The crystal and molecular structure of anti-α-bromoacetophenone oxime

Abstract

The structure of anti-e-bromoacetophenone oxime (CsHsNOBr) was solved by Fourier methods and refined by full-matrix least-squares analysis to a final RI = 0.046; space group: 14, Z= 8. The distances and angles are similar to those observed in other oxime structures. The phenyl group and the oxime function are not coplanar, the angle between their normals being 54.3 °. Molecules are linked into tetramers by O-H.--N hydrogen bonds about an $4 axis at -}, 0, z, with both the oxygens and nitrogens assuming nearly tetrahedral arrangements. A cluster of four bromine atoms make van der Waals contacts of 3.681 ,~ about an $4 axis at 0, 0, z.

Source of Cooperativity in Halogen‐Bonded Haloamine Tetramers

“…[10] That analysisw as aimed at the characterization of as tructural motif found in crystal structure of anti-abromoacetophenone oxime. [9] Some very weak synergy (À0.47 kcal mol À1 )o ccurred in the models ystem, [10] but the origin of the cooperativity has not yetb een revealed. Therefore, the mixingo ft he orbitals in these systemsa ppeared to be too vague for ad etailed analysisw ith the Kohn-ShamM O theorya nd the energy decomposition analysis( EDA), as described in the Computational Methods Section.…”

The Chemistry of α-Haloketones and Their Utility in Heterocyclic Synthesis

“…The only crystal and molecular structures of acetophenones found in the literature are reported for anti-α-bromoacetophen-one oxime ( Figure 3 ) [ 32 , 33 ].…”

Graphical enumeration of hydrogen-bonded structures

“…In some cases H bonding leads to the cyclic aggregates I2(3), 12(4) and 12(6) present in the structures of acetone oxime (Bierlein & Lingafelter, 1951), anti-a-bromoacetophenone oxime (Wetherington & Moncrief, 1973), and (+)-fl-promedol alcohol (De Camp & Ahmed, 1972). The unique H-bonded layer L~(2,8) occurs in the structure of methyl 5-thio-fl-D-ribopyranoside (Girling & Jeffrey, 1973).…”