Crystal structures of two 1,3-thiazolidin-4-one derivatives featuring sulfide and sulfone functional groups

Hemant P. Yennawar, Lee J. Silverberg, Kevin Cannon, Deepa Gandla, Sandeep K. Kondaveeti, Michael J. Zdilla, Ahmed Nuriye

Research output: Contribution to journalArticle

Abstract

The crystal structures of two closely related compounds, 1-cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one, C15H18N2O3S, (1) and 1-cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one 1,1-dioxide, C15H18N2O5S, (2), are presented. These compounds are comprised of three types of rings: thiazolidinone, nitrophenyl and cyclohexyl. In both structures, the rings are close to mutually perpendicular, with interplanar dihedral angles greater than 80° in each case. The thiazolidinone rings in both structures exhibit envelope puckering with the S atom as flap and the cyclohexyl rings are in their expected chair conformations. The two structures superpose fairly well, except for the orientation of the nitro groups with respect to their host phenyl ring, with a difference of about 10° between 1 and 2. The extended structure of 1 has two kinds of weak C - H⋯O interactions, giving rise to a closed ring formation involving three symmetry-related molecules. Structure 2 has four C - H⋯O interactions, two of which are exclusively between symmetry-related thiazolidinone dioxide moieties and have a parallel 'give-and-take-fashion' counterpart. In the other two interactions, the nitrophenyl ring and the cyclohexane ring each offer an H atom to the two O atoms on the sulfone group. Additionally, a C - H⋯π interaction between a C - H group of the cyclohexane ring and the nitrophenyl ring of an adjacent molecule helps to consolidate the structure.

Original languageEnglish (US)
Pages (from-to)1695-1699
Number of pages5
JournalActa Crystallographica Section E: Crystallographic Communications
Volume74
DOIs
StatePublished - Jan 1 2018

Fingerprint

Sulfones
sulfones
Sulfides
Functional groups
sulfides
Crystal structure
Cyclohexane
Derivatives
Atoms
crystal structure
rings
Molecules
Dihedral angle
Conformations
dioxides
cyclohexane
interactions
atoms
symmetry
seats

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

Cite this

@article{7332ec45664349c79f52c56987faccae,
title = "Crystal structures of two 1,3-thiazolidin-4-one derivatives featuring sulfide and sulfone functional groups",
abstract = "The crystal structures of two closely related compounds, 1-cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one, C15H18N2O3S, (1) and 1-cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one 1,1-dioxide, C15H18N2O5S, (2), are presented. These compounds are comprised of three types of rings: thiazolidinone, nitrophenyl and cyclohexyl. In both structures, the rings are close to mutually perpendicular, with interplanar dihedral angles greater than 80° in each case. The thiazolidinone rings in both structures exhibit envelope puckering with the S atom as flap and the cyclohexyl rings are in their expected chair conformations. The two structures superpose fairly well, except for the orientation of the nitro groups with respect to their host phenyl ring, with a difference of about 10° between 1 and 2. The extended structure of 1 has two kinds of weak C - H⋯O interactions, giving rise to a closed ring formation involving three symmetry-related molecules. Structure 2 has four C - H⋯O interactions, two of which are exclusively between symmetry-related thiazolidinone dioxide moieties and have a parallel 'give-and-take-fashion' counterpart. In the other two interactions, the nitrophenyl ring and the cyclohexane ring each offer an H atom to the two O atoms on the sulfone group. Additionally, a C - H⋯π interaction between a C - H group of the cyclohexane ring and the nitrophenyl ring of an adjacent molecule helps to consolidate the structure.",
author = "Yennawar, {Hemant P.} and Silverberg, {Lee J.} and Kevin Cannon and Deepa Gandla and Kondaveeti, {Sandeep K.} and Zdilla, {Michael J.} and Ahmed Nuriye",
year = "2018",
month = "1",
day = "1",
doi = "10.1107/S2056989018015098",
language = "English (US)",
volume = "74",
pages = "1695--1699",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",

}

TY - JOUR

T1 - Crystal structures of two 1,3-thiazolidin-4-one derivatives featuring sulfide and sulfone functional groups

AU - Yennawar, Hemant P.

AU - Silverberg, Lee J.

AU - Cannon, Kevin

AU - Gandla, Deepa

AU - Kondaveeti, Sandeep K.

AU - Zdilla, Michael J.

AU - Nuriye, Ahmed

PY - 2018/1/1

Y1 - 2018/1/1

N2 - The crystal structures of two closely related compounds, 1-cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one, C15H18N2O3S, (1) and 1-cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one 1,1-dioxide, C15H18N2O5S, (2), are presented. These compounds are comprised of three types of rings: thiazolidinone, nitrophenyl and cyclohexyl. In both structures, the rings are close to mutually perpendicular, with interplanar dihedral angles greater than 80° in each case. The thiazolidinone rings in both structures exhibit envelope puckering with the S atom as flap and the cyclohexyl rings are in their expected chair conformations. The two structures superpose fairly well, except for the orientation of the nitro groups with respect to their host phenyl ring, with a difference of about 10° between 1 and 2. The extended structure of 1 has two kinds of weak C - H⋯O interactions, giving rise to a closed ring formation involving three symmetry-related molecules. Structure 2 has four C - H⋯O interactions, two of which are exclusively between symmetry-related thiazolidinone dioxide moieties and have a parallel 'give-and-take-fashion' counterpart. In the other two interactions, the nitrophenyl ring and the cyclohexane ring each offer an H atom to the two O atoms on the sulfone group. Additionally, a C - H⋯π interaction between a C - H group of the cyclohexane ring and the nitrophenyl ring of an adjacent molecule helps to consolidate the structure.

AB - The crystal structures of two closely related compounds, 1-cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one, C15H18N2O3S, (1) and 1-cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one 1,1-dioxide, C15H18N2O5S, (2), are presented. These compounds are comprised of three types of rings: thiazolidinone, nitrophenyl and cyclohexyl. In both structures, the rings are close to mutually perpendicular, with interplanar dihedral angles greater than 80° in each case. The thiazolidinone rings in both structures exhibit envelope puckering with the S atom as flap and the cyclohexyl rings are in their expected chair conformations. The two structures superpose fairly well, except for the orientation of the nitro groups with respect to their host phenyl ring, with a difference of about 10° between 1 and 2. The extended structure of 1 has two kinds of weak C - H⋯O interactions, giving rise to a closed ring formation involving three symmetry-related molecules. Structure 2 has four C - H⋯O interactions, two of which are exclusively between symmetry-related thiazolidinone dioxide moieties and have a parallel 'give-and-take-fashion' counterpart. In the other two interactions, the nitrophenyl ring and the cyclohexane ring each offer an H atom to the two O atoms on the sulfone group. Additionally, a C - H⋯π interaction between a C - H group of the cyclohexane ring and the nitrophenyl ring of an adjacent molecule helps to consolidate the structure.

UR - http://www.scopus.com/inward/record.url?scp=85058049314&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85058049314&partnerID=8YFLogxK

U2 - 10.1107/S2056989018015098

DO - 10.1107/S2056989018015098

M3 - Article

C2 - 30574358

AN - SCOPUS:85058049314

VL - 74

SP - 1695

EP - 1699

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

ER -