Startseite Crystal structure of methyl 2-((1-(2-(methoxycarbonyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1-naphthoate, C24H21N3O5
Artikel Open Access

Crystal structure of methyl 2-((1-(2-(methoxycarbonyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1-naphthoate, C24H21N3O5

  • Yutong Sun , Wei Hong EMAIL logo und Hao Wang EMAIL logo
Veröffentlicht/Copyright: 8. September 2018

Abstract

C24H21N3O5, orthorhombic, Pbca (no. 61), a = 8.4167(7) Å, b = 14.0370(10) Å, c = 34.664(3) Å, V = 4095.4(6) Å3, Z = 8, Rgt(F) = 0.0457, wRref(F2) = 0.1001, T = 150(2) K.

CCDC no.: 1569462

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:

Crystal collection and handling.

Crystal:Block, colorless
Size:0.320 × 0.290 × 0.120 mm
Wavelength:Mo Kα radiation (λ = 0.71073 Å)
μ:0.100 mm−1
Diffractometer, scan mode:Rigaku Saturn 724 CCD, Φ and ω-scans
θmax, completeness:25.0°, 100%
N(hkl)measured, N(hkl)unique, Rint:21579, 3601, 0.0533
Criterion for Iobs, N(hkl)gt:Iobs > 2σ(Iobs), 2554
N(param)refined:291
Programs:Bruker programs [1], SHELX [2, 3]
Table 2:

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

AtomxyzUiso*/Ueq
O10.51320(18)0.93696(10)0.33939(4)0.0365(4)
O20.36574(18)0.81591(10)0.36067(4)0.0371(4)
O30.55205(17)0.50811(10)0.39811(4)0.0344(4)
O40.33380(16)0.51874(9)0.34033(4)0.0309(4)
O50.49816(18)0.50273(10)0.28999(4)0.0367(4)
N10.35294(19)0.74176(11)0.44629(4)0.0247(4)
N20.4092(2)0.73249(12)0.48247(5)0.0360(5)
N30.4973(2)0.65466(12)0.48293(5)0.0344(4)
C10.5165(3)0.89175(16)0.30203(6)0.0453(6)
H1A0.5813890.9297760.2843210.068
H1B0.4080010.8869280.2919320.068
H1C0.5622010.8278250.3044530.068
C20.4279(2)0.89182(15)0.36639(5)0.0274(5)
C30.4191(2)0.94782(14)0.40299(5)0.0238(5)
C40.4949(2)1.03615(15)0.40526(6)0.0291(5)
H40.5554441.0581070.3839060.035
C50.4838(2)1.09244(15)0.43798(6)0.0310(5)
H50.5374211.1519500.4390970.037
C60.3947(2)1.06165(15)0.46888(6)0.0300(5)
H60.3846251.1003970.4912170.036
C70.3197(2)0.97368(14)0.46721(6)0.0288(5)
H70.2594110.9526120.4887510.035
C80.3304(2)0.91565(14)0.43486(5)0.0238(5)
C90.2446(2)0.82078(14)0.43689(6)0.0275(5)
H9A0.1603310.8243920.4567520.033
H9B0.1930550.8078760.4117580.033
C100.4024(2)0.66959(13)0.42383(5)0.0232(5)
H100.3782290.6590550.3974050.028
C110.4945(2)0.61497(14)0.44724(5)0.0239(5)
C120.5779(2)0.52400(14)0.43830(5)0.0260(5)
H12A0.6928410.5294660.4439240.031
H12B0.5333290.4710370.4537530.031
C130.5886(2)0.42117(14)0.38275(5)0.0256(5)
C140.6789(2)0.35339(14)0.40330(6)0.0305(5)
H140.7093050.3652880.4292470.037
C150.7220(2)0.27074(15)0.38558(6)0.0332(5)
H150.7851070.2260930.3993580.040
C160.6760(2)0.24937(15)0.34740(6)0.0298(5)
C170.5800(2)0.31595(14)0.32715(5)0.0267(5)
C180.5396(2)0.40414(14)0.34538(5)0.0249(5)
C190.5269(3)0.29033(15)0.28966(6)0.0346(5)
H190.4581150.3319940.2759840.042
C200.5734(3)0.20661(16)0.27298(6)0.0422(6)
H200.5360760.1908340.2479190.051
C210.6757(3)0.14346(16)0.29239(7)0.0435(6)
H210.7104240.0866340.2801240.052
C220.7244(3)0.16428(15)0.32876(7)0.0403(6)
H220.7921570.1210580.3419610.048
C230.4576(2)0.47959(14)0.32212(5)0.0250(5)
C240.2563(3)0.59621(15)0.32001(6)0.0358(5)
H24A0.2190970.5736000.2948330.054
H24B0.3319340.6485040.3162980.054
H24C0.1655840.6188680.3351630.054

Source of material

Methyl 2-(prop-2-yn-1-yloxy)-1-naphthoate (250 mg, 1.05 mmol) and methy 2-(azidomethyl)benzoate (200 mg, 1.05 mmol) were added to tert-butanol: water = 8 mL: 8 mL in a 50 mL flask, then CuSO4 ⋅ 5H2O (50 mg, 0.21 mmol) and VcNa (100 mg, 0.52 mmol) were added. The mixture was stirred at room temperature for 15 h. The solution was diluted with water and extracted with ethyl acetate. The organic layer was dried over Na2SO4. After being filtered and concentrated, the organic residue was purified by silica gel column chromatography, eluted with ethyl acetate and petroleum ether (1:1, v/v) to give a white solid (yield 68%, 310 mg); m.p. 84.9–85.7 °C; 1H NMR (400 MHz, CDCl3) d 8.02 (m, J = 8.0, 1H, Ar-H), 7.87 (d, J = 8.0, 1H, Ar-H), 7.79 (dd, J = 8.0, 1H, Ar-H), 7.73 (d, J = 12.0, 2H, Ar-H), 7.49 (ddd, J = 16.0, 1H, Ar-H), 7.39 (ddt, J = 24.0, 4H, Ar-H), 7.07 (dd, J = 8.0, 1H, Ar-H), 5.95 (s, 2H, CH2), 5.41 (s, 2H, CH2), 3.95 (s, 3H, CH3), 3.89 (s, 3H, CH3). Single crystals of the title compound were obtained from the solvents (ethyl acetate: petroleum ether = 1: 4).

Experimental details

All H-atoms were placed in calculated positions and treated as riding: C—H = 0.95–0.99 Å, with Uiso(H) = 1.2 or 1.5Ueq (parent C-atom).

Discussion

1,2,3-triazole is a five-membered heterocyclic aromatic compound, first reported by Michael in 1893 [4]. The 1,2,3-triazole has unique physical properties, and it is very stable in the metabolic transformation, redox, acid and alkali environment and thermal conditions [5]. In recent years, 1,2,3-triazole derivatives promoted the development in medicine [6], in pesticides [7] and material research [8] as well as inorganic and organic synthesis [9].

The crystal structure shows that the triazole ring connects the benzyl and the naphthyl moiety. It contains one molecule per asymmetric unit and is held together by van der Waals forces. All intramolecular bond lengths are normal. The dihedral angle between the triazole ring and the naphthyl moiety is 8.25°. So the backbone is nearly coplanar. The bond lengths and angles are in the expected ranges. The molecular confirmation and the crystal packing is stabilized by weak intermolecular C—H⋯O and C—H⋯N hydrogen bonds.

Award Identifier / Grant number: 81460538

Award Identifier / Grant number: 81773582

Funding statement: This work was supported by the National Natural Science Foundation of China (Nos. 81460538, 81773582). The authors would also like to thank Dr. Qingfeng Yang for the help with the analysis of the crystal structure data.

References

Bruker. APEX2 (Version 2.1.4), SAINT (Version 7.34A) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, WI, USA (2005).Suche in Google Scholar

Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Cryst. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar PubMed PubMed Central

Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Suche in Google Scholar PubMed

Michael, A.: Über die Einwirkung von Diazobenzolimid auf Acetylendicarbonsäure-methylester. J. Prakt. Chem. 48 (1893) 94–95.10.1002/prac.18930480114Suche in Google Scholar

Malow, M.; Wehrstedt, K. D.; Neuenfeld, S.: On the explosive properties of 1-benzotriazole and 1-1,2,3-triazole. Tetrahedron Lett. 48 (2007) 1233–1235.10.1016/j.tetlet.2006.12.046Suche in Google Scholar

Irastorza, A.; Aizpurua, J. M.; Correa, A.: Triazole-directed Pd catalyzed C(sp2)-H oxygenation of arenes and alkenes. Org. Lett. 18 (2016) 1080–1081.10.1021/acs.orglett.6b00195Suche in Google Scholar PubMed

Wei, J.; Chen, J.; Xu, J.; Cao, L.; Deng, H.; Sheng, W.; Zhang, H.; Cao, W.: Scope and regioselectivity of the 1,3-dipolar cycloaddition of azides with methyl 2-perfluoroalkynoates for an easy, metal-free route to perfluoroalkylated 1,2,3-triazoles. J. Fluorine. Chem. 133 (2012) 146–154.10.1016/j.jfluchem.2011.09.009Suche in Google Scholar

Astruc, D.; Liang, L.; Rapakousiou, A.; Ruiz, J.: Click dendrimers and triazole-related aspects: catalysts, mechanism, synthesis, and functions. A bridge between dendritic architectures and nanomaterials. Acc. Chem. Res. 45 (2012) 630–632.10.1021/ar200235mSuche in Google Scholar PubMed

Gonda, Z.; Lorincz, K.; Novak, Z.: Efficient synthesis of deuterated 1,2,3-triazoles. Tetrahedron Lett. 51 (2010) 6275–6277.10.1016/j.tetlet.2010.09.097Suche in Google Scholar

Received: 2018-04-07
Accepted: 2018-08-09
Published Online: 2018-09-08
Published in Print: 2018-11-27

©2018 Yutong Sun 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 4.10.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2018-0040/html
Button zum nach oben scrollen