Crystal structures of (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)sulfide and the corresponding disulfane

Matthew J. Henley; Alayne L. Schroll; Victor G. Young; George Barany

doi:10.1107/S2056989015018289

Crystal structures of (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)sulfide and the corresponding disulfane

Matthew J. Henley, Alayne L. Schroll, Victor G. Young, George Barany

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

Abstract

The title compounds, (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)sulfide, C₁₅H₁₆N₂OS, (I), and (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)disulfane, C₁₅H₁₆N₂OS₂, (II), are stable derivatives of (chlorocarbonyl)sulfenyl chloride and (chlorocarbonyl)disulfanyl chloride, respectively. The torsion angle about the S - S bond in (II) is -92.62 (6)°, which is close to the theoretical value of 90°. In the crystal of (II), non-classical intermolecular C - H⋯O hydrogen bonds form centrosymmetric cyclic dimers [graph set R₂²(10)], while inter-dimer C - H⋯S interactions generate chains extending along the b axis.

Original language	English (US)
Pages (from-to)	1371-1374
Number of pages	4
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	71
DOIs	https://doi.org/10.1107/S2056989015018289
State	Published - 2015

Keywords

crystal structure
disulfane
hydrogen bonding
organosulfur chemistry
sulfide

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10.1107/S2056989015018289

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title = "Crystal structures of (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)sulfide and the corresponding disulfane",

abstract = "The title compounds, (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)sulfide, C15H16N2OS, (I), and (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)disulfane, C15H16N2OS2, (II), are stable derivatives of (chlorocarbonyl)sulfenyl chloride and (chlorocarbonyl)disulfanyl chloride, respectively. The torsion angle about the S - S bond in (II) is -92.62 (6)°, which is close to the theoretical value of 90°. In the crystal of (II), non-classical intermolecular C - H⋯O hydrogen bonds form centrosymmetric cyclic dimers [graph set R22(10)], while inter-dimer C - H⋯S interactions generate chains extending along the b axis.",

keywords = "crystal structure, disulfane, hydrogen bonding, organosulfur chemistry, sulfide",

author = "Henley, {Matthew J.} and Schroll, {Alayne L.} and Young, {Victor G.} and George Barany",

year = "2015",

doi = "10.1107/S2056989015018289",

language = "English (US)",

volume = "71",

pages = "1371--1374",

journal = "Acta Crystallographica Section E: Crystallographic Communications",

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TY - JOUR

T1 - Crystal structures of (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)sulfide and the corresponding disulfane

AU - Henley, Matthew J.

AU - Schroll, Alayne L.

AU - Young, Victor G.

AU - Barany, George

PY - 2015

Y1 - 2015

N2 - The title compounds, (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)sulfide, C15H16N2OS, (I), and (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)disulfane, C15H16N2OS2, (II), are stable derivatives of (chlorocarbonyl)sulfenyl chloride and (chlorocarbonyl)disulfanyl chloride, respectively. The torsion angle about the S - S bond in (II) is -92.62 (6)°, which is close to the theoretical value of 90°. In the crystal of (II), non-classical intermolecular C - H⋯O hydrogen bonds form centrosymmetric cyclic dimers [graph set R22(10)], while inter-dimer C - H⋯S interactions generate chains extending along the b axis.

AB - The title compounds, (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)sulfide, C15H16N2OS, (I), and (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)disulfane, C15H16N2OS2, (II), are stable derivatives of (chlorocarbonyl)sulfenyl chloride and (chlorocarbonyl)disulfanyl chloride, respectively. The torsion angle about the S - S bond in (II) is -92.62 (6)°, which is close to the theoretical value of 90°. In the crystal of (II), non-classical intermolecular C - H⋯O hydrogen bonds form centrosymmetric cyclic dimers [graph set R22(10)], while inter-dimer C - H⋯S interactions generate chains extending along the b axis.

KW - crystal structure

KW - disulfane

KW - hydrogen bonding

KW - organosulfur chemistry

KW - sulfide

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U2 - 10.1107/S2056989015018289

DO - 10.1107/S2056989015018289

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SP - 1371

EP - 1374

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

ER -

Crystal structures of (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)sulfide and the corresponding disulfane

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