4-(8-Ethoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4-yl)butane-1-peroxol

In the title molecule, C18H23NO3, the hydroperoxybutyl substituent is nearly fully extended, with the four torsion angles in the range 170.23 (10)–178.71 (9)°. The O—O distance in the hydroperoxide group is 1.4690 (13) Å. This group acts as an intermolecular hydrogen-bond donor to a quinoline N atom. This results in dimeric units about the respective inversion centers, with graph-set notation R 2 2(18).

In the title molecule, C 18 H 23 NO 3 , the hydroperoxybutyl substituent is nearly fully extended, with the four torsion angles in the range 170.23 (10)-178.71 (9) . The O-O distance in the hydroperoxide group is 1.4690 (13) Å . This group acts as an intermolecular hydrogen-bond donor to a quinoline N atom. This results in dimeric units about the respective inversion centers, with graph-set notation R 2 2 (18).
Here we are reporting the characterization of that compound using 1 H-and 13 C-NMR spectroscopy, mass spectrometry, and single-crystal diffraction.
The molecular structure of the title compound is illustrated in Fig. 1. The 10-atom quinoline ring system is essentially planar, with mean deviation 0.009 Å and maximum deviation 0.017 (1) Å for both N1 and C11. The five-membered ring has the envelope conformation, with C9 at the flap position, 0.340 (2) Å out of the quinoline plane. The hydroperoxybutyl chain is extended, with torsion angle magnitudes in the range 170.23 (10) to 178.71 (9)°, and the best plane of its four C and two The hydroperoxide donates an intermolecular hydrogen bond to quinoline N1, with O···N distance 2.7466 (14) Å, forming discrete dimers having graph set (Etter, 1990) R 2 2 (18) about inversion centers, as illustrated in Fig. 2.

Experimental
The title compound was prepared by heating to reflux for three days, a mixture of p-phenitidine (500 mg, 3.6 mmol) and cyclopentanone (10 ml, large excess) in the presence of catalytic amounts of iodine (93 mg) and benzoyl peroxide (8.8 mg).
After appropriate work-up, and purification on a silica gel column, crystals were carefully grown at room temperature, in a mixture of hexanes-dichloromethane, over the course of a week.