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Crystal structure of (1S,2R,6R,7R,8S,12S)-4,10,17-triphenyl-15-thia-4,10-diaza-penta-cyclo[5.5.5.0(1,16).0(2,6).0(8,12)]hepta-deca-13,16-diene-3,5,9,11-tetrone p-xylene hemisolvate.

Noland WE, Kroll NJ, Huisenga MP, Yue RA, Lang SB, Klein ND, Tritch KJ - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: The title tetrone compound, C32H22N2O4S· 0.5C8H10, is the major product (50% yield) of an attempted Diels-Alder reaction of 2-(α-styr-yl)thio-phene with N-phenyl-male-imide (2 equivalents) in toluene.Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene mol-ecule is located about an inversion center.In the crystal, the primary tetrone contacts are between a carbonyl O atom and the four flagpole H atoms of the bi-cyclo-[2.2.2]octene core, forming chains along [001].

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.

ABSTRACT
The title tetrone compound, C32H22N2O4S· 0.5C8H10, is the major product (50% yield) of an attempted Diels-Alder reaction of 2-(α-styr-yl)thio-phene with N-phenyl-male-imide (2 equivalents) in toluene. Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene mol-ecule is located about an inversion center. In the crystal, the primary tetrone contacts are between a carbonyl O atom and the four flagpole H atoms of the bi-cyclo-[2.2.2]octene core, forming chains along [001].

No MeSH data available.


Related in: MedlinePlus

Twisting of N-phenyl rings (C27 forward, C33 behind) viewed along [514], normal to the thio­phene moiety.
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fig5: Twisting of N-phenyl rings (C27 forward, C33 behind) viewed along [514], normal to the thio­phene moiety.

Mentions: In compound (3) (Fig, 1), the N-phenyl rings (C24–C29) and (C30–C35) are twisted out of the plane of their respective succinimido rings, (N4/C3/C2/C6/C5) and (N10/C9/C8/C12/C11), by 54.83 (8) and 54.97 (8)°, respectively, with the same chirality, giving helical character along the major axis (C27 to C33). Figs. 4 ▶ and 5 ▶ show a left-handed mol­ecule. The bi­cyclo­[2.2.2]octene rings have a typical boat shape. The other rings are nearly planar; the r.m.s. deviations from their respective mean planes are 0.026 and 0.030 Å for the succin­imido rings (N4/C3/C2/C6/C5) and (N10/C9/C8/C12/C11), respectively, and 0.01 Å for the 3-hydro­thieno ring (S15/C16/C1/C13/C14). The two succinimido rings are inclined to one another by 29.24 (8)° and the N-phenyl rings are inclined to one another by 54.55 (8)°. The phenyl ring (C18–23) is inclined to the the N-phenyl rings, (C24–C29) and (C30–C35), by 89.89 (8) and 64.82 (8)°, respectively. There is an intra­molecular C—H⋯O hydrogen bond present (Table 1 ▶).


Crystal structure of (1S,2R,6R,7R,8S,12S)-4,10,17-triphenyl-15-thia-4,10-diaza-penta-cyclo[5.5.5.0(1,16).0(2,6).0(8,12)]hepta-deca-13,16-diene-3,5,9,11-tetrone p-xylene hemisolvate.

Noland WE, Kroll NJ, Huisenga MP, Yue RA, Lang SB, Klein ND, Tritch KJ - Acta Crystallogr Sect E Struct Rep Online (2014)

Twisting of N-phenyl rings (C27 forward, C33 behind) viewed along [514], normal to the thio­phene moiety.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257460&req=5

fig5: Twisting of N-phenyl rings (C27 forward, C33 behind) viewed along [514], normal to the thio­phene moiety.
Mentions: In compound (3) (Fig, 1), the N-phenyl rings (C24–C29) and (C30–C35) are twisted out of the plane of their respective succinimido rings, (N4/C3/C2/C6/C5) and (N10/C9/C8/C12/C11), by 54.83 (8) and 54.97 (8)°, respectively, with the same chirality, giving helical character along the major axis (C27 to C33). Figs. 4 ▶ and 5 ▶ show a left-handed mol­ecule. The bi­cyclo­[2.2.2]octene rings have a typical boat shape. The other rings are nearly planar; the r.m.s. deviations from their respective mean planes are 0.026 and 0.030 Å for the succin­imido rings (N4/C3/C2/C6/C5) and (N10/C9/C8/C12/C11), respectively, and 0.01 Å for the 3-hydro­thieno ring (S15/C16/C1/C13/C14). The two succinimido rings are inclined to one another by 29.24 (8)° and the N-phenyl rings are inclined to one another by 54.55 (8)°. The phenyl ring (C18–23) is inclined to the the N-phenyl rings, (C24–C29) and (C30–C35), by 89.89 (8) and 64.82 (8)°, respectively. There is an intra­molecular C—H⋯O hydrogen bond present (Table 1 ▶).

Bottom Line: The title tetrone compound, C32H22N2O4S· 0.5C8H10, is the major product (50% yield) of an attempted Diels-Alder reaction of 2-(α-styr-yl)thio-phene with N-phenyl-male-imide (2 equivalents) in toluene.Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene mol-ecule is located about an inversion center.In the crystal, the primary tetrone contacts are between a carbonyl O atom and the four flagpole H atoms of the bi-cyclo-[2.2.2]octene core, forming chains along [001].

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.

ABSTRACT
The title tetrone compound, C32H22N2O4S· 0.5C8H10, is the major product (50% yield) of an attempted Diels-Alder reaction of 2-(α-styr-yl)thio-phene with N-phenyl-male-imide (2 equivalents) in toluene. Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene mol-ecule is located about an inversion center. In the crystal, the primary tetrone contacts are between a carbonyl O atom and the four flagpole H atoms of the bi-cyclo-[2.2.2]octene core, forming chains along [001].

No MeSH data available.


Related in: MedlinePlus