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Halogenated C , N ‐diarylacetamides: molecular conformations and supramolecular assembly
Author(s) -
Nayak Prakash S.,
Jasinski Jerry P.,
Golen James A.,
Narayana Badiadka,
Kaur Manpreet,
Yathirajan Hemmige S.,
Glidewell Christopher
Publication year - 2014
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229614018713
Subject(s) - chemistry , isostructural , acetamide , ring (chemistry) , molecule , stereochemistry , hydrogen bond , aryl , supramolecular chemistry , medicinal chemistry , crystallography , crystal structure , organic chemistry , alkyl
The structures of four halogenated N ,2‐diarylacetamides are reported and compared with a range of analogues. N ‐(4‐Chloro‐3‐methylphenyl)‐2‐phenylacetamide, C 15 H 14 ClNO, (I), and N ‐(4‐bromo‐3‐methylphenyl)‐2‐phenylacetamide, C 15 H 14 BrNO, (II), are isostructural in the space group P . The molecules of (I) and (II) are linked into chains of rings by a combination of N—H...O and C—H...π(arene) hydrogen bonds. The molecules of N ‐(4‐chloro‐3‐methylphenyl)‐2‐(2,4‐dichlorophenyl)acetamide, C 15 H 12 Cl 3 NO, (III), and N ‐(4‐bromo‐3‐methylphenyl)‐2‐(2‐chlorophenyl)acetamide, C 15 H 13 BrClNO, (IV), are linked into simple C (4) chains by N—H...O hydrogen bonds, but significant C—H...π(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 R 1 CH 2 CONH R 2 , where R 2 represents a halogenated aryl ring and R 1 represents either another halogenated aryl ring or a naphthalen‐1‐yl unit.