1,1''-Bis(prop-2-en-1-yl)-1,1'',2,2''-tetra-hydro-dispiro-[indole-3,7'-[6,9]diaza-tricyclo-[7.3.0.0(2,6)]dodecane-8',3''-indole]-2,2''-dione.

The mol-ecule of the title compound, C(30)H(32)N(4)O(2), lies on a twofold rotation axis that passes through the mid-points of the C-C bonds of the piperazine ring, which adopts a chair conformation. The pyrrolidine ring that is fused to the piperazine ring adopts an envelope conformation (in which the N atom represents the flap). The indoline fused-ring system is nearly planar (r.m.s. deviation = 0.044 Å); the two symmetry-related indoline fused-rings systems are aligned at 71.44 (3)°.

Related literature

For background to the class of dispiro compounds, see: Al Mamari et al. (2012 ▶). For a related structure, see: Sugaleshini et al. (2006 ▶).

Experimental

Crystal data

C30H32N4O2

M = 480.60

Monoclinic,

a = 14.9484 (2) Å

b = 9.9173 (1) Å

c = 17.5713 (3) Å

β = 111.119 (1)°

V = 2429.94 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.18 × 0.16 × 0.14 mm

Data collection

Bruker APEX DUO diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.985, T max = 0.988

13297 measured reflections

2797 independent reflections

2441 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.119

S = 1.00

2797 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019216/xu5527sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019216/xu5527Isup2.hkl

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

C30H32N4O2	F(000) = 1024
Mr = 480.60	Dx = 1.314 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8483 reflections
a = 14.9484 (2) Å	θ = 2.5–32.7°
b = 9.9173 (1) Å	µ = 0.08 mm−1
c = 17.5713 (3) Å	T = 293 K
β = 111.119 (1)°	Prism, colorless
V = 2429.94 (6) Å3	0.18 × 0.16 × 0.14 mm
Z = 4

Bruker APEX DUO diffractometer	2797 independent reflections
Radiation source: fine-focus sealed tube	2441 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→19
Tmin = 0.985, Tmax = 0.988	k = −12→12
13297 measured reflections	l = −22→20

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0678P)2 + 1.2982P] where P = (Fo2 + 2Fc2)/3
2797 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.43126 (6)	0.47958 (9)	0.37259 (6)	0.0390 (2)
N1	0.52761 (7)	0.66607 (10)	0.39788 (6)	0.0315 (2)
N2	0.59105 (6)	0.39146 (9)	0.30977 (6)	0.0285 (2)
C1	0.49026 (7)	0.54901 (11)	0.35787 (6)	0.0283 (2)
C2	0.53923 (7)	0.51947 (10)	0.29458 (6)	0.0255 (2)
C3	0.61013 (7)	0.63591 (11)	0.31150 (7)	0.0272 (2)
C4	0.68373 (8)	0.66113 (12)	0.28314 (8)	0.0348 (3)
H4	0.6923	0.6064	0.2433	0.042*
C5	0.74493 (8)	0.76994 (13)	0.31530 (9)	0.0406 (3)
H5	0.7937	0.7891	0.2958	0.049*
C6	0.73379 (9)	0.84936 (13)	0.37577 (9)	0.0409 (3)
H6	0.7752	0.9215	0.3964	0.049*
C7	0.66169 (9)	0.82346 (12)	0.40655 (8)	0.0373 (3)
H7	0.6546	0.8762	0.4478	0.045*
C8	0.60104 (8)	0.71628 (11)	0.37335 (7)	0.0289 (2)
C9	0.50268 (10)	0.72080 (14)	0.46422 (8)	0.0419 (3)
H9A	0.5611	0.7350	0.5110	0.050*
H9B	0.4644	0.6548	0.4797	0.050*
C10	0.44850 (11)	0.85017 (16)	0.44444 (10)	0.0520 (4)
H10	0.4341	0.8903	0.4865	0.062*
C11	0.41912 (12)	0.91320 (17)	0.37480 (12)	0.0618 (4)
H11A	0.4316	0.8775	0.3307	0.074*
H11B	0.3857	0.9939	0.3691	0.074*
C12	0.66448 (9)	0.37194 (13)	0.39119 (7)	0.0376 (3)
H12A	0.6392	0.3916	0.4337	0.045*
H12B	0.7200	0.4284	0.3989	0.045*
C13	0.68964 (10)	0.22205 (14)	0.39088 (9)	0.0486 (4)
H13A	0.7495	0.2111	0.3819	0.058*
H13B	0.6959	0.1804	0.4425	0.058*
C14	0.60698 (9)	0.15842 (13)	0.32126 (9)	0.0424 (3)
H14A	0.6275	0.1318	0.2770	0.051*
H14B	0.5822	0.0799	0.3401	0.051*
C15	0.53166 (8)	0.26936 (11)	0.29411 (7)	0.0315 (3)
H15	0.4925	0.2690	0.3284	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0364 (4)	0.0421 (5)	0.0445 (5)	−0.0111 (4)	0.0218 (4)	0.0000 (4)
N1	0.0325 (5)	0.0313 (5)	0.0345 (5)	−0.0039 (4)	0.0167 (4)	−0.0031 (4)
N2	0.0229 (4)	0.0263 (5)	0.0318 (5)	0.0005 (3)	0.0046 (4)	0.0013 (4)
C1	0.0253 (5)	0.0298 (5)	0.0297 (5)	−0.0008 (4)	0.0099 (4)	0.0028 (4)
C2	0.0213 (5)	0.0263 (5)	0.0293 (5)	−0.0012 (4)	0.0095 (4)	0.0006 (4)
C3	0.0222 (5)	0.0264 (5)	0.0315 (5)	−0.0012 (4)	0.0078 (4)	0.0021 (4)
C4	0.0276 (5)	0.0384 (6)	0.0411 (6)	−0.0026 (5)	0.0156 (5)	−0.0004 (5)
C5	0.0270 (6)	0.0423 (7)	0.0547 (7)	−0.0064 (5)	0.0173 (5)	0.0041 (6)
C6	0.0289 (6)	0.0313 (6)	0.0579 (8)	−0.0081 (5)	0.0101 (5)	−0.0005 (5)
C7	0.0345 (6)	0.0309 (6)	0.0443 (7)	−0.0042 (5)	0.0116 (5)	−0.0060 (5)
C8	0.0253 (5)	0.0271 (5)	0.0337 (5)	−0.0005 (4)	0.0099 (4)	0.0027 (4)
C9	0.0484 (7)	0.0470 (7)	0.0361 (6)	−0.0057 (6)	0.0223 (6)	−0.0062 (5)
C10	0.0529 (8)	0.0475 (8)	0.0669 (9)	−0.0053 (6)	0.0353 (7)	−0.0185 (7)
C11	0.0509 (9)	0.0482 (9)	0.0854 (12)	0.0068 (7)	0.0234 (9)	−0.0022 (8)
C12	0.0302 (6)	0.0380 (6)	0.0362 (6)	0.0025 (5)	0.0017 (5)	0.0024 (5)
C13	0.0389 (7)	0.0392 (7)	0.0537 (8)	0.0078 (5)	−0.0004 (6)	0.0065 (6)
C14	0.0386 (7)	0.0292 (6)	0.0515 (7)	0.0049 (5)	0.0066 (6)	0.0061 (5)
C15	0.0281 (5)	0.0261 (5)	0.0375 (6)	−0.0008 (4)	0.0085 (5)	0.0022 (4)

O1—C1	1.2178 (13)	C7—H7	0.9300
N1—C1	1.3677 (15)	C9—C10	1.490 (2)
N1—C8	1.4070 (14)	C9—H9A	0.9700
N1—C9	1.4511 (15)	C9—H9B	0.9700
N2—C2	1.4608 (13)	C10—C11	1.301 (3)
N2—C15	1.4677 (14)	C10—H10	0.9300
N2—C12	1.4688 (14)	C11—H11A	0.9300
C1—C2	1.5637 (14)	C11—H11B	0.9300
C2—C3	1.5226 (14)	C12—C13	1.5339 (18)
C2—C2i	1.583 (2)	C12—H12A	0.9700
C3—C4	1.3843 (15)	C12—H12B	0.9700
C3—C8	1.3933 (16)	C13—C14	1.5273 (19)
C4—C5	1.3958 (17)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.380 (2)	C14—C15	1.5226 (16)
C5—H5	0.9300	C14—H14A	0.9700
C6—C7	1.3929 (18)	C14—H14B	0.9700
C6—H6	0.9300	C15—C15i	1.497 (2)
C7—C8	1.3824 (16)	C15—H15	0.9800
C1—N1—C8	111.22 (9)	C10—C9—H9A	108.7
C1—N1—C9	123.71 (10)	N1—C9—H9B	108.7
C8—N1—C9	124.63 (10)	C10—C9—H9B	108.7
C2—N2—C15	115.95 (8)	H9A—C9—H9B	107.6
C2—N2—C12	116.96 (9)	C11—C10—C9	127.15 (14)
C15—N2—C12	105.26 (9)	C11—C10—H10	116.4
O1—C1—N1	124.30 (10)	C9—C10—H10	116.4
O1—C1—C2	127.27 (10)	C10—C11—H11A	120.0
N1—C1—C2	108.39 (9)	C10—C11—H11B	120.0
N2—C2—C3	109.72 (8)	H11A—C11—H11B	120.0
N2—C2—C1	112.72 (8)	N2—C12—C13	102.86 (10)
C3—C2—C1	100.98 (8)	N2—C12—H12A	111.2
N2—C2—C2i	109.62 (6)	C13—C12—H12A	111.2
C3—C2—C2i	114.12 (7)	N2—C12—H12B	111.2
C1—C2—C2i	109.52 (9)	C13—C12—H12B	111.2
C4—C3—C8	119.41 (10)	H12A—C12—H12B	109.1
C4—C3—C2	130.87 (10)	C14—C13—C12	105.93 (10)
C8—C3—C2	109.23 (9)	C14—C13—H13A	110.5
C3—C4—C5	118.94 (11)	C12—C13—H13A	110.5
C3—C4—H4	120.5	C14—C13—H13B	110.5
C5—C4—H4	120.5	C12—C13—H13B	110.5
C6—C5—C4	120.64 (11)	H13A—C13—H13B	108.7
C6—C5—H5	119.7	C15—C14—C13	104.24 (10)
C4—C5—H5	119.7	C15—C14—H14A	110.9
C5—C6—C7	121.24 (11)	C13—C14—H14A	110.9
C5—C6—H6	119.4	C15—C14—H14B	110.9
C7—C6—H6	119.4	C13—C14—H14B	110.9
C8—C7—C6	117.35 (12)	H14A—C14—H14B	108.9
C8—C7—H7	121.3	N2—C15—C15i	107.95 (8)
C6—C7—H7	121.3	N2—C15—C14	102.03 (9)
C7—C8—C3	122.38 (11)	C15i—C15—C14	116.41 (10)
C7—C8—N1	127.46 (11)	N2—C15—H15	110.0
C3—C8—N1	110.04 (9)	C15i—C15—H15	110.0
N1—C9—C10	114.21 (11)	C14—C15—H15	110.0
N1—C9—H9A	108.7
C8—N1—C1—O1	173.93 (11)	C4—C5—C6—C7	0.1 (2)
C9—N1—C1—O1	1.24 (18)	C5—C6—C7—C8	−0.85 (19)
C8—N1—C1—C2	−3.80 (12)	C6—C7—C8—C3	−0.04 (18)
C9—N1—C1—C2	−176.49 (10)	C6—C7—C8—N1	175.65 (11)
C15—N2—C2—C3	−178.61 (9)	C4—C3—C8—C7	1.66 (17)
C12—N2—C2—C3	56.22 (12)	C2—C3—C8—C7	174.50 (10)
C15—N2—C2—C1	69.71 (11)	C4—C3—C8—N1	−174.70 (10)
C12—N2—C2—C1	−55.46 (12)	C2—C3—C8—N1	−1.86 (12)
C15—N2—C2—C2i	−52.56 (13)	C1—N1—C8—C7	−172.47 (11)
C12—N2—C2—C2i	−177.72 (10)	C9—N1—C8—C7	0.14 (19)
O1—C1—C2—N2	−58.18 (14)	C1—N1—C8—C3	3.66 (13)
N1—C1—C2—N2	119.46 (10)	C9—N1—C8—C3	176.27 (11)
O1—C1—C2—C3	−175.17 (11)	C1—N1—C9—C10	−113.01 (14)
N1—C1—C2—C3	2.47 (11)	C8—N1—C9—C10	75.28 (15)
O1—C1—C2—C2i	64.14 (12)	N1—C9—C10—C11	3.0 (2)
N1—C1—C2—C2i	−118.22 (7)	C2—N2—C12—C13	169.82 (10)
N2—C2—C3—C4	52.23 (15)	C15—N2—C12—C13	39.45 (12)
C1—C2—C3—C4	171.40 (11)	N2—C12—C13—C14	−17.94 (15)
C2i—C2—C3—C4	−71.23 (15)	C12—C13—C14—C15	−8.73 (15)
N2—C2—C3—C8	−119.51 (10)	C2—N2—C15—C15i	60.60 (14)
C1—C2—C3—C8	−0.34 (11)	C12—N2—C15—C15i	−168.44 (11)
C2i—C2—C3—C8	117.03 (11)	C2—N2—C15—C14	−176.24 (10)
C8—C3—C4—C5	−2.36 (17)	C12—N2—C15—C14	−45.28 (12)
C2—C3—C4—C5	−173.40 (11)	C13—C14—C15—N2	32.17 (13)
C3—C4—C5—C6	1.51 (19)	C13—C14—C15—C15i	149.40 (12)