Startseite The crystal structure of 2-(naphthalen-2-yloxy)-4-phenyl-6-(prop-2-yn-1-yloxy)-1,3,5-triazine, C22H15N3O2
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The crystal structure of 2-(naphthalen-2-yloxy)-4-phenyl-6-(prop-2-yn-1-yloxy)-1,3,5-triazine, C22H15N3O2

  • Jin Li ORCID logo , Zhenyu Zuo , Yan Chen , Yali Liu und Dachuan Yin EMAIL logo
Veröffentlicht/Copyright: 18. Dezember 2020

Abstract

C22H15N3O2, triclinic, P1 (no. 2), a = 5.7613(4) Å, b = 12.3545(7) Å, c = 13.3427(8) Å, α = 110.002(2)°, β = 98.837(2)°, γ = 94.263(2)°, V = 873.55(9) Å3, Z = 2, Rgt(F) = 0.0471, wRref(F2) = 0.1376, T = 293 K.

CCDC no.: 2042526

Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless block
Size:0.50 × 0.40 × 0.30 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:0.71 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:68.4°, 96%
N(hkl)measured, N(hkl)unique, Rint:7418, 3066, 0.040
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2651
N(param)refined:244
Programs:Bruker [1], SHELX [2], Olex2 [3]
Table 2:

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

AtomxyzUiso*/Ueq
C10.6791 (3)0.80235 (13)0.49698 (11)0.0340 (3)
C20.5614 (3)0.68237 (12)0.57501 (11)0.0322 (3)
C30.9145 (2)0.79381 (12)0.64194 (10)0.0325 (3)
C40.2665 (3)0.70929 (13)0.15173 (11)0.0378 (4)
C51.1372 (3)0.83424 (12)0.72438 (11)0.0340 (3)
C60.2154 (3)0.47962 (13)0.64986 (11)0.0372 (3)
C70.4465 (3)0.81493 (13)0.33863 (11)0.0369 (4)
C81.5257 (3)0.94723 (14)0.79300 (12)0.0418 (4)
H81.64840.99890.78660.050*
C90.0689 (3)0.76997 (14)0.16714 (12)0.0399 (4)
C100.2478 (3)0.87277 (14)0.35597 (12)0.0413 (4)
H100.24220.92690.42580.050*
C111.1665 (3)0.79735 (14)0.81235 (12)0.0406 (4)
H111.04410.74610.81940.049*
C121.3179 (3)0.90983 (13)0.71503 (11)0.0371 (3)
H121.29910.93580.65530.045*
C130.4305 (3)0.55656 (13)0.66080 (11)0.0366 (3)
H13A0.46420.62010.73280.044*
H13B0.56770.51260.65370.044*
C141.5539 (3)0.90919 (15)0.87986 (12)0.0445 (4)
H141.69680.93400.93250.053*
C150.4586 (3)0.73378 (13)0.24121 (12)0.0382 (3)
H150.59320.69390.23270.046*
C161.3748 (3)0.83532 (15)0.89021 (12)0.0462 (4)
H161.39370.81040.95050.055*
C170.2738 (3)0.62900 (15)0.04751 (13)0.0464 (4)
H170.40630.58800.03650.056*
C18−0.1180 (3)0.74880 (17)0.07634 (14)0.0499 (4)
H18−0.25150.78940.08530.060*
C190.0620 (3)0.85032 (15)0.27122 (13)0.0426 (4)
H19−0.07320.88920.28250.051*
C200.0421 (3)0.41615 (14)0.63930 (13)0.0438 (4)
H20−0.09720.36510.63080.053*
C210.0894 (4)0.61021 (17)−0.03798 (13)0.0551 (5)
H210.09440.5558−0.10770.066*
C22−0.1065 (3)0.67124 (19)−0.02254 (14)0.0573 (5)
H22−0.23240.6579−0.08220.069*
N10.8839 (2)0.84255 (11)0.56690 (9)0.0352 (3)
N20.7583 (2)0.71178 (10)0.64955 (9)0.0336 (3)
N30.5076 (2)0.72386 (10)0.49517 (9)0.0334 (3)
O10.65067 (19)0.85193 (10)0.42123 (8)0.0420 (3)
O20.38915 (18)0.60368 (9)0.57509 (7)0.0365 (3)

Source of material

To a suspension of 2-chloro-4-phenyl-6-(prop-2-yn-1-yloxy)-1,3,5-triazine (2.46 g, 0.01 mol) in 60 mL of tetrahydrofuran was added K2CO3 (2.76 g, 0.02 mol) and naphthalen-2-ol (1.44 g, 0.01 mol). The mixture was refluxed for 12 h and then filtered to get a yellow solution. The solvent was evaporated under reduced pressure to get a yellow solid, which was purified by chromatography on silica gel to afford 2-(naphthalen-2-yloxy)-4-phenyl-6-(prop-2-yn-1-yloxy)-1,3,5-triazine as a white solid (2.19 g, 62%). The crystal suitable for X-ray diffraction was obtained by recrystallization in petroleum ether.

Experimental details

The data were scaled and corrected for absorption using SADABS-2016/2 (Bruker, APEX-II CCD). The hydrogen atoms were placed at calculated positions and refined as riding atoms with isotropic displacement parameters.

Comment

In the past years, 1,3,5-triazine derivatives have drawn more and more attentions of the scientists all over the world, for the reason that these compounds demonstrated promising biological activities such as anticancer [4], [5], antiviral [6], antibacterial [7], [8], [9], antifungal [10], anti–Alzheimer’s [11] and anti-inflammatory [12] properties. Thus the synthesis and property studies of novel 1,3,5-triazine derivatives is an active fields in medicinal chemistry. The title 1,3,5-triazine derivative was synthesized by a nucleophilic substitution reaction using 2-chloro-4-phenyl-6-(prop-2-yn-1-yloxy)-1,3,5-triazine as the starting material.

Bond lengths and angles are in the expected ranges (see the Figure) [13], [14]. The torsion angle of C10–C7–O1–C1 is 91.3°, which demonstrated that naphthyl moiety and the 1,3,5-triazine ring are not coplanar. Meanwhile, the torsion angle of C12–C5–C3–N2 is 173.2°, which demonstrated that phenyl ring and the 1,3,5-triazine ring were almost in the same plane (cf. the figure). In molecular packing, non-classical hydrogen bonds were observed as following: C11–H11⋯N2 hydrogen bond (d(H11⋯N2) = 2.47 Å, C20–H20⋯N3 hydrogen bond (d(H20⋯N3) = 2.60 Å.


Corresponding author: Dachuan Yin, Institute for Special Environmental Biophysics, Key Laboratory for Space Bioscience and Space Biotechnology, School of Life Sciences, Northwestern Polytechnical University, Xi’an 710072, Shaanxi, PR China, E-mail:

Funding source: National Key R&D Program of China

Award Identifier / Grant number: 2018YFC1706903

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 81403101

Award Identifier / Grant number: 2017KF05

Award Identifier / Grant number: 19JS019

Funding source: Key R&D plan of Shaanxi Province

Award Identifier / Grant number: 2020SF-315

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: National Key R&D Program of China (2018YFC1706903), National Natural Science Foundation of China (Grant No. 81403101), the Project of Shaanxi Key Laboratory of Basic and New Herbal Medicament Research (Nos. 2017KF05, 19JS019), Key R&D Plan of Shaanxi Province (No. 2020SF-315).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2020-11-06
Accepted: 2020-12-04
Published Online: 2020-12-18
Published in Print: 2021-03-26

© 2020 Jin Li et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of 4-hydroxybenzene-1,3-diaminium dichloride, C6H10Cl2N2O
  4. The crystal structure of 3-chloropropylammonium chloride, C3H9Cl2N
  5. The crystal structure of 1-chloro-2-(dimethylamino)ethane hydrochloride, C4H11Cl2N
  6. Crystal structure of N-(2-(trifluoromethyl)phenyl)hexanamide, C13H16F3NO
  7. Redetermination of the crystal structure of para-toluidine, C7H9
  8. The crystal structure of bis(1,3-dihydroxy-2-methylpropan-2-aminium) carbonate, C9H24N2O7
  9. The crystal structure of 4-chloro-1-methylpiperidin-1-ium chloride, C6H13Cl2N
  10. Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO
  11. The crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H21F2NO4
  12. Crystal structure of 6,6'‐((1E,1'E)‐(propane‐1,3‐diylbis(azaneylylidene))bis(methaneylylidene))bis(3‐bromophenol), C34H32Br4N4O4
  13. The crystal structure of (E)-2-(2-((2-picolinoylhydrazono)methyl)phenoxy)acetic acid dihydrate, C15H17N3O6
  14. Crystal structure of (E)-4-bromo-N′-(3-chloro-2-hydroxybenzylidene)benzohydrazide, C14H10BrClN2O2
  15. Crystal structure of N,N′-bis(4-bromosalicylidene) ethylene-1,2-diaminopropan, C34H32Br4N4O4
  16. Crystal structure of 4-bromo-N′-[(3-bromo-2-hydroxyphenyl)methylidene]benzohydrazide methanol solvate, C15H14Br2N2O3
  17. The crystal structure of 1,2-bis(1H-benzo[d]imidazol-2-yl)ethane-1,2-diol — N-(2-aminophenyl)-3-(1H-benzo[d]imidazol-2-yl)-2,3-dihydroxypropanamide (1/1), C32H30N8O5
  18. The crystal structure of para-trifluoromethyl-aniline hemihydrate, C14H14F6N2O
  19. Redetermination of the crystal structure of 2-amino-2-methyl-propane-1,3-diole, C4H11NO2
  20. The crystal structure of methacholine chloride, C8H18ClNO2
  21. Crystal structure of 5,7,7-trimethyl-4,6,7,8-tetrahydrocyclopenta[g]isochromen-1(3H)-one, C15H18O2
  22. Crystal structure of poly[diammine-bis(μ4-4-hydroxypyridine-3-sulfonato-κ5N:O, O′:O′′:O′′)(μ2-pyrazinyl-κ2N:N′)tetrasilver(I)], C7H8Ag2N3O4S
  23. Crystal structure of ethyl (E)-5-(((3′,6′-bis(ethylamino)-3-oxospiro[isoindoline-1,9′-xanthen]-2-yl)imino)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate — ethanol (1/1), C38H45N5O5
  24. Crystal structure of 4-bromo-N′-[(3-chloro-2-hydroxyphenyl)methylidene]benzohydrazide, C14H7Br2N2O2
  25. Redetermination of the crystal structure of 3,3,3-triphenylpropanoic acid, C21H18O2 – Deposition of hydrogen atomic coordinates
  26. Structure redetermination of dextromethorphan hydrobromide monohydrate, C18H28BrNO2 – localization of hydrogen atoms
  27. Crystal structure of tris(azido-κ1N)-(N-(2-aminoethyl)-N-methyl-1,3-propanediamine-κ3N,N′,N′′)cobalt(III), C7H19CoN12
  28. Crystal structure of tetraaqua-bis(1H-indazole-6-carboxylate-κN)cadmium (II), C16H18CdN4O8
  29. Crystal structure of dichloride-bis(1-propylimidazole-κ1N)zinc(II), C12H20Cl2N4Zn
  30. Crystal structure of (E)-resveratrol 3-O-β-D-xylopyranoside, C19H22O8
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  33. Crystal structure of 6,7-difluoro-1-methyl-3-(trifluoromethyl)quinoxalin-2(1H)-one, C10H5F5N2O
  34. Crystal structure of dichlorido-bis(1-hexyl-1H-benzotriazole-k1N)zinc(II), C24H34N6Cl2Zn
  35. The crystal structre of 2-(4-bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine, C16H12BBrN2
  36. Crystal structure of diethyl 3,9-bis(4-fluorophenyl)-6,12-diphenyl-3,9-diazapentacyclo[6.4.0.02,7.04,11]dodecane-1,5-dicarboxylate, C40H36F2N2O4
  37. Crystal structure of (E)-7-methoxy-2-((5-methoxypyridin-3-yl)methylene)-3,4- dihydronaphthalen-1(2H)-one, C18H17NO3
  38. Crystal structure of (E)-2-chloro-6-(((1,3-dihydroxy-2-(oxidomethyl)propan-2-yl)imino)methyl)phenolate-κ3N,O,O’)manganese(IV), C22H24Cl2MnN2O8
  39. The crystal structure of α-(meta-methoxyphenoxy)-ortho-tolylic acid, C15H14O4
  40. The crystal structure of N-(2-chloroethyl)-N,N-diethylammonium chloride, C6H15Cl2N
  41. The crystal structure of tris(2,3,4,6,7,8,9,10-octahydro-1H-pyrimido[1,2-a]azepin-5-ium) trihydrodecavanadate(V), C27H54N6O28V10
  42. Crystal structure of 1,3-bis(octyl)benzimidazolium perchlorate C23H39ClN2O4
  43. Crystal structure of tetrakis[(Z)-(2-(1-(furan-2-yl)-2-methylpropylidene)-1-phenylhydrazin-1-ido-κ2N,N′)] zirconium(IV), C56H60N8O4Zr
  44. The crystal structure of 2-(naphthalen-2-yloxy)-4-phenyl-6-(prop-2-yn-1-yloxy)-1,3,5-triazine, C22H15N3O2
  45. The crystal structure of trimethylsulfonium tris(trifluoromethylsulfonyl)methanide, C7H9F9O6S4
  46. Crystal structure of 4-bromo-N′-[3,5-dichloro-2-hydroxyphenyl)methylidene]benzohydrazide methanol solvate, C15H13BrCl2N2O3
  47. The crystal structure of 4-(4-bromophenyl)-2-(3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazole, C24H16Br2FN3S
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