TY - JOUR
T1 - Crystal structures of two thiazolidinone derivatives bearing a trichloromethyl substituent at the 2-position
AU - Nuriye, Ahmed
AU - Yennawar, Hemant
AU - Cannon, Kevin
AU - Tierney, John
N1 - Publisher Copyright:
© © Nuriye et al. 2018.
PY - 2018
Y1 - 2018
N2 - The title compounds 2-trichloromethyl-3-phenyl-1,3-thiazolidin-4-one (C 10 H 8 Cl 3 NOS), 1 and 3-(4-chlorophenyl)-2-trichloromethyl-1,3-thiazolidin-4-one (C 10 H 7 Cl 4 NOS) 2, are structurally related with one atom substitution difference in the para position of the benzene ring. In both structures, the thiazolidinone ring adopts an envelope conformation with the S atom as the flap. The dihedral angles between the rings [48.72 (11) in 1 and 48.42 (9)° in 2] are very similar and the molecules are almost superimposable. In both crystal structures, C - H⋯O 'head-to-tail' interactions between the chiral carbon atoms and the thiazolidinone oxygen atoms result in infinite monochiral chains along the direction of the shortest unit-cell parameter, namely a in 1 and b in 2. C - H⋯π interactions between the thiazolidinone carbon atom at the 4-position and the phenyl ring of the neighboring enantiomer also help to stabilize the packing in each case, although the crystals are not isostructural.
AB - The title compounds 2-trichloromethyl-3-phenyl-1,3-thiazolidin-4-one (C 10 H 8 Cl 3 NOS), 1 and 3-(4-chlorophenyl)-2-trichloromethyl-1,3-thiazolidin-4-one (C 10 H 7 Cl 4 NOS) 2, are structurally related with one atom substitution difference in the para position of the benzene ring. In both structures, the thiazolidinone ring adopts an envelope conformation with the S atom as the flap. The dihedral angles between the rings [48.72 (11) in 1 and 48.42 (9)° in 2] are very similar and the molecules are almost superimposable. In both crystal structures, C - H⋯O 'head-to-tail' interactions between the chiral carbon atoms and the thiazolidinone oxygen atoms result in infinite monochiral chains along the direction of the shortest unit-cell parameter, namely a in 1 and b in 2. C - H⋯π interactions between the thiazolidinone carbon atom at the 4-position and the phenyl ring of the neighboring enantiomer also help to stabilize the packing in each case, although the crystals are not isostructural.
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U2 - 10.1107/S2056989018013257
DO - 10.1107/S2056989018013257
M3 - Article
C2 - 30319812
AN - SCOPUS:85054570028
VL - 74
SP - 1509
EP - 1512
JO - Acta Crystallographica Section E: Crystallographic Communications
JF - Acta Crystallographica Section E: Crystallographic Communications
SN - 2056-9890
ER -