The crystal structure of N -(acridin-9-yl)-4-chloro- N - (4-chloro-butanoyl) butanamide, C 21 H 20 Cl 2 N 2 O 2

C 21 H 20 Cl 2 N 2 O 2 , orthorhombic, P 2 1 (no. 4), a = 8.3667(14) Å, b = 15.444(3) Å, c = 15.105(2) Å, V = 1951.9(6) Å 3 , Z = 4, R gt ( F ) = 0.0481, wR ref ( F 2 ) = 0.1574, T = 292 K.


Source of materials
The 9-aminoacridine (0.97 g, 5 mmol) and triethylamine (2.75 ml, 25 mmol) was initially added to 15 mL tetrahydrofuran.Subsequently, the 4-chloro-butyryl chloride (3.5 ml, 25 mmol) was slowly added to the reaction mixture and continued stirring for 120 min at 0 °C.The solvent was removed under reduced pressure and the solid product was dissolved in ethyl acetate.The solids were removed by vacuum filtration, and the filtrate was washed with 100 ml sodium carbonate solution (10 %).The ethyl acetate was removed under reduced pressure to give a solid-liquid mixture.The pure product was obtained by washing the above mixture with ethanol.The solid product was recrystallized from 10 mL of anhydrous diethyl ether.Colorless block crystals were obtained after one day.

Experimental details
The structure was solved by Direct Methods and refined with the SHELX [1,2] crystallographic software package.
Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.The crystal structure was visualized by OLEX2 software package.

Comment
The monosubstituted derivatives of 9-aminacridine have good activity as LSD1 inhibitors [3].In order to investigate the inhibitory activity of 9-aminoacridine bissubstituted derivatives on LSD1, we synthesized a series of compounds, one of which is the title compound.Due to the imide isomeric form of 9-aminoacridine, the location of acylation of the title compound cannot be determined by Nuclear Magnetic Resonance [4,5].Single crystal diffraction is an effective and intuitive method for determining the structure of compounds [6][7][8].
Acknowledgments: The Analysis and Testing Center of Zhengzhou University is acknowledged for the single crystal X-ray diffraction facility.Author contributions: The synthesis of compounds and crystal preparation were completed by Dan Zhou, while the data analysis, writing and revision of the paper were

Table  :
Data collection and handling.

Table  :
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å  ). completed by Chen-Yang Jing, Dan Zhou and Yu-Qian Kan; supervision, Wen Li.All authors have read and agreed to the published version of the manuscript.Competing interests: The authors declare no conflicts of interest regarding this article.Research funding: This work was supported by the Key Technologies R & D Program of Henan Province of China (No. 222102310279 for WL) and Sinopharm Scholarship of Zhengzhou University (For XYZ).