A triclinic polymorph of methyl (3R,3'S)-1',1''-dimethyl-2,2''-dioxodispiro-[indoline-3,2'-pyrrolidine-3',3''-indoline]-4'-carboxyl-ate.

In the title compound, C22H21N3O4, the central pyrrolidine ring adopts a C-envelope conformation with a C atom 0.6593 (13) Å displaced from the mean plane formed by the remaining ring atoms. The indoline ring systems (r.m.s. devisations of 0.0356 and 0.0547 Å) are almost perpendicular to the mean plane of the pyrrolidine ring, making dihedral angles of 89.7 (6) and 82.5 (6)°. The acetate group attached to the pyrrolidine ring assumes an extended conformation. In the crystal,N-H⋯O and C-H⋯O hydrogen bonds connect adjacent molecules, forming an infinite tape extending along [1-1-1]. The crystal packing is further consolidated by strong π-π inter-actions with a centroid-centroid distance of 3.2585 (8) Å. The title compound is a polymorph of previously reported monoclinic structure [Ganesh et al. (2012 ▶). Acta Cryst. E68, o2902-o2903].

Related literature

For background literature and the previously reported polymorph, see: Ganesh et al. (2008). For a related structure, see: Wei et al. (2011 ▶).

Experimental

Crystal data

C22H21N3O4

M = 391.42

Triclinic,

a = 9.4418 (3) Å

b = 10.0132 (3) Å

c = 12.8861 (4) Å

α = 67.465 (2)°

β = 88.237 (2)°

γ = 62.842 (1)°

V = 985.68 (5) Å3

Z = 2

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; Bruker, 2008 ▶) T min = 0.978, T max = 0.983

23829 measured reflections

8469 independent reflections

5108 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.158

S = 1.08

8469 reflections

265 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.27 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, 2012) ▶; software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681204706X/pv2603sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204706X/pv2603Isup2.hkl

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

C22H21N3O4	Z = 2
Mr = 391.42	F(000) = 412
Triclinic, P1	Dx = 1.319 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4418 (3) Å	Cell parameters from 8469 reflections
b = 10.0132 (3) Å	θ = 2.4–34.7°
c = 12.8861 (4) Å	µ = 0.09 mm−1
α = 67.465 (2)°	T = 293 K
β = 88.237 (2)°	Block, colourless
γ = 62.842 (1)°	0.25 × 0.22 × 0.19 mm
V = 985.68 (5) Å3

Bruker APEXII CCD area-detector diffractometer	8469 independent reflections
Radiation source: fine-focus sealed tube	5108 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 34.7°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
Tmin = 0.978, Tmax = 0.983	k = −16→16
23829 measured reflections	l = −20→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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0823P)2 + 0.0657P] where P = (Fo2 + 2Fc2)/3
8469 reflections	(Δ/σ)max < 0.001
265 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.7776 (3)	1.0526 (3)	0.51871 (15)	0.0796 (6)
H1A	0.6672	1.1089	0.5272	0.119*
H1B	0.8311	1.1134	0.5210	0.119*
H1C	0.8314	0.9442	0.5797	0.119*
C2	0.77232 (13)	0.91697 (13)	0.39598 (9)	0.0340 (2)
C3	0.76315 (11)	0.95234 (11)	0.26878 (8)	0.02661 (19)
C4	0.76056 (12)	1.11630 (12)	0.21751 (10)	0.0322 (2)
C5	0.77058 (15)	1.16217 (15)	0.30477 (11)	0.0422 (3)
C6	0.7641 (2)	1.3110 (2)	0.28366 (17)	0.0670 (5)
H6	0.7739	1.3393	0.3429	0.080*
C7	0.7427 (2)	1.41584 (19)	0.17152 (19)	0.0769 (6)
H7	0.7374	1.5172	0.1548	0.092*
C8	0.7291 (2)	1.37485 (16)	0.08406 (16)	0.0648 (4)
H8	0.7136	1.4490	0.0091	0.078*
C9	0.73808 (15)	1.22285 (14)	0.10554 (11)	0.0443 (3)
H9	0.7292	1.1947	0.0461	0.053*
C10	0.61443 (11)	0.95525 (12)	0.21822 (9)	0.0294 (2)
H10	0.5964	0.8689	0.2757	0.035*
C11	0.66671 (12)	0.90746 (15)	0.11868 (10)	0.0370 (2)
H11A	0.6483	0.8173	0.1245	0.044*
H11B	0.6070	1.0006	0.0465	0.044*
C12	0.90212 (11)	0.81284 (11)	0.24386 (8)	0.02558 (18)
C13	0.93053 (14)	0.73661 (15)	0.08136 (10)	0.0399 (3)
H13A	1.0405	0.7158	0.0853	0.060*
H13B	0.8829	0.7789	0.0033	0.060*
H13C	0.9282	0.6357	0.1250	0.060*
C14	0.46237 (12)	1.11772 (13)	0.18539 (10)	0.0347 (2)
C15	0.2897 (3)	1.3079 (2)	0.25589 (17)	0.0936 (7)
H15A	0.3143	1.3946	0.2131	0.140*
H15B	0.2644	1.3125	0.3276	0.140*
H15C	0.1986	1.3214	0.2135	0.140*
C16	0.92790 (12)	0.63976 (11)	0.32962 (8)	0.0289 (2)
C17	1.16767 (12)	0.63888 (13)	0.34810 (9)	0.0326 (2)
C18	1.06891 (11)	0.79224 (12)	0.26043 (9)	0.0299 (2)
C19	1.13393 (14)	0.89045 (15)	0.19952 (12)	0.0440 (3)
H19	1.0693	0.9923	0.1397	0.053*
C20	1.29723 (16)	0.83568 (18)	0.22851 (14)	0.0543 (3)
H20	1.3422	0.9014	0.1880	0.065*
C21	1.39322 (15)	0.68469 (19)	0.31685 (14)	0.0547 (4)
H21	1.5024	0.6499	0.3353	0.066*
C22	1.32993 (14)	0.58367 (17)	0.37874 (12)	0.0482 (3)
H22	1.3946	0.4822	0.4389	0.058*
N1	0.78263 (14)	1.03949 (13)	0.41018 (9)	0.0459 (3)
N2	0.83966 (10)	0.85688 (10)	0.12758 (7)	0.02941 (18)
N3	1.08062 (11)	0.55400 (11)	0.38933 (8)	0.0349 (2)
H3	1.1191	0.4587	0.4458	0.042*
O1	0.77037 (12)	0.79974 (10)	0.47206 (7)	0.0499 (2)
O2	0.83142 (10)	0.58935 (10)	0.33842 (7)	0.0409 (2)
O3	0.38293 (12)	1.20557 (12)	0.09240 (8)	0.0593 (3)
O4	0.42723 (12)	1.15085 (11)	0.27609 (8)	0.0563 (3)

	U11	U22	U33	U12	U13	U23
C1	0.1180 (16)	0.0905 (13)	0.0559 (10)	−0.0537 (12)	0.0155 (10)	−0.0508 (10)
C2	0.0382 (5)	0.0283 (5)	0.0297 (5)	−0.0120 (4)	0.0025 (4)	−0.0110 (4)
C3	0.0304 (4)	0.0215 (4)	0.0268 (5)	−0.0134 (3)	0.0023 (3)	−0.0077 (3)
C4	0.0331 (5)	0.0223 (4)	0.0400 (6)	−0.0148 (4)	0.0053 (4)	−0.0098 (4)
C5	0.0475 (6)	0.0353 (6)	0.0548 (8)	−0.0246 (5)	0.0098 (5)	−0.0234 (5)
C6	0.0847 (11)	0.0541 (8)	0.0965 (13)	−0.0476 (8)	0.0291 (9)	−0.0476 (9)
C7	0.0947 (13)	0.0401 (7)	0.1167 (16)	−0.0464 (9)	0.0458 (11)	−0.0374 (9)
C8	0.0760 (10)	0.0301 (6)	0.0769 (11)	−0.0284 (7)	0.0299 (8)	−0.0089 (7)
C9	0.0500 (6)	0.0282 (5)	0.0453 (7)	−0.0189 (5)	0.0117 (5)	−0.0064 (5)
C10	0.0274 (4)	0.0264 (4)	0.0334 (5)	−0.0130 (4)	0.0027 (4)	−0.0112 (4)
C11	0.0291 (4)	0.0416 (6)	0.0421 (6)	−0.0132 (4)	−0.0001 (4)	−0.0234 (5)
C12	0.0269 (4)	0.0216 (4)	0.0264 (5)	−0.0127 (3)	0.0022 (3)	−0.0067 (3)
C13	0.0400 (5)	0.0421 (6)	0.0370 (6)	−0.0152 (5)	0.0088 (4)	−0.0216 (5)
C14	0.0307 (5)	0.0321 (5)	0.0385 (6)	−0.0134 (4)	0.0060 (4)	−0.0142 (4)
C15	0.0981 (14)	0.0496 (9)	0.0712 (11)	0.0100 (9)	0.0338 (10)	−0.0235 (8)
C16	0.0345 (5)	0.0230 (4)	0.0280 (5)	−0.0140 (4)	0.0065 (4)	−0.0093 (4)
C17	0.0308 (4)	0.0308 (5)	0.0313 (5)	−0.0122 (4)	0.0003 (4)	−0.0110 (4)
C18	0.0280 (4)	0.0275 (4)	0.0323 (5)	−0.0141 (4)	0.0019 (4)	−0.0093 (4)
C19	0.0375 (5)	0.0375 (6)	0.0529 (7)	−0.0237 (5)	0.0029 (5)	−0.0075 (5)
C20	0.0395 (6)	0.0593 (8)	0.0714 (10)	−0.0340 (6)	0.0086 (6)	−0.0215 (7)
C21	0.0313 (5)	0.0623 (8)	0.0714 (9)	−0.0229 (6)	0.0003 (6)	−0.0275 (7)
C22	0.0324 (5)	0.0454 (7)	0.0511 (7)	−0.0102 (5)	−0.0081 (5)	−0.0143 (6)
N1	0.0614 (6)	0.0455 (6)	0.0404 (6)	−0.0272 (5)	0.0053 (5)	−0.0250 (5)
N2	0.0285 (4)	0.0307 (4)	0.0262 (4)	−0.0124 (3)	0.0022 (3)	−0.0112 (3)
N3	0.0359 (4)	0.0236 (4)	0.0309 (5)	−0.0102 (3)	0.0015 (3)	−0.0025 (3)
O1	0.0732 (6)	0.0317 (4)	0.0308 (4)	−0.0189 (4)	0.0122 (4)	−0.0076 (3)
O2	0.0455 (4)	0.0325 (4)	0.0490 (5)	−0.0256 (3)	0.0095 (4)	−0.0125 (4)
O3	0.0468 (5)	0.0492 (5)	0.0499 (6)	0.0017 (4)	−0.0116 (4)	−0.0191 (5)
O4	0.0584 (6)	0.0415 (5)	0.0428 (5)	−0.0039 (4)	0.0154 (4)	−0.0178 (4)

C1—N1	1.4514 (18)	C12—N2	1.4484 (13)
C1—H1A	0.9600	C12—C18	1.5028 (13)
C1—H1B	0.9600	C12—C16	1.5645 (13)
C1—H1C	0.9600	C13—N2	1.4548 (14)
C2—O1	1.2149 (13)	C13—H13A	0.9600
C2—N1	1.3529 (15)	C13—H13B	0.9600
C2—C3	1.5348 (14)	C13—H13C	0.9600
C3—C4	1.5052 (13)	C14—O3	1.1904 (14)
C3—C10	1.5497 (13)	C14—O4	1.3263 (14)
C3—C12	1.5558 (13)	C15—O4	1.4389 (17)
C4—C9	1.3775 (16)	C15—H15A	0.9600
C4—C5	1.3879 (17)	C15—H15B	0.9600
C5—C6	1.3808 (18)	C15—H15C	0.9600
C5—N1	1.4035 (17)	C16—O2	1.2112 (12)
C6—C7	1.376 (3)	C16—N3	1.3565 (13)
C6—H6	0.9300	C17—C22	1.3803 (15)
C7—C8	1.366 (3)	C17—C18	1.3899 (14)
C7—H7	0.9300	C17—N3	1.3946 (14)
C8—C9	1.4003 (18)	C18—C19	1.3748 (15)
C8—H8	0.9300	C19—C20	1.3871 (16)
C9—H9	0.9300	C19—H19	0.9300
C10—C14	1.5048 (14)	C20—C21	1.377 (2)
C10—C11	1.5276 (15)	C20—H20	0.9300
C10—H10	0.9800	C21—C22	1.386 (2)
C11—N2	1.4656 (13)	C21—H21	0.9300
C11—H11A	0.9700	C22—H22	0.9300
C11—H11B	0.9700	N3—H3	0.8600
N1—C1—H1A	109.5	C18—C12—C16	101.43 (7)
N1—C1—H1B	109.5	C3—C12—C16	110.59 (7)
H1A—C1—H1B	109.5	N2—C13—H13A	109.5
N1—C1—H1C	109.5	N2—C13—H13B	109.5
H1A—C1—H1C	109.5	H13A—C13—H13B	109.5
H1B—C1—H1C	109.5	N2—C13—H13C	109.5
O1—C2—N1	125.04 (11)	H13A—C13—H13C	109.5
O1—C2—C3	126.49 (10)	H13B—C13—H13C	109.5
N1—C2—C3	108.47 (9)	O3—C14—O4	123.86 (10)
C4—C3—C2	101.98 (8)	O3—C14—C10	126.06 (10)
C4—C3—C10	113.45 (8)	O4—C14—C10	110.09 (9)
C2—C3—C10	113.21 (8)	O4—C15—H15A	109.5
C4—C3—C12	114.98 (8)	O4—C15—H15B	109.5
C2—C3—C12	113.55 (8)	H15A—C15—H15B	109.5
C10—C3—C12	100.24 (7)	O4—C15—H15C	109.5
C9—C4—C5	120.03 (10)	H15A—C15—H15C	109.5
C9—C4—C3	131.23 (10)	H15B—C15—H15C	109.5
C5—C4—C3	108.51 (10)	O2—C16—N3	126.22 (9)
C6—C5—C4	122.02 (14)	O2—C16—C12	126.37 (9)
C6—C5—N1	128.08 (13)	N3—C16—C12	107.37 (8)
C4—C5—N1	109.88 (10)	C22—C17—C18	121.67 (11)
C7—C6—C5	117.35 (15)	C22—C17—N3	128.28 (10)
C7—C6—H6	121.3	C18—C17—N3	109.88 (9)
C5—C6—H6	121.3	C19—C18—C17	119.80 (10)
C8—C7—C6	121.67 (13)	C19—C18—C12	130.94 (9)
C8—C7—H7	119.2	C17—C18—C12	109.02 (8)
C6—C7—H7	119.2	C18—C19—C20	119.12 (11)
C7—C8—C9	120.99 (15)	C18—C19—H19	120.4
C7—C8—H8	119.5	C20—C19—H19	120.4
C9—C8—H8	119.5	C21—C20—C19	120.50 (12)
C4—C9—C8	117.92 (14)	C21—C20—H20	119.8
C4—C9—H9	121.0	C19—C20—H20	119.8
C8—C9—H9	121.0	C20—C21—C22	121.16 (11)
C14—C10—C11	114.04 (9)	C20—C21—H21	119.4
C14—C10—C3	113.06 (8)	C22—C21—H21	119.4
C11—C10—C3	104.49 (8)	C17—C22—C21	117.72 (12)
C14—C10—H10	108.3	C17—C22—H22	121.1
C11—C10—H10	108.3	C21—C22—H22	121.1
C3—C10—H10	108.3	C2—N1—C5	111.02 (10)
N2—C11—C10	105.43 (8)	C2—N1—C1	122.76 (12)
N2—C11—H11A	110.7	C5—N1—C1	125.37 (12)
C10—C11—H11A	110.7	C12—N2—C13	115.72 (8)
N2—C11—H11B	110.7	C12—N2—C11	108.13 (8)
C10—C11—H11B	110.7	C13—N2—C11	114.45 (8)
H11A—C11—H11B	108.8	C16—N3—C17	111.89 (8)
N2—C12—C18	114.11 (8)	C16—N3—H3	124.1
N2—C12—C3	100.86 (7)	C17—N3—H3	124.1
C18—C12—C3	117.03 (8)	C14—O4—C15	116.15 (12)
N2—C12—C16	113.33 (8)
O1—C2—C3—C4	176.72 (11)	C18—C12—C16—O2	−171.33 (10)
N1—C2—C3—C4	−3.10 (11)	C3—C12—C16—O2	63.84 (13)
O1—C2—C3—C10	54.46 (14)	N2—C12—C16—N3	129.09 (9)
N1—C2—C3—C10	−125.36 (10)	C18—C12—C16—N3	6.33 (10)
O1—C2—C3—C12	−58.99 (14)	C3—C12—C16—N3	−118.50 (9)
N1—C2—C3—C12	121.20 (10)	C22—C17—C18—C19	2.17 (18)
C2—C3—C4—C9	−173.11 (11)	N3—C17—C18—C19	−173.57 (10)
C10—C3—C4—C9	−51.01 (15)	C22—C17—C18—C12	177.20 (10)
C12—C3—C4—C9	63.56 (15)	N3—C17—C18—C12	1.46 (12)
C2—C3—C4—C5	1.16 (11)	N2—C12—C18—C19	47.46 (15)
C10—C3—C4—C5	123.25 (10)	C3—C12—C18—C19	−69.93 (15)
C12—C3—C4—C5	−122.17 (10)	C16—C12—C18—C19	169.68 (12)
C9—C4—C5—C6	−2.22 (19)	N2—C12—C18—C17	−126.83 (9)
C3—C4—C5—C6	−177.24 (12)	C3—C12—C18—C17	115.78 (10)
C9—C4—C5—N1	176.11 (10)	C16—C12—C18—C17	−4.61 (11)
C3—C4—C5—N1	1.09 (13)	C17—C18—C19—C20	−1.35 (19)
C4—C5—C6—C7	1.7 (2)	C12—C18—C19—C20	−175.14 (12)
N1—C5—C6—C7	−176.26 (14)	C18—C19—C20—C21	0.2 (2)
C5—C6—C7—C8	−0.3 (3)	C19—C20—C21—C22	0.1 (2)
C6—C7—C8—C9	−0.6 (3)	C18—C17—C22—C21	−1.76 (19)
C5—C4—C9—C8	1.18 (18)	N3—C17—C22—C21	173.13 (12)
C3—C4—C9—C8	174.90 (12)	C20—C21—C22—C17	0.6 (2)
C7—C8—C9—C4	0.2 (2)	O1—C2—N1—C5	−175.84 (11)
C4—C3—C10—C14	−33.41 (12)	C3—C2—N1—C5	3.98 (13)
C2—C3—C10—C14	82.20 (10)	O1—C2—N1—C1	−5.9 (2)
C12—C3—C10—C14	−156.52 (8)	C3—C2—N1—C1	173.94 (13)
C4—C3—C10—C11	91.15 (10)	C6—C5—N1—C2	174.92 (14)
C2—C3—C10—C11	−153.24 (8)	C4—C5—N1—C2	−3.28 (15)
C12—C3—C10—C11	−31.96 (9)	C6—C5—N1—C1	5.3 (2)
C14—C10—C11—N2	132.27 (9)	C4—C5—N1—C1	−172.92 (14)
C3—C10—C11—N2	8.34 (11)	C18—C12—N2—C13	62.19 (11)
C4—C3—C12—N2	−77.70 (9)	C3—C12—N2—C13	−171.46 (8)
C2—C3—C12—N2	165.37 (8)	C16—C12—N2—C13	−53.25 (11)
C10—C3—C12—N2	44.33 (8)	C18—C12—N2—C11	−167.94 (8)
C4—C3—C12—C18	46.69 (12)	C3—C12—N2—C11	−41.58 (9)
C2—C3—C12—C18	−70.23 (11)	C16—C12—N2—C11	76.63 (10)
C10—C3—C12—C18	168.72 (8)	C10—C11—N2—C12	21.22 (11)
C4—C3—C12—C16	162.12 (8)	C10—C11—N2—C13	151.79 (9)
C2—C3—C12—C16	45.19 (10)	O2—C16—N3—C17	171.68 (10)
C10—C3—C12—C16	−75.85 (9)	C12—C16—N3—C17	−5.99 (11)
C11—C10—C14—O3	1.20 (16)	C22—C17—N3—C16	−172.33 (12)
C3—C10—C14—O3	120.39 (13)	C18—C17—N3—C16	3.04 (12)
C11—C10—C14—O4	−178.99 (9)	O3—C14—O4—C15	−3.9 (2)
C3—C10—C14—O4	−59.81 (12)	C10—C14—O4—C15	176.33 (15)
N2—C12—C16—O2	−48.57 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1i	0.86	2.10	2.9107 (12)	157
C15—H15B···O1ii	0.96	2.47	3.363 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1i	0.86	2.10	2.9107 (12)	157
C15—H15B⋯O1ii	0.96	2.47	3.363 (2)	155

Symmetry codes: (i) ; (ii) .