3-(Ferrocen-1-ylcarbon­yl)-1-methyl-4-(4-methyl­phen­yl)spiro­[pyrrolidine-2,11′-indeno­[1,2-b]quinoxaline]

B Vijayakumar; D Gavaskar; T Srinivasan; R Raghunathan; D Velmurugan

doi:10.1107/S1600536812036951

. 2012 Sep 15;68(Pt 10):m1274. doi: 10.1107/S1600536812036951

3-(Ferrocen-1-ylcarbonyl)-1-methyl-4-(4-methylphenyl)spiro[pyrrolidine-2,11′-indeno[1,2-b]quinoxaline]

B Vijayakumar ^a, D Gavaskar ^b, T Srinivasan ^a, R Raghunathan ^b, D Velmurugan ^a,^*

PMCID: PMC3470153 PMID: 23125597

Abstract

In the title compound, [Fe(C₅H₅)(C₃₂H₂₆N₃O)], the pyrrolidine ring adopts a twist conformation. The indeno–quinoxaline ring system [86.44 (5)°], the methylphenyl ring [86.06 (7)°] and the ferrocene rings [82.00 (7) and 83.95 (9)°] are almost perpendicular to the pyrrolidine ring. The two cyclopentadienyl rings adopt an eclipsed conformation. The crystal structure features C—H⋯N 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: Satis Kumar et al.(2007 ▶); Kamala et al. (2009 ▶); Gunasekaran et al. (2010 ▶); For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

[Fe(C₅H₅)(C₃₂H₂₆N₃O)]
M _r = 589.50
Monoclinic,
a = 11.5966 (3) Å
b = 11.8658 (3) Å
c = 20.9383 (6) Å
β = 90.616 (2)°
V = 2881.01 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.56 mm⁻¹
T = 293 K
0.2 × 0.2 × 0.2 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
26509 measured reflections
7145 independent reflections
5247 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.110
S = 1.02
7145 reflections
381 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.31 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, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036951/bt6825sup1.cif

e-68-m1274-sup1.cif^{(48.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036951/bt6825Isup2.hkl

e-68-m1274-Isup2.hkl^{(349.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812036951/bt6825Isup4.mol

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
C28—H28⋯N3ⁱ	0.93	2.49	3.416 (2)	176

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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 thanks the University Grant Commission (UGC), Government of India, New Delhi, for a Meritorious Fellowship.

supplementary crystallographic information

Comment

Ferrocene attached compounds have prominent biological activities like antitumor (Jaouen et al., 2004), antimalarial and antifungal (Biot et al., 2004), and antibacterial (Fouda et al., 2007) and find applications in medicinal chemistry. In this background, X-ray study of the title compound was carried out to obtain the information of molecular conformations and crystal packing in the solid state.

X-ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The bond lengths and angles of titled compound agree with those observed in other ferrocene derivative 4'-Ferrocenyl-3'- 4-methoxybenzoyl)-1'-methylspiro[1H-indole-3(2H), 2'-pyrrolidin]-2-one (Satis Kumar et al., 2007). The dihedral angle between indeno-quinoxaline ring system and the pyrrolidine ring is 87.84 (7)° and the dihedral angle between pyrrolidine ring and the phenyl ring is 86.06 (9) °. The dihedral angle between pyrrolidine ring and the ferrocene rings are 81.00 (10)° and 83.94 (12)°. This clearly shows that the indeno-quinoxaline ring system, the phenyl and ferrocene rings are almost perpendicular to the pyrrolidine ring.

The pyrrolidine ring adopts a twisted conformation with the puckering parameters q₂ and φ (Cremer & Pople, 1975) and the smallest displacement asymmetric parameters, δ, (Nardelli, 1983) as follows: q₂ = 0.3858 (16) Å, φ = 343.1 (3)° and Δ₂ (C16) = 2.13 (15)°. In the ferrocene, Cg3 and Cg4 are the centroids of the C27—C31 and C32—C36 rings, respectively. Fe1—Cg3 and Fe1—Cg4 distances are 1.6430 (8) and 1.6495 (10) Å, respectively and the Cg3—Fe1—Cg4 angle is 177.74 (6)°. In addition to the van der Waals interactions, the crystal packing is stabilized by C—H···N interaction (Table. 1 & Fig. 2).

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.