3′-(4-Meth­oxy­phen­yl)-4′-phenyl-3H,4′H-spiro­[1-benzothio­phene-2,5′-isoxazol]-3-one

Adil Boughaleb; Hafid Zouihri; Said Gmouh; Abdelali Kerbal; Mohamed El yazidi

doi:10.1107/S1600536811024408

. 2011 Jun 30;67(Pt 7):o1850. doi: 10.1107/S1600536811024408

3′-(4-Methoxyphenyl)-4′-phenyl-3H,4′H-spiro[1-benzothiophene-2,5′-isoxazol]-3-one

Adil Boughaleb ^a, Hafid Zouihri ^b, Said Gmouh ^c, Abdelali Kerbal ^a, Mohamed El yazidi ^a,^*

PMCID: PMC3151806 PMID: 21837215

Abstract

In the title compound, C₂₃H₁₇NO₃S, the thiophene and isoxazole rings each have an envelope conformation with the spiro C atom linking them forming the flap of the envelope in each case. The dihedral angle between the mean planes of the benzothiophene ring and isoxazole rings is 81.35 (7)°. In the crystal, an intermolecular C—H⋯O hydrogen bond links the molecules into a chain running parallel to the a axis.

Related literature

For general background to dipolar-1,3 cycloaddition reactions, see: Al Houari et al. (2010 ▶); Toth et al. (1999 ▶); El yazidi et al. (1994 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₃H₁₇NO₃S
M _r = 387.44
Triclinic,
a = 9.3644 (13) Å
b = 9.8132 (14) Å
c = 11.1502 (15) Å
α = 103.575 (8)°
β = 90.360 (8)°
γ = 106.089 (8)°
V = 954.2 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.24 × 0.22 × 0.16 mm

Data collection

Bruker APEXII CCD detector diffractometer
14395 measured reflections
4336 independent reflections
3389 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.117
S = 1.08
4336 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.25 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/S1600536811024408/lw2066sup1.cif

e-67-o1850-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024408/lw2066Isup2.hkl

e-67-o1850-Isup2.hkl^{(212.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811024408/lw2066Isup3.cml

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⋯O1ⁱ	0.93	2.60	3.345 (2)	138

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

1,3-dipolar cyclo-addition of arylnitriloxides with ethylenic dipolarophiles produce isoxazolines in which the electron attracting or withdrawing substitutuent of the dipolarophile is at position 5 (IUPAC numbering) of the isoxazoline [Al Houari, et al. 2010; Toth et al. 1999 and El yazidi et al. 1994].

C₂₃H₁₇NO₃S, Figure 1, is the product of the reaction of the p-anisylnitriloxide with (Z)-2-benzylidenebenzo[b]thiophen-3(2H)- one. The X-ray crystal structure study shows that the hydrogen atom attached to C9 is cis to the carbonyl group attached to C7.

The thiophene and isoxazole rings have envelope conformations, the spiro carbon atom linking them forming the flap of the envelope in each case.

The dihedral angles between the of mean planes of the benzothiophene ring, BTh ,(atoms S1 sequentially to C8), the the isoxazole ring, Iso, (atoms N1-O3-C8-C9-C10), the phenyl ring, MPh, (atoms C17 to C22) and the the phenyl ring, Ph, (atoms C11 to C16) are: Bth/Iso = 81.35 (7)°, BTh/MPh = 88.46 (7)°, BTh/Ph = 84.21 (7)°, Iso/MPh = 7.57 (9)°, Iso/Ph = 84.58 (9) and MPh/Ph = 86.41 (9)°.

The C—H···O hydrogen bonds [C13—H13··· O1 (1+x, y, z) (Table 1)] generates C8 chains, (Bernstein et al., 1995), which run parallel to the aaxis (Figure. 2).

Experimental

In a 100 ml flask, 2 mmoles of the (Z)-2-arylidenebenzo[b]thiophen-3(2H)-one and 2.2 mmoles of p-anisyloxime were dissolved in 20 ml of chloroform. The mixture was cooled to 0°C under magnetic stirring in an ice bath. Then 15 ml of bleach (NaOCl) at 24°Chl(chlorometric degree) was added in small amounts without exceeding the temperature of 5°C. The mixture was left under magnetic stirring for 4 h at room temperature, washed with water until pH was neutral and dried on sodium sulfate. The solvent was evaporated using a rotary evaporator and the oily residue dissolved in ethanol. The resulting precipitate was then re-crystallized in ethanol.