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-oxadiazineN,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, C21H14F2N2, (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 fromN,N-dimethylformamide to give the monosolvate, C22H16F2N2O3·C3H7NO, (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.