Home Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5
Article Open Access

Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5

  • Shiyin Huang , Minlei Yin , Yuxin Lin , Heyi Yang , Jie Chen ORCID logo EMAIL logo and Ting Qiu EMAIL logo
Published/Copyright: April 24, 2024

Abstract

C16H14O5, monoclinic, P21/c (no. 14), a = 11.1420(17) Å, b = 8.4700(12) Å, c = 15.429(2) Å, β = 104.624(4)°, V = 1408.9(4) Å3, Z = 4, R gt(F) = 0.0513, wR ref(F 2) = 0.1243, T = 296(2) K.

CCDC no.: 2334088

The molecular structure is shown in the figure. 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: Colorless block
Size: 0.22 × 0.20 × 0.18 mm
Wavelength: MoKα radiation (0.71073 Å)
μ: 0.10 mm−1
Diffractometer, scan mode: Bruker D8 Quest, φ and ω
θ max, completeness: 25.1°, 99 %
N(hkl)measured, N(hkl)unique, R int: 21309, 2470, 0.074
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 1566
N(param)refined: 192
Programs: Bruker [1], Shelx [2, 3]
Table 2:

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

Atom x y z U iso */U eq
C1 1.1650 (2) 0.9047 (3) 0.52117 (19) 0.0539 (7)
H1 1.2046 0.9239 0.5809 0.065*
C2 1.05368 (19) 0.8041 (3) 0.50297 (16) 0.0430 (6)
C3 0.98582 (19) 0.7741 (3) 0.41546 (16) 0.0454 (6)
H3 1.0093 0.8200 0.3675 0.055*
C4 0.8832 (2) 0.6756 (3) 0.40005 (15) 0.0434 (6)
C5 0.84947 (19) 0.6099 (2) 0.47331 (16) 0.0405 (6)
C6 0.9162 (2) 0.6387 (3) 0.55908 (16) 0.0475 (6)
H6 0.8929 0.5926 0.6070 0.057*
C7 1.0188 (2) 0.7370 (3) 0.57429 (16) 0.0477 (6)
H7 1.0642 0.7577 0.6326 0.057*
C8 0.8557 (2) 0.6697 (4) 0.24285 (17) 0.0698 (8)
H8A 0.8023 0.6227 0.1905 0.105*
H8B 0.9383 0.6295 0.2510 0.105*
H8C 0.8562 0.7822 0.2356 0.105*
C9 0.63412 (19) 0.5543 (2) 0.42516 (14) 0.0398 (6)
C10 0.5975 (2) 0.7069 (3) 0.43386 (16) 0.0474 (6)
H10 0.6549 0.7825 0.4616 0.057*
C11 0.4736 (2) 0.7468 (3) 0.40067 (16) 0.0517 (7)
H11 0.4480 0.8498 0.4069 0.062*
C12 0.3879 (2) 0.6358 (3) 0.35856 (15) 0.0462 (6)
C13 0.4258 (2) 0.4810 (3) 0.35023 (15) 0.0451 (6)
H13 0.3684 0.4058 0.3220 0.054*
C14 0.5482 (2) 0.4393 (2) 0.38366 (15) 0.0407 (6)
C15 0.5101 (2) 0.1684 (3) 0.34668 (19) 0.0655 (8)
H15A 0.4669 0.1903 0.2858 0.098*
H15B 0.4516 0.1612 0.3827 0.098*
H15C 0.5539 0.0702 0.3493 0.098*
C16 0.2593 (2) 0.6818 (3) 0.31959 (19) 0.0628 (7)
H16 0.2384 0.7864 0.3269 0.075*
O1 1.20977 (16) 0.9648 (2) 0.46522 (13) 0.0672 (5)
O2 0.81204 (14) 0.6325 (2) 0.31810 (11) 0.0627 (5)
O3 0.75318 (13) 0.50078 (17) 0.45858 (11) 0.0494 (4)
O4 0.59560 (14) 0.29136 (17) 0.37947 (12) 0.0578 (5)
O5 0.17784 (16) 0.5966 (2) 0.27880 (13) 0.0742 (6)

1 Source of material

A 150 mL three-neck flask was charged with vanillin (0.01 mol), 4-chloro-3-methoxybenzaldehyde (0.01 mol), potassium carbonate (0.01 mol), and N,N-dimethylformamide (40 mL). This mixture was stirred at room temperature for 8 h, with the progress of the reaction monitored by thin-layer chromatography (TLC) until completion. Upon completion, the reaction was quenched by the addition of water. The organic phase was extracted three times with dichloromethane (30 mL × 3). After removing the solvent under reduced pressure via rotary evaporation, the crude product was purified using silica gel column chromatography, yielding 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde.

2 Experimental details

The C–H atoms were constrained to an ideal geometry, with C–H distances of 0.93 Å–0.98 Å. The U iso values of the hydrogen atoms of methyl groups were set to 1.5U eq(Cmethyl) and the U iso values of all other hydrogen atoms were set to 1.2U eq(C).

3 Comment

Diphenyl ether herbicides are the earliest commercialized class of herbicides in the family of protoporphyrinogen oxidase inhibitors, and there are still a variety of products on the market, which are widely used because of their excellent characteristics, such as high efficiency, low toxicity, and broad spectrum [4], [5], [6]. Therefore, 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde and its derivatives have potential herbicidal potential in the field of pesticides. The crystal structure of the compound was analyzed to provide a precise structure for predicting the binding conformation of the small molecule ligand to the target binding site from the molecular level. The crystalline structure elucidates that the two phenyl rings are not coplanar [7]. The dihedral angle between the best planes of the benzene ring (C2/C3/C4/C5/C6/C7) and benzene ring (C9/C10/C11/C12/C13/C14) is 83.79°. In the crystal, molecular cohesion is maintained through C–H…O hydrogen bond interactions.


Corresponding authors: Jie Chen, College of Chemical Engineering, Fuzhou University, Fuzhou, 350108, People’s Republic of China, E-mail: ; and Ting Qiu, College of Chemical Engineering, Fuzhou University, Fuzhou, 350108, People’s Republic of China; and Fuzhou University International Joint Laboratory of Thermochemical Conversion of Biomass, Fuzhou, People’s Republic of China, E-mail:
Shiyin Huang and Minlei Yin contributed equally.

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: (Grant No. 22108040 and 22278077)

Funding source: Key Program of Qingyuan Innovation Laboratory

Award Identifier / Grant number: (Grant No. 00221004)

Funding source: Natural Science Foundation of Fujian Province

Award Identifier / Grant number: (Grant No. 2020J05130)

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

  2. Research funding: National Natural Science Foundation of China (Grant No. 22108040 and 22278077), Key Program of Qingyuan Innovation Laboratory (Grant No. 00221004), and Natural Science Foundation of Fujian Province (Grant No. 2020J05130).

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

References

1. Bruker . Apex2, Saint and Sanabs; Brucker AXS Inc.: Madison, WI, USA, 2012.Search in Google Scholar

2. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112–122; https://doi.org/10.1107/s0108767307043930.Search in Google Scholar PubMed

3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

4. Yang, F. W., Cui, Y. W., Yu, H., Guo, Y. H., Cheng, Y. L., Yao, W. R., Xie, Y. F. Identifying potential thyroid hormone disrupting effects among diphenyl ether structure pesticides and their metabolites in silico. Chemosphere 2022, 288, 132575; https://doi.org/10.1016/j.chemosphere.2021.132575.Search in Google Scholar PubMed

5. Zhao, L. X., Jiang, M. J., Hu, J. J., Zou, Y. L., Ye, F. Herbicidal activity and molecular docking study of novel PPO inhibitors. Weed Sci. 2020, 68, 1–34; https://doi.org/10.1017/wsc.2020.66.Search in Google Scholar

6. Wang, D. W., Liang, L., Xue, Z. Y., Yu, S. Y., Xi, Z. Discovery of n-phenylaminomethylthioacetylpyrimidine-2,4-diones as protoporphyrinogen ix oxidase inhibitors through a reaction intermediate derivation approach. J. Agric. Food Chem. 2021, 69, 4081–4092; https://doi.org/10.1021/acs.jafc.1c00796.Search in Google Scholar PubMed

7. Hafeez, A., Akhter, Z., Gallagher, J. F., Khan, N. A., Gul, A., Shah, F. U. Synthesis, crystal structures, and spectroscopic characterization of bis-aldehyde monomers and their electrically conductive pristine polyazomethines. Polymers 2019, 11, 1498; https://doi.org/10.3390/polym11091498.Search in Google Scholar PubMed PubMed Central

Received: 2024-02-28
Accepted: 2024-03-27
Published Online: 2024-04-24
Published in Print: 2024-08-27

© 2024 the author(s), published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of hexaquazinc(II) poly[hexakis(μ2-4-methylbenzenesulfinato-κ2O:O′) dizinc(II)]
  4. The crystal structure of poly[((2-(4,5-dihydro-1H-pyrazol-4-yl)-1,3-dioxoisoindoline-5-carbonyl)oxy)(1-(dimethylamino)ethoxy)zinc[II]], C16H14ZnN4O5
  5. Crystal structure of bis[(triaqua-4-iodopyridine-2,6-dicarboxylato-κ 3 N,O,O )cobalt(II)] trihydrate, C14H22N2O17I2Co2
  6. Crystal structure of bis(methanol-κO)-bis(nitrato-kO)-bis(1-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole-κN)cadmium(II), C40H42O14N8Cl4Cd
  7. Crystal structure of poly[μ2-dichlorido-(μ2-1-[(2,4-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2N:N′)cadmium(II)], C11H12CdN6Cl2
  8. The crystal structure of (3aS, 4R, 7S, 7aR)-hexahydro-4, 7-methano-1H-isoindole-1, 3-(2H)-dione, C9H11NO2
  9. The crystal structure of N-(acridin-9-yl)-4-chloro-N-(4-chloro-butanoyl) butanamide, C21H20Cl2N2O2
  10. Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5
  11. The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4
  12. Crystal structure of methyl-1-(naphthalen-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H20N2O2
  13. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  14. Crystal structure of 6,6′-((1E,1′E)-((2-phenylpyrimidine-4,6-diyl)bis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))bis(2-methoxyphenol)monohydrate, C26H26N6O5
  15. Crystal structure of bis(N,N,N-trimethylbutanaminium) tetrathiotungstate(VI), (BuMe3N)2[WS4]
  16. The crystal structure of 2,3,9-triphenyl-9-(2-phenylbenzofuran-3-yl)-9H-9λ 5-benzo[4,5][1,2]oxaphospholo[2,3-b][1,2,5]oxadiphosphole 2-oxide, C40H28O4P2
  17. Crystal structure of 1–methyl-3-propyl-4-nitro-1H-pyrazole-5-carboxylic acid, C8H11N3O4
  18. Crystal structure of N-(benzo[d]thiazol-2-yl)-2-chloroacetamide, C9H7ClN2OS
  19. The crystal structure of N-benzyl-2-chloro-N-(p-tolyl) acetamide, C16H16ClNO
  20. Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
  21. Crystal structure of 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, C26H28N2O6
  22. Crystal structure of poly[(μ3-5-bromoisophthalato-κ4 O,O′ :O″,O‴)-(μ2-1,2-bis(1,2,4-triazole-1-ylmethyl)benzene-κ2 N:N′)cobalt(II)], C20H15BrCoN6O4
  23. The crystal structure of bis(2-(piperidin-1-ium-4-yl)-1Hbenzo[d]imidazol-3-ium) dihydrogen decavanadate, C24H36N6O28V10
  24. Crystal structure of diaqua-bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine3-carboxylato-O,O′)-cobalt(ii)dihydrate, C26H36N4O14Co
  25. Crystal structure of poly[(μ2-5-bromoisophthalato-κ4 O,O :O ,O )-(μ2-1,4-bis(2-methylimidazol-1-ylmethyl)benzene-N:N)cadmium(II)], C24H21BrCdN4O4
  26. The crystal structure of dimethyl 8-(3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl)-4-methyl-1-(p-tolyl)-1,3a,4,8b-tetrahydro-3H-furo[3,4-b]indole-3,3-dicarboxylate. C28H29NO9
  27. Crystal structure of (3R)-1-(3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate chloride, C21H23ClN2O4
  28. Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S
  29. The crystal structure of hexaaquamagnesium(II) bis-3-(1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-α]pyridin-1-yl)benzoate, C36H42N4O10Mg
  30. Crystal structure of 4-formyl-2-methoxyphenyl 2-acetoxybenzoate, C17H14O6
  31. Crystal structure of poly[octakis(μ-oxido)-tris(μ-1,1′-[[1,1′-biphenyl]-4,4′-diylbis(methylene)]bis(1H-imidazole))-tetrakis(oxido)-tetra-vanadium-dimanganese(II)dihydrate], C30H29MnN6O7V2
  32. Crystal structure of 4,8a-bis(4-chlorophenyl)-1,5,6-tris(4-fluorobenzyl)-1,4,4a,4b,5,6,8a,8b-octahydrocyclobuta[1,2-b:3,4-c′]dipyridine-3,8-dicarbonitrile, C45H33Cl2F3N4
  33. Crystal structure of benzo[d][1,3]dioxol-5-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H20O5
  34. Crystal structure of N-benzoyl-N-phenylhydroxylaminato-dicarbonylrhodium(I), [Rh(BNA)CO2]
  35. The crystal structure of N-(2-((2-methoxynaphthalen-1-yl)ethynyl)phenyl)-4-methylbenzenesulfonamide, C26H21NO3S
  36. The crystal structure of methyl ((4-aminobenzyl)sulfonyl)-d-prolinate, C13H18N2O4S
  37. The crystal structure of dichlorido-(N-isopropyl-N-(pyridin-2-ylmethyl)propan-2-amine-κ 2 N, N′)palladium(II), C12H20N2PdCl2
  38. Crystal structure of poly[(μ 2-5-hydroxyisophthalato-κ4 O,O′:O″,O‴)-(μ 2-1,4-bis(2-methylimidazolyl)-1-butene-N:N′)nickel(II)], C20H20NiN4O5
  39. The crystal structure of {hexakis(1-methyl-1H-imidazole-κ 1 N)cobalt(II)}(μ 2-oxido)-hexaoxido-dimolybdenum(VI)— 1-methyl-1H-imidazole (1/2), C32H48CoMo2N16O7
  40. Synthesis, crystal structure and nonlinear optical property of 1-((propan-2-ylideneamino)oxy)propan-2-yl-4-methylbenzenesulfonate, C13H19O4NS
  41. The crystal structure of N,N-(ethane-1,1-diyl)dibenzamide, C16H16N2O2
  42. Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P
  43. The crystal structure of fac-tricarbonyl(bis(3,5-dimethyl-4H-pyrazole)-κ1 N)-((nitrato)-κ1 O)-rhenium(I)— 3,5-dimethyl-4H-pyrazole(1/1), C18H23N7O6Re
  44. The crystal structure of 4′-chloro-griseofulvin: (2S,6′R)-4′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-3′-ene-2′,3-dione, C16H14Cl2O5
  45. Crystal structure of tetraethylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  46. Crystal structure of 1-cyclohexyl-4-p-tolyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester, C22H27NO4
  47. The crystal structure of catena-poly(μ2-1,4-bis-(1H-imidazol-1-yl)benzene-copper(I)) dichloridocopper(I), {[CuC12H10N4]+[CuCl2]} n
  48. The crystal structure of propane-1-aminium-2-carbamate, C4H10N2O2
  49. Crystal structure of 5,6,3′,4′,5′-pentamethoxy-flavone dihydrate, C20H24O9
  50. Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3
  51. Crystal structure of methyl (3R)-1-(2-bromo-4-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride hydrate, C19H19BrClFN2O3
  52. The crystal structure of 1-(2-chlorophenyl)-3-(p-tolyl)urea, C14H13ClN2O
  53. The crystal structure of 1-cyclohexyl-3-(p-tolyl)urea, C14H20N2O
  54. Crystal structure of ((benzyl(hydroxy)-amino)(4-chlorophenyl)methyl)-diphenylphosphine oxide, C26H23ClNO2P
  55. The crystal structure of ethyl 3-(1-methyl-1H-indole-2-carbonyl)-2-phenylquinoline-4-carboxylate, C28H22N2O3
  56. The crystal structure of 1,4-bis(1H-imidazol-3-ium-1-yl)benzene dinitrate, C12H12N4 2+·2(NO3 )
  57. Crystal structure of tris(hexafluoroacetylacetonato-κ2O,O′) bis(triphenylphosphine oxide-κ1O)samarium(III), C51H33F18O8P2Sm
  58. Crystal structure of 1-(4-(dimethylamino)phenyl)-2,3-bis(diphenylphosphoryl)propan-1-one, C35H33NO3P2
  59. Crystal structure of diaqua[bis(μ 2-pyridine 2,6-dicarboxylato) bismuth(III) potassium(I)], C14H10BiKN2O10
  60. Crystal structure of (R)-N, N -dimethyl-[1, 1′-binaphthalene]-2, 2′-diamine, C22H20N2
  61. Crystal structure of 1-phenyl-4-(2-furoyl)-3-furyl-1H-pyrazol-5-ol, C18H12N2O4
  62. Crystal structure of bis(14,34-dimethyl[11,21:23,31-terphenyl]-22-yl)diselane, C40H34Se2
Downloaded on 15.10.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2024-0095/html?lang=en&srsltid=AfmBOopb5uwAK9MDwY9w--TUX0DiSj5r2gX_Szcu2RRv1gSleJW9VGCv
Scroll to top button