(1R,4R,5R)-1,3,4-Triphenyl-7-[(R)-1-phenyl­ethyl]-2-oxa-3,7-diaza­spiro­[4.5]decan-10-one

A Malathy; R Suresh Kumar; S Perumal; J Suresh; Nilantha Lakshman

doi:10.1107/S1600536807067256

. 2007 Dec 21;64(Pt 1):o343. doi: 10.1107/S1600536807067256

(1R,4R,5R)-1,3,4-Triphenyl-7-[(R)-1-phenylethyl]-2-oxa-3,7-diazaspiro[4.5]decan-10-one

A Malathy ^a, R Suresh Kumar ^b, S Perumal ^b, J Suresh ^c, Nilantha Lakshman ^d,^*

PMCID: PMC2915384 PMID: 21200905

Abstract

In the title compound, C₃₃H₃₂N₂O₂, the polysubstituted piperidine ring adopts a chair conformation. The isoxazolidine ring is in an envelope conformation. In the crystal structure, intra- and intermolecular C—H⋯π interactions involving the phenyl rings are observed.

Related literature

For related literature, see: Ali Dondas et al. (2001 ▶); Alibés et al. (2003 ▶); Blanarikova-Hlobilova et al. (2003 ▶); Carda et al. (2000 ▶); Carruthers (1990 ▶); Herrera et al. (2001 ▶); Huisgen (1963 ▶); Ishar et al. (2000 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₃₃H₃₂N₂O₂
M _r = 488.61
Orthorhombic,
a = 10.589 (5) Å
b = 14.582 (7) Å
c = 17.443 (8) Å
V = 2693 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 273 (2) K
0.20 × 0.16 × 0.12 mm

Data collection

Nonius MACH-3 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.986, T _max = 0.991
13617 measured reflections
2701 independent reflections
1899 reflections with I > 2σ(I)
R _int = 0.074
2 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.118
S = 1.09
2701 reflections
335 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067256/ci2540sup1.cif

e-64-0o343-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067256/ci2540Isup2.hkl

e-64-0o343-Isup2.hkl^{(129.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1, Cg2 and Cg3 are the centroids of the phenyl rings C71–C76, C91–C96 and C81–C86, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1	0.98	2.35	2.775 (5)	106
C26—H26⋯O2	0.93	2.29	2.623 (5)	101
C82—H82⋯O2	0.93	2.43	2.757 (5)	101
C3—H3A⋯Cg1	0.97	2.90	3.659 (5)	136
C2—H2A⋯Cg2ⁱ	0.97	2.93	3.707 (5)	138
C74—H74⋯Cg3ⁱⁱ	0.93	2.96	3.722 (6)	141

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

Acknowledgments

SP thanks the CSIR, New Delhi, for a Major Research Project.

supplementary crystallographic information

Comment

1,3-Dipolar cycloaddition is a versatile reaction for the construction of five-membered ring heterocycles of biological importance (Huisgen, 1963). Among the 1,3-dipoles, nitrones have been subjected to numerous 1,3-dipolar cycloadditions, ascribable to their stability and ease of generation (Blanarikova-Hlobilova et al., 2003; Herrera et al., 2001). The 1,3-dipolar cycloaddition of nitrones to alkenes afford isoxazolidines with generation of as many as three new contiguous stereocenters in a single step (Ishar et al., 2000; Carda et al., 2000; Ali Dondas et al., 2001; Alibés et al., 2003). These isoxazolidines can be further elaborated into polyfunctional cyclic or acyclic bioactive compounds with complete control of relative stereochemistry (Carruthers, 1990).

The molecular structure of (I) is shown in Fig.1. The five-membered isoxazolidine ring has an envelope conformation, as indicated by the Cremer & Pople (1975) puckering parameters Q = 0.454 (3) Å and φ = 3.3 (5)°. The piperidine ring adopts a chair conformation. The dihedral angle between the C21–C26 and C71–C76 phenyl rings is 77.7 (1)°. The C21–C26, C71–C76 and C81–C86 phenyl rings form dihedral angles of 35.8 (2)°, 77.5 (1)° and 72.3 (2)°, respectively, with the N2/C7/C5/C8 plane.

Weak intramolecular C—H···O and C—H···π interactions are observed in the molecular structure. The packing of molecules is governed by weak C—H···π interactions (Table 1) and van der Walls interactions. In the Table 1, Cg1, Cg2 and Cg3 denote the centroids of the C71–C76, C91–C96 and C81–C86 phenyl rings.

Experimental

A mixture of [(R)-1-phenylethyl]-3-[(E)-phenylmethylidene]tetrahydro-4(1H)- pyridinone (0.300 g, 1 mmol) and nitrone (0.244 g, 1.2 mmol) in toluene (25 ml) was refluxed for 10 h. The progress of the reaction was monitored by thin-layer chromatography (TLC) and after completion of the reaction, the solvent was evaporated in vacuo. The residue was then subjected to flash column chromatography on silica gel using petroleum ether-ethyl acetate (10:1) as eluent to obtain crystals of the title compound in 8% yield (0.040 g) along with two other products in semi-solid form.