title: An additional methylene group driving the conformation and assembly of two arylsulfonamide para-alkoxychalcone hybrids.
abstract: The structures of two arylsulfonamide para-alkoxychalcones, namely, N-{4-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide, C22H19NO4S, (I), and N-{4-[(E)-3-(4-ethoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide, C23H21NO4S, (II), reveal the effect of the inclusion of one -CH2- group between the CH3 branch and the alkoxy O atom on the conformation and crystal structure. Although the molecular conformations and one-dimensional chain motifs are the same in both structures, their crystallographic symmetry, number of independent molecules and crystal packing are different. The crystal packing of (I) is stabilized by weak C-H...π and π-π interactions, while only C-H...π contacts occur in the structure of (II). The role of the additional methylene group in the crystal packing can also be seen in the fact that the alkoxy O atom is an acceptor in nonclassical hydrogen bonds only in the para-ethoxy analogue, (II). The remarkable similarity between the crystal packing features of (I) and (II) lies in the formation of N-H...O hydrogen-bonded ribbons, a synthon commonly found in related compounds.
authors: Institute of Chemistry, Federal University of Goiás, Goiânia, GO 74001-970, Brazil.
authors: Mirian R C
authors: MR
authors: de Castro
authors: Angelo Q
authors: AQ
authors: Aragão
authors: Hamilton B
authors: HB
authors: Napolitano
authors: Caridad
authors: C
authors: Noda-Perez
authors: Felipe T
authors: FT
authors: Martins
mesh_terms: D047188:Chalcones / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D015394:Molecular Structure; D013449:Sulfonamides / Q000737:chemistry*; D000096926:Benzenesulfonamides
chemical_list: D047188:Chalcones; D013449:Sulfonamides; D000096926:Benzenesulfonamides; C580897:N-(4-((E)-3-(4-methoxyphenyl)prop-2-enoyl)phenyl)benzenesulfonamide