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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.

ABSTRACT: 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].

SUBMITTER: Karthikeyan S

PROVIDER: S-EPMC3998486 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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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.

Karthikeyan S S Sethusankar K K Devaraj Anthonisamy A Bakthadoss Manickam M

Acta crystallographica. Section E, Structure reports online 20140212 Pt 3

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 ...[more]

PMID: 24764986

Similar Datasets

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

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

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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].

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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.

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

Project description: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.

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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

1'-Methyl-2-oxo-5'-phenyl-spiro-[indoline-3,3'-pyrrolidine]-4',4'-dicarbo-nitrile.

Project description:The title spiro-compound, C(20)H(16)N(4)O, crystallizes with four independent mol-ecules in the asymmetric unit. In all of them, the oxindole unit is planar, the r.m.s. deviations ranging from 0.07 to 0.08 Å, while the pyrrolinyl ring adopts an envelope conformation (with the N atom representing the flap). In the crystal, adjacent mol-ecules are linked by N-H⋯N and N-H⋯O hydrogen bonds.

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4-Hydr-oxy-3-(1'-methyl-2-oxo-4'-phenyl-spiro-[indoline-3,2'-pyrrolidine]-3'-yl-carbon-yl)quinolin-2(1H)-one.

Project description:In the title compound, C(28)H(23)N(3)O(4), the dihedral angle between the quinoline and indole ring systems is 29.30 (5)°. The pyrrolidine ring adopts a twist conformation. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. A weak intra-molecular C3-H3⋯O3 inter-action is also observed. In the crystal, mol-ecules are linked by two sets of N-H⋯O hydrogen bonds, forming centrosymmetric dimers containing two R(2) (2)(8) ring motifs. The dimers are linked via C-H⋯π inter-actions.

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Methyl 4'-(3-bromo-phen-yl)-3'-(2,5-di-methyl-benz-yl)-1'-methyl-2-oxo-spiro-[indo-line-3,2'-pyrrolidine]-3'-carboxyl-ate.

Project description:In the title compound, C29H29BrN2O3, the indole ring system is essentially planar (r.m.s. deviation = 0.079 Å) and makes a dihedral angle of 85.23 (10)° with the mean plane of the 4-methyl-pyrrolidine ring. This ring adopts an envelope conformation with the N atom at the flap. The pyrrolidine 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. In the crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(14) ring motif. These dimers are further linked by N-H⋯O and C-H⋯O hydrogen bonds, forming two-dimensional networks lying parallel to (10-1).

| S-EPMC3998460 | 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 π-π inter-actions [centroid-centroid distance = 3.2032 (11) Å].

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