2-Propenyl 4-ferrocenyl-4-oxobutanoate

Giraldés, J.; McLaughlin, M.L.; Fronczek, F.R.

doi:10.1107/S1600536801014659

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2-Propenyl 4-ferrocenyl-4-oxobutanoate

J. Giraldés, M. L. McLaughlin and F. R. Fronczek

The title compound, C₁₇H₁₈FeO₃ or [Fe(C₅H₅)(C₁₂H₁₃O₃)], has the cyclopentadienyl rings essentially eclipsed and nearly parallel, forming a 2.5 (2)° dihedral angle. The Fe atom lies 1.6388 (8) Å out of the plane of the substituted ring and 1.6472 (9) Å out of the unsubstituted ring plane. The torsion angle about the central C-C bond of the 4-oxobutanoate group is -79.7 (2)°, and the O-C-C=CH₂ torsion angle is 131.0 (2)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801014659/om6053sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801014659/om6053Isup2.hkl Contains datablock I

CCDC reference: 175323

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R factor = 0.039
wR factor = 0.091
Data-to-parameter ratio = 23.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           31.90
         From the CIF: _reflns_number_total               4409
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         4942
         Completeness (_total/calc)             89.21%
          Alert B: < 90% complete (theta max?)

Author response: We were not able to measure the 10 k l and 11 k l data at very high angle. The data are 94% complete to theta=30 degrees. Including the 30.02sigma(I). We feel that they are worth keeping in the refinement, as they increase the data:parameter and precision slightly and do not appear to bias the results.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           31.90
         From the CIF: _reflns_number_total               4409
         From the CIF: _diffrn_reflns_limit_ max hkl    9.   16.   49.
         From the CIF: _diffrn_reflns_limit_ min hkl   -9.  -16.  -48.
         TEST1: Expected hkl limits for theta max
         Calculated maximum hkl   11.   16.   50.
         Calculated minimum hkl  -11.  -16.  -50.
          ALERT: Expected hkl max differ from CIF values


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

Comment top

With the rapid development of solid-phase synthesis, there is a great deal of interest in developing new solid-phase linkers. We report here the synthesis of 2-propenyl 4-ferrocenyl-4-oxobutanoate, (I), a ferrocenylamide-based linker precursor. This allyl ester ferrocene derivative was prepared to be used as a linker in solid-phase peptide synthesis (SPPS). The mild conditions used to remove allyl groups are compatible with classical Fmoc/tBu methods (Kates et al., 1993; Trzeciak & Bannwarth, 1992; Merrifield, 1995). The allyl ester serves as a protecting group and is easily cleaved without disrupting the other protecting groups by using palladium catalysts under neutral conditions. Upon reductive amination of the ketone and peptide synthesis, the ferrocenyl–amine bond will be easily cleaved (Blanchet et al., 2000) making the ferrocenyl cation which is more stable than the traditional benzylic cations used in SPPS (Watts, 1979). The crystal structure of the title compound was determined to prove its successful synthesis.

The cyclopentadienyl (Cp) rings are essentially eclipsed, forming C—Centroid—Centroid—C torsion angles which average 3.3 (2)°. The rings are nearly parallel, forming a 2.5 (2)° dihedral angle. The Fe atom lies 1.6388 (8) Å out of Cp ring C1–C5 and 1.6472 (9) Å out of Cp ring C13–C17. These are typical geometric features [see, for example, Gallagher et al. (1997)]. The carbonyl C6═O1 is twisted by 11.2 (3)° out of the Cp ring to which it is attached. The conformation of the remainder of the substituent on Cp ring C1—C5 (Table 1) is such that the ester carbonyl O3 atom forms an intramolecular C—H···O hydrogen bond with the unsubstituted Cp ring. The C13···O3 distance is 3.289 (2) Å, the H···O distance is 2.39 Å, and the angle about H is 159°.

Experimental top

To a solution of 4-ferrocenyl-4-oxobutanoic acid (0.95 g, 3.3 mmol) in 20 ml acetone, K₂CO₃ (1.58 g,12 mmol) and allyl bromide (2.66 g, 22 mmol) were added under argon. The mixture was refluxed at 373 K overnight. After cooling, HCl (10 ml, 4 N) was added to the mixture and extracted with (3 x 20 ml) dichloromethane. The organic layers were combined and dried over sodium sulfate and evaporated in vacuo. The product was purified by column chromatography (2:1, hexane–ethyl acetate). Diffraction-quality crystals were grown by dissolving the solid material in a hot ethanol solution, followed by slow evaporation of the solvent. Yield 0.91 g (85%). MS, m/e (M⁺): 326.

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The atom-umbering scheme and ellipsoids at the 50% probability level for (I).

2-Propenyl 4-ferrocenyl-4-oxobutanoate top

Crystal data top

[Fe(C₅H₅)(C₁₂H₁₃O₃)]	D_x = 1.508 Mg m⁻³
M_r = 326.16	Melting point: 313 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 7.7561 (1) Å	Cell parameters from 4495 reflections
b = 10.8931 (2) Å	θ = 2.5–31.9°
c = 34.0120 (6) Å	µ = 1.06 mm⁻¹
V = 2873.60 (8) Å³	T = 120 K
Z = 8	Plate, orange
F(000) = 1360	0.32 × 0.20 × 0.05 mm

Data collection top

KappaCCD diffractometer (with Oxford Cryosystems Cryostream cooler)	4409 independent reflections
Radiation source: fine-focus sealed tube	3031 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans with κ offsets	θ_max = 31.9°, θ_min = 2.9°
Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997)	h = −9→9
T_min = 0.844, T_max = 0.949	k = −16→16
19653 measured reflections	l = −48→49

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0325P)² + 1.0286P] where P = (F_o² + 2F_c²)/3
4409 reflections	(Δ/σ)_max = 0.003
190 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₂H₁₃O₃)]	V = 2873.60 (8) Å³
M_r = 326.16	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.7561 (1) Å	µ = 1.06 mm⁻¹
b = 10.8931 (2) Å	T = 120 K
c = 34.0120 (6) Å	0.32 × 0.20 × 0.05 mm

Data collection top

KappaCCD diffractometer (with Oxford Cryosystems Cryostream cooler)	4409 independent reflections
Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997)	3031 reflections with I > 2σ(I)
T_min = 0.844, T_max = 0.949	R_int = 0.038
19653 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.01	Δρ_max = 0.33 e Å⁻³
4409 reflections	Δρ_min = −0.58 e Å⁻³
190 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Fe1	0.45489 (4)	0.14941 (2)	0.568335 (7)	0.01796 (8)
O1	0.54470 (18)	0.15132 (11)	0.67736 (4)	0.0251 (3)
O2	0.50402 (18)	0.49114 (12)	0.71968 (4)	0.0254 (3)
O3	0.4741 (2)	0.48972 (13)	0.65390 (4)	0.0338 (4)
C1	0.6237 (2)	0.10907 (15)	0.61192 (5)	0.0181 (4)
C2	0.7139 (3)	0.13360 (15)	0.57593 (5)	0.0212 (4)
H2	0.7967	0.1966	0.5719	0.025*
C3	0.6580 (3)	0.04753 (16)	0.54745 (5)	0.0232 (4)
H3	0.6974	0.0426	0.5211	0.028*
C4	0.5327 (3)	−0.03033 (15)	0.56508 (5)	0.0208 (4)
H4	0.4740	−0.0959	0.5524	0.025*
C5	0.5103 (2)	0.00670 (15)	0.60477 (5)	0.0196 (4)
H5	0.4341	−0.0295	0.6233	0.024*
C6	0.6245 (2)	0.18366 (15)	0.64817 (5)	0.0193 (4)
C7	0.7320 (3)	0.29945 (15)	0.64771 (5)	0.0213 (4)
H7A	0.7013	0.3480	0.6241	0.026*
H7B	0.8551	0.2764	0.6454	0.026*
C8	0.7092 (3)	0.37977 (16)	0.68389 (5)	0.0226 (4)
H8A	0.7056	0.3265	0.7075	0.027*
H8B	0.8109	0.4341	0.6864	0.027*
C9	0.5496 (3)	0.45745 (15)	0.68308 (5)	0.0217 (4)
C10	0.3607 (3)	0.57710 (16)	0.72340 (6)	0.0277 (4)
H10A	0.2994	0.5618	0.7485	0.033*
H10B	0.2782	0.5636	0.7016	0.033*
C11	0.4224 (3)	0.70637 (16)	0.72243 (6)	0.0249 (4)
H11	0.5161	0.7285	0.7390	0.030*
C12	0.3547 (3)	0.79118 (18)	0.70000 (6)	0.0327 (5)
H12A	0.2609	0.7715	0.6832	0.039*
H12B	0.3992	0.8724	0.7006	0.039*
C13	0.3238 (3)	0.30135 (17)	0.58654 (6)	0.0307 (5)
H13	0.3439	0.3460	0.6101	0.037*
C14	0.4030 (3)	0.32361 (17)	0.54977 (7)	0.0325 (5)
H14	0.4857	0.3857	0.5443	0.039*
C15	0.3378 (3)	0.23740 (18)	0.52256 (6)	0.0334 (5)
H15	0.3688	0.2313	0.4956	0.040*
C16	0.2181 (3)	0.16173 (17)	0.54248 (6)	0.0310 (5)
H16	0.1546	0.0960	0.5312	0.037*
C17	0.2097 (3)	0.20114 (19)	0.58213 (6)	0.0299 (5)
H17	0.1397	0.1664	0.6022	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.01903 (17)	0.01857 (11)	0.01628 (13)	0.00217 (10)	−0.00046 (11)	0.00120 (9)
O1	0.0276 (9)	0.0277 (6)	0.0198 (6)	−0.0050 (6)	0.0036 (6)	0.0010 (5)
O2	0.0268 (9)	0.0261 (6)	0.0234 (7)	0.0046 (6)	0.0025 (6)	−0.0003 (5)
O3	0.0407 (10)	0.0358 (7)	0.0247 (8)	0.0118 (7)	−0.0091 (7)	−0.0033 (6)
C1	0.0167 (10)	0.0180 (7)	0.0196 (9)	0.0038 (7)	−0.0007 (8)	0.0023 (6)
C2	0.0166 (11)	0.0222 (8)	0.0247 (10)	0.0012 (7)	0.0045 (8)	0.0008 (6)
C3	0.0246 (12)	0.0237 (8)	0.0214 (9)	0.0040 (8)	0.0033 (8)	−0.0017 (7)
C4	0.0221 (11)	0.0175 (7)	0.0229 (9)	0.0028 (7)	−0.0021 (8)	−0.0019 (6)
C5	0.0205 (11)	0.0179 (7)	0.0204 (9)	0.0004 (7)	−0.0010 (7)	0.0041 (6)
C6	0.0162 (10)	0.0214 (7)	0.0202 (9)	0.0030 (7)	−0.0004 (8)	0.0030 (6)
C7	0.0194 (11)	0.0229 (8)	0.0216 (9)	−0.0017 (7)	0.0023 (8)	−0.0006 (7)
C8	0.0234 (12)	0.0222 (8)	0.0221 (9)	−0.0012 (7)	−0.0020 (8)	−0.0012 (6)
C9	0.0232 (11)	0.0190 (7)	0.0228 (9)	−0.0030 (7)	0.0001 (8)	−0.0017 (6)
C10	0.0235 (12)	0.0284 (9)	0.0314 (11)	0.0023 (8)	0.0072 (9)	0.0000 (7)
C11	0.0221 (12)	0.0285 (9)	0.0242 (10)	0.0010 (8)	0.0021 (8)	−0.0073 (7)
C12	0.0271 (12)	0.0312 (10)	0.0400 (12)	0.0025 (9)	0.0032 (10)	−0.0005 (8)
C13	0.0308 (13)	0.0298 (9)	0.0315 (11)	0.0145 (9)	−0.0086 (10)	−0.0091 (8)
C14	0.0317 (13)	0.0212 (8)	0.0445 (13)	0.0059 (8)	−0.0012 (11)	0.0073 (8)
C15	0.0431 (15)	0.0366 (10)	0.0206 (10)	0.0175 (10)	−0.0029 (10)	0.0042 (8)
C16	0.0270 (13)	0.0287 (9)	0.0372 (11)	0.0052 (9)	−0.0147 (10)	−0.0044 (8)
C17	0.0191 (12)	0.0380 (10)	0.0327 (11)	0.0110 (9)	0.0005 (9)	0.0054 (8)

Geometric parameters (Å, º) top

Fe1—C1	2.0260 (18)	C6—C7	1.512 (2)
Fe1—C2	2.033 (2)	C7—C8	1.520 (2)
Fe1—C5	2.0339 (17)	C7—H7A	0.9900
Fe1—C17	2.038 (2)	C7—H7B	0.9900
Fe1—C13	2.0386 (18)	C8—C9	1.500 (3)
Fe1—C14	2.0399 (18)	C8—H8A	0.9900
Fe1—C16	2.040 (2)	C8—H8B	0.9900
Fe1—C15	2.0415 (19)	C10—C11	1.488 (3)
Fe1—C4	2.0517 (16)	C10—H10A	0.9900
Fe1—C3	2.0534 (19)	C10—H10B	0.9900
O1—C6	1.222 (2)	C11—C12	1.308 (3)
O2—C9	1.345 (2)	C11—H11	0.9500
O2—C10	1.459 (2)	C12—H12A	0.9500
O3—C9	1.205 (2)	C12—H12B	0.9500
C1—C2	1.435 (2)	C13—C17	1.414 (3)
C1—C5	1.441 (3)	C13—C14	1.414 (3)
C1—C6	1.477 (2)	C13—H13	0.9500
C2—C3	1.416 (2)	C14—C15	1.412 (3)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.422 (3)	C15—C16	1.414 (3)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.420 (2)	C16—C17	1.417 (3)
C4—H4	0.9500	C16—H16	0.9500
C5—H5	0.9500	C17—H17	0.9500

C1—Fe1—C2	41.41 (7)	C3—C4—H4	125.8
C1—Fe1—C5	41.58 (7)	Fe1—C4—H4	127.0
C2—Fe1—C5	69.46 (7)	C4—C5—C1	107.79 (16)
C1—Fe1—C17	119.64 (8)	C4—C5—Fe1	70.35 (10)
C2—Fe1—C17	156.39 (8)	C1—C5—Fe1	68.92 (10)
C5—Fe1—C17	105.55 (8)	C4—C5—H5	126.1
C1—Fe1—C13	106.02 (8)	C1—C5—H5	126.1
C2—Fe1—C13	121.53 (8)	Fe1—C5—H5	126.2
C5—Fe1—C13	122.73 (8)	O1—C6—C1	121.18 (16)
C17—Fe1—C13	40.57 (8)	O1—C6—C7	121.89 (16)
C1—Fe1—C14	123.75 (8)	C1—C6—C7	116.92 (15)
C2—Fe1—C14	108.24 (8)	C6—C7—C8	114.06 (15)
C5—Fe1—C14	160.26 (8)	C6—C7—H7A	108.7
C17—Fe1—C14	68.29 (9)	C8—C7—H7A	108.7
C13—Fe1—C14	40.58 (9)	C6—C7—H7B	108.7
C1—Fe1—C16	155.67 (9)	C8—C7—H7B	108.7
C2—Fe1—C16	161.76 (8)	H7A—C7—H7B	107.6
C5—Fe1—C16	120.19 (8)	C9—C8—C7	113.93 (16)
C17—Fe1—C16	40.64 (8)	C9—C8—H8A	108.8
C13—Fe1—C16	68.21 (8)	C7—C8—H8A	108.8
C14—Fe1—C16	68.16 (9)	C9—C8—H8B	108.8
C1—Fe1—C15	161.32 (8)	C7—C8—H8B	108.8
C2—Fe1—C15	125.19 (9)	H8A—C8—H8B	107.7
C5—Fe1—C15	156.56 (8)	O3—C9—O2	123.69 (18)
C17—Fe1—C15	68.32 (9)	O3—C9—C8	125.53 (18)
C13—Fe1—C15	68.20 (8)	O2—C9—C8	110.73 (16)
C14—Fe1—C15	40.49 (9)	O2—C10—C11	111.11 (17)
C16—Fe1—C15	40.54 (9)	O2—C10—H10A	109.4
C1—Fe1—C4	69.05 (7)	C11—C10—H10A	109.4
C2—Fe1—C4	68.62 (7)	O2—C10—H10B	109.4
C5—Fe1—C4	40.66 (7)	C11—C10—H10B	109.4
C17—Fe1—C4	123.41 (8)	H10A—C10—H10B	108.0
C13—Fe1—C4	159.68 (9)	C12—C11—C10	123.5 (2)
C14—Fe1—C4	158.28 (8)	C12—C11—H11	118.3
C16—Fe1—C4	107.71 (8)	C10—C11—H11	118.3
C15—Fe1—C4	122.53 (8)	C11—C12—H12A	120.0
C1—Fe1—C3	68.91 (7)	C11—C12—H12B	120.0
C2—Fe1—C3	40.55 (7)	H12A—C12—H12B	120.0
C5—Fe1—C3	68.64 (7)	C17—C13—C14	108.09 (18)
C17—Fe1—C3	160.85 (8)	C17—C13—Fe1	69.70 (11)
C13—Fe1—C3	157.86 (9)	C14—C13—Fe1	69.76 (11)
C14—Fe1—C3	123.16 (8)	C17—C13—H13	126.0
C16—Fe1—C3	125.22 (8)	C14—C13—H13	126.0
C15—Fe1—C3	109.34 (8)	Fe1—C13—H13	126.2
C4—Fe1—C3	40.54 (7)	C15—C14—C13	108.06 (19)
C9—O2—C10	117.11 (15)	C15—C14—Fe1	69.82 (11)
C2—C1—C5	107.32 (15)	C13—C14—Fe1	69.66 (11)
C2—C1—C6	127.43 (16)	C15—C14—H14	126.0
C5—C1—C6	124.70 (17)	C13—C14—H14	126.0
C2—C1—Fe1	69.54 (11)	Fe1—C14—H14	126.1
C5—C1—Fe1	69.50 (10)	C14—C15—C16	107.97 (19)
C6—C1—Fe1	119.63 (12)	C14—C15—Fe1	69.69 (11)
C3—C2—C1	108.10 (16)	C16—C15—Fe1	69.68 (11)
C3—C2—Fe1	70.51 (12)	C14—C15—H15	126.0
C1—C2—Fe1	69.04 (11)	C16—C15—H15	126.0
C3—C2—H2	125.9	Fe1—C15—H15	126.2
C1—C2—H2	125.9	C15—C16—C17	108.06 (18)
Fe1—C2—H2	126.1	C15—C16—Fe1	69.78 (12)
C2—C3—C4	108.41 (16)	C17—C16—Fe1	69.60 (12)
C2—C3—Fe1	68.94 (11)	C15—C16—H16	126.0
C4—C3—Fe1	69.67 (11)	C17—C16—H16	126.0
C2—C3—H3	125.8	Fe1—C16—H16	126.2
C4—C3—H3	125.8	C13—C17—C16	107.83 (19)
Fe1—C3—H3	127.2	C13—C17—Fe1	69.73 (12)
C5—C4—C3	108.37 (16)	C16—C17—Fe1	69.75 (12)
C5—C4—Fe1	68.99 (9)	C13—C17—H17	126.1
C3—C4—Fe1	69.79 (10)	C16—C17—H17	126.1
C5—C4—H4	125.8	Fe1—C17—H17	126.0

C5—Fe1—C1—C2	118.61 (14)	C5—C1—C6—O1	11.2 (3)
C17—Fe1—C1—C2	−161.56 (10)	Fe1—C1—C6—O1	95.69 (18)
C13—Fe1—C1—C2	−119.79 (11)	C2—C1—C6—C7	0.1 (3)
C14—Fe1—C1—C2	−79.13 (13)	C5—C1—C6—C7	−170.34 (16)
C16—Fe1—C1—C2	167.80 (16)	Fe1—C1—C6—C7	−85.86 (19)
C15—Fe1—C1—C2	−50.7 (3)	O1—C6—C7—C8	−8.9 (3)
C4—Fe1—C1—C2	81.02 (11)	C1—C6—C7—C8	172.68 (16)
C3—Fe1—C1—C2	37.44 (10)	C6—C7—C8—C9	−79.7 (2)
C2—Fe1—C1—C5	−118.61 (14)	C10—O2—C9—O3	−3.6 (3)
C17—Fe1—C1—C5	79.83 (13)	C10—O2—C9—C8	174.14 (15)
C13—Fe1—C1—C5	121.60 (12)	C7—C8—C9—O3	−24.3 (3)
C14—Fe1—C1—C5	162.27 (12)	C7—C8—C9—O2	158.09 (15)
C16—Fe1—C1—C5	49.2 (2)	C9—O2—C10—C11	−89.2 (2)
C15—Fe1—C1—C5	−169.3 (2)	O2—C10—C11—C12	131.0 (2)
C4—Fe1—C1—C5	−37.59 (11)	C1—Fe1—C13—C17	−117.11 (12)
C3—Fe1—C1—C5	−81.16 (11)	C2—Fe1—C13—C17	−159.45 (12)
C2—Fe1—C1—C6	122.28 (18)	C5—Fe1—C13—C17	−74.89 (14)
C5—Fe1—C1—C6	−119.11 (19)	C14—Fe1—C13—C17	119.29 (18)
C17—Fe1—C1—C6	−39.28 (17)	C16—Fe1—C13—C17	37.87 (12)
C13—Fe1—C1—C6	2.49 (16)	C15—Fe1—C13—C17	81.68 (13)
C14—Fe1—C1—C6	43.16 (18)	C4—Fe1—C13—C17	−44.3 (3)
C16—Fe1—C1—C6	−69.9 (2)	C3—Fe1—C13—C17	169.59 (18)
C15—Fe1—C1—C6	71.6 (3)	C1—Fe1—C13—C14	123.60 (13)
C4—Fe1—C1—C6	−156.70 (16)	C2—Fe1—C13—C14	81.27 (14)
C3—Fe1—C1—C6	159.73 (16)	C5—Fe1—C13—C14	165.82 (13)
C5—C1—C2—C3	−0.5 (2)	C17—Fe1—C13—C14	−119.29 (18)
C6—C1—C2—C3	−172.20 (18)	C16—Fe1—C13—C14	−81.42 (14)
Fe1—C1—C2—C3	−59.93 (13)	C15—Fe1—C13—C14	−37.60 (14)
C5—C1—C2—Fe1	59.48 (12)	C4—Fe1—C13—C14	−163.6 (2)
C6—C1—C2—Fe1	−112.27 (19)	C3—Fe1—C13—C14	50.3 (3)
C1—Fe1—C2—C3	119.24 (14)	C17—C13—C14—C15	0.1 (2)
C5—Fe1—C2—C3	80.76 (11)	Fe1—C13—C14—C15	59.47 (14)
C17—Fe1—C2—C3	162.59 (18)	C17—C13—C14—Fe1	−59.38 (13)
C13—Fe1—C2—C3	−162.65 (11)	C1—Fe1—C14—C15	166.41 (13)
C14—Fe1—C2—C3	−120.04 (12)	C2—Fe1—C14—C15	123.26 (14)
C16—Fe1—C2—C3	−44.6 (3)	C5—Fe1—C14—C15	−156.8 (2)
C15—Fe1—C2—C3	−78.41 (13)	C17—Fe1—C14—C15	−81.61 (15)
C4—Fe1—C2—C3	37.09 (11)	C13—Fe1—C14—C15	−119.2 (2)
C5—Fe1—C2—C1	−38.48 (10)	C16—Fe1—C14—C15	−37.69 (13)
C17—Fe1—C2—C1	43.4 (2)	C4—Fe1—C14—C15	45.4 (3)
C13—Fe1—C2—C1	78.11 (12)	C3—Fe1—C14—C15	81.02 (15)
C14—Fe1—C2—C1	120.72 (11)	C1—Fe1—C14—C13	−74.34 (15)
C16—Fe1—C2—C1	−163.9 (2)	C2—Fe1—C14—C13	−117.49 (13)
C15—Fe1—C2—C1	162.35 (10)	C5—Fe1—C14—C13	−37.6 (3)
C4—Fe1—C2—C1	−82.15 (10)	C17—Fe1—C14—C13	37.63 (13)
C3—Fe1—C2—C1	−119.24 (14)	C16—Fe1—C14—C13	81.56 (14)
C1—C2—C3—C4	0.4 (2)	C15—Fe1—C14—C13	119.2 (2)
Fe1—C2—C3—C4	−58.63 (13)	C4—Fe1—C14—C13	164.6 (2)
C1—C2—C3—Fe1	59.01 (13)	C3—Fe1—C14—C13	−159.73 (12)
C1—Fe1—C3—C2	−38.21 (10)	C13—C14—C15—C16	0.0 (2)
C5—Fe1—C3—C2	−82.98 (11)	Fe1—C14—C15—C16	59.39 (14)
C17—Fe1—C3—C2	−158.6 (2)	C13—C14—C15—Fe1	−59.38 (14)
C13—Fe1—C3—C2	42.4 (2)	C1—Fe1—C15—C14	−37.6 (3)
C14—Fe1—C3—C2	79.13 (13)	C2—Fe1—C15—C14	−76.35 (15)
C16—Fe1—C3—C2	164.39 (11)	C5—Fe1—C15—C14	160.48 (19)
C15—Fe1—C3—C2	121.95 (12)	C17—Fe1—C15—C14	81.51 (15)
C4—Fe1—C3—C2	−120.24 (15)	C13—Fe1—C15—C14	37.68 (14)
C1—Fe1—C3—C4	82.03 (12)	C16—Fe1—C15—C14	119.19 (18)
C2—Fe1—C3—C4	120.24 (15)	C4—Fe1—C15—C14	−161.79 (13)
C5—Fe1—C3—C4	37.26 (11)	C3—Fe1—C15—C14	−118.79 (14)
C17—Fe1—C3—C4	−38.3 (3)	C1—Fe1—C15—C16	−156.8 (2)
C13—Fe1—C3—C4	162.66 (19)	C2—Fe1—C15—C16	164.46 (11)
C14—Fe1—C3—C4	−160.62 (12)	C5—Fe1—C15—C16	41.3 (3)
C16—Fe1—C3—C4	−75.37 (14)	C17—Fe1—C15—C16	−37.68 (12)
C15—Fe1—C3—C4	−117.80 (12)	C13—Fe1—C15—C16	−81.51 (13)
C2—C3—C4—C5	−0.2 (2)	C14—Fe1—C15—C16	−119.19 (18)
Fe1—C3—C4—C5	−58.35 (12)	C4—Fe1—C15—C16	79.02 (14)
C2—C3—C4—Fe1	58.18 (13)	C3—Fe1—C15—C16	122.02 (12)
C1—Fe1—C4—C5	38.42 (11)	C14—C15—C16—C17	−0.1 (2)
C2—Fe1—C4—C5	82.98 (12)	Fe1—C15—C16—C17	59.28 (14)
C17—Fe1—C4—C5	−74.04 (14)	C14—C15—C16—Fe1	−59.40 (14)
C13—Fe1—C4—C5	−41.1 (3)	C1—Fe1—C16—C15	162.14 (16)
C14—Fe1—C4—C5	168.7 (2)	C2—Fe1—C16—C15	−44.4 (3)
C16—Fe1—C4—C5	−116.00 (12)	C5—Fe1—C16—C15	−162.32 (11)
C15—Fe1—C4—C5	−158.06 (12)	C17—Fe1—C16—C15	119.30 (16)
C3—Fe1—C4—C5	120.07 (16)	C13—Fe1—C16—C15	81.50 (13)
C1—Fe1—C4—C3	−81.66 (12)	C14—Fe1—C16—C15	37.64 (12)
C2—Fe1—C4—C3	−37.10 (11)	C4—Fe1—C16—C15	−119.67 (12)
C5—Fe1—C4—C3	−120.07 (16)	C3—Fe1—C16—C15	−78.35 (13)
C17—Fe1—C4—C3	165.89 (11)	C1—Fe1—C16—C17	42.8 (2)
C13—Fe1—C4—C3	−161.1 (2)	C2—Fe1—C16—C17	−163.7 (2)
C14—Fe1—C4—C3	48.6 (3)	C5—Fe1—C16—C17	78.38 (13)
C16—Fe1—C4—C3	123.93 (12)	C13—Fe1—C16—C17	−37.80 (12)
C15—Fe1—C4—C3	81.87 (14)	C14—Fe1—C16—C17	−81.66 (13)
C3—C4—C5—C1	−0.1 (2)	C15—Fe1—C16—C17	−119.30 (16)
Fe1—C4—C5—C1	−58.95 (12)	C4—Fe1—C16—C17	121.03 (12)
C3—C4—C5—Fe1	58.84 (13)	C3—Fe1—C16—C17	162.34 (11)
C2—C1—C5—C4	0.3 (2)	C14—C13—C17—C16	−0.2 (2)
C6—C1—C5—C4	172.37 (16)	Fe1—C13—C17—C16	−59.58 (14)
Fe1—C1—C5—C4	59.85 (12)	C14—C13—C17—Fe1	59.42 (14)
C2—C1—C5—Fe1	−59.50 (12)	C15—C16—C17—C13	0.2 (2)
C6—C1—C5—Fe1	112.52 (17)	Fe1—C16—C17—C13	59.56 (13)
C1—Fe1—C5—C4	−119.04 (16)	C15—C16—C17—Fe1	−59.39 (14)
C2—Fe1—C5—C4	−80.71 (12)	C1—Fe1—C17—C13	79.85 (14)
C17—Fe1—C5—C4	123.59 (12)	C2—Fe1—C17—C13	48.3 (2)
C13—Fe1—C5—C4	164.27 (12)	C5—Fe1—C17—C13	122.54 (12)
C14—Fe1—C5—C4	−167.6 (2)	C14—Fe1—C17—C13	−37.64 (13)
C16—Fe1—C5—C4	82.11 (13)	C16—Fe1—C17—C13	−118.96 (17)
C15—Fe1—C5—C4	52.4 (3)	C15—Fe1—C17—C13	−81.37 (13)
C3—Fe1—C5—C4	−37.16 (11)	C4—Fe1—C17—C13	163.10 (12)
C2—Fe1—C5—C1	38.33 (10)	C3—Fe1—C17—C13	−168.0 (2)
C17—Fe1—C5—C1	−117.38 (12)	C1—Fe1—C17—C16	−161.20 (11)
C13—Fe1—C5—C1	−76.70 (13)	C2—Fe1—C17—C16	167.30 (17)
C14—Fe1—C5—C1	−48.6 (3)	C5—Fe1—C17—C16	−118.50 (12)
C16—Fe1—C5—C1	−158.85 (11)	C13—Fe1—C17—C16	118.96 (17)
C15—Fe1—C5—C1	171.40 (19)	C14—Fe1—C17—C16	81.32 (13)
C4—Fe1—C5—C1	119.04 (16)	C15—Fe1—C17—C16	37.59 (12)
C3—Fe1—C5—C1	81.88 (12)	C4—Fe1—C17—C16	−77.94 (13)
C2—C1—C6—O1	−178.39 (18)	C3—Fe1—C17—C16	−49.1 (3)

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₂H₁₃O₃)]
M_r	326.16
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	120
a, b, c (Å)	7.7561 (1), 10.8931 (2), 34.0120 (6)
V (Å³)	2873.60 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.06
Crystal size (mm)	0.32 × 0.20 × 0.05

Data collection
Diffractometer	KappaCCD diffractometer (with Oxford Cryosystems Cryostream cooler)
Absorption correction	Multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.844, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	19653, 4409, 3031
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.744

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.091, 1.01
No. of reflections	4409
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.58

Computer programs: COLLECT (Nonius, 1999), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top

Fe1—C1	2.0260 (18)	Fe1—C4	2.0517 (16)
Fe1—C2	2.033 (2)	Fe1—C3	2.0534 (19)
Fe1—C5	2.0339 (17)	O1—C6	1.222 (2)
Fe1—C17	2.038 (2)	O2—C9	1.345 (2)
Fe1—C13	2.0386 (18)	O2—C10	1.459 (2)
Fe1—C14	2.0399 (18)	O3—C9	1.205 (2)
Fe1—C16	2.040 (2)	C11—C12	1.308 (3)
Fe1—C15	2.0415 (19)

C5—C1—C6—O1	11.2 (3)	C10—O2—C9—C8	174.14 (15)
O1—C6—C7—C8	−8.9 (3)	C7—C8—C9—O2	158.09 (15)
C6—C7—C8—C9	−79.7 (2)	O2—C10—C11—C12	131.0 (2)

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