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. 2025 May 2;10(Pt 5):x250384.
doi: 10.1107/S2414314625003840. eCollection 2025 May.

N, N'-[Oxybis(benzene-4,1-di-yl)]diacetamide

Rao M Uppu  1 , Ogad A Agu  2 , Sainath Babu  1 , Patrick F Mensah  2 , Frank R Fronczek  3
Affiliations

N, N'-[Oxybis(benzene-4,1-di-yl)]diacetamide

Rao M Uppu et al. IUCrdata. .

Abstract

In the title compound, C16H16N2O3, 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.

Keywords: N,N′-(oxybis(4,1-phenyl­ene))diacetamide; acetamino­phen impurity N; anilide analgesics; crystal structure.

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Figures

Figure 1
Figure 1
The asymmetric unit of the title compound with 50% ellipsoids.
Figure 2
Figure 2
Detail of the the hydrogen bonding with 50% ellipsoids.
Figure 3
Figure 3
The unit-cell packing. Only NH hydrogen atoms are shown.
See this image and copyright information in PMC

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