4′-(p-Methoxy­phenyl)-1′-methyl-1H-indole-3-spiro-2′-pyrrolidine-3′-spiro-1′′-cyclo­pentane-2(3H),2′′-dione

The indole moiety of the title compound, C₂₃H₂₄N₂O₃, is planar; but the pyrrolidine ring adopts an envelope conform­ation. The conformation is stabilized by intramolecular C—H...O interactions and the packing of the mol­ecules is stabilized by strong N—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.048
• wR factor = 0.141
• Data-to-parameter ratio = 16.6

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
ABSTY02_ALERT_1_C  An _exptl_absorpt_correction_type has been given without
            a literature citation. This should be contained in the
            _exptl_absorpt_process_details field.
            Absorption correction given as multi-scan
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           28.03
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               4209
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         4608
           Completeness (_total/calc)             91.34%
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C23 H24 N2 O3

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

   2 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
   2 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: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

4'-(p-Methoxyphenyl)-1'-methyl-1H-indole-3-spiro-2'-pyrrolidine- 3'-spiro-1''-cyclopentane-2(3H),2''-dione

Crystal data

C23H24N2O3	Z = 2
Mr = 376.44	F(000) = 400
Triclinic, P1	Dx = 1.317 Mg m^−3
a = 6.3317 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.5470 (8) Å	Cell parameters from 2626 reflections
c = 14.1402 (10) Å	θ = 3.1–27.9°
α = 72.240 (1)°	µ = 0.09 mm^−1
β = 77.366 (1)°	T = 293 K
γ = 77.773 (1)°	Block, colourless
V = 948.93 (12) Å^3	0.24 × 0.20 × 0.18 mm

Data collection

CCD Area Detector diffractometer	4209 independent reflections
Radiation source: fine-focus sealed tube	3390 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
ω scans	θmax = 28.0°, θmin = 1.9°
Absorption correction: multi-scan	h = −8→7
Tmin = 0.979, Tmax = 0.984	k = −15→15
6064 measured reflections	l = −18→9

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.082P)^2 + 0.136P] where P = (Fo^2 + 2Fc^2)/3
4209 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.16 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
O10	0.12503 (16)	0.03041 (10)	0.62503 (9)	0.0467 (3)
O20	−0.67989 (18)	0.17388 (13)	0.81362 (11)	0.0651 (4)
O27	−0.1684 (2)	−0.52773 (11)	0.91755 (10)	0.0659 (4)
N1	0.1307 (2)	0.23036 (11)	0.61723 (10)	0.0415 (3)
H1	0.2694	0.2306	0.5987	0.050*
N11	−0.34948 (18)	0.15396 (11)	0.59620 (9)	0.0363 (3)
C2	−0.0203 (2)	0.33247 (13)	0.63345 (11)	0.0393 (3)
C3	0.0168 (3)	0.45057 (15)	0.62026 (13)	0.0510 (4)
H3	0.1578	0.4703	0.6007	0.061*
C4	−0.1620 (4)	0.53846 (15)	0.63700 (13)	0.0576 (5)
H4	−0.1404	0.6182	0.6296	0.069*
C5	−0.3701 (3)	0.51053 (15)	0.66419 (14)	0.0576 (5)
H5	−0.4878	0.5713	0.6750	0.069*
C6	−0.4073 (3)	0.39183 (15)	0.67591 (13)	0.0501 (4)
H6	−0.5491	0.3733	0.6931	0.060*
C7	−0.2305 (2)	0.30243 (13)	0.66160 (11)	0.0377 (3)
C8	−0.2196 (2)	0.16858 (12)	0.66575 (11)	0.0341 (3)
C9	0.0321 (2)	0.13077 (13)	0.63415 (10)	0.0361 (3)
C12	−0.2731 (3)	0.20971 (15)	0.48962 (12)	0.0486 (4)
H12A	−0.2771	0.2964	0.4785	0.073*
H12B	−0.3665	0.1973	0.4496	0.073*
H12C	−0.1257	0.1721	0.4707	0.073*
C13	−0.3487 (2)	0.02108 (13)	0.62038 (11)	0.0378 (3)
H13A	−0.2071	−0.0206	0.5957	0.045*
H13B	−0.4606	0.0036	0.5918	0.045*
C14	−0.3979 (2)	−0.01763 (13)	0.73505 (11)	0.0362 (3)
H14	−0.5576	−0.0018	0.7537	0.043*
C15	−0.3057 (2)	0.07684 (13)	0.76851 (10)	0.0346 (3)
C16	−0.1434 (2)	0.02862 (15)	0.84379 (12)	0.0434 (4)
H16A	−0.1785	−0.0475	0.8924	0.052*
H16B	0.0055	0.0138	0.8089	0.052*
C17	−0.1691 (3)	0.12944 (18)	0.89566 (14)	0.0564 (4)
H17A	−0.1215	0.0962	0.9607	0.068*
H17B	−0.0838	0.1933	0.8548	0.068*
C18	−0.4113 (3)	0.17986 (18)	0.90775 (13)	0.0535 (4)
H18A	−0.4855	0.1413	0.9741	0.064*
H18B	−0.4350	0.2682	0.8983	0.064*
C19	−0.4935 (2)	0.14929 (14)	0.82744 (12)	0.0420 (3)
C21	−0.3278 (2)	−0.15267 (13)	0.78198 (11)	0.0383 (3)
C22	−0.1108 (2)	−0.21002 (14)	0.76941 (12)	0.0444 (4)
H22	−0.0033	−0.1636	0.7304	0.053*
C23	−0.0506 (3)	−0.33412 (15)	0.81332 (13)	0.0479 (4)
H23	0.0958	−0.3700	0.8045	0.057*
C24	−0.2093 (3)	−0.40443 (14)	0.87034 (12)	0.0474 (4)
C25	−0.4258 (3)	−0.35009 (15)	0.88319 (13)	0.0525 (4)
H25	−0.5330	−0.3972	0.9213	0.063*
C26	−0.4836 (3)	−0.22632 (15)	0.83975 (12)	0.0460 (4)
H26	−0.6302	−0.1910	0.8492	0.055*
C28	0.0488 (4)	−0.59010 (17)	0.90118 (16)	0.0688 (6)
H28A	0.0542	−0.6753	0.9381	0.103*
H28B	0.1447	−0.5536	0.9237	0.103*
H28C	0.0947	−0.5837	0.8307	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O10	0.0313 (5)	0.0439 (6)	0.0652 (7)	−0.0022 (4)	−0.0021 (5)	−0.0221 (5)
O20	0.0321 (6)	0.0862 (9)	0.0894 (10)	0.0034 (6)	−0.0069 (6)	−0.0526 (8)
O27	0.0797 (9)	0.0381 (6)	0.0680 (9)	−0.0056 (6)	−0.0055 (7)	−0.0043 (6)
N1	0.0327 (6)	0.0440 (7)	0.0490 (7)	−0.0119 (5)	−0.0041 (5)	−0.0122 (6)
N11	0.0338 (6)	0.0373 (6)	0.0401 (6)	−0.0044 (5)	−0.0093 (5)	−0.0121 (5)
C2	0.0455 (8)	0.0385 (8)	0.0360 (7)	−0.0089 (6)	−0.0130 (6)	−0.0070 (6)
C3	0.0653 (11)	0.0428 (9)	0.0499 (9)	−0.0191 (8)	−0.0203 (8)	−0.0054 (7)
C4	0.0908 (14)	0.0355 (8)	0.0537 (10)	−0.0121 (9)	−0.0274 (9)	−0.0100 (7)
C5	0.0758 (12)	0.0375 (8)	0.0606 (11)	0.0082 (8)	−0.0231 (9)	−0.0180 (8)
C6	0.0490 (9)	0.0445 (9)	0.0581 (10)	0.0027 (7)	−0.0139 (7)	−0.0188 (8)
C7	0.0413 (8)	0.0349 (7)	0.0389 (7)	−0.0040 (6)	−0.0107 (6)	−0.0113 (6)
C8	0.0278 (6)	0.0349 (7)	0.0409 (7)	−0.0026 (5)	−0.0054 (5)	−0.0138 (6)
C9	0.0307 (7)	0.0408 (8)	0.0375 (7)	−0.0067 (6)	−0.0044 (5)	−0.0117 (6)
C12	0.0560 (10)	0.0485 (9)	0.0410 (8)	−0.0079 (7)	−0.0115 (7)	−0.0096 (7)
C13	0.0343 (7)	0.0380 (7)	0.0445 (8)	−0.0050 (6)	−0.0083 (6)	−0.0152 (6)
C14	0.0271 (6)	0.0381 (7)	0.0446 (8)	−0.0053 (5)	−0.0045 (5)	−0.0139 (6)
C15	0.0275 (6)	0.0381 (7)	0.0389 (7)	−0.0034 (5)	−0.0048 (5)	−0.0130 (6)
C16	0.0377 (8)	0.0492 (9)	0.0426 (8)	−0.0043 (6)	−0.0115 (6)	−0.0098 (7)
C17	0.0572 (10)	0.0673 (12)	0.0538 (10)	−0.0103 (9)	−0.0206 (8)	−0.0210 (9)
C18	0.0546 (10)	0.0652 (11)	0.0467 (9)	−0.0092 (8)	−0.0035 (7)	−0.0274 (8)
C19	0.0329 (7)	0.0477 (8)	0.0469 (8)	−0.0061 (6)	−0.0011 (6)	−0.0190 (7)
C21	0.0382 (7)	0.0385 (7)	0.0395 (8)	−0.0071 (6)	−0.0042 (6)	−0.0135 (6)
C22	0.0398 (8)	0.0402 (8)	0.0506 (9)	−0.0084 (6)	−0.0009 (6)	−0.0117 (7)
C23	0.0456 (9)	0.0423 (8)	0.0533 (9)	−0.0003 (7)	−0.0044 (7)	−0.0165 (7)
C24	0.0615 (10)	0.0373 (8)	0.0424 (8)	−0.0075 (7)	−0.0064 (7)	−0.0107 (6)
C25	0.0541 (10)	0.0472 (9)	0.0527 (10)	−0.0191 (8)	−0.0003 (8)	−0.0070 (7)
C26	0.0386 (8)	0.0475 (9)	0.0501 (9)	−0.0100 (7)	−0.0015 (6)	−0.0125 (7)
C28	0.0946 (15)	0.0417 (9)	0.0654 (12)	0.0091 (10)	−0.0199 (11)	−0.0165 (9)

Geometric parameters (Å, º)

O10—C9	1.2146 (17)	C13—H13B	0.9700
O20—C19	1.1984 (18)	C14—C21	1.508 (2)
O27—C24	1.3709 (19)	C14—C15	1.5685 (19)
O27—C28	1.416 (2)	C14—H14	0.9800
N1—C9	1.3567 (18)	C15—C16	1.541 (2)
N1—C2	1.3958 (19)	C15—C19	1.5423 (19)
N1—H1	0.8600	C16—C17	1.519 (2)
N11—C12	1.463 (2)	C16—H16A	0.9700
N11—C13	1.465 (2)	C16—H16B	0.9700
N11—C8	1.478 (2)	C17—C18	1.513 (2)
C2—C3	1.382 (2)	C17—H17A	0.9700
C2—C7	1.390 (2)	C17—H17B	0.9700
C3—C4	1.382 (3)	C18—C19	1.505 (2)
C3—H3	0.9300	C18—H18A	0.9700
C4—C5	1.367 (3)	C18—H18B	0.9700
C4—H4	0.9300	C21—C22	1.392 (2)
C5—C6	1.394 (2)	C21—C26	1.394 (2)
C5—H5	0.9300	C22—C23	1.383 (2)
C6—C7	1.378 (2)	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.382 (2)
C7—C8	1.5159 (19)	C23—H23	0.9300
C8—C9	1.5631 (18)	C24—C25	1.379 (2)
C8—C15	1.578 (2)	C25—C26	1.377 (2)
C12—H12A	0.9600	C25—H25	0.9300
C12—H12B	0.9600	C26—H26	0.9300
C12—H12C	0.9600	C28—H28A	0.9600
C13—C14	1.524 (2)	C28—H28B	0.9600
C13—H13A	0.9700	C28—H28C	0.9600
C24—O27—C28	118.07 (15)	C16—C15—C19	100.63 (11)
C9—N1—C2	111.8 (1)	C16—C15—C14	119.25 (12)
C9—N1—H1	124.1	C19—C15—C14	109.88 (11)
C2—N1—H1	124.1	C16—C15—C8	114.79 (11)
C12—N11—C13	113.4 (2)	C19—C15—C8	108.38 (11)
C12—N11—C8	114.5 (1)	C14—C15—C8	103.63 (11)
C13—N11—C8	105.1 (1)	C17—C16—C15	105.32 (12)
C3—C2—C7	121.43 (15)	C17—C16—H16A	110.7
C3—C2—N1	128.54 (15)	C15—C16—H16A	110.7
C7—C2—N1	109.95 (12)	C17—C16—H16B	110.7
C4—C3—C2	117.98 (17)	C15—C16—H16B	110.7
C4—C3—H3	121.0	H16A—C16—H16B	108.8
C2—C3—H3	121.0	C18—C17—C16	104.95 (14)
C5—C4—C3	121.29 (16)	C18—C17—H17A	110.8
C5—C4—H4	119.4	C16—C17—H17A	110.8
C3—C4—H4	119.4	C18—C17—H17B	110.8
C4—C5—C6	120.61 (16)	C16—C17—H17B	110.8
C4—C5—H5	119.7	H17A—C17—H17B	108.8
C6—C5—H5	119.7	C19—C18—C17	105.04 (13)
C7—C6—C5	118.87 (17)	C19—C18—H18A	110.7
C7—C6—H6	120.6	C17—C18—H18A	110.7
C5—C6—H6	120.6	C19—C18—H18B	110.7
C6—C7—C2	119.80 (14)	C17—C18—H18B	110.7
C6—C7—C8	130.90 (14)	H18A—C18—H18B	108.8
C2—C7—C8	109.22 (12)	O20—C19—C18	124.85 (14)
N11—C8—C7	112.24 (11)	O20—C19—C15	124.83 (14)
N11—C8—C9	112.57 (11)	C18—C19—C15	110.27 (12)
C7—C8—C9	100.87 (11)	C22—C21—C26	117.02 (14)
N11—C8—C15	102.36 (10)	C22—C21—C14	122.94 (13)
C7—C8—C15	118.97 (11)	C26—C21—C14	120.03 (13)
C9—C8—C15	110.20 (11)	C23—C22—C21	121.86 (14)
O10—C9—N1	125.35 (13)	C23—C22—H22	119.1
O10—C9—C8	126.47 (12)	C21—C22—H22	119.1
N1—C9—C8	108.17 (11)	C24—C23—C22	119.61 (15)
N11—C12—H12A	109.5	C24—C23—H23	120.2
N11—C12—H12B	109.5	C22—C23—H23	120.2
H12A—C12—H12B	109.5	O27—C24—C25	115.70 (15)
N11—C12—H12C	109.5	O27—C24—C23	124.61 (16)
H12A—C12—H12C	109.5	C25—C24—C23	119.69 (15)
H12B—C12—H12C	109.5	C26—C25—C24	120.18 (15)
N11—C13—C14	103.26 (11)	C26—C25—H25	119.9
N11—C13—H13A	111.1	C24—C25—H25	119.9
C14—C13—H13A	111.1	C25—C26—C21	121.63 (15)
N11—C13—H13B	111.1	C25—C26—H26	119.2
C14—C13—H13B	111.1	C21—C26—H26	119.2
H13A—C13—H13B	109.1	O27—C28—H28A	109.5
C21—C14—C13	114.33 (11)	O27—C28—H28B	109.5
C21—C14—C15	117.50 (12)	H28A—C28—H28B	109.5
C13—C14—C15	105.05 (11)	O27—C28—H28C	109.5
C21—C14—H14	106.4	H28A—C28—H28C	109.5
C13—C14—H14	106.4	H28B—C28—H28C	109.5
C15—C14—H14	106.4
C9—N1—C2—C3	−177.30 (14)	C21—C14—C15—C8	131.26 (12)
C9—N1—C2—C7	−0.60 (17)	C13—C14—C15—C8	2.87 (13)
C7—C2—C3—C4	0.7 (2)	N11—C8—C15—C16	155.18 (11)
N1—C2—C3—C4	177.06 (15)	C7—C8—C15—C16	−80.46 (15)
C2—C3—C4—C5	−1.0 (3)	C9—C8—C15—C16	35.23 (15)
C3—C4—C5—C6	0.1 (3)	N11—C8—C15—C19	−93.25 (12)
C4—C5—C6—C7	1.3 (3)	C7—C8—C15—C19	31.10 (16)
C5—C6—C7—C2	−1.6 (2)	C9—C8—C15—C19	146.79 (11)
C5—C6—C7—C8	−177.88 (15)	N11—C8—C15—C14	23.45 (12)
C3—C2—C7—C6	0.7 (2)	C7—C8—C15—C14	147.80 (12)
N1—C2—C7—C6	−176.33 (13)	C9—C8—C15—C14	−96.51 (12)
C3—C2—C7—C8	177.66 (13)	C19—C15—C16—C17	−34.39 (15)
N1—C2—C7—C8	0.68 (16)	C14—C15—C16—C17	−154.50 (13)
C12—N11—C8—C7	63.20 (15)	C8—C15—C16—C17	81.72 (15)
C13—N11—C8—C7	−171.71 (11)	C15—C16—C17—C18	37.26 (17)
C12—N11—C8—C9	−49.79 (15)	C16—C17—C18—C19	−23.71 (19)
C13—N11—C8—C9	75.30 (13)	C17—C18—C19—O20	179.41 (17)
C12—N11—C8—C15	−168.09 (11)	C17—C18—C19—C15	1.87 (19)
C13—N11—C8—C15	−43.00 (12)	C16—C15—C19—O20	−157.52 (17)
C6—C7—C8—N11	56.0 (2)	C14—C15—C19—O20	−30.9 (2)
C2—C7—C8—N11	−120.54 (13)	C8—C15—C19—O20	81.69 (19)
C6—C7—C8—C9	176.08 (16)	C16—C15—C19—C18	20.02 (16)
C2—C7—C8—C9	−0.48 (14)	C14—C15—C19—C18	146.64 (13)
C6—C7—C8—C15	−63.4 (2)	C8—C15—C19—C18	−100.77 (15)
C2—C7—C8—C15	120.07 (13)	C13—C14—C21—C22	61.05 (19)
C2—N1—C9—O10	179.56 (14)	C15—C14—C21—C22	−62.78 (19)
C2—N1—C9—C8	0.26 (16)	C13—C14—C21—C26	−117.97 (15)
N11—C8—C9—O10	−59.34 (19)	C15—C14—C21—C26	118.20 (15)
C7—C8—C9—O10	−179.16 (14)	C26—C21—C22—C23	−1.0 (2)
C15—C8—C9—O10	54.24 (18)	C14—C21—C22—C23	179.96 (14)
N11—C8—C9—N1	119.95 (13)	C21—C22—C23—C24	0.9 (3)
C7—C8—C9—N1	0.14 (14)	C28—O27—C24—C25	175.7 (2)
C15—C8—C9—N1	−126.47 (12)	C28—O27—C24—C23	−4.8 (3)
C12—N11—C13—C14	171.33 (11)	C22—C23—C24—O27	−179.72 (15)
C8—N11—C13—C14	45.50 (13)	C22—C23—C24—C25	−0.2 (3)
N11—C13—C14—C21	−158.81 (11)	O27—C24—C25—C26	179.28 (15)
N11—C13—C14—C15	−28.55 (13)	C23—C24—C25—C26	−0.2 (3)
C21—C14—C15—C16	2.19 (18)	C24—C25—C26—C21	0.1 (3)
C13—C14—C15—C16	−126.19 (13)	C22—C21—C26—C25	0.5 (2)
C21—C14—C15—C19	−113.11 (13)	C14—C21—C26—C25	179.56 (15)
C13—C14—C15—C19	118.51 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O20	0.93	2.59	3.238 (2)	128
C13—H13A···O10	0.97	2.45	3.040 (2)	119
C14—H14···O20	0.98	2.35	2.876 (2)	113
C16—H16B···O10	0.97	2.50	3.183 (2)	127
C22—H22···O10	0.93	2.47	3.327 (2)	153
N1—H1···N11^i	0.86	2.38	3.194 (2)	157

Symmetry code: (i) x+1, y, z.