3-(4-Chloro­phen­yl)-7-methyl-4-(4-methyl­phen­yl)-1-oxa-2,7-diaza­spiro­[4.5]dec-2-en-10-one

D Gayathri; D Velmurugan; R Ranjith Kumar; S Perumal; K Ravikumar

doi:10.1107/S1600536807068717

. 2008 Jan 9;64(Pt 2):o398. doi: 10.1107/S1600536807068717

3-(4-Chlorophenyl)-7-methyl-4-(4-methylphenyl)-1-oxa-2,7-diazaspiro[4.5]dec-2-en-10-one

D Gayathri ^a, D Velmurugan ^a,^*, R Ranjith Kumar ^b, S Perumal ^b, K Ravikumar ^c

PMCID: PMC2960192 PMID: 21201426

Abstract

In the title compound, C₂₁H₂₁ClN₂O₂, the dihydroisoxazole ring adopts an envelope conformation and the piperidinone ring is in a chair conformation. The dihedral angle between the two benzene rings is 84.2 (1)°. The crystal used was an inversion twin.

Related literature

For general background, see: Diana et al. (1985 ▶); Huisgen (1984 ▶); Lepage et al. (1992 ▶); Ryng et al. (1998 ▶); Torssell (1988 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶).

Experimental

Crystal data

C₂₁H₂₁ClN₂O₂
M _r = 368.85
Orthorhombic,
a = 11.4585 (8) Å
b = 16.1132 (11) Å
c = 10.1038 (7) Å
V = 1865.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 (2) K
0.24 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: none
16236 measured reflections
4350 independent reflections
3771 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.111
S = 1.03
4350 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ▶), with 1846 Friedel pairs
Flack parameter: 0.65 (6)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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, 2003 ▶); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068717/ci2543sup1.cif

e-64-0o398-sup1.cif^{(20.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068717/ci2543Isup2.hkl

e-64-0o398-Isup2.hkl^{(208.9KB, hkl)}

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

Acknowledgments

DG thanks the Council of Scientific and Industrial Research (CSIR), India, for a Senior Research Fellowship. The University Grants Commission (UGC–SAP) and the Department of Science and Technology (DST–FIST), Government of India, are acknowledged by DV for providing facilities to the department.

supplementary crystallographic information

Comment

1,3-Dipolar cycloaddition of nitrile oxides to alkenes and alkynes affords isoxazoles and isoxazolines (Torssell, 1988). Apart from exhibiting important biological activities such as antiviral (Diana et al., 1985), anticonvulsant (Lepage et al., 1992) and immunostimulatory (Ryng et al., 1998), isoxazolines are valuable synthons in the synthesis of α,β-unsaturated ketones, β-hydroxy ketones and γ-amino alcohols (Huisgen, 1984). In view of the above facts, we have undertaken the X-ray crystal structure determination of the title compound.

The sum of the bond angles around N2 (331.7°) indicates the sp³-hybridization. The dihydro-isoxazole ring (C1—C3/O1/N1) adopts an envelope conformation with atom C1 deviating by 0.350 (2) Å from the plane of rest of the atoms in the ring. The piperidinone ring adopts a chair conformation. The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) for the dihydro-isoxazole ring are q₂ = 0.220 (2) Å, φ = 142.2 (4)° and Δ_s(C₁) = 1.1 (2)°, and for the piperidinone ring q₂ = 0.074 (2) Å, q₃ = 0.569 (2) Å, Q_T = 0.574 (2) Å and θ = 7.5 (2)°. The dihedral angle between the two benzene rings (C9—C14 and C16—C21) is 84.2 (1)°. The chlorine atom deviates by -0.065 (1) Å from the plane of the attached C16—C21 benzene ring, and the methyl carbon atom C15 deviates by 0.082 (2) Å from the plane of the C9—C14 benzene ring.

The crystal packing is stabilized by van der Waals forces.

Experimental

To a well stirred mixture of 1-methyl-3-[(E)-4-methylphenylmethylidene]tetrahydro-4(1H)-pyridinone (1 mmol) and 4-chlorobenzohydroximoyl chloride (3 mmol) in benzene (15 ml), triethylamine (3 mmol) was added dropwise over a period of 10 min and stirring was continued for 5 h at ambient temperature. The triethylamine hydrochloride was filtered off, solvent evaporated in vacuo, and the product was purified by column chromatography using petroleum ether-ethyl acetate (4:1 v/v) mixture. The compound was then recrystallized from ethanol-ethyl acetate (1:1 v/v).