5-Chloro-5''-(4-chloro-benzyl-idene)-4'-(4-chloro-phen-yl)-1',1''-dimethyldi-spiro-[indoline-3,2'-pyrrolidine-3',3''-piperidine]-2,4''-dione.

The racemic title compound, C30H26Cl3N3O2, comprises two spiro links, the first connecting the piperidine and pyrrolidine rings and the other connecting the indole and pyrrolidine rings. The piperidine ring adopts a half-chair conformation, while the pyrrolidine ring has an envelope conformation with the unsubstituted C atom as the flap. The dihedral angles between the two p-Cl-substituted benzene rings and the indole ring are 33.13 (14) and 54.11 (14)°. In the crystal, mol-ecules form inversion dimers through pairs of N-H⋯O hydrogen bonds [graph set R 2 (2)(8)]. Aromatic C-H⋯O hydrogen bonds extend these dimers into a ribbon structure, enclosing R (2) 2(14) ring motifs, along the a-axis direction.

Related literature

For the biological activity of related di­spiro-oxindole analogues, see: Girgis et al. (2009a ▶,b ▶, 2012 ▶); George et al. (2013 ▶). For related structural studies, see: Farag et al. (2014a ▶,b ▶,c ▶); Moustafa et al. (2012 ▶). For the synthesis of the precursor mol­ecule, see: Modzelewska et al. (2006 ▶). For graph-set analysis, see: Etter et al. (1990 ▶). For details of the weighting scheme used, see: Watkin et al. (1994 ▶). H atoms were refined with riding constraints (Cooper et al., 2010 ▶).

Experimental

Crystal data

C30H26Cl3N3O2

M = 566.91

Triclinic,

a = 11.2102 (3) Å

b = 11.5909 (3) Å

c = 12.3569 (4) Å

α = 99.0734 (8)°

β = 90.1887 (9)°

γ = 116.4041 (10)°

V = 1415.22 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 298 K

0.35 × 0.19 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan [Görbitz (1999 ▶) and DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶)] T min = 0.630, T max = 0.876

16419 measured reflections

6508 independent reflections

3663 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.111

S = 1.01

3663 reflections

344 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.54 e Å−3

Data collection: COLLECT (Nonius, 2001 ▶).; cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶) and DIAMOND (Brandenburg, 2012 ▶); software used to prepare material for publication: CRYSTALS; software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) New_Global_Publ_Block, I. DOI: 10.1107/S1600536814004309/zs2286sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004309/zs2286Isup2.hkl

CCDC reference: 988672

Additional supporting information: crystallographic information; 3D view; checkCIF report

C30H26Cl3N3O2	Z = 2
Mr = 566.91	F(000) = 588
Triclinic, P1	Dx = 1.330 Mg m−3
Hall symbol: -P 1	Melting point = 510–512 K
a = 11.2102 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.5909 (3) Å	Cell parameters from 8506 reflections
c = 12.3569 (4) Å	θ = 3–27°
α = 99.0734 (8)°	µ = 0.36 mm−1
β = 90.1887 (9)°	T = 298 K
γ = 116.4041 (10)°	Plate, pale yellow
V = 1415.22 (7) Å3	0.35 × 0.19 × 0.10 mm

Nonius KappaCCD diffractometer	3663 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
φ and ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan [Görbitz (1999) and DENZO/SCALEPACK (Otwinowski & Minor, 1997)]	h = −14→13
Tmin = 0.630, Tmax = 0.876	k = −14→15
16419 measured reflections	l = −13→16
6508 independent reflections

Refinement on F2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.057	Method, part 1, Chebychev polynomial, (Watkin et al., 1994) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 100. 168. 111. 49.9 14.3
wR(F2) = 0.111	(Δ/σ)max = 0.001
S = 1.01	Δρmax = 0.55 e Å−3
3663 reflections	Δρmin = −0.54 e Å−3
344 parameters	Extinction correction: Larson (1970), Equation 22
0 restraints	Extinction coefficient: 400 (70)

	x	y	z	Uiso*/Ueq
Cl1	0.60430 (10)	0.03618 (8)	0.26749 (8)	0.0754
C2	0.6044 (3)	0.1352 (3)	0.3894 (3)	0.0503
C3	0.6541 (3)	0.1232 (3)	0.4866 (3)	0.0529
C4	0.6557 (3)	0.2027 (3)	0.5831 (3)	0.0487
C5	0.6067 (3)	0.2943 (2)	0.5838 (2)	0.0417
C6	0.5543 (3)	0.3014 (3)	0.4848 (2)	0.0492
C7	0.5530 (3)	0.2237 (3)	0.3873 (3)	0.0542
C8	0.6072 (2)	0.3840 (2)	0.6877 (2)	0.0409
C9	0.5750 (3)	0.3253 (3)	0.7914 (3)	0.0516
N10	0.6166 (2)	0.4411 (2)	0.8759 (2)	0.0492
C11	0.7498 (3)	0.5363 (2)	0.8520 (2)	0.0397
C12	0.7408 (2)	0.5121 (2)	0.7215 (2)	0.0354
C13	0.8657 (2)	0.5050 (2)	0.6782 (2)	0.0400
N14	0.9809 (2)	0.6228 (2)	0.73096 (19)	0.0418
C15	1.1053 (3)	0.6102 (3)	0.7277 (3)	0.0639
C16	0.9952 (3)	0.7356 (2)	0.6850 (2)	0.0432
C17	0.8667 (3)	0.7462 (2)	0.6750 (2)	0.0367
C18	0.7363 (3)	0.6297 (2)	0.6818 (2)	0.0374
O19	0.63054 (19)	0.62778 (19)	0.65825 (18)	0.0539
C20	0.8581 (3)	0.8543 (2)	0.6587 (2)	0.0402
C21	0.9613 (3)	0.9854 (3)	0.6496 (2)	0.0406
C22	1.0951 (3)	1.0193 (3)	0.6338 (2)	0.0477
C23	1.1861 (3)	1.1452 (3)	0.6272 (3)	0.0532
C24	1.1446 (3)	1.2413 (3)	0.6355 (3)	0.0522
Cl25	1.25982 (10)	1.40017 (8)	0.62645 (10)	0.0835
C26	1.0126 (3)	1.2121 (3)	0.6494 (3)	0.0598
C27	0.9234 (3)	1.0851 (3)	0.6562 (3)	0.0521
C28	0.8616 (3)	0.5122 (3)	0.9037 (2)	0.0482
O29	0.8737 (2)	0.4106 (2)	0.88320 (18)	0.0582
N30	0.9342 (3)	0.6146 (2)	0.9844 (2)	0.0591
C31	0.8905 (3)	0.7109 (3)	0.9914 (3)	0.0578
C32	0.7834 (3)	0.6724 (3)	0.9147 (2)	0.0466
C33	0.7187 (3)	0.7487 (3)	0.9109 (3)	0.0559
C34	0.7670 (5)	0.8668 (3)	0.9847 (3)	0.0756
Cl35	0.68788 (17)	0.96581 (12)	0.98031 (12)	0.1253
C36	0.8741 (5)	0.9054 (4)	1.0601 (3)	0.0925
C37	0.9380 (5)	0.8278 (4)	1.0642 (3)	0.0812
C38	0.6049 (4)	0.4161 (4)	0.9884 (3)	0.0741
H31	0.6875	0.0600	0.4875	0.0634*
H41	0.6912	0.1947	0.6508	0.0584*
H61	0.5179	0.3622	0.4839	0.0591*
H71	0.5171	0.2309	0.3194	0.0651*
H81	0.5398	0.4108	0.6738	0.0490*
H91	0.6249	0.2780	0.8011	0.0619*
H92	0.4813	0.2684	0.7906	0.0619*
H131	0.8702	0.4292	0.6959	0.0480*
H132	0.8631	0.5003	0.5999	0.0480*
H151	1.1779	0.6908	0.7637	0.0769*
H152	1.0970	0.5405	0.7648	0.0769*
H153	1.1224	0.5912	0.6526	0.0769*
H161	1.0599	0.8133	0.7317	0.0518*
H162	1.0265	0.7293	0.6131	0.0518*
H201	0.7683	0.8438	0.6517	0.0482*
H221	1.1247	0.9526	0.6274	0.0572*
H231	1.2778	1.1659	0.6168	0.0638*
H261	0.9835	1.2790	0.6542	0.0717*
H271	0.8317	1.0649	0.6659	0.0624*
H331	0.6431	0.7215	0.8593	0.0669*
H361	0.9045	0.9868	1.1105	0.1110*
H371	1.0133	0.8547	1.1160	0.0974*
H381	0.6343	0.4974	1.0388	0.0890*
H382	0.6594	0.3746	1.0027	0.0890*
H383	0.5134	0.3597	0.9977	0.0890*
H301	1.0063	0.6204	1.0307	0.0710*

	U11	U22	U33	U12	U13	U23
Cl1	0.0825 (6)	0.0603 (5)	0.0685 (6)	0.0259 (4)	0.0069 (5)	−0.0100 (4)
C2	0.0439 (16)	0.0407 (15)	0.0535 (19)	0.0097 (13)	0.0027 (14)	0.0021 (13)
C3	0.0552 (19)	0.0391 (15)	0.067 (2)	0.0250 (14)	0.0025 (16)	0.0058 (14)
C4	0.0498 (17)	0.0480 (16)	0.0542 (18)	0.0276 (14)	−0.0035 (14)	0.0085 (14)
C5	0.0327 (14)	0.0361 (13)	0.0516 (17)	0.0129 (11)	−0.0049 (12)	0.0032 (12)
C6	0.0486 (17)	0.0442 (15)	0.0554 (19)	0.0226 (13)	−0.0095 (14)	0.0053 (14)
C7	0.0500 (18)	0.0528 (17)	0.056 (2)	0.0208 (15)	−0.0087 (14)	0.0062 (15)
C8	0.0321 (14)	0.0375 (13)	0.0520 (17)	0.0160 (11)	−0.0036 (12)	0.0044 (12)
C9	0.0406 (16)	0.0400 (15)	0.065 (2)	0.0101 (13)	0.0063 (14)	0.0100 (14)
N10	0.0506 (14)	0.0472 (13)	0.0492 (15)	0.0193 (11)	0.0139 (11)	0.0150 (11)
C11	0.0409 (15)	0.0392 (13)	0.0391 (16)	0.0179 (12)	0.0033 (12)	0.0083 (11)
C12	0.0338 (14)	0.0341 (12)	0.0392 (15)	0.0161 (11)	−0.0021 (11)	0.0067 (11)
C13	0.0385 (15)	0.0359 (13)	0.0483 (17)	0.0200 (12)	−0.0008 (12)	0.0055 (12)
N14	0.0338 (12)	0.0379 (11)	0.0572 (15)	0.0182 (10)	0.0009 (10)	0.0117 (10)
C15	0.0433 (17)	0.0531 (18)	0.105 (3)	0.0271 (15)	0.0038 (18)	0.0238 (19)
C16	0.0409 (15)	0.0358 (13)	0.0547 (18)	0.0187 (12)	0.0050 (13)	0.0090 (12)
C17	0.0420 (14)	0.0401 (14)	0.0332 (14)	0.0227 (12)	0.0008 (11)	0.0072 (11)
C18	0.0391 (15)	0.0421 (14)	0.0345 (14)	0.0222 (12)	−0.0022 (11)	0.0043 (11)
O19	0.0432 (12)	0.0533 (12)	0.0723 (15)	0.0251 (10)	−0.0040 (10)	0.0206 (10)
C20	0.0426 (15)	0.0426 (14)	0.0399 (16)	0.0227 (12)	0.0008 (12)	0.0091 (12)
C21	0.0491 (17)	0.0409 (14)	0.0338 (15)	0.0222 (13)	−0.0027 (12)	0.0059 (11)
C22	0.0560 (18)	0.0423 (15)	0.0528 (18)	0.0289 (14)	0.0095 (14)	0.0096 (13)
C23	0.0528 (18)	0.0480 (16)	0.064 (2)	0.0260 (15)	0.0117 (15)	0.0129 (14)
C24	0.0551 (19)	0.0389 (14)	0.060 (2)	0.0192 (13)	0.0050 (15)	0.0075 (13)
Cl25	0.0753 (6)	0.0397 (4)	0.1315 (9)	0.0217 (4)	0.0239 (6)	0.0166 (5)
C26	0.066 (2)	0.0391 (15)	0.080 (2)	0.0298 (15)	0.0029 (17)	0.0089 (15)
C27	0.0483 (17)	0.0483 (16)	0.066 (2)	0.0277 (14)	−0.0018 (14)	0.0101 (14)
C28	0.0530 (18)	0.0491 (16)	0.0441 (17)	0.0219 (14)	0.0003 (13)	0.0164 (14)
O29	0.0642 (14)	0.0510 (12)	0.0678 (14)	0.0315 (11)	−0.0091 (11)	0.0171 (10)
N30	0.0666 (17)	0.0545 (15)	0.0520 (16)	0.0234 (13)	−0.0198 (13)	0.0101 (13)
C31	0.074 (2)	0.0489 (17)	0.0404 (17)	0.0196 (16)	−0.0052 (15)	0.0071 (14)
C32	0.0567 (17)	0.0461 (15)	0.0370 (16)	0.0218 (14)	0.0102 (13)	0.0110 (13)
C33	0.074 (2)	0.0544 (17)	0.0493 (19)	0.0361 (16)	0.0206 (16)	0.0134 (14)
C34	0.115 (3)	0.059 (2)	0.066 (2)	0.050 (2)	0.029 (2)	0.0090 (19)
Cl35	0.1911 (15)	0.0969 (8)	0.1324 (11)	0.1058 (10)	0.0520 (10)	0.0150 (8)
C36	0.153 (4)	0.057 (2)	0.054 (2)	0.040 (3)	0.007 (3)	−0.0053 (18)
C37	0.119 (3)	0.061 (2)	0.043 (2)	0.025 (2)	−0.011 (2)	−0.0012 (17)
C38	0.085 (3)	0.074 (2)	0.062 (2)	0.030 (2)	0.0281 (19)	0.0254 (19)

Cl1—C2	1.743 (3)	C16—H162	0.960
C2—C3	1.375 (4)	C17—C18	1.500 (4)
C2—C7	1.386 (4)	C17—C20	1.345 (3)
C3—C4	1.382 (4)	C18—O19	1.209 (3)
C3—H31	0.960	C20—C21	1.467 (4)
C4—C5	1.394 (4)	C20—H201	0.960
C4—H41	0.960	C21—C22	1.395 (4)
C5—C6	1.386 (4)	C21—C27	1.389 (4)
C5—C8	1.517 (4)	C22—C23	1.376 (4)
C6—C7	1.382 (4)	C22—H221	0.960
C6—H61	0.960	C23—C24	1.375 (4)
C7—H71	0.960	C23—H231	0.960
C8—C9	1.514 (4)	C24—Cl25	1.739 (3)
C8—C12	1.563 (3)	C24—C26	1.381 (4)
C8—H81	0.960	C26—C27	1.380 (4)
C9—N10	1.452 (4)	C26—H261	0.960
C9—H91	0.960	C27—H271	0.960
C9—H92	0.960	C28—O29	1.230 (3)
N10—C11	1.474 (3)	C28—N30	1.352 (4)
N10—C38	1.459 (4)	N30—C31	1.397 (4)
C11—C12	1.588 (4)	N30—H301	0.960
C11—C28	1.556 (4)	C31—C32	1.385 (4)
C11—C32	1.521 (4)	C31—C37	1.378 (5)
C12—C13	1.532 (4)	C32—C33	1.376 (4)
C12—C18	1.540 (3)	C33—C34	1.393 (5)
C13—N14	1.450 (3)	C33—H331	0.960
C13—H131	0.960	C34—Cl35	1.741 (4)
C13—H132	0.960	C34—C36	1.376 (6)
N14—C15	1.464 (3)	C36—C37	1.382 (6)
N14—C16	1.452 (3)	C36—H361	0.960
C15—H151	0.960	C37—H371	0.960
C15—H152	0.960	C38—H381	0.960
C15—H153	0.960	C38—H382	0.960
C16—C17	1.505 (4)	C38—H383	0.960
C16—H161	0.960
Cl1—C2—C3	119.5 (2)	C17—C16—H161	108.5
Cl1—C2—C7	119.7 (3)	N14—C16—H162	108.5
C3—C2—C7	120.8 (3)	C17—C16—H162	108.5
C2—C3—C4	119.5 (3)	H161—C16—H162	109.5
C2—C3—H31	120.2	C16—C17—C18	119.6 (2)
C4—C3—H31	120.2	C16—C17—C20	124.7 (2)
C3—C4—C5	121.2 (3)	C18—C17—C20	115.6 (2)
C3—C4—H41	119.4	C12—C18—C17	117.8 (2)
C5—C4—H41	119.4	C12—C18—O19	120.7 (2)
C4—C5—C6	117.8 (3)	C17—C18—O19	121.5 (2)
C4—C5—C8	122.9 (3)	C17—C20—C21	131.5 (3)
C6—C5—C8	119.3 (2)	C17—C20—H201	114.2
C5—C6—C7	121.9 (3)	C21—C20—H201	114.3
C5—C6—H61	119.0	C20—C21—C22	125.7 (2)
C7—C6—H61	119.0	C20—C21—C27	117.8 (3)
C2—C7—C6	118.7 (3)	C22—C21—C27	116.5 (2)
C2—C7—H71	120.6	C21—C22—C23	122.1 (3)
C6—C7—H71	120.7	C21—C22—H221	119.0
C5—C8—C9	116.7 (2)	C23—C22—H221	119.0
C5—C8—C12	115.4 (2)	C22—C23—C24	119.4 (3)
C9—C8—C12	104.3 (2)	C22—C23—H231	120.3
C5—C8—H81	106.6	C24—C23—H231	120.3
C9—C8—H81	106.6	C23—C24—Cl25	119.3 (2)
C12—C8—H81	106.6	C23—C24—C26	120.7 (3)
C8—C9—N10	101.9 (2)	Cl25—C24—C26	120.1 (2)
C8—C9—H91	111.3	C24—C26—C27	118.8 (3)
N10—C9—H91	111.3	C24—C26—H261	120.6
C8—C9—H92	111.3	C27—C26—H261	120.6
N10—C9—H92	111.3	C21—C27—C26	122.5 (3)
H91—C9—H92	109.5	C21—C27—H271	118.7
C9—N10—C11	107.0 (2)	C26—C27—H271	118.7
C9—N10—C38	114.9 (2)	C11—C28—O29	125.7 (3)
C11—N10—C38	115.6 (3)	C11—C28—N30	108.9 (2)
N10—C11—C12	103.0 (2)	O29—C28—N30	125.0 (3)
N10—C11—C28	110.9 (2)	C28—N30—C31	111.0 (2)
C12—C11—C28	113.1 (2)	C28—N30—H301	124.5
N10—C11—C32	110.3 (2)	C31—N30—H301	124.5
C12—C11—C32	119.1 (2)	N30—C31—C32	110.5 (3)
C28—C11—C32	100.6 (2)	N30—C31—C37	128.0 (3)
C8—C12—C11	103.6 (2)	C32—C31—C37	121.5 (3)
C8—C12—C13	115.0 (2)	C11—C32—C31	108.8 (2)
C11—C12—C13	111.2 (2)	C11—C32—C33	130.2 (3)
C8—C12—C18	111.9 (2)	C31—C32—C33	120.7 (3)
C11—C12—C18	108.90 (19)	C32—C33—C34	117.6 (3)
C13—C12—C18	106.2 (2)	C32—C33—H331	121.2
C12—C13—N14	107.5 (2)	C34—C33—H331	121.2
C12—C13—H131	109.9	C33—C34—Cl35	118.5 (4)
N14—C13—H131	109.9	C33—C34—C36	121.5 (3)
C12—C13—H132	110.0	Cl35—C34—C36	120.0 (3)
N14—C13—H132	110.0	C34—C36—C37	120.6 (3)
H131—C13—H132	109.5	C34—C36—H361	119.7
C13—N14—C15	113.2 (2)	C37—C36—H361	119.7
C13—N14—C16	111.3 (2)	C36—C37—C31	118.1 (4)
C15—N14—C16	110.6 (2)	C36—C37—H371	121.0
N14—C15—H151	109.5	C31—C37—H371	121.0
N14—C15—H152	109.5	N10—C38—H381	109.5
H151—C15—H152	109.5	N10—C38—H382	109.5
N14—C15—H153	109.4	H381—C38—H382	109.5
H151—C15—H153	109.5	N10—C38—H383	109.4
H152—C15—H153	109.5	H381—C38—H383	109.5
N14—C16—C17	113.3 (2)	H382—C38—H383	109.5
N14—C16—H161	108.5
Cl1—C2—C7—C6	−179.9 (3)	C11—C32—C33—C34	175.1 (3)
C34—C36—C37—C31	−0.1 (6)	C20—C21—C27—C26	179.6 (3)
C12—C13—N14—C15	160.2 (2)	O29—C28—N30—C31	−175.9 (3)
C8—C12—C18—O19	20.1 (3)	N30—C31—C32—C11	1.4 (4)
N14—C16—C17—C18	−16.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H61···O19i	0.96	2.47	3.168 (5)	130
N30—H301···O29ii	0.96	1.90	2.844 (5)	167
C38—H381···Cg	0.95	2.63	2.818 (5)	91 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H61⋯O19i	0.96	2.47	3.168 (5)	130
N30—H301⋯O29ii	0.96	1.90	2.844 (5)	167

Symmetry codes: (i) ; (ii) .