The effect of hydrogen bonding on the conformations of 2-(1H-indol-3-yl)-2- oxoacetamide and 2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide

Vijayakumar N. Sonar, Sean Parkin, Peter A. Crooks

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

In the title compounds, C10H8N2O 2, (I), and C12H12N2O2, (II), the two carbonyl groups are oriented with torsion angles of -149.3 (3) and -88.55 (15)°, respectively. The single-bond distances linking the two carbonyl groups are 1.528 (4) and 1.5298 (17) Å, respectively. In (I), the molecules are linked by an elaborate system of N - H⋯O hydrogen bonds, which form adjacent R22(8) and R4 2(8) ring motifs to generate a ladder-like construct. Adjacent ladders are further linked by N - H⋯O hydrogen bonds to build a three-dimensional network. The hydrogen bonding in (II) is far simpler, consisting of helical chains of N - H⋯O-linked molecules that follow the 21 screw of the b axis. It is the presence of an elaborate hydrogen-bonding system in the crystal structure of (I) that leads to the different torsion angle for the orientation of the two adjacent carbonyl groups from that in (II).

Original languageEnglish
Pages (from-to)o405-o407
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume68
Issue number10
DOIs
StatePublished - Oct 2012

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology (all)

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