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Methyl 4,5-diacet-oxy-1-oxo-2-phenyl-perhydro-4,6-epoxy-cyclo-penta-[c]pyridine-7-carboxyl-ate ethanol solvate.

ABSTRACT: The title compound, the product of an acid-catalysed Wagner-Meerwein skeletal rearrangement, crystallizes as an ethanol monosolvate, C(20)H(21)NO(8)·C(2)H(6)O. The title mol-ecule comprises a fused tricyclic system containing two five-membered rings (cyclo-pentane and tetra-hydro-furan) in the usual envelope conformations and one six-membered ring (piperidinone) adopting a flattened twist-boat conformation.

SUBMITTER: Gurbanov AV

PROVIDER: S-EPMC2971959 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature

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Methyl 4,5-diacet-oxy-1-oxo-2-phenyl-perhydro-4,6-epoxy-cyclo-penta-[c]pyridine-7-carboxyl-ate ethanol solvate.

Gurbanov Atash V AV Nikitina Eugeniya V EV Airiyan Inga K IK Zaytsev Vladimir P VP Khrustalev Victor N VN

Acta crystallographica. Section E, Structure reports online 20091104 Pt 12

The title compound, the product of an acid-catalysed Wagner-Meerwein skeletal rearrangement, crystallizes as an ethanol monosolvate, C(20)H(21)NO(8)·C(2)H(6)O. The title mol-ecule comprises a fused tricyclic system containing two five-membered rings (cyclo-pentane and tetra-hydro-furan) in the usual envelope conformations and one six-membered ring (piperidinone) adopting a flattened twist-boat conformation. ...[more]

PMID: 21578721

Similar Datasets

Methyl 7,8-diacet-oxy-11-oxo-5-(2-oxo-pyrrolidin-1-yl)-7,9-epoxy-cyclo-penta-[4,5]pyrido[1,2-a]quinoline-10-carboxyl-ate sesquihydrate.

Project description:The title compound, C(26)H(28)N(2)O(9)·1.5H(2)O, the product of an acid-catalysed Wagner-Meerwein skeletal rearrangement, crystallizes as a sesquihydrate with the O atom of one of the two independent water mol-ecules occupying a special position on a twofold axis. The organic mol-ecule comprises a fused penta-cyclic system containing two five-membered rings (cyclo-pentane and tetra-hydro-furan) and three six-membered rings (piperidinone, tetra-hydro-pyridine and benzene). The five-membered rings have the usual envelope conformations, and the central six-membered piperidinone and tetra-hydro-pyridine rings adopt boat and sofa conformations, respectively. In the crystal, there are three independent O-H⋯O hydrogen bonds, which link the organic mol-ecules and water mol-ecules into complex two-tier layers parallel to (001). The layers are further linked into a three-dimensional framework by attractive inter-molecular carbon-yl-carbonyl inter-actions.

| S-EPMC2980137 | biostudies-literature

Methyl 4,6-bis-(4-fluoro-phen-yl)-2-oxo-cyclo-hex-3-ene-1-carboxyl-ate.

Project description:The 3-cyclo-hexene units adopt envelope conformations in each of the two independent mol-ecules that comprise the asymmetric unit of the title compound, C(20)H(16)F(2)O(3). The dihedral angles between the two fluoro-phenyl rings are 79.7 (2) and 73.7 (2)° in the two mol-ecules. In one of the mol-ecules, two C-H groups of the cyclo-hexene ring are disordered over two sets of sites in a 0.818 (13):0.182 (13) ratio, the major and minor components corresponding to the two enanti-omeric forms of the mol-ecule. Weak inter-molecular C-H⋯O inter-actions help to stabilize the crystal structure.

| S-EPMC2983895 | biostudies-literature

8b,8c-Diphenyl-2,6-bis(4-pyridyl-meth-yl)-perhydro-2,3a,4a,6,7a,8a-hexa-aza-cyclo-penta-[def]fluorene-4,8-dithione chloro-form solvate.

Project description:In the thio-glycoluril system of the title compound, C(32)H(30)N(8)S(2)·CHCl(3), the two pyridine rings are roughly parallel, forming a dihedral angle of 7.2 (1)°, and the distance between the centroids of the two phenyl rings is 3.951 (5) Å. The chloro-form solvent mol-ecule is linked to the main mol-ecule via a weak C-H⋯N hydrogen bond.

| S-EPMC3006766 | biostudies-literature

Ethyl 5-hy-droxy-6-oxo-4-phenyl-5,6-dihydro-4H-cyclo-penta-[b]thio-phene-5-carboxyl-ate.

Project description:In the title mol-ecule, C(16)H(14)O(4)S, the dihydro-cyclo-penta-thio-phenone ring system is almost planar, with an r.m.s. deviation of 0.060 Å from the best fit plane through all nine non-H atoms. The cyclo-penta-none ring adopts a severely flattened envelope conformation with the C atom carrying the OH and ethylcarboxylate substituents at the flap. This atom lies only 0.185 (3) Å from the plane through the other four C atoms. The phenyl substituent is inclined at 43.37 (5)° to the dihydro-cyclo-penta-thio-phenone mean plane. In the crystal, mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming inversion dimers with R(2) (2)(10) ring motifs. Weak C-H⋯O hydrogen bonds also link mol-ecules into chains along c, while an approximately orthogonal set of C-H⋯O contacts form chains along b, resulting in layers lying parallel to (100). Inversion dimers also form through weaker R(2) (2)(12) C-H⋯S contacts, which combine with C-H⋯O contacts to form stacks along b.

| S-EPMC3201281 | biostudies-literature

Methyl 9-hy-droxy-15-methyl-2-oxo-11-(pyren-1-yl)-10-oxa-15-aza-tetra-cyclo-[7.6.0.0(1,12).0(3,8)]penta-deca-3(8),4,6-triene-12-carboxyl-ate.

Project description:In the title compound, C32H25NO5, the furan and pyrrole rings each adopt an envelope conformation, the respective flap atoms being the C atom bearing the pyrene substituent and the CH2 atom adjacent to the N atom. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond. In the crystal, C-H⋯O contacts link the mol-ecules, forming a two-dimensional network parallel to (001).

| S-EPMC3790429 | biostudies-literature

4,5-Dihydro-cyclo-penta-[b]thio-phen-6-one.

Project description:The title compound, C(7)H(6)OS, crystallizes with two similar mol-ecules, 1 and 2, in the asymmetric unit. Both mol-ecules are essentially planar with r.m.s. deviations of 0.0193 and 0.0107 Å for the planes through the nine non-H atoms of mol-ecules 1 and 2, respectively. The thio-phene and 4,5-dihydro-cyclo-penta-dienone rings are inclined at 2.40 (13)° in 1 and 0.64 (13)° in 2. In the crystal structure π-π [3.6542 (17) Å] and C-H⋯π contacts stack the mol-ecules into columns in an inverse fashion along the b axis. An extensive series of C-H⋯O hydrogen bonds links the columns, generating an extended network structure.

| S-EPMC3275050 | biostudies-literature

Bis(2-cyclo-hexyl-imino-methyl-4,6-disulfanylphenolato)nickel(II) acetonitrile solvate.

Project description:In the title compound, [Ni(C(13)H(16)NOS(2))(2)]·CH(3)CN, the Ni(II) atom is four-coordinated by two N,O-bidentate Schiff base ligands, resulting in a distorted tetra-hedral coordination for the metal ion.

| S-EPMC2970037 | biostudies-literature

Dichlorido(9-methyl-adenine-κN)(η-penta-methyl-cyclo-penta-dien-yl)iridium(III) dichloromethane solvate.

Project description:In the title complex, [Ir(C(10)H(15))Cl(2)(C(6)H(7)N(5))]·CH(2)Cl(2) or [Ir(η(5)-C(5)Me(5))Cl(2)(9-MeAde-κN(7))]·CH(2)Cl(2) (9-MeAde = 9-methyl-adenine), the coordination geometry of the Ir(III) atom approximates to a three-legged piano stool. The 9-methyl-adenine ligand is coordinated in a monodentate fashion to the Ir centre through its N-7 atom. The crystal structure contains centrosymmetric pairs of mol-ecules, inter-acting through two N-H⋯N hydrogen bonds. An intra-molecular N-H⋯Cl hydrogen bond is formed between the H atom of an NH(2) group and a chlorido ligand. Further short intra- and inter-molecular C-H⋯Cl contacts are observed.

| S-EPMC2960857 | biostudies-literature

Ethyl 5-oxo-2,3-diphenyl-cyclo-pentane-1-carboxyl-ate.

Project description:The title compound, C(20)H(20)O(3), was prepared by an acyl-oin-type condensation reaction in the presence of sodium sand and dry ether using ethyl cinnamate as the starting material. The C-O bond lengths for the carbonyl groups are 1.191 (2) and 1.198 (2) Å, while the C-O bond in the ester group is 1.335 (2) Å. The C-C bond lengths in the phenyl groups average 1.375 Å, while the C-C bonds in the cyclo-penta-none ring average 1.525 Å, indicating single C-C bonds in the latter.

| S-EPMC2979171 | biostudies-literature

(1R,2S)-Methyl 1-(4-chloro-phen-yl)-3-oxo-1,2,3,4-tetra-hydro-cyclo-penta-[b]indole-2-carboxyl-ate 0.2-hydrate.

Project description:The title compound, C(19)H(14)ClNO(3)·0.2H(2)O, crystallizes with five mol-ecules and a disordered water mol-ecule in the asymmetric unit. Four of the five mol-ecules form hydrogen-bonded dimers via N-H⋯O hydrogen bonds towards another symmetry-independent mol-ecule, whereas the fifth mol-ecule forms a hydrogen-bonded dimer with its symmetry equivalent, also via N-H⋯O hydrogen bonds. The dihedral angle between the planes of the fused benzene ring and the five-membered ring to which it is attached is 79.45 (13), 49.00 (15), 72.49 (16), 81.91 (18) and 76.38 (16)° for the five mol-ecules in the asymmetric unit.

| S-EPMC3247393 | biostudies-literature

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