N-(2,6-Dibromophenyl)formamide

Abstract

In the crystal structure of the title compound, C(7)H(5)Br(2)NO, molecules related by translation are linked through N-H...O hydrogen bonds to form chains in the crystallographic a direction, with the aryl rings stacked parallel to each other along the chain. Besides the N-H...O hydrogen bonds, Br...O and Br...Br intermolecular interactions complete the packing of molecules in the crystal structure.

Supramolecular Packing of a Series ofN-Phenylamides and the Role of NH···O═C Interactions

“…This tetramer has already been reported as a Nphenylformamide cocrystal directed by hydrogen-bonding NH•••OC, although without a supramolecular study. 20 Therefore, it is remarkable that this same tetramer is still formed in solution, 22 reinforcing the idea that this can be treated as the minimum unit, i.e., M1 for this compound. The stabilization energy of −33.76 kcal mol −1 was obtained for the tetramer (G tetramer ) by theoretical calculations.…”

“…The structures used in this study are available in the CSD through the following numbers: (1) 785065, 45 (2) 239624, 46 (3) 965773, 47 (5) 1314188, 48 (6) 747306, 49 (7) 682820. 20 Crystal structure parameters of compound 4 are listed in Table S1 in the Supporting Information. Experimental essays for crystallization of compound 4 failed with the aim to obtain crystals with good quality for X-ray data collection.…”

“…Compounds 1−3 and 5−6 presented one molecule in the asymmetric unit (Z′ = 1), and compounds 4 and 7 presented two molecules (Z′ = 2). Compound 7 has two conformational isomers: Z (7A) and E (7B), which were presented as a cocrystal by Levendis et al 20 Cable et al 21 reported that the Z isomer adopts a planar structure and is 2.5 kcal mol −1 more stable than its E isomer. In the solution, 1 H NMR experiments determined the existence of the mixture of species Z and E with almost the same abundance in a chloroform solution.…”

N-(2,6-Diisopropylphenyl)thioamide

“…For related thioamide structures, see: Chitanda et al (2008); Michta et al (2008); Omondi et al (2009a); Jarchow & Schmalle (1977). For related N-2,6-disubstituted-arylformamides, see: Omondi et al (2008Omondi et al ( , 2009b. For phase transformations in N-2,6-phenylformamides and N-2,6dichlorophenylformamide, see: Omondi et al (2005); Gowda et al (2000).…”

“…The synthesis of arylthioamides related to the title compound has been described (Fernandes & Reid, 2003) as have the structures of related thioamides (Chitanda et al, 2008;Michta et al, 2008;Omondi et al, 2009a;Jarchow & Schmalle, 1977) and N-2,6-disubstituted-arylformamides (Omondi et al, 2009b;Omondi et al, 2009c;Omondi et al, 2008). In a previous study of 2,6-disubstituted N-arylformamides (Omondi et al, 2005), we analyzed the effect of chloro-methyl exchange and the role of weak interactions on the structural and thermal properties of the compounds studied.…”