9-(4-Hy­droxy-3-meth­oxy­phen­yl)-3,3,6,6-tetra­methyl-1,2,3,4,5,6,7,8,9,10-deca­hydro­acridine-1,8-dione

Rajni Kant; Vivek K Gupta; Kamini Kapoor; D R Patil; P P Patil; Madhukar B Deshmukh

doi:10.1107/S1600536812050568

. 2012 Dec 15;69(Pt 1):o100. doi: 10.1107/S1600536812050568

9-(4-Hydroxy-3-methoxyphenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione

Rajni Kant ^a,^*, Vivek K Gupta ^a, Kamini Kapoor ^a, D R Patil ^b, P P Patil ^c, Madhukar B Deshmukh ^b

PMCID: PMC3588262 PMID: 23476363

Abstract

In the title molecule, C₂₄H₂₉NO₄, the central ring of the acridinedione system adopts a flat boat conformation and the four essentially planar atoms of this ring [maximum deviation = 0.001 (2) Å] form a dihedral angle of 85.99 (12)° with the benzene ring. The two outer rings of the acridinedione system adopt sofa conformations. In the crystal, O—H⋯O and N—H⋯O hydrogen bonds link the molecules, forming a two-dimensional network parallel to (100).

Related literature

For applications of acridines, see: Murugan et al. (1998 ▶); Josephrajan et al. (2005 ▶); Srividya et al. (1998 ▶,1996 ▶). For related structures, see: Balamurugan et al. (2009 ▶); Zhao & Teng (2008 ▶). For ring conformations, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C₂₄H₂₉NO₄
M _r = 395.48
Monoclinic,
a = 10.4828 (3) Å
b = 14.8973 (4) Å
c = 14.2059 (3) Å
β = 101.609 (2)°
V = 2173.09 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.970, T _max = 1.000
63634 measured reflections
4264 independent reflections
2958 reflections with I > 2σ(I)
R _int = 0.078

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.116
S = 1.02
4264 reflections
267 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Click here for additional data file.^{(30.1KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050568/lh5567sup1.cif

e-69-0o100-sup1.cif^{(30.1KB, cif)}

Click here for additional data file.^{(204.7KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050568/lh5567Isup2.hkl

e-69-0o100-Isup2.hkl^{(204.7KB, hkl)}

Click here for additional data file.^{(8.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812050568/lh5567Isup3.cml

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⋯O4ⁱ	0.82	2.12	2.800 (2)	141
N10—H10⋯O3ⁱⁱ	0.86	1.95	2.802 (2)	174

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

supplementary crystallographic information

Comment

Acridines, the earliest known antibiotics, are toxic towards bacteria. Some acridinedione derivatives show good inhibition against the pathogen Vibrio isolate-I (Josephrajan et al., 2005). Certain acridine-1,8-diones exhibit fluorescence activities (Murugan et al., 1998) and a few acridinedione derivatives also show photophysical (Srividya et al., 1998) and electrochemical properties (Srividya et al., 1996). Thus, the accurate description of crystal structures of substituted acridinediones are expected to provide useful information on the role of substituents in influencing molecular conformation which has a direct relationship to biological activity. This paper deals with the crystal structure of a 4-hydroxy-3-methoxyphenyl substituted tetramethyl acridinedione, (I).

In (I) (Fig.1), all bond lengths and angles are normal and correspond to those observed in related structures (Balamurugan et al.,2009; Zhao & Teng 2008). The central ring (C4A/C5A/C8A/C9A/C9/N10) of the acridinedione moiety adopts a boat conformation (ΔCs(N10) = 0.129 & ΔCs (C5A—C8A) = 10.84) and the four essentially planar atoms (C4A/C5A/C8A/C9A) of this ring (maximum deviation 0.001 (2)Å for all atoms) forms a dihedral angle of 85.99 (12)° with benzene ring. Both the outer rings adopt sofa conformations (ΔCs (C6) = 1.55; ΔCs (C3) = 7.45) (Duax & Norton, 1975). In the crystal, O1—H1···O4ⁱ and N10—H10···O3ⁱⁱ hydrogen bonds (Table 1) link molecules to form a two-dimensional network parallel to (100) (Fig. 2).

Experimental

In a 50 ml rounded bottom flask, a mixture of dimedone (2 mmole), 4-hydroxy, 3-methoxy benzaldehyde (1 mmole) and ammonium acetate (1.2 mmole) in mixture of aqueous ethanol (7 ml) was stirred at RT for 5 min. To this mixture 3-carboxymethyl-1-methylimidazolium(HSO₄) (20 mol%) was added and the reaction mixture heated at 348-353K for 1.5 hrs. The progress of reaction was monitored by TLC. After completion of reaction, the mixture was cooled to RT and poured on iced water under stirring, The precipitate was filter and dried. The crude product were recrystallized from ethanol to afford X-ray quality crystals. M.P.: 568–571 K, Yield: 82%. IR(KBr): 3274,3168,3049,1623,1511,1370 cm-1. 1H NMR(300 MHz, DMSO-d6): δ = 8.7(s,1H,OH);7.7 (s, 1H, NH); 6.7 (s, 1H, Ar—H); 6.5(s,2H,Ar—H); 4.7 (s, 1H, CH); 3.67 (s, 3H, OCH3); 2.4–2.0 (m, 8H, CH2); 1.0 (s, 6H, CH3); 0.9 (s,6H, CH3).