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3'-[(1H-Indol-3-yl)carbon-yl]-1'-methyl-2-oxo-4'-(thio-phen-2-yl)-spiro-[indoline-3,2'-pyrrolidine]-3'-carbo-nitrile.

ABSTRACT: In the title compound, C26H20N4O2S, the central pyrrolidine ring adopts a twist conformation on the C-C bond involving the spiro C atom. Its mean plane makes dihedral angles of 78.83?(14), 65.91?(15) and 44.49?(18)° with the mean planes of the adjacent oxindole ring system, the indole system and the thio-phene ring, respectively. The indole and indoline units are essentially planar, with maximum deviations of 0.019?(3) and 0.090?(3)?Å, respectively. In the oxindole fused-ring system, the pyrrole ring adopts an envelope conformation with the spiro C atom as the flap. In the crystal, pairs of N-H?O hydrogen bonds link the mol-ecules, forming inversion dimers with an R (2) 2(8) ring motif. The dimers are linked by further N-H?O hydrogen bonds, forming a two-dimensional network lying parallel to (100).

SUBMITTER: Inglebert SA

PROVIDER: S-EPMC3790442 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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3'-[(1H-Indol-3-yl)carbon-yl]-1'-methyl-2-oxo-4'-(thio-phen-2-yl)-spiro-[indoline-3,2'-pyrrolidine]-3'-carbo-nitrile.

Inglebert S Antony SA Arun Yuvaraj Y Sethusankar K K Perumal Paramasivam T PT

Acta crystallographica. Section E, Structure reports online 20130925 Pt 10

In the title compound, C26H20N4O2S, the central pyrrolidine ring adopts a twist conformation on the C-C bond involving the spiro C atom. Its mean plane makes dihedral angles of 78.83 (14), 65.91 (15) and 44.49 (18)° with the mean planes of the adjacent oxindole ring system, the indole system and the thio-phene ring, respectively. The indole and indoline units are essentially planar, with maximum deviations of 0.019 (3) and 0.090 (3) Å, respectively. In the oxindole fused-ring system, the pyrrole ...[more]

PMID: 24098261

Similar Datasets

4'-(1H-Imidazol-2-yl)-3'-[(1H-indol-3-yl)carbon-yl]-1'-methyl-2-oxo-spiro-[indoline-3,2'-pyrrolidine]-3'-carbo-nitrile 0.15-hydrate.

Project description:In the title compound, C25H20N6O2·0.15H2O, the dihedral angles between the least-squares planes of the indole and pyrrolidine rings and between the oxindole and imidazole rings are 77.66?(7) and 45.31?(7)°, respectively. The pyrrolidine ring and the fused five-membered pyrrolidine ring of the oxindole moiety exhibit twisted conformations. The amide N atom is involved in both intra- and inter-molecular hydrogen bonding, having a bifurcated character. The mol-ecular structure is characterized by an intra-molecular N-H?O hydrogen bond, which generates an S(7) ring motif while an inter-molecular N-H?O hydrogen bond links the organic and solvent water mol-ecules. In the crystal, N-H?N hydrogen bonds generate a zigzag chain running parallel to c-axis direction. The H atoms of the solvent water mol-ecule were not located.

| S-EPMC3884395 | biostudies-literature

Crystal structure of 3'-(1H-indole-3-carbon-yl)-1'-methyl-2-oxo-4'-(4-oxo-4H-chromen-3-yl)spiro-[indoline-3,2'-pyrrolidine]-3'-carbo-nitrile.

Project description:In the title compound, C31H22N4O4, the pyrrolidine ring adopts a twist conformation on the N-CH2 bond. The indolin-2-one and the 1H-indole rings are nearly planar (r.m.s. deviations = 0.06 and 0.011?Å, respectively) and are inclined to one another by 34.19?(9)°. The chromene ring system is also nearly planar (r.m.s. deviation = 0.029?Å). It is almost normal to the 1H-indole ring system, with a dihedral angle of 88.71?(8)°, and is inclined to the indolin-2-one ring system by 72.76?(8)°. In the crystal, mol-ecules are linked via N-H?O hydrogen bonds, forming slabs parallel to (10-1). The slabs are linked by C-H?O hydrogen bonds, forming a three-dimensional structure.

| S-EPMC4645027 | biostudies-literature

1-Ethyl-4'-(1H-indol-3-ylcarbon-yl)-1'-methyl-2,2''-dioxodi-spiro-[indoline-3,2'-pyrrolidine-3',3''-indoline]-4'-carbo-nitrile dimethyl sulfoxide monosolvate.

Project description:In the title compound, C31H25N5O3·C2H6OS, the three indole/indoline units are all essentially planar with maximum deviations of 0.0172?(3), 0.053?(2) and 0.07?(2)?Å. The pyrrolidine ring adopts an envelope conformation with the C atoms bearing the 1-ethyl-2-oxo-indole substituent (in which the five-membered ring adopts a twisted conformation) as the flap. The dimethyl sulfoxide solvent mol-ecule is disordered over two positions, with an occupancy factor ratio of 0.871?(4):0.129?(4). The solvent components are linked to the heterocyclic mol-ecule via C-H?O and C-H?S hydrogen bonds. In the crystal, the solvent components are linked to the heterocyclic molecule via C-H?O and C-H?S inter-actions, forming R 2 (2)(10) ring motifs. The mol-ecules are further connected into a chain along the a-axis direction via N-H?O hydrogen bonds.

| S-EPMC3793813 | 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.

| S-EPMC2980256 | biostudies-literature

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

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?? inter-actions.

| S-EPMC2983794 | 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

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 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

3'-[Hy-droxy(4-oxo-4H-chromen-3-yl)meth-yl]-2-oxospiro-[indoline-3,2'-pyrrolidine]-3'-carbonitrile.

Project description:In the title compound, C(23)H(19)N(3)O(4), the pyran ring adopts a half-chair conformation, while the pyrrolidine (with a C atom as the flap atom) and the five-membered ring in the indoline (with a C atom as the flap atom) ring system adopt slight envelope conformations. The pyrrolidine ring makes dihedral angles of 83.3?(1) and 60.4?(1)° with the mean plane through all non-H atoms of the indoline and chromene ring systems, respectively. In the crystal, mol-ecules are connected by two unique N-H?O and O-H?O hydrogen-bonding inter-actions, which form centrosymmetric patterns described by graph-set motifs R(2) (2)(18) and R(2) (2)(14). These two motifs combine to form a hydrogen-bonded chain which propagates in the a-axis direction. The crystal structure is also stablized by C-H?O inter-actions and by aromatic ?-? stacking inter-actions between the pyran and benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.755?(1)?Å and slippage = 1.371?(2)?Å].

| S-EPMC3254481 | biostudies-literature

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