4-tert-Butyl-3′,4′-bis­(4-methyl­phen­yl)-3,4-dihydro-1H,4′H-spiro­[naphthalene-2,5′-[1,2]oxazol]-1-one

Mohamed Akhazzane; Hafid Zouihri; AKella Bennani; Abdelali Kerbal; Ghali Al Houari

doi:10.1107/S1600536811025086

. 2011 Jun 30;67(Pt 7):o1862. doi: 10.1107/S1600536811025086

4-tert-Butyl-3′,4′-bis(4-methylphenyl)-3,4-dihydro-1H,4′H-spiro[naphthalene-2,5′-[1,2]oxazol]-1-one

Mohamed Akhazzane ^a,^*, Hafid Zouihri ^b, AKella Bennani ^a, Abdelali Kerbal ^a, Ghali Al Houari ^a

PMCID: PMC3152001 PMID: 21837226

Abstract

In the title compound, C₃₀H₃₁NO₂, the cyclohexanone ring in the naphthalene fused-ring system adopts a half-chair conformation, presumably due to conjugation of the benzene ring. The naphthalene ring system makes dihedral angles of 86.63 (7), 65.15 (8) and 63.18 (8)° with respect to the two methylbenzene planes and the 1,2-oxazole ring system. Intermolecular C—H⋯O and C—H⋯N hydrogen bonding and C—H⋯π interactions stabilize the crystal structure. The H atoms of the two methyl groups of the methylphenyl groups are disordered over two positions with equal occupancies.

Related literature

For general background to dipolar-1,3 cycloaddition reactions, see: Al Houari et al. (2008 ▶, 2010 ▶). For a related structure, see: Akhazzane et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₃₀H₃₁NO₂
M _r = 437.56
Monoclinic,
a = 6.9158 (2) Å
b = 25.0737 (5) Å
c = 13.8747 (3) Å
β = 94.359 (1)°
V = 2398.98 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.23 × 0.21 × 0.14 mm

Data collection

Bruker APEXII CCD detector diffractometer
25446 measured reflections
4473 independent reflections
3577 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.111
S = 1.06
4473 reflections
301 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811025086/fj2437sup1.cif

e-67-o1862-sup1.cif^{(30.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025086/fj2437Isup2.hkl

e-67-o1862-Isup2.hkl^{(219.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811025086/fj2437Isup3.cml

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

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

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24⋯O1ⁱ	0.93	2.54	3.4254 (17)	160
C29—H29F⋯N1ⁱⁱ	0.96	2.62	3.546 (2)	161
C26—H26A⋯Cg2ⁱ	0.96	2.77	3.6643 (16)	155

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

Acknowledgments

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

supplementary crystallographic information

Comment

In this paper we studied the regiochemistry and stereochemistry in the reaction of the p-tolylnitriloxide with the 4-tert-butyl-2-(4-methylbenzylidene)-3,4-dihydronaphthalen-1-one.The X-ray crystal structure study shows that the carbonyl group is in position 5 of the isoxazoline. We also found out with this study, that the disposition of the ethyl group imposes an exclusive anti approach of the dipole. This stereochemistry is due to steric effects [Al Houari, et al. (2010) and Al Houari et al. (2008)].

In the title compound, as shown in Fig. 1, all bond lengths and angles are normal and comparable with those reported for the related structure [Akhazzane et al., (2010)].

The cyclohexanone ring in the dihydronaphthalene fused-ring system adopts a half-chair conformation, presumably due to conjugation of the planar annulated benzo ring,, with the puckering parameters of: Q(2) = 0.5212 (14) Å, Phi(2) = 130.12 (15)°, Q(3) = 0.0845 (14) Å (Cremer & Pople, 1975). The dihedral angles between rings are 4'-methylbenzene (E) /naphthalene = 86.63 (7)°, 3'-methylbenzene (D) /naphthalene = 65.15 (8)°, oxazol (C) /naphthalene = 63.18 (8)°, 4'-methylbenzene (E) /3'-methylbenzene (D) = 75.77 (9)°, 3'-methylbenzene (D) /oxazol (C) = 14.55 (9)° and 4'-methylbenzene (E) /oxazol (C) = 89.68 (9)°.

The crystal packing of the title compound is illustrated in Fig. 2. Intermolecular C—H···O and C—H···N hydrogen bonding and C—H···π interactions stabilize the crystal structure.

Experimental

In a100 ml flask, we dissolve 2 mmoles of the 4-tert-butyl-2-(4-methylbenzylidene)-3,4-dihydronaphthalen-1-one and 2.4 mmoles of p-tolyloxime in 20 ml of chloroform. The mixture is cooled to 0°C under magnetic stirring in an ice bath. Then 15 ml of bleach (NaOCl) at 18°Chl (chlorometric degree) is added in small doses without exceeding the temperature of 5°C. The mixture is left under magnetic stirring for 16 h at room temperature, then washed with water until pH is neutral and dried on sodium sulfate. The solvent is evaporated with a rotating evaporator and the oily residue is dissolved in ethanol. The precipitated cycloadduct is then recrystallized in ethanol.