Halogenated C,N-di­aryl­acetamides: mol­ecular conformations and supra­molecular assembly

Nayak, Prakash S. and Jasinski, Jerry P. and Golen, James A. and Narayana, B. and Kaur, Manpreet and Yathirajan, H. S. and Glidewell, Christopher (2014) Halogenated C,N-di­aryl­acetamides: mol­ecular conformations and supra­molecular assembly. Acta Crystallographica Section C, 70 (9). pp. 889-894. ISSN 2053-2296

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Official URL: https://doi.org/10.1107/S2053229614018713


The structures of four halogenated N,2-diaryl­acetamides are reported and compared with a range of analogues. N-(4-Chloro-3-methyl­phen­yl)-2-phenyl­acetamide, C15H14ClNO, (I), and N-(4-bromo-3-methyl­phen­yl)-2-phenyl­acetamide, C15H14BrNO, (II), are isostructural in the space group P\overline{1}. The mol­ecules of (I) and (II) are linked into chains of rings by a combination of N-H...O and C-H...[pi](arene) hydrogen bonds. The mol­ecules of N-(4-chloro-3-methyl­phen­yl)-2-(2,4-di­chloro­phen­yl)acetamide, C15H12Cl3NO, (III), and N-(4-bromo-3-methyl­phen­yl)-2-(2-chloro­phen­yl)acetamide, C15H13BrClNO, (IV), are linked into simple C(4) chains by N-H...O hydrogen bonds, but significant C-H...[pi](arene) inter­actions are absent. The N-aryl groups in compounds (III) and (IV) adopt a different orientation, by ca 180°, from that of the corresponding groups in compounds (I) and (II), but otherwise the conformations of (I)-(IV) are very similar. Comparisons are drawn between compounds (I) and (IV) and a range of analogues of the type R1CH2CONHR2, where R2 represents a halogenated aryl ring and R1 represents either another halogenated aryl ring or a naphthalen-1-yl unit.

Item Type: Article
Uncontrolled Keywords: crystal structure, acetamides, C,N-diarylacetamides, molecular conformation, supramolecular assembly, hydrogen bonding, benzyl penicillins
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: MUL SWAPNA user
Date Deposited: 24 Oct 2019 05:05
Last Modified: 24 Oct 2019 05:05
URI: http://eprints.uni-mysore.ac.in/id/eprint/9477

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