4′-(3-Chloro­phenyl)-1-methyl-1H-indole-3-spiro-2′-pyrrolidine-3′-spiro-2′′-indan-2,1′′,3′′-trione

The pyrrolidine ring of the title compound, C₂₆H₁₉ClN₂O₃, adopts a half-chair conformation. The molecular structure is stabilized by C—H...O interactions and the packing of the mol­ecule is stabilized by C—H...O and N—H...O intermolecular interactions. A dimer is formed between symmetry-related mol­ecules through N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.056
• wR factor = 0.171
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.91

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           27.98
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               4731
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         5189
           Completeness (_total/calc)             91.17%

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990)'; software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

'1-N-methyl-Spiro-[2 - 3'] oxindole-spiro-[3–2"] indan-1",3"dione 4-[2"'- chlorophenyl] pyrrolidine.'

Crystal data

C26H19ClN2O3	Z = 2
Mr = 442.88	F(000) = 460
Triclinic, P1	Dx = 1.367 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8394 (6) Å	Cell parameters from 2195 reflections
b = 11.6760 (9) Å	θ = 2.4–26.9°
c = 11.8628 (10) Å	µ = 0.21 mm^−1
α = 85.657 (1)°	T = 293 K
β = 89.752 (1)°	Needles, yellow
γ = 83.726 (2)°	0.18 × 0.16 × 0.16 mm
V = 1076.22 (15) Å^3

Data collection

CCD Area Detector diffractometer	4731 independent reflections
Radiation source: fine-focus sealed tube	3499 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
ω scans	θmax = 28.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
Tmin = 0.954, Tmax = 0.970	k = −11→15
6811 measured reflections	l = −15→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.172	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
4731 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	1.12014 (10)	0.23162 (6)	0.79817 (8)	0.0904 (3)
N1	0.5643 (2)	0.97302 (16)	0.64645 (16)	0.0529 (5)
H1	0.4832	1.0173	0.6117	0.063*
C2	0.6575 (3)	0.8836 (2)	0.60032 (19)	0.0478 (5)
O3	0.6543 (2)	0.86163 (15)	0.50139 (13)	0.0639 (5)
C4	0.7706 (2)	0.81532 (17)	0.69708 (17)	0.0394 (5)
C5	0.7443 (2)	0.89634 (17)	0.79082 (17)	0.0395 (5)
C6	0.8250 (3)	0.89675 (18)	0.89303 (19)	0.0458 (5)
H6	0.9137	0.8399	0.9148	0.055*
C7	0.7724 (3)	0.9831 (2)	0.9633 (2)	0.0521 (6)
H7	0.8261	0.9841	1.0330	0.063*
C8	0.6413 (3)	1.0676 (2)	0.9312 (2)	0.0558 (6)
H8	0.6057	1.1238	0.9804	0.067*
C9	0.5625 (3)	1.07019 (19)	0.8278 (2)	0.0531 (6)
H9	0.4755	1.1281	0.8057	0.064*
C10	0.6160 (3)	0.98456 (18)	0.75767 (18)	0.0432 (5)
C11	0.7084 (2)	0.69304 (17)	0.72368 (15)	0.0353 (4)
C12	0.7996 (2)	0.62445 (18)	0.62895 (16)	0.0411 (5)
H12	0.7295	0.6443	0.5606	0.049*
C13	0.9667 (3)	0.6801 (2)	0.6082 (2)	0.0525 (6)
H13A	1.0644	0.6278	0.6365	0.063*
H13B	0.9824	0.6988	0.5280	0.063*
N14	0.9494 (2)	0.78474 (15)	0.66898 (15)	0.0443 (4)
C15	1.0402 (3)	0.8780 (2)	0.6198 (3)	0.0702 (8)
H15A	1.1569	0.8489	0.6050	0.105*
H15B	1.0386	0.9375	0.6715	0.105*
H15C	0.9854	0.9092	0.5503	0.105*
C16	0.8133 (2)	0.49386 (18)	0.64942 (15)	0.0391 (5)
C17	0.9480 (3)	0.42956 (18)	0.70856 (18)	0.0442 (5)
H17	1.0352	0.4663	0.7384	0.053*
C18	0.9522 (3)	0.31120 (19)	0.72299 (19)	0.0478 (5)
C19	0.8263 (3)	0.2534 (2)	0.68047 (19)	0.0526 (6)
H19	0.8320	0.1733	0.6907	0.063*
C20	0.6922 (3)	0.3162 (2)	0.6226 (2)	0.0593 (6)
H20	0.6052	0.2788	0.5934	0.071*
C21	0.6864 (3)	0.4346 (2)	0.60769 (19)	0.0540 (6)
H21	0.5945	0.4761	0.5684	0.065*
C22	0.7557 (2)	0.64951 (15)	0.84612 (15)	0.0326 (4)
O23	0.89755 (16)	0.61738 (13)	0.88181 (12)	0.0429 (4)
C24	0.5945 (2)	0.65307 (16)	0.91230 (15)	0.0326 (4)
C25	0.5729 (3)	0.63121 (16)	1.02736 (16)	0.0390 (4)
H25	0.6667	0.6165	1.0761	0.047*
C26	0.4063 (3)	0.63201 (18)	1.06737 (17)	0.0450 (5)
H26	0.3882	0.6184	1.1445	0.054*
C27	0.2665 (3)	0.6527 (2)	0.99511 (19)	0.0483 (5)
H27	0.1565	0.6510	1.0245	0.058*
C28	0.2870 (3)	0.67559 (19)	0.88060 (18)	0.0442 (5)
H28	0.1930	0.6904	0.8321	0.053*
C29	0.4543 (2)	0.67565 (17)	0.84029 (16)	0.0356 (4)
C30	0.5122 (2)	0.69247 (18)	0.72226 (17)	0.0403 (5)
O31	0.42343 (19)	0.70120 (18)	0.63869 (13)	0.0634 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0779 (5)	0.0586 (5)	0.1269 (7)	0.0177 (4)	−0.0318 (5)	0.0083 (4)
N1	0.0490 (11)	0.0523 (11)	0.0490 (11)	0.0201 (9)	−0.0011 (8)	0.0137 (8)
C2	0.0439 (11)	0.0519 (13)	0.0411 (12)	0.0104 (10)	0.0041 (9)	0.0159 (9)
O3	0.0735 (12)	0.0697 (12)	0.0384 (9)	0.0241 (9)	−0.0002 (8)	0.0145 (7)
C4	0.0340 (10)	0.0411 (11)	0.0385 (11)	0.0066 (8)	0.0028 (8)	0.0107 (8)
C5	0.0329 (10)	0.0362 (10)	0.0467 (12)	0.0000 (8)	0.0024 (8)	0.0086 (8)
C6	0.0406 (11)	0.0384 (11)	0.0564 (13)	−0.0015 (9)	−0.0048 (9)	0.0060 (9)
C7	0.0560 (13)	0.0440 (13)	0.0569 (14)	−0.0094 (10)	−0.0053 (10)	−0.0019 (10)
C8	0.0637 (15)	0.0381 (12)	0.0661 (16)	−0.0074 (11)	0.0082 (12)	−0.0051 (10)
C9	0.0468 (12)	0.0396 (12)	0.0686 (16)	0.0057 (9)	0.0088 (11)	0.0092 (10)
C10	0.0361 (10)	0.0387 (11)	0.0509 (13)	0.0025 (8)	0.0037 (9)	0.0114 (9)
C11	0.0282 (9)	0.0437 (11)	0.0314 (10)	0.0028 (8)	0.0013 (7)	0.0044 (8)
C12	0.0367 (10)	0.0510 (12)	0.0320 (10)	0.0065 (9)	0.0018 (8)	0.0036 (8)
C13	0.0451 (12)	0.0539 (14)	0.0548 (14)	0.0039 (10)	0.0182 (10)	0.0058 (10)
N14	0.0336 (9)	0.0398 (9)	0.0550 (11)	0.0036 (7)	0.0112 (7)	0.0144 (8)
C15	0.0531 (15)	0.0521 (15)	0.099 (2)	−0.0005 (11)	0.0255 (14)	0.0249 (14)
C16	0.0371 (10)	0.0498 (12)	0.0287 (10)	0.0023 (8)	0.0037 (7)	−0.0033 (8)
C17	0.0377 (11)	0.0451 (12)	0.0490 (12)	0.0013 (9)	−0.0041 (9)	−0.0062 (9)
C18	0.0464 (12)	0.0463 (13)	0.0482 (13)	0.0049 (9)	0.0010 (9)	−0.0016 (9)
C19	0.0629 (15)	0.0501 (13)	0.0463 (13)	−0.0107 (11)	0.0100 (11)	−0.0072 (10)
C20	0.0611 (15)	0.0715 (17)	0.0502 (14)	−0.0229 (13)	−0.0003 (11)	−0.0141 (12)
C21	0.0465 (13)	0.0728 (17)	0.0414 (12)	−0.0019 (11)	−0.0107 (9)	−0.0014 (11)
C22	0.0304 (9)	0.0306 (9)	0.0356 (10)	−0.0016 (7)	−0.0007 (7)	0.0019 (7)
O23	0.0303 (7)	0.0508 (9)	0.0445 (8)	0.0014 (6)	−0.0071 (6)	0.0088 (6)
C24	0.0347 (9)	0.0310 (9)	0.0321 (9)	−0.0038 (7)	0.0017 (7)	−0.0022 (7)
C25	0.0466 (11)	0.0333 (10)	0.0374 (11)	−0.0046 (8)	−0.0004 (8)	−0.0049 (8)
C26	0.0583 (13)	0.0416 (12)	0.0360 (11)	−0.0078 (10)	0.0142 (9)	−0.0057 (9)
C27	0.0412 (11)	0.0510 (13)	0.0533 (13)	−0.0054 (9)	0.0157 (10)	−0.0081 (10)
C28	0.0318 (10)	0.0499 (12)	0.0512 (13)	−0.0035 (9)	0.0034 (8)	−0.0091 (10)
C29	0.0302 (9)	0.0377 (10)	0.0387 (10)	−0.0026 (7)	0.0029 (7)	−0.0038 (8)
C30	0.0322 (10)	0.0485 (12)	0.0379 (11)	0.0044 (8)	−0.0017 (8)	−0.0012 (8)
O31	0.0384 (8)	0.1086 (15)	0.0395 (9)	0.0055 (8)	−0.0105 (6)	−0.0004 (8)

Geometric parameters (Å, º)

Cl1—C18	1.735 (2)	N14—C15	1.450 (3)
N1—C2	1.356 (3)	C15—H15A	0.9600
N1—C10	1.402 (3)	C15—H15B	0.9600
N1—H1	0.8600	C15—H15C	0.9600
C2—O3	1.221 (3)	C16—C17	1.387 (3)
C2—C4	1.567 (3)	C16—C21	1.386 (3)
C4—N14	1.452 (2)	C17—C18	1.376 (3)
C4—C5	1.513 (3)	C17—H17	0.9300
C4—C11	1.568 (3)	C18—C19	1.373 (3)
C5—C10	1.394 (3)	C19—C20	1.369 (3)
C5—C6	1.371 (3)	C19—H19	0.9300
C6—C7	1.384 (3)	C20—C21	1.376 (4)
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.379 (3)	C21—H21	0.9300
C7—H7	0.9300	C22—O23	1.202 (2)
C8—C9	1.372 (3)	C22—C24	1.483 (2)
C8—H8	0.9300	C24—C29	1.385 (3)
C9—C10	1.378 (3)	C24—C25	1.383 (3)
C9—H9	0.9300	C25—C26	1.387 (3)
C11—C22	1.535 (3)	C25—H25	0.9300
C11—C30	1.539 (3)	C26—C27	1.384 (3)
C11—C12	1.555 (3)	C26—H26	0.9300
C12—C16	1.518 (3)	C27—C28	1.377 (3)
C12—C13	1.535 (3)	C27—H27	0.9300
C12—H12	0.9800	C28—C29	1.394 (3)
C13—N14	1.459 (3)	C28—H28	0.9300
C13—H13A	0.9700	C29—C30	1.476 (3)
C13—H13B	0.9700	C30—O31	1.205 (2)
C2—N1—C10	111.9 (2)	C15—N14—C13	115.2 (2)
C2—N1—H1	124.1	N14—C15—H15A	109.5
C10—N1—H1	124.1	N14—C15—H15B	109.5
O3—C2—N1	126.0 (2)	H15A—C15—H15B	109.5
O3—C2—C4	126.7 (2)	N14—C15—H15C	109.5
N1—C2—C4	107.3 (2)	H15A—C15—H15C	109.5
N14—C4—C5	113.9 (2)	H15B—C15—H15C	109.5
N14—C4—C2	115.6 (2)	C17—C16—C21	117.6 (2)
C5—C4—C2	101.38 (16)	C17—C16—C12	123.14 (18)
N14—C4—C11	101.4 (2)	C21—C16—C12	119.27 (19)
C5—C4—C11	115.41 (15)	C18—C17—C16	119.8 (2)
C2—C4—C11	109.70 (16)	C18—C17—H17	120.1
C10—C5—C6	119.8 (2)	C16—C17—H17	120.1
C10—C5—C4	108.56 (18)	C17—C18—C19	122.1 (2)
C6—C5—C4	131.62 (18)	C17—C18—Cl1	119.5 (2)
C5—C6—C7	118.9 (2)	C19—C18—Cl1	118.5 (2)
C5—C6—H6	120.5	C20—C19—C18	118.6 (2)
C7—C6—H6	120.5	C20—C19—H19	120.7
C8—C7—C6	120.7 (2)	C18—C19—H19	120.7
C8—C7—H7	119.7	C19—C20—C21	119.9 (2)
C6—C7—H7	119.7	C19—C20—H20	120.1
C7—C8—C9	121.1 (2)	C21—C20—H20	120.1
C7—C8—H8	119.5	C20—C21—C16	122.1 (2)
C9—C8—H8	119.5	C20—C21—H21	119.0
C10—C9—C8	118.1 (2)	C16—C21—H21	119.0
C10—C9—H9	120.9	O23—C22—C24	126.1 (2)
C8—C9—H9	120.9	O23—C22—C11	126.3 (2)
C5—C10—C9	121.3 (2)	C24—C22—C11	107.64 (15)
C5—C10—N1	109.9 (2)	C29—C24—C25	120.91 (17)
C9—C10—N1	128.7 (2)	C29—C24—C22	109.99 (16)
C22—C11—C30	102.62 (14)	C25—C24—C22	128.98 (17)
C22—C11—C12	116.74 (15)	C26—C25—C24	117.53 (19)
C30—C11—C12	112.91 (16)	C26—C25—H25	121.2
C22—C11—C4	109.43 (15)	C24—C25—H25	121.2
C30—C11—C4	114.32 (16)	C25—C26—C27	121.50 (19)
C12—C11—C4	101.29 (15)	C25—C26—H26	119.3
C16—C12—C11	115.39 (16)	C27—C26—H26	119.3
C16—C12—C13	117.53 (17)	C28—C27—C26	121.27 (19)
C11—C12—C13	104.09 (17)	C28—C27—H27	119.4
C16—C12—H12	106.3	C26—C27—H27	119.4
C11—C12—H12	106.3	C29—C28—C27	117.32 (19)
C13—C12—H12	106.3	C29—C28—H28	121.3
N14—C13—C12	106.1 (2)	C27—C28—H28	121.3
N14—C13—H13A	110.5	C24—C29—C28	121.46 (18)
C12—C13—H13A	110.5	C24—C29—C30	110.09 (16)
N14—C13—H13B	110.5	C28—C29—C30	128.39 (18)
C12—C13—H13B	110.5	O31—C30—C29	126.52 (18)
H13A—C13—H13B	108.7	O31—C30—C11	125.5 (2)
C4—N14—C15	116.1 (2)	C29—C30—C11	108.0 (2)
C4—N14—C13	109.9 (2)
C10—N1—C2—O3	−171.0 (2)	C11—C4—N14—C13	36.3 (2)
C10—N1—C2—C4	8.4 (2)	C12—C13—N14—C4	−16.5 (2)
O3—C2—C4—N14	45.5 (3)	C12—C13—N14—C15	−149.87 (19)
N1—C2—C4—N14	−133.86 (19)	C11—C12—C16—C17	−87.5 (2)
O3—C2—C4—C5	169.3 (2)	C13—C12—C16—C17	36.0 (3)
N1—C2—C4—C5	−10.1 (2)	C11—C12—C16—C21	92.5 (2)
O3—C2—C4—C11	−68.3 (3)	C13—C12—C16—C21	−144.1 (2)
N1—C2—C4—C11	112.34 (19)	C21—C16—C17—C18	0.5 (3)
N14—C4—C5—C10	133.39 (17)	C12—C16—C17—C18	−179.5 (2)
C2—C4—C5—C10	8.5 (2)	C16—C17—C18—C19	0.0 (3)
C11—C4—C5—C10	−109.91 (18)	C16—C17—C18—Cl1	−179.42 (15)
N14—C4—C5—C6	−44.7 (3)	C17—C18—C19—C20	−0.4 (3)
C2—C4—C5—C6	−169.5 (2)	Cl1—C18—C19—C20	178.99 (17)
C11—C4—C5—C6	72.0 (3)	C18—C19—C20—C21	0.4 (3)
C10—C5—C6—C7	2.4 (3)	C19—C20—C21—C16	0.1 (3)
C4—C5—C6—C7	−179.7 (2)	C17—C16—C21—C20	−0.6 (3)
C5—C6—C7—C8	−0.2 (3)	C12—C16—C21—C20	179.46 (19)
C6—C7—C8—C9	−1.7 (3)	C30—C11—C22—O23	166.57 (19)
C7—C8—C9—C10	1.2 (3)	C12—C11—C22—O23	42.6 (3)
C6—C5—C10—C9	−2.9 (3)	C4—C11—C22—O23	−71.7 (2)
C4—C5—C10—C9	178.75 (19)	C30—C11—C22—C24	−12.85 (19)
C6—C5—C10—N1	174.06 (18)	C12—C11—C22—C24	−136.87 (17)
C4—C5—C10—N1	−4.3 (2)	C4—C11—C22—C24	108.92 (16)
C8—C9—C10—C5	1.1 (3)	O23—C22—C24—C29	−169.72 (19)
C8—C9—C10—N1	−175.2 (2)	C11—C22—C24—C29	9.7 (2)
C2—N1—C10—C5	−2.8 (2)	O23—C22—C24—C25	6.3 (3)
C2—N1—C10—C9	173.8 (2)	C11—C22—C24—C25	−174.26 (18)
N14—C4—C11—C22	82.96 (17)	C29—C24—C25—C26	0.4 (3)
C5—C4—C11—C22	−40.7 (2)	C22—C24—C25—C26	−175.23 (18)
C2—C4—C11—C22	−154.36 (15)	C24—C25—C26—C27	0.7 (3)
N14—C4—C11—C30	−162.61 (16)	C25—C26—C27—C28	−1.3 (3)
C5—C4—C11—C30	73.8 (2)	C26—C27—C28—C29	0.8 (3)
C2—C4—C11—C30	−39.9 (2)	C25—C24—C29—C28	−0.9 (3)
N14—C4—C11—C12	−40.89 (18)	C22—C24—C29—C28	175.49 (17)
C5—C4—C11—C12	−164.49 (16)	C25—C24—C29—C30	−178.31 (17)
C2—C4—C11—C12	81.79 (17)	C22—C24—C29—C30	−1.9 (2)
C22—C11—C12—C16	43.1 (2)	C27—C28—C29—C24	0.3 (3)
C30—C11—C12—C16	−75.5 (2)	C27—C28—C29—C30	177.15 (19)
C4—C11—C12—C16	161.78 (16)	C24—C29—C30—O31	171.5 (2)
C22—C11—C12—C13	−87.2 (2)	C28—C29—C30—O31	−5.6 (4)
C30—C11—C12—C13	154.19 (17)	C24—C29—C30—C11	−6.6 (2)
C4—C11—C12—C13	31.48 (19)	C28—C29—C30—C11	176.20 (19)
C16—C12—C13—N14	−139.89 (18)	C22—C11—C30—O31	−166.4 (2)
C11—C12—C13—N14	−10.9 (2)	C12—C11—C30—O31	−39.8 (3)
C5—C4—N14—C15	−66.1 (3)	C4—C11—C30—O31	75.3 (3)
C2—C4—N14—C15	50.7 (3)	C22—C11—C30—C29	11.8 (2)
C11—C4—N14—C15	169.3 (2)	C12—C11—C30—C29	138.34 (17)
C5—C4—N14—C13	160.95 (17)	C4—C11—C30—C29	−106.56 (18)
C2—C4—N14—C13	−82.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O3	0.98	2.59	3.154 (3)	117
N1—H1···O3^i	0.86	2.09	2.920 (2)	163
C15—H15A···O31^ii	0.96	2.57	3.452 (3)	152

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1, y, z.