TY - JOUR
T1 - Crystal structures of three (trichloromethyl)(carbamoyl)disulfanes
AU - Goldenberg, Barbara L.
AU - Young, Victor G.
AU - Barany, George
N1 - Publisher Copyright:
© 2015.
PY - 2015
Y1 - 2015
N2 - The present paper reports crystallographic studies on three related compounds that were of interest as precursors for synthetic and mechanistic work in organosulfur chemistry, as well as to model nitrogen-protecting groups: (N-methylcarbamoyl)(trichloromethyl)disulfane, C3H4Cl3NOS2, (1), (N-benzylcarbamoyl)(trichloromethyl)disulfane, C9H8Cl3NOS2, (2), and (N-methyl-N-phenylcarbamoyl)(trichloromethyl)disulfane, C9H8Cl3NOS2, (3). Their molecular structures, with similar bond lengths and angles for the CCl3SS(C=O)N moieties, are confirmed. Compounds (1) and (3) both crystallized with two independent molecules in the asymmetric unit. Classical hydrogen bonding, as well as chlorine-dense regions, are evident in the crystal packing for (1) and (2). In the crystal of (1), molecules are linked via N - H⋯O hydrogen bonds forming chains along [110], which are linked by short Cl⋯Cl and S⋯O contacts forming sheets parallel to (001). In the crystal of (2), molecules are linked via N - H⋯O hydrogen bonds forming chains along [001], which in turn are linked by pairs of short O⋯Cl contacts forming ribbons along the c-axis direction. In the crystal of (3), there are no classical hydrogen bonds present and the chlorine-dense regions observed in (1) and (2) are lacking.
AB - The present paper reports crystallographic studies on three related compounds that were of interest as precursors for synthetic and mechanistic work in organosulfur chemistry, as well as to model nitrogen-protecting groups: (N-methylcarbamoyl)(trichloromethyl)disulfane, C3H4Cl3NOS2, (1), (N-benzylcarbamoyl)(trichloromethyl)disulfane, C9H8Cl3NOS2, (2), and (N-methyl-N-phenylcarbamoyl)(trichloromethyl)disulfane, C9H8Cl3NOS2, (3). Their molecular structures, with similar bond lengths and angles for the CCl3SS(C=O)N moieties, are confirmed. Compounds (1) and (3) both crystallized with two independent molecules in the asymmetric unit. Classical hydrogen bonding, as well as chlorine-dense regions, are evident in the crystal packing for (1) and (2). In the crystal of (1), molecules are linked via N - H⋯O hydrogen bonds forming chains along [110], which are linked by short Cl⋯Cl and S⋯O contacts forming sheets parallel to (001). In the crystal of (2), molecules are linked via N - H⋯O hydrogen bonds forming chains along [001], which in turn are linked by pairs of short O⋯Cl contacts forming ribbons along the c-axis direction. In the crystal of (3), there are no classical hydrogen bonds present and the chlorine-dense regions observed in (1) and (2) are lacking.
KW - Z = 16
KW - Z′ = 2
KW - carbamoyl disulfanes
KW - crystal structures
KW - halogen bonding
KW - hydrogen bonding
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U2 - 10.1107/S2056989015015893
DO - 10.1107/S2056989015015893
M3 - Article
C2 - 26594398
AN - SCOPUS:84947930532
SN - 2056-9890
VL - 71
SP - 1169
EP - 1173
JO - Acta Crystallographica Section E: Crystallographic Communications
JF - Acta Crystallographica Section E: Crystallographic Communications
ER -