Home The crystal structure of (4-(2-bromoethoxy)-phenyl)(phenyl)methanone, C15H13BrO2
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The crystal structure of (4-(2-bromoethoxy)-phenyl)(phenyl)methanone, C15H13BrO2

  • Bofan Xu ORCID logo , Yuxing Ren and Zhenyu Zuo EMAIL logo
Published/Copyright: August 8, 2022

Abstract

C15H13BrO2, monoclinic, P21/c (no. 14), a = 5.6574(9) Å, b = 9.7821(16) Å, c = 24.251(4) Å, β = 93.265(4)°, V = 1339.9(4) Å3, Z = 4, R gt(F) = 0.0428, wR ref(F 2) = 0.0930, T = 273 K.

CCDC no.: 2176960

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: 0.19 × 0.17 × 0.15 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 3.06 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 28.5°, 99%
N(hkl)measured, N(hkl)unique, R int: 9101, 3338, 0.036
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2414
N(param)refined: 163
Programs: CrysAlis PRO [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
Br1 −0.04588 (5) 0.87602 (3) 0.43624 (2) 0.05795 (13)
O1 0.2492 (3) 0.60096 (17) 0.45573 (8) 0.0494 (5)
O2 0.4810 (4) 0.0087 (2) 0.37092 (10) 0.0732 (6)
C1 0.2513 (5) 0.8380 (3) 0.47695 (12) 0.0510 (7)
H1A 0.3485 0.9198 0.4780 0.061*
H1B 0.2204 0.8141 0.5147 0.061*
C2 0.3833 (5) 0.7244 (3) 0.45167 (11) 0.0468 (6)
H2A 0.4068 0.7448 0.4132 0.056*
H2B 0.5374 0.7137 0.4708 0.056*
C3 0.3308 (4) 0.4886 (3) 0.43006 (10) 0.0404 (5)
C4 0.1916 (4) 0.3713 (3) 0.43342 (12) 0.0484 (6)
H4 0.0553 0.3732 0.4531 0.058*
C5 0.2558 (5) 0.2533 (3) 0.40765 (12) 0.0490 (6)
H5 0.1635 0.1752 0.4105 0.059*
C6 0.4567 (4) 0.2487 (3) 0.37740 (11) 0.0445 (6)
C7 0.5256 (5) 0.1191 (3) 0.35046 (12) 0.0514 (6)
C8 0.6517 (5) 0.1263 (3) 0.29837 (12) 0.0508 (6)
C9 0.8241 (6) 0.0312 (4) 0.28794 (14) 0.0719 (9)
H9 0.8603 −0.0375 0.3135 0.086*
C10 0.9426 (8) 0.0375 (4) 0.23996 (16) 0.0887 (12)
H10 1.0606 −0.0259 0.2337 0.106*
C11 0.8877 (8) 0.1367 (4) 0.20143 (15) 0.0836 (11)
H11 0.9675 0.1398 0.1690 0.100*
C12 0.5958 (4) 0.3649 (3) 0.37511 (11) 0.0469 (6)
H12 0.7313 0.3628 0.3551 0.056*
C13 0.5376 (4) 0.4835 (3) 0.40180 (11) 0.0466 (6)
H13 0.6359 0.5595 0.4009 0.056*
C14 0.7176 (8) 0.2303 (4) 0.21048 (13) 0.0751 (10)
H14 0.6798 0.2970 0.1841 0.090*
C15 0.6003 (6) 0.2264 (3) 0.25880 (12) 0.0612 (8)
H15 0.4853 0.2917 0.2650 0.073*

Source of material

4-Hydroxybenzophenone (1.98 g, 10 mmol), 1,2-dibromoethane (9.4 g, 50 mmol) and K2CO3 (4.1 g, 30 mmol) were added to 60 mL of acetone at room temperature. The mixture was refluxed for 48 h and then cooled to room temperature. The reaction solution was filtered and the filtrate evaporated under reduced pressure to get an yellow oil. The product was purified by silica gel column chromatography (dichloromethane as the eluent) to obtain a white solid, which is recrystallized from methanol to obtain a white block crystal.

Experimental details

The data were scaled and corrected for absorption using SADABS-2016/2 [2, 3]. The hydrogen atoms were placed at calculated positions as riding atoms.

Comment

With the advantages of simple synthesis and low price, benzophenone derivatives were widely used in the areas of photoinitiator [4], sunscreen [5], [6], [7], photoluminescent materials [8, 9], organic field-effect transistor [10], pesticide [11] and so on. In the field of hydrogen scavenging photoinitiator, different fuctional groups (such as acryloyl, acylamino, propargyl ect.) can be introduced into the backbone of benzophenone to improve photoinitiating activities [12], [13], [14]. So design, synthesis and photoinitiation activity study of novel benzophenone derivatives obviously become an important subject. Due to the bromine atom at the end of the skeleton in the title molecular structure, water-soluble photoinitiators with novel structures can be prepared using (4-(2- bromoethoxy)phenyl)(phenyl)methanone as reactant in a nucleophilic reaction (introducing polysiloxane or quaternary ammonium ions) [15].

In the structure of the title molecule, the bond length of C1–Br1 is 1.937(3) Å. The bond lengths of C2–O1, C7–O2 and C12–C13 are 1.433(3), 1.220(3) and 1.377(4) Å respectively, which are in normal range [16]. A comparison of the corresponding torsion angle of 121.32° in the molecular structure of benzophenone [17], showed that the torsion angle of C15–C8–C7–C6 36.005° in the title structure is relatively small. In molecular packing, non-classical hydrogen bond was observed as following: C14–H14⋯O2 (d(H14⋯O2) = 2.60 Å.


Corresponding author: Zhenyu Zuo, College of Pharmacy, Shaanxi University of Chinese Medicine, Xi’an, Shaanxi, 712046, China, E-mail:

Funding source: Key project of Shaanxi Provincial Education Department

Award Identifier / Grant number: 20JS033

Funding source: Key R & D projects of Shaanxi Province

Award Identifier / Grant number: 2021SF-366

Funding source: Cultivation project of Shaanxi University of Chinese Medicine

Award Identifier / Grant number: 2016PY16

Acknowledgments

We acknowledge the supports by Key project of Shaanxi Provincial Education Department (20JS033), Key R & D projects of Shaanxi Province (2021SF-366). Cultivation project of Shaanxi University of Chinese Medicine (2016PY16).

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

  2. Research funding: Key project of Shaanxi Provincial Education Department (20JS033), Key R & D projects of Shaanxi Province (2021SF-366). Cultivation project of Shaanxi University of Chinese Medicine (2016PY16).

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

References

1. Rigaku Oxford Diffraction. CrysAlisPro 1.171.39.46, 2018.Search in Google Scholar

2. Sheldrick, G. M. SHELXTL – Integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Search in Google Scholar

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. Cesur, B., Karahan, O., Agopcan, S., Eren, T. N., Okte, N., Avci, D. Difunctional monomeric and polymeric photoinitiators: synthesis and photoinitiating behaviors. Prog. Org. Coating 2015, 86, 71–78; https://doi.org/10.1016/j.porgcoat.2015.04.010.Search in Google Scholar

5. Felix, T., Hall, B. J., Brodbelt, J. S. Determination of benzophenon-3 and metabolites in water and human urine by solid-phase microextraction and quadrupole ion trap GC–MS. Anal. Chim. Acta 1998, 371, 195–203.10.1016/S0003-2670(98)00293-1Search in Google Scholar

6. Zenker, A., Schmutz, H., Fent, K. Simultaneous trace determination of nine organic UV-absorbing compounds (UV filters) in environmental samples. J. Chromatogr. A 2008, 1202, 64–74; https://doi.org/10.1016/j.chroma.2008.06.041.Search in Google Scholar PubMed

7. Yu, S., Du, J., Zheng, Y., Yan, L. Synthesis and characterization of carboxymethyl chitosan containing functional ultraviolet absorber substituent. J. Appl. Polym. Sci. 2007, 106, 4098–4103; https://doi.org/10.1002/app.26947.Search in Google Scholar

8. Idelson, A., Sterzenbach, C., Jester, S.-S., Tschierske, C., Baumeister, U., Höger, S. A liquid-crystalline phenylene-based shape persistent molecular spoked wheel. J. Am. Chem. Soc. 2017, 139, 4429–4434; https://doi.org/10.1021/jacs.6b13020.Search in Google Scholar PubMed

9. Xu, J., Zhu, X., Guo, J., Fan, J., Zeng, J., Chen, S., Zhao, Z., Tang, B. Z. Aggregation-induced delayed fluorescence luminogens with accelerated reverse intersystem crossing for high-performance OLEDs. ACS Mater. Lett. 2019, 1, 613–619; https://doi.org/10.1021/acsmaterialslett.9b00369.Search in Google Scholar

10. Wang, K., Dong, H., Zhou, D., Ito, Y., Hu, L., Zhang, Z., Zhu, X. Facile fabrication of semiconducting single walled carbon nanotubes patterns on flexible substrate based on a photoimmobilization technique. ACS Appl. Mater. Interfaces 2020, 12, 8722–8729; https://doi.org/10.1021/acsami.9b21142.Search in Google Scholar PubMed

11. Micale, N., Sarrob, G. D., Ferrerib, G., Zappalá, M., Grasso, S., Puiac, G., Micheli, C. D. Design of 1-substituted 2-arylmethyl-4, 5-methylenedioxybenzene derivatives as antiseizure agents. Bioorg. Med. Chem. 2004, 12, 3703–3709; https://doi.org/10.1016/j.bmc.2004.04.015.Search in Google Scholar PubMed

12. Karahana, Ö., Baltab, D. K., Arsub, N., Avcia, D. Synthesis and evaluations of novel photoinitiators with side-chainbenzophenone, derived from alkyl-hydroxymethacrylates. J. Photochem. Photobiol. A 2014, 274, 43–49; https://doi.org/10.1016/j.jphotochem.2013.09.010.Search in Google Scholar

13. Wei, J., Wang, B. A highly efficient polymerizable photoinitiator comprising benzophenone, thio moieties, and n-arylmaleimide. Macromol. Chem. Phys. 2011, 212, 88–95; https://doi.org/10.1002/macp.201000535.Search in Google Scholar

14. Roth, M., Hennen, D., Oesterreicher, A., Mostegel, F. H., Kappaun, S., Edler, M., Griesser, T. Exploring functionalized benzophenones as low-migration photoinitiators for vinyl carbonate/thiol formulations. Eur. Polym. J. 2017, 88, 403–411; https://doi.org/10.1016/j.eurpolymj.2016.11.004.Search in Google Scholar

15. Wang, J., Cheng, J., Liu, J., Gao, Y., Sun, F. Self-floating ability and initiating gradient photopolymerization of acrylamide aqueous solution of a water-soluble polysiloxane benzophenone photoinitiator. Green Chem. 2013, 15, 2457–2465; https://doi.org/10.1039/c3gc40704g.Search in Google Scholar

16. Zuo, Z., Hu, K., Song, X., Zhang, H., Tang, Z. The crystal structure of 1,5-di(naphthalen-2-yl)-3-(pyridin-2-yl)pentane-1,5-dione, C30H23NO2. Z. Kristallogr. N. Cryst. Struct. 2019, 2345, 325–326; https://doi.org/10.1515/ncrs-2018-0378.Search in Google Scholar

17. Bernstein, J., Ellern, A., Henck, J.-O. CCDC 118986. Experimental Crystal Structure Determination; Cambridge Crystallographic Data Centre: Cambridge, 2002. https://doi.org/10.5517/cc3zt84.Search in Google Scholar

Received: 2022-06-20
Accepted: 2022-07-15
Published Online: 2022-08-08
Published in Print: 2022-10-26

© 2022 the author(s), published by De Gruyter, Berlin/Boston

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

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