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). Cryst­EngComm, 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[rightwards arrow]CN on the benzene­sul­fon­amide ring and OMe[rightwards arrow]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.