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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.

ABSTRACT: 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.

SUBMITTER: Constantinides CP 

PROVIDER: S-EPMC8512425 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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

Constantinides Christos P CP   Koyioni Maria M   Bazzi Fadwat F   Manoli Maria M   Lawson Daniel B DB   Koutentis Panayiotis A PA  

Molecules (Basel, Switzerland) 20210928 19

The crystal structure and solid-state packing of 4-chloro-5<i>H</i>-1,2,3-dithiazol-5-one and two polymorphs of 4-chloro-5<i>H</i>-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 S<sup>δ+</sup>  ...[more]

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