1-Methyl-3-phenyl­sulfonyl-2-piperidone

The piperidone ring in the title compound, C12H15NO3S, has a slightly distorted half-chair conformation with the methyl, carbonyl and phenyl­sulfonyl ring substituents occupying equatorial, equatorial and axial positions, respectively. Mol­ecules are connected into centrosymmetric dimers via C—H⋯O inter­actions and these associate into layers via C—H⋯O—S contacts. Further C—H⋯O inter­actions involving both the carbonyl and sulfonyl O atoms consolidate the crystal packing by providing connections between the layers

2-[(4-Chlorophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal structure and Hirshfeld surface analysis

The title compound, C15H13ClO2S, comprises (4-chlorophenyl)sulfanyl, benzaldehyde and methoxy residues linked at a chiral methine-C atom (the crystal is racemic). A twist in the methine-C—C(carbonyl) bond [O—C—C—O torsion angle = 19.3 (7)⁰] leads to a dihedral angle of 22.2 (5)⁰ between the benzaldehyde and methine+methoxy residues. The chlorobenzene ring is folded to lie over the O atoms, with the dihedral angle between the benzene rings being 42.9 (2)⁰. In the crystal, the carbonyl-O atom accepts two C—H...O interactions with methyl- and methine-C—H atoms being the donors. The result is an helical supramolecular chain aligned along the c axis; chains pack with no directional interactions between them. An analysis of the Hirshfeld surface points to the important contributions of weak H...H and C...C contacts to the molecular packing

1-(4-Bromo­phen­yl)-2-ethyl­sulfinyl-2-(phenyl­selan­yl)ethanone monohydrate

In the title hydrate, C16H15BrO2SSe·H2O, the sulfinyl O atom lies on the opposite side of the mol­ecule to the Se and carbonyl O atoms. The benzene rings form a dihedral angle of 51.66 (17)° and are splayed with respect to each other. The observed conformation allows the water mol­ecules to bridge sulfinyl O atoms via O—H⋯O hydrogen bonds, generating a linear supra­molecular chain along the b axis; the chain is further stabilized by C—H⋯O contacts. The chains are held in place in the crystal structure by C⋯H⋯π and C—Br⋯π inter­actions

4-Methyl-3-(2-phenoxy­acet­yl)-5-phenyl-1,3,4-oxadiazinan-2-one

The 1,3,4-oxadiazinane ring in the title compound, C18H18N2O4, is in a twisted boat conformation. The two carbonyl groups are orientated towards the same side of the mol­ecule. The dihedral angle between the planes of the benzene rings is 76.6 (3)°. Mol­ecules are sustained in the three-dimensional structure by a combination of C—H⋯O, C—H⋯π and π–π [shortest centroid–centroid distance = 3.672 (6) Å] inter­actions

Spectroscopic and Theoretical Studies of Some 3-(4 '-Substituted phenylsulfanyl)-1-methyl-2-piperidones

The analysis of the IR carbonyl bands of some 3-(4 '-substituted phenylsulfanyl)1- methyl-2-piperidones 1-6 bearing substituents: NO2 (compound 1), Br (compound 2), Cl (compound 3), H (compound 4) Me (compound 5) and OMe (compound 6) supported by B3LYP/ 6-31+ G(d, p) and PCM calculations along with NBO analysis (for compound 4) and X-ray diffraction (for 2) indicated the existence of two stable conformations, i.e., axial (ax) and equatorial (eq), the former corresponding to the most stable and the least polar one in the gas phase calculations. the sum of the energy contributions of the orbital interactions (NBO analysis) and the electrostatic interactions correlate well with the populations and the vCO frequencies of the ax and eq conformers found in the gas phase. Unusually, in solution of the non-polar solvents n-C6H14 and CCl4, the more intense higher IR carbonyl frequency can be ascribed to the ax conformer, while the less intense lower IR doublet component to the eq one. the same.CO frequency trend also holds in polar solvents, that is nu(CO(eq)) < nu(CO(ax)). However, a reversal of the ax/eq intensity ratio occurs going from non-polar to polar solvents, with the ax conformer component that progressively decreases with respect to the eq one in CHCl3 and CH2Cl2, and is no longer detectable in the most polar solvent CH3CN. the PCM method applied to compound 4 supports these findings. in fact, it predicts the progressive increase of the eq/ax population ratio as the relative permittivity of the solvent increases. Moreover, it indicates that the computed.CO frequencies of the ax and eq conformers do not change in the non-polar solvents n-C6H14 and CCl4, while the.CO frequencies of the eq conformer become progressively lower than that of the ax one going from CHCl3 to CH2Cl2 and to CH3CN, in agreement with the experimental IR values. the analysis of the geometries of the ax and eq conformers shows that the carbonyl oxygen atom of the eq conformer is free for solvation, while the O-[CO]center dot center dot center dot H[o-Ph] hydrogen bond that takes place in the ax conformer partially hinders the approach of the solvent molecules to the carbonyl oxygen atom. Therefore, the larger solvation that occurs in the carbonyl oxygen atom of the eq conformer is responsible for the observed and calculated decrease of the corresponding frequency. the X-ray single crystal analysis of 2 indicates that this compound adopts the most polar eq geometry in the solid. in fact, in order to obtain the largest energy gain, the molecules are arranged in the crystal in a helical fashion due to dipole moment coupling along with C-H center dot center dot center dot O and C-H center dot center dot center dot pi(Ph) hydrogen bonds.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)MIUR (PRIN)Univ São Paulo, Inst Chem, Conformat Anal & Elect Interact Lab, BR-05513970 São Paulo, BrazilUniversidade Federal de São Paulo, UNIFESP, Inst Environm Chem & Pharmaceut Sci, BR-09972270 Diadema, SP, BrazilUniv Fed Sao Carlos, Dept Chem, BR-13565905 Sao Carlos, SP, BrazilUniv Ferrara, Dept Chem, I-44100 Ferrara, ItalyUniversidade Federal de São Paulo, UNIFESP, Inst Environm Chem & Pharmaceut Sci, BR-09972270 Diadema, SP, BrazilCAPES: 808/2009Web of Scienc

Crystal structure of ethyl 4-methyl-2-oxo-5-phenyl-1,3,4-oxadiazinane-3-carboxylate, C13H16N2O4

C13H16N2O4, orthorhombic, P212121 (no. 19), a = 6.7876(2) Å, b = 8.8984(2) Å, c = 22.3399(6) Å, V = 1349.30(6) Å3, Z = 4, Rgt(F) = 0.0384, wRref(F2) = 0.0947, T = 293(2) K

2-(4-Methoxy­phenyl­sulfin­yl)cyclo­hexan-1-one

The cyclo­hexa­none ring in the title compound, C13H16O3S, is in a distorted chair conformation. The intra­molecular S⋯Ocarbon­yl distance is 2.814 (2) Å. Mol­ecules are connected into a two-dimensional array via C—H⋯O contacts involving the carbonyl and sulfinyl O atoms

2-[(4-Bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry

The title compound, C15H13BrO2S, comprises three different substituents bound to a central (and chiral) methine-C atom, i.e. (4-bromophenyl)sulfanyl, benzaldehyde and methoxy residues: crystal symmetry generates a racemic mixture. A twist in the molecule is evident about the methine-C—C(carbonyl) bond as evidenced by the O—C—C—O torsion angle of -20.8 (7)⁰. The dihedral angle between the bromobenzene and phenyl rings is 43.2 (2)⁰, with the former disposed to lie over the oxygen atoms. The most prominent feature of the packing is the formation of helical supramolecular chains as a result of methyland methine-C—H...O(carbonyl) interactions. The chains assemble into a three-dimensional architecture without directional interactions between them. The nature of the weak points of contacts has been probed by a combination of Hirshfeld surface analysis, non-covalent interaction plots and interaction energy calculations. These point to the importance of weaker H...H and C—H...C interactions in the consolidation of the structure

(R)-2-Phen­oxy-1-(4-phenyl-2-sulfan­ylidene-1,3-oxazolidin-3-yl)ethanone

The central 1,3-oxazolidine-2-thione ring in the title compound, C17H15NO3S, is approximately planar with maximum deviations of 0.036 (4) and −0.041 (5) Å for the O and methyl­ene-C atoms, respectively. The dihedral angles formed between this plane and the two benzene rings, which lie to the same side of the central plane, are 86.5 (2) [ring-bound benzene] and 50.6 (3)°. The ethan-1-one residue is also twisted out of the central plane, forming a O—C—N—C torsion angle of 151.5 (5)°. The dihedral angle formed by the benzene rings is 62.8 (2)° so that overall, the mol­ecule has a twisted U-shape. In the crystal, mol­ecules are linked into supra­molecular arrays two mol­ecules thick in the bc plane through C—H⋯O, C—H⋯S and C—H⋯π inter­actions