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A diastereomer of methyl (1R,3'S)-1',1''-dimethyl-2,2''-dioxo-2H-dispiro-[ace-naphthyl-ene-1,2'-pyrrolidine-3',3''-indoline]-4'-carboxyl-ate.

ABSTRACT: In the title compound, C26H22N2O4, the central pyrrolidine ring adopts a twist conformation and the cyclo-pentane ring of the dihydro-acenapthylene group adopts an envelope conformation with the spiro C atom as the flap. The naphthalene ring system of the dihydro-acenaphthyl-ene group forms dihedral angles of 83.4?(9) and 61.3?(7)°, respectively, with the mean planes of the pyrrolidine and indole rings. The crystal packing is stabilized by inter-molecular C-H?O hydrogen bonds. The title compound is a diastereomer of a previously reported structure.

SUBMITTER: Ganesh G

PROVIDER: S-EPMC3588527 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

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A diastereomer of methyl (1R,3'S)-1',1''-dimethyl-2,2''-dioxo-2H-dispiro-[ace-naphthyl-ene-1,2'-pyrrolidine-3',3''-indoline]-4'-carboxyl-ate.

Ganesh Gnanavelu G Yuvaraj Panneerselvam P Kannan Piskala Subburaman PS Reddy Boreddy Siva Rami BS Subbiahpandi Arunachalathevar A

Acta crystallographica. Section E, Structure reports online 20130223 Pt 3

In the title compound, C26H22N2O4, the central pyrrolidine ring adopts a twist conformation and the cyclo-pentane ring of the dihydro-acenapthylene group adopts an envelope conformation with the spiro C atom as the flap. The naphthalene ring system of the dihydro-acenaphthyl-ene group forms dihedral angles of 83.4 (9) and 61.3 (7)°, respectively, with the mean planes of the pyrrolidine and indole rings. The crystal packing is stabilized by inter-molecular C-H⋯O hydrogen bonds. The title compound ...[more]

PMID: 23476610

Similar Datasets

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

1'-Methyl-4'-phenyl-dispiro-[chromane-3,3'-pyrrolidine-2',3''-indoline]-2,2''-dione.

Project description:In the title compound, C(26)H(22)N(2)O(3), the pyrrolidine ring adopts an envelope conformation with the N atom as the flap. In the crystal, pairs of centrosymmetrically related mol-ecules are linked into dimers by N-H⋯O hydrogen bonds. In addition, there are C-H⋯O hydrogen bonds.

| S-EPMC3297956 | biostudies-literature

Crystal structure of 1,2-di-benzoyl-ace-naphthyl-ene.

Project description:The title mol-ecule, C26H16O2, crystallizes as a mol-ecular crystal with no strong inter-molecular inter-actions (the shortest C-H⋯O contact is longer than 3.4 Å). Two flat ace-naphthyl-ene groups of neigboring 1,2-di-benzoyl-ace-naphthyl-ene mol-ecules are related by a crystallographic center of symmetry and are stacked with the distance between their mean planes of 3.37 (1) Å, apparently making an optimal close packing for these bulky aromatic moieties. Both carbonyl groups are oriented towards the same side of the planar ace-naphthyl-ene. The angles between the flat ace-naphthyl-ene group and the benzoyl groups are 62.6 (1) and 57.8 (1)°. Because rotation of the benzoyl groups is sterically hindered, we expect that the mol-ecules will remain locked in this 'pseudo-cis' orientation in solution. As a result, reduction of 1,2-di-benzoyl-ace-naphthyl-ene at low temperature with sodium di-thio-nite yields the cis-isomer of 1,2-dibenzoyl-1,2-di-hydro-ace-naphthyl-ene, which is sterically favorable. This isomer is thermodynamically less favorable than the trans isomer, but it converts to the more stable isomer only on long-term heating (Greenberg & Schenendorf (1980 ▸).

| S-EPMC4518958 | biostudies-literature

4'-(4-Methoxy-phen-yl)-1,1',1''-trimethyl-dispiro-[indoline-3,2'-pyrrolidine-3',3''-pyrrolidine]-2,2'',5''-trione.

Project description:In the title compound, C(24)H(25)N(3)O(4), the pyrrolidine ring adopts an envelope conformation while the pyrrolidine-2'',5''-dione ring adopts a twist conformation. The indoline unit is planar [maximum deviation of -0.050?(9)?Å] and forms a dihedral angle of 40.36?(4)° with the methoxy-phenyl ring. Intra-molecular C-H?O hydrogen bonds are observed. In the crystal, mol-ecules are linked into a two-dimensional network parallel to the ab plane by inter-molecular C-H?O hydrogen bonds and C-H?? inter-actions.

| S-EPMC2969413 | biostudies-literature

1'-Methyl-4'-(4-methyl-phen-yl)dispiro-[indane-2,3'-pyrrolidine-2',3''-indoline]-1,2''-dione.

Project description:In the title mol-ecule, C(27)H(24)N(2)O(2), the pyrrolidin-2-one ring is almost planar (r.m.s. deviation = 0.003 Å), the pyrrolidine ring has an envelope conformation (the N atom is the flap atom) and the cyclo-penta-none ring is twisted about the C(q)-C(m) bond (q = quaternary and m = methylene). The ketone O atoms are directed to opposite sides of the mol-ecule. Supra-molecular chains along the a axis are formed in the crystal packing mediated by N-H⋯N and C-H⋯O inter-actions. These are connected into layers in the ab plane via C-H⋯π inter-actions.

| S-EPMC3393996 | biostudies-literature

1'-Methyl-4'-phenyl-2''-sulfanylidene-dispiro-[indoline-3,2'-pyrrolidine-3',5''-1,3-thia-zolidine]-2,4''-dione.

Project description:The title compound, C(20)H(17)N(3)O(2)S(2), crystallizes with two mol-ecules in the asymmetric unit. The pyrrolo-dine rings have envelope conformations in both mol-ecules, the N atoms deviating by 0.574?(3) and 0.612?(2)?Å from the mean planes through the other ring atoms. The 1'-methyl and 4'-phenyl groups on the pyrrolidine rings are substituted in equatorial positions. In the crystal, mol-ecules are linked into a three-dimensional network by N-H?O, N-H?N and C-H?O and N-H?? hydrogen bonds.

| S-EPMC3275027 | biostudies-literature

1',6-Dimethyl-4'-phenyl-dispiro-[1-benzopyran-3(4H),3'-pyrrolidine-2',3''-indoline]-2,2''-dione.

Project description:In the title compound, C(27)H(24)N(2)O(3), the five-membered pyrroldine ring adopts an envelope conformation (with the N atom in the flap position) and the six-membered pyran-one ring of the coumarine ring system adopts a slightly distorted boat conformation. The oxindole unit makes dihedral angles of 89.7 (1) and 25.6 (1)°, respectively, with the pyrrolidine ring and the coumarin ring system. The mol-ecular structure is stabilized by two intra-molecular C-H⋯O contacts and two intra-molecular π-π inter-actions [centroid-centroid seperations of 3.514 (1) and 3.623 (1) Å]. The crystal packing features N-H⋯O hydrogen bonds, which link the mol-ecules into cyclic centrosymmetric R(2) (2)(8) dimers, and C-H⋯π inter-actions.

| S-EPMC3239137 | biostudies-literature

Selective construction of dispiro[indoline-3,2'-quinoline-3',3''-indoline] and dispiro[indoline-3,2'-pyrrole-3',3''-indoline] via three-component reaction.

Project description:A convenient synthetic procedure for the construction of novel dispirooxindole motifs was successfully developed by base-promoted three-component reaction of ammonium acetate, isatins and in situ-generated 3-isatyl-1,4-dicarbonyl compounds. The piperidine-promoted three-component reaction of ammonium acetate, isatins and the in situ-generated dimedone adducts of 3-ethoxycarbonylmethyleneoxindoles afforded mutlifunctionalized dispiro[indoline-3,2'-quinoline-3',3''-indoline] derivatives in good yields and with high diastereoselectivity. On the other hand, a similar reaction of the dimedone adducts of 3-phenacylideneoxindoles afforded unique dispiro[indoline-3,2'-pyrrole-3',3''-indoline] derivatives with a cyclohexanedione substituent. A plausible reaction mechanism is proposed to explain the formation of the different spirooxindoles.

| S-EPMC10478003 | biostudies-literature

Crystal structures of ethyl (2S*,2'R*)-1'-methyl-2'',3-dioxo-2,3-di-hydro-dispiro-[1-benzo-thio-phene-2,3'-pyrrolidine-2',3''-indoline]-4'-carboxyl-ate and ethyl (2S*,2'R*)-5''-chloro-1'-methyl-2'',3-dioxo-2,3-di-hydro-dispiro-[1-benzo-thio-phene-2,3'-pyrrolidine-2',3''-indoline]-4'-carboxyl-ate.

Project description:In the title compounds, C22H20N2O4S, (I), and C22H19ClN2O4S, (II), the pyrrolidine rings have twist conformations on the spiro-spiro C-C bonds. In (I), the five-membered ring of the oxindole moiety has an envelope conformation with the spiro C atom as the flap, while in (II) this ring is flat (r.m.s. deviation = 0.042?Å). The mean planes of the pyrrolidine rings are inclined to the mean planes of the indole units [r.m.s deviations = 0.073 and 0.069?Å for (I) and (II), respectively] and the benzo-thio-phene ring systems (r.m.s. deviations = 0.019 and 0.034?Å for (I) and (II), respectively) by 79.57?(8) and 88.61?(7)° for (I), and by 81.99?(10) and 88.79?(10)° for (II). In both compounds, the eth-oxy-carbonyl group occupies an equatorial position with an extended conformation. The overall conformation of the two mol-ecules differs in the angle of inclination of the indole unit with respect to the benzo-thio-phene ring system, with a dihedral angle between the planes of 71.59?(5) in (I) and 82.27?(7)° in (II). In the crystal of (I), mol-ecules are linked via pairs of N-H?O hydrogen bonds, forming inversion dimers enclosing R 2 (2)(14) loops. The dimers are linked via C-H?O and bifurcated C-H?O(O) hydrogen bonds, forming sheets lying parallel to (100). In the crystal of (II), mol-ecules are again linked via pairs of N-H?O hydrogen bonds, forming inversion dimers but enclosing smaller R 2 (2)(8) loops. Here, the dimers are linked by C-H?O hydrogen bonds, forming ribbons propagating along [010].

| S-EPMC4158536 | biostudies-other

(1S,1'S,2'R,4a'S,9a'S,9b'R)-1'-Acet-yloxy-2,4'-dioxo-2',4',4a',7',8',9',9a',9b'-octa-hydro-1'H,2H-spiro-[ace-naphthyl-ene-1,5'-pyrano[4,3-a]pyrrolizin]-2'-ylmethyl acetate.

Project description:In the title compound C26H25NO7, the mean plane through the lactone-substituted ring of the pyrrolizidine moiety forms dihedral angles of 78.46?(6) and 58.28?(8)° with the ace-naphthyl-ene moiety and the sugar based-lactone ring, respectively. The sum of the angles at the the N atom of the pyrrolizidine ring (335.0°) is in accordance with sp (3) hybridization. Some atoms of the acetate group are disordered and were refined using a split model [occupancy ratio 0.673?(10):0.327?(10)].

| S-EPMC3884278 | biostudies-literature

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