1'-Methyl-4'-(4-methyl-phen-yl)dispiro-[indane-2,3'-pyrrolidine-2',3''-indoline]-1,2''-dione.

In the title mol-ecule, C(27)H(24)N(2)O(2), the pyrrolidin-2-one ring is almost planar (r.m.s. deviation = 0.003 Å), the pyrrolidine ring has an envelope conformation (the N atom is the flap atom) and the cyclo-penta-none ring is twisted about the C(q)-C(m) bond (q = quaternary and m = methylene). The ketone O atoms are directed to opposite sides of the mol-ecule. Supra-molecular chains along the a axis are formed in the crystal packing mediated by N-H⋯N and C-H⋯O inter-actions. These are connected into layers in the ab plane via C-H⋯π inter-actions.

Related literature

For the biological activity of spiro­pyrrolidinyl-oxindolyl analogues, see: James & Williams (1972 ▶); Cui et al. (1996a ▶,b ▶); Palmisano et al. (1996 ▶); Garcia Prado et al. (2007 ▶); Girgis (2009b ▶); Girgis et al. (2012 ▶). For related structures, see: Moustafa et al. (2008 ▶); Li et al. (2008 ▶). For the synthesis, see: Girgis et al. (2009a ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C27H24N2O2

M = 408.48

Triclinic,

a = 6.2414 (2) Å

b = 11.3954 (5) Å

c = 15.5563 (7) Å

α = 78.386 (2)°

β = 87.165 (2)°

γ = 77.046 (2)°

V = 1056.17 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.25 × 0.08 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing 1995 ▶) T min = 0.852, T max = 0.991

12225 measured reflections

4833 independent reflections

2335 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.154

S = 1.01

4833 reflections

285 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028012/qm2073sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028012/qm2073Isup2.hkl

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

C27H24N2O2	Z = 2
Mr = 408.48	F(000) = 432
Triclinic, P1	Dx = 1.284 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2414 (2) Å	Cell parameters from 12225 reflections
b = 11.3954 (5) Å	θ = 3.0–27.5°
c = 15.5563 (7) Å	µ = 0.08 mm−1
α = 78.386 (2)°	T = 293 K
β = 87.165 (2)°	Block, colourless
γ = 77.046 (2)°	0.25 × 0.08 × 0.05 mm
V = 1056.17 (7) Å3

Nonius KappaCCD diffractometer	4833 independent reflections
Radiation source: fine-focus sealed tube	2335 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	Rint = 0.081
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ & ω scans	h = −8→7
Absorption correction: multi-scan (SORTAV; Blessing 1995)	k = −11→14
Tmin = 0.852, Tmax = 0.991	l = −15→20
12225 measured reflections

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0631P)2 + 0.0079P] where P = (Fo2 + 2Fc2)/3
4833 reflections	(Δ/σ)max < 0.001
285 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.23 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.6791 (2)	0.04076 (16)	0.60805 (11)	0.0457 (5)
O2	−0.0672 (2)	0.20742 (16)	0.77463 (11)	0.0496 (5)
N1	0.6771 (3)	0.24335 (18)	0.60219 (12)	0.0393 (5)
H1N	0.8160 (17)	0.240 (2)	0.5962 (15)	0.047*
N2	0.1836 (3)	0.16036 (17)	0.58965 (11)	0.0343 (5)
C1	0.5853 (3)	0.1437 (2)	0.61737 (14)	0.0351 (6)
C2	0.5274 (3)	0.3484 (2)	0.61858 (14)	0.0363 (6)
C3	0.5576 (4)	0.4665 (2)	0.60611 (16)	0.0481 (7)
H3	0.6932	0.4843	0.5882	0.058*
C4	0.3809 (4)	0.5584 (2)	0.62086 (16)	0.0530 (7)
H4	0.3977	0.6389	0.6130	0.064*
C5	0.1796 (4)	0.5311 (2)	0.64715 (16)	0.0511 (7)
H5	0.0621	0.5937	0.6565	0.061*
C6	0.1508 (4)	0.4119 (2)	0.65968 (16)	0.0441 (6)
H6	0.0150	0.3944	0.6774	0.053*
C7	0.3261 (3)	0.3190 (2)	0.64565 (14)	0.0340 (6)
C8	0.3426 (3)	0.1840 (2)	0.64811 (14)	0.0323 (6)
C9	0.2032 (3)	0.0270 (2)	0.61042 (14)	0.0381 (6)
H9A	0.3381	−0.0154	0.5865	0.046*
H9B	0.0793	0.0047	0.5876	0.046*
C10	0.2052 (3)	−0.0030 (2)	0.71083 (14)	0.0352 (6)
H10	0.0507	0.0121	0.7294	0.042*
C11	0.3042 (3)	0.1001 (2)	0.73840 (14)	0.0320 (5)
C12	0.2139 (4)	0.2079 (2)	0.49617 (15)	0.0470 (7)
H12A	0.2007	0.2951	0.4866	0.070*
H12B	0.1037	0.1902	0.4629	0.070*
H12C	0.3571	0.1696	0.4777	0.070*
C13	0.3025 (3)	−0.1357 (2)	0.74969 (15)	0.0368 (6)
C14	0.5212 (3)	−0.1917 (2)	0.73573 (16)	0.0425 (6)
H14	0.6127	−0.1465	0.7016	0.051*
C15	0.6024 (4)	−0.3142 (2)	0.77248 (17)	0.0515 (7)
H15	0.7496	−0.3489	0.7639	0.062*
C16	0.4717 (4)	−0.3865 (2)	0.82152 (17)	0.0529 (7)
C17	0.2557 (4)	−0.3311 (2)	0.83404 (17)	0.0548 (7)
H17	0.1634	−0.3771	0.8667	0.066*
C18	0.1730 (4)	−0.2087 (2)	0.79924 (16)	0.0471 (7)
H18	0.0264	−0.1743	0.8093	0.057*
C19	0.5612 (5)	−0.5205 (3)	0.8587 (2)	0.0880 (11)
H19A	0.6731	−0.5539	0.8203	0.132*
H19B	0.4444	−0.5639	0.8640	0.132*
H19C	0.6229	−0.5290	0.9155	0.132*
C20	0.1271 (3)	0.1721 (2)	0.79323 (15)	0.0368 (6)
C21	0.2297 (4)	0.1875 (2)	0.87198 (15)	0.0395 (6)
C22	0.1345 (4)	0.2491 (3)	0.93741 (17)	0.0552 (7)
H22	−0.0138	0.2875	0.9357	0.066*
C23	0.2674 (5)	0.2515 (3)	1.00543 (18)	0.0648 (8)
H23	0.2083	0.2927	1.0500	0.078*
C24	0.4867 (5)	0.1933 (3)	1.00763 (18)	0.0597 (8)
H24	0.5738	0.1965	1.0536	0.072*
C25	0.5791 (4)	0.1306 (2)	0.94330 (16)	0.0495 (7)
H25	0.7268	0.0909	0.9459	0.059*
C26	0.4486 (3)	0.1274 (2)	0.87431 (14)	0.0359 (6)
C27	0.5096 (3)	0.0624 (2)	0.79916 (14)	0.0395 (6)
H27A	0.5459	−0.0258	0.8200	0.047*
H27B	0.6354	0.0871	0.7677	0.047*

	U11	U22	U33	U12	U13	U23
O1	0.0351 (9)	0.0427 (11)	0.0610 (12)	−0.0061 (8)	0.0061 (7)	−0.0184 (9)
O2	0.0313 (9)	0.0638 (12)	0.0546 (11)	−0.0040 (8)	0.0022 (7)	−0.0210 (9)
N1	0.0286 (10)	0.0458 (14)	0.0456 (12)	−0.0113 (10)	0.0011 (9)	−0.0106 (10)
N2	0.0328 (10)	0.0362 (12)	0.0346 (12)	−0.0074 (8)	−0.0043 (8)	−0.0077 (9)
C1	0.0329 (12)	0.0411 (16)	0.0336 (14)	−0.0103 (12)	−0.0009 (10)	−0.0098 (12)
C2	0.0377 (13)	0.0376 (15)	0.0346 (14)	−0.0091 (11)	−0.0036 (10)	−0.0078 (11)
C3	0.0484 (15)	0.0461 (18)	0.0523 (17)	−0.0180 (13)	−0.0077 (12)	−0.0054 (13)
C4	0.0685 (18)	0.0400 (17)	0.0524 (18)	−0.0164 (14)	−0.0126 (13)	−0.0054 (14)
C5	0.0603 (17)	0.0402 (18)	0.0508 (17)	−0.0013 (13)	−0.0068 (13)	−0.0132 (14)
C6	0.0415 (14)	0.0424 (17)	0.0482 (16)	−0.0053 (12)	−0.0008 (11)	−0.0125 (13)
C7	0.0349 (12)	0.0340 (15)	0.0332 (14)	−0.0064 (10)	−0.0031 (10)	−0.0077 (11)
C8	0.0268 (11)	0.0358 (14)	0.0363 (14)	−0.0081 (9)	−0.0015 (9)	−0.0100 (11)
C9	0.0325 (12)	0.0441 (16)	0.0410 (15)	−0.0103 (10)	−0.0031 (10)	−0.0132 (12)
C10	0.0276 (11)	0.0386 (15)	0.0408 (15)	−0.0086 (10)	0.0007 (9)	−0.0095 (11)
C11	0.0303 (11)	0.0361 (14)	0.0309 (13)	−0.0065 (10)	0.0008 (9)	−0.0109 (11)
C12	0.0536 (15)	0.0507 (17)	0.0370 (15)	−0.0110 (12)	−0.0052 (11)	−0.0085 (12)
C13	0.0389 (13)	0.0361 (15)	0.0378 (14)	−0.0104 (11)	−0.0020 (10)	−0.0101 (12)
C14	0.0408 (14)	0.0408 (16)	0.0463 (16)	−0.0063 (11)	0.0001 (11)	−0.0123 (13)
C15	0.0477 (15)	0.0485 (18)	0.0543 (18)	0.0036 (13)	−0.0028 (12)	−0.0161 (14)
C16	0.0678 (18)	0.0447 (18)	0.0440 (16)	−0.0070 (14)	−0.0060 (13)	−0.0077 (14)
C17	0.0659 (18)	0.0479 (19)	0.0518 (18)	−0.0228 (14)	0.0019 (13)	−0.0011 (14)
C18	0.0455 (14)	0.0460 (17)	0.0498 (16)	−0.0120 (12)	−0.0008 (11)	−0.0067 (13)
C19	0.109 (3)	0.048 (2)	0.091 (3)	−0.0015 (18)	−0.0049 (19)	0.0051 (19)
C20	0.0344 (13)	0.0390 (15)	0.0372 (14)	−0.0102 (10)	0.0032 (10)	−0.0066 (11)
C21	0.0463 (14)	0.0419 (16)	0.0330 (14)	−0.0139 (11)	0.0025 (11)	−0.0097 (12)
C22	0.0619 (16)	0.059 (2)	0.0473 (17)	−0.0111 (14)	0.0055 (13)	−0.0205 (15)
C23	0.085 (2)	0.074 (2)	0.0436 (18)	−0.0241 (17)	0.0074 (15)	−0.0248 (16)
C24	0.084 (2)	0.066 (2)	0.0372 (17)	−0.0302 (17)	−0.0091 (14)	−0.0109 (15)
C25	0.0588 (16)	0.0476 (17)	0.0435 (17)	−0.0183 (13)	−0.0117 (13)	−0.0017 (14)
C26	0.0443 (14)	0.0365 (15)	0.0290 (13)	−0.0151 (11)	−0.0003 (10)	−0.0041 (11)
C27	0.0351 (12)	0.0436 (16)	0.0400 (15)	−0.0082 (10)	−0.0037 (10)	−0.0083 (12)

O1—C1	1.222 (3)	C12—H12B	0.9600
O2—C20	1.219 (2)	C12—H12C	0.9600
N1—C1	1.357 (3)	C13—C18	1.386 (3)
N1—C2	1.403 (3)	C13—C14	1.397 (3)
N1—H1N	0.860 (9)	C14—C15	1.387 (3)
N2—C12	1.465 (3)	C14—H14	0.9300
N2—C9	1.467 (3)	C15—C16	1.383 (3)
N2—C8	1.481 (3)	C15—H15	0.9300
C1—C8	1.562 (3)	C16—C17	1.377 (3)
C2—C3	1.375 (3)	C16—C19	1.508 (4)
C2—C7	1.396 (3)	C17—C18	1.380 (3)
C3—C4	1.385 (3)	C17—H17	0.9300
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.384 (3)	C19—H19A	0.9600
C4—H4	0.9300	C19—H19B	0.9600
C5—C6	1.383 (3)	C19—H19C	0.9600
C5—H5	0.9300	C20—C21	1.468 (3)
C6—C7	1.384 (3)	C21—C26	1.383 (3)
C6—H6	0.9300	C21—C22	1.387 (3)
C7—C8	1.511 (3)	C22—C23	1.385 (4)
C8—C11	1.573 (3)	C22—H22	0.9300
C9—C10	1.530 (3)	C23—C24	1.380 (4)
C9—H9A	0.9700	C23—H23	0.9300
C9—H9B	0.9700	C24—C25	1.375 (4)
C10—C13	1.509 (3)	C24—H24	0.9300
C10—C11	1.582 (3)	C25—C26	1.390 (3)
C10—H10	0.9800	C25—H25	0.9300
C11—C20	1.551 (3)	C26—C27	1.496 (3)
C11—C27	1.559 (3)	C27—H27A	0.9700
C12—H12A	0.9600	C27—H27B	0.9700
C1—N1—C2	111.53 (18)	N2—C12—H12C	109.5
C1—N1—H1N	124.0 (16)	H12A—C12—H12C	109.5
C2—N1—H1N	122.8 (16)	H12B—C12—H12C	109.5
C12—N2—C9	113.17 (18)	C18—C13—C14	117.0 (2)
C12—N2—C8	114.51 (16)	C18—C13—C10	120.33 (19)
C9—N2—C8	105.06 (15)	C14—C13—C10	122.6 (2)
O1—C1—N1	125.0 (2)	C15—C14—C13	120.4 (2)
O1—C1—C8	126.6 (2)	C15—C14—H14	119.8
N1—C1—C8	108.4 (2)	C13—C14—H14	119.8
C3—C2—C7	122.1 (2)	C16—C15—C14	122.2 (2)
C3—C2—N1	128.0 (2)	C16—C15—H15	118.9
C7—C2—N1	109.8 (2)	C14—C15—H15	118.9
C2—C3—C4	118.3 (2)	C17—C16—C15	117.1 (2)
C2—C3—H3	120.9	C17—C16—C19	121.5 (3)
C4—C3—H3	120.9	C15—C16—C19	121.4 (3)
C5—C4—C3	120.4 (3)	C16—C17—C18	121.5 (2)
C5—C4—H4	119.8	C16—C17—H17	119.3
C3—C4—H4	119.8	C18—C17—H17	119.3
C6—C5—C4	120.9 (2)	C17—C18—C13	121.8 (2)
C6—C5—H5	119.6	C17—C18—H18	119.1
C4—C5—H5	119.6	C13—C18—H18	119.1
C5—C6—C7	119.4 (2)	C16—C19—H19A	109.5
C5—C6—H6	120.3	C16—C19—H19B	109.5
C7—C6—H6	120.3	H19A—C19—H19B	109.5
C6—C7—C2	118.9 (2)	C16—C19—H19C	109.5
C6—C7—C8	131.74 (19)	H19A—C19—H19C	109.5
C2—C7—C8	109.20 (19)	H19B—C19—H19C	109.5
N2—C8—C7	113.33 (16)	O2—C20—C21	125.7 (2)
N2—C8—C1	112.07 (18)	O2—C20—C11	125.1 (2)
C7—C8—C1	101.14 (16)	C21—C20—C11	109.17 (18)
N2—C8—C11	102.74 (16)	C26—C21—C22	122.0 (2)
C7—C8—C11	118.25 (18)	C26—C21—C20	109.3 (2)
C1—C8—C11	109.57 (16)	C22—C21—C20	128.7 (2)
N2—C9—C10	103.46 (18)	C23—C22—C21	117.8 (2)
N2—C9—H9A	111.1	C23—C22—H22	121.1
C10—C9—H9A	111.1	C21—C22—H22	121.1
N2—C9—H9B	111.1	C24—C23—C22	120.5 (3)
C10—C9—H9B	111.1	C24—C23—H23	119.7
H9A—C9—H9B	109.0	C22—C23—H23	119.7
C13—C10—C9	114.3 (2)	C25—C24—C23	121.3 (3)
C13—C10—C11	118.71 (17)	C25—C24—H24	119.3
C9—C10—C11	104.82 (17)	C23—C24—H24	119.3
C13—C10—H10	106.0	C24—C25—C26	119.0 (2)
C9—C10—H10	106.0	C24—C25—H25	120.5
C11—C10—H10	106.0	C26—C25—H25	120.5
C20—C11—C27	102.80 (17)	C21—C26—C25	119.3 (2)
C20—C11—C8	110.42 (17)	C21—C26—C27	112.04 (19)
C27—C11—C8	112.89 (16)	C25—C26—C27	128.6 (2)
C20—C11—C10	107.69 (16)	C26—C27—C11	106.05 (17)
C27—C11—C10	119.51 (18)	C26—C27—H27A	110.5
C8—C11—C10	103.42 (17)	C11—C27—H27A	110.5
N2—C12—H12A	109.5	C26—C27—H27B	110.5
N2—C12—H12B	109.5	C11—C27—H27B	110.5
H12A—C12—H12B	109.5	H27A—C27—H27B	108.7

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2i	0.86 (1)	2.28 (1)	3.098 (3)	160 (2)
C9—H9B···O1ii	0.97	2.45	3.241 (2)	138
C27—H27B···O2i	0.97	2.56	3.385 (2)	143
C24—H24···Cg1iii	0.93	2.78	3.620 (3)	150
C19—H19B···Cg2iv	0.96	2.97	3.761 (4)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C13–C18 and C21–C26 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2i	0.86 (1)	2.28 (1)	3.098 (3)	160 (2)
C9—H9B⋯O1ii	0.97	2.45	3.241 (2)	138
C27—H27B⋯O2i	0.97	2.56	3.385 (2)	143
C24—H24⋯Cg1iii	0.93	2.78	3.620 (3)	150
C19—H19B⋯Cg2iv	0.96	2.97	3.761 (4)	140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .