Crystal structures of three (trichloromethyl)(carbamoyl)disulfanes

Barbara L. Goldenberg, Victor G. Young, George Barany

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)1169-1173
Number of pages5
JournalActa Crystallographica Section E: Crystallographic Communications
Volume71
DOIs
StatePublished - 2015

Keywords

  • Z = 16
  • Z′ = 2
  • carbamoyl disulfanes
  • crystal structures
  • halogen bonding
  • hydrogen bonding

Fingerprint Dive into the research topics of 'Crystal structures of three (trichloromethyl)(carbamoyl)disulfanes'. Together they form a unique fingerprint.

Cite this