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1-Benzyl-2-(1H-indol-3-yl)-5-oxo-pyrrolidine-2-carbonitrile.

ABSTRACT: In the title compound, C(20)H(17)N(3)O, a potential anti-human immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse-transcriptase inhibitor, the pyrrolidine ring has an envelope conformation. In the crystal structure, adjacent mol-ecules are connected into infinite chains via an N-H?O hydrogen bond.

SUBMITTER: Tamazyan R

PROVIDER: S-EPMC2960201 | biostudies-literature | 2008 Jan

REPOSITORIES: biostudies-literature

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1-Benzyl-2-(1H-indol-3-yl)-5-oxo-pyrrolidine-2-carbonitrile.

Tamazyan Rafael R Armen Ayvazyan A Ashot Martirosyan M Sahak Gasparyan G Schinazi Raymond R

Acta crystallographica. Section E, Structure reports online 20080104 Pt 2

In the title compound, C(20)H(17)N(3)O, a potential anti-human immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse-transcriptase inhibitor, the pyrrolidine ring has an envelope conformation. In the crystal structure, adjacent mol-ecules are connected into infinite chains via an N-H⋯O hydrogen bond. ...[more]

PMID: 21201400

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

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

Project description: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).

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4-(4-Bromo-phen-yl)-6-(1H-indol-3-yl)-2,2'-bipyridine-5-carbonitrile.

Project description:In the title compound, C(25)H(15)BrN(4), the two pyridine rings lie in a common plane [r.m.s. deviation = 0.023?(2)?Å], whereas the bromo-phenyl and indole rings are twisted away from this plane by 52.82?(12) and 28.02?(10)°, respectively. The crystal structure is stabilized by inter-molecular N-H?N inter-actions.

| S-EPMC2968551 | biostudies-literature

4-(2,4-Dichloro-phen-yl)-6-(1H-indol-3-yl)-2,2'-bipyridine-5-carbonitrile.

Project description:The title compound, C(25)H(14)Cl(2)N(4), crystallizes with two independent mol-ecules in the asymmetric unit. The two pyridine rings are almost coplanar, making dihedral angles of 3.2?(1) and 8.6?(1)° in the two independent mol-ecules. The dichloro-phenyl and indole rings are twisted away from the bipyridine ring by 64.32?(5) and 18.46?(4)°, respectively in the first molecule and by 51.0?(1) and 27.99?(5)°, respectively in the second molecule. The crystal packing is stabilized by C-H?N, C-H?Cl, N-H?N and C-H?? inter-actions.

| S-EPMC2977688 | biostudies-literature

Benzyl N-[2-(1H-indol-3-yl)eth-yl]dithio-carbamate.

Project description:The indole and phenyl ring systems in the title compound, C(18)H(18)N(2)S(2), are nearly coplanar, the indole and phenyl planes forming a dihedral angle of 6.5?(1)°. Supra-molecular aggregation is effected by N-H?S, C-H?S, N-H?? and C-H?? inter-actions. The crystal studied exhibited inversion twinning.

| S-EPMC2915340 | biostudies-literature

6-(1H-Indol-3-yl)-4-phenyl-2,2'-bi-pyridine-5-carbonitrile.

Project description:In the mol-ecule of the title compound, C(25)H(16)N(4), the pyridine rings are oriented at a dihedral angle of 0.92?(3)°, while the dihedral angle between the benzene ring and the adjacent pyridine ring is 56.51?(3)°. In the crystal structure, inter-molecular N-H?N hydrogen bonds link the mol-ecules into centrosymmetric dimers, forming R(2) (2)(16) ring motifs. ?-? contacts between the pyridine ring and the indole ring system and between the pyridine rings [centroid-centroid distances = 3.923?(2) and 3.724?(2)?Å] may further stabilize the structure. Two weak C-H?? inter-actions are also present.

| S-EPMC2969709 | biostudies-literature

3-Oxo-5-(piperidin-1-yl)-2,3-dihydro-1H-pyrazole-4-carbonitrile.

Project description:In the title compound, C(9)H(12)N(4)O, the piperidine ring adopts a chair conformation and makes a dihedral angle of 42.49 (11)° with the approximately planar pyrazole moiety [maximum deviation = 0.038 (2) Å]. In the crystal, N-H⋯O and N-H⋯N hydrogen bonds and a weak C-H⋯O inter-action link the mol-ecules into sheets lying parallel to (110).

| S-EPMC3238968 | 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

Diethyl 2-oxo-3-(2-oxo-2,3-dihydro-1H-indol-3-yl-idene)butane-dioate.

Project description:The title compound, C(16)H(15)NO(6), crystallizes with two symmetry-independent mol-ecules in the asymmetric unit. The crystal structure is stabilized by inter-molecular C-H?O and N-H?O hydrogen bonds, and intra-molecular C-H?O hydrogen bonds. In addition, the crystal structure exhibits two inter-molecular C-H?? inter-actions.

| S-EPMC2980112 | biostudies-literature

5-Benzoyl-2-(1H-indol-3-yl)-4-(4-methyl-phen-yl)-4,5-dihydro-furan-3-carbonitrile.

Project description:The furan ring in the title compound, C(27)H(20)N(2)O(2), adopts a twisted conformation about the sp(3)-sp(3) bond. The mol-ecular structure is stabilized by an intra-molecular C-H?O inter-action which generates an S(6) ring motif. The crystal packing is stabilized by N-H?O and C-H?O inter-actions generating centrosymmetric R(2) (2)(18) and C(6) chain motifs, respectively. A weak C-H?? inter-action is also observed.

| S-EPMC3344070 | biostudies-literature

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