<i>N</i>,<i>N</i>′-[Oxybis(benzene-4,1-diyl)]diacetamide

In the title compound, C<sub>16</sub>H<sub>16</sub>N<sub>2</sub>O<sub>3</sub>, the phenyl groups are twisted away from coplanarity with the ether linkage, forming a dihedral angle of 59.49 (4)° with each other. The ether oxygen atom lies somewhat out of both phenyl planes, by 0.066 (2) and 0.097 (2) Å. The acetamide substituents have quite different conformations with respect to the phenyl groups on either side of the mol-ecule. On one side, the C-C-N-C torsion angle is 21.0 (2)°, while on the other side it is 76.4 (2)°. In the crystal, the acetamide N-H groups form inter-molecular N-H⋯O hydrogen bonds to acetamide O atom, with both NH groups donating to the same mol-ecule. Thus, ladder-like chains exist in the [101] direction. One of the methyl groups has its H atoms disordered into two orientations, and the crystal chosen for data collection was found to be twinned.

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Publication Details

Journal
IUCrData
Published
2025-05-02
DOI
https://doi.org/10.1107/s2414314625003840
Citations
2
Primary Topic
Crystal structures of chemical compounds
Type
article
Field-Weighted Citation Impact
1.07

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article

N,N′-[Oxybis(benzene-4,1-diyl)]diacetamide

Rao M. Uppu, S.A. Babu, Frank Rolf Fronczek, Ogad A. Agu et al.
2 citations
IUCrData
Crystal structures of chemical compounds
1.07
article

N,N′-[Oxybis(benzene-4,1-diyl)]diacetamide

Rao M. Uppu, S.A. Babu, Frank Rolf Fronczek, Ogad A. Agu, Patrick F Mensah
article en
2 citations

Abstract

In the title compound, C<sub>16</sub>H<sub>16</sub>N<sub>2</sub>O<sub>3</sub>, the phenyl groups are twisted away from coplanarity with the ether linkage, forming a dihedral angle of 59.49 (4)° with each other. The ether oxygen atom lies somewhat out of both phenyl planes, by 0.066 (2) and 0.097 (2) Å. The acetamide substituents have quite different conformations with respect to the phenyl groups on either side of the mol-ecule. On one side, the C-C-N-C torsion angle is 21.0 (2)°, while on the other side it is 76.4 (2)°. In the crystal, the acetamide N-H groups form inter-molecular N-H⋯O hydrogen bonds to acetamide O atom, with both NH groups donating to the same mol-ecule. Thus, ladder-like chains exist in the [101] direction. One of the methyl groups has its H atoms disordered into two orientations, and the crystal chosen for data collection was found to be twinned.

IUCrDataVol. 10(5)
Louisiana State University (US), Southern University and Agricultural and Mechanical College (US)
National Science Foundation, National Institutes of Health, National Institute of General Medical Sciences, Division of Chemistry
Clean water and sanitation
Openalex Percentile: Top 24%
Crystal structures of chemical compounds
1.07
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