1-(3-Fluorophenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1<i>H</i>)-thione

Yamin, Bohari Mohd.; Lawi, R.L. Mohd; Salem, Halima F.

doi:10.1107/s1600536811023671

Cited by 2 publications

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“…In order to compare the packing modes of 1-4 with similar structures, a search of the crystal structural database (CSD, 48 ConQuest 1.19 (ref. 49)) for the 4,4,6-trimethyl-3,4-dihydropyrimidine-2Ĳ1H)-thione moiety was undertaken, yielding eight hits: two structures corresponding to the meta (IJUGEA) 50,51 and para (DUNZIW) 9 isomers of compound 1; another two related structures containing mono-substituents fluorine (EVEWIM) 52 and bromine (VAGSUR) 53 on the phenyl ring, two structures that are the ortho-methyl (IMARIY) 25 and meta-methyl isomers (PUJYID), 10 and structures related to the unsubstituted compound, which is present as orthorhombic (FAXVOQ-I) 23 and triclinic (FAXVOQ-II) 24 polymorphs. Relevant data for these structures are also included in Table 3.…”

Section: Structural Motifs and Interaction Energiesmentioning

confidence: 99%

Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives

et al. 2017

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The crystal structures of four 1-(R-phenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2Ĳ1H)-thione derivatives [R = 2-chloro (1), 2,3-di-chloro (2), 2,4-di-methyl (3), and 4-methoxy (4)] were determined and analysis of their molecular conformations was carried out. A comparative study of the intermolecular interactions-including eight closely related structures from CSD-was performed and the degree of isostructurality was quantified. The intermolecular interactions were characterized in terms of the periodic system electron density and the topological analysis highlighted the role of N-H⋯SC hydrogen bonds in the stabilization of the different supramolecular architectures. PIXEL lattice energy calculations revealed that the dispersion component was the major contributor, together with the important role of the Coulombic term to the total energy. The interaction energies for molecular pairs involving N-H⋯SC hydrogen bonds indicated a dominant contribution to packing stabilization coming from the Coulombic components. Hirshfeld surfaces and fingerprint plots allowed us to visualize different intermolecular contacts and their relative contributions to the total surface for each compound. Analysis of the electrostatic potentials (ESP) correlated well with the computed energies, thus characterizing the strengths of the different interactions.

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Section: Structural Motifs and Interaction Energiesmentioning

confidence: 99%

Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives

et al. 2017

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“…The title compound is related to 4,4,6-trimethyl-1-phenyl-3,4-dihydropyrimidne-2-(1H)-thione (Yamin et al, 2005;Ismail et al, 2007), and isomeric to (S)-1-(3-fluorophenyl)-4,4,6-trimethyltetrahydropyrimidine-2(1H)-thione (Yamin et al, 2011) in which the dihydropyrimidine rings are in flattened sofa conformations. The dihydropyrimidine ring (N1/N2/C7-C10) in the title compound ( Fig.…”

Section: Structure Descriptionmentioning

confidence: 99%

1-(4-Fluorophenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1H)-thione

et al. 2016

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In the title molecule, C 13 H 15 FN 2 S, the dihydropyrimidine ring is in a flattened boat conformation with deviations of 0.135 (2) and 0.371 (2) Å for the fluorophenyl-substituted N atom and the dimethyl-substituted C atom, respectively, from the four other essentially co-planar atoms. In the crystal, pairs of molecules related by twofold rotation axes are linked by N-HÁ Á ÁS hydrogen bonds, forming dimers. Structure descriptionThe title compound is related to 4,4,6-trimethyl-1-phenyl-3,4-dihydropyrimidne-2-(1H)-thione (Yamin et al., 2005;Ismail et al., 2007), and isomeric to (S)-1-(3-fluorophenyl)-4,4,6-trimethyltetrahydropyrimidine-2(1H)-thione (Yamin et al., 2011) in which the dihydropyrimidine rings are in flattened sofa conformations. The dihydropyrimidine ring (N1/N2/C7-C10) in the title compound (Fig. 1) is in a flattened boat conformation with deviations of 0.135 (2) and 0.371 (2) Å for atoms N1 and C10, respectively, from the mean plane through atoms C7/C8/C9/N2. The benzene (C1-C6) and four planar atoms (C7/C8/ C9/N2) of the dihydropyrimidine ring form a dihedral angle of 85.78 (13) . The bond length and angles are in normal ranges and comparable to those in the above mentioned analogs. In the crystal, pairs of molecules related by twofold rotation axes are linked by N-HÁ Á ÁS hydrogen bonds, forming dimers (Table 1 and Fig. 2). Synthesis and crystallizationA procedure similar to that used for the preparation of 1-(3-fluorophenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1H)-thione (Yamin et al., 2011) was followed. Equi-

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1-(3-Fluorophenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1H)-thione

Cited by 2 publications

References 12 publications

Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives

Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives

1-(4-Fluorophenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1H)-thione

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