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Two closely related 2-(benzofuran-2-yl)-2-oxoethyl benzoates: structural differences and C—H...O hydrogen-bonded supramolecular assemblies

Two closely related 2-(benzofuran-2-yl)-2-oxoethyl benzoates: structural differences and C—H...O hydrogen-bonded supramolecular assemblies

Authors :
Li Yee Then
C. S. Chidan Kumar
Huey Chong Kwong
Yip-Foo Win
Siau Hui Mah
Ching Kheng Quah
S. Naveen
Ismail Warad
Source :
Acta Crystallographica Section E: Crystallographic Communications, Vol 73, Iss 7, Pp 1087-1091 (2017)
Publication Year :
2017
Publisher :
International Union of Crystallography, 2017.

Abstract

The compounds 2-(1-benzofuran-2-yl)-2-oxoethyl 2-nitrobenzoate, C17H11NO6 (I), and 2-(1-benzofuran-2-yl)-2-oxoethyl 2-aminobenzoate, C17H13NO4 (II), were synthesized under mild conditions. Their molecular structures were characterized by both spectroscopic and single-crystal X-ray diffraction analysis. The molecular conformations of both title compounds are generally similar. However, different ortho-substituted moieties at the phenyl ring of the two compounds cause deviations in the torsion angles between the carbonyl group and the attached phenyl ring. In compound (I), the ortho-nitrophenyl ring is twisted away from the adjacent carbonyl group whereas in compound (II), the ortho-aminophenyl ring is almost co-planar with the carbonyl group. In the crystal of compound (I), two C—H...O hydrogen bonds link the molecules into chains propagating along the c-axis direction and the chains are interdigitated, forming sheets parallel to [20-1]. Conversely, pairs of N—H...O hydrogen bonds in compound (II) link inversion-related molecules into dimers, which are further extended by C—H...O hydrogen bonds into dimer chains. These chains are interconnected by π–π interactions involving the furan rings, forming sheets parallel to the ac plane.

Details

Language :
English
ISSN :
20569890
Volume :
73
Issue :
7
Database :
Directory of Open Access Journals
Journal :
Acta Crystallographica Section E: Crystallographic Communications
Publication Type :
Academic Journal
Accession number :
edsdoj.3c36b529b5f43b99c88f08bb1a0b36c
Document Type :
article
Full Text :
https://doi.org/10.1107/S2056989017009422