Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106027314/gd3037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106027314/gd3037Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106027314/gd3037IIsup3.hkl |
CCDC references: 621257; 621258
For the synthesis of each of compounds (I) and (II), a solution of ferrocenoylacetone (5 mmol) and the appropriate aminophenol (5 mmol) in anhydrous ethanol (20 ml) was stirred and refluxed for 20 h. After removal of the solvent, the resulting solids were purified by chromatography on silica gel, with ethyl acetate and dichloromethane [(I): 1:20 v/v; (II): 1:8 v/v] as eluant. Compounds (I) and (II) were recrystallized from dichloromethane/petroleum ether solution to give red crystals of (I) and (II) suitable for single-crystal X-ray diffraction [(I): m.p. 480–481 K, yield 63%; (II): m.p. 490–492 K, yield 67%). For (I), IR (KBr): 3424 (m, OH), 3076 (m, NH), 1588 (vs, O═C), 1523 (m, C═C) cm-1; 1H NMR (600 MHz, CDCl3, p.p.m.): δ 12.502 (1H, s, NH), 9.019 (1H, s, OH), 7.139–7.165, 6.727–6.741, 6.673, 6.590–6.602 (4H, t, d, s, d, C6H4), 5.409 (1H, s, CH), 4.762, 4.397 (2H, 2H, 2m, C5H4), 4.141 (5H, s, C5H5), 2.020 (3H, s, CH3). For (II), IR (KBr): 3426 (m, OH), 3090 (m, NH), 1585 (vs, O═C), 1510 (vs, C═C) cm-1; 1H NMR (600 MHz, CDCl3, p.p.m.): δ 12.367 (1H, s, NH), 6.906–6.919, 6.775–6.788 (2H, d, 2H, d, C6H4), 5.373 (1H, s, CH), 4.720, 4.345 (2H, 2H, 2m, C5H4), 4.142 (6H, s, C5H5, OH), 1.955 (3H, s, CH3).
All H atoms in (I) and (II) were placed at geometrically idealized positions and subsequently treated as riding atoms, with C—H = 0.93 (aromatic and olefinic) and 0.96 Å (CH3), N—H = 0.86 Å and O—H = 0.82 Å at 293 K for (I), and C—H = 0.95 (aromatic and olefinic) and 0.98 Å (CH3), N—H = 0.88 Å and O—H = 0.84 Å at 173 K for (II). Uiso(H) values were set at 1.2Ueq(C,N) or 1.5Ueq(Cmethyl,O).
Data collection: CAD-4 Software (Enraf–Nonius, 1989) for (I); CrystalClear (Rigaku, 2001) for (II). Cell refinement: CAD-4 Software for (I); CrystalClear for (II). Data reduction: XCAD4 (Harms & Wocadlo,1995) for (I); CrystalStructure (Rigaku, 2001) for (II). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
[Fe(C5H5)(C15H14NO2)] | Z = 4 |
Mr = 361.21 | F(000) = 752 |
TriclinicP1 | Dx = 1.430 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.768 (2) Å | Cell parameters from 25 reflections |
b = 10.804 (2) Å | θ = 9–12° |
c = 16.244 (3) Å | µ = 0.91 mm−1 |
α = 91.39 (3)° | T = 293 K |
β = 97.05 (3)° | Block, red |
γ = 99.22 (3)° | 0.30 × 0.20 × 0.20 mm |
V = 1677.7 (6) Å3 |
Enraf–Nonius CAD-4 diffractometer | 3837 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 26.0°, θmin = 1.3° |
ω–2θ scan | h = 0→12 |
Absorption correction: psi-scan ψ scan (North et al., 1968) | k = −13→13 |
Tmin = 0.772, Tmax = 0.839 | l = −19→19 |
6988 measured reflections | 3 standard reflections every 200 reflections |
6576 independent reflections | intensity decay: none |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0365P)2 + 0.8184P] where P = (Fo2 + 2Fc2)/3 |
6576 reflections | (Δ/σ)max < 0.001 |
437 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
[Fe(C5H5)(C15H14NO2)] | γ = 99.22 (3)° |
Mr = 361.21 | V = 1677.7 (6) Å3 |
TriclinicP1 | Z = 4 |
a = 9.768 (2) Å | Mo Kα radiation |
b = 10.804 (2) Å | µ = 0.91 mm−1 |
c = 16.244 (3) Å | T = 293 K |
α = 91.39 (3)° | 0.30 × 0.20 × 0.20 mm |
β = 97.05 (3)° |
Enraf–Nonius CAD-4 diffractometer | 3837 reflections with I > 2σ(I) |
Absorption correction: psi-scan ψ scan (North et al., 1968) | Rint = 0.033 |
Tmin = 0.772, Tmax = 0.839 | 3 standard reflections every 200 reflections |
6988 measured reflections | intensity decay: none |
6576 independent reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.50 e Å−3 |
6576 reflections | Δρmin = −0.34 e Å−3 |
437 parameters |
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 | 0.31324 (6) | 0.65967 (6) | 0.41560 (4) | 0.03364 (18) | |
Fe2 | 0.84407 (7) | 0.17112 (7) | 1.09926 (4) | 0.0446 (2) | |
O1 | 0.1030 (3) | 0.7065 (3) | 0.58336 (18) | 0.0420 (8) | |
O4 | 0.3500 (4) | 0.6937 (3) | 0.6720 (2) | 0.0573 (10) | |
H4O | 0.2742 | 0.6903 | 0.6433 | 0.086* | |
O2 | −0.0530 (4) | 1.1801 (3) | 0.8147 (2) | 0.0560 (10) | |
H2O | −0.0999 | 1.2127 | 0.8448 | 0.084* | |
N1 | −0.0783 (4) | 0.8562 (3) | 0.6084 (2) | 0.0398 (10) | |
H1N | −0.0121 | 0.8177 | 0.6285 | 0.048* | |
C11 | 0.0597 (4) | 0.7100 (4) | 0.5069 (3) | 0.0319 (10) | |
C35 | 0.4825 (5) | 0.4693 (4) | 0.8084 (3) | 0.0395 (12) | |
N2 | 0.6085 (4) | 0.4540 (4) | 0.8583 (2) | 0.0461 (11) | |
H2N | 0.6531 | 0.3982 | 0.8408 | 0.055* | |
C39 | 0.3505 (5) | 0.5882 (4) | 0.7148 (3) | 0.0398 (12) | |
C40 | 0.4750 (5) | 0.5750 (4) | 0.7619 (3) | 0.0408 (12) | |
H40 | 0.5534 | 0.6366 | 0.7625 | 0.049* | |
C12 | −0.0413 (4) | 0.7818 (4) | 0.4768 (3) | 0.0332 (10) | |
H12 | −0.0649 | 0.7819 | 0.4196 | 0.040* | |
O3 | 0.7953 (4) | 0.3060 (3) | 0.8977 (2) | 0.0557 (10) | |
C31 | 0.8237 (5) | 0.3661 (4) | 0.9665 (3) | 0.0407 (11) | |
C32 | 0.7676 (5) | 0.4761 (4) | 0.9823 (3) | 0.0391 (11) | |
H32 | 0.8024 | 0.5231 | 1.0313 | 0.047* | |
C10 | 0.1155 (4) | 0.6320 (4) | 0.4461 (3) | 0.0336 (10) | |
C5 | 0.4936 (5) | 0.6904 (5) | 0.4948 (3) | 0.0500 (13) | |
H5 | 0.5149 | 0.6439 | 0.5407 | 0.060* | |
C8 | 0.2166 (5) | 0.4788 (4) | 0.3897 (3) | 0.0499 (14) | |
H8 | 0.2600 | 0.4090 | 0.3841 | 0.060* | |
C33 | 0.6654 (5) | 0.5176 (4) | 0.9299 (3) | 0.0384 (11) | |
C4 | 0.5212 (5) | 0.6667 (5) | 0.4132 (4) | 0.0578 (16) | |
H4 | 0.5637 | 0.6013 | 0.3959 | 0.069* | |
C6 | 0.1144 (4) | 0.6486 (4) | 0.3595 (3) | 0.0398 (12) | |
H6 | 0.0787 | 0.7118 | 0.3302 | 0.048* | |
C13 | −0.1082 (4) | 0.8524 (4) | 0.5255 (3) | 0.0313 (10) | |
C15 | −0.1462 (5) | 0.9182 (4) | 0.6665 (3) | 0.0354 (11) | |
C38 | 0.2359 (5) | 0.4951 (5) | 0.7127 (3) | 0.0445 (12) | |
H38 | 0.1523 | 0.5033 | 0.6807 | 0.053* | |
C20 | −0.0715 (5) | 1.0197 (4) | 0.7128 (3) | 0.0381 (11) | |
H20 | 0.0204 | 1.0491 | 0.7045 | 0.046* | |
C9 | 0.1811 (5) | 0.5258 (4) | 0.4640 (3) | 0.0397 (11) | |
H9 | 0.1977 | 0.4931 | 0.5160 | 0.048* | |
C2 | 0.4167 (5) | 0.8395 (4) | 0.4130 (3) | 0.0446 (12) | |
H2 | 0.3783 | 0.9091 | 0.3952 | 0.054* | |
C19 | −0.1330 (5) | 1.0794 (4) | 0.7725 (3) | 0.0364 (11) | |
C1 | 0.4276 (5) | 0.7976 (4) | 0.4940 (3) | 0.0420 (12) | |
H1 | 0.3969 | 0.8339 | 0.5393 | 0.050* | |
C30 | 0.9149 (5) | 0.3192 (4) | 1.0332 (3) | 0.0409 (12) | |
C7 | 0.1763 (5) | 0.5538 (5) | 0.3257 (3) | 0.0512 (14) | |
H7 | 0.1883 | 0.5430 | 0.2702 | 0.061* | |
C14 | −0.2104 (4) | 0.9306 (4) | 0.4878 (3) | 0.0394 (11) | |
H14A | −0.3025 | 0.8966 | 0.4998 | 0.059* | |
H14B | −0.2097 | 0.9302 | 0.4288 | 0.059* | |
H14C | −0.1849 | 1.0151 | 0.5106 | 0.059* | |
C18 | −0.2691 (5) | 1.0351 (5) | 0.7844 (3) | 0.0450 (13) | |
H18 | −0.3109 | 1.0745 | 0.8239 | 0.054* | |
C29 | 0.9948 (5) | 0.2211 (5) | 1.0252 (3) | 0.0529 (14) | |
H29 | 1.0045 | 0.1796 | 0.9760 | 0.063* | |
C16 | −0.2826 (5) | 0.8722 (4) | 0.6788 (3) | 0.0438 (12) | |
H16 | −0.3326 | 0.8022 | 0.6480 | 0.053* | |
C26 | 0.9319 (5) | 0.3556 (5) | 1.1197 (3) | 0.0526 (14) | |
H26 | 0.8923 | 0.4186 | 1.1431 | 0.063* | |
C36 | 0.3686 (5) | 0.3757 (5) | 0.8053 (3) | 0.0477 (13) | |
H36 | 0.3745 | 0.3037 | 0.8349 | 0.057* | |
C28 | 1.0570 (5) | 0.1982 (5) | 1.1060 (4) | 0.0597 (16) | |
H28 | 1.1142 | 0.1385 | 1.1186 | 0.072* | |
C17 | −0.3434 (5) | 0.9322 (5) | 0.7377 (3) | 0.0475 (13) | |
H17 | −0.4353 | 0.9026 | 0.7459 | 0.057* | |
C21 | 0.7189 (6) | 0.0133 (5) | 1.0448 (4) | 0.0686 (17) | |
H21 | 0.7295 | −0.0279 | 0.9956 | 0.082* | |
C37 | 0.2447 (5) | 0.3900 (5) | 0.7576 (3) | 0.0506 (13) | |
H37 | 0.1667 | 0.3276 | 0.7561 | 0.061* | |
C22 | 0.6413 (6) | 0.1120 (6) | 1.0525 (4) | 0.0680 (17) | |
H22 | 0.5926 | 0.1475 | 1.0089 | 0.082* | |
C34 | 0.6090 (5) | 0.6337 (4) | 0.9523 (3) | 0.0533 (14) | |
H34A | 0.6306 | 0.6965 | 0.9130 | 0.080* | |
H34B | 0.6510 | 0.6650 | 1.0069 | 0.080* | |
H34C | 0.5094 | 0.6138 | 0.9513 | 0.080* | |
C24 | 0.7326 (6) | 0.0713 (6) | 1.1813 (4) | 0.0705 (18) | |
H24 | 0.7545 | 0.0746 | 1.2387 | 0.085* | |
C23 | 0.6500 (6) | 0.1469 (6) | 1.1359 (4) | 0.0709 (18) | |
H23 | 0.6082 | 0.2095 | 1.1579 | 0.085* | |
C27 | 1.0179 (6) | 0.2807 (5) | 1.1634 (4) | 0.0654 (17) | |
H27 | 1.0445 | 0.2849 | 1.2205 | 0.078* | |
C3 | 0.4743 (5) | 0.7576 (5) | 0.3631 (3) | 0.0559 (14) | |
H3 | 0.4798 | 0.7635 | 0.3065 | 0.067* | |
C25 | 0.7771 (6) | −0.0109 (5) | 1.1252 (4) | 0.0695 (17) | |
H25 | 0.8345 | −0.0702 | 1.1389 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0304 (4) | 0.0344 (4) | 0.0376 (4) | 0.0099 (3) | 0.0051 (3) | −0.0038 (3) |
Fe2 | 0.0417 (4) | 0.0518 (5) | 0.0427 (4) | 0.0158 (4) | 0.0033 (3) | 0.0034 (4) |
O1 | 0.0448 (19) | 0.057 (2) | 0.0285 (17) | 0.0248 (16) | 0.0011 (15) | 0.0010 (15) |
O4 | 0.049 (2) | 0.064 (2) | 0.056 (2) | 0.0118 (19) | −0.0112 (18) | 0.0177 (19) |
O2 | 0.063 (2) | 0.053 (2) | 0.055 (2) | 0.0200 (19) | 0.0078 (19) | −0.0187 (18) |
N1 | 0.040 (2) | 0.047 (2) | 0.039 (2) | 0.0249 (19) | 0.0043 (18) | −0.0007 (18) |
C11 | 0.030 (2) | 0.035 (3) | 0.032 (3) | 0.006 (2) | 0.005 (2) | 0.004 (2) |
C35 | 0.039 (3) | 0.051 (3) | 0.030 (3) | 0.018 (2) | 0.001 (2) | −0.006 (2) |
N2 | 0.046 (2) | 0.059 (3) | 0.038 (2) | 0.029 (2) | −0.0024 (19) | −0.008 (2) |
C39 | 0.048 (3) | 0.048 (3) | 0.026 (2) | 0.019 (3) | 0.002 (2) | 0.002 (2) |
C40 | 0.039 (3) | 0.050 (3) | 0.034 (3) | 0.010 (2) | 0.004 (2) | 0.001 (2) |
C12 | 0.034 (3) | 0.036 (3) | 0.030 (2) | 0.008 (2) | 0.002 (2) | 0.002 (2) |
O3 | 0.066 (2) | 0.067 (2) | 0.040 (2) | 0.040 (2) | −0.0063 (18) | −0.0133 (18) |
C31 | 0.040 (3) | 0.045 (3) | 0.039 (3) | 0.013 (2) | 0.003 (2) | 0.003 (2) |
C32 | 0.040 (3) | 0.044 (3) | 0.033 (3) | 0.012 (2) | −0.001 (2) | −0.004 (2) |
C10 | 0.028 (2) | 0.035 (3) | 0.038 (3) | 0.007 (2) | 0.002 (2) | −0.003 (2) |
C5 | 0.035 (3) | 0.047 (3) | 0.065 (4) | 0.005 (2) | −0.008 (3) | 0.007 (3) |
C8 | 0.047 (3) | 0.035 (3) | 0.069 (4) | 0.009 (2) | 0.014 (3) | −0.016 (3) |
C33 | 0.042 (3) | 0.037 (3) | 0.036 (3) | 0.010 (2) | 0.002 (2) | −0.005 (2) |
C4 | 0.030 (3) | 0.051 (3) | 0.095 (5) | 0.013 (3) | 0.012 (3) | −0.020 (3) |
C6 | 0.036 (3) | 0.049 (3) | 0.036 (3) | 0.014 (2) | 0.000 (2) | −0.002 (2) |
C13 | 0.024 (2) | 0.029 (2) | 0.041 (3) | 0.0030 (19) | 0.004 (2) | 0.006 (2) |
C15 | 0.044 (3) | 0.038 (3) | 0.029 (2) | 0.020 (2) | 0.008 (2) | 0.000 (2) |
C38 | 0.037 (3) | 0.060 (3) | 0.036 (3) | 0.013 (3) | −0.003 (2) | −0.005 (2) |
C20 | 0.044 (3) | 0.037 (3) | 0.036 (3) | 0.014 (2) | 0.006 (2) | 0.002 (2) |
C9 | 0.039 (3) | 0.035 (3) | 0.045 (3) | 0.004 (2) | 0.007 (2) | 0.002 (2) |
C2 | 0.045 (3) | 0.037 (3) | 0.054 (3) | 0.010 (2) | 0.013 (3) | 0.003 (2) |
C19 | 0.048 (3) | 0.033 (3) | 0.031 (3) | 0.016 (2) | 0.007 (2) | 0.002 (2) |
C1 | 0.036 (3) | 0.040 (3) | 0.048 (3) | 0.003 (2) | 0.004 (2) | −0.008 (2) |
C30 | 0.039 (3) | 0.048 (3) | 0.038 (3) | 0.017 (2) | 0.001 (2) | 0.003 (2) |
C7 | 0.041 (3) | 0.065 (4) | 0.043 (3) | 0.006 (3) | 0.001 (2) | −0.020 (3) |
C14 | 0.033 (3) | 0.042 (3) | 0.047 (3) | 0.016 (2) | 0.004 (2) | 0.003 (2) |
C18 | 0.055 (3) | 0.052 (3) | 0.037 (3) | 0.026 (3) | 0.016 (2) | 0.004 (2) |
C29 | 0.038 (3) | 0.075 (4) | 0.048 (3) | 0.018 (3) | 0.004 (2) | 0.014 (3) |
C16 | 0.044 (3) | 0.041 (3) | 0.048 (3) | 0.010 (2) | 0.008 (2) | −0.003 (2) |
C26 | 0.062 (4) | 0.048 (3) | 0.045 (3) | 0.007 (3) | −0.001 (3) | 0.000 (3) |
C36 | 0.054 (3) | 0.048 (3) | 0.042 (3) | 0.012 (3) | 0.004 (3) | 0.003 (2) |
C28 | 0.039 (3) | 0.069 (4) | 0.073 (4) | 0.016 (3) | −0.002 (3) | 0.026 (3) |
C17 | 0.042 (3) | 0.051 (3) | 0.054 (3) | 0.012 (3) | 0.017 (3) | 0.009 (3) |
C21 | 0.064 (4) | 0.062 (4) | 0.076 (5) | 0.004 (3) | 0.004 (3) | −0.009 (3) |
C37 | 0.042 (3) | 0.063 (4) | 0.044 (3) | 0.003 (3) | 0.003 (2) | 0.004 (3) |
C22 | 0.040 (3) | 0.072 (4) | 0.088 (5) | 0.007 (3) | −0.008 (3) | 0.008 (4) |
C34 | 0.061 (4) | 0.049 (3) | 0.053 (3) | 0.027 (3) | −0.002 (3) | −0.008 (3) |
C24 | 0.067 (4) | 0.085 (5) | 0.064 (4) | 0.013 (4) | 0.026 (3) | 0.021 (4) |
C23 | 0.053 (4) | 0.076 (4) | 0.094 (5) | 0.021 (3) | 0.038 (4) | 0.013 (4) |
C27 | 0.072 (4) | 0.068 (4) | 0.049 (3) | 0.004 (3) | −0.018 (3) | 0.011 (3) |
C3 | 0.052 (3) | 0.061 (4) | 0.053 (3) | 0.000 (3) | 0.015 (3) | −0.005 (3) |
C25 | 0.064 (4) | 0.057 (4) | 0.093 (5) | 0.018 (3) | 0.018 (4) | 0.015 (4) |
Fe1—C9 | 2.020 (5) | C8—C9 | 1.401 (6) |
Fe1—C6 | 2.025 (4) | C8—H8 | 0.9300 |
Fe1—C5 | 2.026 (5) | C4—C3 | 1.390 (7) |
Fe1—C4 | 2.026 (5) | C4—H4 | 0.9300 |
Fe1—C1 | 2.029 (4) | C6—C7 | 1.403 (6) |
Fe1—C10 | 2.030 (4) | C6—H6 | 0.9300 |
Fe1—C8 | 2.039 (5) | C15—C20 | 1.367 (6) |
Fe1—C3 | 2.040 (5) | C15—C16 | 1.386 (6) |
Fe1—C7 | 2.044 (5) | C38—C37 | 1.374 (6) |
Fe1—C2 | 2.045 (5) | C38—H38 | 0.9300 |
Fe2—C30 | 2.024 (5) | C20—C19 | 1.398 (6) |
Fe2—C22 | 2.027 (5) | C20—H20 | 0.9300 |
Fe2—C29 | 2.029 (5) | C9—H9 | 0.9300 |
Fe2—C23 | 2.036 (5) | C2—C1 | 1.398 (6) |
Fe2—C25 | 2.042 (6) | C2—C3 | 1.412 (6) |
Fe2—C26 | 2.042 (5) | C2—H2 | 0.9300 |
Fe2—C28 | 2.042 (5) | C19—C18 | 1.378 (6) |
Fe2—C24 | 2.043 (6) | C1—H1 | 0.9300 |
Fe2—C21 | 2.044 (6) | C30—C29 | 1.425 (6) |
Fe2—C27 | 2.057 (5) | C30—C26 | 1.432 (6) |
O1—C11 | 1.265 (5) | C7—H7 | 0.9300 |
O4—C39 | 1.350 (5) | C14—H14A | 0.9600 |
O4—H4O | 0.8200 | C14—H14B | 0.9600 |
O2—C19 | 1.350 (5) | C14—H14C | 0.9600 |
O2—H2O | 0.8200 | C18—C17 | 1.380 (6) |
N1—C13 | 1.340 (5) | C18—H18 | 0.9300 |
N1—C15 | 1.429 (5) | C29—C28 | 1.421 (7) |
N1—H1N | 0.8600 | C29—H29 | 0.9300 |
C10—C11 | 1.491 (6) | C16—C17 | 1.385 (6) |
C11—C12 | 1.400 (5) | C16—H16 | 0.9300 |
C13—C14 | 1.493 (5) | C26—C27 | 1.402 (7) |
C35—C36 | 1.373 (6) | C26—H26 | 0.9300 |
C35—C40 | 1.390 (6) | C36—C37 | 1.387 (6) |
N2—H2N | 0.8600 | C36—H36 | 0.9300 |
C39—C38 | 1.377 (6) | C28—C27 | 1.402 (7) |
C39—C40 | 1.385 (6) | C28—H28 | 0.9300 |
C40—H40 | 0.9300 | C17—H17 | 0.9300 |
C12—C13 | 1.376 (6) | C21—C25 | 1.408 (8) |
C12—H12 | 0.9300 | C21—C22 | 1.415 (8) |
O3—C31 | 1.256 (5) | C21—H21 | 0.9300 |
N2—C33 | 1.348 (5) | C37—H37 | 0.9300 |
N2—C35 | 1.423 (5) | C22—C23 | 1.387 (8) |
C30—C31 | 1.470 (6) | C22—H22 | 0.9300 |
C31—C32 | 1.417 (6) | C34—H34A | 0.9600 |
C32—C33 | 1.369 (6) | C34—H34B | 0.9600 |
C33—C34 | 1.503 (6) | C34—H34C | 0.9600 |
C32—H32 | 0.9300 | C24—C23 | 1.398 (7) |
C10—C6 | 1.420 (6) | C24—C25 | 1.410 (8) |
C10—C9 | 1.420 (6) | C24—H24 | 0.9300 |
C5—C4 | 1.409 (7) | C23—H23 | 0.9300 |
C5—C1 | 1.412 (6) | C27—H27 | 0.9300 |
C5—H5 | 0.9300 | C3—H3 | 0.9300 |
C8—C7 | 1.391 (7) | C25—H25 | 0.9300 |
C9—Fe1—C6 | 68.46 (19) | C5—C4—Fe1 | 69.6 (3) |
C9—Fe1—C5 | 107.0 (2) | C3—C4—H4 | 125.7 |
C6—Fe1—C5 | 166.0 (2) | C5—C4—H4 | 125.7 |
C9—Fe1—C4 | 127.3 (2) | Fe1—C4—H4 | 125.6 |
C6—Fe1—C4 | 152.5 (2) | C7—C6—C10 | 108.5 (4) |
C5—Fe1—C4 | 40.7 (2) | C7—C6—Fe1 | 70.5 (3) |
C9—Fe1—C1 | 117.92 (19) | C10—C6—Fe1 | 69.7 (2) |
C6—Fe1—C1 | 128.49 (18) | C7—C6—H6 | 125.7 |
C5—Fe1—C1 | 40.77 (18) | C10—C6—H6 | 125.7 |
C4—Fe1—C1 | 68.3 (2) | Fe1—C6—H6 | 125.6 |
C9—Fe1—C10 | 41.05 (17) | N1—C13—C12 | 120.2 (4) |
C6—Fe1—C10 | 41.00 (17) | N1—C13—C14 | 118.5 (4) |
C5—Fe1—C10 | 127.0 (2) | C12—C13—C14 | 121.2 (4) |
C4—Fe1—C10 | 165.3 (2) | C20—C15—C16 | 120.6 (4) |
C1—Fe1—C10 | 107.44 (18) | C20—C15—N1 | 118.7 (4) |
C9—Fe1—C8 | 40.39 (18) | C16—C15—N1 | 120.6 (4) |
C6—Fe1—C8 | 67.6 (2) | C37—C38—C39 | 120.1 (4) |
C5—Fe1—C8 | 118.1 (2) | C37—C38—H38 | 120.0 |
C4—Fe1—C8 | 108.4 (2) | C39—C38—H38 | 120.0 |
C1—Fe1—C8 | 151.8 (2) | C15—C20—C19 | 120.1 (5) |
C10—Fe1—C8 | 68.34 (18) | C15—C20—H20 | 119.9 |
C9—Fe1—C3 | 165.2 (2) | C19—C20—H20 | 119.9 |
C6—Fe1—C3 | 119.8 (2) | C8—C9—C10 | 108.2 (4) |
C5—Fe1—C3 | 67.9 (2) | C8—C9—Fe1 | 70.5 (3) |
C4—Fe1—C3 | 40.0 (2) | C10—C9—Fe1 | 69.9 (3) |
C1—Fe1—C3 | 68.0 (2) | C8—C9—H9 | 125.9 |
C10—Fe1—C3 | 153.0 (2) | C10—C9—H9 | 125.9 |
C8—Fe1—C3 | 128.5 (2) | Fe1—C9—H9 | 125.3 |
C9—Fe1—C7 | 67.9 (2) | C1—C2—C3 | 108.1 (4) |
C6—Fe1—C7 | 40.35 (17) | C1—C2—Fe1 | 69.3 (3) |
C5—Fe1—C7 | 151.7 (2) | C3—C2—Fe1 | 69.6 (3) |
C4—Fe1—C7 | 118.9 (2) | C1—C2—H2 | 126.0 |
C1—Fe1—C7 | 166.8 (2) | C3—C2—H2 | 126.0 |
C10—Fe1—C7 | 68.47 (18) | Fe1—C2—H2 | 126.7 |
C8—Fe1—C7 | 39.84 (19) | O2—C19—C18 | 123.9 (4) |
C3—Fe1—C7 | 109.6 (2) | O2—C19—C20 | 116.5 (4) |
C9—Fe1—C2 | 152.17 (19) | C18—C19—C20 | 119.6 (5) |
C6—Fe1—C2 | 109.6 (2) | C2—C1—C5 | 108.0 (4) |
C5—Fe1—C2 | 67.9 (2) | C2—C1—Fe1 | 70.6 (3) |
C4—Fe1—C2 | 67.6 (2) | C5—C1—Fe1 | 69.5 (3) |
C1—Fe1—C2 | 40.14 (18) | C2—C1—H1 | 126.0 |
C10—Fe1—C2 | 118.80 (18) | C5—C1—H1 | 126.0 |
C8—Fe1—C2 | 166.6 (2) | Fe1—C1—H1 | 125.5 |
C3—Fe1—C2 | 40.43 (18) | C29—C30—C26 | 106.7 (4) |
C7—Fe1—C2 | 129.7 (2) | C29—C30—C31 | 126.4 (4) |
C30—Fe2—C22 | 106.8 (2) | C26—C30—C31 | 126.8 (4) |
C30—Fe2—C29 | 41.17 (18) | C29—C30—Fe2 | 69.6 (3) |
C22—Fe2—C29 | 122.1 (2) | C26—C30—Fe2 | 70.0 (3) |
C30—Fe2—C23 | 122.0 (2) | C31—C30—Fe2 | 121.6 (3) |
C22—Fe2—C23 | 39.9 (2) | C8—C7—C6 | 108.0 (4) |
C29—Fe2—C23 | 157.9 (2) | C8—C7—Fe1 | 69.9 (3) |
C30—Fe2—C25 | 158.8 (2) | C6—C7—Fe1 | 69.1 (3) |
C22—Fe2—C25 | 68.0 (2) | C8—C7—H7 | 126.0 |
C29—Fe2—C25 | 122.8 (2) | C6—C7—H7 | 126.0 |
C23—Fe2—C25 | 68.0 (2) | Fe1—C7—H7 | 126.6 |
C30—Fe2—C26 | 41.25 (18) | C13—C14—H14A | 109.5 |
C22—Fe2—C26 | 123.8 (2) | C13—C14—H14B | 109.5 |
C29—Fe2—C26 | 68.5 (2) | H14A—C14—H14B | 109.5 |
C23—Fe2—C26 | 108.5 (2) | C13—C14—H14C | 109.5 |
C25—Fe2—C26 | 158.7 (2) | H14A—C14—H14C | 109.5 |
C30—Fe2—C28 | 68.83 (19) | H14B—C14—H14C | 109.5 |
C22—Fe2—C28 | 158.6 (3) | C19—C18—C17 | 119.9 (4) |
C29—Fe2—C28 | 40.86 (19) | C19—C18—H18 | 120.1 |
C23—Fe2—C28 | 160.1 (3) | C17—C18—H18 | 120.1 |
C25—Fe2—C28 | 108.2 (2) | C28—C29—C30 | 107.7 (5) |
C26—Fe2—C28 | 67.5 (2) | C28—C29—Fe2 | 70.1 (3) |
C30—Fe2—C24 | 158.4 (2) | C30—C29—Fe2 | 69.2 (3) |
C22—Fe2—C24 | 67.2 (3) | C28—C29—H29 | 126.2 |
C29—Fe2—C24 | 159.8 (2) | C30—C29—H29 | 126.2 |
C23—Fe2—C24 | 40.1 (2) | Fe2—C29—H29 | 126.1 |
C25—Fe2—C24 | 40.4 (2) | C17—C16—C15 | 119.1 (5) |
C26—Fe2—C24 | 123.4 (2) | C17—C16—H16 | 120.5 |
C28—Fe2—C24 | 124.4 (2) | C15—C16—H16 | 120.5 |
C30—Fe2—C21 | 122.4 (2) | C27—C26—C30 | 108.8 (5) |
C22—Fe2—C21 | 40.7 (2) | C27—C26—Fe2 | 70.6 (3) |
C29—Fe2—C21 | 106.9 (2) | C30—C26—Fe2 | 68.7 (3) |
C23—Fe2—C21 | 67.8 (3) | C27—C26—H26 | 125.6 |
C25—Fe2—C21 | 40.3 (2) | C30—C26—H26 | 125.6 |
C26—Fe2—C21 | 159.8 (2) | Fe2—C26—H26 | 126.7 |
C28—Fe2—C21 | 122.8 (3) | C35—C36—C37 | 119.2 (5) |
C24—Fe2—C21 | 67.5 (3) | C35—C36—H36 | 120.4 |
C30—Fe2—C27 | 68.7 (2) | C37—C36—H36 | 120.4 |
C22—Fe2—C27 | 159.7 (3) | C27—C28—C29 | 108.7 (5) |
C29—Fe2—C27 | 68.3 (2) | C27—C28—Fe2 | 70.6 (3) |
C23—Fe2—C27 | 124.5 (3) | C29—C28—Fe2 | 69.1 (3) |
C25—Fe2—C27 | 123.3 (2) | C27—C28—H28 | 125.6 |
C26—Fe2—C27 | 39.98 (19) | C29—C28—H28 | 125.6 |
C28—Fe2—C27 | 40.0 (2) | Fe2—C28—H28 | 126.3 |
C24—Fe2—C27 | 109.3 (2) | C18—C17—C16 | 120.8 (5) |
C21—Fe2—C27 | 158.5 (2) | C18—C17—H17 | 119.6 |
C39—O4—H4O | 109.5 | C16—C17—H17 | 119.6 |
C19—O2—H2O | 109.5 | C25—C21—C22 | 107.4 (6) |
C13—N1—C15 | 126.2 (4) | C25—C21—Fe2 | 69.8 (3) |
C13—N1—H1N | 116.9 | C22—C21—Fe2 | 69.0 (3) |
C15—N1—H1N | 116.9 | C25—C21—H21 | 126.3 |
O1—C11—C12 | 122.8 (4) | C22—C21—H21 | 126.3 |
O1—C11—C10 | 118.9 (4) | Fe2—C21—H21 | 126.5 |
C12—C11—C10 | 118.2 (4) | C38—C37—C36 | 120.8 (5) |
C36—C35—C40 | 120.3 (4) | C38—C37—H37 | 119.6 |
C36—C35—N2 | 118.6 (4) | C36—C37—H37 | 119.6 |
C40—C35—N2 | 121.1 (4) | C23—C22—C21 | 108.7 (6) |
C33—N2—C35 | 126.9 (4) | C23—C22—Fe2 | 70.4 (3) |
C33—N2—H2N | 116.5 | C21—C22—Fe2 | 70.3 (3) |
C35—N2—H2N | 116.5 | C23—C22—H22 | 125.7 |
O4—C39—C38 | 123.5 (4) | C21—C22—H22 | 125.7 |
O4—C39—C40 | 116.8 (4) | Fe2—C22—H22 | 125.2 |
C38—C39—C40 | 119.7 (4) | C33—C34—H34A | 109.5 |
C39—C40—C35 | 119.9 (4) | C33—C34—H34B | 109.5 |
C39—C40—H40 | 120.1 | H34A—C34—H34B | 109.5 |
C35—C40—H40 | 120.1 | C33—C34—H34C | 109.5 |
C13—C12—C11 | 124.9 (4) | H34A—C34—H34C | 109.5 |
C13—C12—H12 | 117.5 | H34B—C34—H34C | 109.5 |
C11—C12—H12 | 117.5 | C23—C24—C25 | 108.5 (6) |
O3—C31—C32 | 122.0 (4) | C23—C24—Fe2 | 69.7 (3) |
O3—C31—C30 | 119.0 (4) | C25—C24—Fe2 | 69.8 (3) |
C32—C31—C30 | 119.0 (4) | C23—C24—H24 | 125.7 |
C33—C32—C31 | 124.0 (4) | C25—C24—H24 | 125.7 |
C33—C32—H32 | 118.0 | Fe2—C24—H24 | 126.4 |
C31—C32—H32 | 118.0 | C22—C23—C24 | 108.0 (6) |
C6—C10—C9 | 106.5 (4) | C22—C23—Fe2 | 69.7 (3) |
C6—C10—C11 | 127.3 (4) | C24—C23—Fe2 | 70.2 (3) |
C9—C10—C11 | 126.2 (4) | C22—C23—H23 | 126.0 |
C6—C10—Fe1 | 69.3 (3) | C24—C23—H23 | 126.0 |
C9—C10—Fe1 | 69.1 (2) | Fe2—C23—H23 | 125.6 |
C11—C10—Fe1 | 126.2 (3) | C26—C27—C28 | 108.1 (5) |
C4—C5—C1 | 107.5 (5) | C26—C27—Fe2 | 69.4 (3) |
C4—C5—Fe1 | 69.7 (3) | C28—C27—Fe2 | 69.4 (3) |
C1—C5—Fe1 | 69.7 (3) | C26—C27—H27 | 126.0 |
C4—C5—H5 | 126.3 | C28—C27—H27 | 126.0 |
C1—C5—H5 | 126.3 | Fe2—C27—H27 | 126.8 |
Fe1—C5—H5 | 125.9 | C4—C3—C2 | 108.0 (5) |
C7—C8—C9 | 108.7 (4) | C4—C3—Fe1 | 69.5 (3) |
C7—C8—Fe1 | 70.3 (3) | C2—C3—Fe1 | 70.0 (3) |
C9—C8—Fe1 | 69.1 (3) | C4—C3—H3 | 126.0 |
C7—C8—H8 | 125.6 | C2—C3—H3 | 126.0 |
C9—C8—H8 | 125.6 | Fe1—C3—H3 | 126.1 |
Fe1—C8—H8 | 126.6 | C21—C25—C24 | 107.4 (5) |
N2—C33—C32 | 121.6 (4) | C21—C25—Fe2 | 69.9 (3) |
N2—C33—C34 | 117.7 (4) | C24—C25—Fe2 | 69.8 (3) |
C32—C33—C34 | 120.7 (4) | C21—C25—H25 | 126.3 |
C3—C4—C5 | 108.5 (5) | C24—C25—H25 | 126.3 |
C3—C4—Fe1 | 70.6 (3) | Fe2—C25—H25 | 125.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.86 | 1.96 | 2.642 (5) | 136 |
N2—H2N···O3 | 0.86 | 1.99 | 2.645 (5) | 132 |
O2—H2O···O3i | 0.82 | 1.82 | 2.629 (5) | 170 |
O4—H4O···O1 | 0.82 | 1.86 | 2.679 (5) | 172 |
C2—H2···Cg3ii | 0.93 | 2.85 | 3.686 (5) | 150 |
C4—H4···Cg6iii | 0.93 | 2.89 | 3.614 (6) | 135 |
C28—H28···Cg3iv | 0.93 | 2.96 | 3.655 (6) | 133 |
Symmetry codes: (i) x−1, y+1, z; (ii) −x, −y+2, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z+2. |
[Fe(C5H5)(C15H14NO2)] | Z = 4 |
Mr = 361.21 | F(000) = 752 |
TriclinicP1 | Dx = 1.472 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71070 Å |
a = 7.4100 (11) Å | Cell parameters from 5287 reflections |
b = 14.687 (2) Å | θ = 3.1–25.3° |
c = 15.5601 (19) Å | µ = 0.94 mm−1 |
α = 80.370 (7)° | T = 173 K |
β = 77.677 (7)° | Block, red |
γ = 86.297 (8)° | 0.30 × 0.15 × 0.12 mm |
V = 1630.3 (4) Å3 |
Rigaku Mercury diffractometer | 5891 independent reflections |
Radiation source: fine-focus sealed tube | 4742 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.4°, θmin = 3.1° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −17→16 |
Tmin = 0.767, Tmax = 0.896 | l = −18→17 |
15645 measured reflections |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0406P)2 + 1.0012P] where P = (Fo2 + 2Fc2)/3 |
5891 reflections | (Δ/σ)max = 0.001 |
438 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
[Fe(C5H5)(C15H14NO2)] | γ = 86.297 (8)° |
Mr = 361.21 | V = 1630.3 (4) Å3 |
TriclinicP1 | Z = 4 |
a = 7.4100 (11) Å | Mo Kα radiation |
b = 14.687 (2) Å | µ = 0.94 mm−1 |
c = 15.5601 (19) Å | T = 173 K |
α = 80.370 (7)° | 0.30 × 0.15 × 0.12 mm |
β = 77.677 (7)° |
Rigaku Mercury diffractometer | 5891 independent reflections |
Absorption correction: multi-scan (Jacobson, 1998) | 4742 reflections with I > 2σ(I) |
Tmin = 0.767, Tmax = 0.896 | Rint = 0.036 |
15645 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.47 e Å−3 |
5891 reflections | Δρmin = −0.38 e Å−3 |
438 parameters |
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 | 0.07183 (6) | 0.40931 (3) | 0.32592 (3) | 0.02270 (13) | |
Fe2 | 0.24808 (6) | 1.08742 (3) | 0.82459 (3) | 0.02250 (13) | |
O1 | 0.2716 (3) | 0.62051 (14) | 0.18972 (14) | 0.0308 (5) | |
O2 | 1.1341 (3) | 0.81905 (15) | −0.15364 (15) | 0.0342 (6) | |
H2O | 1.1219 | 0.8567 | −0.1991 | 0.051* | |
O3 | 0.1237 (3) | 0.92476 (14) | 0.69309 (14) | 0.0311 (5) | |
O4 | 0.4398 (3) | 0.61088 (15) | 0.32530 (16) | 0.0365 (6) | |
H4O | 0.3737 | 0.6134 | 0.2873 | 0.055* | |
N1 | 0.4737 (4) | 0.65813 (17) | 0.02983 (16) | 0.0266 (6) | |
H1N | 0.4384 | 0.6693 | 0.0849 | 0.032* | |
N2 | 0.2527 (4) | 0.89164 (17) | 0.53037 (17) | 0.0262 (6) | |
H2N | 0.2124 | 0.8718 | 0.5875 | 0.031* | |
C10 | 0.0400 (4) | 0.5087 (2) | 0.2208 (2) | 0.0237 (7) | |
C9 | −0.0663 (4) | 0.5320 (2) | 0.3025 (2) | 0.0286 (7) | |
H9 | −0.0540 | 0.5857 | 0.3272 | 0.034* | |
C8 | −0.1929 (4) | 0.4613 (2) | 0.3400 (2) | 0.0333 (8) | |
H8 | −0.2816 | 0.4596 | 0.3942 | 0.040* | |
C7 | −0.1662 (4) | 0.3937 (2) | 0.2838 (2) | 0.0317 (8) | |
H7 | −0.2329 | 0.3385 | 0.2938 | 0.038* | |
C6 | −0.0230 (4) | 0.4221 (2) | 0.2099 (2) | 0.0280 (7) | |
H6 | 0.0232 | 0.3895 | 0.1615 | 0.034* | |
C1 | 0.3405 (4) | 0.4013 (2) | 0.3384 (2) | 0.0284 (7) | |
H1 | 0.4372 | 0.4384 | 0.3022 | 0.034* | |
C5 | 0.2243 (5) | 0.4223 (2) | 0.4174 (2) | 0.0319 (8) | |
H5 | 0.2281 | 0.4759 | 0.4436 | 0.038* | |
C4 | 0.1010 (5) | 0.3488 (2) | 0.4505 (2) | 0.0382 (9) | |
H4 | 0.0081 | 0.3442 | 0.5034 | 0.046* | |
C3 | 0.1397 (5) | 0.2840 (2) | 0.3917 (2) | 0.0359 (9) | |
H3 | 0.0765 | 0.2283 | 0.3977 | 0.043* | |
C2 | 0.2887 (4) | 0.3156 (2) | 0.3219 (2) | 0.0305 (8) | |
H2 | 0.3439 | 0.2850 | 0.2731 | 0.037* | |
C11 | 0.1875 (4) | 0.5647 (2) | 0.1591 (2) | 0.0239 (7) | |
C12 | 0.2260 (4) | 0.5558 (2) | 0.0684 (2) | 0.0236 (7) | |
H12 | 0.1528 | 0.5156 | 0.0492 | 0.028* | |
C13 | 0.3650 (4) | 0.6025 (2) | 0.0051 (2) | 0.0248 (7) | |
C14 | 0.3925 (5) | 0.5925 (2) | −0.0912 (2) | 0.0301 (7) | |
H14A | 0.3307 | 0.6445 | −0.1227 | 0.045* | |
H14B | 0.3399 | 0.5345 | −0.0961 | 0.045* | |
H14C | 0.5250 | 0.5919 | −0.1176 | 0.045* | |
C15 | 0.6384 (4) | 0.7020 (2) | −0.0198 (2) | 0.0256 (7) | |
C16 | 0.6425 (4) | 0.7622 (2) | −0.0992 (2) | 0.0275 (7) | |
H16 | 0.5330 | 0.7757 | −0.1220 | 0.033* | |
C17 | 0.8070 (4) | 0.8028 (2) | −0.1451 (2) | 0.0269 (7) | |
H17 | 0.8101 | 0.8431 | −0.1999 | 0.032* | |
C18 | 0.9672 (4) | 0.7847 (2) | −0.1114 (2) | 0.0255 (7) | |
C19 | 0.9592 (5) | 0.7280 (2) | −0.0294 (2) | 0.0276 (7) | |
H19 | 1.0660 | 0.7182 | −0.0040 | 0.033* | |
C20 | 0.7971 (4) | 0.6861 (2) | 0.0150 (2) | 0.0273 (7) | |
H20 | 0.7939 | 0.6460 | 0.0699 | 0.033* | |
C30 | 0.1145 (4) | 1.0779 (2) | 0.7250 (2) | 0.0235 (7) | |
C29 | 0.1937 (5) | 1.1670 (2) | 0.7117 (2) | 0.0279 (7) | |
H29 | 0.2829 | 1.1927 | 0.6615 | 0.033* | |
C28 | 0.1153 (5) | 1.2098 (2) | 0.7867 (2) | 0.0337 (8) | |
H28 | 0.1424 | 1.2694 | 0.7956 | 0.040* | |
C27 | −0.0100 (5) | 1.1485 (2) | 0.8457 (2) | 0.0340 (8) | |
H27 | −0.0826 | 1.1602 | 0.9011 | 0.041* | |
C26 | −0.0102 (4) | 1.0667 (2) | 0.8089 (2) | 0.0276 (7) | |
H26 | −0.0810 | 1.0139 | 0.8355 | 0.033* | |
C21 | 0.4314 (5) | 0.9787 (2) | 0.8337 (2) | 0.0313 (8) | |
H21 | 0.4458 | 0.9295 | 0.7999 | 0.038* | |
C25 | 0.5272 (4) | 1.0624 (2) | 0.8092 (2) | 0.0316 (8) | |
H25 | 0.6172 | 1.0793 | 0.7562 | 0.038* | |
C24 | 0.4653 (5) | 1.1162 (2) | 0.8772 (2) | 0.0368 (9) | |
H24 | 0.5060 | 1.1760 | 0.8781 | 0.044* | |
C23 | 0.3322 (5) | 1.0660 (3) | 0.9439 (2) | 0.0398 (9) | |
H23 | 0.2681 | 1.0860 | 0.9975 | 0.048* | |
C22 | 0.3113 (5) | 0.9805 (2) | 0.9166 (2) | 0.0359 (8) | |
H22 | 0.2307 | 0.9330 | 0.9486 | 0.043* | |
C31 | 0.1550 (4) | 1.0097 (2) | 0.6627 (2) | 0.0240 (7) | |
C32 | 0.2176 (4) | 1.0410 (2) | 0.5708 (2) | 0.0239 (7) | |
H32 | 0.2304 | 1.1056 | 0.5517 | 0.029* | |
C33 | 0.2616 (4) | 0.9833 (2) | 0.5070 (2) | 0.0233 (7) | |
C34 | 0.3192 (5) | 1.0240 (2) | 0.4104 (2) | 0.0289 (7) | |
H34A | 0.4136 | 0.9836 | 0.3804 | 0.043* | |
H34B | 0.3698 | 1.0851 | 0.4055 | 0.043* | |
H34C | 0.2117 | 1.0300 | 0.3823 | 0.043* | |
C35 | 0.2997 (4) | 0.8218 (2) | 0.47540 (19) | 0.0225 (7) | |
C40 | 0.4240 (4) | 0.7509 (2) | 0.4972 (2) | 0.0269 (7) | |
H40 | 0.4793 | 0.7507 | 0.5470 | 0.032* | |
C39 | 0.4668 (4) | 0.6809 (2) | 0.4465 (2) | 0.0285 (7) | |
H39 | 0.5509 | 0.6325 | 0.4620 | 0.034* | |
C38 | 0.3886 (4) | 0.6804 (2) | 0.3733 (2) | 0.0241 (7) | |
C37 | 0.2612 (4) | 0.7499 (2) | 0.3526 (2) | 0.0254 (7) | |
H37 | 0.2048 | 0.7495 | 0.3033 | 0.030* | |
C36 | 0.2168 (4) | 0.8194 (2) | 0.4040 (2) | 0.0264 (7) | |
H36 | 0.1282 | 0.8663 | 0.3902 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0190 (2) | 0.0261 (3) | 0.0229 (3) | −0.00200 (18) | −0.00653 (19) | −0.00018 (18) |
Fe2 | 0.0236 (3) | 0.0250 (2) | 0.0204 (2) | 0.00144 (18) | −0.00741 (19) | −0.00525 (18) |
O1 | 0.0425 (14) | 0.0291 (12) | 0.0222 (12) | −0.0090 (10) | −0.0061 (10) | −0.0056 (9) |
O2 | 0.0326 (13) | 0.0331 (13) | 0.0341 (14) | −0.0048 (10) | −0.0072 (11) | 0.0045 (10) |
O3 | 0.0436 (14) | 0.0279 (12) | 0.0218 (12) | −0.0102 (10) | −0.0047 (10) | −0.0033 (9) |
O4 | 0.0441 (15) | 0.0321 (13) | 0.0412 (15) | 0.0091 (11) | −0.0198 (12) | −0.0184 (11) |
N1 | 0.0333 (16) | 0.0284 (14) | 0.0179 (13) | −0.0071 (12) | −0.0026 (12) | −0.0037 (11) |
N2 | 0.0335 (16) | 0.0268 (14) | 0.0184 (14) | −0.0045 (12) | −0.0040 (12) | −0.0042 (11) |
C10 | 0.0215 (16) | 0.0270 (17) | 0.0226 (16) | 0.0027 (13) | −0.0072 (14) | −0.0017 (13) |
C9 | 0.0256 (17) | 0.0296 (17) | 0.0308 (18) | 0.0074 (14) | −0.0087 (15) | −0.0051 (14) |
C8 | 0.0188 (17) | 0.045 (2) | 0.0332 (19) | 0.0045 (15) | −0.0041 (15) | 0.0000 (16) |
C7 | 0.0229 (17) | 0.0378 (19) | 0.037 (2) | −0.0072 (14) | −0.0159 (16) | 0.0011 (16) |
C6 | 0.0273 (18) | 0.0340 (18) | 0.0263 (17) | 0.0000 (14) | −0.0156 (15) | −0.0027 (14) |
C1 | 0.0207 (17) | 0.0346 (19) | 0.0295 (18) | −0.0029 (14) | −0.0106 (15) | 0.0037 (14) |
C5 | 0.037 (2) | 0.0367 (19) | 0.0278 (18) | 0.0044 (15) | −0.0203 (16) | −0.0050 (15) |
C4 | 0.037 (2) | 0.048 (2) | 0.0244 (18) | 0.0015 (17) | −0.0058 (16) | 0.0090 (16) |
C3 | 0.0297 (19) | 0.0282 (18) | 0.047 (2) | −0.0064 (15) | −0.0128 (17) | 0.0094 (16) |
C2 | 0.0294 (18) | 0.0290 (18) | 0.0346 (19) | 0.0089 (14) | −0.0123 (16) | −0.0057 (14) |
C11 | 0.0262 (17) | 0.0202 (16) | 0.0260 (17) | 0.0058 (13) | −0.0098 (14) | −0.0024 (13) |
C12 | 0.0249 (17) | 0.0244 (16) | 0.0231 (17) | −0.0007 (13) | −0.0097 (14) | −0.0022 (13) |
C13 | 0.0307 (18) | 0.0239 (16) | 0.0215 (16) | 0.0047 (14) | −0.0104 (14) | −0.0035 (13) |
C14 | 0.0312 (18) | 0.0341 (18) | 0.0260 (18) | −0.0030 (15) | −0.0075 (15) | −0.0044 (14) |
C15 | 0.0338 (19) | 0.0220 (16) | 0.0228 (17) | 0.0004 (14) | −0.0073 (15) | −0.0077 (13) |
C16 | 0.0327 (19) | 0.0224 (16) | 0.0283 (18) | 0.0000 (14) | −0.0099 (15) | −0.0024 (13) |
C17 | 0.040 (2) | 0.0191 (15) | 0.0224 (17) | −0.0011 (14) | −0.0090 (15) | −0.0014 (13) |
C18 | 0.0293 (18) | 0.0201 (15) | 0.0273 (17) | −0.0006 (13) | −0.0042 (15) | −0.0065 (13) |
C19 | 0.0329 (19) | 0.0250 (16) | 0.0277 (18) | 0.0054 (14) | −0.0116 (15) | −0.0076 (13) |
C20 | 0.038 (2) | 0.0225 (16) | 0.0206 (16) | −0.0012 (14) | −0.0063 (15) | −0.0026 (13) |
C30 | 0.0213 (16) | 0.0285 (17) | 0.0231 (17) | 0.0027 (13) | −0.0114 (13) | −0.0034 (13) |
C29 | 0.0357 (19) | 0.0270 (17) | 0.0225 (17) | 0.0020 (14) | −0.0123 (15) | −0.0015 (13) |
C28 | 0.049 (2) | 0.0242 (17) | 0.0339 (19) | 0.0130 (15) | −0.0223 (17) | −0.0086 (14) |
C27 | 0.0291 (19) | 0.048 (2) | 0.0277 (18) | 0.0143 (16) | −0.0082 (15) | −0.0155 (16) |
C26 | 0.0211 (17) | 0.0393 (19) | 0.0241 (17) | 0.0009 (14) | −0.0064 (14) | −0.0081 (14) |
C21 | 0.0332 (19) | 0.0290 (18) | 0.036 (2) | 0.0107 (14) | −0.0179 (16) | −0.0074 (15) |
C25 | 0.0201 (17) | 0.042 (2) | 0.035 (2) | 0.0002 (15) | −0.0091 (15) | −0.0077 (16) |
C24 | 0.034 (2) | 0.040 (2) | 0.047 (2) | 0.0027 (16) | −0.0241 (18) | −0.0172 (17) |
C23 | 0.048 (2) | 0.055 (2) | 0.0227 (18) | 0.0160 (18) | −0.0207 (17) | −0.0131 (17) |
C22 | 0.041 (2) | 0.035 (2) | 0.032 (2) | 0.0002 (16) | −0.0152 (17) | 0.0047 (15) |
C31 | 0.0201 (16) | 0.0296 (17) | 0.0244 (17) | −0.0003 (13) | −0.0083 (13) | −0.0058 (13) |
C32 | 0.0244 (16) | 0.0228 (16) | 0.0249 (17) | 0.0006 (13) | −0.0076 (14) | −0.0020 (13) |
C33 | 0.0189 (16) | 0.0304 (17) | 0.0220 (16) | 0.0011 (13) | −0.0075 (13) | −0.0045 (13) |
C34 | 0.0342 (19) | 0.0304 (17) | 0.0223 (17) | 0.0002 (14) | −0.0072 (15) | −0.0033 (14) |
C35 | 0.0248 (17) | 0.0231 (16) | 0.0182 (15) | −0.0047 (13) | −0.0019 (13) | −0.0012 (12) |
C40 | 0.0288 (18) | 0.0316 (18) | 0.0217 (17) | −0.0051 (14) | −0.0106 (14) | −0.0002 (13) |
C39 | 0.0289 (18) | 0.0242 (17) | 0.0337 (19) | 0.0029 (14) | −0.0129 (15) | −0.0014 (14) |
C38 | 0.0246 (17) | 0.0239 (16) | 0.0237 (17) | −0.0040 (13) | −0.0011 (14) | −0.0069 (13) |
C37 | 0.0274 (18) | 0.0284 (17) | 0.0232 (17) | −0.0031 (14) | −0.0115 (14) | −0.0034 (13) |
C36 | 0.0257 (17) | 0.0266 (17) | 0.0276 (18) | 0.0013 (13) | −0.0076 (14) | −0.0039 (13) |
Fe1—C9 | 2.032 (3) | C15—C20 | 1.387 (4) |
Fe1—C1 | 2.035 (3) | C15—C16 | 1.389 (4) |
Fe1—C5 | 2.036 (3) | C16—C17 | 1.389 (4) |
Fe1—C3 | 2.039 (3) | C16—H16 | 0.9500 |
Fe1—C8 | 2.040 (3) | C17—C18 | 1.390 (4) |
Fe1—C4 | 2.043 (3) | C17—H17 | 0.9500 |
Fe1—C10 | 2.045 (3) | C18—C19 | 1.394 (4) |
Fe1—C2 | 2.045 (3) | C19—C20 | 1.377 (4) |
Fe1—C7 | 2.046 (3) | C19—H19 | 0.9500 |
Fe1—C6 | 2.049 (3) | C20—H20 | 0.9500 |
Fe2—C26 | 2.028 (3) | C30—C26 | 1.420 (4) |
Fe2—C21 | 2.035 (3) | C30—C29 | 1.434 (4) |
Fe2—C30 | 2.036 (3) | O3—C31 | 1.275 (4) |
Fe2—C29 | 2.042 (3) | O4—C38 | 1.353 (4) |
Fe2—C22 | 2.043 (3) | O4—H4O | 0.8400 |
Fe2—C27 | 2.045 (3) | N2—C33 | 1.337 (4) |
Fe2—C25 | 2.047 (3) | N2—C35 | 1.423 (4) |
Fe2—C24 | 2.051 (3) | N2—H2N | 0.8800 |
Fe2—C23 | 2.052 (3) | C30—C31 | 1.481 (4) |
Fe2—C28 | 2.052 (3) | C29—C28 | 1.416 (5) |
O1—C11 | 1.269 (4) | C29—H29 | 0.9500 |
O2—C18 | 1.356 (4) | C28—C27 | 1.408 (5) |
O2—H2O | 0.8400 | C28—H28 | 0.9500 |
N1—C13 | 1.336 (4) | C27—C26 | 1.414 (5) |
N1—C15 | 1.427 (4) | C27—H27 | 0.9500 |
N1—H1N | 0.8800 | C26—H26 | 0.9500 |
C10—C11 | 1.482 (4) | C21—C22 | 1.405 (5) |
C11—C12 | 1.406 (4) | C21—C25 | 1.415 (5) |
C12—C13 | 1.391 (4) | C21—H21 | 0.9500 |
C12—H12 | 0.9500 | C25—C24 | 1.408 (5) |
C13—C14 | 1.498 (4) | C25—H25 | 0.9500 |
C10—C9 | 1.427 (4) | C24—C23 | 1.412 (5) |
C10—C6 | 1.430 (4) | C24—H24 | 0.9500 |
C9—C8 | 1.410 (5) | C23—C22 | 1.420 (5) |
C9—H9 | 0.9500 | C23—H23 | 0.9500 |
C8—C7 | 1.407 (5) | C22—H22 | 0.9500 |
C8—H8 | 0.9500 | C31—C32 | 1.413 (4) |
C7—C6 | 1.414 (5) | C32—C33 | 1.386 (4) |
C7—H7 | 0.9500 | C32—H32 | 0.9500 |
C6—H6 | 0.9500 | C33—C34 | 1.502 (4) |
C1—C5 | 1.410 (5) | C34—H34A | 0.9800 |
C1—C2 | 1.418 (5) | C34—H34B | 0.9800 |
C1—H1 | 0.9500 | C34—H34C | 0.9800 |
C5—C4 | 1.416 (5) | C35—C36 | 1.385 (4) |
C5—H5 | 0.9500 | C35—C40 | 1.393 (4) |
C4—C3 | 1.404 (5) | C40—C39 | 1.379 (4) |
C4—H4 | 0.9500 | C40—H40 | 0.9500 |
C3—C2 | 1.413 (5) | C39—C38 | 1.385 (4) |
C3—H3 | 0.9500 | C39—H39 | 0.9500 |
C2—H2 | 0.9500 | C38—C37 | 1.390 (4) |
C14—H14A | 0.9800 | C37—C36 | 1.382 (4) |
C14—H14B | 0.9800 | C37—H37 | 0.9500 |
C14—H14C | 0.9800 | C36—H36 | 0.9500 |
C9—Fe1—C1 | 122.34 (13) | C5—C4—Fe1 | 69.43 (18) |
C9—Fe1—C5 | 106.77 (14) | C3—C4—H4 | 125.9 |
C1—Fe1—C5 | 40.53 (13) | C5—C4—H4 | 125.9 |
C9—Fe1—C3 | 158.93 (14) | Fe1—C4—H4 | 126.5 |
C1—Fe1—C3 | 68.03 (13) | C4—C3—C2 | 108.5 (3) |
C5—Fe1—C3 | 68.22 (14) | C4—C3—Fe1 | 70.02 (19) |
C9—Fe1—C8 | 40.53 (13) | C2—C3—Fe1 | 69.99 (18) |
C1—Fe1—C8 | 156.55 (14) | C4—C3—H3 | 125.8 |
C5—Fe1—C8 | 120.10 (14) | C2—C3—H3 | 125.8 |
C3—Fe1—C8 | 122.80 (13) | Fe1—C3—H3 | 125.8 |
C9—Fe1—C4 | 122.76 (14) | C3—C2—C1 | 107.2 (3) |
C1—Fe1—C4 | 67.93 (13) | C3—C2—Fe1 | 69.52 (19) |
C5—Fe1—C4 | 40.62 (14) | C1—C2—Fe1 | 69.27 (18) |
C3—Fe1—C4 | 40.24 (14) | C3—C2—H2 | 126.4 |
C8—Fe1—C4 | 105.91 (14) | C1—C2—H2 | 126.4 |
C9—Fe1—C10 | 40.98 (12) | Fe1—C2—H2 | 126.4 |
C1—Fe1—C10 | 109.57 (12) | O1—C11—C12 | 122.3 (3) |
C5—Fe1—C10 | 124.92 (13) | O1—C11—C10 | 118.8 (3) |
C3—Fe1—C10 | 158.39 (14) | C12—C11—C10 | 118.9 (3) |
C8—Fe1—C10 | 68.32 (13) | C13—C12—C11 | 123.9 (3) |
C4—Fe1—C10 | 160.63 (14) | C13—C12—H12 | 118.1 |
C9—Fe1—C2 | 158.69 (13) | C11—C12—H12 | 118.1 |
C1—Fe1—C2 | 40.67 (13) | N1—C13—C12 | 119.8 (3) |
C5—Fe1—C2 | 68.47 (14) | N1—C13—C14 | 119.5 (3) |
C3—Fe1—C2 | 40.49 (13) | C12—C13—C14 | 120.7 (3) |
C8—Fe1—C2 | 160.09 (13) | C13—C14—H14A | 109.5 |
C4—Fe1—C2 | 68.01 (14) | C13—C14—H14B | 109.5 |
C10—Fe1—C2 | 123.55 (13) | H14A—C14—H14B | 109.5 |
C9—Fe1—C7 | 68.30 (13) | C13—C14—H14C | 109.5 |
C1—Fe1—C7 | 162.57 (14) | H14A—C14—H14C | 109.5 |
C5—Fe1—C7 | 155.02 (14) | H14B—C14—H14C | 109.5 |
C3—Fe1—C7 | 107.10 (13) | C20—C15—C16 | 119.6 (3) |
C8—Fe1—C7 | 40.28 (14) | C20—C15—N1 | 118.1 (3) |
C4—Fe1—C7 | 119.95 (14) | C16—C15—N1 | 122.3 (3) |
C10—Fe1—C7 | 68.39 (13) | C15—C16—C17 | 119.9 (3) |
C2—Fe1—C7 | 124.89 (14) | C15—C16—H16 | 120.0 |
C9—Fe1—C6 | 68.66 (13) | C17—C16—H16 | 120.0 |
C1—Fe1—C6 | 126.78 (13) | C16—C17—C18 | 120.4 (3) |
C5—Fe1—C6 | 162.78 (13) | C16—C17—H17 | 119.8 |
C3—Fe1—C6 | 122.04 (14) | C18—C17—H17 | 119.8 |
C8—Fe1—C6 | 67.96 (14) | O2—C18—C17 | 123.9 (3) |
C4—Fe1—C6 | 155.90 (14) | O2—C18—C19 | 116.9 (3) |
C10—Fe1—C6 | 40.90 (12) | C17—C18—C19 | 119.2 (3) |
C2—Fe1—C6 | 109.39 (13) | C20—C19—C18 | 120.3 (3) |
C7—Fe1—C6 | 40.39 (13) | C20—C19—H19 | 119.9 |
C26—Fe2—C21 | 119.76 (13) | C18—C19—H19 | 119.9 |
C26—Fe2—C30 | 40.91 (12) | C19—C20—C15 | 120.6 (3) |
C21—Fe2—C30 | 108.55 (13) | C19—C20—H20 | 119.7 |
C26—Fe2—C29 | 68.92 (13) | C15—C20—H20 | 119.7 |
C21—Fe2—C29 | 127.73 (13) | C26—C30—C29 | 107.6 (3) |
C30—Fe2—C29 | 41.17 (12) | C26—C30—C31 | 126.1 (3) |
C26—Fe2—C22 | 106.86 (14) | C29—C30—C31 | 126.3 (3) |
C21—Fe2—C22 | 40.29 (13) | C26—C30—Fe2 | 69.26 (17) |
C30—Fe2—C22 | 126.06 (13) | C29—C30—Fe2 | 69.63 (17) |
C29—Fe2—C22 | 164.49 (13) | C31—C30—Fe2 | 126.5 (2) |
C26—Fe2—C27 | 40.64 (13) | C28—C29—C30 | 107.8 (3) |
C21—Fe2—C27 | 153.92 (14) | C28—C29—Fe2 | 70.15 (18) |
C30—Fe2—C27 | 68.27 (13) | C30—C29—Fe2 | 69.19 (17) |
C29—Fe2—C27 | 68.00 (14) | C28—C29—H29 | 126.1 |
C22—Fe2—C27 | 119.19 (14) | C30—C29—H29 | 126.1 |
C26—Fe2—C25 | 155.11 (13) | Fe2—C29—H29 | 126.1 |
C21—Fe2—C25 | 40.57 (13) | C27—C28—C29 | 108.1 (3) |
C30—Fe2—C25 | 121.07 (13) | C27—C28—Fe2 | 69.62 (18) |
C29—Fe2—C25 | 109.12 (14) | C29—C28—Fe2 | 69.39 (18) |
C22—Fe2—C25 | 68.03 (14) | C27—C28—H28 | 126.0 |
C27—Fe2—C25 | 163.49 (14) | C29—C28—H28 | 126.0 |
C26—Fe2—C24 | 162.62 (14) | Fe2—C28—H28 | 126.6 |
C21—Fe2—C24 | 67.84 (14) | C28—C27—C26 | 108.8 (3) |
C30—Fe2—C24 | 155.39 (14) | C28—C27—Fe2 | 70.18 (19) |
C29—Fe2—C24 | 120.42 (14) | C26—C27—Fe2 | 69.07 (18) |
C22—Fe2—C24 | 67.99 (15) | C28—C27—H27 | 125.6 |
C27—Fe2—C24 | 126.00 (14) | C26—C27—H27 | 125.6 |
C25—Fe2—C24 | 40.18 (13) | Fe2—C27—H27 | 126.8 |
C26—Fe2—C23 | 125.18 (14) | C27—C26—C30 | 107.7 (3) |
C21—Fe2—C23 | 67.86 (14) | C27—C26—Fe2 | 70.30 (18) |
C30—Fe2—C23 | 163.09 (14) | C30—C26—Fe2 | 69.83 (17) |
C29—Fe2—C23 | 153.96 (14) | C27—C26—H26 | 126.1 |
C22—Fe2—C23 | 40.58 (14) | C30—C26—H26 | 126.1 |
C27—Fe2—C23 | 107.24 (14) | Fe2—C26—H26 | 125.3 |
C25—Fe2—C23 | 67.77 (14) | C22—C21—C25 | 108.5 (3) |
C24—Fe2—C23 | 40.27 (15) | C22—C21—Fe2 | 70.17 (19) |
C26—Fe2—C28 | 68.46 (14) | C25—C21—Fe2 | 70.16 (18) |
C21—Fe2—C28 | 164.90 (14) | C22—C21—H21 | 125.8 |
C30—Fe2—C28 | 68.55 (13) | C25—C21—H21 | 125.8 |
C29—Fe2—C28 | 40.46 (13) | Fe2—C21—H21 | 125.5 |
C22—Fe2—C28 | 153.39 (14) | C24—C25—C21 | 107.7 (3) |
C27—Fe2—C28 | 40.20 (14) | C24—C25—Fe2 | 70.07 (19) |
C25—Fe2—C28 | 127.15 (14) | C21—C25—Fe2 | 69.27 (18) |
C24—Fe2—C28 | 108.24 (14) | C24—C25—H25 | 126.1 |
C23—Fe2—C28 | 119.30 (14) | C21—C25—H25 | 126.1 |
C18—O2—H2O | 109.5 | Fe2—C25—H25 | 126.1 |
C38—O4—H4O | 109.5 | C25—C24—C23 | 108.2 (3) |
C13—N1—C15 | 129.5 (3) | C25—C24—Fe2 | 69.75 (18) |
C13—N1—H1N | 115.2 | C23—C24—Fe2 | 69.89 (19) |
C15—N1—H1N | 115.2 | C25—C24—H24 | 125.9 |
C33—N2—C35 | 128.7 (3) | C23—C24—H24 | 125.9 |
C33—N2—H2N | 115.6 | Fe2—C24—H24 | 126.1 |
C35—N2—H2N | 115.6 | C24—C23—C22 | 107.8 (3) |
C9—C10—C6 | 107.3 (3) | C24—C23—Fe2 | 69.84 (19) |
C9—C10—C11 | 125.9 (3) | C22—C23—Fe2 | 69.40 (19) |
C6—C10—C11 | 126.8 (3) | C24—C23—H23 | 126.1 |
C9—C10—Fe1 | 69.05 (17) | C22—C23—H23 | 126.1 |
C6—C10—Fe1 | 69.71 (17) | Fe2—C23—H23 | 126.3 |
C11—C10—Fe1 | 126.7 (2) | C21—C22—C23 | 107.7 (3) |
C8—C9—C10 | 107.8 (3) | C21—C22—Fe2 | 69.54 (18) |
C8—C9—Fe1 | 70.00 (18) | C23—C22—Fe2 | 70.02 (19) |
C10—C9—Fe1 | 69.97 (17) | C21—C22—H22 | 126.1 |
C8—C9—H9 | 126.1 | C23—C22—H22 | 126.1 |
C10—C9—H9 | 126.1 | Fe2—C22—H22 | 125.9 |
Fe1—C9—H9 | 125.5 | O3—C31—C32 | 121.8 (3) |
C7—C8—C9 | 108.7 (3) | O3—C31—C30 | 118.9 (3) |
C7—C8—Fe1 | 70.12 (18) | C32—C31—C30 | 119.2 (3) |
C9—C8—Fe1 | 69.47 (18) | C33—C32—C31 | 124.0 (3) |
C7—C8—H8 | 125.6 | C33—C32—H32 | 118.0 |
C9—C8—H8 | 125.6 | C31—C32—H32 | 118.0 |
Fe1—C8—H8 | 126.4 | N2—C33—C32 | 120.6 (3) |
C8—C7—C6 | 108.2 (3) | N2—C33—C34 | 119.6 (3) |
C8—C7—Fe1 | 69.60 (18) | C32—C33—C34 | 119.8 (3) |
C6—C7—Fe1 | 69.91 (17) | C33—C34—H34A | 109.5 |
C8—C7—H7 | 125.9 | C33—C34—H34B | 109.5 |
C6—C7—H7 | 125.9 | H34A—C34—H34B | 109.5 |
Fe1—C7—H7 | 126.2 | C33—C34—H34C | 109.5 |
C7—C6—C10 | 107.9 (3) | H34A—C34—H34C | 109.5 |
C7—C6—Fe1 | 69.71 (18) | H34B—C34—H34C | 109.5 |
C10—C6—Fe1 | 69.39 (17) | C36—C35—C40 | 119.1 (3) |
C7—C6—H6 | 126.1 | C36—C35—N2 | 121.7 (3) |
C10—C6—H6 | 126.1 | C40—C35—N2 | 119.0 (3) |
Fe1—C6—H6 | 126.4 | C39—C40—C35 | 119.9 (3) |
C5—C1—C2 | 108.6 (3) | C39—C40—H40 | 120.0 |
C5—C1—Fe1 | 69.77 (18) | C35—C40—H40 | 120.0 |
C2—C1—Fe1 | 70.06 (18) | C40—C39—C38 | 120.8 (3) |
C5—C1—H1 | 125.7 | C40—C39—H39 | 119.6 |
C2—C1—H1 | 125.7 | C38—C39—H39 | 119.6 |
Fe1—C1—H1 | 126.0 | O4—C38—C39 | 117.8 (3) |
C1—C5—C4 | 107.5 (3) | O4—C38—C37 | 122.9 (3) |
C1—C5—Fe1 | 69.70 (18) | C39—C38—C37 | 119.3 (3) |
C4—C5—Fe1 | 69.95 (19) | C36—C37—C38 | 119.8 (3) |
C1—C5—H5 | 126.3 | C36—C37—H37 | 120.1 |
C4—C5—H5 | 126.3 | C38—C37—H37 | 120.1 |
Fe1—C5—H5 | 125.7 | C37—C36—C35 | 120.9 (3) |
C3—C4—C5 | 108.3 (3) | C37—C36—H36 | 119.6 |
C3—C4—Fe1 | 69.74 (19) | C35—C36—H36 | 119.6 |
C1—Fe1—C10—C9 | −117.16 (19) | C21—Fe2—C30—C26 | 114.34 (19) |
C5—Fe1—C10—C9 | −74.5 (2) | C29—Fe2—C30—C26 | −119.0 (3) |
C3—Fe1—C10—C9 | 163.2 (3) | C22—Fe2—C30—C26 | 73.0 (2) |
C8—Fe1—C10—C9 | 37.86 (19) | C27—Fe2—C30—C26 | −38.05 (19) |
C4—Fe1—C10—C9 | −38.2 (5) | C25—Fe2—C30—C26 | 157.18 (19) |
C2—Fe1—C10—C9 | −160.26 (19) | C24—Fe2—C30—C26 | −168.5 (3) |
C7—Fe1—C10—C9 | 81.3 (2) | C23—Fe2—C30—C26 | 39.6 (5) |
C6—Fe1—C10—C9 | 118.8 (3) | C28—Fe2—C30—C26 | −81.4 (2) |
C9—Fe1—C10—C6 | −118.8 (3) | C26—Fe2—C30—C29 | 119.0 (3) |
C1—Fe1—C10—C6 | 124.06 (19) | C21—Fe2—C30—C29 | −126.63 (19) |
C5—Fe1—C10—C6 | 166.71 (19) | C22—Fe2—C30—C29 | −168.0 (2) |
C3—Fe1—C10—C6 | 44.5 (4) | C27—Fe2—C30—C29 | 81.0 (2) |
C8—Fe1—C10—C6 | −80.9 (2) | C25—Fe2—C30—C29 | −83.8 (2) |
C4—Fe1—C10—C6 | −156.9 (4) | C24—Fe2—C30—C29 | −49.5 (4) |
C2—Fe1—C10—C6 | 81.0 (2) | C23—Fe2—C30—C29 | 158.6 (4) |
C7—Fe1—C10—C6 | −37.43 (19) | C28—Fe2—C30—C29 | 37.59 (19) |
C9—Fe1—C10—C11 | 119.8 (3) | C26—Fe2—C30—C31 | −120.2 (3) |
C1—Fe1—C10—C11 | 2.7 (3) | C21—Fe2—C30—C31 | −5.9 (3) |
C5—Fe1—C10—C11 | 45.3 (3) | C29—Fe2—C30—C31 | 120.7 (3) |
C3—Fe1—C10—C11 | −76.9 (4) | C22—Fe2—C30—C31 | −47.2 (3) |
C8—Fe1—C10—C11 | 157.7 (3) | C27—Fe2—C30—C31 | −158.3 (3) |
C4—Fe1—C10—C11 | 81.7 (5) | C25—Fe2—C30—C31 | 37.0 (3) |
C2—Fe1—C10—C11 | −40.4 (3) | C24—Fe2—C30—C31 | 71.2 (4) |
C7—Fe1—C10—C11 | −158.8 (3) | C23—Fe2—C30—C31 | −80.7 (5) |
C6—Fe1—C10—C11 | −121.4 (3) | C28—Fe2—C30—C31 | 158.3 (3) |
C6—C10—C9—C8 | −0.6 (3) | C26—C30—C29—C28 | −0.7 (3) |
C11—C10—C9—C8 | 179.1 (3) | C31—C30—C29—C28 | 179.2 (3) |
Fe1—C10—C9—C8 | −60.0 (2) | Fe2—C30—C29—C28 | −59.8 (2) |
C6—C10—C9—Fe1 | 59.4 (2) | C26—C30—C29—Fe2 | 59.1 (2) |
C11—C10—C9—Fe1 | −120.8 (3) | C31—C30—C29—Fe2 | −121.0 (3) |
C1—Fe1—C9—C8 | −158.5 (2) | C26—Fe2—C29—C28 | 81.1 (2) |
C5—Fe1—C9—C8 | −117.0 (2) | C21—Fe2—C29—C28 | −166.9 (2) |
C3—Fe1—C9—C8 | −44.2 (5) | C30—Fe2—C29—C28 | 119.0 (3) |
C4—Fe1—C9—C8 | −75.5 (2) | C22—Fe2—C29—C28 | 158.0 (5) |
C10—Fe1—C9—C8 | 118.6 (3) | C27—Fe2—C29—C28 | 37.3 (2) |
C2—Fe1—C9—C8 | 169.4 (3) | C25—Fe2—C29—C28 | −125.3 (2) |
C7—Fe1—C9—C8 | 37.1 (2) | C24—Fe2—C29—C28 | −82.6 (2) |
C6—Fe1—C9—C8 | 80.6 (2) | C23—Fe2—C29—C28 | −47.0 (4) |
C1—Fe1—C9—C10 | 82.9 (2) | C26—Fe2—C29—C30 | −37.86 (18) |
C5—Fe1—C9—C10 | 124.38 (19) | C21—Fe2—C29—C30 | 74.1 (2) |
C3—Fe1—C9—C10 | −162.8 (3) | C22—Fe2—C29—C30 | 39.1 (6) |
C8—Fe1—C9—C10 | −118.6 (3) | C27—Fe2—C29—C30 | −81.7 (2) |
C4—Fe1—C9—C10 | 165.90 (18) | C25—Fe2—C29—C30 | 115.69 (19) |
C2—Fe1—C9—C10 | 50.8 (4) | C24—Fe2—C29—C30 | 158.45 (19) |
C7—Fe1—C9—C10 | −81.6 (2) | C23—Fe2—C29—C30 | −166.0 (3) |
C6—Fe1—C9—C10 | −38.03 (18) | C28—Fe2—C29—C30 | −119.0 (3) |
C10—C9—C8—C7 | 0.7 (4) | C30—C29—C28—C27 | 0.1 (4) |
Fe1—C9—C8—C7 | −59.3 (2) | Fe2—C29—C28—C27 | −59.1 (2) |
C10—C9—C8—Fe1 | 60.0 (2) | C30—C29—C28—Fe2 | 59.2 (2) |
C9—Fe1—C8—C7 | 120.0 (3) | C26—Fe2—C28—C27 | 37.17 (19) |
C1—Fe1—C8—C7 | 171.1 (3) | C21—Fe2—C28—C27 | 163.0 (5) |
C5—Fe1—C8—C7 | −159.48 (19) | C30—Fe2—C28—C27 | 81.3 (2) |
C3—Fe1—C8—C7 | −77.3 (2) | C29—Fe2—C28—C27 | 119.5 (3) |
C4—Fe1—C8—C7 | −117.8 (2) | C22—Fe2—C28—C27 | −47.6 (4) |
C10—Fe1—C8—C7 | 81.7 (2) | C25—Fe2—C28—C27 | −165.2 (2) |
C2—Fe1—C8—C7 | −48.7 (5) | C24—Fe2—C28—C27 | −124.7 (2) |
C6—Fe1—C8—C7 | 37.50 (19) | C23—Fe2—C28—C27 | −82.1 (2) |
C1—Fe1—C8—C9 | 51.1 (4) | C26—Fe2—C28—C29 | −82.4 (2) |
C5—Fe1—C8—C9 | 80.5 (2) | C21—Fe2—C28—C29 | 43.5 (6) |
C3—Fe1—C8—C9 | 162.7 (2) | C30—Fe2—C28—C29 | −38.23 (19) |
C4—Fe1—C8—C9 | 122.2 (2) | C22—Fe2—C28—C29 | −167.1 (3) |
C10—Fe1—C8—C9 | −38.27 (19) | C27—Fe2—C28—C29 | −119.5 (3) |
C2—Fe1—C8—C9 | −168.7 (4) | C25—Fe2—C28—C29 | 75.2 (2) |
C7—Fe1—C8—C9 | −120.0 (3) | C24—Fe2—C28—C29 | 115.8 (2) |
C6—Fe1—C8—C9 | −82.5 (2) | C23—Fe2—C28—C29 | 158.4 (2) |
C9—C8—C7—C6 | −0.5 (4) | C29—C28—C27—C26 | 0.5 (4) |
Fe1—C8—C7—C6 | −59.4 (2) | Fe2—C28—C27—C26 | −58.4 (2) |
C9—C8—C7—Fe1 | 58.9 (2) | C29—C28—C27—Fe2 | 58.9 (2) |
C9—Fe1—C7—C8 | −37.28 (19) | C26—Fe2—C27—C28 | −120.3 (3) |
C1—Fe1—C7—C8 | −168.2 (4) | C21—Fe2—C27—C28 | −170.0 (3) |
C5—Fe1—C7—C8 | 45.9 (4) | C30—Fe2—C27—C28 | −82.0 (2) |
C3—Fe1—C7—C8 | 120.9 (2) | C29—Fe2—C27—C28 | −37.52 (19) |
C4—Fe1—C7—C8 | 79.0 (2) | C22—Fe2—C27—C28 | 157.7 (2) |
C10—Fe1—C7—C8 | −81.5 (2) | C25—Fe2—C27—C28 | 45.6 (5) |
C2—Fe1—C7—C8 | 161.83 (19) | C24—Fe2—C27—C28 | 74.9 (2) |
C6—Fe1—C7—C8 | −119.4 (3) | C23—Fe2—C27—C28 | 115.3 (2) |
C9—Fe1—C7—C6 | 82.1 (2) | C21—Fe2—C27—C26 | −49.7 (4) |
C1—Fe1—C7—C6 | −48.7 (5) | C30—Fe2—C27—C26 | 38.30 (18) |
C5—Fe1—C7—C6 | 165.3 (3) | C29—Fe2—C27—C26 | 82.8 (2) |
C3—Fe1—C7—C6 | −119.7 (2) | C22—Fe2—C27—C26 | −81.9 (2) |
C8—Fe1—C7—C6 | 119.4 (3) | C25—Fe2—C27—C26 | 165.9 (4) |
C4—Fe1—C7—C6 | −161.6 (2) | C24—Fe2—C27—C26 | −164.7 (2) |
C10—Fe1—C7—C6 | 37.90 (19) | C23—Fe2—C27—C26 | −124.4 (2) |
C2—Fe1—C7—C6 | −78.7 (2) | C28—Fe2—C27—C26 | 120.3 (3) |
C8—C7—C6—C10 | 0.2 (4) | C28—C27—C26—C30 | −1.0 (4) |
Fe1—C7—C6—C10 | −59.1 (2) | Fe2—C27—C26—C30 | −60.1 (2) |
C8—C7—C6—Fe1 | 59.3 (2) | C28—C27—C26—Fe2 | 59.1 (2) |
C9—C10—C6—C7 | 0.3 (3) | C29—C30—C26—C27 | 1.0 (3) |
C11—C10—C6—C7 | −179.5 (3) | C31—C30—C26—C27 | −178.9 (3) |
Fe1—C10—C6—C7 | 59.3 (2) | Fe2—C30—C26—C27 | 60.3 (2) |
C9—C10—C6—Fe1 | −59.0 (2) | C29—C30—C26—Fe2 | −59.3 (2) |
C11—C10—C6—Fe1 | 121.3 (3) | C31—C30—C26—Fe2 | 120.8 (3) |
C9—Fe1—C6—C7 | −81.2 (2) | C21—Fe2—C26—C27 | 157.3 (2) |
C1—Fe1—C6—C7 | 163.7 (2) | C30—Fe2—C26—C27 | −118.5 (3) |
C5—Fe1—C6—C7 | −158.8 (4) | C29—Fe2—C26—C27 | −80.4 (2) |
C3—Fe1—C6—C7 | 78.4 (2) | C22—Fe2—C26—C27 | 115.4 (2) |
C8—Fe1—C6—C7 | −37.41 (19) | C25—Fe2—C26—C27 | −170.6 (3) |
C4—Fe1—C6—C7 | 42.2 (4) | C24—Fe2—C26—C27 | 45.5 (5) |
C10—Fe1—C6—C7 | −119.3 (3) | C23—Fe2—C26—C27 | 74.7 (2) |
C2—Fe1—C6—C7 | 121.5 (2) | C28—Fe2—C26—C27 | −36.8 (2) |
C9—Fe1—C6—C10 | 38.11 (18) | C21—Fe2—C26—C30 | −84.3 (2) |
C1—Fe1—C6—C10 | −77.0 (2) | C29—Fe2—C26—C30 | 38.09 (18) |
C5—Fe1—C6—C10 | −39.5 (5) | C22—Fe2—C26—C30 | −126.12 (19) |
C3—Fe1—C6—C10 | −162.28 (18) | C27—Fe2—C26—C30 | 118.5 (3) |
C8—Fe1—C6—C10 | 81.9 (2) | C25—Fe2—C26—C30 | −52.1 (4) |
C4—Fe1—C6—C10 | 161.4 (3) | C24—Fe2—C26—C30 | 163.9 (4) |
C2—Fe1—C6—C10 | −119.24 (19) | C23—Fe2—C26—C30 | −166.89 (18) |
C7—Fe1—C6—C10 | 119.3 (3) | C28—Fe2—C26—C30 | 81.67 (19) |
C9—Fe1—C1—C5 | 77.6 (2) | C26—Fe2—C21—C22 | −80.9 (2) |
C3—Fe1—C1—C5 | −81.7 (2) | C30—Fe2—C21—C22 | −124.4 (2) |
C8—Fe1—C1—C5 | 40.8 (4) | C29—Fe2—C21—C22 | −166.3 (2) |
C4—Fe1—C1—C5 | −38.2 (2) | C27—Fe2—C21—C22 | −46.0 (4) |
C10—Fe1—C1—C5 | 121.27 (19) | C25—Fe2—C21—C22 | 119.2 (3) |
C2—Fe1—C1—C5 | −119.6 (3) | C24—Fe2—C21—C22 | 81.6 (2) |
C7—Fe1—C1—C5 | −158.6 (4) | C23—Fe2—C21—C22 | 38.0 (2) |
C6—Fe1—C1—C5 | 163.89 (19) | C28—Fe2—C21—C22 | 159.4 (5) |
C9—Fe1—C1—C2 | −162.77 (19) | C26—Fe2—C21—C25 | 159.85 (19) |
C5—Fe1—C1—C2 | 119.6 (3) | C30—Fe2—C21—C25 | 116.4 (2) |
C3—Fe1—C1—C2 | 37.9 (2) | C29—Fe2—C21—C25 | 74.5 (2) |
C8—Fe1—C1—C2 | 160.4 (3) | C22—Fe2—C21—C25 | −119.2 (3) |
C4—Fe1—C1—C2 | 81.5 (2) | C27—Fe2—C21—C25 | −165.3 (3) |
C10—Fe1—C1—C2 | −119.09 (19) | C24—Fe2—C21—C25 | −37.6 (2) |
C7—Fe1—C1—C2 | −39.0 (5) | C23—Fe2—C21—C25 | −81.2 (2) |
C6—Fe1—C1—C2 | −76.5 (2) | C28—Fe2—C21—C25 | 40.1 (6) |
C2—C1—C5—C4 | 0.5 (4) | C22—C21—C25—C24 | −0.2 (4) |
Fe1—C1—C5—C4 | 60.0 (2) | Fe2—C21—C25—C24 | 59.7 (2) |
C2—C1—C5—Fe1 | −59.5 (2) | C22—C21—C25—Fe2 | −60.0 (2) |
C9—Fe1—C5—C1 | −120.49 (19) | C26—Fe2—C25—C24 | −164.2 (3) |
C3—Fe1—C5—C1 | 81.2 (2) | C21—Fe2—C25—C24 | −118.9 (3) |
C8—Fe1—C5—C1 | −162.51 (18) | C30—Fe2—C25—C24 | 158.7 (2) |
C4—Fe1—C5—C1 | 118.4 (3) | C29—Fe2—C25—C24 | 114.8 (2) |
C10—Fe1—C5—C1 | −79.2 (2) | C22—Fe2—C25—C24 | −81.4 (2) |
C2—Fe1—C5—C1 | 37.51 (19) | C27—Fe2—C25—C24 | 37.9 (6) |
C7—Fe1—C5—C1 | 165.0 (3) | C23—Fe2—C25—C24 | −37.5 (2) |
C6—Fe1—C5—C1 | −48.6 (5) | C28—Fe2—C25—C24 | 73.2 (3) |
C9—Fe1—C5—C4 | 121.1 (2) | C26—Fe2—C25—C21 | −45.3 (4) |
C1—Fe1—C5—C4 | −118.4 (3) | C30—Fe2—C25—C21 | −82.4 (2) |
C3—Fe1—C5—C4 | −37.2 (2) | C29—Fe2—C25—C21 | −126.2 (2) |
C8—Fe1—C5—C4 | 79.1 (2) | C22—Fe2—C25—C21 | 37.5 (2) |
C10—Fe1—C5—C4 | 162.4 (2) | C27—Fe2—C25—C21 | 156.8 (4) |
C2—Fe1—C5—C4 | −80.9 (2) | C24—Fe2—C25—C21 | 118.9 (3) |
C7—Fe1—C5—C4 | 46.6 (4) | C23—Fe2—C25—C21 | 81.4 (2) |
C6—Fe1—C5—C4 | −167.0 (4) | C28—Fe2—C25—C21 | −167.84 (19) |
C1—C5—C4—C3 | −0.8 (4) | C21—C25—C24—C23 | 0.3 (4) |
Fe1—C5—C4—C3 | 59.1 (2) | Fe2—C25—C24—C23 | 59.5 (2) |
C1—C5—C4—Fe1 | −59.9 (2) | C21—C25—C24—Fe2 | −59.2 (2) |
C9—Fe1—C4—C3 | 163.20 (19) | C26—Fe2—C24—C25 | 157.4 (4) |
C1—Fe1—C4—C3 | −81.6 (2) | C21—Fe2—C24—C25 | 37.9 (2) |
C5—Fe1—C4—C3 | −119.7 (3) | C30—Fe2—C24—C25 | −48.4 (4) |
C8—Fe1—C4—C3 | 122.3 (2) | C29—Fe2—C24—C25 | −83.9 (2) |
C10—Fe1—C4—C3 | −168.0 (3) | C22—Fe2—C24—C25 | 81.6 (2) |
C2—Fe1—C4—C3 | −37.58 (19) | C27—Fe2—C24—C25 | −167.5 (2) |
C7—Fe1—C4—C3 | 81.1 (2) | C23—Fe2—C24—C25 | 119.4 (3) |
C6—Fe1—C4—C3 | 50.9 (4) | C28—Fe2—C24—C25 | −126.5 (2) |
C9—Fe1—C4—C5 | −77.1 (2) | C26—Fe2—C24—C23 | 38.1 (6) |
C1—Fe1—C4—C5 | 38.1 (2) | C21—Fe2—C24—C23 | −81.4 (2) |
C3—Fe1—C4—C5 | 119.7 (3) | C30—Fe2—C24—C23 | −167.8 (3) |
C8—Fe1—C4—C5 | −118.0 (2) | C29—Fe2—C24—C23 | 156.8 (2) |
C10—Fe1—C4—C5 | −48.3 (5) | C22—Fe2—C24—C23 | −37.8 (2) |
C2—Fe1—C4—C5 | 82.1 (2) | C27—Fe2—C24—C23 | 73.1 (3) |
C7—Fe1—C4—C5 | −159.2 (2) | C25—Fe2—C24—C23 | −119.4 (3) |
C6—Fe1—C4—C5 | 170.6 (3) | C28—Fe2—C24—C23 | 114.1 (2) |
C5—C4—C3—C2 | 0.7 (4) | C25—C24—C23—C22 | −0.2 (4) |
Fe1—C4—C3—C2 | 59.6 (2) | Fe2—C24—C23—C22 | 59.2 (2) |
C5—C4—C3—Fe1 | −58.9 (2) | C25—C24—C23—Fe2 | −59.4 (2) |
C9—Fe1—C3—C4 | −42.5 (5) | C26—Fe2—C23—C24 | −167.0 (2) |
C1—Fe1—C3—C4 | 81.3 (2) | C21—Fe2—C23—C24 | 81.4 (2) |
C5—Fe1—C3—C4 | 37.5 (2) | C30—Fe2—C23—C24 | 162.3 (4) |
C8—Fe1—C3—C4 | −75.1 (2) | C29—Fe2—C23—C24 | −50.8 (4) |
C10—Fe1—C3—C4 | 169.2 (3) | C22—Fe2—C23—C24 | 119.1 (3) |
C2—Fe1—C3—C4 | 119.4 (3) | C27—Fe2—C23—C24 | −125.9 (2) |
C7—Fe1—C3—C4 | −116.4 (2) | C25—Fe2—C23—C24 | 37.4 (2) |
C6—Fe1—C3—C4 | −158.0 (2) | C28—Fe2—C23—C24 | −83.8 (2) |
C9—Fe1—C3—C2 | −162.0 (3) | C26—Fe2—C23—C22 | 73.9 (3) |
C1—Fe1—C3—C2 | −38.1 (2) | C21—Fe2—C23—C22 | −37.7 (2) |
C5—Fe1—C3—C2 | −81.9 (2) | C30—Fe2—C23—C22 | 43.2 (5) |
C8—Fe1—C3—C2 | 165.4 (2) | C29—Fe2—C23—C22 | −170.0 (3) |
C4—Fe1—C3—C2 | −119.4 (3) | C27—Fe2—C23—C22 | 115.0 (2) |
C10—Fe1—C3—C2 | 49.8 (4) | C25—Fe2—C23—C22 | −81.7 (2) |
C7—Fe1—C3—C2 | 124.1 (2) | C24—Fe2—C23—C22 | −119.1 (3) |
C6—Fe1—C3—C2 | 82.5 (2) | C28—Fe2—C23—C22 | 157.0 (2) |
C4—C3—C2—C1 | −0.4 (4) | C25—C21—C22—C23 | 0.1 (4) |
Fe1—C3—C2—C1 | 59.2 (2) | Fe2—C21—C22—C23 | −59.9 (2) |
C4—C3—C2—Fe1 | −59.7 (2) | C25—C21—C22—Fe2 | 59.9 (2) |
C5—C1—C2—C3 | −0.1 (4) | C24—C23—C22—C21 | 0.1 (4) |
Fe1—C1—C2—C3 | −59.4 (2) | Fe2—C23—C22—C21 | 59.6 (2) |
C5—C1—C2—Fe1 | 59.3 (2) | C24—C23—C22—Fe2 | −59.5 (2) |
C9—Fe1—C2—C3 | 162.2 (3) | C26—Fe2—C22—C21 | 116.4 (2) |
C1—Fe1—C2—C3 | 118.6 (3) | C30—Fe2—C22—C21 | 75.5 (2) |
C5—Fe1—C2—C3 | 81.3 (2) | C29—Fe2—C22—C21 | 44.6 (6) |
C8—Fe1—C2—C3 | −38.3 (5) | C27—Fe2—C22—C21 | 158.7 (2) |
C4—Fe1—C2—C3 | 37.4 (2) | C25—Fe2—C22—C21 | −37.7 (2) |
C10—Fe1—C2—C3 | −160.3 (2) | C24—Fe2—C22—C21 | −81.2 (2) |
C7—Fe1—C2—C3 | −74.7 (2) | C23—Fe2—C22—C21 | −118.8 (3) |
C6—Fe1—C2—C3 | −117.0 (2) | C28—Fe2—C22—C21 | −168.2 (3) |
C9—Fe1—C2—C1 | 43.5 (4) | C26—Fe2—C22—C23 | −124.9 (2) |
C5—Fe1—C2—C1 | −37.39 (19) | C21—Fe2—C22—C23 | 118.8 (3) |
C3—Fe1—C2—C1 | −118.6 (3) | C30—Fe2—C22—C23 | −165.7 (2) |
C8—Fe1—C2—C1 | −157.0 (4) | C29—Fe2—C22—C23 | 163.4 (5) |
C4—Fe1—C2—C1 | −81.3 (2) | C27—Fe2—C22—C23 | −82.5 (2) |
C10—Fe1—C2—C1 | 81.1 (2) | C25—Fe2—C22—C23 | 81.0 (2) |
C7—Fe1—C2—C1 | 166.71 (19) | C24—Fe2—C22—C23 | 37.5 (2) |
C6—Fe1—C2—C1 | 124.36 (19) | C28—Fe2—C22—C23 | −49.4 (4) |
C9—C10—C11—O1 | 24.6 (5) | C26—C30—C31—O3 | −22.4 (5) |
C6—C10—C11—O1 | −155.7 (3) | C29—C30—C31—O3 | 157.7 (3) |
Fe1—C10—C11—O1 | −64.7 (4) | Fe2—C30—C31—O3 | 67.3 (4) |
C9—C10—C11—C12 | −153.7 (3) | C26—C30—C31—C32 | 154.3 (3) |
C6—C10—C11—C12 | 25.9 (5) | C29—C30—C31—C32 | −25.6 (5) |
Fe1—C10—C11—C12 | 116.9 (3) | Fe2—C30—C31—C32 | −116.0 (3) |
O1—C11—C12—C13 | 3.9 (5) | O3—C31—C32—C33 | −4.2 (5) |
C10—C11—C12—C13 | −177.8 (3) | C30—C31—C32—C33 | 179.2 (3) |
C15—N1—C13—C12 | 170.2 (3) | C35—N2—C33—C32 | −177.0 (3) |
C15—N1—C13—C14 | −10.9 (5) | C35—N2—C33—C34 | 3.2 (5) |
C11—C12—C13—N1 | 1.5 (5) | C31—C32—C33—N2 | −2.5 (5) |
C11—C12—C13—C14 | −177.4 (3) | C31—C32—C33—C34 | 177.4 (3) |
C13—N1—C15—C20 | −124.1 (3) | C33—N2—C35—C36 | −57.6 (4) |
C13—N1—C15—C16 | 58.5 (5) | C33—N2—C35—C40 | 126.3 (3) |
C20—C15—C16—C17 | 2.9 (5) | C36—C35—C40—C39 | 1.7 (4) |
N1—C15—C16—C17 | −179.7 (3) | N2—C35—C40—C39 | 177.9 (3) |
C15—C16—C17—C18 | −1.1 (5) | C35—C40—C39—C38 | 0.5 (5) |
C16—C17—C18—O2 | 177.7 (3) | C40—C39—C38—O4 | 178.5 (3) |
C16—C17—C18—C19 | −2.3 (5) | C40—C39—C38—C37 | −2.0 (5) |
O2—C18—C19—C20 | −176.2 (3) | O4—C38—C37—C36 | −179.3 (3) |
C17—C18—C19—C20 | 3.8 (5) | C39—C38—C37—C36 | 1.3 (4) |
C18—C19—C20—C15 | −2.0 (5) | C38—C37—C36—C35 | 0.9 (4) |
C16—C15—C20—C19 | −1.4 (5) | C40—C35—C36—C37 | −2.4 (4) |
N1—C15—C20—C19 | −178.9 (3) | N2—C35—C36—C37 | −178.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.88 | 1.89 | 2.607 (3) | 138 |
N2—H2N···O3 | 0.88 | 1.91 | 2.623 (3) | 137 |
O2—H2O···O3i | 0.84 | 1.80 | 2.632 (3) | 170 |
O4—H4O···O1 | 0.84 | 1.82 | 2.651 (3) | 169 |
C4—H4···Cg6ii | 0.95 | 2.94 | 3.696 (4) | 137 |
C6—H6···Cg3iii | 0.95 | 2.76 | 3.673 (3) | 161 |
C23—H23···Cg3iv | 0.95 | 2.84 | 3.592 (4) | 137 |
C29—H29···Cg6iv | 0.95 | 2.92 | 3.786 (4) | 152 |
C37—H37···Cg5v | 0.95 | 2.97 | 3.710 (3) | 135 |
C40—H40···Cg1vi | 0.95 | 2.93 | 3.663 (3) | 135 |
Symmetry codes: (i) x+1, y, z−1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+2, −z+1; (v) −x, −y+2, −z+1; (vi) −x+1, −y+1, −z+1. |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | [Fe(C5H5)(C15H14NO2)] | [Fe(C5H5)(C15H14NO2)] |
Mr | 361.21 | 361.21 |
Crystal system, space group | TriclinicP1 | TriclinicP1 |
Temperature (K) | 293 | 173 |
a, b, c (Å) | 9.768 (2), 10.804 (2), 16.244 (3) | 7.4100 (11), 14.687 (2), 15.5601 (19) |
α, β, γ (°) | 91.39 (3), 97.05 (3), 99.22 (3) | 80.370 (7), 77.677 (7), 86.297 (8) |
V (Å3) | 1677.7 (6) | 1630.3 (4) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.91 | 0.94 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 | 0.30 × 0.15 × 0.12 |
Data collection | ||
Diffractometer | Enraf–Nonius CAD-4 diffractometer | Rigaku Mercury diffractometer |
Absorption correction | Psi-scan ψ scan (North et al., 1968) | Multi-scan (Jacobson, 1998) |
Tmin, Tmax | 0.772, 0.839 | 0.767, 0.896 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6988, 6576, 3837 | 15645, 5891, 4742 |
Rint | 0.033 | 0.036 |
(sin θ/λ)max (Å−1) | 0.616 | 0.602 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.126, 1.01 | 0.048, 0.105, 1.10 |
No. of reflections | 6576 | 5891 |
No. of parameters | 437 | 438 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.50, −0.34 | 0.47, −0.38 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CrystalClear (Rigaku, 2001), CAD-4 Software, CrystalClear, XCAD4 (Harms & Wocadlo,1995), CrystalStructure (Rigaku, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.
O1—C11 | 1.265 (5) | N2—C33 | 1.348 (5) |
N1—C13 | 1.340 (5) | N2—C35 | 1.423 (5) |
N1—C15 | 1.429 (5) | C30—C31 | 1.470 (6) |
C10—C11 | 1.491 (6) | C31—C32 | 1.417 (6) |
C11—C12 | 1.400 (5) | C32—C33 | 1.369 (6) |
C13—C14 | 1.493 (5) | C33—C34 | 1.503 (6) |
O3—C31 | 1.256 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.86 | 1.96 | 2.642 (5) | 136 |
N2—H2N···O3 | 0.86 | 1.99 | 2.645 (5) | 132 |
O2—H2O···O3i | 0.82 | 1.82 | 2.629 (5) | 170 |
O4—H4O···O1 | 0.82 | 1.86 | 2.679 (5) | 172 |
C2—H2···Cg3ii | 0.93 | 2.85 | 3.686 (5) | 150 |
C4—H4···Cg6iii | 0.93 | 2.89 | 3.614 (6) | 135 |
C28—H28···Cg3iv | 0.93 | 2.96 | 3.655 (6) | 133 |
Symmetry codes: (i) x−1, y+1, z; (ii) −x, −y+2, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z+2. |
O1—C11 | 1.269 (4) | O3—C31 | 1.275 (4) |
N1—C13 | 1.336 (4) | N2—C33 | 1.337 (4) |
N1—C15 | 1.427 (4) | N2—C35 | 1.423 (4) |
C10—C11 | 1.482 (4) | C30—C31 | 1.481 (4) |
C11—C12 | 1.406 (4) | C31—C32 | 1.413 (4) |
C12—C13 | 1.391 (4) | C32—C33 | 1.386 (4) |
C13—C14 | 1.498 (4) | C33—C34 | 1.502 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.88 | 1.89 | 2.607 (3) | 138 |
N2—H2N···O3 | 0.88 | 1.91 | 2.623 (3) | 137 |
O2—H2O···O3i | 0.84 | 1.80 | 2.632 (3) | 170 |
O4—H4O···O1 | 0.84 | 1.82 | 2.651 (3) | 169 |
C4—H4···Cg6ii | 0.95 | 2.94 | 3.696 (4) | 137 |
C6—H6···Cg3iii | 0.95 | 2.76 | 3.673 (3) | 161 |
C23—H23···Cg3iv | 0.95 | 2.84 | 3.592 (4) | 137 |
C29—H29···Cg6iv | 0.95 | 2.92 | 3.786 (4) | 152 |
C37—H37···Cg5v | 0.95 | 2.97 | 3.710 (3) | 135 |
C40—H40···Cg1vi | 0.95 | 2.93 | 3.663 (3) | 135 |
Symmetry codes: (i) x+1, y, z−1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+2, −z+1; (v) −x, −y+2, −z+1; (vi) −x+1, −y+1, −z+1. |
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It has been shown (Shi, Yang, Shen et al., 2004; Shi, Yang, Song & Liu, 2004) that primary amines, Ar'NH2, react smoothly with β–diketones, ArCOCH2COR, to give enaminones, ArCOCH═C(NHAr')R, in good yields. In continuation of our investigation of the chemistry of ferrocenyl enaminones (Shi et al., 2005), we have synthesized the title compounds, (C5H5)FeC5H4COCH═C(NHAr')CH3 [Ar' = 3-HOC6H4 for (I) and Ar' = 4-HOC6H4 for (II)]. We report here the molecular and supramolecular structures of these isomeric organometallic compounds.
The title compounds crystallize with Z' = 2 in space group P1 (Figs. 1 and 3). In the two independent molecules, the bond lengths (Tables 1 and 3) are almost identical. As noted in the compounds previously reported, the O═C—C═C—N unit is planar and the bond lengths indicate electron delocalization (Gilli et al., 2000; Shi, Yang, Shen et al., 2004; Shi, Yang, Song & Liu, 2004). However, for each of the compounds (I) and (II), the two distinct molecules show different conformations. The O═C—C═C—N plane is twisted with respect to the benzene and substituted cyclopentadienyl rings by 70.5 (2) and 21.0 (3)° for (Ia), 66.4 (2) and 19.5 (3)° for (Ib), 53.56 (15) and 26.07 (17)° for (IIa), and 57.24 (15) and 24.95 (18)° for (IIb). Consistent with the large dihedral angles between the O═C—C═C—N plane and the substituted cyclopentadienyl ring, the C10—C11 and C30—C31 bonds linking the O═C—C═C—N group and the substituted cyclopentadienyl ring are typical of a single bond (Csp2—Csp2), so suggesting that the substituted cyclopentadienyl ring is not involved in the conjugation of the O═ C—C═C—N group.
Although two compounds in the solid state have strong N—H···O═C intramolecular hydrogen bonds (Tables 2 and 4), their packing modes are markedly different. For compound (I), atom O2 in the type 1 molecule (Fig. 1a) at (x, y, z) acts as a hydrogen-bond donor to carbonyl atom O3 in the type 2 molecule at (x - 1, 1 + y, z), so generating two infinite one-dimensional chains in the [110] direction, which are linked by an O—H···O═C hydrogen bond, viz. atom O4 in the type 2 molecule (Fig. 1b) at (x, y, z) acts as a donor to the type 1 atom O1 in the same asymmetric unit (Fig. 2). For compound (II), atom O2 in the type 1 molecule (Fig. 3a) at (x, y, z) acts as a hydrogen-bond donor to carbonyl atom O3 in the type 2 molecule at (1 + x, y, z - 1), thus resulting in two [101] infinite one-dimensional chains which are linked by an O—H···O═C hydrogen bond from atom O4 in the type 2 molecule (Fig. 3b) at (x, y, z) and the type 1 atom O1 in the same asymmetric unit (Fig. 4).
In addition to the above strong hydrogen bonds, weak C—H···π(arene) hydrogen bonds are present in compounds (I) and (II) (Tables 2 and 4). For compound (I), atom C2 in the type 1 molecule at (x, y, z) acts as a hydrogen-bond donor to the C15–C20 ring in the type 1 molecule at (-x, 2 - y, 1 - z), whereas atom C4 in the type 1 molecule at (x, y, z) acts as a donor to the C35–C40 ring in the type 2 molecule at (1 - x, 1 - y, 1 - z) (Fig. 2). Atom C28 in the type 2 molecule at (x, y, z) acts as a hydrogen-bond donor to the C15–C20 ring in the type 1 molecule at (1 - x, 1 - y, 2 - z). For compound (II), atoms C4 and C6 in the type 1 molecule at (x, y, z) act as hydrogen-bond donors to the C35–C40 ring in the type 2 molecule at (-x, 1 - y, 1 - z) and to the C15–C20 ring in the type 1 molecule at (1 - x, 1 - y, -z), respectively. Atoms C23 and C29 in the type 2 molecule at (x, y, z) act as donors to the C15–C20 ring in the type 1 molecule at (1 - x, 2 - y, 1 - z) and to the C35–C40 ring in the type 2 molecule at (1 - x, 2 - y, 1 - z), respectively. Unlike compound (I), hydrogen bonds involving the cyclopentadienyl rings as acceptors are also observed; benzene atoms C37 and C40 in the type 2 molecule at (x, y, z) act as hydrogen-bond donors to the C26–C30 ring in the type 2 molecule at (-x, 2 - y, 1 - z) and to the C1–C5 ring in the type 1 molecule at (1 - x, 1 - y, 1 - z), respectively (Fig. 4).