Crystal structure of N, N-diisopropyl-4-methyl-benzene-sulfonamide

Brock A Stenfors; Richard J Staples; Shannon M Biros; Felix N Ngassa

doi:10.1107/S2056989020007185

Crystal structure of N, N-diisopropyl-4-methyl-benzene-sulfonamide

Acta Crystallogr E Crystallogr Commun. 2020 Jun 5;76(Pt 7):1018-1021. doi: 10.1107/S2056989020007185. eCollection 2020 Jul 1.

Authors

Brock A Stenfors¹, 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 synthesis of the title compound, C₁₃H₂₁NO₂S, is reported here along with its crystal structure. This compound crystallizes with two mol-ecules in the asymmetric unit. The sulfonamide functional group of this structure features S=O bond lengths ranging from 1.433 (3) to 1.439 (3) Å, S-C bond lengths of 1.777 (3) and 1.773 (4) Å, and S-N bond lengths of 1.622 (3) and 1.624 (3) Å. When viewing the mol-ecules down the S-N bond, the isopropyl groups are gauche to the aromatic ring. On each mol-ecule, two methyl hydrogen atoms of one isopropyl group are engaged in intra-molecular C-H⋯O hydrogen bonds with a nearby sulfonamide oxygen atom. Inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions link mol-ecules of the title compound in the solid state.

Keywords: crystal structure; intermolecular C—H⋯O hydrogen bond; intermolecular C—H⋯π interaction; intramolecular C—H⋯O hydrogen bond; sulfonamide.

Grants and funding

This work was funded by National Science Foundation, Directorate for Mathematical and Physical Sciences grants MRI CHE-1725699 and MRI CHE-1919817. GVSU Chemistry Department’s Weldon Fund grant .