Home Crystal structure of 1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone O-benzyl oxime, C22H19BrN2O2
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Crystal structure of 1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone O-benzyl oxime, C22H19BrN2O2

  • Yan-Bin Wang EMAIL logo
Published/Copyright: April 19, 2017

Abstract

C22H19BrN2O2, monoclinic, P21/c (no. 14), a = 18.4760(16) Å, b = 4.8400(3) Å, c = 21.6410(18) Å, b = 96.162(1)°, V = 1924.0(3) Å3, Z = 4, Rgt(F) = 0.0542, wRref(F2) = 0.1719, T = 298(2) K.

CCDC no.:: 1541179

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Orange-red prism
Size:0.45 × 0.16 × 0.14 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:21.6 cm−1
Diffractometer, scan mode:Bruker SMART, φ and ω
2θmax, completeness:50°, >99%
N(hkl)measured, N(hkl)unique, Rint:9013, 3385, 0.078
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1637
N(param)refined:245
Programs:SHELX [1], Bruker programs [2]
Table 2

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
N10.1967(2)−0.3033(9)0.48276(19)0.0460(12)
N20.3880(3)0.3823(10)0.4277(2)0.0492(12)
O10.1386(2)−0.4843(8)0.48751(16)0.0557(11)
O20.4651(2)0.5419(10)0.33787(18)0.0675(13)
H20.45560.45350.36830.101*
Br10.20930(4)1.25505(15)0.24170(3)0.0826(4)
C10.2174(3)−0.3982(15)0.5955(2)0.0679(19)
H1A0.1675−0.45760.59140.102*
H1B0.2251−0.26650.62870.102*
H1C0.2486−0.55470.60450.102*
C20.2342(3)−0.2663(11)0.5359(2)0.0423(13)
C30.3001(3)−0.0926(11)0.5346(2)0.0395(13)
C40.3099(3)0.0779(11)0.4837(2)0.0414(13)
H40.27220.09750.45190.050*
C50.3751(3)0.2180(11)0.4801(2)0.0455(14)
C60.4307(3)0.1904(13)0.5278(3)0.0625(17)
H60.47510.27710.52510.075*
C70.4203(4)0.0350(15)0.5793(3)0.074(2)
H70.45670.02770.61240.088*
C80.3563(3)−0.1108(13)0.5825(3)0.0582(17)
H80.3510−0.22140.61680.070*
C90.3358(3)0.5265(11)0.4010(2)0.0454(14)
H90.29110.52150.41700.054*
C100.3430(3)0.6999(11)0.3464(2)0.0442(14)
C110.4070(3)0.7040(13)0.3173(3)0.0542(16)
C120.4114(4)0.8727(16)0.2660(3)0.068(2)
H120.45370.87390.24620.081*
C130.3538(4)1.0376(14)0.2443(3)0.0668(19)
H130.35791.15270.21040.080*
C140.2893(4)1.0352(13)0.2722(2)0.0583(17)
C150.2858(3)0.8683(13)0.3237(2)0.0529(16)
H150.24370.86940.34370.063*
C160.1068(3)−0.5483(13)0.4253(3)0.0572(16)
H16A0.0798−0.71970.42640.069*
H16B0.1457−0.57810.39930.069*
C170.0570(3)−0.3295(11)0.3961(3)0.0471(15)
C18−0.0021(3)−0.2426(13)0.4251(3)0.0680(18)
H18−0.0097−0.31810.46340.082*
C19−0.0500(4)−0.0469(15)0.3987(3)0.074(2)
H19−0.09000.00650.41850.089*
C20−0.0379(4)0.0687(15)0.3426(3)0.0695(19)
H20−0.06960.20220.32450.083*
C210.0203(4)−0.0121(15)0.3135(3)0.072(2)
H210.02820.06540.27540.087*
C220.0677(3)−0.2091(13)0.3405(3)0.0608(17)
H220.1077−0.26120.32050.073*

Source of material

To an ethanol solution (4 mL) of 1-(3-aminophenyl)ethanone O-benzyl oxime (403.7 mg, 1.57 mmol) was added an ethanol solution (4 mL) of 5-bromo-2-hydroxybenzaldehyde (335.0 mg, 1.67 mmol). The mixture was stirred at 55–60 °C for 12 h, the solvent was removed under reduced pressure and the residue was washed successively with ethanol and ethanol/hexane (1:4 v/v), respectively. The product was dried in vacuo, and a yellow crystalline solid was obtained. Yield 79.4%. m.p. 90–91 °C. Anal. Calcd. for C22H19BrN2O2 (%): C, 62.42%; H, 4.52%; N, 6.62%; Found: C, 62.45%; H, 4.49%; N, 6.65%.

Experimental details

Hydrogen atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C).

Discussion

Some of oxime-type compounds have received long-lasting research interest in forming homo- and heteronuclear metal complexes with interesting properties [3], [4], [5], [6], such as luminescent materials [7], [8], [9], magnetic properties [10, 11] and building blocks for cyclic supramolecular structures [12], [13], [14], [15].

The crystal structure of the title compound is only built up by one molecule, in which all bond lengths are in normal ranges. In the crystal structure, one intramolecular O2-H2⋯N2 hydrogen bond between the hydroxyl group and the N2 atom forms a six-membered ring in each molecule. Weak intramolecular C-H⋯O hydrogen bonds may be present. In addition, the structure of the title compound contains an infinite chain along b via C16-H16A⋯π (C17–C22) and C9-H9⋯N1 hydrogen bond interactions.

References

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Received: 2016-11-2
Accepted: 2017-3-30
Published Online: 2017-4-19
Published in Print: 2017-5-24

©2017 Yan-Bin Wang, published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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