Acta Crystallographica Section B

Structural Science

Volume 58, Part 1 (February 2002)

research papers

Acta Cryst. (2002). B58, 94-108 [ doi:10.1107/S0108768101016858 ]

Iodo-nitroarenesulfonamides: interplay of hard and soft hydrogen bonds, IO interactions and aromatic stacking interactions

C. J. Kelly, J. M. S. Skakle, J. L. Wardell, S. M. S. V. Wardell, J. N. Low and C. Glidewell

Abstract: Molecules of N-(4'-iodophenylsulfonyl)-4-nitroaniline, 4-O₂NC₆H₄NHSO₂C₆H₄I-4' (1), are linked by three-centre IO₂N interactions into chains and these chains are linked into a three-dimensional framework by C-HO hydrogen bonds. In the isomeric N-(4'-nitrophenylsulfonyl)-4-iodoaniline, 4-IC₆H₄NHSO₂C₆H₄NO₂-4' (2), the chains generated by the IO₂N interactions are again linked into a three-dimensional framework by C-HO hydrogen bonds. Molecules of N,N-bis(3'-nitrophenylsulfonyl)-4-iodoaniline, 4-IC₆H₄N(SO₂C₆H₄NO₂-3')₂ (3), lie across twofold rotation axes in space group C2/c and they are linked into chains by paired IO=S interactions: these chains are linked into sheets by a C-HO hydrogen bond, and the sheets are linked into a three-dimensional framework by aromatic [bold pi] stacking interactions. In N-(4'-iodophenylsulfonyl)-3-nitroaniline, 3-O₂NC₆H₄NHSO₂C₆H₄I-4' (4), there are R²₂(8) rings formed by hard N-HO=S hydrogen bonds and R²₂(24) rings formed by two-centre Initro interactions, which together generate a chain of fused rings: the combination of a C-HO hydrogen bond and aromatic [bold pi] stacking interactions links the chains into sheets. Molecules of N-(4'-iodophenylsulfonyl)-4-methyl-2-nitroaniline, 4-CH₃-2-O₂NC₆H₃NHSO₂C₆H₄I-4' (5), are linked by N-HO=S and C-HO(nitro) hydrogen bonds into a chain containing alternating R²₂(8) and R²₂(10) rings, but there are no IO interactions of either type. There are two molecules in the asymmetric unit of N-(4'-iodophenylsulfonyl)-2-nitroaniline, 2-O₂NC₆H₄NHSO₂C₆H₄I-4' (6), and the combination of an IO=S interaction and a hard N-HO(nitro) hydrogen bond links the two types of molecule to form a cyclic, centrosymmetric four-component aggregate. C-HO hydrogen bonds link these four-molecule aggregates to form a molecular ladder. Comparisons are made with structures retrieved from the Cambridge Structural Database.

Keywords: hydrogen bonds; stacking interactions; aggregates; Cambridge Structural Database.


	Structure factor file (CIF format) (151.6 kbytes) Contains datablock I

	Structure factor file (CIF format) (130.6 kbytes) Contains datablock 2

	Structure factor file (CIF format) (117.0 kbytes) Contains datablock 3

	Structure factor file (CIF format) (149.0 kbytes) Contains datablock 4

	Structure factor file (CIF format) (155.7 kbytes) Contains datablock V

	Structure factor file (CIF format) (252.7 kbytes) Contains datablock 6

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