NDLI: Synthesis, Spectroscopic Characterization and X-ray Structure Analysis of 6-(2,5-Dichlorothiophen-3-yl)-3,4-dihydro-4-(4-methoxyphenyl)pyrimidine-2(1H)-thione

Content Provider	Springer Nature Link
Author	Al Refai, Mahmoud Geyer, Armin Marsch, Michael Ali, Basem F.
Copyright Year	2014
Abstract	The title compound was prepared by the condensation of (E)-1-(2,5-dichlorothiophen-3-yl)-3-(4-methoxy)prop-2-en-1-one and thiourea in the presence of KOH. In the title compound, C$_{34}$H$_{28}$Cl$_{16}$N$_{4}$O$_{2}$S$_{4}$, the asymmetric unit consists of two independent molecules and four independent chloroform molecules. The heterocyclic pyrimidine-2(1H)-thione rings adopt a flattened boat conformation. The methoxyphenyl rings are perpendicular to the pyrimidine-2(1H)-thione rings with dihedral angles of 81.20 and 79.85° in both independent molecules. The dichlorothiophene rings are twisted compared to the pyrimidine-2(1H)-thione rings with dihedral angles of 40.59 and 39.36° in the independent molecules. The methoxyphenyl group has an axial orientation. Intermolecular C–H···S, C–H···O, C–H··· π vertex-to-face intermolecular interactions between chloroform C–H groups and the center of the phenyl rings and extensive Cl···Cl intermolecular interactions are found in the crystal structure. All interactions consolidate a three dimensional network. The molecular structure was further analyzed using spectroscopic methods. Mass ESI-HMRS measurements were performed. The HRESIMS analysis revealed the molecular formula, C$_{15}$H$_{12}$Cl$_{2}$N$_{2}$OS$_{2}$, with [M+H]$^{+}$ and [M+H+2]$^{+}$ and [M+H+4]$^{+}$ isotopic clusters characteristic for a dichlorinated compound. The compound was also thoroughly characterized by $^{1}$H, $^{13}$C, NMR spectra and 2D NMR spectra (COSY, HSQC and HMBC).Synthesis, characterization, molecular, crystal structure and crystal supramolecularity of the three dimensional network structure of 6-(2,5-dichlorothiophen-3-yl)-3,4-dihydro-4-(4-methoxyphenyl)pyrimidine-2(1H)-thione are reported.
Starting Page	407
Ending Page	414
Page Count	8
File Format	PDF
ISSN	10741542
Journal	Journal of Chemical Crystallography
Volume Number	44
Issue Number	8
e-ISSN	15728854
Language	English
Publisher	Springer US
Publisher Date	2014-07-17
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Pyrimidine-2(1H)-thione Chalcones Spectroscopic characterization Crystal supramolecularity C–H···S/O Cl···Cl interactions C–H··· π interactions Organometallic Chemistry Crystallography Physical Chemistry Inorganic Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics

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