Methyl 9-p-tolyl-8a,9,9a,10,11,12,13,14a-octa­hydro-8H-benzo[f]chromeno[3,4-b]indolizine-8a-carboxyl­ate

B Gunasekaran; S Kathiravan; R Raghunathan; V Manivannan

doi:10.1107/S1600536809049447

. 2009 Nov 25;65(Pt 12):o3188. doi: 10.1107/S1600536809049447

Methyl 9-p-tolyl-8a,9,9a,10,11,12,13,14a-octahydro-8H-benzo[f]chromeno[3,4-b]indolizine-8a-carboxylate

B Gunasekaran ^a, S Kathiravan ^b, R Raghunathan ^b, V Manivannan ^c,^*

PMCID: PMC2972086 PMID: 21578900

Abstract

In the title compound, C₂₈H₂₉NO₃, the fused pyrrolidine and piperidine rings of the octahydroindolizine unit exhibit envelope and chair conformations, respectively. The dihedral angle between the naphthalene ring system and the benzene ring is 40.37 (5)°. The crystal packing is stabilized by weak intermolecular C—H⋯O interactions.

Related literature

For the biological activity of indolizine derivatives, see: Campagna et al. (1990 ▶); Malonne et al. (1998 ▶); Medda et al. (2003 ▶); Pearson & Guo (2001 ▶); Sonnet et al. (2000 ▶). For related structures, see: Gunasekaran et al. (2009 ▶); Kamala et al. (2009 ▶). For details of ring conformations, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶). graphic file with name e-65-o3188-scheme1.jpg

Experimental

Crystal data

C₂₈H₂₉NO₃
M _r = 427.52
Monoclinic,
a = 11.4842 (9) Å
b = 23.0129 (14) Å
c = 9.1642 (5) Å
β = 112.725 (2)°
V = 2233.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.976, T _max = 0.984
27595 measured reflections
5875 independent reflections
3629 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.141
S = 1.01
5875 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049447/is2492sup1.cif

e-65-o3188-sup1.cif^{(24.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049447/is2492Isup2.hkl

e-65-o3188-Isup2.hkl^{(281.8KB, 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
C13—H13⋯O2ⁱ	0.98	2.58	3.496 (2)	156
C7—H7⋯O1ⁱⁱ	0.93	2.55	3.198 (2)	127

Open in a new tab

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

Acknowledgments

BG thanks AMET University management, India, for their kind support. BG also acknowledge SAIF, IITMadras, India, for the data collection.

supplementary crystallographic information

Comment

The synthesis of biologically active indolizine derivatives continues to attract the attention of organic chemists, because of their wide spectrum of biological activity. Indolizine derivatives have been found to possess a variety of biological activities such as antiinflammatory (Malonne et al., 1998), antiviral (Medda et al., 2003), aromatase inhibitory (Sonnet et al., 2000), analgestic (Campagna et al., 1990) and antitumor (Pearson & Guo, 2001) activities.

The geometric parameters of the title compound (Fig. 1) agree well with reported similar structures (Gunasekaran et al., 2009; Kamala et al., 2009). The mean plane of the naphthalene ring system makes a dihedral angle of 40.37 (5)° with the methyl benzene ring. In the molecule the pyrrolidine ring N1/C13/C12/C19/C18 exhibits an envelope conformation with envelope on C13 with an asymmetry parameter (Nardelli, 1983) ΔC_s (C13) = 14.17 (3) and with the puckering parameters (Cremer & Pople, 1975) q2 = 0.4960 (2) Å and φ2 = 205.68 (9)°. The six membered ring N1/C14—C18 exhibits chair conformation with asymmetry parameters ΔC_s (N1) = 1.78 (1)/(C16) = 1.78 (1) and with the puckering parameters Q = 0.5855 (2) Å, Θ = 3.86 (3)° and φ = 335.84 (8)°. The sum of bond angles around N1 [333.20 (12)°] indicates sp³ hybridization. The crystal packing is stabilized by weak intermolecular C—H···O interactions.

Experimental

A mixture of (Z)-methyl 2-[(1-formylnaphthalen-2-yloxy)methyl]-3-tolylacrylate (20 mmol) and pipecolinic acid (30 mmol) 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. Chloroform and methanol (1:1) solvent mixture was used for the crystallization under slow evaporation method.