Home Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-(p-tolyl)furan, C23H23BrO2
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Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-(p-tolyl)furan, C23H23BrO2

  • Xue-Li Xu ORCID logo EMAIL logo and Jihong Li
Published/Copyright: July 29, 2021

Abstract

C23H23BrO2, monoclinic, P21/c (no. 14), a = 24.193(4) Å, b = 5.8614(10) Å, c = 13.873(3) Å, β = 93.168(3), V = 1964.3(6) Å3, Z = 4, R gt (F) = 0.0316, wR ref (F2) = 0.0915, T = 296(2) K.

CCDC no.: 2096421

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: 0.23 × 0.20 × 0.18 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 2.11 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint: 11421, 3446, 0.025
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2735
N(param)refined: 237
Programs: Bruker [1], SHELX [2]
Table 2:

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

Atom x y z Uiso*/Ueq
Br1 0.80538 (2) 1.43349 (4) 0.48348 (2) 0.05837 (13)
C1 0.79563 (10) 0.7833 (4) 0.73815 (16) 0.0444 (6)
C2 0.76754 (10) 0.8672 (4) 0.65802 (17) 0.0444 (6)
C3 0.71187 (10) 0.7817 (4) 0.65917 (17) 0.0443 (6)
C4 0.70978 (10) 0.6509 (4) 0.73957 (17) 0.0446 (6)
C5 0.85237 (10) 0.7944 (4) 0.77971 (17) 0.0442 (6)
C6 0.88782 (12) 0.9727 (5) 0.7614 (2) 0.0590 (7)
H6 0.875137 1.090814 0.721215 0.071*
C7 0.94177 (12) 0.9807 (5) 0.8012 (2) 0.0614 (7)
H7 0.964986 1.100834 0.786586 0.074*
C8 0.96056 (11) 0.8094 (5) 0.86247 (19) 0.0586 (7)
C9 0.92545 (12) 0.6305 (5) 0.8828 (2) 0.0609 (7)
H9 0.937952 0.514510 0.924245 0.073*
C10 0.87257 (11) 0.6236 (5) 0.84238 (18) 0.0522 (6)
H10 0.849606 0.502614 0.856966 0.063*
C11 1.04803 (14) 0.9908 (7) 0.8911 (3) 0.0909 (11)
H11A 1.055427 0.999513 0.823958 0.136*
H11B 1.082181 0.970264 0.928745 0.136*
H11C 1.030582 1.129354 0.910380 0.136*
C12 0.66853 (11) 0.5015 (4) 0.77978 (17) 0.0451 (6)
C13 0.61223 (11) 0.5440 (5) 0.7682 (2) 0.0569 (7)
H13 0.599808 0.673532 0.734945 0.068*
C14 0.57443 (12) 0.3972 (5) 0.8053 (2) 0.0625 (8)
H14 0.536855 0.429549 0.796664 0.075*
C15 0.59108 (11) 0.2030 (5) 0.85518 (19) 0.0567 (7)
C16 0.64687 (12) 0.1608 (5) 0.8672 (2) 0.0602 (7)
H16 0.658970 0.031381 0.900903 0.072*
C17 0.68540 (11) 0.3058 (5) 0.83044 (18) 0.0531 (6)
H17 0.722922 0.272755 0.839533 0.064*
C18 0.54915 (14) 0.0422 (6) 0.8964 (3) 0.0786 (10)
H18A 0.564734 −0.108086 0.902175 0.118*
H18B 0.516369 0.037798 0.854175 0.118*
H18C 0.539854 0.095433 0.958928 0.118*
C19 0.66637 (11) 0.8182 (5) 0.58225 (18) 0.0605 (7)
H19A 0.644691 0.679356 0.575172 0.073*
H19B 0.682870 0.846961 0.521274 0.073*
C20 0.62741 (14) 1.0176 (6) 0.6038 (2) 0.0694 (8)
H20 0.643218 1.147781 0.631967 0.083*
C21 0.57506 (16) 1.0176 (7) 0.5859 (3) 0.0918 (11)
H21A 0.557757 0.890465 0.557761 0.110*
H21B 0.554234 1.144762 0.601016 0.110*
C22 0.79033 (11) 1.0073 (4) 0.57863 (18) 0.0466 (6)
H22A 0.774486 0.954221 0.516896 0.056*
H22B 0.830102 0.985830 0.579059 0.056*
C23 0.77790 (12) 1.2574 (4) 0.58950 (19) 0.0578 (7)
H23A 0.794968 1.312255 0.650027 0.069*
H23B 0.738215 1.278718 0.591334 0.069*
O1 0.76068 (7) 0.6490 (3) 0.78880 (11) 0.0459 (4)
O2 1.01226 (8) 0.8026 (4) 0.90646 (15) 0.0781 (6)

Source of material

(4-Methoxyphenyl)(1-(p-tolylethynyl)cyclopropyl)methanone (0.2 mmol, 1.0 eq.), allyl bromide (0.4 mmol, 2.0 eq.), PdBr2 (0.03 eq.) and acetonitrile (5 mL) were added to a screw-capped Schlenk tube containing a magnetic stir bar, which was evacuated and refilled with nitrogen for three times. The resulting mixture was stirred at room temperature for 3 h. After the reaction was complete, the reaction mixture was concentrated under reduced pressure, and the residue was purified with petroleum ether-ethyl acetate (15:1, v/v) as eluent by silica gel chromatography column to obtain a colourless solid. Crystals were obtained by slow evaporation of a tetrahydrofuran solution at room temperature after three days.

Experimental details

All hydrogen atoms were placed in calculated positions (C–H = 0.93–0.97 Å) and refined as riding atoms. The Uiso values were set to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms.

Comment

In recent years, furans as an important class of heterocycles have always been a hot topic due to their wide use in drug science, material science, and synthetic chemistry [3], [4], [5], [6], [7], [8], [9]. Now, we report the synthesis and crystal structure of the title compound (cf. Figure).

In the crystal structure, the asymmetric unit consists of one molecule with bonding parameters in the normal ranges [10, 11]. The title compound is a non-planar molecule. The dihedral angles of A/B, A/C, B/B are 21.091(1), 22.889(1), and 30.229(1)°, respectively, in which A, B, C representing aromatic rings [C5/C6/C7/C8/C9/C10], [C12/C13/C14/C15/C16/C17], and furan ring [C1/C2/C3/C4/O1], respectively. The intermolecular and weak C–H⃛Br hydrogen bonds link molecules into chains.


Corresponding author: Xue‐Li Xu, School of Biological and Chemical Engineering, Nanyang Institute of Technology, 473004, Nanyang, Henan, People’s Republic of 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.

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Received: 2021-06-23
Accepted: 2021-07-14
Published Online: 2021-07-29
Published in Print: 2021-12-20

© 2021 Xue-Li Xu and Jihong Li, published by De Gruyter, Berlin/Boston

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

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