1-Allyl-3,3-di-p-tolyl-indolin-2-one.

In the title compound, C(25)H(23)NO, the indoline system is essentially planar. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯N inter-actions and the crystal packing is determined by inter-molecular C-H⋯π inter-actions.

Related literature

For related literature, see: Harris & Uhle (1960 ▶); Ho et al. (1986 ▶); Rajeswaran et al. (1999 ▶); Stevenson et al. (2000 ▶); Sethusankar et al. (2002 ▶).

Experimental

Crystal data

C25H23NO

M = 353.44

Triclinic,

a = 9.3311 (2) Å

b = 9.5793 (2) Å

c = 11.5736 (2) Å

α = 92.163 (1)°

β = 103.192 (1)°

γ = 101.520 (1)°

V = 983.15 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 293 (2) K

0.26 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.982, T max = 0.986

25969 measured reflections

6260 independent reflections

4310 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.156

S = 0.99

6260 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.24 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/S1600536808010088/gw2036sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010088/gw2036Isup2.hkl

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

C25H23NO	Z = 2
Mr = 353.44	F000 = 376
Triclinic, P1	Dx = 1.194 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.3311 (2) Å	Cell parameters from 9112 reflections
b = 9.5793 (2) Å	θ = 2.3–30.1º
c = 11.5736 (2) Å	µ = 0.07 mm−1
α = 92.1630 (10)º	T = 293 (2) K
β = 103.1920 (10)º	Prism, colourless
γ = 101.5200 (10)º	0.26 × 0.20 × 0.20 mm
V = 983.15 (3) Å3

Bruker Kappa APEXII diffractometer	6260 independent reflections
Radiation source: fine-focus sealed tube	4310 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
T = 293(2) K	θmax = 31.0º
ω and φ scan	θmin = 2.2º
Absorption correction: multi-scan(Blessing, 1995)	h = −13→13
Tmin = 0.982, Tmax = 0.986	k = −13→13
25969 measured reflections	l = −16→16

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)] = 0.051	H-atom parameters constrained
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.0731P)2 + 0.1889P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
6260 reflections	Δρmax = 0.25 e Å−3
244 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	0.21981 (13)	0.10769 (13)	0.14416 (10)	0.0403 (2)
C3	0.29661 (11)	0.03653 (12)	0.25302 (9)	0.0361 (2)
C4	0.45434 (12)	0.05217 (12)	0.23447 (10)	0.0391 (2)
C5	0.57669 (13)	0.00390 (15)	0.29710 (12)	0.0497 (3)
H5	0.5699	−0.0478	0.3628	0.060*
C6	0.71037 (15)	0.03411 (17)	0.26019 (15)	0.0602 (4)
H6	0.7938	0.0024	0.3018	0.072*
C7	0.72086 (16)	0.10999 (18)	0.16332 (16)	0.0629 (4)
H7	0.8116	0.1295	0.1405	0.075*
C8	0.59809 (17)	0.15830 (17)	0.09859 (14)	0.0587 (4)
H8	0.6049	0.2096	0.0327	0.070*
C9	0.46580 (14)	0.12724 (13)	0.13582 (11)	0.0443 (3)
C10	0.29599 (19)	0.24323 (18)	−0.01709 (12)	0.0614 (4)
H10A	0.1917	0.2102	−0.0604	0.074*
H10B	0.3589	0.2267	−0.0701	0.074*
C11	0.32409 (19)	0.39967 (19)	0.01642 (16)	0.0658 (4)
H11	0.3133	0.4583	−0.0458	0.079*
C12	0.3620 (2)	0.4623 (2)	0.12318 (19)	0.0749 (5)
H12A	0.3742	0.4084	0.1885	0.090*
H12B	0.3770	0.5612	0.1347	0.090*
C13	0.22090 (12)	−0.12027 (12)	0.25034 (10)	0.0391 (2)
C14	0.24490 (16)	−0.19198 (15)	0.35239 (13)	0.0541 (3)
H14	0.3029	−0.1423	0.4237	0.065*
C15	0.18392 (18)	−0.33608 (16)	0.34970 (16)	0.0626 (4)
H15	0.2020	−0.3818	0.4194	0.075*
C16	0.09700 (17)	−0.41371 (15)	0.24620 (16)	0.0592 (4)
C17	0.07309 (17)	−0.34194 (16)	0.14492 (15)	0.0603 (4)
H17	0.0145	−0.3920	0.0739	0.072*
C18	0.13362 (15)	−0.19778 (14)	0.14583 (12)	0.0490 (3)
H18	0.1156	−0.1526	0.0759	0.059*
C19	0.0294 (3)	−0.57073 (17)	0.2435 (2)	0.0907 (6)
H19A	−0.0262	−0.6064	0.1639	0.136*
H19B	−0.0372	−0.5842	0.2963	0.136*
H19C	0.1083	−0.6216	0.2686	0.136*
C20	0.28928 (12)	0.12652 (12)	0.36267 (10)	0.0372 (2)
C21	0.40937 (13)	0.23204 (14)	0.42458 (11)	0.0445 (3)
H21	0.5003	0.2467	0.4020	0.053*
C22	0.39541 (16)	0.31600 (15)	0.51984 (12)	0.0530 (3)
H22	0.4778	0.3858	0.5605	0.064*
C23	0.26275 (17)	0.29871 (17)	0.55575 (12)	0.0553 (3)
C24	0.14184 (16)	0.19372 (17)	0.49283 (13)	0.0561 (3)
H24	0.0506	0.1801	0.5150	0.067*
C25	0.15471 (14)	0.10923 (15)	0.39803 (12)	0.0483 (3)
H25	0.0721	0.0398	0.3573	0.058*
C26	0.2485 (3)	0.3901 (3)	0.65992 (18)	0.0932 (7)
H26A	0.1485	0.3626	0.6718	0.140*
H26B	0.2675	0.4889	0.6439	0.140*
H26C	0.3204	0.3771	0.7304	0.140*
N1	0.32609 (13)	0.15965 (12)	0.08421 (9)	0.0484 (3)
O1	0.08971 (10)	0.11949 (10)	0.11825 (8)	0.0515 (2)

	U11	U22	U33	U12	U13	U23
C2	0.0417 (5)	0.0399 (6)	0.0385 (5)	0.0124 (4)	0.0053 (4)	0.0024 (4)
C3	0.0306 (5)	0.0386 (6)	0.0381 (5)	0.0075 (4)	0.0059 (4)	0.0061 (4)
C4	0.0342 (5)	0.0399 (6)	0.0429 (6)	0.0077 (4)	0.0094 (4)	0.0027 (4)
C5	0.0372 (6)	0.0554 (8)	0.0569 (7)	0.0132 (5)	0.0086 (5)	0.0103 (6)
C6	0.0364 (6)	0.0650 (9)	0.0805 (10)	0.0145 (6)	0.0135 (6)	0.0057 (8)
C7	0.0444 (7)	0.0637 (9)	0.0859 (11)	0.0079 (6)	0.0305 (7)	0.0025 (8)
C8	0.0586 (8)	0.0602 (9)	0.0656 (9)	0.0114 (7)	0.0317 (7)	0.0128 (7)
C9	0.0444 (6)	0.0442 (6)	0.0468 (6)	0.0109 (5)	0.0148 (5)	0.0051 (5)
C10	0.0757 (10)	0.0732 (10)	0.0455 (7)	0.0298 (8)	0.0202 (7)	0.0229 (7)
C11	0.0697 (9)	0.0666 (10)	0.0719 (10)	0.0222 (8)	0.0280 (8)	0.0323 (8)
C12	0.0729 (11)	0.0612 (10)	0.0954 (13)	0.0132 (8)	0.0299 (10)	0.0153 (9)
C13	0.0318 (5)	0.0389 (6)	0.0461 (6)	0.0085 (4)	0.0074 (4)	0.0048 (5)
C14	0.0522 (7)	0.0470 (7)	0.0556 (7)	0.0060 (6)	0.0005 (6)	0.0122 (6)
C15	0.0626 (9)	0.0476 (8)	0.0785 (10)	0.0132 (6)	0.0152 (7)	0.0224 (7)
C16	0.0542 (7)	0.0368 (7)	0.0920 (11)	0.0108 (6)	0.0280 (7)	0.0023 (7)
C17	0.0582 (8)	0.0462 (8)	0.0716 (9)	0.0058 (6)	0.0133 (7)	−0.0137 (7)
C18	0.0499 (7)	0.0470 (7)	0.0480 (6)	0.0096 (5)	0.0092 (5)	−0.0022 (5)
C19	0.0989 (14)	0.0380 (8)	0.1420 (19)	0.0073 (8)	0.0500 (14)	0.0009 (10)
C20	0.0339 (5)	0.0404 (6)	0.0373 (5)	0.0077 (4)	0.0078 (4)	0.0079 (4)
C21	0.0372 (5)	0.0475 (7)	0.0461 (6)	0.0038 (5)	0.0097 (5)	0.0032 (5)
C22	0.0521 (7)	0.0519 (8)	0.0491 (7)	0.0055 (6)	0.0063 (6)	−0.0046 (6)
C23	0.0607 (8)	0.0625 (9)	0.0456 (7)	0.0186 (7)	0.0145 (6)	0.0007 (6)
C24	0.0486 (7)	0.0701 (9)	0.0558 (7)	0.0148 (6)	0.0229 (6)	0.0056 (7)
C25	0.0361 (5)	0.0550 (7)	0.0522 (7)	0.0046 (5)	0.0121 (5)	0.0027 (6)
C26	0.0965 (14)	0.1150 (17)	0.0707 (11)	0.0262 (12)	0.0279 (10)	−0.0268 (11)
N1	0.0520 (6)	0.0551 (6)	0.0434 (5)	0.0188 (5)	0.0140 (5)	0.0154 (5)
O1	0.0433 (4)	0.0595 (6)	0.0515 (5)	0.0207 (4)	0.0023 (4)	0.0074 (4)

C2—O1	1.2114 (14)	C14—C15	1.380 (2)
C2—N1	1.3621 (16)	C14—H14	0.9300
C2—C3	1.5535 (15)	C15—C16	1.376 (2)
C3—C4	1.5143 (15)	C15—H15	0.9300
C3—C13	1.5228 (16)	C16—C17	1.378 (2)
C3—C20	1.5294 (16)	C16—C19	1.507 (2)
C4—C5	1.3788 (16)	C17—C18	1.382 (2)
C4—C9	1.3853 (17)	C17—H17	0.9300
C5—C6	1.3895 (19)	C18—H18	0.9300
C5—H5	0.9300	C19—H19A	0.9600
C6—C7	1.371 (2)	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600
C7—C8	1.391 (2)	C20—C21	1.3847 (16)
C7—H7	0.9300	C20—C25	1.3885 (16)
C8—C9	1.3798 (19)	C21—C22	1.3857 (19)
C8—H8	0.9300	C21—H21	0.9300
C9—N1	1.4046 (16)	C22—C23	1.375 (2)
C10—N1	1.4508 (16)	C22—H22	0.9300
C10—C11	1.489 (2)	C23—C24	1.390 (2)
C10—H10A	0.9700	C23—C26	1.509 (2)
C10—H10B	0.9700	C24—C25	1.380 (2)
C11—C12	1.293 (3)	C24—H24	0.9300
C11—H11	0.9300	C25—H25	0.9300
C12—H12A	0.9300	C26—H26A	0.9600
C12—H12B	0.9300	C26—H26B	0.9600
C13—C18	1.3852 (17)	C26—H26C	0.9600
C13—C14	1.3853 (17)
O1—C2—N1	125.45 (11)	C16—C15—C14	121.51 (14)
O1—C2—C3	126.57 (11)	C16—C15—H15	119.2
N1—C2—C3	107.95 (9)	C14—C15—H15	119.2
C4—C3—C13	111.14 (9)	C15—C16—C17	117.38 (13)
C4—C3—C20	113.55 (9)	C15—C16—C19	121.49 (17)
C13—C3—C20	112.94 (9)	C17—C16—C19	121.13 (17)
C4—C3—C2	101.28 (9)	C16—C17—C18	121.93 (14)
C13—C3—C2	111.74 (9)	C16—C17—H17	119.0
C20—C3—C2	105.46 (9)	C18—C17—H17	119.0
C5—C4—C9	119.89 (11)	C17—C18—C13	120.39 (13)
C5—C4—C3	130.70 (11)	C17—C18—H18	119.8
C9—C4—C3	109.40 (9)	C13—C18—H18	119.8
C4—C5—C6	118.68 (13)	C16—C19—H19A	109.5
C4—C5—H5	120.7	C16—C19—H19B	109.5
C6—C5—H5	120.7	H19A—C19—H19B	109.5
C7—C6—C5	120.88 (13)	C16—C19—H19C	109.5
C7—C6—H6	119.6	H19A—C19—H19C	109.5
C5—C6—H6	119.6	H19B—C19—H19C	109.5
C6—C7—C8	121.13 (13)	C21—C20—C25	117.95 (11)
C6—C7—H7	119.4	C21—C20—C3	122.56 (10)
C8—C7—H7	119.4	C25—C20—C3	119.36 (10)
C9—C8—C7	117.48 (14)	C20—C21—C22	120.67 (12)
C9—C8—H8	121.3	C20—C21—H21	119.7
C7—C8—H8	121.3	C22—C21—H21	119.7
C8—C9—C4	121.93 (12)	C23—C22—C21	121.62 (13)
C8—C9—N1	128.51 (12)	C23—C22—H22	119.2
C4—C9—N1	109.54 (10)	C21—C22—H22	119.2
N1—C10—C11	113.55 (13)	C22—C23—C24	117.66 (13)
N1—C10—H10A	108.9	C22—C23—C26	121.35 (15)
C11—C10—H10A	108.9	C24—C23—C26	120.99 (15)
N1—C10—H10B	108.9	C25—C24—C23	121.17 (13)
C11—C10—H10B	108.9	C25—C24—H24	119.4
H10A—C10—H10B	107.7	C23—C24—H24	119.4
C12—C11—C10	126.66 (15)	C24—C25—C20	120.91 (12)
C12—C11—H11	116.7	C24—C25—H25	119.5
C10—C11—H11	116.7	C20—C25—H25	119.5
C11—C12—H12A	120.0	C23—C26—H26A	109.5
C11—C12—H12B	120.0	C23—C26—H26B	109.5
H12A—C12—H12B	120.0	H26A—C26—H26B	109.5
C18—C13—C14	117.85 (12)	C23—C26—H26C	109.5
C18—C13—C3	121.72 (11)	H26A—C26—H26C	109.5
C14—C13—C3	120.33 (10)	H26B—C26—H26C	109.5
C15—C14—C13	120.95 (13)	C2—N1—C9	111.71 (10)
C15—C14—H14	119.5	C2—N1—C10	122.67 (11)
C13—C14—H14	119.5	C9—N1—C10	125.57 (12)
O1—C2—C3—C4	178.68 (12)	C14—C15—C16—C17	0.0 (2)
N1—C2—C3—C4	−3.41 (12)	C14—C15—C16—C19	−179.48 (16)
O1—C2—C3—C13	60.29 (16)	C15—C16—C17—C18	0.2 (2)
N1—C2—C3—C13	−121.80 (11)	C19—C16—C17—C18	179.68 (15)
O1—C2—C3—C20	−62.78 (15)	C16—C17—C18—C13	−0.2 (2)
N1—C2—C3—C20	115.14 (10)	C14—C13—C18—C17	0.1 (2)
C13—C3—C4—C5	−57.30 (16)	C3—C13—C18—C17	176.45 (12)
C20—C3—C4—C5	71.33 (16)	C4—C3—C20—C21	11.87 (15)
C2—C3—C4—C5	−176.12 (13)	C13—C3—C20—C21	139.58 (11)
C13—C3—C4—C9	121.92 (11)	C2—C3—C20—C21	−98.13 (12)
C20—C3—C4—C9	−109.45 (11)	C4—C3—C20—C25	−172.36 (10)
C2—C3—C4—C9	3.10 (12)	C13—C3—C20—C25	−44.66 (14)
C9—C4—C5—C6	1.0 (2)	C2—C3—C20—C25	77.64 (13)
C3—C4—C5—C6	−179.88 (12)	C25—C20—C21—C22	0.88 (18)
C4—C5—C6—C7	−0.2 (2)	C3—C20—C21—C22	176.71 (11)
C5—C6—C7—C8	−0.4 (2)	C20—C21—C22—C23	−0.5 (2)
C6—C7—C8—C9	0.2 (2)	C21—C22—C23—C24	−0.2 (2)
C7—C8—C9—C4	0.7 (2)	C21—C22—C23—C26	179.75 (16)
C7—C8—C9—N1	−177.86 (14)	C22—C23—C24—C25	0.4 (2)
C5—C4—C9—C8	−1.2 (2)	C26—C23—C24—C25	−179.55 (16)
C3—C4—C9—C8	179.45 (12)	C23—C24—C25—C20	0.1 (2)
C5—C4—C9—N1	177.52 (12)	C21—C20—C25—C24	−0.69 (19)
C3—C4—C9—N1	−1.79 (14)	C3—C20—C25—C24	−176.65 (12)
N1—C10—C11—C12	−4.5 (3)	O1—C2—N1—C9	−179.43 (12)
C4—C3—C13—C18	−91.47 (13)	C3—C2—N1—C9	2.63 (14)
C20—C3—C13—C18	139.57 (11)	O1—C2—N1—C10	3.1 (2)
C2—C3—C13—C18	20.86 (15)	C3—C2—N1—C10	−174.88 (12)
C4—C3—C13—C14	84.82 (14)	C8—C9—N1—C2	178.07 (13)
C20—C3—C13—C14	−44.14 (14)	C4—C9—N1—C2	−0.58 (15)
C2—C3—C13—C14	−162.84 (11)	C8—C9—N1—C10	−4.5 (2)
C18—C13—C14—C15	0.1 (2)	C4—C9—N1—C10	176.83 (13)
C3—C13—C14—C15	−176.30 (13)	C11—C10—N1—C2	88.62 (17)
C13—C14—C15—C16	−0.2 (2)	C11—C10—N1—C9	−88.53 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cgi	0.93	2.94	3.740 (2)	145
C12—H12A···N1	0.93	2.54	2.858 (2)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cgi	0.93	2.94	3.740 (2)	145
C12—H12A⋯N1	0.93	2.54	2.858 (2)	100

Symmetry code: (i) . Cg denotes the centroid of the C20–C25 ring.