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BY-NC-ND 4.0 license Open Access Published by De Gruyter (O) November 15, 2017

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

  • Peng-Peng Li , Li Zhao EMAIL logo , Ji-Xing Zhao and Zhao-Bin Zhu

Abstract

C19H23N3O2, monoclinic, P21/n (no. 14), a = 17.8421(15) Å, b = 9.4778(9) Å, c = 22.116(2) Å, β = 108.230(10)°, Z = 8, V = 3552.2(6) Å3, Rgt(F) = 0.0649, wRref(F2) = 0.1506, T = 293(2) K.

CCDC no.: 1581469

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:Block, clear light yellow
Size:0.33 × 0.31 × 0.23 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:0.64 mm−1
Diffractometer, scan mode:SuperNova, ω-scans
θmax, completeness:70.2°, >96.9%
N(hkl)measured, N(hkl)unique, Rint:12972, 6558, 0.039
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3553
N(param)refined:446
Programs:CrysAlisPRO [1], SHELX [2], OLEX2 [3]
Table 2:

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

AtomxyzUiso*/Ueq
O10.71151(12)0.7864(2)0.09344(11)0.0542(6)
O21.20727(12)0.6934(3)0.47063(11)0.0679(7)
H2A1.20820.69370.50790.102*
O31.30637(13)1.3894(3)0.35409(16)0.0837(9)
H31.25991.37010.33630.126*
O40.74617(12)1.0546(3)0.12949(14)0.0725(8)
H4A0.73150.97630.11480.109*
N10.44416(14)0.6325(3)0.03029(13)0.0538(7)
N20.80871(14)0.6938(3)0.20193(12)0.0505(7)
N31.12874(14)0.6869(3)0.43078(12)0.0548(7)
N41.55787(16)1.1725(4)0.43286(18)0.0855(11)
N51.18722(14)1.2407(3)0.28582(13)0.0543(7)
N60.82973(14)1.0574(3)0.15334(14)0.0568(7)
C10.65467(17)0.7138(3)0.10506(14)0.0448(7)
C20.57813(16)0.7164(3)0.06382(14)0.0458(7)
H20.56620.77620.02880.055*
C30.51790(17)0.6323(3)0.07285(15)0.0473(7)
C40.5366(2)0.5447(4)0.12805(17)0.0591(9)
H40.49790.48720.13510.071*
C50.6100(2)0.5451(4)0.16996(17)0.0597(9)
H50.62030.48820.20590.072*
C60.67203(17)0.6276(3)0.16204(14)0.0468(7)
C70.74625(18)0.6233(4)0.20672(15)0.0540(8)
H70.75300.56730.24260.065*
C80.88589(17)0.6895(3)0.24576(14)0.0479(8)
C90.94488(19)0.7528(4)0.22766(15)0.0585(9)
H90.93280.79720.18830.070*
C101.02227(19)0.7511(4)0.26779(16)0.0614(10)
H101.06160.79240.25440.074*
C111.04201(17)0.6889(4)0.32751(14)0.0492(8)
C120.98163(18)0.6258(4)0.34457(15)0.0538(8)
H120.99360.58200.38410.065*
C130.90410(18)0.6253(4)0.30518(15)0.0543(8)
H130.86480.58270.31820.065*
C141.12358(18)0.6920(4)0.37199(15)0.0534(8)
C151.1930(2)0.7038(5)0.34810(18)0.0869(14)
H15A1.17790.67450.30440.130*
H15B1.23480.64440.37310.130*
H15C1.21070.79990.35150.130*
C160.42241(19)0.7318(4)−0.02271(17)0.0655(10)
H16A0.37490.6981−0.05450.079*
H16B0.46420.7341−0.04210.079*
C170.4083(2)0.8782(4)−0.0039(2)0.0946(15)
H17A0.39670.9389−0.04040.142*
H17B0.45460.91180.02830.142*
H17C0.36450.87810.01260.142*
C180.3819(2)0.5382(4)0.03603(19)0.0713(11)
H18A0.40540.44940.05410.086*
H18B0.34600.5189−0.00620.086*
C190.3360(3)0.5959(6)0.0761(2)0.120(2)
H19A0.31260.68420.05870.179*
H19B0.37060.61040.11860.179*
H19C0.29530.53050.07680.179*
C201.35082(18)1.2724(4)0.35771(17)0.0569(9)
C211.42974(18)1.2807(4)0.39314(17)0.0601(9)
H211.45011.36460.41350.072*
C221.47921(18)1.1636(4)0.39849(17)0.0614(10)
C231.44664(19)1.0394(4)0.36634(18)0.0670(10)
H231.47840.96060.36840.080*
C241.36802(19)1.0338(4)0.33186(17)0.0642(10)
H241.34760.94990.31160.077*
C251.31757(17)1.1487(4)0.32605(15)0.0485(8)
C261.23508(17)1.1368(4)0.29151(15)0.0523(8)
H261.21571.05100.27260.063*
C271.10501(17)1.2233(3)0.25418(16)0.0503(8)
C281.05433(18)1.3096(4)0.27315(18)0.0627(10)
H281.07461.37720.30450.075*
C290.97340(19)1.2964(4)0.24577(18)0.0623(10)
H290.94011.35530.25920.075*
C300.94111(17)1.1975(4)0.19888(17)0.0526(8)
C310.99234(18)1.1154(4)0.17833(17)0.0636(10)
H310.97211.05060.14580.076*
C321.07367(18)1.1279(4)0.20539(17)0.0617(9)
H321.10711.07200.19070.074*
C330.85469(18)1.1811(4)0.17210(17)0.0544(8)
C340.8015(2)1.3053(4)0.1698(2)0.0809(13)
H34A0.75741.30110.13150.121*
H34B0.83031.39110.17030.121*
H34C0.78301.30300.20610.121*
C351.5932(2)1.2996(6)0.4682(2)0.1011(16)
H35A1.64961.29760.47530.121*
H35B1.57211.38170.44230.121*
C361.5795(3)1.3152(6)0.5290(3)0.132(2)
H36A1.52391.32170.52240.199*
H36B1.60511.39930.54960.199*
H36C1.60061.23490.55520.199*
C371.6135(2)1.0547(5)0.4317(2)0.0997(14)
H37A1.59811.01200.38970.120*
H37B1.66651.09190.44050.120*
C381.6127(3)0.9501(6)0.4783(3)0.140(2)
H38A1.56080.90990.46820.209*
H38B1.62660.99310.51960.209*
H38C1.65010.87720.47830.209*
H10.748(5)0.749(3)0.125(3)0.48(7)*

Source of material

All chemicals used were of the analytical reagent grade available. 4-Amino acetophenone oxime was prepared by a similar method reported earlier [4]. To an ethanol solution (5 mL) of 4-amino acetophenone oxime (164.0 mg, 1 mmol) was added an ethanol solution (5 mL) of 4–(diethylamino)salicylaldehyde (200.0 mg, 1 mmol). After the solution had been stirred at 330 K for 12 h, the mixture was filtered, washed successively with dichloromethane and ethanol/hexane (1:4), respectively. The isolated compound was dried under reduced pressure and purified with recrystallization from ethanol to obtained yellow crystalline solid (yield 65.7%, m.p. 432–435 K). The single crystals were obtained by slow evaporation from a mixture of ethanol and dichloromethane (1:2) at room temperature. Elemental analysis – Anal. calcd. for C19H23N3O2: C, 70.13%; H, 7.12%; N, 12.91%; Found: C, 70.15%; H, 7.14%; N, 12.87%.

Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

Discussion

Oxime-type compounds are considered a very important class of organic ligands possessing diverse applications. 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.

All bond lengths are in normal ranges [18]. The asymmetric unit of the title structure contains two crystallographically independent but chemically identical molecules (cf. the figure). In the molecules, there are strong intramolecular O—H⋯N hydrogen bonds (O1—H1⋯N2: d(O1⋯N2) = 2.633 Å; O3—H3⋯N5: d(O3⋯N5) = 2.603(3) Å). In addition, the structure of the title compound formed a chain structure via strong intermolecular O2—H2A⋯O1, O4—H4A⋯O1, hydrogen bonds.

Acknowledgements

This work was supported by the Science Foundation of Gansu Education Department of China (2017A-023).

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Received: 2017-7-12
Accepted: 2017-10-23
Published Online: 2017-11-15
Published in Print: 2018-1-26

©2018 Peng-Peng Li et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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