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

ABSTRACT: 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.

SUBMITTER: Yennawar HP

PROVIDER: S-EPMC3998299 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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

Yennawar Hemant P HP Silverberg Lee J LJ

Acta crystallographica. Section E, Structure reports online 20140115 Pt 2

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. ...[more]

PMID: 24764860

Similar Datasets

2,3-Diphenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one.

Project description:In the title compound, C20H15NOS, the dihedral angle between the phenyl rings is 74.25 (6)°. The six-membered 1,3-thia-zine ring has an envelope conformation with the C atom at the 2-position forming the flap. The crystal structure features weak C-H⋯O inter-actions, which lead to the formation of a tape motif along [110].

| S-EPMC3998534 | biostudies-literature

2,3-Diphenyl-2,3-di-hydro-4H-pyrido[3,2-e][1,3]thia-zin-4-one.

Project description:In the racemic title compound, C19H14N2OS, the two phenyl substituents on the 1,3-thia-zine ring are almost perpendicular to the pyridine ring which is fused to the thia-zine ring [inter-ring dihedral angles = 87.90?(8) and 85.54?(7)°]. The dihedral angle between the two phenyl rings is 75.11?(7)°. The six-membered thia-zine ring has an envelope conformation with the ortho-related C atom forming the flap. The crystals exhibit face-to-edge aromatic-ring interactions with the nearest C-H?C distance equal to 3.676?(3)?Å.

| S-EPMC4051078 | biostudies-other

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.

| S-EPMC5946966 | biostudies-literature

Crystal structures of 2-(4-nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one and 2-(2-nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one.

Project description:The crystal structures are reported of the isomeric compounds 2-(4-nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one, (I), and 2-(2-nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one, (II), both C20H14N2O3S, being the para-nitro and ortho-nitro forms, respectively, the meta-form of which is known [Yennawar et al. (2013). Acta Cryst. E69, o1679]. The six-membered thia-zone ring fused with a benzene ring displays a screw-boat conformation with a total puckering amplitude of 0.627 (1) Å in (I), and a near screw-boat conformation with a total puckering amplitude of 0.600 (1) Å in (II). The dihedral angles between the planes of the substituent nitrophenyl and phenyl and rings with the benzene ring of the parent benzo-thia-zone moiety are 75.93 (5) and 82.61 (5)° [in (I)], and 76.79 (6) and 71.66 (6)° [in (II)]. Weak inter-molecular C-H⋯O hydrogen-bonding inter-actions between aromatic H-atom donors and both a nitro-O atom and a thia-zone O-atom acceptor in (I) and a thia-zone O atom in (II) are present, forming in (I) a centrosymmetric 22-membered cyclic dimer which is extended through a similar inversion-related 14-membered cyclic hydrogen-bonding association into a zigzag chain structure extending along c. In (II), a single inter-molecular C-H⋯O hydrogen bond gives a chain structure extending along b. In addition, weak C-H⋯π inter-actions are present in both structures [minimum C⋯ring-centroid separations = 3.630 (2) and 3.581 (2) Å, respectively].

| S-EPMC4438845 | biostudies-literature

2-(3-Nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one.

Project description:The title compound, C20H14N2O3S, has three aromatic rings, viz. (i) a phenyl ring, (ii) a 3-nitro-phenyl and (iii) a 1,3-benzo-thia-zine fused-ring system. The dihedral angle between (i) and (ii) is 85.31?(15)°, between (ii) and (iii) is 81.33?(15)° and between (i) and (iii) is 75.73?(15)°. The six-membered 1,3-thia-zine ring has an envelope conformation with the C atom in the 2-position forming the flap. In the crystal, mol-ecules are linked by weak C-H?O inter-actions, forming a three-dimensional network.

| S-EPMC3884335 | biostudies-literature

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.

| S-EPMC5598846 | biostudies-literature

Crystal structure of the 1:1 adduct of 2,3-diphenyl-3,4,5,6-tetra-hydro-2H-1,3-thia-zin-4-one with tri-phenyl-tin chloride.

Project description:The title adduct, chlorido-(2,3-diphenyl-3,4,5,6-tetra-hydro-2H-1,3-thia-zin-4-one-κO)tri-phenyl-tin, [Sn(C6H5)3Cl(C16H15NOS)], resulted from reaction of 2,3-diphenyl-3,4,5,6-tetra-hydro-2H-1,3-thia-zin-4-one with tri-phenyl-tin chloride. The thia-zine ring has an envelope conformation with the S atom forming the flap. The mol-ecule has five phenyl rings, two of them attached to the thia-zine ring at positions 2 and 3, and three in coordination with the Sn(IV) atom. The three rings of the tri-phenyl-tin group are involved in intra-molecular inter-actions of different types, C-H⋯O, edge-to-face (or T-type) π-π inter-actions with the 3-phenyl ring of the thia-zine, T-type inter-actions with both phenyl rings of the thia-zine etc. On the other hand, all the phenyl rings participate in inter-molecular π-π inter-actions. There is one instance of a 'parallel-displaced'-type inter-action extending continuously along the a-axis direction and seven instances of T-type inter-actions stabilizing the crystal lattice.

| S-EPMC4778843 | biostudies-literature

2,3-Diphenyl-1,3-thia-zolidin-4-one.

Project description:The title compound, C15H13NOS, is a chiral mol-ecule crystallized as a racemate, with two molecules in the asymmetric unit. In each of the mol-ecules, the five-membered thia-zine ring has an envelope conformation, with the S atom forming the flap. In one mol-ecule, the angle between the two phenyl-ring planes is 82.77?(7)°, while in the other it is 89.12?(6)°. In the crystal, mol-ecules are linked into chains along the b-axis direction by C-H?O hydrogen bonds.

| S-EPMC4158525 | biostudies-literature

Crystal structures of two 2,3-diaryl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-ones.

Project description:The syntheses and crystal structures of 2,3-bis-[3-(tri-fluoro-meth-yl)phen-yl]-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one (di-m-CF3; C22H13F6NOS) (1) and 2,3-bis-(4-methyl-phen-yl)-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one (di-p-CH3; C22H19NOS) (2) are reported. Each structure is racemic: the asymmetric unit of 2 consists of two mol-ecules. In both 1 and 2, the six-membered 1,3-thia-zine ring is close to an envelope conformation with the chiral C atom forming the flap. In 1, the 2-aryl group is pseudo-equatorial, while in 2 it is pseudo-axial. In 1, the pendant aryl rings form a V shape with an inter-centroid distance of 3.938?(3)?Å and an acute dihedral angle of 48.3?(2)° between them. Both CF3 groups are disordered over two orientations in 0.687?(19):0.313?(19) and 0.667?(16):0.33?(16) ratios. In each of the independent mol-ecules of 2, the aryl rings are almost orthogonal to each other [dihedral angles = 85.50?(12) and 86.07?(11)°]. In both structures, the chiral C atom and the O atoms participate in C-H?O-type hydrogen bonding between symmetry-related mol-ecules of 1 or the independent enanti-omers in 2, forming chains along the c-axis direction in 1 and the b-axis direction in 2. Additionally, in 1, ?-? contacts of both face-to-face and edge-to-face type, as well as ?-H?O and ?-H?F inter-actions are observed. In 2, a racemic mixture of mol-ecules forms layers in the ac plane linked by weak ?-? and C-H?? inter-actions.

| S-EPMC5947804 | biostudies-other

Crystal structure of meso-3,3'-(1,4-phenyl-ene)bis-(2-phenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one).

Project description:The crystal structure of the title compound - meso-C26H24N2O2S2 with two stereocenters - has half the mol-ecule in the asymmetric unit with the other half generated by a crystallographic center of inversion. The thia-zine ring is in a conformation that is between half-chair and envelope [θ = 52.51 (17)°]. The phenyl ring on the 2-carbon atom of the thia-zine ring is pseudo-axial. The central phenyl ring of the mol-ecule is close to orthogonal to the phenyl rings on either side with an angle of 76.85 (11)° between those planes. In the crystal, pairwise, weak C-H⋯O hydrogen bonds between the central phenyl ring and the oxygen atoms of neighboring mol-ecules result in continuous strips propagating along the a-axis direction. Hydro-phobic inter-actions of the C-H⋯π type are also observed.

| S-EPMC6176446 | biostudies-literature

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