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.
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.
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] |
Atom | x | y | z | Uiso*/Ueq |
---|---|---|---|---|
O1 | 0.71151(12) | 0.7864(2) | 0.09344(11) | 0.0542(6) |
O2 | 1.20727(12) | 0.6934(3) | 0.47063(11) | 0.0679(7) |
H2A | 1.2082 | 0.6937 | 0.5079 | 0.102* |
O3 | 1.30637(13) | 1.3894(3) | 0.35409(16) | 0.0837(9) |
H3 | 1.2599 | 1.3701 | 0.3363 | 0.126* |
O4 | 0.74617(12) | 1.0546(3) | 0.12949(14) | 0.0725(8) |
H4A | 0.7315 | 0.9763 | 0.1148 | 0.109* |
N1 | 0.44416(14) | 0.6325(3) | 0.03029(13) | 0.0538(7) |
N2 | 0.80871(14) | 0.6938(3) | 0.20193(12) | 0.0505(7) |
N3 | 1.12874(14) | 0.6869(3) | 0.43078(12) | 0.0548(7) |
N4 | 1.55787(16) | 1.1725(4) | 0.43286(18) | 0.0855(11) |
N5 | 1.18722(14) | 1.2407(3) | 0.28582(13) | 0.0543(7) |
N6 | 0.82973(14) | 1.0574(3) | 0.15334(14) | 0.0568(7) |
C1 | 0.65467(17) | 0.7138(3) | 0.10506(14) | 0.0448(7) |
C2 | 0.57813(16) | 0.7164(3) | 0.06382(14) | 0.0458(7) |
H2 | 0.5662 | 0.7762 | 0.0288 | 0.055* |
C3 | 0.51790(17) | 0.6323(3) | 0.07285(15) | 0.0473(7) |
C4 | 0.5366(2) | 0.5447(4) | 0.12805(17) | 0.0591(9) |
H4 | 0.4979 | 0.4872 | 0.1351 | 0.071* |
C5 | 0.6100(2) | 0.5451(4) | 0.16996(17) | 0.0597(9) |
H5 | 0.6203 | 0.4882 | 0.2059 | 0.072* |
C6 | 0.67203(17) | 0.6276(3) | 0.16204(14) | 0.0468(7) |
C7 | 0.74625(18) | 0.6233(4) | 0.20672(15) | 0.0540(8) |
H7 | 0.7530 | 0.5673 | 0.2426 | 0.065* |
C8 | 0.88589(17) | 0.6895(3) | 0.24576(14) | 0.0479(8) |
C9 | 0.94488(19) | 0.7528(4) | 0.22766(15) | 0.0585(9) |
H9 | 0.9328 | 0.7972 | 0.1883 | 0.070* |
C10 | 1.02227(19) | 0.7511(4) | 0.26779(16) | 0.0614(10) |
H10 | 1.0616 | 0.7924 | 0.2544 | 0.074* |
C11 | 1.04201(17) | 0.6889(4) | 0.32751(14) | 0.0492(8) |
C12 | 0.98163(18) | 0.6258(4) | 0.34457(15) | 0.0538(8) |
H12 | 0.9936 | 0.5820 | 0.3841 | 0.065* |
C13 | 0.90410(18) | 0.6253(4) | 0.30518(15) | 0.0543(8) |
H13 | 0.8648 | 0.5827 | 0.3182 | 0.065* |
C14 | 1.12358(18) | 0.6920(4) | 0.37199(15) | 0.0534(8) |
C15 | 1.1930(2) | 0.7038(5) | 0.34810(18) | 0.0869(14) |
H15A | 1.1779 | 0.6745 | 0.3044 | 0.130* |
H15B | 1.2348 | 0.6444 | 0.3731 | 0.130* |
H15C | 1.2107 | 0.7999 | 0.3515 | 0.130* |
C16 | 0.42241(19) | 0.7318(4) | −0.02271(17) | 0.0655(10) |
H16A | 0.3749 | 0.6981 | −0.0545 | 0.079* |
H16B | 0.4642 | 0.7341 | −0.0421 | 0.079* |
C17 | 0.4083(2) | 0.8782(4) | −0.0039(2) | 0.0946(15) |
H17A | 0.3967 | 0.9389 | −0.0404 | 0.142* |
H17B | 0.4546 | 0.9118 | 0.0283 | 0.142* |
H17C | 0.3645 | 0.8781 | 0.0126 | 0.142* |
C18 | 0.3819(2) | 0.5382(4) | 0.03603(19) | 0.0713(11) |
H18A | 0.4054 | 0.4494 | 0.0541 | 0.086* |
H18B | 0.3460 | 0.5189 | −0.0062 | 0.086* |
C19 | 0.3360(3) | 0.5959(6) | 0.0761(2) | 0.120(2) |
H19A | 0.3126 | 0.6842 | 0.0587 | 0.179* |
H19B | 0.3706 | 0.6104 | 0.1186 | 0.179* |
H19C | 0.2953 | 0.5305 | 0.0768 | 0.179* |
C20 | 1.35082(18) | 1.2724(4) | 0.35771(17) | 0.0569(9) |
C21 | 1.42974(18) | 1.2807(4) | 0.39314(17) | 0.0601(9) |
H21 | 1.4501 | 1.3646 | 0.4135 | 0.072* |
C22 | 1.47921(18) | 1.1636(4) | 0.39849(17) | 0.0614(10) |
C23 | 1.44664(19) | 1.0394(4) | 0.36634(18) | 0.0670(10) |
H23 | 1.4784 | 0.9606 | 0.3684 | 0.080* |
C24 | 1.36802(19) | 1.0338(4) | 0.33186(17) | 0.0642(10) |
H24 | 1.3476 | 0.9499 | 0.3116 | 0.077* |
C25 | 1.31757(17) | 1.1487(4) | 0.32605(15) | 0.0485(8) |
C26 | 1.23508(17) | 1.1368(4) | 0.29151(15) | 0.0523(8) |
H26 | 1.2157 | 1.0510 | 0.2726 | 0.063* |
C27 | 1.10501(17) | 1.2233(3) | 0.25418(16) | 0.0503(8) |
C28 | 1.05433(18) | 1.3096(4) | 0.27315(18) | 0.0627(10) |
H28 | 1.0746 | 1.3772 | 0.3045 | 0.075* |
C29 | 0.97340(19) | 1.2964(4) | 0.24577(18) | 0.0623(10) |
H29 | 0.9401 | 1.3553 | 0.2592 | 0.075* |
C30 | 0.94111(17) | 1.1975(4) | 0.19888(17) | 0.0526(8) |
C31 | 0.99234(18) | 1.1154(4) | 0.17833(17) | 0.0636(10) |
H31 | 0.9721 | 1.0506 | 0.1458 | 0.076* |
C32 | 1.07367(18) | 1.1279(4) | 0.20539(17) | 0.0617(9) |
H32 | 1.1071 | 1.0720 | 0.1907 | 0.074* |
C33 | 0.85469(18) | 1.1811(4) | 0.17210(17) | 0.0544(8) |
C34 | 0.8015(2) | 1.3053(4) | 0.1698(2) | 0.0809(13) |
H34A | 0.7574 | 1.3011 | 0.1315 | 0.121* |
H34B | 0.8303 | 1.3911 | 0.1703 | 0.121* |
H34C | 0.7830 | 1.3030 | 0.2061 | 0.121* |
C35 | 1.5932(2) | 1.2996(6) | 0.4682(2) | 0.1011(16) |
H35A | 1.6496 | 1.2976 | 0.4753 | 0.121* |
H35B | 1.5721 | 1.3817 | 0.4423 | 0.121* |
C36 | 1.5795(3) | 1.3152(6) | 0.5290(3) | 0.132(2) |
H36A | 1.5239 | 1.3217 | 0.5224 | 0.199* |
H36B | 1.6051 | 1.3993 | 0.5496 | 0.199* |
H36C | 1.6006 | 1.2349 | 0.5552 | 0.199* |
C37 | 1.6135(2) | 1.0547(5) | 0.4317(2) | 0.0997(14) |
H37A | 1.5981 | 1.0120 | 0.3897 | 0.120* |
H37B | 1.6665 | 1.0919 | 0.4405 | 0.120* |
C38 | 1.6127(3) | 0.9501(6) | 0.4783(3) | 0.140(2) |
H38A | 1.5608 | 0.9099 | 0.4682 | 0.209* |
H38B | 1.6266 | 0.9931 | 0.5196 | 0.209* |
H38C | 1.6501 | 0.8772 | 0.4783 | 0.209* |
H1 | 0.748(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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©2018 Peng-Peng Li et al., published by De Gruyter, Berlin/Boston
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