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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.

ABSTRACT: In the title compound, C33H23ClN4O3S·CHCl3, the thia-zole ring adopts an envelope conformation with the N atom as the flap, and the pyrrolidine ring adopts a half-chair conformation. The thia-zole ring mean plane makes a dihedral angle of 59.31?(1)° with the pyrrolidine ring mean plane, 71.67?(1)° with the chromene ring and 82.59?(1)° with the chloro-benzene ring. An intra-molecular C-H?N hydrogen bond occurs. In the crystal, a second C-H?N hydrogen bond links the main and solvent mol-ecules. The solvent chloroform molecule is disordered about two positions with an occupancy ratio of 0.508?(14):0.492?(14).

SUBMITTER: Sivakumar N

PROVIDER: S-EPMC4257185 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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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.

Sivakumar Nithya N Viswanathan Vijayan V Rao Jonnalagadda Naga Siva JN Raghunathan Raghavachary R Velmurugan Devadasan D

Acta crystallographica. Section E, Structure reports online 20140920 Pt 10

In the title compound, C33H23ClN4O3S·CHCl3, the thia-zole ring adopts an envelope conformation with the N atom as the flap, and the pyrrolidine ring adopts a half-chair conformation. The thia-zole ring mean plane makes a dihedral angle of 59.31 (1)° with the pyrrolidine ring mean plane, 71.67 (1)° with the chromene ring and 82.59 (1)° with the chloro-benzene ring. An intra-molecular C-H⋯N hydrogen bond occurs. In the crystal, a second C-H⋯N hydrogen bond links the main and solvent mol-ecules. Th ...[more]

PMID: 25484701

Similar Datasets

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-6a,6b,8,9,10,12a-hexa-hydro-6H,7H-spiro[chromeno[3,4-a]indolizine-12,11'-indeno-[1,2-b]quinoxaline].

Project description:The title compound, C35H27ClN4O3, crystallized with two independent mol-ecules (A and B) in the asymmetric unit. In both mol-ecules, the pyran and pyridine rings adopt envelope and chair conformations, respectively. The conformation of the pyrrolidine and cyclo-pentene rings differ in the two mol-ecules; twisted and flat, respectively, in mol-ecule A, but envelope and twisted, respectively, in mol-ecule B. In both mol-ecules, there is a C-H?N intra-molecular hydrogen bond present. In both mol-ecules, the oxygen atoms of the nitro groups are disordered as is the chlorine atom in mol-ecule B. In the crystal, the B mol-ecules are linked by C-H?O hydrogen bonds, forming -B-B-B- chains along [010], and by C-H?? inter-actions. The A and B mol-ecules are also linked by a number of C-H?? inter-actions, resulting in the formation a supra-molecular three-dimensional structure. In mol-ecule A, the nitro group oxygen atoms are disordered over two positions with refined occupancy ratios of the nitro group oxygen atoms O3A and O4A in 0.59?(2):0.41?(2) while in molecule B one of the nitro O atoms is disordered over two positions with a refined occupancy ratio of 0.686?(13):0.314?(13) and the chlorine atoms is disordered over two positions with a refined occupancy ratio of 0.72?(3):0.28?(3).

| S-EPMC6362633 | biostudies-literature

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

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.

| S-EPMC3685125 | biostudies-literature

6-Ferrocenoyl-7-phenyl-spiro-[hexa-hydro-pyrrolo-[1,2-c][1,3]thia-zole-5,11'-indeno-[1,2-b]quinoxaline].

Project description:In the title compound, [Fe(C5H5)(C32H24N3OS)], both the thia-zolidine ring and the pyrrolidine ring adopt an envelope conformation, with the S atom and the phenyl-bearing C atom, respectively, as the flaps. The thia-zolidine ring mean plane makes a dihedral angle of 59.08?(11)° with the pyrrolidine ring mean plane, which in turn makes a dihedral angle of 83.40?(10)° with the cyclo-pentane ring, indicating that the latter two rings are almost orthogonal to one another. In the crystal, a pair of C-H?O hydrogen bonds link the mol-ecules forming inversion dimers. The dimers are linked via ?-? inter-actions [centroid-centroid distance = 3.7764?(10)?Å] involving the quinoxaline moieties forming chains propagating along [1-10].

| S-EPMC3884422 | biostudies-literature

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.

Project description: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.

| S-EPMC3772479 | biostudies-literature

6-Ferrocenoyl-7-(4-fluoro-phen-yl)spiro-[hexa-hydro-pyrrolo-[1,2-c][1,3]thia-zole-5,11'-indeno-[1,2-b]quinoxaline].

Project description:In the title compound, [Fe(C5H5)(C32H23FN3OS)], both the thia-zolidine ring and the pyrrolidine ring adopt a twist conformation on the N-C(H) bridging bond. Their mean planes are inclined to one another by 10.05?(10)°, and they make dihedral angles of 82.09?(10) and 89.67?(11)°, respectively, with the cyclo-pentane ring. The F atom deviates by -0.0238?(2)?Å from the benzene ring to which it is attached. In the crystal, mol-ecules are linked by a pair of C-H?O hydrogen bonds, forming inversion dimers.

| S-EPMC3884446 | biostudies-literature

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.

Project description:The title compounds, C20H16N2O3S, (I), and C21H18N2O3S, (II), differ by the presence of a methyl group in position 5 on the 1H-indole-2-one ring of compound (II). The two compounds have a structural overlap r.m.s. deviation of 0.48?Å. There is a significant difference in the conformation of the thia-zolidine ring: it has a twisted conformation on the fused N-C bond in (I), but an envelope conformation in compound (II) with the S atom as the flap. The planar pyrrolidine ring of the indole ring system is normal to the mean plane of the five-membered pyrrolidine ring of the pyrrolo-thia-zole unit in both compounds, with dihedral angles of 88.71?(9) and 84.59?(8)°. The pyran rings in both structures have envelope conformations with the methyl-ene C atom adjacent to the C=O group as the flap. In both compounds, there is a short intra-molecular C-H?O contact present. In the crystal of (I), mol-ecules are linked by C-H?O hydrogen bonds forming chains propagating along the b-axis direction. The chains are linked by N-H?? inter-actions, forming layers parallel to (10). In the crystal of (II), mol-ecules are linked by pairs of N-H?O hydrogen bonds, forming inversion dimers which are linked by C-H?O hydrogen bonds to form a three-dimensional structure.

| S-EPMC6362654 | biostudies-literature

2-(4-Bromo-benzo-yl)-1-ferrocenyl-spiro-[11H-pyrrolidizine-3,11'-indeno-[1,2-b]quinoxaline].

Project description:In the title compound, [Fe(C5H5)(C33H25BrN3O)], the fused four-ring system, 11H-indeno-[1,2-b]quinoxaline is essentially planar, with a maximum deviation of 0.087?(3)?Å from the least-squares plane of the attached benzene ring. The pyrrolidine rings adopt envelope conformation and make a dihedral angle of 51.76?(19)° with each other. The cyclopentadiene rings of the ferrocenyl moiety have an eclipsed conformation. The Br atom deviates by 0.0190?(9)?Å from the attached benzene ring. The mol-ecular structure features an intra-molecular C-H?N inter-action, which generates an S(8) ring motif. The crystal packing features C-H?O inter-actions, which generate R 2 (2)(18) centrosymmetric dimers, as well as C-H?? inter-actions.

| S-EPMC3884418 | biostudies-literature

4-Ferrocenyl-1-methyl-3-benzoyl-spiro-[pyrrolidine-2,11'-indeno-[1,2-b]quinoxaline].

Project description:In the title compound, [Fe(C5H5)(C31H24N3O)], the pyrrolidine ring adopts a twist conformation. The pyrrolidine ring is almost perpendicular to the indeno-quinoxaline ring system, making a dihedral angle of 84.44?(5)°. The cyclo-penta-dienyl rings of the ferrocene moiety adopt an eclipsed conformation. The crystal packing features weak C-H?N and C-H?? inter-actions.

| S-EPMC3588807 | biostudies-other

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