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

36 Citations (Scopus)

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

    Fingerprint

ASJC Scopus subject areas

  • Medicine(all)
  • Biochemistry, Genetics and Molecular Biology(all)

Cite this