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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
- 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