title: Hydrogen-bonded chains in 3,5-bis(4-fluorophenyl)-1-phenyl-1H-pyrazole and complex hydrogen-bonded sheets in (5RS,6SR)-6-(4-fluorobenzoyl)-5-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5,6-dihydro-4H-1,3,4-oxadiazine N,N-dimethylformamide monosolvate.
abstract: Two different heterocycles, a pyrazole and an oxadiazine, are formed by the reactions of a common precursor, (2RS,3SR)-2,3-dibromo-1,3-bis(4-fluorophenyl)propan-1-one, with different simple hydrazines. In 3,5-bis(4-fluorophenyl)-1-phenyl-1H-pyrazole, C(21)H(14)F(2)N(2), (I), formed using phenylhydrazine, there is some aromatic-type delocalization in the pyrazole ring, and the molecules are linked into simple chains by a single C-H...π(arene) hydrogen bond. The reaction with 4-hydroxybenzohydrazide gives (5RS,6SR)-6-(4-fluorobenzoyl)-5-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5,6-dihydro-4H-1,3,4-oxadiazine, which was crystallized from N,N-dimethylformamide to give the monosolvate, C(22)H(16)F(2)N(2)O(3) · C(3)H(7)NO, (II), in which the solvent molecule is disordered over two sets of atomic sites having occupancies of 0.557 (10) and 0.443 (10). The oxadiazine molecules in (II) are linked by a combination of N-H...N and C-H...O hydrogen bonds to form complex sheets, having the hydrogen bonds in the central layer and with the solvent molecules attached at the outer faces by O-H...O hydrogen bonds.
authors.affiliation: Department of Studies in Chemistry, Mangalore University, Manasagangotri, Mysore 570 006, India.
authors.forename: Seranthimata
authors.initials: S
authors.lastname: Samshuddin
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: Department of Studies in Chemistry, University of Mysore, Mysore 570 006, India.
authors.forename: Hemmige S
authors.initials: HS
authors.lastname: Yathirajan
authors.affiliation: School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland.
authors.forename: Christopher
authors.initials: C
authors.lastname: Glidewell
mesh_terms: D018360:Crystallography, X-Ray; D005559:Formamides / Q000737:chemistry*; D006834:Hydrazines / Q000737:chemistry*; D006860:Hydrogen Bonding; D062385:Hydroxybenzoates / Q000737:chemistry*; D010078:Oxazines / Q000737:chemistry*; D011720:Pyrazoles / Q000737:chemistry*
chemical_list: C000593281:(5RS,6SR)-6-(4-fluorobenzoyl)-5-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5,6-dihydro-4H-1,3,4-oxadiazine N,N-dimethylformamide; C000593280:3,5-bis(4-fluorophenyl)-1-phenyl-1H-pyrazole; D005559:Formamides; D006834:Hydrazines; D062385:Hydroxybenzoates; D010078:Oxazines; D011720:Pyrazoles; C002429:4-hydroxybenzoic acid hydrazide
keywords: biological activity; crystal structure; hydrogen bonding; oxadiazines; pyrazoles