title: Crystal structures of (R S)-N-[(1R,2S)-2-benz-yloxy-1-(2,6-di-methyl-phen-yl)prop-yl]-2-methyl-propane-2-sulfinamide and (R S)-N-[(1S,2R)-2-benz-yloxy-1-(2,4,6-tri-methyl-phen-yl)prop-yl]-2-methyl-propane-2-sulfinamide: two related protected 1,2-amino alcohols.
abstract: The title compounds, C22H31NO2S, (1), and C23H33NO2S, (2), are related protected 1,2-amino alcohols. They differ in the substituents on the benzene ring, viz. 2,6-di-methyl-phenyl in (1) and 2,4,6-tri-methyl-phenyl in (2). The plane of the phenyl ring is inclined to that of the benzene ring by 28.52 (7)° in (1) and by 44.65 (19)° in (2). In the crystal of (1), N-H⋯O=S and C-H⋯O=S hydrogen bonds link mol-ecules, forming chains along [100], while in (2), similar hydrogen bonds link mol-ecules into chains along [010]. The absolute structures of both compounds were determined by resonance scattering.
authors.affiliation: Department of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USA.
authors.forename: Matthew R
authors.initials: MR
authors.lastname: Carbone
authors.affiliation: Department of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USA.
authors.forename: Garrick A
authors.initials: GA
authors.lastname: Centola
authors.affiliation: Department of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USA.
authors.forename: Adam
authors.initials: A
authors.lastname: Haas
authors.affiliation: Department of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USA.
authors.forename: Kevin P
authors.initials: KP
authors.lastname: McClelland
authors.affiliation: Department of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USA.
authors.forename: Michael D
authors.initials: MD
authors.lastname: Moskowitz
authors.affiliation: Department of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USA.
authors.forename: Angelo M
authors.initials: AM
authors.lastname: Verderame
authors.affiliation: Department of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USA.
authors.forename: Mikael S
authors.initials: MS
authors.lastname: Olezeski
authors.affiliation: Department of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USA.
authors.forename: Louis J
authors.initials: LJ
authors.lastname: Papa
authors.affiliation: Department of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USA.
authors.forename: Stephanie C M
authors.initials: SC
authors.lastname: Dorn
authors.affiliation: Department of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USA.
authors.forename: William W
authors.initials: WW
authors.lastname: Brennessel
authors.affiliation: Department of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USA.
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Weix
keywords: NMR; amino alcohol; column chromatography; crystal structure; diastereomer; hydrogen bonding; sulfinamide