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

Samshuddin, Seranthimata and Jasinski, Jerry P. and Golen, James A. and Narayana, B. and Yathirajan, H. S. and Glidewell, Christopher (2014) 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. Acta Crystallographica Section C, 70 (9). pp. 867-871. ISSN 2053-2296

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Official URL: https://doi.org/10.1107/S2053229614017707

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...[pi](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, 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.

Item Type: Article
Uncontrolled Keywords: crystal structure, hydrogen bonding, biological activity, pyrazoles, oxadiazines
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: MUL SWAPNA user
Date Deposited: 08 Nov 2019 06:17
Last Modified: 08 Nov 2019 06:17
URI: http://eprints.uni-mysore.ac.in/id/eprint/9893

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