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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.

Carbone MR, Centola GA, Haas A, McClelland KP, Moskowitz MD, Verderame AM, Olezeski MS, Papa LJ, Dorn SC, Brennessel WW, Weix DJ - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: 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.

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Affiliation: Department of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USA.

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.

No MeSH data available.


A partial view of the crystal packing of compound (1), illustrating the formation of the hydrogen-bonded chains along [100] (hydrogen bonds are shown as dashed lines; see Table 1 ▶ for details). Displacement ellipsoids are drawn at the 50% probability level.
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fig4: A partial view of the crystal packing of compound (1), illustrating the formation of the hydrogen-bonded chains along [100] (hydrogen bonds are shown as dashed lines; see Table 1 ▶ for details). Displacement ellipsoids are drawn at the 50% probability level.

Mentions: In the crystals of both (1) and (2), chains are formed via inter­molecular hydrogen bonding (Tables 1 ▶ and 2 ▶). In (1), mol­ecules are linked along the [100] direction by a combination of classical (N—H⋯O=S) and non-classical (C—H⋯O=S) hydrogen bonds (Table 1 ▶ and Fig. 4 ▶). In (2), mol­ecules are linked along the [010] direction also by classical (N—H⋯O=S) and non-classical (C—H⋯O=S) hydrogen bonds (Table 2 ▶ and Fig. 5 ▶).


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.

Carbone MR, Centola GA, Haas A, McClelland KP, Moskowitz MD, Verderame AM, Olezeski MS, Papa LJ, Dorn SC, Brennessel WW, Weix DJ - Acta Crystallogr Sect E Struct Rep Online (2014)

A partial view of the crystal packing of compound (1), illustrating the formation of the hydrogen-bonded chains along [100] (hydrogen bonds are shown as dashed lines; see Table 1 ▶ for details). Displacement ellipsoids are drawn at the 50% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257314&req=5

fig4: A partial view of the crystal packing of compound (1), illustrating the formation of the hydrogen-bonded chains along [100] (hydrogen bonds are shown as dashed lines; see Table 1 ▶ for details). Displacement ellipsoids are drawn at the 50% probability level.
Mentions: In the crystals of both (1) and (2), chains are formed via inter­molecular hydrogen bonding (Tables 1 ▶ and 2 ▶). In (1), mol­ecules are linked along the [100] direction by a combination of classical (N—H⋯O=S) and non-classical (C—H⋯O=S) hydrogen bonds (Table 1 ▶ and Fig. 4 ▶). In (2), mol­ecules are linked along the [010] direction also by classical (N—H⋯O=S) and non-classical (C—H⋯O=S) hydrogen bonds (Table 2 ▶ and Fig. 5 ▶).

Bottom Line: 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.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USA.

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.

No MeSH data available.