Crystal structures of 2,3-bis(4-chlorophenyl)-1,3-thiazolidin-4-one and trans-2,3-bis(4-chlorophen-yl)-1,3-thiazolidin-4-one 1-oxide

Hemant P. Yennawar, John Tierney, Patrick D. Hullihen, Lee Jonathan Silverberg, H. Stoeckli-Evans

Research output: Contribution to journalArticle

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Abstract

In the crystal structures of the title compounds, C15H11Cl2NOS, (1), and C15H11Cl2NO2S, (2), wherein (2) is the oxidized form of (1), the thiazolidine ring is attached to two chlorophenyl rings. The chlorophenyl ring on the 2-carbon atom position points in the same direction as that of the S atom in (1), while in (2), the S atom points in the opposite direction. The O atom on the chiral S atom in (2) is trans to the chlorophenyl ring on the 2-carbon. The chlorophenyl ring planes in each structure are close to orthogonal, making dihedral angles of 78.61 (6) and 87.46 (8)° in (1) and (2), respectively. The thiazolidine ring has a twisted conformation on the S - Cmethine bond in (1), and an envelope conformation with the S atom 0.715 (3) Å out of the plane of other four atoms in (2). In the crystal of (1), molecules are linked by C - H⋯O hydrogen bonds, as well as by slipped parallel π-π interactions [inter-centroid distance = 3.840 (3) Å] between inversion-related phenyl rings, forming sheets parallel to (001). In the crystal of (2), molecules are linked via C - H⋯O and C - H⋯Cl hydrogen bonds, forming slabs parallel to (001).

Original languageEnglish (US)
Pages (from-to)264-267
Number of pages4
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number3
DOIs
StatePublished - Mar 1 2015

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Oxides
Crystal structure
Atoms
crystal structure
oxides
rings
atoms
Thiazolidines
Conformations
Hydrogen bonds
Carbon
hydrogen bonds
Crystals
Molecules
carbon
Chemical bonds
Dihedral angle
centroids
crystals
dihedral angle

All Science Journal Classification (ASJC) codes

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

Cite this

@article{f64b221ac2414058a07b49159d859643,
title = "Crystal structures of 2,3-bis(4-chlorophenyl)-1,3-thiazolidin-4-one and trans-2,3-bis(4-chlorophen-yl)-1,3-thiazolidin-4-one 1-oxide",
abstract = "In the crystal structures of the title compounds, C15H11Cl2NOS, (1), and C15H11Cl2NO2S, (2), wherein (2) is the oxidized form of (1), the thiazolidine ring is attached to two chlorophenyl rings. The chlorophenyl ring on the 2-carbon atom position points in the same direction as that of the S atom in (1), while in (2), the S atom points in the opposite direction. The O atom on the chiral S atom in (2) is trans to the chlorophenyl ring on the 2-carbon. The chlorophenyl ring planes in each structure are close to orthogonal, making dihedral angles of 78.61 (6) and 87.46 (8)° in (1) and (2), respectively. The thiazolidine ring has a twisted conformation on the S - Cmethine bond in (1), and an envelope conformation with the S atom 0.715 (3) {\AA} out of the plane of other four atoms in (2). In the crystal of (1), molecules are linked by C - H⋯O hydrogen bonds, as well as by slipped parallel π-π interactions [inter-centroid distance = 3.840 (3) {\AA}] between inversion-related phenyl rings, forming sheets parallel to (001). In the crystal of (2), molecules are linked via C - H⋯O and C - H⋯Cl hydrogen bonds, forming slabs parallel to (001).",
author = "Yennawar, {Hemant P.} and John Tierney and Hullihen, {Patrick D.} and Silverberg, {Lee Jonathan} and H. Stoeckli-Evans",
year = "2015",
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day = "1",
doi = "10.1107/S2056989015001954",
language = "English (US)",
volume = "71",
pages = "264--267",
journal = "Acta Crystallographica Section E: Structure Reports Online",
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publisher = "International Union of Crystallography",
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Crystal structures of 2,3-bis(4-chlorophenyl)-1,3-thiazolidin-4-one and trans-2,3-bis(4-chlorophen-yl)-1,3-thiazolidin-4-one 1-oxide. / Yennawar, Hemant P.; Tierney, John; Hullihen, Patrick D.; Silverberg, Lee Jonathan; Stoeckli-Evans, H.

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, No. 3, 01.03.2015, p. 264-267.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Crystal structures of 2,3-bis(4-chlorophenyl)-1,3-thiazolidin-4-one and trans-2,3-bis(4-chlorophen-yl)-1,3-thiazolidin-4-one 1-oxide

AU - Yennawar, Hemant P.

AU - Tierney, John

AU - Hullihen, Patrick D.

AU - Silverberg, Lee Jonathan

AU - Stoeckli-Evans, H.

PY - 2015/3/1

Y1 - 2015/3/1

N2 - In the crystal structures of the title compounds, C15H11Cl2NOS, (1), and C15H11Cl2NO2S, (2), wherein (2) is the oxidized form of (1), the thiazolidine ring is attached to two chlorophenyl rings. The chlorophenyl ring on the 2-carbon atom position points in the same direction as that of the S atom in (1), while in (2), the S atom points in the opposite direction. The O atom on the chiral S atom in (2) is trans to the chlorophenyl ring on the 2-carbon. The chlorophenyl ring planes in each structure are close to orthogonal, making dihedral angles of 78.61 (6) and 87.46 (8)° in (1) and (2), respectively. The thiazolidine ring has a twisted conformation on the S - Cmethine bond in (1), and an envelope conformation with the S atom 0.715 (3) Å out of the plane of other four atoms in (2). In the crystal of (1), molecules are linked by C - H⋯O hydrogen bonds, as well as by slipped parallel π-π interactions [inter-centroid distance = 3.840 (3) Å] between inversion-related phenyl rings, forming sheets parallel to (001). In the crystal of (2), molecules are linked via C - H⋯O and C - H⋯Cl hydrogen bonds, forming slabs parallel to (001).

AB - In the crystal structures of the title compounds, C15H11Cl2NOS, (1), and C15H11Cl2NO2S, (2), wherein (2) is the oxidized form of (1), the thiazolidine ring is attached to two chlorophenyl rings. The chlorophenyl ring on the 2-carbon atom position points in the same direction as that of the S atom in (1), while in (2), the S atom points in the opposite direction. The O atom on the chiral S atom in (2) is trans to the chlorophenyl ring on the 2-carbon. The chlorophenyl ring planes in each structure are close to orthogonal, making dihedral angles of 78.61 (6) and 87.46 (8)° in (1) and (2), respectively. The thiazolidine ring has a twisted conformation on the S - Cmethine bond in (1), and an envelope conformation with the S atom 0.715 (3) Å out of the plane of other four atoms in (2). In the crystal of (1), molecules are linked by C - H⋯O hydrogen bonds, as well as by slipped parallel π-π interactions [inter-centroid distance = 3.840 (3) Å] between inversion-related phenyl rings, forming sheets parallel to (001). In the crystal of (2), molecules are linked via C - H⋯O and C - H⋯Cl hydrogen bonds, forming slabs parallel to (001).

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JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

SN - 1600-5368

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