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

Ali N Khalilov; Antar A Abdelhamid; Atash V Gurbanov; Seik Weng Ng

doi:10.1107/S1600536811013481

. 2011 Apr 16;67(Pt 5):o1146. doi: 10.1107/S1600536811013481

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

Ali N Khalilov ^a, Antar A Abdelhamid ^a, Atash V Gurbanov ^b, Seik Weng Ng ^c,^*

PMCID: PMC3089333 PMID: 21754454

Abstract

The dihydropyridine ring in the title compound, C₂₆H₃₂BrNO₄, adopts an envelope conformation with the methine C atom representing the flap. The cyclohexenone rings also adopt envelope conformations. The phenolic hydroxy group forms an intramolecular hydrogen bond to one of the two keto O atoms. Intermolecular weak C—H⋯O hydrogen bonding is present in the crystal structure. The hydroxypropyl group is disordered over two sets of sites with an occupancy ratio of 0.636 (6):0.364 (6).

Related literature

For a related structure, see: Abdelhamid et al. (2011 ▶).

Experimental

Crystal data

C₂₆H₃₂BrNO₄
M _r = 502.44
Monoclinic,
a = 10.6685 (4) Å
b = 16.8190 (5) Å
c = 14.1260 (5) Å
β = 106.303 (3)°
V = 2432.76 (14) Å³
Z = 4
Mo Kα radiation
μ = 1.72 mm⁻¹
T = 100 K
0.20 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.725, T _max = 0.919
11939 measured reflections
5402 independent reflections
3939 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.135
S = 1.03
5402 reflections
302 parameters
24 restraints
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013481/xu5192sup1.cif

e-67-o1146-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013481/xu5192Isup2.hkl

e-67-o1146-Isup2.hkl^{(264.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84	1.78	2.621 (4)	176
C10—H10A⋯O1ⁱ	0.99	2.54	3.417 (5)	147

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank Manchester Metropolitan University, Baku State University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

In an earlier study, we reported 10-(2-hydroxyethyl)-9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione, which was synthesized by the reaction of dimedone, salicyladehyde and 2-aminoethanol (Abdelhamid et al., 2011). In the present study, we replaced 2-aminoethanol by 1-amino-2-propanol and also used a bromine-subsituted salicyladehyde to form the title analog (Scheme I). The dihydropyridine ring in the C₂₆H₃₂BrNO₄ adopts an envelope conformation with the methine C atom representing the flap. The cyclohexenone rings also adopt envelope conformations with the C atoms bearing the methyl C atoms representing the flaps. The phenolic hydroxy group forms an intramolecular hydrogen bond to one of the two keto O atoms (Fig. 1).

Experimental

5-Bromo-2-hydroxybenzaldehyde (10 mmol), 1-amino-2-propanol (10 mol) and 20 dimedone (20 mmol) were heated in pyridine (50 ml) for 5 h. The solid that was isolated from the cool solution was collected and recrystallized from ethano; m.p. 508 K.