Download citation
Download citation
link to html
Owing to increasing inter­est in the use of N-heterocyclic carbenes (NHCs) based on imidazolidinium ions as ligands in the design of highly efficient transition-metal-based homogeneous catalysts, the characterizations of the 1-ferrocenylmethyl-3-(2,4,6-trimethyl­benzyl)imidazolidin-3-ium iodide salt, [Fe(C5H5)(C19H24N2)]I, (I), and the palladium complex trans-bis­(3-benzyl-1-ferrocenylmethyl-1H-imidazolidin-2-yl­idene)diiodidopalladium(II), [Fe2Pd(C5H5)2(C16H17N2)2I2], (II), are re­ported. Compound (I) has two iodide anions and two imidazolidinium cations within the asymmetric unit (Z′ = 2). The two cations have distinctly different con­formations, with the ferrocene groups orientated exo and endo with respect to the N-heterocyclic carbene. Weak C—H donor hydrogen bonds to both the iodide anions and the π system of the mesitylene group combine to form two-dimensional layers perpendicular to the crystallographic c direction. Only one of the formally charged imidazolidinium rings forms a near-linear hydrogen bond with an iodide anion. Complex (II) shows square-planar coordination around the PdII metal, which is located on an inversion centre (Z′ = 0.5). The ferrocene and benzyl substituents are in a transanti arrangement. The Pd—C bond distance between the N-heterocyclic carbene ligands and the metal atom is 2.036 (7) Å. A survey of related structures shows that the lengthening of the N—C bonds and the closure of the N—C—N angle seen here on metal complexation is typical of similar NHCs and their complexes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112000601/ky3008sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112000601/ky3008Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112000601/ky3008IIsup3.hkl
Contains datablock II

CCDC references: 867007; 867008

Comment top

In recent years, N-heterocyclic carbenes (NHCs) based on imidazolium ions have emerged as useful ligands in the design of highly efficient transition metal-based homogeneous catalysts (Peris & Crabtree, 2004; Cavell & McGuinness, 2004; Glorius, 2007; Sommer & Weck, 2007; Gonzalez et al., 2009; Melaimi et al., 2010). Ferrocenyl-substituted carbenes are interesting compounds because of the influence of the metallocenyl groups with respect to steric protection, electron donation and reversible redox chemistry. Pioneered by Bildstein et al. (1998), this expanding field (Bildstein, 2001) contains a broad range of NHCs (Bildstein, Malaun, Kopacka, Ongania & Wurst, 1999; Bildstein, Malaun, Kopacka, Wurst et al., 1999); Jackstell et al., 2002; Demirhan et al., 2003; Bertoog et al., 2005; Siemeling et al., 2009; Varnado et al., 2009), including derivatives with additional donor groups (Yuan et al., 2005; Gischig & Togni, 2005; Labande et al., 2007; Gülcemal et al., 2009) that can be used as multidentate ligands. Such ferrocenyl-substituted carbene ligands have been shown to be effective in transition metal-catalysed reactions. Some ferrocenyl-substituted NHCs derived from imidazolin-2-ylidene and benzimidazol-2-ylidene have also been structurally characterized by Bildstein and co-workers (Bildstein et al., 1998; Bildstein, Malaun, Kopacka, Ongania & Wurst, 1999; Bildstein, Malaun, Kopacka, Wurst et al., 1999).

Recently, we reported the synthesis and electrochemistry of the title salt, 1-ferrocenylmethyl-3-(2,4,6-trimethylbenzyl)-1H-imidazolium iodide, (I), and the title complex, trans-bis(3-benzyl-1-ferrocenylmethyl-1H-imidazol-2-ylidene)diiodidopalladium(II), (II). The latter is derived from 1-ferrocenylmethyl-3-benzylimidazolium iodide salt (Demirhan et al., 2003). The ferrocene imidazolium salt, (I), can be shown to act as an anion receptor and is used in preparing chiral carbene ligands and their complexes. In complex (II), the ferrocenylmethyl acts as a pendant group on the N atom of imidazol-2-ylidene. It is a new ferrocenyl-substituted carbene and it is hoped that it may prove useful, given its potential applications in homogenous catalysis and electrocatalysis. Initially, the compounds were isolated as microcrystalline solids that were not suitable for structure determination through X-ray diffraction. After several unsuccessful attempts, X-ray quality crystals were obtained and we report here the crystal structures of (I) and (II).

In compound (I), the asymmetric unit contains two 1-ferrocenylmethyl-3-(2,4,6-trimethylbenzyl)-1H-imidazolium cations and two iodide anions (Z' = 2, see Fig. 1). The value of the Flack parameter refined to 0.22 (2), and this is normally taken to indicate the occurrence of a twin by inversion. The two cations have different conformations, as is clearly shown in the molecular overlap representation in Fig. 2. In molecule A, the N-heterocyclic carbene ring is oriented somewhat endo with respect to atom Fe1 and the Cp ring to which it is attached, whereas in molecule B it is exo with respect to atom Fe2 and the related Cp ring. This is clearly shown by the positions of atoms N11 and N21 with respect to the mean planes of the C11–C15 and C21–C25 Cp rings, -0.124 (9) Å out of plane for N11 and 1.045 (9) Å for N21. This difference in conformation is also reflected in the C12—C11—C111—N11 and C22—C21—C211—N21 torsion angles, with values of -168.5 (4) and -111.8 (5)°, respectively. The two imidazolium rings deviate slightly from planarity, with the largest deviations from the least-squares mean planes being 0.047 (3) and -0.060 (3) Å for the methylene atoms C112 and C212. Thus, the two imidazolidinium groups, N11—C1—N12—C112—C113 and N21—C2—N22—C212—C213, display slightly twisted conformations on, respectively, the C112—C113 bond [puckering parameters Q2 = 0.079 (5) Å and ϕ2 = 313 (4)°; Cremer & Pople, 1975; Evans & Boeyens, 1989] for molecule A and the C212—C213 bond [puckering parameters Q2 = 0.102 (5) Å and ϕ2 = 133 (3)°] for molecule B. The conformation of molecule B of (I) is closely related to that of the salt 1-ferrocenylmethyl-3-benzylimidazolium iodide (Hua et al., 2004). The C—C and C—N distances within the imidazolium rings agree with the values observed in this latter salt and with values found in the literature for related Fc-containing compounds (Cambridge Structural Database, Version?; Allen, 2002), as can be seen in Table 2. However, it is interesting to note that the N—C—N angles of 114.5 (4) and 113.6 (4)° in (I) are generally larger than the range found for these related species (108.1–113.9°).

The least-squares planes of the mesitylene rings and imidazolidinium cations of (I) make dihedral angles of 79.94 (14) and 65.52 (14)° in molecules A and B, respectively. The bond lengths and angles within the ferrocene moiety are within expected limits. The Cp rings of the Fc groups are slightly twisted away from the ideal eclipsed conformation [by 8.5 (6) and 6.7 (5)°, respectively; mean value calculated from the five possible C—CgCg—C torsion angles, where Cg are the centroids of the Cp rings] and they are also slightly bent, making dihedral angles between the rings of 5.1 (3)° for molecule A and 1.9 (3)° for molecule B. The displacement parameters for the Cp ring that contains atom C16 indicate some rotational movement, which decreases the accuracy of the geometric parameters associated with this group.

The more pronounced bending for molecule A might be related to the rather short and linear C—H···I interaction between the carbene and the iodide (Table 1). There is no such linear hydrogen-bonding interaction for the B cation. Atom C2 does in fact make a closer contact with the iodide [3.541 (4) Å in molecule B and 3.811 (5) Å in molecule A], but only the linear interaction of molecule A gives a short H···I distance.

The packing within the crystal structure of (I) is governed by weak C—H···I and C—H···π interactions. The latter involve the centroids of the rings C16–C20 (Cg1), C122–C127 (Cg2) and C26–C30 (Cg3) (Table 1) and thus act as a link between cations. All these weak interactions combine to give a layered structure parallel to the (001) plane (Fig. 3).

Compound (II) has a crystallographically imposed centrosymmetric molecular geometry (Z' = 0.5), with the Pd position occupying a centre of symmetry. It shows the expected square-planar coordination with trans-carbene ligands (Fig. 4). Indeed, the ferrocenylmethyl and benzyl substituents in (II) are in a transanti arrangement. The imidazoline rings are twisted against the square-planar coordination arrangement by 87.4 (3)°. This is similar to what is observed in other imidazoline-2-ylidene PdII complexes. The Cp rings of the Fc group are much more staggered than in (I), with a rotation angle of 33.3 (6)°. They are also slightly bent, as shown by the dihedral angle between the two Cp ring planes of 1.6 (5)°. The bond lengths and angles within the ferrocene moiety are within expected limits. The Pd1—C1 distance of 2.036 (7) Å and the Pd1—I1 distance of 2.6168 (6) Å are also as observed for related square-planar PdII complexes (Bildstein et al., 1998; Bertoog et al., 2005; Huynh & Wu, 2009).

The carbene-centred N1—C1—N2 ring angle in (II) is 108.4 (6)°. This is within the range of values observed for other NHC–metal complexes, but as with (I) it is at the high end of the range [103.3 (11)–108.4 (12)°; see Table 3]. It is noted that the other large angles are also observed for complexes that contain iodide ligands. The literature survey also shows that coordination of the carbene C atom to metal results, as expected, in a lengthening of the C—N bonds [ranging from 1.329 (8) Å in (II) to 1.41 (2) Å] compared with the free ligands [ranging from 1.292 (5) in (I) to 1.339 (9) Å; Tables 2 and 3]. In both (I) and (II), the C—N carbene bond involving the N atom attached to the ferrocene moiety through the methylene bridge is significantly shorter than the C—N bond involving the N atom attached to the mesitylene or phenyl groups. This slight difference is certainly related to an electronic effect caused by the proximity of the electron-rich ferrocene moiety.

Related literature top

For related literature, see: Allen (2002); Bertoog et al. (2005); Bildstein (2001); Bildstein et al. (1998); Bildstein, Malaun, Kopacka, Ongania & Wurst (1999); Bildstein, Malaun, Kopacka, Wurst, Mitterböck, Ongania, Opromolla & Zanello (1999); Cavell & McGuinness (2004); Cremer & Pople (1975); Demirhan et al. (2003); Evans & Boeyens (1989); Gülcemal et al. (2009); Gischig & Togni (2005); Glorius (2007); Gonzalez et al. (2009); Hua et al. (2004); Huynh & Wu (2009); Jackstell et al. (2002); Labande et al. (2007); Melaimi et al. (2010); Peris & Crabtree (2004); Sheldrick (2008); Siemeling et al. (2009); Sommer & Weck (2007); Varnado, Lynch & Bielawski (2009); Yuan et al. (2005).

Experimental top

The syntheses and spectroscopic characterizations of the title compounds have been detailed in the study by Demirhan et al. (2003). Crystals of (I) and (II) were grown from methanol–diethyl ether (Solvent ratio?) and dichloromethane–diethyl ether (Solvent ratio?), respectively.

Refinement top

All H atoms were placed in geometrically idealized positions and treated as riding, with C—H = 0.98 (methyl), 0.99 (methylene) or 0.95 Å (aromatic), and with Uiso(H) = 1.2Ueq(Caromatic, Cmethylene) or 1.5Ueq(Cmethyl).

In molecule A of (I), the C atoms of the unsubstituted Cp ring display rather elongated displacement ellipsoids, but attempts to model a disordered system did not improve the quality of the refinement. Moreover, the anistropic displacement parameters for all the disordered C atoms were unrealistic and needed to be severely restrained using EADP commands (SHELXL97; Sheldrick, 2008). Thus, the non-disordered model was preferred.

Computing details top

For both compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008). Molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009) for (I); ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997) for (II). For both compounds, software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Dashed lines indicate C—H···I and C—H···π interactions. [Please check added text]
[Figure 2] Fig. 2. An overlay view, showing the differing molecular geometries of the two independent molecules of (I). [Which is which? Arrows could be used]
[Figure 3] Fig. 3. A partial packing view for (I), along the b direction, showing the formation of layers parallel to the (001) plane through C—H···I and C—H···π interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.
[Figure 4] Fig. 4. The molecular structure of (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) -x + 1, -y + 1, -z + 1.]
(I) 1-ferrocenylmethyl-3-(2,4,6-trimethylbenzyl)imidazolidin-3-ium iodide salt top
Crystal data top
[Fe(C5H5)(C19H24N2)]IF(000) = 1064
Mr = 528.24Dx = 1.574 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 19197 reflections
a = 10.6277 (12) Åθ = 2.8–28.2°
b = 7.4514 (8) ŵ = 2.07 mm1
c = 28.293 (3) ÅT = 180 K
β = 95.603 (9)°Flattened, yellow
V = 2229.8 (4) Å30.44 × 0.29 × 0.03 mm
Z = 4
Data collection top
Oxford Xcalibur
diffractometer
10405 independent reflections
Radiation source: fine-focus sealed tube7372 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ω and ϕ scansθmax = 28.2°, θmin = 2.8°
Absorption correction: analytical
[Analytical numerical absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid, implemented in CrysAlis RED (Oxford Diffraction, 2006)]
h = 1314
Tmin = 0.654, Tmax = 0.964k = 99
19193 measured reflectionsl = 3537
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.064 w = 1/[σ2(Fo2) + (0.0212P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.84(Δ/σ)max = 0.011
10405 reflectionsΔρmax = 0.67 e Å3
512 parametersΔρmin = 0.63 e Å3
1 restraintAbsolute structure: Flack (1983), with 4503 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.220 (15)
Crystal data top
[Fe(C5H5)(C19H24N2)]IV = 2229.8 (4) Å3
Mr = 528.24Z = 4
Monoclinic, P21Mo Kα radiation
a = 10.6277 (12) ŵ = 2.07 mm1
b = 7.4514 (8) ÅT = 180 K
c = 28.293 (3) Å0.44 × 0.29 × 0.03 mm
β = 95.603 (9)°
Data collection top
Oxford Xcalibur
diffractometer
10405 independent reflections
Absorption correction: analytical
[Analytical numerical absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid, implemented in CrysAlis RED (Oxford Diffraction, 2006)]
7372 reflections with I > 2σ(I)
Tmin = 0.654, Tmax = 0.964Rint = 0.044
19193 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.064Δρmax = 0.67 e Å3
S = 0.84Δρmin = 0.63 e Å3
10405 reflectionsAbsolute structure: Flack (1983), with 4503 Friedel pairs
512 parametersAbsolute structure parameter: 0.220 (15)
1 restraint
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
I10.95888 (3)0.08368 (4)0.750410 (13)0.04257 (11)
Fe10.62330 (5)0.78071 (9)0.58868 (2)0.01734 (14)
C10.7567 (5)0.5055 (7)0.75213 (18)0.0328 (12)
H10.80030.39450.75110.039*
C110.6942 (4)0.5650 (6)0.62842 (15)0.0207 (10)
C120.6524 (4)0.5138 (6)0.58061 (15)0.0218 (11)
H120.58870.42780.57140.026*
C130.7219 (4)0.6129 (6)0.54963 (16)0.0236 (10)
H130.71350.60420.51600.028*
C140.8062 (4)0.7271 (6)0.57707 (15)0.0221 (11)
H140.86390.80870.56500.026*
C150.7897 (3)0.6990 (6)0.62607 (14)0.0218 (10)
H150.83410.75860.65230.026*
C160.4425 (4)0.8404 (7)0.5647 (3)0.0537 (18)
H160.38220.75670.55100.064*
C170.4634 (6)0.8834 (9)0.6130 (3)0.062 (2)
H170.42000.83540.63790.074*
C180.5604 (6)1.0107 (8)0.6174 (2)0.0584 (19)
H180.59441.06510.64630.070*
C190.5978 (5)1.0436 (7)0.5740 (3)0.0443 (16)
H190.66321.12380.56730.053*
C200.5245 (5)0.9405 (8)0.54076 (18)0.0410 (14)
H200.53020.93950.50750.049*
N110.6882 (3)0.5707 (6)0.71584 (13)0.0291 (10)
N120.7609 (3)0.6064 (6)0.79084 (13)0.0306 (11)
C1110.6537 (4)0.4739 (6)0.67164 (16)0.0321 (11)
H11A0.56070.45840.66760.039*
H11B0.69220.35280.67410.039*
C1120.6271 (5)0.7340 (7)0.72953 (16)0.0385 (14)
H11C0.53460.71720.72900.046*
H11D0.64410.83460.70820.046*
C1130.6872 (4)0.7684 (7)0.78016 (15)0.0290 (11)
H11E0.74200.87600.78150.035*
H11F0.62180.78390.80250.035*
C1210.8510 (4)0.5853 (8)0.83298 (16)0.0388 (12)
H12A0.92370.66690.83070.047*
H12B0.88340.46060.83450.047*
C1220.7890 (4)0.6273 (7)0.87790 (16)0.0285 (13)
C1230.7051 (5)0.5106 (7)0.89601 (17)0.0348 (12)
C1240.6464 (4)0.5586 (8)0.93567 (17)0.0359 (13)
H1240.58860.47720.94770.043*
C1250.6692 (4)0.7207 (6)0.95825 (16)0.0311 (13)
C1260.7549 (4)0.8333 (7)0.94080 (16)0.0322 (12)
H1260.77370.94400.95660.039*
C1270.8158 (4)0.7916 (8)0.90064 (15)0.0311 (11)
C1280.6757 (5)0.3254 (8)0.87397 (19)0.0551 (16)
H12C0.64140.33980.84080.083*
H12D0.61350.26410.89160.083*
H12E0.75340.25400.87540.083*
C1290.6002 (4)0.7766 (8)1.00007 (16)0.0466 (13)
H12F0.57250.66951.01630.070*
H12G0.52640.84920.98890.070*
H12H0.65700.84741.02220.070*
C1300.9085 (4)0.9263 (7)0.88393 (18)0.0420 (14)
H13A0.92151.02360.90720.063*
H13B0.87480.97570.85320.063*
H13C0.98940.86670.88060.063*
I20.48223 (3)0.17674 (4)0.752716 (11)0.03052 (8)
Fe20.12131 (5)0.25983 (9)0.58461 (2)0.01750 (14)
C210.1751 (4)0.4428 (6)0.63545 (16)0.0234 (10)
C220.1436 (4)0.5301 (6)0.59129 (17)0.0228 (11)
H220.08040.61950.58510.027*
C230.2223 (4)0.4613 (6)0.55806 (17)0.0253 (11)
H230.21980.49330.52550.030*
C240.3057 (4)0.3354 (6)0.58232 (16)0.0244 (10)
H240.37000.27000.56870.029*
C250.2777 (4)0.3234 (6)0.62965 (15)0.0246 (10)
H250.31950.24910.65360.029*
C260.0382 (4)0.1415 (6)0.60485 (16)0.0342 (13)
H260.08090.17430.63150.041*
C270.0613 (4)0.2108 (6)0.55810 (16)0.0318 (12)
H270.12270.29880.54790.038*
C280.0216 (4)0.1276 (6)0.52983 (15)0.0269 (12)
H280.02600.14920.49690.032*
C290.0974 (4)0.0070 (6)0.55772 (18)0.0319 (12)
H290.16220.06670.54730.038*
C300.0596 (5)0.0152 (7)0.60425 (18)0.0375 (13)
H300.09460.05320.63070.045*
N210.1756 (3)0.5537 (6)0.71863 (13)0.0266 (10)
N220.2803 (3)0.5910 (6)0.78801 (14)0.0274 (9)
C20.2258 (4)0.4778 (6)0.75701 (17)0.0241 (11)
H20.22340.35200.76220.029*
C2110.1055 (4)0.4608 (6)0.67892 (15)0.0270 (11)
H21A0.02550.52630.67020.032*
H21B0.08320.33930.68960.032*
C2120.2036 (5)0.7449 (7)0.71842 (18)0.0326 (13)
H21C0.12580.81730.71160.039*
H21D0.26390.77440.69500.039*
C2130.2631 (5)0.7735 (8)0.76974 (17)0.0343 (13)
H21E0.34510.83700.77030.041*
H21F0.20600.84300.78850.041*
C2210.3523 (4)0.5484 (6)0.83365 (15)0.0293 (11)
H22A0.43620.60710.83490.035*
H22B0.36630.41720.83560.035*
C2220.2868 (4)0.6082 (7)0.87614 (16)0.0251 (11)
C2230.1949 (4)0.4987 (6)0.89363 (17)0.0306 (11)
C2240.1349 (4)0.5571 (8)0.93268 (17)0.0358 (13)
H2240.07330.48240.94490.043*
C2250.1631 (4)0.7205 (7)0.95390 (16)0.0298 (13)
C2260.2553 (4)0.8241 (7)0.93705 (16)0.0331 (12)
H2260.27730.93460.95240.040*
C2270.3183 (4)0.7732 (7)0.89802 (15)0.0282 (11)
C2280.1598 (5)0.3181 (7)0.87233 (19)0.0485 (15)
H22C0.09940.25890.89130.073*
H22D0.23590.24390.87220.073*
H22E0.12120.33400.83970.073*
C2290.0944 (4)0.7852 (8)0.99512 (16)0.0437 (13)
H22F0.06460.68161.01220.066*
H22G0.02190.85900.98310.066*
H22H0.15210.85681.01670.066*
C2300.4171 (4)0.8988 (6)0.88118 (17)0.0332 (12)
H23A0.43550.99420.90470.050*
H23B0.38500.95190.85070.050*
H23C0.49460.83130.87730.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0444 (2)0.0393 (2)0.0470 (2)0.00838 (18)0.01985 (17)0.01140 (19)
Fe10.0177 (3)0.0155 (3)0.0189 (3)0.0013 (3)0.0018 (2)0.0004 (3)
C10.044 (3)0.027 (3)0.027 (3)0.017 (2)0.003 (2)0.001 (2)
C110.026 (2)0.014 (2)0.022 (2)0.0071 (19)0.0029 (18)0.0013 (19)
C120.026 (3)0.020 (3)0.019 (3)0.0035 (19)0.001 (2)0.007 (2)
C130.025 (2)0.025 (3)0.021 (2)0.0045 (19)0.0013 (19)0.002 (2)
C140.015 (2)0.026 (3)0.024 (2)0.0054 (18)0.0009 (18)0.0026 (19)
C150.023 (2)0.022 (3)0.020 (2)0.003 (2)0.0017 (17)0.006 (2)
C160.020 (3)0.024 (3)0.113 (6)0.002 (2)0.016 (3)0.007 (3)
C170.055 (4)0.058 (5)0.081 (5)0.043 (3)0.049 (4)0.047 (4)
C180.074 (5)0.051 (4)0.046 (4)0.049 (4)0.017 (3)0.025 (3)
C190.031 (3)0.019 (3)0.083 (5)0.005 (2)0.004 (3)0.003 (3)
C200.046 (3)0.058 (4)0.019 (3)0.032 (3)0.001 (2)0.008 (3)
N110.042 (2)0.029 (2)0.016 (2)0.007 (2)0.0010 (17)0.005 (2)
N120.032 (2)0.042 (3)0.017 (2)0.017 (2)0.0006 (17)0.001 (2)
C1110.052 (3)0.021 (3)0.023 (3)0.001 (2)0.002 (2)0.000 (2)
C1120.057 (3)0.033 (3)0.025 (3)0.026 (3)0.000 (2)0.001 (2)
C1130.033 (3)0.023 (2)0.030 (3)0.008 (2)0.000 (2)0.007 (2)
C1210.038 (3)0.054 (3)0.022 (3)0.019 (3)0.005 (2)0.001 (3)
C1220.031 (3)0.038 (4)0.016 (3)0.013 (2)0.002 (2)0.002 (2)
C1230.047 (3)0.033 (3)0.022 (3)0.008 (3)0.010 (2)0.001 (2)
C1240.035 (3)0.047 (4)0.025 (3)0.005 (3)0.003 (2)0.011 (3)
C1250.032 (3)0.041 (4)0.020 (2)0.004 (2)0.001 (2)0.005 (2)
C1260.036 (3)0.038 (3)0.020 (3)0.000 (2)0.010 (2)0.002 (2)
C1270.025 (3)0.047 (3)0.020 (3)0.000 (2)0.005 (2)0.006 (3)
C1280.069 (4)0.051 (4)0.041 (4)0.004 (3)0.013 (3)0.003 (3)
C1290.044 (3)0.060 (4)0.037 (3)0.006 (3)0.008 (2)0.001 (3)
C1300.038 (3)0.060 (4)0.027 (3)0.009 (3)0.001 (2)0.008 (3)
I20.03428 (17)0.02951 (17)0.02813 (18)0.00323 (16)0.00477 (13)0.00067 (16)
Fe20.0168 (3)0.0171 (3)0.0180 (3)0.0019 (3)0.0011 (2)0.0004 (3)
C210.025 (2)0.021 (2)0.024 (3)0.007 (2)0.000 (2)0.004 (2)
C220.023 (2)0.019 (3)0.025 (3)0.0023 (19)0.006 (2)0.003 (2)
C230.026 (3)0.027 (3)0.022 (3)0.007 (2)0.000 (2)0.003 (2)
C240.015 (2)0.026 (3)0.032 (3)0.0035 (19)0.003 (2)0.005 (2)
C250.020 (2)0.025 (3)0.026 (3)0.0013 (19)0.0064 (19)0.002 (2)
C260.038 (3)0.039 (4)0.029 (3)0.022 (2)0.018 (2)0.013 (2)
C270.017 (2)0.032 (3)0.044 (3)0.002 (2)0.010 (2)0.005 (2)
C280.030 (2)0.033 (3)0.016 (2)0.013 (2)0.0034 (19)0.0014 (19)
C290.026 (3)0.024 (3)0.046 (3)0.001 (2)0.004 (2)0.017 (2)
C300.045 (3)0.033 (3)0.031 (3)0.014 (3)0.017 (2)0.014 (2)
N210.033 (2)0.029 (3)0.016 (2)0.0011 (19)0.0007 (17)0.0014 (19)
N220.030 (2)0.030 (2)0.022 (2)0.005 (2)0.0025 (17)0.002 (2)
C20.030 (3)0.019 (2)0.025 (3)0.001 (2)0.008 (2)0.002 (2)
C2110.028 (3)0.034 (3)0.018 (3)0.009 (2)0.0020 (19)0.003 (2)
C2120.047 (3)0.023 (3)0.028 (3)0.003 (2)0.000 (2)0.003 (2)
C2130.039 (3)0.028 (3)0.035 (3)0.010 (3)0.003 (2)0.013 (3)
C2210.028 (3)0.035 (3)0.024 (3)0.008 (2)0.0016 (19)0.006 (2)
C2220.021 (2)0.032 (3)0.021 (3)0.009 (2)0.0076 (19)0.001 (2)
C2230.040 (3)0.025 (3)0.025 (3)0.001 (2)0.004 (2)0.004 (2)
C2240.031 (3)0.049 (4)0.026 (3)0.007 (3)0.000 (2)0.009 (3)
C2250.026 (3)0.045 (4)0.018 (2)0.006 (2)0.0019 (19)0.000 (2)
C2260.040 (3)0.035 (3)0.022 (3)0.007 (2)0.007 (2)0.009 (2)
C2270.025 (3)0.036 (3)0.023 (3)0.002 (2)0.001 (2)0.001 (3)
C2280.058 (4)0.044 (4)0.044 (3)0.009 (3)0.004 (3)0.002 (3)
C2290.046 (3)0.055 (3)0.031 (3)0.006 (3)0.010 (2)0.001 (3)
C2300.041 (3)0.037 (3)0.022 (3)0.008 (2)0.001 (2)0.001 (2)
Geometric parameters (Å, º) top
Fe1—C192.015 (5)Fe2—C212.024 (4)
Fe1—C202.020 (4)Fe2—C232.031 (5)
Fe1—C162.024 (5)Fe2—C302.033 (5)
Fe1—C132.027 (4)Fe2—C222.034 (5)
Fe1—C122.029 (4)Fe2—C292.038 (5)
Fe1—C182.038 (5)Fe2—C262.042 (4)
Fe1—C142.042 (4)Fe2—C282.043 (4)
Fe1—C172.043 (5)Fe2—C272.044 (4)
Fe1—C112.061 (4)Fe2—C242.046 (4)
Fe1—C152.062 (4)Fe2—C252.049 (4)
C1—N111.294 (5)C21—C221.419 (6)
C1—N121.325 (6)C21—C251.430 (6)
C1—H10.9500C21—C2111.502 (6)
C11—C151.430 (5)C22—C231.414 (6)
C11—C121.434 (6)C22—H220.9500
C11—C1111.498 (6)C23—C241.421 (6)
C12—C131.409 (6)C23—H230.9500
C12—H120.9500C24—C251.403 (6)
C13—C141.412 (5)C24—H240.9500
C13—H130.9500C25—H250.9500
C14—C151.430 (6)C26—C301.404 (6)
C14—H140.9500C26—C271.419 (6)
C15—H150.9500C26—H260.9500
C16—C201.376 (8)C27—C281.393 (6)
C16—C171.398 (8)C27—H270.9500
C16—H160.9500C28—C291.398 (6)
C17—C181.398 (8)C28—H280.9500
C17—H170.9500C29—C301.414 (7)
C18—C191.350 (8)C29—H290.9500
C18—H180.9500C30—H300.9500
C19—C201.392 (7)N21—C21.292 (5)
C19—H190.9500N21—C2121.455 (6)
C20—H200.9500N21—C2111.461 (5)
N11—C1121.450 (6)N22—C21.311 (5)
N11—C1111.459 (6)N22—C2131.460 (7)
N12—C1131.454 (6)N22—C2211.470 (5)
N12—C1211.463 (5)C2—H20.9500
C111—H11A0.9900C211—H21A0.9900
C111—H11B0.9900C211—H21B0.9900
C112—C1131.532 (6)C212—C2131.541 (6)
C112—H11C0.9900C212—H21C0.9900
C112—H11D0.9900C212—H21D0.9900
C113—H11E0.9900C213—H21E0.9900
C113—H11F0.9900C213—H21F0.9900
C121—C1221.520 (6)C221—C2221.514 (6)
C121—H12A0.9900C221—H22A0.9900
C121—H12B0.9900C221—H22B0.9900
C122—C1231.379 (7)C222—C2231.400 (7)
C122—C1271.400 (7)C222—C2271.402 (7)
C123—C1241.383 (7)C223—C2241.398 (7)
C123—C1281.534 (7)C223—C2281.506 (7)
C124—C1251.377 (7)C224—C2251.378 (7)
C124—H1240.9500C224—H2240.9500
C125—C1261.365 (6)C225—C2261.369 (7)
C125—C1291.510 (6)C225—C2291.514 (6)
C126—C1271.397 (6)C226—C2271.399 (6)
C126—H1260.9500C226—H2260.9500
C127—C1301.514 (7)C227—C2301.517 (6)
C128—H12C0.9800C228—H22C0.9800
C128—H12D0.9800C228—H22D0.9800
C128—H12E0.9800C228—H22E0.9800
C129—H12F0.9800C229—H22F0.9800
C129—H12G0.9800C229—H22G0.9800
C129—H12H0.9800C229—H22H0.9800
C130—H13A0.9800C230—H23A0.9800
C130—H13B0.9800C230—H23B0.9800
C130—H13C0.9800C230—H23C0.9800
C19—Fe1—C2040.4 (2)C21—Fe2—C2369.04 (18)
C19—Fe1—C1667.2 (2)C21—Fe2—C30119.1 (2)
C20—Fe1—C1639.8 (2)C23—Fe2—C30163.7 (2)
C19—Fe1—C13123.6 (2)C21—Fe2—C2240.95 (17)
C20—Fe1—C13105.09 (19)C23—Fe2—C2240.70 (18)
C16—Fe1—C13118.5 (2)C30—Fe2—C22154.2 (2)
C19—Fe1—C12161.5 (2)C21—Fe2—C29154.7 (2)
C20—Fe1—C12125.3 (2)C23—Fe2—C29126.6 (2)
C16—Fe1—C12109.13 (19)C30—Fe2—C2940.7 (2)
C13—Fe1—C1240.67 (17)C22—Fe2—C29163.5 (2)
C19—Fe1—C1838.9 (2)C21—Fe2—C26106.04 (18)
C20—Fe1—C1866.6 (2)C23—Fe2—C26154.93 (19)
C16—Fe1—C1867.1 (2)C30—Fe2—C2640.31 (18)
C13—Fe1—C18160.7 (3)C22—Fe2—C26119.59 (19)
C12—Fe1—C18158.3 (3)C29—Fe2—C2668.21 (18)
C19—Fe1—C14105.6 (2)C21—Fe2—C28162.51 (18)
C20—Fe1—C14116.6 (2)C23—Fe2—C28109.23 (18)
C16—Fe1—C14151.3 (2)C30—Fe2—C2867.52 (18)
C13—Fe1—C1440.60 (15)C22—Fe2—C28126.52 (18)
C12—Fe1—C1468.44 (17)C29—Fe2—C2840.05 (17)
C18—Fe1—C14125.7 (2)C26—Fe2—C2867.74 (18)
C19—Fe1—C1766.8 (2)C21—Fe2—C27124.98 (18)
C20—Fe1—C1767.0 (2)C23—Fe2—C27120.87 (19)
C16—Fe1—C1740.2 (2)C30—Fe2—C2767.68 (19)
C13—Fe1—C17154.9 (3)C22—Fe2—C27107.98 (18)
C12—Fe1—C17123.1 (2)C29—Fe2—C2767.58 (18)
C18—Fe1—C1740.1 (2)C26—Fe2—C2740.64 (18)
C14—Fe1—C17164.5 (3)C28—Fe2—C2739.85 (17)
C19—Fe1—C11154.8 (2)C21—Fe2—C2468.42 (17)
C20—Fe1—C11164.6 (2)C23—Fe2—C2440.79 (16)
C16—Fe1—C11129.7 (2)C30—Fe2—C24126.21 (19)
C13—Fe1—C1168.62 (17)C22—Fe2—C2468.12 (18)
C12—Fe1—C1141.02 (16)C29—Fe2—C24109.11 (18)
C18—Fe1—C11123.7 (2)C26—Fe2—C24162.12 (19)
C14—Fe1—C1168.43 (16)C28—Fe2—C24122.41 (18)
C17—Fe1—C11112.3 (2)C27—Fe2—C24156.29 (18)
C19—Fe1—C15118.9 (2)C21—Fe2—C2541.10 (17)
C20—Fe1—C15151.9 (2)C23—Fe2—C2568.50 (17)
C16—Fe1—C15167.3 (2)C30—Fe2—C25107.51 (18)
C13—Fe1—C1568.56 (16)C22—Fe2—C2568.49 (18)
C12—Fe1—C1568.66 (17)C29—Fe2—C25120.65 (18)
C18—Fe1—C15110.0 (2)C26—Fe2—C25124.81 (18)
C14—Fe1—C1540.78 (15)C28—Fe2—C25155.83 (18)
C17—Fe1—C15129.6 (2)C27—Fe2—C25162.38 (18)
C11—Fe1—C1540.59 (16)C24—Fe2—C2540.06 (16)
N11—C1—N12114.5 (4)C22—C21—C25107.5 (4)
N11—C1—H1122.8C22—C21—C211126.0 (4)
N12—C1—H1122.8C25—C21—C211126.3 (4)
C15—C11—C12107.3 (4)C22—C21—Fe269.9 (2)
C15—C11—C111128.0 (4)C25—C21—Fe270.4 (2)
C12—C11—C111124.2 (4)C211—C21—Fe2121.0 (3)
C15—C11—Fe169.7 (2)C23—C22—C21108.4 (4)
C12—C11—Fe168.3 (2)C23—C22—Fe269.5 (3)
C111—C11—Fe1132.8 (3)C21—C22—Fe269.1 (3)
C13—C12—C11108.3 (4)C23—C22—H22125.8
C13—C12—Fe169.6 (2)C21—C22—H22125.8
C11—C12—Fe170.7 (2)Fe2—C22—H22127.1
C13—C12—H12125.8C22—C23—C24107.4 (4)
C11—C12—H12125.8C22—C23—Fe269.8 (3)
Fe1—C12—H12125.4C24—C23—Fe270.2 (2)
C12—C13—C14108.5 (4)C22—C23—H23126.3
C12—C13—Fe169.7 (2)C24—C23—H23126.3
C14—C13—Fe170.3 (2)Fe2—C23—H23125.4
C12—C13—H13125.8C25—C24—C23108.8 (4)
C14—C13—H13125.8C25—C24—Fe270.1 (2)
Fe1—C13—H13125.8C23—C24—Fe269.0 (2)
C13—C14—C15108.3 (4)C25—C24—H24125.6
C13—C14—Fe169.1 (2)C23—C24—H24125.6
C15—C14—Fe170.4 (2)Fe2—C24—H24126.9
C13—C14—H14125.9C24—C25—C21107.8 (4)
C15—C14—H14125.9C24—C25—Fe269.9 (2)
Fe1—C14—H14126.2C21—C25—Fe268.5 (2)
C14—C15—C11107.6 (3)C24—C25—H25126.1
C14—C15—Fe168.9 (2)C21—C25—H25126.1
C11—C15—Fe169.7 (2)Fe2—C25—H25127.1
C14—C15—H15126.2C30—C26—C27107.1 (4)
C11—C15—H15126.2C30—C26—Fe269.5 (3)
Fe1—C15—H15126.8C27—C26—Fe269.8 (2)
C20—C16—C17108.0 (5)C30—C26—H26126.5
C20—C16—Fe170.0 (3)C27—C26—H26126.5
C17—C16—Fe170.6 (3)Fe2—C26—H26125.9
C20—C16—H16126.0C28—C27—C26108.1 (4)
C17—C16—H16126.0C28—C27—Fe270.0 (2)
Fe1—C16—H16125.0C26—C27—Fe269.6 (2)
C18—C17—C16106.8 (5)C28—C27—H27125.9
C18—C17—Fe169.8 (3)C26—C27—H27125.9
C16—C17—Fe169.2 (3)Fe2—C27—H27126.0
C18—C17—H17126.6C27—C28—C29108.9 (4)
C16—C17—H17126.6C27—C28—Fe270.1 (2)
Fe1—C17—H17126.1C29—C28—Fe269.8 (2)
C19—C18—C17108.7 (5)C27—C28—H28125.5
C19—C18—Fe169.7 (3)C29—C28—H28125.5
C17—C18—Fe170.2 (3)Fe2—C28—H28126.1
C19—C18—H18125.6C28—C29—C30107.3 (4)
C17—C18—H18125.6C28—C29—Fe270.2 (3)
Fe1—C18—H18126.1C30—C29—Fe269.5 (3)
C18—C19—C20108.7 (5)C28—C29—H29126.3
C18—C19—Fe171.4 (3)C30—C29—H29126.3
C20—C19—Fe170.0 (3)Fe2—C29—H29125.6
C18—C19—H19125.7C26—C30—C29108.5 (4)
C20—C19—H19125.7C26—C30—Fe270.2 (3)
Fe1—C19—H19124.5C29—C30—Fe269.9 (3)
C16—C20—C19107.8 (5)C26—C30—H30125.7
C16—C20—Fe170.2 (3)C29—C30—H30125.7
C19—C20—Fe169.6 (3)Fe2—C30—H30125.8
C16—C20—H20126.1C2—N21—C212111.3 (4)
C19—C20—H20126.1C2—N21—C211125.2 (4)
Fe1—C20—H20125.6C212—N21—C211123.4 (4)
C1—N11—C112109.6 (4)C2—N22—C213109.3 (4)
C1—N11—C111124.7 (4)C2—N22—C221127.4 (5)
C112—N11—C111124.2 (4)C213—N22—C221123.3 (4)
C1—N12—C113109.0 (4)N21—C2—N22113.6 (4)
C1—N12—C121125.4 (4)N21—C2—H2123.2
C113—N12—C121123.7 (4)N22—C2—H2123.2
N11—C111—C11114.0 (4)N21—C211—C21114.7 (3)
N11—C111—H11A108.7N21—C211—H21A108.6
C11—C111—H11A108.7C21—C211—H21A108.6
N11—C111—H11B108.7N21—C211—H21B108.6
C11—C111—H11B108.7C21—C211—H21B108.6
H11A—C111—H11B107.6H21A—C211—H21B107.6
N11—C112—C113103.5 (4)N21—C212—C213101.3 (4)
N11—C112—H11C111.1N21—C212—H21C111.5
C113—C112—H11C111.1C213—C212—H21C111.5
N11—C112—H11D111.1N21—C212—H21D111.5
C113—C112—H11D111.1C213—C212—H21D111.5
H11C—C112—H11D109.0H21C—C212—H21D109.3
N12—C113—C112102.9 (4)N22—C213—C212103.3 (4)
N12—C113—H11E111.2N22—C213—H21E111.1
C112—C113—H11E111.2C212—C213—H21E111.1
N12—C113—H11F111.2N22—C213—H21F111.1
C112—C113—H11F111.2C212—C213—H21F111.1
H11E—C113—H11F109.1H21E—C213—H21F109.1
N12—C121—C122110.9 (4)N22—C221—C222113.2 (3)
N12—C121—H12A109.5N22—C221—H22A108.9
C122—C121—H12A109.5C222—C221—H22A108.9
N12—C121—H12B109.5N22—C221—H22B108.9
C122—C121—H12B109.5C222—C221—H22B108.9
H12A—C121—H12B108.1H22A—C221—H22B107.8
C123—C122—C127119.4 (5)C223—C222—C227120.0 (4)
C123—C122—C121122.0 (5)C223—C222—C221120.0 (4)
C127—C122—C121118.6 (5)C227—C222—C221120.0 (4)
C122—C123—C124119.8 (5)C224—C223—C222119.1 (4)
C122—C123—C128122.0 (5)C224—C223—C228118.7 (5)
C124—C123—C128118.2 (5)C222—C223—C228122.2 (5)
C125—C124—C123122.0 (5)C225—C224—C223121.5 (5)
C125—C124—H124119.0C225—C224—H224119.2
C123—C124—H124119.0C223—C224—H224119.2
C126—C125—C124117.7 (5)C226—C225—C224118.6 (4)
C126—C125—C129120.4 (5)C226—C225—C229120.3 (5)
C124—C125—C129121.9 (5)C224—C225—C229121.1 (5)
C125—C126—C127122.4 (5)C225—C226—C227122.4 (5)
C125—C126—H126118.8C225—C226—H226118.8
C127—C126—H126118.8C227—C226—H226118.8
C126—C127—C122118.6 (5)C226—C227—C222118.3 (5)
C126—C127—C130118.3 (5)C226—C227—C230118.7 (5)
C122—C127—C130123.1 (5)C222—C227—C230123.0 (4)
C123—C128—H12C109.5C223—C228—H22C109.5
C123—C128—H12D109.5C223—C228—H22D109.5
H12C—C128—H12D109.5H22C—C228—H22D109.5
C123—C128—H12E109.5C223—C228—H22E109.5
H12C—C128—H12E109.5H22C—C228—H22E109.5
H12D—C128—H12E109.5H22D—C228—H22E109.5
C125—C129—H12F109.5C225—C229—H22F109.5
C125—C129—H12G109.5C225—C229—H22G109.5
H12F—C129—H12G109.5H22F—C229—H22G109.5
C125—C129—H12H109.5C225—C229—H22H109.5
H12F—C129—H12H109.5H22F—C229—H22H109.5
H12G—C129—H12H109.5H22G—C229—H22H109.5
C127—C130—H13A109.5C227—C230—H23A109.5
C127—C130—H13B109.5C227—C230—H23B109.5
H13A—C130—H13B109.5H23A—C230—H23B109.5
C127—C130—H13C109.5C227—C230—H23C109.5
H13A—C130—H13C109.5H23A—C230—H23C109.5
H13B—C130—H13C109.5H23B—C230—H23C109.5
C19—Fe1—C11—C1542.8 (6)C23—Fe2—C21—C2237.1 (2)
C20—Fe1—C11—C15150.0 (7)C30—Fe2—C21—C22158.5 (3)
C16—Fe1—C11—C15168.4 (3)C29—Fe2—C21—C22170.3 (4)
C13—Fe1—C11—C1581.6 (2)C26—Fe2—C21—C22116.9 (3)
C12—Fe1—C11—C15119.3 (3)C28—Fe2—C21—C2250.4 (7)
C18—Fe1—C11—C1581.5 (3)C27—Fe2—C21—C2276.6 (3)
C14—Fe1—C11—C1537.8 (2)C24—Fe2—C21—C2281.0 (3)
C17—Fe1—C11—C15125.5 (3)C25—Fe2—C21—C22118.0 (4)
C19—Fe1—C11—C12162.1 (5)C23—Fe2—C21—C2580.9 (3)
C20—Fe1—C11—C1230.7 (8)C30—Fe2—C21—C2583.5 (3)
C16—Fe1—C11—C1272.3 (4)C22—Fe2—C21—C25118.0 (4)
C13—Fe1—C11—C1237.7 (2)C29—Fe2—C21—C2552.2 (5)
C18—Fe1—C11—C12159.1 (3)C26—Fe2—C21—C25125.0 (3)
C14—Fe1—C11—C1281.5 (3)C28—Fe2—C21—C25168.5 (5)
C17—Fe1—C11—C12115.2 (3)C27—Fe2—C21—C25165.3 (3)
C15—Fe1—C11—C12119.3 (3)C24—Fe2—C21—C2537.0 (3)
C19—Fe1—C11—C11180.8 (7)C23—Fe2—C21—C211157.8 (4)
C20—Fe1—C11—C11186.4 (8)C30—Fe2—C21—C21137.8 (4)
C16—Fe1—C11—C11144.8 (5)C22—Fe2—C21—C211120.7 (5)
C13—Fe1—C11—C111154.8 (5)C29—Fe2—C21—C21169.0 (6)
C12—Fe1—C11—C111117.1 (5)C26—Fe2—C21—C2113.8 (4)
C18—Fe1—C11—C11142.0 (5)C28—Fe2—C21—C21170.2 (8)
C14—Fe1—C11—C111161.4 (5)C27—Fe2—C21—C21144.1 (4)
C17—Fe1—C11—C1111.9 (5)C24—Fe2—C21—C211158.3 (4)
C15—Fe1—C11—C111123.6 (5)C25—Fe2—C21—C211121.3 (5)
C15—C11—C12—C130.7 (5)C25—C21—C22—C232.1 (5)
C111—C11—C12—C13172.5 (4)C211—C21—C22—C23172.9 (4)
Fe1—C11—C12—C1359.7 (3)Fe2—C21—C22—C2358.6 (3)
C15—C11—C12—Fe159.0 (3)C25—C21—C22—Fe260.7 (3)
C111—C11—C12—Fe1127.9 (4)C211—C21—C22—Fe2114.3 (4)
C19—Fe1—C12—C1336.6 (7)C21—Fe2—C22—C23120.2 (4)
C20—Fe1—C12—C1370.5 (3)C30—Fe2—C22—C23167.5 (4)
C16—Fe1—C12—C13111.9 (3)C29—Fe2—C22—C2345.1 (7)
C18—Fe1—C12—C13172.1 (5)C26—Fe2—C22—C23159.6 (3)
C14—Fe1—C12—C1337.6 (2)C28—Fe2—C22—C2376.6 (3)
C17—Fe1—C12—C13154.2 (3)C27—Fe2—C22—C23116.7 (3)
C11—Fe1—C12—C13119.0 (3)C24—Fe2—C22—C2338.4 (3)
C15—Fe1—C12—C1381.5 (3)C25—Fe2—C22—C2381.6 (3)
C19—Fe1—C12—C11155.6 (6)C23—Fe2—C22—C21120.2 (4)
C20—Fe1—C12—C11170.4 (3)C30—Fe2—C22—C2147.3 (5)
C16—Fe1—C12—C11129.1 (3)C29—Fe2—C22—C21165.3 (6)
C13—Fe1—C12—C11119.0 (3)C26—Fe2—C22—C2180.2 (3)
C18—Fe1—C12—C1153.1 (6)C28—Fe2—C22—C21163.2 (3)
C14—Fe1—C12—C1181.5 (3)C27—Fe2—C22—C21123.1 (3)
C17—Fe1—C12—C1186.7 (3)C24—Fe2—C22—C2181.8 (3)
C15—Fe1—C12—C1137.5 (2)C25—Fe2—C22—C2138.6 (2)
C11—C12—C13—C140.6 (5)C21—C22—C23—C242.0 (5)
Fe1—C12—C13—C1459.8 (3)Fe2—C22—C23—C2460.3 (3)
C11—C12—C13—Fe160.4 (3)C21—C22—C23—Fe258.3 (3)
C19—Fe1—C13—C12166.9 (3)C21—Fe2—C23—C2237.3 (3)
C20—Fe1—C13—C12127.1 (3)C30—Fe2—C23—C22160.4 (6)
C16—Fe1—C13—C1286.5 (3)C29—Fe2—C23—C22165.5 (3)
C18—Fe1—C13—C12171.2 (5)C26—Fe2—C23—C2245.7 (5)
C14—Fe1—C13—C12119.4 (4)C28—Fe2—C23—C22124.1 (3)
C17—Fe1—C13—C1259.2 (6)C27—Fe2—C23—C2281.8 (3)
C11—Fe1—C13—C1238.0 (2)C24—Fe2—C23—C22118.2 (4)
C15—Fe1—C13—C1281.8 (3)C25—Fe2—C23—C2281.6 (3)
C19—Fe1—C13—C1473.7 (3)C21—Fe2—C23—C2480.9 (3)
C20—Fe1—C13—C14113.5 (3)C30—Fe2—C23—C2442.2 (8)
C16—Fe1—C13—C14154.1 (3)C22—Fe2—C23—C24118.2 (4)
C12—Fe1—C13—C14119.4 (4)C29—Fe2—C23—C2476.3 (3)
C18—Fe1—C13—C1451.7 (7)C26—Fe2—C23—C24163.9 (4)
C17—Fe1—C13—C14178.7 (4)C28—Fe2—C23—C24117.7 (3)
C11—Fe1—C13—C1481.4 (3)C27—Fe2—C23—C24160.1 (3)
C15—Fe1—C13—C1437.6 (2)C25—Fe2—C23—C2436.6 (3)
C12—C13—C14—C150.2 (5)C22—C23—C24—C251.2 (5)
Fe1—C13—C14—C1559.7 (3)Fe2—C23—C24—C2558.9 (3)
C12—C13—C14—Fe159.5 (3)C22—C23—C24—Fe260.1 (3)
C19—Fe1—C14—C13124.0 (3)C21—Fe2—C24—C2537.9 (3)
C20—Fe1—C14—C1382.1 (3)C23—Fe2—C24—C25120.4 (4)
C16—Fe1—C14—C1353.1 (5)C30—Fe2—C24—C2573.1 (3)
C12—Fe1—C14—C1337.6 (3)C22—Fe2—C24—C2582.2 (3)
C18—Fe1—C14—C13161.3 (3)C29—Fe2—C24—C25115.2 (3)
C17—Fe1—C14—C13177.9 (7)C26—Fe2—C24—C2537.1 (7)
C11—Fe1—C14—C1381.9 (3)C28—Fe2—C24—C25157.5 (3)
C15—Fe1—C14—C13119.5 (4)C27—Fe2—C24—C25167.2 (4)
C19—Fe1—C14—C15116.5 (3)C21—Fe2—C24—C2382.5 (3)
C20—Fe1—C14—C15158.4 (3)C30—Fe2—C24—C23166.5 (3)
C16—Fe1—C14—C15172.6 (4)C22—Fe2—C24—C2338.3 (3)
C13—Fe1—C14—C15119.5 (4)C29—Fe2—C24—C23124.3 (3)
C12—Fe1—C14—C1581.9 (3)C26—Fe2—C24—C23157.5 (6)
C18—Fe1—C14—C1579.1 (3)C28—Fe2—C24—C2382.0 (3)
C17—Fe1—C14—C1558.4 (8)C27—Fe2—C24—C2346.7 (6)
C11—Fe1—C14—C1537.6 (2)C25—Fe2—C24—C23120.4 (4)
C13—C14—C15—C110.2 (5)C23—C24—C25—C210.1 (5)
Fe1—C14—C15—C1159.2 (3)Fe2—C24—C25—C2158.2 (3)
C13—C14—C15—Fe158.9 (3)C23—C24—C25—Fe258.3 (3)
C12—C11—C15—C140.6 (5)C22—C21—C25—C241.4 (5)
C111—C11—C15—C14172.2 (4)C211—C21—C25—C24173.6 (4)
Fe1—C11—C15—C1458.6 (3)Fe2—C21—C25—C2459.0 (3)
C12—C11—C15—Fe158.1 (3)C22—C21—C25—Fe260.4 (3)
C111—C11—C15—Fe1129.1 (4)C211—C21—C25—Fe2114.6 (4)
C19—Fe1—C15—C1480.1 (3)C21—Fe2—C25—C24119.6 (4)
C20—Fe1—C15—C1444.4 (5)C23—Fe2—C25—C2437.3 (3)
C16—Fe1—C15—C14163.7 (8)C30—Fe2—C25—C24126.0 (3)
C13—Fe1—C15—C1437.5 (3)C22—Fe2—C25—C2481.2 (3)
C12—Fe1—C15—C1481.3 (3)C29—Fe2—C25—C2483.5 (3)
C18—Fe1—C15—C14121.9 (3)C26—Fe2—C25—C24167.0 (3)
C17—Fe1—C15—C14162.8 (3)C28—Fe2—C25—C2452.0 (5)
C11—Fe1—C15—C14119.2 (3)C27—Fe2—C25—C24162.8 (6)
C19—Fe1—C15—C11160.7 (3)C23—Fe2—C25—C2182.3 (3)
C20—Fe1—C15—C11163.6 (4)C30—Fe2—C25—C21114.4 (3)
C16—Fe1—C15—C1144.5 (10)C22—Fe2—C25—C2138.4 (3)
C13—Fe1—C15—C1181.7 (3)C29—Fe2—C25—C21156.9 (3)
C12—Fe1—C15—C1137.9 (2)C26—Fe2—C25—C2173.4 (3)
C18—Fe1—C15—C11118.9 (3)C28—Fe2—C25—C21171.6 (4)
C14—Fe1—C15—C11119.2 (3)C27—Fe2—C25—C2143.2 (7)
C17—Fe1—C15—C1178.0 (4)C24—Fe2—C25—C21119.6 (4)
C19—Fe1—C16—C2038.1 (3)C21—Fe2—C26—C30116.3 (3)
C13—Fe1—C16—C2079.0 (4)C23—Fe2—C26—C30169.0 (4)
C12—Fe1—C16—C20122.6 (3)C22—Fe2—C26—C30158.5 (3)
C18—Fe1—C16—C2080.4 (4)C29—Fe2—C26—C3037.7 (3)
C14—Fe1—C16—C2042.7 (6)C28—Fe2—C26—C3081.0 (3)
C17—Fe1—C16—C20118.5 (5)C27—Fe2—C26—C30118.2 (4)
C11—Fe1—C16—C20164.0 (3)C24—Fe2—C26—C3047.1 (7)
C15—Fe1—C16—C20159.7 (8)C25—Fe2—C26—C3075.3 (3)
C19—Fe1—C16—C1780.4 (4)C21—Fe2—C26—C27125.5 (3)
C20—Fe1—C16—C17118.5 (5)C23—Fe2—C26—C2750.8 (5)
C13—Fe1—C16—C17162.5 (3)C30—Fe2—C26—C27118.2 (4)
C12—Fe1—C16—C17119.0 (4)C22—Fe2—C26—C2783.3 (3)
C18—Fe1—C16—C1738.1 (3)C29—Fe2—C26—C2780.5 (3)
C14—Fe1—C16—C17161.2 (4)C28—Fe2—C26—C2737.2 (3)
C11—Fe1—C16—C1777.5 (4)C24—Fe2—C26—C27165.3 (5)
C15—Fe1—C16—C1741.2 (10)C25—Fe2—C26—C27166.5 (3)
C20—C16—C17—C180.4 (6)C30—C26—C27—C280.1 (5)
Fe1—C16—C17—C1859.9 (4)Fe2—C26—C27—C2859.7 (3)
C20—C16—C17—Fe160.3 (4)C30—C26—C27—Fe259.7 (3)
C19—Fe1—C17—C1836.4 (3)C21—Fe2—C27—C28168.1 (3)
C20—Fe1—C17—C1880.4 (4)C23—Fe2—C27—C2883.3 (3)
C16—Fe1—C17—C18118.1 (5)C30—Fe2—C27—C2881.2 (3)
C13—Fe1—C17—C18156.7 (5)C22—Fe2—C27—C28126.0 (3)
C12—Fe1—C17—C18161.4 (3)C29—Fe2—C27—C2837.1 (3)
C14—Fe1—C17—C1826.6 (9)C26—Fe2—C27—C28119.3 (4)
C11—Fe1—C17—C18116.3 (4)C24—Fe2—C27—C2849.6 (6)
C15—Fe1—C17—C1872.8 (4)C25—Fe2—C27—C28158.6 (5)
C19—Fe1—C17—C1681.7 (4)C21—Fe2—C27—C2672.7 (3)
C20—Fe1—C17—C1637.7 (3)C23—Fe2—C27—C26157.5 (3)
C13—Fe1—C17—C1638.6 (6)C30—Fe2—C27—C2638.1 (3)
C12—Fe1—C17—C1680.5 (4)C22—Fe2—C27—C26114.8 (3)
C18—Fe1—C17—C16118.1 (5)C29—Fe2—C27—C2682.2 (3)
C14—Fe1—C17—C16144.7 (7)C28—Fe2—C27—C26119.3 (4)
C11—Fe1—C17—C16125.6 (3)C24—Fe2—C27—C26168.8 (4)
C15—Fe1—C17—C16169.1 (3)C25—Fe2—C27—C2639.3 (7)
C16—C17—C18—C190.3 (6)C26—C27—C28—C290.2 (5)
Fe1—C17—C18—C1959.2 (4)Fe2—C27—C28—C2959.2 (3)
C16—C17—C18—Fe159.5 (4)C26—C27—C28—Fe259.4 (3)
C20—Fe1—C18—C1938.2 (3)C21—Fe2—C28—C2734.3 (7)
C16—Fe1—C18—C1981.6 (4)C23—Fe2—C28—C27115.5 (3)
C13—Fe1—C18—C1929.7 (8)C30—Fe2—C28—C2781.6 (3)
C12—Fe1—C18—C19166.0 (5)C22—Fe2—C28—C2773.3 (3)
C14—Fe1—C18—C1968.7 (4)C29—Fe2—C28—C27120.0 (4)
C17—Fe1—C18—C19119.8 (5)C26—Fe2—C28—C2737.9 (3)
C11—Fe1—C18—C19154.9 (3)C24—Fe2—C28—C27158.7 (3)
C15—Fe1—C18—C19111.7 (3)C25—Fe2—C28—C27164.3 (4)
C19—Fe1—C18—C17119.8 (5)C21—Fe2—C28—C29154.4 (6)
C20—Fe1—C18—C1781.6 (4)C23—Fe2—C28—C29124.5 (3)
C16—Fe1—C18—C1738.2 (3)C30—Fe2—C28—C2938.4 (3)
C13—Fe1—C18—C17149.5 (6)C22—Fe2—C28—C29166.7 (3)
C12—Fe1—C18—C1746.2 (7)C26—Fe2—C28—C2982.2 (3)
C14—Fe1—C18—C17171.5 (3)C27—Fe2—C28—C29120.0 (4)
C11—Fe1—C18—C1785.3 (4)C24—Fe2—C28—C2981.2 (3)
C15—Fe1—C18—C17128.5 (4)C25—Fe2—C28—C2944.3 (5)
C17—C18—C19—C200.9 (6)C27—C28—C29—C300.4 (5)
Fe1—C18—C19—C2060.4 (4)Fe2—C28—C29—C3059.8 (3)
C17—C18—C19—Fe159.5 (4)C27—C28—C29—Fe259.4 (3)
C20—Fe1—C19—C18118.8 (5)C21—Fe2—C29—C28162.3 (4)
C16—Fe1—C19—C1881.3 (4)C23—Fe2—C29—C2875.8 (3)
C13—Fe1—C19—C18168.7 (3)C30—Fe2—C29—C28118.2 (4)
C12—Fe1—C19—C18163.5 (6)C22—Fe2—C29—C2840.6 (7)
C14—Fe1—C19—C18128.2 (4)C26—Fe2—C29—C2880.9 (3)
C17—Fe1—C19—C1837.4 (4)C27—Fe2—C29—C2836.9 (3)
C11—Fe1—C19—C1856.0 (6)C24—Fe2—C29—C28118.0 (3)
C15—Fe1—C19—C1886.3 (4)C25—Fe2—C29—C28160.6 (3)
C16—Fe1—C19—C2037.5 (3)C21—Fe2—C29—C3044.0 (5)
C13—Fe1—C19—C2072.6 (4)C23—Fe2—C29—C30166.0 (3)
C12—Fe1—C19—C2044.8 (7)C22—Fe2—C29—C30158.9 (6)
C18—Fe1—C19—C20118.8 (5)C26—Fe2—C29—C3037.3 (3)
C14—Fe1—C19—C20113.0 (3)C28—Fe2—C29—C30118.2 (4)
C17—Fe1—C19—C2081.4 (4)C27—Fe2—C29—C3081.4 (3)
C11—Fe1—C19—C20174.8 (4)C24—Fe2—C29—C30123.8 (3)
C15—Fe1—C19—C20154.9 (3)C25—Fe2—C29—C3081.2 (3)
C17—C16—C20—C190.9 (6)C27—C26—C30—C290.3 (5)
Fe1—C16—C20—C1959.8 (3)Fe2—C26—C30—C2959.6 (3)
C17—C16—C20—Fe160.7 (4)C27—C26—C30—Fe259.9 (3)
C18—C19—C20—C161.1 (6)C28—C29—C30—C260.5 (5)
Fe1—C19—C20—C1660.2 (4)Fe2—C29—C30—C2659.8 (3)
C18—C19—C20—Fe161.3 (4)C28—C29—C30—Fe260.2 (3)
C19—Fe1—C20—C16118.6 (5)C21—Fe2—C30—C2680.4 (3)
C13—Fe1—C20—C16116.7 (4)C23—Fe2—C30—C26163.3 (6)
C12—Fe1—C20—C1677.2 (4)C22—Fe2—C30—C2646.9 (5)
C18—Fe1—C20—C1681.8 (4)C29—Fe2—C30—C26119.5 (4)
C14—Fe1—C20—C16158.6 (3)C28—Fe2—C30—C2681.6 (3)
C17—Fe1—C20—C1638.0 (3)C27—Fe2—C30—C2638.4 (3)
C11—Fe1—C20—C1653.0 (8)C24—Fe2—C30—C26163.8 (3)
C15—Fe1—C20—C16170.7 (4)C25—Fe2—C30—C26123.6 (3)
C16—Fe1—C20—C19118.6 (5)C21—Fe2—C30—C29160.2 (3)
C13—Fe1—C20—C19124.6 (3)C23—Fe2—C30—C2943.8 (8)
C12—Fe1—C20—C19164.2 (3)C22—Fe2—C30—C29166.4 (4)
C18—Fe1—C20—C1936.8 (3)C26—Fe2—C30—C29119.5 (4)
C14—Fe1—C20—C1982.8 (4)C28—Fe2—C30—C2937.8 (3)
C17—Fe1—C20—C1980.6 (4)C27—Fe2—C30—C2981.1 (3)
C11—Fe1—C20—C19171.6 (6)C24—Fe2—C30—C2976.7 (3)
C15—Fe1—C20—C1952.0 (5)C25—Fe2—C30—C29116.9 (3)
N12—C1—N11—C1124.1 (6)C212—N21—C2—N225.3 (6)
N12—C1—N11—C111170.5 (4)C211—N21—C2—N22178.0 (4)
N11—C1—N12—C1131.5 (6)C213—N22—C2—N212.0 (6)
N11—C1—N12—C121166.0 (5)C221—N22—C2—N21176.0 (4)
C1—N11—C111—C11122.4 (5)C2—N21—C211—C21106.6 (5)
C112—N11—C111—C1173.1 (6)C212—N21—C211—C2169.7 (6)
C15—C11—C111—N1119.8 (6)C22—C21—C211—N21111.8 (5)
C12—C11—C111—N11168.5 (4)C25—C21—C211—N2174.1 (6)
Fe1—C11—C111—N1177.3 (5)Fe2—C21—C211—N21161.5 (3)
C1—N11—C112—C1137.5 (5)C2—N21—C212—C2139.6 (5)
C111—N11—C112—C113174.0 (4)C211—N21—C212—C213173.6 (4)
C1—N12—C113—C1126.0 (5)C2—N22—C213—C2127.8 (5)
C121—N12—C113—C112170.7 (4)C221—N22—C213—C212170.3 (4)
N11—C112—C113—N127.8 (5)N21—C212—C213—N229.9 (5)
C1—N12—C121—C122144.3 (5)C2—N22—C221—C222112.0 (5)
C113—N12—C121—C12253.4 (6)C213—N22—C221—C22270.2 (6)
N12—C121—C122—C12374.3 (6)N22—C221—C222—C22384.1 (5)
N12—C121—C122—C127103.9 (5)N22—C221—C222—C22796.0 (5)
C127—C122—C123—C1241.4 (7)C227—C222—C223—C2240.5 (7)
C121—C122—C123—C124176.8 (4)C221—C222—C223—C224179.5 (4)
C127—C122—C123—C128177.5 (4)C227—C222—C223—C228178.4 (4)
C121—C122—C123—C1284.2 (7)C221—C222—C223—C2281.6 (7)
C122—C123—C124—C1250.3 (7)C222—C223—C224—C2250.8 (7)
C128—C123—C124—C125178.7 (4)C228—C223—C224—C225179.7 (4)
C123—C124—C125—C1261.4 (7)C223—C224—C225—C2262.3 (7)
C123—C124—C125—C129176.9 (4)C223—C224—C225—C229177.9 (4)
C124—C125—C126—C1272.0 (7)C224—C225—C226—C2272.5 (7)
C129—C125—C126—C127176.4 (4)C229—C225—C226—C227177.7 (4)
C125—C126—C127—C1220.8 (7)C225—C226—C227—C2221.2 (7)
C125—C126—C127—C130179.5 (4)C225—C226—C227—C230178.6 (4)
C123—C122—C127—C1260.9 (7)C223—C222—C227—C2260.3 (6)
C121—C122—C127—C126177.4 (4)C221—C222—C227—C226179.7 (4)
C123—C122—C127—C130178.7 (4)C223—C222—C227—C230179.8 (4)
C121—C122—C127—C1303.0 (7)C221—C222—C227—C2300.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···I10.952.873.811 (5)173
C113—H11E···I1i0.992.983.878 (5)152
C211—H21B···I1ii0.992.963.877 (5)154
C212—H21C···I1iii0.992.953.797 (5)145
C213—H21E···I2i0.992.993.860 (6)148
C24—H24···Cg1iv0.952.903.688 (5)141
C230—H23C···Cg20.982.903.781 (5)150
C14—H14···Cg3v0.952.703.579 (5)154
Symmetry codes: (i) x, y+1, z; (ii) x1, y, z; (iii) x1, y+1, z; (iv) x, y1, z; (v) x+1, y+1, z.
(II) trans-bis(3-benzyl-1-ferrocenylmethyl-1H-imidazolidin- 2-ylidene)diiodidopalladium(II) top
Crystal data top
[Fe2Pd(C5H5)2(C16H17N2)2I2]F(000) = 1056
Mr = 1076.71Dx = 1.817 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1729 reflections
a = 9.5185 (16) Åθ = 2.9–32.2°
b = 11.7851 (17) ŵ = 2.78 mm1
c = 17.569 (2) ÅT = 180 K
β = 92.835 (12)°Needle, yellow
V = 1968.5 (5) Å30.17 × 0.07 × 0.06 mm
Z = 2
Data collection top
Oxford Xcalibur
diffractometer
3890 independent reflections
Radiation source: fine-focus sealed tube2082 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.084
ω and ϕ scansθmax = 26.0°, θmin = 2.9°
Absorption correction: multi-scan
(Blessing, 1997)
h = 1111
Tmin = 0.727, Tmax = 0.797k = 1411
14178 measured reflectionsl = 2121
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 0.85 w = 1/[σ2(Fo2) + (0.0293P)2]
where P = (Fo2 + 2Fc2)/3
3890 reflections(Δ/σ)max < 0.001
232 parametersΔρmax = 0.94 e Å3
0 restraintsΔρmin = 0.71 e Å3
Crystal data top
[Fe2Pd(C5H5)2(C16H17N2)2I2]V = 1968.5 (5) Å3
Mr = 1076.71Z = 2
Monoclinic, P21/nMo Kα radiation
a = 9.5185 (16) ŵ = 2.78 mm1
b = 11.7851 (17) ÅT = 180 K
c = 17.569 (2) Å0.17 × 0.07 × 0.06 mm
β = 92.835 (12)°
Data collection top
Oxford Xcalibur
diffractometer
3890 independent reflections
Absorption correction: multi-scan
(Blessing, 1997)
2082 reflections with I > 2σ(I)
Tmin = 0.727, Tmax = 0.797Rint = 0.084
14178 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 0.85Δρmax = 0.94 e Å3
3890 reflectionsΔρmin = 0.71 e Å3
232 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Pd10.50000.50000.50000.0277 (2)
I10.65918 (6)0.66957 (4)0.46153 (3)0.03860 (17)
Fe10.34269 (11)0.58179 (9)0.17695 (5)0.0308 (3)
N10.2374 (6)0.5960 (5)0.4199 (3)0.0297 (15)
N20.2610 (6)0.6553 (4)0.5369 (3)0.0312 (15)
C10.3204 (7)0.5924 (6)0.4829 (4)0.0278 (17)
C20.1043 (7)0.6556 (6)0.4286 (4)0.0369 (19)
H2A0.02320.60300.42310.044*
H2B0.09150.71780.39100.044*
C30.1222 (8)0.7014 (6)0.5091 (4)0.043 (2)
H3A0.12270.78540.50930.052*
H3B0.04610.67410.54090.052*
C110.2933 (8)0.6239 (5)0.2853 (4)0.0295 (18)
C120.1887 (7)0.6658 (6)0.2310 (4)0.0312 (17)
H120.09150.64730.22890.037*
C130.2564 (10)0.7398 (6)0.1811 (4)0.049 (2)
H130.21210.77950.13940.059*
C140.3989 (10)0.7446 (6)0.2032 (4)0.045 (2)
H140.46800.78830.17920.054*
C150.4236 (7)0.6732 (6)0.2678 (4)0.0356 (19)
H150.51150.66090.29440.043*
C160.2568 (9)0.4904 (7)0.0885 (5)0.052 (2)
H160.16650.50260.06450.062*
C170.3810 (10)0.5393 (7)0.0675 (4)0.045 (2)
H170.39040.59110.02660.055*
C180.4900 (9)0.4998 (8)0.1163 (5)0.056 (3)
H180.58690.51830.11430.067*
C190.4280 (12)0.4258 (7)0.1702 (5)0.063 (3)
H190.47590.38780.21150.076*
C200.2866 (10)0.4201 (7)0.1510 (5)0.051 (2)
H200.21990.37550.17620.061*
C1110.2697 (8)0.5408 (5)0.3471 (4)0.0342 (19)
H11A0.19070.49020.33080.041*
H11B0.35490.49330.35530.041*
C2110.3105 (8)0.6668 (6)0.6150 (3)0.0379 (19)
H21A0.40260.62800.62190.045*
H21B0.24390.62760.64760.045*
C2120.3270 (7)0.7869 (6)0.6418 (4)0.0326 (19)
C2130.3704 (8)0.8732 (6)0.5951 (4)0.038 (2)
H2130.38950.85610.54380.046*
C2140.3869 (8)0.9843 (7)0.6209 (5)0.047 (2)
H2140.41571.04210.58740.057*
C2150.3609 (8)1.0097 (7)0.6959 (5)0.050 (2)
H2150.37381.08460.71490.060*
C2160.3158 (8)0.9242 (7)0.7424 (5)0.047 (2)
H2160.29640.94160.79370.056*
C2170.2982 (7)0.8155 (6)0.7172 (4)0.0353 (19)
H2170.26640.75870.75070.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.0364 (5)0.0248 (4)0.0220 (4)0.0042 (4)0.0019 (4)0.0005 (4)
I10.0510 (4)0.0356 (3)0.0290 (3)0.0070 (3)0.0011 (2)0.0025 (3)
Fe10.0400 (7)0.0357 (6)0.0173 (5)0.0025 (6)0.0071 (5)0.0041 (5)
N10.038 (4)0.031 (4)0.020 (3)0.009 (3)0.005 (3)0.003 (3)
N20.055 (4)0.021 (3)0.019 (3)0.014 (3)0.005 (3)0.005 (3)
C10.031 (5)0.028 (4)0.024 (4)0.005 (4)0.004 (3)0.001 (3)
C20.026 (4)0.050 (5)0.035 (5)0.008 (4)0.003 (3)0.010 (4)
C30.047 (6)0.051 (6)0.032 (5)0.001 (4)0.013 (4)0.000 (4)
C110.046 (5)0.030 (4)0.012 (4)0.002 (4)0.001 (4)0.006 (3)
C120.025 (4)0.041 (5)0.028 (4)0.010 (4)0.002 (3)0.009 (4)
C130.091 (8)0.031 (5)0.023 (5)0.015 (5)0.009 (5)0.000 (4)
C140.077 (7)0.034 (5)0.026 (5)0.015 (5)0.023 (4)0.005 (4)
C150.026 (5)0.055 (5)0.026 (4)0.002 (4)0.001 (3)0.018 (4)
C160.053 (6)0.062 (6)0.041 (5)0.013 (5)0.003 (5)0.030 (5)
C170.059 (6)0.051 (6)0.028 (5)0.002 (5)0.020 (5)0.012 (4)
C180.032 (5)0.078 (7)0.058 (6)0.009 (5)0.004 (5)0.038 (6)
C190.111 (9)0.042 (6)0.035 (5)0.027 (6)0.007 (6)0.004 (5)
C200.065 (7)0.044 (6)0.047 (6)0.015 (5)0.036 (5)0.011 (5)
C1110.050 (5)0.030 (4)0.024 (4)0.009 (4)0.005 (4)0.006 (3)
C2110.063 (6)0.038 (5)0.012 (4)0.003 (4)0.000 (3)0.005 (4)
C2120.034 (5)0.036 (5)0.028 (4)0.007 (4)0.001 (4)0.002 (4)
C2130.041 (5)0.037 (5)0.037 (5)0.006 (4)0.012 (4)0.002 (4)
C2140.048 (6)0.045 (6)0.048 (6)0.006 (5)0.003 (4)0.010 (5)
C2150.046 (6)0.044 (6)0.060 (6)0.005 (5)0.001 (5)0.023 (5)
C2160.051 (6)0.047 (6)0.044 (5)0.001 (5)0.011 (4)0.018 (5)
C2170.045 (5)0.045 (5)0.017 (4)0.002 (4)0.011 (3)0.006 (4)
Geometric parameters (Å, º) top
Pd1—C1i2.036 (7)C13—H130.9500
Pd1—C12.036 (7)C14—C151.423 (9)
Pd1—I1i2.6168 (6)C14—H140.9500
Pd1—I12.6168 (6)C15—H150.9500
Fe1—C192.015 (8)C16—C171.382 (10)
Fe1—C202.025 (8)C16—C201.392 (11)
Fe1—C162.029 (7)C16—H160.9500
Fe1—C172.038 (7)C17—C181.393 (10)
Fe1—C132.038 (8)C17—H170.9500
Fe1—C142.039 (7)C18—C191.435 (11)
Fe1—C122.041 (6)C18—H180.9500
Fe1—C152.044 (6)C19—C201.373 (11)
Fe1—C112.044 (6)C19—H190.9500
Fe1—C182.045 (7)C20—H200.9500
N1—C11.329 (8)C111—H11A0.9900
N1—C21.464 (8)C111—H11B0.9900
N1—C1111.481 (7)C211—C2121.497 (9)
N2—C11.350 (8)C211—H21A0.9900
N2—C2111.435 (7)C211—H21B0.9900
N2—C31.488 (8)C212—C2131.382 (9)
C2—C31.516 (9)C212—C2171.408 (9)
C2—H2A0.9900C213—C2141.392 (9)
C2—H2B0.9900C213—H2130.9500
C3—H3A0.9900C214—C2151.386 (10)
C3—H3B0.9900C214—H2140.9500
C11—C151.417 (9)C215—C2161.379 (10)
C11—C121.432 (9)C215—H2150.9500
C11—C1111.487 (9)C216—C2171.364 (9)
C12—C131.414 (10)C216—H2160.9500
C12—H120.9500C217—H2170.9500
C13—C141.394 (10)
C1i—Pd1—C1180.0 (4)C13—C12—H12126.2
C1i—Pd1—I1i92.64 (18)C11—C12—H12126.2
C1—Pd1—I1i87.36 (18)Fe1—C12—H12126.2
C1i—Pd1—I187.36 (18)C14—C13—C12108.6 (7)
C1—Pd1—I192.64 (18)C14—C13—Fe170.1 (5)
I1i—Pd1—I1180.0C12—C13—Fe169.9 (4)
C19—Fe1—C2039.7 (3)C14—C13—H13125.7
C19—Fe1—C1667.6 (4)C12—C13—H13125.7
C20—Fe1—C1640.2 (3)Fe1—C13—H13126.0
C19—Fe1—C1768.2 (3)C13—C14—C15108.5 (7)
C20—Fe1—C1767.3 (3)C13—C14—Fe170.0 (5)
C16—Fe1—C1739.7 (3)C15—C14—Fe169.8 (4)
C19—Fe1—C13178.6 (3)C13—C14—H14125.7
C20—Fe1—C13139.9 (4)C15—C14—H14125.7
C16—Fe1—C13111.4 (4)Fe1—C14—H14126.1
C17—Fe1—C13110.4 (3)C11—C15—C14107.7 (6)
C19—Fe1—C14140.3 (4)C11—C15—Fe169.7 (4)
C20—Fe1—C14179.9 (4)C14—C15—Fe169.4 (4)
C16—Fe1—C14139.8 (4)C11—C15—H15126.1
C17—Fe1—C14112.8 (3)C14—C15—H15126.1
C13—Fe1—C1440.0 (3)Fe1—C15—H15126.3
C19—Fe1—C12140.4 (4)C17—C16—C20108.4 (8)
C20—Fe1—C12111.9 (3)C17—C16—Fe170.5 (4)
C16—Fe1—C12110.0 (3)C20—C16—Fe169.8 (5)
C17—Fe1—C12136.4 (3)C17—C16—H16125.8
C13—Fe1—C1240.6 (3)C20—C16—H16125.8
C14—Fe1—C1268.0 (3)Fe1—C16—H16125.6
C19—Fe1—C15112.9 (3)C16—C17—C18108.4 (8)
C20—Fe1—C15139.2 (4)C16—C17—Fe169.8 (4)
C16—Fe1—C15178.2 (3)C18—C17—Fe170.3 (4)
C17—Fe1—C15142.0 (3)C16—C17—H17125.8
C13—Fe1—C1568.1 (3)C18—C17—H17125.8
C14—Fe1—C1540.8 (3)Fe1—C17—H17125.7
C12—Fe1—C1568.4 (3)C17—C18—C19106.9 (8)
C19—Fe1—C11112.8 (3)C17—C18—Fe169.8 (4)
C20—Fe1—C11111.6 (3)C19—C18—Fe168.2 (5)
C16—Fe1—C11137.7 (3)C17—C18—H18126.5
C17—Fe1—C11177.0 (3)C19—C18—H18126.5
C13—Fe1—C1168.5 (3)Fe1—C18—H18127.0
C14—Fe1—C1168.3 (3)C20—C19—C18107.3 (8)
C12—Fe1—C1141.0 (2)C20—C19—Fe170.5 (5)
C15—Fe1—C1140.6 (3)C18—C19—Fe170.4 (4)
C19—Fe1—C1841.4 (3)C20—C19—H19126.3
C20—Fe1—C1867.5 (3)C18—C19—H19126.3
C16—Fe1—C1867.1 (3)Fe1—C19—H19124.3
C17—Fe1—C1839.9 (3)C19—C20—C16108.9 (8)
C13—Fe1—C18137.6 (4)C19—C20—Fe169.8 (5)
C14—Fe1—C18112.6 (4)C16—C20—Fe170.1 (5)
C12—Fe1—C18176.3 (3)C19—C20—H20125.6
C15—Fe1—C18114.5 (3)C16—C20—H20125.6
C11—Fe1—C18142.7 (3)Fe1—C20—H20126.2
C1—N1—C2114.3 (5)N1—C111—C11112.8 (5)
C1—N1—C111124.4 (6)N1—C111—H11A109.0
C2—N1—C111121.2 (6)C11—C111—H11A109.0
C1—N2—C211126.5 (6)N1—C111—H11B109.0
C1—N2—C3111.5 (6)C11—C111—H11B109.0
C211—N2—C3121.5 (5)H11A—C111—H11B107.8
N1—C1—N2108.4 (6)N2—C211—C212114.5 (6)
N1—C1—Pd1126.9 (5)N2—C211—H21A108.6
N2—C1—Pd1124.6 (5)C212—C211—H21A108.6
N1—C2—C3102.1 (5)N2—C211—H21B108.6
N1—C2—H2A111.3C212—C211—H21B108.6
C3—C2—H2A111.3H21A—C211—H21B107.6
N1—C2—H2B111.3C213—C212—C217117.4 (7)
C3—C2—H2B111.3C213—C212—C211122.6 (6)
H2A—C2—H2B109.2C217—C212—C211120.0 (6)
N2—C3—C2103.5 (5)C212—C213—C214122.1 (7)
N2—C3—H3A111.1C212—C213—H213119.0
C2—C3—H3A111.1C214—C213—H213119.0
N2—C3—H3B111.1C215—C214—C213119.3 (8)
C2—C3—H3B111.1C215—C214—H214120.3
H3A—C3—H3B109.0C213—C214—H214120.3
C15—C11—C12107.5 (6)C216—C215—C214118.8 (8)
C15—C11—C111126.4 (7)C216—C215—H215120.6
C12—C11—C111126.0 (7)C214—C215—H215120.6
C15—C11—Fe169.7 (4)C217—C216—C215122.0 (7)
C12—C11—Fe169.4 (4)C217—C216—H216119.0
C111—C11—Fe1124.7 (4)C215—C216—H216119.0
C13—C12—C11107.6 (7)C216—C217—C212120.3 (7)
C13—C12—Fe169.6 (4)C216—C217—H217119.9
C11—C12—Fe169.6 (4)C212—C217—H217119.9
C2—N1—C1—N25.3 (8)C20—Fe1—C15—C14179.9 (6)
C111—N1—C1—N2177.6 (6)C17—Fe1—C15—C1458.6 (7)
C2—N1—C1—Pd1170.7 (5)C13—Fe1—C15—C1437.0 (4)
C111—N1—C1—Pd16.5 (10)C12—Fe1—C15—C1480.8 (5)
C211—N2—C1—N1174.8 (6)C11—Fe1—C15—C14119.0 (6)
C3—N2—C1—N12.8 (8)C18—Fe1—C15—C1496.7 (6)
C211—N2—C1—Pd11.3 (10)C19—Fe1—C16—C1782.4 (6)
C3—N2—C1—Pd1173.3 (5)C20—Fe1—C16—C17119.2 (8)
I1i—Pd1—C1—N185.6 (6)C13—Fe1—C16—C1796.7 (6)
I1—Pd1—C1—N194.4 (6)C14—Fe1—C16—C1760.9 (8)
I1i—Pd1—C1—N289.7 (6)C12—Fe1—C16—C17140.1 (5)
I1—Pd1—C1—N290.3 (6)C11—Fe1—C16—C17177.8 (5)
C1—N1—C2—C35.4 (8)C18—Fe1—C16—C1737.4 (5)
C111—N1—C2—C3177.4 (6)C19—Fe1—C16—C2036.8 (5)
C1—N2—C3—C20.5 (8)C17—Fe1—C16—C20119.2 (8)
C211—N2—C3—C2172.0 (6)C13—Fe1—C16—C20144.2 (5)
N1—C2—C3—N23.2 (7)C14—Fe1—C16—C20179.9 (6)
C19—Fe1—C11—C1599.1 (6)C12—Fe1—C16—C20100.7 (5)
C20—Fe1—C11—C15142.2 (5)C11—Fe1—C16—C2063.1 (7)
C16—Fe1—C11—C15179.6 (5)C18—Fe1—C16—C2081.8 (5)
C13—Fe1—C11—C1581.1 (5)C20—C16—C17—C180.3 (9)
C14—Fe1—C11—C1537.9 (4)Fe1—C16—C17—C1860.0 (5)
C12—Fe1—C11—C15118.8 (6)C20—C16—C17—Fe159.7 (5)
C18—Fe1—C11—C1561.3 (7)C19—Fe1—C17—C1680.7 (6)
C19—Fe1—C11—C12142.1 (5)C20—Fe1—C17—C1637.6 (5)
C20—Fe1—C11—C1299.1 (5)C13—Fe1—C17—C1699.2 (6)
C16—Fe1—C11—C1260.9 (6)C14—Fe1—C17—C16142.3 (6)
C13—Fe1—C11—C1237.7 (4)C12—Fe1—C17—C1660.8 (7)
C14—Fe1—C11—C1280.9 (5)C15—Fe1—C17—C16179.5 (6)
C15—Fe1—C11—C12118.8 (6)C18—Fe1—C17—C16119.3 (8)
C18—Fe1—C11—C12179.9 (6)C19—Fe1—C17—C1838.6 (5)
C19—Fe1—C11—C11121.9 (8)C20—Fe1—C17—C1881.7 (6)
C20—Fe1—C11—C11121.2 (8)C16—Fe1—C17—C18119.3 (8)
C16—Fe1—C11—C11159.4 (8)C13—Fe1—C17—C18141.5 (6)
C13—Fe1—C11—C111158.0 (7)C14—Fe1—C17—C1898.4 (6)
C14—Fe1—C11—C111158.9 (7)C12—Fe1—C17—C18179.8 (5)
C12—Fe1—C11—C111120.3 (8)C15—Fe1—C17—C1861.2 (7)
C15—Fe1—C11—C111121.0 (8)C16—C17—C18—C191.4 (9)
C18—Fe1—C11—C11159.7 (9)Fe1—C17—C18—C1958.3 (5)
C15—C11—C12—C130.1 (8)C16—C17—C18—Fe159.6 (5)
C111—C11—C12—C13178.0 (6)C19—Fe1—C18—C17118.8 (7)
Fe1—C11—C12—C1359.4 (5)C20—Fe1—C18—C1780.9 (5)
C15—C11—C12—Fe159.5 (5)C16—Fe1—C18—C1737.2 (5)
C111—C11—C12—Fe1118.6 (6)C13—Fe1—C18—C1759.9 (7)
C19—Fe1—C12—C13178.5 (6)C14—Fe1—C18—C1799.1 (5)
C20—Fe1—C12—C13143.0 (5)C15—Fe1—C18—C17143.7 (5)
C16—Fe1—C12—C1399.8 (5)C11—Fe1—C18—C17177.5 (5)
C17—Fe1—C12—C1363.4 (6)C20—Fe1—C18—C1937.9 (5)
C14—Fe1—C12—C1337.0 (4)C16—Fe1—C18—C1981.6 (6)
C15—Fe1—C12—C1381.1 (5)C17—Fe1—C18—C19118.8 (7)
C11—Fe1—C12—C13118.9 (6)C13—Fe1—C18—C19178.7 (6)
C19—Fe1—C12—C1162.6 (7)C14—Fe1—C18—C19142.1 (6)
C20—Fe1—C12—C1198.1 (5)C15—Fe1—C18—C1997.5 (6)
C16—Fe1—C12—C11141.2 (5)C11—Fe1—C18—C1958.7 (8)
C17—Fe1—C12—C11177.7 (5)C17—C18—C19—C201.9 (9)
C13—Fe1—C12—C11118.9 (6)Fe1—C18—C19—C2061.2 (6)
C14—Fe1—C12—C1181.9 (5)C17—C18—C19—Fe159.3 (5)
C15—Fe1—C12—C1137.8 (4)C16—Fe1—C19—C2037.2 (5)
C11—C12—C13—C140.1 (8)C17—Fe1—C19—C2080.2 (5)
Fe1—C12—C13—C1459.5 (5)C14—Fe1—C19—C20179.9 (5)
C11—C12—C13—Fe159.4 (5)C12—Fe1—C19—C2057.6 (7)
C20—Fe1—C13—C14179.9 (5)C15—Fe1—C19—C20141.0 (5)
C16—Fe1—C13—C14144.1 (5)C11—Fe1—C19—C2096.8 (5)
C17—Fe1—C13—C14101.5 (5)C18—Fe1—C19—C20117.5 (7)
C12—Fe1—C13—C14119.6 (6)C20—Fe1—C19—C18117.5 (7)
C15—Fe1—C13—C1437.7 (4)C16—Fe1—C19—C1880.3 (5)
C11—Fe1—C13—C1481.5 (5)C17—Fe1—C19—C1837.3 (5)
C18—Fe1—C13—C1465.2 (6)C14—Fe1—C19—C1862.6 (7)
C20—Fe1—C13—C1260.3 (6)C12—Fe1—C19—C18175.0 (5)
C16—Fe1—C13—C1296.2 (5)C15—Fe1—C19—C18101.6 (5)
C17—Fe1—C13—C12138.9 (5)C11—Fe1—C19—C18145.8 (5)
C14—Fe1—C13—C12119.6 (6)C18—C19—C20—C161.8 (9)
C15—Fe1—C13—C1281.9 (4)Fe1—C19—C20—C1659.4 (6)
C11—Fe1—C13—C1238.1 (4)C18—C19—C20—Fe161.1 (5)
C18—Fe1—C13—C12175.2 (5)C17—C16—C20—C191.0 (9)
C12—C13—C14—C150.1 (8)Fe1—C16—C20—C1959.2 (6)
Fe1—C13—C14—C1559.3 (5)C17—C16—C20—Fe160.1 (5)
C12—C13—C14—Fe159.4 (5)C16—Fe1—C20—C19120.0 (7)
C19—Fe1—C14—C13177.9 (5)C17—Fe1—C20—C1982.8 (5)
C16—Fe1—C14—C1357.8 (7)C13—Fe1—C20—C19177.9 (6)
C17—Fe1—C14—C1395.1 (5)C12—Fe1—C20—C19144.5 (5)
C12—Fe1—C14—C1337.6 (4)C15—Fe1—C20—C1962.6 (7)
C15—Fe1—C14—C13119.7 (6)C11—Fe1—C20—C19100.2 (5)
C11—Fe1—C14—C1381.9 (5)C18—Fe1—C20—C1939.4 (5)
C18—Fe1—C14—C13138.5 (5)C19—Fe1—C20—C16120.0 (7)
C19—Fe1—C14—C1562.4 (7)C17—Fe1—C20—C1637.2 (5)
C16—Fe1—C14—C15177.4 (5)C13—Fe1—C20—C1657.9 (7)
C17—Fe1—C14—C15145.3 (5)C12—Fe1—C20—C1695.4 (5)
C13—Fe1—C14—C15119.7 (6)C15—Fe1—C20—C16177.4 (5)
C12—Fe1—C14—C1582.1 (4)C11—Fe1—C20—C16139.8 (5)
C11—Fe1—C14—C1537.7 (4)C18—Fe1—C20—C1680.6 (5)
C18—Fe1—C14—C15101.9 (5)C1—N1—C111—C11113.7 (7)
C12—C11—C15—C140.1 (7)C2—N1—C111—C1169.4 (8)
C111—C11—C15—C14178.0 (6)C15—C11—C111—N189.9 (8)
Fe1—C11—C15—C1459.2 (5)C12—C11—C111—N192.3 (8)
C12—C11—C15—Fe159.3 (4)Fe1—C11—C111—N1179.2 (5)
C111—C11—C15—Fe1118.8 (6)C1—N2—C211—C212128.2 (7)
C13—C14—C15—C110.0 (8)C3—N2—C211—C21260.6 (9)
Fe1—C14—C15—C1159.4 (5)N2—C211—C212—C21335.1 (10)
C13—C14—C15—Fe159.4 (5)N2—C211—C212—C217145.0 (7)
C19—Fe1—C15—C1198.9 (5)C217—C212—C213—C2140.7 (11)
C20—Fe1—C15—C1160.8 (6)C211—C212—C213—C214179.2 (7)
C17—Fe1—C15—C11177.6 (5)C212—C213—C214—C2150.8 (12)
C13—Fe1—C15—C1182.0 (5)C213—C214—C215—C2161.6 (12)
C14—Fe1—C15—C11119.0 (6)C214—C215—C216—C2171.0 (12)
C12—Fe1—C15—C1138.2 (4)C215—C216—C217—C2120.4 (12)
C18—Fe1—C15—C11144.2 (5)C213—C212—C217—C2161.2 (11)
C19—Fe1—C15—C14142.1 (6)C211—C212—C217—C216178.7 (7)
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

(I)(II)
Crystal data
Chemical formula[Fe(C5H5)(C19H24N2)]I[Fe2Pd(C5H5)2(C16H17N2)2I2]
Mr528.241076.71
Crystal system, space groupMonoclinic, P21Monoclinic, P21/n
Temperature (K)180180
a, b, c (Å)10.6277 (12), 7.4514 (8), 28.293 (3)9.5185 (16), 11.7851 (17), 17.569 (2)
β (°) 95.603 (9) 92.835 (12)
V3)2229.8 (4)1968.5 (5)
Z42
Radiation typeMo KαMo Kα
µ (mm1)2.072.78
Crystal size (mm)0.44 × 0.29 × 0.030.17 × 0.07 × 0.06
Data collection
DiffractometerOxford Xcalibur
diffractometer
Oxford Xcalibur
diffractometer
Absorption correctionAnalytical
[Analytical numerical absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid, implemented in CrysAlis RED (Oxford Diffraction, 2006)]
Multi-scan
(Blessing, 1997)
Tmin, Tmax0.654, 0.9640.727, 0.797
No. of measured, independent and
observed [I > 2σ(I)] reflections
19193, 10405, 7372 14178, 3890, 2082
Rint0.0440.084
(sin θ/λ)max1)0.6650.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.064, 0.84 0.046, 0.091, 0.85
No. of reflections104053890
No. of parameters512232
No. of restraints10
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.67, 0.630.94, 0.71
Absolute structureFlack (1983), with 4503 Friedel pairs?
Absolute structure parameter0.220 (15)?

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
C1—H1···I10.952.873.811 (5)173.3
C113—H11E···I1i0.992.983.878 (5)151.5
C211—H21B···I1ii0.992.963.877 (5)153.9
C212—H21C···I1iii0.992.953.797 (5)144.7
C213—H21E···I2i0.992.993.860 (6)147.7
C24—H24···Cg1iv0.952.903.688 (5)141
C230—H23C···Cg20.982.903.781 (5)150
C14—H14···Cg3v0.952.703.579 (5)154
Symmetry codes: (i) x, y+1, z; (ii) x1, y, z; (iii) x1, y+1, z; (iv) x, y1, z; (v) x+1, y+1, z.
Comparison of selected C—N distances (Å) and N—C—N angles (°) within the diaminocarbene moiety for Fc-bearing ligands related to (I) top
References: (a) Hua et al. (2004); (b) Bildstein, Malaun, Kopacka, Ongania & Wurst (1999); (c) Bildstein et al. (1998); (d) Bildstein, Malaun, Kopacka, Wurst et al. (1999); (e) Bertoog et al. (2005); (f) Gischig & Togni (2005); (g) Coleman et al. (2005); (h) Varnado et al. (2009); (i) Labande et al. (2007); (j) Gülcemal et al. (2009).
CompoundN—CC—NN—C—NReference
(IA)1.294 (5)1.325 (6)114.5 (4)This study
(IB)1.292 (5)1.311 (5)113.6 (4)This study
C21H21FeIN21.321 (4)1.317 (4)109.0 (3)a
C18H17BF4FeN21.332 (5)1.312 (5)110.9 (3)b
C19H19FeIN2.H2O.(CH3OH)1/41.339 (9)1.335 (9)109.9 (8)c
C25H25Fe2IN21.317 (5)1.329 (5)109.0 (3)c
C47H41BFe2N21.334 (5)1.325 (5)108.4 (4)d
C23H23F6Fe2N2P1.304 (3)1.304 (3)113.9 (3)d
C25H25Fe2IN21.327 (3)1.332 (3)108.6 (2)e
C23H21Fe2IN21.329 (8)1.329 (8)108.4 (8)e
C59H39F24Fe2N2P2.I.CH2Cl21.336 (8)1.325 (7)109.3 (5)f
C26H36Cl2 FeN4.CH2Cl21.325 (7)1.326 (7)108.1 (5)g
C28H28B2F8FeN41.351 (5)1.327 (6)109.6 (4)h
C27H26BF4FeN2PS1.324 (5)1.313 (5)108.6 (3)i
C27H26BF4FeN2PS1.317 (3)1.309 (4)109.7 (3)i
C40H38BF4FeN2P1.321 (3)1.331 (3)110.5 (2)j
(C30H33FeIN2)21.321 (6)1.321 (6)110.4 (6)j
Comparison of the C—N distances (Å) and N—C—N angles (°) in (II) with those in related complexes found in the literature top
References: (a) Bildstein, Malaun, Kopacka, Ongania & Wurst (1999); (b) Bildstein et al. (1998); (c) Bildstein, Malaun, Kopacka, Wurst et al. (1999); (d) Bertoog et al. (2005); (e) Gischig & Togni (2005); (f) Coleman et al. (2005); (g) Varnado et al. (2009); (h) Labande et al. (2007); (i) Gülcemal et al. (2009).
CompoundN—CC—NN—C—NReference
(II)1.329 (8)1.350 (8)108.4 (6)This study
C23H16FeN2O5W1.384 (7)1.366 (6)104.0 (4)a
C40H32Fe2N4O4W.CH2Cl21.41 (2)1.36 (2)103.7 (11)a
C34H26Fe2N2O5W1.350 (2)1.357 (14)103.3 (11)b
C58H52Fe4I2N4Pd.(CH2Cl2)41.355 (9)1.354 (9)106.0 (6)b
C38H36Fe2Hg2I4N41.348 (10)1.338 (10)106.4 (6)b
C70H60AgBFe4N4.0.5CHCl3.1.5MeO1.364 (5)1.354 (5)103.8 (3)c
1.369 (5)1.350 (5)104.1 (3)c
C43H39Fe2I2N2PPd1.351 (4)1.359 (4)104.9 (3)d
C59H38F24Fe2IN2P2Pd.PF6.3(CHCl3)1.344 (16)1.330 (16)108.4 (12)e
C53H49Fe2N3P2Pd.2(PF6).C2H6O.C4H10O1.330 (11)1.330 (11)106.1 (8)e
C26H34Cl2FeN4Pd.2CH2Cl21.359 (4)1.363 (4)104.7 (2)f
C44H50Cl2FeIr2N41.371 (5)1.355 (5)105.8 (3)g
C33H27Cl5FeIr2O4N41.353 (5)1.359 (5)106.0 (3)g
C35H37BF4FeN2PRh1.359 (4)1.357 (4)104.5 (2)h
C46H45BF4FeN2PRh1.355 (8)1.362 (8)105.5 (6)i
C50H51BF4FeN2PRh1.367 (5)1.373 (6)105.2 (4)i
C36H40FeIN2Rh1.366 (3)1.360 (3)106.02 (18)i
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds