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

1 Scopus citations

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

Bibliographical note

Funding Information:
We appreciate the financial support from national Project 973 (Grant No. 2007 CB607601), Fund for Creative Research Groups (Grant No. 50721062), and the National Natural Science Foundation (Grant No. 50773089).

Keywords

crystal structure
disulfane
hydrogen bonding
organosulfur chemistry
sulfide

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10.1107/S2056989015018289

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@article{638aa39678804318bff296f8774c1ca7,

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",

note = "Funding Information: We appreciate the financial support from national Project 973 (Grant No. 2007 CB607601), Fund for Creative Research Groups (Grant No. 50721062), and the National Natural Science Foundation (Grant No. 50773089).",

year = "2015",

doi = "10.1107/S2056989015018289",

language = "English (US)",

volume = "71",

pages = "1371--1374",

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

issn = "2056-9890",

publisher = "International Union of Crystallography",

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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

N1 - Funding Information: We appreciate the financial support from national Project 973 (Grant No. 2007 CB607601), Fund for Creative Research Groups (Grant No. 50721062), and the National Natural Science Foundation (Grant No. 50773089).

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

M3 - Article

C2 - 26594513

AN - SCOPUS:84948466532

SN - 2056-9890

VL - 71

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

Abstract

Bibliographical note

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