Structural analysis of 2-iodo-benzamide and 2-iodo- N-phenyl-benzamide

Keshab M Bairagi; Vipin B S Kumar; Subhrajyoti Bhandary; Katharigatta N Venugopala; Susanta K Nayak

doi:10.1107/S2056989018010162

Structural analysis of 2-iodo-benzamide and 2-iodo- N-phenyl-benzamide

Acta Crystallogr E Crystallogr Commun. 2018 Jul 20;74(Pt 8):1130-1133. doi: 10.1107/S2056989018010162. eCollection 2018 Aug 1.

Authors

Keshab M Bairagi¹, Vipin B S Kumar¹, Subhrajyoti Bhandary², Katharigatta N Venugopala³, Susanta K Nayak¹

Affiliations

¹ Department of Chemistry, Visvesvaraya National Institute of Technology, Nagpur 440 010, Maharashtra, India.
² Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal 462 066, Madhya Pradesh, India.
³ Department of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South Africa.

Abstract

The title compounds, 2-iodo-benzamide, C₇H₆INO (I), and 2-iodo-N-phenyl-benzamide, C₁₃H₁₀INO (II), were both synthesized from 2-iodo-benzoic acid. In the crystal structure of (I), N-H⋯O and hydrogen bonds form two sets of closed rings, generating dimers and tetra-mers. These combine with C-I⋯π(ring) halogen bonds to form sheets of mol-ecules in the bc plane. For (II), N-H⋯O hydrogen bonds form chains along the a-axis direction, while inversion-related C-I⋯π(ring) contacts supported by C-H⋯π(ring) interactions generate sheets of mol-ecules along the ab diagonal.

Keywords: C—I⋯π(ring) interactions; benzamide; crystal structure; dimer; hydrogen bonds; tetramer.

Grants and funding

This work was funded by Visvesvaraya Technological University grant . National Research Foundation grants 91995 and 96807. Durban University of Technology grant .