{1′-Phenyl-1′,2′,5′,6′,7′,7a’-hexa­hydro­spiro­[indeno­[1,2-b]quinoxaline-11,3′-pyrrolizin]-2′-yl}(p-tol­yl)methanone

T Srinivasan; S Suhitha; S Purushothaman; R Raghunathan; D Velmurugan

doi:10.1107/S1600536812031480

. 2012 Jul 18;68(Pt 8):o2469. doi: 10.1107/S1600536812031480

{1′-Phenyl-1′,2′,5′,6′,7′,7a’-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolizin]-2′-yl}(p-tolyl)methanone

T Srinivasan ^a, S Suhitha ^a, S Purushothaman ^b, R Raghunathan ^b, D Velmurugan ^a,^*

PMCID: PMC3414925 PMID: 22904912

Abstract

In the title compound, C₃₅H₂₉N₃O, the quinoxaline and indene systems are essentially planar, with maximum deviations of 0.047 (2) and 0.032 (2) Å for C atoms, respectively. The quinoxaline system forms a dihedral angle of 4.75 (3)° with the indene system. The pyrrolizine system is folded. The substituted five-membered ring adopts an envelope conformation. In the other five-membered ring, one C atom is disordered with a site-occupancy ratio of 0.676 (12):0.324 (12). In the crystal, molecules are linked via C—H⋯O hydrogen bonds involving the bifurcated carbonyl O atom.

Related literature

For the uses of pyrrolidine and quinoxaline derivatives, see: Amal Raj et al. (2003 ▶); Zarranz et al. (2003 ▶). For a related structure, see: Gayathri et al. (2005 ▶).;

Experimental

Crystal data

C₃₅H₂₉N₃O
M _r = 507.61
Orthorhombic,
a = 16.4102 (6) Å
b = 16.4371 (6) Å
c = 20.0648 (7) Å
V = 5412.2 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
47718 measured reflections
6643 independent reflections
3751 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.144
S = 1.01
6643 reflections
363 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008 ▶); 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/S1600536812031480/bt5959sup1.cif

e-68-o2469-sup1.cif^{(38KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031480/bt5959Isup2.hkl

e-68-o2469-Isup2.hkl^{(325.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812031480/bt5959Isup3.cml

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
C1—H1C⋯O1ⁱ	0.96	2.56	3.483 (2)	161
C22—H22⋯O1ⁱⁱ	0.93	2.48	3.361 (3)	158

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

Acknowledgments

TS and DV thank TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for data collection and TS thanks DST for an Inspire fellowship.

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 shown antibacterial, antiviral and anticancer properties (Zarranz et al., 2003). As spiro pyrrolidine compounds are of great medicinal properties, we have undertaken the three dimensional structure of the title compound.

X-ray analysis confirms the molecular structure and atom connectivity of the compound as illustrated in Fig. 1. The quinoxaline moiety is essentially planar with a maximum deviation of -0.0472 (23) Å for C21 atom, and it forms the dihedral angles of 4.75 (3), 54.94 (5) and 29.70 (6) ° with the indene moiety, phenyl rings (C2–C7) and (C30–C35), respectively. The indene moiety is also essentially planar with a maximum deviation of 0.0320 (16) Å for C18 atom, and it forms the dihedral angles of 51.75 (6) and 32.41 (6) ° with the phenyl rings (C2–C7) and (C30–C35), respectively.

The pyrrolizine moiety is folded and twisted about the N—C bond common to the two five membered rings. The indene fused with quinoxaline, subsituted five membered ring adopts twisted conformation on C9 and C29 atoms with the puckering parameters of Q₂ = 0.3846 (17) Å, φ₂ = 95.8 (3) °. The unsubsituted five-membered ring has a disordered C atom with occupancy factor of 0.676 (12)/0.324 (12). The five-membered ring (N1/C25/C26A/C27/C28) adopts an envelope conformation on C26A for major occupancy atom with the puckering parameters Q₂ = 0.309 (4) Å, φ₂ = 77.9 (5) °. The five-membered ring (N1/C25/C26B/C27/C28) adopts an envelope conformation on C26B for minor occupancy atom with the puckering parameters Q₂ = 0.238 (6) Å, φ₂ = 247.0 (10) °. The title compound exhibits structural similarities with the already reported related structures (Gayathri et al.2005).

In the crystal packing, molecules are linked via bifurcated C—H···O intermolecular hydrogen bonds involving the carbonyl group O atom as a single acceptor (Table. 1). The packing view of the compound is shown in Fig. 2.

Experimental

A mixture of ninhydrin (1 mmol) and 1, 2-phenylenediamine (1 mmol) was stirred for 10 min in 10 mL of toluene followed by the addition of L-proline (1 mmol) and a solution of (E)-3-phenyl-1-p-tolylprop-2-en-1-one (1 mmol) in 10 ml of toluene. The mixture was then refluxed until completion of the reaction as evidenced by TLC. The solvent was removed in vacuo and the crude product was subjected to column chromatography using petroleum ether/ethyl acetate (4:1) as eluent.