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

Boughaleb, A.; Zouihri, H.; Gmouh, S.; Kerbal, A.; El yazidi, M.

doi:10.1107/S1600536811024408

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1850

doi:10.1107/S1600536811024408

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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 and Mohamed El yazidi ^a ^*

^aDépartement de Chimie, Faculté des Sciences, Dhar Mehraz, BP 1796 Atlas, 30000 Fés, Morocco, ^bLaboratoires de Diffraction des Rayons X, Centre Nationale pour la Recherche Scientifique et Technique, Rabat, Morocco, and ^cCentre Nationale pour la Recherche, Scientifique et Technique, Rabat, Morocco
^*Correspondence e-mail: elyazidimohamed@hotmail.com

(Received 14 June 2011; accepted 21 June 2011; online 30 June 2011)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.040
wR(F²) = 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

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
Symmetry code: (i) x+1, y, z.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811024408/lw2066sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811024408/lw2066Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top

	Fig. 1. Molecular view of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view showing the chain formed by C—H···O. H atoms not involved in hydrogen bonds have been omitted for clarity.

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

Crystal data top

C₂₃H₁₇NO₃S	Z = 2
M_r = 387.44	F(000) = 404
Triclinic, P1	D_x = 1.348 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3644 (13) Å	Cell parameters from 312 reflections
b = 9.8132 (14) Å	θ = 2.6–26.4°
c = 11.1502 (15) Å	µ = 0.19 mm⁻¹
α = 103.575 (8)°	T = 296 K
β = 90.360 (8)°	Prism, colourless
γ = 106.089 (8)°	0.24 × 0.22 × 0.16 mm
V = 954.2 (2) Å³

Data collection top

Bruker APEXII CCD detector diffractometer	3389 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 27.5°, θ_min = 2.5°
ω and ϕ scans	h = −12→12
14395 measured reflections	k = −12→12
4336 independent reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.055P)² + 0.2963P] where P = (F_o² + 2F_c²)/3
4336 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₃H₁₇NO₃S	γ = 106.089 (8)°
M_r = 387.44	V = 954.2 (2) Å³
Triclinic, P1	Z = 2
a = 9.3644 (13) Å	Mo Kα radiation
b = 9.8132 (14) Å	µ = 0.19 mm⁻¹
c = 11.1502 (15) Å	T = 296 K
α = 103.575 (8)°	0.24 × 0.22 × 0.16 mm
β = 90.360 (8)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.08	Δρ_max = 0.30 e Å⁻³
4336 reflections	Δρ_min = −0.25 e Å⁻³
254 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.38947 (5)	0.17699 (5)	0.10614 (4)	0.04579 (15)
C9	0.48093 (15)	0.45610 (16)	0.28184 (14)	0.0289 (3)
H9	0.4698	0.4578	0.3695	0.035*
C11	0.63503 (15)	0.44522 (16)	0.25013 (14)	0.0291 (3)
C8	0.35039 (16)	0.33637 (17)	0.20326 (14)	0.0311 (3)
C17	0.53370 (17)	0.74164 (17)	0.31717 (15)	0.0329 (3)
C7	0.21820 (16)	0.27837 (17)	0.27795 (14)	0.0318 (3)
C10	0.45054 (16)	0.59076 (17)	0.25599 (14)	0.0309 (3)
C12	0.72587 (18)	0.41734 (17)	0.33436 (15)	0.0359 (3)
H12	0.6920	0.4043	0.4103	0.043*
C16	0.68582 (18)	0.46342 (19)	0.13698 (16)	0.0389 (4)
H16	0.6253	0.4825	0.0803	0.047*
C1	0.21339 (18)	0.06249 (18)	0.12568 (16)	0.0387 (4)
C6	0.13572 (17)	0.12766 (18)	0.21660 (15)	0.0356 (3)
C18	0.63321 (19)	0.77176 (18)	0.41909 (16)	0.0395 (4)
H18	0.6484	0.6947	0.4475	0.047*
C14	0.91775 (19)	0.4278 (2)	0.19263 (18)	0.0458 (4)
H14	1.0132	0.4233	0.1738	0.055*
C19	0.7104 (2)	0.91401 (19)	0.47948 (17)	0.0443 (4)
H19	0.7767	0.9320	0.5477	0.053*
C22	0.5151 (2)	0.8598 (2)	0.27498 (17)	0.0437 (4)
H22	0.4502	0.8424	0.2060	0.052*
C21	0.5915 (2)	1.0009 (2)	0.33447 (19)	0.0498 (5)
H21	0.5781	1.0782	0.3053	0.060*
C13	0.86727 (19)	0.4089 (2)	0.30515 (18)	0.0457 (4)
H13	0.9284	0.3905	0.3617	0.055*
C20	0.6883 (2)	1.02933 (18)	0.43755 (17)	0.0424 (4)
C15	0.82683 (19)	0.4533 (2)	0.10813 (18)	0.0442 (4)
H15	0.8601	0.4637	0.0315	0.053*
C5	−0.0038 (2)	0.0500 (2)	0.24311 (18)	0.0490 (4)
H5	−0.0552	0.0939	0.3045	0.059*
C2	0.1529 (2)	−0.0820 (2)	0.0605 (2)	0.0548 (5)
H2	0.2046	−0.1271	0.0003	0.066*
C3	0.0136 (3)	−0.1569 (2)	0.0876 (2)	0.0628 (6)
H3	−0.0285	−0.2536	0.0442	0.075*
C4	−0.0650 (2)	−0.0928 (2)	0.1771 (2)	0.0617 (6)
H4	−0.1589	−0.1457	0.1928	0.074*
C23	0.8590 (3)	1.2094 (3)	0.5952 (2)	0.0779 (7)
H23A	0.8091	1.1682	0.6589	0.117*
H23B	0.8948	1.3139	0.6248	0.117*
H23C	0.9416	1.1708	0.5735	0.117*
O1	0.19215 (13)	0.35372 (14)	0.37248 (11)	0.0448 (3)
O2	0.75789 (18)	1.17292 (14)	0.48941 (14)	0.0628 (4)
O3	0.28865 (12)	0.40970 (13)	0.12447 (10)	0.0405 (3)
N1	0.34693 (15)	0.56346 (15)	0.17074 (13)	0.0389 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0348 (2)	0.0447 (3)	0.0485 (3)	0.00839 (18)	0.00969 (18)	−0.00299 (19)
C9	0.0243 (7)	0.0343 (7)	0.0270 (7)	0.0066 (6)	0.0000 (5)	0.0077 (6)
C11	0.0248 (7)	0.0287 (7)	0.0324 (8)	0.0065 (6)	−0.0008 (6)	0.0062 (6)
C8	0.0265 (7)	0.0363 (8)	0.0300 (7)	0.0095 (6)	0.0015 (6)	0.0068 (6)
C17	0.0298 (7)	0.0372 (8)	0.0339 (8)	0.0119 (6)	0.0038 (6)	0.0102 (6)
C7	0.0239 (7)	0.0397 (8)	0.0324 (8)	0.0087 (6)	−0.0005 (6)	0.0104 (6)
C10	0.0251 (7)	0.0380 (8)	0.0315 (8)	0.0110 (6)	0.0031 (6)	0.0101 (6)
C12	0.0358 (8)	0.0379 (8)	0.0358 (8)	0.0132 (7)	−0.0012 (6)	0.0096 (7)
C16	0.0319 (8)	0.0512 (10)	0.0393 (9)	0.0150 (7)	0.0033 (7)	0.0185 (8)
C1	0.0359 (8)	0.0380 (8)	0.0394 (9)	0.0075 (7)	−0.0017 (7)	0.0077 (7)
C6	0.0319 (8)	0.0387 (8)	0.0350 (8)	0.0065 (6)	0.0001 (6)	0.0109 (7)
C18	0.0442 (9)	0.0353 (8)	0.0398 (9)	0.0119 (7)	−0.0041 (7)	0.0107 (7)
C14	0.0287 (8)	0.0481 (10)	0.0607 (12)	0.0151 (7)	0.0047 (8)	0.0087 (9)
C19	0.0482 (10)	0.0418 (9)	0.0392 (9)	0.0088 (8)	−0.0066 (8)	0.0077 (7)
C22	0.0437 (9)	0.0457 (10)	0.0456 (10)	0.0155 (8)	−0.0049 (8)	0.0155 (8)
C21	0.0590 (11)	0.0386 (9)	0.0568 (12)	0.0165 (8)	−0.0005 (9)	0.0187 (8)
C13	0.0376 (9)	0.0507 (10)	0.0528 (11)	0.0209 (8)	−0.0076 (8)	0.0109 (8)
C20	0.0453 (9)	0.0343 (8)	0.0446 (10)	0.0085 (7)	0.0072 (8)	0.0074 (7)
C15	0.0358 (9)	0.0522 (10)	0.0475 (10)	0.0138 (8)	0.0133 (7)	0.0164 (8)
C5	0.0388 (9)	0.0551 (11)	0.0472 (10)	0.0018 (8)	0.0070 (8)	0.0147 (9)
C2	0.0566 (12)	0.0413 (10)	0.0575 (12)	0.0094 (9)	0.0010 (9)	0.0005 (9)
C3	0.0654 (13)	0.0394 (10)	0.0675 (14)	−0.0046 (9)	−0.0059 (11)	0.0061 (9)
C4	0.0480 (11)	0.0546 (12)	0.0682 (14)	−0.0106 (9)	0.0027 (10)	0.0180 (11)
C23	0.0882 (18)	0.0500 (12)	0.0695 (16)	−0.0054 (12)	−0.0139 (13)	−0.0046 (11)
O1	0.0353 (6)	0.0540 (7)	0.0383 (6)	0.0110 (5)	0.0076 (5)	0.0005 (6)
O2	0.0791 (10)	0.0359 (7)	0.0628 (9)	0.0036 (7)	−0.0049 (8)	0.0074 (6)
O3	0.0368 (6)	0.0441 (6)	0.0361 (6)	0.0029 (5)	−0.0108 (5)	0.0124 (5)
N1	0.0353 (7)	0.0421 (8)	0.0398 (8)	0.0098 (6)	−0.0037 (6)	0.0128 (6)

Geometric parameters (Å, º) top

S1—C1	1.7667 (18)	C15—C16	1.386 (3)
S1—C8	1.8111 (17)	C17—C18	1.387 (2)
O1—C7	1.206 (2)	C17—C22	1.401 (3)
O2—C20	1.360 (2)	C18—C19	1.385 (3)
O2—C23	1.420 (3)	C19—C20	1.385 (3)
O3—N1	1.4196 (19)	C20—C21	1.385 (3)
O3—C8	1.465 (2)	C21—C22	1.372 (3)
N1—C10	1.281 (2)	C2—H2	0.9300
C1—C2	1.388 (3)	C3—H3	0.9300
C1—C6	1.389 (2)	C4—H4	0.9300
C2—C3	1.382 (3)	C5—H5	0.9300
C3—C4	1.380 (3)	C9—H9	0.9800
C4—C5	1.378 (3)	C12—H12	0.9300
C5—C6	1.391 (3)	C13—H13	0.9300
C6—C7	1.462 (2)	C14—H14	0.9300
C7—C8	1.548 (2)	C15—H15	0.9300
C8—C9	1.533 (2)	C16—H16	0.9300
C9—C10	1.515 (2)	C18—H18	0.9300
C9—C11	1.514 (2)	C19—H19	0.9300
C10—C17	1.464 (2)	C21—H21	0.9300
C11—C12	1.386 (2)	C22—H22	0.9300
C11—C16	1.384 (2)	C23—H23A	0.9600
C12—C13	1.386 (3)	C23—H23B	0.9600
C13—C14	1.378 (3)	C23—H23C	0.9600
C14—C15	1.376 (3)

C1—S1—C8	91.79 (8)	C18—C19—C20	119.55 (17)
C20—O2—C23	118.54 (17)	O2—C20—C19	124.60 (17)
N1—O3—C8	109.06 (11)	O2—C20—C21	115.76 (16)
O3—N1—C10	109.34 (13)	C19—C20—C21	119.62 (17)
S1—C1—C2	125.36 (14)	C20—C21—C22	120.64 (18)
S1—C1—C6	114.40 (13)	C17—C22—C21	120.68 (17)
C2—C1—C6	120.23 (17)	C1—C2—H2	121.00
C1—C2—C3	118.11 (19)	C3—C2—H2	121.00
C2—C3—C4	122.11 (19)	C2—C3—H3	119.00
C3—C4—C5	119.72 (19)	C4—C3—H3	119.00
C4—C5—C6	119.07 (18)	C3—C4—H4	120.00
C1—C6—C5	120.74 (16)	C5—C4—H4	120.00
C1—C6—C7	112.67 (15)	C4—C5—H5	120.00
C5—C6—C7	126.58 (16)	C6—C5—H5	120.00
O1—C7—C6	127.74 (15)	C8—C9—H9	109.00
O1—C7—C8	121.67 (15)	C10—C9—H9	109.00
C6—C7—C8	110.59 (13)	C11—C9—H9	109.00
S1—C8—O3	108.71 (10)	C11—C12—H12	120.00
S1—C8—C7	106.43 (11)	C13—C12—H12	120.00
S1—C8—C9	117.97 (11)	C12—C13—H13	120.00
O3—C8—C7	103.57 (12)	C14—C13—H13	120.00
O3—C8—C9	105.03 (12)	C13—C14—H14	120.00
C7—C8—C9	114.10 (12)	C15—C14—H14	120.00
C8—C9—C10	100.13 (12)	C14—C15—H15	120.00
C8—C9—C11	115.78 (13)	C16—C15—H15	120.00
C10—C9—C11	112.61 (13)	C11—C16—H16	120.00
N1—C10—C9	114.45 (14)	C15—C16—H16	120.00
N1—C10—C17	120.87 (15)	C17—C18—H18	119.00
C9—C10—C17	124.63 (14)	C19—C18—H18	119.00
C9—C11—C12	120.14 (14)	C18—C19—H19	120.00
C9—C11—C16	120.12 (14)	C20—C19—H19	120.00
C12—C11—C16	119.75 (15)	C20—C21—H21	120.00
C11—C12—C13	119.81 (16)	C22—C21—H21	120.00
C12—C13—C14	120.29 (17)	C17—C22—H22	120.00
C13—C14—C15	119.98 (17)	C21—C22—H22	120.00
C14—C15—C16	120.16 (18)	O2—C23—H23A	109.00
C11—C16—C15	120.01 (16)	O2—C23—H23B	110.00
C10—C17—C18	120.82 (15)	O2—C23—H23C	109.00
C10—C17—C22	121.19 (15)	H23A—C23—H23B	109.00
C18—C17—C22	117.99 (16)	H23A—C23—H23C	109.00
C17—C18—C19	121.50 (16)	H23B—C23—H23C	109.00

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1ⁱ	0.93	2.60	3.345 (2)	138

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇NO₃S
M_r	387.44
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.3644 (13), 9.8132 (14), 11.1502 (15)
α, β, γ (°)	103.575 (8), 90.360 (8), 106.089 (8)
V (Å³)	954.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.24 × 0.22 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14395, 4336, 3389
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.117, 1.08
No. of reflections	4336
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.25

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1ⁱ	0.93	2.60	3.345 (2)	138

Symmetry code: (i) x+1, y, z.

Acknowledgements

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

References

Al Houari, G., Bennani, A. K., Bennani, B., Daoudi, M., Benlarbi, N., El yazidi, M., Garrigues, B. & Kerbal, A. (2010). J. Mar. Chim. Heterocycl. 9, 36–43. CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, I. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
El yazidi, M., Daou, B., Bougrin, K. & Soufiaoui, M. (1994). J. Soc. Mar. Chim. 3, 54–51. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Toth, G., Balazs, B., Levai, A., Fisera, L. & Jedlovska, E. (1999). J. Mol. Struct. 508, 29–36. Web of Science CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Page o1850

doi:10.1107/S1600536811024408

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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