A simple hydrogen-bonded chain in (3Z)-3-{1-[(5-phenyl-1H-pyrazol-3-yl)amino]ethylidene}-4,5-dihydrofuran-2(3H)-one, and a hydrogen-bonded ribbon of centrosymmetric rings in the self-assembled adduct (3Z)-3-{1-[(5-methyl-1H-pyrazol-3-yl)amino]ethylidene}-4,5-dihydrofuran-2(3H)-one-6-(2-hydroxyethyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7(4H)-one (1/1).
(3Z)-3-{1-[(5-Phenyl-1H-pyrazol-3-yl)amino]ethylidene}-4,5-dihydrofuran-2(3H)-one, C(15)H(15)N(3)O(2), (I), and the stoichiometric adduct (3Z)-3-{1-[(5-methyl-1H-pyrazol-3-yl)amino]ethylidene}-4,5-dihydrofuran-2(3H)-one-6-(2-hydroxyethyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7(4H)-one (1/1), C(10)H(13)N(3)O(2).C(10)H(13)N(3)O(2), (II), in which the two components have the same composition but different constitutions, are formed in the reactions of 2-acetyl-4-butyrolactone with 5-amino-3-phenyl-1H-pyrazole and 5-amino-3-methyl-1H-pyrazole, respectively. In each compound, the furanone component contains an intramolecular N-H...O hydrogen bond. The molecules of (I) are linked into a chain by a single intermolecular N-H...O hydrogen bond, while in (II), a combination of one O-H...N hydrogen bond, within the selected asymmetric unit, and two N-H...O hydrogen bonds link the molecular components into a ribbon containing alternating centrosymmetric R(4)(4)(20) and R(6)(6)(22) rings.
Quiroga
Jairo
J
Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia.
Portilla
Jaime
J
Cobo
Justo
J
Glidewell
Christopher
C
D018360:Crystallography, X-Ray; D005663:Furans / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D011720:Pyrazoles / Q000737:chemistry*; D011744:Pyrimidinones / Q000737:chemistry*
C547118:(3Z)-3-(1-((5-methyl-1H-pyrazol-3-yl)amino)ethylidene)-4,5-dihydrofuran-2(3H)-one-6-(2-hydroxyethyl)-2,5-dimethylpyrazolo(1,5-a)pyrimidin-7(4H)-one; C547117:(3Z)-3-(1-((5-phenyl-1H-pyrazol-3-yl)amino)ethylidene)-4,5-dihydrofuran-2(3H)-one; D005663:Furans; D011720:Pyrazoles; D011744:Pyrimidinones