title: Halogenated C,N-diarylacetamides: molecular conformations and supramolecular assembly.
abstract: The structures of four halogenated N,2-diarylacetamides are reported and compared with a range of analogues. N-(4-Chloro-3-methylphenyl)-2-phenylacetamide, C(15)H(14)ClNO, (I), and N-(4-bromo-3-methylphenyl)-2-phenylacetamide, C(15)H(14)BrNO, (II), are isostructural in the space group P-1. The molecules of (I) and (II) are linked into chains of rings by a combination of N-H...O and C-H...π(arene) hydrogen bonds. The molecules of N-(4-chloro-3-methylphenyl)-2-(2,4-dichlorophenyl)acetamide, C(15)H(12)Cl(3)NO, (III), and N-(4-bromo-3-methylphenyl)-2-(2-chlorophenyl)acetamide, C(15)H(13)BrClNO, (IV), are linked into simple C(4) chains by N-H...O hydrogen bonds, but significant C-H...π(arene) interactions are absent. The N-aryl groups in compounds (III) and (IV) adopt a different orientation, by ca 180°, from that of the corresponding groups in compounds (I) and (II), but otherwise the conformations of (I)-(IV) are very similar. Comparisons are drawn between compounds (I) and (IV) and a range of analogues of the type R(1)CH(2)CONHR(2), where R(2) represents a halogenated aryl ring and R(1) represents either another halogenated aryl ring or a naphthalen-1-yl unit.
authors.affiliation: Department of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India.
authors.forename: Prakash S
authors.initials: PS
authors.lastname: Nayak
authors.affiliation: Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA.
authors.forename: Jerry P
authors.initials: JP
authors.lastname: Jasinski
authors.affiliation: Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA.
authors.forename: James A
authors.initials: JA
authors.lastname: Golen
authors.affiliation: Department of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India.
authors.forename: Badiadka
authors.initials: B
authors.lastname: Narayana
authors.affiliation: University of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India.
authors.forename: Manpreet
authors.initials: M
authors.lastname: Kaur
authors.affiliation: University of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India.
authors.forename: Hemmige S
authors.initials: HS
authors.lastname: Yathirajan
authors.affiliation: School of Chemistry, University of St Andrews, Fife KY16 9ST, England.
authors.forename: Christopher
authors.initials: C
authors.lastname: Glidewell
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D054879:Halogenation; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*
chemical_list: D000081:Acetamides; C000593295:N-(4-bromo-3-methylphenyl)-2-phenylacetamide; C000593294:N-(4-chloro-3-methylphenyl)-2-phenylacetamide; D009281:Naphthalenes; C030686:acetamide
keywords: C,N-diarylacetamides; acetamides; benzyl penicillins; crystal structure; hydrogen bonding; molecular conformation; supramolecular assembly