1-Allyl-3,3-diphenyl-indolin-2-one.

In the title compound, C(23)H(19)NO, the oxindole residue is essentially planar and is almost perpendicular to the phenyl rings [dihedral angles = 72.1 (6) and 77.6 (6)°]. The mol-ecular packing is stabilized by C-H⋯O hydrogen bonds and C-H⋯N inter-actions.

Related literature

For related literature, see: Bandini et al. (2005 ▶); Florin et al. (1980 ▶); Govind et al. (2003 ▶); Rajeswaran et al. (1999 ▶); Ramirez & Garcia-Rubio (2003 ▶).

Experimental

Crystal data

C23H19NO

M = 325.39

Orthorhombic,

a = 8.8449 (3) Å

b = 12.3879 (4) Å

c = 16.0377 (4) Å

V = 1757.25 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 (2) K

0.30 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEX2 diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.978, T max = 0.985

14793 measured reflections

3559 independent reflections

2611 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.141

S = 1.09

3559 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009446/gw2038sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009446/gw2038Isup2.hkl

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

C23H19NO	F000 = 688
Mr = 325.39	Dx = 1.230 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: p 2ac 2ab	Cell parameters from 4984 reflections
a = 8.8449 (3) Å	θ = 2.5–30.3º
b = 12.3879 (4) Å	µ = 0.08 mm−1
c = 16.0377 (4) Å	T = 293 (2) K
V = 1757.25 (9) Å3	Prism, yellow
Z = 4	0.30 × 0.24 × 0.20 mm

Bruker Kappa APEX2 diffractometer	3559 independent reflections
Radiation source: fine-focus sealed tube	2611 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 293(2) K	θmax = 32.6º
ω and φ scans	θmin = 2.5º
Absorption correction: multi-scan(Blessing, 1995)	h = −13→11
Tmin = 0.978, Tmax = 0.985	k = −18→14
14793 measured reflections	l = −20→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0653P)2 + 0.2107P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
3559 reflections	Δρmax = 0.31 e Å−3
226 parameters	Δρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C2	0.7623 (2)	0.14099 (15)	0.09508 (12)	0.0367 (4)
C3	0.7846 (2)	0.02597 (14)	0.13122 (10)	0.0331 (3)
C4	0.8751 (2)	−0.02725 (15)	0.06249 (11)	0.0349 (4)
C5	0.9240 (3)	−0.13195 (17)	0.05340 (13)	0.0454 (5)
H5	0.9017	−0.1836	0.0937	0.055*
C6	1.0075 (3)	−0.1595 (2)	−0.01711 (14)	0.0523 (5)
H6	1.0420	−0.2299	−0.0239	0.063*
C7	1.0390 (3)	−0.0829 (2)	−0.07656 (14)	0.0570 (6)
H7	1.0952	−0.1025	−0.1231	0.068*
C8	0.9897 (3)	0.0220 (2)	−0.06920 (13)	0.0517 (5)
H8	1.0119	0.0733	−0.1097	0.062*
C9	0.9059 (2)	0.04807 (16)	0.00085 (11)	0.0387 (4)
C10	0.8516 (3)	0.24727 (19)	−0.02570 (15)	0.0543 (6)
H10A	0.9527	0.2513	−0.0490	0.065*
H10B	0.8404	0.3073	0.0126	0.065*
C11	0.7411 (3)	0.2612 (2)	−0.09456 (17)	0.0675 (7)
H11	0.7486	0.3252	−0.1246	0.081*
C12	0.6406 (4)	0.1988 (3)	−0.1170 (2)	0.0792 (9)
H12A	0.6272	0.1334	−0.0894	0.095*
H12B	0.5781	0.2170	−0.1614	0.095*
C13	0.8731 (2)	0.03991 (15)	0.21273 (11)	0.0363 (4)
C14	0.8029 (3)	0.08647 (16)	0.28170 (13)	0.0439 (4)
H14	0.7018	0.1067	0.2784	0.053*
C15	0.8814 (3)	0.10282 (19)	0.35467 (14)	0.0534 (6)
H15	0.8327	0.1333	0.4004	0.064*
C16	1.0312 (3)	0.0745 (2)	0.36051 (15)	0.0643 (7)
H16	1.0845	0.0863	0.4097	0.077*
C17	1.1015 (3)	0.0285 (3)	0.29290 (17)	0.0782 (9)
H17	1.2028	0.0090	0.2964	0.094*
C18	1.0225 (3)	0.0110 (3)	0.21964 (15)	0.0597 (6)
H18	1.0713	−0.0208	0.1745	0.072*
C19	0.6328 (2)	−0.03049 (15)	0.14321 (11)	0.0347 (4)
C20	0.5121 (2)	−0.00927 (18)	0.09117 (14)	0.0446 (5)
H20	0.5221	0.0426	0.0496	0.054*
C21	0.3761 (3)	−0.0640 (2)	0.09980 (17)	0.0548 (6)
H21	0.2957	−0.0484	0.0645	0.066*
C22	0.3604 (3)	−0.1413 (2)	0.16061 (17)	0.0572 (6)
H22	0.2690	−0.1775	0.1669	0.069*
C23	0.4792 (3)	−0.1650 (2)	0.21185 (15)	0.0596 (6)
H23	0.4688	−0.2178	0.2526	0.072*
C24	0.6155 (3)	−0.11038 (18)	0.20325 (13)	0.0500 (5)
H24	0.6961	−0.1275	0.2381	0.060*
N1	0.8393 (2)	0.14731 (13)	0.02162 (10)	0.0414 (4)
O1	0.69142 (19)	0.21379 (12)	0.12636 (10)	0.0505 (4)

	U11	U22	U33	U12	U13	U23
C2	0.0361 (9)	0.0371 (9)	0.0367 (8)	−0.0015 (7)	0.0006 (7)	0.0024 (7)
C3	0.0331 (8)	0.0371 (8)	0.0290 (7)	0.0005 (7)	0.0027 (6)	0.0012 (7)
C4	0.0326 (8)	0.0408 (9)	0.0313 (8)	−0.0012 (7)	0.0004 (7)	−0.0026 (7)
C5	0.0469 (11)	0.0442 (10)	0.0452 (10)	0.0025 (9)	0.0027 (9)	−0.0034 (9)
C6	0.0480 (12)	0.0570 (12)	0.0518 (12)	0.0076 (10)	0.0008 (10)	−0.0170 (10)
C7	0.0455 (12)	0.0809 (17)	0.0446 (11)	−0.0002 (11)	0.0090 (10)	−0.0169 (11)
C8	0.0486 (12)	0.0700 (14)	0.0363 (10)	−0.0056 (11)	0.0102 (9)	0.0001 (10)
C9	0.0349 (9)	0.0463 (9)	0.0351 (8)	−0.0051 (8)	0.0027 (7)	0.0006 (8)
C10	0.0559 (13)	0.0514 (11)	0.0557 (13)	−0.0076 (10)	0.0055 (11)	0.0204 (11)
C11	0.0746 (17)	0.0706 (17)	0.0574 (15)	0.0029 (15)	−0.0022 (14)	0.0130 (13)
C12	0.088 (2)	0.084 (2)	0.0650 (17)	0.0092 (19)	0.0007 (16)	−0.0026 (15)
C13	0.0369 (9)	0.0391 (9)	0.0329 (8)	−0.0001 (7)	0.0011 (7)	0.0000 (7)
C14	0.0458 (11)	0.0473 (10)	0.0386 (10)	0.0052 (9)	0.0013 (8)	−0.0040 (8)
C15	0.0651 (15)	0.0582 (13)	0.0369 (10)	0.0023 (12)	0.0004 (10)	−0.0089 (9)
C16	0.0631 (16)	0.0861 (18)	0.0437 (12)	−0.0075 (14)	−0.0126 (11)	−0.0102 (12)
C17	0.0463 (13)	0.126 (3)	0.0618 (15)	0.0108 (17)	−0.0163 (12)	−0.0218 (18)
C18	0.0395 (11)	0.0917 (18)	0.0479 (11)	0.0075 (12)	−0.0028 (9)	−0.0165 (12)
C19	0.0354 (9)	0.0368 (8)	0.0319 (8)	−0.0017 (7)	0.0050 (6)	0.0008 (7)
C20	0.0394 (10)	0.0457 (10)	0.0489 (11)	0.0001 (8)	0.0001 (8)	0.0063 (9)
C21	0.0343 (10)	0.0569 (13)	0.0730 (15)	−0.0010 (9)	−0.0001 (10)	−0.0082 (12)
C22	0.0471 (12)	0.0530 (12)	0.0713 (15)	−0.0151 (10)	0.0185 (11)	−0.0132 (12)
C23	0.0773 (17)	0.0548 (13)	0.0468 (11)	−0.0253 (12)	0.0135 (12)	0.0028 (10)
C24	0.0602 (14)	0.0513 (12)	0.0387 (10)	−0.0141 (11)	−0.0024 (9)	0.0105 (9)
N1	0.0439 (9)	0.0401 (8)	0.0401 (8)	−0.0042 (7)	0.0052 (7)	0.0081 (7)
O1	0.0565 (9)	0.0411 (7)	0.0539 (9)	0.0091 (7)	0.0066 (7)	0.0007 (6)

C2—O1	1.207 (2)	C12—H12B	0.9300
C2—N1	1.363 (2)	C13—C18	1.374 (3)
C2—C3	1.551 (3)	C13—C14	1.393 (3)
C3—C4	1.513 (2)	C14—C15	1.376 (3)
C3—C19	1.526 (3)	C14—H14	0.9300
C3—C13	1.533 (2)	C15—C16	1.374 (4)
C4—C5	1.375 (3)	C15—H15	0.9300
C4—C9	1.387 (3)	C16—C17	1.373 (4)
C5—C6	1.393 (3)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.384 (3)
C6—C7	1.374 (3)	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.375 (4)	C19—C20	1.380 (3)
C7—H7	0.9300	C19—C24	1.389 (3)
C8—C9	1.384 (3)	C20—C21	1.388 (3)
C8—H8	0.9300	C20—H20	0.9300
C9—N1	1.404 (3)	C21—C22	1.374 (4)
C10—N1	1.456 (3)	C21—H21	0.9300
C10—C11	1.485 (4)	C22—C23	1.366 (4)
C10—H10A	0.9700	C22—H22	0.9300
C10—H10B	0.9700	C23—C24	1.390 (3)
C11—C12	1.232 (4)	C23—H23	0.9300
C11—H11	0.9300	C24—H24	0.9300
C12—H12A	0.9300
O1—C2—N1	125.14 (18)	C18—C13—C14	118.21 (19)
O1—C2—C3	126.65 (17)	C18—C13—C3	122.03 (18)
N1—C2—C3	108.20 (15)	C14—C13—C3	119.73 (17)
C4—C3—C19	110.95 (15)	C15—C14—C13	120.7 (2)
C4—C3—C13	113.58 (15)	C15—C14—H14	119.6
C19—C3—C13	113.16 (14)	C13—C14—H14	119.6
C4—C3—C2	101.25 (14)	C16—C15—C14	120.5 (2)
C19—C3—C2	110.88 (15)	C16—C15—H15	119.8
C13—C3—C2	106.26 (14)	C14—C15—H15	119.8
C5—C4—C9	119.81 (17)	C17—C16—C15	119.2 (2)
C5—C4—C3	130.89 (17)	C17—C16—H16	120.4
C9—C4—C3	109.29 (16)	C15—C16—H16	120.4
C4—C5—C6	118.9 (2)	C16—C17—C18	120.5 (2)
C4—C5—H5	120.5	C16—C17—H17	119.8
C6—C5—H5	120.5	C18—C17—H17	119.8
C7—C6—C5	120.1 (2)	C13—C18—C17	120.8 (2)
C7—C6—H6	119.9	C13—C18—H18	119.6
C5—C6—H6	119.9	C17—C18—H18	119.6
C6—C7—C8	121.9 (2)	C20—C19—C24	118.03 (18)
C6—C7—H7	119.0	C20—C19—C3	121.12 (16)
C8—C7—H7	119.0	C24—C19—C3	120.69 (18)
C7—C8—C9	117.4 (2)	C19—C20—C21	121.1 (2)
C7—C8—H8	121.3	C19—C20—H20	119.4
C9—C8—H8	121.3	C21—C20—H20	119.4
C8—C9—C4	121.79 (19)	C22—C21—C20	119.9 (2)
C8—C9—N1	128.49 (18)	C22—C21—H21	120.0
C4—C9—N1	109.72 (16)	C20—C21—H21	120.0
N1—C10—C11	115.9 (2)	C23—C22—C21	119.9 (2)
N1—C10—H10A	108.3	C23—C22—H22	120.0
C11—C10—H10A	108.3	C21—C22—H22	120.0
N1—C10—H10B	108.3	C22—C23—C24	120.2 (2)
C11—C10—H10B	108.3	C22—C23—H23	119.9
H10A—C10—H10B	107.4	C24—C23—H23	119.9
C12—C11—C10	128.2 (3)	C19—C24—C23	120.7 (2)
C12—C11—H11	115.9	C19—C24—H24	119.6
C10—C11—H11	115.9	C23—C24—H24	119.6
C11—C12—H12A	120.0	C2—N1—C9	111.39 (15)
C11—C12—H12B	120.0	C2—N1—C10	122.46 (18)
H12A—C12—H12B	120.0	C9—N1—C10	126.12 (17)
O1—C2—C3—C4	177.4 (2)	C3—C13—C14—C15	−177.99 (18)
N1—C2—C3—C4	−3.70 (18)	C13—C14—C15—C16	0.7 (4)
O1—C2—C3—C19	59.6 (2)	C14—C15—C16—C17	−0.7 (4)
N1—C2—C3—C19	−121.48 (16)	C15—C16—C17—C18	0.1 (5)
O1—C2—C3—C13	−63.8 (2)	C14—C13—C18—C17	−0.6 (4)
N1—C2—C3—C13	115.17 (16)	C3—C13—C18—C17	177.3 (3)
C19—C3—C4—C5	−57.8 (3)	C16—C17—C18—C13	0.6 (5)
C13—C3—C4—C5	71.0 (3)	C4—C3—C19—C20	−80.4 (2)
C2—C3—C4—C5	−175.6 (2)	C13—C3—C19—C20	150.58 (17)
C19—C3—C4—C9	120.96 (17)	C2—C3—C19—C20	31.3 (2)
C13—C3—C4—C9	−110.24 (17)	C4—C3—C19—C24	95.0 (2)
C2—C3—C4—C9	3.23 (18)	C13—C3—C19—C24	−34.0 (2)
C9—C4—C5—C6	1.6 (3)	C2—C3—C19—C24	−153.30 (18)
C3—C4—C5—C6	−179.68 (19)	C24—C19—C20—C21	1.6 (3)
C4—C5—C6—C7	−0.5 (3)	C3—C19—C20—C21	177.17 (19)
C5—C6—C7—C8	−0.3 (4)	C19—C20—C21—C22	−0.5 (4)
C6—C7—C8—C9	−0.2 (4)	C20—C21—C22—C23	−0.7 (4)
C7—C8—C9—C4	1.4 (3)	C21—C22—C23—C24	0.6 (4)
C7—C8—C9—N1	−177.8 (2)	C20—C19—C24—C23	−1.7 (3)
C5—C4—C9—C8	−2.2 (3)	C3—C19—C24—C23	−177.3 (2)
C3—C4—C9—C8	178.88 (19)	C22—C23—C24—C19	0.6 (4)
C5—C4—C9—N1	177.21 (18)	O1—C2—N1—C9	−178.1 (2)
C3—C4—C9—N1	−1.7 (2)	C3—C2—N1—C9	3.0 (2)
N1—C10—C11—C12	−0.3 (4)	O1—C2—N1—C10	3.8 (3)
C4—C3—C13—C18	3.0 (3)	C3—C2—N1—C10	−175.20 (18)
C19—C3—C13—C18	130.7 (2)	C8—C9—N1—C2	178.5 (2)
C2—C3—C13—C18	−107.4 (2)	C4—C9—N1—C2	−0.8 (2)
C4—C3—C13—C14	−179.13 (17)	C8—C9—N1—C10	−3.4 (4)
C19—C3—C13—C14	−51.5 (2)	C4—C9—N1—C10	177.25 (19)
C2—C3—C13—C14	70.4 (2)	C11—C10—N1—C2	−96.5 (3)
C18—C13—C14—C15	−0.1 (3)	C11—C10—N1—C9	85.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···N1	0.93	2.59	2.905 (4)	100
C10—H10A···O1i	0.97	2.49	3.446 (3)	170
C23—H23···O1ii	0.93	2.55	3.356 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯N1	0.93	2.59	2.905 (4)	100
C10—H10A⋯O1i	0.97	2.49	3.446 (3)	170
C23—H23⋯O1ii	0.93	2.55	3.356 (3)	146

Symmetry codes: (i) ; (ii) .