title: Crystal structure of 5-{4'-[(2-{2-[2-(2-ammonio-eth-oxy)eth-oxy]eth-oxy}eth-yl)carbamo-yl]-4-meth-oxy-[1,1'-biphen-yl]-3-yl}-3-oxo-1,2,5-thia-diazo-lidin-2-ide 1,1-dioxide: a potential inhibitor of the enzyme protein tyrosine phosphatase 1B (PTP1B).
abstract: The title compound, C24H32N4O8S, (I), crystallizes as a zwitterion. The terminal amine N atom of the [(2-{2-[2-(2-ammonio-eth-oxy)eth-oxy]eth-oxy}eth-yl)carbamo-yl] side chain is protonated, while the 1,2,5-thia-diazo-lidin-3-one 1,1-dioxide N atom is deprotonated. The side chain is turned over on itself with an intra-molecular N-H⋯O hydrogen bond. The 1,2,5-thia-diazo-lidin-3-one 1,1-dioxide ring has an envelope conformation with the aryl-substituted N atom as the flap. Its mean plane is inclined by 62.87 (8)° to the aryl ring to which it is attached, while the aryl rings of the biphenyl unit are inclined to one another by 20.81 (8)°. In the crystal, mol-ecules are linked by N-H⋯O and N-H⋯N hydrogen bonds, forming slabs lying parallel to (010). Within the slabs there are C-H⋯O and C-H⋯N hydrogen bonds and C-H⋯π inter-actions present.
authors.affiliation: 125 Chemistry Bldg, University of Missouri Columbia, MO 65211, USA.
authors.forename: Kasi Viswanatharaju
authors.initials: KV
authors.lastname: Ruddraraju
authors.affiliation: 125 Chemistry Bldg, University of Missouri Columbia, MO 65211, USA.
authors.forename: Roman
authors.initials: R
authors.lastname: Hillebrand
authors.affiliation: 125 Chemistry Bldg, University of Missouri Columbia, MO 65211, USA.
authors.forename: Charles L
authors.initials: CL
authors.lastname: Barnes
authors.affiliation: 125 Chemistry Bldg, University of Missouri Columbia, MO 65211, USA.
authors.forename: Kent S
authors.initials: KS
authors.lastname: Gates
keywords: 1,2,5-thia­diazo­lidin-3-one 1,1-dioxide; PTP1B; crystal structure; hydrogen bonding; inhibitor