Crystal Structure and Solid-State Packing of 4-Chloro-5H-1,2,3-dithiazol-5-one and 4-Chloro-5H-1,2,3-dithiazole-5-thione

The crystal structure and solid-state packing of 4-chloro-5H-1,2,3-dithiazol-5-one and two polymorphs of 4-chloro-5H-1,2,3-dithiazole-5-thione were analyzed and compared to structural data of similar systems. These five-membered S,N-rich heterocycles are planar with considerable bond localization. A...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2021-09, Vol.26 (19), p.5875
Main Authors: Constantinides, Christos P., Koyioni, Maria, Bazzi, Fadwat, Manoli, Maria, Lawson, Daniel B., Koutentis, Panayiotis A.
Format: Article
Language:English
Subjects:
1,2,3-dithiazol-5-one
1,2,3-dithiazole-5-thione
1,2,3-dithiazoles
Appel’s salt
Aromaticity
Chemistry
Crystal structure
dithiazines
Expected values
Localization
Solid state
Symmetry
thiazoles
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Summary:The crystal structure and solid-state packing of 4-chloro-5H-1,2,3-dithiazol-5-one and two polymorphs of 4-chloro-5H-1,2,3-dithiazole-5-thione were analyzed and compared to structural data of similar systems. These five-membered S,N-rich heterocycles are planar with considerable bond localization. All three structures demonstrate tight solid-state packing without voids which is attributed to a rich network of short intermolecular electrostatic contacts. These include Sδ+…Nδ−, Sδ+…Oδ−, Sδ+…Clδ− and Sδ+…Sδ− interactions that are well within the sum of their van der Waals radii (∑VDW). B3LYP, BLYP, M06, mPW1PW, PBE and MP2 were employed to calculate their intramolecular geometrical parameters, the Fukui condensed functions to probe their reactivity, the bond order, Bird Index and NICS(1) to establish their aromaticity.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules26195875