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Crystal structures of the sulfones of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one

ABSTRACT: The title sulfones crystallize in space group P21/n with two molecules in each of the asymmetric units and have almost identical unit cells and extended structures. In both structures, the thiazine rings exhibit a screw-boat pucker. The title sulfones, 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazine-1,1,4-trione, C20H15NO3S, and 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazine-1,1,4-trione, C19H14N2O3S, crystallize in space group P21/n with two molecules in each of the asymmetric units and have almost identical unit cells and extended structures. In both structures, the thiazine rings exhibit a screw-boat pucker. The intermolecular interactions 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 molecules within each asymmetric unit, and also connecting to molecules with translational periodicity in the a-axis direction in what can be described as columns (two per asymmetric unit) of stacked molecules with alternating chirality. The pendant phenyl groups of both molecules do not participate in aromatic ring interactions.

SUBMITTER: Yennawar H

PROVIDER: S-EPMC9993925 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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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.

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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].

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Crystal structures of two solvated 2-aryl-3-phenyl-2,3-di-hydro-4H-pyrido[3,2-e][1,3]thia-zin-4-ones.

Project description:The synthesis and crystal structures of 2-(4-fluoro-phen-yl)-3-phenyl-2,3-di-hydro-4H-pyrido[3,2-e][1,3]thia-zin-4-one toluene hemisolvate (1), C19H13FN2OS·0.5C7H8, and 2-(4-nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-pyrido[3,2-e][1,3]thia-zin-4-one iso-propanol 0.25-solvate 0.0625-hydrate (2), C19H13N3O3S·0.25C3H7O·0.0625H2O, are reported. Both are racemic mixtures (centrosymmetric crystal structures) of the individual com-pounds and incorporate solvent mol-ecules in their structures. Compound 2 has four thia-zine mol-ecules in the asymmetric unit. All the thia-zine rings in this study show an envelope pucker, with the C atom bearing the substituted phenyl ring displaced from the other atoms. The phenyl and aryl rings in each of the mol-ecules are roughly orthogonal to each other, with dihedral angles of about 75°. The extended structures of 1 and 2 are consolidated by C-H⋯O and C-H⋯N(π), as well as T-type (C-H⋯π) inter-actions. Parallel aromatic ring inter-actions (π-π stacking) are observed only in 2.

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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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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.

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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].

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2,4-Diphenyl-4,5-dihydro-3H-pyrido[2,3-b][1,4]diazepine.

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

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