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, S. and Jasinski, J. 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: Structural Chemistry, 70. pp. 867-871. ISSN 2053-2296

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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(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,Ndimethylformamide 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-HN and C-HO 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-HO hydrogen bonds.

Item Type:	Article
Uncontrolled Keywords:	3, Crystal structure, Hydrogen bonds, Molecules, chemistry, pyrazole derivative, Pyrazoles, Crystallography, hydrogen bond, Hydrogen Bonding, X ray crystallography, X-Ray, Bioactivity, Chains, Complexation, hydroxybenzoic acid derivative, oxazine derivative, Oxazines, Hydrogen bonded sheets, (5RS, 4-hydroxybenzoic acid hydrazide, 4-oxadiazine N, 5-bis(4-fluorophenyl)-1-phenyl-1H-pyrazole, 6-dihydro-4H-1, 6SR)-6-(4-fluorobenzoyl)-5-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5, Delocalizations, formamide derivative, Formamides, hydrazine derivative, Hydrazines, Hydrogen-bonded chains, Hydroxybenzoates, N, N-dimethylformamide, N-Dimethylformamide, oxadiazines, Phenylhydrazine, Solvent molecules
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	Arshiya Kousar Library Assistant
Date Deposited:	31 Aug 2019 05:35
Last Modified:	25 Jul 2022 07:26
URI:	http://eprints.uni-mysore.ac.in/id/eprint/4296

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