Open Access2‐(2‐Acetylamino‐5‐chlorophenyl)‐2,2‐difluoroethanoic acid and 2‐(2‐acetylamino‐5‐methylphenyl)‐2,2‐difluoroethanoic acid, and 2‐(2‐acetylaminophenyl)‐2,2‐difluoro‐ N ‐phenylacetamide and 2‐(2‐acetylaminophenyl)‐ N ‐(4‐chlorophenyl)‐2,2‐difluoroacetamide: examples of variation in molecular packing and hydrogen‐bonding motif induced by substituent change
Author(s) -
Boechat Nubia,
Maciel Lindalva C.,
Pinto Angelo C.,
Wardell Solange M. S. V.,
Skakle Janet M. S.,
Howie R. Alan
Publication year - 2005
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s0108270105007547
Subject(s) - substituent , chemistry , hydrogen bond , medicinal chemistry , stereochemistry , molecule , organic chemistry
Among the title compounds, viz . the acids C 10 H 8 ClF 2 NO 3 , (I), and C 11 H 11 F 2 NO 3 , (II), and the amides C 14 H 14 F 2 N 2 O 2 , (III), and C 14 H 13 ClF 2 N 2 O 2 , (IV), the change of substituent from Cl in (I) to methyl in (II) has a dramatic effect upon the hydrogen bonding between the molecules, which occur in layers in both cases. In the structures of (III) and (IV), hydrogen bonds connect the molecules to form chains, but the introduction of a chloro substituent in (IV) has a profound effect on the orientation of the molecules within the chains and the packing of the chains in the structure as a whole.