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. Issue 9 (7th August 2014)

• Record Type: Journal Article
• Authors: Samshuddin, Seranthimata; Jasinski, Jerry P.; Golen, James A.; Narayana, Badiadka; Yathirajan, Hemmige S.; Glidewell, Christopher
• Is Part Of: Acta crystallographica. Volume 70:Issue 9(2014:Sep.)
• Page Start: 867
• Page End: 871
• Publication Date: 2014-08-07
• Subjects: Crystallography -- Periodicals; Crystals -- Periodicals; 548.3
• DOI: 10.1107/S2053229614017707
• Languages: English
• ISSNs: 2053-2296

Abstract

<abstract abstract-type="main" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Two different heterocycles, a pyrazole and an oxadiazine, are formed by the reactions of a common precursor, (2<italic>RS</italic>, 3<italic>SR</italic>)‐2, 3‐dibromo‐1, 3‐bis(4‐fluorophenyl)propan‐1‐one, with different simple hydrazines. In 3, 5‐bis(4‐fluorophenyl)‐1‐phenyl‐1<italic>H</italic>‐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 (5<italic>RS</italic>, 6<italic>SR</italic>)‐6‐(4‐fluorobenzoyl)‐5‐(4‐fluorophenyl)‐2‐(4‐hydroxyphenyl)‐5, 6‐dihydro‐4<italic>H</italic>‐1, 3, 4‐oxadiazine, which was crystallized from <italic>N</italic>, <italic>N</italic>‐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.</p> </abstract>