4-Methyl-<i>N</i>-[(<i>S</i>)-1-phenylethyl]benzenesulfonamide

Keleşoğlu, Zeynep; Gültekin, Zeynep; Büyükgüngör, Orhan

doi:10.1107/s1600536810032113

Cited by 2 publications

(3 citation statements)

References 14 publications

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“…Crystal structures, Hirshfeld surfaces, fingerprint plots, and close contacts (% surface area) of toluenesulfonamides (left) in comparison to trifluorotoluenesulfonamides (right). From top to bottom: ( S )-1-phenylethylamine (CSD: SUZRUB, , 1 ), 4-toluidine (CSD: KUSVOK, , 2 ), 1,4-phenylenediamine (CSD: HAVQIE, , 3 ), 1,3-xylylenediamine (CSD: YAWBIJ, , 4 ), tris(2-aminoethyl)amine (CSD: TAQGEY, , 5 ), 2-aminopyridine (CSD: CERWAX, , 6 ), 5-trifluoromethyl-2-aminopyridine (CSD: VEGVOU, , VEGTOS , ), 4-anisidine (CSD: QAKPUP, , CEDCEV , ), 2-phenylaziridine (CSD: KOSQAM, , SUHSAR , ), and 1,2-phenylenediamine (CSD: LAQDAJ, , XARFAA , ). For structures whose asymmetric units consist of two unique molecules (tris(2-aminoethyl)amine, , 2-aminopyridine, , and 1,2-phenylenediamine , ), analysis was performed on each molecule, showing differences of less than 3% (Figure S1).…”

Section: Resultsmentioning

confidence: 99%

“…Electrostatic potential surface (in au) of Ts (left, CSD: SUZRUB)- , and F 3 Ts-( S )-1-phenylamine (right, 1 ).…”

Section: Resultsmentioning

confidence: 99%

“… a References and . b References and . c References and . d References and . e References and . f These values were extrapolated from calculations using larger pixel sizes (see the Supporting Information). g References and . h References and . i References and . j References and . k References and . l References and . m References and . n References and . …”

Section: Resultsmentioning

confidence: 99%

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Statistical Prevalence versus Energetic Contributions of F···F, F···H, and F···C Intermolecular Interactions in 4-Trifluorotoluenesulfonamide Crystals

Sibley

Ruohoniemi

North

et al. 2019

Crystal Growth & Design

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CSD- and PDB-wide surveys of CF3-containing compounds have identified very divergent rates of isostructrality between CH3/CF3 analogues and a variety of behaviors for the CF3 groups ranging from nucleophilic to electrophilic. We present 13 crystal structures containing the 4-trifluorotoluenesulfonamide (F3TsN) moiety and then analyze these structures and 10 pairs of CF3/CH3 toluenesulfonamide analogues using PIXEL-calculated lattice energies, Hirshfeld surfaces, ratios of frequencies, and electrostatic potential energy maps. The F3TsN group is directly and representatively interesting from a pharmaceutical context, given its strong additional intermolecular forces (H bonding and π stacking). Unsurprisingly, many C–F···F angles correspond to type I halogen–halogen interactions, with several presenting at distances shorter than the sum of the van der Waals radii. Only 1 of 10 pairs in our study are isostructural, likely resulting from numerous but individually weak F···H and F···C intermolecular interactions. A ratio of frequencies analysis shows that C[unsat]–F contacts occur much more frequently in F3Ts structures than in the general population of fluorinated structures. We suggest that a detailed analysis of increasing pools of structural data for specific moieties can complement database-wide surveys and lead to more definitive conclusions and eventually design principles.

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