Methyl (3R*,3'S*)-1',1''-dimethyl-2,2''-dioxodispiro-[indoline-3,2'-pyrrolidine-3',3''-indoline]-4'-carboxyl-ate.

In the title compound, C(22)H(21)N(3)O(4), the central pyrrolidine ring adopts an envelope conformation with the N atom in the flap position. The indoline ring systems are almost perpendic-ular to the mean plane of the pyrrolidine ring, making dihedral angles of 86.4 (8) and 83.1 (8)°. The acetate group attached to the pyrrolidine ring assumes an extended conformation. In thecrystal, N-H⋯O hydrogen bonds result in the formation of a C(7) chain running along [100]. The crystal packing also features π-π inter-actions [centroid-centroid distance = 3.2032 (11) Å].

Related literature

For the biological activity of spiro-pyrrolidine derivatives, see: Obniska et al. (2003 ▶); Peddi et al. (2004 ▶); Kaminski & Obniska (2008 ▶); Stylianakis et al. (2003 ▶); Waldmann (1995 ▶); Suzuki et al. (1994 ▶); Huryn et al. (1991 ▶). For a related structure, see: Wei et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶).

Experimental

Crystal data

C22H21N3O4

M = 391.42

Monoclinic,

a = 9.8244 (4) Å

b = 12.7193 (5) Å

c = 15.7630 (6) Å

β = 95.474 (2)°

V = 1960.75 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.983

17984 measured reflections

3691 independent reflections

2716 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.110

S = 1.01

3691 reflections

265 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.18 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/S1600536812037440/bx2423sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037440/bx2423Isup2.hkl

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

C22H21N3O4	F(000) = 824
Mr = 391.42	Dx = 1.326 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3691 reflections
a = 9.8244 (4) Å	θ = 2.1–25.7°
b = 12.7193 (5) Å	µ = 0.09 mm−1
c = 15.7630 (6) Å	T = 293 K
β = 95.474 (2)°	Block, colourless
V = 1960.75 (13) Å3	0.25 × 0.22 × 0.19 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3691 independent reflections
Radiation source: fine-focus sealed tube	2716 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω and φ scans	θmax = 25.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.978, Tmax = 0.983	k = −15→15
17984 measured reflections	l = −19→15

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0457P)2 + 0.6361P] where P = (Fo2 + 2Fc2)/3
3691 reflections	(Δ/σ)max < 0.001
265 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.18 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	−0.1007 (2)	−0.03758 (15)	0.60269 (11)	0.0486 (5)
H1A	−0.0871	0.0299	0.5761	0.058*
H1B	−0.1229	−0.0896	0.5586	0.058*
C2	0.02541 (18)	−0.06977 (13)	0.65991 (11)	0.0382 (4)
H2	0.0738	−0.0054	0.6791	0.046*
C3	−0.03026 (17)	−0.12230 (12)	0.74001 (10)	0.0320 (4)
C4	−0.18972 (17)	−0.12132 (12)	0.71699 (10)	0.0335 (4)
C5	−0.3439 (2)	−0.01745 (19)	0.61685 (14)	0.0640 (6)
H5A	−0.3650	−0.0755	0.5789	0.096*
H5B	−0.3472	0.0468	0.5848	0.096*
H5C	−0.4096	−0.0146	0.6582	0.096*
C6	0.1228 (2)	−0.13630 (15)	0.61579 (13)	0.0488 (5)
C7	0.3381 (3)	−0.2173 (2)	0.6299 (2)	0.1044 (10)
H7A	0.3031	−0.2878	0.6288	0.157*
H7B	0.4230	−0.2146	0.6654	0.157*
H7C	0.3531	−0.1961	0.5730	0.157*
C8	−0.30396 (19)	−0.03885 (14)	0.84650 (11)	0.0446 (5)
H8	−0.2595	0.0255	0.8446	0.053*
C9	−0.3969 (2)	−0.05603 (16)	0.90536 (12)	0.0519 (5)
H9	−0.4152	−0.0026	0.9429	0.062*
C10	−0.4627 (2)	−0.15059 (17)	0.90921 (13)	0.0588 (6)
H10	−0.5229	−0.1614	0.9504	0.071*
C11	−0.4404 (2)	−0.23012 (16)	0.85248 (14)	0.0596 (6)
H11	−0.4859	−0.2941	0.8540	0.071*
C12	−0.34875 (19)	−0.21128 (13)	0.79372 (12)	0.0425 (4)
C13	−0.27769 (17)	−0.11765 (12)	0.79085 (10)	0.0348 (4)
C14	−0.23636 (18)	−0.22843 (13)	0.67501 (11)	0.0388 (4)
C15	0.04532 (19)	−0.32158 (13)	0.73222 (12)	0.0412 (4)
H15	0.0074	−0.3327	0.6766	0.049*
C16	0.1163 (2)	−0.40147 (14)	0.77744 (13)	0.0497 (5)
H16	0.1263	−0.4664	0.7516	0.060*
C17	0.1718 (2)	−0.38606 (15)	0.85940 (13)	0.0531 (5)
H17	0.2176	−0.4411	0.8887	0.064*
C18	0.1611 (2)	−0.29021 (15)	0.89939 (13)	0.0509 (5)
H18	0.1992	−0.2793	0.9550	0.061*
C19	0.09178 (18)	−0.21159 (13)	0.85362 (11)	0.0381 (4)
C20	0.03200 (17)	−0.22564 (12)	0.77117 (10)	0.0330 (4)
C21	0.00958 (17)	−0.04954 (13)	0.81677 (11)	0.0353 (4)
C22	0.1426 (3)	−0.06320 (19)	0.95731 (14)	0.0729 (7)
H22A	0.1281	0.0114	0.9576	0.109*
H22B	0.2389	−0.0775	0.9601	0.109*
H22C	0.1056	−0.0941	1.0057	0.109*
N1	−0.20775 (16)	−0.03125 (11)	0.66017 (9)	0.0420 (4)
N2	−0.31930 (16)	−0.27579 (12)	0.72636 (10)	0.0502 (4)
H2A	−0.3505	−0.3386	0.7185	0.060*
N3	0.07510 (16)	−0.10775 (11)	0.87955 (9)	0.0424 (4)
O1	0.1005 (2)	−0.17271 (15)	0.54647 (10)	0.0875 (6)
O2	0.24061 (15)	−0.14729 (11)	0.66334 (10)	0.0639 (4)
O3	−0.20458 (14)	−0.26255 (10)	0.60748 (8)	0.0524 (4)
O4	−0.00852 (13)	0.04480 (9)	0.82033 (8)	0.0467 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0598 (13)	0.0488 (11)	0.0373 (10)	0.0048 (9)	0.0044 (9)	0.0115 (8)
C2	0.0463 (11)	0.0311 (9)	0.0376 (10)	−0.0019 (7)	0.0053 (8)	0.0030 (7)
C3	0.0364 (9)	0.0272 (8)	0.0316 (9)	0.0002 (7)	−0.0011 (7)	0.0005 (7)
C4	0.0381 (10)	0.0287 (8)	0.0322 (9)	0.0003 (7)	−0.0030 (7)	0.0000 (7)
C5	0.0575 (14)	0.0739 (15)	0.0581 (13)	0.0212 (11)	−0.0077 (11)	0.0133 (11)
C6	0.0589 (14)	0.0418 (10)	0.0472 (12)	−0.0001 (9)	0.0133 (10)	0.0041 (9)
C7	0.0647 (17)	0.100 (2)	0.153 (3)	0.0295 (16)	0.0350 (19)	0.003 (2)
C8	0.0471 (11)	0.0401 (10)	0.0467 (11)	−0.0054 (8)	0.0052 (9)	−0.0079 (8)
C9	0.0553 (13)	0.0555 (12)	0.0463 (11)	0.0004 (10)	0.0114 (10)	−0.0108 (9)
C10	0.0611 (14)	0.0611 (13)	0.0573 (13)	0.0019 (11)	0.0223 (11)	0.0040 (10)
C11	0.0616 (14)	0.0442 (11)	0.0761 (15)	−0.0083 (10)	0.0230 (12)	0.0033 (10)
C12	0.0453 (11)	0.0330 (9)	0.0490 (11)	0.0002 (8)	0.0039 (9)	−0.0017 (8)
C13	0.0363 (9)	0.0324 (8)	0.0347 (9)	0.0006 (7)	−0.0022 (7)	−0.0002 (7)
C14	0.0396 (10)	0.0368 (9)	0.0377 (10)	0.0023 (8)	−0.0083 (8)	−0.0044 (8)
C15	0.0454 (11)	0.0338 (9)	0.0438 (10)	0.0007 (8)	0.0014 (8)	−0.0018 (8)
C16	0.0527 (12)	0.0321 (9)	0.0648 (13)	0.0088 (8)	0.0088 (10)	0.0004 (9)
C17	0.0518 (12)	0.0457 (11)	0.0610 (13)	0.0157 (9)	0.0019 (10)	0.0157 (10)
C18	0.0537 (12)	0.0548 (12)	0.0426 (11)	0.0146 (10)	−0.0042 (9)	0.0074 (9)
C19	0.0402 (10)	0.0384 (9)	0.0354 (10)	0.0053 (8)	0.0016 (8)	0.0014 (7)
C20	0.0335 (9)	0.0306 (8)	0.0345 (9)	0.0005 (7)	0.0019 (7)	0.0016 (7)
C21	0.0337 (9)	0.0328 (9)	0.0387 (10)	−0.0011 (7)	−0.0009 (8)	−0.0043 (7)
C22	0.0833 (17)	0.0762 (15)	0.0525 (13)	0.0234 (13)	−0.0287 (12)	−0.0264 (11)
N1	0.0463 (9)	0.0408 (8)	0.0379 (8)	0.0079 (7)	−0.0011 (7)	0.0096 (6)
N2	0.0509 (10)	0.0338 (8)	0.0666 (11)	−0.0094 (7)	0.0093 (8)	−0.0138 (7)
N3	0.0491 (9)	0.0421 (8)	0.0334 (8)	0.0079 (7)	−0.0091 (7)	−0.0070 (6)
O1	0.1076 (15)	0.1034 (14)	0.0525 (10)	0.0297 (11)	0.0128 (9)	−0.0193 (9)
O2	0.0449 (9)	0.0626 (9)	0.0854 (11)	0.0047 (7)	0.0118 (8)	0.0021 (8)
O3	0.0633 (9)	0.0526 (8)	0.0396 (7)	0.0027 (7)	−0.0040 (6)	−0.0150 (6)
O4	0.0511 (8)	0.0309 (7)	0.0558 (8)	0.0023 (5)	−0.0061 (6)	−0.0089 (6)

C1—N1	1.455 (2)	C9—H9	0.9300
C1—C2	1.517 (3)	C10—C11	1.381 (3)
C1—H1A	0.9700	C10—H10	0.9300
C1—H1B	0.9700	C11—C12	1.373 (3)
C2—C6	1.498 (3)	C11—H11	0.9300
C2—C3	1.572 (2)	C12—C13	1.383 (2)
C2—H2	0.9800	C12—N2	1.394 (2)
C3—C20	1.512 (2)	C14—O3	1.217 (2)
C3—C21	1.544 (2)	C14—N2	1.345 (2)
C3—C4	1.574 (2)	C15—C20	1.378 (2)
C4—N1	1.454 (2)	C15—C16	1.390 (2)
C4—C13	1.516 (2)	C15—H15	0.9300
C4—C14	1.564 (2)	C16—C17	1.368 (3)
C5—N1	1.454 (2)	C16—H16	0.9300
C5—H5A	0.9600	C17—C18	1.381 (3)
C5—H5B	0.9600	C17—H17	0.9300
C5—H5C	0.9600	C18—C19	1.375 (2)
C6—O1	1.188 (2)	C18—H18	0.9300
C6—O2	1.325 (2)	C19—C20	1.386 (2)
C7—O2	1.444 (3)	C19—N3	1.397 (2)
C7—H7A	0.9600	C21—O4	1.2151 (19)
C7—H7B	0.9600	C21—N3	1.349 (2)
C7—H7C	0.9600	C22—N3	1.452 (2)
C8—C13	1.372 (2)	C22—H22A	0.9600
C8—C9	1.380 (3)	C22—H22B	0.9600
C8—H8	0.9300	C22—H22C	0.9600
C9—C10	1.369 (3)	N2—H2A	0.8600
N1—C1—C2	104.04 (13)	C12—C11—H11	121.2
N1—C1—H1A	110.9	C10—C11—H11	121.2
C2—C1—H1A	110.9	C11—C12—C13	122.53 (17)
N1—C1—H1B	110.9	C11—C12—N2	127.46 (17)
C2—C1—H1B	110.9	C13—C12—N2	109.86 (16)
H1A—C1—H1B	109.0	C8—C13—C12	118.78 (16)
C6—C2—C1	113.46 (15)	C8—C13—C4	132.01 (15)
C6—C2—C3	114.81 (14)	C12—C13—C4	108.98 (14)
C1—C2—C3	105.38 (14)	O3—C14—N2	125.97 (16)
C6—C2—H2	107.6	O3—C14—C4	126.24 (16)
C1—C2—H2	107.6	N2—C14—C4	107.79 (14)
C3—C2—H2	107.6	C20—C15—C16	118.90 (17)
C20—C3—C21	101.66 (13)	C20—C15—H15	120.6
C20—C3—C2	118.00 (14)	C16—C15—H15	120.6
C21—C3—C2	107.05 (13)	C17—C16—C15	121.00 (17)
C20—C3—C4	116.40 (13)	C17—C16—H16	119.5
C21—C3—C4	110.38 (13)	C15—C16—H16	119.5
C2—C3—C4	103.08 (13)	C16—C17—C18	121.11 (17)
N1—C4—C13	113.82 (13)	C16—C17—H17	119.4
N1—C4—C14	114.33 (13)	C18—C17—H17	119.4
C13—C4—C14	100.74 (13)	C19—C18—C17	117.26 (18)
N1—C4—C3	102.03 (13)	C19—C18—H18	121.4
C13—C4—C3	116.81 (13)	C17—C18—H18	121.4
C14—C4—C3	109.61 (13)	C18—C19—C20	122.87 (16)
N1—C5—H5A	109.5	C18—C19—N3	126.89 (17)
N1—C5—H5B	109.5	C20—C19—N3	110.20 (14)
H5A—C5—H5B	109.5	C15—C20—C19	118.84 (15)
N1—C5—H5C	109.5	C15—C20—C3	132.68 (16)
H5A—C5—H5C	109.5	C19—C20—C3	108.35 (14)
H5B—C5—H5C	109.5	O4—C21—N3	124.74 (15)
O1—C6—O2	123.6 (2)	O4—C21—C3	126.93 (15)
O1—C6—C2	125.3 (2)	N3—C21—C3	108.27 (13)
O2—C6—C2	111.05 (17)	N3—C22—H22A	109.5
O2—C7—H7A	109.5	N3—C22—H22B	109.5
O2—C7—H7B	109.5	H22A—C22—H22B	109.5
H7A—C7—H7B	109.5	N3—C22—H22C	109.5
O2—C7—H7C	109.5	H22A—C22—H22C	109.5
H7A—C7—H7C	109.5	H22B—C22—H22C	109.5
H7B—C7—H7C	109.5	C5—N1—C4	115.91 (15)
C13—C8—C9	119.40 (17)	C5—N1—C1	113.71 (15)
C13—C8—H8	120.3	C4—N1—C1	106.69 (13)
C9—C8—H8	120.3	C14—N2—C12	112.12 (15)
C10—C9—C8	120.93 (18)	C14—N2—H2A	123.9
C10—C9—H9	119.5	C12—N2—H2A	123.9
C8—C9—H9	119.5	C21—N3—C19	111.43 (14)
C9—C10—C11	120.68 (19)	C21—N3—C22	123.54 (16)
C9—C10—H10	119.7	C19—N3—C22	123.99 (15)
C11—C10—H10	119.7	C6—O2—C7	115.6 (2)
C12—C11—C10	117.60 (18)
N1—C1—C2—C6	148.17 (15)	C15—C16—C17—C18	−1.1 (3)
N1—C1—C2—C3	21.75 (17)	C16—C17—C18—C19	0.4 (3)
C6—C2—C3—C20	7.8 (2)	C17—C18—C19—C20	1.0 (3)
C1—C2—C3—C20	133.43 (15)	C17—C18—C19—N3	−176.25 (18)
C6—C2—C3—C21	121.57 (16)	C16—C15—C20—C19	1.0 (3)
C1—C2—C3—C21	−112.84 (15)	C16—C15—C20—C3	176.17 (17)
C6—C2—C3—C4	−122.00 (16)	C18—C19—C20—C15	−1.7 (3)
C1—C2—C3—C4	3.59 (16)	N3—C19—C20—C15	175.92 (15)
C20—C3—C4—N1	−158.29 (13)	C18—C19—C20—C3	−177.98 (17)
C21—C3—C4—N1	86.55 (14)	N3—C19—C20—C3	−0.31 (19)
C2—C3—C4—N1	−27.49 (15)	C21—C3—C20—C15	−173.52 (18)
C20—C3—C4—C13	76.93 (18)	C2—C3—C20—C15	−56.9 (3)
C21—C3—C4—C13	−38.23 (18)	C4—C3—C20—C15	66.5 (2)
C2—C3—C4—C13	−152.27 (13)	C21—C3—C20—C19	2.00 (17)
C20—C3—C4—C14	−36.75 (19)	C2—C3—C20—C19	118.66 (16)
C21—C3—C4—C14	−151.91 (13)	C4—C3—C20—C19	−117.97 (15)
C2—C3—C4—C14	94.05 (14)	C20—C3—C21—O4	174.00 (17)
C1—C2—C6—O1	−8.8 (3)	C2—C3—C21—O4	49.6 (2)
C3—C2—C6—O1	112.5 (2)	C4—C3—C21—O4	−61.9 (2)
C1—C2—C6—O2	169.32 (15)	C20—C3—C21—N3	−3.08 (17)
C3—C2—C6—O2	−69.4 (2)	C2—C3—C21—N3	−127.46 (15)
C13—C8—C9—C10	0.3 (3)	C4—C3—C21—N3	121.04 (15)
C8—C9—C10—C11	−2.0 (3)	C13—C4—N1—C5	−62.0 (2)
C9—C10—C11—C12	1.2 (3)	C14—C4—N1—C5	53.0 (2)
C10—C11—C12—C13	1.2 (3)	C3—C4—N1—C5	171.25 (15)
C10—C11—C12—N2	−174.0 (2)	C13—C4—N1—C1	170.24 (14)
C9—C8—C13—C12	2.0 (3)	C14—C4—N1—C1	−74.73 (18)
C9—C8—C13—C4	175.81 (18)	C3—C4—N1—C1	43.49 (16)
C11—C12—C13—C8	−2.8 (3)	C2—C1—N1—C5	−170.83 (16)
N2—C12—C13—C8	173.15 (16)	C2—C1—N1—C4	−41.80 (18)
C11—C12—C13—C4	−177.96 (18)	O3—C14—N2—C12	−172.78 (17)
N2—C12—C13—C4	−2.0 (2)	C4—C14—N2—C12	6.5 (2)
N1—C4—C13—C8	−46.1 (3)	C11—C12—N2—C14	172.67 (19)
C14—C4—C13—C8	−168.94 (19)	C13—C12—N2—C14	−3.0 (2)
C3—C4—C13—C8	72.5 (2)	O4—C21—N3—C19	−174.02 (17)
N1—C4—C13—C12	128.17 (16)	C3—C21—N3—C19	3.14 (19)
C14—C4—C13—C12	5.34 (17)	O4—C21—N3—C22	−5.3 (3)
C3—C4—C13—C12	−113.25 (16)	C3—C21—N3—C22	171.91 (18)
N1—C4—C14—O3	49.8 (2)	C18—C19—N3—C21	175.70 (18)
C13—C4—C14—O3	172.23 (17)	C20—C19—N3—C21	−1.8 (2)
C3—C4—C14—O3	−64.1 (2)	C18—C19—N3—C22	7.0 (3)
N1—C4—C14—N2	−129.55 (15)	C20—C19—N3—C22	−170.56 (19)
C13—C4—C14—N2	−7.07 (17)	O1—C6—O2—C7	−6.8 (3)
C3—C4—C14—N2	116.63 (15)	C2—C6—O2—C7	175.05 (19)
C20—C15—C16—C17	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4i	0.86	2.08	2.8935 (19)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4i	0.86	2.08	2.8935 (19)	157

Symmetry code: (i) .