6-[(2-Hydroxyethyl)amino]-7H-dibenzo[de,h]quinolin-7-one

The title compound, C18H14N2O2, is a new oxoisoaporphine derivative synthesized by alkylation of 6-chloro-1-azabenzanthrone. The oxoisoaporphine fragment deviates significantly from planarity with a dihedral angle of 5.1 (1)° between the heterocycle and the remote benzene ring. The amino and oxo groups are involved in an intramolecular N—H⋯O hydrogen bond, while the hydroxy groups form intermolecular O—H⋯N hydrogen bonds, which link pairs of molecules into inversion dimers. In the dimer, two approximately parallel oxoisoaporphine fragments exhibit π–π interactions between the aromatic rings, the shortest centroid–centroid distance being 3.649 (3) Å.

The title compound, C 18 H 14 N 2 O 2 , is a new oxoisoaporphine derivative synthesized by alkylation of 6-chloro-1-azabenzanthrone. The oxoisoaporphine fragment deviates significantly from planarity with a dihedral angle of 5.1 (1) between the heterocycle and the remote benzene ring. The amino and oxo groups are involved in an intramolecular N-HÁ Á ÁO hydrogen bond, while the hydroxy groups form intermolecular O-HÁ Á ÁN hydrogen bonds, which link pairs of molecules into inversion dimers. In the dimer, two approximately parallel oxoisoaporphine fragments exhibit interactions between the aromatic rings, the shortest centroid-centroid distance being 3.649 (3) Å .

Related literature
For related oxoisoaporphine alkaloids, see: Tang et al. (2011Tang et al. ( , 2012. For background to the synthesis of 6-chloro-1-azabenzanthrone, see: Iwashima et al. (1984).  Table 1 Hydrogen-bond geometry (Å , ). Oxoisoaporphine alkaloids are known due to their pharmaceutical activities, such as antitumoral and antidemential activities. As a continuation of our study of novel oxoisoaporphine-based inhibitors (Tang et al., 2012), we present here the title compound (I), which is a new oxoisoaporphine synthesized by alkylation of 6-chloro-1-azabenzanthrone. It is structurally similar to the recently reported crystal structure of a new halogenated oxoisoaporphine by us, in which a chlorine atom replaced the 10-hydrogen atom but without substitution on the 6-position (Tang et al., 2012).

Experimental
In (I) (Fig. 1), the conjugated aromatic fragments of the oxoisoaporphine, including the heterocyclic isoquinoline and the remote benzene ring, is not entirely co-planar. The dihedral angle between the heterocycle of isoquinolinol and the remote benzene ring is 5.1 (1)°. The 2-hydroxyethylamino group on the 6-position of oxoisoaporphine plane is nearly vertical to the plane, with N2-C17-C18 bond angle of 113.18 (13)°. There exists intramolecular hydrogen bonds of N -H···O from the 7-carbonyl oxygen atom to the 6-imino group (-NH). Furthermore, every two oxoisoaporphines form a centrosymmetric dimer (Fig. 2), linked by intermolecular O-H···N hydrogen bonds (Table 1), in which N atom is the heterocyclic nitrogen atom of one oxoisoaporphine and O atom is the hydroxyethyl oxygen atom of another oxoisoaporphine. Each dimer is also stablized by π-π interaction between the two approximately parallel oxoisoaporphine fragments with the shortest centroid-centroid distance of 3.649 (3) Å.
Experimental 6-Chloro-1-azabenzanthrone (3.0 mmol), ethanolamine (15 mmol), and NaI (0.1 g) were mixed in pentanol. The mixture was stirred and refluxed for 8 h, and then cooled at room temperature. The mixture was diluted with chloroform and made basic by 5% KOH solution. The organic layer was washed with water and brine and dried over anhydrous MgSO 4 .

Figure 1
The molecular structure of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.  A hydrogen-bonded (dashed lines) dimer in (I). Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.