9-(3-Bromo-5-chloro-2-hydroxyphenyl)-10-(2-hydroxyethyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione

In the title compound, C21H21BrClNO4, the dihydropyridine ring adopts a flattened boat conformation. The 3-bromo-5-chloro-2-hydroxyphenyl ring forms a dihedral angles of 84.44 (7)° with the dihydropyridine mean plane. 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 and C—H⋯O hydrogen bonds link the molecules, forming a three-dimensional network.

In the title compound, C 21 H 21 BrClNO 4 , the dihydropyridine ring adopts a flattened boat conformation. The 3-bromo-5chloro-2-hydroxyphenyl ring forms a dihedral angles of 84.44 (7) with the dihydropyridine mean plane. 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 and C-HÁ Á ÁO hydrogen bonds link the molecules, forming a three-dimensional network.
The molecular conformation 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 and C-H···O hydrogen bonds, forming three dimensional network Table 1).

Experimental
A mixture of 112 mg (0.001 mol) cyclohexane-1,3-dione, 236 mg (0.001 mol) 3-bromo-5-chloro-2-hydroxybenzaldehyde and 61 mg (0.001 mol) 2-aminoethanol in 50 ml ethanol was refluxed at 350 K and monitored by TLC till completion after 2 h. A mass solid precipitate was deposited on cooling, filtered and dried under vacuum then washed with cold ethanol and dried again.. The raw product was recrystallized from dimethyl formamide then triturated with ether to afford a good yield (73%) of high quality yellow plats (m.p. 483 K) that were suitable for X-ray difraction.

Refinement
All H-atoms were placed in calculated positions with O-H = 0.84 Å, and C-H = 0.95 for aromatic, 0.99 for methylene and 1.00 Å for methine C-H = 0.97 Å for methylene U iso (H) = 1.2 U eq (C). They were refined using a riding model approximation with U iso (H) = 1.5U eq (O) for hydroxyl and U iso (H) = 1.2 U eq (C) for the other H atoms.

Special details
Experimental. Rigaku CrystalClear-SM Expert 3.1 b5 Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs 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.