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Goldenberg BL, Young VG, Barany G. Crystal structures of three (trichloromethyl)(carbamoyl)disulfanes. Acta Crystallogr E Crystallogr Commun. 2015;71:1169-73doi: 10.1107/S2056989015015893.
Goldenberg, B. L., Young, V. G., & Barany, G. (2015). Crystal structures of three (trichloromethyl)(carbamoyl)disulfanes. Acta crystallographica. Section E, Crystallographic communications, 711169-73. https://doi.org/10.1107/S2056989015015893
Goldenberg, Barbara L, et al. "Crystal structures of three (trichloromethyl)(carbamoyl)disulfanes." Acta crystallographica. Section E, Crystallographic communications vol. 71 (2015): 1169-73. doi: https://doi.org/10.1107/S2056989015015893
Goldenberg BL, Young VG, Barany G. Crystal structures of three (trichloromethyl)(carbamoyl)disulfanes. Acta Crystallogr E Crystallogr Commun. 2015 Sep 12;71:1169-73. doi: 10.1107/S2056989015015893. eCollection 2015 Oct 01. PMID: 26594398; PMCID: PMC4647414.
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Acta Crystallogr E Crystallogr Commun. 2015 Sep 12;71:1169-73. doi: 10.1107/S2056989015015893. eCollection 2015 Oct 01.

Crystal structures of three (trichloromethyl)(carbamoyl)disulfanes.

Acta crystallographica. Section E, Crystallographic communications

Barbara L Goldenberg, Victor G Young, George Barany

Affiliations

  1. Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.

PMID: 26594398 PMCID: PMC4647414 DOI: 10.1107/S2056989015015893

Abstract

The present paper reports crystallographic studies on three related compounds that were of inter-est as precursors for synthetic and mechanistic work in organosulfur chemistry, as well as to model nitro-gen-protecting groups: (N-methyl-carbamo-yl)(tri-chloro-meth-yl)disulfane, C3H4Cl3NOS2, (1), (N-benzyl-carbamo-yl)(tri-chloro-meth-yl)disulfane, C9H8Cl3NOS2, (2), and (N-methyl-N-phenyl-carbamo-yl)(tri-chloro-meth-yl)disulfane, C9H8Cl3NOS2, (3). Their mol-ecular 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 mol-ecules 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), mol-ecules 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), mol-ecules 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.

Keywords: Z = 16; Z′ = 2; carbamoyl disulfanes; crystal structures; halogen bonding; hydrogen bonding

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