Five symmetrically substituted 2-aryl-3-benzyl-1,3-thiazolidin-4-ones: Supramolecular structures in zero, one and two dimensions

W. Cunico, L. R. Capri, C. R. B. Gomes, S. M. S. V. Wardell, John N Low, C. Glidewell

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Abstract

There are no direction-specific interactions between the molecules of 3-(2-methoxybenzyl)-2-(2-methoxyphenyl)-1,3-thiazolidin-4-one, C18H19NO3S, (I); the molecules of 3-(4-nitrobenzyl)-2-(4-nitrophenyl)-1,3-thiazolidin-4-one, C16H13N3O5S, (II), are linked by four independent C-H...O hydrogen bonds into complex chains of fused rings. In 3-(4-methoxybenzyl)-2-(4-methoxyphenyl)-1,3-thiazolidin-4-one, (III), isomeric with (I), the molecules are linked into sheets by a combination of C-H...O and C-H...p(arene) hydrogen bonds, while in 3-(2-nitrobenzyl)-2-(2-nitrophenyl)-1,3-thiazolidin-4-one, (IV), isomeric with (II), the sheets are built from three independent C-H...O hydrogen bonds and one C-H...p(arene) hydrogen bond, and reinforced by an aromatic p-p stacking interaction. In 3-(2-fluorobenzyl)-2-(2-fluorophenyl)-1,3-thiazolidin-4-one, C16H13F2NOS, (V), where the 2-aryl ring exhibits orientational disorder, the molecules are linked into sheets by a combination of C-H...O and C-H...p(arene) hydrogen bonds, and the sheets are linked in pairs, forming bilayers, by an aromatic p-p stacking interaction.

Original languageEnglish
Pages (from-to)o102-o107
Number of pages6
JournalActa Crystallographica Section C, Crystal Structure Communications
Volume63
Issue number2
DOIs
Publication statusPublished - Feb 2007

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Five symmetrically substituted 2-aryl-3-benzyl-1,3-thiazolidin-4-ones : Supramolecular structures in zero, one and two dimensions. / Cunico, W.; Capri, L. R.; Gomes, C. R. B.; Wardell, S. M. S. V.; Low, John N; Glidewell, C.

In: Acta Crystallographica Section C, Crystal Structure Communications, Vol. 63, No. 2, 02.2007, p. o102-o107.

Research output: Contribution to journalArticle

Cunico, W. ; Capri, L. R. ; Gomes, C. R. B. ; Wardell, S. M. S. V. ; Low, John N ; Glidewell, C. / Five symmetrically substituted 2-aryl-3-benzyl-1,3-thiazolidin-4-ones : Supramolecular structures in zero, one and two dimensions. In: Acta Crystallographica Section C, Crystal Structure Communications. 2007 ; Vol. 63, No. 2. pp. o102-o107.
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abstract = "There are no direction-specific interactions between the molecules of 3-(2-methoxybenzyl)-2-(2-methoxyphenyl)-1,3-thiazolidin-4-one, C18H19NO3S, (I); the molecules of 3-(4-nitrobenzyl)-2-(4-nitrophenyl)-1,3-thiazolidin-4-one, C16H13N3O5S, (II), are linked by four independent C-H...O hydrogen bonds into complex chains of fused rings. In 3-(4-methoxybenzyl)-2-(4-methoxyphenyl)-1,3-thiazolidin-4-one, (III), isomeric with (I), the molecules are linked into sheets by a combination of C-H...O and C-H...p(arene) hydrogen bonds, while in 3-(2-nitrobenzyl)-2-(2-nitrophenyl)-1,3-thiazolidin-4-one, (IV), isomeric with (II), the sheets are built from three independent C-H...O hydrogen bonds and one C-H...p(arene) hydrogen bond, and reinforced by an aromatic p-p stacking interaction. In 3-(2-fluorobenzyl)-2-(2-fluorophenyl)-1,3-thiazolidin-4-one, C16H13F2NOS, (V), where the 2-aryl ring exhibits orientational disorder, the molecules are linked into sheets by a combination of C-H...O and C-H...p(arene) hydrogen bonds, and the sheets are linked in pairs, forming bilayers, by an aromatic p-p stacking interaction.",
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AU - Capri, L. R.

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AU - Low, John N

AU - Glidewell, C.

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N2 - There are no direction-specific interactions between the molecules of 3-(2-methoxybenzyl)-2-(2-methoxyphenyl)-1,3-thiazolidin-4-one, C18H19NO3S, (I); the molecules of 3-(4-nitrobenzyl)-2-(4-nitrophenyl)-1,3-thiazolidin-4-one, C16H13N3O5S, (II), are linked by four independent C-H...O hydrogen bonds into complex chains of fused rings. In 3-(4-methoxybenzyl)-2-(4-methoxyphenyl)-1,3-thiazolidin-4-one, (III), isomeric with (I), the molecules are linked into sheets by a combination of C-H...O and C-H...p(arene) hydrogen bonds, while in 3-(2-nitrobenzyl)-2-(2-nitrophenyl)-1,3-thiazolidin-4-one, (IV), isomeric with (II), the sheets are built from three independent C-H...O hydrogen bonds and one C-H...p(arene) hydrogen bond, and reinforced by an aromatic p-p stacking interaction. In 3-(2-fluorobenzyl)-2-(2-fluorophenyl)-1,3-thiazolidin-4-one, C16H13F2NOS, (V), where the 2-aryl ring exhibits orientational disorder, the molecules are linked into sheets by a combination of C-H...O and C-H...p(arene) hydrogen bonds, and the sheets are linked in pairs, forming bilayers, by an aromatic p-p stacking interaction.

AB - There are no direction-specific interactions between the molecules of 3-(2-methoxybenzyl)-2-(2-methoxyphenyl)-1,3-thiazolidin-4-one, C18H19NO3S, (I); the molecules of 3-(4-nitrobenzyl)-2-(4-nitrophenyl)-1,3-thiazolidin-4-one, C16H13N3O5S, (II), are linked by four independent C-H...O hydrogen bonds into complex chains of fused rings. In 3-(4-methoxybenzyl)-2-(4-methoxyphenyl)-1,3-thiazolidin-4-one, (III), isomeric with (I), the molecules are linked into sheets by a combination of C-H...O and C-H...p(arene) hydrogen bonds, while in 3-(2-nitrobenzyl)-2-(2-nitrophenyl)-1,3-thiazolidin-4-one, (IV), isomeric with (II), the sheets are built from three independent C-H...O hydrogen bonds and one C-H...p(arene) hydrogen bond, and reinforced by an aromatic p-p stacking interaction. In 3-(2-fluorobenzyl)-2-(2-fluorophenyl)-1,3-thiazolidin-4-one, C16H13F2NOS, (V), where the 2-aryl ring exhibits orientational disorder, the molecules are linked into sheets by a combination of C-H...O and C-H...p(arene) hydrogen bonds, and the sheets are linked in pairs, forming bilayers, by an aromatic p-p stacking interaction.

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JO - Acta Crystallographica Section C, Crystal Structure Communications

JF - Acta Crystallographica Section C, Crystal Structure Communications

SN - 0108-2701

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