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

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

doi:10.1107/S1600536811006969

. 2011 Feb 26;67(Pt 3):o744. doi: 10.1107/S1600536811006969

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

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

PMCID: PMC3051986 PMID: 21522483

Abstract

The dihydropyridine ring in the title compound, C₂₅H₃₁NO₄, 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. The hydroxy group of the N-bonded alkyl chain forms an intermolecular hydrogen bond to the other keto O atom of an adjacent molecule. The latter hydrogen bond leads to the formation of a helical chain running along the b axis.

Related literature

For a related structure, see: Jang et al. (2005 ▶).

Experimental

Crystal data

C₂₅H₃₁NO₄
M _r = 409.51
Monoclinic,
a = 9.7037 (2) Å
b = 16.5123 (3) Å
c = 13.8847 (3) Å
β = 102.132 (3)°
V = 2175.06 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.979, T _max = 0.988
19082 measured reflections
4915 independent reflections
3770 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.123
S = 1.03
4915 reflections
279 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.26 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/S1600536811006969/im2270sup1.cif

e-67-0o744-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006969/im2270Isup2.hkl

e-67-0o744-Isup2.hkl^{(240.7KB, 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)	1.84 (1)	2.659 (2)	166 (2)
O4—H4⋯O3ⁱ	0.85 (1)	1.98 (1)	2.818 (2)	166 (2)

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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

Substituted benzaldehydes react with dimedone along with a primary amine to yield N-substituted 1,2,3,4,5,6,7,8,9,10-decahydro-acridine-1,8-diones. The title compound has a hydroxy group in 2-position of the aromatic ring. This permits intramolecular hydrogen bonding, a feature also noted in the related 9-(2,6-dihydroxyphenyl)-3,3,6,6-tetramethyl-N-(4-methylphenyl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahydroacridine (Jang et al., 2005). The second hydroxy unit in this case engages in intermolecular hydrogen bonding to afford a centrosymmetric dimer. The title compound (Scheme I, Fig. 1) has another hydroxy unit in the N bonded hydroxyethyl substituent. This groups engages in intermolecular hydrogen bond furnishing a linear chain that runs along the c-axis of the monoclinic unit cell.

Experimental

Dimedone (20 mmol), salicylic aldehyde (10 mmol) and 2-amino-ethanol (10 mmol) were heated in ethanol (100 ml) for 5 h. After cooling the solution the product was collected by filtration and crystallized from ethanol; m.p. 462 K.