Home Crystal structure of 1,4-dibromo-2,5-bis(2-methoxyethoxy)benzene-1,4-diol, C12H16Br2O4
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Crystal structure of 1,4-dibromo-2,5-bis(2-methoxyethoxy)benzene-1,4-diol, C12H16Br2O4

  • Zhi-Yong Wang , Wan-Li Lu , Xu Zhou , Xian-Jiong Yang , Qi-Long Zhang ORCID logo EMAIL logo and Hong Xu
Published/Copyright: October 10, 2023

Abstract

C12H16Br2O4, monoclinic, P21/n (no. 14), a = 12.594(5) Å, b = 4.4613(16) Å, c = 12.878(4) Å, β = 91.209(12), V = 723.4(4) Å3, Z = 2, R gt(F) = 0.0450, wR ref(F 2) = 0.1103, T = 293 (2) K.

CCDC no.: 2297810

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 × 0.14 × 0.13 mm
Wavelength: MoKα radiation (0.71073 Å)
μ: 5.61 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 25.0°, 99 %
N(hkl)measured, N(hkl)uniqueR int: 4000, 1256, 0.066
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 883
N(param)refined: 83
Programs: Olex2 [1], Bruker [2], SHELX [3], Diamond [4]
Table 2:

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

Atom x y z U iso*/U eq
Br1 1.19091 (5) 0.22701 (13) 0.64583 (4) 0.0550 (3)
O2 0.7896 (3) 0.4046 (8) 0.5450 (3) 0.0479 (10)
O1 0.5907 (3) 0.3804 (9) 0.6528 (3) 0.0630 (11)
C1 0.4789 (5) 0.3470 (15) 0.6446 (6) 0.080 (2)
H1A 0.4577 0.3365 0.5726 0.119*
H1B 0.4452 0.5156 0.6764 0.119*
H1C 0.4582 0.1662 0.6791 0.119*
C2 0.6449 (5) 0.1354 (12) 0.6104 (4) 0.0488 (15)
H2A 0.6238 0.1116 0.5380 0.059*
H2B 0.6257 −0.0462 0.6470 0.059*
C3 0.7619 (5) 0.1801 (11) 0.6187 (4) 0.0443 (14)
H3A 0.7820 0.2440 0.6884 0.053*
H3B 0.7985 −0.0059 0.6039 0.053*
C4 0.8939 (4) 0.4446 (11) 0.5251 (4) 0.0364 (12)
C6 1.0814 (4) 0.3853 (11) 0.5603 (4) 0.0371 (12)
C5 0.9769 (4) 0.3302 (10) 0.5863 (4) 0.0393 (13)
H5 0.9622 0.2164 0.6447 0.047*

1 Source of materials

Weigh 2,5-dibromobenzene-1,4-diol (1.33 g, 5 mmol) and 2-bromoethyl methyl ether (3.48 g, 25 mmol) into a 100 mL circular bottom flask, add 60 mL of N, N-dimethylformamide, react at 100 C for 72 h, cool to room temperature, filter, remove solvent under reduced pressure, separate by column chromatography, and use dichloromethane as eluent to obtain a white solid. Take a small amount of the solid, dissolve it in ethanol, let it evaporate at room temperature for 7 days, and grow crystals.

2 Experimental details

Using Olex2 [1], the structure was solved using Charge Flipping and refined with the ShelXL [3] refinement. All hydrogen atoms were positioned geometrically, with the d(C–H) = 0.97–0.99 Å, U iso(H) = 1.2 times U eq(C) and U iso(H) = 1.5 times U eq(O).

3 Comment

The bromine atom of dibromobenzene is prone to react with vinyl pyridine to form compounds with large conjugated structures, which have excellent luminescent properties and have attracted the attention of researchers [5]. Modifying the alkyl chain on the benzene ring can regulate the hydrophobicity of the compound [6] and may be useful as an intermediate for synthesizing polymer materials [7]. The asymmetric unit of the title compound, C12H16Br2O4, contains one half molecule located around an inversion center. The bond lengths and bond angles are within the normal range, and literature reports that alkyl chains with similar structures have a serrated structure [8]. Due to the presence of oxygen atoms in the alkyl chain of this target compound, it is not a serrated structure. The molecules contain atypical C1–H1B⃛Br1 hydrogen bonds.


Corresponding author: Qi-Long Zhang, School of Basic Medical Science, Guizhou Medical University, Guiyang, 550025, People’s Republic of China, E-mail:

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

  2. Competing interest: The authors declare no conflicts of interest regarding this article.

  3. Research funding: This work was supported by the Science and Technology Foundation of Guizhou Province (grant number ZK[2022]395, 19NSP042, 26222030209), the Provincial General Project of University Student Innovation and Entrepreneurship Fund, China (No. 202210660048).

References

1. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

2. Bruker. APEX2, SAINT and SADABS; Bruker AXS Inc.: Madison, Wisconsin, USA, 2012.Search in Google Scholar

3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Cryst 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

4. Brandenburg, K. Diamond. Visual Crystal Structure Information System. Ver. 4.0; Crystal Impact: Bonn, Germany, 2015.Search in Google Scholar

5. Zhang, X., Su, S. Y., Chen, X. T., Shen, L. Y., Zhang, Q. L., Ni, X. L., Xu, H., Wang, Z. Y., Redshaw, C. A new cationic fluorescent probe for HSO3− based on bisulfite induced aggregation self-assembly. Molecules 2022, 27, 2378; https://doi.org/10.3390/molecules27082378.Search in Google Scholar PubMed PubMed Central

6. Zhang, R. Y., Niu, G. L., Li, X. C., Guo, L. F., Zhang, H. M., Yang, R., Chen, Y. C., Yu, X. Q., Tang, B. Z. Reaction-free and MMP-independent fluorescent probes for long-term mitochondria visualization and tracking. Chem. Sci. 2019, 10, 1994–2000; https://doi.org/10.1039/c8sc05119d.Search in Google Scholar PubMed PubMed Central

7. Vazquez-Molina, D. A., Pope, G. M., Ezazi, A. A., Mendoza-Cortes, J. L., Harper, J. K., Uribe-Romo, F. J. Framework vs. side-chain amphidynamic behaviour in oligo-(ethylene oxide) functionalised covalent-organic frameworks. Chem. Commun. 2018, 54, 6947–6950; https://doi.org/10.1039/c8cc04292f.Search in Google Scholar PubMed

8. Teh, C. H., Salleh, M. M., Tahir, M. I. M., Daika, R., Kassima, M. B. 1,4-Dibromo-2,5-dibutoxybenzene. Acta Cryst 2012, E68, o2683; https://doi.org/10.1107/s1600536812033338.Search in Google Scholar PubMed PubMed Central

Received: 2023-09-04
Accepted: 2023-09-27
Published Online: 2023-10-10
Published in Print: 2023-12-15

© 2023 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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