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The title compounds, both [Fe(C5H5)(C15H14NO2)], crystallize with Z′ = 2 in the centrosymmetric space group P\overline{1}. In each compound, there is an intra­molecular N—H...O=C hydrogen bond, and pairs of inter­molecular O—H...O=C hydrogen bonds link the mol­ecules into chains, parallel to [1\overline{1}0] in the 3-hydr­oxy compound and parallel to [10\overline{1}] in the 4-hydr­oxy compound.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106027314/gd3037sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106027314/gd3037Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106027314/gd3037IIsup3.hkl
Contains datablock II

CCDC references: 621257; 621258

Comment top

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, ArCOCHC(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)FeC5H4COCHC(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 OC—CC—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 OC—CC—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 OC—CC—N plane and the substituted cyclopentadienyl ring, the C10—C11 and C30—C31 bonds linking the OC—CC—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—CC—N group.

Although two compounds in the solid state have strong N—H···OC 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···OC 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···OC 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).

Experimental top

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, OC), 1523 (m, CC) 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, OC), 1510 (vs, CC) 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).

Refinement top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The two independent molecules of (I), showing the atom-labelling schemes for (a) molecule 1 and (b) molecule 2. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of the [110] chain linked by the O—H···OC hydrogen bonds. For clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an ampersand (&) and a dollar sign ($) are at the symmetry positions (1 + x, y - 1, z) and (x - 1, 1 + y, z), respectively; Cg6# is at the symmetry position (1 - x, 1 - y, 1 - z).
[Figure 3] Fig. 3. The two independent molecules of (II), showing the atom-labelling schemes for (a) molecule 1 and (b) molecule 2. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 4] Fig. 4. Part of the crystal structure of (II), showing the formation of the [101] chain linked by the O—H···OC hydrogen bonds. For clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an ampersand (&) and a dollar sign ($) are at the symmetry positions (x - 1, y, 1 + z) and (1 + x, y, z - 1), respectively; Cg1# is at the symmetry position (1 - x, 1 - y, 1 - z).
(I) (Z)-1-Ferrocenyl-3-(3-hydroxyanilino)but-2-en-1-one top
Crystal data top
[Fe(C5H5)(C15H14NO2)]Z = 4
Mr = 361.21F(000) = 752
TriclinicP1Dx = 1.430 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.768 (2) ÅCell parameters from 25 reflections
b = 10.804 (2) Åθ = 9–12°
c = 16.244 (3) ŵ = 0.91 mm1
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
Data collection top
Enraf–Nonius CAD-4
diffractometer
3837 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 26.0°, θmin = 1.3°
ω–2θ scanh = 012
Absorption correction: psi-scan
ψ scan (North et al., 1968)
k = 1313
Tmin = 0.772, Tmax = 0.839l = 1919
6988 measured reflections3 standard reflections every 200 reflections
6576 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-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 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
[Fe(C5H5)(C15H14NO2)]γ = 99.22 (3)°
Mr = 361.21V = 1677.7 (6) Å3
TriclinicP1Z = 4
a = 9.768 (2) ÅMo Kα radiation
b = 10.804 (2) ŵ = 0.91 mm1
c = 16.244 (3) ÅT = 293 K
α = 91.39 (3)°0.30 × 0.20 × 0.20 mm
β = 97.05 (3)°
Data collection top
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 = 0.8393 standard reflections every 200 reflections
6988 measured reflections intensity decay: none
6576 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.01Δρmax = 0.50 e Å3
6576 reflectionsΔρmin = 0.34 e Å3
437 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.31324 (6)0.65967 (6)0.41560 (4)0.03364 (18)
Fe20.84407 (7)0.17112 (7)1.09926 (4)0.0446 (2)
O10.1030 (3)0.7065 (3)0.58336 (18)0.0420 (8)
O40.3500 (4)0.6937 (3)0.6720 (2)0.0573 (10)
H4O0.27420.69030.64330.086*
O20.0530 (4)1.1801 (3)0.8147 (2)0.0560 (10)
H2O0.09991.21270.84480.084*
N10.0783 (4)0.8562 (3)0.6084 (2)0.0398 (10)
H1N0.01210.81770.62850.048*
C110.0597 (4)0.7100 (4)0.5069 (3)0.0319 (10)
C350.4825 (5)0.4693 (4)0.8084 (3)0.0395 (12)
N20.6085 (4)0.4540 (4)0.8583 (2)0.0461 (11)
H2N0.65310.39820.84080.055*
C390.3505 (5)0.5882 (4)0.7148 (3)0.0398 (12)
C400.4750 (5)0.5750 (4)0.7619 (3)0.0408 (12)
H400.55340.63660.76250.049*
C120.0413 (4)0.7818 (4)0.4768 (3)0.0332 (10)
H120.06490.78190.41960.040*
O30.7953 (4)0.3060 (3)0.8977 (2)0.0557 (10)
C310.8237 (5)0.3661 (4)0.9665 (3)0.0407 (11)
C320.7676 (5)0.4761 (4)0.9823 (3)0.0391 (11)
H320.80240.52311.03130.047*
C100.1155 (4)0.6320 (4)0.4461 (3)0.0336 (10)
C50.4936 (5)0.6904 (5)0.4948 (3)0.0500 (13)
H50.51490.64390.54070.060*
C80.2166 (5)0.4788 (4)0.3897 (3)0.0499 (14)
H80.26000.40900.38410.060*
C330.6654 (5)0.5176 (4)0.9299 (3)0.0384 (11)
C40.5212 (5)0.6667 (5)0.4132 (4)0.0578 (16)
H40.56370.60130.39590.069*
C60.1144 (4)0.6486 (4)0.3595 (3)0.0398 (12)
H60.07870.71180.33020.048*
C130.1082 (4)0.8524 (4)0.5255 (3)0.0313 (10)
C150.1462 (5)0.9182 (4)0.6665 (3)0.0354 (11)
C380.2359 (5)0.4951 (5)0.7127 (3)0.0445 (12)
H380.15230.50330.68070.053*
C200.0715 (5)1.0197 (4)0.7128 (3)0.0381 (11)
H200.02041.04910.70450.046*
C90.1811 (5)0.5258 (4)0.4640 (3)0.0397 (11)
H90.19770.49310.51600.048*
C20.4167 (5)0.8395 (4)0.4130 (3)0.0446 (12)
H20.37830.90910.39520.054*
C190.1330 (5)1.0794 (4)0.7725 (3)0.0364 (11)
C10.4276 (5)0.7976 (4)0.4940 (3)0.0420 (12)
H10.39690.83390.53930.050*
C300.9149 (5)0.3192 (4)1.0332 (3)0.0409 (12)
C70.1763 (5)0.5538 (5)0.3257 (3)0.0512 (14)
H70.18830.54300.27020.061*
C140.2104 (4)0.9306 (4)0.4878 (3)0.0394 (11)
H14A0.30250.89660.49980.059*
H14B0.20970.93020.42880.059*
H14C0.18491.01510.51060.059*
C180.2691 (5)1.0351 (5)0.7844 (3)0.0450 (13)
H180.31091.07450.82390.054*
C290.9948 (5)0.2211 (5)1.0252 (3)0.0529 (14)
H291.00450.17960.97600.063*
C160.2826 (5)0.8722 (4)0.6788 (3)0.0438 (12)
H160.33260.80220.64800.053*
C260.9319 (5)0.3556 (5)1.1197 (3)0.0526 (14)
H260.89230.41861.14310.063*
C360.3686 (5)0.3757 (5)0.8053 (3)0.0477 (13)
H360.37450.30370.83490.057*
C281.0570 (5)0.1982 (5)1.1060 (4)0.0597 (16)
H281.11420.13851.11860.072*
C170.3434 (5)0.9322 (5)0.7377 (3)0.0475 (13)
H170.43530.90260.74590.057*
C210.7189 (6)0.0133 (5)1.0448 (4)0.0686 (17)
H210.72950.02790.99560.082*
C370.2447 (5)0.3900 (5)0.7576 (3)0.0506 (13)
H370.16670.32760.75610.061*
C220.6413 (6)0.1120 (6)1.0525 (4)0.0680 (17)
H220.59260.14751.00890.082*
C340.6090 (5)0.6337 (4)0.9523 (3)0.0533 (14)
H34A0.63060.69650.91300.080*
H34B0.65100.66501.00690.080*
H34C0.50940.61380.95130.080*
C240.7326 (6)0.0713 (6)1.1813 (4)0.0705 (18)
H240.75450.07461.23870.085*
C230.6500 (6)0.1469 (6)1.1359 (4)0.0709 (18)
H230.60820.20951.15790.085*
C271.0179 (6)0.2807 (5)1.1634 (4)0.0654 (17)
H271.04450.28491.22050.078*
C30.4743 (5)0.7576 (5)0.3631 (3)0.0559 (14)
H30.47980.76350.30650.067*
C250.7771 (6)0.0109 (5)1.1252 (4)0.0695 (17)
H250.83450.07021.13890.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0304 (4)0.0344 (4)0.0376 (4)0.0099 (3)0.0051 (3)0.0038 (3)
Fe20.0417 (4)0.0518 (5)0.0427 (4)0.0158 (4)0.0033 (3)0.0034 (4)
O10.0448 (19)0.057 (2)0.0285 (17)0.0248 (16)0.0011 (15)0.0010 (15)
O40.049 (2)0.064 (2)0.056 (2)0.0118 (19)0.0112 (18)0.0177 (19)
O20.063 (2)0.053 (2)0.055 (2)0.0200 (19)0.0078 (19)0.0187 (18)
N10.040 (2)0.047 (2)0.039 (2)0.0249 (19)0.0043 (18)0.0007 (18)
C110.030 (2)0.035 (3)0.032 (3)0.006 (2)0.005 (2)0.004 (2)
C350.039 (3)0.051 (3)0.030 (3)0.018 (2)0.001 (2)0.006 (2)
N20.046 (2)0.059 (3)0.038 (2)0.029 (2)0.0024 (19)0.008 (2)
C390.048 (3)0.048 (3)0.026 (2)0.019 (3)0.002 (2)0.002 (2)
C400.039 (3)0.050 (3)0.034 (3)0.010 (2)0.004 (2)0.001 (2)
C120.034 (3)0.036 (3)0.030 (2)0.008 (2)0.002 (2)0.002 (2)
O30.066 (2)0.067 (2)0.040 (2)0.040 (2)0.0063 (18)0.0133 (18)
C310.040 (3)0.045 (3)0.039 (3)0.013 (2)0.003 (2)0.003 (2)
C320.040 (3)0.044 (3)0.033 (3)0.012 (2)0.001 (2)0.004 (2)
C100.028 (2)0.035 (3)0.038 (3)0.007 (2)0.002 (2)0.003 (2)
C50.035 (3)0.047 (3)0.065 (4)0.005 (2)0.008 (3)0.007 (3)
C80.047 (3)0.035 (3)0.069 (4)0.009 (2)0.014 (3)0.016 (3)
C330.042 (3)0.037 (3)0.036 (3)0.010 (2)0.002 (2)0.005 (2)
C40.030 (3)0.051 (3)0.095 (5)0.013 (3)0.012 (3)0.020 (3)
C60.036 (3)0.049 (3)0.036 (3)0.014 (2)0.000 (2)0.002 (2)
C130.024 (2)0.029 (2)0.041 (3)0.0030 (19)0.004 (2)0.006 (2)
C150.044 (3)0.038 (3)0.029 (2)0.020 (2)0.008 (2)0.000 (2)
C380.037 (3)0.060 (3)0.036 (3)0.013 (3)0.003 (2)0.005 (2)
C200.044 (3)0.037 (3)0.036 (3)0.014 (2)0.006 (2)0.002 (2)
C90.039 (3)0.035 (3)0.045 (3)0.004 (2)0.007 (2)0.002 (2)
C20.045 (3)0.037 (3)0.054 (3)0.010 (2)0.013 (3)0.003 (2)
C190.048 (3)0.033 (3)0.031 (3)0.016 (2)0.007 (2)0.002 (2)
C10.036 (3)0.040 (3)0.048 (3)0.003 (2)0.004 (2)0.008 (2)
C300.039 (3)0.048 (3)0.038 (3)0.017 (2)0.001 (2)0.003 (2)
C70.041 (3)0.065 (4)0.043 (3)0.006 (3)0.001 (2)0.020 (3)
C140.033 (3)0.042 (3)0.047 (3)0.016 (2)0.004 (2)0.003 (2)
C180.055 (3)0.052 (3)0.037 (3)0.026 (3)0.016 (2)0.004 (2)
C290.038 (3)0.075 (4)0.048 (3)0.018 (3)0.004 (2)0.014 (3)
C160.044 (3)0.041 (3)0.048 (3)0.010 (2)0.008 (2)0.003 (2)
C260.062 (4)0.048 (3)0.045 (3)0.007 (3)0.001 (3)0.000 (3)
C360.054 (3)0.048 (3)0.042 (3)0.012 (3)0.004 (3)0.003 (2)
C280.039 (3)0.069 (4)0.073 (4)0.016 (3)0.002 (3)0.026 (3)
C170.042 (3)0.051 (3)0.054 (3)0.012 (3)0.017 (3)0.009 (3)
C210.064 (4)0.062 (4)0.076 (5)0.004 (3)0.004 (3)0.009 (3)
C370.042 (3)0.063 (4)0.044 (3)0.003 (3)0.003 (2)0.004 (3)
C220.040 (3)0.072 (4)0.088 (5)0.007 (3)0.008 (3)0.008 (4)
C340.061 (4)0.049 (3)0.053 (3)0.027 (3)0.002 (3)0.008 (3)
C240.067 (4)0.085 (5)0.064 (4)0.013 (4)0.026 (3)0.021 (4)
C230.053 (4)0.076 (4)0.094 (5)0.021 (3)0.038 (4)0.013 (4)
C270.072 (4)0.068 (4)0.049 (3)0.004 (3)0.018 (3)0.011 (3)
C30.052 (3)0.061 (4)0.053 (3)0.000 (3)0.015 (3)0.005 (3)
C250.064 (4)0.057 (4)0.093 (5)0.018 (3)0.018 (4)0.015 (4)
Geometric parameters (Å, º) top
Fe1—C92.020 (5)C8—C91.401 (6)
Fe1—C62.025 (4)C8—H80.9300
Fe1—C52.026 (5)C4—C31.390 (7)
Fe1—C42.026 (5)C4—H40.9300
Fe1—C12.029 (4)C6—C71.403 (6)
Fe1—C102.030 (4)C6—H60.9300
Fe1—C82.039 (5)C15—C201.367 (6)
Fe1—C32.040 (5)C15—C161.386 (6)
Fe1—C72.044 (5)C38—C371.374 (6)
Fe1—C22.045 (5)C38—H380.9300
Fe2—C302.024 (5)C20—C191.398 (6)
Fe2—C222.027 (5)C20—H200.9300
Fe2—C292.029 (5)C9—H90.9300
Fe2—C232.036 (5)C2—C11.398 (6)
Fe2—C252.042 (6)C2—C31.412 (6)
Fe2—C262.042 (5)C2—H20.9300
Fe2—C282.042 (5)C19—C181.378 (6)
Fe2—C242.043 (6)C1—H10.9300
Fe2—C212.044 (6)C30—C291.425 (6)
Fe2—C272.057 (5)C30—C261.432 (6)
O1—C111.265 (5)C7—H70.9300
O4—C391.350 (5)C14—H14A0.9600
O4—H4O0.8200C14—H14B0.9600
O2—C191.350 (5)C14—H14C0.9600
O2—H2O0.8200C18—C171.380 (6)
N1—C131.340 (5)C18—H180.9300
N1—C151.429 (5)C29—C281.421 (7)
N1—H1N0.8600C29—H290.9300
C10—C111.491 (6)C16—C171.385 (6)
C11—C121.400 (5)C16—H160.9300
C13—C141.493 (5)C26—C271.402 (7)
C35—C361.373 (6)C26—H260.9300
C35—C401.390 (6)C36—C371.387 (6)
N2—H2N0.8600C36—H360.9300
C39—C381.377 (6)C28—C271.402 (7)
C39—C401.385 (6)C28—H280.9300
C40—H400.9300C17—H170.9300
C12—C131.376 (6)C21—C251.408 (8)
C12—H120.9300C21—C221.415 (8)
O3—C311.256 (5)C21—H210.9300
N2—C331.348 (5)C37—H370.9300
N2—C351.423 (5)C22—C231.387 (8)
C30—C311.470 (6)C22—H220.9300
C31—C321.417 (6)C34—H34A0.9600
C32—C331.369 (6)C34—H34B0.9600
C33—C341.503 (6)C34—H34C0.9600
C32—H320.9300C24—C231.398 (7)
C10—C61.420 (6)C24—C251.410 (8)
C10—C91.420 (6)C24—H240.9300
C5—C41.409 (7)C23—H230.9300
C5—C11.412 (6)C27—H270.9300
C5—H50.9300C3—H30.9300
C8—C71.391 (7)C25—H250.9300
C9—Fe1—C668.46 (19)C5—C4—Fe169.6 (3)
C9—Fe1—C5107.0 (2)C3—C4—H4125.7
C6—Fe1—C5166.0 (2)C5—C4—H4125.7
C9—Fe1—C4127.3 (2)Fe1—C4—H4125.6
C6—Fe1—C4152.5 (2)C7—C6—C10108.5 (4)
C5—Fe1—C440.7 (2)C7—C6—Fe170.5 (3)
C9—Fe1—C1117.92 (19)C10—C6—Fe169.7 (2)
C6—Fe1—C1128.49 (18)C7—C6—H6125.7
C5—Fe1—C140.77 (18)C10—C6—H6125.7
C4—Fe1—C168.3 (2)Fe1—C6—H6125.6
C9—Fe1—C1041.05 (17)N1—C13—C12120.2 (4)
C6—Fe1—C1041.00 (17)N1—C13—C14118.5 (4)
C5—Fe1—C10127.0 (2)C12—C13—C14121.2 (4)
C4—Fe1—C10165.3 (2)C20—C15—C16120.6 (4)
C1—Fe1—C10107.44 (18)C20—C15—N1118.7 (4)
C9—Fe1—C840.39 (18)C16—C15—N1120.6 (4)
C6—Fe1—C867.6 (2)C37—C38—C39120.1 (4)
C5—Fe1—C8118.1 (2)C37—C38—H38120.0
C4—Fe1—C8108.4 (2)C39—C38—H38120.0
C1—Fe1—C8151.8 (2)C15—C20—C19120.1 (5)
C10—Fe1—C868.34 (18)C15—C20—H20119.9
C9—Fe1—C3165.2 (2)C19—C20—H20119.9
C6—Fe1—C3119.8 (2)C8—C9—C10108.2 (4)
C5—Fe1—C367.9 (2)C8—C9—Fe170.5 (3)
C4—Fe1—C340.0 (2)C10—C9—Fe169.9 (3)
C1—Fe1—C368.0 (2)C8—C9—H9125.9
C10—Fe1—C3153.0 (2)C10—C9—H9125.9
C8—Fe1—C3128.5 (2)Fe1—C9—H9125.3
C9—Fe1—C767.9 (2)C1—C2—C3108.1 (4)
C6—Fe1—C740.35 (17)C1—C2—Fe169.3 (3)
C5—Fe1—C7151.7 (2)C3—C2—Fe169.6 (3)
C4—Fe1—C7118.9 (2)C1—C2—H2126.0
C1—Fe1—C7166.8 (2)C3—C2—H2126.0
C10—Fe1—C768.47 (18)Fe1—C2—H2126.7
C8—Fe1—C739.84 (19)O2—C19—C18123.9 (4)
C3—Fe1—C7109.6 (2)O2—C19—C20116.5 (4)
C9—Fe1—C2152.17 (19)C18—C19—C20119.6 (5)
C6—Fe1—C2109.6 (2)C2—C1—C5108.0 (4)
C5—Fe1—C267.9 (2)C2—C1—Fe170.6 (3)
C4—Fe1—C267.6 (2)C5—C1—Fe169.5 (3)
C1—Fe1—C240.14 (18)C2—C1—H1126.0
C10—Fe1—C2118.80 (18)C5—C1—H1126.0
C8—Fe1—C2166.6 (2)Fe1—C1—H1125.5
C3—Fe1—C240.43 (18)C29—C30—C26106.7 (4)
C7—Fe1—C2129.7 (2)C29—C30—C31126.4 (4)
C30—Fe2—C22106.8 (2)C26—C30—C31126.8 (4)
C30—Fe2—C2941.17 (18)C29—C30—Fe269.6 (3)
C22—Fe2—C29122.1 (2)C26—C30—Fe270.0 (3)
C30—Fe2—C23122.0 (2)C31—C30—Fe2121.6 (3)
C22—Fe2—C2339.9 (2)C8—C7—C6108.0 (4)
C29—Fe2—C23157.9 (2)C8—C7—Fe169.9 (3)
C30—Fe2—C25158.8 (2)C6—C7—Fe169.1 (3)
C22—Fe2—C2568.0 (2)C8—C7—H7126.0
C29—Fe2—C25122.8 (2)C6—C7—H7126.0
C23—Fe2—C2568.0 (2)Fe1—C7—H7126.6
C30—Fe2—C2641.25 (18)C13—C14—H14A109.5
C22—Fe2—C26123.8 (2)C13—C14—H14B109.5
C29—Fe2—C2668.5 (2)H14A—C14—H14B109.5
C23—Fe2—C26108.5 (2)C13—C14—H14C109.5
C25—Fe2—C26158.7 (2)H14A—C14—H14C109.5
C30—Fe2—C2868.83 (19)H14B—C14—H14C109.5
C22—Fe2—C28158.6 (3)C19—C18—C17119.9 (4)
C29—Fe2—C2840.86 (19)C19—C18—H18120.1
C23—Fe2—C28160.1 (3)C17—C18—H18120.1
C25—Fe2—C28108.2 (2)C28—C29—C30107.7 (5)
C26—Fe2—C2867.5 (2)C28—C29—Fe270.1 (3)
C30—Fe2—C24158.4 (2)C30—C29—Fe269.2 (3)
C22—Fe2—C2467.2 (3)C28—C29—H29126.2
C29—Fe2—C24159.8 (2)C30—C29—H29126.2
C23—Fe2—C2440.1 (2)Fe2—C29—H29126.1
C25—Fe2—C2440.4 (2)C17—C16—C15119.1 (5)
C26—Fe2—C24123.4 (2)C17—C16—H16120.5
C28—Fe2—C24124.4 (2)C15—C16—H16120.5
C30—Fe2—C21122.4 (2)C27—C26—C30108.8 (5)
C22—Fe2—C2140.7 (2)C27—C26—Fe270.6 (3)
C29—Fe2—C21106.9 (2)C30—C26—Fe268.7 (3)
C23—Fe2—C2167.8 (3)C27—C26—H26125.6
C25—Fe2—C2140.3 (2)C30—C26—H26125.6
C26—Fe2—C21159.8 (2)Fe2—C26—H26126.7
C28—Fe2—C21122.8 (3)C35—C36—C37119.2 (5)
C24—Fe2—C2167.5 (3)C35—C36—H36120.4
C30—Fe2—C2768.7 (2)C37—C36—H36120.4
C22—Fe2—C27159.7 (3)C27—C28—C29108.7 (5)
C29—Fe2—C2768.3 (2)C27—C28—Fe270.6 (3)
C23—Fe2—C27124.5 (3)C29—C28—Fe269.1 (3)
C25—Fe2—C27123.3 (2)C27—C28—H28125.6
C26—Fe2—C2739.98 (19)C29—C28—H28125.6
C28—Fe2—C2740.0 (2)Fe2—C28—H28126.3
C24—Fe2—C27109.3 (2)C18—C17—C16120.8 (5)
C21—Fe2—C27158.5 (2)C18—C17—H17119.6
C39—O4—H4O109.5C16—C17—H17119.6
C19—O2—H2O109.5C25—C21—C22107.4 (6)
C13—N1—C15126.2 (4)C25—C21—Fe269.8 (3)
C13—N1—H1N116.9C22—C21—Fe269.0 (3)
C15—N1—H1N116.9C25—C21—H21126.3
O1—C11—C12122.8 (4)C22—C21—H21126.3
O1—C11—C10118.9 (4)Fe2—C21—H21126.5
C12—C11—C10118.2 (4)C38—C37—C36120.8 (5)
C36—C35—C40120.3 (4)C38—C37—H37119.6
C36—C35—N2118.6 (4)C36—C37—H37119.6
C40—C35—N2121.1 (4)C23—C22—C21108.7 (6)
C33—N2—C35126.9 (4)C23—C22—Fe270.4 (3)
C33—N2—H2N116.5C21—C22—Fe270.3 (3)
C35—N2—H2N116.5C23—C22—H22125.7
O4—C39—C38123.5 (4)C21—C22—H22125.7
O4—C39—C40116.8 (4)Fe2—C22—H22125.2
C38—C39—C40119.7 (4)C33—C34—H34A109.5
C39—C40—C35119.9 (4)C33—C34—H34B109.5
C39—C40—H40120.1H34A—C34—H34B109.5
C35—C40—H40120.1C33—C34—H34C109.5
C13—C12—C11124.9 (4)H34A—C34—H34C109.5
C13—C12—H12117.5H34B—C34—H34C109.5
C11—C12—H12117.5C23—C24—C25108.5 (6)
O3—C31—C32122.0 (4)C23—C24—Fe269.7 (3)
O3—C31—C30119.0 (4)C25—C24—Fe269.8 (3)
C32—C31—C30119.0 (4)C23—C24—H24125.7
C33—C32—C31124.0 (4)C25—C24—H24125.7
C33—C32—H32118.0Fe2—C24—H24126.4
C31—C32—H32118.0C22—C23—C24108.0 (6)
C6—C10—C9106.5 (4)C22—C23—Fe269.7 (3)
C6—C10—C11127.3 (4)C24—C23—Fe270.2 (3)
C9—C10—C11126.2 (4)C22—C23—H23126.0
C6—C10—Fe169.3 (3)C24—C23—H23126.0
C9—C10—Fe169.1 (2)Fe2—C23—H23125.6
C11—C10—Fe1126.2 (3)C26—C27—C28108.1 (5)
C4—C5—C1107.5 (5)C26—C27—Fe269.4 (3)
C4—C5—Fe169.7 (3)C28—C27—Fe269.4 (3)
C1—C5—Fe169.7 (3)C26—C27—H27126.0
C4—C5—H5126.3C28—C27—H27126.0
C1—C5—H5126.3Fe2—C27—H27126.8
Fe1—C5—H5125.9C4—C3—C2108.0 (5)
C7—C8—C9108.7 (4)C4—C3—Fe169.5 (3)
C7—C8—Fe170.3 (3)C2—C3—Fe170.0 (3)
C9—C8—Fe169.1 (3)C4—C3—H3126.0
C7—C8—H8125.6C2—C3—H3126.0
C9—C8—H8125.6Fe1—C3—H3126.1
Fe1—C8—H8126.6C21—C25—C24107.4 (5)
N2—C33—C32121.6 (4)C21—C25—Fe269.9 (3)
N2—C33—C34117.7 (4)C24—C25—Fe269.8 (3)
C32—C33—C34120.7 (4)C21—C25—H25126.3
C3—C4—C5108.5 (5)C24—C25—H25126.3
C3—C4—Fe170.6 (3)Fe2—C25—H25125.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.861.962.642 (5)136
N2—H2N···O30.861.992.645 (5)132
O2—H2O···O3i0.821.822.629 (5)170
O4—H4O···O10.821.862.679 (5)172
C2—H2···Cg3ii0.932.853.686 (5)150
C4—H4···Cg6iii0.932.893.614 (6)135
C28—H28···Cg3iv0.932.963.655 (6)133
Symmetry codes: (i) x1, y+1, z; (ii) x, y+2, z+1; (iii) x+1, y+1, z+1; (iv) x+1, y+1, z+2.
(II) (Z)-1-Ferrocenyl-3-(4-hydroxyanilino)but-2-en-1-one top
Crystal data top
[Fe(C5H5)(C15H14NO2)]Z = 4
Mr = 361.21F(000) = 752
TriclinicP1Dx = 1.472 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71070 Å
a = 7.4100 (11) ÅCell parameters from 5287 reflections
b = 14.687 (2) Åθ = 3.1–25.3°
c = 15.5601 (19) ŵ = 0.94 mm1
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
Data collection top
Rigaku Mercury
diffractometer
5891 independent reflections
Radiation source: fine-focus sealed tube4742 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 7.31 pixels mm-1θmax = 25.4°, θmin = 3.1°
ω scansh = 88
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1716
Tmin = 0.767, Tmax = 0.896l = 1817
15645 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-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 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
[Fe(C5H5)(C15H14NO2)]γ = 86.297 (8)°
Mr = 361.21V = 1630.3 (4) Å3
TriclinicP1Z = 4
a = 7.4100 (11) ÅMo Kα radiation
b = 14.687 (2) ŵ = 0.94 mm1
c = 15.5601 (19) ÅT = 173 K
α = 80.370 (7)°0.30 × 0.15 × 0.12 mm
β = 77.677 (7)°
Data collection top
Rigaku Mercury
diffractometer
5891 independent reflections
Absorption correction: multi-scan
(Jacobson, 1998)
4742 reflections with I > 2σ(I)
Tmin = 0.767, Tmax = 0.896Rint = 0.036
15645 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 1.10Δρmax = 0.47 e Å3
5891 reflectionsΔρmin = 0.38 e Å3
438 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.07183 (6)0.40931 (3)0.32592 (3)0.02270 (13)
Fe20.24808 (6)1.08742 (3)0.82459 (3)0.02250 (13)
O10.2716 (3)0.62051 (14)0.18972 (14)0.0308 (5)
O21.1341 (3)0.81905 (15)0.15364 (15)0.0342 (6)
H2O1.12190.85670.19910.051*
O30.1237 (3)0.92476 (14)0.69309 (14)0.0311 (5)
O40.4398 (3)0.61088 (15)0.32530 (16)0.0365 (6)
H4O0.37370.61340.28730.055*
N10.4737 (4)0.65813 (17)0.02983 (16)0.0266 (6)
H1N0.43840.66930.08490.032*
N20.2527 (4)0.89164 (17)0.53037 (17)0.0262 (6)
H2N0.21240.87180.58750.031*
C100.0400 (4)0.5087 (2)0.2208 (2)0.0237 (7)
C90.0663 (4)0.5320 (2)0.3025 (2)0.0286 (7)
H90.05400.58570.32720.034*
C80.1929 (4)0.4613 (2)0.3400 (2)0.0333 (8)
H80.28160.45960.39420.040*
C70.1662 (4)0.3937 (2)0.2838 (2)0.0317 (8)
H70.23290.33850.29380.038*
C60.0230 (4)0.4221 (2)0.2099 (2)0.0280 (7)
H60.02320.38950.16150.034*
C10.3405 (4)0.4013 (2)0.3384 (2)0.0284 (7)
H10.43720.43840.30220.034*
C50.2243 (5)0.4223 (2)0.4174 (2)0.0319 (8)
H50.22810.47590.44360.038*
C40.1010 (5)0.3488 (2)0.4505 (2)0.0382 (9)
H40.00810.34420.50340.046*
C30.1397 (5)0.2840 (2)0.3917 (2)0.0359 (9)
H30.07650.22830.39770.043*
C20.2887 (4)0.3156 (2)0.3219 (2)0.0305 (8)
H20.34390.28500.27310.037*
C110.1875 (4)0.5647 (2)0.1591 (2)0.0239 (7)
C120.2260 (4)0.5558 (2)0.0684 (2)0.0236 (7)
H120.15280.51560.04920.028*
C130.3650 (4)0.6025 (2)0.0051 (2)0.0248 (7)
C140.3925 (5)0.5925 (2)0.0912 (2)0.0301 (7)
H14A0.33070.64450.12270.045*
H14B0.33990.53450.09610.045*
H14C0.52500.59190.11760.045*
C150.6384 (4)0.7020 (2)0.0198 (2)0.0256 (7)
C160.6425 (4)0.7622 (2)0.0992 (2)0.0275 (7)
H160.53300.77570.12200.033*
C170.8070 (4)0.8028 (2)0.1451 (2)0.0269 (7)
H170.81010.84310.19990.032*
C180.9672 (4)0.7847 (2)0.1114 (2)0.0255 (7)
C190.9592 (5)0.7280 (2)0.0294 (2)0.0276 (7)
H191.06600.71820.00400.033*
C200.7971 (4)0.6861 (2)0.0150 (2)0.0273 (7)
H200.79390.64600.06990.033*
C300.1145 (4)1.0779 (2)0.7250 (2)0.0235 (7)
C290.1937 (5)1.1670 (2)0.7117 (2)0.0279 (7)
H290.28291.19270.66150.033*
C280.1153 (5)1.2098 (2)0.7867 (2)0.0337 (8)
H280.14241.26940.79560.040*
C270.0100 (5)1.1485 (2)0.8457 (2)0.0340 (8)
H270.08261.16020.90110.041*
C260.0102 (4)1.0667 (2)0.8089 (2)0.0276 (7)
H260.08101.01390.83550.033*
C210.4314 (5)0.9787 (2)0.8337 (2)0.0313 (8)
H210.44580.92950.79990.038*
C250.5272 (4)1.0624 (2)0.8092 (2)0.0316 (8)
H250.61721.07930.75620.038*
C240.4653 (5)1.1162 (2)0.8772 (2)0.0368 (9)
H240.50601.17600.87810.044*
C230.3322 (5)1.0660 (3)0.9439 (2)0.0398 (9)
H230.26811.08600.99750.048*
C220.3113 (5)0.9805 (2)0.9166 (2)0.0359 (8)
H220.23070.93300.94860.043*
C310.1550 (4)1.0097 (2)0.6627 (2)0.0240 (7)
C320.2176 (4)1.0410 (2)0.5708 (2)0.0239 (7)
H320.23041.10560.55170.029*
C330.2616 (4)0.9833 (2)0.5070 (2)0.0233 (7)
C340.3192 (5)1.0240 (2)0.4104 (2)0.0289 (7)
H34A0.41360.98360.38040.043*
H34B0.36981.08510.40550.043*
H34C0.21171.03000.38230.043*
C350.2997 (4)0.8218 (2)0.47540 (19)0.0225 (7)
C400.4240 (4)0.7509 (2)0.4972 (2)0.0269 (7)
H400.47930.75070.54700.032*
C390.4668 (4)0.6809 (2)0.4465 (2)0.0285 (7)
H390.55090.63250.46200.034*
C380.3886 (4)0.6804 (2)0.3733 (2)0.0241 (7)
C370.2612 (4)0.7499 (2)0.3526 (2)0.0254 (7)
H370.20480.74950.30330.030*
C360.2168 (4)0.8194 (2)0.4040 (2)0.0264 (7)
H360.12820.86630.39020.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0190 (2)0.0261 (3)0.0229 (3)0.00200 (18)0.00653 (19)0.00018 (18)
Fe20.0236 (3)0.0250 (2)0.0204 (2)0.00144 (18)0.00741 (19)0.00525 (18)
O10.0425 (14)0.0291 (12)0.0222 (12)0.0090 (10)0.0061 (10)0.0056 (9)
O20.0326 (13)0.0331 (13)0.0341 (14)0.0048 (10)0.0072 (11)0.0045 (10)
O30.0436 (14)0.0279 (12)0.0218 (12)0.0102 (10)0.0047 (10)0.0033 (9)
O40.0441 (15)0.0321 (13)0.0412 (15)0.0091 (11)0.0198 (12)0.0184 (11)
N10.0333 (16)0.0284 (14)0.0179 (13)0.0071 (12)0.0026 (12)0.0037 (11)
N20.0335 (16)0.0268 (14)0.0184 (14)0.0045 (12)0.0040 (12)0.0042 (11)
C100.0215 (16)0.0270 (17)0.0226 (16)0.0027 (13)0.0072 (14)0.0017 (13)
C90.0256 (17)0.0296 (17)0.0308 (18)0.0074 (14)0.0087 (15)0.0051 (14)
C80.0188 (17)0.045 (2)0.0332 (19)0.0045 (15)0.0041 (15)0.0000 (16)
C70.0229 (17)0.0378 (19)0.037 (2)0.0072 (14)0.0159 (16)0.0011 (16)
C60.0273 (18)0.0340 (18)0.0263 (17)0.0000 (14)0.0156 (15)0.0027 (14)
C10.0207 (17)0.0346 (19)0.0295 (18)0.0029 (14)0.0106 (15)0.0037 (14)
C50.037 (2)0.0367 (19)0.0278 (18)0.0044 (15)0.0203 (16)0.0050 (15)
C40.037 (2)0.048 (2)0.0244 (18)0.0015 (17)0.0058 (16)0.0090 (16)
C30.0297 (19)0.0282 (18)0.047 (2)0.0064 (15)0.0128 (17)0.0094 (16)
C20.0294 (18)0.0290 (18)0.0346 (19)0.0089 (14)0.0123 (16)0.0057 (14)
C110.0262 (17)0.0202 (16)0.0260 (17)0.0058 (13)0.0098 (14)0.0024 (13)
C120.0249 (17)0.0244 (16)0.0231 (17)0.0007 (13)0.0097 (14)0.0022 (13)
C130.0307 (18)0.0239 (16)0.0215 (16)0.0047 (14)0.0104 (14)0.0035 (13)
C140.0312 (18)0.0341 (18)0.0260 (18)0.0030 (15)0.0075 (15)0.0044 (14)
C150.0338 (19)0.0220 (16)0.0228 (17)0.0004 (14)0.0073 (15)0.0077 (13)
C160.0327 (19)0.0224 (16)0.0283 (18)0.0000 (14)0.0099 (15)0.0024 (13)
C170.040 (2)0.0191 (15)0.0224 (17)0.0011 (14)0.0090 (15)0.0014 (13)
C180.0293 (18)0.0201 (15)0.0273 (17)0.0006 (13)0.0042 (15)0.0065 (13)
C190.0329 (19)0.0250 (16)0.0277 (18)0.0054 (14)0.0116 (15)0.0076 (13)
C200.038 (2)0.0225 (16)0.0206 (16)0.0012 (14)0.0063 (15)0.0026 (13)
C300.0213 (16)0.0285 (17)0.0231 (17)0.0027 (13)0.0114 (13)0.0034 (13)
C290.0357 (19)0.0270 (17)0.0225 (17)0.0020 (14)0.0123 (15)0.0015 (13)
C280.049 (2)0.0242 (17)0.0339 (19)0.0130 (15)0.0223 (17)0.0086 (14)
C270.0291 (19)0.048 (2)0.0277 (18)0.0143 (16)0.0082 (15)0.0155 (16)
C260.0211 (17)0.0393 (19)0.0241 (17)0.0009 (14)0.0064 (14)0.0081 (14)
C210.0332 (19)0.0290 (18)0.036 (2)0.0107 (14)0.0179 (16)0.0074 (15)
C250.0201 (17)0.042 (2)0.035 (2)0.0002 (15)0.0091 (15)0.0077 (16)
C240.034 (2)0.040 (2)0.047 (2)0.0027 (16)0.0241 (18)0.0172 (17)
C230.048 (2)0.055 (2)0.0227 (18)0.0160 (18)0.0207 (17)0.0131 (17)
C220.041 (2)0.035 (2)0.032 (2)0.0002 (16)0.0152 (17)0.0047 (15)
C310.0201 (16)0.0296 (17)0.0244 (17)0.0003 (13)0.0083 (13)0.0058 (13)
C320.0244 (16)0.0228 (16)0.0249 (17)0.0006 (13)0.0076 (14)0.0020 (13)
C330.0189 (16)0.0304 (17)0.0220 (16)0.0011 (13)0.0075 (13)0.0045 (13)
C340.0342 (19)0.0304 (17)0.0223 (17)0.0002 (14)0.0072 (15)0.0033 (14)
C350.0248 (17)0.0231 (16)0.0182 (15)0.0047 (13)0.0019 (13)0.0012 (12)
C400.0288 (18)0.0316 (18)0.0217 (17)0.0051 (14)0.0106 (14)0.0002 (13)
C390.0289 (18)0.0242 (17)0.0337 (19)0.0029 (14)0.0129 (15)0.0014 (14)
C380.0246 (17)0.0239 (16)0.0237 (17)0.0040 (13)0.0011 (14)0.0069 (13)
C370.0274 (18)0.0284 (17)0.0232 (17)0.0031 (14)0.0115 (14)0.0034 (13)
C360.0257 (17)0.0266 (17)0.0276 (18)0.0013 (13)0.0076 (14)0.0039 (13)
Geometric parameters (Å, º) top
Fe1—C92.032 (3)C15—C201.387 (4)
Fe1—C12.035 (3)C15—C161.389 (4)
Fe1—C52.036 (3)C16—C171.389 (4)
Fe1—C32.039 (3)C16—H160.9500
Fe1—C82.040 (3)C17—C181.390 (4)
Fe1—C42.043 (3)C17—H170.9500
Fe1—C102.045 (3)C18—C191.394 (4)
Fe1—C22.045 (3)C19—C201.377 (4)
Fe1—C72.046 (3)C19—H190.9500
Fe1—C62.049 (3)C20—H200.9500
Fe2—C262.028 (3)C30—C261.420 (4)
Fe2—C212.035 (3)C30—C291.434 (4)
Fe2—C302.036 (3)O3—C311.275 (4)
Fe2—C292.042 (3)O4—C381.353 (4)
Fe2—C222.043 (3)O4—H4O0.8400
Fe2—C272.045 (3)N2—C331.337 (4)
Fe2—C252.047 (3)N2—C351.423 (4)
Fe2—C242.051 (3)N2—H2N0.8800
Fe2—C232.052 (3)C30—C311.481 (4)
Fe2—C282.052 (3)C29—C281.416 (5)
O1—C111.269 (4)C29—H290.9500
O2—C181.356 (4)C28—C271.408 (5)
O2—H2O0.8400C28—H280.9500
N1—C131.336 (4)C27—C261.414 (5)
N1—C151.427 (4)C27—H270.9500
N1—H1N0.8800C26—H260.9500
C10—C111.482 (4)C21—C221.405 (5)
C11—C121.406 (4)C21—C251.415 (5)
C12—C131.391 (4)C21—H210.9500
C12—H120.9500C25—C241.408 (5)
C13—C141.498 (4)C25—H250.9500
C10—C91.427 (4)C24—C231.412 (5)
C10—C61.430 (4)C24—H240.9500
C9—C81.410 (5)C23—C221.420 (5)
C9—H90.9500C23—H230.9500
C8—C71.407 (5)C22—H220.9500
C8—H80.9500C31—C321.413 (4)
C7—C61.414 (5)C32—C331.386 (4)
C7—H70.9500C32—H320.9500
C6—H60.9500C33—C341.502 (4)
C1—C51.410 (5)C34—H34A0.9800
C1—C21.418 (5)C34—H34B0.9800
C1—H10.9500C34—H34C0.9800
C5—C41.416 (5)C35—C361.385 (4)
C5—H50.9500C35—C401.393 (4)
C4—C31.404 (5)C40—C391.379 (4)
C4—H40.9500C40—H400.9500
C3—C21.413 (5)C39—C381.385 (4)
C3—H30.9500C39—H390.9500
C2—H20.9500C38—C371.390 (4)
C14—H14A0.9800C37—C361.382 (4)
C14—H14B0.9800C37—H370.9500
C14—H14C0.9800C36—H360.9500
C9—Fe1—C1122.34 (13)C5—C4—Fe169.43 (18)
C9—Fe1—C5106.77 (14)C3—C4—H4125.9
C1—Fe1—C540.53 (13)C5—C4—H4125.9
C9—Fe1—C3158.93 (14)Fe1—C4—H4126.5
C1—Fe1—C368.03 (13)C4—C3—C2108.5 (3)
C5—Fe1—C368.22 (14)C4—C3—Fe170.02 (19)
C9—Fe1—C840.53 (13)C2—C3—Fe169.99 (18)
C1—Fe1—C8156.55 (14)C4—C3—H3125.8
C5—Fe1—C8120.10 (14)C2—C3—H3125.8
C3—Fe1—C8122.80 (13)Fe1—C3—H3125.8
C9—Fe1—C4122.76 (14)C3—C2—C1107.2 (3)
C1—Fe1—C467.93 (13)C3—C2—Fe169.52 (19)
C5—Fe1—C440.62 (14)C1—C2—Fe169.27 (18)
C3—Fe1—C440.24 (14)C3—C2—H2126.4
C8—Fe1—C4105.91 (14)C1—C2—H2126.4
C9—Fe1—C1040.98 (12)Fe1—C2—H2126.4
C1—Fe1—C10109.57 (12)O1—C11—C12122.3 (3)
C5—Fe1—C10124.92 (13)O1—C11—C10118.8 (3)
C3—Fe1—C10158.39 (14)C12—C11—C10118.9 (3)
C8—Fe1—C1068.32 (13)C13—C12—C11123.9 (3)
C4—Fe1—C10160.63 (14)C13—C12—H12118.1
C9—Fe1—C2158.69 (13)C11—C12—H12118.1
C1—Fe1—C240.67 (13)N1—C13—C12119.8 (3)
C5—Fe1—C268.47 (14)N1—C13—C14119.5 (3)
C3—Fe1—C240.49 (13)C12—C13—C14120.7 (3)
C8—Fe1—C2160.09 (13)C13—C14—H14A109.5
C4—Fe1—C268.01 (14)C13—C14—H14B109.5
C10—Fe1—C2123.55 (13)H14A—C14—H14B109.5
C9—Fe1—C768.30 (13)C13—C14—H14C109.5
C1—Fe1—C7162.57 (14)H14A—C14—H14C109.5
C5—Fe1—C7155.02 (14)H14B—C14—H14C109.5
C3—Fe1—C7107.10 (13)C20—C15—C16119.6 (3)
C8—Fe1—C740.28 (14)C20—C15—N1118.1 (3)
C4—Fe1—C7119.95 (14)C16—C15—N1122.3 (3)
C10—Fe1—C768.39 (13)C15—C16—C17119.9 (3)
C2—Fe1—C7124.89 (14)C15—C16—H16120.0
C9—Fe1—C668.66 (13)C17—C16—H16120.0
C1—Fe1—C6126.78 (13)C16—C17—C18120.4 (3)
C5—Fe1—C6162.78 (13)C16—C17—H17119.8
C3—Fe1—C6122.04 (14)C18—C17—H17119.8
C8—Fe1—C667.96 (14)O2—C18—C17123.9 (3)
C4—Fe1—C6155.90 (14)O2—C18—C19116.9 (3)
C10—Fe1—C640.90 (12)C17—C18—C19119.2 (3)
C2—Fe1—C6109.39 (13)C20—C19—C18120.3 (3)
C7—Fe1—C640.39 (13)C20—C19—H19119.9
C26—Fe2—C21119.76 (13)C18—C19—H19119.9
C26—Fe2—C3040.91 (12)C19—C20—C15120.6 (3)
C21—Fe2—C30108.55 (13)C19—C20—H20119.7
C26—Fe2—C2968.92 (13)C15—C20—H20119.7
C21—Fe2—C29127.73 (13)C26—C30—C29107.6 (3)
C30—Fe2—C2941.17 (12)C26—C30—C31126.1 (3)
C26—Fe2—C22106.86 (14)C29—C30—C31126.3 (3)
C21—Fe2—C2240.29 (13)C26—C30—Fe269.26 (17)
C30—Fe2—C22126.06 (13)C29—C30—Fe269.63 (17)
C29—Fe2—C22164.49 (13)C31—C30—Fe2126.5 (2)
C26—Fe2—C2740.64 (13)C28—C29—C30107.8 (3)
C21—Fe2—C27153.92 (14)C28—C29—Fe270.15 (18)
C30—Fe2—C2768.27 (13)C30—C29—Fe269.19 (17)
C29—Fe2—C2768.00 (14)C28—C29—H29126.1
C22—Fe2—C27119.19 (14)C30—C29—H29126.1
C26—Fe2—C25155.11 (13)Fe2—C29—H29126.1
C21—Fe2—C2540.57 (13)C27—C28—C29108.1 (3)
C30—Fe2—C25121.07 (13)C27—C28—Fe269.62 (18)
C29—Fe2—C25109.12 (14)C29—C28—Fe269.39 (18)
C22—Fe2—C2568.03 (14)C27—C28—H28126.0
C27—Fe2—C25163.49 (14)C29—C28—H28126.0
C26—Fe2—C24162.62 (14)Fe2—C28—H28126.6
C21—Fe2—C2467.84 (14)C28—C27—C26108.8 (3)
C30—Fe2—C24155.39 (14)C28—C27—Fe270.18 (19)
C29—Fe2—C24120.42 (14)C26—C27—Fe269.07 (18)
C22—Fe2—C2467.99 (15)C28—C27—H27125.6
C27—Fe2—C24126.00 (14)C26—C27—H27125.6
C25—Fe2—C2440.18 (13)Fe2—C27—H27126.8
C26—Fe2—C23125.18 (14)C27—C26—C30107.7 (3)
C21—Fe2—C2367.86 (14)C27—C26—Fe270.30 (18)
C30—Fe2—C23163.09 (14)C30—C26—Fe269.83 (17)
C29—Fe2—C23153.96 (14)C27—C26—H26126.1
C22—Fe2—C2340.58 (14)C30—C26—H26126.1
C27—Fe2—C23107.24 (14)Fe2—C26—H26125.3
C25—Fe2—C2367.77 (14)C22—C21—C25108.5 (3)
C24—Fe2—C2340.27 (15)C22—C21—Fe270.17 (19)
C26—Fe2—C2868.46 (14)C25—C21—Fe270.16 (18)
C21—Fe2—C28164.90 (14)C22—C21—H21125.8
C30—Fe2—C2868.55 (13)C25—C21—H21125.8
C29—Fe2—C2840.46 (13)Fe2—C21—H21125.5
C22—Fe2—C28153.39 (14)C24—C25—C21107.7 (3)
C27—Fe2—C2840.20 (14)C24—C25—Fe270.07 (19)
C25—Fe2—C28127.15 (14)C21—C25—Fe269.27 (18)
C24—Fe2—C28108.24 (14)C24—C25—H25126.1
C23—Fe2—C28119.30 (14)C21—C25—H25126.1
C18—O2—H2O109.5Fe2—C25—H25126.1
C38—O4—H4O109.5C25—C24—C23108.2 (3)
C13—N1—C15129.5 (3)C25—C24—Fe269.75 (18)
C13—N1—H1N115.2C23—C24—Fe269.89 (19)
C15—N1—H1N115.2C25—C24—H24125.9
C33—N2—C35128.7 (3)C23—C24—H24125.9
C33—N2—H2N115.6Fe2—C24—H24126.1
C35—N2—H2N115.6C24—C23—C22107.8 (3)
C9—C10—C6107.3 (3)C24—C23—Fe269.84 (19)
C9—C10—C11125.9 (3)C22—C23—Fe269.40 (19)
C6—C10—C11126.8 (3)C24—C23—H23126.1
C9—C10—Fe169.05 (17)C22—C23—H23126.1
C6—C10—Fe169.71 (17)Fe2—C23—H23126.3
C11—C10—Fe1126.7 (2)C21—C22—C23107.7 (3)
C8—C9—C10107.8 (3)C21—C22—Fe269.54 (18)
C8—C9—Fe170.00 (18)C23—C22—Fe270.02 (19)
C10—C9—Fe169.97 (17)C21—C22—H22126.1
C8—C9—H9126.1C23—C22—H22126.1
C10—C9—H9126.1Fe2—C22—H22125.9
Fe1—C9—H9125.5O3—C31—C32121.8 (3)
C7—C8—C9108.7 (3)O3—C31—C30118.9 (3)
C7—C8—Fe170.12 (18)C32—C31—C30119.2 (3)
C9—C8—Fe169.47 (18)C33—C32—C31124.0 (3)
C7—C8—H8125.6C33—C32—H32118.0
C9—C8—H8125.6C31—C32—H32118.0
Fe1—C8—H8126.4N2—C33—C32120.6 (3)
C8—C7—C6108.2 (3)N2—C33—C34119.6 (3)
C8—C7—Fe169.60 (18)C32—C33—C34119.8 (3)
C6—C7—Fe169.91 (17)C33—C34—H34A109.5
C8—C7—H7125.9C33—C34—H34B109.5
C6—C7—H7125.9H34A—C34—H34B109.5
Fe1—C7—H7126.2C33—C34—H34C109.5
C7—C6—C10107.9 (3)H34A—C34—H34C109.5
C7—C6—Fe169.71 (18)H34B—C34—H34C109.5
C10—C6—Fe169.39 (17)C36—C35—C40119.1 (3)
C7—C6—H6126.1C36—C35—N2121.7 (3)
C10—C6—H6126.1C40—C35—N2119.0 (3)
Fe1—C6—H6126.4C39—C40—C35119.9 (3)
C5—C1—C2108.6 (3)C39—C40—H40120.0
C5—C1—Fe169.77 (18)C35—C40—H40120.0
C2—C1—Fe170.06 (18)C40—C39—C38120.8 (3)
C5—C1—H1125.7C40—C39—H39119.6
C2—C1—H1125.7C38—C39—H39119.6
Fe1—C1—H1126.0O4—C38—C39117.8 (3)
C1—C5—C4107.5 (3)O4—C38—C37122.9 (3)
C1—C5—Fe169.70 (18)C39—C38—C37119.3 (3)
C4—C5—Fe169.95 (19)C36—C37—C38119.8 (3)
C1—C5—H5126.3C36—C37—H37120.1
C4—C5—H5126.3C38—C37—H37120.1
Fe1—C5—H5125.7C37—C36—C35120.9 (3)
C3—C4—C5108.3 (3)C37—C36—H36119.6
C3—C4—Fe169.74 (19)C35—C36—H36119.6
C1—Fe1—C10—C9117.16 (19)C21—Fe2—C30—C26114.34 (19)
C5—Fe1—C10—C974.5 (2)C29—Fe2—C30—C26119.0 (3)
C3—Fe1—C10—C9163.2 (3)C22—Fe2—C30—C2673.0 (2)
C8—Fe1—C10—C937.86 (19)C27—Fe2—C30—C2638.05 (19)
C4—Fe1—C10—C938.2 (5)C25—Fe2—C30—C26157.18 (19)
C2—Fe1—C10—C9160.26 (19)C24—Fe2—C30—C26168.5 (3)
C7—Fe1—C10—C981.3 (2)C23—Fe2—C30—C2639.6 (5)
C6—Fe1—C10—C9118.8 (3)C28—Fe2—C30—C2681.4 (2)
C9—Fe1—C10—C6118.8 (3)C26—Fe2—C30—C29119.0 (3)
C1—Fe1—C10—C6124.06 (19)C21—Fe2—C30—C29126.63 (19)
C5—Fe1—C10—C6166.71 (19)C22—Fe2—C30—C29168.0 (2)
C3—Fe1—C10—C644.5 (4)C27—Fe2—C30—C2981.0 (2)
C8—Fe1—C10—C680.9 (2)C25—Fe2—C30—C2983.8 (2)
C4—Fe1—C10—C6156.9 (4)C24—Fe2—C30—C2949.5 (4)
C2—Fe1—C10—C681.0 (2)C23—Fe2—C30—C29158.6 (4)
C7—Fe1—C10—C637.43 (19)C28—Fe2—C30—C2937.59 (19)
C9—Fe1—C10—C11119.8 (3)C26—Fe2—C30—C31120.2 (3)
C1—Fe1—C10—C112.7 (3)C21—Fe2—C30—C315.9 (3)
C5—Fe1—C10—C1145.3 (3)C29—Fe2—C30—C31120.7 (3)
C3—Fe1—C10—C1176.9 (4)C22—Fe2—C30—C3147.2 (3)
C8—Fe1—C10—C11157.7 (3)C27—Fe2—C30—C31158.3 (3)
C4—Fe1—C10—C1181.7 (5)C25—Fe2—C30—C3137.0 (3)
C2—Fe1—C10—C1140.4 (3)C24—Fe2—C30—C3171.2 (4)
C7—Fe1—C10—C11158.8 (3)C23—Fe2—C30—C3180.7 (5)
C6—Fe1—C10—C11121.4 (3)C28—Fe2—C30—C31158.3 (3)
C6—C10—C9—C80.6 (3)C26—C30—C29—C280.7 (3)
C11—C10—C9—C8179.1 (3)C31—C30—C29—C28179.2 (3)
Fe1—C10—C9—C860.0 (2)Fe2—C30—C29—C2859.8 (2)
C6—C10—C9—Fe159.4 (2)C26—C30—C29—Fe259.1 (2)
C11—C10—C9—Fe1120.8 (3)C31—C30—C29—Fe2121.0 (3)
C1—Fe1—C9—C8158.5 (2)C26—Fe2—C29—C2881.1 (2)
C5—Fe1—C9—C8117.0 (2)C21—Fe2—C29—C28166.9 (2)
C3—Fe1—C9—C844.2 (5)C30—Fe2—C29—C28119.0 (3)
C4—Fe1—C9—C875.5 (2)C22—Fe2—C29—C28158.0 (5)
C10—Fe1—C9—C8118.6 (3)C27—Fe2—C29—C2837.3 (2)
C2—Fe1—C9—C8169.4 (3)C25—Fe2—C29—C28125.3 (2)
C7—Fe1—C9—C837.1 (2)C24—Fe2—C29—C2882.6 (2)
C6—Fe1—C9—C880.6 (2)C23—Fe2—C29—C2847.0 (4)
C1—Fe1—C9—C1082.9 (2)C26—Fe2—C29—C3037.86 (18)
C5—Fe1—C9—C10124.38 (19)C21—Fe2—C29—C3074.1 (2)
C3—Fe1—C9—C10162.8 (3)C22—Fe2—C29—C3039.1 (6)
C8—Fe1—C9—C10118.6 (3)C27—Fe2—C29—C3081.7 (2)
C4—Fe1—C9—C10165.90 (18)C25—Fe2—C29—C30115.69 (19)
C2—Fe1—C9—C1050.8 (4)C24—Fe2—C29—C30158.45 (19)
C7—Fe1—C9—C1081.6 (2)C23—Fe2—C29—C30166.0 (3)
C6—Fe1—C9—C1038.03 (18)C28—Fe2—C29—C30119.0 (3)
C10—C9—C8—C70.7 (4)C30—C29—C28—C270.1 (4)
Fe1—C9—C8—C759.3 (2)Fe2—C29—C28—C2759.1 (2)
C10—C9—C8—Fe160.0 (2)C30—C29—C28—Fe259.2 (2)
C9—Fe1—C8—C7120.0 (3)C26—Fe2—C28—C2737.17 (19)
C1—Fe1—C8—C7171.1 (3)C21—Fe2—C28—C27163.0 (5)
C5—Fe1—C8—C7159.48 (19)C30—Fe2—C28—C2781.3 (2)
C3—Fe1—C8—C777.3 (2)C29—Fe2—C28—C27119.5 (3)
C4—Fe1—C8—C7117.8 (2)C22—Fe2—C28—C2747.6 (4)
C10—Fe1—C8—C781.7 (2)C25—Fe2—C28—C27165.2 (2)
C2—Fe1—C8—C748.7 (5)C24—Fe2—C28—C27124.7 (2)
C6—Fe1—C8—C737.50 (19)C23—Fe2—C28—C2782.1 (2)
C1—Fe1—C8—C951.1 (4)C26—Fe2—C28—C2982.4 (2)
C5—Fe1—C8—C980.5 (2)C21—Fe2—C28—C2943.5 (6)
C3—Fe1—C8—C9162.7 (2)C30—Fe2—C28—C2938.23 (19)
C4—Fe1—C8—C9122.2 (2)C22—Fe2—C28—C29167.1 (3)
C10—Fe1—C8—C938.27 (19)C27—Fe2—C28—C29119.5 (3)
C2—Fe1—C8—C9168.7 (4)C25—Fe2—C28—C2975.2 (2)
C7—Fe1—C8—C9120.0 (3)C24—Fe2—C28—C29115.8 (2)
C6—Fe1—C8—C982.5 (2)C23—Fe2—C28—C29158.4 (2)
C9—C8—C7—C60.5 (4)C29—C28—C27—C260.5 (4)
Fe1—C8—C7—C659.4 (2)Fe2—C28—C27—C2658.4 (2)
C9—C8—C7—Fe158.9 (2)C29—C28—C27—Fe258.9 (2)
C9—Fe1—C7—C837.28 (19)C26—Fe2—C27—C28120.3 (3)
C1—Fe1—C7—C8168.2 (4)C21—Fe2—C27—C28170.0 (3)
C5—Fe1—C7—C845.9 (4)C30—Fe2—C27—C2882.0 (2)
C3—Fe1—C7—C8120.9 (2)C29—Fe2—C27—C2837.52 (19)
C4—Fe1—C7—C879.0 (2)C22—Fe2—C27—C28157.7 (2)
C10—Fe1—C7—C881.5 (2)C25—Fe2—C27—C2845.6 (5)
C2—Fe1—C7—C8161.83 (19)C24—Fe2—C27—C2874.9 (2)
C6—Fe1—C7—C8119.4 (3)C23—Fe2—C27—C28115.3 (2)
C9—Fe1—C7—C682.1 (2)C21—Fe2—C27—C2649.7 (4)
C1—Fe1—C7—C648.7 (5)C30—Fe2—C27—C2638.30 (18)
C5—Fe1—C7—C6165.3 (3)C29—Fe2—C27—C2682.8 (2)
C3—Fe1—C7—C6119.7 (2)C22—Fe2—C27—C2681.9 (2)
C8—Fe1—C7—C6119.4 (3)C25—Fe2—C27—C26165.9 (4)
C4—Fe1—C7—C6161.6 (2)C24—Fe2—C27—C26164.7 (2)
C10—Fe1—C7—C637.90 (19)C23—Fe2—C27—C26124.4 (2)
C2—Fe1—C7—C678.7 (2)C28—Fe2—C27—C26120.3 (3)
C8—C7—C6—C100.2 (4)C28—C27—C26—C301.0 (4)
Fe1—C7—C6—C1059.1 (2)Fe2—C27—C26—C3060.1 (2)
C8—C7—C6—Fe159.3 (2)C28—C27—C26—Fe259.1 (2)
C9—C10—C6—C70.3 (3)C29—C30—C26—C271.0 (3)
C11—C10—C6—C7179.5 (3)C31—C30—C26—C27178.9 (3)
Fe1—C10—C6—C759.3 (2)Fe2—C30—C26—C2760.3 (2)
C9—C10—C6—Fe159.0 (2)C29—C30—C26—Fe259.3 (2)
C11—C10—C6—Fe1121.3 (3)C31—C30—C26—Fe2120.8 (3)
C9—Fe1—C6—C781.2 (2)C21—Fe2—C26—C27157.3 (2)
C1—Fe1—C6—C7163.7 (2)C30—Fe2—C26—C27118.5 (3)
C5—Fe1—C6—C7158.8 (4)C29—Fe2—C26—C2780.4 (2)
C3—Fe1—C6—C778.4 (2)C22—Fe2—C26—C27115.4 (2)
C8—Fe1—C6—C737.41 (19)C25—Fe2—C26—C27170.6 (3)
C4—Fe1—C6—C742.2 (4)C24—Fe2—C26—C2745.5 (5)
C10—Fe1—C6—C7119.3 (3)C23—Fe2—C26—C2774.7 (2)
C2—Fe1—C6—C7121.5 (2)C28—Fe2—C26—C2736.8 (2)
C9—Fe1—C6—C1038.11 (18)C21—Fe2—C26—C3084.3 (2)
C1—Fe1—C6—C1077.0 (2)C29—Fe2—C26—C3038.09 (18)
C5—Fe1—C6—C1039.5 (5)C22—Fe2—C26—C30126.12 (19)
C3—Fe1—C6—C10162.28 (18)C27—Fe2—C26—C30118.5 (3)
C8—Fe1—C6—C1081.9 (2)C25—Fe2—C26—C3052.1 (4)
C4—Fe1—C6—C10161.4 (3)C24—Fe2—C26—C30163.9 (4)
C2—Fe1—C6—C10119.24 (19)C23—Fe2—C26—C30166.89 (18)
C7—Fe1—C6—C10119.3 (3)C28—Fe2—C26—C3081.67 (19)
C9—Fe1—C1—C577.6 (2)C26—Fe2—C21—C2280.9 (2)
C3—Fe1—C1—C581.7 (2)C30—Fe2—C21—C22124.4 (2)
C8—Fe1—C1—C540.8 (4)C29—Fe2—C21—C22166.3 (2)
C4—Fe1—C1—C538.2 (2)C27—Fe2—C21—C2246.0 (4)
C10—Fe1—C1—C5121.27 (19)C25—Fe2—C21—C22119.2 (3)
C2—Fe1—C1—C5119.6 (3)C24—Fe2—C21—C2281.6 (2)
C7—Fe1—C1—C5158.6 (4)C23—Fe2—C21—C2238.0 (2)
C6—Fe1—C1—C5163.89 (19)C28—Fe2—C21—C22159.4 (5)
C9—Fe1—C1—C2162.77 (19)C26—Fe2—C21—C25159.85 (19)
C5—Fe1—C1—C2119.6 (3)C30—Fe2—C21—C25116.4 (2)
C3—Fe1—C1—C237.9 (2)C29—Fe2—C21—C2574.5 (2)
C8—Fe1—C1—C2160.4 (3)C22—Fe2—C21—C25119.2 (3)
C4—Fe1—C1—C281.5 (2)C27—Fe2—C21—C25165.3 (3)
C10—Fe1—C1—C2119.09 (19)C24—Fe2—C21—C2537.6 (2)
C7—Fe1—C1—C239.0 (5)C23—Fe2—C21—C2581.2 (2)
C6—Fe1—C1—C276.5 (2)C28—Fe2—C21—C2540.1 (6)
C2—C1—C5—C40.5 (4)C22—C21—C25—C240.2 (4)
Fe1—C1—C5—C460.0 (2)Fe2—C21—C25—C2459.7 (2)
C2—C1—C5—Fe159.5 (2)C22—C21—C25—Fe260.0 (2)
C9—Fe1—C5—C1120.49 (19)C26—Fe2—C25—C24164.2 (3)
C3—Fe1—C5—C181.2 (2)C21—Fe2—C25—C24118.9 (3)
C8—Fe1—C5—C1162.51 (18)C30—Fe2—C25—C24158.7 (2)
C4—Fe1—C5—C1118.4 (3)C29—Fe2—C25—C24114.8 (2)
C10—Fe1—C5—C179.2 (2)C22—Fe2—C25—C2481.4 (2)
C2—Fe1—C5—C137.51 (19)C27—Fe2—C25—C2437.9 (6)
C7—Fe1—C5—C1165.0 (3)C23—Fe2—C25—C2437.5 (2)
C6—Fe1—C5—C148.6 (5)C28—Fe2—C25—C2473.2 (3)
C9—Fe1—C5—C4121.1 (2)C26—Fe2—C25—C2145.3 (4)
C1—Fe1—C5—C4118.4 (3)C30—Fe2—C25—C2182.4 (2)
C3—Fe1—C5—C437.2 (2)C29—Fe2—C25—C21126.2 (2)
C8—Fe1—C5—C479.1 (2)C22—Fe2—C25—C2137.5 (2)
C10—Fe1—C5—C4162.4 (2)C27—Fe2—C25—C21156.8 (4)
C2—Fe1—C5—C480.9 (2)C24—Fe2—C25—C21118.9 (3)
C7—Fe1—C5—C446.6 (4)C23—Fe2—C25—C2181.4 (2)
C6—Fe1—C5—C4167.0 (4)C28—Fe2—C25—C21167.84 (19)
C1—C5—C4—C30.8 (4)C21—C25—C24—C230.3 (4)
Fe1—C5—C4—C359.1 (2)Fe2—C25—C24—C2359.5 (2)
C1—C5—C4—Fe159.9 (2)C21—C25—C24—Fe259.2 (2)
C9—Fe1—C4—C3163.20 (19)C26—Fe2—C24—C25157.4 (4)
C1—Fe1—C4—C381.6 (2)C21—Fe2—C24—C2537.9 (2)
C5—Fe1—C4—C3119.7 (3)C30—Fe2—C24—C2548.4 (4)
C8—Fe1—C4—C3122.3 (2)C29—Fe2—C24—C2583.9 (2)
C10—Fe1—C4—C3168.0 (3)C22—Fe2—C24—C2581.6 (2)
C2—Fe1—C4—C337.58 (19)C27—Fe2—C24—C25167.5 (2)
C7—Fe1—C4—C381.1 (2)C23—Fe2—C24—C25119.4 (3)
C6—Fe1—C4—C350.9 (4)C28—Fe2—C24—C25126.5 (2)
C9—Fe1—C4—C577.1 (2)C26—Fe2—C24—C2338.1 (6)
C1—Fe1—C4—C538.1 (2)C21—Fe2—C24—C2381.4 (2)
C3—Fe1—C4—C5119.7 (3)C30—Fe2—C24—C23167.8 (3)
C8—Fe1—C4—C5118.0 (2)C29—Fe2—C24—C23156.8 (2)
C10—Fe1—C4—C548.3 (5)C22—Fe2—C24—C2337.8 (2)
C2—Fe1—C4—C582.1 (2)C27—Fe2—C24—C2373.1 (3)
C7—Fe1—C4—C5159.2 (2)C25—Fe2—C24—C23119.4 (3)
C6—Fe1—C4—C5170.6 (3)C28—Fe2—C24—C23114.1 (2)
C5—C4—C3—C20.7 (4)C25—C24—C23—C220.2 (4)
Fe1—C4—C3—C259.6 (2)Fe2—C24—C23—C2259.2 (2)
C5—C4—C3—Fe158.9 (2)C25—C24—C23—Fe259.4 (2)
C9—Fe1—C3—C442.5 (5)C26—Fe2—C23—C24167.0 (2)
C1—Fe1—C3—C481.3 (2)C21—Fe2—C23—C2481.4 (2)
C5—Fe1—C3—C437.5 (2)C30—Fe2—C23—C24162.3 (4)
C8—Fe1—C3—C475.1 (2)C29—Fe2—C23—C2450.8 (4)
C10—Fe1—C3—C4169.2 (3)C22—Fe2—C23—C24119.1 (3)
C2—Fe1—C3—C4119.4 (3)C27—Fe2—C23—C24125.9 (2)
C7—Fe1—C3—C4116.4 (2)C25—Fe2—C23—C2437.4 (2)
C6—Fe1—C3—C4158.0 (2)C28—Fe2—C23—C2483.8 (2)
C9—Fe1—C3—C2162.0 (3)C26—Fe2—C23—C2273.9 (3)
C1—Fe1—C3—C238.1 (2)C21—Fe2—C23—C2237.7 (2)
C5—Fe1—C3—C281.9 (2)C30—Fe2—C23—C2243.2 (5)
C8—Fe1—C3—C2165.4 (2)C29—Fe2—C23—C22170.0 (3)
C4—Fe1—C3—C2119.4 (3)C27—Fe2—C23—C22115.0 (2)
C10—Fe1—C3—C249.8 (4)C25—Fe2—C23—C2281.7 (2)
C7—Fe1—C3—C2124.1 (2)C24—Fe2—C23—C22119.1 (3)
C6—Fe1—C3—C282.5 (2)C28—Fe2—C23—C22157.0 (2)
C4—C3—C2—C10.4 (4)C25—C21—C22—C230.1 (4)
Fe1—C3—C2—C159.2 (2)Fe2—C21—C22—C2359.9 (2)
C4—C3—C2—Fe159.7 (2)C25—C21—C22—Fe259.9 (2)
C5—C1—C2—C30.1 (4)C24—C23—C22—C210.1 (4)
Fe1—C1—C2—C359.4 (2)Fe2—C23—C22—C2159.6 (2)
C5—C1—C2—Fe159.3 (2)C24—C23—C22—Fe259.5 (2)
C9—Fe1—C2—C3162.2 (3)C26—Fe2—C22—C21116.4 (2)
C1—Fe1—C2—C3118.6 (3)C30—Fe2—C22—C2175.5 (2)
C5—Fe1—C2—C381.3 (2)C29—Fe2—C22—C2144.6 (6)
C8—Fe1—C2—C338.3 (5)C27—Fe2—C22—C21158.7 (2)
C4—Fe1—C2—C337.4 (2)C25—Fe2—C22—C2137.7 (2)
C10—Fe1—C2—C3160.3 (2)C24—Fe2—C22—C2181.2 (2)
C7—Fe1—C2—C374.7 (2)C23—Fe2—C22—C21118.8 (3)
C6—Fe1—C2—C3117.0 (2)C28—Fe2—C22—C21168.2 (3)
C9—Fe1—C2—C143.5 (4)C26—Fe2—C22—C23124.9 (2)
C5—Fe1—C2—C137.39 (19)C21—Fe2—C22—C23118.8 (3)
C3—Fe1—C2—C1118.6 (3)C30—Fe2—C22—C23165.7 (2)
C8—Fe1—C2—C1157.0 (4)C29—Fe2—C22—C23163.4 (5)
C4—Fe1—C2—C181.3 (2)C27—Fe2—C22—C2382.5 (2)
C10—Fe1—C2—C181.1 (2)C25—Fe2—C22—C2381.0 (2)
C7—Fe1—C2—C1166.71 (19)C24—Fe2—C22—C2337.5 (2)
C6—Fe1—C2—C1124.36 (19)C28—Fe2—C22—C2349.4 (4)
C9—C10—C11—O124.6 (5)C26—C30—C31—O322.4 (5)
C6—C10—C11—O1155.7 (3)C29—C30—C31—O3157.7 (3)
Fe1—C10—C11—O164.7 (4)Fe2—C30—C31—O367.3 (4)
C9—C10—C11—C12153.7 (3)C26—C30—C31—C32154.3 (3)
C6—C10—C11—C1225.9 (5)C29—C30—C31—C3225.6 (5)
Fe1—C10—C11—C12116.9 (3)Fe2—C30—C31—C32116.0 (3)
O1—C11—C12—C133.9 (5)O3—C31—C32—C334.2 (5)
C10—C11—C12—C13177.8 (3)C30—C31—C32—C33179.2 (3)
C15—N1—C13—C12170.2 (3)C35—N2—C33—C32177.0 (3)
C15—N1—C13—C1410.9 (5)C35—N2—C33—C343.2 (5)
C11—C12—C13—N11.5 (5)C31—C32—C33—N22.5 (5)
C11—C12—C13—C14177.4 (3)C31—C32—C33—C34177.4 (3)
C13—N1—C15—C20124.1 (3)C33—N2—C35—C3657.6 (4)
C13—N1—C15—C1658.5 (5)C33—N2—C35—C40126.3 (3)
C20—C15—C16—C172.9 (5)C36—C35—C40—C391.7 (4)
N1—C15—C16—C17179.7 (3)N2—C35—C40—C39177.9 (3)
C15—C16—C17—C181.1 (5)C35—C40—C39—C380.5 (5)
C16—C17—C18—O2177.7 (3)C40—C39—C38—O4178.5 (3)
C16—C17—C18—C192.3 (5)C40—C39—C38—C372.0 (5)
O2—C18—C19—C20176.2 (3)O4—C38—C37—C36179.3 (3)
C17—C18—C19—C203.8 (5)C39—C38—C37—C361.3 (4)
C18—C19—C20—C152.0 (5)C38—C37—C36—C350.9 (4)
C16—C15—C20—C191.4 (5)C40—C35—C36—C372.4 (4)
N1—C15—C20—C19178.9 (3)N2—C35—C36—C37178.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.881.892.607 (3)138
N2—H2N···O30.881.912.623 (3)137
O2—H2O···O3i0.841.802.632 (3)170
O4—H4O···O10.841.822.651 (3)169
C4—H4···Cg6ii0.952.943.696 (4)137
C6—H6···Cg3iii0.952.763.673 (3)161
C23—H23···Cg3iv0.952.843.592 (4)137
C29—H29···Cg6iv0.952.923.786 (4)152
C37—H37···Cg5v0.952.973.710 (3)135
C40—H40···Cg1vi0.952.933.663 (3)135
Symmetry codes: (i) x+1, y, z1; (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)]
Mr361.21361.21
Crystal system, space groupTriclinicP1TriclinicP1
Temperature (K)293173
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)
V3)1677.7 (6)1630.3 (4)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.910.94
Crystal size (mm)0.30 × 0.20 × 0.200.30 × 0.15 × 0.12
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Rigaku Mercury
diffractometer
Absorption correctionPsi-scan
ψ scan (North et al., 1968)
Multi-scan
(Jacobson, 1998)
Tmin, Tmax0.772, 0.8390.767, 0.896
No. of measured, independent and
observed [I > 2σ(I)] reflections
6988, 6576, 3837 15645, 5891, 4742
Rint0.0330.036
(sin θ/λ)max1)0.6160.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.126, 1.01 0.048, 0.105, 1.10
No. of reflections65765891
No. of parameters437438
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.50, 0.340.47, 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.

Selected bond lengths (Å) for (I) top
O1—C111.265 (5)N2—C331.348 (5)
N1—C131.340 (5)N2—C351.423 (5)
N1—C151.429 (5)C30—C311.470 (6)
C10—C111.491 (6)C31—C321.417 (6)
C11—C121.400 (5)C32—C331.369 (6)
C13—C141.493 (5)C33—C341.503 (6)
O3—C311.256 (5)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.861.962.642 (5)136
N2—H2N···O30.861.992.645 (5)132
O2—H2O···O3i0.821.822.629 (5)170
O4—H4O···O10.821.862.679 (5)172
C2—H2···Cg3ii0.932.853.686 (5)150
C4—H4···Cg6iii0.932.893.614 (6)135
C28—H28···Cg3iv0.932.963.655 (6)133
Symmetry codes: (i) x1, y+1, z; (ii) x, y+2, z+1; (iii) x+1, y+1, z+1; (iv) x+1, y+1, z+2.
Selected bond lengths (Å) for (II) top
O1—C111.269 (4)O3—C311.275 (4)
N1—C131.336 (4)N2—C331.337 (4)
N1—C151.427 (4)N2—C351.423 (4)
C10—C111.482 (4)C30—C311.481 (4)
C11—C121.406 (4)C31—C321.413 (4)
C12—C131.391 (4)C32—C331.386 (4)
C13—C141.498 (4)C33—C341.502 (4)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.881.892.607 (3)138
N2—H2N···O30.881.912.623 (3)137
O2—H2O···O3i0.841.802.632 (3)170
O4—H4O···O10.841.822.651 (3)169
C4—H4···Cg6ii0.952.943.696 (4)137
C6—H6···Cg3iii0.952.763.673 (3)161
C23—H23···Cg3iv0.952.843.592 (4)137
C29—H29···Cg6iv0.952.923.786 (4)152
C37—H37···Cg5v0.952.973.710 (3)135
C40—H40···Cg1vi0.952.933.663 (3)135
Symmetry codes: (i) x+1, y, z1; (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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