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1. Crystal structure of 4-methyl- N -propylbenzenesulfonamide

   https://doi.org/10.1107/S2056989020007756  

   Stenfors, Brock A.; Collins, Rachel C.; Duran, Jonah R.; Staples, Richard J.; Biros, Shannon M.; Ngassa, Felix N. (July 2020, Acta Crystallographica Section E Crystallographic Communications)

   The crystal structure of the title sulfonamide, C 10 H 15 NO 2 S, comprises two molecules in the asymmetric unit. The S=O bond lengths of the sulfonamide functional group range from 1.428 (2) to 1.441 (2) Å, with S—C bond lengths of 1.766 (3) Å (for both molecules in the asymmetric unit), and S—N bond lengths of 1.618 (2) and 1.622 (3) Å, respectively. When both molecules are viewed down the N—S bond, the propyl group is gauche to the toluene moiety. In the crystal structure, molecules of the title compound are arranged in an intricate three-dimensional network that is formed via intermolecular C—H...O and N—H...O hydrogen bonds. The crystal structure was refined from a crystal twinned by inversion. 

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2. Crystal structure of N -allyl-4-methylbenzenesulfonamide

   https://doi.org/10.1107/S2056989018010290  

   Patel, Zeel S.; Stevens, Amanda C.; Bookout, Erin C.; Staples, Richard J.; Biros, Shannon M.; Ngassa, Felix N. (August 2018, Acta Crystallographica Section E Crystallographic Communications)

   The title compound, C 10 H 13 NO 2 S, was synthesized by a nucleophilic substitution reaction between allyl amine and p -toluenesulfonyl chloride. The sulfonate S—O bond lengths are 1.4282 (17) and 1.4353 (17) Å, and the C—N—S—C torsion angle involving the sulfonamide moiety is −61.0 (2)°. In the crystal, centrosymmetric dimers of the title compound are present via intermolecular N—H...O hydrogen bonds between sulfonamide groups. These dimers are linked into ribbons along the c -axis direction through offset π–π interactions. 

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3. Crystal structure of 1-[(4-methylbenzene)sulfonyl]pyrrolidine

   https://doi.org/10.1107/S205698902000208X  

   Stenfors, Brock A.; Staples, Richard J.; Biros, Shannon M.; Ngassa, Felix N. (March 2020, Acta Crystallographica Section E Crystallographic Communications)

   The molecular structure of the title compound, C 11 H 15 NO 2 S, features a sulfonamide group with S=O bond lengths of 1.4357 (16) and 1.4349 (16) Å, an S—N bond length of 1.625 (2) Å, and an S—C bond length of 1.770 (2) Å. When viewing the molecule down the S—N bond, both N—C bonds of the pyrrolidine ring are oriented gauche to the S—C bond with torsion angles of −65.6 (2)° and 76.2 (2)°. The crystal structure features both intra- and intermolecular C—H...O hydrogen bonds, as well as intermolecular C—H...π and π–π interactions, leading to the formation of sheets parallel to the ac plane. 

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4. N -(3,5-Dichloro-4-hydroxyphenyl)acetamide

   https://doi.org/10.1107/S2414314626000751  

   Uppu, Rao M; Fronczek, Frank R (January 2026, IUCrData)

   The title compound, C₈H₇Cl₂NO₂, crystallizes in the triclinic space groupP1with three molecules in the asymmetric unit. Two of them are essentially planar, with mean deviations of 13 non-hydrogen atoms of 0.029 and 0.030 Å, and differ only in the conformation of the O—H hydrogen atom. The third molecule is quite nonplanar, with the CCNO acetamide plane forming a dihedral angle of 67.56 (5)° with the remainder of the molecule. In the extended structure, the two almost planar molecules form antiparallel hydrogen-bonded chains through N—H...O interactions of the acetamide substituents. The N—H group of the nonplanar molecule donates a bifurcated hydrogen bond to the O—H group and a Cl substituent of one of the planar molecules. The O—H groups of all molecules form intermolecular hydrogen bonds to other O—H groups or carbonyl O atoms. Together, the hydrogen bonds generate a three-dimensional network. 

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5. 2-Chloro-4-hydroxyanilinium chloride

   https://doi.org/10.1107/S2414314625008934  

   Bai, Sindhu V; Mensah, Patrick F; Li, Guoqiang; Fronczek, Frank R; Uppu, Rao M (October 2025, IUCrData)

   The title compound, C₆H₇ClNO⁺·Cl⁻, crystallizes in orthorhombic space groupPnmawith both cations and anions lying on a mirror plane in the crystal. The C—Cl distance is 1.7289 (6) Å, the C—N distance is 1.4590 (8) Å, and the C—O distance is 1.3617 (8) Å. Parallel molecules form stacks with interplanar spacing 3.1473 (2) Å, but slipped by 1.97 Å. The NH₃⁺substituent donates three intermolecular hydrogen bonds to chloride ions having N...Cl distances in the range 3.1514 (6)–3.3019 (2) Å, and the OH group donates an intermolecular hydrogen bond to chloride with O...Cl distance 3.0671 (6) Å. The chloro substituent and OH group do not accept hydrogen bonds from NH or OH. 

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