Methyl 5-phenyl-1,2,3,4,4a,5,5a,13c-octahydro-6H-benzo[f]chromeno[3,4-b]indolizine-5a-carboxyl­ate

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

doi:10.1107/S1600536809026774

. 2009 Jul 18;65(Pt 8):o1923–o1924. doi: 10.1107/S1600536809026774

Methyl 5-phenyl-1,2,3,4,4a,5,5a,13c-octahydro-6H-benzo[f]chromeno[3,4-b]indolizine-5a-carboxylate

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

PMCID: PMC2977337 PMID: 21583607

Abstract

In the title compound, C₂₇H₂₇NO₃, the pyrrolidine ring exhibits a twist conformation and the piperidine ring exhibits a chair conformation. The pyrrolidine ring makes dihedral angles of 54.47 (5), 51.50 (5) and 73.37 (6)° with the napthalene ring system and the tetrahydropyran and phenyl rings, respectively. The structure is stabilized by intramolecular C—H⋯O and C—H⋯N interactions.

Related literature

For general background to the applications and biological activity of indolizine derivatives, see: Gubin et al. (1992 ▶); Gupta et al. (2003 ▶); Poty et al. (1994 ▶); Hema et al. (2003 ▶); Malonne et al. (1998 ▶); Medda et al. (2003 ▶). For puckering parameters, see: Cremer and Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶).

Experimental

Crystal data

C₂₇H₂₇NO₃
M _r = 413.50
Triclinic,
a = 9.4201 (3) Å
b = 10.6752 (3) Å
c = 11.0761 (3) Å
α = 78.262 (2)°
β = 77.911 (2)°
γ = 87.346 (2)°
V = 1066.34 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.975, T _max = 0.988
22685 measured reflections
4641 independent reflections
3461 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.122
S = 1.00
4641 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.23 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: 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: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809026774/bt2988sup1.cif

e-65-o1923-sup1.cif^{(21.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026774/bt2988Isup2.hkl

e-65-o1923-Isup2.hkl^{(222.7KB, 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
C8—H8⋯O3	0.98	2.47	2.8240 (19)	101
C19—H19B⋯N1	0.97	2.55	2.885 (2)	100

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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 SRM Management, for their support.

supplementary crystallographic information

Comment

Indolizines, the nitrogen containing heterocyclic systems, are widely distributed in nature; in particular, indolizine derivatives are an important class of heterocyclic bioactive compounds with a wide range of applications, such as pharmaceutical drugs, potential central nervous system depressants, calcium entry blockers, cardiovascular agents, spectral sensitizers and novel dyes(Gubin et al., 1992; Gupta et al., 2003; Poty et al., 1994; Hema et al., 2003).Moreover indolizine derivatives have been found to possess a variety of biological activities such as antiinflammatory (Malonne et al., 1998), antiviral (Medda et al., 2003).

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/C5/C6/C7/C8 exhibits twist conformation with assymetry parameters (Nardelli, 1983) ΔC_s(N1) =23.66 (1)/ (C8) = 14.95 (1) and with the puckering parameters (Cremer and Pople, 1975) q2 = 0.4749 (1)Å and φ2 = 155.74 (2)°. The six membered ring N1/C1—C5 exhibits chair conformation with assymetry parameters ΔC_s(N1) = 2.78 (1)/(C3) = 2.78 (1) and with the puckering parameters Q = 0.5788 (2) Å, Θ = 175.62 (2)° and φ = 145 (2)°. The sum of bond angles around N1 [331.99 (3)°] indicates sp³ hybridization. The pyrrolidine ring makes dihedral angles of 54.47 (5)°, 51.50 (5)° and 73.37 (6)° with the napthalene,tetrahydro pyran and phenyl rings respectively. The napthalene and tetrahydro pyran rings are almost planar with each other with a dihedral angle of 8.88 (4)°,

In the crystal packing, atom O3 is involved in intramolecular C - H···O interactions and atom N1 contributes to C - H···N intramolecular interactions.

Experimental

A mixture of (Z)-methyl 2-(1-formylnaphthalen-2-yloxy)-3-p-tolylacrylate and pipecolinic acid were refluxed in benzene for 20 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.