Ethyl 1′′-benzyl-1′-methyl-2′′-oxodi­spiro­[indeno­[1,2-b]quinoxaline-11,3′-pyrrolidine-2′,3′′-indoline]-4′-carboxyl­ate

Piskala Subburaman Kannan; Srinu Lanka; Sathiah Thennarasu; Elumalai Govindan; Arunachalathevar SubbiahPandi

doi:10.1107/S1600536813011525

. 2013 May 4;69(Pt 6):o822. doi: 10.1107/S1600536813011525

Ethyl 1′′-benzyl-1′-methyl-2′′-oxodispiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolidine-2′,3′′-indoline]-4′-carboxylate

Piskala Subburaman Kannan ^a, Srinu Lanka ^b, Sathiah Thennarasu ^b, Elumalai Govindan ^c, Arunachalathevar SubbiahPandi ^c,^*

PMCID: PMC3684912 PMID: 23795014

Abstract

In the title compound, C₃₆H₃₀N₄O₃, the quinoxaline–indene system is roughly planar, with a maximum deviation from the mean plane of 0.218 Å for the C atom shared with the central pyrrolidine ring. This latter ring forms dihedral angles of 84.54 (7) and 83.91 (8)° with the quinoxaline–indene system and the indole ring, respectively. The central pyrrolidine ring has an envelope conformation with the N atom as the flap, while the pyrrolidine and five-membered rings of the indole group adopt twisted conformation and envelope (with the C atom bearing the quinoxaline–indene system as the flap) conformations, respectively. In the crystal, molecules are linked via weak C—H⋯N hydrogen bonds, forming a chain running along [100].

Related literature

For details of the synthesis, see: Azizian et al. (2005 ▶). For uses of pyrrolidine and quinoxaline derivatives, see: Amal Raj et al. (2003 ▶); Zarranz et al. (2003 ▶). For a related structure, see: Srinivasan et al. (2012 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₃₆H₃₀N₄O₃
M _r = 566.64
Triclinic,
a = 11.1927 (2) Å
b = 11.4535 (3) Å
c = 12.1206 (3) Å
α = 87.637 (2)°
β = 86.048 (1)°
γ = 70.564 (2)°
V = 1461.50 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.971, T _max = 0.980
21785 measured reflections
5987 independent reflections
4956 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.134
S = 1.04
5987 reflections
388 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.28 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(29KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813011525/bg2503sup1.cif

e-69-0o822-sup1.cif^{(29KB, cif)}

Click here for additional data file.^{(293KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011525/bg2503Isup2.hkl

e-69-0o822-Isup2.hkl^{(293KB, 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
C27—H27⋯N4ⁱ	0.93	2.60	3.446 (2)	152

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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, Chennai, India, for the data collection.

supplementary crystallographic information

Comment

Pyrrolidine derivatives are found to have anticonvulsant, antimicrobial and antifungal activities against various pathogens (Amal Raj et al., 2003). Quinoxaline derivatives may show antibacterial, antiviral and anticancer properties (Zarranz et al., 2003). As spiro pyrrolidine compounds are of interest due to their potential medicinal properties, we have undertaken the study of the three dimensional structure of the title compound C₃₆H₃₀N₄O₃, (I).

Fig 1 presents a molecular view of (I). The quinoxaline-indene system C1-C15/N1-N2), is essentially planar, with maximum deviation from the mean plane of 0.218Å for atom C15.

The central pyrrolidine ring (N4/C15-C16/C34-C35) forms dihedral angles of 84.54 (7) and 83.91 (8)° with the quinoxaline-indene and the (C16-C23/N3 indole groups, respectively. The central pyrrolidine ring is enveloped on N4 with puckering parameters q₂ = 0.4000 (2) Å, φ = 359.20 (2)° (Cremer & Pople, 1975). The pyrrolidine in the indole group adopts a twisted conformation on C17-C16 with puckering parameters of q₂ = 0.1265 (2) Å, φ = 51.90 (7)°, while the (C7-C9/C14-C15) five membered ring envelopes on C15 with puckering parameters q₂ = 0.1135 (2) Å, φ = 322.40 (8)°.

In the crystal packing, molecules are linked via weak C-H···N intermolecular hydrogen bonds (Table 1) to form chains along [100], as shown in Fig.2.

Experimental

A mixture of benzyl Isatin(0.25 mmol), sarcosine(0.3 mmol), ethyl indeno[1,2-b]quinoxalin-11-ylideneacetate(0.25 mmol) in ethanol was refluxed for 60 min (Azizian et al., 2005). The progress of the reaction was followed by TLC. After completion, the solvent was removed under reduced pressure and the resulting crude product was subjected to column chromatography. The product was recrystallised from methanol. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.