Startseite Crystal structure of 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol, C37H36Cl2OSi
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Crystal structure of 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol, C37H36Cl2OSi

  • Shu-Liang Zhang , Zhao-Zhao Zhou und Xi Chen ORCID logo EMAIL logo
Veröffentlicht/Copyright: 13. Dezember 2023

Abstract

C37H36Cl2OSi, monoclinic P21/n (no. 14), a = 10.4363(14) Å, b = 17.128(2) Å, c = 17.875(3) Å, β = 90.934(2)°, V = 3194.8(8) Å3, Z = 4, R gt (F) = 0.0491, wR ref (F2) = 0.1449, T = 296.15 K.

CCDC no.: 2294926

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: Colourless block
Size: 0.12 × 0.11 × 0.08 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.27 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 27.4°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 18,849, 7173, 0.030
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 4927
N(param)refined: 382
Programs: CrysAlisPro [1], SHELX [2, 3], Diamond [4]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.4110 (2) 0.38280 (13) 0.89461 (12) 0.0413 (5)
C2 0.4680 (3) 0.37858 (17) 0.97448 (13) 0.0568 (7)
C3 0.2924 (2) 0.32905 (17) 0.89086 (16) 0.0592 (7)
C4 0.3661 (3) 0.46710 (16) 0.87892 (17) 0.0610 (7)
C5 0.6962 (2) 0.39311 (13) 0.83799 (12) 0.0387 (5)
C6 0.7158 (3) 0.46516 (15) 0.87236 (15) 0.0544 (6)
C7 0.8369 (3) 0.49780 (19) 0.8807 (2) 0.0760 (9)
C8 0.9423 (3) 0.4586 (2) 0.85429 (19) 0.0818 (10)
C9 0.9268 (3) 0.3873 (2) 0.82068 (17) 0.0722 (9)
C10 0.8053 (2) 0.35490 (17) 0.81292 (14) 0.0529 (6)
C11 0.5509 (2) 0.23854 (12) 0.83889 (12) 0.0361 (5)
C12 0.6332 (2) 0.20960 (14) 0.89511 (14) 0.0482 (6)
C13 0.6387 (3) 0.13056 (16) 0.91247 (17) 0.0609 (7)
C14 0.5637 (3) 0.07835 (15) 0.87313 (18) 0.0643 (8)
C15 0.4824 (3) 0.10414 (15) 0.81750 (18) 0.0636 (8)
C16 0.4756 (3) 0.18340 (14) 0.80053 (15) 0.0518 (6)
C17 0.4507 (2) 0.36066 (13) 0.72768 (12) 0.0345 (5)
C18 0.49834 (19) 0.40564 (11) 0.65783 (11) 0.0315 (4)
C19 0.5053 (2) 0.49315 (12) 0.67961 (11) 0.0354 (5)
C20 0.3962 (2) 0.54074 (14) 0.67906 (15) 0.0514 (6)
C21 0.4019 (3) 0.61707 (15) 0.70533 (17) 0.0622 (7)
C22 0.5156 (3) 0.64795 (15) 0.73170 (16) 0.0615 (8)
C23 0.6237 (3) 0.60274 (14) 0.73229 (15) 0.0554 (7)
C24 0.6182 (2) 0.52604 (13) 0.70675 (13) 0.0440 (5)
C25 0.62576 (19) 0.37517 (12) 0.62846 (11) 0.0330 (4)
C26 0.6687 (2) 0.29965 (13) 0.64399 (13) 0.0440 (5)
C27 0.7802 (3) 0.27077 (17) 0.61177 (15) 0.0595 (7)
C28 0.8491 (3) 0.31643 (19) 0.56355 (17) 0.0644 (8)
C29 0.8086 (2) 0.39063 (17) 0.54715 (15) 0.0554 (7)
C30 0.6988 (2) 0.42010 (13) 0.57962 (13) 0.0416 (5)
C31 0.3906 (2) 0.39440 (13) 0.59428 (11) 0.0373 (5)
C32 0.3595 (2) 0.30944 (14) 0.57629 (12) 0.0404 (5)
C33 0.2567 (3) 0.27159 (18) 0.61096 (14) 0.0606 (8)
C34 0.2315 (4) 0.1923 (2) 0.60193 (19) 0.0885 (13)
C35 0.3063 (5) 0.1491 (2) 0.5555 (2) 0.0947 (13)
C36 0.4003 (4) 0.18283 (17) 0.51649 (18) 0.0711 (9)
C37 0.4253 (2) 0.26193 (15) 0.52568 (13) 0.0481 (6)
Cl1 0.14991 (7) 0.32299 (7) 0.66617 (5) 0.0914 (3)
Cl2 0.54013 (7) 0.29926 (5) 0.46575 (4) 0.0664 (2)
H00A 0.312120 0.415468 0.615897 0.045*
H00D 0.673162 0.470878 0.568640 0.050*
H00F 0.622512 0.268122 0.676217 0.053*
H00G 0.692384 0.495976 0.707931 0.053*
H00H 0.685547 0.244241 0.921510 0.058*
H00I 0.796519 0.306244 0.790320 0.063*
H00K 0.419719 0.200133 0.762789 0.062*
H00L 0.645447 0.492285 0.890302 0.065*
H00M 0.318714 0.520987 0.660866 0.062*
H00N 0.701018 0.623307 0.749786 0.067*
H00O 0.854773 0.421340 0.514199 0.067*
H00P 0.518915 0.699135 0.748991 0.074*
H00Q 0.328167 0.647547 0.705064 0.075*
H00E 0.256822 0.329467 0.840988 0.089*
H00J 0.229378 0.347467 0.925211 0.089*
H00R 0.317086 0.276790 0.904061 0.089*
H00T 0.807922 0.220452 0.622975 0.071*
H00U 0.923164 0.296936 0.542108 0.077*
H00S 0.498778 0.326670 0.984133 0.085*
H00V 0.403085 0.391529 1.009837 0.085*
H00W 0.537709 0.414899 0.979276 0.085*
H00X 0.693080 0.113025 0.950636 0.073*
H 0.308469 0.483325 0.917241 0.092*
HA 0.322897 0.469177 0.831140 0.092*
H00Y 0.439017 0.501258 0.878629 0.092*
H00Z 0.568105 0.025385 0.884314 0.077*
H00 0.431712 0.068681 0.791019 0.076*
H00B 0.366 (2) 0.3832 (13) 0.7388 (12) 0.040 (6)*
H00C 0.433 (2) 0.3072 (14) 0.7114 (13) 0.045 (7)*
H004 0.479602 0.427307 0.511119 0.077*
H010 0.997759 0.360589 0.803019 0.087*
H011 0.846969 0.545990 0.904040 0.091*
H012 0.448356 0.153344 0.483470 0.085*
H013 0.164485 0.168925 0.627263 0.106*
H014 1.023538 0.480501 0.859271 0.098*
H015 0.291980 0.095749 0.550824 0.114*
O1 0.41224 (17) 0.44062 (10) 0.53036 (9) 0.0514 (4)
Si1 0.53266 (5) 0.34733 (3) 0.82295 (3) 0.03081 (14)

1 Source of materials

An improved synthesis was performed which was similar to the previously report [5], [6], [7], [8]. To the solution of 2,6-dichlorobenzaldehyde (1.75 g, 10.0 mmol) in anhydrous 1,4-dioxane (100 mL) was added tert-butyldiphenylsilanecarboxylic acid (4.26 g, 15.0 mmol), 1,1-diphenylethylene (2.70 g, 15.0 mmol), NaHCO3 (0.84 g, 10.0 mmol) and organic photo catalyst 4CzIPN (394 mg, 0.5 mmol) under argon atmosphere. After addition, the reaction mixture was irradiated under 440 nm Kessil light for 12 h. TLC detection showed the reaction was finished. After simple filtration by silicon gel, the solvent was removed in vacuo. The obtained residue was dissolved in dichloromethane (100 mL), washed with water (50 mL × 2), brine (50 mL × 2), and dried over anhydrous MgSO4. After filtration, the solvent was evaporated in vacuo. The obtained residue was purified by column chromatography to afford white solid of 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol (4.38 g, 72 %), which was further purified by recrystallization from hexane and ethyl acetate. Crystals were obtained by slow evaporation from the solution at 268–270 K.

2 Experimental details

Carbon bound hydrogen atoms were included using riding models. For the OH group additionally a rotation about the C–O bond was allowed.

3 Comment

The 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol is a product formed by the reductive radical polar crossover (RPC)-type reaction [9], in which the anion is generated from single-electron reduction. RPC reactions have been proven useful in the formation of multiple bonds in a single transformation, including a multicomponent reaction (MCR) manifold [10]. In this paper, a silane radical was produced through single electron oxidation and decarboxylation of tert-butyldiphenylsilanecarboxylic acid anion, which then was added to the olefin to form carbon-centered radical. Next, carbon anion was achieved after single-electron reduction with low-valence organic photo catalyst 4CzIPN. Finally, carbon anion can then be added to aldehyde to provide the 3-silyl-propan-1-ol derivative. Different from Nozaki–Hiyama-Kishi type reaction [11], multicomponent strategy of reductive RPC reactions without alkyl metal species was rarely reported [8], especially with silane radical. Crystals of 3-(tert-butyl diphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol were obtained by continuous adjustment of crystallization conditions, which revealed the specific structure of the multicomponent RPC reaction product with silanecarboxylic acid for the first time. In the meantime, this result also provides direct structural proof for the structure of the previous report [8], which is very significant for further understanding 3-silyl-propan-1-ol derivative and multicomponent RPC reaction. The title structure (see the Figure) was reported for the first time in this paper. This crystal structure is a racemic alcohol with a chiral carbon atom (C31). The propyl alcohol was linked to a 2,6-dichlorophenyl at C31, two phenyl at C18, and a silyl group at C17. The bond lengths and angles are in the expected ranges [12, 13].


Corresponding author: Xi Chen, Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, P.R. China, E-mail:

Funding source: Nanchang Normal University

Award Identifier / Grant number: NSBSJJ2020009

Funding source: Ph.D. Programs Foundation of Jiangxi Science and Technology Normal University

Funding source: Science and Technology project of Jiangxi Provincial Education Office

Award Identifier / Grant number: GJJ2201329

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

  2. Research funding: This work was supported by from the Nanchang Normal University (NSBSJJ2020009), the Ph.D. Programs Foundation of Jiangxi Science and Technology Normal University,the Science and Technology project of Jiangxi Provincial Education Office (GJJ2201329).

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

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Received: 2023-10-12
Accepted: 2023-11-13
Published Online: 2023-12-13
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
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  14. The crystal structure of 1,2-bis(2,4-dinitrophenyl) hydrazine, C12H8N6O8
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  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
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  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
  34. Crystal structure of tetraaqua-[(1-(carboxymethyl)-1H-pyrazole-3-carboxylato-κ2N,O)cobalt(II)], C6H12CoN2O8
  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
  36. Crystal structure of 2-((2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)amino)benzoic acid, C18H14Cl2N2O3
  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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  41. Crystal structure of 4-bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, C13H7BrClF3N2
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  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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