Iodo-nitroarenesulfonamides

Interplay of hard and soft hydrogen bonds, I⋯O interactions and aromatic π⋯π stacking interactions

Craig J. Kelly, Janet M.S. Skakle, James L. Wardell, Solange M.S.V. Wardell, John N. Low, Christopher Glidewell*

*Corresponding author for this work

Research output: Contribution to journalArticle

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Abstract

Molecules of N-(4′-iodophenylsulfonyl)-4-nitroaniline, 4-O2NC6H4NHSO2C6H 4I-4′ (1), are linked by three-centre I⋯O2N interactions into chains and these chains are linked into a three-dimensional framework by C-H⋯O hydrogen bonds. In the isomeric N-(4′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4NHSO2C6H4NO 2-4′ (2), the chains generated by the I⋯O2N interactions are again linked into a three-dimensional framework by C-H⋯O hydrogen bonds. Molecules of N,N-bis(3′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4N(SO2C6H4NO 2-3′)2 (3), lie across twofold rotation axes in space group C2/c and they are linked into chains by paired I⋯O=S interactions: these chains are linked into sheets by a C-H⋯O hydrogen bond, and the sheets are linked into a three-dimensional framework by aromatic π⋯π stacking interactions. In N-(4′-iodophenylsulfonyl)-3-nitroaniline. 3-O2NC6H4NHSO2C6H 4I4′ (4). there are R22(8) rings formed by hard N-H⋯O=S hydrogen bonds and R22(24) rings formed by two-centre I⋯nitro interactions, which together generate a chain of fused rings: the combination of a C-H⋯O hydrogen bond and aromatic π⋯π stacking interactions links the chains into sheets. Molecules of N-(4′-iodophenylsulfonvl)-4-methyl-2-nitroaniline, 4-CH3-2-O2NC6H3NHSO 2C6H4I-4′ (5), are linked by N-H⋯O=S and C-H⋯O(nitro) hydrogen bonds into a chain containing alternating R22(8) and R22(10) rings, but there are no I⋯O interactions of either type. There are two molecules in the asymmetric unit of N-(4′-iodophenylsulfonyl)-2-nitroaniline, 2-O2NC6H4NHSO2C6H 4I-4′ (6). and the combination of an I⋯O=S interaction and a hard N-H⋯O(nitro) hydrogen bond links the two types of molecule to form a cyclic, centrosymmetric four-component aggregate. C-H⋯O hydrogen bonds link these four-molecule aggregates to form a molecular ladder. Comparisons are made with structures retrieved from the Cambridge Structural Database.

Original languageEnglish
Pages (from-to)94-108
Number of pages15
JournalActa Crystallographica Section B: Structural Science
Volume58
Issue number1
DOIs
Publication statusPublished - 1 Feb 2002

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Iodo-nitroarenesulfonamides : Interplay of hard and soft hydrogen bonds, I⋯O interactions and aromatic π⋯π stacking interactions. / Kelly, Craig J.; Skakle, Janet M.S.; Wardell, James L.; Wardell, Solange M.S.V.; Low, John N.; Glidewell, Christopher.

In: Acta Crystallographica Section B: Structural Science, Vol. 58, No. 1, 01.02.2002, p. 94-108.

Research output: Contribution to journalArticle

Kelly, Craig J. ; Skakle, Janet M.S. ; Wardell, James L. ; Wardell, Solange M.S.V. ; Low, John N. ; Glidewell, Christopher. / Iodo-nitroarenesulfonamides : Interplay of hard and soft hydrogen bonds, I⋯O interactions and aromatic π⋯π stacking interactions. In: Acta Crystallographica Section B: Structural Science. 2002 ; Vol. 58, No. 1. pp. 94-108.
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title = "Iodo-nitroarenesulfonamides: Interplay of hard and soft hydrogen bonds, I⋯O interactions and aromatic π⋯π stacking interactions",
abstract = "Molecules of N-(4′-iodophenylsulfonyl)-4-nitroaniline, 4-O2NC6H4NHSO2C6H 4I-4′ (1), are linked by three-centre I⋯O2N interactions into chains and these chains are linked into a three-dimensional framework by C-H⋯O hydrogen bonds. In the isomeric N-(4′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4NHSO2C6H4NO 2-4′ (2), the chains generated by the I⋯O2N interactions are again linked into a three-dimensional framework by C-H⋯O hydrogen bonds. Molecules of N,N-bis(3′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4N(SO2C6H4NO 2-3′)2 (3), lie across twofold rotation axes in space group C2/c and they are linked into chains by paired I⋯O=S interactions: these chains are linked into sheets by a C-H⋯O hydrogen bond, and the sheets are linked into a three-dimensional framework by aromatic π⋯π stacking interactions. In N-(4′-iodophenylsulfonyl)-3-nitroaniline. 3-O2NC6H4NHSO2C6H 4I4′ (4). there are R22(8) rings formed by hard N-H⋯O=S hydrogen bonds and R22(24) rings formed by two-centre I⋯nitro interactions, which together generate a chain of fused rings: the combination of a C-H⋯O hydrogen bond and aromatic π⋯π stacking interactions links the chains into sheets. Molecules of N-(4′-iodophenylsulfonvl)-4-methyl-2-nitroaniline, 4-CH3-2-O2NC6H3NHSO 2C6H4I-4′ (5), are linked by N-H⋯O=S and C-H⋯O(nitro) hydrogen bonds into a chain containing alternating R22(8) and R22(10) rings, but there are no I⋯O interactions of either type. There are two molecules in the asymmetric unit of N-(4′-iodophenylsulfonyl)-2-nitroaniline, 2-O2NC6H4NHSO2C6H 4I-4′ (6). and the combination of an I⋯O=S interaction and a hard N-H⋯O(nitro) hydrogen bond links the two types of molecule to form a cyclic, centrosymmetric four-component aggregate. C-H⋯O hydrogen bonds link these four-molecule aggregates to form a molecular ladder. Comparisons are made with structures retrieved from the Cambridge Structural Database.",
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AU - Kelly, Craig J.

AU - Skakle, Janet M.S.

AU - Wardell, James L.

AU - Wardell, Solange M.S.V.

AU - Low, John N.

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N2 - Molecules of N-(4′-iodophenylsulfonyl)-4-nitroaniline, 4-O2NC6H4NHSO2C6H 4I-4′ (1), are linked by three-centre I⋯O2N interactions into chains and these chains are linked into a three-dimensional framework by C-H⋯O hydrogen bonds. In the isomeric N-(4′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4NHSO2C6H4NO 2-4′ (2), the chains generated by the I⋯O2N interactions are again linked into a three-dimensional framework by C-H⋯O hydrogen bonds. Molecules of N,N-bis(3′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4N(SO2C6H4NO 2-3′)2 (3), lie across twofold rotation axes in space group C2/c and they are linked into chains by paired I⋯O=S interactions: these chains are linked into sheets by a C-H⋯O hydrogen bond, and the sheets are linked into a three-dimensional framework by aromatic π⋯π stacking interactions. In N-(4′-iodophenylsulfonyl)-3-nitroaniline. 3-O2NC6H4NHSO2C6H 4I4′ (4). there are R22(8) rings formed by hard N-H⋯O=S hydrogen bonds and R22(24) rings formed by two-centre I⋯nitro interactions, which together generate a chain of fused rings: the combination of a C-H⋯O hydrogen bond and aromatic π⋯π stacking interactions links the chains into sheets. Molecules of N-(4′-iodophenylsulfonvl)-4-methyl-2-nitroaniline, 4-CH3-2-O2NC6H3NHSO 2C6H4I-4′ (5), are linked by N-H⋯O=S and C-H⋯O(nitro) hydrogen bonds into a chain containing alternating R22(8) and R22(10) rings, but there are no I⋯O interactions of either type. There are two molecules in the asymmetric unit of N-(4′-iodophenylsulfonyl)-2-nitroaniline, 2-O2NC6H4NHSO2C6H 4I-4′ (6). and the combination of an I⋯O=S interaction and a hard N-H⋯O(nitro) hydrogen bond links the two types of molecule to form a cyclic, centrosymmetric four-component aggregate. C-H⋯O hydrogen bonds link these four-molecule aggregates to form a molecular ladder. Comparisons are made with structures retrieved from the Cambridge Structural Database.

AB - Molecules of N-(4′-iodophenylsulfonyl)-4-nitroaniline, 4-O2NC6H4NHSO2C6H 4I-4′ (1), are linked by three-centre I⋯O2N interactions into chains and these chains are linked into a three-dimensional framework by C-H⋯O hydrogen bonds. In the isomeric N-(4′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4NHSO2C6H4NO 2-4′ (2), the chains generated by the I⋯O2N interactions are again linked into a three-dimensional framework by C-H⋯O hydrogen bonds. Molecules of N,N-bis(3′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4N(SO2C6H4NO 2-3′)2 (3), lie across twofold rotation axes in space group C2/c and they are linked into chains by paired I⋯O=S interactions: these chains are linked into sheets by a C-H⋯O hydrogen bond, and the sheets are linked into a three-dimensional framework by aromatic π⋯π stacking interactions. In N-(4′-iodophenylsulfonyl)-3-nitroaniline. 3-O2NC6H4NHSO2C6H 4I4′ (4). there are R22(8) rings formed by hard N-H⋯O=S hydrogen bonds and R22(24) rings formed by two-centre I⋯nitro interactions, which together generate a chain of fused rings: the combination of a C-H⋯O hydrogen bond and aromatic π⋯π stacking interactions links the chains into sheets. Molecules of N-(4′-iodophenylsulfonvl)-4-methyl-2-nitroaniline, 4-CH3-2-O2NC6H3NHSO 2C6H4I-4′ (5), are linked by N-H⋯O=S and C-H⋯O(nitro) hydrogen bonds into a chain containing alternating R22(8) and R22(10) rings, but there are no I⋯O interactions of either type. There are two molecules in the asymmetric unit of N-(4′-iodophenylsulfonyl)-2-nitroaniline, 2-O2NC6H4NHSO2C6H 4I-4′ (6). and the combination of an I⋯O=S interaction and a hard N-H⋯O(nitro) hydrogen bond links the two types of molecule to form a cyclic, centrosymmetric four-component aggregate. C-H⋯O hydrogen bonds link these four-molecule aggregates to form a molecular ladder. Comparisons are made with structures retrieved from the Cambridge Structural Database.

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