Home The crystal structure of 3-(1-fluoro-2-(naphthalen-2-yl)-2-oxoethyl)-2-methoxy-3,4-dihydroisoquinolin-1(2H)-one, C22H18FNO3
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The crystal structure of 3-(1-fluoro-2-(naphthalen-2-yl)-2-oxoethyl)-2-methoxy-3,4-dihydroisoquinolin-1(2H)-one, C22H18FNO3

  • Jiang-Bin Huang , Zhao Yin , Hai-Ping Wang ORCID logo EMAIL logo and Jia-Qiang Wu EMAIL logo
Published/Copyright: September 2, 2025

Abstract

C22H18FNO3, monoclinic, P21/n, (no. 14), a = 11.0201(3) Å, b = 7.3436(2) Å, c = 21.6386(6) Å, β = 94.376(2), V = 1746.05(8) Å3, Z = 4, R gt (F) = 0.0391, wR ref (F2) = 0.1090, T = 213 K.

CCDC no.: 2445379

The molecular structure is shown in the figure. Table 1 contains the crystallographic data and the list of the atoms including atomic coordinates and displacement parameters can be found in the cif-file attached to this article.

Table 1:

Data collection and handling.

Crystal: Clear light white plate
Size: 0.20 × 0.03 × 0.01 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 0.82 mm−1
Diffractometer, scan mode: Rigaku Synergy, ω scans
θmax, completeness: 78.6°, 100 %
N(hkl)measured, N(hkl)unique, Rint: 11495, 3518, 0.029
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2967
N(param)refined: 245
Programs: Bruker, 1 Shelx, 2 Olex2 3

1 Source of materials

N-Methoxybenzamide (30.2 mg, 0.2 mmol), 2,2-difluoro-1-(naphthalen-2-yl) but-3-en-1-one (69.6 mg, 0.3 mmol), Rh cat. (8.3 mg, 5 mol%), sodium dihydrogenphosphate (31.2 mg, 0.2 mmol), and MeOH (2 mL) were placed in a 10 mL glass tube. The mixture was stirred at 50 °C. After 24 h the mixture was concentrated in vacuo. The residue was purified through flash chromatography. Finally, the crude product was recrystallized from dichloromethane and hexane (2 mL/4 mL). Clear light white plate, yield 80.2 %.

2 Experimental details

The SHELXL 2 refinement package was employed to refine the crystal structure. The Olex2 3 was used to visualize the crystal structure. All hydrogen atoms were placed in idealized positions. Their Uiso values were set to 1.2Ueq of the parent atoms.

3 Comment

Fluorine chemistry is widely prevalent in the fields of organic chemistry and pharmaceutical chemistry. The introduction of fluorine atoms or fluorine-containing groups into biologically active compounds often alters their biological activity and physicochemical properties. 4 , 5 This unique characteristic of fluorine means that introducing fluorine atoms or fluorine-containing groups into molecular structures can significantly alter relevant molecular properties, including physical, chemical, and biological characteristics. 6 There are two main basic strategies for forming C–F bonds in organic fluorine compounds: fluorination and building block methods. 7 In addition, dihydroisoquinolinone series compounds exhibit numerous important biological activities such as antimalarial, 8 antitussive, 9 and antiparkinsonian properties, 10 and so on. We have enriched the library of fluorine-containing compounds by using a rhodium-catalyzed fluorine-modification method for the synthesis of dihydroisoquinoline derivatives.

In this study, the crystal structure was determined to gain a better understanding of its molecular conformation and intermolecular interactions. The title molecule, is shown in the figure. The bond distance of F1–C11 is 1.3926(15) Å. The bond lengths of O1–C1, O2–N1 and O3–C12 are 1.2284(16), 1.4025(14) and 1.2113(17) Å. The N1–O2–C10, and O2–N1–C9 angles are 110.32(11) and 112.69°, respectively, while those for C1–N1–C9 is 127.67(11)°. All of the hydrogen atoms were placed in the calculated positions. The bond lengths and angles within the molecule are within the expected ranges, indicating a well-ordered structure. 11 , 12


Corresponding author: Hai-Ping Wang, School of Environmental and Chemical Engineering, Wuyi University, Jiangmen, Guangdong, 529020, P.R. China, E-mail: ; and Jia-Qiang Wu, School of Pharmacy and Food Engineering, Wuyi University, Jiangmen, Guangdong, 529020, P.R. China, E-mail:
Jiang-Bin Huang and Zhao Yin contributed equally to this work.

Funding source: NSFC of China

Award Identifier / Grant number: 21901188

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

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

  3. Research funding: NSFC of China (21901188).

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Received: 2025-04-28
Accepted: 2025-07-02
Published Online: 2025-09-02
Published in Print: 2025-12-17

© 2025 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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