132 | 0.026 (2) | 0.0229 (19) | 0.034 (2) | 0.0029 (17) | 0.0042 (17) | 0.0071 (16) |
C133 | 0.018 (2) | 0.0234 (18) | 0.0189 (17) | 0.0084 (16) | 0.0040 (15) | −0.0024 (14) |
C134 | 0.018 (2) | 0.0282 (19) | 0.0166 (16) | 0.0085 (16) | 0.0011 (14) | 0.0030 (14) |
C135 | 0.017 (2) | 0.0245 (18) | 0.0221 (17) | 0.0077 (16) | 0.0072 (15) | 0.0044 (14) |
C21 | 0.021 (2) | 0.0235 (19) | 0.0217 (17) | 0.0078 (16) | 0.0056 (15) | −0.0031 (14) |
C22 | 0.031 (2) | 0.0261 (19) | 0.0200 (17) | 0.0043 (17) | 0.0095 (16) | −0.0060 (15) |
C23 | 0.020 (2) | 0.037 (2) | 0.034 (2) | −0.0021 (17) | 0.0090 (17) | −0.0069 (18) |
C24 | 0.021 (2) | 0.035 (2) | 0.029 (2) | 0.0064 (17) | −0.0049 (16) | −0.0131 (17) |
C25 | 0.025 (2) | 0.0254 (19) | 0.0247 (18) | 0.0089 (17) | −0.0002 (16) | −0.0038 (15) |
Fe1 | 0.0253 (3) | 0.0217 (3) | 0.0183 (2) | 0.0056 (2) | 0.0036 (2) | −0.00126 (19) |
C31 | 0.021 (2) | 0.032 (2) | 0.030 (2) | 0.0087 (17) | 0.0090 (17) | −0.0026 (16) |
C32 | 0.033 (2) | 0.030 (2) | 0.0231 (18) | 0.0142 (18) | 0.0030 (17) | 0.0039 (15) |
C33 | 0.035 (2) | 0.0217 (19) | 0.0235 (18) | 0.0131 (17) | 0.0033 (16) | 0.0000 (15) |
C34 | 0.039 (2) | 0.033 (2) | 0.0180 (17) | 0.0175 (19) | −0.0009 (16) | −0.0057 (15) |
C35 | 0.042 (3) | 0.031 (2) | 0.0260 (19) | 0.0141 (19) | 0.0156 (18) | 0.0078 (16) |
C1—C2 | 1.344 (4) | C13—C135 | 1.342 (4) |
C1—C9 | 1.370 (5) | C13—C131 | 1.345 (4) |
C1—C11 | 1.439 (5) | C131—C132 | 1.346 (4) |
C2—C3 | 1.365 (4) | C131—H131 | 0.9300 |
C2—H2 | 0.9300 | C132—C133 | 1.366 (4) |
C3—C4 | 1.341 (4) | C132—H132 | 0.9300 |
C3—H3 | 0.9300 | C133—C134 | 1.357 (4) |
C4—N2 | 1.376 (4) | C133—C21 | 1.448 (4) |
C4—C10 | 1.409 (4) | C134—C135 | 1.350 (4) |
N2—C18 | 1.437 (4) | C134—H134 | 0.9300 |
N2—C14 | 1.441 (4) | C135—H135 | 0.9300 |
C14—C15 | 1.496 (5) | C21—C25 | 1.397 (4) |
C14—H14A | 0.9700 | C21—C22 | 1.402 (4) |
C14—H14B | 0.9700 | C21—Fe1 | 1.996 (3) |
C15—C16 | 1.494 (5) | C22—C23 | 1.389 (4) |
C15—H15A | 0.9700 | C22—Fe1 | 1.987 (4) |
C15—H15B | 0.9700 | C22—H22 | 0.9300 |
C16—C17 | 1.485 (5) | C23—C24 | 1.383 (5) |
C16—H16A | 0.9700 | C23—Fe1 | 2.001 (4) |
C16—H16B | 0.9700 | C23—H23 | 0.9300 |
C17—C18 | 1.482 (5) | C24—C25 | 1.378 (4) |
C17—H17A | 0.9700 | C24—Fe1 | 1.999 (4) |
C17—H17B | 0.9700 | C24—H24 | 0.9300 |
C18—H18A | 0.9700 | C25—Fe1 | 1.991 (4) |
C18—H18B | 0.9700 | C25—H25 | 0.9300 |
C5—C6 | 1.339 (4) | Fe1—C32 | 1.980 (4) |
C5—C10 | 1.365 (4) | Fe1—C31 | 1.992 (4) |
C5—H5 | 0.9300 | Fe1—C33 | 1.994 (4) |
C6—C7 | 1.376 (4) | Fe1—C34 | 2.001 (4) |
C6—H6 | 0.9300 | Fe1—C35 | 2.006 (4) |
C7—C8 | 1.338 (4) | C31—C32 | 1.378 (4) |
C7—H7 | 0.9300 | C31—C35 | 1.380 (4) |
C8—C9 | 1.380 (4) | C31—H31 | 0.9300 |
C8—C12 | 1.447 (4) | C32—C33 | 1.386 (4) |
C9—C10 | 1.406 (4) | C32—H32 | 0.9300 |
C11—O11 | 1.187 (4) | C33—C34 | 1.386 (4) |
C11—N1 | 1.372 (4) | C33—H33 | 0.9300 |
C12—O12 | 1.193 (4) | C34—C35 | 1.382 (5) |
C12—N1 | 1.364 (4) | C34—H34 | 0.9300 |
N1—C13 | 1.428 (4) | C35—H35 | 0.9300 |
C2—C1—C9 | 119.5 (3) | C21—C22—Fe1 | 69.72 (18) |
C2—C1—C11 | 119.8 (3) | C23—C22—H22 | 125.9 |
C9—C1—C11 | 120.6 (3) | C21—C22—H22 | 125.9 |
C1—C2—C3 | 121.1 (3) | Fe1—C22—H22 | 125.8 |
C1—C2—H2 | 119.4 | C24—C23—C22 | 108.2 (3) |
C3—C2—H2 | 119.4 | C24—C23—Fe1 | 69.7 (2) |
C4—C3—C2 | 121.6 (3) | C22—C23—Fe1 | 69.1 (2) |
C4—C3—H3 | 119.2 | C24—C23—H23 | 125.9 |
C2—C3—H3 | 119.2 | C22—C23—H23 | 125.9 |
C3—C4—N2 | 123.0 (3) | Fe1—C23—H23 | 126.9 |
C3—C4—C10 | 119.1 (3) | C25—C24—C23 | 108.1 (3) |
N2—C4—C10 | 117.8 (3) | C25—C24—Fe1 | 69.5 (2) |
C4—N2—C18 | 116.5 (3) | C23—C24—Fe1 | 69.9 (2) |
C4—N2—C14 | 116.7 (3) | C25—C24—H24 | 125.9 |
C18—N2—C14 | 111.0 (3) | C23—C24—H24 | 125.9 |
N2—C14—C15 | 109.2 (3) | Fe1—C24—H24 | 126.3 |
N2—C14—H14A | 109.8 | C24—C25—C21 | 108.9 (3) |
C15—C14—H14A | 109.8 | C24—C25—Fe1 | 70.1 (2) |
N2—C14—H14B | 109.8 | C21—C25—Fe1 | 69.65 (19) |
C15—C14—H14B | 109.8 | C24—C25—H25 | 125.5 |
H14A—C14—H14B | 108.3 | C21—C25—H25 | 125.5 |
C16—C15—C14 | 110.4 (3) | Fe1—C25—H25 | 126.3 |
C16—C15—H15A | 109.6 | C32—Fe1—C22 | 104.70 (14) |
C14—C15—H15A | 109.6 | C32—Fe1—C25 | 155.51 (13) |
C16—C15—H15B | 109.6 | C22—Fe1—C25 | 68.67 (14) |
C14—C15—H15B | 109.6 | C32—Fe1—C31 | 40.59 (13) |
H15A—C15—H15B | 108.1 | C22—Fe1—C31 | 122.36 (14) |
C17—C16—C15 | 110.3 (3) | C25—Fe1—C31 | 121.76 (14) |
C17—C16—H16A | 109.6 | C32—Fe1—C33 | 40.83 (13) |
C15—C16—H16A | 109.6 | C22—Fe1—C33 | 119.13 (14) |
C17—C16—H16B | 109.6 | C25—Fe1—C33 | 163.07 (12) |
C15—C16—H16B | 109.6 | C31—Fe1—C33 | 68.48 (14) |
H16A—C16—H16B | 108.1 | C32—Fe1—C21 | 118.53 (14) |
C18—C17—C16 | 110.5 (3) | C22—Fe1—C21 | 41.21 (13) |
C18—C17—H17A | 109.5 | C25—Fe1—C21 | 41.03 (12) |
C16—C17—H17A | 109.5 | C31—Fe1—C21 | 105.82 (14) |
C18—C17—H17B | 109.5 | C33—Fe1—C21 | 154.23 (13) |
C16—C17—H17B | 109.5 | C32—Fe1—C24 | 160.97 (13) |
H17A—C17—H17B | 108.1 | C22—Fe1—C24 | 68.54 (14) |
N2—C18—C17 | 109.8 (3) | C25—Fe1—C24 | 40.42 (12) |
N2—C18—H18A | 109.7 | C31—Fe1—C24 | 158.00 (14) |
C17—C18—H18A | 109.7 | C33—Fe1—C24 | 125.60 (14) |
N2—C18—H18B | 109.7 | C21—Fe1—C24 | 68.85 (14) |
C17—C18—H18B | 109.7 | C32—Fe1—C34 | 68.31 (14) |
H18A—C18—H18B | 108.2 | C22—Fe1—C34 | 155.87 (13) |
C6—C5—C10 | 121.5 (3) | C25—Fe1—C34 | 127.05 (14) |
C6—C5—H5 | 119.2 | C31—Fe1—C34 | 68.20 (14) |
C10—C5—H5 | 119.2 | C33—Fe1—C34 | 40.60 (13) |
C5—C6—C7 | 120.0 (3) | C21—Fe1—C34 | 162.61 (13) |
C5—C6—H6 | 120.0 | C24—Fe1—C34 | 110.20 (14) |
C7—C6—H6 | 120.0 | C32—Fe1—C23 | 123.09 (15) |
C8—C7—C6 | 120.2 (3) | C22—Fe1—C23 | 40.76 (13) |
C8—C7—H7 | 119.9 | C25—Fe1—C23 | 68.09 (15) |
C6—C7—H7 | 119.9 | C31—Fe1—C23 | 159.45 (14) |
C7—C8—C9 | 121.0 (3) | C33—Fe1—C23 | 107.17 (15) |
C7—C8—C12 | 119.1 (3) | C21—Fe1—C23 | 68.90 (14) |
C9—C8—C12 | 119.8 (3) | C24—Fe1—C23 | 40.44 (14) |
C1—C9—C8 | 120.9 (3) | C34—Fe1—C23 | 122.43 (15) |
C1—C9—C10 | 120.4 (3) | C32—Fe1—C35 | 67.95 (14) |
C8—C9—C10 | 118.5 (3) | C22—Fe1—C35 | 160.32 (13) |
C5—C10—C9 | 118.6 (3) | C25—Fe1—C35 | 110.01 (14) |
C5—C10—C4 | 123.2 (3) | C31—Fe1—C35 | 40.37 (13) |
C9—C10—C4 | 118.0 (3) | C33—Fe1—C35 | 68.05 (14) |
O11—C11—N1 | 119.4 (3) | C21—Fe1—C35 | 124.77 (14) |
O11—C11—C1 | 124.0 (3) | C24—Fe1—C35 | 124.08 (15) |
N1—C11—C1 | 116.6 (3) | C34—Fe1—C35 | 40.33 (13) |
O12—C12—N1 | 120.0 (3) | C23—Fe1—C35 | 158.47 (13) |
O12—C12—C8 | 122.9 (3) | C32—C31—C35 | 107.8 (3) |
N1—C12—C8 | 117.0 (3) | C32—C31—Fe1 | 69.2 (2) |
C12—N1—C11 | 124.9 (3) | C35—C31—Fe1 | 70.4 (2) |
C12—N1—C13 | 117.0 (3) | C32—C31—H31 | 126.1 |
C11—N1—C13 | 118.0 (3) | C35—C31—H31 | 126.1 |
C135—C13—C131 | 120.3 (3) | Fe1—C31—H31 | 125.9 |
C135—C13—N1 | 120.5 (3) | C31—C32—C33 | 108.5 (3) |
C131—C13—N1 | 119.2 (3) | C31—C32—Fe1 | 70.2 (2) |
C13—C131—C132 | 119.8 (3) | C33—C32—Fe1 | 70.1 (2) |
C13—C131—H131 | 120.1 | C31—C32—H32 | 125.8 |
C132—C131—H131 | 120.1 | C33—C32—H32 | 125.8 |
C131—C132—C133 | 121.0 (3) | Fe1—C32—H32 | 125.5 |
C131—C132—H132 | 119.5 | C32—C33—C34 | 107.4 (3) |
C133—C132—H132 | 119.5 | C32—C33—Fe1 | 69.03 (19) |
C134—C133—C132 | 118.0 (3) | C34—C33—Fe1 | 70.0 (2) |
C134—C133—C21 | 120.6 (3) | C32—C33—H33 | 126.3 |
C132—C133—C21 | 121.4 (3) | C34—C33—H33 | 126.3 |
C135—C134—C133 | 120.8 (3) | Fe1—C33—H33 | 126.3 |
C135—C134—H134 | 119.6 | C35—C34—C33 | 108.0 (3) |
C133—C134—H134 | 119.6 | C35—C34—Fe1 | 70.04 (19) |
C13—C135—C134 | 120.0 (3) | C33—C34—Fe1 | 69.4 (2) |
C13—C135—H135 | 120.0 | C35—C34—H34 | 126.0 |
C134—C135—H135 | 120.0 | C33—C34—H34 | 126.0 |
C25—C21—C22 | 106.6 (3) | Fe1—C34—H34 | 126.1 |
C25—C21—C133 | 127.0 (3) | C31—C35—C34 | 108.3 (3) |
C22—C21—C133 | 126.3 (3) | C31—C35—Fe1 | 69.3 (2) |
C25—C21—Fe1 | 69.32 (19) | C34—C35—Fe1 | 69.6 (2) |
C22—C21—Fe1 | 69.08 (18) | C31—C35—H35 | 125.8 |
C133—C21—Fe1 | 124.6 (2) | C34—C35—H35 | 125.8 |
C23—C22—C21 | 108.2 (3) | Fe1—C35—H35 | 126.9 |
C23—C22—Fe1 | 70.2 (2) | ||
C9—C1—C2—C3 | 1.1 (5) | C25—C21—Fe1—C24 | −37.0 (2) |
C11—C1—C2—C3 | 176.9 (3) | C22—C21—Fe1—C24 | 81.2 (2) |
C1—C2—C3—C4 | 1.3 (5) | C133—C21—Fe1—C24 | −158.4 (3) |
C2—C3—C4—N2 | 179.8 (3) | C25—C21—Fe1—C34 | 53.2 (5) |
C2—C3—C4—C10 | −4.4 (5) | C22—C21—Fe1—C34 | 171.4 (4) |
C3—C4—N2—C18 | −118.0 (4) | C133—C21—Fe1—C34 | −68.2 (6) |
C10—C4—N2—C18 | 66.1 (4) | C25—C21—Fe1—C23 | −80.5 (2) |
C3—C4—N2—C14 | 16.3 (5) | C22—C21—Fe1—C23 | 37.7 (2) |
C10—C4—N2—C14 | −159.5 (3) | C133—C21—Fe1—C23 | 158.1 (3) |
C4—N2—C14—C15 | 161.4 (3) | C25—C21—Fe1—C35 | 80.6 (2) |
C18—N2—C14—C15 | −61.9 (4) | C22—C21—Fe1—C35 | −161.3 (2) |
N2—C14—C15—C16 | 57.5 (4) | C133—C21—Fe1—C35 | −40.8 (3) |
C14—C15—C16—C17 | −54.3 (5) | C25—C24—Fe1—C32 | 154.2 (4) |
C15—C16—C17—C18 | 54.4 (5) | C23—C24—Fe1—C32 | 34.8 (5) |
C4—N2—C18—C17 | −160.9 (3) | C25—C24—Fe1—C22 | 81.9 (2) |
C14—N2—C18—C17 | 62.3 (4) | C23—C24—Fe1—C22 | −37.50 (19) |
C16—C17—C18—N2 | −58.0 (4) | C23—C24—Fe1—C25 | −119.4 (3) |
C10—C5—C6—C7 | −1.1 (5) | C25—C24—Fe1—C31 | −42.3 (4) |
C5—C6—C7—C8 | −2.1 (5) | C23—C24—Fe1—C31 | −161.7 (3) |
C6—C7—C8—C9 | 2.4 (5) | C25—C24—Fe1—C33 | −166.91 (19) |
C6—C7—C8—C12 | −173.8 (3) | C23—C24—Fe1—C33 | 73.7 (2) |
C2—C1—C9—C8 | 175.9 (3) | C25—C24—Fe1—C21 | 37.50 (19) |
C11—C1—C9—C8 | 0.1 (5) | C23—C24—Fe1—C21 | −81.9 (2) |
C2—C1—C9—C10 | −0.1 (5) | C25—C24—Fe1—C34 | −123.9 (2) |
C11—C1—C9—C10 | −175.9 (3) | C23—C24—Fe1—C34 | 116.7 (2) |
C7—C8—C9—C1 | −175.5 (3) | C25—C24—Fe1—C23 | 119.4 (3) |
C12—C8—C9—C1 | 0.6 (5) | C25—C24—Fe1—C35 | −81.0 (2) |
C7—C8—C9—C10 | 0.5 (5) | C23—C24—Fe1—C35 | 159.66 (19) |
C12—C8—C9—C10 | 176.6 (3) | C24—C23—Fe1—C32 | −167.17 (19) |
C6—C5—C10—C9 | 4.0 (5) | C22—C23—Fe1—C32 | 73.0 (2) |
C6—C5—C10—C4 | 179.2 (3) | C24—C23—Fe1—C22 | 119.8 (3) |
C1—C9—C10—C5 | 172.4 (3) | C24—C23—Fe1—C25 | 37.51 (19) |
C8—C9—C10—C5 | −3.6 (4) | C22—C23—Fe1—C25 | −82.3 (2) |
C1—C9—C10—C4 | −3.0 (4) | C24—C23—Fe1—C31 | 160.4 (3) |
C8—C9—C10—C4 | −179.1 (3) | C22—C23—Fe1—C31 | 40.6 (5) |
C3—C4—C10—C5 | −170.0 (3) | C24—C23—Fe1—C33 | −125.2 (2) |
N2—C4—C10—C5 | 6.0 (5) | C22—C23—Fe1—C33 | 115.0 (2) |
C3—C4—C10—C9 | 5.2 (4) | C24—C23—Fe1—C21 | 81.8 (2) |
N2—C4—C10—C9 | −178.8 (3) | C22—C23—Fe1—C21 | −38.1 (2) |
C2—C1—C11—O11 | 3.1 (5) | C22—C23—Fe1—C24 | −119.8 (3) |
C9—C1—C11—O11 | 178.9 (3) | C24—C23—Fe1—C34 | −83.4 (2) |
C2—C1—C11—N1 | −174.7 (3) | C22—C23—Fe1—C34 | 156.8 (2) |
C9—C1—C11—N1 | 1.1 (4) | C24—C23—Fe1—C35 | −51.7 (5) |
C7—C8—C12—O12 | −3.6 (5) | C22—C23—Fe1—C35 | −171.5 (3) |
C9—C8—C12—O12 | −179.7 (3) | C22—Fe1—C31—C32 | 73.9 (2) |
C7—C8—C12—N1 | 173.8 (3) | C25—Fe1—C31—C32 | 157.30 (19) |
C9—C8—C12—N1 | −2.4 (4) | C33—Fe1—C31—C32 | −37.83 (19) |
O12—C12—N1—C11 | −178.8 (3) | C21—Fe1—C31—C32 | 115.6 (2) |
C8—C12—N1—C11 | 3.8 (4) | C24—Fe1—C31—C32 | −171.8 (3) |
O12—C12—N1—C13 | 3.9 (4) | C34—Fe1—C31—C32 | −81.7 (2) |
C8—C12—N1—C13 | −173.5 (3) | C23—Fe1—C31—C32 | 43.7 (5) |
O11—C11—N1—C12 | 178.9 (3) | C35—Fe1—C31—C32 | −118.8 (3) |
C1—C11—N1—C12 | −3.1 (4) | C32—Fe1—C31—C35 | 118.8 (3) |
O11—C11—N1—C13 | −3.8 (4) | C22—Fe1—C31—C35 | −167.3 (2) |
C1—C11—N1—C13 | 174.1 (3) | C25—Fe1—C31—C35 | −83.9 (2) |
C12—N1—C13—C135 | −90.2 (4) | C33—Fe1—C31—C35 | 81.0 (2) |
C11—N1—C13—C135 | 92.3 (4) | C21—Fe1—C31—C35 | −125.6 (2) |
C12—N1—C13—C131 | 89.1 (4) | C24—Fe1—C31—C35 | −53.0 (4) |
C11—N1—C13—C131 | −88.4 (4) | C34—Fe1—C31—C35 | 37.2 (2) |
C135—C13—C131—C132 | 0.5 (5) | C23—Fe1—C31—C35 | 162.5 (4) |
N1—C13—C131—C132 | −178.8 (3) | C35—C31—C32—C33 | −0.1 (4) |
C13—C131—C132—C133 | 0.1 (6) | Fe1—C31—C32—C33 | 59.9 (2) |
C131—C132—C133—C134 | −1.1 (5) | C35—C31—C32—Fe1 | −60.1 (3) |
C131—C132—C133—C21 | 179.6 (3) | C22—Fe1—C32—C31 | −123.0 (2) |
C132—C133—C134—C135 | 1.5 (5) | C25—Fe1—C32—C31 | −52.3 (4) |
C21—C133—C134—C135 | −179.2 (3) | C33—Fe1—C32—C31 | 119.2 (3) |
C131—C13—C135—C134 | 0.0 (5) | C21—Fe1—C32—C31 | −80.9 (2) |
N1—C13—C135—C134 | 179.2 (3) | C24—Fe1—C32—C31 | 170.6 (4) |
C133—C134—C135—C13 | −1.0 (5) | C34—Fe1—C32—C31 | 81.4 (2) |
C134—C133—C21—C25 | 6.4 (5) | C23—Fe1—C32—C31 | −163.19 (19) |
C132—C133—C21—C25 | −174.3 (3) | C35—Fe1—C32—C31 | 37.76 (19) |
C134—C133—C21—C22 | −176.3 (3) | C22—Fe1—C32—C33 | 117.8 (2) |
C132—C133—C21—C22 | 3.0 (5) | C25—Fe1—C32—C33 | −171.6 (3) |
C134—C133—C21—Fe1 | 95.5 (4) | C31—Fe1—C32—C33 | −119.2 (3) |
C132—C133—C21—Fe1 | −85.2 (4) | C21—Fe1—C32—C33 | 159.82 (19) |
C25—C21—C22—C23 | −0.4 (4) | C24—Fe1—C32—C33 | 51.3 (5) |
C133—C21—C22—C23 | −178.1 (3) | C34—Fe1—C32—C33 | −37.9 (2) |
Fe1—C21—C22—C23 | −59.8 (2) | C23—Fe1—C32—C33 | 77.6 (2) |
C25—C21—C22—Fe1 | 59.4 (2) | C35—Fe1—C32—C33 | −81.5 (2) |
C133—C21—C22—Fe1 | −118.3 (3) | C31—C32—C33—C34 | −0.3 (4) |
C21—C22—C23—C24 | 0.6 (4) | Fe1—C32—C33—C34 | 59.7 (2) |
Fe1—C22—C23—C24 | −58.9 (3) | C31—C32—C33—Fe1 | −60.0 (2) |
C21—C22—C23—Fe1 | 59.5 (2) | C22—Fe1—C33—C32 | −78.4 (2) |
C22—C23—C24—C25 | −0.6 (4) | C25—Fe1—C33—C32 | 168.0 (4) |
Fe1—C23—C24—C25 | −59.2 (3) | C31—Fe1—C33—C32 | 37.6 (2) |
C22—C23—C24—Fe1 | 58.5 (3) | C21—Fe1—C33—C32 | −44.2 (4) |
C23—C24—C25—C21 | 0.4 (4) | C24—Fe1—C33—C32 | −161.8 (2) |
Fe1—C24—C25—C21 | −59.0 (2) | C34—Fe1—C33—C32 | 118.8 (3) |
C23—C24—C25—Fe1 | 59.4 (3) | C23—Fe1—C33—C32 | −121.1 (2) |
C22—C21—C25—C24 | 0.0 (4) | C35—Fe1—C33—C32 | 81.2 (2) |
C133—C21—C25—C24 | 177.7 (3) | C32—Fe1—C33—C34 | −118.8 (3) |
Fe1—C21—C25—C24 | 59.3 (2) | C22—Fe1—C33—C34 | 162.8 (2) |
C22—C21—C25—Fe1 | −59.3 (2) | C25—Fe1—C33—C34 | 49.2 (6) |
C133—C21—C25—Fe1 | 118.4 (4) | C31—Fe1—C33—C34 | −81.2 (2) |
C23—C22—Fe1—C32 | −124.1 (2) | C21—Fe1—C33—C34 | −163.0 (3) |
C21—C22—Fe1—C32 | 116.7 (2) | C24—Fe1—C33—C34 | 79.5 (3) |
C23—C22—Fe1—C25 | 80.8 (2) | C23—Fe1—C33—C34 | 120.1 (2) |
C21—C22—Fe1—C25 | −38.4 (2) | C35—Fe1—C33—C34 | −37.6 (2) |
C23—C22—Fe1—C31 | −164.3 (2) | C32—C33—C34—C35 | 0.6 (4) |
C21—C22—Fe1—C31 | 76.5 (2) | Fe1—C33—C34—C35 | 59.7 (2) |
C23—C22—Fe1—C33 | −82.6 (2) | C32—C33—C34—Fe1 | −59.1 (2) |
C21—C22—Fe1—C33 | 158.2 (2) | C32—Fe1—C34—C35 | −81.0 (2) |
C23—C22—Fe1—C21 | 119.2 (3) | C22—Fe1—C34—C35 | −158.3 (3) |
C23—C22—Fe1—C24 | 37.2 (2) | C25—Fe1—C34—C35 | 76.9 (3) |
C21—C22—Fe1—C24 | −82.0 (2) | C31—Fe1—C34—C35 | −37.2 (2) |
C23—C22—Fe1—C34 | −54.5 (4) | C33—Fe1—C34—C35 | −119.1 (3) |
C21—C22—Fe1—C34 | −173.7 (3) | C21—Fe1—C34—C35 | 35.7 (6) |
C21—C22—Fe1—C23 | −119.2 (3) | C24—Fe1—C34—C35 | 119.3 (2) |
C23—C22—Fe1—C35 | 170.7 (4) | C23—Fe1—C34—C35 | 162.6 (2) |
C21—C22—Fe1—C35 | 51.5 (5) | C32—Fe1—C34—C33 | 38.1 (2) |
C24—C25—Fe1—C32 | −160.0 (3) | C22—Fe1—C34—C33 | −39.2 (4) |
C21—C25—Fe1—C32 | −39.9 (4) | C25—Fe1—C34—C33 | −164.0 (2) |
C24—C25—Fe1—C22 | −81.5 (2) | C31—Fe1—C34—C33 | 81.9 (2) |
C21—C25—Fe1—C22 | 38.6 (2) | C21—Fe1—C34—C33 | 154.8 (4) |
C24—C25—Fe1—C31 | 162.7 (2) | C24—Fe1—C34—C33 | −121.6 (2) |
C21—C25—Fe1—C31 | −77.1 (2) | C23—Fe1—C34—C33 | −78.2 (3) |
C24—C25—Fe1—C33 | 39.2 (6) | C35—Fe1—C34—C33 | 119.1 (3) |
C21—C25—Fe1—C33 | 159.4 (4) | C32—C31—C35—C34 | 0.5 (4) |
C24—C25—Fe1—C21 | −120.1 (3) | Fe1—C31—C35—C34 | −58.8 (3) |
C21—C25—Fe1—C24 | 120.1 (3) | C32—C31—C35—Fe1 | 59.3 (2) |
C24—C25—Fe1—C34 | 77.3 (3) | C33—C34—C35—C31 | −0.7 (4) |
C21—C25—Fe1—C34 | −162.5 (2) | Fe1—C34—C35—C31 | 58.6 (3) |
C24—C25—Fe1—C23 | −37.5 (2) | C33—C34—C35—Fe1 | −59.3 (3) |
C21—C25—Fe1—C23 | 82.6 (2) | C32—Fe1—C35—C31 | −37.95 (19) |
C24—C25—Fe1—C35 | 119.5 (2) | C22—Fe1—C35—C31 | 33.4 (5) |
C21—C25—Fe1—C35 | −120.4 (2) | C25—Fe1—C35—C31 | 115.9 (2) |
C25—C21—Fe1—C32 | 162.40 (19) | C33—Fe1—C35—C31 | −82.1 (2) |
C22—C21—Fe1—C32 | −79.5 (2) | C21—Fe1—C35—C31 | 72.3 (2) |
C133—C21—Fe1—C32 | 41.0 (3) | C24—Fe1—C35—C31 | 158.83 (19) |
C25—C21—Fe1—C22 | −118.1 (3) | C34—Fe1—C35—C31 | −120.0 (3) |
C133—C21—Fe1—C22 | 120.5 (4) | C23—Fe1—C35—C31 | −163.3 (4) |
C22—C21—Fe1—C25 | 118.1 (3) | C32—Fe1—C35—C34 | 82.0 (2) |
C133—C21—Fe1—C25 | −121.4 (4) | C22—Fe1—C35—C34 | 153.4 (4) |
C25—C21—Fe1—C31 | 120.5 (2) | C25—Fe1—C35—C34 | −124.2 (2) |
C22—C21—Fe1—C31 | −121.4 (2) | C31—Fe1—C35—C34 | 120.0 (3) |
C133—C21—Fe1—C31 | −0.9 (3) | C33—Fe1—C35—C34 | 37.8 (2) |
C25—C21—Fe1—C33 | −166.3 (3) | C21—Fe1—C35—C34 | −167.7 (2) |
C22—C21—Fe1—C33 | −48.2 (4) | C24—Fe1—C35—C34 | −81.2 (3) |
C133—C21—Fe1—C33 | 72.2 (4) | C23—Fe1—C35—C34 | −43.3 (5) |