Crystal structure of 2,3-diphenyl-2,3-dihydro-4<i>H</i>-1,3-benzothiazin-4-one 1-oxide

Yennawar, Hemant P.; Fox, Ryan; Moyer, Quentin J.; Yang, Ziwei; Silverberg, Lee J.

doi:10.1107/s2056989017010313

Cited by 4 publications

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References 19 publications

(24 reference statements)

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“…We have previously reported the preparation of the title sulfones 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one 1,1-dioxide 1 and 2,3-diphenyl-2,3-dihydro-4Hpyrido[3,2-e][1,3]thiazin-4-one 1,1-dioxide 2 (Silverberg, 2020). We have also described the X-ray crystal structures of the corresponding sulfides 3 and 4 and sulfoxides 5 and 6 (Yennawar, Bendinsky et al, 2014;Yennawar, Singh et al, 2014;Yennawar, Fox et al, 2017;Yennawar, Noble et al, 2017). Herein we report the crystal structures of 1 and 2, along with a more complete characterization than previously reported (Silverberg, 2020).…”

Section: Chemical Contextmentioning

confidence: 70%

“…The structures of 1 and 2 both display a screw-boat (pucker) conformation for the four thiazine rings in the two asymmetric units [puckering amplitude Q ranging between 0.616 (4) and 0.6449 (16) A ˚, and the and ' values, after accounting for the absolute conformation transformations, are between 60.7 (4) and 63.02 (16) , and 140.53 (18) and 142.9 (4) , respectively]. The puckering observed is similar to that in the sulfoxides 5 and 6 (Yennawar, Fox et al 2017;Yennawar, Noble et al 2017), but is different from the envelope conformations seen in the sulfides 3 and 4 (Yennawar, Bendinsky et al, 2014;Yennawar, Singh et al, 2014). Each molecule contains one stereogenic center, which lies between the N atom and the SO 2 group of the heterocyclic ring: in the asymmetric unit of 1, C8 has an S configuration and C28 an R configuration, thus generating a racemic pair.…”

Section: Structural Commentarymentioning

confidence: 76%

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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

et al. 2023

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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.

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Section: Chemical Contextmentioning

confidence: 70%

Section: Structural Commentarymentioning

confidence: 76%

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

et al. 2023

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“…The sulfur in various 2,3-dihydro-1,3-thiazin-4-ones was oxidized selectively to the sulfoxides 500-503 using Oxone® (Scheme 158). [242][243][244][245]…”

Section: Scheme 157mentioning

confidence: 99%

“…247 However, attempts to make the complex of 2,3-diphenyl-5,6-dihydro-1,3benzothiazin-4-one 514 gave only the sulfoxide 502. 244…”

Section: Scheme 161mentioning

confidence: 99%

Chemistry of 1,3-thiazin-4-ones and their derivatives, 1995 - mid-2018

Silverberg¹,

Moyer²

2019

Arkivoc

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This review updates an earlier review published in 1996 by Ryabukhin, Korzhavina, and Suzdalev, which covered the literature through 1994. It deals with the synthesis and reactivity of 1,3-thiazin-4-ones and their derivatives. These include reduced compounds, 2-imino or 2-amino compounds, compounds with fused arenes or heterocycles, bridged compounds, and compounds combining various of these attributes.

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Crystal structure of (1S,2S,5R)-5-acetylamino-4-oxo-2,3-diphenyl-1,3-thiazinan-1-ium-1-olate

2017

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The asymmetric unit of the enantiomerically pure title compound, C18H18N2O3S, comprises two independent molecules (AandB) having almost identical conformations. When overlayed, the alignment–r.m.s. deviation value is 0.30 Å. The six-membered heterocycle has a twisted half-chair conformation in both molecules. The O atom on the S atom of the ring is pseudo-axial on the thiazine ring andtransto both a phenyl group substituent and the acetamide group in each case. The two benzene rings in each molecule are almost orthogonal to each other, with interplanar dihedral angles of 83.79 (17) and 86.95 (16)°. The acetamide group is pseudo-equatorial and a phenyl ring is pseudo-axial on the thiazine ring. Both molecules show a weak intramolecular C—H...O interaction between H-atom donors of one of the phenyl rings and the acetamide group. In the crystal, an intermolecular N—H...O(thiazine) hydrogen bond linksBmolecules along the 21(b) screw axis and, in addition, an N—H...O(acetamide) hydrogen bond linksAandBmolecules acrossa. A two-dimensional layered structure lying parallel to (001) is generated, also involving weak intermolecular C—H...O interactions.

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Crystal structure of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one 1-oxide

Cited by 4 publications

References 19 publications

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

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

Chemistry of 1,3-thiazin-4-ones and their derivatives, 1995 - mid-2018

Crystal structure of (1S,2S,5R)-5-acetylamino-4-oxo-2,3-diphenyl-1,3-thiazinan-1-ium-1-olate

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