Open AccessMonoclinic pseudosymmetry in 2‐phenoxybenzenesulfonamide, a triclinic structure having Z ′ = 4, and spontaneous resolution in monoclinic N ‐methyl‐2‐phenoxybenzenesulfonamide
Author(s) -
Glidewell Christopher,
Low John N.,
Skakle Janet M. S.,
Wardell James L.
Publication year - 2004
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s010827010400719x
Subject(s) - monoclinic crystal system , triclinic crystal system , hydrogen bond , crystallography , chemistry , amide , benzene , group (periodic table) , stereochemistry , crystal structure , resolution (logic) , molecule , organic chemistry , artificial intelligence , computer science
2‐Phenoxybenzenesulfonamide, C 12 H 11 NO 3 S, (I), crystallizes in space group P with Z ′ = 4, but the structure closely mimics the monoclinic space group P 2 1 / b with Z ′ = 2. The molecules of (I) are linked by a combination of N—H⋯O and C—H⋯O hydrogen bonds into two independent chains of centrosymmetric edge‐fused R (18) and R (34) rings. N ‐Methyl‐2‐phenoxybenzenesulfonamide, C 13 H 13 NO 3 S, (II), crystallizes in space group P 2 1 with Z ′ = 1, and is an example of spontaneous resolution. The molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds into chains of spiro‐fused R (12) rings, and these chains are linked into sheets by a single C—H⋯π(arene) hydrogen bond.