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Eight isostructural 4,4'-disubstituted N-phenylbenzenesulfonamides

Eight isostructural 4,4'-disubstituted N-phenylbenzenesulfonamides
Eight isostructural 4,4'-disubstituted N-phenylbenzenesulfonamides
The isostructural crystals of 4-cyano-N-(4-methoxyphenyl)benzenesulfonamide, C14H12N2O3S, (I), N-(4-methoxyphenyl)-4-(trifluoromethyl) benzenesulfonamide, C14H12F3NO3S, (II), 4-iodo-N-(4-methoxyphenyl) benzenesulfonamide, C13H12INO3S, (III), 4-bromo-N-(4-methoxyphenyl) benzenesulfonamide, C13H12BrNO3S, (IV), 4-chloro-N-(4-methoxyphenyl) benzenesulfonamide, C13H12ClNO3S, (V), 4-fluoro-N-(4-methoxyphenyl) benzenesulfonamide, C13H12FNO3S, (VI), N-(4-chlorophenyl)-4-methoxybenzenesulfonamide, C13H12ClNO3S, (VII), and 4-cyano-N-phenylbenzenesulfonamide, C13H10N2O2S, (VIII), contain infinite chains composed of N-H ··· O(sulfonyl) hydrogen-bonded molecules. The crystal structures of (I)-(VIII) have been compared using the XPac software and quantitative descriptors of isostructurality were generated [Gelbrich, Threlfall & Hursthouse (2012). Cryst-EngComm, 14, 5454-5464]. Certain isostructural relationships in this series involve molecules with substantially different spatial demands, e. g. (VI) and (VIII) are related by the simultaneous interchange of F -> CN on the benzenesulfonamide ring and OMe -> H on the N-phenyl ring, which indicates that the geometry of the three-dimensional crystal-packing mode of (I)-(VIII) is unusually adaptable to different molecular shapes.
0108-2701
o421-o426
Gelbrich, Thomas
42309d69-eaf1-4bb7-ba2e-db61f338e370
Threlfall, Terence L.
26a8854d-5a4e-46fa-b2fd-00ebe67747d8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Gelbrich, Thomas
42309d69-eaf1-4bb7-ba2e-db61f338e370
Threlfall, Terence L.
26a8854d-5a4e-46fa-b2fd-00ebe67747d8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da

Gelbrich, Thomas, Threlfall, Terence L. and Hursthouse, Michael B. (2012) Eight isostructural 4,4'-disubstituted N-phenylbenzenesulfonamides. Acta Crystallographica Section C: Crystal Structure Communications, 68 (10), o421-o426. (doi:10.1107/S0108270112039297).

Record type: Article

Abstract

The isostructural crystals of 4-cyano-N-(4-methoxyphenyl)benzenesulfonamide, C14H12N2O3S, (I), N-(4-methoxyphenyl)-4-(trifluoromethyl) benzenesulfonamide, C14H12F3NO3S, (II), 4-iodo-N-(4-methoxyphenyl) benzenesulfonamide, C13H12INO3S, (III), 4-bromo-N-(4-methoxyphenyl) benzenesulfonamide, C13H12BrNO3S, (IV), 4-chloro-N-(4-methoxyphenyl) benzenesulfonamide, C13H12ClNO3S, (V), 4-fluoro-N-(4-methoxyphenyl) benzenesulfonamide, C13H12FNO3S, (VI), N-(4-chlorophenyl)-4-methoxybenzenesulfonamide, C13H12ClNO3S, (VII), and 4-cyano-N-phenylbenzenesulfonamide, C13H10N2O2S, (VIII), contain infinite chains composed of N-H ··· O(sulfonyl) hydrogen-bonded molecules. The crystal structures of (I)-(VIII) have been compared using the XPac software and quantitative descriptors of isostructurality were generated [Gelbrich, Threlfall & Hursthouse (2012). Cryst-EngComm, 14, 5454-5464]. Certain isostructural relationships in this series involve molecules with substantially different spatial demands, e. g. (VI) and (VIII) are related by the simultaneous interchange of F -> CN on the benzenesulfonamide ring and OMe -> H on the N-phenyl ring, which indicates that the geometry of the three-dimensional crystal-packing mode of (I)-(VIII) is unusually adaptable to different molecular shapes.

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More information

Published date: October 2012
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 347314
URI: http://eprints.soton.ac.uk/id/eprint/347314
ISSN: 0108-2701
PURE UUID: 5e21a6e4-d851-45bb-99ca-2c562415d1bd

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Date deposited: 21 Jan 2013 10:06
Last modified: 14 Mar 2024 12:46

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Author: Thomas Gelbrich
Author: Terence L. Threlfall

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