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

Mahfoud, A.; Al Houari, G.; El Yazidi, M.; Saadi, M.; El Ammari, L.

doi:10.1107/S2056989015019581

organic compounds

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ISSN: 2056-9890

Volume 71| Part 11| November 2015| Pages o873-o874

https://doi.org/10.1107/S2056989015019581

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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 and Lahcen El Ammari ^b

^aLaboratoire de Chimie Organique, Faculté des Sciences Dhar el Mahraz, Université Sidi Mohammed Ben Abdellah, BP 1796 Atlas, 30000 Fès, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: asmae.mahfoud@yahoo.fr

Edited by H. Ishida, Okayama University, Japan (Received 6 October 2015; accepted 15 October 2015; online 24 October 2015)

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.

CCDC reference: 1431561

1. 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 ).

2. Experimental

2.1. Crystal data

C₃₀H₂₃NO₂
M_r = 429.49
Monoclinic, P 2₁ /n
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

2.2. Data collection

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

2.3. Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O1ⁱ	0.98	2.47	3.4169 (18)	163
C2—H2⋯N1ⁱⁱ	0.93	2.56	3.280 (2)	135
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

CCDC reference: 1431561

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015019581/is5427sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015019581/is5427Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015019581/is5427Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

	Fig. 1. 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.
	Fig. 2. : Partial crystal packing for the title compound showing molecules linked by hydrogen bonds as dashed lines.

3,4'-Diphenyl-3'-p-tolyl-4'H-spiro[indan-2,5'-[1,2]oxazol]-1-one top

Crystal data top

C₃₀H₂₃NO₂	F(000) = 904
M_r = 429.49	D_x = 1.239 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.7381 (7) Å	Cell parameters from 5942 reflections
b = 20.5072 (14) Å	θ = 2.4–28.7°
c = 11.8261 (8) Å	µ = 0.08 mm⁻¹
β = 102.836 (2)°	T = 296 K
V = 2302.7 (3) Å³	Block, colourless
Z = 4	0.42 × 0.31 × 0.26 mm

Data collection top

Bruker X8 APEX diffractometer	3783 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.042
Graphite monochromator	θ_max = 28.7°, θ_min = 2.4°
φ and ω scans	h = −12→13
38803 measured reflections	k = −27→27
5942 independent reflections	l = −15→15

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.150	w = 1/[σ²(F_o²) + (0.0706P)² + 0.3191P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
5942 reflections	Δρ_max = 0.21 e Å⁻³
298 parameters	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₃₀H₂₃NO₂	V = 2302.7 (3) Å³
M_r = 429.49	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7381 (7) Å	µ = 0.08 mm⁻¹
b = 20.5072 (14) Å	T = 296 K
c = 11.8261 (8) Å	0.42 × 0.31 × 0.26 mm
β = 102.836 (2)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
5942 reflections	Δρ_min = −0.21 e Å⁻³
298 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.

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

	x	y	z	U_iso*/U_eq
C1	0.63361 (17)	0.65004 (7)	0.77155 (13)	0.0434 (4)
C2	0.7018 (2)	0.67536 (9)	0.87761 (15)	0.0615 (5)
H2	0.7760	0.7046	0.8828	0.074*
C3	0.6574 (3)	0.65632 (12)	0.97544 (16)	0.0798 (6)
H3	0.7009	0.6739	1.0469	0.096*
C4	0.5499 (3)	0.61194 (12)	0.96970 (17)	0.0823 (7)
H4	0.5226	0.5999	1.0372	0.099*
C5	0.4821 (2)	0.58502 (10)	0.86457 (16)	0.0646 (5)
H5	0.4103	0.5546	0.8602	0.078*
C6	0.52553 (17)	0.60528 (7)	0.76583 (13)	0.0451 (4)
C7	0.47174 (15)	0.58614 (7)	0.64401 (12)	0.0391 (3)
C8	0.52976 (15)	0.63745 (6)	0.57117 (12)	0.0363 (3)
C9	0.66333 (16)	0.66398 (7)	0.65309 (12)	0.0406 (3)
H9	0.6690	0.7112	0.6424	0.049*
C10	0.52416 (15)	0.61711 (6)	0.44621 (11)	0.0355 (3)
H10	0.5327	0.5696	0.4410	0.043*
C11	0.37483 (16)	0.63844 (7)	0.39210 (13)	0.0397 (3)
C12	0.29663 (16)	0.62078 (7)	0.27526 (13)	0.0419 (3)
C13	0.17247 (17)	0.65406 (9)	0.22408 (15)	0.0541 (4)
H13	0.1390	0.6870	0.2649	0.065*
C14	0.1000 (2)	0.63836 (10)	0.11407 (16)	0.0629 (5)
H14	0.0188	0.6615	0.0811	0.075*
C15	0.1444 (2)	0.58901 (10)	0.05096 (15)	0.0603 (5)
C16	0.2661 (2)	0.55529 (9)	0.10290 (15)	0.0598 (5)
H16	0.2973	0.5213	0.0629	0.072*
C17	0.34171 (18)	0.57134 (8)	0.21307 (14)	0.0500 (4)
H17	0.4236	0.5486	0.2454	0.060*
C18	0.0653 (3)	0.57206 (13)	−0.07049 (18)	0.0886 (7)
H18A	0.1121	0.5368	−0.0998	0.133*
H18B	−0.0290	0.5592	−0.0690	0.133*
H18C	0.0627	0.6094	−0.1198	0.133*
C19	0.79899 (16)	0.63248 (8)	0.63886 (12)	0.0439 (4)
C20	0.81576 (18)	0.56531 (9)	0.64447 (14)	0.0526 (4)
H20	0.7438	0.5392	0.6596	0.063*
C21	0.9383 (2)	0.53679 (12)	0.62782 (17)	0.0737 (6)
H21	0.9476	0.4916	0.6306	0.088*
C22	1.0455 (2)	0.57422 (17)	0.6073 (2)	0.0898 (8)
H22	1.1276	0.5547	0.5960	0.108*
C23	1.0322 (2)	0.64040 (16)	0.60343 (19)	0.0884 (8)
H23	1.1060	0.6660	0.5902	0.106*
C24	0.9092 (2)	0.66999 (11)	0.61901 (16)	0.0648 (5)
H24	0.9011	0.7152	0.6161	0.078*
C25	0.62860 (15)	0.65060 (7)	0.38786 (12)	0.0388 (3)
C26	0.62869 (19)	0.71794 (8)	0.37655 (15)	0.0535 (4)
H26	0.5615	0.7427	0.4020	0.064*
C27	0.7283 (2)	0.74848 (9)	0.32761 (17)	0.0659 (5)
H27	0.7285	0.7937	0.3213	0.079*
C28	0.8269 (2)	0.71204 (11)	0.28830 (16)	0.0674 (5)
H28	0.8938	0.7326	0.2555	0.081*
C29	0.8263 (2)	0.64531 (10)	0.29763 (16)	0.0623 (5)
H29	0.8927	0.6207	0.2708	0.075*
C30	0.72750 (17)	0.61456 (8)	0.34679 (13)	0.0470 (4)
H30	0.7274	0.5693	0.3523	0.056*
N1	0.32254 (14)	0.67817 (6)	0.45484 (11)	0.0485 (3)
O1	0.39627 (12)	0.54081 (5)	0.60560 (10)	0.0516 (3)
O2	0.42173 (12)	0.68874 (5)	0.56063 (9)	0.0479 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0497 (9)	0.0408 (8)	0.0407 (8)	0.0036 (7)	0.0121 (7)	−0.0042 (6)
C2	0.0716 (12)	0.0627 (11)	0.0474 (9)	−0.0014 (9)	0.0075 (9)	−0.0116 (8)
C3	0.1003 (18)	0.0979 (16)	0.0397 (9)	0.0050 (14)	0.0127 (10)	−0.0130 (9)
C4	0.0994 (18)	0.1110 (18)	0.0431 (10)	0.0056 (15)	0.0299 (11)	0.0040 (10)
C5	0.0721 (13)	0.0765 (12)	0.0525 (10)	0.0011 (10)	0.0297 (9)	0.0065 (9)
C6	0.0502 (9)	0.0455 (8)	0.0424 (8)	0.0034 (7)	0.0163 (7)	0.0007 (6)
C7	0.0387 (8)	0.0359 (7)	0.0450 (8)	0.0019 (6)	0.0143 (6)	−0.0006 (6)
C8	0.0380 (8)	0.0327 (6)	0.0386 (7)	0.0019 (6)	0.0095 (6)	−0.0007 (5)
C9	0.0474 (9)	0.0342 (7)	0.0400 (7)	−0.0052 (6)	0.0092 (6)	−0.0037 (6)
C10	0.0365 (7)	0.0336 (7)	0.0367 (7)	0.0011 (6)	0.0087 (6)	0.0011 (5)
C11	0.0376 (8)	0.0384 (7)	0.0432 (8)	0.0009 (6)	0.0091 (6)	0.0056 (6)
C12	0.0380 (8)	0.0449 (8)	0.0421 (8)	−0.0041 (6)	0.0071 (6)	0.0079 (6)
C13	0.0424 (9)	0.0596 (10)	0.0571 (10)	0.0033 (8)	0.0043 (8)	0.0058 (8)
C14	0.0469 (10)	0.0764 (12)	0.0578 (10)	0.0000 (9)	−0.0045 (8)	0.0142 (9)
C15	0.0549 (11)	0.0763 (12)	0.0443 (9)	−0.0159 (9)	−0.0007 (8)	0.0122 (8)
C16	0.0639 (12)	0.0685 (11)	0.0448 (9)	−0.0030 (9)	0.0077 (8)	−0.0029 (8)
C17	0.0474 (9)	0.0564 (9)	0.0434 (8)	0.0023 (7)	0.0044 (7)	0.0032 (7)
C18	0.0867 (16)	0.1143 (18)	0.0518 (11)	−0.0168 (14)	−0.0127 (11)	0.0055 (11)
C19	0.0387 (8)	0.0588 (9)	0.0328 (7)	−0.0071 (7)	0.0048 (6)	−0.0054 (6)
C20	0.0466 (9)	0.0609 (10)	0.0495 (9)	0.0062 (8)	0.0086 (7)	−0.0033 (7)
C21	0.0593 (13)	0.0976 (15)	0.0604 (12)	0.0261 (12)	0.0052 (10)	−0.0129 (10)
C22	0.0490 (13)	0.153 (2)	0.0647 (13)	0.0147 (15)	0.0076 (10)	−0.0331 (15)
C23	0.0452 (12)	0.158 (3)	0.0641 (13)	−0.0305 (14)	0.0169 (10)	−0.0259 (14)
C24	0.0526 (11)	0.0887 (13)	0.0540 (10)	−0.0245 (10)	0.0137 (8)	−0.0125 (9)
C25	0.0376 (8)	0.0438 (8)	0.0339 (7)	−0.0015 (6)	0.0059 (6)	0.0043 (5)
C26	0.0528 (10)	0.0465 (9)	0.0632 (10)	0.0021 (8)	0.0168 (8)	0.0103 (7)
C27	0.0689 (13)	0.0532 (10)	0.0760 (12)	−0.0082 (9)	0.0166 (10)	0.0216 (9)
C28	0.0603 (12)	0.0833 (14)	0.0628 (11)	−0.0131 (10)	0.0230 (9)	0.0221 (10)
C29	0.0580 (11)	0.0778 (13)	0.0579 (10)	−0.0001 (9)	0.0277 (9)	0.0075 (9)
C30	0.0486 (9)	0.0516 (9)	0.0431 (8)	−0.0007 (7)	0.0153 (7)	0.0022 (6)
N1	0.0471 (8)	0.0489 (7)	0.0481 (7)	0.0095 (6)	0.0079 (6)	0.0031 (6)
O1	0.0489 (7)	0.0466 (6)	0.0612 (7)	−0.0109 (5)	0.0165 (5)	−0.0027 (5)
O2	0.0516 (7)	0.0433 (6)	0.0473 (6)	0.0134 (5)	0.0082 (5)	−0.0046 (4)

Geometric parameters (Å, º) top

C1—C2	1.383 (2)	C15—C18	1.512 (3)
C1—C6	1.387 (2)	C16—C17	1.386 (2)
C1—C9	1.519 (2)	C16—H16	0.9300
C2—C3	1.379 (3)	C17—H17	0.9300
C2—H2	0.9300	C18—H18A	0.9600
C3—C4	1.377 (3)	C18—H18B	0.9600
C3—H3	0.9300	C18—H18C	0.9600
C4—C5	1.386 (3)	C19—C24	1.382 (2)
C4—H4	0.9300	C19—C20	1.387 (2)
C5—C6	1.391 (2)	C20—C21	1.382 (3)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.473 (2)	C21—C22	1.360 (4)
C7—O1	1.2093 (17)	C21—H21	0.9300
C7—C8	1.544 (2)	C22—C23	1.363 (4)
C8—O2	1.4730 (17)	C22—H22	0.9300
C8—C10	1.5248 (19)	C23—C24	1.391 (3)
C8—C9	1.5384 (19)	C23—H23	0.9300
C9—C19	1.513 (2)	C24—H24	0.9300
C9—H9	0.9800	C25—C30	1.385 (2)
C10—C25	1.515 (2)	C25—C26	1.387 (2)
C10—C11	1.517 (2)	C26—C27	1.384 (2)
C10—H10	0.9800	C26—H26	0.9300
C11—N1	1.2813 (19)	C27—C28	1.377 (3)
C11—C12	1.467 (2)	C27—H27	0.9300
C12—C17	1.380 (2)	C28—C29	1.373 (3)
C12—C13	1.403 (2)	C28—H28	0.9300
C13—C14	1.374 (2)	C29—C30	1.382 (2)
C13—H13	0.9300	C29—H29	0.9300
C14—C15	1.383 (3)	C30—H30	0.9300
C14—H14	0.9300	N1—O2	1.4171 (16)
C15—C16	1.391 (3)

C2—C1—C6	119.92 (16)	C14—C15—C18	121.76 (19)
C2—C1—C9	127.88 (16)	C16—C15—C18	120.6 (2)
C6—C1—C9	112.18 (12)	C17—C16—C15	121.30 (18)
C3—C2—C1	118.52 (19)	C17—C16—H16	119.4
C3—C2—H2	120.7	C15—C16—H16	119.4
C1—C2—H2	120.7	C12—C17—C16	120.64 (16)
C4—C3—C2	121.51 (19)	C12—C17—H17	119.7
C4—C3—H3	119.2	C16—C17—H17	119.7
C2—C3—H3	119.2	C15—C18—H18A	109.5
C3—C4—C5	120.86 (19)	C15—C18—H18B	109.5
C3—C4—H4	119.6	H18A—C18—H18B	109.5
C5—C4—H4	119.6	C15—C18—H18C	109.5
C4—C5—C6	117.4 (2)	H18A—C18—H18C	109.5
C4—C5—H5	121.3	H18B—C18—H18C	109.5
C6—C5—H5	121.3	C24—C19—C20	118.24 (17)
C1—C6—C5	121.73 (16)	C24—C19—C9	120.75 (16)
C1—C6—C7	108.98 (13)	C20—C19—C9	121.00 (14)
C5—C6—C7	129.29 (16)	C21—C20—C19	120.65 (19)
O1—C7—C6	128.81 (14)	C21—C20—H20	119.7
O1—C7—C8	125.55 (13)	C19—C20—H20	119.7
C6—C7—C8	105.63 (12)	C22—C21—C20	120.5 (2)
O2—C8—C10	104.02 (10)	C22—C21—H21	119.7
O2—C8—C9	106.79 (11)	C20—C21—H21	119.7
C10—C8—C9	123.38 (12)	C21—C22—C23	119.8 (2)
O2—C8—C7	101.00 (11)	C21—C22—H22	120.1
C10—C8—C7	114.55 (11)	C23—C22—H22	120.1
C9—C8—C7	104.63 (11)	C22—C23—C24	120.5 (2)
C19—C9—C1	111.84 (12)	C22—C23—H23	119.7
C19—C9—C8	114.58 (11)	C24—C23—H23	119.7
C1—C9—C8	101.92 (12)	C19—C24—C23	120.2 (2)
C19—C9—H9	109.4	C19—C24—H24	119.9
C1—C9—H9	109.4	C23—C24—H24	119.9
C8—C9—H9	109.4	C30—C25—C26	118.82 (15)
C25—C10—C11	110.78 (11)	C30—C25—C10	120.50 (13)
C25—C10—C8	115.75 (11)	C26—C25—C10	120.67 (14)
C11—C10—C8	98.88 (11)	C27—C26—C25	120.40 (17)
C25—C10—H10	110.3	C27—C26—H26	119.8
C11—C10—H10	110.3	C25—C26—H26	119.8
C8—C10—H10	110.3	C28—C27—C26	120.10 (17)
N1—C11—C12	120.82 (14)	C28—C27—H27	120.0
N1—C11—C10	113.96 (13)	C26—C27—H27	120.0
C12—C11—C10	125.06 (13)	C29—C28—C27	119.91 (17)
C17—C12—C13	118.23 (15)	C29—C28—H28	120.0
C17—C12—C11	121.54 (14)	C27—C28—H28	120.0
C13—C12—C11	120.23 (15)	C28—C29—C30	120.25 (18)
C14—C13—C12	120.46 (18)	C28—C29—H29	119.9
C14—C13—H13	119.8	C30—C29—H29	119.9
C12—C13—H13	119.8	C29—C30—C25	120.50 (16)
C13—C14—C15	121.73 (17)	C29—C30—H30	119.7
C13—C14—H14	119.1	C25—C30—H30	119.7
C15—C14—H14	119.1	C11—N1—O2	109.14 (12)
C14—C15—C16	117.61 (16)	N1—O2—C8	107.42 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1ⁱ	0.98	2.47	3.4169 (18)	163
C2—H2···N1ⁱⁱ	0.93	2.56	3.280 (2)	135

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1ⁱ	0.98	2.47	3.4169 (18)	163
C2—H2···N1ⁱⁱ	0.93	2.56	3.280 (2)	135

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+3/2, z+1/2.

Acknowledgements

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

References

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Al Houari, G., Bennani-Kella, A., Bennani, B., Daoudi, M., Benlarbi, N., El Yazidi, M., Garrigues, B. & Kerbal, A. (2010). J. Marocain Chim. Heterocycl. 9, 36–43. CAS Google Scholar
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Volume 71| Part 11| November 2015| Pages o873-o874

https://doi.org/10.1107/S2056989015019581

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

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

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

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