Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111021536/gg3253sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111021536/gg3253IVsup2.hkl |
CCDC reference: 745627
All experiments were conducted in air using reagent-grade solvents, and all chemicals were from commercial sources and used without further purification. CHN elemental analysis was performed on a CE Instruments Eager 300 apparatus. Crystals of (IV) of sufficient quality for X-ray diffraction analysis were obtained by the diffusion of hexane into a CH2Cl2 solution.
The synthesis and purification procedure for (IV) were carried out as follows. Oxindole (I) (?mg, ?mmol) and ferrocene-1,1'-dicarbaldehyde, (II) (?mg, ?mmol), were combined in ethanol (10 ml) and piperidine (3 drops), and heated for 3 h at 353 K. After cooling, the reaction mixture was concentrated in vacuo. The resulting residue was dissolved in ethyl acetate (20 ml), washed with brine solution (10 ml) and then dried (MgSO4). Removal of the MgSO4 followed by concentration of the solvent afforded an oil, which was taken up in CH2Cl2 (5 ml), and a dark-brown precipitate formed upon addition of hexane (20 ml). The precipitate, (IV), was collected by filtration and dried in vacuo. Analysis, found: C 68.48; H 4.39, N 6.02%; C28H20FeN2O2.0.25CH2Cl2 requires: C 68.75, H 4.19, N 5.68%. HRMS: m/z calculated for C28H20FeN2O2.0.25CH2Cl2 ([M+Na for 56Fe]+): 493.0815; found: 493.0815. While the empirical formula was found to contain only 0.25 molecules of CH2Cl2 per ferrocene complex by elemental analysis and HRMS, the crystal structure was found to contain two molecules of dichloromethane per ferrocene unit. NMR spectra were measured on a JEOL EX270 spectrometer at 270 MHz (1H). 1H NMR (probable mixture of isomers; δ, p.p.m.): 10.49 (1H, m), 8.19 (1H, m), 7.80 (1H, m), 7.38–6.68 (5H, m), 5.39 (3H, m), 4.96 (2H, m), 4.60 (1H, m),4.56 (6H, m).
All H atoms were added at calculated positions and refined using a riding model, with C—H = 0.95 for aromatic H or 0.99 Å for methylene H, and N—H = 0.88 Å, with Uiso(H) = 1.2Ueq(C,N).
The R factor is rather high, at 0.085. It is thought that this may be the result of the long unit-cell axis (c is nearly 50 Å) and the low intensity of the diffraction data, especially at higher 2θ angles. In an effort to deal with these issues, this was the second data set collected on this compound. The data were collected with a molybdenum rotating-anode X-ray source that is approximately ten times more intense than a normal laboratory X-ray source, and the crystal-to-detector distance used was 75 mm, to ensure separation of the reflections. This longer distance obviously led to even lower intensity at the detector. There was no access to a copper X-ray source. To ensure the maximum possible intensity, the data collection was completed in approximately 17 h. The data reduction was carried out carefully to maximize the quality of the data set, but the low intensity of the diffraction at higher angles frustrated these efforts to some degree, leading to the rather high agreement statistics.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: WinGX (Farrugia, 1999), Mercury (Version 2.4; Macrae et al., 2008) and PARST95 (Nardelli, 1995).
[Fe(C28H20N2O2)]·2CH2Cl2 | F(000) = 2624 |
Mr = 642.16 | Dx = 1.544 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 95670 reflections |
a = 7.8609 (2) Å | θ = 2.9–27.5° |
b = 14.1905 (4) Å | µ = 0.97 mm−1 |
c = 49.5413 (12) Å | T = 120 K |
β = 90.099 (1)° | Lath, red |
V = 5526.3 (2) Å3 | 0.17 × 0.04 × 0.03 mm |
Z = 8 |
Bruker Nonius APEX II CCD camera on κ-goniostat diffractometer | 9612 independent reflections |
Radiation source: Bruker Nonius FR591 rotating anode | 7846 reflections with I > 2σ(I) |
10cm confocal mirrors monochromator | Rint = 0.063 |
Detector resolution: 4096x4096pixels/62x62mm pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
ϕ and ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | k = −16→16 |
Tmin = 0.853, Tmax = 0.972 | l = −58→58 |
54405 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)] = 0.085 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.173 | H-atom parameters constrained |
S = 1.17 | w = 1/[σ2(Fo2) + 47.692P] where P = (Fo2 + 2Fc2)/3 |
9612 reflections | (Δ/σ)max < 0.001 |
703 parameters | Δρmax = 0.63 e Å−3 |
0 restraints | Δρmin = −0.55 e Å−3 |
[Fe(C28H20N2O2)]·2CH2Cl2 | V = 5526.3 (2) Å3 |
Mr = 642.16 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.8609 (2) Å | µ = 0.97 mm−1 |
b = 14.1905 (4) Å | T = 120 K |
c = 49.5413 (12) Å | 0.17 × 0.04 × 0.03 mm |
β = 90.099 (1)° |
Bruker Nonius APEX II CCD camera on κ-goniostat diffractometer | 9612 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | 7846 reflections with I > 2σ(I) |
Tmin = 0.853, Tmax = 0.972 | Rint = 0.063 |
54405 measured reflections |
R[F2 > 2σ(F2)] = 0.085 | 0 restraints |
wR(F2) = 0.173 | H-atom parameters constrained |
S = 1.17 | w = 1/[σ2(Fo2) + 47.692P] where P = (Fo2 + 2Fc2)/3 |
9612 reflections | Δρmax = 0.63 e Å−3 |
703 parameters | Δρmin = −0.55 e Å−3 |
Experimental. SADABS was used to perform the absorption correction. Estimated minimum and maximum transmission from SADABS: 0.6446 and 0.7456. The given Tmin and Tmax were generated using the SHELX SIZE command. NMR spectra were measured on a JEOL EX270 spectrometer at 270 MHz (1H). 1H NMR (probable mixture of isomers) 10.49 (1H, m), 8.19 (1H,m), 7.80 (1H, m), 7.38–6.68 (5H, m), 5.39 (3H, m), 4.96 (2H, m), 4.60 (1H, m),4.56 (6H, m). HRMS: m/z calculated for C28H20FeN2O2.0.25CH2Cl2 ([M+Na for 56Fe]+): 493.0815; found: 493.0815. |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | −0.5988 (8) | 0.4197 (4) | 0.08115 (12) | 0.0233 (14) | |
C2 | −0.6071 (8) | 0.5072 (5) | 0.09587 (13) | 0.0275 (15) | |
H2 | −0.5666 | 0.5178 | 0.1137 | 0.033* | |
C3 | −0.6862 (8) | 0.5745 (5) | 0.07901 (13) | 0.0323 (16) | |
H3 | −0.7101 | 0.6380 | 0.0838 | 0.039* | |
C4 | −0.7240 (8) | 0.5329 (5) | 0.05401 (14) | 0.0325 (16) | |
H4 | −0.7781 | 0.5631 | 0.0392 | 0.039* | |
C5 | −0.6675 (7) | 0.4378 (5) | 0.05466 (13) | 0.0245 (14) | |
H5 | −0.6738 | 0.3939 | 0.0402 | 0.029* | |
C6 | −0.2115 (8) | 0.5003 (5) | 0.06288 (13) | 0.0245 (14) | |
C7 | −0.2498 (8) | 0.5954 (5) | 0.07069 (14) | 0.0307 (15) | |
H7 | −0.2240 | 0.6231 | 0.0877 | 0.037* | |
C8 | −0.3324 (9) | 0.6411 (5) | 0.04894 (14) | 0.0342 (17) | |
H8 | −0.3694 | 0.7048 | 0.0487 | 0.041* | |
C9 | −0.3502 (8) | 0.5750 (5) | 0.02754 (14) | 0.0328 (16) | |
H9 | −0.4023 | 0.5866 | 0.0105 | 0.039* | |
C10 | −0.2764 (8) | 0.4883 (5) | 0.03610 (13) | 0.0292 (15) | |
H10 | −0.2710 | 0.4320 | 0.0258 | 0.035* | |
C11 | −0.5185 (8) | 0.3302 (5) | 0.08846 (13) | 0.0263 (14) | |
H11 | −0.4730 | 0.2954 | 0.0738 | 0.032* | |
C12 | −0.4996 (7) | 0.2899 (4) | 0.11263 (12) | 0.0211 (13) | |
C13 | −0.3977 (8) | 0.2006 (5) | 0.11450 (13) | 0.0252 (14) | |
C14 | −0.4774 (7) | 0.2393 (4) | 0.15674 (12) | 0.0222 (13) | |
C15 | −0.5502 (8) | 0.3095 (4) | 0.14043 (13) | 0.0241 (14) | |
C16 | −0.6580 (8) | 0.3751 (4) | 0.15251 (13) | 0.0266 (15) | |
H16 | −0.7124 | 0.4221 | 0.1419 | 0.032* | |
C17 | −0.6848 (9) | 0.3710 (5) | 0.18001 (14) | 0.0316 (16) | |
H17 | −0.7582 | 0.4157 | 0.1882 | 0.038* | |
C18 | −0.6075 (9) | 0.3035 (5) | 0.19581 (14) | 0.0326 (16) | |
H18 | −0.6268 | 0.3031 | 0.2147 | 0.039* | |
C19 | −0.5007 (8) | 0.2356 (4) | 0.18424 (12) | 0.0251 (14) | |
H19 | −0.4466 | 0.1888 | 0.1950 | 0.030* | |
C20 | −0.1402 (7) | 0.4322 (5) | 0.08138 (13) | 0.0241 (14) | |
H20 | −0.1537 | 0.4478 | 0.0999 | 0.029* | |
C21 | −0.0586 (8) | 0.3511 (5) | 0.07691 (12) | 0.0261 (15) | |
C22 | −0.0083 (8) | 0.2928 (5) | 0.10055 (13) | 0.0252 (14) | |
C23 | 0.0934 (8) | 0.2208 (5) | 0.06279 (13) | 0.0291 (15) | |
C24 | 0.0082 (8) | 0.3024 (5) | 0.05309 (13) | 0.0275 (15) | |
C25 | 0.0160 (8) | 0.3213 (5) | 0.02561 (13) | 0.0282 (15) | |
H25 | −0.0367 | 0.3762 | 0.0185 | 0.034* | |
C26 | 0.1005 (8) | 0.2602 (5) | 0.00865 (13) | 0.0306 (16) | |
H26 | 0.1051 | 0.2733 | −0.0101 | 0.037* | |
C27 | 0.1784 (9) | 0.1804 (5) | 0.01854 (14) | 0.0348 (17) | |
H27 | 0.2340 | 0.1389 | 0.0064 | 0.042* | |
C28 | 0.1777 (8) | 0.1591 (5) | 0.04594 (14) | 0.0320 (16) | |
H28 | 0.2329 | 0.1045 | 0.0528 | 0.038* | |
N1 | −0.3842 (7) | 0.1777 (4) | 0.14070 (11) | 0.0264 (12) | |
H1 | −0.3242 | 0.1300 | 0.1469 | 0.032* | |
N2 | 0.0794 (6) | 0.2164 (4) | 0.09089 (10) | 0.0275 (12) | |
H2A | 0.1212 | 0.1709 | 0.1010 | 0.033* | |
O1 | −0.3339 (6) | 0.1574 (3) | 0.09524 (9) | 0.0305 (11) | |
O2 | −0.0382 (6) | 0.3068 (3) | 0.12460 (9) | 0.0311 (11) | |
Fe1 | −0.46894 (12) | 0.52616 (6) | 0.061441 (18) | 0.0243 (2) | |
C101 | 0.0718 (8) | −0.2528 (4) | 0.16621 (12) | 0.0212 (13) | |
C102 | 0.2059 (8) | −0.2991 (4) | 0.15215 (12) | 0.0222 (13) | |
H102 | 0.2482 | −0.2825 | 0.1348 | 0.027* | |
C103 | 0.2656 (8) | −0.3747 (5) | 0.16857 (13) | 0.0267 (15) | |
H103 | 0.3530 | −0.4180 | 0.1639 | 0.032* | |
C104 | 0.1730 (8) | −0.3741 (5) | 0.19281 (13) | 0.0282 (15) | |
H104 | 0.1875 | −0.4168 | 0.2074 | 0.034* | |
C105 | 0.0551 (8) | −0.2995 (4) | 0.19180 (12) | 0.0252 (14) | |
H105 | −0.0224 | −0.2828 | 0.2057 | 0.030* | |
C106 | 0.3907 (8) | −0.1135 (4) | 0.18866 (12) | 0.0242 (14) | |
C107 | 0.5210 (8) | −0.1812 (5) | 0.18140 (13) | 0.0255 (14) | |
H107 | 0.5825 | −0.1820 | 0.1649 | 0.031* | |
C108 | 0.5413 (8) | −0.2456 (5) | 0.20282 (13) | 0.0295 (15) | |
H108 | 0.6200 | −0.2963 | 0.2035 | 0.035* | |
C109 | 0.4239 (8) | −0.2213 (5) | 0.22311 (13) | 0.0278 (15) | |
H109 | 0.4107 | −0.2534 | 0.2398 | 0.033* | |
C110 | 0.3293 (8) | −0.1421 (4) | 0.21490 (12) | 0.0236 (14) | |
H110 | 0.2408 | −0.1127 | 0.2248 | 0.028* | |
C111 | −0.0271 (7) | −0.1694 (4) | 0.15994 (12) | 0.0202 (13) | |
H111 | −0.0775 | −0.1401 | 0.1752 | 0.024* | |
C112 | −0.0605 (7) | −0.1258 (4) | 0.13626 (12) | 0.0211 (13) | |
C113 | −0.1531 (7) | −0.0335 (4) | 0.13666 (12) | 0.0210 (13) | |
C114 | −0.0697 (8) | −0.0634 (4) | 0.09344 (12) | 0.0225 (13) | |
C115 | −0.0179 (7) | −0.1437 (4) | 0.10791 (12) | 0.0206 (13) | |
C116 | 0.0432 (7) | −0.2202 (5) | 0.09347 (13) | 0.0245 (14) | |
H116 | 0.0711 | −0.2772 | 0.1025 | 0.029* | |
C117 | 0.0630 (8) | −0.2129 (5) | 0.06578 (13) | 0.0313 (16) | |
H117 | 0.1058 | −0.2650 | 0.0558 | 0.038* | |
C118 | 0.0210 (8) | −0.1305 (5) | 0.05244 (13) | 0.0306 (16) | |
H118 | 0.0401 | −0.1261 | 0.0336 | 0.037* | |
C119 | −0.0485 (8) | −0.0540 (5) | 0.06607 (13) | 0.0286 (15) | |
H119 | −0.0798 | 0.0022 | 0.0569 | 0.034* | |
C120 | 0.3356 (8) | −0.0402 (4) | 0.17034 (12) | 0.0215 (13) | |
H120 | 0.3717 | −0.0494 | 0.1522 | 0.026* | |
C121 | 0.2430 (7) | 0.0384 (4) | 0.17404 (12) | 0.0216 (13) | |
C122 | 0.1908 (8) | 0.0958 (4) | 0.15007 (12) | 0.0234 (14) | |
C123 | 0.0609 (8) | 0.1587 (4) | 0.18659 (12) | 0.0248 (14) | |
C124 | 0.1585 (8) | 0.0847 (4) | 0.19714 (12) | 0.0218 (13) | |
C125 | 0.1695 (8) | 0.0746 (5) | 0.22498 (12) | 0.0254 (14) | |
H125 | 0.2414 | 0.0278 | 0.2326 | 0.031* | |
C126 | 0.0757 (8) | 0.1329 (5) | 0.24150 (13) | 0.0275 (15) | |
H126 | 0.0813 | 0.1251 | 0.2605 | 0.033* | |
C127 | −0.0278 (8) | 0.2035 (5) | 0.23048 (14) | 0.0298 (15) | |
H127 | −0.0935 | 0.2424 | 0.2420 | 0.036* | |
C128 | −0.0349 (8) | 0.2168 (5) | 0.20264 (14) | 0.0301 (15) | |
H128 | −0.1042 | 0.2648 | 0.1950 | 0.036* | |
N101 | −0.1470 (7) | 0.0011 (4) | 0.11117 (10) | 0.0246 (12) | |
H101 | −0.1862 | 0.0567 | 0.1063 | 0.029* | |
N102 | 0.0832 (6) | 0.1625 (4) | 0.15876 (10) | 0.0250 (12) | |
H10A | 0.0328 | 0.2037 | 0.1481 | 0.030* | |
O101 | −0.2215 (5) | 0.0043 (3) | 0.15619 (8) | 0.0276 (10) | |
O102 | 0.2362 (5) | 0.0845 (3) | 0.12643 (8) | 0.0286 (10) | |
Fe11 | 0.29568 (11) | −0.24844 (6) | 0.187934 (17) | 0.0210 (2) | |
C201 | 0.4288 (10) | −0.0732 (6) | 0.09020 (14) | 0.0385 (18) | |
H20A | 0.3033 | −0.0776 | 0.0913 | 0.046* | |
H20B | 0.4652 | −0.0172 | 0.1006 | 0.046* | |
Cl21 | 0.4894 (3) | −0.05986 (15) | 0.05659 (4) | 0.0478 (5) | |
Cl22 | 0.5211 (2) | −0.17618 (14) | 0.10453 (4) | 0.0403 (4) | |
C301 | 0.3279 (10) | −0.1579 (5) | −0.02580 (15) | 0.0421 (19) | |
H30A | 0.4234 | −0.1427 | −0.0381 | 0.050* | |
H30B | 0.2310 | −0.1799 | −0.0369 | 0.050* | |
Cl31 | 0.3906 (3) | −0.24859 (15) | −0.00332 (5) | 0.0568 (6) | |
Cl32 | 0.2683 (3) | −0.05626 (14) | −0.00801 (4) | 0.0467 (5) | |
C401 | −0.2004 (15) | 0.4667 (8) | 0.1677 (2) | 0.084 (4) | |
H40A | −0.2741 | 0.4146 | 0.1614 | 0.101* | |
H40B | −0.0818 | 0.4503 | 0.1630 | 0.101* | |
Cl41 | −0.2570 (3) | 0.56897 (19) | 0.15025 (5) | 0.0639 (6) | |
Cl42 | −0.2150 (4) | 0.47350 (19) | 0.20177 (5) | 0.0823 (9) | |
C501 | −0.2521 (9) | −0.0170 (5) | 0.22222 (13) | 0.0307 (15) | |
H50A | −0.3145 | −0.0452 | 0.2069 | 0.037* | |
H50B | −0.1683 | 0.0283 | 0.2149 | 0.037* | |
Cl51 | −0.1450 (2) | −0.10604 (13) | 0.24014 (4) | 0.0413 (4) | |
Cl52 | −0.3971 (2) | 0.04349 (14) | 0.24338 (4) | 0.0435 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.019 (3) | 0.024 (3) | 0.027 (3) | −0.002 (3) | 0.000 (3) | 0.003 (3) |
C2 | 0.028 (4) | 0.029 (4) | 0.026 (3) | 0.004 (3) | 0.005 (3) | 0.007 (3) |
C3 | 0.032 (4) | 0.033 (4) | 0.032 (4) | 0.013 (3) | 0.010 (3) | 0.006 (3) |
C4 | 0.028 (4) | 0.034 (4) | 0.035 (4) | 0.005 (3) | −0.002 (3) | 0.013 (3) |
C5 | 0.018 (3) | 0.024 (3) | 0.031 (3) | −0.005 (3) | −0.002 (3) | 0.001 (3) |
C6 | 0.018 (3) | 0.026 (4) | 0.029 (3) | 0.002 (3) | 0.003 (3) | 0.006 (3) |
C7 | 0.028 (4) | 0.028 (4) | 0.036 (4) | −0.005 (3) | 0.002 (3) | 0.001 (3) |
C8 | 0.038 (4) | 0.024 (4) | 0.041 (4) | −0.001 (3) | 0.011 (3) | 0.008 (3) |
C9 | 0.030 (4) | 0.039 (4) | 0.030 (4) | 0.009 (3) | 0.007 (3) | 0.017 (3) |
C10 | 0.026 (4) | 0.031 (4) | 0.031 (4) | 0.005 (3) | 0.003 (3) | 0.002 (3) |
C11 | 0.023 (3) | 0.030 (4) | 0.026 (3) | −0.003 (3) | −0.002 (3) | −0.003 (3) |
C12 | 0.016 (3) | 0.021 (3) | 0.026 (3) | −0.003 (3) | 0.000 (2) | −0.001 (3) |
C13 | 0.020 (3) | 0.023 (4) | 0.032 (4) | 0.000 (3) | −0.003 (3) | −0.002 (3) |
C14 | 0.014 (3) | 0.021 (3) | 0.032 (3) | 0.000 (3) | 0.001 (2) | 0.002 (3) |
C15 | 0.021 (3) | 0.021 (3) | 0.030 (3) | 0.000 (3) | −0.003 (3) | 0.002 (3) |
C16 | 0.030 (4) | 0.010 (3) | 0.040 (4) | −0.001 (3) | 0.004 (3) | 0.002 (3) |
C17 | 0.037 (4) | 0.022 (4) | 0.036 (4) | 0.004 (3) | 0.007 (3) | −0.002 (3) |
C18 | 0.034 (4) | 0.033 (4) | 0.031 (4) | −0.011 (3) | 0.011 (3) | 0.000 (3) |
C19 | 0.024 (3) | 0.022 (3) | 0.029 (3) | −0.003 (3) | −0.001 (3) | 0.007 (3) |
C20 | 0.017 (3) | 0.030 (4) | 0.025 (3) | −0.003 (3) | −0.004 (2) | −0.003 (3) |
C21 | 0.020 (3) | 0.035 (4) | 0.023 (3) | −0.007 (3) | −0.002 (3) | 0.003 (3) |
C22 | 0.016 (3) | 0.028 (4) | 0.031 (4) | −0.005 (3) | −0.003 (3) | 0.004 (3) |
C23 | 0.023 (3) | 0.034 (4) | 0.030 (4) | −0.008 (3) | 0.003 (3) | 0.001 (3) |
C24 | 0.020 (3) | 0.031 (4) | 0.032 (4) | −0.002 (3) | 0.001 (3) | 0.002 (3) |
C25 | 0.019 (3) | 0.037 (4) | 0.028 (4) | −0.006 (3) | 0.000 (3) | −0.001 (3) |
C26 | 0.025 (3) | 0.039 (4) | 0.028 (3) | −0.008 (3) | 0.004 (3) | −0.002 (3) |
C27 | 0.029 (4) | 0.043 (5) | 0.033 (4) | −0.002 (3) | 0.004 (3) | −0.005 (3) |
C28 | 0.029 (4) | 0.031 (4) | 0.036 (4) | 0.001 (3) | −0.001 (3) | 0.001 (3) |
N1 | 0.025 (3) | 0.017 (3) | 0.037 (3) | 0.004 (2) | −0.002 (2) | 0.001 (2) |
N2 | 0.022 (3) | 0.031 (3) | 0.029 (3) | 0.004 (2) | 0.000 (2) | 0.005 (2) |
O1 | 0.036 (3) | 0.025 (3) | 0.030 (2) | 0.009 (2) | 0.006 (2) | 0.001 (2) |
O2 | 0.029 (3) | 0.040 (3) | 0.024 (2) | 0.004 (2) | −0.0014 (19) | 0.002 (2) |
Fe1 | 0.0259 (5) | 0.0219 (5) | 0.0251 (5) | 0.0021 (4) | 0.0007 (4) | 0.0026 (4) |
C101 | 0.022 (3) | 0.020 (3) | 0.022 (3) | −0.001 (3) | −0.001 (2) | −0.003 (3) |
C102 | 0.024 (3) | 0.023 (3) | 0.021 (3) | −0.006 (3) | −0.001 (2) | −0.005 (3) |
C103 | 0.020 (3) | 0.029 (4) | 0.031 (4) | 0.002 (3) | −0.006 (3) | 0.000 (3) |
C104 | 0.030 (4) | 0.029 (4) | 0.026 (3) | −0.005 (3) | −0.004 (3) | 0.007 (3) |
C105 | 0.025 (3) | 0.025 (4) | 0.025 (3) | −0.003 (3) | −0.002 (3) | 0.001 (3) |
C106 | 0.027 (3) | 0.019 (3) | 0.027 (3) | −0.002 (3) | −0.003 (3) | −0.003 (3) |
C107 | 0.019 (3) | 0.030 (4) | 0.027 (3) | −0.003 (3) | −0.006 (3) | −0.006 (3) |
C108 | 0.018 (3) | 0.032 (4) | 0.038 (4) | 0.001 (3) | −0.010 (3) | −0.001 (3) |
C109 | 0.028 (4) | 0.026 (4) | 0.029 (3) | −0.007 (3) | −0.009 (3) | 0.002 (3) |
C110 | 0.024 (3) | 0.023 (3) | 0.024 (3) | 0.002 (3) | −0.001 (3) | −0.005 (3) |
C111 | 0.013 (3) | 0.026 (3) | 0.022 (3) | −0.005 (3) | 0.001 (2) | −0.006 (3) |
C112 | 0.012 (3) | 0.028 (4) | 0.023 (3) | 0.001 (3) | −0.001 (2) | −0.004 (3) |
C113 | 0.014 (3) | 0.020 (3) | 0.028 (3) | −0.002 (3) | 0.001 (2) | 0.004 (3) |
C114 | 0.020 (3) | 0.022 (3) | 0.026 (3) | 0.002 (3) | 0.000 (3) | 0.001 (3) |
C115 | 0.014 (3) | 0.023 (3) | 0.025 (3) | −0.002 (3) | −0.005 (2) | −0.004 (3) |
C116 | 0.017 (3) | 0.025 (4) | 0.031 (4) | 0.005 (3) | −0.006 (3) | −0.001 (3) |
C117 | 0.028 (4) | 0.038 (4) | 0.028 (4) | 0.010 (3) | −0.006 (3) | −0.007 (3) |
C118 | 0.029 (4) | 0.041 (4) | 0.023 (3) | 0.001 (3) | −0.002 (3) | −0.004 (3) |
C119 | 0.026 (3) | 0.029 (4) | 0.031 (4) | 0.001 (3) | −0.009 (3) | 0.005 (3) |
C120 | 0.028 (3) | 0.012 (3) | 0.025 (3) | 0.001 (3) | 0.006 (3) | −0.002 (2) |
C121 | 0.020 (3) | 0.024 (3) | 0.020 (3) | −0.006 (3) | 0.002 (2) | 0.000 (3) |
C122 | 0.023 (3) | 0.023 (3) | 0.025 (3) | −0.005 (3) | −0.001 (3) | −0.003 (3) |
C123 | 0.028 (3) | 0.020 (3) | 0.026 (3) | −0.006 (3) | 0.005 (3) | 0.000 (3) |
C124 | 0.020 (3) | 0.016 (3) | 0.029 (3) | −0.004 (3) | 0.002 (3) | 0.001 (3) |
C125 | 0.020 (3) | 0.031 (4) | 0.026 (3) | −0.005 (3) | 0.001 (3) | −0.002 (3) |
C126 | 0.030 (4) | 0.025 (4) | 0.027 (3) | −0.003 (3) | 0.004 (3) | −0.008 (3) |
C127 | 0.029 (4) | 0.025 (4) | 0.036 (4) | −0.008 (3) | 0.010 (3) | −0.009 (3) |
C128 | 0.027 (4) | 0.020 (3) | 0.044 (4) | −0.001 (3) | 0.005 (3) | −0.004 (3) |
N101 | 0.030 (3) | 0.016 (3) | 0.028 (3) | 0.002 (2) | 0.000 (2) | 0.002 (2) |
N102 | 0.023 (3) | 0.025 (3) | 0.027 (3) | 0.006 (2) | 0.001 (2) | 0.001 (2) |
O101 | 0.028 (2) | 0.028 (3) | 0.027 (2) | 0.006 (2) | 0.0018 (19) | −0.0006 (19) |
O102 | 0.027 (2) | 0.033 (3) | 0.026 (2) | 0.005 (2) | −0.0019 (19) | −0.001 (2) |
Fe11 | 0.0213 (5) | 0.0196 (5) | 0.0220 (4) | 0.0003 (4) | −0.0007 (3) | −0.0001 (4) |
C201 | 0.039 (4) | 0.046 (5) | 0.031 (4) | 0.001 (4) | 0.001 (3) | 0.005 (3) |
Cl21 | 0.0476 (12) | 0.0593 (13) | 0.0365 (10) | 0.0051 (10) | 0.0064 (8) | 0.0128 (9) |
Cl22 | 0.0356 (10) | 0.0483 (12) | 0.0369 (10) | −0.0023 (9) | −0.0016 (8) | 0.0078 (8) |
C301 | 0.047 (5) | 0.038 (5) | 0.041 (4) | −0.003 (4) | −0.001 (4) | −0.002 (3) |
Cl31 | 0.0431 (12) | 0.0392 (12) | 0.0880 (16) | 0.0005 (10) | −0.0180 (11) | 0.0063 (11) |
Cl32 | 0.0659 (13) | 0.0402 (11) | 0.0342 (10) | 0.0066 (10) | 0.0049 (9) | 0.0049 (8) |
C401 | 0.098 (8) | 0.083 (8) | 0.070 (7) | 0.055 (7) | −0.040 (6) | −0.031 (6) |
Cl41 | 0.0548 (14) | 0.0768 (17) | 0.0599 (14) | −0.0060 (12) | −0.0022 (11) | −0.0203 (12) |
Cl42 | 0.123 (2) | 0.0540 (15) | 0.0697 (17) | −0.0297 (16) | 0.0208 (16) | −0.0127 (13) |
C501 | 0.031 (4) | 0.035 (4) | 0.026 (3) | −0.001 (3) | −0.003 (3) | −0.002 (3) |
Cl51 | 0.0337 (10) | 0.0381 (11) | 0.0521 (11) | 0.0045 (8) | 0.0028 (8) | 0.0081 (9) |
Cl52 | 0.0294 (9) | 0.0422 (11) | 0.0587 (12) | 0.0053 (8) | −0.0001 (8) | −0.0174 (9) |
C1—C5 | 1.441 (8) | C103—Fe11 | 2.045 (7) |
C1—C2 | 1.442 (9) | C103—H103 | 0.9500 |
C1—C11 | 1.464 (9) | C104—C105 | 1.408 (9) |
C1—Fe1 | 2.070 (6) | C104—Fe11 | 2.042 (7) |
C2—C3 | 1.412 (9) | C104—H104 | 0.9500 |
C2—Fe1 | 2.041 (6) | C105—Fe11 | 2.034 (6) |
C2—H2 | 0.9500 | C105—H105 | 0.9500 |
C3—C4 | 1.404 (10) | C106—C110 | 1.446 (9) |
C3—Fe1 | 2.038 (6) | C106—C120 | 1.446 (8) |
C3—H3 | 0.9500 | C106—C107 | 1.450 (9) |
C4—C5 | 1.421 (9) | C106—Fe11 | 2.056 (6) |
C4—Fe1 | 2.040 (7) | C107—C108 | 1.410 (9) |
C4—H4 | 0.9500 | C107—Fe11 | 2.038 (6) |
C5—Fe1 | 2.030 (6) | C107—H107 | 0.9500 |
C5—H5 | 0.9500 | C108—C109 | 1.408 (9) |
C6—C10 | 1.430 (9) | C108—Fe11 | 2.066 (6) |
C6—C7 | 1.437 (9) | C108—H108 | 0.9500 |
C6—C20 | 1.444 (9) | C109—C110 | 1.406 (9) |
C6—Fe1 | 2.058 (6) | C109—Fe11 | 2.048 (6) |
C7—C8 | 1.415 (10) | C109—H109 | 0.9500 |
C7—Fe1 | 2.035 (7) | C110—Fe11 | 2.032 (6) |
C7—H7 | 0.9500 | C110—H110 | 0.9500 |
C8—C9 | 1.423 (10) | C111—C112 | 1.352 (8) |
C8—Fe1 | 2.049 (7) | C111—H111 | 0.9500 |
C8—H8 | 0.9500 | C112—C115 | 1.466 (8) |
C9—C10 | 1.424 (9) | C112—C113 | 1.498 (8) |
C9—Fe1 | 2.044 (6) | C113—O101 | 1.231 (7) |
C9—H9 | 0.9500 | C113—N101 | 1.356 (8) |
C10—Fe1 | 2.040 (6) | C114—C119 | 1.373 (9) |
C10—H10 | 0.9500 | C114—C115 | 1.405 (8) |
C11—C12 | 1.335 (9) | C114—N101 | 1.408 (8) |
C11—H11 | 0.9500 | C115—C116 | 1.387 (8) |
C12—C15 | 1.461 (9) | C116—C117 | 1.385 (9) |
C12—C13 | 1.501 (9) | C116—H116 | 0.9500 |
C13—O1 | 1.241 (7) | C117—C118 | 1.383 (10) |
C13—N1 | 1.342 (8) | C117—H117 | 0.9500 |
C14—C19 | 1.376 (9) | C118—C119 | 1.391 (9) |
C14—N1 | 1.390 (8) | C118—H118 | 0.9500 |
C14—C15 | 1.405 (8) | C119—H119 | 0.9500 |
C15—C16 | 1.394 (9) | C120—C121 | 1.345 (8) |
C16—C17 | 1.380 (9) | C120—H120 | 0.9500 |
C16—H16 | 0.9500 | C121—C124 | 1.478 (8) |
C17—C18 | 1.377 (10) | C121—C122 | 1.497 (8) |
C17—H17 | 0.9500 | C122—O102 | 1.236 (7) |
C18—C19 | 1.402 (9) | C122—N102 | 1.341 (8) |
C18—H18 | 0.9500 | C123—C128 | 1.372 (9) |
C19—H19 | 0.9500 | C123—N102 | 1.392 (8) |
C20—C21 | 1.336 (9) | C123—C124 | 1.401 (9) |
C20—H20 | 0.9500 | C124—C125 | 1.389 (8) |
C21—C24 | 1.466 (9) | C125—C126 | 1.378 (9) |
C21—C22 | 1.487 (9) | C125—H125 | 0.9500 |
C22—O2 | 1.231 (7) | C126—C127 | 1.401 (9) |
C22—N2 | 1.372 (8) | C126—H126 | 0.9500 |
C23—C28 | 1.380 (9) | C127—C128 | 1.393 (9) |
C23—N2 | 1.398 (8) | C127—H127 | 0.9500 |
C23—C24 | 1.421 (9) | C128—H128 | 0.9500 |
C24—C25 | 1.389 (9) | N101—H101 | 0.8800 |
C25—C26 | 1.379 (9) | N102—H10A | 0.8800 |
C25—H25 | 0.9500 | C201—Cl21 | 1.743 (7) |
C26—C27 | 1.376 (10) | C201—Cl22 | 1.779 (8) |
C26—H26 | 0.9500 | C201—H20A | 0.9900 |
C27—C28 | 1.391 (9) | C201—H20B | 0.9900 |
C27—H27 | 0.9500 | C301—Cl32 | 1.754 (8) |
C28—H28 | 0.9500 | C301—Cl31 | 1.771 (8) |
N1—H1 | 0.8800 | C301—H30A | 0.9900 |
N2—H2A | 0.8800 | C301—H30B | 0.9900 |
C101—C102 | 1.425 (8) | C401—Cl42 | 1.694 (10) |
C101—C105 | 1.436 (8) | C401—Cl41 | 1.747 (11) |
C101—C111 | 1.450 (9) | C401—H40A | 0.9900 |
C101—Fe11 | 2.062 (6) | C401—H40B | 0.9900 |
C102—C103 | 1.424 (9) | C501—Cl51 | 1.759 (7) |
C102—Fe11 | 2.038 (6) | C501—Cl52 | 1.771 (7) |
C102—H102 | 0.9500 | C501—H50A | 0.9900 |
C103—C104 | 1.405 (9) | C501—H50B | 0.9900 |
C5—C1—C2 | 106.9 (5) | C104—C103—C102 | 108.2 (6) |
C5—C1—C11 | 122.7 (6) | C104—C103—Fe11 | 69.7 (4) |
C2—C1—C11 | 130.0 (6) | C102—C103—Fe11 | 69.3 (4) |
C5—C1—Fe1 | 67.9 (3) | C104—C103—H103 | 125.9 |
C2—C1—Fe1 | 68.4 (3) | C102—C103—H103 | 125.9 |
C11—C1—Fe1 | 122.5 (4) | Fe11—C103—H103 | 126.6 |
C3—C2—C1 | 107.7 (6) | C103—C104—C105 | 108.4 (6) |
C3—C2—Fe1 | 69.6 (4) | C103—C104—Fe11 | 70.0 (4) |
C1—C2—Fe1 | 70.5 (3) | C105—C104—Fe11 | 69.5 (4) |
C3—C2—H2 | 126.2 | C103—C104—H104 | 125.8 |
C1—C2—H2 | 126.2 | C105—C104—H104 | 125.8 |
Fe1—C2—H2 | 125.3 | Fe11—C104—H104 | 126.2 |
C4—C3—C2 | 109.2 (6) | C104—C105—C101 | 108.5 (6) |
C4—C3—Fe1 | 70.0 (4) | C104—C105—Fe11 | 70.1 (4) |
C2—C3—Fe1 | 69.9 (4) | C101—C105—Fe11 | 70.5 (4) |
C4—C3—H3 | 125.4 | C104—C105—H105 | 125.8 |
C2—C3—H3 | 125.4 | C101—C105—H105 | 125.8 |
Fe1—C3—H3 | 126.4 | Fe11—C105—H105 | 125.2 |
C3—C4—C5 | 108.3 (6) | C110—C106—C120 | 131.8 (6) |
C3—C4—Fe1 | 69.8 (4) | C110—C106—C107 | 105.9 (5) |
C5—C4—Fe1 | 69.2 (4) | C120—C106—C107 | 122.1 (6) |
C3—C4—H4 | 125.8 | C110—C106—Fe11 | 68.4 (3) |
C5—C4—H4 | 125.8 | C120—C106—Fe11 | 123.4 (4) |
Fe1—C4—H4 | 126.8 | C107—C106—Fe11 | 68.6 (3) |
C4—C5—C1 | 107.8 (6) | C108—C107—C106 | 108.8 (6) |
C4—C5—Fe1 | 69.9 (4) | C108—C107—Fe11 | 71.0 (4) |
C1—C5—Fe1 | 70.9 (3) | C106—C107—Fe11 | 69.9 (3) |
C4—C5—H5 | 126.1 | C108—C107—H107 | 125.6 |
C1—C5—H5 | 126.1 | C106—C107—H107 | 125.6 |
Fe1—C5—H5 | 124.7 | Fe11—C107—H107 | 125.1 |
C10—C6—C7 | 106.7 (6) | C109—C108—C107 | 107.7 (6) |
C10—C6—C20 | 130.3 (6) | C109—C108—Fe11 | 69.3 (4) |
C7—C6—C20 | 122.6 (6) | C107—C108—Fe11 | 68.8 (3) |
C10—C6—Fe1 | 68.9 (3) | C109—C108—H108 | 126.1 |
C7—C6—Fe1 | 68.6 (4) | C107—C108—H108 | 126.1 |
C20—C6—Fe1 | 121.5 (4) | Fe11—C108—H108 | 127.3 |
C8—C7—C6 | 108.8 (6) | C110—C109—C108 | 109.6 (6) |
C8—C7—Fe1 | 70.3 (4) | C110—C109—Fe11 | 69.2 (3) |
C6—C7—Fe1 | 70.3 (4) | C108—C109—Fe11 | 70.7 (4) |
C8—C7—H7 | 125.6 | C110—C109—H109 | 125.2 |
C6—C7—H7 | 125.6 | C108—C109—H109 | 125.2 |
Fe1—C7—H7 | 125.4 | Fe11—C109—H109 | 126.5 |
C7—C8—C9 | 108.0 (6) | C109—C110—C106 | 107.9 (6) |
C7—C8—Fe1 | 69.2 (4) | C109—C110—Fe11 | 70.5 (4) |
C9—C8—Fe1 | 69.4 (4) | C106—C110—Fe11 | 70.2 (3) |
C7—C8—H8 | 126.0 | C109—C110—H110 | 126.0 |
C9—C8—H8 | 126.0 | C106—C110—H110 | 126.0 |
Fe1—C8—H8 | 127.0 | Fe11—C110—H110 | 124.9 |
C8—C9—C10 | 107.9 (6) | C112—C111—C101 | 131.5 (6) |
C8—C9—Fe1 | 69.9 (4) | C112—C111—H111 | 114.2 |
C10—C9—Fe1 | 69.5 (4) | C101—C111—H111 | 114.2 |
C8—C9—H9 | 126.0 | C111—C112—C115 | 135.1 (6) |
C10—C9—H9 | 126.0 | C111—C112—C113 | 118.8 (5) |
Fe1—C9—H9 | 126.2 | C115—C112—C113 | 106.0 (5) |
C9—C10—C6 | 108.6 (6) | O101—C113—N101 | 126.1 (6) |
C9—C10—Fe1 | 69.7 (4) | O101—C113—C112 | 127.2 (5) |
C6—C10—Fe1 | 70.2 (4) | N101—C113—C112 | 106.7 (5) |
C9—C10—H10 | 125.7 | C119—C114—C115 | 123.2 (6) |
C6—C10—H10 | 125.7 | C119—C114—N101 | 127.3 (6) |
Fe1—C10—H10 | 125.9 | C115—C114—N101 | 109.5 (5) |
C12—C11—C1 | 129.9 (6) | C116—C115—C114 | 118.1 (6) |
C12—C11—H11 | 115.1 | C116—C115—C112 | 135.2 (6) |
C1—C11—H11 | 115.1 | C114—C115—C112 | 106.4 (5) |
C11—C12—C15 | 137.2 (6) | C117—C116—C115 | 119.5 (6) |
C11—C12—C13 | 118.4 (6) | C117—C116—H116 | 120.3 |
C15—C12—C13 | 104.4 (5) | C115—C116—H116 | 120.3 |
O1—C13—N1 | 126.4 (6) | C118—C117—C116 | 120.6 (6) |
O1—C13—C12 | 125.8 (6) | C118—C117—H117 | 119.7 |
N1—C13—C12 | 107.8 (5) | C116—C117—H117 | 119.7 |
C19—C14—N1 | 127.8 (6) | C117—C118—C119 | 121.4 (6) |
C19—C14—C15 | 122.8 (6) | C117—C118—H118 | 119.3 |
N1—C14—C15 | 109.4 (5) | C119—C118—H118 | 119.3 |
C16—C15—C14 | 118.3 (6) | C114—C119—C118 | 116.8 (6) |
C16—C15—C12 | 134.3 (6) | C114—C119—H119 | 121.6 |
C14—C15—C12 | 107.2 (5) | C118—C119—H119 | 121.6 |
C17—C16—C15 | 119.3 (6) | C121—C120—C106 | 132.3 (6) |
C17—C16—H16 | 120.4 | C121—C120—H120 | 113.9 |
C15—C16—H16 | 120.4 | C106—C120—H120 | 113.9 |
C18—C17—C16 | 121.5 (6) | C120—C121—C124 | 135.9 (6) |
C18—C17—H17 | 119.2 | C120—C121—C122 | 119.4 (5) |
C16—C17—H17 | 119.2 | C124—C121—C122 | 104.4 (5) |
C17—C18—C19 | 120.7 (6) | O102—C122—N102 | 125.4 (6) |
C17—C18—H18 | 119.7 | O102—C122—C121 | 127.0 (6) |
C19—C18—H18 | 119.7 | N102—C122—C121 | 107.6 (5) |
C14—C19—C18 | 117.3 (6) | C128—C123—N102 | 128.4 (6) |
C14—C19—H19 | 121.3 | C128—C123—C124 | 122.4 (6) |
C18—C19—H19 | 121.3 | N102—C123—C124 | 109.2 (5) |
C21—C20—C6 | 131.0 (6) | C125—C124—C123 | 118.7 (6) |
C21—C20—H20 | 114.5 | C125—C124—C121 | 134.1 (6) |
C6—C20—H20 | 114.5 | C123—C124—C121 | 106.9 (5) |
C20—C21—C24 | 135.4 (6) | C126—C125—C124 | 119.7 (6) |
C20—C21—C22 | 118.4 (6) | C126—C125—H125 | 120.2 |
C24—C21—C22 | 106.1 (6) | C124—C125—H125 | 120.2 |
O2—C22—N2 | 124.2 (6) | C125—C126—C127 | 120.6 (6) |
O2—C22—C21 | 128.4 (6) | C125—C126—H126 | 119.7 |
N2—C22—C21 | 107.3 (5) | C127—C126—H126 | 119.7 |
C28—C23—N2 | 127.8 (6) | C128—C127—C126 | 120.4 (6) |
C28—C23—C24 | 122.6 (6) | C128—C127—H127 | 119.8 |
N2—C23—C24 | 109.6 (6) | C126—C127—H127 | 119.8 |
C25—C24—C23 | 117.9 (6) | C123—C128—C127 | 118.1 (6) |
C25—C24—C21 | 135.6 (6) | C123—C128—H128 | 121.0 |
C23—C24—C21 | 106.3 (6) | C127—C128—H128 | 121.0 |
C26—C25—C24 | 119.8 (7) | C113—N101—C114 | 111.2 (5) |
C26—C25—H25 | 120.1 | C113—N101—H101 | 124.4 |
C24—C25—H25 | 120.1 | C114—N101—H101 | 124.4 |
C27—C26—C25 | 121.0 (6) | C122—N102—C123 | 111.8 (5) |
C27—C26—H26 | 119.5 | C122—N102—H10A | 124.1 |
C25—C26—H26 | 119.5 | C123—N102—H10A | 124.1 |
C26—C27—C28 | 121.6 (7) | C110—Fe11—C105 | 108.8 (3) |
C26—C27—H27 | 119.2 | C110—Fe11—C102 | 151.4 (3) |
C28—C27—H27 | 119.2 | C105—Fe11—C102 | 68.6 (2) |
C23—C28—C27 | 117.1 (7) | C110—Fe11—C107 | 69.2 (3) |
C23—C28—H28 | 121.5 | C105—Fe11—C107 | 171.8 (3) |
C27—C28—H28 | 121.5 | C102—Fe11—C107 | 109.1 (2) |
C13—N1—C14 | 111.1 (5) | C110—Fe11—C104 | 129.2 (3) |
C13—N1—H1 | 124.5 | C105—Fe11—C104 | 40.4 (3) |
C14—N1—H1 | 124.5 | C102—Fe11—C104 | 68.4 (3) |
C22—N2—C23 | 110.7 (5) | C107—Fe11—C104 | 147.0 (3) |
C22—N2—H2A | 124.7 | C110—Fe11—C103 | 166.7 (3) |
C23—N2—H2A | 124.7 | C105—Fe11—C103 | 68.0 (3) |
C5—Fe1—C7 | 170.4 (3) | C102—Fe11—C103 | 40.8 (2) |
C5—Fe1—C3 | 68.5 (3) | C107—Fe11—C103 | 115.8 (3) |
C7—Fe1—C3 | 116.8 (3) | C104—Fe11—C103 | 40.2 (3) |
C5—Fe1—C10 | 107.9 (3) | C110—Fe11—C109 | 40.3 (2) |
C7—Fe1—C10 | 68.7 (3) | C105—Fe11—C109 | 116.3 (3) |
C3—Fe1—C10 | 167.2 (3) | C102—Fe11—C109 | 167.3 (3) |
C5—Fe1—C4 | 40.9 (3) | C107—Fe11—C109 | 67.7 (3) |
C7—Fe1—C4 | 148.1 (3) | C104—Fe11—C109 | 107.2 (3) |
C3—Fe1—C4 | 40.3 (3) | C103—Fe11—C109 | 128.3 (3) |
C10—Fe1—C4 | 129.1 (3) | C110—Fe11—C106 | 41.4 (2) |
C5—Fe1—C2 | 69.3 (3) | C105—Fe11—C106 | 131.9 (3) |
C7—Fe1—C2 | 109.1 (3) | C102—Fe11—C106 | 118.0 (2) |
C3—Fe1—C2 | 40.5 (3) | C107—Fe11—C106 | 41.5 (2) |
C10—Fe1—C2 | 151.2 (3) | C104—Fe11—C106 | 169.5 (3) |
C4—Fe1—C2 | 68.5 (3) | C103—Fe11—C106 | 149.9 (3) |
C5—Fe1—C9 | 115.2 (3) | C109—Fe11—C106 | 68.4 (3) |
C7—Fe1—C9 | 68.5 (3) | C110—Fe11—C101 | 118.4 (2) |
C3—Fe1—C9 | 128.4 (3) | C105—Fe11—C101 | 41.0 (2) |
C10—Fe1—C9 | 40.8 (3) | C102—Fe11—C101 | 40.7 (2) |
C4—Fe1—C9 | 106.6 (3) | C107—Fe11—C101 | 132.2 (2) |
C2—Fe1—C9 | 167.3 (3) | C104—Fe11—C101 | 68.4 (2) |
C5—Fe1—C8 | 147.7 (3) | C103—Fe11—C101 | 68.3 (2) |
C7—Fe1—C8 | 40.5 (3) | C109—Fe11—C101 | 150.2 (3) |
C3—Fe1—C8 | 107.5 (3) | C106—Fe11—C101 | 110.3 (2) |
C10—Fe1—C8 | 68.5 (3) | C110—Fe11—C108 | 68.3 (3) |
C4—Fe1—C8 | 115.0 (3) | C105—Fe11—C108 | 147.3 (3) |
C2—Fe1—C8 | 129.6 (3) | C102—Fe11—C108 | 129.7 (3) |
C9—Fe1—C8 | 40.7 (3) | C107—Fe11—C108 | 40.2 (3) |
C5—Fe1—C6 | 130.6 (3) | C104—Fe11—C108 | 114.6 (3) |
C7—Fe1—C6 | 41.1 (3) | C103—Fe11—C108 | 107.0 (3) |
C3—Fe1—C6 | 150.5 (3) | C109—Fe11—C108 | 40.0 (3) |
C10—Fe1—C6 | 40.9 (2) | C106—Fe11—C108 | 68.7 (3) |
C4—Fe1—C6 | 168.7 (3) | C101—Fe11—C108 | 169.4 (3) |
C2—Fe1—C6 | 118.2 (3) | Cl21—C201—Cl22 | 111.0 (4) |
C9—Fe1—C6 | 68.8 (3) | Cl21—C201—H20A | 109.4 |
C8—Fe1—C6 | 68.7 (3) | Cl22—C201—H20A | 109.4 |
C5—Fe1—C1 | 41.2 (2) | Cl21—C201—H20B | 109.4 |
C7—Fe1—C1 | 131.6 (3) | Cl22—C201—H20B | 109.4 |
C3—Fe1—C1 | 68.3 (3) | H20A—C201—H20B | 108.0 |
C10—Fe1—C1 | 117.7 (3) | Cl32—C301—Cl31 | 110.8 (4) |
C4—Fe1—C1 | 68.5 (3) | Cl32—C301—H30A | 109.5 |
C2—Fe1—C1 | 41.1 (3) | Cl31—C301—H30A | 109.5 |
C9—Fe1—C1 | 149.5 (3) | Cl32—C301—H30B | 109.5 |
C8—Fe1—C1 | 169.4 (3) | Cl31—C301—H30B | 109.5 |
C6—Fe1—C1 | 109.8 (2) | H30A—C301—H30B | 108.1 |
C102—C101—C105 | 106.7 (5) | Cl42—C401—Cl41 | 115.4 (5) |
C102—C101—C111 | 132.0 (6) | Cl42—C401—H40A | 108.4 |
C105—C101—C111 | 121.0 (5) | Cl41—C401—H40A | 108.4 |
C102—C101—Fe11 | 68.7 (3) | Cl42—C401—H40B | 108.4 |
C105—C101—Fe11 | 68.4 (3) | Cl41—C401—H40B | 108.4 |
C111—C101—Fe11 | 123.0 (4) | H40A—C401—H40B | 107.5 |
C103—C102—C101 | 108.1 (5) | Cl51—C501—Cl52 | 110.9 (4) |
C103—C102—Fe11 | 69.9 (4) | Cl51—C501—H50A | 109.5 |
C101—C102—Fe11 | 70.6 (3) | Cl52—C501—H50A | 109.5 |
C103—C102—H102 | 125.9 | Cl51—C501—H50B | 109.5 |
C101—C102—H102 | 125.9 | Cl52—C501—H50B | 109.5 |
Fe11—C102—H102 | 125.2 | H50A—C501—H50B | 108.0 |
C5—C1—C2—C3 | 2.7 (7) | C105—C101—C102—C103 | 1.9 (7) |
C11—C1—C2—C3 | 174.9 (6) | C111—C101—C102—C103 | 175.8 (6) |
Fe1—C1—C2—C3 | 59.9 (4) | Fe11—C101—C102—C103 | 60.0 (4) |
C5—C1—C2—Fe1 | −57.2 (4) | C105—C101—C102—Fe11 | −58.1 (4) |
C11—C1—C2—Fe1 | 115.0 (7) | C111—C101—C102—Fe11 | 115.8 (7) |
C1—C2—C3—C4 | −1.5 (7) | C101—C102—C103—C104 | −1.4 (7) |
Fe1—C2—C3—C4 | 59.0 (5) | Fe11—C102—C103—C104 | 59.1 (4) |
C1—C2—C3—Fe1 | −60.5 (4) | C101—C102—C103—Fe11 | −60.5 (4) |
C2—C3—C4—C5 | −0.4 (8) | C102—C103—C104—C105 | 0.3 (7) |
Fe1—C3—C4—C5 | 58.6 (5) | Fe11—C103—C104—C105 | 59.1 (4) |
C2—C3—C4—Fe1 | −59.0 (5) | C102—C103—C104—Fe11 | −58.8 (4) |
C3—C4—C5—C1 | 2.1 (7) | C103—C104—C105—C101 | 0.9 (7) |
Fe1—C4—C5—C1 | 61.1 (4) | Fe11—C104—C105—C101 | 60.3 (4) |
C3—C4—C5—Fe1 | −59.0 (5) | C103—C104—C105—Fe11 | −59.4 (5) |
C2—C1—C5—C4 | −3.0 (7) | C102—C101—C105—C104 | −1.8 (7) |
C11—C1—C5—C4 | −175.9 (6) | C111—C101—C105—C104 | −176.5 (5) |
Fe1—C1—C5—C4 | −60.5 (4) | Fe11—C101—C105—C104 | −60.0 (4) |
C2—C1—C5—Fe1 | 57.5 (4) | C102—C101—C105—Fe11 | 58.3 (4) |
C11—C1—C5—Fe1 | −115.4 (6) | C111—C101—C105—Fe11 | −116.4 (5) |
C10—C6—C7—C8 | −1.4 (7) | C110—C106—C107—C108 | −2.1 (7) |
C20—C6—C7—C8 | −174.5 (6) | C120—C106—C107—C108 | −177.5 (6) |
Fe1—C6—C7—C8 | −60.0 (5) | Fe11—C106—C107—C108 | −60.6 (4) |
C10—C6—C7—Fe1 | 58.6 (4) | C110—C106—C107—Fe11 | 58.5 (4) |
C20—C6—C7—Fe1 | −114.5 (6) | C120—C106—C107—Fe11 | −116.9 (6) |
C6—C7—C8—C9 | 1.3 (8) | C106—C107—C108—C109 | 1.4 (7) |
Fe1—C7—C8—C9 | −58.7 (5) | Fe11—C107—C108—C109 | −58.6 (4) |
C6—C7—C8—Fe1 | 60.0 (4) | C106—C107—C108—Fe11 | 59.9 (4) |
C7—C8—C9—C10 | −0.7 (8) | C107—C108—C109—C110 | −0.1 (7) |
Fe1—C8—C9—C10 | −59.2 (5) | Fe11—C108—C109—C110 | −58.4 (4) |
C7—C8—C9—Fe1 | 58.6 (5) | C107—C108—C109—Fe11 | 58.3 (4) |
C8—C9—C10—C6 | −0.2 (7) | C108—C109—C110—C106 | −1.2 (7) |
Fe1—C9—C10—C6 | −59.7 (4) | Fe11—C109—C110—C106 | −60.5 (4) |
C8—C9—C10—Fe1 | 59.5 (5) | C108—C109—C110—Fe11 | 59.2 (5) |
C7—C6—C10—C9 | 1.0 (7) | C120—C106—C110—C109 | 176.8 (6) |
C20—C6—C10—C9 | 173.4 (6) | C107—C106—C110—C109 | 2.0 (7) |
Fe1—C6—C10—C9 | 59.4 (4) | Fe11—C106—C110—C109 | 60.7 (4) |
C7—C6—C10—Fe1 | −58.4 (4) | C120—C106—C110—Fe11 | 116.2 (7) |
C20—C6—C10—Fe1 | 114.0 (7) | C107—C106—C110—Fe11 | −58.7 (4) |
C5—C1—C11—C12 | −155.5 (7) | C102—C101—C111—C112 | 22.6 (11) |
C2—C1—C11—C12 | 33.4 (11) | C105—C101—C111—C112 | −164.2 (6) |
Fe1—C1—C11—C12 | 121.4 (7) | Fe11—C101—C111—C112 | 112.7 (7) |
C1—C11—C12—C15 | 3.5 (13) | C101—C111—C112—C115 | 1.8 (12) |
C1—C11—C12—C13 | −174.8 (6) | C101—C111—C112—C113 | −173.4 (6) |
C11—C12—C13—O1 | −3.3 (10) | C111—C112—C113—O101 | −8.9 (9) |
C15—C12—C13—O1 | 177.9 (6) | C115—C112—C113—O101 | 174.6 (6) |
C11—C12—C13—N1 | 175.0 (6) | C111—C112—C113—N101 | 171.0 (5) |
C15—C12—C13—N1 | −3.9 (7) | C115—C112—C113—N101 | −5.5 (6) |
C19—C14—C15—C16 | −3.6 (9) | C119—C114—C115—C116 | −6.1 (9) |
N1—C14—C15—C16 | 176.0 (5) | N101—C114—C115—C116 | 172.6 (5) |
C19—C14—C15—C12 | −179.3 (6) | C119—C114—C115—C112 | 179.3 (6) |
N1—C14—C15—C12 | 0.3 (7) | N101—C114—C115—C112 | −2.0 (7) |
C11—C12—C15—C16 | 8.9 (13) | C111—C112—C115—C116 | 15.7 (12) |
C13—C12—C15—C16 | −172.6 (7) | C113—C112—C115—C116 | −168.7 (7) |
C11—C12—C15—C14 | −176.4 (7) | C111—C112—C115—C114 | −171.1 (7) |
C13—C12—C15—C14 | 2.1 (6) | C113—C112—C115—C114 | 4.6 (6) |
C14—C15—C16—C17 | 2.2 (9) | C114—C115—C116—C117 | 4.8 (9) |
C12—C15—C16—C17 | 176.5 (7) | C112—C115—C116—C117 | 177.4 (6) |
C15—C16—C17—C18 | 0.0 (10) | C115—C116—C117—C118 | −0.6 (10) |
C16—C17—C18—C19 | −1.1 (10) | C116—C117—C118—C119 | −2.6 (10) |
N1—C14—C19—C18 | −177.0 (6) | C115—C114—C119—C118 | 3.0 (9) |
C15—C14—C19—C18 | 2.5 (9) | N101—C114—C119—C118 | −175.5 (6) |
C17—C18—C19—C14 | −0.1 (10) | C117—C118—C119—C114 | 1.5 (10) |
C10—C6—C20—C21 | 27.5 (11) | C110—C106—C120—C121 | 19.8 (12) |
C7—C6—C20—C21 | −161.1 (7) | C107—C106—C120—C121 | −166.1 (7) |
Fe1—C6—C20—C21 | 115.6 (7) | Fe11—C106—C120—C121 | 109.7 (7) |
C6—C20—C21—C24 | 7.8 (13) | C106—C120—C121—C124 | 0.0 (13) |
C6—C20—C21—C22 | −176.4 (6) | C106—C120—C121—C122 | −173.4 (6) |
C20—C21—C22—O2 | 3.4 (10) | C120—C121—C122—O102 | −7.2 (10) |
C24—C21—C22—O2 | −179.7 (6) | C124—C121—C122—O102 | 177.5 (6) |
C20—C21—C22—N2 | −177.3 (6) | C120—C121—C122—N102 | 172.3 (6) |
C24—C21—C22—N2 | −0.3 (7) | C124—C121—C122—N102 | −2.9 (6) |
C28—C23—C24—C25 | −2.0 (10) | C128—C123—C124—C125 | −5.3 (9) |
N2—C23—C24—C25 | 176.7 (6) | N102—C123—C124—C125 | 173.1 (5) |
C28—C23—C24—C21 | −177.7 (6) | C128—C123—C124—C121 | −180.0 (6) |
N2—C23—C24—C21 | 1.1 (7) | N102—C123—C124—C121 | −1.5 (7) |
C20—C21—C24—C25 | 1.2 (13) | C120—C121—C124—C125 | 15.2 (12) |
C22—C21—C24—C25 | −174.9 (7) | C122—C121—C124—C125 | −170.8 (7) |
C20—C21—C24—C23 | 175.7 (7) | C120—C121—C124—C123 | −171.4 (7) |
C22—C21—C24—C23 | −0.4 (7) | C122—C121—C124—C123 | 2.6 (6) |
C23—C24—C25—C26 | 1.8 (9) | C123—C124—C125—C126 | 4.5 (9) |
C21—C24—C25—C26 | 175.8 (7) | C121—C124—C125—C126 | 177.3 (6) |
C24—C25—C26—C27 | −0.3 (10) | C124—C125—C126—C127 | −1.4 (9) |
C25—C26—C27—C28 | −1.1 (10) | C125—C126—C127—C128 | −1.2 (10) |
N2—C23—C28—C27 | −177.8 (6) | N102—C123—C128—C127 | −175.3 (6) |
C24—C23—C28—C27 | 0.7 (10) | C124—C123—C128—C127 | 2.8 (10) |
C26—C27—C28—C23 | 0.9 (10) | C126—C127—C128—C123 | 0.4 (10) |
O1—C13—N1—C14 | −177.6 (6) | O101—C113—N101—C114 | −175.7 (6) |
C12—C13—N1—C14 | 4.2 (7) | C112—C113—N101—C114 | 4.5 (7) |
C19—C14—N1—C13 | 176.6 (6) | C119—C114—N101—C113 | 177.0 (6) |
C15—C14—N1—C13 | −2.9 (7) | C115—C114—N101—C113 | −1.6 (7) |
O2—C22—N2—C23 | −179.6 (6) | O102—C122—N102—C123 | −178.3 (6) |
C21—C22—N2—C23 | 1.0 (7) | C121—C122—N102—C123 | 2.1 (7) |
C28—C23—N2—C22 | 177.3 (6) | C128—C123—N102—C122 | 177.9 (6) |
C24—C23—N2—C22 | −1.3 (7) | C124—C123—N102—C122 | −0.4 (7) |
C4—C5—Fe1—C3 | 37.0 (4) | C109—C110—Fe11—C105 | 108.8 (4) |
C1—C5—Fe1—C3 | −81.1 (4) | C106—C110—Fe11—C105 | −132.9 (4) |
C4—C5—Fe1—C10 | −129.9 (4) | C109—C110—Fe11—C102 | −171.5 (5) |
C1—C5—Fe1—C10 | 112.0 (4) | C106—C110—Fe11—C102 | −53.2 (7) |
C1—C5—Fe1—C4 | −118.1 (5) | C109—C110—Fe11—C107 | −79.7 (4) |
C4—C5—Fe1—C2 | 80.6 (4) | C106—C110—Fe11—C107 | 38.7 (4) |
C1—C5—Fe1—C2 | −37.5 (4) | C109—C110—Fe11—C104 | 68.2 (5) |
C4—C5—Fe1—C9 | −86.5 (4) | C106—C110—Fe11—C104 | −173.4 (4) |
C1—C5—Fe1—C9 | 155.4 (4) | C109—C110—Fe11—C103 | 34.9 (13) |
C4—C5—Fe1—C8 | −52.0 (7) | C106—C110—Fe11—C103 | 153.3 (10) |
C1—C5—Fe1—C8 | −170.2 (5) | C106—C110—Fe11—C109 | 118.4 (5) |
C4—C5—Fe1—C6 | −169.5 (4) | C109—C110—Fe11—C106 | −118.4 (5) |
C1—C5—Fe1—C6 | 72.4 (5) | C109—C110—Fe11—C101 | 152.6 (4) |
C4—C5—Fe1—C1 | 118.1 (5) | C106—C110—Fe11—C101 | −89.0 (4) |
C8—C7—Fe1—C3 | −85.9 (5) | C109—C110—Fe11—C108 | −36.4 (4) |
C6—C7—Fe1—C3 | 154.7 (4) | C106—C110—Fe11—C108 | 81.9 (4) |
C8—C7—Fe1—C10 | 81.4 (4) | C104—C105—Fe11—C110 | −129.0 (4) |
C6—C7—Fe1—C10 | −38.0 (4) | C101—C105—Fe11—C110 | 112.0 (4) |
C8—C7—Fe1—C4 | −49.6 (7) | C104—C105—Fe11—C102 | 81.3 (4) |
C6—C7—Fe1—C4 | −169.0 (5) | C101—C105—Fe11—C102 | −37.7 (4) |
C8—C7—Fe1—C2 | −129.3 (4) | C101—C105—Fe11—C104 | −119.1 (5) |
C6—C7—Fe1—C2 | 111.3 (4) | C104—C105—Fe11—C103 | 37.2 (4) |
C8—C7—Fe1—C9 | 37.4 (4) | C101—C105—Fe11—C103 | −81.8 (4) |
C6—C7—Fe1—C9 | −82.0 (4) | C104—C105—Fe11—C109 | −85.9 (4) |
C6—C7—Fe1—C8 | −119.4 (6) | C101—C105—Fe11—C109 | 155.1 (4) |
C8—C7—Fe1—C6 | 119.4 (6) | C104—C105—Fe11—C106 | −169.6 (4) |
C8—C7—Fe1—C1 | −169.8 (4) | C101—C105—Fe11—C106 | 71.3 (5) |
C6—C7—Fe1—C1 | 70.8 (5) | C104—C105—Fe11—C101 | 119.1 (5) |
C4—C3—Fe1—C5 | −37.6 (4) | C104—C105—Fe11—C108 | −50.1 (6) |
C2—C3—Fe1—C5 | 82.9 (4) | C101—C105—Fe11—C108 | −169.1 (5) |
C4—C3—Fe1—C7 | 151.1 (4) | C103—C102—Fe11—C110 | −171.0 (5) |
C2—C3—Fe1—C7 | −88.4 (5) | C101—C102—Fe11—C110 | −52.3 (7) |
C4—C3—Fe1—C10 | 38.4 (15) | C103—C102—Fe11—C105 | −80.7 (4) |
C2—C3—Fe1—C10 | 158.9 (12) | C101—C102—Fe11—C105 | 38.1 (4) |
C2—C3—Fe1—C4 | 120.5 (6) | C103—C102—Fe11—C107 | 107.7 (4) |
C4—C3—Fe1—C2 | −120.5 (6) | C101—C102—Fe11—C107 | −133.5 (4) |
C4—C3—Fe1—C9 | 68.2 (5) | C103—C102—Fe11—C104 | −37.1 (4) |
C2—C3—Fe1—C9 | −171.3 (4) | C101—C102—Fe11—C104 | 81.6 (4) |
C4—C3—Fe1—C8 | 108.3 (4) | C101—C102—Fe11—C103 | 118.7 (5) |
C2—C3—Fe1—C8 | −131.2 (4) | C103—C102—Fe11—C109 | 34.7 (13) |
C4—C3—Fe1—C6 | −174.1 (5) | C101—C102—Fe11—C109 | 153.5 (11) |
C2—C3—Fe1—C6 | −53.6 (7) | C103—C102—Fe11—C106 | 152.2 (4) |
C4—C3—Fe1—C1 | −82.0 (4) | C101—C102—Fe11—C106 | −89.1 (4) |
C2—C3—Fe1—C1 | 38.5 (4) | C103—C102—Fe11—C101 | −118.7 (5) |
C9—C10—Fe1—C5 | 108.1 (4) | C103—C102—Fe11—C108 | 67.5 (5) |
C6—C10—Fe1—C5 | −132.3 (4) | C101—C102—Fe11—C108 | −173.7 (4) |
C9—C10—Fe1—C7 | −81.4 (4) | C108—C107—Fe11—C110 | 80.6 (4) |
C6—C10—Fe1—C7 | 38.2 (4) | C106—C107—Fe11—C110 | −38.6 (4) |
C9—C10—Fe1—C3 | 36.5 (15) | C108—C107—Fe11—C102 | −129.7 (4) |
C6—C10—Fe1—C3 | 156.1 (12) | C106—C107—Fe11—C102 | 111.0 (4) |
C9—C10—Fe1—C4 | 67.7 (5) | C108—C107—Fe11—C104 | −50.3 (6) |
C6—C10—Fe1—C4 | −172.7 (4) | C106—C107—Fe11—C104 | −169.5 (4) |
C9—C10—Fe1—C2 | −172.5 (5) | C108—C107—Fe11—C103 | −86.0 (4) |
C6—C10—Fe1—C2 | −52.9 (7) | C106—C107—Fe11—C103 | 154.8 (4) |
C6—C10—Fe1—C9 | 119.6 (6) | C108—C107—Fe11—C109 | 37.2 (4) |
C9—C10—Fe1—C8 | −37.7 (4) | C106—C107—Fe11—C109 | −82.1 (4) |
C6—C10—Fe1—C8 | 81.9 (4) | C108—C107—Fe11—C106 | 119.3 (5) |
C9—C10—Fe1—C6 | −119.6 (6) | C108—C107—Fe11—C101 | −169.4 (4) |
C9—C10—Fe1—C1 | 151.7 (4) | C106—C107—Fe11—C101 | 71.4 (5) |
C6—C10—Fe1—C1 | −88.7 (4) | C106—C107—Fe11—C108 | −119.3 (5) |
C3—C4—Fe1—C5 | 119.9 (6) | C103—C104—Fe11—C110 | −168.7 (4) |
C3—C4—Fe1—C7 | −54.7 (7) | C105—C104—Fe11—C110 | 71.6 (5) |
C5—C4—Fe1—C7 | −174.6 (5) | C103—C104—Fe11—C105 | 119.6 (5) |
C5—C4—Fe1—C3 | −119.9 (6) | C103—C104—Fe11—C102 | 37.6 (4) |
C3—C4—Fe1—C10 | −169.7 (4) | C105—C104—Fe11—C102 | −82.0 (4) |
C5—C4—Fe1—C10 | 70.4 (5) | C103—C104—Fe11—C107 | −54.4 (6) |
C3—C4—Fe1—C2 | 37.0 (4) | C105—C104—Fe11—C107 | −174.0 (4) |
C5—C4—Fe1—C2 | −82.9 (4) | C105—C104—Fe11—C103 | −119.6 (5) |
C3—C4—Fe1—C9 | −130.6 (4) | C103—C104—Fe11—C109 | −129.8 (4) |
C5—C4—Fe1—C9 | 109.5 (4) | C105—C104—Fe11—C109 | 110.6 (4) |
C3—C4—Fe1—C8 | −87.8 (4) | C103—C104—Fe11—C106 | 166.7 (13) |
C5—C4—Fe1—C8 | 152.3 (4) | C105—C104—Fe11—C106 | 47.1 (15) |
C3—C4—Fe1—C6 | 165.0 (12) | C103—C104—Fe11—C101 | 81.5 (4) |
C5—C4—Fe1—C6 | 45.1 (15) | C105—C104—Fe11—C101 | −38.1 (4) |
C3—C4—Fe1—C1 | 81.3 (4) | C103—C104—Fe11—C108 | −87.5 (4) |
C5—C4—Fe1—C1 | −38.6 (4) | C105—C104—Fe11—C108 | 152.9 (4) |
C3—C2—Fe1—C5 | −80.8 (4) | C104—C103—Fe11—C110 | 41.3 (12) |
C1—C2—Fe1—C5 | 37.6 (4) | C102—C103—Fe11—C110 | 161.0 (10) |
C3—C2—Fe1—C7 | 109.3 (4) | C104—C103—Fe11—C105 | −37.4 (4) |
C1—C2—Fe1—C7 | −132.4 (4) | C102—C103—Fe11—C105 | 82.3 (4) |
C1—C2—Fe1—C3 | 118.4 (6) | C104—C103—Fe11—C102 | −119.7 (5) |
C3—C2—Fe1—C10 | −170.5 (5) | C104—C103—Fe11—C107 | 150.5 (4) |
C1—C2—Fe1—C10 | −52.1 (7) | C102—C103—Fe11—C107 | −89.7 (4) |
C3—C2—Fe1—C4 | −36.8 (4) | C102—C103—Fe11—C104 | 119.7 (5) |
C1—C2—Fe1—C4 | 81.6 (4) | C104—C103—Fe11—C109 | 69.4 (5) |
C3—C2—Fe1—C9 | 32.5 (15) | C102—C103—Fe11—C109 | −170.8 (4) |
C1—C2—Fe1—C9 | 150.9 (12) | C104—C103—Fe11—C106 | −175.2 (5) |
C3—C2—Fe1—C8 | 68.5 (5) | C102—C103—Fe11—C106 | −55.4 (6) |
C1—C2—Fe1—C8 | −173.1 (4) | C104—C103—Fe11—C101 | −81.8 (4) |
C3—C2—Fe1—C6 | 153.3 (4) | C102—C103—Fe11—C101 | 37.9 (4) |
C1—C2—Fe1—C6 | −88.4 (4) | C104—C103—Fe11—C108 | 108.2 (4) |
C3—C2—Fe1—C1 | −118.4 (6) | C102—C103—Fe11—C108 | −132.0 (4) |
C8—C9—Fe1—C5 | 152.3 (4) | C108—C109—Fe11—C110 | −120.9 (6) |
C10—C9—Fe1—C5 | −88.5 (4) | C110—C109—Fe11—C105 | −88.5 (4) |
C8—C9—Fe1—C7 | −37.3 (4) | C108—C109—Fe11—C105 | 150.6 (4) |
C10—C9—Fe1—C7 | 81.9 (4) | C110—C109—Fe11—C102 | 161.3 (11) |
C8—C9—Fe1—C3 | 70.5 (5) | C108—C109—Fe11—C102 | 40.3 (13) |
C10—C9—Fe1—C3 | −170.3 (4) | C110—C109—Fe11—C107 | 83.7 (4) |
C8—C9—Fe1—C10 | −119.2 (6) | C108—C109—Fe11—C107 | −37.3 (4) |
C8—C9—Fe1—C4 | 109.3 (4) | C110—C109—Fe11—C104 | −131.1 (4) |
C10—C9—Fe1—C4 | −131.5 (4) | C108—C109—Fe11—C104 | 108.0 (4) |
C8—C9—Fe1—C2 | 44.1 (14) | C110—C109—Fe11—C103 | −170.4 (4) |
C10—C9—Fe1—C2 | 163.3 (12) | C108—C109—Fe11—C103 | 68.7 (5) |
C10—C9—Fe1—C8 | 119.2 (6) | C110—C109—Fe11—C106 | 38.8 (4) |
C8—C9—Fe1—C6 | −81.6 (4) | C108—C109—Fe11—C106 | −82.2 (4) |
C10—C9—Fe1—C6 | 37.6 (4) | C110—C109—Fe11—C101 | −54.6 (7) |
C8—C9—Fe1—C1 | −175.0 (5) | C108—C109—Fe11—C101 | −175.5 (5) |
C10—C9—Fe1—C1 | −55.8 (7) | C110—C109—Fe11—C108 | 120.9 (6) |
C7—C8—Fe1—C5 | −171.6 (5) | C120—C106—Fe11—C110 | −126.7 (7) |
C9—C8—Fe1—C5 | −51.8 (7) | C107—C106—Fe11—C110 | 118.1 (5) |
C9—C8—Fe1—C7 | 119.8 (6) | C110—C106—Fe11—C105 | 68.8 (5) |
C7—C8—Fe1—C3 | 111.0 (4) | C120—C106—Fe11—C105 | −58.0 (6) |
C9—C8—Fe1—C3 | −129.2 (4) | C107—C106—Fe11—C105 | −173.1 (4) |
C7—C8—Fe1—C10 | −81.9 (4) | C110—C106—Fe11—C102 | 154.3 (4) |
C9—C8—Fe1—C10 | 37.8 (4) | C120—C106—Fe11—C102 | 27.6 (6) |
C7—C8—Fe1—C4 | 153.7 (4) | C107—C106—Fe11—C102 | −87.6 (4) |
C9—C8—Fe1—C4 | −86.6 (4) | C110—C106—Fe11—C107 | −118.1 (5) |
C7—C8—Fe1—C2 | 71.7 (5) | C120—C106—Fe11—C107 | 115.2 (7) |
C9—C8—Fe1—C2 | −168.6 (4) | C110—C106—Fe11—C104 | 29.1 (15) |
C7—C8—Fe1—C9 | −119.8 (6) | C120—C106—Fe11—C104 | −97.6 (14) |
C7—C8—Fe1—C6 | −37.9 (4) | C107—C106—Fe11—C104 | 147.3 (13) |
C9—C8—Fe1—C6 | 81.9 (4) | C110—C106—Fe11—C103 | −168.1 (5) |
C7—C8—Fe1—C1 | 46.2 (16) | C120—C106—Fe11—C103 | 65.2 (8) |
C9—C8—Fe1—C1 | 166.0 (13) | C107—C106—Fe11—C103 | −50.0 (6) |
C10—C6—Fe1—C5 | 68.0 (5) | C110—C106—Fe11—C109 | −37.8 (4) |
C7—C6—Fe1—C5 | −173.2 (4) | C120—C106—Fe11—C109 | −164.5 (6) |
C20—C6—Fe1—C5 | −57.2 (6) | C107—C106—Fe11—C109 | 80.3 (4) |
C10—C6—Fe1—C7 | −118.8 (5) | C110—C106—Fe11—C101 | 110.3 (4) |
C20—C6—Fe1—C7 | 116.0 (7) | C120—C106—Fe11—C101 | −16.4 (6) |
C10—C6—Fe1—C3 | −169.5 (5) | C107—C106—Fe11—C101 | −131.6 (4) |
C7—C6—Fe1—C3 | −50.7 (7) | C110—C106—Fe11—C108 | −80.9 (4) |
C20—C6—Fe1—C3 | 65.3 (8) | C120—C106—Fe11—C108 | 152.3 (6) |
C7—C6—Fe1—C10 | 118.8 (5) | C107—C106—Fe11—C108 | 37.2 (4) |
C20—C6—Fe1—C10 | −125.2 (7) | C102—C101—Fe11—C110 | 154.6 (4) |
C10—C6—Fe1—C4 | 30.4 (15) | C105—C101—Fe11—C110 | −86.4 (4) |
C7—C6—Fe1—C4 | 149.1 (13) | C111—C101—Fe11—C110 | 27.5 (6) |
C20—C6—Fe1—C4 | −94.9 (14) | C102—C101—Fe11—C105 | −119.1 (5) |
C10—C6—Fe1—C2 | 154.1 (4) | C111—C101—Fe11—C105 | 113.9 (6) |
C7—C6—Fe1—C2 | −87.1 (4) | C105—C101—Fe11—C102 | 119.1 (5) |
C20—C6—Fe1—C2 | 28.9 (6) | C111—C101—Fe11—C102 | −127.1 (7) |
C10—C6—Fe1—C9 | −37.6 (4) | C102—C101—Fe11—C107 | 67.7 (5) |
C7—C6—Fe1—C9 | 81.2 (4) | C105—C101—Fe11—C107 | −173.2 (4) |
C20—C6—Fe1—C9 | −162.8 (6) | C111—C101—Fe11—C107 | −59.4 (6) |
C10—C6—Fe1—C8 | −81.3 (4) | C102—C101—Fe11—C104 | −81.5 (4) |
C7—C6—Fe1—C8 | 37.4 (4) | C105—C101—Fe11—C104 | 37.6 (4) |
C20—C6—Fe1—C8 | 153.4 (6) | C111—C101—Fe11—C104 | 151.4 (6) |
C10—C6—Fe1—C1 | 109.9 (4) | C102—C101—Fe11—C103 | −38.1 (4) |
C7—C6—Fe1—C1 | −131.4 (4) | C105—C101—Fe11—C103 | 81.0 (4) |
C20—C6—Fe1—C1 | −15.4 (6) | C111—C101—Fe11—C103 | −165.2 (6) |
C2—C1—Fe1—C5 | −119.8 (5) | C102—C101—Fe11—C109 | −168.6 (5) |
C11—C1—Fe1—C5 | 115.7 (7) | C105—C101—Fe11—C109 | −49.6 (7) |
C5—C1—Fe1—C7 | −171.0 (4) | C111—C101—Fe11—C109 | 64.3 (7) |
C2—C1—Fe1—C7 | 69.2 (5) | C102—C101—Fe11—C106 | 109.7 (4) |
C11—C1—Fe1—C7 | −55.4 (6) | C105—C101—Fe11—C106 | −131.2 (4) |
C5—C1—Fe1—C3 | 81.8 (4) | C111—C101—Fe11—C106 | −17.4 (6) |
C2—C1—Fe1—C3 | −38.0 (4) | C102—C101—Fe11—C108 | 27.3 (16) |
C11—C1—Fe1—C3 | −162.5 (6) | C105—C101—Fe11—C108 | 146.3 (13) |
C5—C1—Fe1—C10 | −85.7 (4) | C111—C101—Fe11—C108 | −99.8 (14) |
C2—C1—Fe1—C10 | 154.5 (4) | C109—C108—Fe11—C110 | 36.7 (4) |
C11—C1—Fe1—C10 | 30.0 (6) | C107—C108—Fe11—C110 | −83.0 (4) |
C5—C1—Fe1—C4 | 38.3 (4) | C109—C108—Fe11—C105 | −54.6 (7) |
C2—C1—Fe1—C4 | −81.4 (4) | C107—C108—Fe11—C105 | −174.3 (5) |
C11—C1—Fe1—C4 | 154.0 (6) | C109—C108—Fe11—C102 | −169.3 (4) |
C5—C1—Fe1—C2 | 119.8 (5) | C107—C108—Fe11—C102 | 71.0 (5) |
C11—C1—Fe1—C2 | −124.5 (7) | C109—C108—Fe11—C107 | 119.7 (6) |
C5—C1—Fe1—C9 | −48.0 (6) | C109—C108—Fe11—C104 | −87.8 (4) |
C2—C1—Fe1—C9 | −167.8 (5) | C107—C108—Fe11—C104 | 152.5 (4) |
C11—C1—Fe1—C9 | 67.6 (7) | C109—C108—Fe11—C103 | −130.2 (4) |
C5—C1—Fe1—C8 | 150.1 (14) | C107—C108—Fe11—C103 | 110.1 (4) |
C2—C1—Fe1—C8 | 30.3 (16) | C107—C108—Fe11—C109 | −119.7 (6) |
C11—C1—Fe1—C8 | −94.2 (15) | C109—C108—Fe11—C106 | 81.4 (4) |
C5—C1—Fe1—C6 | −129.7 (4) | C107—C108—Fe11—C106 | −38.3 (4) |
C2—C1—Fe1—C6 | 110.5 (4) | C109—C108—Fe11—C101 | 167.8 (13) |
C11—C1—Fe1—C6 | −14.1 (6) | C107—C108—Fe11—C101 | 48.1 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O101 | 0.88 | 2.01 | 2.876 (7) | 168 |
N2—H2A···O102 | 0.88 | 1.98 | 2.849 (7) | 171 |
N101—H101···O1 | 0.88 | 1.92 | 2.774 (7) | 163 |
N102—H10A···O2 | 0.88 | 1.95 | 2.822 (7) | 169 |
Experimental details
Crystal data | |
Chemical formula | [Fe(C28H20N2O2)]·2CH2Cl2 |
Mr | 642.16 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 7.8609 (2), 14.1905 (4), 49.5413 (12) |
β (°) | 90.099 (1) |
V (Å3) | 5526.3 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.97 |
Crystal size (mm) | 0.17 × 0.04 × 0.03 |
Data collection | |
Diffractometer | Bruker Nonius APEX II CCD camera on κ-goniostat diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2007) |
Tmin, Tmax | 0.853, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 54405, 9612, 7846 |
Rint | 0.063 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.085, 0.173, 1.17 |
No. of reflections | 9612 |
No. of parameters | 703 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + 47.692P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.63, −0.55 |
Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), WinGX (Farrugia, 1999), Mercury (Version 2.4; Macrae et al., 2008) and PARST95 (Nardelli, 1995).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O101 | 0.88 | 2.01 | 2.876 (7) | 167.6 |
N2—H2A···O102 | 0.88 | 1.98 | 2.849 (7) | 171.0 |
N101—H101···O1 | 0.88 | 1.92 | 2.774 (7) | 163.0 |
N102—H10A···O2 | 0.88 | 1.95 | 2.822 (7) | 169.4 |
Interaction | D—H | H···A | D···A | D—H···A |
C201—H20B···O102 | 0.99 | 2.64 | 3.245 (9) | 120 |
C27—H27···Cl32 | 0.95 | 2.87 | 3.676 (7) | 143 |
C118—H118···Cl32 | 0.95 | 2.91 | 3.725 (7) | 145 |
C501—H50A···O101 | 0.99 | 2.71 | 3.294 (8) | 118 |
C501—H50B···Cg1 | 0.99 | 2.49 | 3.430 (8) | 160 |
Cg1 is the centroid of the C123–C128 phenyl ring. |
The chemistry of ferrocenes continues to flourish (van Staveren & Metzler-Nolte, 2004; Ren, 2008; Diallo et al., 2009, and references therein) and spans a plethora of disciplines, including medicinal chemistry (Dubar et al., 2008; Auzias et al., 2009; Higgins & Gellett, 2009), catalysis (Togni & Hayashi, 1995), novel materials (Shoji et al., 2009), sensors (Oton et al., 2006; Qing et al., 2009), supramolecular chemistry (Tan et al., 2008) and the design of extended molecular architectures, which often exploit intra- or intermolecular hydrogen bonding (Stepnicka et al., 2008; Hirao, 2009, and references therein; Lataifeh et al., 2009). We and others have recently published the synthesis of the isomeric ferrocenyl oxindoles, (E)- and (Z)-(III), which are readily separated and have excellent anticancer properties (see scheme). We have shown that (E)- and (Z)-(III) display intermolecular hydrogen bonding in the solid state of the type NH···O═C (Silva et al., 2008; Spencer et al., 2009).
To extend the hydrogen-bond capability in related systems, we have now reacted (I) with ferrocene-1,1'-dicarbaldehyde, (II), with a view to synthesizing 1,1'-ferrocenyl oxindoles (see scheme; Connell et al., 2009). Analysis of the reaction mixture by 1H NMR spectroscopy revealed a complex spectroscopic pattern, indicating fluxionality or a mixture of isomers (see Experimental). Single crystals suitable for X-ray crystallographic analysis were obtained from solution in dichloromethane–hexane and the structure of the remarkable title complex, (IV), was determined (Figs. 1 and 2). Analysis of the single crystals by 1H NMR spectroscopy gave a similar complex spectrum to that of the reaction mixture and thin-layer chromatographic analysis revealed one spot, distinct from either the starting aldehyde or oxindole.
The crystal structure of (IV) contains two crystallographically independent ferrocene complexes with two molecules of dichloromethane per molecule (Fig. 1). Of interest, three of a set of seven substituted 3-methylidene-indolin-2-ones (Spencer et al., 2010) and one of the two isomeric ferrocenyl oxindoles (Spencer et al., 2009) previously reported by us also have Z' > 1. The geometry of both crystallographically independent ferrocene species in (IV) compares closely with the ferrocenyl oxindoles and substituted oxindoles previously reported by us and others (Silva et al., 2008; Spencer et al., 2009, 2010) and with fragments found in a search of the Cambridge Structural Database (CSD, Version 5.32; Allen, 2002). All four oxindole units in (IV) exist as the E isomers, with the average of the four bond angles C11/C111—C12/C112—C13/C113 and C20/C120—C21/C121—C22/C122 being 118.8 (5)°. This is in excellent agreement with the equivalent bond angles in previously reported E isomers [averages of 118.5 (6)° from Spencer et al. (2009) and 118.9 (2)° from Spencer et al. (2010)].
While the bond lengths and angles in the two crystallographically independent ferrocene complexes of (IV) are very similar, differences are found in the interplanar distances and angles between the two oxindole units of each complex. The perpendicular separation between the mean plane through the oxindole unit O1/N1/C12–C19 and the centroid of the oxindole unit O2/N2/C21–C28 is 3.0 Å, and the angle between the two planes is 4.2 (1)°. The equivalent separation in the other complex, between the mean plane through O101/N101/C112–C119 and the centroid of O102/N102/C121–C128, is a little longer at 3.2 Å and the angle between the planes is much larger at 15.2 (1)°. The crystallographically independent molecules also show differences in the angles between the planes of the oxindole units and the cyclopentadienyl units to which they are bonded. The angle between the mean plane through the oxindole unit O1/N1/C12–C19 and that of the C1–C5 ring is 32.2 (2)°, and that between O2/N2/C21–C28 and C6–C10 is 30.2 (2)°. By contrast, the equivalent angles in the other complex are much smaller, with the angle between O101/N101/C112–C119 and C101–C105 being 22.3 (2)° and that between O102/N102/C121–C128 and C106–C110 being 19.5 (2)°.
In common with all the previously reported oxindole-based structures (Spencer et al., 2009, 2010), molecular dimers are formed through intermolecular N—H···O═C hydrogen bonding. In the case of (IV), the crystallographically independent molecules form molecular dimers through intermolecular N—H···O═C hydrogen bonding between two pairs of adjacent oxindole units (Figs. 1 and 2; Table 1). The hydrogen-bonding motif leading to the formation of the molecular dimers can be described as an R22(8) ring (Etter et al., 1990). The dimers are packed into double columns along the (100) direction through π–π stacking interactions (Hunter & Sanders, 1990) between the oxindole units N1/O1/C12–C19 and N102/O102/C121–C128, with an interplanar separation of approximately 3.3 Å (Fig. 2).
One of the dichloromethane molecules, Cl51—C501—Cl52, forms a short C—H···π(arene) interaction with the C123–C128 phenyl ring (Mocilac et al., 2010) (Fig. 3 and Table 2). In addition, three of the four dichloromethane molecules form some kind of weak C—H···Cl or C—H···O interaction with the ferrocene residues (Table 2).
In conclusion, the condensation of ferrocene-1,1'-dicarbaldehyde, (II), with oxindole (I) affords a 1,1'-disubstituted ferrocene, (IV), which displays intermolecular hydrogen bonding (NH···O═C) between two adjacent ferrocenes and four oxindole units. The possibility of engineering further extended hydrogen-bonded networks is currently under investigation in our laboratory.