Crystal structure of 1-(4-{[(E)-5-bromo-2-hydroxybenzylidene]- amino}phenyl)ethanone oxime, C15H13BrN2O2

Abstract

Source of materialTo an ethanol solution (5 ml) of 2-hydroxy-5-bromobenzaldehyde (202.6mg, 1.01 mmol) was added an ethanol solution (5 ml) of 4-aminophenylethanone oxime(151.9 mg, 1.01 mmol). After the solution had been stirred at 327 Kfor 5h,the mixture was filtered. Ther esidue was washed successively with ethanol and hexane, respectively. Theisolated compound was dried under reduced pressure to yield 262.8 mg of yellow solid (yield 78 %, m.p. 493-494 K). The single crystals were obtained by slow evaporation from an acetonitrile solution at room temperature. Elemental analysis -found: C, 54.07 %; H, 3.93 %; N, 8.41 %; Br, 23.98 %; calculated for C 15 H 13 BrN 2 O 2 :C ,5 4.23 %; H, 3.98 %; N, 8.32 %; Br, 23.87 %. DiscussionThe Schiff base compounds and their derivatives have been playing an important role in the development of coordination chemistry[1,2] because they can accommodate one, two or more metal centers and form homo-and heteronuclear metal complexes [3-6], being excellent catalysts for epoxidation, aziridination [7], models of reaction centers of metalloenzymes [8],and nonlinear optical materials [9]. Moreover, in biological and artificial systems, allosteric regulation is effective in controlling molecular functions, such as molecular recognition and biological activity [10].Schiff base compounds are easily prepared from the corresponding carbonyl compounds and amine. Most of Schiff base derivatives are stable in solution and solid state, and are stable to hydrolysis compared with the corresponding imines [11,12]. The title crystal structure is only built up by the C 15 H 13 BrN 2 O 2 molecules, in which all bond lengths are in normalranges. The two benzene rings form ad ihedral angle of 43.11°. Therea re strong intramolecular O-H×××Nh ydrogen bonds between the hydroxyl( O2-H2)g roups and the Schiff base nitrogen (N2) atoms, with d(N2×××O2) =2 .615 Å. The molecules are held together by two pairs of intermolecular O1-H1×××N1 and C5-H5×××O2 hydrogen bonds, forming an infinite 1D supramolecular structure along the c axis [13,14].

Crystal structure of (E)-1-(4-{[(E)-4-Diethylamino-2-hydroxybenzene methylene]amino}phenyl)ethanone methoxy oxime, C20H27ClN3O3

“…And all bond lengths are in normal ranges [4]. In the title compound, there are weak non-classical intermolecular C-H· · · Cl and C-H· · · O hydrogen bonds.…”

“…4-Aminoacetophenone methoxy oxime was prepared by a similar method reported earlier [4]. 4-Aminoacetophenone methoxy oxime (148.2 mg, 1 mmol) dissolved in ethanol solution (5 mL) was added to 4-(diethylamino)salicylaldehyde (200.0 mg, 1 mmol) dissolved in ethanol solution (5 mL).…”

Crystal structure of (E)-1-(4-(((E)-4-(diethylamino)-2-hydroxybenzylidene)amino)phenyl)ethan-1-one oxime, C19H23N3O2

“…Recently particular attention has been paid to the synthesis [5][6][7]. The application of oxime-type compounds and their complexes, for instance: they have been used to identify metal ions [8,9], have fascinating magnetic properties [10], many other fields of materials sciences [11][12][13][14][15][16][17] materials.…”

Synthesis and crystal structure of bis(μ2-acetato-κ2 O:O′)-bis{μ2-4-chloro-2-(8-(4-(diethylamino)-2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)phenolato-κ6 O:O,N,N′,O′:O′}trizinc(II), C44H49Cl2N6O12Zn3

“…Salen-type compounds and their transition metal complexes have been investigated for many decades with a focus on modified ligand systems in the last years [1][2][3][4]. New research fields are the use of such complexes in a very wide and diversified subjects such as, optical and magnetic materials [5][6][7][8][9][10] and supramolecular architectures [11][12][13][14][15][16].…”