N,N′-[1,3-Phenylenebis(methylene)]di-p-toluenesulfonamide

Abstract

Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.005 Å; R factor = 0.062; wR factor = 0.187; data-to-parameter ratio = 19.8.In the title compound, C 22 H 24 N 2 O 4 S 2 , the dihedral angles between the central benzene ring and the pendant rings are 66.96 (13) and 69.37 (13) . The torsion angles for the C-N-S-C fragments are À68.5 (3) and À72.6 (3). In the crystal, molecules are linked by N-HÁ Á ÁO hydrogen bonds to generate infinite (001) sheets containing R 4 4 (28) loops. A weak aromatic -stacking contact between one of the terminal benzene rings and its inversion-related partner is also observed [centroid-to-centroid separation = 3.796 (2) Å and slippage = 1.581 Å ], as are two possible C-HÁ Á Á contacts. Related literature Data collectionBruker APEXII CCD diffractometer 19493 measured reflections 5417 independent reflections 3937 reflections with I > 2(I) R int = 0.030

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

“…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).…”

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