1'-Butyl-2-methyl-1',2,2',3,4,9-hexa-hydro-spiro-[benzo[f]isoindole-1,3'-indole]-2',4,9-trione.

In the title compound, C(24)H(22)N(2)O(3), the indoline and pyrrole-fused naphtho-quinone units are both essentially planar [r.m.s. deviations = 0.042 (3) and 0.133 (3) Å, respectively]. The pyrrole ring adopts a C-envelope conformation. The dihedral angle between the mean planes of the two five-membered rings is 89.94 (9)°. The O atoms deviate from the mean planes of the pyrrolidine and naphthalene rings by 0.0311 (2), 0.2570 (2) and 0.1669 (2) Å. In the crystal, C-H⋯O inter-actions generate dimers with R(2) (2)(16) and R(2) (2)(18) graph-set motifs. The carbonyl O atom is involved in bifurcated hydrogen bonding. C-H⋯π inter-actions also occur.

Related literature

For the biological activity of indole derivatives, see: Stevenson et al. (2000 ▶); Rajeswaran et al. (1999 ▶); Amal Raj et al. (2003 ▶). For a related structure, see: McSweeney et al. (2004) ▶. For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C24H22N2O3

M = 386.44

Monoclinic,

a = 21.5855 (12) Å

b = 15.7999 (7) Å

c = 14.7469 (7) Å

β = 127.207 (3)°

V = 4005.7 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.975, T max = 0.979

32353 measured reflections

3336 independent reflections

2446 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.178

S = 1.00

3336 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026748/pv2556sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026748/pv2556Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026748/pv2556Isup3.cml

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

C24H22N2O3	F(000) = 1632
Mr = 386.44	Dx = 1.282 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3336 reflections
a = 21.5855 (12) Å	θ = 2.6–24.5°
b = 15.7999 (7) Å	µ = 0.09 mm−1
c = 14.7469 (7) Å	T = 293 K
β = 127.207 (3)°	Block, colourless
V = 4005.7 (3) Å3	0.30 × 0.30 × 0.25 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	3336 independent reflections
Radiation source: fine-focus sealed tube	2446 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω scans	θmax = 24.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −24→25
Tmin = 0.975, Tmax = 0.979	k = −18→18
32353 measured reflections	l = −17→17

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1024P)2 + 2.8296P] where P = (Fo2 + 2Fc2)/3
3336 reflections	(Δ/σ)max < 0.001
264 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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	0.29896 (13)	0.09126 (16)	1.2560 (2)	0.0614 (6)
H1	0.2836	0.0457	1.2781	0.074*
C2	0.32375 (15)	0.16635 (19)	1.3171 (2)	0.0729 (7)
H2	0.3246	0.1715	1.3807	0.088*
C3	0.34705 (16)	0.23335 (18)	1.2847 (2)	0.0726 (7)
H3	0.3634	0.2831	1.3269	0.087*
C4	0.34673 (14)	0.22839 (15)	1.1912 (2)	0.0627 (6)
H4	0.3627	0.2737	1.1697	0.075*
C5	0.32181 (12)	0.15374 (14)	1.13096 (18)	0.0528 (5)
C6	0.29768 (12)	0.08615 (14)	1.16220 (18)	0.0517 (5)
C7	0.27195 (12)	0.01504 (14)	1.07856 (18)	0.0530 (5)
C8	0.28365 (13)	0.05586 (15)	0.99368 (19)	0.0570 (6)
C9	0.34151 (14)	0.18855 (18)	0.9826 (2)	0.0682 (7)
H9A	0.3220	0.2454	0.9752	0.082*
H9B	0.3202	0.1682	0.9068	0.082*
C10	0.42958 (16)	0.1916 (2)	1.0533 (3)	0.0835 (8)
H10A	0.4439	0.2389	1.0275	0.100*
H10B	0.4509	0.2023	1.1320	0.100*
C11	0.4655 (2)	0.1146 (2)	1.0486 (3)	0.1005 (10)
H11A	0.4417	0.0655	1.0556	0.121*
H11B	0.5204	0.1142	1.1123	0.121*
C12	0.4562 (3)	0.1083 (3)	0.9369 (4)	0.1450 (17)
H12A	0.4026	0.1172	0.8736	0.217*
H12B	0.4722	0.0532	0.9311	0.217*
H12C	0.4878	0.1506	0.9363	0.217*
C13	0.39189 (15)	−0.06776 (18)	1.1579 (3)	0.0791 (8)
H13A	0.3876	−0.0662	1.0893	0.119*
H13B	0.4171	−0.1193	1.1984	0.119*
H13C	0.4219	−0.0202	1.2049	0.119*
C14	0.26445 (14)	−0.13602 (16)	1.0647 (2)	0.0708 (7)
H14A	0.2738	−0.1827	1.1144	0.085*
H14B	0.2716	−0.1555	1.0092	0.085*
C15	0.18559 (13)	−0.09920 (15)	1.0084 (2)	0.0585 (6)
C16	0.11206 (14)	−0.14631 (16)	0.94742 (19)	0.0608 (6)
C17	0.04098 (13)	−0.09477 (16)	0.90004 (18)	0.0575 (6)
C18	−0.03032 (16)	−0.13453 (19)	0.8497 (2)	0.0751 (7)
H18	−0.0335	−0.1933	0.8458	0.090*
C19	−0.09628 (16)	−0.0870 (2)	0.8056 (2)	0.0864 (9)
H19	−0.1438	−0.1138	0.7722	0.104*
C20	−0.09242 (15)	−0.0007 (2)	0.8106 (2)	0.0816 (8)
H20	−0.1373	0.0308	0.7807	0.098*
C21	−0.02266 (14)	0.03991 (18)	0.8594 (2)	0.0679 (7)
H21	−0.0205	0.0987	0.8621	0.081*
C22	0.04459 (12)	−0.00674 (15)	0.90473 (17)	0.0544 (6)
C23	0.11946 (13)	0.03774 (15)	0.95638 (18)	0.0557 (6)
C24	0.18925 (12)	−0.01533 (14)	1.01543 (18)	0.0517 (5)
N1	0.31470 (11)	0.13398 (12)	1.03225 (15)	0.0557 (5)
N2	0.31480 (11)	−0.06413 (12)	1.12956 (18)	0.0637 (5)
O1	0.26952 (10)	0.02136 (12)	0.90967 (14)	0.0752 (5)
O2	0.12328 (10)	0.11375 (12)	0.94839 (17)	0.0800 (6)
O3	0.11025 (11)	−0.22243 (12)	0.93678 (18)	0.0870 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0563 (13)	0.0760 (16)	0.0590 (13)	−0.0028 (11)	0.0386 (11)	0.0025 (12)
C2	0.0712 (16)	0.094 (2)	0.0621 (14)	−0.0040 (14)	0.0448 (13)	−0.0125 (14)
C3	0.0728 (16)	0.0749 (17)	0.0730 (16)	−0.0092 (13)	0.0455 (14)	−0.0187 (13)
C4	0.0618 (14)	0.0595 (14)	0.0696 (15)	−0.0063 (11)	0.0413 (12)	−0.0041 (12)
C5	0.0454 (11)	0.0626 (14)	0.0508 (12)	0.0019 (9)	0.0292 (10)	0.0007 (10)
C6	0.0413 (11)	0.0606 (13)	0.0526 (12)	0.0003 (9)	0.0281 (10)	−0.0001 (10)
C7	0.0468 (11)	0.0573 (13)	0.0564 (12)	0.0012 (9)	0.0320 (10)	−0.0013 (10)
C8	0.0451 (12)	0.0731 (16)	0.0541 (13)	0.0041 (10)	0.0306 (10)	−0.0044 (11)
C9	0.0639 (15)	0.0821 (17)	0.0672 (14)	0.0016 (12)	0.0441 (13)	0.0125 (13)
C10	0.0699 (17)	0.101 (2)	0.0929 (19)	−0.0033 (15)	0.0563 (16)	0.0024 (16)
C11	0.084 (2)	0.107 (3)	0.115 (3)	−0.0042 (18)	0.063 (2)	0.003 (2)
C12	0.150 (4)	0.175 (4)	0.137 (3)	0.007 (3)	0.101 (3)	−0.034 (3)
C13	0.0517 (14)	0.0852 (19)	0.0931 (19)	0.0096 (12)	0.0399 (14)	0.0035 (15)
C14	0.0615 (15)	0.0609 (15)	0.0879 (18)	0.0039 (11)	0.0441 (14)	0.0010 (13)
C15	0.0546 (13)	0.0578 (14)	0.0625 (13)	−0.0003 (10)	0.0351 (11)	−0.0022 (11)
C16	0.0642 (15)	0.0571 (15)	0.0627 (14)	−0.0050 (11)	0.0392 (12)	−0.0010 (11)
C17	0.0549 (13)	0.0713 (15)	0.0502 (12)	−0.0077 (11)	0.0339 (11)	−0.0039 (11)
C18	0.0649 (16)	0.0880 (19)	0.0735 (16)	−0.0184 (14)	0.0423 (14)	−0.0115 (14)
C19	0.0568 (16)	0.124 (3)	0.0774 (18)	−0.0200 (16)	0.0404 (15)	−0.0171 (18)
C20	0.0521 (15)	0.121 (3)	0.0659 (16)	0.0077 (15)	0.0326 (13)	−0.0033 (16)
C21	0.0536 (14)	0.0880 (18)	0.0578 (14)	0.0083 (12)	0.0315 (12)	0.0010 (12)
C22	0.0477 (12)	0.0713 (15)	0.0448 (11)	0.0013 (10)	0.0283 (10)	0.0014 (10)
C23	0.0550 (13)	0.0609 (15)	0.0529 (12)	0.0029 (10)	0.0335 (11)	0.0030 (10)
C24	0.0484 (12)	0.0550 (13)	0.0524 (12)	0.0002 (9)	0.0308 (10)	−0.0016 (10)
N1	0.0547 (11)	0.0645 (12)	0.0546 (10)	−0.0010 (9)	0.0365 (9)	0.0006 (9)
N2	0.0489 (11)	0.0605 (12)	0.0736 (13)	0.0066 (8)	0.0328 (10)	0.0030 (10)
O1	0.0700 (11)	0.0974 (13)	0.0652 (10)	−0.0079 (9)	0.0446 (9)	−0.0194 (10)
O2	0.0657 (11)	0.0588 (11)	0.1013 (14)	0.0054 (8)	0.0430 (10)	0.0115 (9)
O3	0.0802 (13)	0.0600 (12)	0.1113 (15)	−0.0097 (9)	0.0528 (12)	−0.0038 (10)

C1—C6	1.369 (3)	C12—H12B	0.9600
C1—C2	1.386 (4)	C12—H12C	0.9600
C1—H1	0.9300	C13—N2	1.451 (3)
C2—C3	1.376 (4)	C13—H13A	0.9600
C2—H2	0.9300	C13—H13B	0.9600
C3—C4	1.376 (3)	C13—H13C	0.9600
C3—H3	0.9300	C14—N2	1.459 (3)
C4—C5	1.375 (3)	C14—C15	1.489 (3)
C4—H4	0.9300	C14—H14A	0.9700
C5—C6	1.384 (3)	C14—H14B	0.9700
C5—N1	1.403 (3)	C15—C24	1.328 (3)
C6—C7	1.505 (3)	C15—C16	1.468 (3)
C7—N2	1.464 (3)	C16—O3	1.211 (3)
C7—C24	1.508 (3)	C16—C17	1.486 (3)
C7—C8	1.558 (3)	C17—C22	1.392 (3)
C8—O1	1.212 (3)	C17—C18	1.390 (3)
C8—N1	1.355 (3)	C18—C19	1.377 (4)
C9—N1	1.459 (3)	C18—H18	0.9300
C9—C10	1.519 (4)	C19—C20	1.365 (4)
C9—H9A	0.9700	C19—H19	0.9300
C9—H9B	0.9700	C20—C21	1.373 (4)
C10—C11	1.467 (5)	C20—H20	0.9300
C10—H10A	0.9700	C21—C22	1.387 (3)
C10—H10B	0.9700	C21—H21	0.9300
C11—C12	1.536 (5)	C22—C23	1.482 (3)
C11—H11A	0.9700	C23—O2	1.214 (3)
C11—H11B	0.9700	C23—C24	1.464 (3)
C12—H12A	0.9600
C6—C1—C2	118.1 (2)	H12B—C12—H12C	109.5
C6—C1—H1	121.0	N2—C13—H13A	109.5
C2—C1—H1	121.0	N2—C13—H13B	109.5
C3—C2—C1	120.7 (2)	H13A—C13—H13B	109.5
C3—C2—H2	119.6	N2—C13—H13C	109.5
C1—C2—H2	119.6	H13A—C13—H13C	109.5
C2—C3—C4	121.5 (2)	H13B—C13—H13C	109.5
C2—C3—H3	119.2	N2—C14—C15	102.05 (19)
C4—C3—H3	119.2	N2—C14—H14A	111.4
C3—C4—C5	117.3 (2)	C15—C14—H14A	111.4
C3—C4—H4	121.3	N2—C14—H14B	111.4
C5—C4—H4	121.3	C15—C14—H14B	111.4
C4—C5—C6	121.7 (2)	H14A—C14—H14B	109.2
C4—C5—N1	128.0 (2)	C24—C15—C16	123.0 (2)
C6—C5—N1	110.27 (19)	C24—C15—C14	110.6 (2)
C1—C6—C5	120.6 (2)	C16—C15—C14	126.3 (2)
C1—C6—C7	130.1 (2)	O3—C16—C15	121.4 (2)
C5—C6—C7	109.27 (19)	O3—C16—C17	122.7 (2)
N2—C7—C6	114.30 (18)	C15—C16—C17	115.9 (2)
N2—C7—C24	100.92 (17)	C22—C17—C18	119.2 (2)
C6—C7—C24	117.14 (18)	C22—C17—C16	120.9 (2)
N2—C7—C8	114.02 (18)	C18—C17—C16	119.9 (2)
C6—C7—C8	100.99 (18)	C19—C18—C17	120.0 (3)
C24—C7—C8	110.01 (17)	C19—C18—H18	120.0
O1—C8—N1	126.4 (2)	C17—C18—H18	120.0
O1—C8—C7	124.9 (2)	C20—C19—C18	120.5 (3)
N1—C8—C7	108.61 (18)	C20—C19—H19	119.7
N1—C9—C10	112.7 (2)	C18—C19—H19	119.7
N1—C9—H9A	109.1	C19—C20—C21	120.4 (3)
C10—C9—H9A	109.1	C19—C20—H20	119.8
N1—C9—H9B	109.1	C21—C20—H20	119.8
C10—C9—H9B	109.1	C20—C21—C22	120.0 (3)
H9A—C9—H9B	107.8	C20—C21—H21	120.0
C11—C10—C9	114.7 (3)	C22—C21—H21	120.0
C11—C10—H10A	108.6	C21—C22—C17	119.7 (2)
C9—C10—H10A	108.6	C21—C22—C23	119.6 (2)
C11—C10—H10B	108.6	C17—C22—C23	120.67 (19)
C9—C10—H10B	108.6	O2—C23—C24	121.2 (2)
H10A—C10—H10B	107.6	O2—C23—C22	122.4 (2)
C10—C11—C12	111.9 (3)	C24—C23—C22	116.4 (2)
C10—C11—H11A	109.2	C15—C24—C23	122.3 (2)
C12—C11—H11A	109.2	C15—C24—C7	110.99 (19)
C10—C11—H11B	109.2	C23—C24—C7	126.4 (2)
C12—C11—H11B	109.2	C8—N1—C5	110.76 (18)
H11A—C11—H11B	107.9	C8—N1—C9	124.99 (19)
C11—C12—H12A	109.5	C5—N1—C9	124.2 (2)
C11—C12—H12B	109.5	C13—N2—C14	115.3 (2)
H12A—C12—H12B	109.5	C13—N2—C7	116.1 (2)
C11—C12—H12C	109.5	C14—N2—C7	109.86 (18)
H12A—C12—H12C	109.5
C6—C1—C2—C3	−0.6 (4)	C20—C21—C22—C23	179.5 (2)
C1—C2—C3—C4	−0.1 (4)	C18—C17—C22—C21	0.1 (3)
C2—C3—C4—C5	0.3 (4)	C16—C17—C22—C21	179.7 (2)
C3—C4—C5—C6	0.2 (3)	C18—C17—C22—C23	−179.2 (2)
C3—C4—C5—N1	178.6 (2)	C16—C17—C22—C23	0.5 (3)
C2—C1—C6—C5	1.1 (3)	C21—C22—C23—O2	−9.4 (3)
C2—C1—C6—C7	−178.1 (2)	C17—C22—C23—O2	169.8 (2)
C4—C5—C6—C1	−0.9 (3)	C21—C22—C23—C24	172.3 (2)
N1—C5—C6—C1	−179.54 (19)	C17—C22—C23—C24	−8.5 (3)
C4—C5—C6—C7	178.4 (2)	C16—C15—C24—C23	−4.1 (4)
N1—C5—C6—C7	−0.2 (2)	C14—C15—C24—C23	173.1 (2)
C1—C6—C7—N2	−59.5 (3)	C16—C15—C24—C7	−177.4 (2)
C5—C6—C7—N2	121.3 (2)	C14—C15—C24—C7	−0.3 (3)
C1—C6—C7—C24	58.2 (3)	O2—C23—C24—C15	−167.8 (2)
C5—C6—C7—C24	−121.0 (2)	C22—C23—C24—C15	10.5 (3)
C1—C6—C7—C8	177.7 (2)	O2—C23—C24—C7	4.4 (3)
C5—C6—C7—C8	−1.6 (2)	C22—C23—C24—C7	−177.30 (19)
N2—C7—C8—O1	57.6 (3)	N2—C7—C24—C15	−13.6 (2)
C6—C7—C8—O1	−179.4 (2)	C6—C7—C24—C15	−138.4 (2)
C24—C7—C8—O1	−55.0 (3)	C8—C7—C24—C15	107.1 (2)
N2—C7—C8—N1	−120.1 (2)	N2—C7—C24—C23	173.4 (2)
C6—C7—C8—N1	2.9 (2)	C6—C7—C24—C23	48.6 (3)
C24—C7—C8—N1	127.36 (19)	C8—C7—C24—C23	−65.9 (3)
N1—C9—C10—C11	72.8 (3)	O1—C8—N1—C5	179.1 (2)
C9—C10—C11—C12	76.8 (4)	C7—C8—N1—C5	−3.3 (2)
N2—C14—C15—C24	14.2 (3)	O1—C8—N1—C9	−4.3 (4)
N2—C14—C15—C16	−168.8 (2)	C7—C8—N1—C9	173.35 (19)
C24—C15—C16—O3	175.6 (2)	C4—C5—N1—C8	−176.2 (2)
C14—C15—C16—O3	−1.1 (4)	C6—C5—N1—C8	2.2 (2)
C24—C15—C16—C17	−4.2 (3)	C4—C5—N1—C9	7.1 (3)
C14—C15—C16—C17	179.0 (2)	C6—C5—N1—C9	−174.4 (2)
O3—C16—C17—C22	−173.9 (2)	C10—C9—N1—C8	−104.7 (3)
C15—C16—C17—C22	5.9 (3)	C10—C9—N1—C5	71.5 (3)
O3—C16—C17—C18	5.8 (4)	C15—C14—N2—C13	−156.7 (2)
C15—C16—C17—C18	−174.4 (2)	C15—C14—N2—C7	−23.2 (3)
C22—C17—C18—C19	−0.3 (4)	C6—C7—N2—C13	−77.4 (3)
C16—C17—C18—C19	−179.9 (2)	C24—C7—N2—C13	155.9 (2)
C17—C18—C19—C20	0.2 (4)	C8—C7—N2—C13	38.1 (3)
C18—C19—C20—C21	0.2 (4)	C6—C7—N2—C14	149.4 (2)
C19—C20—C21—C22	−0.4 (4)	C24—C7—N2—C14	22.8 (2)
C20—C21—C22—C17	0.3 (3)	C8—C7—N2—C14	−95.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1i	0.93	2.39	3.232 (4)	151
C9—H9A···O2ii	0.97	2.45	3.230 (3)	137
C20—H20···O1iii	0.93	2.52	3.205 (3)	131
C11—H11B···Cg1iv	0.97	2.82	3.759 (4)	164

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1i	0.93	2.39	3.232 (4)	151
C9—H9A⋯O2ii	0.97	2.45	3.230 (3)	137
C20—H20⋯O1iii	0.93	2.52	3.205 (3)	131
C11—H11B⋯Cg1iv	0.97	2.82	3.759 (4)	164

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