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Crystal structure of rac-2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1-oxide.

ABSTRACT: In the title compound, C₁₆H₁₅NO₂S [alternative name: rac-2,3-diphenyl-1,3-thia-zinan-4-one 1-oxide], the thia-zine ring exhibits an envelope conformation, with the S atom forming the flap. The sulfoxide O atom is in a pseudo-axial position on the thia-zine ring and is trans to the phenyl group on C-2. The phenyl rings form a dihedral angle of 89.47 (19)°. In this racemate crystal, homochiral mol-ecules form slabs parallel to (010) of thickness b/2 which then stack with alternating chirality in the b-axis direction. The stacking is aided by edge-to-face inter-actions between the phenyl rings of racemic mol-ecules. Within each of the single-enanti-omer slabs, the mol-ecules are held by C-H⋯O-type inter-actions, with an H⋯O distance of 2.30 Å, forming infinite chains along the c-axis direction, as well by the edge-to-face inter-actions between phenyl rings of neighboring mol-ecules in the a-axis direction.

SUBMITTER: Yennawar HP

PROVIDER: S-EPMC5095828 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature

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Crystal structure of rac-2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1-oxide.

Yennawar Hemant P HP Yang Ziwei Z Silverberg Lee J LJ

Acta crystallographica. Section E, Crystallographic communications 20161007 Pt 11

In the title compound, C16H15NO2S [alternative name: rac-2,3-diphenyl-1,3-thia-zinan-4-one 1-oxide], the thia-zine ring exhibits an envelope conformation, with the S atom forming the flap. The sulfoxide O atom is in a pseudo-axial position on the thia-zine ring and is trans to the phenyl group on C-2. The phenyl rings form a dihedral angle of 89.47 (19)°. In this racemate crystal, homochiral mol-ecules form slabs parallel to (010) of thickness b< ...[more]

PMID: 27840703

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2,3-Diphenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one.

Project description:The six-membered thia-zine ring in the title compound, C16H15NOS, adopts a half-chair conformation, with the S atom forming the back of the chair. The base of the chair has a slight twist reflected in the r.m.s. deviation (0.0756 Å) of those five atoms from the plane defined by them. The phenyl substituents are almost perpendicular to each other [dihedral angle 87.06 (9)°]. In the crystal, mol-ecules are linked into chains parallel to the c axis through C-H⋯O inter-actions.

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Crystal structure of 2,3-diphenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one 1-oxide.

Project description:In the racemic title compound, C20H15NO2S, the planes of the two phenyl substituents form dihedral angles of 48.97 (15) and 69.26 (15)° with that of the fused benzene ring of the parent benzo-thia-zine ring, while the heterocyclic thia-zine ring exhibits a screw-boat pucker. The O atom on the S atom of the ring is pseudo-axial on the thia-zine ring and trans to the 2-phenyl group. In the crystal, mol-ecules are arranged in layers in the ac plane, the layers being linked across b through inter-molecular C-H⋯O hydrogen-bonding inter-actions.

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Crystal structures of rac-2,3-diphenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zine-1,1,4-trione and N-[(2S,5R)-1,1,4-trioxo-2,3-diphenyl-1,3-thia-zinan-5-yl]acet-amide.

Project description:The syntheses and crystal structures of two thia-zinone compounds, namely, rac-2,3-diphenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zine-1,1,4-trione, C16H15NO3S, in its racemic form, and N-[(2S,5R)-1,1,4-trioxo-2,3-diphenyl-1,3-thia-zinan-5-yl]acet-amide, C18H18N2O4S, in an enanti-opure form, are reported. The thia-zine rings in the two structures differ in their puckering, as a half-chair in the first and a boat pucker in the second. The extended structures for both compounds have only C-H⋯O-type inter-actions between symmetry-related mol-ecules, and exhibit no π-π stacking inter-actions in spite of each having two phenyl rings.

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Crystal structures of the sulfones of 2,3-diphenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one and 2,3-diphenyl-2,3-di-hydro-4H-pyrido[3,2-e][1,3]thia-zin-4-one.

Project description:The title sulfones, 2,3-diphenyl-2,3-di-hydro-4H-1,3-benzo-thia-zine-1,1,4-trione, C20H15NO3S, and 2,3-diphenyl-2,3-di-hydro-4H-pyrido[3,2-e][1,3]thia-zine-1,1,4-trione, C19H14N2O3S, crystallize in space group P21/n with two mol-ecules in each of the asymmetric units and have almost identical unit cells and extended structures. In both structures, the thia-zine rings exhibit a screw-boat pucker. The inter-molecular inter-actions observed are C-H⋯O-type hydrogen bonds and parallel partial π-π stacking between the fused aromatic rings (benzo- or pyrido-) of the core of the mol-ecules within each asymmetric unit, and also connecting to mol-ecules with translational periodicity in the a-axis direction in what can be described as columns (two per asymmetric unit) of stacked mol-ecules with alternating chirality. The pendant phenyl groups of both mol-ecules do not participate in aromatic ring inter-actions.

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Crystal structures of 2,3-bis-(4-chloro-phen-yl)-1,3-thia-zolidin-4-one and trans-2,3-bis-(4-chloro-phen-yl)-1,3-thia-zolidin-4-one 1-oxide.

Project description:In the crystal structures of the title compounds, C15H11Cl2NOS, (1), and C15H11Cl2NO2S, (2), wherein (2) is the oxidized form of (1), the thia-zolidine ring is attached to two chloro-phenyl rings. The chloro-phenyl ring on the 2-carbon atom position points in the same direction as that of the S atom in (1), while in (2), the S atom points in the opposite direction. The O atom on the chiral S atom in (2) is trans to the chloro-phenyl ring on the 2-carbon. The chloro-phenyl ring planes in each structure are close to orthogonal, making dihedral angles of 78.61 (6) and 87.46 (8)° in (1) and (2), respectively. The thia-zolidine ring has a twisted conformation on the S-Cmethine bond in (1), and an envelope conformation with the S atom 0.715 (3) Å out of the plane of other four atoms in (2). In the crystal of (1), mol-ecules are linked by C-H⋯O hydrogen bonds, as well as by slipped parallel π-π inter-actions [inter-centroid distance = 3.840 (3) Å] between inversion-related phenyl rings, forming sheets parallel to (001). In the crystal of (2), mol-ecules are linked via C-H⋯O and C-H⋯Cl hydrogen bonds, forming slabs parallel to (001).

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rac-(4aR,8aR)-2,3-Diphenyl-4a,5,6,7,8,8a-hexa-hydro-quinoxaline.

Project description:The structure of the title racemic compound, C(20)H(20)N(2), shows close similarity to that of the enanti-omerically pure (4aR,8aR)-2,3-diphenyl-4a,5,6,7,8,8a-hexa-hydro-quinoxaline [Wang & Ye (2008 ▶). Acta Cryst. E64, o359-o359]. The similarity applies to the unit-cell parameters as well as to the packing of the constituent mol-ecules. Similar packing is conditioned by a lack of directed inter-molecular inter-actions such as hydrogen bonds in either structure.

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Spontaneous resolution and crystal structure of (2S)-2-(3-nitro-phen-yl)-3-phenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one; crystal structure of rac-2-(4-nitro-phen-yl)-3-phenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one.

Project description:The crystal structures of isomeric rac-2-(4-nitro-phen-yl)-3-phenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one (C16H14N2O3S) (1) and (2S)-2-(3-nitro-phen-yl)-3-phenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one (C16H14N2O3S) (2) are reported here. While 1 crystallizes in a centrosymmetric space group, the crystal of 2 chosen for data collection has mol-ecules only with (2S) chirality. This is the result of spontaneous resolution during crystallization, as the synthesis produces a racemic mixture. A crystal with (2R) mol-ecules was also found in the same crystallization vial (structure factors available). The six-membered thia-zine ring in both 1 and 2 displays an envelope conformation with the S atom forming the flap. The aryl rings in both structures adopt an approximate V shape with angles between their planes of 46.97 (14)° in 1 and 58.37 (10)° in 2. In both structures, the mol-ecules form layers in the ab plane. Within such a layer in 1, one of the O atoms of the nitro-phenyl group accepts a C-H⋯O hydrogen bond from the CH group at position 5 of the thia-zine ring of a mol-ecule of opposite chirality, forming chains along the a-axis direction. Each of the thia-zine rings also participate in C-H⋯O bonds with the same carbon atom as above, resulting in chains along the b-axis direction, albeit of monochiral type. Adjacent layers are consolidated along the c-axis direction by pairs of parallel hydrogen bonds (C-H⋯O type) between the nitro-phenyl groups of enanti-omers. In 2, the two C-H⋯O hydrogen bonds contribute to chain formation along the b-axis direction. Weak edge-to-face inter-actions between the aryl groups of neighbouring mol-ecules in 1, and C-H⋯π inter-actions between a thia-zine ring CH group and a phenyl group of a neighboring mol-ecule in 2 are also observed.

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