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March 3, 2026IUCrData0 citationsOpen Access

N -(3,5-Dichloro-4-hydroxyphenyl)acetamide

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RURao M. UppuFFFrank R. Fronczek

Key Points

  • The structure forms a three-dimensional network via hydrogen bonds, enhancing its stability and properties.
  • Two planar molecules have minor mean deviation differences, indicating close spatial relationships in their conformations.
  • The study employs crystallization techniques to analyze molecular arrangements and hydrogen-bond interactions within the compound.
  • Implications suggest that understanding these interactions could lead to insights in molecular design or pharmaceutical applications.

Abstract

The title compound, C8H7Cl2NO2, crystallizes in the triclinic space group P1 with three mol-ecules in the asymmetric unit. Two of them are essentially planar, with mean deviations of 13 non-hydrogen atoms of 0.029 and 0.030 Å, and differ only in the conformation of the O-H hydrogen atom. The third mol-ecule is quite nonplanar, with the CCNO acetamide plane forming a dihedral angle of 67.56 (5)° with the remainder of the mol-ecule. In the extended structure, the two almost planar mol-ecules form anti-parallel hydrogen-bonded chains through N-H⋯O inter-actions of the acetamide substituents. The N-H group of the nonplanar mol-ecule donates a bifurcated hydrogen bond to the O-H group and a Cl substituent of one of the planar mol-ecules. The O-H groups of all mol-ecules form inter-molecular hydrogen bonds to other O-H groups or carbonyl O atoms. Together, the hydrogen bonds generate a three-dimensional network.

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Cite This Study

Uppu et al. (2026) studied this question.

synapsesocial.com/papers/69a75f9ec6e9836116a2b1d9https://doi.org/10.1107/s2414314626000751
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