Home Crystal structure of cyclopropane-1,2,3-triyltris(phenylmethanone), C24H18O3
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Crystal structure of cyclopropane-1,2,3-triyltris(phenylmethanone), C24H18O3

  • Li Zeng , Gui-Yun Tang , Yu-Cai Wang and Chun-Yan Liu ORCID logo EMAIL logo
Published/Copyright: May 6, 2021

Abstract

C24H18O3, monoclinic, P21/n (no. 14), a = 5.376(2) Å, b = 15.787(6) Å, c = 21.103(7) Å, β = 92.356(6)°, V = 1789.5(11) Å3, Z = 4, Rgt(F) = 0.0569, wRref(F2) = 0.1166, T = 296 K.

CCDC no.: 2074969

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:0.16 × 0.15 × 0.14 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.09 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:26.0°, 99%
N(hkl)measured, N(hkl)unique, Rint:9832, 3508, 0.053
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2022
N(param)refined:245
Programs:Bruker [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
O10.2425 (3)0.28771 (11)0.55328 (8)0.0549 (5)
O20.1949 (4)0.11728 (12)0.46971 (9)0.0642 (6)
O30.9109 (3)0.29520 (12)0.39309 (8)0.0572 (5)
C10.5241 (4)0.39952 (15)0.57561 (11)0.0374 (6)
C20.3931 (5)0.43072 (17)0.62563 (13)0.0555 (8)
H20.2545680.4012980.6388030.067*
C30.4630 (6)0.50394 (19)0.65613 (14)0.0652 (9)
H30.3745550.5229300.6903140.078*
C40.6599 (6)0.54872 (18)0.63679 (14)0.0638 (9)
H40.7042740.5990600.6571720.077*
C50.7939 (6)0.52066 (19)0.58768 (16)0.0750 (10)
H50.9299540.5514950.5745860.090*
C60.7266 (6)0.44613 (18)0.55741 (14)0.0644 (9)
H60.8194770.4268800.5240830.077*
C70.4481 (5)0.31887 (16)0.54495 (11)0.0406 (6)
C80.6232 (5)0.27616 (15)0.50297 (10)0.0398 (6)
H80.7964280.2954700.5069160.048*
C90.5278 (5)0.25487 (15)0.43641 (11)0.0399 (6)
H90.3506230.2657070.4270300.048*
C100.5867 (5)0.18541 (15)0.48269 (11)0.0415 (6)
H100.7418750.1552330.4750030.050*
C110.3816 (5)0.12973 (16)0.50414 (13)0.0457 (7)
C120.4165 (5)0.08660 (16)0.56687 (13)0.0467 (7)
C130.2393 (6)0.02760 (17)0.58440 (14)0.0608 (8)
H130.1050900.0145960.5569040.073*
C140.2643 (8)−0.01169 (19)0.64321 (18)0.0798 (11)
H140.146956−0.0512870.6551310.096*
C150.4633 (7)0.0080 (2)0.68397 (16)0.0749 (10)
H150.479573−0.0178440.7235160.090*
C160.6353 (6)0.0654 (2)0.66607 (15)0.0720 (9)
H160.7693220.0786230.6935530.086*
C170.6131 (6)0.10419 (18)0.60755 (13)0.0584 (8)
H170.7335200.1427320.5957330.070*
C180.6977 (5)0.27017 (15)0.38316 (11)0.0424 (6)
C190.5970 (5)0.25345 (15)0.31761 (11)0.0397 (6)
C200.7241 (5)0.28491 (17)0.26662 (12)0.0531 (7)
H200.8688300.3163340.2737410.064*
C210.6356 (7)0.2695 (2)0.20559 (13)0.0652 (9)
H210.7172880.2926620.1716510.078*
C220.4308 (6)0.2211 (2)0.19454 (14)0.0650 (9)
H220.3768560.2090050.1530850.078*
C230.3028 (6)0.18975 (19)0.24420 (14)0.0629 (8)
H230.1598340.1575970.2364040.076*
C240.3859 (5)0.20591 (16)0.30599 (13)0.0508 (7)
H240.2987840.1845700.3396610.061*
  1. *Indicates the coordinates of the inverted lattice space to distinguish the positive lattice space.

Source of material

Acetophenone (0.5 mmol), di-tert-butyl peroxide (3 equiv.) and copper(II) iodide (0.05 mol) were added in a round bottom flask, and 4,4′-di-tert-butyl-2,2′-dipyridine (0.1 mol) were dissolved in chlorinated benzene (2.0 mL) and reflux reaction was carried out for 8 h [4]. There are many other ways to synthesize the target compound, such as using samarium compounds as catalysts [5], and para-substituted methoxy analogues [6]. The product was obtained by column chromatography eluting with petroleum ether and n-hexane 4:1. The resulting solution was evaporated to dryness to get some colorless crystals.

Experimental details

All hydrogen atoms were placed in the calculated positions and all the non-hydrogen atoms were refined anisotropically.

Comment

Intermolecular cyclotrimerization is one of the most effective methods to synthesize complex products from simple building blocks in one step [7]. The results of the regioselective formation of a variety of benzenes have made [2+2] ring trimers widely used in the synthesis of materials, drugs and biologically active compounds [8], [9]. The [2+2] and [2+2+2] cyclotrimerization of acetophenones provides a regioselective approach to poly-substituted compounds. Those processes occur under mild reaction conditions and produce water as a by-product.

In the crystal structure, bond lengths and angles are in the expected ranges. In detail, the C–C bonds in the cyclopropane moiety range from 1.494(3) to 1.513 Å.


Corresponding author: Chun-Yan Liu, School of Pharmacy, North China University of Science and Technology, 063210, Caofeidian District, Tangshan, P. R. China, E-mail:

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

  2. Research funding: None declared.

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

References

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Received: 2021-04-06
Accepted: 2021-04-22
Published Online: 2021-05-06
Published in Print: 2021-07-27

© 2021 Li Zeng et al., published by De Gruyter, Berlin/Boston

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

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