Methyl 5-ferrocenyl-5a-hydr­oxy-1-methyl-10-oxo-2,3,3a,4,5a,10-hexa­hydro-1H-indeno[1,2:2′,3′]furo[3′,4′-b]pyrrole-3a-carboxyl­ate

E Theboral Sugi Kamala; S Nirmala; L Sudha; S Kathiravan; R Raghunathan

doi:10.1107/S1600536809018583

. 2009 May 29;65(Pt 6):m687–m688. doi: 10.1107/S1600536809018583

Methyl 5-ferrocenyl-5a-hydroxy-1-methyl-10-oxo-2,3,3a,4,5a,10-hexahydro-1H-indeno[1,2:2′,3′]furo[3′,4′-b]pyrrole-3a-carboxylate

E Theboral Sugi Kamala ^a, S Nirmala ^a, L Sudha ^b,^*, S Kathiravan ^c, R Raghunathan ^c

PMCID: PMC2969822 PMID: 21583045

Abstract

In the title compound, [Fe(C₅H₅)(C₂₁H₂₀NO₅)], the pyrrolidine and cyclopentanone rings exhibit a twist conformation. The pyrrolidine ring is almost perpendicular to the cyclopentanone ring, making a dihedral angle of 81.91 (6)°. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond and C—H⋯O interactions. The crystal structure is stabilized by intermolecular C—H⋯O interactions.

Related literature

For general background and uses of ferrocene-based ligands, see Gomez Arrayas et al. (2006 ▶); Blaser & Schmidt (2004 ▶); Johnson & Sames (2000 ▶); Baar et al. (2000 ▶); Staveren & Metzler-Nolte (2004 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶).

Experimental

Crystal data

[Fe(C₅H₅)(C₂₁H₂₀NO₅)]
M _r = 487.32
Monoclinic,
a = 7.7292 (2) Å
b = 24.7713 (7) Å
c = 11.8120 (4) Å
β = 93.4450 (10)°
V = 2257.47 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.71 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.816, T _max = 0.872
32884 measured reflections
7917 independent reflections
6016 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.123
S = 1.05
7917 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: APEX2 and SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018583/bt2949sup1.cif

e-65-0m687-sup1.cif^{(35.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018583/bt2949Isup2.hkl

e-65-0m687-Isup2.hkl^{(379.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O4ⁱ	0.93	2.46	3.157 (2)	131
C15—H15⋯O3ⁱⁱ	0.98	2.52	3.303 (2)	137
C16—H16⋯O4ⁱⁱ	0.98	2.59	3.547 (2)	166
C13—H13⋯O5	0.98	2.40	2.820 (2)	105
C24—H24B⋯O3	0.96	2.42	3.014 (3)	120
O2—H2C⋯N1	0.82	2.15	2.6414 (19)	119
C2—H2A⋯O4	0.97	2.42	2.761 (2)	100

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

ETSK thanks Professors M. N. Ponnusamy and D. Velmurugan, Department of Crystallography and Biophysics, University of Madras, India, for their guidance and valuable suggestions. ETSK also thanks Dr Babu Varghese, SAIF, IIT-Madras, and the SRM management for their support.

supplementary crystallographic information

Comment

Ferrocene-based ligands incorporating chirality are very important (Gomez Arrayas et al., 2006) and some of them have already been applied in industrial processes because of their stability, low price and unique structure (Blaser & Schmidt, 2004). Transition metal complexes derived from ferrocene have attracted great intrest due to their applications as precursors for the synthesis of organic as well as organometallic compounds (Johnson & Sames, 2000), in homogeneous catalysis (Baar et al., 2000), or even in biological chemistry (Staveren & Metzler-Nolte, 2004).

Fig. 1 shows the ORTEP plot of compound (I). Bond lengths and angles are comparable with other reported values.

In the molecule the pyrrolidine ring N1/C1/C2/C3/C4 exhibits twist conformation with assymetry parameters (Nardelli, 1983) ΔC_s(C1) = 12.47 (2)/ (C2) = 17.76 (21) and with the puckering parameters (Cremer & Pople, 1975) q2 = 0.3819 (2) Å and φ2 = 53.2 (2)°. The cyclopentanone ring also exhibits twist conformation with assymetry parameters ΔC_s(C4) = 4.07 (2)/ (C12) = 4.11 (2) and with the puckering parameters q2 = 0.1106 (2) Å and φ2 = 343.6 (8)°. The sum of bond angles around N1 [341.70 (4)°] indicates sp² hybridization. The pyrrolidine ring is almost perpendicular to the cyclopentanone ring making a dihedral angle of 81.91 (6)° and the ferrocene ring is perpendicular to the phenyl ring with a dihedral angle of 84.37 (8)°. The cyclopentanone and the phenyl rings are planar with each other making an angle of 5.06 (5)°.

In the crystal packing, atoms O3 and O4 are involved in intermolecular C—H···O interactions and atom O2 contributes to N—H···O intramolecular interactions.

Experimental

A mixture of ferrocenyl Baylis–Hillman adduct, sarcosine and ninhydrin were refluxed in 1,2-dichloethane for 35 h and the solvent was removed under reduced pressure. The crude product was subjected to column chromatography to get the pure product. The product was recrystallized from dry benzene by slow evaporation.