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

Chunbao Miao; Changsheng Yao; Shujiang Tu; Xiaoqiang Sun

doi:10.1107/S1600536808017212

. 2008 Jun 13;64(Pt 7):o1262. doi: 10.1107/S1600536808017212

3,3-Dimethyl-10-(4-methoxyphenyl)-9-(4-nitrophenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione¹

Chunbao Miao ^a, Changsheng Yao ^b, Shujiang Tu ^b, Xiaoqiang Sun ^a,^*

PMCID: PMC2961676 PMID: 21202896

Abstract

The title compound, C₂₈H₂₈N₂O₅, consists of a partially hydrogenated acridine ring system with two substituted phenyl substituents on the dihydropyridine ring which are both nearly perpendicular to the mean plane of the acridine unit [dihedral angles of 81.3 (1) and 89.6 (1)° between the central ring of acridine and the methoxyphenyl and nitrophenyl rings, respectively]. The dihydropyridine ring is almost planar, whereas both the outer unsymmetrical six-membered rings adopt half-chair conformations.

Related literature

For related literature, see: Ganesh et al. (1998 ▶); Jang et al. (2005 ▶); Shanmugasundaram et al. (1996 ▶); Wang et al. (2003 ▶). graphic file with name e-64-o1262-scheme1.jpg

Experimental

Crystal data

C₂₈H₂₈N₂O₅
M _r = 472.52
Monoclinic,
a = 12.463 (2) Å
b = 12.104 (2) Å
c = 16.408 (3) Å
β = 98.251 (5)°
V = 2449.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.80 × 0.59 × 0.58 mm

Data collection

Rigaku Mercury diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2001 ▶) T _min = 0.760, T _max = 0.950
23202 measured reflections
4466 independent reflections
3901 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.123
S = 1.17
4466 reflections
338 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: CrystalClear (Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017212/sg2245sup1.cif

e-64-o1262-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017212/sg2245Isup2.hkl

e-64-o1262-Isup2.hkl^{(218.8KB, hkl)}

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

Table 1. Selected bond lengths (Å).

O1—C6	1.227 (2)
O2—C12	1.222 (2)

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Acknowledgments

We thank the National Natural Science Foundation of China (No. 20272019)

supplementary crystallographic information

Comment

With a 1,4-DHP parent nucleus, acridine-1,8-diones have been shown to have very high lasing efficiencies and have been used as photoinitiators (Shanmugasundaram, et al., 1996). Symmetrical acridinediones which contain two identical cyclohexanone rings fused to the DHP rings have been reported (Ganesh, et al., 1998; Jang, et al., 2005; Wang, et al., 2003). However, the structures of acridinediones whose dihydropyridine ring linking two unsymmetrical cyclohexanone rings are rare. Here we report the structure of unsymmetrical acridinedione(I). It was synthesized by the reaction of 4-nitrobenzaldehydes, 3-(4-Methoxy-phenylamino)-5,5-dimethyl-cyclohex-2-enone and 1,3-cyclohexanedione in refluxing water.

The acridine moiety (Figure 1) is nearly coplanar; the dihedral angle between the aromatic ring which is linked to the carbon and pyridine ring is 81.31°; the dihedral angle between the aromatic ring linked to the nitrogen and pyridine ring is 89.57°. The packing arrangement in a unit cell of the title molecule is shown in Fig. 2.

Experimental

3,3-dimethyl-9-(4-nitrophenyl)-10-(4-methoxylphenyl)-decahydroacridine -1,8-dione were dissolved in ethanol. The mixture was set aside to crystallize. Suitable crystals for single-crystal X-ray diffraction were selected directly from the sample as prepared.