Molecular conformation and supramolecular aggregation in four 2,3,4,5-tetrahydro-3,4-diphenylbenzothiazepines
Abstract:In (2RS,4RS)-1-acetyl-2,3,4,5-tetrahydro-2,4-diphenyl-1,5-benzothiazepine, C23H21NOS, (I), and (2RS,4RS)-1-chloroacetyl-2,3,4,5-tetrahydro-2,4-diphenyl-1,5-benzothiazepine,C23H20ClNOS, (II), the seven-membered rings have boat conformations, whereas in (2RS,4RS)-1-benzoyl-2,3,4,5-tetrahydro-2,4-diphenyl-1,5-benzothiazepine, C28H23NOS, (III), this ring has a conformation intermediate between the boat and twist-boat forms. The molecules of (I) are linked into isolated (16) dimers by two C—H…O hydrogen bonds [H…O = 2.41 and 2.47 Å, C…O = 3.268 (3) and 3.336 (3) Å, and C—H…O = 150 and 152°]. In (II), the molecules are again linked by two C—H…O hydrogen bonds [H…O = 2.42 and 2.48 Å, C…O = 3.295 (3) and 3.364 (2) Å, and C—H…O = 153 and 154°], forming chains of alternating (18) and (22) rings. Two C—H…O hydrogen bonds [H…O = 2.49 and 2.53 Å, C…O = 3.347 (2) and 3.295 (2) Å, and C—H…O = 150 and 138°] link the molecules of (III) into sheets containing alternating (22) and (30) rings. Re-examination of the published structure of (2RS,4RS)-2,3,4,5-tetrahydro-2,4-diphenyl-1,5-benzothiazepine shows that the molecules are linked by three C—H…(arene) hydrogen bonds into a three-dimensional framework.
Document Type: Research Article
Publication date: June 1, 2004