Startseite Naturwissenschaften The crystal structure of 5′-(furan-2-yl)-3′-((4-methylphenyl)sulfonamido)-3′,4′,5′,6′-tetrahydro-[1,1′:3′,1″-terphenyl]-4′-carboxylic acid, C30H27NO5S
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The crystal structure of 5′-(furan-2-yl)-3′-((4-methylphenyl)sulfonamido)-3′,4′,5′,6′-tetrahydro-[1,1′:3′,1″-terphenyl]-4′-carboxylic acid, C30H27NO5S

  • Xulan Wang , Guoyong Luo ORCID logo , Jianghai Ye ORCID logo , Jiangping Wang , Yunlong Liu und Tianqiong Lang EMAIL logo
Veröffentlicht/Copyright: 8. Dezember 2023

Abstract

C30H27NO5S, monoclinic, P21 (no. 4), a = 10.4329(16) Å, b = 11.6208(18) Å, c = 11.8268(18) Å, β = 114.257(5)°, V = 1307.3(4) Å3, Z = 2, R gt (F) = 0.0685, wR ref (F2) = 0.1547, T = 273(2) K.

CCDC no.: 2301380

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: Yellow needle
Size: 0.24 × 0.19 × 0.13 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.17 mm−1
Diffractometer, scan mode: Bruker APEX-II
θmax, completeness: 32.1°, 99 %
N (hkl)measured, N(hkl)unique, Rint: 16,448, 8845, 0.059
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 4334
N(param)refined: 336
Programs: Bruker [1], SHELX [2, 3]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.2876 (4) 0.3462 (3) 0.5984 (4) 0.0388 (9)
C2 0.2714 (4) 0.4295 (3) 0.5169 (4) 0.0404 (9)
C3 0.2906 (5) 0.5542 (4) 0.5545 (4) 0.0513 (11)
C4 0.3520 (5) 0.5723 (3) 0.6941 (4) 0.0428 (10)
C5 0.2820 (4) 0.4877 (3) 0.7527 (4) 0.0355 (9)
C6 0.3209 (4) 0.3623 (3) 0.7354 (3) 0.0350 (8)
C7 0.2313 (4) 0.4042 (3) 0.3840 (4) 0.0395 (9)
C8 0.1254 (5) 0.3255 (4) 0.3217 (5) 0.0592 (13)
C9 0.0868 (6) 0.3023 (4) 0.1963 (5) 0.0717 (16)
C10 0.1545 (6) 0.3566 (5) 0.1330 (5) 0.0699 (15)
C11 0.2582 (6) 0.4341 (5) 0.1937 (5) 0.0622 (14)
C12 0.2948 (5) 0.4589 (4) 0.3170 (4) 0.0496 (11)
C13 0.2345 (4) 0.2771 (3) 0.7752 (4) 0.0382 (9)
C14 0.2943 (5) 0.2068 (4) 0.8767 (5) 0.0526 (12)
C15 0.2132 (7) 0.1312 (5) 0.9112 (6) 0.0708 (16)
C16 0.0712 (7) 0.1258 (5) 0.8425 (6) 0.0722 (16)
C17 0.0107 (6) 0.1961 (5) 0.7416 (6) 0.0672 (15)
C18 0.0911 (5) 0.2704 (4) 0.7071 (4) 0.0534 (11)
C19 0.3430 (5) 0.6956 (4) 0.7277 (4) 0.0474 (11)
C20 0.4383 (5) 0.7724 (4) 0.7932 (4) 0.0585 (12)
C21 0.3669 (7) 0.8738 (4) 0.7985 (5) 0.0702 (15)
C22 0.2322 (7) 0.8511 (4) 0.7373 (5) 0.0727 (16)
C23 0.3188 (5) 0.5232 (3) 0.8844 (4) 0.0419 (10)
C24 0.6632 (4) 0.3420 (4) 0.7127 (4) 0.0443 (10)
C25 0.7755 (5) 0.4122 (4) 0.7806 (5) 0.0591 (13)
C26 0.8407 (6) 0.4761 (5) 0.7209 (6) 0.0685 (15)
C27 0.7947 (5) 0.4712 (4) 0.5932 (5) 0.0545 (12)
C28 0.6822 (5) 0.3999 (5) 0.5281 (5) 0.0587 (13)
C29 0.6164 (5) 0.3352 (4) 0.5867 (4) 0.0528 (12)
C30 0.8677 (6) 0.5359 (5) 0.5261 (5) 0.0756 (16)
H1A 0.507903 0.391914 0.876635 0.049*
H2 0.917621 0.600226 0.575578 0.113*
H2A 0.247937 0.613197 0.965108 0.084*
H3 0.200114 0.592562 0.517648 0.062*
H3A 0.932782 0.485673 0.512137 0.113*
H4 0.916345 0.523085 0.767013 0.082*
H5 0.807135 0.416459 0.866332 0.071*
H5A 0.179995 0.495575 0.707244 0.043*
H6 0.390914 0.209818 0.923429 0.063*
H7 0.255383 0.084507 0.980587 0.085*
H8 0.048270 0.316468 0.637284 0.064*
H9 −0.086078 0.193629 0.695622 0.081*
H10 0.016289 0.074863 0.864225 0.087*
H10A 0.129781 0.340611 0.049552 0.084*
H11 0.015171 0.249965 0.155434 0.086*
H12 0.079843 0.287904 0.364157 0.071*
H13 0.304789 0.470599 0.151492 0.075*
H14 0.363841 0.513776 0.355923 0.060*
H15 0.352032 0.589987 0.521622 0.062*
H16 0.160196 0.902788 0.727204 0.087*
H17 0.406781 0.942531 0.837317 0.084*
H18 0.535174 0.761398 0.829318 0.070*
H19 0.451920 0.552272 0.726321 0.051*
H21 0.277685 0.270986 0.569149 0.047*
H22 0.541235 0.287538 0.541057 0.063*
H23 0.649795 0.395437 0.442316 0.070*
H24 0.799205 0.563059 0.448008 0.113*
N1 0.4729 (3) 0.3484 (3) 0.8123 (3) 0.0410 (8)
O1 0.4316 (3) 0.5073 (3) 0.9683 (3) 0.0660 (10)
O2 0.2166 (3) 0.5799 (3) 0.8981 (3) 0.0560 (8)
O3 0.2119 (3) 0.7415 (3) 0.6905 (3) 0.0607 (9)
O4 0.5042 (3) 0.1702 (2) 0.7112 (3) 0.0586 (9)
O5 0.6877 (3) 0.2360 (3) 0.9114 (3) 0.0580 (9)
S1 0.58051 (11) 0.26194 (8) 0.79045 (11) 0.0438 (3)

1 Source of materials

The title compound was obtained via the following synthetic procedure: N-((E)-1,3-diphenylbut-2-en-1-ylidene)-4-methylbenzenesulfonamide (0.2 mmol, 1 eq) and (E)-3-(furan-2-yl)acrylaldehyde (2 eq) were added into a dry Schlenk tube, which was filled with (R)-diphenylprolinol trimethyl silyl ether (0.2 eq), dipotassium phosphate (1 eq), monopotassium phosphate (1 eq) and sodium chloride (1 eq). The tube was heated at 60 °C to initiate the reaction under nitrogen atmosphere with 2 mL of MeOH/H2O (99:1) as solvent. After 12 h, the reaction mixture was separated over silica gel chromatography eluted with petroleum ether/ethyl acetate (7:1) to obtain the intermediate in 55 % yield, which was further transformed to the title compound in 64 % yield using KMnO4 (2 eq) as the oxidant. The structure of the title compound was determined by NMR analyses before XRD analyses. The yellow needles were obtained via recrystallization in dichloromethane/ethyl acetate.

2 Experimental details

The structure was solved and refined using the Bruker SHELXTL Software Package [2, 3].

3 Comment

The title compound belongs to cyclic β-amino acids characterized by well-defined and controllable conformational preferences, demonstrating its potential as building blocks in the field of foldamer research [4, 5]. Additionally, cyclic β-amino acids also exhibited various bioactivities such as anti-tumor and anti-influenza [6], [7], [8]. Thus, it has attracted an increased interest in the past two decades, and several effective methods have been developed to access cyclic β-amino acids [9, 10].

There is one crystallographically independent molecule in the asymmetric unit of the title compound with all geometric parameters in normal ranges [11]. The cyclohexene skeleton was shown in its half-chair conformation with C1–C2–C3–C6 almost in the same plane. The dihedral angle between phenyl plane at C2 with C1–C2–C3 plane was determined as 44.5°. Only one intramolecular hydrogen bond was observed between N1–H1A and O1 with donor–acceptor distance of 2.078 Å, and the molecules were packed through the intermolecular hydrogen bond between O2–H2A from the carboxyl group with O5 from the sulfonyl group with donor-acceptor distance of 1.953 Å.


Corresponding author: Tianqiong Lang, School of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, China, E-mail:

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

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

  3. Research funding: Scientific and Technological Outstanding Talent Plan from Educational Commission of Guizhou Province (QJJ[2022]082), and the 1000 Talent Plan (Qian Cengci) of Guizhou Province (GZY[ZQ2018002]).

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Received: 2023-10-19
Accepted: 2023-11-23
Published Online: 2023-12-08
Published in Print: 2024-02-26

© 2023 the author(s), 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. Crystal structure of poly[diaqua-(μ4-3,3′-di(1H-1,2,4-triazol-1-yl)-[1,1′-biphenyl]-4,4′-dicarboxylate-N:N′:O:O′)cadmium(II)], C18H14N6O6Cd
  4. Crystal structure of (8R,8′S,13S,13′R)-8,8′-bis(hydroxymethyl)-9,9′,10,10′-tetramethoxy-5,5′,6,6′,8,8′,13,13′-octahydro-[13,13′-bi[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline]-7,7′-diium chloride-methanol (1/2), C46H58N2O14Cl2
  5. The crystal structure of 8-methoxy-2,2-diphenyl-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C29H25BN2O3S
  6. Crystal structure of aqua-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)copper(II) 5-carboxyisophthalate tetrahydrate, C25H50N4CuO11
  7. The crystal structure of 1-(naphthalen-2-ylsulfonyl)-2,2-diphenyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinoline, C31H23BN2O2S
  8. Crystal structure of iodido-(η6-benzene) (1-(pyridin-2-yl)-N-(p-fluoro-methanamine)-κ2N,Nʹ)ruthenium(II) hexaflourophosphate, (C18H15F7IN2RuP)
  9. The crystal structure of 1-(3-oxo-1-phenyl-3-(p-tolyl) propylidene)-1,3-dihydro-2H-inden-2-one, C25H20O2
  10. Crystal structure of tricyclohexyl[4-(4H-1,2,4-triazol-4-yl)-benzoato-κO]tin(IV), C27H39N3O2Sn
  11. Crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)cadmium(II)]monohydrate, C12H15NO9Cd
  12. Crystal structure of ethyl 2-((4-(3,5-dimethylisoxazol-4-yl)-2,6-difluorophenyl)amino)benzoate, C20H18F2N2O3
  13. The crystal structure of 2-(hydroxymethyl)-2-(4H-1,2,4-triazol-4-yl)propane-1,3-diol, C6H11N3O3
  14. The crystal structure of 1,2-bis(2,4-dinitrophenyl) hydrazine, C12H8N6O8
  15. Crystal structure of 1-(2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one, C19H14Cl2N2O3
  16. The crystal structure of 5-amino-5-oxo-4-(1-oxo-4-(2-oxopyrrolidin-1-yl)isoindolin-2-yl)pentanoic acid, C17H19N3O5
  17. Crystal structure of N2,N6-bis(2-(((Z)-5-bromo-2-hydroxybenzylidene)amino) phenyl)pyridine-2,6-dicarboxamide, C33H23Br2N5O4
  18. The crystal structure of (E)-2-methoxy-6-(((5-methyl-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C11H11N3O2S
  19. The crystal structure of 3-((tert-butyldiphenylsilyl)methyl)-5,5-diphenyl-6-(p-tolyl) tetrahydro-2H-pyran-2-one, C41H42O2Si
  20. Crystal structure of 9-fluoro-4-(6-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  21. The crystal structure of 2-bromo-5-(4-cyanophenoxy)benzyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate, C21H19BrN2O3
  22. Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-isopropyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C10H14F6N2P
  23. The crystal structure of 2,2-di(thiophen-3-yl)-1-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C24H19BN2O2S3
  24. Crystal structure of 5-bromo-1-(2-iodobenzoyl)-1H-indole-3-carbaldehyde, C16H9BrINO2
  25. The crystal structure of monocarbonyl-2-carboxypyridinato-κ2N,O-triphenylphosphine-rhodium(I) acetonitrile solvate, C26H20.50N1.50O3PRh
  26. Crystal structure of dichlorido-tetrakis(1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ1N)manganese(II), C60H68O4N12Cl10Mn
  27. Crystal structure of 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol, C37H36Cl2OSi
  28. Crystal structure of langite from Mine du Pradet (France)
  29. The crystal structure of 5′-(furan-2-yl)-3′-((4-methylphenyl)sulfonamido)-3′,4′,5′,6′-tetrahydro-[1,1′:3′,1″-terphenyl]-4′-carboxylic acid, C30H27NO5S
  30. Synthesis and crystal structure of bis{2-(((4-acetophenone)imino)methyl)-4-fluorophenolato-κ2N,O}zinc(II), C30H22F2N2O4Zn
  31. The crystal structure of poly[(tripyridine-κ3N,N′,N″) μ3-(pyridine-3,4-dicarboxylate-κ3N:O:O′) manganese(II)], C22H22N4O8Mn
  32. The crystal structure of (E)-4-chloro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15ClN2O2
  33. Synthesis and crystal structure of bis{2-(tert-butyl)-6-((E)-((4-((E)-1-(methoxyimino) ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II), C40H46CoN4O4
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  35. (6R,7S)-2,3,13-trimethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3′,4′]cycloocta [1′,2′:4,5]benzo[1,2-d][1,3]dioxol-1-ol, C22H26O6
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  37. Crystal structure of (5aS,6aS,8aR,9R,11aS, 11bS,13R,13aS)-1,1,8a,11a-tetramethyl-9-((S)-1-((S)-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3-oxo-1,7,8,8a,9,10,11,11a,11b,12,13,13a-dodecahydro-3H,6H-cyclopenta[5,6]cyclopropa[1,8a]naphtho[2,1-c]oxepin-13-yl acetate, C32H44O6
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  45. The crystal structure of 1,3,5-tris(dibromomethyl)benzene, C9H6Br6
  46. Crystal structure of (Z)-3-(4-methoxyphenyl)-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-N-phenylthiazol-2(3H)-imine, C25H21N5OS
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