N-(3-Chloro-4-fluorophenyl)-2-(naphthalen-1-yl)acetamide

Abstract

In the title compound, C18H13ClFNO, the dihedral angle between the mean planes of the chloro- and fluoro-substituted benzene ring and the naphthalene ring system is 60.5 (8)°. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds, forming a zigzag chain along [101].

HalogenatedC,N-diarylacetamides: molecular conformations and supramolecular assembly

“…Compounds (VIII) and (IX) crystallize in the space groups P2 1 /c and Pbca, respectively, and, whereas in (VIII) molecules related by translation are linked into simple C(4) chains by N-HÁ Á ÁO hydrogen bonds, in (IX) molecules related by a b-glide plane are linked by N-HÁ Á ÁO hydrogen bonds modestly reinforced by C-HÁ Á ÁO hydrogen bonds to form a C(4)C(4)[R 1 2 (6)] chain of rings. In each of compounds (X) (Praveen et al, 2011) planes, respectively, are linked by N-HÁ Á ÁO hydrogen bonds to form C(4) chains running parallel to [101] and [001] respectively. In addition, there are two aromaticstacking interactions in each structure, although these were not mentioned in the original structure reports.…”

“…stereoview of part of the crystal structure of compound (X), showing the formation of a -stacked sheet of hydrogen-bonded chains parallel to (010). The original atomic coordinates(Praveen et al, 2011) have been used. Hydrogen bonds are shown as dashed lines and, for the sake of clarity, H atoms not involved in the motif shown have been omitted.…”

N-(4-Bromophenyl)-2-(naphthalen-1-yl)acetamide

“…For studies of amides in therapy, myocardial infarction and ischemic disease, see: Dorsch et al (2002); Wang, Li & Li (2010); Wang, Beck et al (2010). For related structures, see: Fun et al (2010); Li & Wu (2010); Xiao et al (2010); Praveen et al (2011). For standard bond-length data, see: Allen et al (1987).…”

“…Amides are also used as ligands due to their excellent coordination abilities (Wu et al, 2008(Wu et al, , 2010 and for the therapy of thromboembolic disorder and effective anticoagulants for myocardial infarction and ischemic disease (Dorsch et al, 2002;Wang, Li & Li, 2010;Wang, Beck et al, 2010). Crystal structures of some acetamide derivatives, viz., 2-(4-bromophenyl)-N-(2-methoxyphenyl)acetamide (Xiao et al, 2010), N-benzyl-2-(2-bromophenyl)-2-(2-nitrophenoxy) acetamide (Li & Wu, 2010) and N-(3-chloro-4fluorophenyl)-2-(naphthalen-1-yl)acetamide (Praveen et al, 2011) have been reported. In view of the importance of amides, we report herein the crystal structure of the title compound.…”

3-Chloro-N-(4-methoxyphenyl)propanamide

“…For the coordination abilities of amides, see: Wu et al (2008Wu et al ( , 2010. For related structures, see: Akkurt et al (2010); Huang & Xu, (2006); Moreno-Fuquen et al (2011); Praveen et al (2011). For the crystal structure of another compound featuring C-HÁ Á ÁO contacts, see: Betz et al (2011).…”