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6-(4-Meth-oxy-phen-yl)-6a-nitro-6,6a,6b,7,8,9,10,12a-octa-hydro-spiro-[chromeno[3,4-a]indolizine-12,3'-indolin]-2'-one.

ABSTRACT: In the title compound, C29H27N3O5, the hydropyran ring adopts an envelope conformation with the methine C atom bearing the para-meth-oxy-benzene ring as the flap. The central pyrrolidine ring has a twist conformation on the N-C bond involving the spiro C atom. The piperidine ring adopts a chair conformation. An intra-molecular C-H?O contact closes an S(7) ring. In the crystal, inversion dimers linked by C-H?O inter-actions generate R 2 (2)(18) loops and N-H?O hydrogen bonds connect the dimers into [100] chains.

SUBMITTER: Devi SK

PROVIDER: S-EPMC3772479 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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6-(4-Meth-oxy-phen-yl)-6a-nitro-6,6a,6b,7,8,9,10,12a-octa-hydro-spiro-[chromeno[3,4-a]indolizine-12,3'-indolin]-2'-one.

Devi Seenivasan Karthiga SK Srinivasan Thothadri T Rao Jonnalagadda Naga Siva JN Raghunathan Raghavachary R Velmurugan Devadasan D

Acta crystallographica. Section E, Structure reports online 20130608 Pt 7

In the title compound, C29H27N3O5, the hydropyran ring adopts an envelope conformation with the methine C atom bearing the para-meth-oxy-benzene ring as the flap. The central pyrrolidine ring has a twist conformation on the N-C bond involving the spiro C atom. The piperidine ring adopts a chair conformation. An intra-molecular C-H⋯O contact closes an S(7) ring. In the crystal, inversion dimers linked by C-H⋯O inter-actions generate R 2 (2)(18) loops and N-H⋯O hydrogen bonds connect the dimers in ...[more]

PMID: 24046622

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6a-Nitro-6-phenyl-6,6a,6b,7,8,9,10,12a-octa-hydro-spiro-[chromeno[3,4-a]indol-izine-12,3'-indolin]-2'-one.

Project description:In the title compound, C28H25N3O4, the central pyrrolidine ring adopts adopts an envelope conformation with the N atom as the flap and the piperidine ring adopts a chair conformation. The pendant pyrrolidine ring is almost planar (r.m.s. deviation = 0.008 Å). An intra-molecular C-H⋯O inter-action closes an S(6) ring. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R 2 (2)(8) loops.

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The crystal structures and Hirshfeld surface analysis of 6-(naphthalen-1-yl)-6a-nitro-6,6a,6b,7,9,11a-hexa-hydro-spiro-[chromeno[3',4':3,4]pyrrolo-[1,2-c]thia-zole-11,11'-indeno-[1,2-b]quinoxaline] and 6'-(naphthalen-1-yl)-6a'-nitro-6',6a',6b',7',8',9',10',12a'-octa-hydro-2H-spiro-[ace-naphthyl-ene-1,12'-chromeno[3,4-a]indolizin]-2-one.

Project description:The title compounds, 6-(naphthalen-1-yl)-6a-nitro-6,6a,6 b,7,9,11a-hexa-hydro-spiro-[chromeno[3',4':3,4]pyrrolo-[1,2-c]thia-zole-11,11'-indeno-[1,2-b]quinoxaline], C37H26N4O3S, (I), and 6'-(naphthalen-1-yl)-6a'-nitro-6',6a',6b',7',8',9',10',12a'-octa-hydro-2H-spiro-[ace-naphthyl-ene-1,12'-chromeno[3,4-a]indolizin]-2-one, C36H28N2O4, (II), are new spiro derivatives, in which both the pyrrolidine rings adopt twisted conformations. In (I), the five-membered thia-zole ring adopts an envelope conformation, while the eight-membered pyrrolidine-thia-zole ring adopts a boat conformation. An intra-molecular C-H⋯N hydrogen bond occurs, involving a C atom of the pyran ring and an N atom of the pyrazine ring. In (II), the six-membered piperidine ring adopts a chair conformation. An intra-molecular C-H⋯O hydrogen bond occurs, involving a C atom of the pyrrolidine ring and the keto O atom. For both compounds, the crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonds. In (I), the C-H⋯O hydrogen bonds link adjacent mol-ecules, forming R 2 2(16) loops propagating along the b-axis direction, while in (II) they form zigzag chains along the b-axis direction. In both compounds, C-H⋯π inter-actions help to consolidate the structure, but no significant π-π inter-actions with centroid-centroid distances of less than 4 Å are observed.

| S-EPMC6775748 | biostudies-literature

Crystal structure of 6-(4-chloro-phen-yl)-6a-nitro-6,6a,6b,7,9,11a-hexa-hydro-spiro[chromeno[3',4':3,4]pyrrolo-[1,2-c]thia-zole-11,11'-indeno-[1,2-b]quinoxaline] chloro-form monosolvate.

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| S-EPMC4257185 | biostudies-literature

Crystal structure of 6-(4-chloro-phen-yl)-6a-nitro-6a,6b,8,9,10,12a-hexa-hydro-6H,7H-spiro[chromeno[3,4-a]indolizine-12,11'-indeno-[1,2-b]quinoxaline].

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Crystal structures of 6a,6b,7,11a-tetra-hydro-6H,9H-spiro-[chromeno[3',4':3,4]pyrrolo-[1,2-c]thia-zole-11,3'-indoline]-2',6-dione and 5'-methyl-6a,6b,7,11a-tetra-hydro-6H,9H-spiro-[chromeno[3',4':3,4]pyrrolo-[1,2-c]thia-zole-11,3'-indoline]-2',6-dione.

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| S-EPMC6362654 | biostudies-literature

Methyl 9-(4-bromo-phen-yl)-8a,9,9a,10,11,12,13,14a-octa-hydro-8H-benzo[f]chromeno[3,4-b]indolizine-8a-car-box-ylate.

Project description:In the title compound, C(27)H(26)BrNO(3), the mean plane of the naphthalene ring system makes a dihedral angle of 22.0?(1)° with the bromo-substituted benzene ring. The pyrrolidine and piperidine rings exhibit envelope and chair conformations, respectively. An inter-molecular C-H?Br inter-action is observed.

| S-EPMC2970191 | biostudies-literature

2-Methyl-4-(naphthalen-2-yl)-3a-nitro-3,3a,4,9b-tetra-hydro-2H-spiro-[chromeno[3,4-c]pyrrole-1,3'-indolin]-2'-one.

Project description:In the title compound, C29H23N3O4, the 2-methylpyrrolidine ring adopts a twist conformation on the N-C bond involving the spiro C atom, while the hydropyran ring adopts an envelope conformation with the methine C atom bonded to the O atom as the flap. The mean plane of the indoline-2-one ring system is almost perpendicular to the mean plane of the pyrrolidine ring, making a dihedral angle of 89.73 (8)°. The latter ring makes dihedral angles of 47.80 (8) with the naphthalene ring system and 32.38 (8)° with the hydropyran ring mean plane. There is an intra-molecular C-H⋯O hydrogen bond involving the indoline-2-one O atom. In the crystal, adjacent mol-ecules are linked via N-H⋯O hydrogen bonds, forming chains propagating along [100]. The chains are linked via weak C-H⋯O hydrogen bonds, forming two-dimensional networks, lying parallel to (101), and consolidated by C-H⋯π inter-actions.

| S-EPMC3772478 | biostudies-literature

Methyl 9-p-tolyl-8a,9,9a,10,11,12,13,14a-octa-hydro-8H-benzo[f]chromeno[3,4-b]indolizine-8a-carboxyl-ate.

Project description:In the title compound, C(28)H(29)NO(3), the fused pyrrolidine and piperidine rings of the octa-hydro-indolizine unit exhibit envelope and chair conformations, respectively. The dihedral angle between the naphthalene ring system and the benzene ring is 40.37?(5)°. The crystal packing is stabilized by weak inter-molecular C-H?O inter-actions.

| S-EPMC2972086 | biostudies-other

6a-Nitro-6-(2,2,7,7-tetra-methyl-tetra-hydro-3aH-bis-[1,3]dioxolo[4,5-b:4',5'-d]pyran-5-yl)-6a,6b,7,8,9,11a-hexa-hydro-6H-spiro-[chromeno[3,4-a]pyrrolizine-11,11'-indeno-[1,2-b]quinoxaline].

Project description:In the title compound, C39H38N4O8, the quinoxaline and indene subunits are essentially planar, with maximum deviations of 0.071?(2) and 0.009?(2)?Å, respectively. The indeno-quinoxaline system forms a dihedral angle of 72.81?(3)° with the chromenopyrrolizine system. The two dioxolane rings, as well as the pyran ring of the chromeno group and the terminal pyrrolizine, each adopt an envelope conformation with O and C as flap atoms. The central pyrrolizine ring adopts a twisted conformation. Intra-molecular C-H?O and C-H?N hydrogen bonds occur. The crystal structure exhibits C-H?O hydrogen bonds, and is further stablized by C-H?? inter-actions, forming a two-dimensional network along the bc plane.

| S-EPMC3914082 | biostudies-other

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.

Project description: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.

| S-EPMC4571432 | biostudies-literature

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