3-Acetyl-4-benzoyl-2-methyl-5-phenyl-3,3a-dihydropyrazolo[2,3-c]pyrimidine-7(6H)-thione

Abstract

The molecule of the title compound, C(22)H(19)N(3)O(2)S, is not planar. The dihedral angle between the two phenyl rings is 27.46 (7) degrees and in the dihydropyrazolopyrimidine ring the total puckering amplitude Q(T) is 0.526 (3) A. The structure is stabilized by both intra- and intermolecular C-H.O interaction, and by an intermolecular N-H.S hydrogen bond.

1,3-Dibenzoylimidazolidine-2-thione and 1,3-dibenzoyl-3,4,5,6-tetrahydropyrimidine-2(1H)-thione

“…The molecule of (I), showing the atom-labelling scheme and 40% probability displacement ellipsoids. a double bond and are similar to those in other reported heterocyclic thione derivatives containing imidazolethione and pyrimidinethione rings (O È zbey et al, 1991Akkurt et al, 1992Akkurt et al, , 2000Cox et al, 1996;Liu et al, 2003;Brito et al, 2004). The C8ÐN1 bond distances in both compounds are intermediate between standard single CÐN (1.47 A Ê ) and double C N (1.28 A Ê ) bonds, being signi®cantly shorter than the C9ÐN1 bonds, because atom C8 is in an sp 2 -hybridized state, while atom C9 is sp 3 .…”

“…The dihedral angle between the two planar benzoyl fragments is 75.92 (3) in (I) and 61.08 (4) in (II). A nonplanar disposition of the three rings has been observed in other reported heterocyclic thione derivatives with similar compositions (O È zbey et al, 1991;Cox et al, 1996;Akkurt et al, 2000;O È zc Ëelik et al, 2004).…”

Crystal Structure of 5-(4-Methylbenzoyl)-1-(methyl-4-methylphenyl-methylene amino)-4-(4-methylphenyl)-1H-pyrimidine-2-thione

“…The C1-S1 [1.664(3)Å] double-bond length of the pyrimidine ring is the same as the C=S doublebond length [1.664(2)Å] in 3-acetyl-4-benzoyl-2-methyl-5-phenyl-3,3a-dihydropyrazolo[2,3-c]-pyrimidine-7(6H)-thione. 4 The three phenyl rings (B (C5-C10), C (C13-C18) and D (C22-C27)) are planar, with maximum deviations of -0.021(4)Å for C5 and -0.020(4)Å for C8 from the least-squares planes. The molecular structure of the title compound is closely related to that of 5-(4-methylbenzoyl)-4-(4-methylphenyl)-1-(methylphenyl-methylenamino)-1H-pyrimidin-2-one and 1-[(4-methylbenzylidene)amino]-5-(4-methylbenzoyl)-4-(ptolyl)pyrimidin-2(1H)-one.…”