9-(3-Bromo-5-chloro-2-hydroxyphenyl)-10-(2-hydroxyethyl)-3,6-diphenyl-3,4,9,10-tetrahydroacridine-1,8(2H,5H)-dione

In the title compound, C33H27BrClNO4, the dihydropyridine ring adopts a flattened boat conformation. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen bond, with an S(8) ring motif. In the crystal, O—H⋯O, C—H⋯O and C—H⋯Cl hydrogen bonds, and C—H⋯π interactions link the molecules, forming a three-dimensional network. In the acridinedione ring system, the two ring C atoms at the 2- and 3-positions, and the C atom at the 6-position and the atoms of the phenyl ring attached to the C atom at the 6-position are disordered over two sets of sites with occupancy ratios of 0.783 (5):0.217 (5) and 0.526 (18):0.474 (18), respectively.

In the title compound, C 33 H 27 BrClNO 4 , the dihydropyridine ring adopts a flattened boat conformation. The molecular conformation is stabilized by an intramolecular O-HÁ Á ÁO hydrogen bond, with an S(8) ring motif. In the crystal, O-HÁ Á ÁO, C-HÁ Á ÁO and C-HÁ Á ÁCl hydrogen bonds, and C-HÁ Á Á interactions link the molecules, forming a threedimensional network. In the acridinedione ring system, the two ring C atoms at the 2-and 3-positions, and the C atom at the 6-position and the atoms of the phenyl ring attached to the C atom at the 6-position are disordered over two sets of sites with occupancy ratios of 0.783 (5):0.217 (5) and 0.526 (18):0.474 (18), respectively.
The molecular conformation of (I) is stabilized by an intramolecular O-H···O hydrogen bond (Table 1), which forms a pseudo-eight-membered ring with graph set S(8) (Bernstein et al., 1995).
In the crystal, molecules are linked by O-H···O, C-H···O and C-H···Cl hydrogen bonds, forming three dimensional network (Table 1, Fig. 2). Furthermore, C-H···π interactions (Table 1) contribute to the stabilization of the molecular packing.

Experimental
A mixture of 1 mmol (235 mg) of 3-bromo-5-chloro-2-hydroxybenzaldehyde, 2 mmol (372 mg) of 5-phenylcyclohexane-1,3-dione and 1 mmol (61 mg) of 2-aminoethanol in 30 ml e thanol was refluxed for 2 h at 350 K. The reaction mixture was cooled at ambient temperature and the precipitated product was filtered off, washed with cold ethanol and recrystallized from ethanol. Suitable crystals for X-ray diffractions were obtained by slow evaporation method of an ethanolic solution of (I) at room temperature over two days.

Refinement
The hydroxyl H atoms were found from a difference Fourier map [O2-H2O = 0.873 (19) Å and O4-H4O = 0.826 (17) Å]. Their coordinates were freely refined and U iso (H) were set to 1.5U eq (O). The H atoms attached to C2 and C12 were located in a difference map and refined freely. The other H-atoms were placed in calculated positions and refined by using a riding model with C- In the 3,4,9,10-tetrahydroacridine-1,8(2H,5H)-dione ring system, the two ring C atoms (C3 and C4) at the 2 and 3poisitions are disordered over two positions with the site occupancy factors of 0.783 (5) and 0.217 (5). For the C4A and C4B atoms of disorder, the EXYZ instruction was used in the refinement.
The C atom (C11) at the 6-positions of the mentioned ring system and the atoms of the phenyl ring (C28-C33) attached to the C11 atom are disordered over two positions; the site occupancy factors are 0.526 (18) and 0.474 (18).
The atoms of disorder were set to equal each other by an EADP. The disordered phenyl ring (C28A/B-C33A/B) was constrained to a rigid hexagon with the AFIX 66 instruction, and the SIMU and DELU instructions were used in the refinement procedure.

Figure 1
View of the title compound with 30% probability displacement ellipsoids. Only the major components of the disorders are shown.  Perspective view of the hydrogen bonding and packing of the title compound. Only the major components of the disorders are shown.  130.1 (15) C25-C20-C7 120.6 (2) C3A_a-C2-H2B