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.

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.

Crystal structure of methyl 3-(3-fluoro-phen-yl)-1-methyl-1,3a,4,9b-tetra-hydro-3H-thio-chromeno[4,3-c]isoxazole-3a-carboxyl-ate.

In the title compound, C19H18FNO3S, the five-membered oxazolidine ring adopts an envelope conformation with the methine C atom of the fused bond as the flap. Its mean plane is oriented at a dihedral angle of 50.38 (1)° with respect to the fluoro-phenyl ring. The six-membered thio-pyran ring has a half-chair conformation and its mean plane is almost coplanar with the fused benzene ring, making a dihedral angle of 4.94 (10)°. The two aromatic rings are inclined to one another by 85.96 (11)°, and the mean planes of the oxazolidine and thio-pyran rings are inclined to one another by 57.64 (12)°. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming a three-dimensional structure.

Crystal structure of methyl 7-phenyl-6a,7,7a,8,9,10-hexa-hydro-6H,11aH-thio-chromeno[3,4-b]pyrrolizine-6a--carbox-ylate.

In the title compound, C22H23NO2S, the inner pyrrolidine ring (A) adopts an envelope conformation with the methine C atom opposite the fused C-N bond as the flap. The thio-pyran ring (C) has a half-chair conformation and its mean plane is inclined to the fused benzene ring by 1.74 (11)°, and by 60.52 (11)° to the mean plane of pyrrolidine ring A. In the outer pyrrolidine ring (B), the C atom opposite the fused C-N bond is disordered [site-occupancy ratio = 0.427 (13):0.573 (13)] and both rings have envelope conformations, with the disordered C atom as the flap. The planes of the phenyl ring and the benzene ring of the thio-chromane unit are inclined to one another by 65.52 (14)°. In the crystal, mol-ecules are linked by a pair of C-H⋯O hydrogen bonds forming inversion dimers.

Crystal structure of 14-methyl-11-(3-methyl-phen-yl)-12-oxa-8,14-di-aza-tetra-cyclo-[8.3.3.0(1,10).0(2,7)]hexa-deca-2(7),3,5-triene-9,13-dione.

In the title compound, C21H20N2O3, the lactone ring adopts an envelope conformation with the quaternary C atom bonded to two other C atoms as the flap. The fused pyrrolidine ring adopts a twisted conformation about the Cq-N (q = quaternary) bond. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R 2 (2)(8) loops. The dimers are linked into [110] chains by pairs of C-H⋯O inter-actions, which generate R 2 (2)(14) loops.

Crystal structure of methyl 1-methyl-2-oxo-spiro-[indoline-3,2'-oxirane]-3'-carboxyl-ate.

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.

Crystal structure of 11-(2,3-di-meth-oxy-phen-yl)-14-methyl-12-oxa-8,14-di-aza-tetra-cyclo-[8.3.3.0(1,10).0(2,7)]hexa-deca-2(7),3,5-triene-9,13-dione.

The title compound, C22H22N2O5, contains two conformationally similar mol-ecules (A and B) in its the asymmetric unit (r.m.s. overlay fit for the 29 non-H atoms = 0.194 Å). In each mol-ecule, the lactone ring has an envelope conformation with the spiro C atom as the flap. In the crystal, A+A and B+B inversion dimers linked by pairs of N-H⋯O hydrgen bonds occur; in both cases, R 2 (2)(8) loops are generated. A weak C-H⋯O inter-action is also observed, which links the dimers into [010] chains.

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.

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].

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.

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).

Crystal structure of 15-(naphthalen-1-yl)-7,7a,8,9,10,11-hexa-hydro-6a,12a-(methano-epoxy-methano)-indolizino[2,3-c]quinoline-6,13(5H)-dione.

In the title compound, C27H24N2O3, the dihedral angle between the mean planes of the di-hydro-furan and 3,4-di-hydro-quinoline ring systems is 70.65 (9)°. The di-hydro-furan ring adopts an envelope conformation with the C atom adjacent to the methyl-ene C atom of the pyrrolidine ring as the flap. The five-membered pyrrolidine ring adopts a twist conformation on the N-C(tetra-substituted) bond. 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 pairs of C-H⋯O hydrogen bonds, forming ribbons enclosing R 2 (2)(12) ring motifs lying in a plane parallel to (01-1).

Crystal structure of methyl (E)-2-(1-methyl-2-oxoindolin-3-yl-idene)acetate.

The title compound, C12H11NO3, is essentially planar, with the mean plane of the acetate side chain [-C-C(=O)-O-C] being inclined to the mean plane of the indole ring system by 12.49 (7)°. The five- and six-membered rings of the indole group are almost coplanar, making a dihedral angle of 1.76 (8)°. The conformation about the C=C bond is E and there is an intra-molecular C-H⋯O hydrogen bond present. In the crystal, mol-ecules are linked by pairs of C-H⋯O hydrogen bonds forming inversion dimers, with an R 2 (2)(16) ring motif. The dimers are linked by a second pair of C-H⋯O hydrogen bonds, enclosing R 2 (2)(16) ring motifs, forming ribbons lying parallel to (-114). The ribbons are linked via C-H⋯π inter-actions, forming a three-dimensional structure.

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.

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 Šfor (I) and (II), respectively] and the benzo-thio-phene ring systems (r.m.s. deviations = 0.019 and 0.034 Šfor (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].