Crystal structures of 4-bromo-2-formyl-1-tosyl-1 H-pyrrole, (E)-4-bromo-2-(2-nitro-vin-yl)-1-tosyl-1 H-pyrrole and 6-(4-bromo-1-tosyl-pyrrol-2-yl)-4,4-dimethyl-5-nitro-hexan-2-one

Christopher J Kingsbury; Harry C Sample; Mathias O Senge

doi:10.1107/S2056989021002280

Crystal structures of 4-bromo-2-formyl-1-tosyl-1 H-pyrrole, (E)-4-bromo-2-(2-nitro-vin-yl)-1-tosyl-1 H-pyrrole and 6-(4-bromo-1-tosyl-pyrrol-2-yl)-4,4-dimethyl-5-nitro-hexan-2-one

Acta Crystallogr E Crystallogr Commun. 2021 Mar 5;77(Pt 4):341-345. doi: 10.1107/S2056989021002280. eCollection 2021 Apr 1.

Authors

Christopher J Kingsbury¹, Harry C Sample¹, Mathias O Senge¹

Affiliation

¹ Chair of Organic Chemistry, School of Chemistry, Trinity Biomedical Science Institute, 152-160 Pearse Street, Trinity College Dublin, The University of Dublin, Dublin 2, Ireland.

Abstract

The crystal structures of three inter-mediate compounds in the synthesis of 8-bromo-2,3,4,5-tetra-hydro-1,3,3-tri-methyl-dipyrrin are reported; 4-bromo-2-formyl-1-tosyl-1H-pyrrole, C₁₂H₁₀BrNO₃S, (E)-4-bromo-2-(2-nitro-vin-yl)-1-tosyl-1H-pyrrole, C₁₃H₁₁BrN₂O₄S, and 6-(4-bromo-1-tosyl-pyrrol-2-yl)-4,4-dimethyl-5-nitro-hexan-2-one, C₁₉H₂₃BrN₂O₅S. The compounds show multitudinous inter-molecular C-H⋯O inter-actions, with bond distances and angle consistent in the series and within expectations, as well as varied packing types. The merits of collecting data beyond the standard resolution usually reported for small mol-ecules are discussed.

Keywords: chemical intermediates; crystal structure; high-resolution; pyrrole.

Grants and funding

This work was funded by H2020 Marie Sklodowska-Curie Actions grant 764837 to Mathias O. Senge.