Crystal structure of N-allyl-4-methyl-benzene-sulfonamide

Zeel S Patel; Amanda C Stevens; Erin C Bookout; Richard J Staples; Shannon M Biros; Felix N Ngassa

doi:10.1107/S2056989018010290

Crystal structure of N-allyl-4-methyl-benzene-sulfonamide

Acta Crystallogr E Crystallogr Commun. 2018 Jul 20;74(Pt 8):1126-1129. doi: 10.1107/S2056989018010290. eCollection 2018 Aug 1.

Authors

Zeel S Patel¹, Amanda C Stevens¹, Erin C Bookout¹, Richard J Staples², Shannon M Biros¹, Felix N Ngassa¹

Affiliations

¹ Department of Chemistry, Grand Valley State University, 1 Campus Dr., Allendale, MI 49401, USA.
² Center for Crystallographic Research, Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA.

Abstract

The title compound, C₁₀H₁₃NO₂S, was synthesized by a nucleophilic substitution reaction between allyl amine and p-toluene-sulfonyl 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 inter-molecular N-H⋯O hydrogen bonds between sulfonamide groups. These dimers are linked into ribbons along the c-axis direction through offset π-π inter-actions.

Keywords: aryl sulfonamide; crystal structure; hydrogen bond; offset π–π interaction.

Grants and funding

This work was funded by National Science Foundation grants CCLI CHE-0087655 and MRI CHE-1725699. GVSU Chemistry Department’s Weldon Fund grant .