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Methyl 5''-chloro-1',1''-dimethyl-2,2''-dioxodi-spiro-[indoline-3,2'-pyrrolidine-3',3''-indoline]-4'-carboxyl-ate.

ABSTRACT: In the title compound, C22H20ClN3O4, the central pyrrolidine ring adopts an envelope conformation on the N atom. The indolinone systems are individually roughly planar, with maximum deviations from their mean planes of 0.130 Å for the spiro C atom of the indolinone unit and 0.172 Å for the carbonyl C atom of the 5-chloro-1-methyl-indolinone unit. They make dihedral angles of 77.7 (8) and 86.1 (8)° with the mean plane through the central pyrrolidine ring. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds supported by C-H⋯O contacts into chains along the ab diagonal. The structure also features C-H⋯O hydrogen bonds, forming R 2 (2)(8) and R 2 (2)(16) rings and generating a three-dimensional array.

SUBMITTER: Kannan PS

PROVIDER: S-EPMC3684914 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Methyl 3'-benzyl-4'-(2-chloro-phen-yl)-1'-methyl-2-oxo-spiro-[indoline-3,2'-pyrrolidine]-3'-carboxyl-ate.

Project description:In the title compound, C27H25ClN2O3, the methyl-pyrrolidine ring adopts an envelope conformation with the N atom at the flap. The mean plane of the pyrrolidine ring makes dihedral angles of 82.1?(1), 84.4?(1) and 79.8?(1)°, respectively, with the adjacent benzene ring, the mean plane of the indoline ring system and the phenyl ring. The mol-ecular structure is stabilized by intra-molecular C-H?O hydrogen bonds. In the crystal, mol-ecules are linked into chains along [101] by N-H?O hydrogen bonds. C-H?? inter-actions are observed between the chains.

| S-EPMC3793722 | biostudies-literature

Methyl 3'-benzyl-4'-(2,4-di-chloro-phen-yl)-1'-methyl-2-oxo-spiro-[indoline-3,2'-pyrrolidine]-3'-carboxyl-ate.

Project description:In the title compound, C27H24Cl2N2O3, the indole ring system is essentially planar, with a maximum deviation of 0.082 (2) Å for the carbonyl C atom. It makes a dihedral angle of 88.53 (6)° with the mean plane of the 4-methyl-pyrrolidine ring, which adopts an envelope conformation with the N atom at the flap position. The mol-ecular structure is stabilized by intra-molecular C-H⋯O hydrogen bonds, which generate S(6) and S(7) ring motifs, and an intra-molecular π-π inter-action involving the benzyl and di-chloro-substituted benzene rings [centroid-centroid distance = 3.6291 (11) Å]. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds, forming C(7) chains running parallel to [10-1].

| S-EPMC3998484 | biostudies-literature

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

Project description: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 ?-? 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].

| S-EPMC3589042 | biostudies-literature

Methyl 3'-(2,5-di-methyl-benz-yl)-1'-methyl-2-oxo-4'-phenyl-spiro-[indoline-3,2'-pyrrolidine]-3'-carboxyl-ate chloro-form monosolvate.

Project description:In the title solvate, C29H30N2O3·CHCl3, the dihedral angle between the indole ring system (r.m.s. deviation = 0.050 Å) and the 4-methyl-pyrrolidine ring is 88.88 (8)°. The latter ring adopts an envelope conformation with the N atom as the flap. Its mean plane makes dihedral angles of 86.94 (11) and 42.08 (9)° with the phenyl and di-methyl-benzene rings, respectively. The mol-ecular conformation is stabilized by intra-molecular C-H⋯O hydrogen bonds, which generate S(6) and S(9) ring motifs. The chloro-form solvent mol-ecule is linked to the organic mol-ecule by a C-H⋯O hydrogen bond involving the carbonyl O atom of the carboxyl-ate group. In the crystal, mol-ecules are linked via bifurcated N-H⋯(N,O) and C-H⋯O hydrogen bonds, forming chains propagating along [001].

| S-EPMC3998463 | biostudies-literature

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

Project description: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 ?-? inter-actions [centroid-centroid distance = 3.2032?(11)?Å].

| S-EPMC3470252 | biostudies-other

Crystal structure of methyl 1-methyl-2-oxo-spiro-[indoline-3,2'-oxirane]-3'-carboxyl-ate.

Project description:In the title compound, C12H11NO4, the dihedral angle between the indole ring system (r.m.s. deviation = 0.019 Å) and the oxirane ring is 88.8 (2)°. The oxirane O atom and the bridging ester O atom are in an approximate syn conformation [O-C-C-O = -25.4 (3)°] In the crystal, inversion dimers linked by pair of C-H⋯O hydrogen bonds generate R 2 (2)(8) loops, where the C-H donor group forms part of the oxirane ring. A second C-H⋯O inter-action arising from one of the C-H groups of the benzene ring links the dimers into [001] double chains.

| S-EPMC4420098 | biostudies-literature

Methyl 3'-benzyl-4'-(2,4-di-chloro-phen-yl)-1'-methyl-2-oxo-1-propyl-spiro-[indoline-3,2'-pyrrolidine]-3'-carboxy-l-ate.

Project description:In the title compound, C30H30Cl2N2O3, the indole ring system is roughly planar, with a maximum deviation of 0.1039 (18) Å for the carbonyl C atom, and makes a dihedral angle of 86.61 (9)° with the mean plane of the pyrrolidine ring. This spiro pyrrolidine ring adopts an envelope conformation with the N atom at the flap position. The pyrrole ring of the indole ring system adopts a twisted conformation on the C-C(=O) bond. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O hydrogen bond, which generates an S(6) ring motif, and a π-π inter-action [centroid-centroid distance = 3.6577 (12) Å] involving the 2,4-di-chloro-phenyl ring and the benzyl ring. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming C(9) chains running parallel to [10-1].

| S-EPMC3998486 | biostudies-literature

Ethyl 8''-chloro-1'-methyl-2,12''-dioxo-12''H-di-spiro-[indoline-3,2'-pyrrolidine- 3',6''-indolo[2,1-b]quinazoline]-4'-carboxyl-ate.

Project description:In the title compound, C29H23ClN4O4, the quinazoline-indole system and the indolin-2-one system are each essentially planar, with maximum deviations from their mean planes of 0.150?(2) and 0.072?(2)?Å, respectively. The central pyrrolidine ring adopts a twisted conformation on the C-C bond involving the spiro C atoms. Its mean plane forms dihedral angles of 83.37?(9) and 86.56?(8)°, respectively, with the indole rings of the indolin-2-one and quinazoline-indole systems. In the crystal, mol-ecules are linked via pairs of N-H?O hydrogen bonds, forming inversion dimers. The dimers are linked via C-H?O hydrogen bonds, forming chains propagating along [001].

| S-EPMC3772491 | biostudies-other

rac-Methyl (1R,3'S)-1',1''-dimethyl-2,2''-dioxo-2H-dispiro-[acenaphthyl-ene-1,2'-pyrrolidine-3',3''-indoline]-4'-carboxyl-ate.

Project description:In the title compound, C(26)H(22)N(2)O(4), the pyrrolidine ring adopts a twisted conformation and the other five-membered rings adopt envelope conformations with the spiro C atoms as the flap atoms. The naphthalene ring system of the dihydro-acenaphthyl-ene group forms dihedral angles of 89.2?(9) and 75.5?(6)° with the pyrrolidine and indole rings, respectively. The pyrrolidine ring makes a dihedral angle of 80.1?(9)° with the indole ring. In the crystal, mol-ecules are linked by weak C-H?O hydrogen bonds, forming chains along the b-axis direction.

| S-EPMC3569768 | biostudies-literature

Methyl (3S,10b'S)-5-chloro-9'-fluoro-1-methyl-2-oxo-5'-phenyl-10b'H-spiro-[indoline-3,1'-pyrazolo-[3,2-a]iso-quinoline]-2'-carboxyl-ate.

Project description:In the title compound, C27H19ClFN3O3, the pyrazole ring has a twist conformation and the six-membered ring to which it is fused has a screw-boat conformation. The mean plane of the pyrazole ring is inclined to the 2-methyl-indoline ring by 85.03?(9) and by 28.17?(8)° to the mean plane of the iso-quinoline ring system. In the crystal, mol-ecules are linked by pairs of C-H?F hydrogen bonds, forming inversion dimers. These dimers are linked via C-H?O hydrogen bonds, forming a two-dimensional network lying parallel to (10-1).

| S-EPMC3684913 | biostudies-literature

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