1',3',3'-Trimethyl-2,3-diphenyl-2,3-di-hydro-isoxazole-5(4H)-spiro-2'-indoline.

Two diastereoisomers of the title compound, C(25)H(26)N(2)O, have been prepared by cyclo-addition between 1,3,3-trimethyl-2-methyl-eneindoline and C-phenyl-N-phenyl-nitrone. The stereochemistry of the major diastereoisomer, viz. S,R/R,S, is confirmed by the X-ray analysis. The oxazole and the pyrole rings have envelope conformations. The packing is stabilized by weak C-H⋯π inter-actions involving the phenyl ring attached to the N atom of the oxazole and the phenyl ring of the indole fragment.

Related literature

For general background, see: Alonso-Perarnau et al. (1997 ▶); Cacciarini et al. (2000 ▶); Pariera et al. (1993 ▶). For related studies, see: Daran et al. (2006 ▶); Fihi et al. (1995 ▶, 2004 ▶); Roussel et al. (2000 ▶, 2003 ▶). For the synthetic procedure, see: Brüning et al. (1973 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C25H26N2O

M = 370.48

Orthorhombic,

a = 18.0393 (18) Å

b = 8.9854 (7) Å

c = 12.3947 (9) Å

V = 2009.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 180 (2) K

0.48 × 0.36 × 0.28 mm

Data collection

Stoe IPDS diffractometer

Absorption correction: none

19030 measured reflections

2021 independent reflections

1581 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.105

S = 1.15

2021 reflections

256 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.15 e Å−3

Data collection: IPDS (Stoe & Cie, 2000 ▶); cell refinement: IPDS; data reduction: X-RED (Stoe & Cie, 1996 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002062/fl2228sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002062/fl2228Isup2.hkl

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

Enhanced figure: interactive version of Fig. 1

C25H26N2O	F(000) = 792
Mr = 370.48	Dx = 1.225 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8000 reflections
a = 18.0393 (18) Å	θ = 1.7–26.2°
b = 8.9854 (7) Å	µ = 0.08 mm−1
c = 12.3947 (9) Å	T = 180 K
V = 2009.1 (3) Å3	Prism, colorless
Z = 4	0.48 × 0.36 × 0.28 mm

Stoe IPDS diffractometer	1581 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
graphite	θmax = 26.0°, θmin = 2.5°
φ scans	h = −22→22
19030 measured reflections	k = −11→11
2021 independent reflections	l = −14→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.061P)2] where P = (Fo2 + 2Fc2)/3
2021 reflections	(Δ/σ)max = 0.007
256 parameters	Δρmax = 0.26 e Å−3
1 restraint	Δρmin = −0.15 e Å−3

Experimental. The data were collected on a Stoe Imaging Plate Diffraction System (IPDS). The crystal-to-detector distance was 70 mm. 167 frames (4 min per frame) were obtained with 0 < φ < 250.5° and with the crystals rotated through 1.5° in φ. Coverage of the unique set was over 97.4% complete to at least 26.04°. Crystal decay was monitored by measuring 200 reflections per frame.

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.

	x	y	z	Uiso*/Ueq
C1	0.43438 (17)	0.9280 (3)	0.0510 (3)	0.0360 (7)
C2	0.52004 (18)	0.9356 (3)	0.0701 (3)	0.0398 (7)
C3	0.53941 (16)	1.0776 (3)	0.0091 (3)	0.0346 (7)
C4	0.60643 (18)	1.1346 (4)	−0.0231 (3)	0.0470 (8)
H4	0.6508	1.0802	−0.0111	0.056*
C5	0.6086 (2)	1.2734 (4)	−0.0738 (3)	0.0523 (9)
H5	0.6547	1.3141	−0.0964	0.063*
C6	0.5439 (2)	1.3510 (4)	−0.0909 (3)	0.0482 (9)
H6	0.5460	1.4452	−0.1256	0.058*
C7	0.47568 (18)	1.2952 (3)	−0.0588 (3)	0.0412 (7)
H7	0.4312	1.3493	−0.0710	0.049*
C8	0.47495 (15)	1.1576 (3)	−0.0082 (3)	0.0327 (7)
C9	0.34450 (16)	0.7260 (3)	0.0744 (3)	0.0363 (7)
H9	0.2955	0.7656	0.0500	0.044*
C10	0.38766 (19)	0.8462 (4)	0.1354 (3)	0.0458 (8)
H10A	0.3531	0.9161	0.1713	0.055*
H10B	0.4199	0.8006	0.1908	0.055*
C21	0.36716 (14)	0.6294 (3)	−0.1120 (2)	0.0294 (6)
C22	0.40480 (18)	0.6491 (3)	−0.2083 (3)	0.0367 (7)
H22	0.4453	0.7164	−0.2117	0.044*
C23	0.38362 (18)	0.5708 (3)	−0.2998 (3)	0.0429 (7)
H23	0.4091	0.5856	−0.3660	0.051*
C24	0.32514 (17)	0.4710 (4)	−0.2943 (3)	0.0438 (8)
H24	0.3110	0.4163	−0.3565	0.053*
C25	0.28787 (18)	0.4513 (4)	−0.1993 (3)	0.0414 (8)
H25	0.2482	0.3821	−0.1959	0.050*
C26	0.30746 (15)	0.5317 (3)	−0.1074 (3)	0.0352 (7)
H26	0.2803	0.5199	−0.0423	0.042*
C91	0.33383 (16)	0.5862 (3)	0.1405 (3)	0.0359 (7)
C92	0.39087 (17)	0.4871 (3)	0.1574 (3)	0.0418 (8)
H92	0.4380	0.5056	0.1259	0.050*
C93	0.3806 (2)	0.3610 (4)	0.2195 (3)	0.0511 (9)
H93	0.4205	0.2936	0.2302	0.061*
C94	0.3131 (2)	0.3330 (4)	0.2658 (3)	0.0537 (9)
H94	0.3064	0.2460	0.3082	0.064*
C95	0.2549 (2)	0.4299 (4)	0.2513 (3)	0.0532 (9)
H95	0.2083	0.4109	0.2841	0.064*
C96	0.26512 (18)	0.5563 (4)	0.1878 (3)	0.0462 (8)
H96	0.2249	0.6229	0.1767	0.055*
C111	0.33893 (17)	1.1202 (4)	0.0002 (4)	0.0526 (9)
H11A	0.3290	1.2248	0.0175	0.079*
H11B	0.3032	1.0567	0.0380	0.079*
H11C	0.3342	1.1051	−0.0778	0.079*
C211	0.5371 (2)	0.9600 (4)	0.1901 (3)	0.0531 (9)
H21A	0.5894	0.9871	0.1986	0.080*
H21B	0.5270	0.8682	0.2301	0.080*
H21C	0.5058	1.0403	0.2181	0.080*
C212	0.5604 (2)	0.7992 (4)	0.0285 (4)	0.0576 (11)
H21D	0.5484	0.7845	−0.0479	0.086*
H21E	0.5448	0.7117	0.0698	0.086*
H21F	0.6139	0.8134	0.0366	0.086*
N1	0.41386 (13)	1.0819 (2)	0.0341 (2)	0.0369 (6)
N2	0.39329 (13)	0.7023 (2)	−0.0180 (2)	0.0323 (6)
O1	0.41789 (11)	0.8501 (2)	−0.04964 (17)	0.0370 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0486 (17)	0.0268 (14)	0.0327 (18)	−0.0061 (13)	0.0006 (14)	−0.0026 (13)
C2	0.0508 (18)	0.0289 (15)	0.040 (2)	0.0018 (13)	−0.0082 (15)	0.0004 (13)
C3	0.0405 (16)	0.0306 (15)	0.0327 (19)	−0.0027 (12)	0.0001 (13)	0.0003 (12)
C4	0.0412 (17)	0.0488 (19)	0.051 (2)	−0.0023 (14)	0.0057 (15)	−0.0044 (17)
C5	0.061 (2)	0.052 (2)	0.045 (2)	−0.0220 (17)	0.0183 (17)	−0.0051 (16)
C6	0.075 (2)	0.0369 (18)	0.033 (2)	−0.0124 (16)	0.0080 (16)	−0.0010 (14)
C7	0.0545 (18)	0.0294 (16)	0.040 (2)	−0.0016 (13)	−0.0020 (15)	0.0007 (14)
C8	0.0393 (15)	0.0278 (15)	0.0308 (17)	−0.0033 (11)	0.0016 (13)	−0.0016 (12)
C9	0.0392 (16)	0.0353 (15)	0.0344 (19)	−0.0024 (13)	0.0062 (13)	−0.0029 (12)
C10	0.0589 (19)	0.0389 (17)	0.040 (2)	−0.0125 (14)	0.0075 (16)	−0.0062 (15)
C21	0.0326 (14)	0.0234 (13)	0.0322 (18)	0.0021 (11)	−0.0030 (12)	−0.0014 (12)
C22	0.0439 (16)	0.0333 (15)	0.0328 (19)	−0.0024 (12)	0.0017 (13)	0.0000 (13)
C23	0.0537 (18)	0.0432 (17)	0.0318 (18)	0.0047 (14)	0.0002 (15)	−0.0054 (15)
C24	0.0491 (18)	0.0433 (17)	0.039 (2)	0.0008 (13)	−0.0094 (16)	−0.0094 (15)
C25	0.0419 (16)	0.0399 (16)	0.042 (2)	−0.0044 (13)	−0.0055 (15)	−0.0063 (15)
C26	0.0323 (14)	0.0364 (15)	0.0369 (18)	−0.0013 (12)	−0.0045 (13)	0.0005 (14)
C91	0.0445 (16)	0.0323 (15)	0.0307 (17)	−0.0099 (13)	0.0010 (14)	−0.0021 (13)
C92	0.0427 (16)	0.0409 (17)	0.042 (2)	−0.0040 (13)	−0.0009 (14)	−0.0015 (15)
C93	0.061 (2)	0.0437 (19)	0.048 (2)	−0.0014 (15)	−0.0055 (17)	0.0017 (16)
C94	0.066 (2)	0.0429 (19)	0.052 (2)	−0.0193 (17)	−0.0025 (18)	0.0060 (17)
C95	0.054 (2)	0.058 (2)	0.047 (2)	−0.0182 (18)	0.0122 (17)	0.0016 (18)
C96	0.0472 (17)	0.0453 (18)	0.046 (2)	−0.0044 (14)	0.0023 (16)	−0.0026 (16)
C111	0.0396 (17)	0.0475 (18)	0.071 (3)	0.0017 (14)	−0.0049 (18)	−0.0098 (18)
C211	0.066 (2)	0.0489 (19)	0.045 (2)	−0.0085 (16)	−0.0146 (18)	0.0061 (17)
C212	0.055 (2)	0.0375 (18)	0.081 (3)	0.0098 (16)	−0.0048 (19)	−0.0012 (18)
N1	0.0374 (13)	0.0269 (12)	0.0464 (17)	−0.0029 (11)	0.0025 (11)	−0.0012 (12)
N2	0.0410 (13)	0.0248 (12)	0.0311 (15)	−0.0095 (10)	0.0016 (10)	−0.0016 (11)
O1	0.0570 (13)	0.0239 (10)	0.0302 (12)	−0.0113 (8)	0.0029 (10)	−0.0018 (9)

C1—N1	1.446 (4)	C23—C24	1.386 (5)
C1—O1	1.461 (4)	C23—H23	0.9500
C1—C10	1.531 (5)	C24—C25	1.367 (5)
C1—C2	1.565 (4)	C24—H24	0.9500
C2—C212	1.516 (5)	C25—C26	1.395 (4)
C2—C3	1.523 (4)	C25—H25	0.9500
C2—C211	1.534 (5)	C26—H26	0.9500
C3—C4	1.372 (4)	C91—C92	1.377 (4)
C3—C8	1.384 (4)	C91—C96	1.397 (4)
C4—C5	1.397 (5)	C92—C93	1.382 (5)
C4—H4	0.9500	C92—H92	0.9500
C5—C6	1.376 (5)	C93—C94	1.369 (6)
C5—H5	0.9500	C93—H93	0.9500
C6—C7	1.388 (5)	C94—C95	1.375 (6)
C6—H6	0.9500	C94—H94	0.9500
C7—C8	1.387 (4)	C95—C96	1.393 (5)
C7—H7	0.9500	C95—H95	0.9500
C8—N1	1.397 (4)	C96—H96	0.9500
C9—N2	1.460 (4)	C111—N1	1.457 (4)
C9—C91	1.512 (4)	C111—H11A	0.9800
C9—C10	1.531 (4)	C111—H11B	0.9800
C9—H9	1.0000	C111—H11C	0.9800
C10—H10A	0.9900	C211—H21A	0.9800
C10—H10B	0.9900	C211—H21B	0.9800
C21—C22	1.384 (4)	C211—H21C	0.9800
C21—C26	1.390 (4)	C212—H21D	0.9800
C21—N2	1.417 (4)	C212—H21E	0.9800
C22—C23	1.388 (5)	C212—H21F	0.9800
C22—H22	0.9500	N2—O1	1.454 (3)
N1—C1—O1	106.4 (2)	C25—C24—H24	120.0
N1—C1—C10	114.6 (3)	C23—C24—H24	120.0
O1—C1—C10	104.0 (2)	C24—C25—C26	120.8 (3)
N1—C1—C2	103.5 (2)	C24—C25—H25	119.6
O1—C1—C2	110.6 (2)	C26—C25—H25	119.6
C10—C1—C2	117.4 (3)	C21—C26—C25	119.3 (3)
C212—C2—C3	113.4 (3)	C21—C26—H26	120.3
C212—C2—C211	110.5 (3)	C25—C26—H26	120.3
C3—C2—C211	108.4 (3)	C92—C91—C96	118.4 (3)
C212—C2—C1	112.8 (3)	C92—C91—C9	121.6 (3)
C3—C2—C1	100.8 (2)	C96—C91—C9	120.0 (3)
C211—C2—C1	110.6 (3)	C91—C92—C93	120.9 (3)
C4—C3—C8	120.1 (3)	C91—C92—H92	119.5
C4—C3—C2	131.2 (3)	C93—C92—H92	119.5
C8—C3—C2	108.6 (3)	C94—C93—C92	120.2 (3)
C3—C4—C5	119.3 (3)	C94—C93—H93	119.9
C3—C4—H4	120.4	C92—C93—H93	119.9
C5—C4—H4	120.4	C93—C94—C95	120.5 (3)
C6—C5—C4	119.9 (3)	C93—C94—H94	119.8
C6—C5—H5	120.1	C95—C94—H94	119.8
C4—C5—H5	120.1	C94—C95—C96	119.3 (3)
C5—C6—C7	121.7 (3)	C94—C95—H95	120.3
C5—C6—H6	119.2	C96—C95—H95	120.3
C7—C6—H6	119.2	C95—C96—C91	120.7 (3)
C8—C7—C6	117.4 (3)	C95—C96—H96	119.7
C8—C7—H7	121.3	C91—C96—H96	119.7
C6—C7—H7	121.3	N1—C111—H11A	109.5
C3—C8—C7	121.7 (3)	N1—C111—H11B	109.5
C3—C8—N1	110.6 (3)	H11A—C111—H11B	109.5
C7—C8—N1	127.7 (3)	N1—C111—H11C	109.5
N2—C9—C91	112.4 (2)	H11A—C111—H11C	109.5
N2—C9—C10	100.6 (2)	H11B—C111—H11C	109.5
C91—C9—C10	112.6 (3)	C2—C211—H21A	109.5
N2—C9—H9	110.3	C2—C211—H21B	109.5
C91—C9—H9	110.3	H21A—C211—H21B	109.5
C10—C9—H9	110.3	C2—C211—H21C	109.5
C1—C10—C9	106.4 (3)	H21A—C211—H21C	109.5
C1—C10—H10A	110.5	H21B—C211—H21C	109.5
C9—C10—H10A	110.5	C2—C212—H21D	109.5
C1—C10—H10B	110.5	C2—C212—H21E	109.5
C9—C10—H10B	110.5	H21D—C212—H21E	109.5
H10A—C10—H10B	108.6	C2—C212—H21F	109.5
C22—C21—C26	119.7 (3)	H21D—C212—H21F	109.5
C22—C21—N2	119.1 (2)	H21E—C212—H21F	109.5
C26—C21—N2	121.0 (3)	C8—N1—C1	108.5 (2)
C21—C22—C23	120.3 (3)	C8—N1—C111	120.6 (3)
C21—C22—H22	119.8	C1—N1—C111	120.4 (2)
C23—C22—H22	119.8	C21—N2—O1	107.6 (2)
C24—C23—C22	119.8 (3)	C21—N2—C9	120.8 (2)
C24—C23—H23	120.1	O1—N2—C9	105.2 (2)
C22—C23—H23	120.1	N2—O1—C1	105.6 (2)
C25—C24—C23	120.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg1i	0.95	2.89	3.735 (3)	149
C23—H23···Cg2ii	0.95	2.95	3.803 (4)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1is the centroid of the C21–C26 ring and Cg2 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg1i	0.95	2.89	3.735 (3)	149
C23—H23⋯Cg2ii	0.95	2.95	3.803 (4)	150

Symmetry codes: (i) ; (ii) .