title: Three anilides of 2,2'-thiodibenzoic acid.
abstract: The structures of N,N'-bis(2-methylphenyl)-2,2'-thiodibenzamide, C(28)H(24)N(2)O(2)S, (Ia), N,N'-bis(2-ethylphenyl)-2,2'-thiodibenzamide, C(30)H(28)N(2)O(2)S, (Ib), and N,N'-bis(2-bromophenyl)-2,2'-thiodibenzamide, C(26)H(18)Br(2)N(2)O(2)S, (Ic), are compared with each other. For the 19 atoms of the consistent thiodibenzamide core, the r.m.s. deviations of the molecules in pairs are 0.29, 0.90 and 0.80 Å for (Ia)/(Ib), (Ia)/(Ic) and (Ib)/(Ic), respectively. The conformations of the central parts of molecules (Ia) and (Ib) are similar due to an intramolecular N-H···O hydrogen-bonding interaction. The molecules of (Ia) are further linked into infinite chains along the c axis by intermolecular N-H···O interactions, whereas the molecules of (Ib) are linked into chains along b by an intermolecular N-H···π contact. The conformation of (Ic) is quite different from those of (Ia) and (Ib), since there is no intramolecular N-H···O hydrogen bond, but instead there is a possible intramolecular N-H···Br hydrogen bond. The molecules are linked into chains along c by intermolecular N-H···O hydrogen bonds.
authors.affiliation: School of Chemistry, University of Manchester, England, UK.
authors.forename: Madeleine
authors.initials: M
authors.lastname: Helliwell
authors.forename: Salma
authors.initials: S
authors.lastname: Moosun
authors.forename: Minu G
authors.initials: MG
authors.lastname: Bhowon
authors.forename: Sabina
authors.initials: S
authors.lastname: Jhaumeer-Laulloo
authors.forename: John A
authors.initials: JA
authors.lastname: Joule
mesh_terms: D000813:Anilides / Q000737:chemistry*; D001565:Benzoates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D015394:Molecular Structure; D013854:Thioamides / Q000737:chemistry*
chemical_list: C577134:2,2'-thiodibenzoic acid; D000813:Anilides; D001565:Benzoates; C577019:N,N'-bis(2-bromophenyl)-2,2'-thiodibenzamide; C577018:N,N'-bis(2-methylphenyl)-2,2'-thiodibenzamide; D013854:Thioamides