Startseite The crystal structure of N,N-diethyl-4,6-bis(naphthalen-2-yloxy)-1,3,5-triazin-2-amine, C27H24N4O2
Artikel Open Access

The crystal structure of N,N-diethyl-4,6-bis(naphthalen-2-yloxy)-1,3,5-triazin-2-amine, C27H24N4O2

  • Zhenyu Zuo EMAIL logo , Fuhou Lei , Xiao Song und Lu Wang
Veröffentlicht/Copyright: 31. August 2018

Abstract

C27H24N4O2 monoclinic, P21/c (no. 14), a = 5.8073(2) Å, b = 31.2564(9) Å, c = 24.8105(8) Å, β = 90.13°, V = 4503.5(2) Å3, Z = 8, Rgt(F) = 0.0644, wRref(F2) = 0.1854, T = 150(2) K.

CCDC no.: 1816720

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
Size:0.19 × 0.18 × 0.17 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:0.67 mm−1
Diffractometer, scan mode:Bruker, φ and ω-scans
θmax, completeness:66°, >99%
N(hkl)measured, N(hkl)unique, Rint:13522, 6998, 0.058
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5443
N(param)refined:604
Programs:Bruker programs [1], SHELX [2], Olex2 [3]
Table 2:

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

AtomxyzUiso*/Ueq
N11.0425(5)0.11384(9)0.24328(13)0.0351(7)
N21.1338(5)0.04868(8)0.28875(12)0.0315(6)
N30.9303(5)0.04699(9)0.20495(12)0.0324(6)
N41.0215(5)−0.01517(9)0.25004(13)0.0389(8)
N50.5394(5)0.36321(9)0.19920(13)0.0341(7)
N60.4232(5)0.29812(8)0.24128(12)0.0317(6)
N70.6241(5)0.29671(8)0.15714(12)0.0319(6)
N80.5073(6)0.23435(9)0.19873(13)0.0390(8)
O11.2335(5)0.11476(8)0.32150(11)0.0403(6)
O20.8532(5)0.11169(7)0.16529(11)0.0406(6)
O30.3489(5)0.36429(7)0.27750(11)0.0394(6)
O40.7292(5)0.36153(8)0.12125(11)0.0399(6)
C11.5751(6)0.07623(12)0.34842(16)0.0366(8)
H11.62640.07610.31210.044*
C21.7076(6)0.05881(11)0.38842(16)0.0364(8)
H21.85220.04640.37980.044*
C31.6317(6)0.05909(11)0.44264(16)0.0334(8)
C41.7662(7)0.04089(12)0.48427(17)0.0406(9)
H41.91080.02830.47610.049*
C51.6897(8)0.04135(14)0.5358(2)0.0532(12)
H51.78090.02870.56340.064*
C61.4750(8)0.06052(13)0.54948(18)0.0469(10)
H61.42520.06100.58590.056*
C71.3397(7)0.07839(12)0.50970(17)0.0417(9)
H71.19560.09090.51860.050*
C81.4162(6)0.07808(10)0.45559(16)0.0322(8)
C91.2810(6)0.09590(10)0.41331(15)0.0324(8)
H91.13640.10880.42080.039*
C101.3619(6)0.09421(11)0.36213(15)0.0315(8)
C111.1321(6)0.09058(10)0.28290(15)0.0320(8)
C120.9434(6)0.08907(10)0.20643(15)0.0315(7)
C130.7102(6)0.09100(11)0.12761(16)0.0347(8)
C140.7709(6)0.09341(11)0.07486(16)0.0344(8)
H140.91320.10600.06470.041*
C150.6197(7)0.07690(11)0.03513(16)0.0357(9)
C160.6779(8)0.07841(13)−0.02049(17)0.0462(10)
H160.81790.0912−0.03190.055*
C170.5286(10)0.06103(14)−0.0574(2)0.0587(13)
H170.56720.0617−0.09450.070*
C180.3182(10)0.04211(14)−0.0413(2)0.0601(14)
H180.21790.0303−0.06760.072*
C190.2588(8)0.04078(13)0.01185(19)0.0498(11)
H190.11690.02820.02240.060*
C200.3554(7)0.05669(12)0.10643(18)0.0431(9)
H200.21370.04430.11750.052*
C210.4092(7)0.05827(12)0.05161(17)0.0385(9)
C220.5038(7)0.07274(12)0.14474(17)0.0392(9)
H220.46650.07140.18200.047*
C231.0287(6)0.02736(11)0.24803(14)0.0304(8)
C241.1161(8)−0.03971(12)0.29590(18)0.0467(10)
H24A1.1979−0.06520.28190.056*
H24B1.2300−0.02170.31520.056*
C250.9380(10)−0.05380(15)0.3344(2)0.0658(14)
H25A0.8307−0.07330.31620.099*
H25B0.8536−0.02880.34780.099*
H25C1.0113−0.06860.36470.099*
C26a0.9123(8)−0.04028(13)0.20664(19)0.0478(10)
H26Aa0.8312−0.06500.22270.057*
H26Ba0.7960−0.02230.18820.057*
H26Ca0.9740−0.03100.17140.057*
H26Da0.9500−0.07090.21140.057*
C27a1.076(2)−0.0557(3)0.1673(4)0.0594(18)
H27Aa1.1447−0.03130.14840.089*
H27Ba0.9969−0.07410.14120.089*
H27Ca1.1972−0.07200.18560.089*
C27A0.6726(18)−0.0350(3)0.2070(4)0.0594(18)
H27Da0.6130−0.04180.24290.089*
H27Ea0.6026−0.05420.18040.089*
H27Fa0.6346−0.00530.19790.089*
C280.2088(6)0.34473(11)0.31667(16)0.0351(8)
C290.2708(6)0.34842(11)0.36882(16)0.0361(8)
H290.41300.36160.37810.043*
C300.1234(7)0.33262(11)0.41012(16)0.0334(8)
C310.1821(7)0.33443(12)0.46515(16)0.0403(9)
H310.32290.34730.47590.048*
C320.0373(8)0.31770(13)0.50331(18)0.0502(12)
H320.07830.31920.54030.060*
C33−0.1677(8)0.29871(13)0.48833(19)0.0485(11)
H33−0.26590.28690.51510.058*
C34−0.2295(7)0.29683(12)0.43564(19)0.0450(10)
H34−0.37160.28380.42600.054*
C35−0.0875(6)0.31378(11)0.39474(16)0.0355(9)
C36−0.1483(7)0.31129(12)0.33946(16)0.0379(8)
H36−0.29070.29870.32920.046*
C37−0.0035(6)0.32677(12)0.30109(16)0.0371(8)
H37−0.04530.32550.26410.045*
C380.4394(6)0.33986(10)0.23771(15)0.0309(7)
C390.6280(6)0.33865(11)0.16087(15)0.0312(7)
C400.8579(6)0.33952(10)0.08214(15)0.0315(8)
C411.0685(6)0.32137(11)0.09718(16)0.0367(9)
H411.11690.32160.13380.044*
C421.2034(6)0.30331(11)0.05835(16)0.0359(8)
H421.34640.29080.06840.043*
C431.1358(6)0.30275(11)0.00397(16)0.0325(8)
C441.2720(7)0.28453(11)−0.03711(17)0.0411(9)
H441.41570.2718−0.02810.049*
C451.2006(7)0.28486(13)−0.08966(18)0.0481(10)
H451.29470.2723−0.11660.058*
C460.9911(8)0.30346(13)−0.10412(18)0.0484(11)
H460.94250.3034−0.14070.058*
C470.8562(6)0.32180(12)−0.06549(16)0.0376(8)
H470.71480.3349−0.07560.045*
C480.9234(6)0.32168(10)−0.01065(15)0.0315(8)
C490.7856(6)0.34034(11)0.03025(15)0.0321(8)
H490.64280.35340.02120.039*
C500.5183(6)0.27707(10)0.19906(15)0.0307(8)
C510.4014(7)0.21090(12)0.24350(18)0.0448(10)
H51A0.32430.18490.22960.054*
H51B0.28380.22910.26100.054*
C520.5881(9)0.19825(14)0.2850(2)0.0581(12)
H52A0.70560.18070.26740.087*
H52B0.51720.18190.31430.087*
H52C0.65970.22410.29970.087*
C530.6119(8)0.20937(12)0.15564(18)0.0483(10)
H53A0.70010.18520.17110.058*
H53B0.71940.22750.13480.058*
C540.4187(12)0.19216(17)0.1181(2)0.0810(18)
H54A0.48610.17330.09080.122*
H54B0.34170.21620.10020.122*
H54C0.30630.17610.13950.122*
  1. aOccupancy: 0.5.

Source of material

To the solution of cyanuric chloride (3.69 g, 0.02 mol) and 2-naphthol (5.77 g, 0.04 mol) in tetrahydrofuran (50 mL) was added K2CO3 (5.52 g, 0.04 mol). The mixture was stirred at room temperature for 6 h and filtered. The filtrate was evaporated under reduced pressure to get a yellow solid, which was purified by silica gel to afford the intermediate product 2-chloro-4,6-bi(2-naphthoxyl)-1,3,5-triazine (4.90 g, yield 72%). To the solution of 2-chloro-4,6-bi(2-naphthoxyl)-1,3,5-triazine (2.00 g, 0.005 mol) in tetrahydrofuran (30 mL) was added HN(C2H5)2 (0.439 g, 0.006 mol) at room temperature. After the mixture was stirred for 2 h, the solvent was evaporated under reduced pressure to get a white solid, which was recrystallized with petroleum ether to afford the title compound (1.88 g, yield 86%) 1H NMR: 7.86–7.76 ppm (m, 6H), 7.65 ppm (s, 2H), 7.48 ppm (dd, J = 3.6 HZ, J = 4.8 HZ, 4H), 7.36 ppm (d, J = 8.8 HZ, 2H) 3.45 ppm (q, J = 6.8 HZ, 4H), 1.08 ppm (t, J = 6.8 HZ, 6H). Crystals were obtained by recrystallization with petroleum ether at room temperature.

Experimental details

The data were scaled and corrected for absorption using SADABS-2016/2 [1]. The hydrogen atoms were placed at calculated positions and refined as riding atoms with fixed isotropic displacement parameters. There is a 1/1 disorder at one of the ethyl groups (cf. table 2)

Discussion

Azo compounds containing a heterocyclic moiety were widely used in material field (such as molecular memory storages, nonlinear optical elements, printing system), pharmacy, agriculture, chemical industry and so on. As one of the most important class of azo compounds, s-triazines and its new derivative have drawn more and more attention of scientists from all over the world due to its diverse pharmacological activity [4] (such as antitumor [5], anti-inflammatory), biological activities (such as antibacteria [6], [7], antimycotic, herbicidal, insecticidal activities), high catalyst activity, abundant optoelectronic properties [8] and so on. In this paper, a new s-triazines derivative was synthesized by substitution reactions using 2,4,6-trichloro-1,3,5-triazine as starting material. Its structure was characterized by 1H NMR and X-ray single crystal diffraction.

There are two cystallographically independent molecules (cf. the figure) in the asymmetric unit, in which all bond lengths are in normal ranges. The geometric parameters of both crystallographically independent molecules are similar and are in accord with another symmetrically substituted triazine [9]. In molecular packing diagram, there are obvious π-π stacking interactions between the adjacent naphthalenyl moieties. The distance between adjacent naphthalenyl moieties is less than 3.585 Å, which is within normal range [10]. No classic hydrogen bonds were observed as following: C51—H51B⋯N6 hydrogen bond (d(H51B⋯N6) = 2.36 Å), C53—H53A⋯O2 hydrogen bond (d(H53A⋯O2) = 2.47 Å) and C53—H53B⋯N7 hydrogen bond (d(H53B⋯N7) = 2.30 Å).

Acknowledgements

We acknowledge the supports by Key project of Shaanxi Provincial Education Department (17JS029), Natural Science Basic Research Program of Shaanxi (2017JM8070). China Postdoctoral Science Foundation funded project (2016M602994).

References

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Received: 2018-06-14
Accepted: 2018-08-09
Published Online: 2018-08-31
Published in Print: 2018-11-27

©2018 Zhenyu Zuo et al., published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of di-μ2-aqua-tetraaqua-bis(4-(1H-1,2,4-triazol-1-yl)benzoato-κN)disodium(I) C18H24N6Na2O10
  3. Crystal structure of diaqua-bis(2-bromo-4-chloro-6-formylphenolato-κ2O,O′)cobalt(II), C16H16Cl2CrN3O7
  4. Crystal structure of catena-poly[(μ2-1-(4-(1H-pyrazol-1-yl)phenyl)ethan-1-one-κ2N:O)-bis(1,1,1-trifluoro-4-oxo-4-(thiophen-2-yl)but-2-en-2-olato-κ2O,O′)copper(II)], C27H18CuF6N2O5S2
  5. Crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C18H15F2NO5
  6. Crystal structure of 5,5′-dimethoxy-2,2′-[1,1′-(ethylenedioxydinitrilo)diethylidyne]diphenol, C20H24N2O6
  7. Crystal structure of (E)-1-(4-(((E)-3,5-dichloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H14Cl2N2O2
  8. Crystal structure of 2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyanine - trichloromethane (1/2), C98H84Cl6N8O8
  9. Crystal structure of methyl 2-((1-(2-(methoxycarbonyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1-naphthoate, C24H21N3O5
  10. Crystal structure of catena-poly[(μ2-3,3′-thiodipropionato-κ2O:O′)-(bipyridine-κ2N,N′)copper(II)] C16H16CuN2O4S
  11. Crystal structure of [4-chloro-2-(((2-((3-ethoxy-2-oxidobenzylidene)amino)phenyl)imino)(phenyl)methyl)phenolato-κ4N,N′,O,O′}nickel(II) - ethyl acetate (1/1), C32H29ClN2NiO5
  12. Crystal structure of (4-(4-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C29H52Cl2N4NiO9
  13. Crystal structure of ethyl 2-amino-4-(3,4-dimethylphenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C20H21NO5
  14. Structure and photochromism of 1,2-bis[2-methyl-5-(3-quinolyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C33H20F6N2S2
  15. Crystal structure of catena-poly[diaqua-bis(μ2-3,5-di(1H-1,2,4-triazol-1-yl)benzoate-κ2N:N′)cobalt(II))] 2.5 hydrate, C22H23CoN12O8.50
  16. The crystal structure of dichlorido(1,3-dimesityl-1H-3λ4-imidazol-2-yl)(morpholine-κN)palladium(IV), C25H33Cl2N3OPd
  17. Crystal structure of catena-poly[bis(4,4′-dipyridylaminium-kN)-(μ2-germanowolframato-κ2O:O′)-(2,2′-bipyridine-κ2N,N′)copper(II)] with a Keggin-type heteropolyoxoanion, [Cu(C10H8N2)(C10H10N3)2][GeW12O40] ⋅ H2O
  18. Crystal structure of diaqua-(N-(1-(pyrazin-2-yl)ethylidene)pyridin-1-ium-4-carbohydrazonate-κ3N,N′,O)-tris[nitrato-κ2O,O′)lanthanum(III), C12H15N8O12La
  19. The crystal structure of 2-hydroxy-4-((2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy)-3,6-dimethylbenzoic acid–methanol (1/1), C20H24O8
  20. Crystal structure of guanidinium tetrapropylammonium bis(hydrogencarbonate) dihydrate, C15H40N4O8
  21. Crystal structure of (Z)-2-bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-phenylprop-2-en-1-one, C23H27BrO2
  22. Crystal structure of 2-(4-(4H-1,2,4-triazol-4-yl)phenyl)acetic acid, C10H9N3O4
  23. Crystal structure of 4,4′-(1,4-phenylene)bis(1H-imidazol-3-ium)bis(2-carboxybenzoate), C30H26N4O8
  24. Crystal structure of 4,4′-(4,10-diphenyl-4,10-dihydropyreno[4,5-d:9,10-d′]diimidazole-5,11-diyl)bis(N,N-diphenylaniline), C66H44N6
  25. Crystal structure of catena-poly[diaqua-bis(μ2-5-(3-(1H-imidazol-5-yl)phenyl)tetrazol-2-ido-κ2N:N′)cobalt(II)], C20H18CoN12O2
  26. Crystal structure of 1,3-dimethyl-2-(p-tolyl)-1H-perimidin-3-ium iodide 1.5 hydrate, C20H22IN2O1.5
  27. Crystal structure of 2-(4-methoxyphenyl)chromane, C16H16O2
  28. Crystal structure of poly[(μ2-2-carboxy-5-nitroisophthalato-κ2O:O′)-(μ2-4-((1H-imidazol-1-yl)methyl)pyridine-κ2N:N′)zinc(II)], C18H12N4O8Zn
  29. Crystal structure of bis(1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ2N:N′)tetraiodidodicadmium(II), [Cd2(C13H15N5)2I4]
  30. Crystal structure of tetramethylammonium bis(acetato-κ1O)-tetrakis(μ3-3-((hydroxyimino)methyl)-5-methoxy-2-oxidobenzoate-κ5O,O′:O′,N:O′′)tetrazinc(II) — N,N′-dimethylformamide — water (1/2/2), C62H96Zn4N10O28
  31. Crystal structure of poly[(μ4-5-tert-butylisophthalato-κ4O:O′:O′′:O′′′)-(1,3-dimethyl-2-imidazolidinone-κO)zinc(II)] C17H22N2O5Zn
  32. Crystal structure of [tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′]-[(pyridine-2,6-dicarboxylato-κ2O,N)]cadmium(II)–methanol (1:3) C34H36CdN8O7
  33. The crystal structure of bis(1H-benzo[d]imidazol-2-amine-κN)-diiodidocadmium(II), C14H14CdI2N6
  34. Crystal structure of tetrakis(1H-benzimidazol-2-amine)-κN)-bis(μ2-sulfonato-κ2O:O′)dizinc(II) - methanol (1/1), C30H36N12O10S2Zn2
  35. Crystal structure of 3β-methoxy-20α-dimethylamino-pregn-5-ene, C24H41NO
  36. Crystal structure of dimethyl 4,4′-oxydibenzoate, C16H14O5
  37. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-3-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)zinc(II)], C17H16I2N4OZn
  38. Crystal structure of 4-((E)-((E)-5-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-4-oxopiperidin-3-ylidene)methyl)benzonitrile, C26H18F2N2O3S
  39. Crystal structure of bis(acetato-κ1O)-bis(1-(pyridin-2-yl)ethan-1-one oxime-κ2N,N′)zinc(II), C18H22N4O6Zn
  40. The crystal structure of 9-butoxy-2-(hydroxymethyl)-2H-imidazo[1,5-a]quinolin-10-ium bromide, C17H21O2N2Br
  41. Crystal stucture of 2-(tert-butyl)-6-(hydroxymethyl)-4-methylphenol, C12H18O2
  42. Crystal structure of catena-poly[(2-(5-chloroquinolin-8-yloxy)-1-(pyrrolidin-1-yl)ethan-1-one-κ3N,O,O′)-(dinitrato-κ2O,O′)mercury(II)], C15H15N4O8ClHg
  43. Crystal structure of dimethyl (3aS,6R,6aS,7S)-1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-3a1,6a-dicarboxylate, C16H16O7
  44. The crystal structure of 2-(dimethoxymethyl)-4-(4-methylphenyl)-1H-imidazole—petroleum ether-chloroform (3/1), C27H33Cl3N4O4
  45. Crystal structure of 8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, C9H5F3N2O
  46. The crystal structure of N,N-diethyl-4,6-bis(naphthalen-2-yloxy)-1,3,5-triazin-2-amine, C27H24N4O2
  47. Crystal structure of 5-bromo-7-chloro-3,3a-dihydrocyclopenta[b]chromen-1(2H)-one, C12H8BrClO2
  48. Crystal structure of 2-(bis(4-fluorophenyl)methylene)hydrazine-1-carbothioamide, C14H11F2N3S
Heruntergeladen am 7.11.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2018-0207/html
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