4-Ferrocenyl-1-methyl-3-benzoyl­spiro­[pyrrolidine-2,11′-indeno­[1,2-b]quinoxaline]

B Vijayakumar; A R Sureshbabu; D Gavaskar; R Raghunathan; D Velmurugan

doi:10.1107/S1600536812048349

. 2012 Nov 30;68(Pt 12):m1576–m1577. doi: 10.1107/S1600536812048349

4-Ferrocenyl-1-methyl-3-benzoylspiro[pyrrolidine-2,11′-indeno[1,2-b]quinoxaline]

B Vijayakumar ^a, A R Sureshbabu ^b, D Gavaskar ^b, R Raghunathan ^b, D Velmurugan ^a,^*

PMCID: PMC3588807 PMID: 23468772

Abstract

In the title compound, [Fe(C₅H₅)(C₃₁H₂₄N₃O)], the pyrrolidine ring adopts a twist conformation. The pyrrolidine ring is almost perpendicular to the indenoquinoxaline ring system, making a dihedral angle of 84.44 (5)°. The cyclopentadienyl rings of the ferrocene moiety adopt an eclipsed conformation. The crystal packing features weak C—H⋯N and C—H⋯π interactions.

Related literature

For the biological activity of ferrocene derivatives, see: Jaouen et al. (2004 ▶); Biot et al. (2004 ▶); Fouda et al. (2007 ▶). For related structures, see: Kamala et al. (2009 ▶); Gunasekaran et al. (2010 ▶); Vijayakumar et al. (2012 ▶); For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

[Fe(C₅H₅)(C₃₁H₂₄N₃O)]
M _r = 575.47
Monoclinic,
a = 10.8091 (18) Å
b = 12.326 (2) Å
c = 20.989 (3) Å
β = 100.654 (8)°
V = 2748.2 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.58 mm⁻¹
T = 293 K
0.2 × 0.2 × 0.2 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.890, T _max = 0.890
27206 measured reflections
6927 independent reflections
5624 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.106
S = 1.01
6927 reflections
371 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(47.1KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812048349/bt6861sup1.cif

e-68-m1576-sup1.cif^{(47.1KB, cif)}

Click here for additional data file.^{(339KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048349/bt6861Isup2.hkl

e-68-m1576-Isup2.hkl^{(339KB, hkl)}

Click here for additional data file.^{(4.3KB, mol)}

Supplementary material file. DOI: 10.1107/S1600536812048349/bt6861Isup3.mol

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

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

Cg3 is the centroid of the C20–C24 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯N3	0.93	2.55	3.351 (2)	144
C35—H35⋯Cg3ⁱ	0.93	2.83	3.616 (2)	143

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. BV also thanks the University Grants Commission (UGC), Government of India, New Delhi, for a Meritorious Fellowship.

supplementary crystallographic information

Comment

Ferrocene attached compounds are well known to have biological activities like antimalarial, antifungal (Biot et al., 2004), antitumor (Jaouen et al., 2004), and antibacterial (Fouda et al., 2007). Against this background, the information of molecular conformations and crystal packing of title compound was obtained and analyzed using X-ray diffraction study. The bond lengths and angles of titled compound agree with those observed in other ferrocene derivative 3'-Ferrocenylcarbonyl-1'-methyl-4'- phenylspiro[indeno[2,3-b]quinoxaline-11,2'-pyrrolidine] (Vijayakumar et al. 2012).

The pyrrolidine ring adopts a twisted conformation with the puckering parameters q₂ and φ and the smallest displacement asymmetric parameters, δ, as follows: q2 = 0.399 (1) A, φ = 26.0 (2)° and Δ₂(C17) =7.29 (14)°. The dihedral angle between the pyrrolidine ring and indeno-quinoxaline ring system is 84.44 (5)° which clearly shows that the both rings are almost perpendicular to each other. The Cg3 (C20—C24) and Cg4 (C25—C29) are the centroids cyclopentadinene rings where the Fe1-Cg3 and Fe1-Cg4 distances are 1.6466 (8) and 1.6512 (10) Å, respectively and the Cg3-Fe1-Cg4 angle is 179.40 (5)°. In addition to the van der Waals interactions, the crystal packing (Fig.2) is stabilized by weak C—H···N and C—H···π interactions (Table 1).

Experimental

Ninhydrin (1 mM) and 1, 2-phenylenediamine (1 mM) were mixed and stirred with 10mL of methanol for 10 min. To this mixture 1 mM of Sarcosine and 1 mM of ferrocene derived dipolarophile were added and was refluxed up to the end of the reaction as observed by TLC. The solvent content from the mixture was removed under reduced pressure and the crude product was obtained. Using column chromatography the crude extract was purified by 4:1 ratio of petroleum ether and ethyl acetate. Finally, single crystals suitable for the X-ray diffraction were obtained by slow evaporation at room temperature.