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Crystal structures of two 1,3-thia-zolidin-4-one derivatives featuring sulfide and sulfone functional groups.


ABSTRACT: The crystal structures of two closely related compounds, 1-cyclo-hexyl-2-(2-nitro-phen-yl)-1,3-thia-zolidin-4-one, C15H18N2O3S, (1) and 1-cyclo-hexyl-2-(2-nitro-phen-yl)-1,3-thia-zolidin-4-one 1,1-dioxide, C15H18N2O5S, (2), are presented. These compounds are comprised of three types of rings: thia-zolidinone, nitrophenyl and cyclo-hexyl. In both structures, the rings are close to mutually perpendicular, with inter-planar dihedral angles greater than 80° in each case. The thia-zol-idinone rings in both structures exhibit envelope puckering with the S atom as flap and the cyclo-hexyl rings are in their expected chair conformations. The two structures superpose fairly well, except for the orientation of the nitro groups with respect to their host phenyl ring, with a difference of about 10° between 1 and 2. The extended structure of 1 has two kinds of weak C-H?O inter-actions, giving rise to a closed ring formation involving three symmetry-related mol-ecules. Structure 2 has four C-H?O inter-actions, two of which are exclusively between symmetry-related thia-zolidinone dioxide moieties and have a parallel 'give-and-take-fashion' counterpart. In the other two inter-actions, the nitrophenyl ring and the cyclo-hexane ring each offer an H atom to the two O atoms on the sulfone group. Additionally, a C-H?? inter-action between a C-H group of the cyclo-hexane ring and the nitrophenyl ring of an adjacent mol-ecule helps to consolidate the structure.

SUBMITTER: Yennawar HP 

PROVIDER: S-EPMC6281102 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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Crystal structures of two 1,3-thia-zolidin-4-one derivatives featuring sulfide and sulfone functional groups.

Yennawar Hemant P HP   Silverberg Lee J LJ   Cannon Kevin K   Gandla Deepa D   Kondaveeti Sandeep K SK   Zdilla Michael J MJ   Nuriye Ahmed A  

Acta crystallographica. Section E, Crystallographic communications 20181106 Pt 12


The crystal structures of two closely related compounds, 1-cyclo-hexyl-2-(2-nitro-phen-yl)-1,3-thia-zolidin-4-one, C<sub>15</sub>H<sub>18</sub>N<sub>2</sub>O<sub>3</sub>S, <b>(1)</b> and 1-cyclo-hexyl-2-(2-nitro-phen-yl)-1,3-thia-zolidin-4-one 1,1-dioxide, C<sub>15</sub>H<sub>18</sub>N<sub>2</sub>O<sub>5</sub>S, <b>(2)</b>, are presented. These compounds are comprised of three types of rings: thia-zolidinone, nitrophenyl and cyclo-hexyl. In both structures, the rings are close to mutually perpen  ...[more]

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