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The title compound, [Fe(C8H11ClO2)(CO)3], has been synthesized, isolated and characterized by single-crystal X-ray diffraction. The mol­ecule crystallizes in the orthorhombic space group P212121. The metal-ligand arrangement is typical of (1,3-diene)­tri­carbonyl­iron complexes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100006399/sx1099sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006399/sx1099Isup2.hkl
Contains datablock I

CCDC reference: 147637

Comment top

The title compound, (I), is a transition metal tricarbonyl and diene π-complex. These kinds of compounds are used extensively in organic synthesis. Those in which the diene has chiral centres are particularly useful because they offer an efficient approach to enantioselective synthesis. It has been reported that the stereocontrol is produced by the metal centre, which effectively hinders access to one side of the molecule (Johnson et al., 1977; Howard et al., 1989). The chiral dienic system in the present structure was prepared by microbial dioxygenation of chlorobenzene (Gibson et al., 1970; Brovetto et al., 1999) to give a homochiral cis-diol, followed by further treatment with methyliodide to obtain the cis-dimethylether. \sch

Fig. 1 shows the molecular structure of (I). The metal-ligand arrangement is similar to that observed in other (cyclohexa-1,3-diene)tricarbonyliron derivatives (Dunand & Robertson, 1982). All bond distances and angles (Table 1) are within the range of expected values (Guy et al., 1976; Anderson & Robertson, 1984).

The determination of the absolute configuration of the molecule agrees with that of the parent dienic cis-diol (Gibson et al., 1970). The chiral centres C5 and C6 (arising from the original enzymatic synthesis) are R and S, respectively. The descriptor for the entire complex is S because the fiduciary atom C1 (bonded to Fe and Cl) is in the S configuration. For all assignments of configuration, the occurrence of bonding to Fe was taken into account.

The diene moiety, C1/C2/C3/C4, is planar. The maximum absolute deviation from the mean plane is 0.014 (3) Å for C3. On the other hand, the planarity of the set C1/C6/C5/C4 is lower, with a maximum absolute deviation 0.06 (2) Å for C5 and C6. The dihedral angle of 41.9 (3)° between the two planes agrees well with the values observed for tricarbonyl[2–5-η-(dimethyl 2,4-cyclohexadiene-1α,2-dicarboxylate)]iron(0) (42.1°; Dunand & Robertson, 1982*), tricarbonyl[2–5-η-(methyl 1α-phenyl-2,4-cyclohexadiene-1β-carboxylate)]iron(0) (42.2**°; Anderson et al., 1982) and tricarbonyl{(4–7-η)-3-acetyl-3a,7a-dihydro-6-methoxy-2-methylbenzo[b]furan)} iron(0) (41.7°; Anderson & Robertson, 1983). Such a high value is characteristic of systems containing both electron-donating and electron-withdrawing ring substituents, as previously reported by Anderson & Robertson (1983). *please check - name and angle are for paper at B38, 2037–2040. **given as 42.4° in orig CIF, 42.2° where cited in B38 2034–2037.

The Fe(CO)3 group and all the substituents are located on the same side of the six-membered ring. The carbonyl (C9/C10/C11) and the diene (C1/C2/C3/C4) planes are not parallel; the dihedral angle between these planes is 13.8 (3)°, with the carbonyl ligand –C10O4 closer to the diene plane. Atom O2 of the methoxy group bonded to C6 is in relatively close contact with the carbonyl group –C11O5, with separations O2···C11 2.903 (5) and O2···O5 3.130 (4) Å.

The presence of the Cl atom (an electron-withdrawing substituent) bonded to C1 removes the C1—C2, C3—C4 bond-length similarity (Dunand & Robertson, 1982), with the C1—C2 bond distance of 1.442 (5) Å significantly longer than the C3—C4 bond distance of 1.416 (6) Å.

The absence of hydrogen bonds and π-contacts suggest that the crystal packing is directed by van der Waals forces.

Our results are consistent with the mechanism described in a previous report (Howard et al., 1989), where the methoxy groups were considered to play an important role in the diastereoface selectivity of the complexation. According to that work, the complexation should first occur via the O atoms belonging to the methoxy groups and take place finally through the more favourable dienic system. Thus, the present work, which demonstrates that the binding of the iron tricarbonyl moiety is located on the same side of the six-membered ring as the methoxy substituents, supports the importance of the methoxy groups for stereocontrol in these homochiral-complexes with planar chirality, making them useful reagents in chiral synthesis.

Experimental top

Compound (I) was synthesized following reported procedures for this type of compound (Howard et al., 1989; Pearson et al., 1992). The starting 1-chloro-cyclohexa-1,3-diene-5,6-diol, obtained by microbial oxidation of chlorobenzene (Gibson et al., 1970; Brovetto et al., 1999), was treated with methyliodide to give the dimethylether, and further reacted with Fe2(CO)9. Suitable crystals were grown as colourless plates from dichloromethane by slow cooling.

Refinement top

All H atoms were found in difference Fourier maps and freely refined, except those belonging to C10 which were placed at geometrically suitable positions and refined with fixed isotropic displacement parameters, Uiso = 1.2Ueq of the parent atom.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: MSC/AFC Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai & Pritzkow, 1995); software used to prepare material for publication: PLATON98 (Spek, 1998).

Figures top
[Figure 1] Fig. 1. The molecular view of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are drawn as spheres of arbitrary radii.
(I) top
Crystal data top
[Fe(CO3)(C8H11O2Cl)]Dx = 1.604 Mg m3
Mr = 314.50Mo Kα radiation, λ = 0.71070 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 7.139 (2) Åθ = 25.1–26.8°
b = 26.763 (2) ŵ = 1.37 mm1
c = 6.815 (2) ÅT = 293 K
V = 1302.0 (6) Å3Plate, colourless
Z = 40.30 × 0.28 × 0.10 mm
F(000) = 640
Data collection top
Rigaku AFC-7S
diffractometer
1793 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.056
Graphite monochromatorθmax = 27.5°, θmin = 3.0°
θ/2θ scansh = 99
Absorption correction: ψ-scan
(MSC/AFC Diffractometer Control Software; Molecular Structure Corporation, 1993)
k = 3234
Tmin = 0.684, Tmax = 0.875l = 78
1996 measured reflections3 standard reflections every 150 reflections
1715 (241) independent reflections intensity decay: 1%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.044Calculated w = 1/[σ2(Fo2) + (0.0877P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.119(Δ/σ)max < 0.001
S = 1.06Δρmax = 1.25 e Å3
1956 reflectionsΔρmin = 0.76 e Å3
197 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.046 (5)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.00 (3)
Crystal data top
[Fe(CO3)(C8H11O2Cl)]V = 1302.0 (6) Å3
Mr = 314.50Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.139 (2) ŵ = 1.37 mm1
b = 26.763 (2) ÅT = 293 K
c = 6.815 (2) Å0.30 × 0.28 × 0.10 mm
Data collection top
Rigaku AFC-7S
diffractometer
1793 reflections with I > 2σ(I)
Absorption correction: ψ-scan
(MSC/AFC Diffractometer Control Software; Molecular Structure Corporation, 1993)
Rint = 0.056
Tmin = 0.684, Tmax = 0.8753 standard reflections every 150 reflections
1996 measured reflections intensity decay: 1%
1715 (241) independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119Δρmax = 1.25 e Å3
S = 1.06Δρmin = 0.76 e Å3
1956 reflectionsAbsolute structure: Flack (1983)
197 parametersAbsolute structure parameter: 0.00 (3)
0 restraints
Special details top

Geometry. NOT INTENDED FOR PUBLICATION

All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Least-squares planes mentioned above ——————————————————————–

Plane 1 − 3.022 (11)*x + 14.35 (56)*y + 4.9778 (12)*z=2.411 (92)

Atoms belonging to the previous plane and deviations (Ang.) from it:

C1 0.0352 (13) C6 − 0.0583 (21) C5 0.0583 (21) C4 − 0.0351 (13)

Plane 2: −3.304 (11)*x + 23.558 (26)*y + 0.714 (25)*z=3.4684 (34)

Atoms belonging to the previous plane and deviations (Ang.) from it:

C1 − 0.0072 (14) C2 0.0134 (25) C3 − 0.0136 (26) C4 0.0075 (14)

Plane 3:

−3.414 (16)*x + 21.742 (39)*y + 2.274 (14)*z=0.8893 (42)

Atoms belonging to the previous plane:

C9 C10 C11

Acute angles between planes (Deg.) —————————————

Plane 1, Plane 2 = 41.9 (3) Plane 2, Plane 3 = 13.8 (3)

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
Fe0.01687 (7)0.078828 (17)0.05939 (7)0.0433 (2)
C100.0840 (8)0.01829 (16)0.0902 (8)0.0683 (12)
O40.1500 (8)0.02029 (14)0.1128 (8)0.1106 (18)
C90.2339 (7)0.05996 (15)0.1688 (7)0.0623 (10)
O30.3758 (6)0.04809 (15)0.2339 (8)0.0938 (14)
C110.0780 (7)0.07363 (14)0.1958 (6)0.0560 (9)
O50.1183 (8)0.06854 (13)0.3538 (5)0.0866 (13)
C10.0722 (5)0.15431 (12)0.0906 (5)0.0439 (7)
Cl0.29768 (15)0.17750 (4)0.14568 (18)0.0625 (3)
C20.0309 (6)0.13568 (14)0.2571 (5)0.0497 (8)
H20.020 (6)0.1348 (16)0.379 (6)0.048 (10)*
C30.1999 (6)0.11237 (16)0.2059 (6)0.0536 (9)
H30.277 (12)0.098 (3)0.279 (12)0.13 (3)*
C40.2429 (6)0.11338 (16)0.0031 (6)0.0520 (8)
H40.349 (9)0.0937 (19)0.048 (8)0.074 (16)*
C50.2193 (5)0.16239 (15)0.1050 (6)0.0476 (7)
H50.308 (7)0.1847 (18)0.052 (8)0.057 (13)*
O10.2486 (4)0.15781 (12)0.3074 (4)0.0573 (7)
C60.0198 (5)0.18388 (12)0.0693 (5)0.0418 (6)
H60.019 (8)0.2187 (16)0.020 (6)0.048 (11)*
C70.4421 (6)0.1571 (2)0.3566 (8)0.0757 (14)
H7A0.4552 (8)0.1541 (3)0.491 (5)0.091*
H7B0.497 (2)0.1865 (10)0.3155 (16)0.091*
H7C0.499 (2)0.1304 (9)0.296 (2)0.091*
O20.0959 (4)0.18149 (9)0.2369 (4)0.0468 (6)
C80.0940 (7)0.22545 (15)0.3529 (7)0.0593 (10)
H8A0.028 (7)0.2341 (18)0.404 (7)0.053 (12)*
H8B0.162 (7)0.2533 (16)0.278 (7)0.058 (13)*
H8C0.172 (8)0.2159 (18)0.475 (7)0.058 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe0.0494 (3)0.0371 (3)0.0434 (3)0.00265 (19)0.0026 (2)0.00332 (16)
C100.083 (3)0.0496 (19)0.072 (3)0.0122 (19)0.011 (3)0.002 (2)
O40.137 (4)0.0566 (18)0.138 (4)0.032 (2)0.028 (4)0.009 (2)
C90.067 (2)0.0514 (19)0.069 (2)0.0047 (19)0.006 (2)0.0120 (19)
O30.073 (2)0.080 (2)0.128 (4)0.012 (2)0.023 (3)0.024 (2)
C110.083 (3)0.0402 (16)0.0448 (18)0.0017 (17)0.0094 (17)0.0016 (14)
O50.141 (4)0.0629 (17)0.0559 (18)0.018 (2)0.021 (2)0.0002 (15)
C10.0432 (15)0.0397 (14)0.0488 (17)0.0027 (12)0.0015 (13)0.0024 (13)
Cl0.0539 (5)0.0675 (6)0.0660 (6)0.0187 (4)0.0107 (4)0.0024 (5)
C20.0575 (19)0.0498 (16)0.0417 (15)0.0016 (16)0.0042 (15)0.0018 (14)
C30.0503 (19)0.059 (2)0.0512 (19)0.0044 (16)0.0170 (16)0.0026 (16)
C40.0413 (17)0.0550 (19)0.060 (2)0.0096 (15)0.0056 (15)0.0027 (16)
C50.0338 (13)0.0553 (17)0.0536 (19)0.0086 (14)0.0073 (13)0.0011 (15)
O10.0428 (13)0.0762 (18)0.0531 (14)0.0079 (13)0.0003 (12)0.0028 (13)
C60.0435 (15)0.0364 (13)0.0456 (14)0.0035 (12)0.0047 (15)0.0001 (11)
C70.052 (2)0.106 (4)0.069 (3)0.007 (2)0.013 (2)0.007 (3)
O20.0481 (12)0.0397 (10)0.0526 (13)0.0072 (10)0.0092 (11)0.0084 (10)
C80.070 (2)0.0473 (17)0.061 (2)0.0049 (18)0.009 (2)0.0113 (18)
Geometric parameters (Å, º) top
Fe—C101.785 (4)C3—H30.83 (8)
Fe—C91.792 (5)C4—C51.514 (5)
Fe—C111.798 (4)C4—H40.99 (6)
Fe—C32.049 (4)C5—O11.400 (5)
Fe—C22.061 (4)C5—C61.555 (5)
Fe—C12.069 (3)C5—H50.95 (5)
Fe—C42.108 (4)O1—C71.421 (5)
C10—O41.145 (6)C6—O21.411 (4)
C9—O31.151 (7)C6—H60.99 (4)
C11—O51.123 (6)C7—H7A0.9221
C1—C21.442 (5)C7—H7B0.9221
C1—C61.498 (5)C7—H7C0.9221
C1—Cl1.765 (4)O2—C81.418 (4)
C2—C31.402 (6)C8—H8A0.97 (5)
C2—H20.91 (4)C8—H8B1.02 (5)
C3—C41.416 (6)C8—H8C1.03 (5)
C10—Fe—C992.5 (2)C2—C3—Fe70.5 (2)
C10—Fe—C1198.1 (2)C4—C3—Fe72.3 (2)
C9—Fe—C1199.8 (2)C2—C3—H3128 (6)
C10—Fe—C392.1 (2)C4—C3—H3117 (6)
C9—Fe—C3125.0 (2)Fe—C3—H3126 (5)
C11—Fe—C3133.5 (2)C3—C4—C5117.9 (4)
C10—Fe—C2121.8 (2)C3—C4—Fe67.9 (2)
C9—Fe—C294.5 (2)C5—C4—Fe111.7 (2)
C11—Fe—C2136.85 (16)C3—C4—H4120 (3)
C3—Fe—C239.91 (17)C5—C4—H4112 (3)
C10—Fe—C1162.0 (2)Fe—C4—H4121 (3)
C9—Fe—C193.86 (17)O1—C5—C4112.8 (3)
C11—Fe—C197.38 (16)O1—C5—C6108.9 (3)
C3—Fe—C170.52 (15)C4—C5—C6110.3 (3)
C2—Fe—C140.86 (14)O1—C5—H5110 (3)
C10—Fe—C493.7 (2)C4—C5—H5107 (3)
C9—Fe—C4163.77 (19)C6—C5—H5109 (3)
C11—Fe—C494.09 (19)C5—O1—C7112.3 (3)
C3—Fe—C439.81 (17)O2—C6—C1107.9 (3)
C2—Fe—C469.48 (17)O2—C6—C5113.1 (3)
C1—Fe—C476.02 (15)C1—C6—C5108.7 (3)
O4—C10—Fe178.8 (5)O2—C6—H6108 (3)
O3—C9—Fe178.0 (5)C1—C6—H6104 (3)
O5—C11—Fe177.3 (4)C5—C6—H6114 (3)
C2—C1—C6122.1 (3)O1—C7—H7A109.5
C2—C1—Cl114.8 (3)O1—C7—H7B109.5
C6—C1—Cl111.6 (2)H7A—C7—H7B109.5
C2—C1—Fe69.24 (19)O1—C7—H7C109.5
C6—C1—Fe110.9 (2)H7A—C7—H7C109.5
Cl—C1—Fe122.62 (18)H7B—C7—H7C109.5
C3—C2—C1113.4 (3)C6—O2—C8114.1 (3)
C3—C2—Fe69.6 (2)O2—C8—H8A114 (3)
C1—C2—Fe69.90 (19)O2—C8—H8B109 (3)
C3—C2—H2124 (3)H8A—C8—H8B116 (4)
C1—C2—H2122 (3)O2—C8—H8C104 (3)
Fe—C2—H2121 (3)H8A—C8—H8C105 (4)
C2—C3—C4114.9 (3)H8B—C8—H8C109 (4)
C9—Fe—C10—O495 (30)C3—Fe—C2—C1126.0 (3)
C11—Fe—C10—O4165 (30)C4—Fe—C2—C192.2 (2)
C3—Fe—C10—O430 (30)C1—C2—C3—C42.8 (5)
C2—Fe—C10—O42 (30)Fe—C2—C3—C458.7 (3)
C1—Fe—C10—O415 (31)C1—C2—C3—Fe55.9 (3)
C4—Fe—C10—O470 (30)C10—Fe—C3—C2141.1 (3)
C10—Fe—C9—O3116 (13)C9—Fe—C3—C246.6 (3)
C11—Fe—C9—O317 (13)C11—Fe—C3—C2115.7 (3)
C3—Fe—C9—O3150 (13)C1—Fe—C3—C234.2 (2)
C2—Fe—C9—O3122 (13)C4—Fe—C3—C2125.5 (4)
C1—Fe—C9—O381 (13)C10—Fe—C3—C493.3 (3)
C4—Fe—C9—O3132 (13)C9—Fe—C3—C4172.1 (3)
C10—Fe—C11—O541 (12)C11—Fe—C3—C49.9 (4)
C9—Fe—C11—O553 (12)C2—Fe—C3—C4125.5 (4)
C3—Fe—C11—O5141 (11)C1—Fe—C3—C491.4 (3)
C2—Fe—C11—O5161 (11)C2—C3—C4—C546.0 (5)
C1—Fe—C11—O5149 (12)Fe—C3—C4—C5103.7 (3)
C4—Fe—C11—O5135 (12)C2—C3—C4—Fe57.7 (3)
C10—Fe—C1—C218.0 (8)C10—Fe—C4—C388.7 (3)
C9—Fe—C1—C292.5 (3)C9—Fe—C4—C323.6 (7)
C11—Fe—C1—C2167.1 (3)C11—Fe—C4—C3172.8 (3)
C3—Fe—C1—C233.4 (2)C2—Fe—C4—C333.9 (2)
C4—Fe—C1—C274.7 (2)C1—Fe—C4—C376.2 (3)
C10—Fe—C1—C699.6 (7)C10—Fe—C4—C5158.9 (3)
C9—Fe—C1—C6149.9 (3)C9—Fe—C4—C588.8 (7)
C11—Fe—C1—C649.5 (3)C11—Fe—C4—C560.4 (3)
C3—Fe—C1—C684.2 (3)C3—Fe—C4—C5112.4 (4)
C2—Fe—C1—C6117.6 (3)C2—Fe—C4—C578.5 (3)
C4—Fe—C1—C642.9 (2)C1—Fe—C4—C536.2 (3)
C10—Fe—C1—Cl124.8 (6)C3—C4—C5—O1174.3 (3)
C9—Fe—C1—Cl14.4 (3)Fe—C4—C5—O198.7 (3)
C11—Fe—C1—Cl86.1 (3)C3—C4—C5—C652.4 (4)
C3—Fe—C1—Cl140.3 (3)Fe—C4—C5—C623.3 (4)
C2—Fe—C1—Cl106.9 (3)C4—C5—O1—C779.8 (5)
C4—Fe—C1—Cl178.5 (3)C6—C5—O1—C7157.5 (4)
C6—C1—C2—C346.6 (5)C2—C1—C6—O2159.9 (3)
Cl—C1—C2—C3173.1 (3)Cl—C1—C6—O258.7 (3)
Fe—C1—C2—C355.7 (3)Fe—C1—C6—O281.9 (3)
C6—C1—C2—Fe102.3 (3)C2—C1—C6—C536.9 (4)
Cl—C1—C2—Fe117.4 (2)Cl—C1—C6—C5178.3 (2)
C10—Fe—C2—C347.6 (3)Fe—C1—C6—C541.1 (3)
C9—Fe—C2—C3143.3 (3)O1—C5—C6—O215.0 (4)
C11—Fe—C2—C3107.1 (3)C4—C5—C6—O2109.2 (3)
C1—Fe—C2—C3126.0 (3)O1—C5—C6—C1134.8 (3)
C4—Fe—C2—C333.8 (2)C4—C5—C6—C110.6 (4)
C10—Fe—C2—C1173.6 (3)C1—C6—O2—C8146.3 (3)
C9—Fe—C2—C190.7 (3)C5—C6—O2—C893.4 (4)
C11—Fe—C2—C118.9 (4)

Experimental details

Crystal data
Chemical formula[Fe(CO3)(C8H11O2Cl)]
Mr314.50
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)7.139 (2), 26.763 (2), 6.815 (2)
V3)1302.0 (6)
Z4
Radiation typeMo Kα
µ (mm1)1.37
Crystal size (mm)0.30 × 0.28 × 0.10
Data collection
DiffractometerRigaku AFC-7S
diffractometer
Absorption correctionψ-scan
(MSC/AFC Diffractometer Control Software; Molecular Structure Corporation, 1993)
Tmin, Tmax0.684, 0.875
No. of measured, independent and
observed [I > 2σ(I)] reflections
1996, 1715 (241), 1793
Rint0.056
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.119, 1.06
No. of reflections1956
No. of parameters197
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.25, 0.76
Absolute structureFlack (1983)
Absolute structure parameter0.00 (3)

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Diffractometer Control Software, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai & Pritzkow, 1995), PLATON98 (Spek, 1998).

Selected geometric parameters (Å, º) top
Fe—C101.785 (4)C1—C21.442 (5)
Fe—C91.792 (5)C1—C61.498 (5)
Fe—C111.798 (4)C2—C31.402 (6)
Fe—C32.049 (4)C3—C41.416 (6)
Fe—C22.061 (4)C4—C51.514 (5)
Fe—C12.069 (3)C5—C61.555 (5)
Fe—C42.108 (4)
C3—Fe—C239.91 (17)C3—C2—C1113.4 (3)
C3—Fe—C170.52 (15)C2—C3—C4114.9 (3)
C2—Fe—C140.86 (14)C3—C4—C5117.9 (4)
C3—Fe—C439.81 (17)C4—C5—C6110.3 (3)
C1—Fe—C476.02 (15)C1—C6—C5108.7 (3)
C2—C1—C6122.1 (3)
C6—C1—C2—C346.6 (5)C3—C4—C5—C652.4 (4)
C1—C2—C3—C42.8 (5)C2—C1—C6—C536.9 (4)
C2—C3—C4—C546.0 (5)C4—C5—C6—C110.6 (4)
 

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