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In the title compound, [Fe(C5H5)(C23H22N2)]PF6, the F atoms of the [PF6] anion are disordered over four different orientations with equal occupancies. In the cation, the five-membered imidazolium ring forms dihedral angles of 71.48 (10) and 19.83 (10)° with the substituted C5H4 ring and the benzene ring of the styryl group, respectively. In the crystal structure, there is a significant C—H...π(η5-C5H4) inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047769/lh2519sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047769/lh2519Isup2.hkl
Contains datablock I

CCDC reference: 667107

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in solvent or counterion
  • R factor = 0.047
  • wR factor = 0.113
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact F4A .. F4A .. 2.49 Ang.
Alert level C PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.02 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C22 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C23 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C24 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C25 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for F1B PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for F1C PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for F2A PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for F2C PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for F3C PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for F4B PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for F5C PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for F6A PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for F2D PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for F4D PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for F5B PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for F6B PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for F6C PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 24.00 Perc. PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 64.00 A   3
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 228
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 23 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 16 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Benzimidazole systems have attracted considerable attention in synthetic and structural as well as in applied biological research (Gallagher, Hanlon & Howarth, 2001; Howarth & Hanlon, 2001; Gallagher, Hanlon, Howarth & Thomas, 2001). The title compound (Figures 1–3) was obtained from a series of reactions involving synthesis of the parent N-Ferrocenylmethyl-2-(3-methylstyryl)benzimidazole from 2-(3-methylstyryl)benzimidazole and (trimethylammonium)ferrocenylmethyl iodide: subsequent treatment of the product with methyl iodide and replacement of the iodo salt with the hexafluorophosphate anion yields the [PF6]- salt.

Bond lengths and angles are normal and similar to those reported in the literature (Gallagher, Hanlon & Howarth, 2001; Gallagher, Hanlon, Howarth & Thomas, 2001). There is no disorder in the cation although the unsubstituted C5H5 ring displays large displacement parameters as could be expected given the geometry and the low energy barrier to rotation for Fe···η5-C5H5 π-bonding. The [PF6]- anion is disordered and a discussion of the treatment of this disorder is detailed below. The C3N2 5-membered imidazolium ring is almost orthogonal to the substituted C5H4 ring at 71.48 (10)° and deviates from co-planarity with the aromatic styryl C6 ring by 19.83 (10)°: the latter C6 ring is oriented at an angle of 85.52 (9)° to the C5H4 ring.

In the crystal structure there is only one intermolecular interaction of note (as detailed in Table 1) and involving C34—H34···Cg1i (where Cg1 is the ring centroid of C5H4 and the symmetry operation i = x - 3/2,3/2 - y,z). Several C—H···F contacts involving the disordered [PF6]- are present but are not important as they are relatively weak and involve the partial occupancy F atom sites.

Related structures include N-ferrocenylmethyl-2-ferrocenylbenzimidazole (Benito et al., 1995) and the salt N-ferrocenylmethyl-2-ferrocenyl-benzimidazolium tetrafluoroborate (Li et al., 1998) which differ from the title compound by having a ferrocenyl moiety at the 2-position of the benzimidazolium ring instead of the 3-methylstyryl group.

Related literature top

For related ferrocene literature, see: Benito et al. (1995); Li et al. (1998); Gallagher, Hanlon & Howarth (2001); Gallagher, Hanlon, Howarth & Thomas (2001); Howarth & Hanlon, (2001). For the chemical synthesis and crystal structure of [FcCH2N(CH3)3]+[I]-, see: Pauson et al. (1966); Ferguson et al. (1994).

Experimental top

Synthesis of the neutral starting material N-Ferrocenylmethyl-2-(3-methylstyryl)benzimidazole [(C5H5)Fe(C5H4)CH2(C7H4N2)CH=CHC6H4CH3]

To a mixture of 2-(3-methylstyryl)benzimidazole (1.9 g, 8 mmol) and K2CO3 (1.66 g, 12 mmol) in CH3CN (100 ml) was added (trimethylammonium)ferrocenylmethyl iodide ([FcCH2N(CH3)3]+[I]-) (3.09 g, 8 mmol) (Pauson et al., 1966; Ferguson et al., 1994) and the mixture was heated to reflux temperatures for 10 h. The reaction was cooled to room temperature, water was added and the suspension extracted into CHCl3. The organic layer was washed with water, dried MgSO4 and evaporated under vacuum to leave a brown semi-solid. The crude product was purified by column chromatography on silica gel using CH2Cl2:CH3OH (97:3) as eluent.

Yield 2.6 g (74%), m.p. 429–433 K (uncorrected). Compound (I) was obtained as a light orange solid. IR (KBr, ν cm-1) (>1500 cm-1): 3062, 2982, 2925, 2685, 2308, 1713, 1632 1604, 1581. 1H NMR [400 MHz, δH (p.p.m.), CDCl3], 7.90 (d, 1H, CH=CH, J=15.6 Hz), 7.69 (m, 1H, benz-H), 7.33 (m, 3H, benz-H + aryl-H), 7.19 (m, 3H, aryl-H + benz H), 7.10 (m, 2H, CH=CH + aryl-H), 5.06 (s, 2H, Fc—CH2), 4.16 (m, 2H, cpd-H), 4.07 (m, 7H, cpd-H), 2.32 (s, 3H, CH3). 13C NMR [δC, CDCl3], 150.93, 143.48, 138.94, 137.71, 136.47, 135.63, 130.35, 129.23, 128.43, 124.74, 123.0, 122.91, 119.78, 113.56, 109.96, 83.96, 69.24, 68.89, 68.84, 43.32, 21.92.

Synthesis of the N-Ferrocenylmethyl-2-(3-methylstyryl)-N'-methylbenzimidazolium iodide and hexafluorophosphate salts, [(C5H5)Fe(C5H4)CH2(C7H4N2CH3)CH=CHC6H4CH3]+ [I]- and [PF6]- salts.

N-Ferrocenylmethyl-2-(3-methylstyryl)benzimidazole (1.3 g, 3 mmol) was heated to reflux in excess methyl iodide (7 ml) for 2 h. The resultant orange precipitate was filtered and washed several times with ether to provide the iodo salt.

Yield 1.46 g (85 mmol) (74%), m.p. 492–495 K (uncorrected). IR (KBr, ν cm-1) (>1500 cm-1): 3062, 2994, 1649, 1637.

1H NMR [400 MHz, δH (p.p.m.), CDCl3], 8.24 (m, 1H, benz-H), 8.06 (m, 1H, benz-H), 7.82 (m, 2H, Aryl-H), 7.78 (m, 2H, CH=CH), 7.72 (m, 2H, Benz-H), 7.50 (t, 1H, aryl-H, J=7.6 Hz), 7.39 (d, 1H, Aryl-H, J=7.6 Hz), 5.74 (s, 2H, Fc—CH2), 4.36 (m, 2H, cpd-H), 4.28 (s, 5H, cpd-H), 4.12 (s, 5H, cpd-H + N—CH3), 2.32 (s, 3H, CH3). 13C NMR [δC, CDCl3], 150.93, 143.48, 138.94, 137.71, 136.47, 135.63, 130.35, 129.23, 128.43, 124.74, 123.0, 122.91, 119.78, 113.56, 109.96, 83.96, 69.24, 68.89, 68.84, 43.32, 21.92.

The [PF6]- salt was obtained by stirring the iodide derivative (from above) (0.4 g, 0.7 mmol) and ammonium hexafluorophosphate (0.12 g, 0.7 mmol) in methanol (50 ml) at room temperature for 24 h. The resultant orange-red precipitate was filtered and washed several times with methanol.

Yield 0.35 g (85%), m.p. 442–445 K (uncorrected). IR (KBr, ν cm-1) (>1500 cm-1): 3062, 2994, 1648, 1639.

1H NMR [400 MHz, δH (p.p.m.), CDCl3], 8.22 (m, 1H, benz-H), 8.06 (m, 1H, benz-H), 7.80 (m, 2H, Aryl-H), 7.76–7.73 (m, 2H, CH=CH), 7.71 (m, 2H, Benz-H), 7.49 (t, 1H, aryl-H, J=7.6 Hz), 7.39 (d, 1H, Aryl-H, J=7.6 Hz), 5.71 (s, 2H, Fc—CH2), 4.35 (m, 2H, cpd-H), 4.28 (s, 5H, cpd-H), 4.14 (s, 5H, cpd-H + N—CH3), 2.43 (s, 3H, CH3). 13C NMR [δC, CDCl3], 148.09, 147.07, 138.89, 134.61, 132.62, 132.28, 130.78, 129.45, 126.96, 125.99, 113.65, 113.57, 108.39, 81.27, 69.32, 68.93, 44.95, 33.81, 21.30.

Analysis for C28H27N2FePF6: Calc. C: 56.78, H: 4.59, 4.73; Found C: 56.78, H 4.55, N 4.80.

Refinement top

In the refinement all H atoms were allowed for as riding atoms with C—H distances of 0.93, 0.97 & 0.96 Å for the aromatic, methylene and methyl C—H [using the SHELXL97 (Sheldrick, 1997) defaults at 294 K].

There is considerable disorder in the hexafluorophosphate anion The commonly observed disorder over two sites of the [PF6]- moiety was further complicated by the presence of significant peaks of electron density between the modelled F atom site positions. The F atom sites were fixed using soft DFIX restraints [in SHELXL97 (Sheldrick, 1997)] for distance (P—F 1.579 Å) and angle (cis-F at 2.233 and trans-F at 3.158 Å) with soft parameters used for the DELU/ISOR restraints [in SHELXL97 (Sheldrick, 1997)]. The P atom is not disordered.

A satisfactory model was developed and the results are as follows: Two orientations of the [PF6]- moiety were discernible and input with 25% site occupancy per F atom for site positions labelled as A/C where A and C are related by a 30° rotation about one of the F—P—F axes (two A/C F atom sites are almost coincident whilst the other four are separated by the 30° rotation). Two remaining [PF6]- orientations (each with 25% F site occupancy) were subsequently included in a reasonable manner in the disorder model. The residual electron density in the final difference maps is +0.26/-0.28 e.Å-3 and therefore the disorder treatment can be said to have achieved a satisfactory conclusion. One PLATON (Spek, 2003) Alert B for a short intermolecular F4A···F4A contact can be disregarded as all F atom sites are modelled with 25% site occupancy.

Overall, the extensive disorder in the [PF6]- counterion is not surprising given that the [PF6]- anion occupies a void in the lattice of volume 215 Å3 or ca 30.7 Å3 per P/F atom: this is almost twice the average value expected for non-H atoms. Two voids of 64 Å3 per unit cell remain after the final refinement and analysis but these voids are featureless and are devoid of electron density.

Structure description top

Benzimidazole systems have attracted considerable attention in synthetic and structural as well as in applied biological research (Gallagher, Hanlon & Howarth, 2001; Howarth & Hanlon, 2001; Gallagher, Hanlon, Howarth & Thomas, 2001). The title compound (Figures 1–3) was obtained from a series of reactions involving synthesis of the parent N-Ferrocenylmethyl-2-(3-methylstyryl)benzimidazole from 2-(3-methylstyryl)benzimidazole and (trimethylammonium)ferrocenylmethyl iodide: subsequent treatment of the product with methyl iodide and replacement of the iodo salt with the hexafluorophosphate anion yields the [PF6]- salt.

Bond lengths and angles are normal and similar to those reported in the literature (Gallagher, Hanlon & Howarth, 2001; Gallagher, Hanlon, Howarth & Thomas, 2001). There is no disorder in the cation although the unsubstituted C5H5 ring displays large displacement parameters as could be expected given the geometry and the low energy barrier to rotation for Fe···η5-C5H5 π-bonding. The [PF6]- anion is disordered and a discussion of the treatment of this disorder is detailed below. The C3N2 5-membered imidazolium ring is almost orthogonal to the substituted C5H4 ring at 71.48 (10)° and deviates from co-planarity with the aromatic styryl C6 ring by 19.83 (10)°: the latter C6 ring is oriented at an angle of 85.52 (9)° to the C5H4 ring.

In the crystal structure there is only one intermolecular interaction of note (as detailed in Table 1) and involving C34—H34···Cg1i (where Cg1 is the ring centroid of C5H4 and the symmetry operation i = x - 3/2,3/2 - y,z). Several C—H···F contacts involving the disordered [PF6]- are present but are not important as they are relatively weak and involve the partial occupancy F atom sites.

Related structures include N-ferrocenylmethyl-2-ferrocenylbenzimidazole (Benito et al., 1995) and the salt N-ferrocenylmethyl-2-ferrocenyl-benzimidazolium tetrafluoroborate (Li et al., 1998) which differ from the title compound by having a ferrocenyl moiety at the 2-position of the benzimidazolium ring instead of the 3-methylstyryl group.

For related ferrocene literature, see: Benito et al. (1995); Li et al. (1998); Gallagher, Hanlon & Howarth (2001); Gallagher, Hanlon, Howarth & Thomas (2001); Howarth & Hanlon, (2001). For the chemical synthesis and crystal structure of [FcCH2N(CH3)3]+[I]-, see: Pauson et al. (1966); Ferguson et al. (1994).

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS (Bruker, 1996); data reduction: XSCANS (Bruker, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PREP8 (Ferguson, 1998).

Figures top
[Figure 1] Fig. 1. A view of the cation with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the C34—H34···π(C5H4) interaction in the crystal structure with atoms drawn as their van der Waals spheres. The C34 atom is labelled with a '*' and the η-C5H4i ring with a '#'.
[Figure 3] Fig. 3. A view of the disorder in the [PF6]- anion with each of the four orientations depicted as coloured spheres of arbitrary radii.
N-Ferrocenylmethyl-2-(3-methylstyryl)-N'-methylbenzimidazolium hexafluorophosphate top
Crystal data top
[Fe(C5H5)(C23H22N2)]PF6F(000) = 1216
Mr = 592.34Dx = 1.483 Mg m3
Monoclinic, P21/aMelting point: 483 K
Hall symbol: -P 2yabMo Kα radiation, λ = 0.71073 Å
a = 13.515 (1) ÅCell parameters from 85 reflections
b = 12.8743 (10) Åθ = 8.9–30.4°
c = 15.2839 (9) ŵ = 0.69 mm1
β = 94.037 (5)°T = 294 K
V = 2652.7 (3) Å3Block, red
Z = 40.29 × 0.25 × 0.17 mm
Data collection top
Bruker P4
diffractometer
3922 reflections with I > 2σ(I)
Radiation source: X-ray tubeRint = 0.025
Graphite monochromatorθmax = 28.0°, θmin = 2.1°
ω scansh = 171
Absorption correction: ψ scan
(North et al., 1968)
k = 117
Tmin = 0.826, Tmax = 0.889l = 2020
8107 measured reflections3 standard reflections every 197 reflections
6387 independent reflections intensity decay: 0.5%
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0435P)2 + 0.5898P]
where P = (Fo2 + 2Fc2)/3
6387 reflections(Δ/σ)max = 0.001
507 parametersΔρmax = 0.26 e Å3
228 restraintsΔρmin = 0.28 e Å3
Crystal data top
[Fe(C5H5)(C23H22N2)]PF6V = 2652.7 (3) Å3
Mr = 592.34Z = 4
Monoclinic, P21/aMo Kα radiation
a = 13.515 (1) ŵ = 0.69 mm1
b = 12.8743 (10) ÅT = 294 K
c = 15.2839 (9) Å0.29 × 0.25 × 0.17 mm
β = 94.037 (5)°
Data collection top
Bruker P4
diffractometer
3922 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.025
Tmin = 0.826, Tmax = 0.8893 standard reflections every 197 reflections
8107 measured reflections intensity decay: 0.5%
6387 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047228 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 1.01Δρmax = 0.26 e Å3
6387 reflectionsΔρmin = 0.28 e Å3
507 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Fe10.82902 (3)0.82379 (3)0.11263 (2)0.04913 (13)
P10.54550 (6)0.93397 (6)0.33825 (5)0.0581 (2)
F1A0.6347 (14)0.8544 (17)0.360 (2)0.106 (11)0.25
F2A0.559 (3)0.919 (2)0.2396 (11)0.143 (11)0.25
F3A0.4607 (14)1.0136 (15)0.321 (2)0.105 (10)0.25
F4A0.533 (2)0.947 (2)0.4403 (8)0.119 (9)0.25
F5A0.4701 (12)0.8394 (9)0.3395 (19)0.083 (10)0.25
F6A0.6243 (14)1.0236 (17)0.345 (2)0.120 (13)0.25
F1C0.6291 (19)0.8609 (17)0.312 (2)0.145 (12)0.25
F2C0.522 (3)0.9619 (16)0.2384 (9)0.115 (9)0.25
F3C0.4564 (14)1.0103 (15)0.362 (2)0.123 (9)0.25
F4C0.5611 (19)0.9047 (17)0.4371 (11)0.106 (9)0.25
F5C0.4652 (18)0.8425 (15)0.3265 (18)0.129 (15)0.25
F6C0.6175 (16)1.0283 (12)0.3520 (15)0.085 (10)0.25
F1B0.4510 (13)0.876 (2)0.3717 (18)0.105 (8)0.25
F2B0.556 (2)0.8398 (15)0.2719 (13)0.100 (7)0.25
F3B0.6385 (12)0.9846 (19)0.303 (2)0.110 (9)0.25
F4B0.531 (3)1.0242 (15)0.4024 (15)0.164 (10)0.25
F5B0.6096 (15)0.8745 (16)0.4128 (13)0.087 (8)0.25
F6B0.4771 (17)0.989 (2)0.2649 (17)0.085 (8)0.25
F1D0.487 (2)0.9106 (15)0.4142 (14)0.107 (6)0.25
F2D0.5115 (15)0.8346 (10)0.2877 (12)0.071 (4)0.25
F3D0.6158 (18)0.9605 (14)0.2560 (13)0.102 (7)0.25
F4D0.5959 (16)1.0353 (11)0.3844 (13)0.077 (7)0.25
F5D0.6401 (15)0.8699 (16)0.3792 (19)0.085 (10)0.25
F6D0.4659 (15)1.008 (2)0.2932 (19)0.087 (10)0.25
N11.00823 (15)1.13875 (16)0.40497 (12)0.0454 (5)
N20.94783 (14)0.99330 (14)0.35027 (12)0.0387 (4)
C10.92886 (17)1.09458 (18)0.36126 (14)0.0409 (5)
C20.88229 (18)0.91633 (18)0.30194 (15)0.0425 (6)
C31.04403 (17)0.97278 (19)0.38485 (14)0.0405 (5)
C41.08141 (18)1.06479 (19)0.41968 (15)0.0433 (6)
C51.1776 (2)1.0705 (2)0.45951 (17)0.0583 (7)
C61.2326 (2)0.9824 (3)0.46061 (19)0.0695 (9)
C71.1952 (2)0.8897 (3)0.42499 (19)0.0686 (8)
C81.0999 (2)0.8825 (2)0.38654 (17)0.0552 (7)
C101.0168 (2)1.2464 (2)0.4364 (2)0.0673 (8)
C110.89295 (17)0.91959 (18)0.20553 (15)0.0394 (5)
C120.83444 (19)0.9779 (2)0.14174 (17)0.0519 (6)
C130.8722 (2)0.9597 (2)0.05876 (17)0.0613 (8)
C140.9536 (2)0.8921 (2)0.07054 (17)0.0562 (7)
C150.96684 (18)0.8670 (2)0.16044 (17)0.0479 (6)
C210.7325 (4)0.7294 (4)0.1683 (3)0.0947 (13)
C220.6852 (3)0.7801 (4)0.0999 (4)0.1069 (14)
C230.7315 (4)0.7541 (5)0.0254 (3)0.1191 (19)
C240.8057 (4)0.6891 (4)0.0457 (4)0.1104 (17)
C250.8105 (4)0.6704 (3)0.1362 (4)0.1108 (16)
C1E0.83780 (19)1.1431 (2)0.32685 (16)0.0471 (6)
C2E0.8272 (2)1.2409 (2)0.30173 (17)0.0511 (6)
C310.73912 (19)1.28689 (19)0.25643 (16)0.0477 (6)
C320.7369 (2)1.3941 (2)0.24249 (18)0.0571 (7)
C330.6559 (2)1.4394 (2)0.19980 (19)0.0632 (8)
C340.5766 (2)1.3800 (2)0.16931 (17)0.0599 (8)
C350.57701 (19)1.2725 (2)0.17876 (17)0.0536 (7)
C360.65917 (19)1.2276 (2)0.22400 (16)0.0503 (6)
C370.4940 (2)1.2062 (3)0.1393 (2)0.0773 (9)
H2A0.81380.93050.31310.051*
H2B0.89850.84720.32370.051*
H51.20271.13200.48410.070*
H61.29730.98390.48590.083*
H71.23540.83100.42720.082*
H81.07460.82050.36310.066*
H10A1.04311.28910.39200.101*
H10B1.06051.24890.48870.101*
H10C0.95251.27170.44900.101*
H120.78101.02040.15260.062*
H130.84730.98770.00560.074*
H140.99210.86800.02670.067*
H151.01560.82350.18600.057*
H210.71640.73270.22650.114*
H220.63120.82440.10270.128*
H230.71340.77850.03080.143*
H240.84760.66050.00640.132*
H250.85550.62820.16830.133*
H1E0.78141.10160.32190.057*
H2E0.88111.28470.31410.061*
H320.79081.43470.26230.069*
H330.65451.51100.19140.076*
H340.52131.41220.14170.072*
H360.66051.15610.23270.060*
H37A0.43311.24480.13730.116*
H37B0.48781.14510.17440.116*
H37C0.50811.18640.08090.116*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0420 (2)0.0572 (2)0.0479 (2)0.01612 (18)0.00050 (15)0.01005 (18)
P10.0602 (5)0.0412 (4)0.0721 (5)0.0013 (4)0.0008 (4)0.0038 (4)
F1A0.106 (15)0.056 (11)0.16 (2)0.005 (8)0.015 (16)0.015 (14)
F2A0.20 (3)0.15 (3)0.073 (10)0.05 (2)0.011 (13)0.037 (14)
F3A0.081 (13)0.090 (13)0.15 (2)0.066 (10)0.021 (13)0.049 (15)
F4A0.170 (18)0.14 (2)0.042 (7)0.016 (17)0.016 (8)0.014 (9)
F5A0.065 (10)0.035 (8)0.15 (3)0.009 (7)0.007 (14)0.021 (10)
F6A0.055 (11)0.11 (2)0.20 (3)0.015 (11)0.030 (14)0.014 (17)
F1C0.108 (17)0.14 (2)0.19 (2)0.003 (14)0.075 (17)0.020 (19)
F2C0.20 (3)0.085 (13)0.063 (8)0.021 (15)0.014 (13)0.004 (7)
F3C0.078 (10)0.099 (12)0.20 (2)0.006 (8)0.036 (12)0.033 (16)
F4C0.119 (17)0.086 (14)0.111 (14)0.037 (12)0.016 (12)0.059 (11)
F5C0.14 (3)0.125 (19)0.12 (2)0.083 (16)0.011 (18)0.022 (14)
F6C0.13 (2)0.039 (9)0.078 (13)0.046 (11)0.006 (12)0.027 (9)
F1B0.079 (11)0.15 (2)0.091 (15)0.010 (12)0.031 (11)0.018 (13)
F2B0.130 (18)0.072 (9)0.106 (10)0.011 (12)0.053 (12)0.029 (8)
F3B0.060 (8)0.105 (18)0.17 (2)0.019 (11)0.017 (14)0.029 (17)
F4B0.18 (2)0.099 (13)0.21 (2)0.051 (18)0.00 (2)0.065 (13)
F5B0.082 (16)0.084 (12)0.090 (12)0.001 (10)0.032 (10)0.002 (10)
F6B0.087 (12)0.078 (14)0.090 (18)0.019 (9)0.002 (9)0.019 (14)
F1D0.15 (2)0.113 (14)0.059 (11)0.002 (13)0.033 (10)0.020 (10)
F2D0.069 (10)0.066 (7)0.078 (11)0.029 (8)0.001 (7)0.002 (8)
F3D0.128 (19)0.089 (10)0.093 (13)0.016 (11)0.043 (11)0.019 (10)
F4D0.078 (12)0.050 (7)0.095 (14)0.016 (9)0.036 (10)0.021 (8)
F5D0.058 (10)0.039 (7)0.15 (2)0.027 (6)0.047 (13)0.021 (11)
F6D0.069 (13)0.096 (16)0.094 (18)0.016 (10)0.017 (12)0.004 (13)
N10.0533 (12)0.0407 (11)0.0415 (11)0.0010 (10)0.0019 (9)0.0064 (9)
N20.0409 (10)0.0370 (11)0.0376 (10)0.0020 (9)0.0025 (8)0.0021 (8)
C10.0445 (13)0.0398 (13)0.0381 (12)0.0008 (11)0.0018 (10)0.0018 (10)
C20.0423 (13)0.0371 (13)0.0472 (13)0.0030 (11)0.0023 (11)0.0001 (11)
C30.0391 (12)0.0449 (14)0.0369 (12)0.0034 (11)0.0026 (10)0.0003 (11)
C40.0445 (13)0.0479 (14)0.0369 (12)0.0011 (12)0.0017 (10)0.0016 (11)
C50.0535 (16)0.0706 (19)0.0491 (15)0.0076 (15)0.0088 (13)0.0081 (14)
C60.0470 (16)0.098 (3)0.0608 (18)0.0082 (17)0.0147 (13)0.0026 (18)
C70.0584 (17)0.077 (2)0.0682 (19)0.0236 (16)0.0116 (15)0.0043 (17)
C80.0582 (16)0.0515 (16)0.0544 (15)0.0113 (14)0.0064 (13)0.0007 (13)
C100.085 (2)0.0451 (16)0.0694 (19)0.0046 (15)0.0150 (16)0.0169 (14)
C110.0372 (12)0.0361 (12)0.0442 (13)0.0058 (10)0.0018 (10)0.0029 (10)
C120.0503 (15)0.0499 (15)0.0545 (15)0.0042 (13)0.0042 (12)0.0005 (13)
C130.0752 (19)0.0642 (18)0.0436 (14)0.0138 (16)0.0023 (14)0.0049 (13)
C140.0522 (16)0.0639 (18)0.0539 (16)0.0187 (14)0.0126 (13)0.0122 (14)
C150.0374 (13)0.0475 (14)0.0586 (15)0.0063 (11)0.0018 (11)0.0084 (12)
C210.109 (3)0.098 (3)0.080 (3)0.068 (3)0.025 (2)0.021 (2)
C220.050 (2)0.119 (3)0.149 (4)0.037 (2)0.006 (3)0.009 (3)
C230.106 (3)0.168 (5)0.079 (3)0.083 (4)0.022 (3)0.015 (3)
C240.094 (3)0.103 (3)0.137 (4)0.052 (3)0.031 (3)0.065 (3)
C250.099 (3)0.055 (2)0.172 (5)0.039 (2)0.034 (3)0.012 (3)
C1E0.0447 (14)0.0464 (14)0.0500 (14)0.0048 (11)0.0009 (11)0.0019 (12)
C2E0.0507 (15)0.0495 (16)0.0525 (15)0.0016 (12)0.0004 (12)0.0014 (12)
C310.0504 (15)0.0443 (14)0.0488 (14)0.0087 (12)0.0060 (12)0.0060 (12)
C320.0613 (17)0.0476 (15)0.0625 (17)0.0062 (14)0.0058 (14)0.0023 (13)
C330.074 (2)0.0455 (16)0.0698 (18)0.0131 (15)0.0060 (16)0.0083 (14)
C340.0616 (18)0.0650 (19)0.0538 (16)0.0264 (16)0.0079 (14)0.0135 (14)
C350.0481 (15)0.0679 (18)0.0454 (14)0.0065 (14)0.0074 (12)0.0093 (13)
C360.0506 (15)0.0484 (15)0.0522 (15)0.0078 (13)0.0057 (12)0.0113 (12)
C370.0588 (18)0.100 (3)0.071 (2)0.0011 (18)0.0060 (16)0.0133 (18)
Geometric parameters (Å, º) top
Fe1—C112.028 (2)C2E—C311.460 (4)
Fe1—C122.034 (3)C31—C361.386 (4)
Fe1—C132.036 (3)C31—C321.396 (4)
Fe1—C142.043 (3)C32—C331.366 (4)
Fe1—C152.030 (2)C33—C341.372 (4)
Fe1—C212.016 (3)C34—C351.391 (4)
Fe1—C222.020 (3)C35—C361.392 (3)
Fe1—C232.018 (3)C35—C371.502 (4)
Fe1—C252.025 (4)C2—H2A0.9700
Fe1—C242.027 (4)C2—H2B0.9700
N1—C11.349 (3)C5—H50.9300
N1—C41.380 (3)C6—H60.9300
N1—C101.469 (3)C7—H70.9300
N2—C11.342 (3)C8—H80.9300
N2—C21.490 (3)C1E—H1E0.9300
N2—C31.394 (3)C2E—H2E0.9300
C1—C1E1.446 (3)C12—H120.9300
C2—C111.491 (3)C13—H130.9300
C3—C41.380 (3)C14—H140.9300
C3—C81.385 (3)C15—H150.9300
C4—C51.398 (3)C21—H210.9300
C5—C61.356 (4)C22—H220.9300
C6—C71.392 (4)C23—H230.9300
C7—C81.380 (4)C24—H240.9300
C11—C151.424 (3)C25—H250.9300
C11—C121.425 (3)C32—H320.9300
C12—C131.420 (4)C33—H330.9300
C13—C141.404 (4)C34—H340.9300
C14—C151.410 (4)C36—H360.9300
C21—C221.355 (6)C10—H10A0.9600
C21—C251.415 (6)C10—H10B0.9600
C22—C231.379 (6)C10—H10C0.9600
C23—C241.326 (6)C37—H37A0.9600
C24—C251.400 (6)C37—H37B0.9600
C1E—C2E1.321 (3)C37—H37C0.9600
C21—Fe1—C2366.35 (17)C15—C11—Fe169.55 (13)
C21—Fe1—C2239.22 (17)C12—C11—Fe169.70 (14)
C23—Fe1—C2239.94 (18)C2—C11—Fe1127.50 (16)
C21—Fe1—C2541.00 (17)C13—C12—C11107.9 (2)
C23—Fe1—C2566.5 (2)C13—C12—Fe169.67 (16)
C22—Fe1—C2567.38 (19)C11—C12—Fe169.21 (14)
C21—Fe1—C2467.33 (17)C13—C12—H12126.1
C23—Fe1—C2438.27 (19)C11—C12—H12126.1
C22—Fe1—C2466.32 (18)Fe1—C12—H12126.6
C25—Fe1—C2440.43 (19)C14—C13—C12108.4 (2)
C21—Fe1—C11109.13 (12)C14—C13—Fe170.12 (16)
C23—Fe1—C11163.6 (2)C12—C13—Fe169.50 (16)
C22—Fe1—C11126.64 (17)C14—C13—H13125.8
C25—Fe1—C11121.36 (17)C12—C13—H13125.8
C24—Fe1—C11156.6 (2)Fe1—C13—H13126.2
C21—Fe1—C15128.19 (16)C13—C14—C15108.1 (2)
C23—Fe1—C15154.1 (2)C13—C14—Fe169.62 (16)
C22—Fe1—C15164.46 (19)C15—C14—Fe169.25 (14)
C25—Fe1—C15108.97 (15)C13—C14—H14125.9
C24—Fe1—C15121.50 (18)C15—C14—H14125.9
C11—Fe1—C1541.08 (9)Fe1—C14—H14126.8
C21—Fe1—C12120.70 (16)C14—C15—C11108.5 (2)
C23—Fe1—C12126.2 (2)C14—C15—Fe170.22 (14)
C22—Fe1—C12108.21 (16)C11—C15—Fe169.36 (13)
C25—Fe1—C12156.2 (2)C14—C15—H15125.7
C24—Fe1—C12161.3 (2)C11—C15—H15125.7
C11—Fe1—C1241.09 (9)Fe1—C15—H15126.2
C15—Fe1—C1268.64 (10)C22—C21—C25108.2 (4)
C21—Fe1—C13154.4 (2)C22—C21—Fe170.6 (2)
C23—Fe1—C13107.88 (16)C25—C21—Fe169.9 (2)
C22—Fe1—C13120.11 (18)C22—C21—H21125.9
C25—Fe1—C13162.1 (2)C25—C21—H21125.9
C24—Fe1—C13124.74 (19)Fe1—C21—H21125.2
C11—Fe1—C1368.93 (10)C21—C22—C23107.7 (4)
C15—Fe1—C1368.17 (11)C21—C22—Fe170.2 (2)
C12—Fe1—C1340.83 (11)C23—C22—Fe170.0 (2)
C21—Fe1—C14164.81 (19)C21—C22—H22126.1
C23—Fe1—C14119.83 (17)C23—C22—H22126.1
C22—Fe1—C14153.94 (19)Fe1—C22—H22125.3
C25—Fe1—C14126.19 (19)C24—C23—C22109.8 (5)
C24—Fe1—C14108.17 (15)C24—C23—Fe171.2 (2)
C11—Fe1—C1468.82 (10)C22—C23—Fe170.1 (2)
C15—Fe1—C1440.52 (10)C24—C23—H23125.1
C12—Fe1—C1468.35 (11)C22—C23—H23125.1
C13—Fe1—C1440.26 (11)Fe1—C23—H23125.2
C1—N1—C4109.00 (19)C23—C24—C25108.8 (4)
C1—N1—C10127.0 (2)C23—C24—Fe170.5 (2)
C4—N1—C10124.0 (2)C25—C24—Fe169.7 (2)
C1—N2—C3108.54 (19)C23—C24—H24125.6
C1—N2—C2126.60 (19)C25—C24—H24125.6
C3—N2—C2124.62 (19)Fe1—C24—H24125.7
N2—C1—N1108.6 (2)C24—C25—C21105.5 (4)
N2—C1—C1E122.7 (2)C24—C25—Fe169.8 (2)
N1—C1—C1E128.7 (2)C21—C25—Fe169.1 (2)
N2—C2—C11112.06 (18)C24—C25—H25127.3
N2—C2—H2A109.2C21—C25—H25127.3
C11—C2—H2A109.2Fe1—C25—H25125.4
N2—C2—H2B109.2C2E—C1E—C1126.1 (3)
C11—C2—H2B109.2C2E—C1E—H1E116.9
H2A—C2—H2B107.9C1—C1E—H1E116.9
C4—C3—C8121.9 (2)C1E—C2E—C31126.3 (3)
C4—C3—N2106.9 (2)C1E—C2E—H2E116.8
C8—C3—N2131.2 (2)C31—C2E—H2E116.8
C3—C4—N1106.9 (2)C36—C31—C32118.8 (2)
C3—C4—C5121.1 (2)C36—C31—C2E122.4 (2)
N1—C4—C5131.9 (2)C32—C31—C2E118.8 (3)
C6—C5—C4117.0 (3)C33—C32—C31120.2 (3)
C6—C5—H5121.5C33—C32—H32119.9
C4—C5—H5121.5C31—C32—H32119.9
C5—C6—C7121.9 (3)C32—C33—C34120.3 (3)
C5—C6—H6119.1C32—C33—H33119.8
C7—C6—H6119.1C34—C33—H33119.8
C8—C7—C6121.8 (3)C33—C34—C35121.5 (3)
C8—C7—H7119.1C33—C34—H34119.3
C6—C7—H7119.1C35—C34—H34119.3
C7—C8—C3116.3 (3)C34—C35—C36117.5 (3)
C7—C8—H8121.9C34—C35—C37121.7 (3)
C3—C8—H8121.9C36—C35—C37120.7 (3)
N1—C10—H10A109.5C31—C36—C35121.6 (3)
N1—C10—H10B109.5C31—C36—H36119.2
H10A—C10—H10B109.5C35—C36—H36119.2
N1—C10—H10C109.5C35—C37—H37A109.5
H10A—C10—H10C109.5C35—C37—H37B109.5
H10B—C10—H10C109.5H37A—C37—H37B109.5
C15—C11—C12107.1 (2)C35—C37—H37C109.5
C15—C11—C2125.8 (2)H37A—C37—H37C109.5
C12—C11—C2127.1 (2)H37B—C37—H37C109.5
C3—N2—C1—N12.5 (3)C23—Fe1—C15—C1448.9 (5)
C2—N2—C1—N1177.06 (19)C22—Fe1—C15—C14162.4 (6)
C3—N2—C1—C1E175.4 (2)C25—Fe1—C15—C14124.0 (3)
C2—N2—C1—C1E0.8 (4)C24—Fe1—C15—C1481.1 (3)
C4—N1—C1—N22.2 (3)C11—Fe1—C15—C14119.7 (2)
C10—N1—C1—N2175.3 (2)C12—Fe1—C15—C1481.25 (17)
C4—N1—C1—C1E175.6 (2)C13—Fe1—C15—C1437.19 (16)
C10—N1—C1—C1E7.0 (4)C21—Fe1—C15—C1174.5 (2)
C1—N2—C2—C1182.7 (3)C23—Fe1—C15—C11168.7 (4)
C3—N2—C2—C1191.1 (3)C22—Fe1—C15—C1142.7 (6)
C1—N2—C3—C41.9 (3)C25—Fe1—C15—C11116.3 (3)
C2—N2—C3—C4176.57 (19)C24—Fe1—C15—C11159.1 (2)
C1—N2—C3—C8176.9 (3)C12—Fe1—C15—C1138.47 (14)
C2—N2—C3—C82.2 (4)C13—Fe1—C15—C1182.53 (16)
C8—C3—C4—N1178.4 (2)C14—Fe1—C15—C11119.7 (2)
N2—C3—C4—N10.5 (3)C23—Fe1—C21—C2238.1 (3)
C8—C3—C4—C50.9 (4)C25—Fe1—C21—C22118.8 (4)
N2—C3—C4—C5179.8 (2)C24—Fe1—C21—C2279.8 (3)
C1—N1—C4—C31.0 (3)C11—Fe1—C21—C22125.0 (3)
C10—N1—C4—C3176.6 (2)C15—Fe1—C21—C22167.1 (3)
C1—N1—C4—C5178.1 (3)C12—Fe1—C21—C2281.2 (3)
C10—N1—C4—C54.3 (4)C13—Fe1—C21—C2244.0 (4)
C3—C4—C5—C61.3 (4)C14—Fe1—C21—C22155.4 (5)
N1—C4—C5—C6177.7 (3)C23—Fe1—C21—C2580.8 (3)
C4—C5—C6—C70.9 (4)C22—Fe1—C21—C25118.8 (4)
C5—C6—C7—C80.1 (5)C24—Fe1—C21—C2539.0 (3)
C6—C7—C8—C30.4 (4)C11—Fe1—C21—C25116.1 (3)
C4—C3—C8—C70.0 (4)C15—Fe1—C21—C2574.1 (3)
N2—C3—C8—C7178.6 (3)C12—Fe1—C21—C25159.9 (3)
N2—C2—C11—C1584.2 (3)C13—Fe1—C21—C25162.9 (3)
N2—C2—C11—C1293.4 (3)C14—Fe1—C21—C2536.6 (6)
N2—C2—C11—Fe1174.77 (15)C25—C21—C22—C230.2 (4)
C21—Fe1—C11—C15126.7 (2)Fe1—C21—C22—C2360.2 (3)
C23—Fe1—C11—C15162.3 (5)C25—C21—C22—Fe160.0 (2)
C22—Fe1—C11—C15166.9 (2)C23—Fe1—C22—C21118.4 (4)
C25—Fe1—C11—C1583.1 (3)C25—Fe1—C22—C2138.5 (3)
C24—Fe1—C11—C1549.7 (4)C24—Fe1—C22—C2182.6 (3)
C12—Fe1—C11—C15118.2 (2)C11—Fe1—C22—C2174.6 (3)
C13—Fe1—C11—C1580.54 (17)C15—Fe1—C22—C2140.9 (7)
C14—Fe1—C11—C1537.24 (15)C12—Fe1—C22—C21116.5 (3)
C21—Fe1—C11—C12115.1 (2)C13—Fe1—C22—C21159.7 (3)
C23—Fe1—C11—C1244.1 (6)C14—Fe1—C22—C21165.6 (3)
C22—Fe1—C11—C1274.9 (3)C21—Fe1—C22—C23118.4 (4)
C25—Fe1—C11—C12158.7 (2)C25—Fe1—C22—C2379.9 (4)
C24—Fe1—C11—C12167.9 (4)C24—Fe1—C22—C2335.7 (3)
C15—Fe1—C11—C12118.2 (2)C11—Fe1—C22—C23167.0 (3)
C13—Fe1—C11—C1237.63 (16)C15—Fe1—C22—C23159.3 (5)
C14—Fe1—C11—C1280.93 (16)C12—Fe1—C22—C23125.1 (3)
C21—Fe1—C11—C26.7 (3)C13—Fe1—C22—C2382.0 (4)
C23—Fe1—C11—C277.7 (6)C14—Fe1—C22—C2347.3 (5)
C22—Fe1—C11—C246.9 (3)C21—C22—C23—C240.0 (5)
C25—Fe1—C11—C236.9 (3)Fe1—C22—C23—C2460.4 (3)
C24—Fe1—C11—C270.3 (4)C21—C22—C23—Fe160.3 (3)
C15—Fe1—C11—C2120.0 (3)C21—Fe1—C23—C2482.9 (3)
C12—Fe1—C11—C2121.8 (3)C22—Fe1—C23—C24120.3 (5)
C13—Fe1—C11—C2159.4 (2)C25—Fe1—C23—C2437.9 (3)
C14—Fe1—C11—C2157.3 (2)C11—Fe1—C23—C24160.1 (5)
C15—C11—C12—C130.6 (3)C15—Fe1—C23—C2447.2 (5)
C2—C11—C12—C13178.6 (2)C12—Fe1—C23—C24165.4 (3)
Fe1—C11—C12—C1359.15 (19)C13—Fe1—C23—C24123.9 (3)
C15—C11—C12—Fe159.78 (16)C14—Fe1—C23—C2481.6 (3)
C2—C11—C12—Fe1122.3 (2)C21—Fe1—C23—C2237.4 (3)
C21—Fe1—C12—C13156.4 (2)C25—Fe1—C23—C2282.3 (3)
C23—Fe1—C12—C1374.7 (3)C24—Fe1—C23—C22120.3 (5)
C22—Fe1—C12—C13115.3 (2)C11—Fe1—C23—C2239.8 (7)
C25—Fe1—C12—C13169.7 (4)C15—Fe1—C23—C22167.5 (3)
C24—Fe1—C12—C1345.6 (5)C12—Fe1—C23—C2274.3 (4)
C11—Fe1—C12—C13119.4 (2)C13—Fe1—C23—C22115.8 (3)
C15—Fe1—C12—C1380.91 (18)C14—Fe1—C23—C22158.2 (3)
C14—Fe1—C12—C1337.20 (16)C22—C23—C24—C250.3 (5)
C21—Fe1—C12—C1184.2 (2)Fe1—C23—C24—C2559.4 (3)
C23—Fe1—C12—C11165.9 (2)C22—C23—C24—Fe159.7 (3)
C22—Fe1—C12—C11125.3 (2)C21—Fe1—C24—C2380.1 (3)
C25—Fe1—C12—C1150.3 (4)C22—Fe1—C24—C2337.3 (3)
C24—Fe1—C12—C11164.9 (4)C25—Fe1—C24—C23119.6 (4)
C15—Fe1—C12—C1138.47 (14)C11—Fe1—C24—C23166.0 (3)
C13—Fe1—C12—C11119.4 (2)C15—Fe1—C24—C23157.9 (3)
C14—Fe1—C12—C1182.17 (16)C12—Fe1—C24—C2339.4 (6)
C11—C12—C13—C140.7 (3)C13—Fe1—C24—C2374.0 (3)
Fe1—C12—C13—C1459.54 (19)C14—Fe1—C24—C23115.4 (3)
C11—C12—C13—Fe158.87 (17)C21—Fe1—C24—C2539.6 (3)
C21—Fe1—C13—C14172.2 (3)C23—Fe1—C24—C25119.6 (4)
C23—Fe1—C13—C14115.3 (3)C22—Fe1—C24—C2582.4 (3)
C22—Fe1—C13—C14157.2 (2)C11—Fe1—C24—C2546.4 (5)
C25—Fe1—C13—C1446.8 (5)C15—Fe1—C24—C2582.4 (3)
C24—Fe1—C13—C1476.6 (3)C12—Fe1—C24—C25159.0 (4)
C11—Fe1—C13—C1481.72 (16)C13—Fe1—C24—C25166.4 (3)
C15—Fe1—C13—C1437.43 (15)C14—Fe1—C24—C25125.0 (3)
C12—Fe1—C13—C14119.6 (2)C23—C24—C25—C210.4 (4)
C21—Fe1—C13—C1252.6 (4)Fe1—C24—C25—C2160.3 (2)
C23—Fe1—C13—C12125.1 (3)C23—C24—C25—Fe159.9 (3)
C22—Fe1—C13—C1283.2 (2)C22—C21—C25—C240.3 (4)
C25—Fe1—C13—C12166.4 (5)Fe1—C21—C25—C2460.8 (2)
C24—Fe1—C13—C12163.8 (2)C22—C21—C25—Fe160.4 (3)
C11—Fe1—C13—C1237.87 (15)C21—Fe1—C25—C24116.4 (4)
C15—Fe1—C13—C1282.16 (17)C23—Fe1—C25—C2436.0 (3)
C14—Fe1—C13—C12119.6 (2)C22—Fe1—C25—C2479.5 (3)
C12—C13—C14—C150.4 (3)C11—Fe1—C25—C24160.3 (3)
Fe1—C13—C14—C1558.71 (18)C15—Fe1—C25—C24116.7 (3)
C12—C13—C14—Fe159.15 (19)C12—Fe1—C25—C24163.4 (3)
C21—Fe1—C14—C13167.1 (5)C13—Fe1—C25—C2439.1 (6)
C23—Fe1—C14—C1382.6 (3)C14—Fe1—C25—C2474.8 (3)
C22—Fe1—C14—C1349.6 (4)C23—Fe1—C25—C2180.4 (3)
C25—Fe1—C14—C13163.9 (2)C22—Fe1—C25—C2136.9 (2)
C24—Fe1—C14—C13122.7 (3)C24—Fe1—C25—C21116.4 (4)
C11—Fe1—C14—C1382.00 (16)C11—Fe1—C25—C2183.3 (3)
C15—Fe1—C14—C13119.7 (2)C15—Fe1—C25—C21127.0 (3)
C12—Fe1—C14—C1337.71 (16)C12—Fe1—C25—C2147.0 (5)
C21—Fe1—C14—C1547.4 (5)C13—Fe1—C25—C21155.5 (4)
C23—Fe1—C14—C15157.7 (3)C14—Fe1—C25—C21168.8 (2)
C22—Fe1—C14—C15169.4 (3)N2—C1—C1E—C2E150.1 (3)
C25—Fe1—C14—C1576.4 (3)N1—C1—C1E—C2E27.4 (4)
C24—Fe1—C14—C15117.5 (3)C1—C1E—C2E—C31171.4 (2)
C11—Fe1—C14—C1537.74 (15)C1E—C2E—C31—C368.8 (4)
C12—Fe1—C14—C1582.03 (16)C1E—C2E—C31—C32173.6 (3)
C13—Fe1—C14—C15119.7 (2)C36—C31—C32—C331.9 (4)
C13—C14—C15—C110.1 (3)C2E—C31—C32—C33179.6 (3)
Fe1—C14—C15—C1158.98 (16)C31—C32—C33—C340.8 (4)
C13—C14—C15—Fe158.93 (19)C32—C33—C34—C351.6 (4)
C12—C11—C15—C140.4 (3)C33—C34—C35—C362.9 (4)
C2—C11—C15—C14178.3 (2)C33—C34—C35—C37175.0 (3)
Fe1—C11—C15—C1459.52 (17)C32—C31—C36—C350.5 (4)
C12—C11—C15—Fe159.87 (16)C2E—C31—C36—C35178.1 (2)
C2—C11—C15—Fe1122.2 (2)C34—C35—C36—C311.8 (4)
C21—Fe1—C15—C14165.8 (2)C37—C35—C36—C31176.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C34—H34···Cg1i0.932.653.472 (3)149
Symmetry code: (i) x3/2, y+3/2, z.

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C23H22N2)]PF6
Mr592.34
Crystal system, space groupMonoclinic, P21/a
Temperature (K)294
a, b, c (Å)13.515 (1), 12.8743 (10), 15.2839 (9)
β (°) 94.037 (5)
V3)2652.7 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.69
Crystal size (mm)0.29 × 0.25 × 0.17
Data collection
DiffractometerBruker P4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.826, 0.889
No. of measured, independent and
observed [I > 2σ(I)] reflections
8107, 6387, 3922
Rint0.025
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.113, 1.01
No. of reflections6387
No. of parameters507
No. of restraints228
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.28

Computer programs: XSCANS (Bruker, 1996), SHELXS97 (Sheldrick, 1997), ORTEX (McArdle, 1995) and PLATON (Spek, 2003), SHELXL97 (Sheldrick, 1997) and PREP8 (Ferguson, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C34—H34···Cg1i0.932.653.472 (3)149
Symmetry code: (i) x3/2, y+3/2, z.
 

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