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(3aR,6S,7aR)-7a-Chloro-6-methyl-2-(4-nitro-phenyl-sulfon-yl)-1,2,3,6,7,7a-hexa-hydro-3a,6-ep-oxy-iso-indole.

ABSTRACT: In the title compound, C15H15ClN2O5S, the tetra-hydro-furan ring adopts an envelope conformation with the O atom as the flap. The pyrrolidine ring adopts an envelope conformation with the chlorine-substituted C atom as the flap. In the crystal, two types of C-H?O hydrogen bonds generate R (2) 2(20) and R (4) 4(26) rings, with adjacent rings running parallel to ac plane. Further C-H?O hydrogen bonds form a C(6) chain, linking the mol-ecules in the b-axis direction.

SUBMITTER: Demircan A

PROVIDER: S-EPMC3884300 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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(3aR,6S,7aR)-7a-Chloro-6-methyl-2-(4-nitro-phenyl-sulfon-yl)-1,2,3,6,7,7a-hexa-hydro-3a,6-ep-oxy-iso-indole.

Demircan Aydın A Temel Ersin E Kandemir Muhammet Kasım MK Colak Medine M Büyükgüngör Orhan O

Acta crystallographica. Section E, Structure reports online 20131009 Pt 11

In the title compound, C15H15ClN2O5S, the tetra-hydro-furan ring adopts an envelope conformation with the O atom as the flap. The pyrrolidine ring adopts an envelope conformation with the chlorine-substituted C atom as the flap. In the crystal, two types of C-H⋯O hydrogen bonds generate R (2) 2(20) and R (4) 4(26) rings, with adjacent rings running parallel to ac plane. Further C-H⋯O hydrogen bonds form a C(6) chain, linking the mol-ecules in the b-axis direction. ...[more]

PMID: 24454076

Similar Datasets

(3aR,6S,7aR)-7a-Chloro-2-[(4-nitro-phen-yl)sulfon-yl]-1,2,3,6,7,7a-hexa-hydro-3a,6-ep-oxy-iso-indole.

Project description:In the title compound, C14H13ClN2O5S, the chlorine-substituted tetrahydrofuran ring adopts a twist conformation and the other tetra-hydro-furan ring an envelope conformation with the O atom as the flap. The pyrrolidine ring adopts a twist conformation. In the crystal, C-H?O hydrogen bonds link the mol-ecules into zigzag chains running along the b-axis direction.

| S-EPMC3790416 | biostudies-literature

(3aR,6S,7aR)-7a-Bromo-2-[(4-methyl-phen-yl)sulfon-yl]-1,2,3,6,7,7a-hexa-hydro-3a,6-ep-oxy-isoindole.

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(3aR,6S,7aR)-7a-Bromo-2-methyl-sulfonyl-1,2,3,6,7,7a-hexa-hydro-3a,6-ep-oxy-isoindole.

Project description:In the title compound, C(9)H(12)BrNO(3)S, the two tetra-hydro-furan rings adopt envelope conformations, the pyrrolidine ring adopts a half-chair conformation and the six-membered ring is in a boat conformation. In the crystal, weak inter-molecular C-H?O hydrogen bonds link the mol-ecules into R(2) (2)(8) and R(2) (2)(14) rings along the b-axis direction.

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(3aR*,6S*,7S*,7aR*)-2-(4-Methoxy-benz-yl)-7-(4-nitro-phen-yl)-6-phenyl-3a,6,7,7a-tetra-hydro-isoindolin-1-one.

Project description:The title compound, C(28)H(26)N(2)O(4), crystallizes as a racemate with four stereogenic centers. In the molecule, the pyrrolidone ring adopts an envelope conformation and the cyclo-hexene ring has a twisted envelope conformation. In the crystal structure, mol-ecules are linked by weak inter-molecular C-H?O hydrogen bonds.

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rac-Methyl (3aR*,4S*,5R*,7aR*)-5,7a-bis-(acet-yloxy)-3-oxo-2-phenyl-octa-hydro-1H-iso-indole-4-carboxyl-ate.

Project description:The title molecule, C20H23NO7, the product of nucleophilic cleavage of the 3a,6-ep-oxy bridge in 1-oxo-2-phenyl-octa-hydro-3a,6-ep-oxy-iso-indole-7-carboxyl-ate, comprises a cis-fused bicyclic system containing a 2-pyrrolidinone ring in an envelope conformation (with the C atom bearing the carboxyl-ate substituent as the flap) and a cyclo-hexane ring in a chair conformation. The carboxyl-ate substituent occupies the equatorial position, whereas the two acet-yloxy substituents are in axial positions. The N atom has a trigonal-planar geometry, the sum of the bond angles being 359.3?(3)°. The dihedral angle between the mean plane of the four planar atoms of the pyrrolidinone ring and the phenyl ring is 25.98?(6)°. In the crystal, mol-ecules are linked into zigzag chains along the c-axis direction by C-H?O hydrogen bonds.

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(3aR,4S,7R,7aS)-2-Phenyl-4-propyl-3a,4,7,7a-tetra-hydro-1H-4,7-epithio-iso-indole-1,3-dione 8-oxide.

Project description:In the tetra-hydro-isoindole moiety of the title compound, C(17)H(17)NO(3)S, the six-membered ring assumes a boat configuration and the -S=O group bridges the prow and stern of the boat. The phenyl ring is oriented at a dihedral angle of 83.2?(1)° with respect to the pyrrole ring. In the crystal, inter-molecular C-H?O hydrogen bonds link the mol-ecules into a three-dimensional network. A weak C-H?? inter-action involving the phenyl ring is also found. The crystal studied was an inversion twin.

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(3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-2-phenyl-4,6-methano-1,3,2-benzodioxaborole.

Project description:The mol-ecule of the title compound, C(16)H(21)BO(2), comprises a chiral fused tricyclic system containing five-membered (1,3,2-dioxaborolane), six-membered (cyclo-hexa-ne) and four-membered (cyclo-butane) rings. The 1,3,2-dioxaborolane ring is almost planar (r.m.s. deviation = 0.035?Å), and the syn H and Me substituents at this ring are in an eclipsed conformation. The cyclo-hexane and cyclo-butane rings adopt sofa and butterfly conformations, respectively. The B atom has a trigonal-planar configuration (sum of the bond angles = 360.0°). The phenyl ring is practically coplanar with the 1,3,2-dioxaborolane ring [dihedral angle between the ring planes = 1.96?(8)°]. The absolute structure was determined from the known configuration of (+)-pinanediol which was used in the synthesis. In the crystal, weak C-H??(Ph) inter-actions occur.

| S-EPMC3515203 | biostudies-other

Crystal structure of rac-(3aR,4S,5aR,6S,9R,10aS,10bR)-3a,5a,9-tri-methyl-tetra-deca-hydro-6,9-ep-oxy-cyclo-hepta-[e]inden-4-ol monohydrate.

Project description:The title hydrate, C17H28O2·H2O, was synthesized in order to determine the relative configuration of the tetra-cyclic framework. The fused 5,6,7-tricarbocyclic core exhibits an entire cis-annulation, featuring a 1,4-cis-relation of the angular methyl groups in the six-membered ring. The oxa bridge of the ep-oxy-cyclo-heptane moiety is oriented towards the concave face of the boat-shaped mol-ecule, whereas the angular methyl groups are directed towards the convex face. The asymmetric unit of the crystal contains two nearly identical formula units, which are related via a pseudo-centre of symmetry. The structure could be solved in the space groups I-4 and I41/a. The refinement in the acentric space group, however, gave significantly better results and these are used in this paper. O-H⋯O hydrogen bonds are observed between the organic mol-ecules, between the organic mol-ecules and the water mol-ecules, and between the water mol-ecules, forming a chain along the c-axis direction.

| S-EPMC4555390 | biostudies-literature

Crystal structure of the thalidomide analog (3aR*,7aS*)-2-(2,6-dioxopiperidin-3-yl)hexa-hydro-1H-iso-indole-1,3(2H)-dione.

Project description:The title compound, C13H16N2O4, crystallizes in the monoclinic centrosymmetric space group, P21/c, with four mol-ecules in the asymmetric unit, thus there is no crystallographically imposed symmetry and it is a racemic mixture. The structure consists of a six-membered unsaturated ring bound to a five-membered pyrrolidine-2,5-dione ring N-bound to a six-membered piperidine-2,6-dione ring and thus has the same basic skeleton as thalidomide, except for the six-membered unsaturated ring substituted for the aromatic ring. In the crystal, the mol-ecules are linked into inversion dimers by R 2 2(8) hydrogen bonding involving the N-H group. In addition, there are bifurcated C-H?O inter-actions involving one of the O atoms on the pyrrolidine-2,5-dione with graph-set notation R 1 2(5). These inter-actions along with C-H?O inter-actions involving one of the O atoms on the piperidine-2,6-dione ring link the mol-ecules into a complex three-dimensional array. There is pseudomerohedral twinning present which results from a 180° rotation about the [100] reciprocal lattice direction and with a twin law of 1 0 0 0 0 0 0 [BASF 0.044?(1)].

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