Crystal structure of 3,4′-diphenyl-3′-p-tolyl-4′H-spiro­[indan-2,5′-[1,2]oxazol]-1-one

Asmae Mahfoud; Ghali Al Houari; Mohamed El Yazidi; Mohamed Saadi; Lahcen El Ammari

doi:10.1107/S2056989015019581

. 2015 Oct 24;71(Pt 11):o873–o874. doi: 10.1107/S2056989015019581

Crystal structure of 3,4′-diphenyl-3′-p-tolyl-4′H-spiro[indan-2,5′-[1,2]oxazol]-1-one

Asmae Mahfoud ^a,^*, Ghali Al Houari ^a, Mohamed El Yazidi ^a, Mohamed Saadi ^b, Lahcen El Ammari ^b

PMCID: PMC4645049 PMID: 26594573

Abstract

In the title compound, C₃₀H₂₃NO₂, the five-membered rings are both in envelope conformations with the same spiro C atom as the flap. The benzene ring and the two phenyl rings are inclined to the mean plane of the indene ring system by 83.98 (8), 81.46 (8) and 72.31 (7)°. In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds into inversion dimers. The dimers are further connected by C—H⋯N interactions, forming layers parallel to (10-1).

Keywords: crystal structure; hydrogen-bonding; 1,3-dipolar cycloaddition reaction

Related literature

For general background to 1,3-dipolar cycloaddition reactions, see: Al Houari et al. (2008 ▸, 2010 ▸). For a related structure, see: Akhazzane et al. (2010 ▸).

Experimental

Crystal data

C₃₀H₂₃NO₂
M _r = 429.49
Monoclinic,
a = 9.7381 (7) Å
b = 20.5072 (14) Å
c = 11.8261 (8) Å
β = 102.836 (2)°
V = 2302.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.42 × 0.31 × 0.26 mm

Data collection

Bruker X8 APEX diffractometer
38803 measured reflections
5942 independent reflections
3783 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.150
S = 1.03
5942 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015019581/is5427sup1.cif

e-71-0o873-sup1.cif^{(1.3MB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015019581/is5427Isup2.hkl

e-71-0o873-Isup2.hkl^{(472.6KB, hkl)}

Click here for additional data file.^{(8.5KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015019581/is5427Isup3.cml

Click here for additional data file.^{(1.4MB, tif)}

. DOI: 10.1107/S2056989015019581/is5427fig1.tif

The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

Click here for additional data file.^{(2MB, tif)}

. DOI: 10.1107/S2056989015019581/is5427fig2.tif

Partial crystal packing for the title compound showing molecules linked by hydrogen bonds as dashed lines.

CCDC reference: 1431561

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
C10H10O1ⁱ	0.98	2.47	3.4169(18)	163
C2H2N1ⁱⁱ	0.93	2.56	3.280(2)	135

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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

S1. Comment

In this paper we studied the stereochemistry in the reaction of p-tolylnitriloxide with (2E)-2-benzylidene-3-phenyl-2,3-dihydro-1H-inden-1-one. The X-Ray crystal study shows that the cabonyl group is in the position 5 of the isoxazoline. We also found that the phenyl group imposes an exclusive anti approach of the dipole. This stereochemistry is due to steric effects (Al Houari et al., 2008, 2010; Akhazzane et al., 2010).

The molecule of the title compound is formed by two fused five- and six-membered rings linked to a phenyl ring and to a five-membered ring which is connected to a phenyl ring and a toluene cycle (Fig. 1). The two five-membered rings (C1/C6–C9) and (N1/O2/C8/C10/C11) adopt envelope conformations on atom C8 as indicated by the total puckering amplitude Q2 = 0.256 (2) Å and spherical polar angle φ2 = 290.0 (4)°, and Q2 = 0.2496 (2) Å and φ2 = 320.0 (3)°. The mean plane through the indene ring (C1–C9) is nearly perpendicular to the benzene and phenyl rings (C12–C17, C19–C24 and C25–C30), making dihedral angles of 83.98 (8), 81.46 (8) and 72.31 (7)° with them. In the crystal, molecules are linked by a pair of C10—H10···O1 hydrogen bonds into an inversion dimer. The dimers are further connected by a C2—H2···N1 interaction (Fig. 2 and Table 1).

S2. Experimental

In a 100 ml flask, we dissolve 2 mmoles of (2E)-2-benzylidene-3-phenyl-2,3-dihydro-1H-inden-1-one and 2.4 mmoles of p-tolyloxime in 20 ml of chloroform. The mixture is cooled to 273 K under magnetic stirring in an ice bath. Then 15 ml of bleach (NaOCl) at 291 K (Chlorometric degree) is added in small doses without exceeding 278 K. The mixture is left under magnetic stirring for 16 h at room temperature, then washed with water until the 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 compound is then recrystallized in ethanol.