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Crystal structure of ethyl 5''-fluoro-2'',3-dioxo-6',7',8',8a'-tetra-hydro-2'H,3H,5'H-di-spiro-[benzo[b]thio-phene-2,1'-indol-izine-3',3''-indoline]-2'-carboxyl-ate.

ABSTRACT: In the title compound, C25H23FN2O4S, the fused piperidine ring of the octa-hydro-indolizine ring system adopts a chair conformation and the five-membered ring has a twisted conformation on the N-C(spiro) bond. The mean planes of the benzo-thio-phene and indoline ring systems are inclined to the mean plane of the pyrrolidine ring by 83.1?(1) and 84.9?(1)°, respectively, and to each other by 29.37?(17)°. In the crystal, mol-ecules are linked via pairs of N-H?O hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif. The dimers are linked via C-H?O hydrogen bonds, forming slabs lying parallel to (100). The packing between the slabs features a short [2.734?(2)?Å] F?F contact.

SUBMITTER: Raja R

PROVIDER: S-EPMC4350745 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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Crystal structure of ethyl 5''-fluoro-2'',3-dioxo-6',7',8',8a'-tetra-hydro-2'H,3H,5'H-di-spiro-[benzo[b]thio-phene-2,1'-indol-izine-3',3''-indoline]-2'-carboxyl-ate.

Raja R R Govindaraj J J Suresh M M Raghunathan R R SubbiahPandi A A

Acta crystallographica. Section E, Crystallographic communications 20150207 Pt 3

In the title compound, C25H23FN2O4S, the fused piperidine ring of the octa-hydro-indolizine ring system adopts a chair conformation and the five-membered ring has a twisted conformation on the N-C(spiro) bond. The mean planes of the benzo-thio-phene and indoline ring systems are inclined to the mean plane of the pyrrolidine ring by 83.1 (1) and 84.9 (1)°, respectively, and to each other by 29.37 (17)°. In the crystal, mol-ecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dim ...[more]

PMID: 25844224

Similar Datasets

Crystal structure of ethyl 1',1''-dimethyl-2'',3-dioxo-3H-di-spiro-[benzo[b]thio-phene-2,3'-pyrrolidine-2',3''-indoline]-4'-carboxyl-ate.

Project description:In the title compound, C23H22N2O4S, the pyrrolidine ring has an envelope conformation with the spiro C atom, shared with the indoline ring system, as the flap. The mean planes of the benzo-thio-phene and indoline ring systems are inclined to the mean plane of the pyrrolidine ring by 88.81 (8) and 79.48 (8)°, respectively, and to each other by 68.12 (5)°. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming chains propagating along [001].

| S-EPMC4350758 | biostudies-literature

Crystal structure of ethyl 1',5-dimethyl-2'',3-dioxo-3H-di-spiro-[benzo[b]thiophene-2,3'-pyrrolidine-2',3''-indoline]-4'-carboxyl-ate.

Project description:The title compound, C23H22N2O4S, crystallized with two independent mol-ecules (A and B) in the asymmetric unit. They have very similar conformations with the pyrrolidine ring having a twisted conformation, on the Cspiro-Cspiro bond, in both mol-ecules. In mol-ecule A, the mean planes of the benzo-thio-phene and indoline ring systems are inclined to the mean plane of the pyrrolidine ring by 87.59 (10) and 84.51 (11)°, respectively, and to one another by 72.69 (7)°. The corresponding angles in mol-ecule B are 87.15 (10), 84.58 (10) and 72.07 (7)°, respectively. In the crystal, the A and B mol-ecules are linked to one another by two N-H⋯O hydrogen bonds, forming a dimer. These dimers are linked via C-H⋯O hydrogen bonds, forming a three-dimensional structure.

| S-EPMC4350727 | biostudies-literature

Crystal structure of ethyl 2'',3-dioxo-7',7a'-di-hydro-1'H,3H,3'H-di-spiro[benzo[b]thio-phene-2,6'-pyrrolo-[1,2-c]thia-zole-5',3''-indoline]-7'-carboxyl-ate.

Project description:In the title compound, C23H20N2O4S2, the central pyrrolidine ring adopts an envelope conformation with the spiro C atom, shared with the benzo-thio-phene ring system, as the flap. The thia-zole ring has a twisted conformation on the S-C bond, where the C atom is that closest to methine C atom. The mean planes of the benzo-thio-phene and indoline ring systems are inclined to the mean plane of the central pyrrolidine ring by 82.75 (8) and 80.03 (8)°, respectively, and to each other by 61.49 (6)°. In the crystal, mol-ecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif. The dimers are linked via C-H⋯O and C-H⋯N hydrogen bonds, forming a three-dimensional structure. The eth-oxy-carbonyl group is disordered over two orientations, with an occupancy ratio of 0.717 (12):0.283 (12).

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2'-Eth-oxy-1,3,3-trimethyl-spiro-[indoline-2,3'-3H-naphtho-[2,1-b][1,4]oxazine].

Project description:In the title compound, C(24)H(24)N(2)O(2), the five-membered ring of the indoline ring system adopts an envelope conformation with the spiro C atom at the flap. The dihedral angle between the benzene ring of the indoline ring system and the naphthalene ring system is 71.70 (7)°. In the crystal structure, pair of weak C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

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5-Chloro-4'-ethyl-3H-spiro-[1,3-benzo-thia-zole-2,1'-cyclo-hexa-ne].

Project description:In the title compound, C(14)H(18)ClNS, the 2,3-dihydro-1,3-thia-zole ring adopts an envelope with the S,N-bound C atom at the flap and the cyclo-hexane ring adopts a chair conformation. In the crystal, N-H?S hydrogen bonds with C(5) motifs connect the mol-ecules into chains parallel to the c axis.

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Methyl 4-(4-bromo-anilino)-2',5-dioxo-5H-spiro-[furan-2,3'-indoline]-3-carboxyl-ate.

Project description:In the title compound, C19H13BrN2O5, the spiro furan ring is almost planar with a maximum deviation of 0.034 (2) Å. The indole unit and the furan ring are normal to each other, making a dihedral angle of 87.82 (8) °. The mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol-ecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers enclosing R (2) 2(8) ring motifs.

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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

Methyl (3S,3'R)-1-methyl-2,2''-dioxo-1',2',3',5',6',7',8',8a'-octa-hydro-dispiro-[indoline-3,2'-indolizine-3',3''-indoline]-1'-carboxyl-ate.

Project description:In the title compound, C(25)H(25)N(3)O(4), the central pyrrolidine ring and the two pyrrolidine rings adopt twisted conformations, whereas the piperidine ring in the octa-hydro-indolizine fused ring system adopts a chair conformation. The indoline ring systems are almost perpendicular with respect to the mean plane of the octa-hydro-indolizine ring system, making dihedral angles of 84.4?(5) and 79.4?(5)°. The acetate group attached to the octa-hydro-indolizine ring system assumes an extended conformation. In the crystal, N-H?O hydrogen bonds result in the formation of a helical C(7) chain running parallel to [101]. The crystal packing features C-H?O hydrogen bonds and C-H?? inter-actions.

| S-EPMC3470251 | 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

Crystal structure of ethyl (2S,2'R)-1'-benzyl-3-oxo-3H-di-spiro-[1-benzo-thio-phene-2,3'-pyrrolidine-2',11''-indeno[1,2-b]quinoxaline]-4'-carboxyl-ate.

Project description:In the title compound, C35H27N3O3S, the spiro-linked five-membered rings both adopt twisted conformations. The pyrrolidine ring makes dihedral angles of 80.5 (1) and 77.4 (9)° with the benzo-thio-phene ring system and the quinoxaline ring system, respectively. The S atom and C=O unit of the benzo-thio-phene ring system are disordered over two opposite orientations in a 0.768 (4):0.232 (4) ratio. The atoms of the ethyl side chain are disordered over two sets of sites in a 0.680 (16):0.320 (16) ratio. In the crystal, mol-ecules are linked by C-H⋯O, C-H⋯N and π-π inter-actions [shortest centroid-centroid distance = 3.4145 (19) Å], resulting in a three-dimensional network.

| S-EPMC4350717 | biostudies-literature

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