Home Physical Sciences Crystal structure of (E)-1-(3-((E)-((2-hydroxynaphthalen-1-yl)methylene)amino)phenyl)ethanone O-benzyl oxime, C26H22N2O2
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Crystal structure of (E)-1-(3-((E)-((2-hydroxynaphthalen-1-yl)methylene)amino)phenyl)ethanone O-benzyl oxime, C26H22N2O2

  • Yan-Bin Wang EMAIL logo and Qiong Su
Published/Copyright: May 20, 2017

Abstract

C26H22N2O2, monoclinic, P21/c (no. 14), a = 21.8152(18) Å, b = 4.3629(2) Å, γ = 22.0099(12) Å, β = 106.951(6)°, V = 2003.8(2) Å3, Z = 4, Rgt(F) = 0.0639, wRref(F2) = 0.1555, T = 298(2) K.

CCDC no.:: 1546077

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

Table 1

Data collection and handling.

Crystal:Yellow block
Size:0.34 × 0.14 × 0.10 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.8 cm−1
Diffractometer, scan mode:SuperNova Dual, ω scans
2θmax, completeness:52°, >99%
N(hkl)measured, N(hkl)unique, Rint:7312, 3943, 0.063
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1984
N(param)refined:310
Programs:SHELX [1], CrysAlisPRO [2]
Table 2

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

AtomxyzUiso*/Ueq
N10.10605(17)0.1082(8)0.47091(17)0.0346(9)
O10.02905(14)−0.0204(7)0.36222(15)0.0445(9)
H10.04200.06580.39670.067*
O20.34938(15)0.9255(8)0.62052(14)0.0454(9)
C110.1495(2)−0.0493(10)0.4551(2)0.0352(11)
H110.1903−0.06040.48370.042*
C90.1856(2)−0.3908(9)0.38058(19)0.0300(10)
C100.13720(19)−0.2081(9)0.39532(19)0.0293(10)
C40.1705(2)−0.5433(10)0.3206(2)0.0341(11)
C170.1829(2)0.4023(10)0.5546(2)0.0335(10)
H170.21500.36650.53530.040*
C120.1223(2)0.2772(9)0.5279(2)0.0332(10)
C70.2917(2)−0.6147(10)0.4054(2)0.0397(12)
H70.3325−0.63640.43360.048*
N20.28790(17)0.7942(9)0.59236(17)0.0400(10)
C160.1964(2)0.5795(10)0.6093(2)0.0334(10)
C80.2481(2)−0.4389(10)0.4221(2)0.0372(11)
H80.2594−0.34720.46190.045*
C30.1090(2)−0.5039(10)0.2768(2)0.0389(11)
H30.0992−0.60080.23750.047*
C60.2770(2)−0.7651(11)0.3464(2)0.0445(12)
H60.3072−0.88780.33580.053*
C20.0640(2)−0.3267(10)0.2914(2)0.0408(12)
H20.0243−0.29980.26160.049*
C10.0770(2)−0.1830(10)0.3511(2)0.0342(11)
C210.4411(2)1.1474(12)0.5997(2)0.0446(12)
C180.2605(2)0.7239(10)0.6344(2)0.0372(11)
C130.0747(2)0.3352(10)0.5575(2)0.0403(12)
H130.03370.25760.53990.048*
C50.2166(2)−0.7258(11)0.3049(2)0.0418(12)
H50.2062−0.82240.26550.050*
C150.1483(2)0.6304(10)0.6388(2)0.0382(11)
H150.15670.74700.67560.046*
C140.0880(2)0.5052(10)0.6122(2)0.0419(12)
H140.05610.53680.63180.050*
C240.5673(3)1.3328(14)0.6474(3)0.0630(16)
H24a0.61021.38100.66610.076*
H24Aa0.60941.40060.66310.076*
C200.3727(2)1.0456(14)0.5710(2)0.0572(15)
H20A0.34661.21790.55080.069*
H20B0.37070.88940.53910.069*
C190.2897(3)0.7842(13)0.7038(2)0.0588(15)
H19A0.33010.67990.71830.088*
H19B0.26150.71070.72680.088*
H19C0.29621.00050.71070.088*
C26a0.4875(5)1.077(3)0.5672(5)0.048(3)
H26a0.47580.96350.52990.057*
C26′a0.4688(5)1.319(3)0.5665(5)0.060(3)
H26′a0.44541.37790.52570.072*
C25a0.5495(6)1.180(3)0.5917(6)0.064(3)
H25a0.57931.14400.56970.077*
C22a0.4598(6)1.322(3)0.6525(5)0.056(3)
H22a0.42981.37960.67290.067*
C23a0.5223(5)1.417(3)0.6766(5)0.064(3)
H23a0.53401.53870.71290.077*
C25′a0.5320(6)1.416(3)0.5903(7)0.067(3)
H25′a0.54961.54150.56560.080*
C22′a0.4770(5)1.052(3)0.6614(5)0.065(4)
H22′a0.45780.93180.68570.078*
C23′a0.5402(5)1.137(3)0.6852(5)0.058(3)
H23′a0.56481.06930.72490.069*

Source of materials

To a hot ethanolic solution (10 mL) of benzaldehyde (290.4 mg, 1 mmol) was added an ethanolic solution (5 mL) of (E)-1-(((3-(1-aminoethyl)phenyl)imino)methyl)naphthalen-2-ol (106.1 mg, 1.00 mmol). After the mixture had been stirred at 338 K for 4 h, the solvent was partially evaporated under reduced pressure. After cooling to room temperature, the mixture was filtered, washed successively with ethanol and hexane. The isolated compound was dried under reduced pressure to yield 302.1 mg of light yellow solid. Yield: 76.5%. m.p. 331–333 K. Block-shaped single crystals suitable for X-ray diffraction studies were obtained by slow evaporation from an ethanolic solution at room temperature. Elemental analysis: Calcd. for C26H22N2O2 [%]: C, 79.16; H, 5.62; N, 7.10; Found: C, 79.16; H, 5.62; N, 7.10.

Experimental details

Molecular structure was refined using the SHELX package. Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms. There is a disorder of the phenyl group.

Comment

Oxime-type compounds and their derivatives play an important role in the development of coordination chemistry [3], [4], [5], [6], [7], because they can accommodate one, two or more metal centers and form homo- and heteronuclear metal complexes [8], [9], [10], [11], [12]. Moreover, oxime-type compounds and its metal complexes studied by the group of W. K. Dong have a significant application in the fields of luminescence and magnetic materials, catalysis and supramolecular chemistry [13], [14], [15], [16].

The crystal structure is only built up from C26H22N2O2 molecules, in which all bond lengths are in normal ranges. The aryl ring (C12—C17) and the naphthyl moiety form a dihedral angle of 34.82(11)°. In addition, there is a strong intramolecular O—H⋯N hydrogen bond interaction between the hydroxyl (O1—H1) group and the Schiff base nitrogen (N1) atom, with the distance of d(N1⋯O1) = 2.552(3) Å [17].

References

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Received: 2017-1-4
Accepted: 2017-5-3
Published Online: 2017-5-20
Published in Print: 2017-7-26

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

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

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  61. Corrigendum
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