Methyl 3 ferrocenyl­propanoate1

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m676

Structure Reports Online

ISSN 1600-5368

Methyl 3-ferrocenylpropanoate

Mario Cetina,a_Draginja

MrvosÏ-Sermek,b_{Marijana JukicÂ}c_and

Vladimir RapicÂc_*

a_{Faculty of Textile Technology, University of} Zagreb, Pierottijeva 6, HR-10000 Zagreb, Croatia,b_{Laboratory of General and Inorganic} Chemistry, Faculty of Science, University of Zagreb, Zvonimirova 8, HR-10000 Zagreb, Croatia, andc_{Laboratory of Organic Chemistry,} Faculty of Food Technology and Biotechnology, Pierottijeva 6, HR-10000 Zagreb, Croatia

Correspondence e-mail: [email protected]

Key indicators Single-crystal X-ray study T= 295 K

Mean(C±C) = 0.003 AÊ Rfactor = 0.036 wRfactor = 0.099

Data-to-parameter ratio = 20.9

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2002 International Union of Crystallography Printed in Great Britain ± all rights reserved

The title compound, [Fe(C5H5)(C9H11O2)], was prepared and

characterized by spectroscopic methods and crystal structure determination. The average values of the bond distances between the C atoms in the cyclopentadienyl rings are 1.422 (3) AÊ in the substituted and 1.404 (4) AÊ in the unsubstituted ring. The FeÐC bond distances range from 2.036 (2) to 2.061 (2) AÊ and the bond angles in both rings range from 107.1 (2) to 108.9 (2)_{. The cyclopentadienyl rings}

are almost parallel and deviate only slightly from the eclipsed conformation. The molecules are connected into dimers by very weak CÐH O intermolecular hydrogen bonds.

Comment

The study of ferrocene compounds has led to important developments in the ®elds of catalysis and biocatalysis (Patti & Nicolosi, 2000), polymers (Gonsalves & Chen, 1995) and bioorganometallic chemistry (Severin et al., 1998; Metzler-Nolte, 2001). Various functional groups on the cyclopenta-dienyl (Cp) rings in¯uence the electronic properties of ferro-cene derivatives and this leads to different applications of these complexes (Oberhoffet al., 1996). The present study of methyl 3-ferrocenylpropanoate, (I), forms part of wider research on differently substituted ferrocene compounds, their synthesis, stereochemistry and structural analysis (ZoricÂet al., 1999; Lapic & RapicÂ, 2000; BarisÏicÂet al., 2002; Cetinaet al., 2002; PavlovicÂet al., 2002).

The molecular structure of (I) is shown in Fig. 1. The distances between the C atoms in the Cp rings are greater in the substituted ring (C1±C5) than in the unsubstituted ring (C6±C10), with average values of 1.422 (3) and 1.404 (4) AÊ, respectively (Table 1). The FeÐC bond distances range from 2.036 (2) to 2.061 (2) AÊ. The longest FeÐC distance is FeÐ C1, as was generally observed in monosubstituted ferrocene derivatives with the isolated -electron system (Allen & Kennard, 1993). The values of the bond angles in the Cp rings range from 107.1 (2) to 108.9 (2) _{(Table 1). The bond}

distances in the ferrocenyl skeleton and the methylcarboxylate group are in agreement with those found in other ferrocenes having a methylcarboxylate group on one of the rings (Luoet

Received 10 September 2002 Accepted 17 October 2002 Online 25 October 2002

al., 1990; Podlaha et al., 1996; Hobi et al., 1997; Beck et al., 2001; Costaet al., 2001). The geometry of the title compound is also in a good agreement with the structure of 3-ferrocenyl-propanoic acid (Cetinaet al., 2002). In these two structures, a difference in the orientation of the Cp rings was observed; in the title compound they deviate only slightly from the eclipsed conformation. The values of the corresponding pseudo-torsion angles de®ned by joining two eclipsing Cp C atoms through the ring centroids (CÐCp1ÐCp2ÐC;Cp1andCp1are the Cp

ring centroids) are in the range 1.9 (2)±2.6 (2)_{. In the}

struc-ture of 3-ferrocenylpropanoic acid, the Cp rings are twisted from the eclipsed conformation by 8.3 (2) _{(average value).}

The Cp rings are almost parallel [dihedral angle 1.3 (1)_{] and}

the largest observed deviation of the C atoms from their mean planes is 0.001 (3) AÊ. Furthermore, the Fe atom is almost equidistant from the centroids of the Cp rings [FeÐCp1 =

1.651 (1) AÊ and FeÐCp2= 1.655 (1) AÊ] and the angle de®ned

by the ring centroids and the Fe atom deviates very slightly from 180_[Cp

1ÐFeÐCp2= 178.9 (1)].

Atom C1 of the ferrocenyl skeleton and atom C13 of the methoxycarbonyl group are antiperiplanar, as are atom C14 of the methyl group and atom C12 of the ferrocenylethyl skeleton. The values of the corresponding torsion angles C1Ð C11ÐC12ÐC13 and C14ÐO2ÐC13ÐC12 areÿ178.7 (2) and

ÿ178.8 (2)_{, respectively. The plane de®ned by the atoms C12,}

C13, O1 and O2 is more twisted with respect to the substituted Cp ring [dihedral angle 19.4 (1)_{], compared to the situation in}

3-ferrocenylpropanoic acid, where they are nearly coplanar. The same plane is also parallel with the shortest crystal-lographic axisb[dihedral angle 0.5 (1)_].

The molecules are connected by a very weak intermolecular hydrogen bond C6ÐH6 O1i _{[symmetry code: (i) ÿx, +y,} 1

2ÿz], forming dimers (Fig. 2). The D A and H A

distances are 3.433 (3) and 2.51 AÊ, respectively, and theDÐ H A angle is 170_{. A survey of the Cambridge Structural}

Database (Allen & Kennard, 1993) lists three structures of ferrocene derivatives with the same type of C(Cp)Ð H O( C) hydrogen-bonded dimers (Kaøuski et al., 1979; AbraÂnet al., 1999; Ansorgeet al., 2000).

Experimental

The title compound (Robertset al., 1967) was prepared by re¯uxing a methanolic solution of 3-ferrocenylpropanoic acid (Hauser & Lindsay, 1957; Cetinaet al., 2002) in the presence of BF3in diethyl

ether. After puri®cation on silica-gel plates (Merck, Kieselgel 60 HF254), using CH2Cl2as eluent, an 87% yield of orange crystals

was obtained [m.p. 310±311 K; literature m.p. 309±310 K (Robertset al., 1967)]. The single crystal used for analysis was obtained by slow evaporation from a cyclohexane solution at room temperature. IR (CH2Cl2,): 3099w(CÐH) ferrocene; 2924w(CÐH) aliphatic; 1732

(s, C O) cmÿ1_.1_{H NMR (CDCl}

3,, p.p.m.): 4.07 (d, 9H, ferrocene),

3.67 (s, 3H, OCH3), 2.65 (t, 2H, CH2CO), 2.54 (t, 2H, FcCH2).13C

NMR (CDCl3,, p.p.m.): 173.72 (C O), 87.23, 68.32, 67.70

(substi-tuted ferrocene ring), 67.18, 60.16 (unsubsti(substi-tuted ferrocene ring), 51.37 (OCH3), 35.22 (FcCH2), 24.58 (CH2). The melting point was

determined using a Buechi apparatus, The IR spectrum was recorded on a Bomen MB100 Mid FT±IR spectrophotometer and the1_{H and} 13_{C NMR spectra were recorded on a Varian Gemini 300}

spectro-meter, with tetramethylsilane as the internal standard.

Crystal data

[Fe(C5H5)(C9H11O2)]

Mr= 272.12 Monoclinic,C2=c a= 29.425 (9) AÊ b= 6.1454 (9) AÊ c= 13.739 (2) AÊ

= 96.38 (1) V= 2469.0 (9) AÊ3

Z= 8

Dx= 1.464 Mg mÿ3 MoKradiation Cell parameters from 28

re¯ections

= 6.2±13.3

= 1.21 mmÿ1

T= 295 (2) K Prism, orange 0.900.750.60 mm

Data collection

Philips PW1100 diffractometer updated by Stoe

!scans

Absorption correction: scan (Northet al., 1968) Tmin= 0.306,Tmax= 0.502

3235 measured re¯ections 3235 independent re¯ections 2526 re¯ections withI> 2(I)

Rint= 0.016

max= 28.9

h=ÿ40!39 k= 0!8 l= 0!18

4 standard re¯ections frequency: 120 min intensity decay: 2.4%

Re®nement

Re®nement onF2

R[F2_{> 2(F}2_{)] = 0.036}

wR(F2_{) = 0.099}

S= 1.07 3235 re¯ections 155 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0571P)2 + 0.5699P]

whereP= (Fo2+ 2Fc2)/3 (/)max= 0.001

max= 0.36 e AÊÿ3

min=ÿ0.22 e AÊÿ3

Extinction correction:SHELXL97 Extinction coef®cient: 0.0027 (4)

Acta Cryst.(2002). E58, m676±m678 Mario Cetinaet al. [Fe(C5H5)(C9H11O2)]

m677

metal-organic papers

Figure 2

Crystal-packing diagram of (I). Figure 1

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Table 1

Selected geometric parameters (AÊ,_). CÐC(Cp)(av.)subst. 1.421 (3) CÐC(Cp)(av.)unsubst. 1.404 (4)

O1ÐC13 1.197 (2)

O2ÐC13 1.338 (2)

O2ÐC14 1.441 (2)

C1ÐC11 1.505 (3)

C11ÐC12 1.510 (3)

C12ÐC13 1.500 (3)

C13ÐO2ÐC14 116.83 (17)

C2ÐC1ÐC5 107.09 (18)

C2ÐC1ÐC11 127.90 (19)

C5ÐC1ÐC11 124.97 (18)

C1ÐC2ÐC3 108.3 (2)

C4ÐC3ÐC2 107.94 (19)

C3ÐC4ÐC5 107.83 (19)

C1ÐC5ÐC4 108.87 (19)

C10ÐC6ÐC7 107.8 (2)

C6ÐC7ÐC8 107.7 (2)

C9ÐC8ÐC7 107.7 (2)

C10ÐC9ÐC8 108.3 (2)

C9ÐC10ÐC6 108.6 (2)

C1ÐC11ÐC12 113.53 (16)

C13ÐC12ÐC11 114.07 (16)

O1ÐC13ÐO2 123.16 (19)

O1ÐC13ÐC12 126.48 (18)

O2ÐC13ÐC12 110.35 (16)

All H atoms were included in calculated positions as riding atoms, withSHELXL97 (Sheldrick, 1997) defaults.

Data collection: STADI4 (Stoe & Cie, 1995); cell re®nement:

STADI4; data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics:WinGX(Farrugia, 1999); software used to prepare material for publication:SHELXL97.

References

AbraÂn, AÂ., CsaÂmpai, A., BoÈcskei, Zs. & SohaÂr, P. (1999).Tetrahedron,55, 5441±5448.

Allen, F. H. & Kennard, O. (1993).Chem. Des. Autom. News,8, 1, 31±37. Ansorge, M., Polborn, K. & MuÈller, T. J. J. (2000).Eur. J. Inorg. Chem.pp.

2003±2009.

BarisÏicÂ, L., RapicÂ, V. & KovacÏ, V. (2002).Croat. Chem. Acta,75, 199±210. Beck, W., Woisetschlager, O. E. & Mayer, P. (2001).Z. Kristallogr. New Cryst.

Struct.216, 403±404.

Cetina, M., Hergold-BrundicÂ, A., Nagl, A., JukicÂ, M. & RapicÂ, V. (2002).Struct. Chem.In the press.

Costa, M., Dalcanale, E., Dias, F. S., Graiff, C., Tiripicchio, A. & Bigliardi, L. (2001).J. Organomet. Chem.619, 179±193.

Farrugia, L. J. (1999).J. Appl. Cryst.32, 837±838.

Gonsalves, K. E. & Chen, X. (1995).Ferrocenes, edited by A. Togni and T. Hayashi, ch. 10, pp. 497±527. Weinheim: VCH.

Hauser, C. R. & Lindsay, J. K. (1957).J. Org. Chem.22, 1246±1247. Hobi, M., Ruppert, O., Gramlich, V. & Togni, A. (1997).Organometallics,16,

1384±1391.

Kaøuski, Z., Skrzypczak-Jankun, E. & Cygler, M. (1979). Acta Cryst.B35, 2699±2702.

LapicÂ, J. & RapicÂ, V. (2000).Croat. Chem. Acta,73, 755±771.

Luo, Y., Barton, R. J. & Robertson, B. E. (1990).Acta Cryst.C46, 1388±1391. Metzler-Nolte, N. (2001).Angew. Chem. Int. Ed.40, 1040±1043.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968).Acta Cryst.A24, 351± 359.

Oberhoff, M., Duda, L., Karl, J., Mohr, R., Erker, G., Frohlich, R. & Grehl, M. (1996).Organometallics,15, 4005±4011.

Patti, A. & Nicolosi, G. (2000).Tetrahedron Asymmetry,11, 815±822. PavlovicÂ, G., BarisÏicÂ, L., RapicÂ, V. & Leban, I. (2002).Acta Cryst.E58, m13±

m15.

Podlaha, J., SÆteÏpnicÏka, P., LudvõÂk, J. & CõÂsarÏovaÂ, I. (1996).Organometallics,15, 543±550.

Roberts, P. T., Little, W. F. & Bursey, M. M. (1967).J. Am. Chem. Soc.89, 6158± 6164.

Severin, K., Bergs, R. & Beck, W. (1998).Angew. Chem. Int. Ed.37, 1634±1654. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of

GoÈttingen, Germany.

Stoe & Cie (1995).Stadi4 andX-RED. Versions 1.05B. Stoe & Cie, Darmstadt, Germany.

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Acta Cryst. (2002). E58, m676–m678

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Acta Cryst. (2002). E58, m676–m678 [https://doi.org/10.1107/S1600536802019141]

Methyl 3-ferrocenylpropanoate

Mario Cetina, Draginja Mrvo

š

-Sermek, Marijana Juki

ć

and Vladimir Rapi

ć

Methyl 3-ferrocenylpropanoate

Crystal data [Fe(C5H5)(C9H11O2)]

Mr = 272.12

Monoclinic, C2/c a = 29.425 (9) Å b = 6.1454 (9) Å c = 13.739 (2) Å β = 96.38 (1)° V = 2469.0 (9) Å3

Z = 8

F(000) = 1136

Dx = 1.464 Mg m−3

Melting point: 310-311 K K Mo Kα radiation, λ = 0.71073 Å Cell parameters from 28 reflections θ = 6.2–13.3°

µ = 1.21 mm−1

T = 295 K Prismatic, orange 0.90 × 0.75 × 0.60 mm

Data collection Philips PW1100

diffractometer updated by Stoe Radiation source: fine-focus sealed tube Graphite monochromator

ω scans

Absorption correction: ψ scan (North et al., 1968)

Tmin = 0.306, Tmax = 0.502

3235 measured reflections

3235 independent reflections 2526 reflections with I > 2σ(I) Rint = 0.016

θmax = 28.9°, θmin = 2.8°

h = −40→39 k = 0→8 l = 0→18

4 standard reflections every 120 min intensity decay: 2.4%

Refinement Refinement on F2

Least-squares matrix: full R[F2 _{> 2σ(F}2_{)] = 0.036}

wR(F2_{) = 0.099}

S = 1.07 3235 reflections 155 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained w = 1/[σ2_(F

o2) + (0.0571P)2 + 0.5699P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.001

Δρmax = 0.36 e Å−3

Δρmin = −0.22 e Å−3

Extinction correction: SHELXL97, Fc*_{=kFc[1+0.001xFc}2_λ3_/sin(2θ)]-1/4

Extinction coefficient: 0.0027 (4)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2₎

x y z Uiso*/Ueq

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Acta Cryst. (2002). E58, m676–m678

O1 0.00024 (5) 0.4304 (3) 0.12230 (13) 0.0702 (5) O2 0.02558 (5) 0.7711 (2) 0.14370 (13) 0.0568 (4) C1 0.13518 (7) 0.1983 (3) 0.23815 (13) 0.0442 (4) C2 0.17506 (7) 0.3304 (4) 0.24491 (14) 0.0508 (4)

H2 0.1765 0.4733 0.2232 0.061*

C3 0.21260 (7) 0.2056 (4) 0.29097 (17) 0.0586 (5)

H3 0.2427 0.2531 0.3043 0.070*

C4 0.19594 (8) −0.0021 (4) 0.31245 (16) 0.0579 (5)

H4 0.2130 −0.1157 0.3425 0.069*

C5 0.14835 (8) −0.0068 (3) 0.28002 (15) 0.0538 (5)

H5 0.1290 −0.1248 0.2853 0.065*

C6 0.11346 (8) 0.3602 (5) 0.45857 (14) 0.0612 (6)

H6 0.0838 0.3948 0.4329 0.073*

C7 0.15144 (9) 0.4999 (4) 0.46429 (16) 0.0633 (6)

H7 0.1514 0.6437 0.4432 0.076*

C8 0.18986 (8) 0.3822 (5) 0.50805 (15) 0.0656 (6)

H8 0.2196 0.4348 0.5206 0.079*

C9 0.17499 (9) 0.1724 (5) 0.52890 (15) 0.0648 (6)

H9 0.1932 0.0613 0.5580 0.078*

C10 0.12835 (8) 0.1588 (5) 0.49862 (15) 0.0648 (6)

H10 0.1101 0.0368 0.5040 0.078*

C11 0.08782 (7) 0.2551 (3) 0.19239 (17) 0.0513 (5)

H11A 0.0657 0.1809 0.2279 0.062*

H11B 0.0840 0.2021 0.1255 0.062*

C12 0.07790 (6) 0.4962 (3) 0.19192 (14) 0.0456 (4)

H12A 0.0825 0.5496 0.2587 0.055*

H12B 0.0997 0.5698 0.1552 0.055*

C13 0.03046 (6) 0.5547 (3) 0.14850 (12) 0.0439 (4) C14 −0.01873 (7) 0.8526 (4) 0.10525 (17) 0.0616 (5)

H14A −0.0181 1.0088 0.1047 0.092*

H14B −0.0413 0.8035 0.1457 0.092*

H14C −0.0263 0.7998 0.0397 0.092*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

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Acta Cryst. (2002). E58, m676–m678

C10 0.0729 (15) 0.0760 (15) 0.0489 (11) −0.0108 (13) 0.0219 (10) 0.0058 (11) C11 0.0534 (11) 0.0455 (10) 0.0519 (10) −0.0009 (8) −0.0080 (9) −0.0098 (8) C12 0.0486 (10) 0.0438 (9) 0.0444 (9) −0.0050 (7) 0.0052 (8) −0.0012 (7) C13 0.0511 (10) 0.0428 (9) 0.0383 (8) −0.0031 (8) 0.0071 (7) 0.0004 (7) C14 0.0637 (13) 0.0537 (12) 0.0679 (13) 0.0091 (10) 0.0091 (10) 0.0101 (10)

Geometric parameters (Å, º)

C—C(Cp)(av.)subst. 1.421 (3) C4—C5 1.422 (3) C—C(Cp)(av.)unsubst. 1.404 (4) C4—H4 0.9300

Fe—C10 2.036 (2) C5—H5 0.9300

Fe—C6 2.038 (2) C6—C10 1.404 (4)

Fe—C4 2.039 (2) C6—C7 1.405 (4)

Fe—C3 2.041 (2) C6—H6 0.9300

Fe—C5 2.0417 (19) C7—C8 1.418 (3)

Fe—C7 2.043 (2) C7—H7 0.9300

Fe—C9 2.044 (2) C8—C9 1.401 (4)

Fe—C8 2.045 (2) C8—H8 0.9300

Fe—C2 2.0492 (19) C9—C10 1.392 (3)

Fe—C1 2.0609 (18) C9—H9 0.9300

O1—C13 1.197 (2) C10—H10 0.9300

O2—C13 1.338 (2) C11—C12 1.510 (3)

O2—C14 1.441 (2) C11—H11A 0.9700

C1—C2 1.422 (3) C11—H11B 0.9700

C1—C5 1.421 (3) C12—C13 1.500 (3)

C1—C11 1.505 (3) C12—H12A 0.9700

C2—C3 1.433 (3) C12—H12B 0.9700

C2—H2 0.9300 C14—H14A 0.9600

C3—C4 1.410 (3) C14—H14B 0.9600

C3—H3 0.9300 C14—H14C 0.9600

C10—Fe—C6 40.33 (11) C3—C4—C5 107.83 (19)

C10—Fe—C4 121.20 (11) C3—C4—Fe 69.84 (12)

C6—Fe—C4 156.93 (11) C5—C4—Fe 69.71 (11)

C10—Fe—C3 156.64 (11) C3—C4—H4 126.1

C6—Fe—C3 161.56 (10) C5—C4—H4 126.1

C4—Fe—C3 40.43 (10) Fe—C4—H4 125.9

C10—Fe—C5 107.36 (10) C1—C5—C4 108.87 (19)

C6—Fe—C5 121.88 (10) C1—C5—Fe 70.46 (11)

C4—Fe—C5 40.78 (8) C4—C5—Fe 69.52 (11)

C3—Fe—C5 68.19 (10) C1—C5—H5 125.6

C10—Fe—C7 67.61 (11) C4—C5—H5 125.6

C6—Fe—C7 40.27 (10) Fe—C5—H5 126.0

C4—Fe—C7 160.62 (10) C10—C6—C7 107.8 (2)

C3—Fe—C7 125.12 (10) C10—C6—Fe 69.76 (12)

C5—Fe—C7 157.79 (10) C7—C6—Fe 70.04 (12)

C10—Fe—C9 39.88 (9) C10—C6—H6 126.1

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Acta Cryst. (2002). E58, m676–m678

C4—Fe—C9 107.05 (10) Fe—C6—H6 125.7

C3—Fe—C9 121.95 (10) C6—C7—C8 107.7 (2)

C5—Fe—C9 123.27 (10) C6—C7—Fe 69.69 (12)

C7—Fe—C9 67.70 (10) C8—C7—Fe 69.78 (12)

C10—Fe—C8 67.38 (10) C6—C7—H7 126.2

C6—Fe—C8 67.87 (10) C8—C7—H7 126.2

C4—Fe—C8 123.46 (10) Fe—C7—H7 125.9

C3—Fe—C8 108.29 (10) C9—C8—C7 107.7 (2)

C5—Fe—C8 159.52 (10) C9—C8—Fe 69.92 (12)

C7—Fe—C8 40.60 (10) C7—C8—Fe 69.62 (11)

C9—Fe—C8 40.08 (11) C9—C8—H8 126.2

C10—Fe—C2 160.61 (9) C7—C8—H8 126.2

C6—Fe—C2 124.80 (9) Fe—C8—H8 125.9

C4—Fe—C2 68.44 (9) C10—C9—C8 108.3 (2)

C3—Fe—C2 41.02 (9) C10—C9—Fe 69.76 (12)

C5—Fe—C2 67.97 (9) C8—C9—Fe 69.99 (12)

C7—Fe—C2 109.15 (9) C10—C9—H9 125.8

C9—Fe—C2 158.45 (10) C8—C9—H9 125.8

C8—Fe—C2 123.54 (10) Fe—C9—H9 126.0

C10—Fe—C1 123.83 (9) C9—C10—C6 108.6 (2)

C6—Fe—C1 108.02 (8) C9—C10—Fe 70.36 (13)

C4—Fe—C1 68.68 (8) C6—C10—Fe 69.91 (11)

C3—Fe—C1 68.66 (9) C9—C10—H10 125.7

C5—Fe—C1 40.54 (8) C6—C10—H10 125.7

C7—Fe—C1 122.85 (9) Fe—C10—H10 125.6

C9—Fe—C1 159.48 (11) C1—C11—C12 113.53 (16)

C8—Fe—C1 158.87 (10) C1—C11—H11A 108.9

C2—Fe—C1 40.47 (8) C12—C11—H11A 108.9

C13—O2—C14 116.83 (17) C1—C11—H11B 108.9

C2—C1—C5 107.09 (18) C12—C11—H11B 108.9

C2—C1—C11 127.90 (19) H11A—C11—H11B 107.7 C5—C1—C11 124.97 (18) C13—C12—C11 114.07 (16)

C2—C1—Fe 69.32 (10) C13—C12—H12A 108.7

C5—C1—Fe 69.00 (11) C11—C12—H12A 108.7

C11—C1—Fe 128.53 (14) C13—C12—H12B 108.7

C1—C2—C3 108.3 (2) C11—C12—H12B 108.7

C1—C2—Fe 70.21 (11) H12A—C12—H12B 107.6

C3—C2—Fe 69.17 (12) O1—C13—O2 123.16 (19)

C1—C2—H2 125.9 O1—C13—C12 126.48 (18)

C3—C2—H2 125.9 O2—C13—C12 110.35 (16)

Fe—C2—H2 126.3 O2—C14—H14A 109.5

C4—C3—C2 107.94 (19) O2—C14—H14B 109.5

C4—C3—Fe 69.73 (12) H14A—C14—H14B 109.5

C2—C3—Fe 69.81 (11) O2—C14—H14C 109.5

C4—C3—H3 126.0 H14A—C14—H14C 109.5

C2—C3—H3 126.0 H14B—C14—H14C 109.5

supporting information

sup-5

Acta Cryst. (2002). E58, m676–m678

supporting information

sup-6

Acta Cryst. (2002). E58, m676–m678

supporting information

sup-7

Acta Cryst. (2002). E58, m676–m678